CA2172670A1 - Use of carboxyl-containing polycondensates as auxiliaries in cosmetic preparations - Google Patents
Use of carboxyl-containing polycondensates as auxiliaries in cosmetic preparationsInfo
- Publication number
- CA2172670A1 CA2172670A1 CA 2172670 CA2172670A CA2172670A1 CA 2172670 A1 CA2172670 A1 CA 2172670A1 CA 2172670 CA2172670 CA 2172670 CA 2172670 A CA2172670 A CA 2172670A CA 2172670 A1 CA2172670 A1 CA 2172670A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- acids
- mol
- hair
- group
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
Classifications
-
- 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)
-
- 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
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/85—Polyesters
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Abstract
The use of carboxyl-containing water-dispersible polycondensation products having glass transition temperatures Tg > 20°C and acid numbers of from 30 to 160, obtainable by condensation of A) from 0.3 to 15 mol% of at least one compound selected from the group consisting of 2,2-dimethylolpropanoic acid, 1,3,5-benzenetricarboxylic acid and its C1-C8-alkyl esters and acid chlorides, and 5-hydroxyisophthalic acids and their acyl derivatives, and B) from 85 to 99.7 mol% of a mixture of B1) a saturated diol or a C2-C8-diamine or mixtures thereof, and B2) at least one compound from the group consisting of the monohydroxycarboxylic acids and their lactones, the di-carboxylic acids excluding the isophthalic acid deriva-tives mentioned under A), and the aminocarboxylic acids, as auxiliaries in cosmetic preparations is described.
Description
Use of carboxyl-containing polycondensates as auxiliaries in cos-metic preparations The present invention relates to the use of carboxyl-containing water-dispersible polycondensation products having glass transi-tion temperatures Tg > 20 C and acid numbers of from 30 to 160, obtainable by condensation of 10 A) from 0.3 to 15 mol% of at least one compound selected from the group consisting of 2,2-dimethylolpropanoic acid, 1,3,5-benzenetricarboxylic acid and its Cl-Cg-alkyl esters and acid chlorides, and 5-hydroxyisophthalic acids and their 5-acyl derivatives, and B) from 85 to 99.7 mol% of a mixture of B1) a saturated diol or a C2-C8-diamine or mixtures thereof, and B2) at least one compound from the group consisting of the monohydroxycarboxylic acids and their lactones, the di-carboxylic acids excluding the isophthalic acid deriva-tives mentioned under A), and the aminocarboxylic acids, as auxiliaries in cosmetic preparations, in particular in hair treatment compositions. The invention furthermore relates to hair treatment compositions containing polycondensation products as film-forming agents.
On account of the continuously growing demand for more environ-mentally tolerable feedstocks, the content of volatile organic constituents (volatile organic compounds - VOC) should also be kept as low as possible or reduced in cosmetic preparations such as hairspray. This means that the alcohol should increasingly be replaced by water as a solvent.
When using conventional hair setting polymers, however, this can cause difficulties, as at relatively high water contents viscos-40 ity and spray behavior of the hair setting compositions and thedrying of the polymer films are unsatisfactory.
US-A 4 300 580 discloses sodium sulfonate-containing linear poly-condensates which are suitable for use in hair treatment composi-tions. Such polycondensates, however, have a poor compatibility ~1 72670 with organic solvents and leave something to be desired with re-spect to washing-out ability.
It is furthermore disclosed in DE-AS 26 33 418 and DE-AS
25 06 461 to employ sodium sulfonate-containing branched polyes-ters in hair-treatment compositions. These compositions as well have unsatisfactory compatibility with organic solvents.
DE-OS 42 24 761 describes carboxyl-containing branched polycon-10 densates for use in cosmetic preparations, which are obtained on the basis of aromatic carboxylic acids having vicinal carboxylic acid groups. These polycondensates have some disadvantages with respect to stability to hydrolysis.
It is an object of the present invention to find polymers for use as film-forming agents in hair setting compositions which make possible increased proportions of water in the corresponding cos-metic preparations without causing a viscosity increase or adversely affecting other application properties such as the 20 spray behavior. After application to the hair, nonsticky, clear films having a good setting action and good washing-out ability should additionally be obtained.
