 Photostable, silylated benzotriazole UV absorbers and compositions stabilized therewith
专利摘要:
The present invention relates to photostable silylated benzotriazole compounds of formula (I) or formula (II). Formula I Formula II In Formula I and Formula II above, At least one of E 1 , E 2 , E 5 , E 8 , E 9 , G 2 and G 7 is a silylated group, G 2 and / or G 7 are electron attracting residues. The compounds of the present invention are photostable and especially miscible in high performance coatings such as organopolysiloxanes. 公开号:KR20030022347A 申请号:KR10-2003-7001515 申请日:2001-07-26 公开日:2003-03-15 发明作者:라비찬드란라마나탄；수하돌닉죠셉；우드머빈게일；슝룽 申请人:시바 스페셜티 케미칼스 홀딩 인크.； IPC主号:
专利说明:
Photostable, silylated benzotriazole UV absorbers and compositions stabilized therewith} [1] The present invention relates to photostable silylated benzotriazole UV absorbers and compositions stabilized using the same. Benzotriazole compounds are novel compounds and exhibit improved durability due to the introduction of electron attracting moieties at the 5 position of the benzo ring. Polymer compositions containing such benzotriazoles are advantageously stable, especially high performance coatings such as organopolysiloxanes. Compounds of the invention are red shifted and exhibit increased absorbance in the 350-400 nm region of the UV spectrum. [2] U. S. Patent No. 4,859, 759 describes siloxane compounds containing at least one benzotriazole and one hindered amine substituent covalently bonded to a silicon atom in the most general manner. The patent does not provide any specific examples of such structures. Certain structures of the invention are not described or suggested in the above patents. [3] U.S. Patents 5,707,690 and 5,756,793 describe the use of silylated benzophenones for protective coatings on wood. European Patent Publication 675,108 B1 describes thioether substituted benzophenone UV absorbers which may also contain silylated substituents. [4] US Pat. Nos. 5,185,445 and 5,837,792 describe polysiloxane light stabilizers containing pendant hydroxyphenyl-diaryl-s-triazine residues. [5] U.S. Pat.Nos. 5,219,905, 5,321,066, 5,418,267, 5,463,058 and 5,578,665 describe hindered amines containing siloxanes and other silyl moieties as stabilizers. [6] U.S. Pat.Nos. 5,391,795 and 5,679,820 describe the preparation of silylated benzophenone UV absorbers and their use. U.S. Patent No. 5,391,795 discloses these silylated benzophenone UV absorbers with silyl, which is 2- {2-hydroxy-5- [3- (3-triethoxysilyl) propylcarbamoyloxy] propylphenyl} -2H-benzotriazole. Compared with the example of the benzotriazole UV absorber. The silylated benzotriazole compound does not contain a bulky substituent in the ortho position relative to the hydroxy group in the phenyl ring and does not contain an electron withdrawing group at the 5 position of the benzo ring. These two substitution patterns have been found to be particularly effective in improving the long term photostability of benzotriazoles. The electron attracting group present at the 5 position of the benzo ring enables the red shift of the UV spectrum of the benzotriazole. [7] U.S. Patent 4,373,061 describes the use of silicone coatings for unprimed plastic substrates and coated articles. The silicone coating contains UV absorbing organic groups bonded to silicon by carbon-silicon bonds. UV absorbers are silylated hydroxybenzophenones. [8] U. S. Patent No. 4,322, 455 describes a method of making an ultraviolet radiation stabilized polymer article containing a UV absorbing composition on the surface of the article. UV absorbers can generally be any known class of compounds, such as benzophenone, benzotriazole, cyanoacrylate or benzylidene malonate, and the like. The only benzotriazoles described are 2- (2-hydroxy-5-tert-octylphenyl) -2H-benzotriazole. [9] US Pat. No. 6,166,218 demonstrates the usefulness that bulky groups are substituted at the 3 position of the phenyl ring and electron attracting residues are substituted at the 5 position of the benzo ring. All of these compounds have an electron withdrawing moiety at the 5 position of the benzo ring. In the case of having a bulky substituent, in particular an α-cumyl group, at the 3-position of the phenyl ring, the light stability of benzotriazole is particularly improved. [10] It is a first object of the present invention to provide a novel monomeric benzotriazole UV absorber containing silicon moieties. [11] Another object of the present invention is to provide a silicone / siloxane hardcoat or softcoat resin composition containing a benzotriazole UV absorber that can be added to or copolymerized with such hardcoat or softcoat resins. [12] It is a further object of the present invention to provide a product containing a silicone / siloxane hardcoat or softcoat composition as barrier layer in a laminate composition as on polycarbonate. [13] Another object of the present invention is to provide an automotive coating composition wherein the compound is a melamine / siloxane crosslinked structure. [14] Another object of the present invention is to provide a polymer composition in which the compound is used in combination with silylated hindered amines, in particular comprising h-amines substituted with N-hydrocarbyloxy and N-hydroxyalkyloxy. [15] Another object of the present invention is a silicone containing other improved benzotriazole after addition which does not contain a silicon moiety in the presence or absence of a hindered amine, N-hydrocarbyloxy or N-hydroxyalkyloxy substituted hindered amine. To provide a siloxane hardcoat or softcoat composition. [16] The present invention relates to benzotriazole compounds of formula (I) or formula (II). [17] [18] [19] In Formula I and Formula II above, [20] G 1 and G 6 are independently hydrogen or halogen, [21] G 2 and G 7 are independently cyano, perfluoroalkyl having 1 to 12 carbon atoms, fluoro, chloro, -CO-G 3 , -COOG 3 , -CONHG 3 , -CON (G 3 ) 2 , E 3 SO-, E 3 SO 2- , -PO (C 6 H 5 ) 2 , [22] , [23] -CO-XT 1 -O-CO-NH-T 2 -Si (OR 2 ) n (R 1 ) 3-n or -CO-XT 1 -Si (OR 2 ) n (R 1 ) 3-n, or [24] G 7 is hydrogen, [25] G 2 may be hydrogen when E 1 is a group of Formula IV or Formula V, [26] T 1 and T 2 are independently alkylene having 1 to 18 carbon atoms, preferably alkylene having 2 or 3 carbon atoms or alkylene-phenylene-alkylene having 8 to 20 carbon atoms, [27] R 1 and R 2 are independently alkyl having 1 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, aryl having 6 to 10 carbon atoms or phenylalkyl having 7 to 20 carbon atoms, preferably alkyl having 1 to 6 carbon atoms or phenyl; , [28] n is 0, 1, 2 or 3, [29] X is -O-, -NE 4 -or -NH-, [30] G 3 is hydrogen, straight or branched chain alkyl having 1 to 24 carbon atoms, straight or branched chain alkenyl having 2 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, phenylalkyl having 7 to 15 carbon atoms, phenyl, or phenyl ring having 1 to 24 carbon atoms. Phenyl or phenylalkyl above substituted with 1-4 alkyl of 4, [31] E 1 is hydrogen, straight or branched chain alkyl having 1 to 24 carbon atoms, straight or branched chain alkenyl having 2 to 24 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, phenylalkyl having 7 to 15 carbon atoms, phenyl, or phenyl ring having 1 to 24 carbon atoms. Or substituted with one to four alkyl of 4 or one or more of the formulas -T 1 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -XT 1 -Si (OR 2 ) n (R 1 ) 3-n or -XT 1- Or phenyl or phenylalkyl above substituted with a group of X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , [32] E 1 is alkyl having 1 to 24 carbon atoms substituted with 1 or 2 hydroxy groups, [33] E 2 and E 9 are independently hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, or The phenyl ring is substituted with 1 to 3 alkyl of 1 to 4 carbon atoms or one or more of the formulas -T 1 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -XT 1 -Si (OR 2 ) n (R 1 ) 3-n Or phenyl or phenylalkyl above substituted with a group of -XT 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , or [34] E 2 and E 9 are independently one or more -OH, -OCOE 11 , -OE 4 , -NCO, -NH 2 , -NHCOE 11 , -NHE 4 , -N (E 4 ) 2 or mixtures thereof, wherein E 4 is straight-chain or branched alkyl having 1 to 24 carbon atoms) or alkyl of 1 to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms, or one or more -O-, -NH-, -NE 4 -Alkyl or alkenyl above, blocked with a group or a mixture thereof and unsubstituted or substituted with one or more -OH, -OE 4 , -NH 2 groups or mixtures thereof, or [35] E 1 , E 2 and E 9 are independently -T 1 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n or —T 1 —CO—XT 2 —Si (OR 2 ) n (R 1 ) 3-n , [36] E 11 is hydrogen, straight or branched chain alkyl of 1 to 18 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aryl of 6 to 14 carbon atoms, or phenylalkyl of 7 to 15 carbon atoms, [37] L is alkylene having 1 to 12 carbon atoms, alkylidene having 2 to 12 carbon atoms, benzylidene, p-xylylene, cycloalkylidene having 5 to 12 carbon atoms, or α, α, α ', α'-tetramethyl-m Xylylene, [38] E 3 is alkyl having 1 to 20 carbon atoms substituted with alkoxycarbonyl having 2 to 9 carbon atoms, hydroxyalkyl having 2 to 20 carbon atoms, alkenyl having 3 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, and having 7 to 15 carbon atoms. Phenylalkyl, aryl of 6 to 10 carbon atoms, or aryl substituted with 1 or 2 alkyl of 1 to 4 carbon atoms, or 1,1,2,2-tetrahydroperfluoroalkyl, wherein perfluoroalkyl The residue has 6 to 16 carbon atoms), [39] E 5 and E 8 are independently the same as E 2 , [40] E 5 and E 8 are independently hydrogen, -XE 1 , -X-CO-E 2 , -X-CO-X 1 , -XT 1 -Si (OR 2 ) n (R 1 ) 3-n or -XT 1- X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , [41] X 1 is -NH-E 4 or -XE 2 , [42] One or more of G 2 , G 7 , E 1 , E 2 , E 5 , E 8 and E 9 may be selected from the formulas -T 1 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -X-CO -XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -XT 1 -Si (OR 2 ) n (R 1 ) 3-n or a group of -XT 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , wherein T 1 and T 2 are independently 1 to 18 carbon atoms Is alkylene or alkylene-phenylene-alkylene having 8 to 20 carbon atoms, R 1 and R 2 are independently alkyl having 1 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, aryl having 6 to 10 carbon atoms or carbon atoms; Phenylalkyl of 7 to 20, preferably alkyl having 1 to 3 carbon atoms, n is 0, 1, 2 or 3). [43] Halogen is fluoro, bromo, chloro or iodo, preferably fluoro or chloro. [44] Alkyl radicals in the various substituents may be straight or branched chains. Examples of alkyl having 1 to 24 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, tert-butyl, pentyl, 2-pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, 3 Class-octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl, octadecyl and eicosyl. [45] Alkenyl having 2 to 24 carbon atoms is a straight or branched radical, for example propenyl, 2-butenyl, 3-butenyl, isobutenyl, n-2,4-pentadienyl, 3-methyl-2- Butenyl, n-2-octenyl, n-2-dodecenyl, iso-dodecenyl, oleyl, n-2-octadecenyl or n-4-octadecenyl. Alkenyl having 3 to 12 carbon atoms is preferable, and alkenyl having 3 to 6 carbon atoms is particularly preferable. [46] Alkynyl having 3 to 18 carbon atoms is a straight or branched chain radical, for example propynyl (-CH 2 -C≡CH), 2-butynyl, 3-butynyl, n-2-octynyl or n-2 Octadecinyl. Alkylyl having 3 to 12 carbon atoms is preferable, and alkynyl having 3 to 6 carbon atoms is particularly preferable. [47] Examples of hydroxy substituted alkyl are hydroxy propyl, hydroxy butyl or hydroxy hexyl. [48] Examples of halogen substituted alkyl are dichloropropyl, monobromobutyl or trichlorohexyl. [49] C 2 -C 18 alkyl blocked by one or more O atoms is, for example, —CH 2 —CH 2 —O—CH 2 —CH 2 —, —CH 2 —CH 2 —O—CH 3 —, or CH 2 -CH 2 -O-CH 2 -CH 2 -CH 2 -O-CH 2 -CH 3- . Preference is given to derived from polyethylene glycol. Typical substrates are-((CH 2 ) a -O) b -H / CH 3 , where a is a number from 1 to 6 and b is a number from 2 to 10. [50] C 2 -C 18 alkyl blocked with one or more NE 4 groups is generally represented by — ((CH 2 ) a -NE 4 ) b -H / CH 3 , where a, b and E 4 are as defined above It may be described. [51] C 5 -C 12 cycloalkyl is usually cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl or trimethylcyclohexyl. [52] C 6 -C 10 aryl is, for example, phenyl or naphthyl, but also includes C 1 -C 4 alkyl substituted phenyl, C 1 -C 4 alkoxy substituted phenyl, hydroxy, halogen or phenyl substituted phenyl. . Examples of alkyl substituted phenyl are ethylbenzene, toluene, xylene and isomers thereof, mesitylene or isopropylbenzene. Halogen substituted phenyl is, for example, dichlorobenzene or bromotoluene. [53] Alkoxy substituents are usually methoxy, ethoxy, propoxy or butoxy and their corresponding isomers. [54] Aralkyl is preferably phenylalkyl. Particular preference is given to C 7 -C 9 phenylalkyl which is benzyl, phenylethyl or phenylpropyl. [55] Perfluoroalkyls are, for example, trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluorobutyl and perfluorohexyl, with trifluoromethyl being preferred. [56] Preferably, the new benzotriazole is a compound of formula la or formula la. [57] [58] [59] In Formula Ia or Formula IIa above, [60] G 1 and G 6 are hydrogen, [61] G 2 and G 7 are independently cyano, CF 3- , fluoro, -CO-G 3 or E 3 SO 2- , or G 7 is hydrogen, [62] G 3 is linear or branched alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or a phenyl ring of 1 to 4 carbon atoms. Phenyl or phenylalkyl above substituted with 1-4 alkyl, [63] E 1 is phenylalkyl, phenyl or phenyl ring having 7 to 15 carbon atoms substituted with 1 to 4 alkyl of 1 to 4 carbon atoms, [64] E 2 and E 9 are independently a straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or a phenyl ring The above phenyl or phenylalkyl substituted with 1 to 3 alkyl of 1 to 4 carbon atoms, or [65] E 2 is at least one -OH, -OCOE 11 , -OE 4 , -NCO, -NH 2 , -NHCOE 11 , -NHE 4 , -N (E 4 ) 2 or mixtures thereof, wherein E 4 is 1 carbon Alkyl of 1 to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms, or one or more -O-, -NH-, -NE 4 -groups or their Alkyl or alkenyl, which may be blocked with a mixture and unsubstituted or substituted with one or more -OH, -OE 4 , -NH 2 groups or mixtures thereof, [66] E 11 is hydrogen, straight or branched chain alkyl of 1 to 18 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aryl of 6 to 14 carbon atoms, or phenylalkyl of 7 to 15 carbon atoms, [67] E 3 is alkyl having 1 to 20 carbons, hydroxyalkyl having 2 to 20 carbon atoms, alkenyl having 3 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, phenylalkyl having 7 to 15 carbon atoms, aryl having 6 to 10 carbon atoms, Or aryl above substituted with one or two alkyl of 1 to 4 carbon atoms, or 1,1,2,2-tetrahydroperfluoroalkyl, wherein the perfluoroalkyl moiety has 6 to 16 carbon atoms, [68] L is methylene, [69] At least one of E 1 , E 2 and E 9 may be selected from the formulas -T 1 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -XT 1 -Si (OR 2 ) n (R 1 ) 3-n or -XT 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) A group of 3-n wherein T 1 and T 2 are independently alkylene of 2 or 3 carbon atoms, and R 1 and R 2 are independent And alkyl or phenyl having 1 to 6 carbon atoms, and n is 0, 1, 2 or 3). [70] Another preferred embodiment of the present invention is a compound of formula la: [71] Formula Ia [72] [73] In Formula Ia above, [74] G 1 is hydrogen, [75] G 2 is CF 3- , fluoro or E 3 SO 2- , [76] E 1 is hydrogen or straight or branched chain alkyl of 2 to 24 carbon atoms, [77] E 2 is as defined above, [78] E 3 is straight or branched chain alkyl of 1 to 7 carbon atoms, [79] E 2 is a chemical formula -T 1 