CA2170567A1 - Sulfo-containing polymers suitable for use in hairsetting compositions - Google Patents
Sulfo-containing polymers suitable for use in hairsetting compositionsInfo
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- CA2170567A1 CA2170567A1 CA 2170567 CA2170567A CA2170567A1 CA 2170567 A1 CA2170567 A1 CA 2170567A1 CA 2170567 CA2170567 CA 2170567 CA 2170567 A CA2170567 A CA 2170567A CA 2170567 A1 CA2170567 A1 CA 2170567A1
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- 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
- 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
- A61K8/8141—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
-
- 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
- A61K8/8141—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
-
- 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)
- A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
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- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cosmetics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Polymers suitable for aqueous hairsetting compositions are obtainable by free-radically initiated solution polymerization of a monomer mixture of A) 50 - 90% by weight of one or more monomers selected from the group consisting of C1-C18-alkyl esters of acrylic or meth-acrylic acid and vinyl esters of C2-C10-monocarboxylic acids, B) 10 - 25% by weight of a sulfo-containing vinyl monomer, and C) 0 - 40% by weight of a further monomer.
Description
Sulfo-containing polymers suitable for use in hairsetting compositions The present invention relates to polymers suitable for use in agueous hairsetting compositions, obtainable by free-radically initiated solution polymerization of a monomer mixture of A) 50 - 90% by weight of one or more monomers selected from the group consisting of Cl-C18-alkyl esters of acrylic or meth-acrylic acid and vinyl esters of C2-C10-monocarboxylic acids, B) 10 - 25% by weight of a sulfo-containing vinyl monomer, and C) 0 - 40~ by weight of a further monomer selected from the group consisting of acrylic acid, methacrylic acid, acryl-amide, methacrylamide, C3-Cg-N-alkylacrylamide, N,N-dimethyl-acrylamide, N-vinylpyrrolidone and N-vinylcaprolactam.
20 The present invention further relates to hairsetting compositions comprising such polymers as film-former.
The rising expectations of the environmental compatibility of cosmetic products are occasioning an increasing need for hair cosmetics polymers which are suitable for such formulations.
US-A-4 859 458 discloses hair cosmetic formulations based on copolymers containing sulfo-contA;n;ng vinyl monomers, the sulfo groups being present as salts of polyethoxylated amines. These 30 formulations have conditioning properties, in particular.
EP-A-521 666, EP-A-522 756 and US-A-5 275 809 describe ampholytic polymers of acrylamidomethylpropanesulfonic acid and diallyldi-methylammonium chloride, which are used in conditioner formula-tions.
Japanese Laid-Open Application J 5 616 109 discloses acrylate-based tetrapolymers which, besides sulfo-cont~;n;ng monomers, also contain hydroxyl-containing monomers. Formulations of these 4~0 polymers confer on hair a rather soft hand combined with less pronounced setting properties.
EP-A-611 566 discloses hairsetting aerosols cont~;n;ng copolymers of su]fo-containing vinyl monomers and N-n,onoal~yl(meth)acryl--amides with or without ~urther, acrylate rnonomers. Such copoly-mers are not j-st commer~islly unattra~tive hccauæe of the relatively high proportion of the coætly sulfonate monomers;
because of the strong polyelectrolyte character they also have relatively high viscosities in aqueous solution coupled with re-stricted compatibility with organic solvents and a certain ten-dency toward tackiness.
It is an object of the present invention to find polymers for use in hairsetting compositions which, as well as having good setting properties, also have good water solubility combined with good drying characteristics.
We have found that this object is achieved by the above-defined polymers and also hairsetting compositions comprising such polymers.
Suitable monomers A) for the purposes of the present invention include for example the Cl-Cl8-alkyl esters of acrylic acid or of methacrylic acid, preferably ethyl acrylate, tert-butyl acrylate, methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, isobutyl methacrylate or tert-butyl methacrylate or else dodecyl 20 or stearyl acrylates and methacrylates. Also suitable for use as monomers A) are the vinyl esters of saturated C2-C10-monocarboxyl-ic acids, in particular vinyl acetate and vinyl propionate or vinyl esters of long-chain linear or branched fatty acids, for example of the Versatic~ acids (from Shell).