We have found that this object is achieved by the use of the polycondensation products defined at the beginning, and cosmetic preparations containing these.
The polycondensation products are obtainable by condensation of the following components.
Components (A) employed are trifunctional compounds, selected from the group consisting of 2,2-dimethylolpropanoic acid, 1,3,5-benzenetricarboxylic acid, 1,3,5-benzenetricarboxylic acid mono- or trialkyl esters having Cl-C8-alkyl radicals, acid chlorides of l,3,5-benzenetricarboxylic acid and 5-acyloxyiso-phthalic acids, preferably 5-acetoxyisophthalic acid. Particu-larly preferred components A) are 2,2-dimethylolpropanoic acid and l,3,5-benzenetricarboxylic acid. If esters or acid chlorides of benzenedicarboxylic acid are used, these are transesterified 40 under the conditions of the condensation such that they are also trifunctional compounds.
The components A) are employed in amounts of from 0.3 to 15 mol%, preferably 1 to 12 mol%, based on the total amount of starting compounds.
21 726~U
Components B) employed are from 85 to 99.7, preferably from 88 to 99 mol% of a mixture of Bl) and B2), B1) preferably being employed in amounts from 10 to 49 mol% and B2) in amounts from 30 to 80 mol%, in each case based on the total amount of A) and B).
The ratio of acid groups employed to hydroxyl groups employed should preferably be from 0.95:1 to 1.2:1.
Possible components Bl) are one or more compounds selected from the group consisting of the saturated diols and the saturated di-10 primary C2-C8-diamines. Suitable diols are, for example, C2-C8-diols such as ethylene glycol, diethylene glycol, 1,2- and 1,3-propanediol, 1,2-butanediol, 1,4-butanediol, neopentyl glycol, l,4-cyclohexyldimethylol or polyether diols having molecular weights up to 500 such as polyoxyethylene glycol, polyoxypropylene glycol or polytetrahydrofuran. Suitable diamines are, for example, ethylenediamine, l,4-butylenediamine or 1,6-hexamethylenediamine.
Possible components B2) are compounds selected from the group 20 consisting of the hydroxycarboxylic acids, dicarboxylic acids and aminocarboxylic acids. Suitable monohydroxycarboxylic acids are, for example, lactic acid, 2-hydroxyacetic acid or 3-hydroxypival-ic acid or lactones such as E-caprolactone. Suitable dicarboxylic acids, which differ from the 5-hydroxyisophthalic acid and its derivatives mentioned under A), are, for example, mononuclear aromatic dicarboxylic acids, for example phthalic acid, trimellitic acid, terephthalic acid or isophthalic acid, which, however, preferably do not carry any vicinal carboxylic acid groups, isophthalic acid being particularly preferred.
30 Furthermore, cycloalkane- or alkanedicarboxylic acids having 2 to 8 C atoms are suitable, for example adipic acid, succinic acid or 1,4-cyclohexyldicarboxylic acid. Possible components B2) are also aminocarboxylic acids having 2 to 8 C atoms or their lactams, for example ~-caprolactam.
Additionally, up to 3 mol%, based on the total number of moles of starting compounds, of a further trifunctional compound or up to 1 mol% of a diisocyanate can be added to increase the molecular weight. Suitable trifunctional compounds are saturated triols 40 such as glycerol or trimethylolpropane. Suitable diisocyanates are, for example, isophorone diisocyanate or hexamethylene diiso-cyanate.
On account of the continuously growing demand for more environ-mentally tolerable feedstocks, the content of volatile organic constituents (volatile organic compounds - VOC) should also be kept as low as possible or reduced in cosmetic preparations such as hairspray. This means that the alcohol should increasingly be replaced by water as a solvent.
When using conventional hair setting polymers, however, this can cause difficulties, as at relatively high water contents viscos-40 ity and spray behavior of the hair setting compositions and thedrying of the polymer films are unsatisfactory.
US-A 4 300 580 discloses sodium sulfonate-containing linear poly-condensates which are suitable for use in hair treatment composi-tions. Such polycondensates, however, have a poor compatibility ~1 72670 with organic solvents and leave something to be desired with re-spect to washing-out ability.