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -XT 1 -Si (OR 2 ) n (R 1 ) 3-n or -XT 1 -X-CO-XT 2 -Si (OR 2 ) a group of n (R 1 ) 3-n wherein T 1 and T 2 are independently alkylene having 2 or 3 carbon atoms, and R 1 and R 2 are independently alkyl or phenyl having 1 to 6 carbon atoms N is 0, 1, 2 or 3). [80] Preferably, T 1 and T 2 are independently alkylene having 2 or 3 carbon atoms. [81] Preferably, R 1 and R 2 are independently alkyl or phenyl having 1 to 6 carbon atoms. [82] Preferably, the compound of formula (I) [83] 5-trifluoromethyl-2- [2-hydroxy-3- (3-triethoxysilyl) propyl-5-tert-octylphenyl] -2H-benzotriazole (a), [84] 5-trifluoromethyl-2- {2-hydroxy-3-tert-butyl-5- [3- (3-triethyloxysilyl) propyl carbamoyloxy) propyl] phenyl} -2H-benzotriazole (b), [85] 5-trifluoromethyl-2- {2-hydroxy-3-tert-butyl-5- [2- (3-triethyloxysilyl) propylcarbamoyloxy) ethyl] phenyl} -2H-benzotriazole (c), [86] 5-trifluoromethyl-2- {2-hydroxy-5- [2- (3-triethyloxysilyl) propyl-carbamoyloxy) ethyl] -phenyl} -2H-benzotriazole (d), [87] 5-trifluoromethyl-2- {2-hydroxy-3-α-cumyl-5- [2- (3-triethyloxysilyl) propylcarbamoyloxy) ethyl] phenyl} -2H-benzotriazole ( e), [88] 5-trifluoromethyl-2- {2-hydroxy-3-tert-butyl-5- [2- (3- (diethoxymethylsilyl) propylaminocarbonylethyl] phenyl} -2H-benzotriazole (f), [89] 5-phenylsulfonyl-2- {2-hydroxy-3-tert-butyl-5- [3- (2-ethoxydimethylsilyl) ethylcarbonyloxy) propyl] phenyl} -2H-benzotriazole ( g), [90] 5-n-butylsulfonyl-2- {2-hydroxy-3-tert-butyl-5- [2- (3-ethoxydimethylsilyl) propyl-oxycarbonyl) ethyl] phenyl} -2H-benzo Triazole (h), [91] 5-trifluoromethyl-2- [2-hydroxy-3- (ethoxydimethylsilyl) propyl-5-tert-octylphenyl] -2H-benzotriazole (i), [92] 5-trifluoromethyl-2- [2-hydroxy-3- (trimethylsilyl) propyl-5-tert-butylphenyl] -2H-benzotriazole (j), [93] 5- [3- (diethoxyethylsilyl) propoxycarbonyl] -2- (2-hydroxy-3-α-cumyl-5-tert-octyl-phenyl) -2H-benzotriazole (k), [94] 5- [3- (diethoxyethylsilyl) propylaminocarbonyl] -2- (2-hydroxy-3-α-cumyl-5-tert-octyl-phenyl) -2H-benzotriazole (l), [95] (m) , [96] (n) , [97] (o) , [98] (p) , [99] (q) , [100] (r) , [101] (s) , [102] (t) or [103] (u) to be. [104] In addition, the present invention provides an organic material (a) that is photoinduced decomposition [105] A composition stabilized from light induced degradation, comprising a stabilizing effective amount of compound (b) of formula (I) or (II). [106] Preferably, the organic material is a natural polymer, semisynthetic polymer or synthetic polymer, in particular thermoplastic polymer. [107] In general, polymers that can be stabilized include: [108] 1. Polymers of monoolefins and diolefins such as polypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene, polyisoprene or polybutadiene), and polymers of cycloolefins Cyclopentene or norbornene, polyethylene, which may be optionally crosslinked, such as high density polyethylene (HDPE), low density polyethylene (LDPE), straight chain low density polyethylene (LLDPE), side chain low density polyethylene (BLDPE) ], [109] The polyolefins, ie polymers of the monoolefins exemplified in the above sentence, preferably polyethylene and polypropylene, can be prepared in different ways and in particular in the following way: [110] (a) radical polymerization (usually under high pressure and elevated temperature) and [111] (b) Catalytic polymerization using a catalyst usually containing one or more metals of Groups IVb, Vb, VIb or VIII of the Periodic Table. These metals may typically have one or more ligands, usually oxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenyls and / or aryls, which may be π- or σ-coordinated. These metal complexes may be in free form or immobilized on a substrate, typically activated magnesium chloride, titanium (III) chloride, alumina or silicon oxide. These catalysts may be soluble or insoluble in the polymerization medium. The catalyst may be used in itself for polymerization or as an additional activator, usually a metal alkyl, metal hydride, metal alkyl halide, metal alkyl oxide or metal alkyloxane, wherein the metal is a group of groups Ia, IIa and / or IIIa Element). The activator can be conveniently modified with additional ester, ether, amine or silyl ether groups. These catalyst systems are commonly referred to as Phillips, Standard Oil Indiana, Ziegler-Natta, TNZ (manufactured by DuPont), metallocene or single site catalyst (SSC). [112] 2. Mixtures of the polymers mentioned in 1 above, for example mixtures of polypropylene and polyisobutylene, mixtures of polypropylene and polyethylene (eg PP / HDPE, PP / LDPE) and mixtures of different kinds of polyethylene (E.g. LDPE / HDPE). [113] 3. Copolymers of monoolefins and diolefins or copolymers of these with other vinyl monomers, for example ethylene / propylene copolymers, linear low density polyethylene (LLDPE) and mixtures of these with low density polyethylene (LDPE) , Propylene / but-1-ene copolymer, propylene / isobutylene copolymer, ethylene / but-1-ene copolymer, ethylene / hexene copolymer, ethylene / methylpentene copolymer, ethylene / heptene copolymer, ethylene / Octene copolymers, propylene / butadiene copolymers, isobutylene / isoprene copolymers, ethylene / alkyl acrylate copolymers, ethylene / alkyl methacrylate copolymers, ethylene / vinyl acetate copolymers and copolymers thereof with carbon monoxide or Ethylene / acrylic acid copolymers and their salts (ionomers), and terpolymers of ethylene with propylene and dienes such as hexadiene, dicyclopentadiene or Ethylidene-norbornene); And mixtures of these copolymers with one another or with these and the polymers mentioned in 1 above, for example polypropylene / ethylene-propylene copolymers, LDPE / ethylene-vinyl acetate copolymers (EVA), LDPE / ethylene- Acrylic acid copolymers (EAA), LLDPE / EVA, LLDPE / EAA and alternating or random polyalkylene / carbon monoxide copolymers and mixtures thereof with other polymers such as polyamides. [114] 4. Hydrocarbon resins such as C 5 -C 9 (including their hydrogenation modifiers such as tackifiers) and mixtures of polyalkylenes and starches. [115] 5. Polystyrene, poly (p-methylstyrene), poly (α-methylstyrene). [116] 6. Copolymers of styrene or α-methylstyrene with diene or acrylic derivatives, for example styrene / butadiene, styrene / acrylonitrile, styrene / alkyl methacrylate, styrene / butadiene / alkyl acrylate, styrene / butadiene / Alkyl methacrylates, styrene / maleic anhydride, styrene / acrylonitrile / methyl acrylate; Mixtures of high impact strength styrene copolymers with other polymers, such as polyacrylates, diene polymers or ethylene / propylene / diene terpolymers, and block copolymers of styrene such as styrene / butadiene / styrene, styrene / Isoprene / styrene, styrene / ethylene / butylene / styrene or styrene / ethylene / propylene / styrene). [117] 7. Graft copolymers of styrene or α-methylstyrene, for example styrene on polybutadiene, styrene on polybutadiene-styrene or polybutadiene-acrylonitrile copolymers; Styrene and acrylonitrile (or methacrylonitrile) on polybutadiene; Styrene, acrylonitrile and methyl methacrylate on polybutadiene; Styrene and maleic anhydride on polybutadiene; Styrene, acrylonitrile and maleic anhydride or maleimide on polybutadiene; Styrene and maleimide on polybutadiene; Styrene and alkyl acrylates or methacrylates on polybutadiene; Styrene and acrylonitrile on ethylene / propylene / diene terpolymers; Styrene and acrylonitrile on polyalkyl acrylate or polyalkyl methacrylate; Styrene and acrylonitrile on acrylate / butadiene copolymers; And mixtures of these with copolymers listed in 6 above, such as copolymer mixtures known as ABS, MBS, ASA or AES polymers. [118] 8. Halogen containing polymers such as polychloroprene, chlorinated rubber, chlorinated or sulfochlorinated polyethylene, copolymers of ethylene with chlorinated ethylene, epichlorohydrin homopolymers and copolymers, especially polymers of halogen containing vinyl compounds (eg : Polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride), and copolymers thereof (e.g. vinyl chloride / vinylidene chloride, vinyl chloride / vinyl acetate or vinylidene chloride / vinyl acetate aerial) coalescence). [119] 9. Polymers derived from α, β-unsaturated acids and derivatives thereof such as polyacrylates and polymethacrylates; Polymethyl methacrylate, polyacrylamide and polyacrylonitrile impact modified with butyl acrylate. [120] 10. The monomers mentioned in 9 above, copolymers of each other or of these with other unsaturated monomers, for example acrylonitrile / butadiene copolymers, acrylonitrile / alkyl acrylate copolymers, acrylonitrile / Alkoxyalkyl acrylate or acrylonitrile / vinyl halide copolymers or acrylonitrile / alkyl methacrylate / butadiene terpolymers. [121] 11. Polymers derived from unsaturated alcohols and amines or acyl derivatives or acetals thereof, such as polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate, polyvinyl butyral, Polyallyl phthalate or polyallyl melamine and copolymers thereof with the olefins mentioned in 1 above. [122] 12. Homopolymers and copolymers of cyclic ethers, such as polyalkylene glycols, polyethylene oxides, polypropylene oxides or copolymers thereof with bisglycidyl ethers. [123] 13. polyacetals such as polyoxymethylene and these polyoxymethylenes containing ethylene oxide as comonomer; Polyacetals modified with thermoplastic polyurethanes, acrylates or MBS. [124] 14. Polyphenylene oxides and sulfides, and mixtures of polyphenylene oxides with styrene polymers or polyamides. [125] 15. Polyurethanes derived from hydroxyl terminated polyethers, polyesters or polybutadienes and on the other hand aliphatic or aromatic polyisocyanates and precursors thereof. [126] 16. Polyamides and copolyamides derived from diamines and dicarboxylic acids and / or aminocarboxylic acids or the corresponding lactams, for example polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6/9 , Aromatic polyamides starting from 6/12, 4/6, 12/12, polyamide 11, polyamide 12, m-xylene diamine and adipic acid; Polyamides prepared from hexamethylenediamine and isophthalic acid and / or terephthalic acid, with or without an elastomer as modifier, for example poly-2,4,4-trimethylhexamethylene terephthalamide or poly-m-phenylene isoph Deamide; And block copolymers of the aforementioned polyamides with polyolefins, olefin copolymers, ionomers or chemically bonded or grafted elastomers; Or block copolymers of the aforementioned polyamides with polyethers such as polyethylene glycol, polypropylene glycol or polytetramethylene glycol; And polyamides or copolyamides modified with EPDM or ABS; And polyamides condensed during processing (RIM polyamide systems). [127] 17. Polyureas, polyimides, polyamide-imides and polybenzimidazoles. [128] 18. Polyesters derived from dicarboxylic acids and diols and / or hydroxycarboxylic acids or the corresponding lactones, for example polyethylene terephthalate, polybutylene terephthalate, poly-1,4-dimethylolcyclohexane terephthalate and poly Hydroxybenzoates, block copolyether esters derived from hydroxyl terminated polyethers, and polyesters modified with polycarbonates or MBS. [129] 19. Polycarbonates and polyester carbonates. [130] 20. Polysulfones, polyether sulfones and polyether ketones. [131] 21. Crosslinked polymers derived from aldehydes on the one hand and phenol, urea and melamine on the other hand, such as phenol / formaldehyde resins, urea / formaldehyde resins and melamine / formaldehyde resins. [132] 22. Dry and Dry Alkyd Resin. [133] 23. Unsaturated polyester resins derived from copolyesters of saturated and unsaturated dicarboxylic acids using polyhydric alcohols and vinyl compounds as crosslinkers, and their halogen-containing modifiers with low flame retardancy. [134] 24. Crosslinkable acrylic resins derived from substituted acrylates, for example epoxy acrylates, urethane acrylates or polyester acrylates. [135] 25. Alkyd resins, polyester resins and acrylate resins crosslinked with melamine resins, urea resins, polyisocyanates or epoxy resins. [136] 26. Crosslinked epoxy resins derived from polyepoxides such as bisglycidyl ether or cycloaliphatic diepoxides. [137] 27. Natural polymers such as cellulose, rubber, gelatin and chemically modified homologous derivatives thereof (such as cellulose acetate, cellulose propionate and cellulose butyrate) or cellulose ethers (such as methyl cellulose), and rosin and these Derivatives of. [138] 28. Blends of the aforementioned polymers (polyblends), for example PP / EPDM, polyamide / EPDM or ABS, PVC / VEA, PVC / ABS, PVC / MBS, PC / ABS, PBTP / ABS, PC / ABA , PC / PBT, PVC / CPE, PVC / acrylate, POM / thermoplastic PUR, PC / thermoplastic PUR, POM / acrylate, POM / MBS, PPO / HIPS, PPO / PA 6.6 and copolymers, PA / HDPE, PA / PP, PA / PPO. [139] 29. Naturally occurring and synthetic organic materials which are pure monomeric compounds or mixtures of such compounds, for example mineral oils, fats and oils of animals and plants, or oils, fats and waxes based on synthetic esters (e.g. Phthalates, adipates, phosphates or trimellitates) and mixtures of synthetic esters with mineral oil in a predetermined weight ratio, those typically used as spinning compositions, and aqueous emulsions of such materials. [140] 30. Aqueous emulsions of natural or synthetic rubber, such as latexes of natural latex or carboxylated styrene / butadiene copolymers. [141] 31. Polysiloxanes such as soft hydrophilic polysiloxanes described in US Pat. No. 4,259,467 and hard polyorganosiloxanes described in US Pat. No. 4,355,147. [142] 32. Polyketimines in combination with unsaturated acrylic polyacetoacetate resins or unsaturated acrylic resins. Unsaturated acrylic resins include urethane acrylates, polyether acrylates, vinyl or acrylic copolymers with pendant unsaturated groups, and acrylated melamine. Polyketimines are prepared from polyamines and ketones in the presence of an acid catalyst. [143] 33. An irradiation curable composition containing an ethylenically unsaturated monomer or oligomer and a polyunsaturated aliphatic oligomer. [144] 34. Epoxymelamine resins, for example light stable resins crosslinked by epoxy functional coetherylated higher solid melamine resins, such as LSE-4103 (manufactured by Monsanto). [145] Preferably, the polymer is a thermoplastic polymer, in particular polyolefin or polycarbonate, in particular polyethylene or polypropylene, most preferably polypropylene, or the polymer is styrene, ABS, nylon, polyester (e.g. poly (ethylene terephthalate) Or poly (butylene terephthalate)), polyurethane, acrylate, rubber modified styrene, poly (vinyl chloride), poly (vinyl butyral), polyacetal (polyoxymethylene), poly (ethylene naphthalenedicarboxylate) , Or other blends or copolymers such as poly (ethylene / 1,4-cyclohexylenedimethylene terephthalate) PETG or ionomers. [146] More preferred are compositions wherein the polymer is polyolefin or polycarbonate. [147] Especially preferably, the polymer is a siloxane coating as a barrier layer on polycarbonate. [148] In another preferred embodiment of the invention, the organic material contains a thermosetting acrylic melamine resin, an acrylic urethane resin, an epoxy carboxy resin, a silane modified acrylic melamine, an acrylic resin or a carbamate group in which the carbamate pendant group is crosslinked with melamine. Is a resin selected from the group consisting of acrylic polyol resins crosslinked with melamine. [149] Such automotive coatings are disclosed in WO 92/20726, WO 92/05225, and H. Furakawa et al., Which describe the curing and properties of acrylosilane coatings. , Progress in Organic Coatings, 24, 81-99 (1994). [150] Most preferably, the resin is a thermosetting acrylic melamine resin or acrylic urethane resin. [151] In