• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    The invention relates to substituted urethanes, in particular the preparation of compounds of the total f-ly [C 8-16F 17-33- (CH 2) 2-O-CH 2 -CH (CH 2CL) -C (O) -NH] -A (Y ) -NH-C (O) -XB, where Y is the group C 8-16F 17-33- (CH 2) 2-OC (O) -NH- or C 8-16F 17-33- (CH 2) 2 -O-CH (CH 2CL) -CH (CH 2CL) -C (O) -NH- A is the group [- (CH 2) 6-NH-C (O)] 2N- (CH 2) 6- X - group a / -Z 2 @ Z 1- b / -Z 1 @ -C (CH 3) 2 @ Z 2- in / -Z 1 @ S (O) 2 @ Z 2- g / Z 1 @ -C (CF 3) 2 @ Z 2- with Z 1 and Z 2 = oxygen or NH [when identical], or oxygen or C [O] - [when different] BH or -C / O / -NH-A- [NH-C (O) -O-CH (CH 2CL) -CH 2 -O-CH (CH 2CL) -CH 2-O (CH 2) 2 group C 8-16F 17-33] 2, or -C (O) -NH-AK-NHC [O] -O-CH [CH 2CL] -CH 2-O-CH [CH 2CL] -CH 2-O / CH 2/2-C 8-16F 17-33 with K = -NH-C [O] -O [CH 2] -C 8-16F 17-33, which can be used for finishing textiles. The goal is to create new modifiers for the specified purpose. The synthesis is carried out by the reaction of the corresponding fluoroalcohol f-crystals C 8-16F 17-33 [CH 2] XO- [CH 2-CH (CH 2CL) -O] YH, where X = 2, Y = 0 or 2, with a triisocyan containing group A. The adducts thus obtained are treated with an appropriate aromatic dioxy, aminooxy or hydroxycarboxylic acid compound [C 8-16F 17-33- (CH 2) 2 O-CH 2 -CH (CH 2CL) -O-CH 2-CH (CH 2CL) -OC (O) -NH] -AN = C = O C 8H 16F 17-33- (CH 2) 2-O-CH 2 -CH (CH 2CL) -O-CH 2 -CH (CH 2CL) -O-C (O) -NH-AK-N = C = O H-X-H, where K and X are indicated above, with the formation of urethanes with B = H. In another case, the urethanes obtained are treated with adducts to form the target urethanes with the value B ≠ hydrogen. New substances give the fabrics oil and water repellency to a better degree than known substances. 3 tab.
    公开号:SU1590038A3
    申请号:SU874202846
    申请日:1987-07-02
    公开日:1990-08-30
    发明作者:Веховски Франк；Клебер Рольф；Жекель Лотар
    申请人:Хехст Аг (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to a method for finishing textile articles for producing urethanes, which are used as various modifying additives:
     (A K-SvG „-С, еГзз) -СН, СН, ОЧСН2СНО) g-SOSh-A-KNOSNGS T
    where Y- (Alk-C8Fi7-Ci6F33) -CH2CH20-CONH- (l)
    I,
    or (ASH-SvGp-S, 5Gzz) -CH2CY, 0- (SNGNO) 2 SakN- (2)
    CHzCl
    - (snlsnso.
    where a is a group of formula (3) (CH2) b
    (CE2) & - mc
    SNS
    . X is a group of formulas 4-7 Z, -, - Z i - (/ C l. / Z 2 -
    ..- J 1A / I -
    (4) SNS (5)
    -Z2
    ., Os ".-.: .-. . ,, | V.CF3 (7)
    where Z, ig, is O or N11, when they both have a hydrogen atom or a group of formulas the same or different; ihsi O or 8 and 9 COO, when they are different, and B is designated-SSH-A-GshKYU- () g QCH CH -lCsF y-C eFaa-A1k)
    fHidl
    Liil iVi
    NHC04oCHCtb;) 2 OCH2CH2- (C8F, 7-Ci6F33-AlK)
    CONH-ASNGS
    i HCO-OCH2CHj- (C8Hi7-Gi5F33-AlK)

    where A has the abovementioned meaning — spruce of the invention — the search for innovation where and when. compounds from the class of urethanes with pepper ..
    fluoroalkyl and epichlorohydrin groups containing an aromatic dioxy, amino, amino or hydroxycarboxyl residue as a modifying group.
    These urethanes have improved qualities and are used to merge textiles.