It is furthermore disclosed in DE-AS 26 33 418 and DE-AS
25 06 461 to employ sodium sulfonate-containing branched polyes-ters in hair-treatment compositions. These compositions as well have unsatisfactory compatibility with organic solvents.
DE-OS 42 24 761 describes carboxyl-containing branched polycon-10 densates for use in cosmetic preparations, which are obtained on the basis of aromatic carboxylic acids having vicinal carboxylic acid groups. These polycondensates have some disadvantages with respect to stability to hydrolysis.
It is an object of the present invention to find polymers for use as film-forming agents in hair setting compositions which make possible increased proportions of water in the corresponding cos-metic preparations without causing a viscosity increase or adversely affecting other application properties such as the 20 spray behavior. After application to the hair, nonsticky, clear films having a good setting action and good washing-out ability should additionally be obtained.
We have found that this object is achieved by the use of the polycondensation products defined at the beginning, and cosmetic preparations containing these.
The polycondensation products are obtainable by condensation of the following components.
Components (A) employed are trifunctional compounds, selected from the group consisting of 2,2-dimethylolpropanoic acid, 1,3,5-benzenetricarboxylic acid, 1,3,5-benzenetricarboxylic acid mono- or trialkyl esters having Cl-C8-alkyl radicals, acid chlorides of l,3,5-benzenetricarboxylic acid and 5-acyloxyiso-phthalic acids, preferably 5-acetoxyisophthalic acid. Particu-larly preferred components A) are 2,2-dimethylolpropanoic acid and l,3,5-benzenetricarboxylic acid. If esters or acid chlorides of benzenedicarboxylic acid are used, these are transesterified 40 under the conditions of the condensation such that they are also trifunctional compounds.
The components A) are employed in amounts of from 0.3 to 15 mol%, preferably 1 to 12 mol%, based on the total amount of starting compounds.
21 726~U
Components B) employed are from 85 to 99.7, preferably from 88 to 99 mol% of a mixture of Bl) and B2), B1) preferably being employed in amounts from 10 to 49 mol% and B2) in amounts from 30 to 80 mol%, in each case based on the total amount of A) and B).
The ratio of acid groups employed to hydroxyl groups employed should preferably be from 0.95:1 to 1.2:1.
Possible components Bl) are one or more compounds selected from the group consisting of the saturated diols and the saturated di-10 primary C2-C8-diamines. Suitable diols are, for example, C2-C8-diols such as ethylene glycol, diethylene glycol, 1,2- and 1,3-propanediol, 1,2-butanediol, 1,4-butanediol, neopentyl glycol, l,4-cyclohexyldimethylol or polyether diols having molecular weights up to 500 such as polyoxyethylene glycol, polyoxypropylene glycol or polytetrahydrofuran. Suitable diamines are, for example, ethylenediamine, l,4-butylenediamine or 1,6-hexamethylenediamine.
Possible components B2) are compounds selected from the group 20 consisting of the hydroxycarboxylic acids, dicarboxylic acids and aminocarboxylic acids. Suitable monohydroxycarboxylic acids are, for example, lactic acid, 2-hydroxyacetic acid or 3-hydroxypival-ic acid or lactones such as E-caprolactone. Suitable dicarboxylic acids, which differ from the 5-hydroxyisophthalic acid and its derivatives mentioned under A), are, for example, mononuclear aromatic dicarboxylic acids, for example phthalic acid, trimellitic acid, terephthalic acid or isophthalic acid, which, however, preferably do not carry any vicinal carboxylic acid groups, isophthalic acid being particularly preferred.
30 Furthermore, cycloalkane- or alkanedicarboxylic acids having 2 to 8 C atoms are suitable, for example adipic acid, succinic acid or 1,4-cyclohexyldicarboxylic acid. Possible components B2) are also aminocarboxylic acids having 2 to 8 C atoms or their lactams, for example ~-caprolactam.
Additionally, up to 3 mol%, based on the total number of moles of starting compounds, of a further trifunctional compound or up to 1 mol% of a diisocyanate can be added to increase the molecular weight. Suitable trifunctional compounds are saturated triols 40 such as glycerol or trimethylolpropane. Suitable diisocyanates are, for example, isophorone diisocyanate or hexamethylene diiso-cyanate.