another preferred embodiment of the invention, the organic material of component (a) is an organosilicon hardcoat or softcoat for the automotive field (e.g. GENIVA coatings) or organosilicon hardcoat for multilayer compositions or Acrylosilane coatings useful for softcoats. [152] In another preferred embodiment of the present invention, the organic material is a recording material. [153] The recording material according to the present invention is suitable for pressure-sensitive copying systems, photocopying systems using microcapsules, heat sensitive copying systems, photographic materials and ink jet printing. [154] The recording material according to the invention is distinguished by an unexpected quality improvement, especially with regard to the fastness to light. [155] The recording material according to the present invention has a structure known for a particular use. These consist of conventional carriers, for example paper or plastic membranes, which are covered with one or more layers. Depending on the type of material, these layers contain appropriately required components, and in the case of photographic materials, for example, silver halide emulsions, dye binders, dyes and the like. Particularly suitable materials for ink jet printing have in particular an ink absorbent layer on a conventional carrier. In addition, uncoated paper can be used for ink jet printing. In this case, the paper acts simultaneously as the carrier material and the ink absorbing layer. Suitable materials for ink jet printing are described, for example, in US Pat. No. 5,073,448, which is incorporated herein by reference. [156] The recording material may also be transparent, for example as in the case of the projection film. [157] The compounds of formula (I) or formula (II) are introduced into the carder material as early as possible, which is added to the paper pulp when making the latter, for example on paper. A second application method is to spray an aqueous solution of a compound of formula (I) or formula (II) to the carder material, or add the compound to the coating composition. [158] Coating compositions for transparent recording materials suitable for projection may contain no particular particles that scatter light, for example pigments and fillers. [159] Dye binding coating compositions can be prepared by a number of other additives, such as antioxidants, light stabilizers (including UV absorbers not included in the scope of the UV absorbers of the present invention), viscosity modifiers, fluorescent brighteners, biocides, and / or It may contain a preservative. [160] The coating composition is usually prepared as follows: the water-soluble component, for example the binder, is dissolved in water and stirred together, and the solid component, for example the filler and other additives already described, are dispersed in the aqueous medium above, It is advantageously dispersed in certain devices, for example ultrasonic systems, turbine stirrers, homogenizers, colloid mills, bead mills, sand mills, high speed stirrers and the like. Compounds of formula (I) or formula (II) can be readily incorporated into coating compositions. [161] The recording material according to the invention preferably contains a compound of formula (I) of 1 to 5000 mg / m 2 , in particular 50 to 1200 mg / m 2 . [162] As mentioned above, the recording material according to the present invention covers various fields. Compounds of formula (I) or formula (II) can be used, for example, in pressure sensitive radiation systems. These may be introduced into the paper to protect the microencapsulated dye precursor from light, or introduced into the binder of the developer layer to protect the formed dye. [163] Photocopy systems using light sensitive microcapsules developed by pressure are described in U.S. Patent Nos. 4,416,966, U.S. Patent 4,483,912, U.S. Patent 4,352,200, U.S. Patent 4,535,050, U.S. Patent 4,535,463, U.S. Patent 4,551,407 US Patent Nos. 4,562,137 and 4,608,330, and 139,479, 162,664, 164,931, 237,024, and 237,025 and European Patent Publication No. 260,129. In all these systems, the compound can be incorporated into the dye receiving layer. However, the compound may be introduced into the donor layer to protect the color former from light. [164] Photographic materials that can be stabilized are photographic dyes and layers containing such dyes or precursors thereof, such as photographic paper and films. Suitable materials are described, for example, in US Pat. No. 5,364,749, which is incorporated herein by reference. Compounds of formula (I) or formula (II) herein serve as UV filters for electrostatic flashes. In color photographic materials, binders and dyes are also protected from photochemical degradation. [165] The compounds of the present invention can be used in all kinds of color photographic materials. For example, they can be used for color paper, color photo paper, direct positive color material, color negative film, color positive film, color photo film, and the like. They are particularly preferably used for photographic color materials containing photographic substrates or forming positives. [166] The color photographic recording material usually contains a blue sensitive and / or green sensitive and / or red sensitive silver halide emulsion layer and, optionally, a protective layer on a support, and the compounds of the present invention preferably are green sensitive or red sensitive. Present in the layer, between the green sensitive layer and the red sensitive layer, or in the top layer of the silver halide emulsion layer. [167] The compounds of formula (I) or formula (II) are also used in recording materials based on the principles of photopolymerization, photoplasticization or microcapsule capture, or dyes with heat sensitive and photosensitive diazonium salts, white dyes with oxidants or Lewis acids Lactone may be used when used. [168] In addition, the compounds of the present invention can be used in recording materials for dye diffusion transfer printing, thermal wax transfer printing and non-matrix printing and for use in electrostatic, electrographic, electrotransfer, magnetic recording and laser electrophotographic printers and pen-plotters. It can be used for recording materials. Among these, recording materials for dye diffusion transfer printing are preferable, for example, as described in EP-A-507,734. [169] The compounds of the present invention may also be used in inks, preferably inks for ink jet printing, as described in US Pat. No. 5,098,477, which is incorporated herein by reference. [170] The compounds of the present invention not only show good hydrolytic stability, handleability and storage stability, but also good extraction resistance when present in stabilized compositions. [171] Methods of preparing the compounds of the present invention are described in the prior art. Intermediates required for the preparation of the compounds of the invention are usually commercially available products. [172] Generally, the compounds of the present invention are used at about 0.01 to about 5 weight percent based on the weight of the stabilized composition, but this will depend on the particular substrate and application. Advantageous ranges are from about 0.05 to about 3%, and in particular from 0.05 to about 1%. However, some high performance membranes or UV absorbing layers of laminates, such as those produced by coextrusion, may contain from 5 to 15% by weight of the compounds of the present invention. Concentrations of 5 to 10 weight percent are typical for certain coextrusion applications. [173] Stabilizers of the present invention can be readily incorporated into organic polymers by conventional techniques at any convenient step prior to making shaped articles therefrom. For example, the stabilizer can be mixed with the polymer in dry powder form or a suspension or emulsion of stabilizer can be mixed with a solution, suspension or emulsion of the polymer. The resulting stabilized polymer compositions of the present invention optionally comprise from about 0.01 to about 5% by weight, preferably from about 0.025 to about 2% by weight, in particular from about 0.1 to about various conventional additives or mixtures thereof, such as the materials described It may contain about 1% by weight. [174] 1. Antioxidant [175] 1.1. Alkylated monophenols , for example [176] 2,6-di-tert-butyl-4-methylphenol, [177] 2-3-butyl-4,6-dimethylphenol, [178] 2,6-di-tert-butyl-4-ethylphenol, [179] 2,6-di-tert-butyl-4-n-butylphenol, [180] 2,6-di-tert-butyl-4-i-butylphenol, [181] 2,6-di-cyclopentyl-4-methylphenol, [182] 2- (α-methylcyclohexyl) -4,6-dimethylphenol, [183] 2,6-di-octadecyl-4-methylphenol, [184] 2,4,6-tri-cyclohexylphenol and [185] 2,6-di-tert-butyl-4-methoxymethylphenol. [186] 1.2. Alkylated hydroquinones, for example [187] 2,6-di-tert-butyl-4-methoxyphenol, [188] 2,5-di-tert-butyl-hydroquinone, [189] 2,5-di-tert-amyl-hydroquinone and [190] 2,6-diphenyl-4-octadecyloxyphenol. [191] 1.3. Hydroxylated thiodiphenyl ethers, for example [192] 2,2'-thio-bis- (6-tert-butyl-4-methylphenol), [193] 2,2'-thio-bis- (4-octylphenol), [194] 4,4'-thio-bis- (6-tert-butyl-3-methylphenol) and [195] 4,4'-thio-bis- (6-tert-butyl-2-methylphenol). [196] 1.4. Alkylidene-bisphenols, for example [197] 2,2'-methylene-bis- (6-tert-butyl-4-methylphenol), [198] 2,2'-methylene-bis- (6-tert-butyl-4-ethylphenol), [199] 2,2'-methylene-bis- [4-methyl-6- (α-methylcyclohexyl) -phenol], [200] 2,2'-methylene-bis- (4-methyl-6-cyclohexylphenol), [201] 2,2'-methylene-bis- (6-nonyl-4-methylphenol), [202] 2,2'-methylene-bis- [6- (α-methylbenzyl) -4-nonylphenol], [203] 2,2'-methylene-bis- [6- (α, α-dimethylbenzyl) -4-nonylphenol], [204] 2,2'-methylene-bis- (4,6-di-tert-butylphenol), [205] 2,2'-ethylidene-bis- (4,6-di-tert-butylphenol), [206] 2,2'-ethylidene-bis- (6-tert-butyl-4-isobutylphenol), [207] 4,4'-methylene-bis- (2,6-di-tert-butylphenol), [208] 4,4'-methylene-bis- (6-tert-butyl-2-methylphenol), [209] 1,1-bis- (5-tert-butyl-4-hydroxy-2-methylphenyl) -butane, [210] 2,6-di- (tert-butyl-5-methyl-2-hydroxybenzyl) -4-methylphenol, [211] 1,1,3-tris- (5-tert-butyl-4-hydroxy-2-methylphenyl) -butane, [212] 1,1-bis- (5-tert-butyl-4-hydroxy-2-methylphenyl) -3-n-dodecylmercaptobutane, [213] Ethylene glycol bis- [3,3-bis- (3'-tert-butyl-4'-hydroxyphenyl) -butyrate], [214] Di- (tert-butyl-4-hydroxy-5-methylphenyl) -dicyclopentadiene and [215] Di- [2- (3'-tert-butyl-2'-hydroxy-5'-methyl-benzyl) -6-tert-butyl-4-methylphenyl] terephthalate. [216] 1.5. Benzyl compounds, for example [217] 1,3,5-tri- (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene, [218] Di- (3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, [219] 3,5-di-tert-butyl-4-hydroxybenzyl-mercapto-acetic acid isooctyl ester, [220] Bis- (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) dithiol terephthalate, [221] 1,3,5-tris- (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, [222] 1,3,5-tris- (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, [223] 3,5-di-tert-butyl-4-hydroxybenzyl-phosphoric acid dioctadecyl ester and [224] 3,5-di-tert-butyl-4-hydroxybenzyl-phosphoric acid monoethyl ester, calcium salt. [225] 1.6. Acylaminophenols, for example [226] 4-hydroxy-lauric acid anhydride, [227] 4-hydroxy-stearic acid anhydride, [228] 2,4-bis-octylmercapto-6- (3,5-tert-butyl-4-hydroxyanilino) -s-triazine and [229] Octyl-N- (3,5-di-tert-butyl-4-hydroxyphenyl) -carbamate. [230] 1.7. Esters of monohydric or polyhydric alcohols with β- (3,5-di-tert-butyl-4-hydroxyphenyl) -propionic acid, for example [231] Methanoldiethylene glycol [232] Octadecanol triethylene glycol [233] 1,6-hexanediol pentaerythritol [234] Neopentyl glycoltris-hydroxyethyl isocyanurate [235] Thiodiethylene glycoldi-hydroxyethyl oxalic acid diamide [236] Triethanolaminetriisopropanolamine [237] 1.8. Esters of monohydric or polyhydric alcohols with β- (5-tert-butyl-4-hydroxy-3-methylphenyl) -propionic acid, for example, [238] Methanoldiethylene glycol [239] Octadecanol triethylene glycol [240] 1,6-hexanediol pentaerythritol [241] Neopentyl glycoltris-hydroxyethyl isocyanurate [242] Thiodiethylene glycoldi-hydroxyethyl oxalic acid diamide [243] Triethanolaminetriisopropanolamine [244] 1.9. amides of β- (3,5-di-tert-butyl-4-hydroxyphenyl) -propionic acid, for example [245] N, N'-di- (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) -hexamethylenediamine, [246] N, N'-di- (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) -trimethylenediamine and [247] N, N'-di- (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) -hydrazine. [248] 1.10. Diarylamines, for example [249] Diphenylamine, N-phenyl-1-naphthylamine, N- (4-tert-octylphenyl) -1-naphthylamine, 4,4'-di-tert-octyl-diphenylamine, N- Reaction product of phenylbenzylamine with 2,4,4-trimethylpentene, reaction product of diphenylamine with 2,4,4-trimethylpentene and 2,4,4-trimethylpentene with N-phenyl-1-naphthylamine Reaction product. [250] 2. UV absorbers and light stabilizers [251] 2.1. 2- (2'-hydroxyphenyl) -benzotriazole, for example [252] 5'-methyl-, 3 ', 5'-di-tert-butyl-, 5'-tert-butyl-, 5'-(1,1,3,3-tetramethylbutyl)-, 5-chloro -3 ', 5'-di-tert-butyl-, 5-chloro-3'-tert-butyl-5'-methyl-, 3'-tert-butyl-5'-tert-butyl-, 4'-octoxy, 3 ', 5'-di-tert-amyl-, 3', 5'-bis- (α, α-dimethylbenzyl), 3'-tert-butyl-5 '-(2 -(Omega-hydroxy-octa- (ethyleneoxy) carbonyl-ethyl)-, 3'-dodecyl-5'-methyl- and 3'-tert-butyl-5 '-(2-octyloxycarbonyl ) Ethyl- and dodecylated-5'-methyl derivatives. [253] 2.2. 