    Example 1. In a glass flask equipped with a stirrer, a reflux condenser, a thermometer, an addition funnel. 8 kg (15.7 mol) of a commercially available perfluoroalkyl ethanol mixture with perfluoroalkyl (number), 8 kg of 1,2,3-trifluorotrichloroethane as solvent and 50 g of boron trifluoride diethyl etherate as catalysis - torus (0.6 wt.% catalyst relative to perfluoroalkylethanol). 2.9 kg (31.4 mol) of epiclorohydrin is added to this solution at 45 ° C, after which the eyelid is kept, the mixture is held at the boiling point of the solvent for 3 hours. Then, the used solvent is distilled off in vacuo (in a vacuum created using water jet pump). A yellow wax product is obtained. In the aliphatic fluoride alcohol obtained in this way, the molar ratio of perfluoroalkyl ethanol and epichlorohydrin is 1: 2 (Y in formula 1 has a value of 2, which is obtained by forming an average value of 1-8 attached epichlorohydrin units)
    The reaction of an aliphatic fluoride alcohol with an isocyanate to obtain an adduct of fluoride alcohol and an isocyanate (adduct 1) is carried out in a glass flask equipped with a stirrer, a reflux condenser with a drying tube, a thermometer and a heating bath. 85.0 g (0.13 g-eq.) Of aliphatic fluoride alcohol and 35.7 g (0.19 g-eq.) Of triisocyanate are used in accordance with formula (3) and this is kept for 4 hours with stirring and at 110 ° C. To the mixture is then added 5 drops of dibutyl tin dilute, after which it is held for the next reaction for 3 hours while stirring at 110 ° C. The resulting adduct of fluoride alcohol and isocyanate (adduct 1) has the appearance of a waxy yellow product.
    The reaction of the adduct 1 with an aromatic. Difunctional compound is carried out
    0
    five
    0
    five
    0
    five
    0
    five
    0
    also in a glass flask equipped with a stirrer, a reflux condenser with a drying tube, a thermometer and a heating bath. 100.0 g (62.6 mg-eq.) of the adduct 1 and 3.5 g (62.8 mg-eq. of pyrocatechin (mol The ratio is 2: 1), all this is maintained for 35 hours with PO C and with stirring to obtain 100.6 g (97.3% by weight of theoretically) of the proposed compound, in the form of a brown waxy product. The gross formula of the molecule of which includes ali-phatic fluoride alcohol, isoc1 aaa1 and pyrocatechin (mol p This ratio is 4: 2: 1), corresponds to the form-: le B "
    Examples 2 and 3. The process is carried out in the same manner as in example 1, except that resorcinol (example 2) and hydroquinone (example 3) are used instead of pyrocatechol, and that aging is carried out not for 35 hours, but in each case for 10 hours at 110 ° C. In each case, 102.0 g (99.0% by weight theoretically) of the desired product is obtained in the form of a brown waxy product. The composition of the compounds obtained by the gross formula, the molecules of which include aliphatic fluoride alcohol, isocyanate and resorcinol or hydroquinone (molar ratio in each case is 4: 2: 1), corresponds to the form -. llamas bj and bj.
    Example 4. A glass flask as described above was charged with 231.4 g. (0.12 g-eq) of adduct 1 from example 1 and 14.2 g (0.12 g-eq.) 2.2 (4,4-dihydroxydiphenyl) -propane, i.e. bisphenol A (molar ratio 2: 1), as well as 62.0 g of adipic acid di-p-butyl ester as ra-. blend and the whole mixture is allowed to stand for 12 hours with and with stirring. To the mixture is added 5 drops of dibutyl tin dilaurate, after which it is held for 4 hours at 110 ° C and with stirring. 304.0 g (99.0% by mass of theoretical) of the proposed compound are obtained in the form of a brown waxy product. The composition of the obtained compound, expressed by the gross formula, the molecule of which includes aliphatic fluoride alcohol, isocyanate
    and bisphenol A (molar ratio 4: 2: 1) corresponds to formula В „
    Example 5. Initial mixture: 154.3 g (80 g-eq.) Of adduct 1 from example 1, 13.4 g (80 g-eq.) 2,2- (4,4-dihydroxydiphenyl) -hexafluoropropane (hexafluorobisphenol A), 42.0 g of adipic acid di-p-butylether.
    The reaction is carried out in the same manner as in Example 4.