It is also possible to use mixtures of monomers A). Preferably the or each monomer A) is chosen so that a homopolymer or copoly-mer made thereof will have a glass transition temperature Tg of >10 C. The monomers A) are used in amounts from 50 to 90, prefer-30 ably from 70 to 85, % by weight.
Suitable monomers B) for the purposes of the present inventionare sulfo-carrying vinyl monomers, for example 2-acrylamide-2-methylpropanesulfonic acid, 2-methacrylamide-2-methylpropanesul-fonic acid, 2-acryloylethanesulfonic acid, 2-methacryloylethane-sulfonic acid, 2-acryloylpropanesulfonic acid, 2-methacryloylpro-panesulfonic acid, styrenesulfonic acid and vinylsulfonic acid.
Preferred monomers B) are 2-acrylamido-2-methylpropanesulfonic acid, 2-acryloyl-2-methylpropanesulfonic acid and 2-methacryloyl-40 2-methylpropanesulfonic acid.
The sulfo groups of monomers B) are preferably converted in whole or in part into the salt form before or during the polymeriza-tion, using an inorganic base or an organic nitrogen base having 1 - 8 carbon atoms. Suitable inorganic bases include in particu-lar alkali metal hydroxides such as sodium hydroxide and potas--sium hydroxide or alkaline earth metal hydroxides such as magnesium hydroxide, calcium hydroxide and barium hydroxide, or else ammonia. Suitable nitrogen base compounds include amines such as methylamine, dimethylamine, ethylamine, diethylamine and the corresponding higher homologs or, preferably, alkanolamines as sanctioned for cosmetics, for example 2-amino-2-methylpropanol or triethanolamine.
Monomers B) are used in amounts from 10 to 25, preferably from 10 to 20, % by weight.
The polymers of the present invention may further contain up to 40% by weight, preferably from 0 to 25% by weight, of a monome-selected from the group consisting of acrylic acid, methacrylic acid, acrylamide, methacrylamide, C3-C8-N-alkylacrylamides, N,N-dimethylacrylamide, N-vinylpyrrolidone and N-vinylcaprolactam, in which case the two last-mentioned monomers are preferred.
The K values range from 15 to 40, preferably from 20 to 35. The K values are determined by the method of H. Fikentscher, 20 Cellulose-Chemie 13 (1932), 58-64, 71-74, in 1% strength by weight N-methylpyrrolidone solution.
The copolymers of the present invention are prepared by the method of free-radical solution polymerization, in alcohols, optionally in a mixture of alcohols and water. Suitable alcohols are Cl-C4-alkanols, preferably the alcohols ethanol and isoprop-anol which are customarily used in cosmetics.
The polymerization is carried out in the presence of suitable 30 amounts of a free-radical polymerization initiator such as an organic azo or peroxo compound.
Examples of suitable initiators are diacyl peroxides such as dilauroyl, didecanoyl or dioctanoyl peroxide and also per-esters such as tert-butyl peroxypivalate, tert-amyl peroxypivalate or tert-butyl peroxyneodecanoate, and also azo compounds such as dimethyl 2,2-azobis(isobutyrate), 2,2-azobis(isobutyronitrile)~
20 The present invention further relates to hairsetting compositions comprising such polymers as film-former.
The rising expectations of the environmental compatibility of cosmetic products are occasioning an increasing need for hair cosmetics polymers which are suitable for such formulations.
US-A-4 859 458 discloses hair cosmetic formulations based on copolymers containing sulfo-contA;n;ng vinyl monomers, the sulfo groups being present as salts of polyethoxylated amines. These 30 formulations have conditioning properties, in particular.
EP-A-521 666, EP-A-522 756 and US-A-5 275 809 describe ampholytic polymers of acrylamidomethylpropanesulfonic acid and diallyldi-methylammonium chloride, which are used in conditioner formula-tions.
Japanese Laid-Open Application J 5 616 109 discloses acrylate-based tetrapolymers which, besides sulfo-cont~;n;ng monomers, also contain hydroxyl-containing monomers. Formulations of these 4~0 polymers confer on hair a rather soft hand combined with less pronounced setting properties.
EP-A-611 566 discloses hairsetting aerosols cont~;n;ng copolymers of su]fo-containing vinyl monomers and N-n,onoal~yl(meth)acryl--amides with or without ~urther, acrylate rnonomers. Such copoly-mers are not j-st commer~islly unattra~tive hccauæe of the relatively high proportion of the coætly sulfonate monomers;
because of the strong polyelectrolyte character they also have relatively high viscosities in aqueous solution coupled with re-stricted compatibility with organic solvents and a certain ten-dency toward tackiness.
