PERSONAL CARE COMPOSITIONS CONTAINING IONIC SILICON AND FILM FORMING AGENT

专利摘要:
Summary "Personal Care Compositions Containing Ionic Silicone and Film-Forming Agent" A personal care composition includes at least one functionally tipped silicone and at least one film-forming agent.
公开号:BR112014016668B1
申请号:R112014016668-4
申请日:2013-01-04
公开日:2019-09-24
发明作者:Alok Sarkar；Anubhav Saxena；Sandip Tiwari；Benjamin Falk；Anne Dussaud
申请人:Momentive Performance Materials Inc.；
IPC主号:

专利说明:

“COMPOSITIONS FOR PERSONAL CARE CONTAINING IONIC SILICON AND FILM FORMING AGENT”
REMISSIVE REFERENCE TO RELATED APPLICATIONS [001] This application is a continuation in part of US patent application Serial No. 13 / 733,482, filed on January 3, 2013, which claims the benefit of provisional US patent application No. . series 61 / 582,914, deposited on January 4, 2012, all the contents of these benefited requests being incorporated by reference.
BACKGROUND OF THE INVENTION [002] This invention relates to personal care compositions containing one or more ionic silicone components and at least one film forming agent.
[003] Personal care products formulated with ionic silicones are known to be a personal care product formulated with chemically cross-linked polymer film former. However, it is believed that personal care products that contain an ionic silicone component and a film-forming agent have not been described so far.
SUMMARY OF THE INVENTION [004] In accordance with the present invention, a composition for personal care is provided, comprising:
(a) at least one ionic silicone with functionalized end of formula:
M ¹ to M ² b M ³ c, D ¹ d D ² and D ³ f T1g T ² h T ³ i Qj (I) where:
M ¹ = R ¹ R ² R ³ SiO1 / 2
M ² = R ⁴ R ⁵ R ⁶ SiO1 / 2
M ³ = R ⁷ R ⁸ R ⁹ SiO1 / 2
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2/43
D ¹ = R ¹⁰ R ¹¹ SiO2 / 2
D ² = R ¹² R ¹³ SiO2 / 2
D ³ = R ¹⁴ R ¹⁵ SiO2 / 2
T ¹ = R ¹⁶ SiO3 / 2
T ² = R ¹⁷ SiO3 / 2
T ³ = R ¹⁸ SiO3 / 2
Q = SiO4 / 2 where
R ¹ , R ² , R ³ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹³ , R ¹⁵ and R ¹⁶ each, independently, is a monovalent aliphatic, aromatic or fluorine having from 1 to 60 carbon atoms;
R ⁴ , R ¹² and R ¹⁷ , each independently is a monovalent group carrying ion pairs and having the formula -AI ^x- Mn ^{y +} , or zwitterion having the formula -R'-N ⁺ (R) 2-R '- | ·, where A is a spacing portion with at least one spacing atom, the spacing portion being selected from the group consisting of the divalent hydrocarbon group and the hydrocarbonoxy group, I is an ionic group, R 'is a divalent hydrocarbon group having 1 to 20 carbon atoms, R is a monovalent hydrocarbon group having 1 to 20 carbon atoms, R''' is a divalent hydrocarbon group having 2 to 20 carbon atoms , and each M, independently, is hydrogen or a cation independently selected from alkali metals, alkaline earth metals, transition metals, quaternary ammonium and phosphonium groups;
R ⁷ , R ¹⁴ and R ¹⁸ each, independently, is -CH2CH (R ¹⁹ ) (CnH2n) -O (C2H4O) O ^- (C3H6O) p ^- (C4H8O) q ^- R ¹⁹ where R ¹⁹ is hydrogen or a group R ¹ as defined above;
superscripts x and y are positive integers subject to the limitation that x = ny; each subscript n independently has a value from 0 to 6 and subscripts o, p and q,
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3/43 each, independently, has a value from 0 to 1000, subject to the limitation that + p + q> 1; e, the subscripts a, c, d, e, f, g, h, iej, each, independently, is zero or a positive integer subject to the limitations that 2 <a + b + c + d + e + f + g + h + i + j <4500 and b> 2; and, (b) from 0.1 to 99 parts by weight of at least one film-forming agent.
[005] The ionic silicone component with functionalized end of the personal care composition of the present invention forms aggregates of the ionic groups for ion-rich domains of specific dimensions that act as the ionic charge of the composition. These ionic aggregates act as cross-links and increase the modulus of the composition. Unlike chemically crosslinked polymer film forming agents where once the crosslinks are broken due to some applied external force (eg heat or shear) it causes the system to permanently lose its integrity, the ionic crosslinks, when subjected this external force causes ionic clusters to disintegrate and reform as aggregates when the applied force is removed. However, due to the relatively lower binding strength of the ionic bond, personal care compositions formulated with ionic silicones alone may not be sufficient to provide the same magnitude of benefits compared to similar personal care compositions formulated with ion forming agents. chemically known and conventional cross-linked polymer films.
DETAILED DESCRIPTION OF THE PREFERENTIAL MODALITIES [006] In the specification and the attached claims, the following terms and expressions should be understood as indicated.
[007] As used in the specification and including the attached claims, the singular forms one, one, and the, include the plural, and the reference to
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4/43 a particular numerical value includes at least that particular value, unless the context clearly indicates otherwise.
[008] In addition to the working examples or where otherwise indicated, the numerical values and ranges of numerical values in this document, whether modified or not by terms such as about and approximately, should be understood to include the value (s) ) indicated (s) and the approximate value (s) to the same (s). When such a range is expressed, another modality includes from the particular value and / or to another particular value. Likewise, when values are expressed as approximations, for example, by using the about modifier, it must be understood that the particular values form another modality.
[009] It will also be understood that any numerical range recited in this document intends to include all sub-ranges within that range.
[010] All of the methods described in this document may be carried out in any appropriate order, unless otherwise indicated or clearly contrary to the context. The use in this document of any and all examples or exemplary language (for example, as such) is intended merely to better illustrate the invention and is not a limitation on the scope of the invention unless otherwise claimed. No language in the specification should be understood to indicate any element not claimed as essential to the practice of the invention.
[011] As used herein, terms comprising, including, containing, characterized by and grammatical equivalents thereof are comprehensive or open terms that do not exclude additional elements not mentioned or steps in the method and should also be understood as including the most common terms. restrictive consisting of and “consisting essentially of”.
[012] It should also be understood that any compound, material or substance that is expressly or implicitly disclosed in the specification
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5/43 and / or recited in a claim as belonging to a group of structurally, compositionally and / or functionally related compounds, materials or substances, includes individual representatives of the group and all combinations thereof.
[013] The ionic silicones with functionalized end (I) of the present invention form aggregates of ionic groups with ion-rich domains, having dimensions, for example, from 40 to 200 nm, which serve as ionic charge in the composition. These ionic aggregates act as cross-links and increase the material's modulus. In addition to acting as cross-links, the aggregates also behave as reinforcement of charge particles and, as such, can further increase the composition module for personal care containing them. In addition, due to the reversible nature of ionic interactions, when heated to a certain level (for example, ca. 180 ° C) the ionic aggregates disintegrate somewhat to form relatively more thermodynamically stable ionic aggregates after cooling. As a consequence of this phenomenon, the viscosity of these materials continues to increase during repeated heating / cooling cycles. In addition, ionic aggregates can be dissolved in a polar solvent such as water, then reformed with solvent removal. The presence of ionic groups also helps to make silicones (I) exceptionally compatible with the hydrophilic and lipophilic components commonly used in such personal care compositions as moisturizers, sunscreens and the like.
[014] It is believed that the foregoing unique physico-chemical properties of ionic silicones with functionalized (I) end play an important role in providing such highly desirable product performance characteristics as high transfer resistance and high gloss in color formulations for lips, controlled release of assets and nouns in
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6/43 sun protection agents and other compositions for personal care, and the like.
[015] In ionic silicone with functionalized end (I) in this document each group R ¹ , R ² , R ³ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹³ , R ¹⁵ and R ¹⁶ is preferably methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl, tert-pentyl; hexyl, such as the n-hexyl group; heptyl, such as the non-heptyl group; octyl, such as the non-octyl and isooctyl groups and the 2,2,4-trimethylpentyl group; nonyl, such as the n-nonyl group; decyl, such as the n-decyl group; cycloalkyl radicals, such as cyclopentyl, cyclohexyl and cycloheptyl and methylcyclohexyl radicals. Representative aromatic groups include phenyl, naphthyl; o-, m- and p-tolyl, xylyl, ethylphenyl and benzyl.
[016] In groups R ⁴ , R ¹² and R ¹⁷ , the divalent hydrocarbon spacing group A of ionic-AI ^x- -Mn ^{y +} can be, for example, an alkylene group such as - (CHR ²⁰ ) -m where R ²⁰ is hydrogen or a group R ¹ as defined above and the subscript m is a positive integer ranging from 1 to 100 and preferably from 1 to 20; or an arylene group, such as - (CHR ²¹ ) kC6H4 (CH2) r - CH2-CH (R ') (CH2) kC6H4- or CH2CH (R ²² ) (CH2) rC6H3R ²³ , where R' is hydrogen or a group R ¹ as defined above, R ²¹ is hydrogen or a group R ¹ as defined above, R ²² is hydrogen or a group R ¹ as defined above, R ²³ is a monovalent radical of 1 to 20 carbon atoms and the subscripts ker are zero or positive integers subject to the limitation of 0 <k + r <100.
[017] The divalent hydrocarbon spacing group A can also be, for example, a divalent hydrocarbonoxy group such as - (CHR ²⁴ ) s- (OCHR ²⁴ CH2) s'-O- (CH2) -t, where R ²⁴ is hydrogen or a group R ¹ as defined above, s has a value from 0 to 50, s 'has a value from 1 to 50 and t has a value from 0 to 50 subject to the limitation of 1 <s + s' + t <100.
[018] I ^- in the group that carries the ionic pair and in the zwitterion it is, preferably, an ionic group such as sulfonate -SO3 ^- , sulfate -OSO3 ^- , and the like.
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7/43 [019] Examples of M + cation include Li, Na, K, Cs, Mg, Ca, Ba, Zn, Cu, Fe, Ni, Ga, Al, Mn, Cr, Ag, Au, Pt, Pd, Ru and Rh.
[020] In zwitterion, R 'is a divalent hydrocarbon radical having from 1 to 20 carbon atoms, for example, - (CH2) s ^- ; R is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, for example, -CH2CH3; and, R '''is a divalent hydrocarbon radical having from 2 to 20 carbon atoms, for example, - (CH2) 4-.
[021] In ionic silicone with functionalized end (I), R ⁷ , R ¹⁴ and R ¹⁸ each, independently, is CH2CH (R ¹⁹ ) (CnH2n) -O- (C2H4O) o- (C3HeO) p (C4H8O) qR ¹⁹ , where R ¹⁹ is hydrogen or a group R ¹ as defined above, each subscript n independently has a value from 0 to 6 and subscripts o, p and q each independently have a value subject to the limitation that the + p + q> 1.
[022] In ionic silicone with functionalized end (I), the subscripts a, c, d, e, f, g, h, iej, each, independently, is zero or a positive number subject to the limitations that 2> a + b + c + d + e + f + g + h + i + j> 4500, b> 2. In one embodiment, the subscript b is 2; the subscripts a, c, e, f, g, h, i, j, k, 1 and m are 0; subscript d is 5 to 1000, more preferably 10 to 500, and most preferably 10 to 200; R ⁵ , R ⁶ , R ¹⁰ and R ¹¹ are methyl or ethyl; R ¹⁰ is -CH2CH (H or CH3) -A-SO3M; A is a divalent benzyl radical; and, M is Li, Na, K, Ag or a group of quaternary ammonium, ammonium salt or a phosphonium group.
[023] Examples of ionic silicone (I) include sodium sulfonate-capped polydimethylsiloxane, silver sulfonate-capped polydimethylsiloxane, magnesium sulfonate-capped polydimethylsiloxane, calcium sulfonate-capped polydimethylsiloxane and zinc-capped polydimethylsilane with sulfonate with triethanolammonium sulfonate.
[024] The film forming agents according to the present invention include, but are not limited to, organosiloxane resins, polymers of
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8/43 hydrocarbons, hydrocarbon polymers containing heteroatoms, hydrocarbon polymers containing a fluorine atom, and clays.
[025] Useful organosiloxane film forming agents may comprise combinations of R3SiOi / 2, R2SiO, RSiO3 / 2, and SiO2 units in ratios that satisfy the RnSiO (4-n) / 2 ratio, where n is a value between 0 and 1.50 and R is independently selected from groups of methyl, trifluoromethyl, phenylenomethyl and phenyl.