The molar amounts of the starting components are preferably pro-portioned such that the resulting polycondensation products have acid numbers of from 30 to 160 mg of KOH/g of substance, prefer-ably from 40 to 100.
Preferred polycondensation products are polyesters according to the invention.
The polycondensation products can be prepared in a manner known 10 per se. Customarily, the condensation can be carried out as a melt condensation at temperatures in the range from 160 to 260 C
during a period of time of several hours (for example from 5 to 20 h) under a nitrogen atmosphere at pressures of from 0.2 to 2 bar, preferably under normal pressure, the resulting water of reaction being removed by distillation. Towards the end of the reaction, water of reaction still present in the product can be removed by distillation at from 1 to 100 mbar at from 210 to 230 C. It can also be recommended to add small amounts of custom-ary catalysts to the reaction mixture, for example tetraisopropyl 20 orthosilicate, amounts in the range from 10 to 100 ppm customar-ily being selected.
The water-dispersible or water-soluble polycondensation products thus obtained are colorless to honey-yellow products having rela-tively low viscosity and K values (measured at 1 % strength in N-methylpyrrolidone) according to Fikentscher, in the range from 20 to 40. The glass transition temperatures are > 20 C.
The polycondensation products are pre~erably used in partially or 30 completely neutralized form in aqueous dispersions, using, for example, 2-amino-2-methylpropanol as a neutralizing agent.
The sulfonate-free polycondensation products are used according to the invention as auxiliaries in cosmetic preparations such as skin creams, skin lotions or nail varnish and in particular in v-hair-cosmetic preparations, especially in hair setting composi-tions such as hairsprays, setting lotions or foam setting agents.
Owing to the good water compatibility purely aqueous preparations 40 can be prepared, the good resistance to hydrolysis being advanta-geous. The polycondensation products, however, are also readily compatible with organic solvents and organic propellants.
On account of the low viscosities, hair-cosmetic preparations with high solid contents can be prepared, so that less solvent is needed.
Besides the good environmental compatibility of the products, with which there are no residual monomer problems, they also, however, have good film-forming properties.
In the hair-cosmetic preparations according to the invention, the polycondensation products can be used both as film-forming agents on their own and as mixtures with conventional polymers suitable for such purposes, mixture ratios of polycondensates to conven-tional polymers of from 1:0.1 to 1:2 being recommended. Suitable 10 conventional hair setting polymers are, for example, anionic polymers such as acrylic acid or methacrylic acid homopolymers or copolymers, copolymers of acrylic acid and acrylamides and copo-lymers based on alkyl vinyl ethers and maleic acid monoalkyl es-ters, amphoteric polymers such as copolymers of octylacrylamide, acrylate and butylaminoethyl methacrylate and nonionic polymers such as vinylpyrrolidone homopolymers, vinylpyrrolidone/vinyl acetate copolymers and copolymers of vinylpyrrolidone, vinyl ace-tate and vinyl propionate.
20 Combinations of polycondensation products with polyvinylcaprolac-tam are particularly suitable.
The hair-cosmetic preparations according to the invention can contain the polycondensation products in amounts of from 0.1 to 25, preferably from 1 to 15, % by weight.
The preparations according to the invention can be used as purely aqueous preparations or in aqueous-alcoholic solution with etha-nol or isopropanol with or without propellant. A suitable propel-30 lant is, for example, dimethyl ether. The preparations accordingto the invention are preferably formulated with up to 80 % by weight of volatile organic solvents.
The hair-cosmetic preparations can furthermore contain customary auxiliaries such as surfactants, emulsifiers or fragrances.
Examples 1 to 10 General procedure for the preparation of the polycondensates A mixture of the starting compounds (for amounts see table) and 50 ppm of tetraisopropyl orthosilicate was heated under a nitro-gen atmosphere with stirring to from 160 to 180 C and kept at this temperature for 3 h, the resulting water of reaction being re-moved by distillation. The clear melt was heated to 200 C for a further 15 h, then the temperature was raised 15 C hourly until it was in the range 220-240 C. It was then additionally heated for 2 1 ~2tj~0 2 h at 20 mbar, residues of the water of reaction being removed.