It is an object of the present invention to find polymers for use in hairsetting compositions which, as well as having good setting properties, also have good water solubility combined with good drying characteristics.
We have found that this object is achieved by the above-defined polymers and also hairsetting compositions comprising such polymers.
Suitable monomers A) for the purposes of the present invention include for example the Cl-Cl8-alkyl esters of acrylic acid or of methacrylic acid, preferably ethyl acrylate, tert-butyl acrylate, methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, isobutyl methacrylate or tert-butyl methacrylate or else dodecyl 20 or stearyl acrylates and methacrylates. Also suitable for use as monomers A) are the vinyl esters of saturated C2-C10-monocarboxyl-ic acids, in particular vinyl acetate and vinyl propionate or vinyl esters of long-chain linear or branched fatty acids, for example of the Versatic~ acids (from Shell).
It is also possible to use mixtures of monomers A). Preferably the or each monomer A) is chosen so that a homopolymer or copoly-mer made thereof will have a glass transition temperature Tg of >10 C. The monomers A) are used in amounts from 50 to 90, prefer-30 ably from 70 to 85, % by weight.
Suitable monomers B) for the purposes of the present inventionare sulfo-carrying vinyl monomers, for example 2-acrylamide-2-methylpropanesulfonic acid, 2-methacrylamide-2-methylpropanesul-fonic acid, 2-acryloylethanesulfonic acid, 2-methacryloylethane-sulfonic acid, 2-acryloylpropanesulfonic acid, 2-methacryloylpro-panesulfonic acid, styrenesulfonic acid and vinylsulfonic acid.
Preferred monomers B) are 2-acrylamido-2-methylpropanesulfonic acid, 2-acryloyl-2-methylpropanesulfonic acid and 2-methacryloyl-40 2-methylpropanesulfonic acid.
The sulfo groups of monomers B) are preferably converted in whole or in part into the salt form before or during the polymeriza-tion, using an inorganic base or an organic nitrogen base having 1 - 8 carbon atoms. Suitable inorganic bases include in particu-lar alkali metal hydroxides such as sodium hydroxide and potas--sium hydroxide or alkaline earth metal hydroxides such as magnesium hydroxide, calcium hydroxide and barium hydroxide, or else ammonia. Suitable nitrogen base compounds include amines such as methylamine, dimethylamine, ethylamine, diethylamine and the corresponding higher homologs or, preferably, alkanolamines as sanctioned for cosmetics, for example 2-amino-2-methylpropanol or triethanolamine.
Monomers B) are used in amounts from 10 to 25, preferably from 10 to 20, % by weight.
The polymers of the present invention may further contain up to 40% by weight, preferably from 0 to 25% by weight, of a monome-selected from the group consisting of acrylic acid, methacrylic acid, acrylamide, methacrylamide, C3-C8-N-alkylacrylamides, N,N-dimethylacrylamide, N-vinylpyrrolidone and N-vinylcaprolactam, in which case the two last-mentioned monomers are preferred.
The K values range from 15 to 40, preferably from 20 to 35. The K values are determined by the method of H. Fikentscher, 20 Cellulose-Chemie 13 (1932), 58-64, 71-74, in 1% strength by weight N-methylpyrrolidone solution.
The copolymers of the present invention are prepared by the method of free-radical solution polymerization, in alcohols, optionally in a mixture of alcohols and water. Suitable alcohols are Cl-C4-alkanols, preferably the alcohols ethanol and isoprop-anol which are customarily used in cosmetics.
The polymerization is carried out in the presence of suitable 30 amounts of a free-radical polymerization initiator such as an organic azo or peroxo compound.
Examples of suitable initiators are diacyl peroxides such as dilauroyl, didecanoyl or dioctanoyl peroxide and also per-esters such as tert-butyl peroxypivalate, tert-amyl peroxypivalate or tert-butyl peroxyneodecanoate, and also azo compounds such as dimethyl 2,2-azobis(isobutyrate), 2,2-azobis(isobutyronitrile)~
2,2-azobis(2-methylbutyronitrile) or 2,2-azobis(2,2-dimethyl-valeronitrile).