2-hydroxy-benzophenone, for example [254] 4-hydroxy-, 4-methoxy-, 4-octoxy, 4-decyloxy-, 4-dodecyloxy-, 4-benzyloxy, 4,2 ', 4'-trihydroxy- and 2 '-Hydroxy-4,4'-dimethoxy derivatives. [255] 2.3. Substituted or unsubstituted esters of benzoic acid, for example [256] Phenyl salicylate, 4-tert-butylphenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis- (4-tert-butylbenzoyl) -resorcinol, benzoyl resorcinol, 3 , 5-di-tert-butyl-4-hydroxybenzoic acid, 2,4-di-tert-butylphenyl ester and 3,5-di-tert-butyl-4-hydroxybenzoic acid hexadecyl ester. [257] 2.4. Acrylates, for example [258] α-cyano-β, β-diphenylacrylic acid ethyl ester or isooctyl ester, α-carbomethoxy-cinnamic acid methyl ester, α-cyano-β-methyl-p-methoxy-cinnamic acid methyl ester or butyl Esters, α-carbomethoxy-p-methoxy-cinnamic acid methyl ester, N- (β-carbomethoxy-β-cyanovinyl) -2-methyl-indolin. [259] 2.5. Nickel compounds, for example [260] 2,2'-thio-bis- [4- (1,1,3,3-tetramethylbutyl)-, optionally with additional ligands such as n-butylamine, triethanolamine or N-cyclohexyl-diethanolamine Phenol] nickel complexes (eg 1: 1 or 1: 2 complexes), nickel dibutyldithiocarbamate, 4-hydroxy-3,5-di-tert-butylbenzylphosphonic acid monoalkyl esters (eg Nickel salts of methyl, ethyl or butyl esters), nickel complexes of ketoximes (eg 2-hydroxy-4-methyl-phenyl undecyl ketoxime), 1-phenyl-4-lauroyl with optionally further ligands Nickel complex of -5-hydroxy-pyrazole. [261] 2.6. Sterically hindered amines, for example, [262] Bis- (2,2,6,6-tetramethylpiperidyl) sebacate, bis- (1,2,2,6,6-pentamethylpiperidyl) sebacate, n-butyl-3,5- Di-tert-butyl-4-hydroxybenzyl malonic acid bis- (1,2,2,6,6-pentanemethylpiperidyl) ester, 1-hydroxyethyl-2,2,6,6-tetra Condensation product of methyl-4-hydroxypiperidine with succinic acid, N, N '-(2,2,6,6-tetramethylpiperidyl) -hexamethylenediamine and 4-tert-octylamino-2 Condensation products with, 6-dichloro-s-triazine, tris- (2,2,6,6-tetramethylpiperidyl) -nitrotriacetate, tetrakis- (2,2,6,6-tetramethyl- 4-piperidyl) 1,2,3,4-butanetetracarboxylate, 1,1 '-(1,2-ethanediyl) -bis- (3,3,5,5-tetramethylpiperazinone) , Bis- (1-octyloxy-2,2,6,6, -tetramethylpiperidin-4-yl) sebacate. [263] 2.7. Oxalic acid diamides, for example [264] 4,4'-di-octyloxy-oxanilide, 2,2'-di-octyloxy-5,5'-di-tert-butyl-oxanylide, 2,2'-di-dodecyloxy -5,5'-di-tert-butyl-oxanilide, 2-ethoxy-2'-ethyl-oxanilide, N, N'-bis- (3-dimethylaminopropyl) -oxalamide, 2-ethoxy-5-tert-butyl-2'-ethyloxanide and mixtures thereof with 2-ethoxy-2'-ethyl-5,4'-di-tert-butyloxanide And mixtures with ortho- and para-methoxy- as well as o- and p-ethoxy disubstituted oxanilides. [265] 2.8. Hydroxyphenyl-s-triazine, for example [266] 2,6-bis- (2,4-dimethylphenyl) -4- (2-hydroxy-4-octyloxyphenyl) -s-triazine, 2,6-bis- (2,4-dimethylphenyl)- 4- (2,4-dihydroxyphenyl) -s-triazine, 2,4-bis (2,4-dihydroxyphenyl) -6- (4-chlorophenyl) -s-triazine, 2, 4-bis [2-hydroxy-4- (2-hydroxyethoxy) phenyl] -6- (4-chlorophenyl) -s-triazine, 2,4-bis [2-hydroxy-4- ( 2-hydroxy-4- (2-hydroxy-ethoxy) phenyl] -6- (2,4-dimethylphenyl) -s-triazine, 2,4-bis [2-hydroxy-4- (2 -Hydroxyethoxy) -phenyl] -6- (4-bromophenyl) -s-triazine, 2,4-bis [2-hydroxy-4- (2-acetoxyethoxy) phenyl] -6 -(4-chlorophenyl) -s-triazine, 2,4-bis (2,4-dihydroxyphenyl) -6- (2,4-dimethylphenyl) -s-triazine. [267] 3. metal deactivators, for example [268] N, N'-diphenyloxalic acid diamide, N-salicyl-N'-salicyloylhydrazine, N, N'-bis-salicyloylhydrazine, N, N'-bis- (3,5-di- Tert-butyl-4-hydroxyphenylpropionyl) -hydrazine, 3-salicyloylamino-1,2,4-triazole, bis-benzylidene oxalic acid dihydrazide. [269] 4. phosphites and phosphonites, eg [270] Triphenyl phosphite, diphenylalkyl phosphite, phenyldialkyl phosphite, tri- (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, di-stearyl-pentaerythritol diphosphite, tris -(2,4-di-tert-butylphenyl) phosphite, di-isodecylpentaerythritol diphosphite, di- (2,4,6-tri-tert-butylphenyl) -pentaerythritol diphosphite , Di- (2,4-di-tert-butyl-6-methylphenyl) -pentaerythritol diphosphite, di- (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, tristearyl Sorbitol triphosphite, tetrakis- (2,4-di-tert-butylphenyl) 4,4'-diphenylylene diphosphonite. [271] 5. compounds that destroy peroxides, eg [272] esters of β-thiodipropionic acid (eg lauryl, stearyl, myristyl or tridecyl ester), zinc salts of mercapto-benzimidazole or 2-mercaptobenzimidazole, zinc dibutyl-dithiocarbamate , Dioctadecyl disulfide, pentaerythritol tetrakis- (β-dodecyl mercapto) -propionate. [273] 6. hydroxylamine, for example [274] N, N-dibenzylhydroxylamine, N, N-diethylhydroxylamine, N, N-dioctylhydroxylamine, N, N-dilaurylhydroxylamine, N, N-ditetradecylhydroxylamine , N, N-dihexadecylhydroxylamine, N, N-dioctadecylhydroxylamine, N-hexadecyl-N-octadecylhydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, hydrogenation N, N-dialkylhydroxylamines derived from resin amines. [275] 7. Nitrons, for example [276] N-benzyl-α-phenyl nitron, N-ethyl-α-methyl nitron, N-octyl-α-heptyl nitron, N-lauryl-α-undecyl nitron, N-tetradecyl-α-tri Decyl nitron, N-hexadecyl-α-pentadecyl nitron, N-octadecyl-α-heptadecylnitrone, N-hexadecyl-α-heptadecyl nitron, N-octadecyl-α-pentadidecyl knit Ron, N-heptadecyl-α-heptadecyl nitron, N-octadecyl-α-hexadecyl nitron, nitron derived from N, N-dialkylhydroxylamine derived from hydrogenated resin amine. [277] 8. Polyamide Stabilizers, for example [278] Copper salts and divalent manganese salts in combination with iodine and / or phosphorus compounds. [279] 9. Basic auxiliary stabilizers, for example [280] Melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids such as Ca stearate, Zn Stearate, Mg stearate, Na ricinolate and K palmitate, antimony pyrocatecholate or zinc pyrocatecholate). [281] 10. Nucleating agents, for example [282] 4-tert-butyl-benzoic acid, adipic acid, diphenylacetic acid. [283] 11. Fillers and reinforcing agents, for example [284] Calcium carbonate, silicate, glass fiber, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite. [285] 12. Other additives, for example [286] Plasticizers, lubricants, emulsifiers, pigments, varnishes, flame retardants, antistatic agents, molding agents, and thio synergists such as lauryl thiodipropionate or distearyl thiodipropionate. [287] 13. Benzofuranone and indolinones, for example [288] Those described in US Pat. No. 4,325,863, US Pat. No. 4,338,244 or US Pat. No. 5,175,312, or 3- [4- (2-acetoxyethoxy) phenyl] -5,7-di-tert-butyl-benzo Furan-2-one, 5,7-di-tert-butyl-3- [4- (2-stearoyloxyethoxy) phenyl] benzofuran-2-one, 3,3'-bis [5, 7-di-tert-butyl-3- (4- [2-hydroxyethoxy] phenyl) benzofuran-2-one], 5,7-di-tert-butyl-3- (4-ethoxy Phenyl) -benzofuran-2-one, 3- (4-acetoxy-3,5-dimethylphenyl) -5,7-di-tert-butyl-benzofuran-2-one, 3- (3,5 -Dimethyl-4-pivaloyloxyphenyl) -5,7-di-tert-butyl-benzofuran-2-one. [289] Auxiliary stabilizers other than benzofuranone described under 13 are added, for example, at concentrations of from 0.01 to 10% by weight, based on the total weight of the material to be stabilized. [290] Further preferred compositions comprise, in addition to components (a) and (b), further additives such as phenolic antioxidants, light stabilizers or process stabilizers. [291] Particularly preferred additives are phenolic antioxidants (item 1 of the list), hindered amines (item 2.6 of the list), phosphite and phosphonite (item 4 of the list), UV absorbers (item 2 of the list) and peroxide destroying compounds (Item 5 of the list). [292] Particularly preferred further additives (stabilizers) are, for example, benzofuran-2-ones as described in US Pat. No. 4,325,863, US Pat. No. 4,338,244 or US Pat. No. 5,175,312. [293] Particularly important phenolic antioxidants are n-octadecyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate, neopentanetetrayl tetrakis (3,5-di-tert-butyl-4- Hydroxyhydrocinnamate), di-n-octadecyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, 1,3,5-tris (3,5-di-tert- Butyl-4-hydroxybenzyl) isocyanurate, thiodiethylene bis (3,5-di-tert-butyl-4-hydroxyhydrocinnamate), 1,3,5-trimethyl-2,4, 6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, 3,6-dioxaoctamethylene bis (3-methyl-5-tert-butyl-4-hydroxyhydrocinna Mate), 2,6-di-tert-butyl-p-cresol, 2,2'-ethylidene-bis (4,6-di-tert-butylphenol), 1,3,5-tris (2 , 6-dimethyl-4-tert-butyl-3-hydroxybenzyl) isocyanurate, 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane, 1,3,5-tris [2- (3,5-di-tert-butyl-4-hydroxyha Drocinnamoyloxy) ethyl] isocyanurate, 3,5-di- (3,5-di-tert-butyl-4-hydroxybenzyl) mesitol, hexamethylene bis (3,5-di-3 Tert-butyl-4-hydroxyhydrocinnamate), 1- (3,5-di-tert-butyl-4-hydroxyanilino) -3,5-di (octylthio) -s-triazine, N, N'-hexamethylene bis (3,5-di-tert-butyl-4-hydroxyhydrocinnaamide), calcium bis (ethyl 3,5-di-tert-butyl-4-hydroxybenzyl- Phosphonate), ethylene bis [3,3-di (3-tert-butyl-4-hydroxyphenyl) butyrate], octyl 3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate , Bis (3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl) hydrazide and N, N'-bis [2- (3,5-di-tert-butyl-4-hydride Hydroxyhydrocinnamoyloxy) -ethyl] -oxamide. [294] Most preferred phenolic antioxidants are neopentanetetrayl tetrakis (3,5-di-tert-butyl-4-hydroxyhydrocinnamate), n-octadecyl 3,5-di-tert-butyl-4 -Hydroxyhydrocinnamate, 1,3,5-trimethyl-2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, 1,3,5-tris ( 3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 2,6-di-tert-butyl-p-cresol or 2,2'-ethylidene-bis (4,6 Di-tert-butylphenol). [295] Particularly important hindered amine compounds are bis (2,2,6,6-tetramethylpiperidin-4-yl) sebacate, bis (1,2,2,6,6-pentamethylpiperidin-4-yl ) Sebacate, di (1,2,2,6,6-pentamethylpiperidin-4-yl) (3,5-di-tert-butyl-4-hydroxybenzyl) butylmalonate, 4- Benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, 3-n-octyl-7,7,9,9- Tetramethyl-1,3,8-triaza-spiro [4.5] decane-2,4-dione, tris (2,2,6,6-tetramethylpiperidin-4-yl) nitrilotriacetate, 1, 2-bis (2,2,6,6-tetramethyl-3-oxopiperazin-4-yl) ethane, 2,2,4,4-tetramethyl-7-oxa-3,20-diaza-21 Oxodisspiro [5.1.11.2] henic acid, 2,4-dichloro-6-tert-octylamino-s-triazine and 4,4'-hexamethylenebis (amino-2,2,6,6- Polycondensation product of tetramethylpiperidine), polycondensation of 1- (2-hydroxyethyl) -2,2,6,6-tetramethyl-4-hydroxypiperidine with succinic acid Product, polycondensation product of 4,4'-hexamethylenebis- (amino-2,2,6,6-tetramethylpiperidine) with 1,2-dibromoethane, tetrakis (2,2, 6,6-tetramethylpiperidin-4-yl) 1,2,3,4-butanetetracarboxylate, tetrakis (1,2,2,6,6-pentamethylpiperidin-4-yl) 1,2,3,4-butanetetracarboxylate, 2,4-dichloro-6-morpholino-s-triazine and 4,4'-hexamethylenebis (amino-2,2,6,6-tetramethyl Polycondensation product with piperidine), N, N ', N ", N'"-tetrakis [(4,6-bis (butyl-1,2,2,6,6-pentamethylpiperidine-) 4-yl) -amino-s-triazin-2-yl] -1,10-diamino-4,7-diazadecan, mixed [2,2,6,6-tetramethylpiperidine-4 -Yl / β, β, β ', β'-tetramethyl-3,9- (2,4,8,10-tetraoxaspiro [5.5] -undecane) diethyl] 1,2,3,4- Butanetetracarboxylate, mixed [1,2,2,6,6-pentamethylpiperidin-4-yl / β, β, β ', β'-tetramethyl-3,9- (2,4, 8,10-tetraoxaspiro [5.5] undecane) diethyl] 1,2,3,4-butanete Lacarboxylate, octamethylene bis (2,2,6,6-tetramethylpiperidine-4-carboxylate), 4,4'-ethylenebis (2,2,6,6-tetramethylpiperazine-3 -On), N-2,2,6,6-tetramethylpiperidin-4-yl-n-dodecylsuccinimide, n-1,2,2,6,6-pentamethylpiperidine- 4-yl-n-dodecylsuccinimide, N-1-acetyl-2,2,6,6-tetramethylpiperidin-4-yl-n-dodecylsuccinimide, 1-acetyl-3- Dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro [4.5] decane-2,4-dione, di- (1-octyloxy-2,2,6,6- Tetramethylpiperidin-4-yl) sebacate, di- (1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate, 1-octyloxy-2 , 2,6,6-tetramethyl-4-hydroxy-piperidine, poly-{[6-tert-octylamino-s-triazine-2,4-diyl] [2- (1-cyclohex Siloxy-2,2,6,6-tetramethylpiperidin-4-yl) imino-hexamethylene- [4- (1-cyclohexyloxy-2,2,6,6-tetramethylpiperi Din-4-yl) imino], 2,4,6-tris [N- (1- Cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) -n-butylamino] -s-triazine and 1- (2-hydroxy-2-ethylpropoxy-4 Octadecanoyloxy-2,2,6,6-tetramethylpiperidine. [296] Most preferred hindered amine compounds are bis (2,2,6,6-tetramethylpiperidin-4-yl) sebacate, bis (1,2,2,6,6-pentamethylpiperidin-4-yl ) Sebacate, di (1,2,2,6,6-pentamethylpiperidin-4-yl) (3,5-di-tert-butyl-4-hydroxybenzyl) butylmalonate, 1- (2-hydroxyethyl) -2,2,6,6-tetramethyl-4-hydroxypiperidine and a polycondensation product of succinic acid, 2,4-dichloro-6-tert-octylamino-s- Polycondensation products of triazine with 4,4'-hexamethylenebis (amino-2,2,6,6-tetramethylpiperidine), N, N ', N ", N'"-tetrakis [(4 , 6-bis (butyl- (1,2,2,6,6-pentamethylpiperidin-4-yl) amino] -s-triazin-2-yl] -1,10-diamino-4, 7-diazadecan, di- (1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, di- (1-cyclohexyloxy-2,2,6 , 6-tetramethylpiperidin-4-yl) succinate, 1-octyloxy-2,2,6,6-tetramethyl-4-hydroxy-piperidine, poly-{[6-tertiary- Octylamino- s-triazine-2,4-diyl] [2- (1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) imino-hexamethylene- [4- ( 1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) imino], 2,4,6-tris [N- (1-cyclohexyloxy-2,2 , 6,6-tetramethylpiperidin-4-yl) -n-butylamino] -s-triazine or 1- (2-hydroxy-2-ethylpropoxy-4-octadecanoyloxy-2, 2,6,6-tetramethylpiperidine. [297] The composition of the present invention may further contain another UV absorber selected from the group consisting of benzotriazole, s-triazine, oxanilide, hydroxybenzophenone, benzoate and α-cyanoacrylate (item 12). Can be. [298] In particular the compounds of the present invention may further contain one or more other 2-hydroxyphenyl-2H-benzotriazoles, tris-aryl-s-triazines or hindered amines or mixtures thereof in an effective stabilizing amount. [299] Preferably, 2-hydroxyphenyl-2H-benzotriazole is 2- (2-hydroxy-3,5-di-tert-amylphenyl) -2H-benzotriazole, [300] 2- [2-hydroxy-3,5-di (α, α-dimethylbenzyl) phenyl] -2H-benzotriazole, [301] 2- [2-hydroxy-3- (α, α-dimethylbenzyl) -5-tert-octylphenyl] -2H-benzotriazole, [302] 2- {2-hydroxy-3-tert-butyl-5- [2- (omega-hydroxy-octa (ethyleneoxy) carbonyl) ethyl] -phenyl} -2H-benzotriazole, [303] 5-chloro-2- (2-hydroxy-3,5-di-tert-butylphenyl) -2H-benzotriazole, [304] 5-chloro-2- (2-hydroxy-3-tert-butyl-5-methylphenyl) -2H-benzotriazole, [305] 2- (2-hydroxy-5-tert-octylphenyl) -2H-benzotriazole, [306] 2- {2-hydroxy-3-tert-butyl-5- [2- (octyloxy) carbonyl) ethyl] phenyl} -2H-benzotriazole, [307] 5-trifluoromethyl-2- (2-hydroxy-3-α-cumyl-5-tert-octylphenyl) -2H-benzotriazole, [308] 5-trifluoromethyl-2- (2-hydroxy-5-tert-octylphenyl) -2H-benzotriazole, [309] 5-trifluoromethyl-2- (2-hydroxy-3,5-di-tert-octylphenyl) -2H-benzotriazole, [310] 2,2'-methylene-bis [6- (5-trifluoromethyl-2H-benzotriazol-2-yl) -4-tert-octylphenol], [311] Methylene-2- [4-tert-octyl-6- (2H-benzotriazol-2-yl) phenol] 2 '-[4-tert-octyl-6- (5-trifluoromethyl-2H- Benzotriazol-2-yl) phenol], [312] 3- (5-trifluoromethyl-2H-benzotriazol-2-yl) -5-tert-butyl-4-hydroxyhydrocinnamic acid, [313] Methyl 3- (5-trifluoromethyl-2H-benzotriazol-2-yl) -5-tert-butyl-4-hydroxyhydrocinnamate, [314] Isooctyl 3- (5-trifluoromethyl-2H-benzotriazol-2-yl) -5-tert-butyl-4-hydroxyhydrocinnamate, [315] 5-trifluoromethyl-2- [2-hydroxy-5- (3-hydroxypropyl) phenyl] -2H-benzotriazole, [316] 5-trifluoromethyl-2- [2-hydroxy-5- (3-acryloyloxypropyl) phenyl] -2H-benzotriazole, [317] 5-trifluoromethyl-2- [2-hydroxy-5- (3-methacryloyloxypropyl) phenyl] -2H-benzotriazole, [318] 5-trifluoromethyl-2- [2-hydroxy-5- (3-acrylylaminopropyl) phenyl] -2H-benzotriazole, [319] 5-trifluoromethyl-2- [2-hydroxy-5- (3-methacrylylaminopropyl) phenyl] -2H-benzotriazole, [320] 5-trifluoromethyl-2- (2-hydroxy-3-α-cumyl-5-tert-butylphenyl) -2H-benzotriazole, [321] 5-trifluoromethyl-2- (2-hydroxy-3-α-cumyl-5-nonylphenyl) -2H-benzotriazole, [322] 5-trifluoromethyl-2- [2-hydroxy-3-α-cumyl-5- (2-hydroxyethyl) phenyl] -2H-benzotriazole, [323] 5-trifluoromethyl-2- [2-hydroxy-3-α-cumyl-5- (3-hydroxypropyl) phenyl] -2H-benzotriazole, [324] 5-trifluoromethyl-2- (2-hydroxy-3,5-di-tert-amylphenyl) -2H-benzotriazole, [325] 5-trifluoromethyl-2- (2-hydroxy-3,5-di-tert-butylphenyl) -2H-benzotriazole, [326] 5-trifluoromethyl-2- (2-hydroxy-3-dodecyl-5-methylphenyl) -2H-benzotriazole, [327] 5-trifluoromethyl-2- [2-hydroxy-3-tert-butyl-5- (3-hydroxypropyl) phenyl) -2H-benzotriazole, [328] 5-trifluoromethyl-2- [2-hydroxy-3-tert-butyl-5- (2-hydroxyethyl) phenyl] -2H-benzotriazole, [329] 5-trifluoromethyl-2- [2-hydroxy-5- (2-hydroxyethyl) phenyl] -2H-benzotriazole, [330] 5-trifluoromethyl-2- (2-hydroxy-3,5-di-α-cumylphenyl) -2H-benzotriazole, [331] 5-fluoro-2- (2-hydroxy-3,5-di-α-cumylphenyl) -2H-benzotriazole, [332] 5-butylsulfonyl-2- (2-hydroxy-3,5-di-α-cumylphenyl) -2H-benzotriazole, [333] 5-butylsulfonyl-2- (2-hydroxy-3,5-di-tert-butylphenyl) -2H-benzotriazole and [334] 5-butylsulfonyl-2- (2-hydroxy-3,5-di-tert-octylphenyl) -2H-benzotriazole. [335] Preferably, the tris-aryl-s-triazole is 2,4-bis (2,4-dimethylphenyl) -6- (2-hydroxy-4-octyloxyphenyl) -s-triazine, 2,4 -Diphenyl-6- (2-hydroxy-4-hexyloxyphenyl) -s-triazine and 2,4-bis (2,4-dimethylphenyl) -6- [2-hydroxy-4- (3 -Do- / tri-decyloxy-2-hydroxypropoxy) -phenyl] -s-triazine. [336] Alkyd resin lacquers which can be stabilized against the action of light and moisture according to the invention are in particular conventional stoving lacquers (car refinery lacquers) which can be used in automotive coatings, for example alkyd / melamine resins and alkyd / acrylic acid / Lockers based on melamine resins [H. Wagner and HF Sarx, "Lackkunstharze" (1977), pages 99-123. Other crosslinkers are glycouril resins, blocked isocyanates or epoxy resins. [337] The lacquers stabilized according to the invention are suitable for both metal refining coatings and solid color tone refining, as well as for various coil coating applications. The lacquers stabilized according to the invention are preferably applied in a conventional manner by two methods, namely single