[026] The hydrocarbon polymer film forming agents useful in accordance with the present invention can be selected from, but are not limited to, polybutene, polyisobutene, polycyclopentadiene, petroleum jelly and mineral oil.
[027] Hydrocarbon polymers containing at least one heteroatom that are useful as film-forming agents according to the present invention can be selected from, but are not limited to, Polyvinylpyrrolidone (PVP) / eicosene copolymer, Copolymer of PVP / hexadecene, acrylate copolymer and polyvinyl alcohol.
[028] Suitable film-forming clays according to the present invention can include a number of modified and unmodified clays, including cloisite 30B, momtmorilite (NaMMT), LDH and bentonite.
[029] Personal care compositions according to the present invention include, but are not limited to, antiperspirant deodorants, deodorants / antiperspirants including sprays, sticks and roll-on products, shaving products, skin lotions, moisturizers , toners, bath products, cleaning products, shampoos, conditioners, shampoo / conditioners combined, mousses, styling gels, hair sprays, hair dyes, hair coloring products, hair bleaches, curling products, straighteners hair, nail polish, nail polish remover, creams and lotions
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9/43 for nails, cuticle softeners, sunscreen, insect repellent, anti-aging products, lipsticks, foundations, facial powders, eye liners, eyeshadows, blushes, makeup, masks, moisturizing preparations, foundations, body and hand preparations , skin care preparations, face and neck preparations, tonics, dressings, hair care aids, fixative aerosols, fragrance preparations, aftershave lotions, makeup preparations, soft focus applications, skin care preparations night and day, non-hair coloring preparations, tanning preparations, synthetic and non-synthetic soap bars, hand liquids, nose strips, non-woven personal care applications, baby lotions, bath lotions and baby shampoos , baby conditioners, shaving preparations, cucumber slices, skin patches, makeup removers, facial cleansers , cold creams, sun protection products, mousses, spritzes, masks and pasty slurries, face masks, colognes and colognes, hair cuticle liners, shower gels, face and body washes, personal care rinse products, gels, bubble baths, scrub cleaners, astringents, nail conditioners, eye shadow sticks, face or eye powders, lip ointments, lip glosses, hair spray pumps and other aerosol free sprays , hair frizz control gel, leave-in hair conditioners, hair polishes, hair detangling products, hair fixers, hair bleaching products, skin lotions, pre-shave and pre-shave creams for shaving with electric shavers, anhydrous creams and lotions, oil / water, water / oil emulsions, multiple and macro and micro emulsions, water-resistant creams and lotions, preparations to ntiacne, mouth rinses, massage oils, toothpastes, whitening gels and sticks, ointment bases, topical wound healing products, aerosol talc, barrier sprays, vitamins and
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10/43 anti-aging, preparations based on herbal extracts, bath salts, body and bath milks, modeling aids, soft solid applications for hair, eyes, nails and skin, controlled-release personal care products, conditioning mists hair, moisturizing mists for skin care, wipes to clean the skin, wipes to clean the pores of the skin, pore cleaners, blemish reducers, skin exfoliators, skin peeling enhancers, wipes and skin towels, depilatory preparations , personal care lubricants, nail coloring preparations, drug delivery systems for the topical application of medicinal compositions to be applied to the skin and combinations comprising at least one of the previous personal care applications.
[030] The personal care composition of the present invention can optionally contain up to 90 parts by weight of one or more pigments. The pigments suitable for use in the present invention are all inorganic and organic pigments / dyes. These are usually aluminum, barium or calcium salts or lacquers. A lacquer is a pigment that is extended or reduced with a solid diluent or an organic pigment that is prepared by precipitation of a water-soluble dye on an absorption surface, which is usually aluminum hydrate. A lacquer also forms precipitation of an insoluble salt of an acidic or basic dye. Calcium and barium lacquers are also used in this document. Other dyes and pigments can also be included in the compositions, such as pearls, titanium oxides, dyes Red 6, Red 21, Blue 1, Orange 5 and Green 5, chalk, talc, iron oxides and titanium micas.
[031] The personal care composition of the present invention can optionally contain up to 99 parts by weight of one or more known or conventional cosmetically acceptable organic film former. Examples of suitable film formers include natural waxes, polymers, such as
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11/43 polyethylene polymers, PVP copolymers, ethylene vinyl acetate, dimethicone gum, resins such as shellac, polyesterpenes, and the like.
[032] The personal care composition of the present invention may optionally include up to 50 parts by weight of blocking and / or absorbing sun protection agents. Blocking sun protection agents are generally inorganic, such as various cesium oxides, chromium oxides, cobalt oxides, iron oxides, red petrolatum, silicone and other treated titanium dioxides, titanium dioxide, zinc oxide, and / or zirconium oxide, BaTiO3, CaTiO3, SrTiO3 and SiC. Sunscreen-absorbing agents, which are generally of organic species, include, but are not limited to, UV-A absorbers, which generally absorb radiation in the region from 320 to 400 nm of the ultraviolet spectrum, for example, anthranilates, benzophenones and dibenzoyl methanes; and, UV-B absorbers, which generally absorb radiation in the 280 to 320 nm region of the ultraviolet spectrum, for example, p-aminobenzoic acid derivatives, camphor derivatives, cinnamates and salicylates.
[033] Specific examples of organic sunscreen agents include p-aminobenzoic acid, avobenzone cinoxate, dioxibenzone, homosalate, menthyl anthranilate, octocrylene, octyl methoxy cinnamate, octyl salicylate, oxybenzone, padimate, phenylbenzobidazone sulfonic acids, sulphisbenzimidone , trolamine salicylate, aminobenzoic acid, amildimethyl p-aminobenzoic acid, diethanolamine pmethoxy cinnamate, digaloyl trioleate, 2-ethylhexyl-2-cyano-3,3-diphenylacrylate, ethylhexyl p -methoxy-cinamate 2, salicylate -hexyl, glyceryl aminobenzoate, homomentyl salicylate, homosalate, 3-imidazol-4-ylacrylic acid and the ethyl ester thereof, methyl anthranilate, octyldimethyl PABA, 2-phenylbenzimidazole-5-sulfonic acid and its salts, sulisobenzone , N, N, N-trimethyl-4- (2-oxoborn-3-ylidene-methyl) anilinium sulfate, aminobenzoate, 4-isopropylbenzyl salicylate, 2-ethylhexyl-4-methoxy kinamate, methyl diPet tion 870190033247, of 5/5/2019, p. 24/64
12/43 isopropyl cinnamate, isoamyl 4-methoxy cinnamate, diethanolamine 4-methoxy cinnamate, 3 (4'-trimethylammonium) -benzyliden-boman-2-one methylsulfate, 2-hydroxy-4-methoxy benzophenone, 2-hydroxy-4-methoxy benzophenone-5-sulfonate, 2,4-dihydroxybenzophenone, 2,2 ', 4,4'-tetrahydroxybenzophenone, 2,2'-dihydroxy-4,4'dimethoxy benzophenone, 2-hydroxy-4-n- otoxy benzophenone, 2-hydroxy-4-methoxy-4'-methoxy benzophenone, ca- (2-oxoborn-3-ylidene) -tolyl-4 sulfonic acid and soluble salts thereof, 3- (4'-sulfo) benziliden- bornan-2-one and soluble salts thereof, 3- (4'methylbenzylidene) -d, l-camphor, 3-benzylidene-d, l-camphor, benzene 1,4-di (3-methylidene-10-camphosulfonic acid) and their salts thereof, urocanic acid, 2,4,6-tris (2'-ethylhexyl-1'-oxycarbonyl) -anilinol 1,3,5-triazine, 2- (p- (tert-butylamido) anilinol- 4,6bis- (p- (2'-ethylhexyl 1'-oxycarbonyl) anilinol 1,3,5-triazine, 2,4-bis {1,4- (2-ethylhexyloxy) -2hydroxy-phenyl} -6- (4-methoxy phenyl) -1,3,5-triazine, the polymer of N- (2 to 4) - ( 2-oxoborn-3iliden) methylbenzyl acrylamide, 1,4-bisbenzimidazolyl-phenylene-3,3 ', 5,5'-tetra-sulfonic acid and salts thereof, the benzalmalonate-substituted polyorganosiloxanes, the polyorganosiloxanes (drometrizol trisiloxane) substituted with benzotriazol 2 , 2'-methylene-bis-1,6- (2H-benzotriazol-2-yl) -4- (1,1,3,3tetramethylbutyl) solubilized phenol, 2-methyl-dibenzoylmethane, 4-methyldibenzoylmethane, 4isopropylbenzoylmethane, 4- tert-butyldibenzoylmethane, 2,4-dimethyldibenzoylmethane, 2,5-dimethyldibenzoylmethane, 4,4'-diisopropylbenzoylmethane, 4,4-dimethoxy dibenzoylmethane, 4-tert-butyl-4'-methoxy dibenzoylmethane, 2-methyl-5- isopropyl-4'-methoxy dibenzoylmethane, 2-methyl-5-tert-butyl-4'-methoxy dibenzoylmethane, 2,4-dimethyl-4'-methoxy dibenzoylmethane, 2,6-dimethyl-4-tert-butyl-4 ' -dibenzoylmethane methoxy, and combinations comprising at least one of the previous sunscreen agents.
[034] In one embodiment, it was found that a combination of at least three sun protection agents is especially effective. In another modality, it was found that a combination of four sunscreen agents is particularly effective, especially where sunscreen agents are used
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13/43 solar chemicals.
[035] The personal care composition of the present invention is specifically formulated for use as a colored cosmetic product, sunscreen, hair conditioner and a moisturizer. Suitable forms and formulations for this application are known to those of ordinary skill in the art. For example, when formulated for use as a sunscreen, the composition can be in the form of a lamellar emulsion, a microemulsion, or a nanoemulsion. In addition, the emulsion may be a single fluid emulsion, a multiple fluid emulsion, a single rigid emulsion, or a multiple rigid emulsion. The single emulsion or multiple emulsion may comprise a continuous aqueous phase containing lipid vesicles or dispersed oil droplets, or lipid vesicles or water droplets dispersed in a continuous grease phase.
[036] In one embodiment, the application of sunscreen is an emulsion having a continuous aqueous phase, and can be in the form of a stick, lotion, gel, spray, and the like. Emulsifiers suitable for forming sun protection emulsions include, for example, ethoxylated surfactants known in the art such as Polysorbate-20, Laureth-7, Laureth-4, Sepigel® 305 available from SEPPIC, oils such as mineral oil and vegetable; animal and / or synthetic waxes such as beeswax, paraffin, rice bran wax, candelilla wax, carnauba wax and derivatives thereof; and hydrocarbon gels or bentone gels, such as Gel SS71, Gel EA2786, Bentonite Quaternium-18, 38 CE, Gel ISD V or Gel ISD; and organosiliconised emulsifiers, such as cetyl dimethicone copolyol-polyglyceryl-4-isostearate-hexilaurate (ABIL® WE 09) available from Goldschmidt Chemical Corporation, behenate dimethicone, cetyl dimethicone copolyol (ABIL® EM 90), (ABIL® EM 97), copolyol of laurylmethicone (5200), cyclomethicone and copolyol of dimethicone (DC 5225 C and DC 3225 C) available from Momentive Performance Materials Inc., cyclopentasiloxane and copolyol of
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14/43 dimethicone, are also available from Momentive Performance Materials, Inc.
[037] Plasticizers can also be added to the sunscreen formulation to improve the flexibility and cosmetic properties of the resulting formulation. Plasticizers are often used to prevent embrittlement and cracking of film-forming polymers, and include, for example, lecithin, polysorbates, dimethicone copolyol, glycols, citrate esters, glycerin and dimethicone. One skilled in the art can routinely vary the amount of plasticizer desired based on the desired properties and intended application.
[038] The composition of the present invention is preferably incorporated into a carrier, especially a volatile carrier that quickly volatilizes after application. The volatile carriers of the present invention are selected from the group consisting of volatile hydrocarbons, volatile silicones, and mixtures thereof. The hydrocarbon oils useful in the present invention include those having boiling points in the range of 60-260 ° C, more preferably, hydrocarbon oils having from about C8 to about C20 of chain lengths, more preferably, from C8 to C20 isoparaffins. The most preferred are selected from the group consisting of isododecane, isohexadecane, isoeocosane, 2,2,4-trimethylpentane, 2,3-dimethylhexane and mixtures thereof. Preferred volatile silicone fluids include cyclomethicone with 3-, 4- and 5-membered ring structures that correspond to the formula (R2SiO) x, where x is about 3 to about 6 or linear methicones corresponding to the formula (R3SiO (R2SiO) xSiR3 where x is about 0 to about 6.
[039] A thickening polymer can be useful in the present invention. The term thickener polymer should be understood for the purposes of the present invention to mean a polymer that has, in solution or dispersion containing 1% by weight of the active material in water or in ethanol at 25 ° C,
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15/43 viscosity greater than 0.02 Pa.s (0.2 poise) at a shear rate of 1 s-I. Viscosity can be measured with a HAAKE RS600 viscometer with THERMO ELECTRON. This viscometer is a voltage controlled viscometer with a cone and plate geometry (for example, having a diameter of 60 mm and an angle of 1 °). Examples of thickeners include; associative thickeners; crosslinked acrylic acid homopolymers; cross-linked copolymers of (meth) acrylic acid and (C1-C6) alkyl acrylate; homopolymers and non-ionic copolymers containing ethylenically unsaturated ester and / or amide monomers; ammonium acrylate homopolymers or ammonium acrylate and acrylamide copolymers; homopolymers and copolymers of (meth) acrylamide (C1C4) alkylsulfonic acids; homopolymers and cross-linked copolymers of methacryloyl (C1 -C4) alkyltri (C1-C4) alkylammonium. Particulate thickeners can also be used. In addition, naturally derived polymers and polymers produced by fermentations can be used, such as polysaccharide gums, xanthan gum, pullulan gum, sclerotium gum, carrageenan gum, locust bean gum, alginate, gelatin gum, cellulose, carboxymethyl cellulose , hydroxyethylcellulose, pectins, starch, chitosan, gelatin and combinations thereof.
[040] The particulates can also be used in combination with the personal care composition of the present invention. The particulates can be organic or inorganic particles. Examples of inorganic particles include microparticles composed of titanium oxide, titanated mica, zirconium oxide, zinc oxide, cerium oxide, magnesium oxide, barium sulfate, calcium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate , talc, cleaved talc, mica, kaolin, sericite, muscovite, synthetic mica, phlogopite, lepidolite, biotite, lithium mica, silicic acid, silicon dioxide, smoked silica, hydrated silicon dioxide, aluminum silicate, magnesium silicate, silicate aluminum and magnesium, silicate
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16/43 calcium, barium silicate, strontium silicate, metal tungstenate salts, hydroxyapatite, vermiculite, higilite, bentonite, montmorillonite, hectorite, zeolite, ceramic, dicalcium phosphate, alumina, aluminum hydroxide, boron nitride, nitride boron or glass. Examples of organic particles include powders consisting of a polyamide, polyacrylic acid / acrylic acid ester, polyester, polyethylene, polypropylene, polystyrene, acrylic acid / styrene copolymer, divinylbenzene / styrene copolymer, polyurethane, vinyl resin, urea resin, resin melamine, benzoguanamine, polymethylbenzoguanamine, tetrafluoroethylene, polymethylmethacrylate (such as poly (methyl methacrylate)), cellulose, silk, nylon, phenolic resin, epoxy or polycarbonate resin.
[041] Useful additives include pH regulators / buffering agents and chelating agents, such as ammonium hydroxide, sodium hydroxide, potassium hydroxide, C12-C15 alkyl benzoate, citric acid, glycolic acid, lactic acid, sodium citrate , triethanolamine, trolamine, disodium EDTA, disodium edetate, pentasodium pentetate, tetrasodium EDTA, trisodium EDTA.
[042] Fragrance ingredients can be incorporated into the personal care composition of the present invention, for example, diacetyl, isoamyl acetate, benzaldehyde, cinnamic aldehyde, ethyl propionate, methyl anthranylate, limonene, ethyl decadienoate, allyl hexanoate , ethyl maltol, ethyl vanillin, methyl salicylate, clary extract, eucalyptus globule oil, grape oil, labdanum oil, masking fragrance, matricaria oil, nopile acetate, phenoxyethanol, rosewood oil, ylang ylang and scented oils. They can also be mentioned as mixtures of scented oils of natural and / or synthetic aromatic substances. Natural aromatic substances include, for example, flower extracts (lilies, lavender, roses, jasmine, neroli, ylang-ylang), from stems and leaves (geranium, patchouli, petitgrain), from fruits (anise, coriander , caraway, juniper), from fruit peels (bergamot, lemon, orange), from
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17/43 roots (apple, angelica, celery, cardamom, costo, iris, calamus), wood (pine, sandalwood, guaiacum wood, cedar, rosewood), from herbs and grasses (tarragon, grass) -lemon, sage, thyme), from needles and branches (fir, pine, wild pine, mountain pine), from resins and balms (galbanum, elemi, benzoin, myrrh, frankincense, Opoponax). Animal raw materials are also taken into account, for example, civet and castor. Typical synthetic aromatic substances include, for example, ester, ether, aldehyde, ketone, alcohol or hydrocarbon products. Compounds of aromatic substances of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate , ethyl methylphenyl glycinate, allylcyclohexyl propionate, styryl propionate and benzyl salicylate.
[043] Ethers include, for example, benzyl ethyl ether; aldehydes include, for example, linear alkanes with 8 to 18 hydrocarbon atoms, citral, citronelal, citronelil oxyacetaldehyde, cyclamen aldehyde, hydroxycitronelal, lilial and bourgeonal; ketones include, for example, ionones, isomethionone and cedryl methyl ketone; alcohols include, for example, anethole, citronelol, eugenol, isoeugenol, geraniol, linalool, phenyl ethyl alcohol and terpinol; and, hydrocarbons include, for example, terpenes and balms.
[044] It is preferable to use mixtures of these and other aromatic substances, in combinations that produce a particularly attractive essence. Ethereal oils of relatively low volatility, which are mainly used as aroma components, are also suitable as scented oils, for example, sage oil, chamomile oil, clove oil, melissa oil, cinnamon leaf oil, oil lemon blossom oil, juniper berry oil, vetiver oil, frankincense oil, galbanum oil, labolane oil and
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18/43 lavender. Preference is given to the use of bergamot oil, dihydromyrcenol, lilial, liral, citronelol, phenyl ethyl alcohol, α, α-hexyl cinnamaldehyde, geraniol, benzyl acetone, cyclamen aldehyde, linalool, boisambrene forte, ambroxane, indole, hedione, sandelice, lemon oil, tangerine oil, orange oil, allyl amyl glycolate, cyclovertal, lavender oil, muscat sage oil, α-damask, bourbon geranium oil, cyclohexyl salicylate, vertofix coeur, iso- E-Super, Fixolide NP, Evernil, iraldein range, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide, Romillat, Irotyl and Floramat individually or in combination with each other.
[045] Flavor ingredients can be used in the personal care composition of the present invention, such as stearyl glycyrretinate, menthol, cinnamyl alcohol, acetic acid, ascorbic acid, citric acid, fumaric acid, malic acid, lactic acid, phosphoric acid , tartaric acid, fruits and plant extracts.
[046] Skin protectors and humectants can be used in the personal care composition of the present invention, such as dimethicone, petrolatum, glycerin, ammonium lactate, lanolin, methyl gluceth-20, PEG-20, sorbitol, 1,2, 6 hexanotriol, butylene glycol, dipropylene glycol, glycerin, hexylene glycol, panthenol, fitanthriol, panthenol, propylene glycol, sodium PCA, sorbitol, triethylene glycol, polyglyceryl sorbitol, glucose, fructose, polydextrose, potassium pea, urea, hydrogenated honey hyaluronic acid, inositol, hexanediol beeswax, hexanotriol beeswax, hydrolyzed elastin, hydrolyzed collagen, hydrolyzed silk, hydrolyzed keratin, erythritol, capryl glycol, and the like.
[047] Hair conditioning agents can be used in this document, for example, hydrocarbons, silicone fluids and cationic materials. Suitable hydrocarbons can be straight or branched and can contain from about 10 to about 16, preferably from about 12 to about 16 carbon atoms. Examples of suitable hydrocarbons include, for example, decane, dodecane, tetradecane, tridecane, and mixtures of
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19/43 same. Examples of suitable silicone fluid conditioning agents include, for example, linear and cyclic polydimethylsiloxanes, phenyl and alkyl phenyl silicones and silicone copolio. Cationic conditioning material agents useful herein include, for example, quaternary ammonium salts and fatty amine salts.
[048] Nail conditioning agents can be incorporated into the present invention, for example, adipic acid, fumaric acid, tricyclodecane dimethanol copolymer, hydrolyzed isostearoyl-AMP silk, Angelica furcijuga flower / leaf extract / keratinase r-bacillus licheniformis, yeast filtrate from ginseng bifid / panax root cell culture extract, bis-aminopropyl dimethicone / IPDI copolymer, IPDI bis-tipprolactone acrylate IPDI, bis-hEMA IPDI, Boswellia carterii gum extract, Boswellia serrata gum extract, calcium hydrolyzed collagen, silk amino acid / capryloyl methyl methionine esters, silk amino acid / capryloyl serine methyl, caulerpa oil extract, citrus fruit juice extract Aurantium amara (bitter orange) , flower / leaf / stem extract from Commelina communis, resin extract from Commiphora myrrha, dihydroxy difluoro chloride ethylcloprostenolamide, deoxyglutamyl fructose, tippro lactone ethoxy acrylate hema IPDI, tippril succinate, dimethyl urea, dipentaerythrityl hexacrylate, dipentaerythrityl pentacrylate, Echinacea angustifolia root extract, fragaria ananassa (strawberry) seed oil, fumaric acid / tricyclic / anhydride / anhydride copolymer ginkgo biloba nut, glycidoxypropyltrimethoxy silane, honey powder, Hydnocarpus pentandrus seed oil, acetophenone / hydrogenated oxymethylene copolymer, hydrolyzed collagen, hydrolyzed keratin, hydrolyzed vinyl acetate / vinyl acetate extract, hydrolyzed root extract, extract extract African Kigelia bark, Leucanthemum vulgare seed extract, Sorbus aucuparia fruit yeast filtrate / Aloe barbadensis leaf / leuconostoc, Lobelia extract
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20/43 inflata, Lupinus texensis seed extract, Lycium barbarum fruit extract, Mentha aquatica extract, methacrylethyl phosphate, methylene glycol, 2-methylpropanal, Momordica charantia extract, narcissus root extract pseudonarcissus extract (daffodil), extract Opuntia tuna leaf, Opuntia vulgaris fruit extract, palmitoil oligopeptide-70, silk amino acid / palmitoil serine methyl, Phaseolus vulgaris extract (kidney shaped beans), Phox drummondii seed extract, polyacrylate-12, polyacrylate-30, polyester-18, rose extract (American beauty), borbonian rose extract, Rosa roxburghii seed oil, Rudbeckia hirta seed extract, silver carp extract, calcium and sodium zinc phosphate, seed oil Sorbus aucuparia, r-spider polypeptide-1, r-spider polypeptide-2, silk amino acid / undecenoyl serine methyl esters, Vaccinium myrtillus leaf extract, alcohol copolymer vi vinyl / vinylformamide, extract of Viscum album (mistletoe), and the like.
[049] Cationic polymers can be used in the personal care composition of the present invention, for example, cationic guar gum derivatives such as hydroxypropyltrimony guar chloride and hydroxypropyltrimony guar hydroxypropyl chloride, available as Jaguar® series from Rhone-Poulenc .
[050] Ultraviolet light absorbers (UV absorbers) can be useful used in the personal care composition of the present invention to protect the composition against chemical or physical deterioration induced by ultraviolet light. UV absorbers, such as sunscreen agents, above, have the ability to convert incident ultraviolet radiation into less harmful infrared radiation (heat). Suitable UV absorbers include, for example, acetaminosalol, allantoin PABA, benzalphthalide, benzophenones such as benzophenone, benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-4, benzophenone-5, benzophenone-6, benzophenone-7, benzophenone-8, benzophenone-9, benzophenone-10, benzophenone-11, and phenone-12, benzotriazolyl dodecyl p-cresol, 3
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21/43 camphor benzylidene, hydrolyzed benzylidenocanfor collagen sulphonamide, camphor-benzylidene sulphonic acid, benzyl salicylate, bis-ethylhexyloxyphenol methoxy phenyl triazine, bornelone, bumetrizol, butyl methoxy dibenzoylmethane, butylmethyl butylamine , Camellia sinensis leaf extract, carotenoids, ceria / silica, ceria / silica talc, cinoxate, DEA methoxy cinnamate, dibenzoxazoil naphthalene, di-t-butyl camphor hydroxybenzylidene, diethyl hexyl butamido triazone, diethyl-hexyl 2,6- naphthalate, digaloyl trioleate, diisopropyl methyl cinnamate, 1- (3,4-dimethoxy phenyl) -4,4-dimethyl-1,3-pentanediene, dimethyl PABA ethyl cetearyldimonium tosylate, dimorpholin pyridazinone, diphenyl carbomethoxy acetone, naphthophenylphenoxyphenyl, bisphenoxy-naphthyriazine disodium, disodium distirylbiphenyl disulfonate, disodium phenyl dibenzimidazole tetrasulfonate, drometrizole, trisiloxane drometrizole, esculin, ethyl di-h idroxypropyl PABA, ethyl diisopropylcinamate, ethylhexyl dimethoxy benzylidene dioxoimidazolidine propionate, ethyl dimethyl PABA, ethylhexyl ferulate, ethylhexylmethoxy kinamate, ethylhexyl salicylate, ethylhexylmethoxy, ethylhexyl triazone, urocanate, etocrylene, ferulic acid, 4- (2-betaglucopyranosiloxy) propoxy-2-hydroxy benzophenone, glyceryl ethylhexanoate dimethoxy cinnamate, glyceryl PABA, glycol salicylate, hexanediol salicylate, homosalate, hydrolyzed lupine protein cinnamate, isopentyl trimethoxy cinnamate trisiloxane, isopropylbenzyl salicylate, isopropyl dibenzoylmethane, isopropyl methoxy cinnamate, menthyl anthranilate, menthyl salicylate, 4-methylbenzylidyl, acetyl, acetyl, acetyl, acetyl, acetyl, acetyl, acetyl, acetyl, acetyl, benzyl phenylbenzimidazole sulfonic acid, Pinus pinaster bark extract, polyacrylamidomethyl benzylidene camphor, polysilicone-15, potá ssio methoxy cinnamate, potassium sulfonate, phenylbenzimidazole, red petrolatum, sodium benzotriazolyl butylphenol sulfonate, sodium isoferulate, sodium phenylbenzimidazole-sulfonate, sodium urocanate, Spirulina platensis powder, TEA-sulfonate-thenylphenol and saline
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22/43 sulfonic, tetrabutyl phenyl hydroxybenzoate, titanium dioxide, tocotrienols, triPABA panthenol, urocanic acid, vinyl acetate / crotonates / methacryloxybenzophenone-1 copolymer and seed extract of Vitis vinifera (grape) and polymeric spheres or hollow spheres as potentializers of SPF. The combination of UV absorbers, such as those described above with SPF enhancers, such as styrene / acrylate copolymer silica beads, spheroidal magnesium silicate, spherical polyamide powder such as cross-linked polymethylmethacrylate with n-lactam polymer (Orgasol ® range, Elf Atochem) (PMMA; micopearl m305 seppic), can enhance UV protection. Holoosphere additives (Sunspheres® ISP, Silica Shells Kobo.) Deflect radiation and the length of the effective photon path is therefore increased. (EP0893119). Some spheres provide a smooth feeling during dispersion. In addition, the optical activity of such spheres, for example, Micropearl M305, can modulate the brightness of the skin, eliminating the reflection phenomena and, indirectly, can disperse UV light.
[051] The personal care composition of the present invention can also contain one or more known and conventional plasticizers in order to improve the flexibility and cosmetic properties of the resulting formulation. Plasticizers are often used to prevent embrittlement and cracking of film-forming polymers and include, for example, lecithin, polysorbates, dimethicone copolyol, glycols, citrate esters, glycerin, and dimethicone. One skilled in the art can routinely vary the amount of plasticizer (s), depending on the formulation of a particular personal care composition and the desired properties.
[052] The personal care composition of the present invention is advantageously formulated with a carrier, in particular, a volatile carrier that rapidly volatilizes after application of the composition. The volatile carriers
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Useful 23/43 can be selected from the group consisting of volatile hydrocarbons, volatile silicones, and mixtures thereof.
[053] Hydrocarbon oils useful for the present invention include those having boiling points in the range of 60-260 ° C, more preferably, hydrocarbon oils having from about Cs to about C20 of chain lengths, more preferably, from Cs to C20 isoparaffins. Most preferred are isododecane, isohexadecane, isoeocosane, 2,2,4-trimethylpentane, 2,3-dimethylhexane and mixtures thereof.
EXAMPLES [054] Examples 1-12 below which illustrate the preparation of ionic silicones with functionalized end (I) by subsequent combination, with film forming agents according to the present invention.
Example 1 [055] Preparation of Tetramethyldisiloxane functionalized with Sulphonic Acid.
[056] A 500 mL three-necked flask was loaded with 18.16 g (154.0 mmol) of alpha-methylstyrene and 27.2x10 ^-5 g of platinum catalyst. The temperature of the resulting mixture was brought to 115 ° C, then 9.40 g (70.0 mmol) of 1,1,3,3 tetramethyldisiloxane were added dropwise, and continued to stir until the hydrosilylation reaction. Complete hydrosilylation was indicated by the disappearance of the silicone hydride peak in 1H NMR. The resulting mixture was extracted in vacuo to remove unreacted alpha-methylstyrene, placing in an oil bath at 150 ° C for 2 hours which gave 23.2 g of aralkylene-substituted disiloxane (Yield: 90%).
[057] For this disiloxane substituted with aralkylene (23.2 g, 62.4 mmol), 29.6 g (252.8 mmol) of chlorosulfonic acid was added dropwise over a period of 30 minutes, while mixing is being stirred at temperature
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24/43 environment. The resulting mixture was kept under stirring for an additional 30 minutes. The completion of the reaction was determined by ¹ H NMR where the total sulfonation of the aromatic ring was indicated by the disappearance of the para-substituted aromatic proton peak. The vacuum extraction of the low pressure reaction mixture provided 33.0 g of the sulfonated disiloxane as a brown viscous oil.
Example 2 [058] Preparation of Tetramethyltetracycline siloxane functionalized with Sulfonic Acid [059] A 500 ml three-necked flask was loaded with 70.08 g (60.0 mmol) of alpha-methyl styrene and 10.0 x 10 ^{- 4} g of platinum catalyst. The temperature of the resulting mixture was brought to 115 ° C, then 30.0 g (120.5 mmol) of 1,3,5,7-tetramethylcyclotetrasiloxane was added dropwise, and stirring was continued. The progress of the reaction mixture was monitored by 1H NMR. After 12h of reaction, the complete conversion of silicone hydride was indicated by NMR. Then, the reaction mixture was extracted under vacuum at 150 ° C for 2 hours to remove unreacted alpha-methylstyrene, which provided 80.5 g of aralkylene-substituted cyclotetrasiloxane (Yield: 95%).
[060] For 14.24 g (20.0 mmol) of the above-substituted aralkylene cyclotetrassiloxane, 18.64 g (160.0 mmol) of chlorosulfonic acid dissolved in 4.0 ml of dichloromethane were added dropwise via a 30 minute period, while the mixture is being stirred at room temperature. The resulting mixture was kept under stirring for an additional 30 minutes. The completion of the reaction was indicated by 1H NMR where the complete sulfonation of the aromatic ring was indicated by the disappearance of the parasitized aromatic proton peak. The vacuum extraction of the low pressure reaction mixture provided 20.6 g of the cyclotetrassiloxane functionalized with sulfonic acid as a brown viscous gum.
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25/43
Example 3 [061] Preparation of Polydimethylsiloxane capped with Sodium Sulphonate.
[062] A 250 ml three-necked flask was loaded with 1.1 g (2.0 mmol) of sulfonated disiloxane (from example 1), 59.3 (200.0 mmol) octamethyltetracyclosiloxane. After reaching a balance of ~ 87% by weight of linear siloxanes, the reaction mixture was neutralized using 0.7 g (8.0 mmol) of sodium bicarbonate moistened at 70 ° C. The vacuum extraction of the low pressure reaction mixture gave 49.0 g of the product as a viscous gum. NMR analysis of the product indicated that the polymer was a sulfonated capped polydimethylsiloxane. The polymer had a viscosity of 53 Pa.s at a shear rate of 10 rad / s when measured by a HAAKE rheometer at 20 ° C.
[063] Likewise, calcium, magnesium, zinc, silver and cobalt sulfonate capped polydimethylsiloxanes (PDMS) were synthesized by neutralizing the capped PDMS with sulfonic acid with the respective oxide.
Example 4 [064] Preparation of Polydimethylsiloxane capped with Sodium Sulphonate.
[065] A 250 ml three-necked flask was loaded with 2.12 g (4.0 mmol) of sulfonated disiloxane (from example 1), 59.3 g (200.0 mmol) octamethyltetracyclosiloxane. The reaction mixture was placed in an oil bath and continued to stir at room temperature. After reaching a balance of ~ 87% by weight of linear siloxanes, the reaction mixture was neutralized using 1.4 g (16.0 mmol) of sodium bicarbonate moistened at 70 ° C. The vacuum extraction of the low pressure reaction mixture gave 53.0 g of the product as a viscous gum. NMR analysis of the product indicated that the polymer was a sulfonated capped polydimethylsiloxane. The polymer had a viscosity of 100 Pa.s at a shear rate of 10 rad / s when measured by a HAAKE rheometer at 20 ° C.
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26/43
Example 5 [066] Preparation of Polydimethylsiloxane capped with Sodium Sulphonate.
[067] A 500 ml three-necked flask was loaded with 10.6 g (20.0 mmol) of sulfonated disiloxane (from example 1), 118.0 g (400.0 mmol) octamethyltetracyclosiloxane. The reaction mixture was placed in an oil bath and continued to stir at room temperature. After reaching a balance of ~ 87% by weight of linear siloxanes, the reaction mixture was neutralized with 6.7 g (80.0 mmol) of sodium bicarbonate moistened at 70 ° C. The vacuum extraction of the low pressure reaction mixture gave 112.0 g of the product as a viscous gum. NMR analysis of the product indicated that the polymer was a sulfonated capped polydimethylsiloxane. The polymer had a viscosity of 1230 Pa.s at a shear rate of 10 rad / s when measured by a HAAKE rheometer at 20 ° C.
Example 6 [068] Preparation of Functional Polyorganosiloxane with Pending Sulphonate [069] For 5.7 g (8.0 mmol) of functional cyclotetrasylloxane with sulfonic acid obtained in example 2, 474.7 g (1600.0 mmol) octamethyltetracyclosiloxane and 2 , 96 g (16.0 mmol) of 1,1,3,3-tetramethyl-1,3-divinyldisiloxane were added and stirring at room temperature was continued. After reaching ~ 87 wt% linear siloxanes balance, the reaction mixture was neutralized using 10.0 g (128.0 mmol) of sodium bicarbonate moistened at 70 ° C. The vacuum extraction of the low pressure reaction mixture provided 411.0 g of the product as a milky oil. NMR analysis of the product indicated that the polymer was a pendant polydimethylsiloxane. The polymer had a viscosity of 5.0 Pa.s at a shear rate of 10 rad / s when measured by a HAAKE rheometer at 20 ° C.
[070] For 5.7 g (8.0 mmol) of functional cyclotetrasylloxane with acid
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27/43 sulfonic obtained in example 2, 474.7 g (1600.0 mmol) of octamethyltetracyclosiloxane and 14.8 g (80.0 mmol) of 1,1,3,3-tetramethyl-1,3-divinyldisiloxane were added and stirring at room temperature was continued. After reaching ~ 87 wt% linear siloxanes balance, the reaction mixture was neutralized using 10.0 g (128.0 mmol) of sodium bicarbonate moistened at 70 ° C. The vacuum extraction of the low pressure reaction mixture gave 427.0 g of the product as a viscous gum. NMR analysis of the product indicated that the polymer was a pendant polydimethylsiloxane.
Example 7 [071] Preparation of Functional Polyorganosiloxane with Pending Sulphonate.
[072] For 5.7 g (8.0 mmol) of functional cyclotetrasiloxane with sulfonic acid obtained in example 2, 474.7 g (1600.0 mmol) of octamethyltetracyclosiloxane and 14.8 g (80.0 mmol) of 1 , 1,3,3-tetramethyl-1,3-divinyldisiloxane was added and stirring at room temperature was continued. After reaching ~ 87 wt% linear siloxanes balance, the reaction mixture was neutralized using 10.0 g (128.0 mmol) of sodium bicarbonate moistened at 70 ° C. The vacuum extraction of the low pressure reaction mixture gave 427.0 g of the product as a viscous gum. NMR analysis of the product indicated that the polymer was a pendant polydimethylsiloxane.
Example 8 [073] Preparation of Functional Polydimethylsiloxane with Sodium Carboxylate [074] A 1000 ml three-necked round-bottom flask equipped with a condenser was loaded with 184.28 g (1 M) of undecenoic acid and 300 ml of toluene . The solution was heated to 70 ° C and 80.7 g (0.5 M) of hexamethyldisilazane was added over the period of 2 h. The solution was stirred at 70-80 ° C for 4 h. The solution was extracted from the solvent and the reaction mass was distilled
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28/43 vacuum at 1-5 Hg pressure and 150-160 ° C to produce trimethylsilylester of undecenoic acid (A).
[075] A 1000 ml three-necked round-bottom flask, equipped with a condenser, was loaded with 1.34 g (0.01 M) of tetramethyldisiloxane, 296.6 g (1 M) of octamethylcyclotetrassiloxane and 6 g of resin of acidic ion exchange. The solution was stirred for 12 hours at 55-60 ° C to produce the hydride-terminated siloxane.
[076] A 1000 ml three-necked round-bottom flask, equipped with a condenser, was loaded with 5.1 g (0.016 M) of compound (A) above, 237.8 g (0.008 M) of compound (B ) and 0.0003 g of platinum Karstedt catalyst and the solution was stirred for 8 h at 90 ° C. Subsequent deprotection and neutralization with sodium bicarbonate produced functional polydimethylsiloxane with sodium carboxylate. The polymer had a viscosity of 18 Pa.s at a shear rate of 10 rad / s, when measured by a HAAKE rheometer at 20 ° C.
Example 9 [077] Preparation of Functional Polydimethylsiloxane with Sodium Carboxylate [078] A 1000 ml three-necked round-bottom flask, equipped with a condenser, was loaded with 184.28 g (1 M) of undecenoic acid and 300 ml of toluene. The solution was heated to 70 ° C and 80.7 g (0.5 M) of hexamethyldisilazane was added over the period of 2 h. The solution was stirred at 70-80 ° C for 4 h. The solution was extracted from the solvent and the reagent was low boiling and the reaction mass was vacuum distilled at 1.34x10 ^-4 to 6.67x10 ^-4 MPa (1-5 mm Hg) pressure and 150-160 ° C to produce trimethylsilylester of undecenoic acid (A).
[079] A 1000 ml three-necked round-bottom flask, equipped with a condenser, was loaded with 6.7 g (0.05 M) of tetramethyldisiloxane, 370.7 g (1.25 M) of octamethylcyclotetrassiloxane and 10 g of acidic ion exchange resin. THE
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The solution was stirred for 12 hours at 55-60 ° C to produce the hydride-terminated siloxane.
[080] A 1000 ml three-necked round-bottom flask, equipped with a condenser, was loaded with 11.3 g (0.044 M) of compound (A) above, 150.7 g (0.02 M) of compound (B) and 0.0001 of Platinum Karstedt catalyst and the solution was stirred for 8 h at 90 ° C. Subsequent deprotection and neutralization with sodium bicarbonate produced the functional polydimethylsiloxane with sodium carboxylate. The polymer had a viscosity of 689 Pa.s at the shear rate of 10 rad / s, when measured by HAAKE rheometer at 20 ° C.
Example 10 [081] Preparation of Functional Polydimethylsiloxane with Sodium Carboxylate [082] A 1000 ml three-necked round-bottom flask, equipped with a condenser, was loaded with 184.28 g (1 M) of undecenoic acid and 300 ml of toluene. The solution was heated to 70 ° C and 80.7 g (0.5 M) of hexamethyldisilazane was added over the period of 2 h. The solution was stirred at 70-80 ° C for 4 h. The solution was extracted from the solvent and low boiling reagent and the reaction mass was vacuum distilled at 1.34x10 ^-4 to 6.67x10 ^-4 MPa (1-5 mm Hg) and 150-160 ° C to produce trimethylsilylester of undecenoic acid (A).
[083] A 1000 ml three-necked round-bottom flask, equipped with a condenser, was loaded with 6.7 g (0.05 M) of tetramethyldisiloxane, 185.4 g (0.625 M) of octamethylcyclotetrassiloxane and 5 g of resin of acidic ion exchange. The solution was stirred for 12 hours at 55-60 ° C to produce the hydride-terminated siloxane.
[084] A 1000 ml three-necked round-bottom flask, equipped with a condenser, was loaded with 10.3 g (0.04 M) of compound (A) above, 76.4 g (0.02 M) of compound (B) and 0.0001 g of platinum Karstedt catalyst and the solution was stirred for 8 h at 90 ° C. Subsequent deprotection and neutralization
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30/43 with sodium bicarbonate produced functional polydimethylsiloxane with sodium carboxylate. The polymer had a viscosity of 283 Pa.s at the shear rate of 10 rad / s, when measured by HAAKE rheometer at 20 ° C.
Example 11 [085] Preparation of Functional Polydimethylsiloxane with Sodium Phosphate.
[086] A 1000 ml three-necked round-bottom flask, equipped with a condenser, was loaded with 256.3 g (2 M) of allylglycidylether and 0.0003 g of platinum Karstedt catalyst, and the solution was heated at 70 ° C. For the above solution, 134.3 g (1 M) of tetramethyldisiloxane was added dropwise over the period of 6 hours at 70-75 ° C and stirred for 6 h at 90 ° C to produce functional tetramethyldisiloxane with epoxy .
[087] A 1000 ml three-necked round-bottom flask, equipped with a condenser, was loaded with 3.9 g (0.03 M) of the above product, 296.6 g (1 M) of octamethyldisiloxane and 6 g of acidic ion exchange resin and the solution was stirred for 16 hours at 70 ° C to produce functional polydimethylsiloxane with epoxy.
[088] A 1000 ml three-necked round-bottom flask, equipped with a condenser, was loaded with 150 g (0.005 M) of the above product and 1.2 g (0.01 M) of phosphoric acid (85%) and the solution was stirred at 85-90 ° C for 4 h. The solution was then cooled to about 15 ° C and 0.8 g (0.02 M) of a solution of sodium hydroxide dissolved in 1 ml of water was added and the solution was stirred at 15-20 ° C for 2 h to produce the functional polydimethylsiloxane with sodium phosphate. NMR analysis of the product indicated that the polymer was a phosphate-functionalized polyorganosiloxane.
Example 12 [089] Preparation of Functional Polydimethylsiloxane with Sodium Phosphate [090] A 1000 ml three-necked round-bottom flask, equipped
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31/43 with a condenser, it was charged with 256.3 g (2 M) of allylglycidyl ether and 0.0003 g of platinum Karstedt catalyst and the solution was heated to 70 ° C. For the above solution, 134.3 g (1M) of tetramethyldisiloxane was added dropwise over the period of 6 hours at 70-75 ° C and stirred for another 6 h at 90 ° C to produce functional tetramethyldisiloxane with epoxy .
[091] A 1000 ml three-necked round-bottom flask, equipped with a condenser, was loaded with 11.7 g (0.03 M) of the above product, 222.5 g (0.75 M) of octamethyldisiloxane and 5 g of acidic ion exchange resin, and the solution was stirred for 16 h at 70 ° C to produce functional polydimethylsiloxane with epoxy.
[092] A 1000 ml three-necked round-bottom flask, equipped with a condenser, was loaded with 152.7 g (0.03 M) of the above product and 7.0 g (0.06 M) of phosphoric acid (85%) and the solution was stirred at 85-90 ° C for 4 h. The solution was then cooled to about 15 ° C and 4.8 g (0.12 M) of a solution of sodium hydroxide dissolved in 5 ml of water was added and the solution was stirred at 15-20 ° C for 2 h to produce the functional polydimethylsiloxane with sodium phosphate. NMR analysis of the product indicated that the polymer was a phosphate-functionalized polyorganosiloxane.
[093] Lip color formulations (CF 1-11) prepared with the functionalized end ionic silicones of Examples 3-12, supra, but without a film forming agent (Comparison Formulations) are shown in Table 1 as follows:
Table 1: Comparison of Lip Color Formulations (CF1-11)
Components, Quantity (g) CF1 CF2 CF3 CF4 CF5 CF6 CF7 CF8 CF9 CF10 CF11 Ionic Silicone of Example 3 2.5 -Ionic Silicone of Example 4 - 2.5 - Ionic Silicone of Example 5 - - 2.5 - - - - - - - - Ionic Silicone of Example 6 - - - 2.5 - - - - - - - Ionic Silicone of Example 7 - - - - 2.5 - - - - - - Ionic Silicone of Example 8 - - - - - 2.5 - - - - -
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Ionic Silicone of Example 9 - - - - - - 2.5 - - - - Ionic Silicone of Example 10 - - - - - - - 2.5 - - - Ionic Silicone of Example 11 - - - - - - - - 2.5 - - Ionic Silicone of Example 12 - - - - - - - - - 2.5 - SE30 (Silicone Gum), Momentive Performance Materials -1.0 SR1000 (Silicone Resin), Momentive Performance Materials - - 1.5 Bentona VS-5 PC V Gel (Thickener), Elementis Specialties Inc. 0.81 0.81 0.81 0.81 0.81 0.81 0.81 0.81 0.81 0.81 0.81 D5 (Solvent), Momentive Performance Materials 4 4 4 4 4 4 4 4 4 4 4 GE Red Shadow Dispersion (Pigment), Intemational Foodcraft Corp. 2.4 2.4 2.4 2.4 2.4 2.4 2.4 2.4 2.4 2.4 2.4 Ti02- MT100 TV (Pigment), Tri-K Industries 0.29 0.29 0.29 0.29 0.29 0.29 0.29 0.29 0.29 0.29 0.29 Water Dl - - - - - 1.24 1.24 1.24 1.24 1.24 - Glycerin (Moisturizer), SigmaAldrich Inc. 1.24 1.24 1.24 1.24 1.24 - - - - - -
[094] The lip color formulations (F1-F30) prepared with a mixture of ionic silicone with functionalized end (I) and a film-forming agent, according to the invention are presented in Tables 2-5 as follows:
[095] Table 2: Lip Color Formulations containing Sulphonated Ion Silicone Blends and Film Forming Agent
Components, Quantity (g) F1 F2 F3 F4 F5 F6 F7 F8 F9 Ionic Silicone of Example 3 1.0 1.0 1.0 1.0 1.0 2.0 1.0 - - Ionic Silicone of Example 4 - - - - - - - 1.0 - Ionic Silicone of Example 5 - 1.0 SR1000 (Silicone Resin), Momentive Performance Material 1.5 - - - - 1.5 1.5 SilForm (Flexible Resin), Momentive Performance Mate- - 1.5 - - - - - - - Cloisite 30B (Nano clay),Southern Clay Products - - 1.5 - - - - - - Montmorilollite K10 (Clay), SigmaAldrich Inc. - - - 1.5 - - - - - Ganex® V-220 (VP / Eicosene Copolymer), ISP Corp. - - - - 1.5 - - - -
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Covacryl E14 (Copolymer ofAcrylate), Sensient Cosmetic Technologies - - - - - 1.5 - - - Koboguard 5400 (Polycyclopentadiene), KoboProducts Inc. - - - - - - 2.15 - - Bentone VS-5 PC V Gel (Thickener), Eiementis Specialties Inc. 0.81 0.81 0.81 0.81 0.81 0.81 0.81 0.81 0.81 D5 (Solvent), Momentive Performance Materials 4 4 4 4 4 4 3.3 4 4 GE Red Shadow Dispersion (Pigment), International Foodcraft Corp. 2.4 2.4 2.4 2.4 2.4 2.4 2.4 2.4 2.4 TiO2- MT100 TV (Pigment), Tri-K Industries 0.29 0.29 0.29 0.29 0.29 0.29 0.29 0.29 0.29 Glycerin (Moisturizer), SigmaAldrich Inc. 1.2 1.24 1.24 1.24 1.24 - 1.24 1.24 1.24
[096] Table 3: Color Formulations for Lips containing Mixtures of
S i ionic sulphonated pendant pendant and film forming agent
Components, Quantity F10 F11 F12 F13 F14 F15 F16 F17 Ionic Silicone of Example 6 1.0 2.0 1.0 1.0 1.0 2.0 1.0 - Ionic Silicone of Example 7 - - - - - - - 1.0 SR1000 (Silicone Resin), Momentive Performance Material 1.5 - - - - - - 1.5 Aerosil 300 (Silica), Evonik Industrial- - 0.5 - - - - - - Cloisite 30B (Nano clay),Southern Clay Products - - 1.5 - - - - - Montmorillolite K10 (Clay), SigmaAldrich Inc. - - - 1.5 - - - - Ganex® V-220 (VP / Eicosene Copolymer), iSp Corp. - - - - 1.5 - - - Covacryl E14 (Acrylate Copolymer), Sensient Cosmetic - - - - - 1.5 - - Koboguard 5400 (polycyclopentadiene), Kobo Products Inc. - - - - - - 2.15 - BentoneVS-5 PC V Gel (Thickener), Elementis Specialties Inc. 0.81 0.81 0.81 0.81 0.81 0.81 0.81 0.81 D5 (Only), Momentive Performance Materials 4 4 4 4 4 4 3.3 4 Red Shadow Dispersion GE (Pigment), International Fo- 2.4 2.4 2.4 2.4 2.4 2.4 2.4 2.4 Ti02- MT100 TV (Pigment), TriK Industries 0.29 0.29 0.29 0.29 0.29 0.29 0.29 0.29 Glycerin (Moisturizer), SigmaAldrich Inc. 1.24 1.24 1.24 1.24 1.24 - 1.24 1.24
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34/43 [097] Table 4: Lip Color Formulations Containing Mixtures of
Ionic Silicone Functionalized with Carboxylate and Film Forming Agent
Components, Quantity (g) F18 F19 F20 F21 F22 F23 F24 F25 F26 Ionic Silicone of Example 8 1.0 2.0 1.0 1.0 1.0 - - - - Ionic Silicone of Example 9 - - - - - 1.0 1.0 1.0 - Ionic Silicone of Example 10 - 1.0 SR1000 (Silicone Resin), Momentive Performance Materials 1.5 - - - - 1.5 - - 1.5 Aerosil 300 (Silica), Evonik Industries - 0.5 - - - - - - - Cloisite 30B (Nano clay), Southern Clay - - 1.5 - - - 1.5 - - Montmorillolite K10 (Clay), Sigma Al- - - - 1.5 - - - 1.5 - Components, Quantity (g) F18 F19 F20 F21 F22 F23 F24 F25 F26 Koboguard 5400 (Polycyclopentadiene), Kobo Products Inc. - - - - 2.15- - - Bentone VS-5 PC V Gel (Thickener), Elementis Specialties Inc. 0.81 0.81 0.81 0.81 0.81 0.81 0.81 0.81 0.81 D5 (Solvent), Momentive Performance 4 4 4 4 3.3 4 4 4 4 Red Shadow Dispersion GE (Pigment), International 2.4 2.4 2.4 2.4 2.4 2.4 2.4 2.4 2.4 Ti02- MT100 TV (Pigment), Tri-K Indusi 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Water Dl 1.24 1.2zl 1.2THE 1.2THE 1.2zl 1.24 1.24 1.24 1.24
[098] Table 5: Color Formulations for Lips Containing Mixtures of
Ionic Silicone functionalized with Phosphate and Film Forming Agent
Components, Quantity (g) F27 F28 F29 F30 Ionic Silicone of Example 11 1.0 2.0 1.0 - Ionic Silicone of Example 12 - - - 1.0 SR1000 (Silicone Resin) Momentive Performance 1.5 - - 1.5 Aerosil 300 (Silica) Evonik Industries - 0.5 - - Cloisite 30B (Nano Clay) Southern Clay Products - - 1.5 - Gel Bentone VS-5 PC V (Thickener) Elementis Spe- 0.81 0.81 0.81 0.81 D5 (Solvent) Momentive Performance Materials 4 4 4 4 Red Shadow Dispersion GE (Pigment) International Foodcraft Corp. 2.4 2.4 2.4 2.4 Ti02- MT100 TV (Pigment) Tri-K industries 0.29 0.29 0.29 0.29 Water Dl 1.24 1.24 1.24 1.24
A. Transfer Resistance Properties
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35/43 [099] Transfer resistance measurements were performed using the method described in U.S. Patent No. 6,074,654 with the following exceptions:
A uniform coating (~ 30 microns thick) of each formulation was made on an artificial skin film (pre-hydrated over 30% aqueous glycerin solution for 24 hours), using an automatic film applicator and dried at 40 ° C. ° C. The films were then subjected to a smear insult using a testing device. A 500 g dough was covered with a piece of white cotton cloth. The set was placed on the surface of the skin coating in vitro. The set was rotated 360 °. The cloth was then imaged electronically and the percentage area darkened by the transferred red lip formulation was determined by the image processing software. The higher the% transference, the more formulation for the lips is transferred from the coated skin in vitro to the white cloth. This process was repeated on the same skin site in vitro. Each rotation (360 °) of the abrasive surface through the dry film was counted as an insult. The upper limit of the transfer cover is considered to be 100%, which means that the entire abrasive surface is covered with a colored material. The lower% of transfer is indicative of a better transfer resistance.
[0100] The results of the transfer test are presented in Tables
6-10 as follows:
[0101] Table 6: Comparison Formulations - Transfer Results (CF1-11)
CF1 CF2 CF3 CF4 CF5 CF6 CF7 CF8 CF9 CF10 CF11 Insult 1 59% 55% 36% 67% 61% 56% 37% 30% 67% 37% 22% Insult 2 23% 19% 13% 24% 19% 17% 11% 4% 18% 11% 19% Insult 3 13% 78% 7% 7% 5% 7% 4% 3% 8% 4% 14% Insult 4 4% 4% 2% 3% 2% 9% 4% 2% 3% 4% 10% Insult 5 3% 3% 2% 3% 1% 3% 1% 0% 3% 1% 5%
[0102] Table 7: Transfer Results - Ionic Silicones capped at the End and Film Forming Agents (F1-9)
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F1 F2 F3 F4 F5 F6 F7 F8 F9 lnsult 1 4% 46% 18% 32% 13% 30% 24% 26% 9% lnsult 2 4% 22% 20% 18% 27% 11% 16% 22% 7% lnsultum 3 6% 11% 15% 10% 18% 6% 8% 20% 9% lnsult 4 4% 5% 7% 7% 7% 3% 6% 7% 3% Insult 5 4% 1% 3% 4% 3% 2% 3% 5% 1%
[0103] Table 8: Transfer Results - Sulphonated ionic silicones
Pending and Training Agents of Fi me (F10lnsult 1 lnsult 2 lnsult 3 lnsult 4 lnsult 5
F10
48%
29%
9%
10%
11%
F11
29%
27%
13%
7%
4%
F12
40%
25%
13%
5%
3%
F13
58% 23%
8%
3%
2%
F14
32%
36%
20%
7%
3%
F15
67% 14% 7%
3%
4%
F16
47%
21%
6%
4%
2%
F17
16%
13%
14%
4%
3% [0104] Table 9: Transfer Results - Ionic silicones functionalized with Carboxylate and Forming Agents. Film (F18-F26)
F18 F19 F20 F21 F22 F23 F24 F25 F26 Insult 1 34% 20% 6% 9% 26% 0% 5% 5% 0% Insult 2 11% 15% 10% 10% 13% 0% 5% 2% 0% Insult 3 5% 7% 15% 13% 10% 0% 4% 2% 1% Insult 4 4% 3% 5% 8% 6% 0% 4% 1% 0% Insult 5 6% 2% 3% 10% 3% 0% 2% 1% 0%
[0105] Table 10: Transfer Results - Tonic silicones
Functionalized with Phosphate and Film Forming Agents (F27-F30)
F27 F28 F29 F30 Insult 1 39% 25% 37% 1% Insult 2 21% 17% 17% 5% Insult 3 9% 12% 9% 9% Insult 4 9% 7% 7% 16% Insult 5 7% 5% 6% 23%
B. Tackiness Properties [0106] The skin in vitro was prepared in the same way as described in the measurement of transfer resistance mentioned in the examples above. Once the formulation was dried on the skin in vitro, the adhesion strength of dry films was measured using the Dia-Stron instrument (MTT 175), the lower the adhesion force, the lower the adhesion. The results of the adherence test are indicated
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37/43 in Table 11 as follows:
[0107] Table 11: Tackiness Properties
F27 F28 F29 F30 Insult 1 39% 25% 37% 1% Insult 2 21% 17% 17% 5% Insult 3 9% 12% 9% 9% Insult 4 9% 7% 7% 16% Insult 5 7% 5% 6% 23%
C. Brightness Properties [0108] A film of uniform thickness for each formulation was made on a standard Leneta card and dried at 40 ° C. Brightness readings at 60 degrees and 85 degrees of dry films were recorded using a BYK gloss meter. The glass test results are shown in Table 12 as follows:
[0109] Table 12: Brightness Properties
CF11 F1 F9 F6 F10 F17 F23 60 degrees 18.5 36.2 20.5 24.1 46.4 22.4 28.1 85 degrees 66.3 78.4 72.1 42.3 77.1 69.0 77.8
D. Trans Epidermal Water Loss Properties (TEWL) [0110] The trans epidermal water loss (TEWL) properties of the cosmetic compositions of the present invention were determined using the method described in US Patent No. 5,679,335 with the following exceptions :
[0111] The skin hydrated in vitro was coated with the individual formulation, dried at 40 ° C overnight. A set of Pyne cups was loaded with 3.00 ml of water and the cups were covered with dry skin in vitro coated with individual formulation. The rate of water loss from the skin surface was measured using a Tewameter® TM 300 probe attached to the MPA 580 instrument. The results of treatment with TEWL are shown in Table 13 as follows:
Huh- F1 F26 F23 TEWL (g / mh ² ) 11.0 7.7 9.3 8.4
[0112] The transfer resistance results here indicate that the
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38/43 lip color formulations with a combination of ionic silicone (I) and a film forming agent have better transfer resistance compared to compositions based on non-functionalized polyorganosiloxanes and other comparative ionic silicones individually. The compositions of the invention also show a significant improvement in the reduction of tackiness, gloss and trans-epidermal water-based compared to a non-functionalized silicone-based composition.
[0113] Hair treatment compositions (HTCs 1-8) were prepared having the formulations shown below (Table 14) and evaluated for hair wave compression strength (results shown in Table 15 below). Each HTC was diluted with D5 cyclodimethicone to form a 5% solids solution in D5. The individual bleached locks (2 g or 6 g of locks) were dipped in each solution for 1 min. The excess liquid was squeezed out and each section was carefully dried to remove D5 using a blow dryer with a section being left in an oven at 45 ° C overnight. Through this procedure, the same amount of silicone was distributed to each strand of hair. The measurements of the lock were made after the balance in a humidity chamber at 50%. The compression force of the hair wave was measured using a Dia-Stron instrument (MTT 175).
[0114] The hair treatment compositions of the invention (HTCs 5-8 in Table 14) showed a significant improvement in hair holding properties with the combination of ionic silicones and silicone resins compared to the hair treatment compositions that contain ionic silicones individually (HTC 1-4 in Table 14).
[0115] Table 14: Compositions of Contend Ionic Silicones Components, Quantities HTC1 HTC2 HTC3 HTC4 HTC5 HTC6 HTC7 HTC8 Ionic Silicone of Example 3 1.25 0.5 Ionic Silicone of Example 81.25 0.5 Example Ionic Silicone 1.25
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Ionic Silicone of Example 9 0.5Example Ionic Silicone 1.25 0.5 SR1000 (Silicone Resin), Momentive Performance 0.75 0.75 0.75 0.75 D5 (Solvent), Momentive Performance Materials 25 25 25 25 25 25 25 25 Deionized water 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5
[0116] Table 15: Multicycle Wave Compression Results
Composition HTC1 HTC2 HTC3 HTC4 HTC5 HTC6 HTC7 HTC8 Mean peak stiffness (gmf) 4.4 7.8 4.3 9.5 4.9 12.1 11.8 11.5
[0117] Additional hair treatment compositions were prepared (HTCs 9-11) having the formulations shown in Table 16 below. The mixtures of resin and ionic silicone with functionalized end were diluted in cyclodimethicone D5 to form a 2% solid solution in relation to D5 (HTCs 9 and 10). A single bleached strand of hair (2 g of weight or 6 g of strand) was dipped in the solution for 1 min. The excess liquid was squeezed out and the lock was carefully dried to remove D5 using a blow dryer, after which the lock was left in an oven at 45 ° C overnight. Through this procedure, the same amount of silicone was distributed to the hair. The measurements of the locks were taken after equilibration in a 50% humidity chamber. The coefficient of friction of the hair μ was measured on a CSM tribometer, on a stretched flat lock, with a flat stainless steel probe. Hair was considered good when μ <0.12. As shown in Table 16, HTC 9 and 10 exhibited a significant reduction in hair friction coefficient (straight hair) and anti-frizz effect compared to HTC 11 untreated hair (comparison).
[0118] Table 3: Hair treatments containing lonic silicones
Components, Quantity (g) HTC9 HTC10 HTC11 (Comparison) SR1000 (Silicone Resin), Momentive Performance Materials 1.13
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SilForm (Flexible Resin), Momentive Performance Materials1.13Ionic Silicone of Example 3 0.87 0.87D5 (Solvent), Momentive Performance 98 98Hair friction coefficient 0.11 0.106 0.16 Hair appearance after 90% of HR Chamber Little curly Little curly Very curly
[0119] When formulated in a hair care product, the mixture of ionic silicone with functionalized end and non-functionalized silicone resin can be diluted with a volatile solvent, such as a volatile silicone, for example, ethyl trisiloxane, octyl trisiloxane, cyclodimethicone, etc., or a volatile organic solvent (isododecane). The diluted mixture can then be applied to the hair in the form of an aqueous or non-aqueous spray, an aqueous or non-aqueous foam, an O / O emulsion or an O / A emulsion.
[0120] These and other conventional and known hair treatment formulations may contain other ingredients used in hair products, such as wetting agents (eg, panthenol, butylene glycol, sorbitol, glycerin, other polyols, etc.), amino acids and natural moisturizing agents (for example, the sodium salt of carbonic acid pyrrolidone), non-ionic waxes (for example, fatty alcohols, ethoxylated waxes, glycerol stearate, beeswaxes, paraffin waxes, etc.), cationic surfactants, esters, triglyceride oils (for example, olive oil, jojoba oil, sunflower oil, coconut oil, argan oil, grape seed oil, etc.), natural butters (for example, shea butter, cocoa butter), emulsifiers (for example, silicone emulsifiers, silicone polyether copolymers, organic emulsifiers, etc.), anionic surfactants and amphoters (eg, ecocobetaine, SLES, isothionate, sugar surfactants, etc.), dispersing agents (eg superdispersing silicone, etc.), solid particles (eg pigments, minerals, talc, mica, iron oxides, boron nitride, titanium oxide, clays, etc.), permanent and semi-permanent hair dyes, fragrances, active agents, such as plant extracts, polyphenols, polysaccharides (for example, chitosan), proteins (for example,
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41/43 keratin, silk protein, wheat proteins, etc.), lipids, sterols and anti-dandruff active ingredients (eg, zinc pyrithione, selenium sulfide, antifungal agents, etc.), salicylic acid, glycolic acid, agents hair growth actives, anti-aging active agents (eg, retinol, alpha-hydroxy acids, etc.), niacinamide, reducing agents (eg, thioglycolates, cysteamine, etc.), sulphites, oxidizing agents (eg, peroxide hydrogen, bromates, etc.), relaxants (eg sodium hydroxides, guanidines, etc.), cross-linking agents (eg, aldehydes, epoxy-containing compounds, silanes, enzymes, etc.), modeling polymers (eg PVP, acrylate copolymers, etc.), thickener polymers (for example, acrylates, polyacrylamide, cellulose, starch, polysaccharide gums, pectins, etc.), deposition aid polymers (for example, cationic heads, cellulose cationic, merquats, etc.), preservatives, biocides (e.g., phenoxyethanol, potassium sorbate, benzoic acid, sorbic acids, etc.), fragrances, antioxidants (e.g. vitamin E), UVA and UVB sunscreens, artificial tanning agents ( for example, dihydroxyacetone, and the like).
[0121] Combing oils (COs) for the treatment of curly hair were prepared as shown in Fig. 17. Each CO was spread over undamaged curly hair (Hair International Inc.) to obtain a dose of hair from 0.25 g / g. The hair was combed completely with a fine comb and the total distance of the comb's distance was measured with a ruler. CO effectiveness is displayed where the comb travel distance is greater than for untreated hair.
[0122] As shown in Table 17, untreated hair (CO3, Comparison) showed poor ease of combing. Comparative 1 was the hair treated with petrolatum, showing some improvement in combability, but a greasy sensation. The lock of hair treated with CO1 showed a better combing ability and a noticeably less greasy sensation.
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[0123] Table 17: Oils for Combing Heads lo Crespo Components, Quantity (g) CO1 CO2 CO3 (Comparison) Petrol Snow White 49 100Ionic Silicone of Example 5 49 Deionized water 2 Length of 5 4 3 Sensation smooth greasy clean
[0124] Water-in-oil emulsions (WOs 1-6) containing various ionic silicones according to the invention were prepared as shown below in
Table 18.
[0125] Table 18: Water-in-Oil Emulsion containing Ionic Icons
Components, Quantity (g) WO1 WO2 WO3 WO4 WO5 WO6 Silform 60A,Momentive Performance Materi- 2 2 2 2 2 2 Isododecane (Solvent), Presperse 10 10 10 10 10 10 Silsoft ETS,Momentive Performance Materi- 10 10 10 10 10 10 SR1000 (Silicone Resin), Momentive Performance 5 5 5 5 5 5 Ionic Silicone of Example 3 2.5 0 0 0 0 0 Ionic Silicone of Example 5 0 2.5 0 0 0 0 Ionic Silicone of Example 6 0 0 2.5 0 0 0 Ionic Silicone of Example 7 0 0 0 2.5 0 0 Ionic Silicone of Example 8 0 0 0 0 2.5 0 Ionic Silicone of Example 11 0 0 0 0 0 2.5 NaCl 0.8 0.8 0.8 0.8 0.8 0.8 Butylene glycol 3 3 3 3 3 3 Deionized water 66.7 66.7 66.7 66.7 66.7 66.7
[0126] Oil-in-water emulsions (OWs 1-7) containing the ionic silicone of Example 5, supra, were prepared as shown below in Table 19.
[0127] Table 19: Oil-in-water emulsion containing ionic silicone
Components, Quantity (g) OW1 OW2 OW3 OW4 OW5 OW6 OW7 AMP-95 (aminomethyl propanol), Dow Chemical 0.560.7 Aculyn 180 (Acrylate / Hydroxyester Acrylate Copolymers), Dow Chemical 2
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Aculyn 88 (Cross Polymer ofAcrylates / Methacrylate Steareth-20), Dow Chemical 5 Celiosize PCG-10 (hydroxyethyl cellulose), Dow Chemical1.5Ucare JR-30M (polycarbonate-10), Dow Chemical0.05Ssepigel 305, SEPPIC 5 Aristoflex AVC, Clariant 2 Carbopol 980, Lubrizol 0.9 Fixate G-100, Lubrizol 2.6 Uitrez 20, Lubrizol 0.2 Carbopol Aqua SF-1 (30%), Luil1glyceryl stearate and PEG-stearate100, 2 6Cetearyl alcohol, Sigma Al- 1 3Sodium hydroxide (18%) 0.2 0.2Panthenol, Sigma Aldrich 0.5 0.5Disodium EDTA 0.05 0.05SR1000 (Silicone Resin), Momentive Performance Materials 5 5 5 5 5 5 5 Ionic Silicone of Example 5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 D5 (Solvent),Momentive Performance Mate- 7 7 7 7 Isododecane (Solvent), Pres-7 7silsoft ETS,Momentive Performance Mate- 7 7 7 Deionized water q.s100 q.s100 q.s100 q.s100 q.s100 q.s100 q.s100
[0128] Although the above description contains many specificities, these specificities should not be interpreted as limitations of the invention, but merely as exemplifications of preferred modalities thereof. Those skilled in the art will envisage many other modalities within the scope and spirit of the invention as defined by the appended claims.

权利要求:
Claims (20)
[1]
1. Composition for personal care, CHARACTERIZED by the fact that it comprises at least one ionic silicone with functionalized end and at least one film forming agent, in which the referred ionic silicone with functionalized end has the formula:
M ¹ to M ² b M ³ c D ¹ d D ² and D ³ f T ¹ g T ² h T ³ i Qj (I) where:
M ¹ = R ¹ R ² R ³ Sim / 2
M ² = R ⁴ R ⁵ R ⁶ SiOi / 2
M ³ = R ⁷ R ⁸ R ⁹ SiOi / 2
D ¹ = R ¹⁰ R ¹¹ SiO2 / 2
D ² = R ¹² R ¹³ SiO2 / 2
D ³ = R ¹⁴ R ¹⁵ SíO2 / 2
T ¹ = R ¹⁶ SiO3 / 2
T ² = R ¹⁷ SiO3 / 2
T ³ = R ¹⁸ SíO3 / 2
Q = SiO4 / 2 where
R ¹ , R ² , R ³ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹³ , R ¹⁵ and R ¹⁶ each, independently, is a monovalent aliphatic, aromatic or fluoro having from 1 to 60 carbon atoms;
R ⁴ , R ¹² and R ¹⁷ , each independently is a monovalent group carrying ion pairs and having the formula -AI ^x- Mn ^{y +} , or zwitterion having the formula -R'-N ⁺ (R) 2-R '-I ^- , where A is a spacing portion with at least one spacing atom, the spacing portion being selected from the group consisting of the divalent hydrocarbon group and the hydrocarbonoxy group, I is an ionic group, R 'is a divalent hydrocarbon group having from 1 to 20
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[2]
2/7 carbon atoms, R is a monovalent hydrocarbon group having 1 to 20 carbon atoms, R '' 'is a divalent hydrocarbon group having 2 to 20 carbon atoms, and each M, independently, is hydrogen or a cation independently selected from alkali metals, alkaline earth metals, transition metals, quaternary ammonium groups and phosphonium groups;
R ⁷ , R ¹⁴ and R ¹⁸ each, independently, is -CH2CH (R ¹⁹ ) (CnH2n) -O (C2H4O) O- (C3H6O) p- (C4H8O) qR ¹⁹ where R ¹⁹ is hydrogen or a group R ¹ as defined above;
superscripts x and y are positive integers subject to the limitation that x = ny;
each subscript n independently has a value from 0 to 6 and subscripts o, p and q, each independently, has a value from 0 to 1000, subject to the limitation that + p + q> 1; e, the subscripts a, c, d, e, f, g, h, iej, each, independently, is zero or a positive integer subject to the limitations that 2 <a + b + c + d + e + f + g + h + i + j <4500 and b> 2;
2. Personal care composition, according to claim 1, CHARACTERIZED by the fact that in ionic silicone with functionalized end (I), each group R ¹ , R ² , R ³ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹³ , R ¹⁵ and R ¹⁶ are independently selected from methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl, tert-pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopentyl, cyclohexyl, cycloheptyl, methylcyclohexyl, naphthyl; tolyl, xylyl, ethylphenyl and benzyl.
[3]
3. Personal care composition according to claim 1, CHARACTERIZED by the fact that in ionic silicone with functionalized end (I), the divalent spacing group A is an alkylene group (CHR ²⁰ ) -m where R ²⁰ is hydrogen or a group R ¹ and the subscript m is a number
Petition 870190033247, of 5/4/2019, p. 58/64
3/7 positive integer ranging from 1 to 100.
[4]
4. Personal care composition according to claim 1, CHARACTERIZED by the fact that in ionic silicone with functionalized end (I), the divalent spacing group A is an arylene group selected from - (CHR ²¹ ) kC6H4 ( CH2) r - CH ² CH (R ') (CH2) kC6H4- or CH2CH (R ²² ) (CH2) rC6H3R ²³ , where R' is hydrogen or an R ¹ group, R ²¹ is hydrogen or an R ¹ group , R ²² is hydrogen or a group R ¹ , R ²³ is a monovalent radical of 1 to 20 carbon atoms and the ker subscripts are zero or positive integers subject to the limitation of 0 <k + r <100.
[5]
5. Personal care composition, according to claim 1, CHARACTERIZED by the fact that in ionic silicone with functionalized end (I), the divalent spacing group A is a hydrocarbonoxy group selected from - (CHR ²⁴ ) s- (O-CHR ²⁴ CH2) s 'and -O- (CH2) t, where R ²⁴ is hydrogen or a group R ¹ , s has a value from 0 to 50, s' has a value from 1 to 50 and t has a value from 0 to 50 subject to the limitation of 1 <s + s' + t <100.
[6]
6. Personal care composition, according to claim 1, CHARACTERIZED by the fact that in the ionic silicone with functionalized end (I), I ^- in the group that carries the ionic pair and in the zwitterion is selected from sulfonate -SO3 ^- and -OSO3 sulfate.
[7]
7. Personal care composition, according to claim 1, CHARACTERIZED by the fact that in ionic silicone with functionalized end (I), M ⁺ is selected from Li, Na, K, Cs, Mg, Ca, Ba, Zn, Cu, Fe, Ni, Ga, Al, Mn, Cr, Ag, Au, Pt, Pd, Ru and Rh.
[8]
8. Personal care composition according to claim 1, CHARACTERIZED by the fact that in ionic silicone with functionalized end (I), in zwitterion, R 'is a divalent hydrocarbon radical having from 1 to 20 carbon atoms, R is a monovalent hydrocarbon radical having to
Petition 870190033247, of 5/4/2019, p. 59/64
4/7
1 to 20 carbon atoms and R 'is a divalent hydrocarbon radical having 2 to 20 carbon atoms.
[9]
9. Personal care composition, according to claim 1, CHARACTERIZED by the fact that in ionic silicone with functionalized end (I), the subscripts a, c, d, e, f, g, h, iej, each, regardless, it is zero or a positive number subject to the limitations that 2> a + b + c + d + e + f + g + h + i + j> 4500, b> 2.
[10]
10. Personal care composition, according to claim 9, CHARACTERIZED by the fact that in ionic silicone with functionalized end (I), the subscript b is 2; subscripts a, c, e, f, g, h, i, j, k, lem are 0; subscript d is from 5 to 1000; R ⁵ , R ⁶ , R ¹⁰ and R ¹¹ are methyl or ethyl; R ¹⁰ is -CH2CH (H or CH3) -A-SO3M; A is a divalent benzyl radical; and, M ⁺ is Li, Na, K, Ag, a group of quaternary ammonium, ammonium salt or a phosphonium group.
[11]
11. Personal care composition according to claim 1, CHARACTERIZED by the fact that the ionic silicone with functionalized end (I) is at least one among sodium sulfonate capped polydimethylsiloxane, silver sulfonate capped polydimethylsiloxane capped with polydimethylsiloxane capped magnesium sulfonate, polydimethylsiloxane capped with calcium sulfonate, polydimethylsiloxane capped with zinc sulfonate and polydimethylsilane capped with triethanolammonium sulfonate.
[12]
12. Personal care composition according to claim 1, CHARACTERIZED by the fact that the film-forming agents are at least one member selected from the group consisting of organosiloxane resins, hydrocarbon polymers, hydrocarbon polymer containing at least minus one heteroatom, hydrocarbon polymers containing fluorine atoms and clays.
[13]
13. Personal care composition according to claim 12,
Petition 870190033247, of 5/4/2019, p. 60/64
5/7
CHARACTERIZED by the fact that the organosiloxane film forming agent contains combinations of R3SÍO1 / 2, R2SÍO, RSÍO3 / 2, and SÍO2 units in ratios to each other that satisfy the RnSiO (4-n) / 2 ratio where n is a value between 0 and 1.50 and R is independently selected from the groups methyl, trifluoromethyl, phenylenomethyl and phenyl.
[14]
14. Personal care composition according to claim 12, CHARACTERIZED by the fact that the hydrocarbon polymer film forming agent is at least one member selected from the group consisting of polybutene, polyisobutene, polycyclopentadiene, jelly of petroleum and mineral oil.
[15]
15. Personal care composition according to claim 12, CHARACTERIZED by the fact that the hydrocarbon polymer containing at least one heteroatom is at least one member selected from the group consisting of polyvinylpyrrolidone (PVP) / eicosene copolymer, PVP / hexadecene copolymer, acrylate copolymer and polyvinyl alcohol.
[16]
16. Personal care composition according to claim 12, CHARACTERIZED by the fact that the film-forming clay is at least one member selected from the group consisting of modified clays, unmodified clays, Cloisite 30B, momtmorilite (NaMMT ), LDH and bentonite.
[17]
17. Personal care composition, according to claim 1, CHARACTERIZED by the fact that it also comprises at least one non-functionalized silicone.
[18]
18. Personal care composition according to claim 1, CHARACTERIZED by the fact that it still comprises at least one organic solvent.
[19]
19. Personal care composition according to claim 1, CHARACTERIZED by the fact that it is formulated as an oil-in-water or water-in-oil emulsion.
Petition 870190033247, of 5/4/2019, p. 61/64
6/7
[20]
20. Personal care composition, according to claim 1, CHARACTERIZED by the fact that said personal care composition is selected from the group consisting of antiperspirant deodorants, sprays, sticks and roll-on products, shaving products, skin lotions, moisturizers, toners, bath products, cleaning products, shampoos, conditioners, shampoo / conditioners combined, mousses, styling gels, hair sprays, hair dyes, hair coloring products, hair bleaches, curling products, hair straighteners, nail polish, nail polish remover, nail creams and lotions, cuticle softeners, sunscreen, insect repellent, anti-aging products, lipsticks, foundations, facial powders, eye liners, eye shadows , blushes, makeup, masks, moisturizing preparations, foundations, body and hand preparations, skin care preparations, preparations face and neck treatments, tonics, dressings, hair care aids, fixing aerosols, fragrance preparations, aftershave lotions, makeup preparations, soft focus applications, night and day skin care preparations, non-preparations hair dyes, tanning preparations, synthetic and non-synthetic soap bars, hand liquids, nose strips, non-woven personal care applications, baby lotions, baby lotions and shampoos, baby conditioners, shaving preparations , cucumber slices, skin patches, make-up removers, facial cleansers, cold creams, sun protection products, mousses, spritzes, masks and sludge, face masks, colognes and colognes, hair cuticle liners, shower gels, face and body washes, personal care rinse products, gels, foam baths, spherical cleaners watering, astringent, nail conditioners, eye shadow sticks, face or eye powders, lip ointments, lip glosses, hair care pump sprays and other sprays without
Petition 870190033247, of 5/4/2019, p. 62/64
7/7 aerosol, hair frizz control gel, leave-in hair conditioners, hair polishes, hair detangling products, hair fixers, hair bleaching products, skin lotions, pre-shave and pre-shave creams -shaving shave with electric shavers, anhydrous creams and lotions, oil / water, water / oil emulsions, multiple and macro and micro emulsions, water-resistant creams and lotions, anti-acne preparations, mouthwash, massage oils, toothpastes, whitening gels and sticks, ointment bases, topical wound healing products, aerosol talc, barrier sprays, vitamins and anti-aging preparations, herbal extract preparations, bath salts, body and bath milks, skin aids hair styling, soft solid applications for hair, eyes, nails and skin, controlled release personal care products, hair conditioning mists abelo, moisturizing mists for skin care, wipes to clean the skin, wipes to clean the pores of the skin, pore cleaners, blemish reducers, exfoliating skin, skin peeling enhancers, skin wipes and towels, depilatory preparations, lubricants for personal care, preparations for coloring the nails, drug delivery systems for the topical application of medicinal compositions that must be applied to the skin and combinations thereof.

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同族专利:

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公开号 | 公开日

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EP2800608B1|2019-03-13|

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JP2015503587A|2015-02-02|

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KR101993188B1|2019-09-30|

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WO2013103832A3|2014-07-10|

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US20130171080A1|2013-07-04|

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CN104136002B|2017-11-24|

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CN104159640A|2014-11-19|

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JP6280048B2|2018-02-14|

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JP2015503584A|2015-02-02|

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EP2800551B1|2019-03-13|

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BR112014016668A2|2017-06-13|

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KR20140119091A|2014-10-08|

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US9895306B2|2018-02-20|

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WO2013103701A3|2014-06-26|

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EP2800608A2|2014-11-12|

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WO2013103701A2|2013-07-11|

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IN2014MN01346A|2015-06-12|

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BR112014016668A8|2017-07-04|

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CN104159640B|2018-01-05|

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KR20140119094A|2014-10-08|

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CN104136002A|2014-11-05|

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WO2013103832A2|2013-07-11|

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EP2800551A2|2014-11-12|

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KR102030429B1|2019-10-10|

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JP6280047B2|2018-02-14|

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法律状态:
2018-03-27| B06F| Objections, documents and/or translations needed after an examination request according art. 34 industrial property law|

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2019-01-08| B07A| Technical examination (opinion): publication of technical examination (opinion)|

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2019-07-16| B09A| Decision: intention to grant|

优先权:

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申请号 | 申请日 | 专利标题

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US201261582914P| true| 2012-01-04|2012-01-04|

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US61/582.914|2012-01-04|

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USPCT/US13/20122|2013-01-03|

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PCT/US2013/020122|WO2013103701A2|2012-01-04|2013-01-03|Personal care compositions containing end-functionalized ionic silicone|

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US13/733.482|2013-01-03|

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US13/733,482|US9895306B2|2012-01-04|2013-01-03|Personal care compositions containing end-functionalized ionic silicone|

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PCT/US2013/020305|WO2013103832A2|2012-01-04|2013-01-04|Personal care compositions containing ionic silicone and film-forming agent|

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