    Yield 205.8 g (98.1% by weight of theoretically) of the desired product as a brown waxy product. The composition of the compound, expressed by the gross formula, the molecule of which includes aliphatic fluoride alcohol, isocyanate and hexafluorobisfekol A (molar ratio 4: 2: 1), corresponds to the formula Eg-.
    Example 6. Initial mixture: 238.5 g (124.0 g-eq.) Of adduct 1 from example 1; 15.3 g (124 g-eq.) Of bis- (4-hydroxyphenyl) sulfone, 64.0 g of adipic acid di-p-butylether.
    The reaction is carried out in the same manner as in Example 4.
    Yield 314.0 g (98.5% by weight theoretically) of the compound as a brown, waxy product. The composition of the compound, expressed by the gross formula, the molecule of which includes aliphatic fluoride alcohol, isocyanate, bis- (4-hydroxyphenyl) sulfone (molar ratio 4: 2: 1) corresponds to formula B.
    Example 7. Initial suspension: 100.0 g (63.0 g-eq.) Of adduct 1 from example 1, 3.4 g (63.0 g-eq.) Of 3-aminophenol.
    The reaction is carried out in the same manner as in Example 1, except that the retention time is not 35 hours, but 6 hours at.
    Yield 102.0 g (98.7% by mass, theoretically) of the compound as a brown waxy product. The composition of the compound, expressed by the gross formula, the molecule of which includes aliphatic fluoride alcohol, isocyanate and 3-aminophenol (molar ratio 4: 2: 1), corresponds to formula B
    Example 8. To obtain another adduct 1, 162.0 g (0.32 g-eq.) Of perfluoroalkyl ethanol from npiiMejpa 1, 216.0 g (0.32 g-eq.) Are placed in the glass flask mentioned in example 1. aliphatic fluoride alcohol pz example 1 and 181.3 g (0.96 g-eq.) triiso



    the cyanate from Example 1 (molar ratio 1: 1: 1), and this was all carried out for 5 hours with and during pepimania. The resulting adduct is based on. fluoride alcohol and isocyanate (adduct 1) is a yellow waxy product.
    To carry out the reaction of this adduct 1 with the aromatic dysfunctional compound, as in Example 1, take 559.0 g (0–32 g-eq.) Of adduct 1, 17.5 g (0.32 g-eq.) Of hydroquinone and 144 , 0 g of adipic acid-di-p-butylether as solvent (2: 1 molar ratio), hold the mixture for 10 hours at 11 ° C and with stirring. 715.0 g (99.2% by weight theoretically) of compound c are obtained. As a brown product. The composition of the compound, which is nfc a gross formula, the molecule of which includes adshfaty fluoride alcohol, isocyanate and hydroquinone (molar ratio 4: 2: 1), corresponds to the formula Bg.
    Example 9. Initial mixture: 289.3 g (0.15 g-eq.) Of adduct 1 from example 1, 37.5 g (0.3 g-eq.) Of bisphenol A.
    The reaction is carried out in the same manner as in Example D, except that the holding is not 35 hours, but 7 hours, at 11, after adding 5 drops of dibutyl tin dilaurate for the subsequent reaction, further exposure is carried out for 6 hours at 110 ° C and at stirring
    Yield 318.0 g (97.5% by weight of theoretically) of the compound as a brown waxy product. The composition of the compound, expressed as 6pytTO-formula, the molecule of which includes aliphatic fluoride alcohol, isocyanate and bisphenol A (molar ratio 2: 1: 1), corresponds to formula B.
    Example 10. The original mixture :. 289.3 g (0.15 g-eq.) Of adduct 1 from example 1, 37.5 g (0.3 g-ek) of bis- (4-hydroxyphenyl) sulfone.
    The reaction was carried out in the same manner as in Example 9.
    Yield 323.4 g (99.0% by mass of theoretically) of the compound as a brown waxy product. The composition of the compound., Expressed by the gross formula, the molecule of which includes aliphatic fluoride alcohol, isocyanate and bis- (4-hydroxyphenyl) sulfone
    1590038 °
    (molar ratio 2; 1i1) respectively - Example 12, Initial mixture:
    formula B, .289.3 g (0.15 g-eq,) of adduct 1 of
    Example 11. Initial mixture: Example 1, 20.7 g (0.15 g-eq.) P-hyd529, 0 g (0.3 g-eq.) Of isroxybenzuric acid adduct 1, example 8, 33.0 g ( 0.6 g-eq.) Hydro-reaction is carried out in the same way as
    quinone.in example 9.