After cooling, clear pale-yellow to yellow products were ob-tained.
Table Composition [mol]
Ex. BTS DMPIPS ADS NPG CHD DEG PPG Mis E-CL. Tg SZ
10 No. A M 450 [C]
1 1 - - - 1.2 - - - 6 - 64 89.7 2 1.5 - 8.5 - 5 - 5 - - - 59 69.8 3 1.2 - 8.75 - 5 - 5 - 5 - 56 84.5 4 1 - 8.6 - 5 - 5 - - 2 48 69 0.6 0.4 8.4 0.2 5 - 5 - 3 1 53 85 6 - 2.5 11 - 8.5 - 1 - 10 - 57 94 7 - 1.5 10 - 8 - 1.5 - 3 - 59 78 8 - 1 9.6 - 7 1 0.5 - - - 59 65.5 9 - 1 10 0.5 7.5 1 0.5 - - - 54 69 - 1.5 10 0.8 9 0.2 - 0.5 - - 53 72 BTS: 1, 3,5-benzenetricarboxylic acid DMPA: 2,2-dimethylolpropanoic acid IPS: isophthalic acid ADS: adipic acid NPG: neopentyl glycol CHDM: 1,4-cyclohexyldimethylol 30 DEG: diethylene glycol PPG 450: polypropylene glycol MW=450 Mis: lactic acid E-CL: E-caprolactone Tg: Glass transition temperature was determined by differential thermal analysis method ASTM D 3418.
SZ: Acid number, [mg of KOH/g of substance]
Formulation examples:
1) Aerosol hairspray: (VOC+)80) Polymer according to Example 5 3.00 % by weight 2-Amino-2-methylpropanol 0.43 % by weight Dist. water 16.67 % by weight Ethanol 45.00 % by weight Dimethyl ether 35.00 % by weight Perfume oil, surfactant q.s.++) corresponding VOC 80 formulations can be obtained using polymer 6 to 10.
2) Hand pump hairspray (VOC 55) Polymer according to Example 5 4.00 % by weight 2-Amino-2-methylpropanol 0.57 % by weight Dist. water 40.43 % by weight Ethanol 55.00 % by weight Perfume oil, surfactant q.s.++) corresponding VOC 55 formulations can be obtained using polymer 6 to 10.
3) Alcohol-free hand pump hairspray (VOC 0) Polymer according to Example 10 4.00 % by weight (neutralized with aminomethylpropanol) Polyvinylcaprolactam 4.00 % by weight (K value 35/1% strength DMF) Dist. water 82.00 % by weight Perfume oil, surfactant q.s.++) corresponding VOC 0 formulations can be obtained using - polymer 6 to 9.
+) VOC = Volatile Organic Content ++) q.s. as desired
Preferred polycondensation products are polyesters according to the invention.
The polycondensation products can be prepared in a manner known 10 per se. Customarily, the condensation can be carried out as a melt condensation at temperatures in the range from 160 to 260 C
during a period of time of several hours (for example from 5 to 20 h) under a nitrogen atmosphere at pressures of from 0.2 to 2 bar, preferably under normal pressure, the resulting water of reaction being removed by distillation. Towards the end of the reaction, water of reaction still present in the product can be removed by distillation at from 1 to 100 mbar at from 210 to 230 C. It can also be recommended to add small amounts of custom-ary catalysts to the reaction mixture, for example tetraisopropyl 20 orthosilicate, amounts in the range from 10 to 100 ppm customar-ily being selected.
The water-dispersible or water-soluble polycondensation products thus obtained are colorless to honey-yellow products having rela-tively low viscosity and K values (measured at 1 % strength in N-methylpyrrolidone) according to Fikentscher, in the range from 20 to 40. The glass transition temperatures are > 20 C.
The polycondensation products are pre~erably used in partially or 30 completely neutralized form in aqueous dispersions, using, for example, 2-amino-2-methylpropanol as a neutralizing agent.
The sulfonate-free polycondensation products are used according to the invention as auxiliaries in cosmetic preparations such as skin creams, skin lotions or nail varnish and in particular in v-hair-cosmetic preparations, especially in hair setting composi-tions such as hairsprays, setting lotions or foam setting agents.