coating method or double coating method. In the latter method, the pigment-containing base coating is applied first, and then the surface coating of the transparent lacquer is applied thereon. [338] In addition, the compounds of the present invention can be used in non-acid catalyzed thermosetting resins (e.g., epoxy, epoxy-polyester, vinyl, alkyd, acrylic resins and polyester resins) optionally modified with silicon, isocyanate or isocyanurate. It should be noted that it is suitable for. Epoxy and epoxy-polyester resins are crosslinked with conventional crosslinkers such as acids, acid anhydrides, amines, and the like. Correspondingly, epoxides can be used as crosslinkers for various acrylic resins or polyester resin systems modified by placing reactive groups on the backbone structure. [339] When used in double coating refining, the compounds of the present invention may be incorporated into either the transparent coating or both the transparent coating and the dyed base coating. [340] If a water soluble, water miscible or water dispersible coating is desired, ammonium salts of the acid groups present in the resin are formed. Powder coating compositions can be prepared by reacting glycidyl methacrylate with a selected alcohol component. [341] The benzotriazoles of the present invention are prepared by conventional methods for preparing such compounds. Common processes include diazolation of substituted o-nitroanilines, followed by coupling of the resulting diazonium with substituted phenols and reduction of the azobenzene intermediate to the corresponding desired benzotriazole. Starting materials for these benzotriazoles are usually commercially available products or can be prepared by conventional organic synthesis methods. [342] Although the benzotriazoles of the present invention with improved durability are particularly suitable for automotive coating applications, they will be particularly useful in other fields where improved durability is required, such as in solar membranes. [343] The following examples are for illustration only. [344] Example 1 [345] 5-trifluoromethyl-2- (2-hydroxy-3-α-cumyl-5-tert-octylphenyl) -2H-benzotriazole [346] a. Diazolation of 4-amino-3-nitro-benzotrifluoride [347] To a 500 ml three-necked flask equipped with a mechanical stirrer was added 41.2 g of 4-amino-3-nitro-benzotrifluoride, 52 ml of concentrated hydrochloric acid and 100 ml of distilled water. The stirred solution was cooled to 5 ° C. and 17.3 g of sodium nitrate dissolved in 50 ml of water was added. The solution is stirred for 2 h at 0-5 ° C., then filtered and stored at −10 ° C. [348] b. Monoazo additives [349] To a 1000 ml flask equipped with a mechanical stirrer, 40 g of sodium hydroxide dissolved in 200 ml of methanol and 32.4 g of 2-α-cumyl-4-tert-octylphenol in 50 ml of xylene are added. The solution is cooled to 5 ° C. and a diazo solution of 4-amino-nitro-benzotrifluoride prepared in part a is added at 0-5 ° C. over 2 hours. Then 100 ml of xylene are added and the organic layer is washed with water, aqueous hydrochloric acid, water, aqueous sodium bicarbonate solution and finally water. The solvent is removed under reduced pressure and the residue is purified by chromatography (silica gel, heptane: ethyl acetate 95: 5) to give 42.1 g of the additional product as a dark red paste. [350] c. Reduction of Monoazo Additives [351] A 1000 ml flask was charged with 20 g of sodium hydroxide, 40 ml of water, 42.1 g of monoazo additive prepared in part b and 400 ml of ethanol. The mixture is warmed to 80 ° C. and 27 g of formamidine sulfinic acid is added in portions with stirring. After 1.5 hours, the solution is cooled to room temperature and 100 ml of water are added. The pH is adjusted to pH 7 with concentrated hydrochloric acid. Ethanol is removed under vacuum and the aqueous layer is extracted with methylene chloride. The solvent is then evaporated in vacuo and the residue is purified by chromatography (silica gel, heptane: toluene 9: 1) and then crystallized from ethanol. The title compound is obtained as a pale yellow solid with a melting point of 119-121 ° C. in a yield of 5.6 g. [352] Example 2 [353] 5-trifluoromethyl-2- (2-hydroxy-5-tert-octylphenyl) -2H-benzotriazole [354] The title compound is prepared according to the general procedure of Example 1, and the diazo compound of 4-amino-3-nitrobenzotrifluoride and 4-tert-octylphenol are purified by chromatography on silica gel. The product is recrystallized from heptane or methanol to give the title compound as white analogous solid at melting point 80-81 ° C. [355] Example 3 [356] 5-trifluoromethyl-2- (2-hydroxy-3-allyl-5-tert-octylphenyl) -2H-benzotriazole [357] The compound prepared in Example 2 (13.01 g, 0.033 mol), potassium hydroxide (2.37 g, 0.036 mol) and ethanol (60 ml) were charged to the reactor and stirred at ambient temperature for 2 hours. Allyl bromide (4.84 g, 0.039 mol) and potassium iodide (0.34 g, 0.002 mol) are added to the reaction mixture and heated to 85 ° C. After holding at 85 ° C. for 4.5 hours, the solvent is removed and replaced with 100 ml of heptane. The mixture is washed twice with 40 ml of water. The solvent is then removed to yield 14.2 g of the corresponding O-allyl ether as off-white solid. [358] Anal: 1 H NMR (CDCl 3 ): δ 0.78 (s, 9H), 1.41 (s, 6H), 1.77 (s, 2H), 4.60-4.65 (d, 2H), 5.16-5.34 (m, 2H) , 5.86-6.00 (m, 1H), 7.06-7.11 (d, 1H), 7.49-7.54 (dd, 1H), 7.61-7.67 (m, 2H), 8.08-8.12 (d, 1H), 8.35 (s, 1H). [359] The O-allyl compound (14.2 g) prepared above was charged to the reactor, heated to 190 to 195 ° C., and maintained at this temperature for 5 hours. Flash column chromatography on silica gel using ethyl acetate / heptane solvent as eluent gave the title compound (yield 12.2 g) as a yellow oil. [360] analysis: [361] Mass spectrum: 432 (M + H) [362] 1 H NMR (CDCl 3 ): δ 0.78 (s, 9H), 1.46 (s, 6H), 1.81 (s, 2H), 3.53-3.64 (d, 2H), 5.06-5.20 (m, 2H), 6.02 -6.18 (m, 1H), 7.29-7.34 (d, 1H), 7.66-7.72 (dd, 1H), 8.05-8.12 (d, 1H), 8.29-8.35 (m, 2H), 11.17 (s, 1H) . [363] Example 4 [364] 5-trifluoromethyl-2- [2-hydroxy-3- (3-triethoxysilyl) propyl-5-tert-octylphenyl] -2H-benzotriazole [365] The title compound was the 5-trifluoromethyl-2- (2-hydroxy-3-allyl-5-tert-octyl-phenyl) -2H-benzotriazole, Karstedt catalyst prepared in Example 3 above. (Complex of divinyl-tetramethyldisiloxane and platinum) and triethoxysilane were prepared by the process of Example 3 of US Pat. No. 5,391,795. It is separated as a viscous yellow oil. [366] 29 Si NMR (CDCl 3 , 500 MHz, Cr (AcAc) 2 ): -44.78 ppm. [367] 1 H NMR (CDCl 3 , 500 MHz): δ 11.50 (s, 1H), 8.32 (d, 1H), 8.27 (d, 1H), 8.09 (d, 1H), 7.69 (dd, 1H), 7.31 (d , 1H), 3.83 (q, 6H), 2.83 (t, 2H), 1.84 (quartet, 2H), 1.80 (s, 2H), 1.45 (s, 6H), 1.22 (t, 9H), 0.78 (s , 9H), 0.76 (t, 2H). [368] 19 F NMR (CDCl 3 , 500 MHz, CF 3 COOH): -68.88 ppm. [369] Example 5 [370] Methyl 3- (trifluoromethyl-2H-benzotriazol-2-yl) -5-tert-butyl-4-hydroxyhydrocinnamate [371] Unseparated solid of the title compound from 62.5 g of 4-amino-3-nitro-benzotrifluoride (= 4-trifluoromethyl-o-nitroaniline) by carrying out the general procedure of part a and b of Example 1 Prepare monoazo intermediates. [372] Monoazo intermediate (84 g, 0.19 mol), xylene (116 g, 1.08 mol), diethylamine (100 g, 1.4 mol) and 5% palladium on charcoal (0.5 g, 50% analysis) are charged to the reactor. Hydrazine (27.4 g, 0.56 mol) is added dropwise in a temperature range of 15 to 45 ° C. over 2 hours. After the addition is complete, the temperature is raised to 80 ° C. and maintained at this temperature for 3 hours. Completion of the reaction is determined by thin layer chromatography. The catalyst is filtered off and the solvent is removed in vacuo to yield 36 g of product. After recrystallization from methanol, the title compound is obtained as a pale yellow needle with a melting point of 105 to 107 ° C. [373] analysis: [374] Mass spectrum: 422 (M + H) [375] 1 H NMR (CDCl 3 ): δ 1.51 (s, 9H), 2.71 (t, 2H), 3.02 (t, 2H), 3.71 (s, 3H), 7.26 (d, 1H), 7.69 (dd, 1H ), 8.07 (d, 1 H), 8.17 (d, 1 H), 11.55 (s, 1 H). [376] Example 6 [377] 5-trifluoromethyl-2- [2-hydroxy-3-tert-butyl-5- (3-hydroxypropyl) phenyl] -2H-benzotriazole [378] The title compound is prepared by reacting the ester compound of Example 5 with lithium aluminum hydride according to the process of Example 19 in US Pat. No. 5,280,124. The title compound is obtained as a solid (yield 80%) with a melting point of 90 to 91 ° C. [379] analysis: [380] 1 H NMR (CDCl 3 ): δ 1.51 (s, 9H), 1.95 (m, 2H), 2.75 (t, 2H), 3.75 (t, 2H), 7.26 (d, 1H), 7.65 (dd, 1H ), 8.05 (d, 1H), 8.14 (d, 1H), 8.26 (s, 1H) [381] Example 7 [382] 5-trifluoromethyl-2- [2-hydroxy-3-tert-butyl-5- (3-allyl-carbamoyloxy) propylphenyl] -2H-benzotriazole [383] The title compound is prepared by reacting the stoichiometric amount of the compound prepared in Example 6 with allyl isocyanate. [384] Example 8 [385] 5-trifluoromethyl-2- {2-hydroxy-3-tert-butyl-5- [3- (3-triethoxyoxylyl) propylcarbamoyloxy) propyl] phenyl} -2H-benzotria Sol [386] The title compound is prepared by reacting the allyl compound of Example 7 with triethoxysilane following the process of Example 4. [387] Example 9 [388] 5-trifluoromethyl-2- [2-hydroxy-3-tert-butyl-5- (2-hydroxyethyl) phenyl] -2H-benzotriazole [389] The title compound is prepared using the general procedure of Example 1, replacing 2-a-cumyl-4-tert-octylphenol with 2-3-butyl-4- (2-hydroxyethyl) phenol. [390] Example 10 [391] 5-trifluoromethyl-2- [2-hydroxy-3-tert-butyl-5- (2-allylcarbamoyloxy) ethylphenyl] -2H-benzotriazole [392] The title compound is prepared by reacting the stoichiometric amount of the compound prepared in Example 9 with allyl isocyanate. [393] Example 11 [394] 5-trifluoromethyl-2- {2-hydroxy-3-tert-butyl-5- [2- (3-triethoxyoxylyl) propylcarbamoyloxy) ethyl] phenyl} -2H-benzotria Sol [395] The title compound is prepared by reacting the compound prepared in Example 10 with triethoxysilane according to the process of Example 4. [396] Example 12 [397] 5-trifluoromethyl-2- [2-hydroxy-5- (2-hydroxyethyl) phenyl] -2H-benzotriazole [398] The title compound is prepared using the general procedure of Example 1, replacing 2-a-cumyl-4-tert-octylphenol with 4- (2-hydroxyethyl) phenol. [399] Example 13 [400] 5-trifluoromethyl-2- [2-hydroxy-5- (2-allylcarbamoyloxy) ethylphenyl] -2H-benzotriazole [401] The title compound is prepared by reacting the stoichiometric amount of the compound prepared in Example 12 with allyl isocyanate. [402] Example 14 [403] 5-trifluoromethyl-2- {2-hydroxy-5- [2- (3-triethoxysilyl) propylcarbamoyloxy) ethyl] phenyl} -2H-benzotriazole [404] The title compound is prepared by reacting the compound prepared in Example 13 with triethoxysilane according to the process of Example 4. [405] Example 15 [406] 5-trifluoromethyl-2- [2-hydroxy-3-α-cumyl-5- (2-hydroxyethyl) phenyl] -2H-benzotriazole [407] The title compound is prepared using the general procedure of Example 1 by replacing 2-a-cumyl-4-tert-octylphenol with 2-a-cumyl-4- (2-hydroxyethyl) phenol. [408] Example 16 [409] 5-trifluoromethyl-2- [2-hydroxy-3-α-cumyl-5- (2-allylcarbamoyloxy) ethylphenyl] -2H-benzotriazole [410] The title compound is prepared by reacting the stoichiometric amount of the compound prepared in Example 15 with allyl isocyanate. [411] Example 17 [412] 5-trifluoromethyl-2- {2-hydroxy-3-α-cumyl-5- [2- (3-triethoxysilyl) propylcarbamoyloxy) ethyl] phenyl} -2H-benzotriazole [413] The title compound is prepared by reacting the compound prepared in Example 16 with triethoxysilane according to the process of Example 4. [414] Example 18 [415] 5-trifluoromethyl-2- [2-hydroxy-3- (3-diethoxymethylsilyl) propyl-5-tert-octylphenyl] -2H-benzotriazole [416] The title compound was the 5-trifluoromethyl-2- (2-hydroxy-3-allyl-5-tert-octyl-phenyl) -2H-benzotriazole, Karstedt catalyst prepared in Example 3 above. (Complex of divinyl-tetramethyldisiloxane and platinum) and diethoxymethylsilane were prepared by the process of Example 1 of US Pat. No. 5,679,820. [417] Very similar to the compounds listed in the following table, starting with triphenylsilane, tribenzylsilane, other trialkylsilanes, trialkoxysilanes, dialkoxyalkylsilanes, alkoxydialkylsilanes and similar silane intermediates, the corresponding silylated benzotriazoles Compounds can be prepared. [418] Examples 19-42 [419] Compounds of formula III can be prepared using reaction conditions similar to those described in Example 18. [420] [421] ExampleG 1 G 2 E 2 R 1 R 219HCF 3 α-cumylmethylethyl 20ClCF 3 α-cumylmethylethyl 21FCF 3 Dodecylmethylethyl 22FFmethylmethylethyl 23ClClLevel 3-Octylmethylethyl 24FClDodecylmethylethyl [422] In each of the compounds of Examples 19-24, E 5 is hydrogen. [423] ExampleG 2 E 3 E 2 R 1 R 225E 3 SO 2 ethylTert-butylmethylethyl 26E 3 SO 2 n-butylLevel 3-Octyln-butylethyl 27E 3 SO 2 n-butylDodecylmethylPhenyl 28E 3 SO 2 **Tert-butylHexylHexyl 29E 3 SO 2 Phenylmethylmethylethyl 30E 3 SO 2 DodecylTert-butylmethylethyl 31-PO (C 6 H 5 ) 2 -Tert-butylmethylethyl [424] ** is CH 3 OCO—CH 2 CH 2 —. [425] In each of the compounds of Examples 25-31 G 1 and E 5 are both hydrogen. [426] ExampleG 2 G 3 E 2 R 1 R 232-COOG 3 methylα-cumylmethylethyl 33-COOG 3 Cyclohexylmethylmethylethyl 34-COOG 3 Dodecylα-cumylmethylethyl 35-CONHG 3 HexylCH 2 CH 2 OHmethylethyl 36-CON (G 3 ) 2 Butylmethylmethylethyl 37Phthalimido-Octylmethylethyl [427] In each of the compounds of Examples 32-37 G 1 and E 5 are both hydrogen. [428] ExampleG 2 E 2 E 5 R 1 R 238CF 3 DodecylMethoxymethylethyl 39CF 3 ButylOctoxymethylethyl 40CF 3 OctylNH-CO-CH 3 methylethyl 41CF 3 methylNHCO-octylmethylethyl 42CF 3 DodecylNH-CH 3 methylethyl [429] In each of the compounds of Examples 38-42, G 1 is hydrogen. [430] Examples 43-61 [431] In Examples 43-46, these materials were prepared by methods analogous to those in Example 5b of US Pat. No. 5,185,445, wherein the appropriately substituted benzotriazol was dissolved in toluene and in the presence of dibutyltin oxide. Heated to 100 ° C. with hydroxy substituted alkyl-silanes or alkyl-siloxanes to form the title compound. [432] In Examples 47-48, these materials are prepared by adding an appropriately substituted benzotriazole with an amino substituted alkyl-silane or alkyl-siloxane to the reaction flask and heating to 120 ° C. A slight vacuum is applied to facilitate removal of the methanol byproduct to afford the title compound. [433] In Examples 49-52, the compounds are prepared by methods analogous to those in Example 6 of US Pat. No. 5,185,445, wherein the appropriate benzotriazole starting material and 3-chloro in aqueous N, N-dimethylacetamide The suspension of propyl diethoxymethylsilane or related silanes and potassium carbonate is heated to 100 ° C. to afford the desired compound. [434] In Example 53, appropriate intermediate benzotriazole is prepared by the process of Example 10. The intermediate is then hydrolyzed with diethoxymethylsilane using the experimental conditions of Example 4 to afford the desired compound. [435] The compounds of Examples 54-58 are prepared in several steps. The first intermediate benzotriazole was prepared by the method of Example 1, but instead of using 2-a-cumyl-4-tert-octylphenol, Michael additives of resorcinol and methyl acrylate were used to prepare the target compound. To obtain. The second intermediate is then prepared by reacting the first intermediate benzotriazole with α-methylstyrene in the presence of p-toluenesulfonic acid. Subsequent intermediate compounds are prepared by reacting the second intermediate in a manner similar to Example 30 of British Patent No. 2,319,035A. Subsequent intermediates are prepared by reacting the last intermediate benzotriazole with allyl alcohol in the presence of a toluene solvent. Finally, allyl substituted benzotriazole is reacted with diethoxymethylsilane using the conditions of Example 4. [436] In addition, the compounds of Examples 59-62 are prepared in several steps. The first intermediate is prepared by a method similar to that of Example 3. In a subsequent step the intermediate benzotriazole is described in Brown in "Boranes in Organic Chemistry", Cornell University Press, Ithaca, NY 1972; and J. March in "Advanced Organic Chemistry", 2nd Edition, McGraw-Hill, New York, 1977, page 718. This intermediate is reacted by the process of Example 10 by reacting 2- (3-hydroxypropyl) substituted benzotriazole with allyl isocyanate. The title compound is prepared by allyl urethane intermediate by reaction with diethoxymethylsilane according to the method of Example 4. [437] According to the general method described above, the compound of formula IV or formula V is prepared. [438] [439] Example * G 1 G 2 E 1 T 3 / T 4 X 2 nR 1 R 243HCF 3 Cu(CH 2 ) 2 / (CH 2 ) 3 -O-3MeEt 44HCF 3 Cu(CH 2 ) 2 / (CH 2 ) 3 -O-2MeEt 45HCF 3 Cu(CH 2 ) 2 / (CH 2 ) 3 -O-OneMeEt 46HCF 3 Cu(CH 2 ) 2 / (CH 2 ) 3 -O-0MeEt 47HCF 3 tBu(CH 2 ) 2 / (CH 2 ) 4 -NH-OneMeMe 48ClCltBu(CH 2 ) 2 / (CH 2 ) 3 -NH-2MeEt [440] In the compounds of Examples 43-58, tBu is tert-butyl, Cu is α-cumyl, Et is ethyl and Me is methyl. [441] In each of Compounds 43-48, E 5 is hydrogen, q is 0, and r, s, and t are each 1. If q, r, s and / or t are zero, this indicates a direct bond. [442] Example * G 2 E 1 T 3 / T 4 X 1 X 2 rs 49FtBu(CH 2 ) 3 / (CH 2 ) 3 -O--00 50**Cu(CH 2 ) 3 / (CH 2 ) 3 -O--00 51**tBu(CH 2 ) 3 / (CH 2 ) 3 -O--00 52**tBu(CH 2 ) 3 / (CH 2 ) 3 -NH--00 53CNtBu(CH 2 ) 2 / (CH 2 ) 3 -O--NH-OneOne [443] TBu is tert-butyl and Cu is α-cumyl for the compounds of Examples 49-53. [444] ** for compound 50 is butyl-SO 2- , ** for compound 51 is phenyl-SO 2 -and ** for compound 52 is dodecyl-SO 2- . [445] In each of compounds 49 to 53, E 5 is hydrogen, q and t are each 1, R 1 is methyl, R 2 is ethyl, G 1 is hydrogen, n is 2. [446] ExampleG 2 E 1 E 5 X 2 n 54CF 3 α-cumylMethoxy-O-2 55CF 3 α-cumylOctyloxy-O-One 56CF 3 t-butylNHCOCH 3 -NH-2 57*α-cumylNHCOC 8 H 17 -NH-One 58COOCH 3 α-cumylHydrogen-NH-2 [447] ** in compound 57 is phenyl-SO 2- . [448] For each of compounds 54 to 58, G 1 is hydrogen, T 3 is ethylene, T 4 is trimethylene, q is 0, r, s and t are each 1, R 1 is methyl, R 2 is ethyl. [449] [450] ExampleG 1 G 2 E 2 T 3 T 459FFα-cumyl(CH 2 ) 3 (CH 2 ) 360HCF 3 methyl(CH 2 ) 3 (CH 2 ) 361HCF 3 t-octyl(CH 2 ) 3 (CH 2 ) 3 [451] In each of compounds 59 to 61, E 5 is hydrogen, X 1 is —O—, X 2 is —NH—, q, r, s and t are each 1, n is 2, R 1 Is methyl, R 2 is ethyl and G 1 is hydrogen. [452] Examples 62-75 [453] In Examples 62-75, suitably substituted benzotriazoles are prepared according to the general method of Example 29 of British Patent Publication No. 2,319,035A and Example 54 of the present invention. The intermediate is reacted with allyl bromide dissolved in ethanol in the presence of potassium hydroxide and potassium iodide. In the case of Example 66, allyl bromide is substituted with 6-bromohex-1-ene. The unsaturated intermediate formed is hydrosilylation with an appropriately substituted silane using the conditions of Example 4. [454] According to the general method described above, the compound of formula VI is prepared. [455] [456] Example * G 2 E 1 E 2 T 3 / T 4 qrnX 62FCuMe(CH 2 ) 3 /-002-O- 63CltButOc(CH 2 ) 3 /-00One-O- 64ClDoMe(CH 2 ) 3 /-002-O- 65CF 3 CutBu(CH 2 ) 3 /-002-O- 66CF 3 tButBu(CH 2 ) 6 /-003-O- 67CF 3 CutBu(CH 2 ) 3 /-000-O- 68**CutBu(CH 2 ) 3 /-002-O- 69**tBuDo(CH 2 ) 3 /-002-O- 70**CuMe(CH 2 ) 3 /-00One-O- 71***CutBu(CH 2 ) 3 /-002-O- 72CF 3 CuMe(CH 2 ) 3 / (CH 2 ) 3 OneOne2-O- 73CF 3 tBuDo(CH 2 ) 3 / (CH 2 ) 3 OneOneOne-O- 74CF 3 CuMe(CH 2 ) 3 /-002-NH- 75CF 3 tButBu(CH 2 ) 3 / (CH 2 ) 3 OneOne2-NH- [457] tBu is tert-butyl, Cu is α-cumyl, Do is dodecyl, Me is methyl and tOc is tert-octyl. [458] In each of the compounds of Examples 62-75, R 1 is methyl, R 2 is ethyl and G 1 is hydrogen (wherein, in compound 64, G 1 is fluoro). [459] ** in compound 68 is phenyl-SO 2- , ** in compound 69 is n-butyl-SO 2 -and ** in compound 70 is dodecyl-SO 2- . [460] *** in compound 71 is (C 6 H 5 ) 2 PO-. [461] Examples 76-92 [462] In Examples 76 to 85, these compounds are prepared in substantially the same reaction scheme. A typical synthesis of the compound of Example 77 is summarized below. [463] 5-carbomethoxy-2- (2-hydroxy-3-α-cumyl-5-tert-octylphenyl) -2H-benzotria synthesized as shown in Example 36 of British Patent Publication No. 2,319,035A The sol is transesterified with excess 1,4-butanediol in the presence of p-toluenesulfonic acid. The intermediate is reacted with allyl isocyanate according to the method of Example 10. The title compound is prepared using allyl urethane substituted benzotriazole intermediate prepared above with diethoxymethylsilane using the conditions of Example 4 of the present invention. [464] In Examples 86-92, these compounds are prepared similar to the methods of Examples 76-85. The required intermediate is prepared as described above for Example 77 except that the transesterification reaction is carried out with allyl alcohol instead of butylene glycol. [465] According to the general method described above, the compound of formula VII is prepared. [466] [467] Example * E 1 E 2 E 5 T 3 / T 4 R 1 R 2 nX 176CuMeH(CH 2 ) 2 / (CH 2 ) 3 MeEt3-O- 77CutOcH(CH 2 ) 4 / (CH 2 ) 3 MeEt2-O- 78tButBuH(CH 2 ) 6 / (CH 2 ) 6 MeEt2-NH- 79CuCuH(CH 2 ) 3 / (CH 2 ) 3 MeBu0-O- 80CuCuOCH 3 (CH 2 ) 3 / (CH 2 ) 3 MeEtOne-O- 81CuCuOOc(CH 2 ) 3 / (CH 2 ) 3 MeEt2-NH- 82DoDoNHCOOc(CH 2 ) 4 / (CH 2 ) 3 MeEtOne-O- 83CutOcNHCOMe(CH 2 ) 4 / (CH 2 ) 3 MeEt2-O- 84CutBuNHCOMe(CH 2 ) 4 / (CH 2 ) 3 EtEt3-NH- 85CuDoH(CH 2 ) 4 / (CH 2 ) 3 HeBu2-O- [468] * Bu is butyl, tBu is tert-butyl, Cu is a-cumyl, Do is dodecyl, Et is ethyl, He is hexyl, Me is methyl, Oc is octyl, tOc is 3 Rapid-octyl. [469] In each of the compounds of Examples 76-85, j is 1. [470] Example * E 1 E 2 E 5 T 3 R 2 R 1 nX 86CutOcH(CH 2 ) 3 MeEt2-O- 87tButBuH(CH 2 ) 3 MeEt3-NH- 88CuMeH(CH 2 ) 6 BuBuOne-O- 89CuCuOCH 3 (CH 2 ) 3 MeEt2-O- 90CuCuOC 8 H 17 (CH 2 ) 3 MeEt2-O- 91CuCuNHCOOc(CH 2 ) 3 MeEtOne-O- 92HHNHCOOc(CH 2 ) 3 MeEt0-O- [471] * Bu is butyl, tBu is tert-butyl, Cu is α-cumyl, Et is ethyl, Me is methyl, Oc is octyl, tOc is tert-octyl. [472] In each of the compounds of Examples 86-92, j is 0 and the T 4 residue is absent. [473] Examples 93-106 [474] Since the compounds of Examples 96-106 are prepared by substantially the same synthetic route, the preparation of the compounds of Example 98 is summarized below. [475] Bay of 2- (2-hydroxy-5-methylphenyl) -2H-benzotriazole using Mannich base form conditions summarized in Examples 34-35 of co-pending patent application 09 / 234,880 Nich base is reacted with methyl 3- (5-trifluoromethyl-2H-benzotriazol-2-yl) -4-hydroxyhydrocinnamate to form ester substituted bis-benzotriazole intermediate. The ester intermediate product is reduced with lithium aluminum hydride to form the corresponding alcohol substituted benzotriazole following the process of Example 19 of US Pat. No. 5,280,124. The hydroxyalkyl intermediate form is converted to the corresponding alkene by reduction with phosphorus tribromide in pyridine. Similar processes are described in G.I. Samokhvalov et al., Proc. Acad. Sci. USSR, 84, 1179 (1952) and J. Gen. Chem. USSR, 26, 3111 (1956). The formed allyl substituted bis-benzotriazole is then silylated with diethoxymethylsilane according to the process of Example 4. [476] According to the general method described above, the compound of formula VIII is prepared. [477] [478] In the above formula (VIII), [479] At least one of G 2 , G 7 , E 2 and E 9 contains a group A or a group B, [480] A is -T 1- [X] q- [CO] r- [X 2 ] s- [T 2 ] t -Si (OR 2 ) n (R 1 ) 3-n , [481] B is -CO-XT 1- [OCO-NH-T 2 ] j -Si (OR 2 ) n (R 1 ) 3-n (where j is 0 or 1). [482] ExampleG 2 G 7 E 2 E 9 n 93CF 3 CF 3 AA3 94C 6 H 5 SO 2 C 6 H 5 SO 2 AA2 95C 4 H 9 SO 2 C 4 H 9 SO 2 AA2 96ClClAA0 97FFAAOne 98CF 3 HACH 3 2 [483] In Examples 93-98, G 1 and G 6 are each hydrogen, T 1 is trimethylene, R 1 is methyl, R 2 is ethyl, q, r, s and t are each 0 And L is methylene. [484] Example * G 2 G 7 E 2 E 9 n 99C 6 H 5 SO 2 HAtOc2 100CNHAtBu0 101CH 3 COOHADoOne 102HHMeA2 103HClMeA3 [485] In the compounds of Examples 99-103, tBu is tert-butyl, Do is dodecyl, Me is methyl and tOc is tert-octyl. [486] In Examples 99-103, G 1 and G 6 are each hydrogen, T 1 is ethylene, T 2 is trimethylene, R 1 is methyl, R 2 is ethyl, and r, s and t are 1 each and L is methylene. [487] In Example 99, X 2 is -O- and q is 0, in Example 100 X is -O-, X 2 is -NH-, q is 1, and in Example 101, X is -NH- and X 2 Is -O- and q is 1, and in Example 102, X 2 is -O- and q is 0. [488] Example * G 2 G 7 E 2 E 9 n 104ClHBMe2 105BClMeMe2 106BHtOctOc0 [489] In the compounds of Examples 104-106, Me is methyl and tOc is tert-octyl. [490] In Example 104, G 1 is chloro, G 6 is hydrogen, T 1 is trimethylene, X is —O—, R 1 and R 2 are each butyl, j is 0 and L is methylene. [491] In Example 105, G 1 and G 6 are each hydrogen, T 1 and T 2 are each trimethylene, X is -NH-, R 1 is methyl, R 2 is ethyl, j is 1 and L is methylene. [492] In Example 106, G 1 and G 6 are each hydrogen, T 1 is trimethylene, X is —O—, R 1 is methyl, R 2 is ethyl, j is 0 and L is methylene. [493] Comparative Example 1 [494] [495] The hydroxybenzophenone compound is prepared according to Example 1 of US Pat. No. 5,391,795. U.S. Patent 5,391,795 is incorporated herein by reference. [496] Comparative Example 2 [497] [498] The allyl substituted hydroxybenzophenone compound is prepared according to Example 2 of US Pat. No. 5,391,795. [499] Comparative Example 3 [500] [501] The triethoxysilylpropyl substituted hydroxybenzophenone compound is prepared according to Example 3 of US Pat. No. 5,391,795. [502] Comparative Example 4 [503] [504] 3- (2H-benzotriazol-2-yl) -5-tert-butyl-4-hydroxyhydrocinnamic acid (5 g, 0.0146 mol), toluene (100 g, 1.08 mol), thionyl chloride (2.55 g, 0.0209 mol) and DMF (0.1 g, 0.0014 mol) are added to the reaction flask and heated to 90 ° C. After 30 minutes, the excess thionyl chloride and 50 g of toluene are distilled off. The resulting solution was added to an addition funnel and, at ambient temperature, H 2 N (CH 2 ) 3 Si (OEt) 3 (3.88 g, 0.0175 mol), toluene (50 g, 0.54 mol) and triethylamine (100 g, 0.98 mol) Is added to the solution. After the addition is complete (about 30 minutes), the slurry is heated to 75 ° C. for 90 minutes. The salt is filtered off and the solvent is distilled off. The resulting oil is chromatographed on silica gel using ethyl acetate / heptane (1: 1) as eluent. The desired product is obtained as a pale yellow solid (6.4 g) with a melting point of 90 to 95 ° C. [505] 1 H NMR (500 MHz, CDCl 3 ): δ 11.80 (s, 1H), 8.15 (d, 1H), 7.94 (m, 2H), 7.49 (m, 2H), 7.22 (d, 1H), 5.73 (broad t, 1H), 3.80 (q, 6H), 3.27 (q, 2H), 3.02 (t, 2H), 2.52 (t, 2H), 1.61 (quartet, 2H), 1.50 (s, 9H), 1.21 ( t, 9H), 0.60 (t, 2H). [506] 29 Si NMR (500 MHz, CDCl 3 , Cr (AcAc) 2 ): -45.4 ppm. [507] Mass spectrum: M / Z = 542 [508] Comparative Example 5 [509] [510] Methyl 3- (2H-benzotriazol-2-yl) -4-hydroxyhydrocinnamate (12 g, 0.04 mol), HO (CH 2 ) 2 Si (CH 3 ) 3 (5 g, 0.042 mol), dibutyl Tin oxide (3.7 g, 0.015 mol) and toluene (54 g, 0.59 mol) are added to the reaction flask and heated to 100 ° C. After 17 hours, the solvent is distilled off and the resulting oil is chromatographed on silica gel using heptane / ethyl acetate (9: 1) as eluent. The desired product is obtained as a white solid with a melting point of 73 to 75 ° C. (12 g). [511] 29 Si NMR (500 MHz, CDCl 3 , Cr (AcAc) 2 ): 0.15 ppm. [512] 1 H NMR (500 MHz, CDCl 3 ): δ 11.20 (s, 1H), 8.25 (d, 1H), 7.94 (m, 2H), 7.49 (m, 2H), 7.25 (d, 1H), 7.15 (d , 1H), 4.20 (t, 2H), 3.00 (t, 2H), 2.65 (t, 2H), 1.00 (t, 2H), 0.15 (s, 9H). [513] Mass spectrum: 382 (M-H). [514] Comparative Example 6 [515] [516] The compound is prepared as a pale yellow solid with a melting point of 35 to 44 ° C. with appropriate starting materials according to the process of Comparative Example 5. [517] 29 Si NMR (500 MHz, CDCl 3 , Cr (AcAc) 2 ): 2.50 ppm. [518] 1 H NMR (500 MHz, CDCl 3 ): δ 11.20 (s, 1H), 8.20 (d, 1H), 7.94 (m, 2H), 7.48 (m, 2H), 7.19 (d, 1H), 4.20 (t , 2H), 2.78 (t, 2H), 2.35 (m, 2H), 2.05 (m, 2H), 1.55 (s, 9H), 0.91 (t, 2H), 0.10 (s, 9H). [519] Mass spectrum: 452 (M-H). [520] Comparative Example 7 [521] [522] According to the process of Comparative Example 4 of the present invention, the compound is prepared as a white solid having a melting point of 128 to 138 ° C with an appropriate starting material. [523] 29 Si NMR (CDCl 3 , 500 MHz, Cr (AcAc) 2 ): -45.44 ppm. [524] 1 H NMR (CDCl 3 , 500 MHz): δ 11.18 (s, 1H), 8.26 (d, 1H), 7.94 (m, 2H), 7.49 (m, 2H), 7.21 (dd, H), 7.12 (d , 1H), 5.72 (broad, 1H), 3.79 (q, 6H), 3.25 (q, 2H), 3.03 (t, 2H), 2.52 (t, 2H), 1.59 (quartet, 2H), 1.21 (t , 9H), 0.58 (t, 2H). [525] Mass spectrum: 897 (M-H). [526] Example 107 [527] 5-trifluoromethyl-2- [2-hydroxy-3- (3-triethoxysilyl) propyl-5-tert-octylphenyl] -2H-benzotriazole [528] [529] The title compound was the 5-trifluoromethyl-2- (2-hydroxy-3-allyl-5-tert-octyl-phenyl) -2H-benzotriazole, Karstedt catalyst prepared in Example 3 above. (Complex of divinyl-tetramethyldisiloxane and platinum) and triethoxysilane were prepared by the process of Example 3 of US Pat. No. 5,391,795. It is separated as a viscous yellow oil. [530] 29 Si NMR (CDCl 3 , 500 MHz, Cr (AcAc) 2 ): -44.78 ppm. [531] 1 H NMR (CDCl 3 , 500 MHz): δ 11.50 (s, 1H), 8.32 (d, 1H), 8.27 (d, 1H), 8.09 (d, 1H), 7.69 (dd, 1H), 7.31 (d , 1H), 3.83 (q, 6H), 2.83 (t, 2H), 1.84 (quartet, 2H), 1.80 (s, 2H), 1.45 (s, 6H), 1.22 (t, 9H), 0.78 (s , 9H), 0.76 (t, 2H). [532] 19 F NMR (CDCl 3 , 500 MHz, CF 3 COOH): -68.88 ppm. [533] Example 108 [534] [535] The compound is prepared as a yellow viscous oil with the appropriate starting materials according to the processes of Examples 3 and 4 of the present invention. [536] 29 Si NMR (CDCl 3 , 500 MHz, Cr (AcAc) 2 ): -44.7 ppm. [537] 1 H NMR (CDCl 3 , 500 MHz): δ 11.51 (s, 1H), 8.30 (d, 1H), 8.25 (d, 1H), 8.09 (d, 1H), 7.69 (dd, 1H), 7.31 (d , 1H), 3.81 (q, 6H), 2.83 (t, 2H), 1.85 (quartet, 2H), 1.25 (t, 9H), 0.78 (s, 9H), 0.76 (t, 2H). [538] 19 F NMR (CDCl 3 , 500 MHz, CF 3 COOH): -68.8 ppm. [539] Example 109 [540] [541] The compound is prepared as a yellow viscous oil with the appropriate starting materials according to the processes of Examples 3 and 4 of the present invention. [542] 29 Si NMR (CDCl 3 , 500 MHz, Cr (AcAc) 2 ): -44.82 ppm. [543] 1 H NMR (CDCl 3 , 500 MHz): δ 11.40 (s, 1H), 8.73 (d, 1H), 8.25 (d, 1H), 8.03 (d, 1H), 8.00 (m, 2H), 7.91 (dd , 1H), 7.61-7.55 (m, 3H), 7.32 (d, 1H), 3.83 (q, 6H), 2.83 (t, 2H), 1.83 (quartet, 2H), 1.39 (s, 9H), 1.23 (t, 9H), 0.76 (t, 2H). [544] Example 110 [545] [546] According to the process of Comparative Example 4 of the present invention, the compound is prepared as a light yellow solid having a melting point of 106 to 116 ° C with an appropriate starting material. [547] 29 Si NMR (CDCl 3 , 500 MHz, Cr (AcAc) 2 ): -45.57 ppm. [548] 1 H NMR (CDCl 3 , 500 MHz): δ 11.56 (s, 1H), 8.28 (d, 1H), 7.84 (m, 2H), 7.49 (d, 1H), 7.45 (m, 2H), 7.28-7.18 (m, 5H), 5.76 (broad, 1H), 3.77 (q, 6H), 3.68 (s, 2H), 3.30 (t, 2H), 1.62 (quartet, 2H), 1.18 (t, 9H), 0.61 (t, 2H). [549] Mass spectrum: 589 (M-H). [550] Example 111 [551] [552] According to the process of Comparative Example 4 of the present invention, the compound is prepared as a light yellow solid having a melting point of 138 to 141 ° C with an appropriate starting material. [553] 29 Si NMR (CDCl 3 , 500 MHz, Cr (AcAc) 2 ): -45.46 ppm. [554] 1 H NMR (CDCl 3 , 500 MHz): δ 11.56 (s, 1H), 8.12 (d, 1H), 7.94 (d, 1H), 7.88 (d, 1H), 7.44 (dd, 1H), 7.24 (d , 1H), 5.72 (broad, 1H), 3.80 (q, 6H), 3.27 (t, 2H), 3.02 (t, 2H), 2.52 (t, 2H), 1.62 (quartet, 2H), 1.50 (s , 9H), 1.22 (t, 9H), 0.61 (t, 2H). [555] Mass spectrum: 575 (M-H). [556] Example 112 [557] [558] According to the process of Comparative Example 4 of the present invention, the compound is prepared as a light yellow solid with a melting point of 143 to 146 ° C with a suitable starting material. [559] 29 Si NMR (CDCl 3 , 500 MHz, Cr (AcAc) 2 ): -45.5 ppm. [560] 1 H NMR (CDCl 3 , 500 MHz): δ 11.53 (s, 1H), 8.29 (d, 1H), 8.16 (d, 1H), 8.06 (d, 1H), 7.68 (dd, 1H), 7.27 (d , 1H), 5.76 (broad, 1H), 3.80 (q, 6H), 3.27 (q, 2H), 3.03 (t, 2H), 2.53 (t, 2H), 1.62 (quartet, 2H), 1.50 (s , 9H), 1.21 (t, 9H), 0.61 (t, 2H). [561] 19 F NMR (CDCl 3 , 500 MHz, CF 3 COOH): -68.9 ppm. [562] Mass spectrum: M / Z = 610. [563] Example 113 [564] [565] According to the process of Comparative Example 4 of the present invention, the compound is prepared as a yellow solid having a melting point of 123 to 130 ° C. with a suitable starting material. [566] 29 Si NMR (CDCl 3 , 500 MHz, Cr (AcAc) 2 ): -45.45 ppm. [567] 1 H NMR (CDCl 3 , 500 MHz): δ 11.43 (s, 1H), 8.71 (d, 1H), 8.13 (d, 1H), 8.03 (d, 3H), 7.90 (dd, 1H), 7.61 (t , 1H), 7.55 (t, 2H), 5.76 (broad, 1H), 3.80 (q, 2H), 3.20 (q, 2H), 3.01 (t, 2H), 2.51 (t, 2H), 1.61 (quartet , 2H), 1.48 (s, 9H), 1.20 (t, 9H), 0.60 (t, 2H). [568] Mass spectrum: 681 (M-H). [569] Example 114 [570] [571] The compound is prepared as a pale yellow solid with a melting point of 55-61 ° C. with suitable starting materials according to the process of Comparative Example 5. [572] 29 Si NMR (CDCl 3 , 500 MHz, Cr (AcAc) 2 ): 0.21 ppm. [573] 1 H NMR (CDCl 3 , 500 MHz): δ 11.56 (s, 1H), 8.36 (d, 1H), 8.21 (d, 1H), 8.11 (d, 1H), 7.71 (d, 1H), 7.27 (d , 1H), 4.24 (q, 2H), 3.01 (t, 2H), 2.69 (t, 2H), 1.55 (s, 9H), 1.01 (t, 2H), 0.15 (s, 9H). [574] Mass spectrum: 506 (M-H). [575] Example 115 [576] [577] The compound is prepared as a yellow viscous oil with the appropriate starting material according to the process of Comparative Example 4. [578] 1 H NMR (CDCl 3 , 500 MHz): δ 11.15 (s, 1H), 8.40 (d, 1H), 8.35 (d, 1H), 7.91 (d, 1H), 7.62 (d, 1H), 7.36 (d , 1H), 7.30-7.15 (m, 4H), 6.65 (broad, 1H), 3.85 (q, 6H), 3.50 (t, 2H), 1.80 (s, 6H), 1.65 (m, 2H), 1.55 ( s, 9H), 1.25 (t, 9H), 0.63 (t, 2H). [579] Application Example 1 [580] Automotive coating compositions [581] The following tests are conducted to ascertain the effect on thermal durability and loss rate from high solid thermosetting acrylic coating compositions containing the benzotriazole UV absorbers of the present invention. [582] High solid thermoset acrylic transparent coatings are prepared by mixing a laboratory acrylic polyol resin with hexamethoxymethylmelamine (Resimene R 747, manufactured by Monsanto) in a solid ratio of 60/40. 0.70% by weight of a dodecylbenzene sulfonic acid catalyst (Nacure R 5225, manufactured by King Industries) is added. A flow aid Moda flow (Modaflow R) (Monsanto Co.) was added 0.25% by weight to form a model acrylic melamine resin system. [583] The model clear coating was reduced by xylene to a viscosity of 26 to 27 seconds using a Zahn # 2 cup and 50 psi (3.5 Kg / kg) onto a 1 "x 3" (2.54 x 7.82) quartz slide through conventional air spraying. cm 2 ). Curing is achieved by baking the slides at 260 ° F. (127 ° C.) for 30 minutes. 1% by weight of the hindered amine light stabilizer bis- (1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate [Tinuvin R (Shiba Corporation) )] To stabilize. Viscosity Test UV absorbers are introduced into the clear coating in an amount of about 5 mmol by weight. The film thickness of the quartz slide is 1.15 to 1.41 mils (0.029 to 0.036 mm). [584] The film on the quartz slide is measured for weather resistance in a xenon arc weather-Ometer with irradiation controlled at 6500 W using an internal quartz and external borosilicate S-type filter. The irradiation cycle is as follows: 40 minutes of direct sunlight without spraying water, followed by 20 minutes of irradiation with light + front spray, followed by 60 minutes of light and finally projection + rear spray (condensation) irradiation. The setting is 0.55 W / m 2 at 1.98 kJ / hour at 340 nm. In the light cycle, the black panel temperature is adjusted to 70 ± 2 ° C. The relative humidity of the light cycle ranges from 50 to 55% and the relative humidity of the dark cycle is 100%. The absorbance of the long wavelength UV band is recorded as a function of xenon arc weathering time. [585] In order to effect the loss of the UV absorber from the clear coating, the UV spectra are measured at regular intervals after the initial and weathering tests. The UV spectrometer uses a reference beam weakening technique to measure in a straight line up to an absorption unit of 5.5 or less. [586] The degradation products from the UV absorbers are assumed not to be involved in the UV spectrum. This is tested by measuring the ratio of band absorbance at about 300 nm and band absorbance at about 340 nm. This ratio does not change with the weathering test of the sample. This suggests that the UV spectra of the weathering tested films corresponded to the amount of UV absorbers remaining in the film, with little photodegradant involved in the spectrum. [587] Representative test compounds are introduced into the high solid thermoset acrylic melamine resin at a concentration of 3% by weight to provide the same molar concentration of the test UV absorber at the same film thickness. Test samples are each exposed for 1461 hours. [588] compoundInitial absorbance unitFinal absorbance unitLoss absorbance unit Uvinul R (1.86%)2.2602.26 Comparative Example 1 (2.95%)6.3806.38 Tinuvin 928 (3.0%)1.981.620.36 [589] Tinuvin R 928 is 2- (2-hydroxy-3-α-cumyl-5-tert-octylphenyl) -2H-benzotriazole (manufactured by Shiva Corporation). Ubinul 3049 is 4,4'-dimethoxy-2,2'-dihydroxybenzophenone (made by BASF Corporation). This example shows the general superiority of the hydroxyphenylbenzotriazole UV absorbers containing the α cumyl group as compared to the benzophenone UV absorbers. [590] Application Example 2 [591] UV absorption spectrum [592] Benzotriazole differs in its substitution at the 5-position of the benzo ring. UV absorption spectra are measured in ethyl acetate at a concentration of approximately 20 mg / L. The compound of the present invention is clearly red shifted compared with the compound having only hydrogen at the 5 position of the benzo ring. [593] compoundλmax (nm)Absorbance at 375nm Comparative Example 53380.09 Comparative Example 63420.20 Example 114 of the present invention3510.32 [594] Application Example 3 [595] UV absorption spectrum [596] UV absorption spectra are measured in ethyl acetate at a concentration of approximately 20 mg / L. The compounds of the present invention are clearly red shifted compared to the compounds described in US Pat. No. 5,391,795. [597] compoundλmax (nm)Absorbance at 375nm Comparative Example 13290.02 Comparative Example 22840.03 Comparative Example 32850.01 Example 107 of the present invention3490.36 Example 109 of the present invention3470.28 [598] Application Example 4 [599] UV absorption spectrum [600] Benzotriazoles differ in their substitution at the 5-position of the benzo ring. UV absorption spectra are measured in ethyl acetate at a concentration of approximately 20 mg / L. The compound of the present invention is clearly red shifted compared with the compound having only hydrogen at the 5 position of the benzo ring. [601] compoundλmax (nm)Absorbance at 375nm Comparative Example 73410.08 Comparative Example 43430.15 Example 111 of the present invention3490.36 Embodiment 112 of the present invention3510.29 Example 113 of the present invention3600.46 Example 115 of the present invention3500.23 [602] Application Example 5 [603] Silicon coating on solid substrate [604] The additive according to the invention is introduced into the silica resin solution according to Application Example 8 to obtain a silicone hardcoat solution with 5% by weight of silylated ultraviolet absorbents based on solids. The solution is applied to a glass slide. After evaporation of the solvent and baking for 1 hour at 100 ° C., an optically clear silicone hardcoat is formed on the glass. The coating is exposed to UV light by passing it five times under two 300 W / in medium pressure mercury lamps using a carrier that moves at about 25 ft / min. [605] The prepared silicone hardcoats containing the silylating additives of the present invention, in particular the compounds of Examples 107-115, exhibit excellent wear resistance (taber wear test), microcrack resistance and low haze to UV exposure. [606] The sample is also exposed to an Atlas Ci35a WeatherOmeter at 340 nm with 0.77 W / m 2 irradiation with S-type borosilicate internal and external filters. The lamp operates at 160 ° C. light bulb temperature and 50% relative humidity (about 65 ° C. black panel temperature) with a light period of 160 minutes and a dark period of 20 minutes. The last 15 minutes of the cancer cycle are carried out with front and rear water sprays. Under these conditions, the sample accumulates 2700 kJ / m 2 at 340 nm under 1100 hours of exposure. This is equivalent to about a year of Florida exposure. The sample is placed on a standard sample holder with a spring clip. [607] The prepared silicone hardcoats containing the silylation additives of the invention, in particular the compounds of Examples 107-115, exhibit excellent microcrack resistance and low haze to UV exposure in weatherometers. [608] Application Example 6 [609] Silicone coating on polycarbonate [610] Bisphenol-A based polycarbonate panels are primed with polymethylmethacrylate and flow coated with a silicone hardcoat prepared according to Application Example 5. The coated sample is baked at 100 ° C. for 90 minutes to obtain a polycarbonate coating having an optically clear 5μ silicone hardcoat. The prepared silicone hardcoats containing the silylating additives of the present invention, in particular the compounds of Examples 107-115, exhibit excellent wear resistance (taber wear test), microcrack resistance and low haze to UV exposure. The composition of the present invention also works particularly well for weatherometer exposure as in Application Example 5. [611] Application Example 7 [612] Colloidal silicone coating [613] 0.5 g of the silylation additive of the present invention is added to 50 g of a silica resin (condensed methyl trimethoxy silane / aqueous colloidal silica resin of about 20% solids in an alcohol solvent) to prepare a mixture. The mixture is stirred overnight and passed through a 0.30 μ filter to yield a silicone hardcoat solution with a 5 pph silylated UV absorber based on a solid. The solution is applied to glass slides and polycarbonate panels as above. [614] The silicone hardcoats prepared containing the silylation additives of the present invention, in particular the compounds of Examples 107-115, exhibit good wear resistance (taber wear test) and microcracks resistance and low haze to UV exposure. In addition, the compositions of the present invention work particularly well for weatherometer exposure as in Application Example 5. [615] Silylation additives of the present invention may be used in all types of commercially available transparent coatings for siloxane automobiles, such as those described in US Pat. Nos. 5,932,667, 5,182,174 and 6,080,816, the disclosures of which are incorporated herein by reference. Can be crosslinked or reacted. In addition, the additives of the present invention may crosslink or react with siloxane coatings as described in US Pat. Nos. 4,373,061, 5,391,795, 5,679,820, the disclosures of which are incorporated herein by reference. [616] Application Example 8 [617] Thermal Performance in Polymeric Coatings [618] The silicone coating is made from methyl trimethoxy silane and 2.5% by weight of additives in the following table. The aqueous acidic coating composition is applied by spin coating onto a 1.5 "diameter quartz disk under conditions that produce a 2 micron dry film thickness. All disks are ignited at room temperature for 20 to 30 minutes, and then one set of disks at 125 ° C. Bake for 60 minutes and another set dry at least overnight at room temperature. [619] The thermal performance of the test compound is measured using the Beer Law equation, which directly relates absorbance to concentration. It is assumed that all UVAs in the ambient cured coatings are retained and not volatilized. Thus, the amount of compound lost by volatilization under these baking conditions is measured by comparing the absorbance from the ambient cured coating and the oven cured coating applied at the same film thickness in the case of a reactive UV absorber, or excluding the unreactable UV absorber. The amount of UV absorber excluded from the ambient cured sample and the oven cured sample is measured by comparison. The results are shown in the following table. [620] compound% UVA lost Tinuvin 3845.6% Embodiment 112 of the present inventionCan be ignored [621] The reactable compounds of the present invention were found to be retained to a significantly high degree. [622] Application Example 9 [623] Absorption Wavelength Range in Polysiloxane [624] The coating is prepared and coated on a quartz disk as in Application Example 8. After oven curing at 125 ° C. for 60 minutes, absorbance scan is operated at 250-450 nm. When two absorption peaks exist, the longer wavelength peak is recorded at the position (nm). The long wavelength spectral range is also obtained by obtaining absorbance values at 375 nm. The results are shown in the following table. [625] compoundPeak absorbance wavelength (nm)Absorbance at 375nm Comparative Example 3287 (nm)0.013 Comparative Example 4343 nm0.155 Embodiment 112 of the present invention353 nm0.216 [626] It can be seen that the compounds of the present invention provide a significantly broader spectral range than the benzoyl resorcinol compounds. [627] Application Example 10 [628] Responsive [629] The coating is prepared and coated on a glass plate as in Application Example 8. After ambient curing for 1 day, the coating is removed from the glass substrate. About 5 mg of the coating is weighed into a 10 ml volumetric flask, which is filled to represent tetrahydrofuran (THF). After sonication for 60 minutes, the solution is filtered and then diluted with THF to a known volume. The amount of extracted UVA is measured by comparing the absorbance of the THF solution with the absorbance of a known standard. The rate of reaction with the coating is calculated from the difference between the amount of UVA present in the coating after baking and the amount extracted. The results are shown in the following table. [630] compoundExtraction ratio Tinuvin 38489% Tinuvin 92897% Comparative Example 45.0% Embodiment 112 of the present invention4.6% [631] The compounds of the present invention have been shown to react successfully with coatings. [632] Application Example 11 [633] color [634] A coating is prepared and coated on a quartz disk as in Example 8. After ambient curing for one week, the CILAB L * , a *, and b * values are obtained using a MacBeth Coloreye spectrometer. In the included specular component, each 10 ° of the D65 emitter and observer is used. Color readings are obtained in a reflective manner on a coated disc using white tile standards as the backing. [635] compoundYI Comparative Example 32.14 Embodiment 112 of the present invention2.07 [636] The coating made with the additive of the present invention is transparent, free of haze, and has an excellent color.
权利要求:
Claims (15) [1" claim-type="Currently amended] Compounds of Formula I or Formula II. Formula I Formula II In Formula I and Formula II above, G 1 and G 6 are independently hydrogen or halogen, G 2 and G 7 are independently cyano, perfluoroalkyl having 1 to 12 carbon atoms, fluoro, chloro, -CO-G 3 , -COOG 3 , -CONHG 3 , -CON (G 3 ) 2 , E 3 SO-, E 3 SO 2- , -PO (C 6 H 5 ) 2 , , -CO-XT 1 -O-CO-NH-T 2 -Si (OR 2 ) n (R 1 ) 3-n or -CO-XT 1 -Si (OR 2 ) n (R 1 ) 3-n, or G 7 is hydrogen, G 2 may be hydrogen when E 1 is a group of Formula IV or Formula V, T 1 and T 2 are independently alkylene having 1 to 18 carbon atoms or alkylene-phenylene-alkylene having 8 to 20 carbon atoms, R 1 and R 2 are independently alkyl having 1 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, aryl having 6 to 10 carbon atoms or phenylalkyl having 7 to 20 carbon atoms, n is 0, 1, 2 or 3, X is -O-, -NE 4 -or -NH-, G 3 is hydrogen, straight or branched chain alkyl having 1 to 24 carbon atoms, straight or branched chain alkenyl having 2 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, phenylalkyl having 7 to 15 carbon atoms, phenyl, or phenyl ring having 1 to 24 carbon atoms. Phenyl or phenylalkyl above substituted with 1-4 alkyl of 4, E 1 is hydrogen, straight or branched chain alkyl having 1 to 24 carbon atoms, straight or branched chain alkenyl having 2 to 24 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, phenylalkyl having 7 to 15 carbon atoms, phenyl, or phenyl ring having 1 to 24 carbon atoms. Or substituted with one to four alkyl of 4 or one or more of the formulas -T 1 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -XT 1 -Si (OR 2 ) n (R 1 ) 3-n or -XT 1- Or phenyl or phenylalkyl above substituted with a group of X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , E 1 is alkyl having 1 to 24 carbon atoms substituted with 1 or 2 hydroxy groups, or E 1 is a group of Formula IV or Formula V: Formula IV Formula V [Wherein E 27 and E 28 are independently alkyl having 1 to 18 carbon atoms or cycloalkyl having 5 to 12 carbon atoms, E 22 , E 23 , E 24 , E 25 and E 26 are independently hydrogen, halogen, straight or branched chain alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms; When E 4 is straight or branched chain alkyl of 1 to 24 carbon atoms or straight or branched chain alkenyl of 2 to 18 carbon atoms, at least one halogen, -OCOE 11 , -OE 4 , -NCO, -NHCOE 11 , -NE 7 E 8 Or alkyl or alkenyl above substituted with mixtures thereof; Or the above alkyl blocked with one or more -O-, -NH-, -NE 4 -groups or mixtures thereof and unsubstituted or substituted with one or more -OH, -OE 4 , -NH 2 or mixtures thereof Or alkenyl, E 22 , E 23 , E 24 , E 25 and E 26 are independently phenyl, -OH, -OCOE 11 , -OE 29 , -NCO, -NHCOE 11 or -NE 7 E 8 , cyano, nitro, 1 carbon To 12 perfluoroalkyl, -COG 3 , -COOG 3 , -CON (G 3 ) 2 , -CONHG 3 , E 3 S-, E 3 SO-, E 3 SO 2- , -P (O) ( C 6 H 5 ) 2 , -P (O) (OG 3 ) 2 or -SO 2 -X 1 -E 29 ; X 1 is -O-, -NH- or -NE 4- , E 29 is straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms; When E 4 is straight or branched chain alkyl of 1 to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms, one or more -OH, -OCOE 11 , -OE 4 , -NCO, -NHCOE 11 , -NE 7 E 8 , phthal Already, , Or alkyl or alkenyl above substituted with mixtures thereof; Or the above alkyl blocked with one or more -O-, -NH-, -NE 4 -groups or mixtures thereof and unsubstituted or substituted with one or more -OH, -OE 4 , -NH 2 or mixtures thereof Or alkenyl, E 29 is phenyl or phenylalkyl having 7 to 15 carbon atoms, or phenyl or phenylalkyl above substituted with 1 to 3 alkyl groups having 1 to 4 carbon atoms, E 2 and E 9 are independently hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, or The phenyl ring is substituted with 1 to 3 alkyl of 1 to 4 carbon atoms or one or more of the formulas -T 1 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -XT 1 -Si (OR 2 ) n (R 1 ) 3-n Or phenyl or phenylalkyl above substituted with a group of -XT 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , or E 2 and E 9 are independently one or more -OH, -OCOE 11 , -OE 4 , -NCO, -NH 2 , -NHCOE 11 , -NHE 4 , -N (E 4 ) 2 or mixtures thereof, wherein E 4 is straight-chain or branched alkyl having 1 to 24 carbon atoms) or alkyl of 1 to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms, or one or more -O-, -NH-, -NE 4 -Alkyl or alkenyl above, blocked with a group or a mixture thereof and unsubstituted or substituted with one or more -OH, -OE 4 , -NH 2 groups or mixtures thereof, or E 1 , E 2 and E 9 are independently -T 1 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n or —T 1 —CO—XT 2 —Si (OR 2 ) n (R 1 ) 3-n , E 11 is hydrogen, straight or branched chain alkyl of 1 to 18 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aryl of 6 to 14 carbon atoms, or phenylalkyl of 7 to 15 carbon atoms, L is alkylene having 1 to 12 carbon atoms, alkylidene having 2 to 12 carbon atoms, benzylidene, p-xylylene, cycloalkylidene having 5 to 12 carbon atoms, or α, α, α ', α'-tetramethyl-m Xylylene, E 3 is alkyl having 1 to 20 carbon atoms substituted with alkoxycarbonyl having 2 to 9 carbon atoms, hydroxyalkyl having 2 to 20 carbon atoms, alkenyl having 3 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, and having 7 to 15 carbon atoms. Phenylalkyl, aryl of 6 to 10 carbon atoms, or aryl substituted with 1 or 2 alkyl of 1 to 4 carbon atoms, or 1,1,2,2-tetrahydroperfluoroalkyl, wherein perfluoroalkyl The residue has 6 to 16 carbon atoms), E 5 and E 8 are independently the same as E 2 , E 5 and E 8 are independently hydrogen, -XE 1 , -X-CO-E 2 , -X-CO-X 1 , -XT 1 -Si (OR 2 ) n (R 1 ) 3-n or -XT 1- X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , X 1 is -NH-E 4 or -XE 2 , At least one of G 2 , E 1 , E 2 and E 5 may be selected from the formulas -T 1 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n or a group of -T 1 -CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , wherein T 1 and T 2 are independently alkyl having 1 to 18 carbon atoms Ethylene or alkylene-phenylene-alkylene having 8 to 20 carbon atoms, R 1 and R 2 are independently alkyl having 1 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, aryl having 6 to 10 carbon atoms or having 7 to 7 carbon atoms; Phenylalkyl of 20 and n is 0, 1, 2 or 3). [2" claim-type="Currently amended] The compound of formula Ia or formula IIa according to claim 1. Formula Ia Formula IIa In Formula Ia or Formula IIa above, G 1 and G 6 are hydrogen, G 2 and G 7 are independently cyano, CF 3- , fluoro, -CO-G 3 or E 3 SO 2- , or G 7 is hydrogen, G 3 is linear or branched alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or a phenyl ring of 1 to 4 carbon atoms. Phenyl or phenylalkyl above substituted with 1-4 alkyl, E 1 is phenylalkyl, phenyl or phenyl ring having 7 to 15 carbon atoms substituted with 1 to 4 alkyl of 1 to 4 carbon atoms, E 2 and E 9 are independently a straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or a phenyl ring The above phenyl or phenylalkyl substituted with 1 to 3 alkyl of 1 to 4 carbon atoms, or E 2 is at least one -OH, -OCOE 11 , -OE 4 , -NCO, -NH 2 , -NHCOE 11 , -NHE 4 , -N (E 4 ) 2 or mixtures thereof, wherein E 4 is 1 carbon Alkyl of 1 to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms, or one or more -O-, -NH-, -NE 4 -groups or their Alkyl or alkenyl, which may be blocked with a mixture and unsubstituted or substituted with one or more -OH, -OE 4 , -NH 2 groups or mixtures thereof, E 11 is hydrogen, straight or branched chain alkyl of 1 to 18 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aryl of 6 to 14 carbon atoms, or phenylalkyl of 7 to 15 carbon atoms, E 3 is alkyl having 1 to 20 carbons, hydroxyalkyl having 2 to 20 carbon atoms, alkenyl having 3 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, phenylalkyl having 7 to 15 carbon atoms, aryl having 6 to 10 carbon atoms, Or aryl above substituted with one or two alkyl of 1 to 4 carbon atoms, or 1,1,2,2-tetrahydroperfluoroalkyl, wherein the perfluoroalkyl moiety has 6 to 16 carbon atoms, L is methylene, At least one of E 1 , E 2 and E 9 may be selected from the formulas -T 1 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -XT 1 -Si (OR 2 ) n (R 1 ) 3-n or -XT 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) A group of 3-n wherein T 1 and T 2 are independently alkylene of 2 or 3 carbon atoms, and R 1 and R 2 are independent And alkyl or phenyl having 1 to 6 carbon atoms, and n is 0, 1, 2 or 3). [3" claim-type="Currently amended] The compound of formula Ia according to claim 1. Formula Ia In Formula Ia above, G 1 is hydrogen, G 2 is CF 3- , fluoro or E 3 SO 2- , E 1 is hydrogen or straight or branched chain alkyl of 2 to 24 carbon atoms, E 2 is as defined in claim 1, E 3 is straight or branched chain alkyl of 1 to 7 carbon atoms, E 2 is a chemical formula -T 1 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -X-CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -T 1 -CO-XT 2 -Si (OR 2 ) n (R 1 ) 3-n , -XT 1 -Si (OR 2 ) n (R 1 ) 3-n or -XT 1 -X-CO-XT 2 -Si (OR 2 ) a group of n (R 1 ) 3-n wherein T 1 and T 2 are independently alkylene having 2 or 3 carbon atoms, and R 1 and R 2 are independently alkyl or phenyl having 1 to 6 carbon atoms N is 0, 1, 2 or 3). [4" claim-type="Currently amended] The compound of claim 1, wherein T 1 and T 2 are independently alkylene having 2 or 3 carbon atoms. [5" claim-type="Currently amended] The compound of claim 1, wherein R 1 and R 2 are independently alkyl or phenyl having 1 to 6 carbon atoms. [6" claim-type="Currently amended] The method of claim 1, 5-trifluoromethyl-2- [2-hydroxy-3- (3-triethoxysilyl) propyl-5-tert-octylphenyl] -2H-benzotriazole (a), 5-trifluoromethyl-2- {2-hydroxy-3-tert-butyl-5- [3- (3-triethyloxysilyl) propyl carbamoyloxy) propyl] phenyl} -2H-benzotriazole (b), 5-trifluoromethyl-2- {2-hydroxy-3-tert-butyl-5- [2- (3-triethyloxysilyl) propylcarbamoyloxy) ethyl] phenyl} -2H-benzotriazole (c), 5-trifluoromethyl-2- {2-hydroxy-5- [2- (3-triethyloxysilyl) propyl-carbamoyloxy) ethyl] -phenyl} -2H-benzotriazole (d), 5-trifluoromethyl-2- {2-hydroxy-3-α-cumyl-5- [2- (3-triethyloxysilyl) propylcarbamoyloxy) ethyl] phenyl} -2H-benzotriazole ( e), 5-trifluoromethyl-2- {2-hydroxy-3-tert-butyl-5- [2- (3- (diethoxymethylsilyl) propylaminocarbonylethyl] phenyl} -2H-benzotriazole (f), 5-phenylsulfonyl-2- {2-hydroxy-3-tert-butyl-5- [3- (2-ethoxydimethylsilyl) ethylcarbonyloxy) propyl] phenyl} -2H-benzotriazole ( g), 5-n-butylsulfonyl-2- {2-hydroxy-3-tert-butyl-5- [2- (3-ethoxydimethylsilyl) propyl-oxycarbonyl) ethyl] phenyl} -2H-benzo Triazole (h), 5-trifluoromethyl-2- [2-hydroxy-3- (ethoxydimethylsilyl) propyl-5-tert-octylphenyl] -2H-benzotriazole (i), 5-trifluoromethyl-2- [2-hydroxy-3- (trimethylsilyl) propyl-5-tert-butylphenyl] -2H-benzotriazole (j), 5- [3- (diethoxyethylsilyl) propoxycarbonyl] -2- (2-hydroxy-3-α-cumyl-5-tert-octyl-phenyl) -2H-benzotriazole (k), 5- [3- (diethoxyethylsilyl) propylaminocarbonyl] -2- (2-hydroxy-3-α-cumyl-5-tert-octyl-phenyl) -2H-benzotriazole (l), (m) , (n) , (o) , (p) , (q) , (r) , (s) , (t) or (u) Compound of formula (I). [7" claim-type="Currently amended] Organic material (a) which is photoinductively decomposed and A composition stabilized from light induced degradation, comprising a stabilizing effective amount of compound (b) of formula (I) or formula (II) according to claim 1. [8" claim-type="Currently amended] 8. The composition of claim 7, wherein component (a) is a natural polymer, semisynthetic polymer or synthetic polymer. [9" claim-type="Currently amended] The polyester, polyurethane, acrylate, rubber modified styrene of claim 8 wherein the polymer is polypropylene or the polymer comprises styrene, ABS, nylon, poly (ethylene terephthalate) or poly (butylene terephthalate). , Including poly (vinyl chloride), poly (vinyl butyral), polyacetal (polyoxymethylene), poly (ethylene naphthalenedicarboxylate) or poly (ethylene / 1,4-cyclohexylenedimethylene terephthalate) PETG Another blend or copolymer, or ionomer. [10" claim-type="Currently amended] 8. The composition of claim 7, wherein the composition comprises a ultraviolet light shielding layer comprising a silicon coating on a solid substrate. [11" claim-type="Currently amended] The composition of claim 8 wherein the polymer is a siloxane coating as a light shielding layer over polycarbonate. [12" claim-type="Currently amended] 8. The organic material of component (a) is selected from the group consisting of thermosetting acrylic melamine resins, acrylic urethane resins, epoxy carboxy resins, silane modified acrylic melamines, acrylic resins in which carbamate pendant groups are crosslinked with melamine, and carbamate. A composition selected from the group consisting of acrylic polyol resins crosslinked to melamine containing groups. [13" claim-type="Currently amended] 8. The composition of claim 7, wherein the organic material of component (a) is an acrylosilane coating useful for organosilicone hardcoats or softcoats for automotive or multilayer compositions. [14" claim-type="Currently amended] 8. The method of claim 7, further comprising another UV absorber selected from the group consisting of benzotriazole, s-triazine, oxanilide, hydroxybenzophenone, benzoate and α-cyanoacrylate as auxiliary additives. Composition. [15" claim-type="Currently amended] 8. The composition of claim 7, further comprising phenolic antioxidants and / or sterically hindered amines as auxiliary additives.
类似技术:
公开号 | 公开日 | 专利标题 AT405936B|1999-12-27|Coating materials stabilized with benzotriazole uv absorbers BE1011550A3|1999-10-05|Compositions containing compounds and their use to stabilize an organic matter. RU2127264C1|1999-03-10|Substituted benzotriazoles, stabilized compositions and covering system EP0309402B1|1995-01-11|N-substituted hindered amine stabilizers US5216156A|1993-06-01|Non-migrating 1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidine 1,3,5-triazine derivatives DE19537291B4|2006-06-22|Until Resorcinyltriazine US6365652B2|2002-04-02|Trisaryl-1,3,5-triazine ultraviolet light absorbers CN1091127C|2002-09-18|Benzotriazole UV absorbers having enhanced durability EP0057160B1|1985-06-19|2-|-benzotriazoles, their use as ultraviolet stabilizers and their preparation AU727251B2|2000-12-07|Stabilizer combination CA1338713C|1996-11-12|2-|-benzotriazole derivatives US6509399B2|2003-01-21|Non-yellowing part-tertiary-alkyl phenyl substituted triazine and pyrimidine ultraviolet light absorbers EP1844049B1|2011-03-23|Long wavelength shifted benzotriazole uv-absorbers and their use DE19712277B4|2014-11-06|hydroxyphenyltriazines US6355708B2|2002-03-12|Trisaryl-1,3,5-triazine ultraviolet light absorbers US7550599B2|2009-06-23|Water compatible sterically hindered alkoxyamines and hydroxy substituted alkoxyamines US6867250B1|2005-03-15|Non-yellowing ortho-dialkyl aryl substituted triazine ultraviolet light absorbers EP0704437B1|2002-09-25|Red-shifted tris-aryl-s-triazines and compositions stabilized therewith US5021486A|1991-06-04|Hindered amine-substituted malonic acid derivatives of s-triazine US6271377B1|2001-08-07|Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith KR100363981B1|2003-01-30|Potential Light Stabilizer NL1018187C2|2001-12-28|Stabilizer mixtures. RU2066682C1|1996-09-20|Photostabilized polymer composition US5679794A|1997-10-21|Polymer stabilizers containing both hindered amine and hydroxylamine moieties US6348591B1|2002-02-19|Red-shifted trisaryl-1,3,5-triazine ultraviolet light absorbers
同族专利:
公开号 | 公开日 AU9370801A|2002-02-18| US20020115753A1|2002-08-22| EP1305320A1|2003-05-02| JP2004505984A|2004-02-26| US6677392B2|2004-01-13| DE60120178T2|2007-04-26| DE60120178D1|2006-07-06| JP4912561B2|2012-04-11| AT327997T|2006-06-15| EP1305320B1|2006-05-31| TW548303B|2003-08-21| WO2002012252A1|2002-02-14|
引用文献:
公开号 | 申请日 | 公开日 | 申请人 | 专利标题
法律状态:
2000-08-03|Priority to US22278300P 2000-08-03|Priority to US60/222,783 2001-07-05|Priority to US30304801P 2001-07-05|Priority to US60/303,048 2001-07-26|Application filed by 시바 스페셜티 케미칼스 홀딩 인크. 2001-07-26|Priority to PCT/EP2001/008663 2003-03-15|Publication of KR20030022347A
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申请号 | 申请日 | 专利标题 US22278300P| true| 2000-08-03|2000-08-03| US60/222,783|2000-08-03| US30304801P| true| 2001-07-05|2001-07-05| US60/303,048|2001-07-05| PCT/EP2001/008663|WO2002012252A1|2000-08-03|2001-07-26|Photostable, silylated benzotriazole uv absorbers and compositions stabilized therewith| 相关专利
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