The copolymers can be prepared batchwise, but they are preferably prepared by the feed stream addition method whereby part of the solution of the monomer mixture is included in the initial charge and the remainder is added over a period of several hours.
It can also be advantageous for the course of the reaction to in-clude the solvent in the initial charge in the reactor and to me-ter in the monomers, the initiator and the neutralizing agent to maintain the required pH under the polymerization conditions.
The monomer addition period is customarily determined so that the released heat of polymerization is safely dissipated under the customary technical conditions.
10 The polymerization is advantageously carried out at temperatures from 60 to 100 C, preferably from 70 to 85 C, and the reaction can be carried out under autogenous pressure, atmospheric pressure or protective gas overpressure. An example of a suitable protective gas is nitrogen.
If the polymers are to be used in purely aqueous formulations or solvents such as methanol, for example, it is advisable to ex-change the organic solvent for water. The exchange of organic solvents for water is customarily effected by adding the corres-20 ponding amount of water to the reaction batch after the polymer-ization has taken place and simultaneously or subsequently distilling the solvent off at atmospheric pressure or reduced pressure. It is particularly advantageous to remove the organic solvent by steam distillation.
The pH of the polymerization mixture is preferably set so that the ester groups of the monomers are stable to acid hydrolysis or transesterification, and the setting can be effected with the abovementioned inorganic or organic bases. A particularly simple 30 procedure comprises adding monomers B) to the polymerization zone as an aqueous solution having a pH of at least 4. However, mono-mers B) can also be added to the reaction mixture in unneutral-ized form together with appropriate amounts of a base in order that the pH may be moved into the desired range.
The aqueous or aqueous-alcoholic polymer solutions customarily contain the polymers in amounts from 10 to 70, preferably from 15 to 50, % by weight.
40 Suitable drying processes for creating pulverulent polymers in-clude all those which are suitable for drying from aqueous solution. Preferred processes are spray drying, spray fluidized bed drying, roller drying and belt drying, and less preferable but still usable processes are freeze drying and freeze concentration.
The polymer powders obtainable according to the invention by dry-ing from an aqueous solution are readily soluble in alcohols, water and mixtures thereof.
A particular advantage of the polymers of the present invention is that they are fully water soluble even at a pH within the range from 5.5 to 7; ie., hair and scalp are not damaged by high alkalinity. The ready water solubility also facilitates the preparation of purely water-based formulations, which is particu-10 larly advantageous from an environmental point of view. The poly-mers of the present invention combine good setting properties with good drying characteristics and low tackiness and are there-fore especially suitable for use as film-formers in hairsetting compositions such as hair sprays, hair lacquers, setting lotions, hair mousses or hair gels.
Examples The cloudiness of the aqueous copolymer solutions was determined 20 by nephelometric turbidity measurement (modified method according to DIN 38 404). In this method of measurement, light is passed through the measurement solution and the scattering of light is determined photometrically by determining the interaction between the light rays and the particles or droplets in the solution whose number and size determine the degree of turbidity. The unit of measurement is the nephelometric turbidity unit (NTU), which is measured at 2S C and in a 10% strength by weight aqueous solu-tion and defined by calibration on the basis of formazine as artificial turbidifier. The higher the NTU value, the greater the 30 turbidity of the solution.
Preparation of polymers Example 1 First the following solutions were pre-prepared:
1. Solution 1, consisting of 150 g of ethyl acrylate, 250 g of isobutyl methacrylate and g of isopropanol.
2. Solution 2, consisting of 100 g of 2-acrylamido-2-methyl-propanesulfonic acid, 17 g of sodium hydroxide and 100 g of water.
The copolymers can be prepared batchwise, but they are preferably prepared by the feed stream addition method whereby part of the solution of the monomer mixture is included in the initial charge and the remainder is added over a period of several hours.
It can also be advantageous for the course of the reaction to in-clude the solvent in the initial charge in the reactor and to me-ter in the monomers, the initiator and the neutralizing agent to maintain the required pH under the polymerization conditions.
The monomer addition period is customarily determined so that the released heat of polymerization is safely dissipated under the customary technical conditions.
10 The polymerization is advantageously carried out at temperatures from 60 to 100 C, preferably from 70 to 85 C, and the reaction can be carried out under autogenous pressure, atmospheric pressure or protective gas overpressure. An example of a suitable protective gas is nitrogen.
If the polymers are to be used in purely aqueous formulations or solvents such as methanol, for example, it is advisable to ex-change the organic solvent for water. The exchange of organic solvents for water is customarily effected by adding the corres-20 ponding amount of water to the reaction batch after the polymer-ization has taken place and simultaneously or subsequently distilling the solvent off at atmospheric pressure or reduced pressure. It is particularly advantageous to remove the organic solvent by steam distillation.
The pH of the polymerization mixture is preferably set so that the ester groups of the monomers are stable to acid hydrolysis or transesterification, and the setting can be effected with the abovementioned inorganic or organic bases. A particularly simple 30 procedure comprises adding monomers B) to the polymerization zone as an aqueous solution having a pH of at least 4. However, mono-mers B) can also be added to the reaction mixture in unneutral-ized form together with appropriate amounts of a base in order that the pH may be moved into the desired range.
The aqueous or aqueous-alcoholic polymer solutions customarily contain the polymers in amounts from 10 to 70, preferably from 15 to 50, % by weight.
40 Suitable drying processes for creating pulverulent polymers in-clude all those which are suitable for drying from aqueous solution. Preferred processes are spray drying, spray fluidized bed drying, roller drying and belt drying, and less preferable but still usable processes are freeze drying and freeze concentration.
The polymer powders obtainable according to the invention by dry-ing from an aqueous solution are readily soluble in alcohols, water and mixtures thereof.
A particular advantage of the polymers of the present invention is that they are fully water soluble even at a pH within the range from 5.5 to 7; ie., hair and scalp are not damaged by high alkalinity. The ready water solubility also facilitates the preparation of purely water-based formulations, which is particu-10 larly advantageous from an environmental point of view. The poly-mers of the present invention combine good setting properties with good drying characteristics and low tackiness and are there-fore especially suitable for use as film-formers in hairsetting compositions such as hair sprays, hair lacquers, setting lotions, hair mousses or hair gels.
Examples The cloudiness of the aqueous copolymer solutions was determined 20 by nephelometric turbidity measurement (modified method according to DIN 38 404). In this method of measurement, light is passed through the measurement solution and the scattering of light is determined photometrically by determining the interaction between the light rays and the particles or droplets in the solution whose number and size determine the degree of turbidity. The unit of measurement is the nephelometric turbidity unit (NTU), which is measured at 2S C and in a 10% strength by weight aqueous solu-tion and defined by calibration on the basis of formazine as artificial turbidifier. The higher the NTU value, the greater the 30 turbidity of the solution.
Preparation of polymers Example 1 First the following solutions were pre-prepared:
1. Solution 1, consisting of 150 g of ethyl acrylate, 250 g of isobutyl methacrylate and g of isopropanol.
2. Solution 2, consisting of 100 g of 2-acrylamido-2-methyl-propanesulfonic acid, 17 g of sodium hydroxide and 100 g of water.
3. Monomer portion, consisting of solution 1 and solution 2.
4. Initiator stream, consisting of 8 g of t-butyl peroxypivalate dissolved in 150 g of isopropanol.
5. Initial charge, consisting of 90 g of monomer portion, 200 g of isopropanol and 0.5 g of t-butyl peroxypivalate.
The initial charge was heated under nitrogen to 78 C under a pres-sure of 1.5 bar. Simultaneously with the onset of the polymeriza-tion, discernible from the exothermic reaction, a start was made lO on the addition of the initiator stream and the remainder of the monomer, the rest of the monomer being added over a period of 8 hours and the initiator over a period of 16 hours. Afterwards the polymerization mixture was maintained at 78 C for a further 3 hours.
Thereafter the solvent exchange was effected by adding water and removing the isopropanol by steam distillation.
The resulting aqueous polymer solution had a solids content of 20 30% by weight. The K value (measured at 1% strength in N-methyl-pyrrolidone) was 33.7. Dilution with water to 10% solids resulted in a solution having an NTU value of 30, while similar dilution with ethanol to 10% solids resulted in a solution with an NTU
value of 15.
Example 2 Example 1 was repeated with a solution 1 containing 150 g of ethyl acrylate and 250 g of tert-butyl acrylate as monomers. The 30 K value was 26.5 (measured at 1% strength in N-methylpyrroli-done). The NTU value of a 5% strength by weight aqueous solution was 12.8.
Example 3 Example 1 was repeated with solution 1 contA;n;ng 350 g of tert-butyl acrylate and 100 g of N-vinylpyrrolidone and solution 2 containing 50 g of 2-acrylamido-2-methylpropanesulfonic acid and 8.5 g of NaOH. The K value was 24.5, and the NTU value of a 5%
40 strength by weight aqueous solution was 16.
Formulation example 1: Pump spray, normal setting 5% by weight of polymer of Example 2 95% by weight of water q.s. preservative q.s. perfume and solubilizer (q.s.: as much as suffices) Formulation example 2: Pump spray, strong setting 10% by weight of polymer of Example 2 90% by weight of water q.s. preservative q.s. perfume and solubilizer 10 Formulation example 3: Hairspray without ethanol, normal setting 5% by weight of polymer of Example 2 65% by weight of water 30% by weight of dimethyl ether ~DME) q.s. perfume and solubilizer Formulation example 4: Hair lotion, normal setting 4% by weight of polymer of Example 2 86% by weight of water q.s. preservative q.s. perfume and solubilizer The polymers of Example 2 can be formulated not only as pure aqueous pump sprays but also as aqueous aerosol sprays with dimethyl ether as propellant. The formulation of an aqueous hair lotion is described in Example 4. The polymers of the present invention have the normal to strong setting effect on hair. The water absorption of the treated hair is minimal, so that the styled hair has a longer hold and is less sticky.
30 Furthermore, the hair setting and hair care compositions of the present invention are notable in that they do not stick the hair together to any practical extent, and are readily combed out. The treated hair has a natural appearance. The hair stiffening effect obtained with compositions according to the present invention is without exception good.
The initial charge was heated under nitrogen to 78 C under a pres-sure of 1.5 bar. Simultaneously with the onset of the polymeriza-tion, discernible from the exothermic reaction, a start was made lO on the addition of the initiator stream and the remainder of the monomer, the rest of the monomer being added over a period of 8 hours and the initiator over a period of 16 hours. Afterwards the polymerization mixture was maintained at 78 C for a further 3 hours.
Thereafter the solvent exchange was effected by adding water and removing the isopropanol by steam distillation.
The resulting aqueous polymer solution had a solids content of 20 30% by weight. The K value (measured at 1% strength in N-methyl-pyrrolidone) was 33.7. Dilution with water to 10% solids resulted in a solution having an NTU value of 30, while similar dilution with ethanol to 10% solids resulted in a solution with an NTU
value of 15.
Example 2 Example 1 was repeated with a solution 1 containing 150 g of ethyl acrylate and 250 g of tert-butyl acrylate as monomers. The 30 K value was 26.5 (measured at 1% strength in N-methylpyrroli-done). The NTU value of a 5% strength by weight aqueous solution was 12.8.
Example 3 Example 1 was repeated with solution 1 contA;n;ng 350 g of tert-butyl acrylate and 100 g of N-vinylpyrrolidone and solution 2 containing 50 g of 2-acrylamido-2-methylpropanesulfonic acid and 8.5 g of NaOH. The K value was 24.5, and the NTU value of a 5%
40 strength by weight aqueous solution was 16.
Formulation example 1: Pump spray, normal setting 5% by weight of polymer of Example 2 95% by weight of water q.s. preservative q.s. perfume and solubilizer (q.s.: as much as suffices) Formulation example 2: Pump spray, strong setting 10% by weight of polymer of Example 2 90% by weight of water q.s. preservative q.s. perfume and solubilizer 10 Formulation example 3: Hairspray without ethanol, normal setting 5% by weight of polymer of Example 2 65% by weight of water 30% by weight of dimethyl ether ~DME) q.s. perfume and solubilizer Formulation example 4: Hair lotion, normal setting 4% by weight of polymer of Example 2 86% by weight of water q.s. preservative q.s. perfume and solubilizer The polymers of Example 2 can be formulated not only as pure aqueous pump sprays but also as aqueous aerosol sprays with dimethyl ether as propellant. The formulation of an aqueous hair lotion is described in Example 4. The polymers of the present invention have the normal to strong setting effect on hair. The water absorption of the treated hair is minimal, so that the styled hair has a longer hold and is less sticky.
30 Furthermore, the hair setting and hair care compositions of the present invention are notable in that they do not stick the hair together to any practical extent, and are readily combed out. The treated hair has a natural appearance. The hair stiffening effect obtained with compositions according to the present invention is without exception good.
Claims (5)
1. Polymers suitable for use in aqueous hairsetting composi-tions, obtainable by free-radically initiated solution poly-merization of a monomer mixture of A) 50 - 90% by weight of one or more monomers selected from the group consisting of C1-C18-alkyl esters of acrylic or methacrylic acid and vinyl esters of saturated C2-C10-monocarboxylic acids, B) 10 - 25% by weight of a sulfo-containing vinyl monomer, and C) 0 - 40% by weight of a further monomer selected from the group consisting of acrylic acid, methacrylic acid, acrylamide, methacrylamide, C3-C8-N-alkylacrylamide, N,N-dimethylacrylamide, N-vinylpyrrolidone and N-vinyl-caprolactam.
2. Polymers as claimed in claim 1, wherefor the sulfo groups of monomer B) are in whole or in part present as salts of inor-ganic bases or of organic C1-C8 nitrogen bases.
3. Polymers as claimed in claim 1 or 2, obtainable from a mono-mer mixture consisting of A) 70 - 85% by weight of one or more C1-C8-alkyl esters of acrylic or methacrylic acid, B) 10 - 20% by weight of 2-acrylamido-2-methylpropane-sulfonic acid, and C) 0 - 25% by weight of N-vinylpyrrolidone.
4. Hairsetting compositions comprising polymers as claimed in any of claims 1 to 3 as film-former.
5. Hairsetting compositions as claimed in claim 4, comprising water as solvent.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1995107249 DE19507249A1 (en) | 1995-03-02 | 1995-03-02 | Polymers containing sulfo groups suitable for use in hair fixatives |
| DE19507249.9 | 1995-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2170567A1 true CA2170567A1 (en) | 1996-09-03 |
Family
ID=7755430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2170567 Abandoned CA2170567A1 (en) | 1995-03-02 | 1996-02-28 | Sulfo-containing polymers suitable for use in hairsetting compositions |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0729987A2 (en) |
| JP (1) | JPH08253536A (en) |
| CN (1) | CN1138592A (en) |
| CA (1) | CA2170567A1 (en) |
| DE (1) | DE19507249A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130102943A1 (en) * | 2009-09-08 | 2013-04-25 | Schoeller Textil Ag | Reloadable finishes for textiles and formulations for loading such finishes |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6537663B1 (en) * | 2000-05-04 | 2003-03-25 | Kimberly-Clark Worldwide, Inc. | Ion-sensitive hard water dispersible polymers and applications therefor |
| JP4536433B2 (en) * | 2004-06-24 | 2010-09-01 | 花王株式会社 | Polymer emulsion for cosmetics |
| DE102004051648A1 (en) * | 2004-10-22 | 2006-04-27 | Basf Ag | Anionic ethyl methacrylate copolymers and their use |
| DE102004051647A1 (en) * | 2004-10-22 | 2006-07-06 | Basf Ag | Cosmetic preparations containing ethyl methacrylate copolymers |
| DE102008054391B4 (en) * | 2008-12-08 | 2019-03-07 | Wacker Chemie Ag | Particulate preparations with dispersing agents and process for the preparation of the preparations |
| CN101735382B (en) * | 2009-12-21 | 2013-03-20 | 广州天赐高新材料股份有限公司 | Forming polymer for amine oxide type amphoteric hair and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS536214B2 (en) * | 1972-08-24 | 1978-03-06 |
-
1995
- 1995-03-02 DE DE1995107249 patent/DE19507249A1/en not_active Withdrawn
-
1996
- 1996-02-26 EP EP96102837A patent/EP0729987A2/en not_active Withdrawn
- 1996-02-28 CA CA 2170567 patent/CA2170567A1/en not_active Abandoned
- 1996-03-01 JP JP4515796A patent/JPH08253536A/en not_active Withdrawn
- 1996-03-02 CN CN 96105534 patent/CN1138592A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130102943A1 (en) * | 2009-09-08 | 2013-04-25 | Schoeller Textil Ag | Reloadable finishes for textiles and formulations for loading such finishes |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1138592A (en) | 1996-12-25 |
| EP0729987A3 (en) | 1996-09-11 |
| JPH08253536A (en) | 1996-10-01 |
| EP0729987A2 (en) | 1996-09-04 |
| DE19507249A1 (en) | 1996-09-05 |
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