Owing to the good water compatibility purely aqueous preparations 40 can be prepared, the good resistance to hydrolysis being advanta-geous. The polycondensation products, however, are also readily compatible with organic solvents and organic propellants.
On account of the low viscosities, hair-cosmetic preparations with high solid contents can be prepared, so that less solvent is needed.
Besides the good environmental compatibility of the products, with which there are no residual monomer problems, they also, however, have good film-forming properties.
In the hair-cosmetic preparations according to the invention, the polycondensation products can be used both as film-forming agents on their own and as mixtures with conventional polymers suitable for such purposes, mixture ratios of polycondensates to conven-tional polymers of from 1:0.1 to 1:2 being recommended. Suitable 10 conventional hair setting polymers are, for example, anionic polymers such as acrylic acid or methacrylic acid homopolymers or copolymers, copolymers of acrylic acid and acrylamides and copo-lymers based on alkyl vinyl ethers and maleic acid monoalkyl es-ters, amphoteric polymers such as copolymers of octylacrylamide, acrylate and butylaminoethyl methacrylate and nonionic polymers such as vinylpyrrolidone homopolymers, vinylpyrrolidone/vinyl acetate copolymers and copolymers of vinylpyrrolidone, vinyl ace-tate and vinyl propionate.
20 Combinations of polycondensation products with polyvinylcaprolac-tam are particularly suitable.
The hair-cosmetic preparations according to the invention can contain the polycondensation products in amounts of from 0.1 to 25, preferably from 1 to 15, % by weight.
The preparations according to the invention can be used as purely aqueous preparations or in aqueous-alcoholic solution with etha-nol or isopropanol with or without propellant. A suitable propel-30 lant is, for example, dimethyl ether. The preparations accordingto the invention are preferably formulated with up to 80 % by weight of volatile organic solvents.
The hair-cosmetic preparations can furthermore contain customary auxiliaries such as surfactants, emulsifiers or fragrances.
Examples 1 to 10 General procedure for the preparation of the polycondensates A mixture of the starting compounds (for amounts see table) and 50 ppm of tetraisopropyl orthosilicate was heated under a nitro-gen atmosphere with stirring to from 160 to 180 C and kept at this temperature for 3 h, the resulting water of reaction being re-moved by distillation. The clear melt was heated to 200 C for a further 15 h, then the temperature was raised 15 C hourly until it was in the range 220-240 C. It was then additionally heated for 2 1 ~2tj~0 2 h at 20 mbar, residues of the water of reaction being removed.
After cooling, clear pale-yellow to yellow products were ob-tained.
Table Composition [mol]
Ex. BTS DMPIPS ADS NPG CHD DEG PPG Mis E-CL. Tg SZ
10 No. A M 450 [C]
1 1 - - - 1.2 - - - 6 - 64 89.7 2 1.5 - 8.5 - 5 - 5 - - - 59 69.8 3 1.2 - 8.75 - 5 - 5 - 5 - 56 84.5 4 1 - 8.6 - 5 - 5 - - 2 48 69 0.6 0.4 8.4 0.2 5 - 5 - 3 1 53 85 6 - 2.5 11 - 8.5 - 1 - 10 - 57 94 7 - 1.5 10 - 8 - 1.5 - 3 - 59 78 8 - 1 9.6 - 7 1 0.5 - - - 59 65.5 9 - 1 10 0.5 7.5 1 0.5 - - - 54 69 - 1.5 10 0.8 9 0.2 - 0.5 - - 53 72 BTS: 1, 3,5-benzenetricarboxylic acid DMPA: 2,2-dimethylolpropanoic acid IPS: isophthalic acid ADS: adipic acid NPG: neopentyl glycol CHDM: 1,4-cyclohexyldimethylol 30 DEG: diethylene glycol PPG 450: polypropylene glycol MW=450 Mis: lactic acid E-CL: E-caprolactone Tg: Glass transition temperature was determined by differential thermal analysis method ASTM D 3418.