    The reaction is carried out in the same way as Yield 297.0 g (95.8% by weight of the theory in example 8.retically) compound as a wake-up 553.0 g (98.5% by weight of theo-JQ different brown product, retically) Compounds in the form of a wax-Compound of the compound, expressed as a brown-colored gross product. The formula, the molecule of which includes the Composition of the compound, a pronounced gross-aliphatic fluoride alcohol, isocirculation, the molecule of which includes nag and p-hydroxybenzoic acid, aliphatic fluoride - J5 (molar ratio 2: 1: 1), respectively cyanate and hydroquinone (the molar ratio corresponds to the formula B j. 2: 1: 1 ratio), corresponds to the form- Chemical formulas of compounds, according to B
    "
    BI D (C -) - СНгСНгО - (СН2СНО) 2 - CONH -А- NHCO- О y (OBi
      e
    BZ G (C8G "-S1bGzz) -Sh2SNgO- (CH2CHO) 2-Csn-A-gaSO-O- -CHzCl
    Bi
    (С8Г17-С, бГзз) -СН2СН20- (СНгСНО} 2-С (ЖН-СН2С1 в J (CgF) -СН2СН20- (Ш2ШО) 2-СОШ --А-ШСО-0-0 -с- 0 -ОБ,
    at,
    (CgF 17-) - СН2СЭ120- (СН2ШО) 2- SOSH-A - NHCO - Q- (Q
    J;
    С1бГзз) -СН2СН20- (СН2СНО) 2- CONH
    . Ghjcl
    С1бГзз) - CH2CH20- (CHjCHO) 2-CONH

    CH, C1
    (С8Г, 7-С1бГзз) -СН2СН20 -ССШН / -Л
    Be :. A-TNSO-OCH OVg
    -, 7-С, бГзз) -И1гСН20- (СН2СНО) 2-СОИН /
     I tT
    VMUOV
    Eg (С8Г.П-) -СН2СН20- (СН2СНО) 2-СОш1-А-ШСО-LCHtCl-
    Lasno examples 1-12 are as follows:
    A-gaSo-O-
    A-NHCO-0 S,
    Obj snake
    SHO) 2- SOSH -
    CH, C1
    -А-1ШСО-0S4O) -OB,
    -A-inso

    CH, C1
    B "F (C8l lI-Ci6F33) -CHzCH20 - (), - CONH
     MS
    -iilloV / l
    at
    eleven
    (SvG, 7-S, bGZe) -SNgSN20-ShSh / YAH „
    A-inso-o-o-it
    X
    (from - SGS) - SNGNGO - (CHzCHOJz - SOSH
    SNGS
    in “G (S8G17-s, bGzz) —sn, CE, o — (sn, sno), —so1 n-A-dasozon LCHjCi
    in formulas in, -в, j А means:
    In formulas B, -B7 B, means
    SOMN-A -H NSO- (OCNII2) 2-OCH2CHN- (SvG17- Stszzzya (8)
    L j2
    CHzCl
    in the formula B Bj means
    /
    1 SWCO- (OCHCH2 2- OCHjCHz-lCgFiy-CiBFss)
    SOSH-A CH Cl
    l HCO-OCHjCHj-fCgFi-С1бГзз)
    The use of the compounds obtained.
    Examples I-XII. The compounds B, -B were tested in polyamide fiber finishing process II using a spinning process using 150 grams of unity for every 1,000 grams of fiber (the fiber finishing solution consisted of water as the main component, ethylated fatty alcohols and long-chain amine oxides as a preparative agent and about - 15% by weight of the obtained compound). i Each of 12 fiber finishing solutions used in the spinning process.
    /- eleven
    ..- A-1YANSO-OL§
    - (CH2) 6-NHCO,
    - (CH2) b- (3) - (CHzle HCO
    (9)

    The walls were trimmed to trim the same polyamide-6-elementary fibers, respectively, in order to apply on such an amount of the compound obtained. The NIN and the preparation means, which would ensure the presence on the fibers of 0.05% by weight of fluorine and 1% by weight of the preparation means (% by weight, respectively, refer to the weight of the fibers). Then the fibers were passed through the fiber finishing solution, dried during the spinning process and kept for 30 s (heat treatment, condensation). From the fibers thus treated, the appropriate kind of fabric was made .. It was from 13
    1590038
    A total of 12 types of fabrics impregnated with the compounds B, -B, j prepared were prepared, with a fluorine layer equal to 0.5 wt.% and a preparative layer equal to 1 wt.% applied to each tissue sample.
