WO1992007011A1 - Polyvinylpyrrolidone reticulee pouvant gonfler et compositions a usage cosmetique preparees a partir de celle-ci - Google Patents

Polyvinylpyrrolidone reticulee pouvant gonfler et compositions a usage cosmetique preparees a partir de celle-ci Download PDF

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Publication number
WO1992007011A1
WO1992007011A1 PCT/US1991/005239 US9105239W WO9207011A1 WO 1992007011 A1 WO1992007011 A1 WO 1992007011A1 US 9105239 W US9105239 W US 9105239W WO 9207011 A1 WO9207011 A1 WO 9207011A1
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Prior art keywords
polymer
polymerization
swellable
hair
crosslinking agent
Prior art date
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PCT/US1991/005239
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English (en)
Inventor
Jenn S. Shih
Jui-Chang Chuang
Terry E. Smith
Carmen D. Bires
Michael W. Helioff
Robert B. Login
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Isp Investments Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US07/599,592 external-priority patent/US5073614A/en
Priority claimed from US07/628,122 external-priority patent/US5139770A/en
Application filed by Isp Investments Inc. filed Critical Isp Investments Inc.
Publication of WO1992007011A1 publication Critical patent/WO1992007011A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8176—Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/008—Preparations for oily hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C08F226/10—N-Vinyl-pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/004—Aftersun preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/02—Shaving preparations

Definitions

  • This invention relates to crosslin ed polyvinylpyrrolidone (PVP) , and more particularly, to strongly s ellable, moderately crosslinked PVP polymers which are prepared directly as fine, white powders by precipitation polymerization of vinylpyrrolidone (VP) , and to cosmetic compositions therewith.
  • PVP polyvinylpyrrolidone
  • Polyvinylpyrrolidone is made by homopolymerization of vinylpyrrolidone in bulk, solution or suspension.
  • the polymer is obtained as (1) water soluble PVP; (2) water insoluble PVP which is variably swellable in water and which may form soft gels if strongly swellable.
  • Water soluble PVPs usually are polymerized in aqueous solution using hydrogen peroxide. Polymerization also can take place in organic solvents such as methanol, isopropanol, toluene, benzene, tetrahydrofuran, acetone and hexane, usually with the production of lower molecular weight polymers than polymerization in water.
  • U.S. Pat. 2,938,017 for example, disclosed that insoluble polymerization products can be obtained by heating VP alone, without the addition of water but in the presence of basic alkali or alkaline earth metal compounds such as the oxides, hydroxides or alkoxides of sodium or potassium.
  • This method produced slightly swellable polymers, which, however, showed strong discoloration due to the high temperature at which polymerization took place. Moreover, the reaction was very difficult to control under these conditions.
  • U.S. Pats. 3,277,066 and 3,306,886 disclosed processes for the manufacture of insoluble PVP in which VP was placed in an autoclave and heated under pressure at about 140°C. in the presence of water and catalysts such as alkali metal hydrides, alkali metal borohydrides and/or alkali or alkaline earth metal hydroxides or alkoxides until the polymerization reaction had started. These processes also produced only sparingly swellable polymers with the disadvantage that elevated temperatures were required to start the polymerization reaction, and this necessitated the use of pressure vessels when water was included. German Patent No.
  • VP can be polymerized in dilute aqueous solution in the presence of a crosslinking agent in the absence of oxygen and additionally in the presence of from 0.05 to 2% by weight, based on VP, of one or more ketocarboxylic acids or their methyl or ethyl esters.
  • a small amount of a base was used concommitantly.
  • polymerization at the high pH of the reaction caused yellowing of the polymers.
  • U.S. Pat. 3,933,766 described the preparation of insoluble PVP which was only slightly swellable by the so-called "popcorn" or proliferous polymerization technique.
  • VP was polymerized to insoluble, slightly swellable, crosslinked PVP by heating an aqueous solution of VP in the presence of a bifunctional cyclic acid amide, but without any radical initiator, at about 80°-100°C.
  • U.S. Pat. 4,451,582 disclosed a process for the preparation of insoluble, particulate PVP polymers which were only slightly swellable in water. These polymers were obtained from basic vinyl heterocycles having a pKa higher than 4, and their copolymers, with as much as 30% by weight of copolymerizable monomers. The monomers were polymerized in the presence of from 0.1 to 10% by weight, based on the total amount of monomers, of a crosslinking agent, in the absence of oxygen and polymerization initiators. The polymers were preferably prepared by precipitation polymerization in water; however, they could be obtained in the absence of solvents for the monomers, by heating the latter to, preferably, 150°-180°C.
  • U.S. Pat. 4,647,637 disclosed a process for making insoluble PVP powders which were only slightly swellable by polymerization of VP and a crosslinking agent in a powder bed in the presence of a heat-transfer medium which was inert to the reactants, and in the absence of oxygen or polymerization initiator, at from 90° to 220°C. , while maintaining the reactants in the powder state, circulating the reaction mass and evaporating the heat-transfer medium from the polymerization zone.
  • U.S. Pat. 2,658,058 disclosed a process for crosslinked linear PVP polymers by treatment of the polymer with hydrazine and hydrogen peroxide; U.S. 3,350,366 used ⁇ - ⁇ , ⁇ /-diolefins and hydrogen peroxide; U.S. 2,658,058 used persulfate; and in J. Phys. Chem. 53_, 1852 (1959) , crosslinking was effected by irradiation.
  • U.S. Pats. 4,330,451 and 4,333,112 disclosed a post-treatment process for rendering PVP more highly viscous.
  • PVP was subjected to a heat treatment in the presence of a water-insoluble peroxide and in the absence of oxygen.
  • this process suffered from the disadvantage of requiring an additional step to produce the desired high-viscosity PVP, and this step was difficult to carry out reproducibly.
  • U.S. 3,669,103 described a process for preparing gels of lightly crosslinked PVP by aqueous, solution polymerization of VP in the presence of crosslinking agents.
  • the reaction product was a coherent mass of gel which was evaporated to dryness and ground to provide a finely particulate product.
  • Yet another object of this invention is to provide strongly swellable, moderately crosslinked PVP polymer powders characterized by an aqueous gel volume of about 15-150 ml/g of polymer and a Brookfield viscosity in 5% aqueous solution of at least 10,000 cps.
  • Still another object of the present invention is to provide crosslinked PVP polymer powders which can show favorable white, fine powder formation during polymerization, and which can be made in a high solids content, and which provide clear solutions of high viscosities, and enhanced stability as measured by their retention of viscosity during storage at 50°C. , and excellent salt tolerance.
  • the selection of components for hair and skin treating formulations presents numerous difficulties involving compatibility.
  • Several hair treatment and shampoo formulations have been developed which aim to provide conditioning action during cleansing so as to leave the hair soft, manageable and lustrous and thus to eliminate a separate application of creme rinses or conditioning treatments. Problems arise from the limited compatibility of anionic detergents with commercial cationic conditioning agents which precipitate out of solution in shampoo formulations.
  • Shampoo formulations have employed conventional anionic surfactants such as sodium lauryl sulfate, ammonium lauryl sulfate, amine lauryl sulfates and sodium lauryl sulfate ethers which have been found to be incompatible with most cationic conditioning agents at effective concentration levels.
  • anionic surfactants such as sodium lauryl sulfate, ammonium lauryl sulfate, amine lauryl sulfates and sodium lauryl sulfate ethers which have been found to be incompatible with most cationic conditioning agents at effective concentration levels.
  • Another object of the invention is to provide cosmetic compositions containing strongly swellable, moderately crosslinked polyvinylpyrrolidone polymers which have excellent hair conditioning and thickening properties when incorporated into a shampoo and having high compatibility with components of hair and skin treating formulations.
  • a sunscreen lotion which is water-resistant.
  • What is provided herein are strongly swellable, moderately crosslinked PVP polymers in the form of fine, white powders having (a) an aqueous gel volume of about 15 to 150 ml/g of polymer, (b) a Brookfield viscosity in 5% aqueous solution of at least about 10,000 cps, which (c) are prepared directly by precipitation polymerization of VP in the presence of a crosslinking agent in the amount of about 0.2 to about 1% by weight of VP.
  • (a) is 25 to 75 ml/g of polymer, (b) is at least 15,000 cps, and (c) is about 0.25 to 0.8%. In an optimum form of the invention, (a) is 30 to 60 ml/g, (b) is about 20,000 to 50,000 cps, and (c) is about 0.35 to 0.6%.
  • Gel volume is a measure of the swelling property of the crosslinked polymer and is defined as the equilibrium aqueous swelling volume of polymer per unit weight, and is expressed in the units of ml/g. Gel volume is determined by first adding 1 g. of the polymer to a suitable graduated cylinder filled with water. This mixture then is shaken and allowed to stand at room temperature for 3 days. The volume of the gel which is produced in water is measured and taken as the gel volume. Similarly, the gel volume concept can be applied to non-aqueous systems.
  • the fine, white powder polymers of the invention are prepared directly by a precipitation polymerization process in an organic solvent, such as an aliphatic hydrocarbon solvent, preferably cyclohexane or heptane, or an aromatic hydrocarbon, such as toluene, in the presence of about 0.2 to 1% by weight of VP of a crosslinking agent, preferably N,N'-divinylimidazolidone, triallyl-1,3,5- triazine-2,4,6(lH, 3H,5H)-trione 2,4,6-triallyloxy- 1,3,5-triazine, and pentaerythritol triallyl ether at about 10 to 50% solids.
  • the cosmetic compositions of the invention are used particularly for the personal care of hair and skin, typically conditioning shampoos, lotions for the treatment of hand and body, and sunscreen formulations which are water-resistant.
  • strongly swellable, moderately crosslinked PVP polymers are prepared directly in the form of fine, white powders by precipitation polymerization of vinylpyrrolidone in the presence of a predetermined amount of a crosslinking agent and free radical polymerization initiator in an organic solvent, preferably an aliphatic hydrocarbon, e.g. a C 3 -C 10 saturated, branched or unbranched, cyclic or acyclic aliphatic hydrocarbon, and most preferably cyclohexane or heptane, or mixtures thereof.
  • an organic solvent preferably an aliphatic hydrocarbon, e.g. a C 3 -C 10 saturated, branched or unbranched, cyclic or acyclic aliphatic hydrocarbon, and most preferably cyclohexane or heptane, or mixtures thereof.
  • the amount of solvent used in the process of the invention should be sufficient to dissolve an appreciable amount of the reactants and to maintain the copolymer precipitate in a stirrable state at the end of the polymerization. Generally, about 10 to 50% solids, preferably 15-30%, is maintained in the reaction mixture.
  • the precipitation polymerization process of the invention is carried out in the presence of a suitable free radical polymerization initiator.
  • Suitable initiators include acyl peroxides such as diacetyl peroxide, dibenzoyl peroxide and dilauryl peroxide; peresters such as t-butylperoxy pivalate, tert-butyl peroxy-2-ethylhexanoate; peroxides such as di-tert-butyl peroxide; percarbonates such as di ⁇ yclohexyl peroxydicarbonate; and azo compounds such as 2,2'-azobis(isobutyronitrile) ,
  • the amount of such initiator may vary widely; generally about 0.2-5.0% is used, based on the weight of total monomers charged.
  • the reaction temperature may vary widely; generally the reaction mixture is maintained at about 40°-150°C, preferably 60°-70°C, during the polymerization. Pressure usually is kept at atmospheric pressure, although higher and lower pressures may be used as well.
  • the reaction mixture should be stirred vigorously under an inert atmosphere, e.g. nitrogen, during the polymerization.
  • a stirring rate of about 100-600 rp in a 1-liter lab reactor is quite adequate to effect the desired polymerization and to keep the precipitate in a stirrable state during the polymerization.
  • Suitable crosslinking agents for use in the invention include such multifunctional compounds as the divinyl ethers of an aliphatic diol, e.g. the divinyl ethers of 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-unidecanediol, and 1,12-dodecanediol; as well as the divinyl ethers of diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, hexaethylene glycol, heptaethylene glycol, octaethylene glycol, nonaethylene glycol, decaethylene glycol and further polyalkylene glycols up to a molecular
  • crosslinking agents include 1,7-octadiene, 1,9-decadiene, 1,13-tetradecadiene, divinylbenzene, N-N'-divinylimidazolidone, and methylene bisacrylamide; acrylates such as polyethylene glycol diacrylate, trimethylolpropane triacrylate, propylene glycol diacrylate; allyl ether derivatives of polyhydric alcohols such as pentaerythritol triallyl ether; or polyhydric alcohols esterified once or twice with acrylic acid; triallylamine, tetraallylethylene- diamine, diallyl phthalate, and the like.
  • Preferred crosslinking agents are the following: N,N'-divinylimidazolidone, pentaerythritol triallyl ether, triallyl-1,3,5-triazine-2,4,6(IH,3H,5H)-trione and 2,4,6-triallyloxy-l,3,5-triazine.
  • the precipitation polymerization process of the invention may be carried out by first precharging a suitable reactor with a predetermined amount of the organic solvent, for example, an aliphatic hydrocarbon solvent, and heating the solvent to a desired reaction temperature while stirring vigorously under an inert gas atmosphere.
  • the initiator is then charged into the reactor.
  • a solution containing selected amounts of vinylpyrrolidone monomer and the crosslinker material is admitted into the reactor over a period of time, generally about an hour or more, and preferably below the surface of the solvent.
  • the reaction mixture is held for an additional period of time for polymerization to be completed.
  • the mixture is cooled to room temperature. Filtering, washing with solvent, and drying provides the desired polymer in yields approaching quantitative.
  • the reaction product may be dried directly to provide the polymer powders.
  • the heterogeneous polymerization process of the invention in cyclohexane or heptane solvent provides the desired PVP polymer product as a fine, white powder, which precipitates readily, in quantitative yield, with substantially the same degree of crosslinking as the charge of VP monomer and crosslinking agent, in a smooth polymerization without excessive swelling of polymer during the course of the process.
  • the solvents of the invention are non-solvents for PVP and enable the polymerization to proceed in the presence of crosslinking agent without excessive building up viscosity of the reaction mixture during polymerization.
  • the present crosslinked polyvinylpyrrolidone polymers possess unique properties, among which is their ability to build viscosity, while simultaneously providing a hair and skin conditioning capability in cosmetic formulations containing anionic surfactants.
  • These compounds are highly compatible with o -olefin sulfonates and anionic surfactant salts conventionally employed in shampoos and skin lotions.
  • Their compatibility is such that up to 5% by weight or more of the polymer compounds can be incorporated in the formulation, a characteristic which permits the formation of effective formulations as liquids or gels, and can be employed in shampoos, hair conditioners and lotions as an agent which incorporates thickening and conditioning qualities in one additive; thus eliminating the need for separate chemical components to accomplish these individual needs.
  • the compounds of this invention are mixed with a standard formulation of shampoo, cream rinse, hand or body lotion or creams, sunscreen, etc., in an effective amount which ranges from between about 0.2 to about 10% by weight, preferably between about 0.5 and about 5% by weight, of the total formulation.
  • the present compounds in concentrations up to 5% by weight show no tendency to precipitate after extended periods including periods up to 6 months or more.
  • an inert solvent such as water, propylene glycol, ethanol, etc.
  • incorporation of the present product is usually affected at room temperature under atmospheric pressure and requires no special formulating technique. However, for certain formulations incorporation of the present product can be effected at temperatures up to about 85°C.
  • Amphoteric-containing shampoo formulations are best prepared by initially preparing an aqueous solution of the polymer and the amphoteric surfactant and then adding the solution to the shampoo formulation.
  • a 2-liter, 4-necked reaction vessel was equipped with a condenser, a constant speed mechanical stirrer, set at 170 rpm with a torque indicator and an anchor agitator having an open radius of 4 and 5/6 inches, an adaptor for admitting nitrogen, and a thermocouple connected to a temperature controller.
  • the vessel was charged with 1000 g. of cyclohexane and heated to 65°C. during 30 minutes while purging with nitrogen. The reactor then was held at 65°C. for an additional 30 minutes. Then 520 microliters of t-butylperoxy pivalate (Lupersol 11, 75% active) polymerization indicator was added. Thereafter a solution of 250 g. of vinylpyrrolidone and 1.25 g.
  • N,N'-divinylimidazolidone crosslinking agent was introduced into the charged reactor over a period of 4 hours while stirring the contents.
  • the feeding rate was about 1.0 ml./min.
  • the mixture was heated to 85°C. over a half-hour and held at that temperature for another half-hour.
  • the mixture was transferred to a 2-liter high pressure reactor and 1.0 g. of
  • Example 1 The procedure of Example 1 was followed using various amounts of different crosslinkers with the following results.
  • PTE pentaerythritol triallyl ether
  • MBA methylene bisacrylamide ** based upon VP used, by weight
  • Example 2 The procedure of Example 1 was followed using heptane as solvent in place of cyclohexane.
  • the feeding rate of the solution of vinylpyrrolidone in crosslinking agent was 0.50-0.55 ml./min.
  • Table II The results are shown in Table II below.
  • Example 1 The reactor of Example 1 was provided with the anchor agitator positioned in the middle of the reactor and extended to within 2 inches of the bottom of the reactor. Two dip tubes were connected to two metering pumps. The thus-equipped reactor then was charged with the solvent which filled the reactor to about 4 inches above the bottom of the dip tubes. In this procedure, the solution of VP and crosslinking agent was admitted into the reactor through the dip tubes to a position below the surface of the solvent. The effect of such subsurface feeding of monomer-crosslinker solution was to reduce build-up of viscosity of the polymer product during the polymerization, resulting in a smoother course for the process, particularly with respect to effective stirring of the reaction mixture. Properties of Polymer of Invention
  • the strongly swellable, moderately crosslinked PVP polymer powders of the invention are characterized by its unique gel volume and viscosity, which properties enable the polymer to thicken aqueous and non-aqueous solutions effectively.
  • the viscosity of the polymer is defined by its Brookfield viscosity in cps, which is determined upon a 5% aqueous solution of the polymer at 25°C. by a standard analytical procedure using Model LTV and Spindle No. 4.
  • an effective thickener product is provided by including crosslinker in the reaction mixture at a suitable concentration of about 0.2 to 1.0 % by weight, based upon VP, preferably about 0.25 to 0.8%, and optimally, at about 0.35 to 0.6%.
  • the crosslinked polymer product exhibits a gel volume of about 15 to 150 ml/g of polymer and a Brookfield viscosity of at least 10,000 cps.
  • the gel volume is about 25 to 75 ml/g of polymer and its Brookfield viscosity is at least 15,000 cps.
  • the polymer exhibits a gel volume of about 30 to 60 ml/g of polymer and a Brookfield viscosity of about 20,000 to 50,000 cps.
  • the viscosity of the crosslinked polymer of the invention is particularly substantially independent of extended storage time even at 50°C, and of pH, and is tolerant of monovalent and multivalent salts in solution.
  • the residual VP monomer content of the polymers obtained herein is less than about 0.1% by weight.
  • the formation of a gel mass during polymerization may trap considerable amounts of VP monomer in the polymeric gel network.
  • Germaben II Ingredients Parts by Weight
  • Germaben II 0.50 colorant qs
  • Germaben II 0.50 colorant qs fragrance qs added inorganic salts as desired for viscosity modification
  • Germaben II 0.50 Ingredients Parts by Weight
  • Carbomer 941 0.20 tetrasodium ethylene diamine tetra- 0.10 acetic acid cetearyl alcohol* and polyethylene 2.50 glycol ether of cetearyl alcohol isopropyl myristate 1.00

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne des polymères de polyvinylpyrrolidone modérément réticulés se présentant sous forme de fines poudres blanches qui se caractérisent par (a) un paramètre de gonflement aqueux défini par son volume en gel compris entre environ 15 et 150 ml/g, (b) une viscosité Brookfield dans une solution aqueuse à 5 % égale à au moins 10,000 cps, et (c) une préparation directe par un procédé de polymérisation par précipitation dans un solvant organique, en présence d'environ 0,2 à 1 % en poids de vinylpirrolidone, d'un agent de réticulation multifonctionelle de préférence suivant un pourcentage compris entre environ 0,25 % et 0,8 %, et de manière optimale suivant un pourcentage compris entre environ 0,35 % et 0,6 %. Suivant des quantités variant de 0,2 % à 10 % en poids, ces polymères sont incorporés dans des compositions cosmétiques destinées au soin des cheveux et de la peau.
PCT/US1991/005239 1990-10-18 1991-07-24 Polyvinylpyrrolidone reticulee pouvant gonfler et compositions a usage cosmetique preparees a partir de celle-ci WO1992007011A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US599,592 1984-04-13
US07/599,592 US5073614A (en) 1990-10-18 1990-10-18 Strongly swellable, moderately crosslinked polyvinylpyrrolidone
US07/628,122 US5139770A (en) 1990-12-17 1990-12-17 Cosmetic compositions containing strongly swellable, moderately crosslinked polyvinylpyrrolidone
US628,122 1990-12-17

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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994001079A1 (fr) * 1992-07-14 1994-01-20 Basf Aktiengesellschaft Produits pour le traitement des cheveux renfermant des copolymerisats servant d'agents filmogenes
EP0709411A2 (fr) * 1994-10-29 1996-05-01 Basf Aktiengesellschaft Copolymères solubles pour la cosmétique pour les cheveux
US5716634A (en) * 1995-09-13 1998-02-10 Isp Investments Inc. Clear, homogenized, flowable hydrogel of crosslinked N-vinyl lactam polymer
EP0966492A2 (fr) * 1997-03-13 1999-12-29 Isp Investments Inc. Polymere de vinylpyrrolidone reticule contenant un agent de reticulation possedant une fraction divynyle pendante et un groupe de chelation capable de complexer des ions de metal lourd dans une solution aqueuse
WO2001080812A2 (fr) * 2000-04-19 2001-11-01 Wella Aktiengesellschaft Agent cosmetique sous forme de gel
WO2002013772A2 (fr) * 2000-08-16 2002-02-21 L'oreal Composition de coiffage comprenant des particules adhesives
WO2004026270A1 (fr) * 2002-09-17 2004-04-01 Henkel Kommanditgesellschaft Auf Aktien Produit de soin capillaire a effet revitalisant
EP0961610B1 (fr) * 1997-01-17 2004-12-01 Ponsus Pharma AB Preparation pour la peau
US7083810B2 (en) 2000-04-19 2006-08-01 Wella Aktiengesellschaft Cosmetic agent in the form of a gel
EP2308461A1 (fr) * 2009-10-07 2011-04-13 The Procter & Gamble Company Composition cosmétique comprenant un polymère réticulé direct
WO2011044306A1 (fr) * 2009-10-07 2011-04-14 The Procter & Gamble Company Compositions cosmétiques à base de polymères à réticulation directe
WO2011020646A3 (fr) * 2009-08-17 2011-04-28 Henkel Ag & Co. Kgaa Compositions de soin capillaire contenant de l'alcool lanolique à teneur élevée en alcools gras à longue chaîne
DE102010022061A1 (de) 2010-05-31 2011-12-01 Beiersdorf Ag Polymerkombinationen für kosmetische Zubereitungen
US20130336905A1 (en) * 2010-04-19 2013-12-19 Isp Investments Inc. Compositions of enhanced viscosity, clarity, or both enhanced viscosity and clarity
FR3044896A1 (fr) * 2015-12-15 2017-06-16 Oreal Composition cosmetique comprenant au moins 10 % en poids d'un tensioactif anionique, un acide gras et un agent nacrant mineral
WO2023099232A1 (fr) * 2021-11-30 2023-06-08 Basf Se Préparation de polymères de n-vinylpyrrolidone, contenant moins de 0,5 % en poids de 2-pyrrolidone

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GB1049027A (en) * 1963-05-29 1966-11-23 Bayer Ag Spontaneously cross-linking polymers
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Cited By (24)

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WO1994001079A1 (fr) * 1992-07-14 1994-01-20 Basf Aktiengesellschaft Produits pour le traitement des cheveux renfermant des copolymerisats servant d'agents filmogenes
CN1087311C (zh) * 1994-10-29 2002-07-10 Basf公司 头发化妆品用的可溶性共聚物
EP0709411A2 (fr) * 1994-10-29 1996-05-01 Basf Aktiengesellschaft Copolymères solubles pour la cosmétique pour les cheveux
EP0709411A3 (fr) * 1994-10-29 1996-09-11 Basf Ag Copolymères solubles pour la cosmétique pour les cheveux
US5716634A (en) * 1995-09-13 1998-02-10 Isp Investments Inc. Clear, homogenized, flowable hydrogel of crosslinked N-vinyl lactam polymer
EP0961610B1 (fr) * 1997-01-17 2004-12-01 Ponsus Pharma AB Preparation pour la peau
EP0966492A2 (fr) * 1997-03-13 1999-12-29 Isp Investments Inc. Polymere de vinylpyrrolidone reticule contenant un agent de reticulation possedant une fraction divynyle pendante et un groupe de chelation capable de complexer des ions de metal lourd dans une solution aqueuse
EP0966492A4 (fr) * 1997-03-13 2000-06-07 Isp Investments Inc Polymere de vinylpyrrolidone reticule contenant un agent de reticulation possedant une fraction divynyle pendante et un groupe de chelation capable de complexer des ions de metal lourd dans une solution aqueuse
WO2001080812A2 (fr) * 2000-04-19 2001-11-01 Wella Aktiengesellschaft Agent cosmetique sous forme de gel
US7083810B2 (en) 2000-04-19 2006-08-01 Wella Aktiengesellschaft Cosmetic agent in the form of a gel
US7455832B2 (en) * 2000-04-19 2008-11-25 Wella Ag Cosmetic preparation in gel form
WO2001080812A3 (fr) * 2000-04-19 2002-04-04 Wella Ag Agent cosmetique sous forme de gel
WO2002013772A3 (fr) * 2000-08-16 2003-02-13 Oreal Composition de coiffage comprenant des particules adhesives
WO2002013772A2 (fr) * 2000-08-16 2002-02-21 L'oreal Composition de coiffage comprenant des particules adhesives
WO2004026270A1 (fr) * 2002-09-17 2004-04-01 Henkel Kommanditgesellschaft Auf Aktien Produit de soin capillaire a effet revitalisant
WO2011020646A3 (fr) * 2009-08-17 2011-04-28 Henkel Ag & Co. Kgaa Compositions de soin capillaire contenant de l'alcool lanolique à teneur élevée en alcools gras à longue chaîne
EP2308461A1 (fr) * 2009-10-07 2011-04-13 The Procter & Gamble Company Composition cosmétique comprenant un polymère réticulé direct
WO2011044306A1 (fr) * 2009-10-07 2011-04-14 The Procter & Gamble Company Compositions cosmétiques à base de polymères à réticulation directe
EP2322141A3 (fr) * 2009-10-07 2011-07-27 The Procter & Gamble Company Compositions cosmétiques comprenant des polymères élastomériques
US20130336905A1 (en) * 2010-04-19 2013-12-19 Isp Investments Inc. Compositions of enhanced viscosity, clarity, or both enhanced viscosity and clarity
DE102010022061A1 (de) 2010-05-31 2011-12-01 Beiersdorf Ag Polymerkombinationen für kosmetische Zubereitungen
WO2011151279A2 (fr) 2010-05-31 2011-12-08 Beiersdorf Ag Combinaisons polymères pour préparations cosmétiques
FR3044896A1 (fr) * 2015-12-15 2017-06-16 Oreal Composition cosmetique comprenant au moins 10 % en poids d'un tensioactif anionique, un acide gras et un agent nacrant mineral
WO2023099232A1 (fr) * 2021-11-30 2023-06-08 Basf Se Préparation de polymères de n-vinylpyrrolidone, contenant moins de 0,5 % en poids de 2-pyrrolidone

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