SZ: Acid number, [mg of KOH/g of substance]
Formulation examples:
1) Aerosol hairspray: (VOC+)80) Polymer according to Example 5 3.00 % by weight 2-Amino-2-methylpropanol 0.43 % by weight Dist. water 16.67 % by weight Ethanol 45.00 % by weight Dimethyl ether 35.00 % by weight Perfume oil, surfactant q.s.++) corresponding VOC 80 formulations can be obtained using polymer 6 to 10.
2) Hand pump hairspray (VOC 55) Polymer according to Example 5 4.00 % by weight 2-Amino-2-methylpropanol 0.57 % by weight Dist. water 40.43 % by weight Ethanol 55.00 % by weight Perfume oil, surfactant q.s.++) corresponding VOC 55 formulations can be obtained using polymer 6 to 10.
3) Alcohol-free hand pump hairspray (VOC 0) Polymer according to Example 10 4.00 % by weight (neutralized with aminomethylpropanol) Polyvinylcaprolactam 4.00 % by weight (K value 35/1% strength DMF) Dist. water 82.00 % by weight Perfume oil, surfactant q.s.++) corresponding VOC 0 formulations can be obtained using - polymer 6 to 9.
+) VOC = Volatile Organic Content ++) q.s. as desired
Claims (10)
1. The use of sulfonate-free carboxyl-containing water-dispers-ible polycondensation products having glass transition tem-peratures Tg > 20 C and acid numbers of from 30 to 160, ob-tainable by condensation of A) from 0.3 to 15 mol% of at least one compound selected from the group consisting of 2,2-dimethylolpropanoic acid, 1,3,5-benzenetricarboxylic acid and its C1-C8-alkyl esters and acid chlorides, and 5-hydroxyisophthalic acids and their acyl derivatives, and B) from 85 to 99.7 mol% of a mixture of B1) a saturated diol or a C2-C8-diamine or mixtures thereof, and B2) at least one compound from the group consisting of the monohydroxycarboxylic acids and their lactones, the dicarboxylic acids excluding the isophthalic acid derivatives mentioned under A), and the aminocarbox-ylic acids, as auxiliaries in cosmetic preparations.
2. The use as claimed in claim 1, from 1 to 12 mol% of the com-ponent A) being employed for the polycondensation products.
3. The use as claimed in claim 1 or 2, polyesters being used as polycondensation products.
4. The use as claimed in one of claims 1 to 3 in hair-cosmetic preparations.
5. The use as claimed in claim 4 as hair setting polymers.
6. A hair-cosmetic preparation, containing as a film-forming agent carboxyl-containing polycondensation products having glass transition temperatures Tg > 20°C and acid numbers of from 30 to 160, obtainable by condensation of A) from 0.3 to 15 mol% of at least one compound selected from the group consisting of 2,2-dimethylolpropanoic acid, 1,3,5-benzenetricarboxylic acid and its C1-C8-alkyl esters and acid chlorides and 5-hydroxyisophthalic acids, and B) from 85 to 99.7 mol% of a mixture of B1) a saturated diol or a C2-C8-diamine or mixtures thereof, and B2) at least one compound from the group consisting of the monohydroxycarboxylic acids and their lactones, the dicarboxylic acids excluding 5-hydroxyisophthalic acids, and the aminocarboxylic acids.
7. A preparation as claimed in claim 6, containing the polycon-densation products in an amount from 0.1 to 25 % by weight, based on the solids content.
8. A preparation as claimed in claim 6, containing the polycon-densation products in the form of an aqueous dispersion or aqueous-ethanolic solution, and customary hair-cosmetic aux-iliaries.