    Every from 12 tissues were tested for oleophobicity (oil-repellent properties) in accordance with the AATCC-118 test standards, 1966 and for hydrophobicity (water-repellent properties) in accordance with DIN 53 888, 1965, namely after the aforementioned condensation and after three steps - J5 of that treatment of condensed fabric by washing with a base in alkali. During this treatment, individual tissue samples were subjected to normal
    tissue (after the exposure time),
    The results are shown below: Control liquid Oil value
    Paraffin oil Paraffin oil: 10: L-Hexadecane 65:35
    repulsive properties 1
    P-Hexadecan 3
    I-tetradecan4
    p-dodecane5
    P-Deccan6
    p-octane7
    o-heptan, 8
    The value of oil-repellent properties equal to 1 means the worst, and a sign of boiling in alkali for 20 gives the best effect of oil for 3 hours, followed by drying; the washing solution consisted of 1 liter of water, 1 g of tri-sodium phosphate and 2 g of polyglycolic fatty acid ester, obtained by oxyethylation of butanediolig-1.4 with 15 mol of ethylene oxide, followed by the esterification of the product of ethoxylation with 1 mol of ol acid.
    The results of the implementation of examples I-XII are tabulated.
    The known compounds showed similar oil and water repellency properties, however they were tested in alkali washing, while the proposed compounds were tested in boiling.
    To determine the oil repellency according to AATCC-118, 1966
    talkivani.
    I.
    To determine the value of the pushing properties, 53 888 is given, the tested textile materials burp under normal conditions, and at the same time the bottom of the web is subjected to mechanical friction. The water resistance is evaluated visually within the range from 1 to 5, with 1 being the worst and a value of 5 being the best water repellent effect. The test results show that when using the proposed urethan, a very high degree of oil and water repellency is achieved, higher than that of the closest analogue in structure and, therefore, the resulting urethanes can be added to the preparation
    thirty
    35
    textile test material, the remaining treatment solutions for textile application put three drops of a specific control liquid. Impact Time 30 Co. Indicates those parameters under which Karfy is applied. 1 and no visible wetting occurs yet: and
    products.
    of
    rete n i
    45
    Formula
    The method of obtaining urethane fbrmuly
    (
     -ed7-С1бГ з) -СН2СН, 0 CH2CHO) 2-CONH A-NHCO-X-B
    J
    Where
    .U - | АЖ1
    or (Alk-CeFn-Xi fv
    r, j. -i :. i
    1590038
    lA
    tissue (after the exposure time),
    The results are shown below: Control liquid Meaning oil
    Paraffin oil Paraffin oil:: L-Hexadecane 65:35
    repulsive properties 1
    P-Hexadecan 3
    I-tetradecan4
    p-dodecane5
    P-Deccan6
    p-octane7
    o-Heptan, 8 C
    An oil repellent value of 1 is the worst, and the best oil effect is the best oil repellent effect.
    I.
    To determine the value of the repulsive properties, data is given to 53 888, the textile materials under test are spiked under normal conditions, and at the same time the underside of the web is subjected to mechanical friction. The water resistance is estimated visually within the range of 1 to 5, with 1 being the worst and a value of 5 being the best water repellent effect. The test results show that using the proposed urethanes a very high degree of oil and water repellency is achieved, higher than that of the closest analogue in structure and, therefore, the resulting urethanes can be added to the preparation
    processing solutions textile solutions
    products.
    of
    rete n i
    Formula
    The method of obtaining urethane fbrmuly
    J
    SNL
    SNGSN O-SOMN- (l)
    i
    W, 0- (CH2CNW) 2-С (ЖН- (z) CHjCl
    X - group of formulas 4-7 :.
    r; -Z,
    -Zi-e SO:
    (four)
    -Z 2
    (6)
    SNS (5)
    -Z
    CF3
    -O- -O-T-g- SGS (7)
    hydrogen atom or group of forms
    where Z, and or yes, when both of them; same or different, or O or ° 9: 000, when they are different and B is designated -:.
    -G SOKN-A-Ш1СО- (ОСНСН2 2 ОНСНгСНг- (С eFi7 - - А1К)
    . iHjCJl
    - CONH-A
    IJHCO - (OCHCH 2) 2 - OGH zCH 2 - (C gfiy C Lz - A1K). ShzS
    INSO - OSI cng- (С gH - С 1bГзз - AIK)
    where A has the indicated value, where R. (C | Fj7 C
    about tl and h and y and with the fact that 2;
    aliphatic fluoride alcohol form-at 0 or 2,
     R V nffH GNP - Nvvod t interaction with the triisoxy / ZJJf x 2, / i / anatom, respectively, a group of the formula
       obtaining adducts of formulas 10
    CH2Cl or 11:
    45
    I (AiR-CeFiT С «Гзз) - (: n2s: n20 - (ds2sno) 2- CONH
    IM, j
    SNFS
    (MK-SzGp-С1бРзз) -СНгСН20-CONH
    (A1K-C gFjT - C 1bGzz) -CH - (CH zCHO) 2 - SOSH
    CH2Cl
    SNS
    SNS (5)
    -Z
    CF3
    -O- -O-T-g- SGS (7)
    a hydrogen atom or a group of formulas
    ° 9:
    -A-NCO
    H
    /
    A-NCO
    17
    where A has the indicated value, and then the resulting adducts are reacted with an aromatic disc, aminooxy or oxycarboxy compound of the following formula
    H - X - H, where X has the specified value,
    about -
    1590038
    creeping Urethanes of formula 1 or 2, where A and X have the indicated meanings and BH,
    and these urethanes are reacted with an adduct according to formula 10 or 11 to obtain the desired product of formulas 1 or 2, where A and X are as defined above, and B corresponds to formulas 8 or 9.
    权利要求:
    Claims (3)
    [1]
    Claim
    The method of producing urethanes of the formula: n 2 clearly) 2 - CONhJ-A-NHC0 -X- where or (Aik- C 8 f J7 - С
    CH 2 CH 2 O-CONH- (1). □ 2 g (ch 2 cho) 2 -conh- (
    [2]
    2)
    CH 2 C1 where A is a group of formula (3):
    1590038, - (CH Z ) 6 -NHCO
    X is a group of formulas 4-7:
    -z 1 -0-so 2 + Q ~ z i! (6) 'l where Z, and Ζ ^ Ό or ΝΗ when they are both the same or different, or 0 or
    Ltd., and when they are different in notation-CONH-A- ^ NHCO- (OCHCH 2) 2 -OCH 2 CH 2 - (C 8 F 17 -C 16 F 33 - Aik) chaet hydrogen atom or a group of the formulas
    8 or 9:
    I
    CH 2 C1
    NHC0- (0CHCH g ^ | 2 - OCH 2 CH 2 - (C 8 F 17 - C 16 F 33 -Aik) -CONH-A ^ CH 2 C1
    NHCO - OCH 2 CH 2 - (C 8 H 17 - C 16 F 33 - Aik) where A has the above meaning, except that the aliphatic fluorine alcohol is form KDSN 2 ) x O (CH 2 CHO) </ - N
    CH 2 C1 | "(A1K ~ C 8 F 17 - C 16 F 33) - CH 2 CH 2 O - (CH 2 CHO) 2 - CONhJ-A-NC0 CH 2 C1 2» (C | Ff7- CoD> 5 = 2;
    = 0 or 2, in interaction with a triisociso group, respectively, where R | x
    U injected by anatomist
    [3]
    3 to obtain adducts of formulas 10 or 11:
    I (Alk-C 8 F l7 -C 16 F 33 ) -CH 2 CH 2 O-CONH X A-NC0 (AIK-C 8 F 17 - C 18 F 33 ) - CH 2 CH 2 0 - (CH 2 CH0 ) 2 - Cow /
    CH 2 C1 where A has the indicated meaning ..... to produce urethanes of the formula 1 or then the resulting adducts are reacted with an aromatic dioxo, aminooxy or hydroxy carboxy compound of the following formula
    H - X - H, where X has the indicated value, ζ, where ail have the indicated values and B = H, and these urethanes are reacted with the adduct according to formula 10 or 11 to obtain the target products of formulas 1 or 2, where A and X have the above meanings, and B corresponds to formulas 8 or 9.
    Examples // tested compounds Oil repellent after Water repellent after condensation boiling wash condensation boiling wash I / B 6 3 5 4 and / in 26 3 5 4 w / h 36 4 5 4 IV / B f5 4 4 4 .. v / B 55 4 4 4 vi / B t• 54 5 4 VII / B 75 4 5 4 VIII / B, 6 5 5 4 IX / B 95 5 5 4 X / B „ 5 4 4 3 XI / B „ 5 4 4 3 XIl / B n5 4 5 4
    类似技术:
    公开号 | 公开日 | 专利标题
    SU1590038A3|1990-08-30|Method of producing urethanes
    US5565564A|1996-10-15|Polyfluoro organic trimer compounds having urea linkage
    US5411766A|1995-05-02|Substrates treated with polyfluoro nitrogen containing organic compounds
    JP3992759B2|2007-10-17|Poly-perfluoroalkyl-substituted alcohols and acids and their derivatives
    US5410073A|1995-04-25|Manufacture of polyfluoro nitrogen containing organic compounds
    CA1038112A|1978-09-12|Durable textile treating adducts
    CA1328461C|1994-04-12|Urethanes containing fluorine and polysiloxane, processes for their preparation and their use
    CA2032813C|2002-09-24|Polyfluoro nitrogen-containing organic compounds
    TWI670285B|2019-09-01|Polyurethanes derived from non-fluorinated or partially fluorinated polymers
    US4014857A|1977-03-29|Fluorinated oily soil release agents
    US5171877A|1992-12-15|Urethanes made from aliphatic fluoro alcohols, isocyanates and carboxylic acids, a process for their preparation and their use
    TWI678384B|2019-12-01|Partially fluorinated urethane based coatings
    US4960543A|1990-10-02|Urethane made from aliphatic fluorinated alcohols, isocyanates and substituted aromatic compounds, a process for their preparation, and their use
    EP0472492B1|1994-10-05|Tris-perfluoroalkyl terminated neopentyl alcohols and derivatives therefrom
    KR940008917B1|1994-09-28|Urethanes with contain perfluoroalkyl groups, epichlorohydrin groups and dialcohol radicals the preparation and use thereof
    US3906049A|1975-09-16|Fluorine and sulfur-containing compositions
    US3894992A|1975-07-15|Fluorinated oily soil release agents
    KR100240859B1|2000-01-15|Fluorocarbammate soil-release agents
    DE1467552A1|1969-01-23|Low-foaming detergents and cleaning agents
    US3285975A|1966-11-15|omega-perfluoroalkyl alkenols
    US3839373A|1974-10-01|Perfluoroalkylalkylmonocarboxylic acid esters derived from cyclo-aliphatic epoxides
    US3818058A|1974-06-18|Aromatic perfluoroalkylalkylmonocarboxylic acid esters
    JP2006188431A|2006-07-20|Fluorine-containing urethane compound and use of the same
    AU602105B2|1990-09-27|Process for the preparation of perfluoroalkyl-containing epoxides and novel perfluoroalkyl-containing epoxides
    Sangsari et al.1990|Competitive hemiacetalization and acetalization: Cross‐linking of cellulose by glyoxal
    同族专利:
    公开号 | 公开日
    JPS6314764A|1988-01-21|
    CA1296018C|1992-02-18|
    ES2023382B3|1992-01-16|
    EP0253186A3|1988-09-21|
    DD257828A5|1988-06-29|
    US4782175A|1988-11-01|
    BR8703371A|1988-03-15|
    AU7505287A|1988-01-07|
    EP0253186B1|1991-06-19|
    EP0253186A2|1988-01-20|
    KR880001581A|1988-04-25|
    DE3770885D1|1991-07-25|
    AT64593T|1991-07-15|
    DE3622284A1|1988-01-07|
    DD257828C4|1989-03-01|
    AU593919B2|1990-02-22|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3681426A|1968-08-30|1972-08-01|Hoechst Ag|Fluorinated polymers having bisurethano side chains|
    US3657320A|1968-11-08|1972-04-18|Allied Chem|Perfluoroalkoxyalkyl-substituted carbamates|
    BE756285A|1969-09-17|1971-03-17|Hoechst Ag|FLUORINE POLYOXETHYLATION PRODUCTS THAT CAN BE USED FOR TEXTILE APPRETATION|
    US4289892A|1970-03-03|1981-09-15|Minnesota Mining And Manufacturing Company|Fluorochemical foam stabilizer and foamed polyurethanes made therewith|
    US3994951A|1975-07-17|1976-11-30|Pennwalt Corporation|Polyoxyalkylene fluoroalkyltrimellitates|
    US4321404A|1980-05-20|1982-03-23|Minnesota Mining And Manufacturing Company|Compositions for providing abherent coatings|
    US4525305A|1982-10-25|1985-06-25|Minnesota Mining And Manufacturing Company|Leather with fluorochemical finish|
    US4958039A|1984-08-24|1990-09-18|E. I. Du Pont De Nemours And Company|Modified fluorocarbonylimino biurets|
    DE3530967A1|1985-08-30|1987-03-05|Hoechst Ag|Urethanes containing perfluoroalkyl and epichlorohydrin groups, aqueous dispersions containing these urethanes, and their use|
    DE3540147A1|1985-11-13|1987-05-14|Hoechst Ag|PERFLUORALKYL GROUPS, EPICHLORHYDRINE GROUPS AND UALETHANE CONTAINING DIALCOHOL RESIDUES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE|DE3722375A1|1987-07-07|1989-01-19|Hoechst Ag|URETHANES CONTAINING FLUOR AND POLYSILOXANE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE|
    DE3744423A1|1987-12-29|1989-07-13|Hoechst Ag|URETHANES OF ALIPHATIC FLUORO ALCOHOL, ISOCYANATES AND SUBSTITUTED AROMATIC COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE|
    US4935535A|1989-01-19|1990-06-19|National Science Council|Ultraviolet-autocurable benzophenone tetracarboxylic dianhydride-based polyurethane acrylate oligomers|
    JP2503657B2|1989-06-05|1996-06-05|大日本インキ化学工業株式会社|Water and oil repellent|
    DE3943127A1|1989-12-28|1991-07-04|Hoechst Ag|URETHANES AS ALIPHATIC FLUORO ALCOHOL, ISOCYANATES AND CARBONIC ACIDS, PROCESS FOR THEIR PREPARATION AND THEIR USE|
    CA2032813C|1989-12-29|2002-09-24|Jack R. Kirchner|Polyfluoro nitrogen-containing organic compounds|
    US5580645A|1989-12-29|1996-12-03|E. I. Du Pont De Nemours And Company|Substrates treated with polyfluoro nitrogen-containing organic compounds|
    US5276175A|1991-04-02|1994-01-04|Minnesota Mining And Manufacturing Company|Isocyanate derivatives comprising flourochemical oligomers|
    AU659229B2|1991-11-12|1995-05-11|Minnesota Mining And Manufacturing Company|Fluoroaliphatic dimer acid derivatives and use thereof|
    JP2523095Y2|1991-11-15|1997-01-22|株式会社テック|Load cell scale|
    US5407728A|1992-01-30|1995-04-18|Reeves Brothers, Inc.|Fabric containing graft polymer thereon|
    US5486210A|1992-01-30|1996-01-23|Reeves Brothers, Inc.|Air bag fabric containing graft polymer thereon|
    WO1993017165A1|1992-02-28|1993-09-02|E.I. Du Pont De Nemours And Company|Fluorocarbamate soil-release agents|
    DE4244951C2|1992-12-01|1998-08-06|Minnesota Mining & Mfg|New poly:siloxane cpd and carboxylic acid derivs., prepn. and use|
    US5496642A|1994-05-09|1996-03-05|Olin Corporation|Low VOC, fluorocompound-containing one-component and two-component coating compositions for slippery coatings|
    DE69605925T2|1996-11-07|2000-07-20|Minnesota Mining & Mfg|Use of amphiphilic copolymers containing fluorine-containing monomer for waterproofing leather|
    US6294103B1|1996-11-07|2001-09-25|3M Innovative Properties Company|Use of amphiphilic copolymers containing a fluorinated monomer to impart waterproofness to leather|
    US7049379B2|1999-05-11|2006-05-23|3M Innovative Properties Company|Alkylated fluorochemical oligomers and use thereof in the treatment of fibrous substrates|
    US6525127B1|1999-05-11|2003-02-25|3M Innovative Properties Company|Alkylated fluorochemical oligomers and use thereof in the treatment of fibrous substrates|
    US20090110840A1|2007-10-24|2009-04-30|Peter Michael Murphy|Hydrophillic fluorinated soil resist copolymers|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19863622284|DE3622284A1|1986-07-03|1986-07-03|URETHANES MADE FROM ALIPHATIC FLUORAL ALCOHOLS, ISOCYANATES AND AROMATIC COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE|
    [返回顶部]