9. A preparation as claimed in claim 6 or 7, containing a poly-ester as a film-forming agent.
10. A preparation as claimed in one of claims 6 to 9, addition-ally containing further polymers customary for hair cos-metics.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1995110684 DE19510684A1 (en) | 1995-03-27 | 1995-03-27 | Use of carboxyl group-containing polycondensates as auxiliaries in cosmetic preparations |
| DE19510684.9 | 1995-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2172670A1 true CA2172670A1 (en) | 1996-09-28 |
Family
ID=7757537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2172670 Abandoned CA2172670A1 (en) | 1995-03-27 | 1996-03-26 | Use of carboxyl-containing polycondensates as auxiliaries in cosmetic preparations |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0734714A3 (en) |
| JP (1) | JPH08268847A (en) |
| CA (1) | CA2172670A1 (en) |
| DE (1) | DE19510684A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5968494A (en) | 1998-02-24 | 1999-10-19 | National Starch And Chemical Investment Holding Corporation | Polyurethanes with carboxylate functionality for hair fixative applications |
| DE102004029310A1 (en) * | 2004-06-17 | 2005-12-29 | Clariant Gmbh | Highly concentrated, aqueous formulations of oligoesters and polyesters |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4179420A (en) * | 1975-10-21 | 1979-12-18 | Schenectady Chemicals, Inc. | Water soluble insulating varnish |
| US4525524A (en) * | 1984-04-16 | 1985-06-25 | The Goodyear Tire & Rubber Company | Polyester composition |
| JP2951784B2 (en) * | 1991-12-24 | 1999-09-20 | 日立化成工業株式会社 | Method for producing polyester resin for paint and paint |
| DE4224761A1 (en) * | 1992-07-27 | 1994-02-03 | Basf Ag | Use of polycondensates and new polycondensates |
| DE4428003A1 (en) * | 1994-08-08 | 1996-02-15 | Basf Ag | Polyamides containing sulfonate groups and their use in hair fixatives |
-
1995
- 1995-03-27 DE DE1995110684 patent/DE19510684A1/en not_active Withdrawn
-
1996
- 1996-03-20 EP EP96104378A patent/EP0734714A3/en not_active Withdrawn
- 1996-03-26 CA CA 2172670 patent/CA2172670A1/en not_active Abandoned
- 1996-03-27 JP JP7251996A patent/JPH08268847A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE19510684A1 (en) | 1996-10-02 |
| EP0734714A3 (en) | 1998-04-15 |
| EP0734714A2 (en) | 1996-10-02 |
| JPH08268847A (en) | 1996-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5674479A (en) | Clear aerosol hair spray formulations containing a linear sulfopolyester in a hydroalcoholic liquid vehicle | |
| US5164177A (en) | Aqueous hair styling aid | |
| CA2120644C (en) | Use of polyurethanes with carboxylate functionality for hair fixative applications | |
| US6156077A (en) | Hair cosmetic composition comprising an oxyalkylenized xanthan gum | |
| KR960016191B1 (en) | Hair treatment composition | |
| US5498690A (en) | Use of polycondensation products, and novel polycondensation products | |
| CA2149425C (en) | Aerosol hair spray formulations | |
| JP2010270131A (en) | Alkoxylated fatty alcohol dicarboxylic acid ester | |
| EP1218430A1 (en) | Cosmetic based on oligomers and polymers containing urethane and/or urea functional group | |
| US6368583B1 (en) | Hair treatment composition | |
| US4961921A (en) | Non-aerosol pump spray compositions | |
| JPH037641B2 (en) | ||
| US7923526B2 (en) | Sulfopolyesters having improved clarity in water-dispersible formulations and products made therefrom | |
| AU5172999A (en) | Compositions containing a polycondensate comprising at least one polyurethane and/or polyurea unit and a silicone comprising at least one carboxylic function | |
| CA2172670A1 (en) | Use of carboxyl-containing polycondensates as auxiliaries in cosmetic preparations | |
| US6998114B2 (en) | Hair grooming formulations and methods for the use thereof | |
| US20070218091A1 (en) | Gel with a High Concentration of Branched Sulphonic Polyester and Method For Preparing Same | |
| KR100284351B1 (en) | Topical composition comprising a hydrrophilic gelling agent of polyester sulphone type | |
| JP2010168293A (en) | Hair cosmetic | |
| JPH03261713A (en) | Hair cosmetic | |
| FR2760636A1 (en) | VAPORIZED GELIFIED COMPOSITION | |
| JPH07145023A (en) | Aerosol spray composition for hair | |
| US6007794A (en) | Clear aerosol hair spray formulations containing a sulfopolyester in a hydroalcoholic liquid vehicle | |
| US5780013A (en) | Gliadin-containing hairspray | |
| JPH11152214A (en) | Hair cosmetic |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |