CA2066226A1 - Hair care preparations - Google Patents
Hair care preparationsInfo
- Publication number
- CA2066226A1 CA2066226A1 CA 2066226 CA2066226A CA2066226A1 CA 2066226 A1 CA2066226 A1 CA 2066226A1 CA 2066226 CA2066226 CA 2066226 CA 2066226 A CA2066226 A CA 2066226A CA 2066226 A1 CA2066226 A1 CA 2066226A1
- Authority
- CA
- Canada
- Prior art keywords
- preparations
- hair
- monomers
- group
- water
- 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
- A61K8/8141—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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
Landscapes
- 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)
- Cosmetics (AREA)
Abstract
SUBSTITUTE
REMPLACEMENT
SECTION is not Present Cette Section est Absente
REMPLACEMENT
SECTION is not Present Cette Section est Absente
Description
HAIR CAR~ PR~PARATION8 This invention relates to hair-treatment preparations containing zwitterionic polymers.
After washing, dyeing, or permanent waving, hair often shows unsatisfactory wet and dry combability, in addition to which the curl retention capacity of dry hair is inade-quate. To remedy this drawback, either appropriate com-ponents have to be added to the hair treatment prepara-tions, or the hair has to be subsequently subjected to a separate treatment with these substances which, for this purpose, are normally formulated as a rinse.
Polymeric compounds are frequently used as active sub-stances of the type in question to improve the properties of hair.
Although cationic polymers, such as for example the cellulose derivatives known from US Patents 3,816,616 and 3,472,840, are capable of distinctly improving wet comb-ability, they effect only unsati~factory hair-~etting and style-holding effects.
The use of zwitterionic polymers containing anionic groups, mostly carboxyl groups, and quaternary ammonium groups in the molecule in hair-treatment preparations is also known. For example, DE-OS 21 50 557 describes the use of polymers of zwitterionic monomers in hair-setting prep-arations. The use of copolymers of dimethylaminoethyl methacrylate, acrylic acid and methyl methacrylate in hair-setting lotions and shampoos is also known from DE-OS 28 17 369.
These known zwitterionic polymers in hair-treatment and hair-setting preparations have the disadvantage, par-ticularly in formulations with anionic surfactants, that their hair-conditioning and hair-setting properties are gradually lost in the event of prolonged storage. Accord-ingly, it was proposed in DE-OS 37 08 451 to use zwitter-ionic polymers consisting of 30 to 70% monomers containing quaternary ammonium groups, 10 to 30% monomeric olefinical-ly unsaturated carboxylic acids, 10 to 30% monomeric ole-finically unsaturated carboxylic acid esters and 0 to 40%
monomers containing tertiary amino groups. These polymers are highly compatible with anionic and cationic surfactants and have good hair-conditioning and style-holding proper-ties.
Although, therefore, suitable polymers are available for obtaining the desired effect~ on the hair, these poly-mers are made up of at least 3 or 4 monomers. According-ly, there is ~till a need for polymers which, for compar-able properties, are less complex in structure, i.e. can be synthesized from a smaller number of different monomers.
It has now surprisingly been found that certain zwit-terionic polymers of monomers containing quaternary ammon-ium groups and monomeric carboxylic acids have wet-comba-bility-improving, hair-conditioning and style-holding properties which, hitherto, have only been achieved with polymers of a larger number of different monomers. In addition, it is possible with these polymers to formulate hair-treatment preparations based on anionic and/or ampho-teric surfactants which, on the basis of their effect on the wet combability of hair, correspond in their perform-ance level to known cationic rinses.
Accordingly, the present in~ention relates to water-based hair-treatment preparations containing zwitterionic polymers, characterized in that the zwitterionic polymers are essentially made up of A) monomers containing quaternary ammonium groups corre-sponding to general formula (I) R1-CH=CR2-Co-Z-(CDH2n)-N(+)R3R4RS A( ) (I) in which R1 and R2 independently of one another rep-resent hydrogen or a methyl group and R3, R4 and R5 independently of one another represent Cl_4 alkyl groups, Z is an NH group or an oxygen atom, n is an integer of 2 to 5 and A( ) is the anion of an organic or inorganic acid and B) monomeric carboxylic acids corresponding to general formula (II) R6-CH=CR7-CooH (II) in which R6 and R7 independently of one another are hydrogen or methyl groups.
Suitable starting monomers are, for example, dimethyl-aminoethyl acrylamide, dimethylaminoethyl methacrylamide, dimethylaminopropyl acrylamide, dimethylaminopropyl meth-acrylamide, and diethylaminoethyl acrylamide in cases where Z i8 an NH group or dimethylaminoethyl acrylate, dimethyl-aminoethyl methacrylate, and diethylaminoethyl acrylate in cases where Z is an oxygen atom.
35¦ The monomers mentioned are prepared by known methods of the type described, for example, in US Patent 3,878,247, DE-PS 28 19 735, DE-PS 28 36 520, DE-PS 34 02 59g or CH-PS 464 891.
The monomers containing a tertiary amino group are then quaternized in known manner, methyl chloride, dimethyl sulfate or diethyl sulfate being particularly suitable al-kylating reagents. The quaternization reaction may takeplace in aqueous solution or in a solvent. Suitable pro-cesses are described, for example, in DE-OS 33 30 326, DE-oS 25 37 378, or DE-OS 32 44 274.
It is of advantage to use monomers corresponding to formula (I) which are derivatives of acrylamide or meth-acrylamide. Other preferred monomers are those which contain halide, methoxysulfate, or ethoxysulfate ions as counterions. Monomers of formula (I), in which R3, R4 and R5 are methyl groups, are also preferred.
Acrylamidopropyl trimethyl ammonium chloride is a particularly preferred monomer of formula (I).
Suitable monomeric carboxylic acids corresponding to formula (II) are acrylic acid, methacrylic acid, crotonic acid and 2-methyl crotonic acid. Acrylic acid or meth-acrylic acid are preferred, acrylic acid being particularlypreferred.
The zwitterionic polymers according to the invention are prepared from monomers corresponding to formulae (I) and (II) by polymerization processes known per se. The polymerization may be carried out either in aqueous solu-tion or in aqueous/alcoholic solution. The alcohols used are Cl_~ alcohols, preferably isopropanol, which simultan-eously act as polymerization regulators. However, other components may be added to the monomer solution as regula-tors, including for example formic acid or mercaptans, suchas thioethanol and thioglycolic acid. The polymerization i8 $nitiated by radical-forming ccmpounds. Redox systems and/or thermally decomposing radical formers of the azo compound type, such as for example azoisobutyronitrile, azo-bis-(cyanopentanoic acid) or azo-bis-(amidinopropane)-dihydrochloride, may be used for this purpose. Suitable redox systems are, for example, combinations of hydrogen peroxide, potassium or ammonium peroxodisulfate and ter-tiary butyl hydroperoxide with sodium ~ulfite, sodium di-thionite or hydroxylamine hydrochloride as reducing com-ponent.
The polymerization may be carried out isothermally or under adiabatic conditions, the reaction temperature being variable over the range from 20 to 200 C, depending on the concentrations used, through the heat of polymerization released. The reaction may have to be carried out under the excess pressure spontaneously established. The reac-tion temperature is preferably in the range from 20 to 100 o C.
The pH value during the copolymerization may vary over a wide range. Polymerization is advantageously carried out at low pH values, although it may also be carried out at pH
values above the neutral point. On completion of polymer-ization, the reaction mixture is adjusted to a pH value of 5 to 10 and preferably 6 to 8 with an aqueous base, for ex-ample sodium hydroxide, potassium hydroxide or ammonia.
Further particulars of the polymerization process can be found in the Examples.
Polymers in which the monomers of formula (I) were present in an excess over the monomers of formula (II) have proved to be particularly effective. In a preferred em-bodiment of the invention, therefore, the polymers used consist of monomers corresponding to formula (I) and mon-omers corresponding to formula (II) in a molar ratio of 60:40 to 95:5 and, more particularly, 75:25 to 95:5.
The zwitterionic polymers mentioned are preferably present in the preparations according to the invention in guantities of 0.1 to 10% by weight, based on the prepara-tion as a whole. The polymers are very effective in im-proving wet combability, even in low concentrations. ~y contrast, their hair-conditioning and hair-setting effects in most cases are cnly observed with concentrations above about 1 % by weight. Accordingly, it is particularly pre-*erred to use the polymers in quantities of about 1 to 5%
by weight.
The zwitterionic polymers according to the invention are preferably used in water-based preparations containing surface-active compounds. Preferred surface-active com-pounds are anior.ic, zwitterionic, amphoteric and/or non-ionic surfactants.
Suitable anionic surfactants for the hair-treatment preparations according to the invention are any anionic surface-active compounds suitable for use on the human body. They are characterized by a water-solubilizing an-ionic group such as, for example, a carboxylate, sulfate, sulfonate, or phosphate group and a lipophilic alkyl group containing about 10 to 22 carbon atoms. In addition, gly-col ether or polyglycol ether groups, ester, ether, and amide groups and also hydroxyl groups may be present in the molecule. Examples of suitable anionic surfactants are the sodium, potassium, and ammonium salts and the mono-, di-and tri-alkanolammonium salts - containing 2 or 3 carbon atoms in the alkanol group - of:
20 - linear fatty acids containing 10 to 22 carbon atoms (soaps);
- ether carboxylic acids corresponding to the formula R-O-(CH2CH20)~-CH2-COOH, in which R is a linear C10_22 alkyl group and x = 0 or 1 to 10;
25 - acyl sarcosides containing 10 to 18 carbon atoms in the acyl group;
- acyl taurides containing 10 to 18 carbon atomQ in the acyl group;
- acyl isethionates containing 10 to 18 carbon atoms in the acyl group;
- sulfosuccinic acid mono- and di-alkyl esters contain-ing 8 to 18 carbon atoms in the alkyl group and sulfo-succinic acid monoalkyl polyethoxyl esters containing 8 to 18 carbon atoms in the alkyl group and 1 to 6 ethoxyl groups;
- linear alkanesulfonates containing 12 to 18 carbon atoms;
- linear ~-olefin sulfonates containing 12 to 18 carbon atoms;
- ~-sulfofatty acid methyl esters o~ fatty acids con-taining 12 to 18 carbon atoms,;
- alkylsulfates and alkyl polyglycol ether sulfates cor-responding to the formula R-O(CH2-CH20)~-OSO3H, in which R is a preferably linear alkyl group containing 10 to 18 carbon atoms and x = O or 1 to 12;
- mixtures of surface-active hydroxysulfonates according to DE-OS 37 25 030;
- sulfated hydroxyalkyl polyethylene and/or hydroxyal-kylene propylene glycol ethers according to DE-OS 37 23 254;
- esters of tartaric acid and citric acid with alcohols which are adducts of about 2 to 15 molecules of ethyl-ene oxide and/or propylene oxide with fatty alcohols containing 8 to 22 carbon atoms.
Preferred anionic surfactants are alkyl sulfates and alkyl polyglycol ether sulfates containing 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule.
Zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one -COO(~) or -S03(-) group in the molecule. Particu-larly suitable zwitterionic surfactants are the so-called betaines, such as N-alkyl-N,N-dimethyl ammonium glycinates, for example coconut oil alkyl N,N-dimethyl ammonium glycin-ate, N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for example coconut oil acylaminopropyl-N,N-dimethyl am-monium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxy-ethyl imidazolines containing 8 to 18 carbon atoms in the alkyl or acyl group, and also coconut oil acylaminoethyl hydroxyethyl carboxymethyl glycinate.
Amphoteric surfactants are understood to be surface-active compounds which, in addition to a C8_18 alkyl or acyl group, contain at least one free amino group and at least one -COOB- or -S03B- group in the molecule and which are 20~6226 capable of forming inner salts. Examples of suitable am-photeric surfactants are N-alkyl glycines, N-alkylamino-propionic acids, N-alkylaminobutyric acids, N-alkyliminodi-propionic acids, N-hydroxyethyl-N-alkylamidopropyl gly-cines, N-alkyl taurines, N-alkyl sarcosines, 2-alkylamino-propionic acids, and alkylaminoacetic acids containing about 8 to 18 carbon atoms in the alkyl group.
Nonionic surfactants are, above all, the adducts of 2 to 20 moles of ethylene oxide with preferably linear alco-hols containing 12 to 18 carbon atoms, with alkylphenolscontaining 8 to 15 carbon atoms in the alkyl group, with fatty acids containing 12 to 18 carbon atoms, with fatty acid partial glycerides, with fatty acid sorbitan partial esters, with fatty alkanolamides, and with methyl glucoside fatty acid esters. Other suitable nonionic surfactants are alkyl(oligo)glycosides, alkylamine oxide surfactants, and fatty acid alkanolamides.
Cationic surfactants may also be present in the prep-arations according to the invention providing they are com-patible with the other components, for example anionic sur-factants. Such cationic surfactants are known, for exam-ple, from DE-OS 34 42 175.
The preparations according to the invention preferably contain surface-active compounds in quantities of 0.1 to 40 % by weight, based on the preparation as a whole.
By virtue of their favorable hair-conditioning and hair-setting properties and their compatibility with the sub6tances typically used in hair-treatment preparations, the zwitterionic polymers according to the invention are suitable as setting and hair-conditioning components in any standard water-based hair-washing and hair-care prepara-tions, æuch as for example shampoos, after-rinses, hair setting lotions, hair setting gels, and water-based color-ing, permanent-wave, and permanent-wave fixing prepara-tions.
Accordingly, the water-based hair-washing and hair-care preparations according to the invention may contain any standard auxiliaries and additives for the particular application envisaged in addition to the compulsory zwit-terionic polymers.
For hair rinses, such auxiliaries and additives are, for example, cationic surfactants, more particularly sur-face-active quaternary ammonium salts, fatty alcohols con-taining 12 to 22 carbon atoms, fatty acid partial glycer-ides, cosmetic oil and fatty components, and water-soluble polymers having a thickening effect. For hair setting lo-tions and hair setting gels, the auxiliaries and additives in question are, for example, cationic surfactants, cation-ic, nonionic, or anionic polymers, and lower alcohols.
Hair-dyeing preparations contain substantive dyes or oxida-tion dye precursors, anionic or nonionic surfactants, am-monia or alkanolamines, and, optionally, antioxidants.
Permanent-wave fixing preparations contain an oxidizing agent, for example H202, H202 adducts, or potassium bromate, and also anionic or nonionic surfactants.
The preparations according to the invention preferably have a pH value of 4 to 10 and, more preferably, 5 to 9.
The following Examples are intended to illustrate the invention without limiting it in any way.
~pl-~
1. Preparation of a polymer of acrylamidopropyl tri--thyl ~-monium ohlorid- an~ aoryl~c aoid in a ~ol~r ratio of 3s1 ~polyn r Pl).
201.17 kg of water, 89.59 kg of a 60% by weiqht aque-ous solution of acrylamidopropyl trimethyl ammonium chlor-ide and 6.25 kg of acrylic acid were introduced into a re-actor equipped with an impeller stirrer, a heating and cooling system, a reflux condenser, and a temperature mea-surinq instrument. A pH value of 3.4 was spontaneously es-tablished. The solution was purged with nitrogen and then heated to 60 C. Solutions of 0.06 kg of azo-bis-(amidin-opropane)-dihydrochloride in 1.00 kg of water, 0.024 kg of potassium peroxodisulfate in 1,000 kg of water, and 0.012 kg of sodium disulfite in 1,000 kg of water were then suc-206622~
cessively added to the mixture with stirring. Only slight heating occurred. The reaction mixture was heated to 80 -85 C and kept at that temperature for 4 hours. The pol-ymerization was then terminated. The viscous solution was S cooled to 30-40 C and neutralized with 5,000 kg of 45%
aqueous sodium hydroxide.
The clear colorless polymer solution had the following characteristic data: pH value 6.9, dry matter 20%, product viscosity 13,800 mPa s, intrinsic viscosity 220 ml/g (in 10% NaCl solution).
After washing, dyeing, or permanent waving, hair often shows unsatisfactory wet and dry combability, in addition to which the curl retention capacity of dry hair is inade-quate. To remedy this drawback, either appropriate com-ponents have to be added to the hair treatment prepara-tions, or the hair has to be subsequently subjected to a separate treatment with these substances which, for this purpose, are normally formulated as a rinse.
Polymeric compounds are frequently used as active sub-stances of the type in question to improve the properties of hair.
Although cationic polymers, such as for example the cellulose derivatives known from US Patents 3,816,616 and 3,472,840, are capable of distinctly improving wet comb-ability, they effect only unsati~factory hair-~etting and style-holding effects.
The use of zwitterionic polymers containing anionic groups, mostly carboxyl groups, and quaternary ammonium groups in the molecule in hair-treatment preparations is also known. For example, DE-OS 21 50 557 describes the use of polymers of zwitterionic monomers in hair-setting prep-arations. The use of copolymers of dimethylaminoethyl methacrylate, acrylic acid and methyl methacrylate in hair-setting lotions and shampoos is also known from DE-OS 28 17 369.
These known zwitterionic polymers in hair-treatment and hair-setting preparations have the disadvantage, par-ticularly in formulations with anionic surfactants, that their hair-conditioning and hair-setting properties are gradually lost in the event of prolonged storage. Accord-ingly, it was proposed in DE-OS 37 08 451 to use zwitter-ionic polymers consisting of 30 to 70% monomers containing quaternary ammonium groups, 10 to 30% monomeric olefinical-ly unsaturated carboxylic acids, 10 to 30% monomeric ole-finically unsaturated carboxylic acid esters and 0 to 40%
monomers containing tertiary amino groups. These polymers are highly compatible with anionic and cationic surfactants and have good hair-conditioning and style-holding proper-ties.
Although, therefore, suitable polymers are available for obtaining the desired effect~ on the hair, these poly-mers are made up of at least 3 or 4 monomers. According-ly, there is ~till a need for polymers which, for compar-able properties, are less complex in structure, i.e. can be synthesized from a smaller number of different monomers.
It has now surprisingly been found that certain zwit-terionic polymers of monomers containing quaternary ammon-ium groups and monomeric carboxylic acids have wet-comba-bility-improving, hair-conditioning and style-holding properties which, hitherto, have only been achieved with polymers of a larger number of different monomers. In addition, it is possible with these polymers to formulate hair-treatment preparations based on anionic and/or ampho-teric surfactants which, on the basis of their effect on the wet combability of hair, correspond in their perform-ance level to known cationic rinses.
Accordingly, the present in~ention relates to water-based hair-treatment preparations containing zwitterionic polymers, characterized in that the zwitterionic polymers are essentially made up of A) monomers containing quaternary ammonium groups corre-sponding to general formula (I) R1-CH=CR2-Co-Z-(CDH2n)-N(+)R3R4RS A( ) (I) in which R1 and R2 independently of one another rep-resent hydrogen or a methyl group and R3, R4 and R5 independently of one another represent Cl_4 alkyl groups, Z is an NH group or an oxygen atom, n is an integer of 2 to 5 and A( ) is the anion of an organic or inorganic acid and B) monomeric carboxylic acids corresponding to general formula (II) R6-CH=CR7-CooH (II) in which R6 and R7 independently of one another are hydrogen or methyl groups.
Suitable starting monomers are, for example, dimethyl-aminoethyl acrylamide, dimethylaminoethyl methacrylamide, dimethylaminopropyl acrylamide, dimethylaminopropyl meth-acrylamide, and diethylaminoethyl acrylamide in cases where Z i8 an NH group or dimethylaminoethyl acrylate, dimethyl-aminoethyl methacrylate, and diethylaminoethyl acrylate in cases where Z is an oxygen atom.
35¦ The monomers mentioned are prepared by known methods of the type described, for example, in US Patent 3,878,247, DE-PS 28 19 735, DE-PS 28 36 520, DE-PS 34 02 59g or CH-PS 464 891.
The monomers containing a tertiary amino group are then quaternized in known manner, methyl chloride, dimethyl sulfate or diethyl sulfate being particularly suitable al-kylating reagents. The quaternization reaction may takeplace in aqueous solution or in a solvent. Suitable pro-cesses are described, for example, in DE-OS 33 30 326, DE-oS 25 37 378, or DE-OS 32 44 274.
It is of advantage to use monomers corresponding to formula (I) which are derivatives of acrylamide or meth-acrylamide. Other preferred monomers are those which contain halide, methoxysulfate, or ethoxysulfate ions as counterions. Monomers of formula (I), in which R3, R4 and R5 are methyl groups, are also preferred.
Acrylamidopropyl trimethyl ammonium chloride is a particularly preferred monomer of formula (I).
Suitable monomeric carboxylic acids corresponding to formula (II) are acrylic acid, methacrylic acid, crotonic acid and 2-methyl crotonic acid. Acrylic acid or meth-acrylic acid are preferred, acrylic acid being particularlypreferred.
The zwitterionic polymers according to the invention are prepared from monomers corresponding to formulae (I) and (II) by polymerization processes known per se. The polymerization may be carried out either in aqueous solu-tion or in aqueous/alcoholic solution. The alcohols used are Cl_~ alcohols, preferably isopropanol, which simultan-eously act as polymerization regulators. However, other components may be added to the monomer solution as regula-tors, including for example formic acid or mercaptans, suchas thioethanol and thioglycolic acid. The polymerization i8 $nitiated by radical-forming ccmpounds. Redox systems and/or thermally decomposing radical formers of the azo compound type, such as for example azoisobutyronitrile, azo-bis-(cyanopentanoic acid) or azo-bis-(amidinopropane)-dihydrochloride, may be used for this purpose. Suitable redox systems are, for example, combinations of hydrogen peroxide, potassium or ammonium peroxodisulfate and ter-tiary butyl hydroperoxide with sodium ~ulfite, sodium di-thionite or hydroxylamine hydrochloride as reducing com-ponent.
The polymerization may be carried out isothermally or under adiabatic conditions, the reaction temperature being variable over the range from 20 to 200 C, depending on the concentrations used, through the heat of polymerization released. The reaction may have to be carried out under the excess pressure spontaneously established. The reac-tion temperature is preferably in the range from 20 to 100 o C.
The pH value during the copolymerization may vary over a wide range. Polymerization is advantageously carried out at low pH values, although it may also be carried out at pH
values above the neutral point. On completion of polymer-ization, the reaction mixture is adjusted to a pH value of 5 to 10 and preferably 6 to 8 with an aqueous base, for ex-ample sodium hydroxide, potassium hydroxide or ammonia.
Further particulars of the polymerization process can be found in the Examples.
Polymers in which the monomers of formula (I) were present in an excess over the monomers of formula (II) have proved to be particularly effective. In a preferred em-bodiment of the invention, therefore, the polymers used consist of monomers corresponding to formula (I) and mon-omers corresponding to formula (II) in a molar ratio of 60:40 to 95:5 and, more particularly, 75:25 to 95:5.
The zwitterionic polymers mentioned are preferably present in the preparations according to the invention in guantities of 0.1 to 10% by weight, based on the prepara-tion as a whole. The polymers are very effective in im-proving wet combability, even in low concentrations. ~y contrast, their hair-conditioning and hair-setting effects in most cases are cnly observed with concentrations above about 1 % by weight. Accordingly, it is particularly pre-*erred to use the polymers in quantities of about 1 to 5%
by weight.
The zwitterionic polymers according to the invention are preferably used in water-based preparations containing surface-active compounds. Preferred surface-active com-pounds are anior.ic, zwitterionic, amphoteric and/or non-ionic surfactants.
Suitable anionic surfactants for the hair-treatment preparations according to the invention are any anionic surface-active compounds suitable for use on the human body. They are characterized by a water-solubilizing an-ionic group such as, for example, a carboxylate, sulfate, sulfonate, or phosphate group and a lipophilic alkyl group containing about 10 to 22 carbon atoms. In addition, gly-col ether or polyglycol ether groups, ester, ether, and amide groups and also hydroxyl groups may be present in the molecule. Examples of suitable anionic surfactants are the sodium, potassium, and ammonium salts and the mono-, di-and tri-alkanolammonium salts - containing 2 or 3 carbon atoms in the alkanol group - of:
20 - linear fatty acids containing 10 to 22 carbon atoms (soaps);
- ether carboxylic acids corresponding to the formula R-O-(CH2CH20)~-CH2-COOH, in which R is a linear C10_22 alkyl group and x = 0 or 1 to 10;
25 - acyl sarcosides containing 10 to 18 carbon atoms in the acyl group;
- acyl taurides containing 10 to 18 carbon atomQ in the acyl group;
- acyl isethionates containing 10 to 18 carbon atoms in the acyl group;
- sulfosuccinic acid mono- and di-alkyl esters contain-ing 8 to 18 carbon atoms in the alkyl group and sulfo-succinic acid monoalkyl polyethoxyl esters containing 8 to 18 carbon atoms in the alkyl group and 1 to 6 ethoxyl groups;
- linear alkanesulfonates containing 12 to 18 carbon atoms;
- linear ~-olefin sulfonates containing 12 to 18 carbon atoms;
- ~-sulfofatty acid methyl esters o~ fatty acids con-taining 12 to 18 carbon atoms,;
- alkylsulfates and alkyl polyglycol ether sulfates cor-responding to the formula R-O(CH2-CH20)~-OSO3H, in which R is a preferably linear alkyl group containing 10 to 18 carbon atoms and x = O or 1 to 12;
- mixtures of surface-active hydroxysulfonates according to DE-OS 37 25 030;
- sulfated hydroxyalkyl polyethylene and/or hydroxyal-kylene propylene glycol ethers according to DE-OS 37 23 254;
- esters of tartaric acid and citric acid with alcohols which are adducts of about 2 to 15 molecules of ethyl-ene oxide and/or propylene oxide with fatty alcohols containing 8 to 22 carbon atoms.
Preferred anionic surfactants are alkyl sulfates and alkyl polyglycol ether sulfates containing 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule.
Zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one -COO(~) or -S03(-) group in the molecule. Particu-larly suitable zwitterionic surfactants are the so-called betaines, such as N-alkyl-N,N-dimethyl ammonium glycinates, for example coconut oil alkyl N,N-dimethyl ammonium glycin-ate, N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for example coconut oil acylaminopropyl-N,N-dimethyl am-monium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxy-ethyl imidazolines containing 8 to 18 carbon atoms in the alkyl or acyl group, and also coconut oil acylaminoethyl hydroxyethyl carboxymethyl glycinate.
Amphoteric surfactants are understood to be surface-active compounds which, in addition to a C8_18 alkyl or acyl group, contain at least one free amino group and at least one -COOB- or -S03B- group in the molecule and which are 20~6226 capable of forming inner salts. Examples of suitable am-photeric surfactants are N-alkyl glycines, N-alkylamino-propionic acids, N-alkylaminobutyric acids, N-alkyliminodi-propionic acids, N-hydroxyethyl-N-alkylamidopropyl gly-cines, N-alkyl taurines, N-alkyl sarcosines, 2-alkylamino-propionic acids, and alkylaminoacetic acids containing about 8 to 18 carbon atoms in the alkyl group.
Nonionic surfactants are, above all, the adducts of 2 to 20 moles of ethylene oxide with preferably linear alco-hols containing 12 to 18 carbon atoms, with alkylphenolscontaining 8 to 15 carbon atoms in the alkyl group, with fatty acids containing 12 to 18 carbon atoms, with fatty acid partial glycerides, with fatty acid sorbitan partial esters, with fatty alkanolamides, and with methyl glucoside fatty acid esters. Other suitable nonionic surfactants are alkyl(oligo)glycosides, alkylamine oxide surfactants, and fatty acid alkanolamides.
Cationic surfactants may also be present in the prep-arations according to the invention providing they are com-patible with the other components, for example anionic sur-factants. Such cationic surfactants are known, for exam-ple, from DE-OS 34 42 175.
The preparations according to the invention preferably contain surface-active compounds in quantities of 0.1 to 40 % by weight, based on the preparation as a whole.
By virtue of their favorable hair-conditioning and hair-setting properties and their compatibility with the sub6tances typically used in hair-treatment preparations, the zwitterionic polymers according to the invention are suitable as setting and hair-conditioning components in any standard water-based hair-washing and hair-care prepara-tions, æuch as for example shampoos, after-rinses, hair setting lotions, hair setting gels, and water-based color-ing, permanent-wave, and permanent-wave fixing prepara-tions.
Accordingly, the water-based hair-washing and hair-care preparations according to the invention may contain any standard auxiliaries and additives for the particular application envisaged in addition to the compulsory zwit-terionic polymers.
For hair rinses, such auxiliaries and additives are, for example, cationic surfactants, more particularly sur-face-active quaternary ammonium salts, fatty alcohols con-taining 12 to 22 carbon atoms, fatty acid partial glycer-ides, cosmetic oil and fatty components, and water-soluble polymers having a thickening effect. For hair setting lo-tions and hair setting gels, the auxiliaries and additives in question are, for example, cationic surfactants, cation-ic, nonionic, or anionic polymers, and lower alcohols.
Hair-dyeing preparations contain substantive dyes or oxida-tion dye precursors, anionic or nonionic surfactants, am-monia or alkanolamines, and, optionally, antioxidants.
Permanent-wave fixing preparations contain an oxidizing agent, for example H202, H202 adducts, or potassium bromate, and also anionic or nonionic surfactants.
The preparations according to the invention preferably have a pH value of 4 to 10 and, more preferably, 5 to 9.
The following Examples are intended to illustrate the invention without limiting it in any way.
~pl-~
1. Preparation of a polymer of acrylamidopropyl tri--thyl ~-monium ohlorid- an~ aoryl~c aoid in a ~ol~r ratio of 3s1 ~polyn r Pl).
201.17 kg of water, 89.59 kg of a 60% by weiqht aque-ous solution of acrylamidopropyl trimethyl ammonium chlor-ide and 6.25 kg of acrylic acid were introduced into a re-actor equipped with an impeller stirrer, a heating and cooling system, a reflux condenser, and a temperature mea-surinq instrument. A pH value of 3.4 was spontaneously es-tablished. The solution was purged with nitrogen and then heated to 60 C. Solutions of 0.06 kg of azo-bis-(amidin-opropane)-dihydrochloride in 1.00 kg of water, 0.024 kg of potassium peroxodisulfate in 1,000 kg of water, and 0.012 kg of sodium disulfite in 1,000 kg of water were then suc-206622~
cessively added to the mixture with stirring. Only slight heating occurred. The reaction mixture was heated to 80 -85 C and kept at that temperature for 4 hours. The pol-ymerization was then terminated. The viscous solution was S cooled to 30-40 C and neutralized with 5,000 kg of 45%
aqueous sodium hydroxide.
The clear colorless polymer solution had the following characteristic data: pH value 6.9, dry matter 20%, product viscosity 13,800 mPa s, intrinsic viscosity 220 ml/g (in 10% NaCl solution).
2. Applioation~ Ex~ples 2.1. Hair rinse No. 1 Components % by weight Fatty alcohol (C12_l4) poly(3EO)glYcol ether lS sulfate, Na salt, 28% aqueous solution S.o Coconut oil acyl(C 2_l8)aminopropyl di-methyl glycine, 30~ aqueous solution 1.0 Polymer Pl (20% active substance in water) 2.5 Water ad 100 The rinse is in the form of a cloudy solution. The wet combability of hair treated with this rinse was very good. No adverse effect on the hair or static charging of the hair was observed.
2.2 Hair rinse No. 2 Components % by weight Fatty alcohol (C~ ) poly(3 EO) glycol ether sulfate, Na salt, 28% aqueous solution 5.0 DehytonO AB 30l 1.0 Polymer Pl (20% active substance in water) 2.5 Water ad 100 Fatty amine derivative of betaine structure, approx.
30% active substance in water, CTFA name: coco-betaine (HENKEL) The rinse is in the form of a cloudy solution. The wet combability of hair treated with this rinse was very 2~66226 good.
2.3 Hair rinse No. 3 Components % by weight Sulfosuccinic acid semiester based on a Cl2-l~ alkyl poly(3 EO)glycol ether, di-sodium salt (40% active substance in water, CTFA name: disodium laurethsulfosuccinate 0.9 Texapon~ K14 S spez.2 1.2 Dehyton~ AB 30 1.0 Polymer P1 (20% active substance in water) 2.5 Water ad lO0 2 Sodium lauryl myristyl ether sulfate, about 30% active substance in water (HENKEL) The wet combability of hair treated with this rinse was good to very good.
2.4 Hair rinse No. 4 Components % by weight Sulfosuccinic acid semiester based on a Cl~ alkyl poly(3 EO)glycol ether, di-so~lum salt (40% active substance in water), CTFA name: disodium laurethsulfosuccinate l.0 DehytonD AB 30 7.5 Polymer P1 (20S active substance in water) 2.5 Water ad 100 The rinse is present in the form of an almost clear solution. The wet combability of hair treated with this rinse was very good.
2.S Hair rinse No. 5 Components % by weight C16_l8 fatty alcohol 3.0 Coconut oil acyl(C 2_18)aminopropyl di-methyl glycine, 30~ agueous solution 8.0 Fatty alcohol (C12_1~) poly(3 EO)glycol ether sulfate, Na salt, 28% agueous 3S solution S.0 Polymer P1 (20% active substance in water) 2.5 Water ad lO0 To prepare this hair rinse, the mixture of surfactants and polymer was introduced into the molten fat phase and emulsified therein. The wet combability of hair treated with this rinse was excellent.
2.6 Hair shampoo No. 1 Components % by weight Fatty alcohol (C12_14) poly(3 EO)glycol ether sulfate, Na salt, 28% aqueous solution 50.0 Coconut oil acyl(Cl2_1B)aminopropyl di-methyl glycine, 30% aqueous solution 10.0 Polymer Pl (20% active substance in water) 5.0 Water ad 100 The wet combability of hair shampooed with this prepa-ration was excellent.
2.7 Hair shampoo No. 2 Components % by weight Fatty alcohol (Cl2_14) poly(3 EO)glycol ether sulfate, Na salt, 28% aqueous solution 45.0 Coconut oil acyl(C12_1~)aminopropyl di-methyl glycine, 30% aqueous solution 15.0 Akypo~ RLM 100 NV3 5.0 Polymer Pl (20% active substance in water) 5.0 Water ad 100
2.2 Hair rinse No. 2 Components % by weight Fatty alcohol (C~ ) poly(3 EO) glycol ether sulfate, Na salt, 28% aqueous solution 5.0 DehytonO AB 30l 1.0 Polymer Pl (20% active substance in water) 2.5 Water ad 100 Fatty amine derivative of betaine structure, approx.
30% active substance in water, CTFA name: coco-betaine (HENKEL) The rinse is in the form of a cloudy solution. The wet combability of hair treated with this rinse was very 2~66226 good.
2.3 Hair rinse No. 3 Components % by weight Sulfosuccinic acid semiester based on a Cl2-l~ alkyl poly(3 EO)glycol ether, di-sodium salt (40% active substance in water, CTFA name: disodium laurethsulfosuccinate 0.9 Texapon~ K14 S spez.2 1.2 Dehyton~ AB 30 1.0 Polymer P1 (20% active substance in water) 2.5 Water ad lO0 2 Sodium lauryl myristyl ether sulfate, about 30% active substance in water (HENKEL) The wet combability of hair treated with this rinse was good to very good.
2.4 Hair rinse No. 4 Components % by weight Sulfosuccinic acid semiester based on a Cl~ alkyl poly(3 EO)glycol ether, di-so~lum salt (40% active substance in water), CTFA name: disodium laurethsulfosuccinate l.0 DehytonD AB 30 7.5 Polymer P1 (20S active substance in water) 2.5 Water ad 100 The rinse is present in the form of an almost clear solution. The wet combability of hair treated with this rinse was very good.
2.S Hair rinse No. 5 Components % by weight C16_l8 fatty alcohol 3.0 Coconut oil acyl(C 2_18)aminopropyl di-methyl glycine, 30~ agueous solution 8.0 Fatty alcohol (C12_1~) poly(3 EO)glycol ether sulfate, Na salt, 28% agueous 3S solution S.0 Polymer P1 (20% active substance in water) 2.5 Water ad lO0 To prepare this hair rinse, the mixture of surfactants and polymer was introduced into the molten fat phase and emulsified therein. The wet combability of hair treated with this rinse was excellent.
2.6 Hair shampoo No. 1 Components % by weight Fatty alcohol (C12_14) poly(3 EO)glycol ether sulfate, Na salt, 28% aqueous solution 50.0 Coconut oil acyl(Cl2_1B)aminopropyl di-methyl glycine, 30% aqueous solution 10.0 Polymer Pl (20% active substance in water) 5.0 Water ad 100 The wet combability of hair shampooed with this prepa-ration was excellent.
2.7 Hair shampoo No. 2 Components % by weight Fatty alcohol (Cl2_14) poly(3 EO)glycol ether sulfate, Na salt, 28% aqueous solution 45.0 Coconut oil acyl(C12_1~)aminopropyl di-methyl glycine, 30% aqueous solution 15.0 Akypo~ RLM 100 NV3 5.0 Polymer Pl (20% active substance in water) 5.0 Water ad 100
3 Aqueous solution of Cl2_l~ alkyl-O-(CH2-CH2-O)l0-CH2-CO~ONa, 22% active substance (CHEM-Y) This sha~poo not only freed the hair from soil and grease, it al50 had a distinct conditioning effect on wet hair and left dry hair with body and volume.
To quantify the effect obtained by the polymer, a lS
cm long strand of hair (2 g) was wound onto a glass tube having a external diameter of 1.7 cm, fixed and treated with 0.2 g of the shampoo. The hair strand was then rinsed with water and dried. A measure of the stability of the curl obtained after withdrawal of the glass rod is the curl retention value. The curl retention value is defined as t(l-l~)/(l-lo)] * 100% where 1 is the length of the hair 2~66226 strand (15 cm~, lo i8 the length of the hair curl immediate-ly after drying and 1~ is the length of the hair curl after storage for 48 h under constant conditions (30C/40% rela-tive air humidity) in a drying cabinet. The curls treated with the shampoo according to the invention had a curl re-tention value of 94.7% whereas curls treated with a similar shampoo to which polymer P1 had not been added showed a curl retention of only 87.1%.
2.8 Hair shampoo No. 3 Components % by weight Texapon~ K14 S spez. 15.0 Sulfosuccinic acid semiester based on a Cl _lq alkyl polyglycol (3 EO) ether, disodium sa~t (40% active substance in water), CTFA name:
disodium laurethsulfosuccinate 12.0 Ethoxylated (g EO) palm kernel oil fatty acid 1.0 Alkyl glucoside APG-600 4.0 Dehyton0 CBs 9-7 Polymer Pl (20% active substance in water) 5.0 Water ad 100 q Aqueous solution of RO(Z)~ with Z = glucose, x = 1.4 and R = n-alkyl(Cl2_l4), (50% active substance) (HORIZON)5 s Aqueous solution of a fatty amine derivative of betaine structure, CTFA name: coco-betaine (approx.
31% active substance, approx. 6.5% NaCl) (HENKEL) The shampoo is clear and colorless. This shampoo had an excellent conditioning effect on the hair.
2.9 Hair shampoo No. 4 Components % by weight Sulfosuccinic acid semiester based on a Cl _lq alkyl polyglycol (3 EO) ether, disodium sa~t (40% active substance in water), CTFA name:
disodium laurethsulfosuccinate 12.0 Ethoxylated (9 EO) palm kernel oil fatty acid 1.0 Dehyton0 CB 10.0 2~66226 Eucarol~ TA6 20.0 Polymer Pl (20% active substance in water) 1.2 Water ad 100 6 Aqueous solution of sodium laureth-7-tartrate, 25%
active substance (ROL) This clear shampoo was distinguished in particular by an excellent conditioning effect coupled with a good clean-ing effect.
2.10 Hair shampoo No. 5 Components % by weight Sulfosuccinic acid semiester based on a C~
alkyl polyglycol (3 EO) ether, disodium sa~t (40% active substance in water), CTFA name:
disodium laurethsulfosuccinate 15.0 Dehyton~ C~ 12.0 Alkyl glucoside APG-600 4.0 Polymer Pl (20% active substance in water) 1.2 Water ad 100 This clear shampoo left the shampooed hair with very good wet combability.
To quantify the effect obtained by the polymer, a lS
cm long strand of hair (2 g) was wound onto a glass tube having a external diameter of 1.7 cm, fixed and treated with 0.2 g of the shampoo. The hair strand was then rinsed with water and dried. A measure of the stability of the curl obtained after withdrawal of the glass rod is the curl retention value. The curl retention value is defined as t(l-l~)/(l-lo)] * 100% where 1 is the length of the hair 2~66226 strand (15 cm~, lo i8 the length of the hair curl immediate-ly after drying and 1~ is the length of the hair curl after storage for 48 h under constant conditions (30C/40% rela-tive air humidity) in a drying cabinet. The curls treated with the shampoo according to the invention had a curl re-tention value of 94.7% whereas curls treated with a similar shampoo to which polymer P1 had not been added showed a curl retention of only 87.1%.
2.8 Hair shampoo No. 3 Components % by weight Texapon~ K14 S spez. 15.0 Sulfosuccinic acid semiester based on a Cl _lq alkyl polyglycol (3 EO) ether, disodium sa~t (40% active substance in water), CTFA name:
disodium laurethsulfosuccinate 12.0 Ethoxylated (g EO) palm kernel oil fatty acid 1.0 Alkyl glucoside APG-600 4.0 Dehyton0 CBs 9-7 Polymer Pl (20% active substance in water) 5.0 Water ad 100 q Aqueous solution of RO(Z)~ with Z = glucose, x = 1.4 and R = n-alkyl(Cl2_l4), (50% active substance) (HORIZON)5 s Aqueous solution of a fatty amine derivative of betaine structure, CTFA name: coco-betaine (approx.
31% active substance, approx. 6.5% NaCl) (HENKEL) The shampoo is clear and colorless. This shampoo had an excellent conditioning effect on the hair.
2.9 Hair shampoo No. 4 Components % by weight Sulfosuccinic acid semiester based on a Cl _lq alkyl polyglycol (3 EO) ether, disodium sa~t (40% active substance in water), CTFA name:
disodium laurethsulfosuccinate 12.0 Ethoxylated (9 EO) palm kernel oil fatty acid 1.0 Dehyton0 CB 10.0 2~66226 Eucarol~ TA6 20.0 Polymer Pl (20% active substance in water) 1.2 Water ad 100 6 Aqueous solution of sodium laureth-7-tartrate, 25%
active substance (ROL) This clear shampoo was distinguished in particular by an excellent conditioning effect coupled with a good clean-ing effect.
2.10 Hair shampoo No. 5 Components % by weight Sulfosuccinic acid semiester based on a C~
alkyl polyglycol (3 EO) ether, disodium sa~t (40% active substance in water), CTFA name:
disodium laurethsulfosuccinate 15.0 Dehyton~ C~ 12.0 Alkyl glucoside APG-600 4.0 Polymer Pl (20% active substance in water) 1.2 Water ad 100 This clear shampoo left the shampooed hair with very good wet combability.
Claims (11)
1. Water-based hair-treatment preparations containing zwitterionic polymers, characterized in that the zwitter-ionic polymers are essentially made up of A) monomers containing quaternary ammonium groups corre-sponding to general formula (I) R1-CH=CR2-CO-Z-(CnH2n)-N(+)R3R4R5 A(-) (I) in which R1 and R2 independently of one another repre-sent hydrogen or a methyl group and R3, R4, and R5 in-dependently of one another represent C1-4 alkyl groups, Z is an NH group or an oxygen atom, n is an integer of 2 to 5, and A(-) is the anion of an organic or inorgan-ic acid and B) monomeric carboxylic acids corresponding to general formula (II) R6-CH=CR7-COOH (II) in which R6 and R7 independently of one another are hydrogen or methyl groups.
2. Preparations as claimed in claim 1, characterized in that the zwitterionic polymers consist of monomers of type (A) and monomers of type (B) in a molar ratio of 60:40 to 95:5 and, more particularly, 75:25 to 95:5.
3. Preparations as claimed in claim 1 or 2, characterized in that, in the monomers of type (A), R3, R4 and R5 are methyl groups, Z is an NH group, and A(-) is a halide, meth-oxysulfate, or ethoxysulfate ion.
4. Preparations as claimed in any of claims 1 to 3, char-acterized in that the monomer of type (A) is acrylamido-propyl trimethyl ammonium chloride.
5. Preparations as claimed in any of claims 1 to 4, char-acterized in that the monomer of type (B) is acrylic acid.
6. Preparations as claimed in any of claims 1 to 5, char-acterized in that they contain the zwitterionic polymers in quantities of 0.1 to 10% by weight and more particularly in quantities of 1 to 5% by weight, based on the preparation as a whole.
7. Preparations as claimed in any of claims 1 to 6, char-acterized in that they contain at least one surface-active compound selected from the group of anionic, zwitterionic, amphoteric and nonionic surfactants.
8. Preparations as claimed in claim 7, characterized in that they contain the surface-active compounds in quanti-ties of 0.1 to 40% by weight, based on the preparation as a whole.
9. Preparations as claimed in any of claims 1 to 8, characterized in that they have a pH value of 4 to 10 and, more particularly, 5 to 9.
10. Preparations as claimed in any of claims 1 to 9, characterized in that they are formulated as shampoos or rinses.
11. The use of the preparations claimed in any of claims 1 to 10 for the treatment of hair.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3929973.2 | 1989-09-08 | ||
| DE19893929973 DE3929973A1 (en) | 1989-09-08 | 1989-09-08 | HAIR CARE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2066226A1 true CA2066226A1 (en) | 1991-03-09 |
Family
ID=6388972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2066226 Abandoned CA2066226A1 (en) | 1989-09-08 | 1990-08-30 | Hair care preparations |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0490982A1 (en) |
| JP (1) | JPH05500220A (en) |
| CA (1) | CA2066226A1 (en) |
| DD (1) | DD297554A5 (en) |
| DE (1) | DE3929973A1 (en) |
| WO (1) | WO1991003229A1 (en) |
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6277386B1 (en) | 1998-02-25 | 2001-08-21 | Basf Aktiengesellschaft | Cosmetic |
| US6365697B1 (en) | 1995-11-06 | 2002-04-02 | Basf Aktiengesellschaft | Water-soluble or water-dispersible polyurethanes with terminal acid groups, the production and the use thereof |
| US6410004B1 (en) | 1999-03-12 | 2002-06-25 | Basf Aktiengesellschaft | Polyureas and water-soluble or water-dispersible polymeric salts |
| US6541032B1 (en) | 1999-10-13 | 2003-04-01 | Basf Aktiengesellschaft | Use of finely divided dye-containing polymers PD as color-imparting constituent in cosmetic compositions |
| US6736862B2 (en) | 2001-01-10 | 2004-05-18 | Henkel Kommanditgesellschaft Auf Aktien | Indole/indoline based hybrid dyes and indole/indoline based hybrid dye intermediate products |
| US6812200B2 (en) | 2000-12-23 | 2004-11-02 | Henkel Kommanditgesellschaft Auf Aktien | Process for coating detergent tablets |
| US6828443B1 (en) | 1999-07-06 | 2004-12-07 | Henkel Kommanditgesellschaft Auf Aktien | Dyes and colorants |
| US6858216B2 (en) | 2000-05-06 | 2005-02-22 | Henkel Kommanditgesellschaft Auf Aktien | Cosmetic agent containing 2-furanone derivatives |
| US6871652B1 (en) | 1999-07-03 | 2005-03-29 | Hans Schwarzkopf Gmbh & Co. Kg | Method for permanently shaping keratin fibers, and agents |
| US6932964B1 (en) | 1998-08-26 | 2005-08-23 | Basf Aktiengesellschaft | Cosmetic composition with water-soluble or water-dispersible polymers |
| US7098178B2 (en) | 2000-03-16 | 2006-08-29 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Silicic acid ester mixtures |
| US7169193B2 (en) | 2000-04-28 | 2007-01-30 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Use of sugar surfactants and fatty acid partial glycerides |
| US7375070B2 (en) | 2002-08-14 | 2008-05-20 | Henkel Kommanditgesellschaft Auf Aktien | Portioned detergent composition |
| US7417019B2 (en) | 2000-07-14 | 2008-08-26 | Henkel Kommanditgesellschaft Auf Aktien | Hollow body with a compartment, containing a portion of a washing, cleaning or rinsing agent |
| US8034888B2 (en) | 2004-10-22 | 2011-10-11 | Basf Se | Amphoteric ethyl methacrylate copolymers and use thereof |
| US8268015B2 (en) | 2008-12-16 | 2012-09-18 | Henkel Ag & Co. Kgaa | Method for decolorizing keratin-containing fibers |
| US8673275B2 (en) | 2010-03-02 | 2014-03-18 | Basf Se | Block copolymers and their use |
| US8753408B2 (en) | 2007-08-23 | 2014-06-17 | Henkel Ag & Co. Kgaa | Reductive decoloration of keratin-containing fibers |
| US8821841B2 (en) | 2005-08-11 | 2014-09-02 | Basf Se | Copolymers for cosmetic applications |
| DE102015218077A1 (en) | 2015-09-21 | 2017-03-23 | Henkel Ag & Co. Kgaa | Hair-friendly oxidation dye or bleaching agent and gentle hair dyeing or bleaching method |
| US10323215B2 (en) | 2013-07-03 | 2019-06-18 | Basf Se | Solid polymer composition obtained by polymerization of an acid group containing monomer in the presence of a polyether compound |
| US11434220B2 (en) | 2017-08-31 | 2022-09-06 | Basf Se | Use of physiological cooling active ingredients, and compositions comprising such active ingredients |
Families Citing this family (142)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5612024A (en) * | 1991-03-27 | 1997-03-18 | Henkel Kommanditgesellschaft Auf Aktien | Cosmetic preparations for the hair |
| US5631003A (en) * | 1991-09-25 | 1997-05-20 | Henkel Kommanditgesellschaft Auf Aktien | Hair treatment prepartation |
| DE4131898A1 (en) * | 1991-09-25 | 1993-04-01 | Henkel Kgaa | PREPARATIONS FOR HAIR TREATMENT |
| EP0648104B1 (en) * | 1992-07-03 | 1998-01-07 | Henkel Kommanditgesellschaft auf Aktien | Hair-treatment agents |
| ES2114057T3 (en) * | 1992-07-03 | 1998-05-16 | Henkel Kgaa | AGENT FOR HAIR TREATMENT. |
| KR100295939B1 (en) * | 1992-09-29 | 2001-11-14 | 한스 크리스토프 빌크, 미하엘 베르크만 | Hair aftertreatment |
| DE4301994C1 (en) * | 1993-01-26 | 1994-08-25 | Wella Ag | Hair and body cleansers |
| DE4401708A1 (en) * | 1994-01-21 | 1995-07-27 | Henkel Kgaa | Polymer concentrate and use |
| DE4405127A1 (en) * | 1994-02-18 | 1995-08-31 | Henkel Kgaa | Hair treatment products |
| DE4414424A1 (en) * | 1994-04-26 | 1995-11-02 | Henkel Kgaa | Hair treatment products |
| FR2773070B1 (en) | 1997-12-31 | 2000-06-30 | Oreal | COMPOSITIONS FOR THE TREATMENT OF KERATINIC MATERIALS COMPRISING THE COMBINATION OF A ZWITTERIONIC POLYMER AND A NON-VOLATILE AND WATER INSOLUBLE SILICONE |
| DE19833516C1 (en) † | 1998-07-25 | 2000-02-03 | Wella Ag | Hair fixatives with amphoteric and acidic polymers |
| DE19940547A1 (en) | 1999-08-26 | 2001-03-01 | Henkel Kgaa | Detergent tablets with partial coating |
| DE10010760A1 (en) | 2000-03-04 | 2001-09-20 | Henkel Kgaa | Laundry and other detergent tablets containing enzymes, e.g. controlled release tablets, have two or more uncompressed parts containing active substances and packaging system with specified water vapor permeability |
| DE10113446A1 (en) | 2001-03-19 | 2002-09-26 | Schwarzkopf Gmbh Hans | Pharmaceutical or cosmetic hair treatment agents, especially for promoting hair growth, contain a betaine, especially carnitine, histidine, taurine, choline or betaine or their derivatives |
| DE10241466B4 (en) * | 2001-12-14 | 2006-05-24 | Henkel Kgaa | Inline blending and shaping of water-soluble polymers |
| FR2833832B1 (en) † | 2001-12-21 | 2005-08-05 | Oreal | COMPOSITION FOR THE OXIDATION STAIN OF KERATIN FIBERS COMPRISING AN OXYALKYLENE CARBOXYLIC ETHER ACID, A NON-IONIC SURFACTANT AND A PARTICULAR POLYMER |
| DE10245260A1 (en) * | 2002-09-27 | 2004-04-15 | Henkel Kgaa | Process for the production of coated detergent or cleaning agent portions |
| DE10344527A1 (en) * | 2003-09-25 | 2005-04-21 | Beiersdorf Ag | Foaming preparations with yield point |
| DE10359538A1 (en) | 2003-12-17 | 2005-07-14 | Hans Schwarzkopf & Henkel Gmbh & Co. Kg | Toning agent in tubes |
| DE10359539A1 (en) | 2003-12-17 | 2005-07-14 | Hans Schwarzkopf & Henkel Gmbh & Co. Kg | Nurturing Oxidant in Tube |
| DE10359557A1 (en) | 2003-12-17 | 2005-07-14 | Hans Schwarzkopf & Henkel Gmbh & Co. Kg | Oxidation dye in tube |
| EP1729853B1 (en) | 2004-02-27 | 2010-04-07 | Henkel AG & Co. KGaA | Use of cationic starch derivatives for promoting colour yield |
| DE102004045274A1 (en) | 2004-09-16 | 2006-03-23 | Henkel Kgaa | Active substance mixture for the treatment of keratinic fibers |
| DE102004062702A1 (en) | 2004-09-16 | 2006-03-23 | Henkel Kgaa | Color-changing agents with Moringa extract |
| DE102004051648A1 (en) | 2004-10-22 | 2006-04-27 | Basf Ag | Anionic ethyl methacrylate copolymers and their use |
| DE102004062428A1 (en) | 2004-12-20 | 2006-07-06 | Henkel Kgaa | Hair color changing shampoo |
| US8147813B2 (en) | 2005-03-30 | 2012-04-03 | L'oreal S.A. | Detergent cosmetic compositions comprising three surfactants and at least one fatty ester, and use thereof |
| FR2887448B1 (en) * | 2005-06-23 | 2009-04-17 | Rhodia Chimie Sa | COSMETIC COMPOSITION COMPRISING AN AMPHOLYTE COPOLYMER |
| DE102005038359A1 (en) | 2005-08-11 | 2007-02-15 | Henkel Kgaa | Amaranth seed oil in hair treatment products |
| DE102005043187A1 (en) | 2005-09-09 | 2007-03-15 | Henkel Kgaa | Polymers with a low molecular weight |
| DE102005062360A1 (en) | 2005-12-23 | 2007-06-28 | Henkel Kgaa | Method for gentle dyeing of keratinic fibers, especially human hair, includes treatment, after oxidation dyeing, with a foam-forming composition that includes a care agent |
| JP5176188B2 (en) | 2006-04-21 | 2013-04-03 | ディーエスエム アイピー アセッツ ビー．ブイ． | Use of opioid receptor antagonists |
| KR101445401B1 (en) | 2006-06-16 | 2014-09-26 | 디에스엠 아이피 어셋츠 비.브이. | Compositions based on hyperbranched condensation polymers and novel hyperbranched condensation polymers |
| KR20090051084A (en) | 2006-08-11 | 2009-05-20 | 바스프 에스이 | The use of cationic copolymerization from amine-holding acrylates and n-vinyl imidazolium salts in hair cosmetic products |
| DE102006039283A1 (en) | 2006-08-22 | 2008-02-28 | Henkel Kgaa | Agent, useful for coating or fixing human hair and for smoothening of textiles, comprises a polymer with a phenyl unit in a carrier |
| US8247507B2 (en) | 2006-09-21 | 2012-08-21 | Basf Se | Cationic polymers as thickeners for aqueous and alcoholic compositions |
| DE102006050650A1 (en) * | 2006-10-24 | 2008-04-30 | Henkel Kgaa | Hair treatment agent, useful to e.g. increase the elasticity of keratinic fibers, comprises a copolymer of first monomer and second monomer comprising e.g. acrylic acid, a silicone and a caring agent comprising e.g. vitamins and ubiquinone |
| DE102006060910A1 (en) | 2006-12-20 | 2008-07-03 | Henkel Kgaa | Suspensions of composite materials |
| DE102006061555A1 (en) | 2006-12-27 | 2008-07-03 | Henkel Kgaa | Cosmetic preparation for the cleaning and treatment of skin and hair, contains, as active ingredients, natural silk or its derivatives and a Sub-Group 1 or 8 metal or metal salt, e.g. gold or silver |
| DE102007005646A1 (en) | 2007-01-31 | 2008-08-07 | Henkel Ag & Co. Kgaa | Colorant containing luminescent pigments which can be excited by visible light |
| DE102007013145A1 (en) | 2007-03-15 | 2008-09-18 | Henkel Ag & Co. Kgaa | Waving agents with hair fiber structure |
| DE102007013144A1 (en) | 2007-03-15 | 2008-09-18 | Henkel Ag & Co. Kgaa | Hair treatment agent with anti-dandruff action |
| DE102007016708A1 (en) | 2007-04-04 | 2008-10-09 | Henkel Ag & Co. Kgaa | Stabilization of surfactant-containing agents |
| DE102007027856A1 (en) | 2007-06-13 | 2008-12-24 | Henkel Ag & Co. Kgaa | Oxidation colorant for coloring keratin-containing fibers with atmospheric oxygen as the sole oxidant |
| DE102007030099A1 (en) | 2007-06-28 | 2009-01-02 | Henkel Ag & Co. Kgaa | Cosmetic composition containing a champagne extract |
| DE102007031202A1 (en) | 2007-07-04 | 2009-03-19 | Henkel Ag & Co. Kgaa | New protein hydrolysate obtained from wool of Vicugna useful as laundry detergent, wool detergent, manual dishwashing agent and cosmetic agent, which is useful for treating skin and hair |
| DE102007033093A1 (en) | 2007-07-13 | 2009-01-15 | Henkel Ag & Co. Kgaa | Agent with anti-irritating agent |
| DE102007033184A1 (en) | 2007-07-13 | 2009-07-02 | Henkel Ag & Co. Kgaa | Cosmetic composition, useful for the care and preservation of natural functions of keratin fibers and increasing the brightness of keratin fibers, preferably human hairs, comprises a powder of a gemstone or semi-precious stone |
| DE102007033091A1 (en) | 2007-07-13 | 2009-01-15 | Henkel Ag & Co. Kgaa | Agent with anti-irritating agent |
| DE102007034482A1 (en) | 2007-07-20 | 2009-01-22 | Henkel Ag & Co. Kgaa | Oxidative hair treatment with Litchi extract and catechins |
| DE102007036499A1 (en) | 2007-08-01 | 2009-02-05 | Henkel Ag & Co. Kgaa | Natural cosmetic hair treatment agent |
| DE102007036911A1 (en) | 2007-08-06 | 2009-02-12 | Henkel Ag & Co. Kgaa | Hair Dye |
| DE102007037432A1 (en) | 2007-08-08 | 2009-02-12 | Henkel Ag & Co. Kgaa | Enzymatic lightening of keratinic fibers |
| DE102007037428A1 (en) | 2007-08-08 | 2009-02-12 | Henkel Ag & Co. Kgaa | Hair treatment agent for increasing volume |
| DE102007040313A1 (en) | 2007-08-24 | 2009-02-26 | Henkel Ag & Co. Kgaa | Hair treatment agents |
| US8673832B2 (en) | 2007-08-24 | 2014-03-18 | The Dial Corporation | Liquid skin cleanser with multiple signals of adequate wash duration with adequate mechanical force |
| DE102007040314A1 (en) | 2007-08-24 | 2009-02-26 | Henkel Ag & Co. Kgaa | Kit for providing colorants |
| DE102007042286A1 (en) | 2007-09-06 | 2009-03-12 | Henkel Ag & Co. Kgaa | Colorants with natural dyes and 1,3-dihydroxyacetone |
| DE102007045974A1 (en) | 2007-09-25 | 2009-04-09 | Henkel Ag & Co. Kgaa | Biotin and silica against hair aging |
| DE102007046628A1 (en) | 2007-09-27 | 2009-04-02 | Henkel Ag & Co. Kgaa | Hair dyeing process with oxidative pretreatment |
| DE102007048140A1 (en) | 2007-10-05 | 2009-04-09 | Henkel Ag & Co. Kgaa | Oxidative hair treatment with reduced hair damage |
| DE102007050767B4 (en) | 2007-10-22 | 2013-10-02 | Henkel Ag & Co. Kgaa | Oral and dental care and cleaning compositions containing 2- and / or 3- and / or 4-piperidone and use of these piperidones |
| DE102008038138A1 (en) | 2008-08-18 | 2010-02-25 | Henkel Ag & Co. Kgaa | Agent, useful for coloring keratin fibers, which are fur, wool or feathers, preferably human hair, comprises a dye starting product and a browning product, where the browning product is obtained by heating sugar |
| DE102007053950A1 (en) | 2007-11-09 | 2009-05-14 | Henkel Ag & Co. Kgaa | Agent with bioflavonoid |
| DE102007053952A1 (en) | 2007-11-09 | 2009-05-14 | Henkel Ag & Co. Kgaa | Agent containing ester compound with wax alcohol component |
| DE102008014368A1 (en) | 2008-03-17 | 2009-10-08 | Henkel Ag & Co. Kgaa | Cosmetic composition for hair treatment, for use e.g. in shampoos, rinses, hair-care products or hair dyes, contains a special flavonoid and a vitamin of the B group, especially tiliroside and pantolactone |
| DE102007054706A1 (en) | 2007-11-14 | 2009-05-20 | Henkel Ag & Co. Kgaa | Hair treatment with Litchi extract and taurine |
| DE102007054708A1 (en) | 2007-11-14 | 2009-05-20 | Henkel Ag & Co. Kgaa | Hair treatment with Litchi extract and imidazole derivatives |
| DE102007056935A1 (en) | 2007-11-23 | 2009-05-28 | Henkel Ag & Co. Kgaa | Two-component aerosol hair color |
| DE102007056934A1 (en) | 2007-11-23 | 2009-05-28 | Henkel Ag & Co. Kgaa | Oxidation colorant for coloring keratin-containing fibers with atmospheric oxygen as the sole oxidant |
| DE102008034386A1 (en) | 2007-11-23 | 2009-07-30 | Henkel Ag & Co. Kgaa | New protein hydrolyzates and derivatives, useful in textile treatment and cosmetic compositions, e.g. hair tonics, are obtained from hairs of mammals with high hair density |
| DE102007060530A1 (en) | 2007-12-13 | 2009-09-17 | Henkel Ag & Co. Kgaa | Hair conditioning agents with cationic behenyl compounds and selected silicones and / or cosmetic oils |
| DE102007060532A1 (en) | 2007-12-13 | 2009-09-17 | Henkel Ag & Co. Kgaa | Hair conditioning agents with cationic compounds and selected silicones and / or cosmetic oils |
| DE102007060528A1 (en) | 2007-12-13 | 2009-06-18 | Henkel Ag & Co. Kgaa | Hair conditioning compositions containing imidazolines and selected silicones and / or cosmetic oils |
| DE102009009004A1 (en) | 2008-02-18 | 2009-09-17 | Seaquist Perfect Dispensing Gmbh | Dispensing device, preferably pump preferably with a sprayable and/or non-sprayable cosmetic liquid, where the cosmetic liquid comprises single phase solution, mixture of non-miscible liquid phases, and oil-in-water-/water-in-oil-emulsion |
| DE102008012059A1 (en) | 2008-02-29 | 2009-09-03 | Henkel Ag & Co. Kgaa | Hair treatment remedy with goji extract |
| DE102008012068A1 (en) | 2008-02-29 | 2009-09-10 | Henkel Ag & Co. Kgaa | Hair treatment with cranberry extract |
| DE102008012058A1 (en) | 2008-02-29 | 2009-09-03 | Henkel Ag & Co. Kgaa | Hair treatment with acai extract |
| DE102008019340A1 (en) | 2008-04-16 | 2009-10-22 | Henkel Ag & Co. Kgaa | Hair treatment with cloudberry fruit extract |
| DE102008031726A1 (en) | 2008-07-04 | 2010-01-07 | Henkel Ag & Co. Kgaa | Hair conditioning agents with imidazolines |
| DE102008031701A1 (en) | 2008-07-04 | 2010-01-07 | Henkel Ag & Co. Kgaa | Hair conditioning agents with imidazolines |
| DE102008031749A1 (en) | 2008-07-04 | 2010-01-07 | Henkel Ag & Co. Kgaa | Hair conditioning agents with imidazolines |
| DE102008031715A1 (en) | 2008-07-04 | 2010-01-07 | Henkel Ag & Co. Kgaa | Hair conditioning agents with imidazolines |
| DE102008031700A1 (en) | 2008-07-04 | 2010-01-07 | Henkel Ag & Co. Kgaa | Hair conditioning agents with imidazolines |
| DE102008031748A1 (en) | 2008-07-04 | 2010-01-07 | Henkel Ag & Co. Kgaa | Hair conditioning agents with imidazolines |
| DE102008031702A1 (en) | 2008-07-04 | 2010-01-07 | Henkel Ag & Co. Kgaa | Hair conditioning agents with imidazolines |
| DE102008032208A1 (en) | 2008-07-09 | 2010-01-14 | Henkel Ag & Co. Kgaa | Oxidation stain with basic amino acid, ammonium sulfate and alkanolamines |
| DE102008032179A1 (en) | 2008-07-09 | 2010-01-21 | Henkel Ag & Co. Kgaa | Surfactant-containing composition, useful for cleaning the skin, comprises a film former and a beneficial substance comprising UV filter substances or tanning agents |
| DE102008034388A1 (en) | 2008-07-23 | 2010-01-28 | Henkel Ag & Co. Kgaa | Surfactant-containing composition with special emulsifier mixture |
| DE102008034845A1 (en) | 2008-07-24 | 2010-02-04 | Henkel Ag & Co. Kgaa | Composition, useful e.g. for coloring and/or lightening keratin fibers, preferably human hair, comprises color-modifying component in a carrier and further contains a combination of thiolactic acid and/or its salt, and functional additive |
| DE102008035172A1 (en) | 2008-07-28 | 2010-02-04 | Henkel Ag & Co. Kgaa | Structured composition with optimal storage stability properties |
| DE102008036073A1 (en) | 2008-08-04 | 2010-02-11 | Henkel Ag & Co. Kgaa | Detergent with terpolymer |
| DE102008036952A1 (en) | 2008-08-08 | 2009-06-10 | Henkel Ag & Co. Kgaa | Lightening material for keratin fibres, especially for bleaching human hair, comprises two separate components, one with hydrogen peroxide, plus an indicator which changes color when the components are mixed |
| DE102008037633A1 (en) | 2008-08-14 | 2010-02-18 | Henkel Ag & Co. Kgaa | Cosmetic composition containing oil from the fruits of the Sumac family |
| DE102008046178A1 (en) | 2008-09-06 | 2010-03-11 | Henkel Ag & Co. Kgaa | Composition, useful for the treatment of skin and keratin fibers (hair), comprises oil extracted from fruits, UV filter e.g. p-aminobenzoic acid, compound having film-forming properties e.g. vitamin B5, and cosmetic carrier |
| DE102008048438A1 (en) | 2008-09-23 | 2010-03-25 | Henkel Ag & Co. Kgaa | Compositions for reducing breakage of keratinic fibers |
| DE102008050430A1 (en) | 2008-10-08 | 2010-04-15 | Henkel Ag & Co. Kgaa | Anti-dandruff and anti-relapse shampoo |
| DE102008062237A1 (en) | 2008-12-16 | 2010-06-17 | Henkel Ag & Co. Kgaa | Reductive discoloration of keratinous fibers |
| DE102008063280A1 (en) | 2008-12-29 | 2010-07-01 | Henkel Ag & Co. Kgaa | Waving agent with aloe vera |
| DE102009026775A1 (en) | 2009-06-05 | 2010-12-09 | Henkel Ag & Co. Kgaa | Surfactant-containing cosmetic cleanser with royal jelly |
| DE102009031432A1 (en) | 2009-07-01 | 2011-01-05 | Henkel Ag & Co. Kgaa | Compact hair spray |
| DE102009028443A1 (en) | 2009-08-11 | 2010-06-10 | Henkel Ag & Co. Kgaa | Cosmetic hair cleaning agent, useful to improve wet and dry hair, and as e.g. liquid soaps and shampoos, comprises mild surfactant from anionic and amphoteric/zwitterionic surfactant, and seed oil of Pentaclethra macroloba plant |
| DE102009029183A1 (en) | 2009-09-03 | 2011-03-10 | Henkel Ag & Co. Kgaa | Permanent Wave System |
| DE102009044920A1 (en) | 2009-09-23 | 2011-04-07 | Henkel Ag & Co. Kgaa | Use of certain amino acids in dyes of keratinic fibers for color intensification |
| DE102009045176A1 (en) | 2009-09-30 | 2011-04-07 | Henkel Ag & Co. Kgaa | Heat-assisting reductive decolorization of keratin-containing fibers |
| DE102009045605A1 (en) | 2009-10-13 | 2011-04-14 | Henkel Ag & Co. Kgaa | Sprayable hair cleanser |
| DE102009045606A1 (en) | 2009-10-13 | 2011-04-14 | Henkel Ag & Co. Kgaa | Sensitive hair cleanser |
| DE102010001360A1 (en) | 2009-11-18 | 2011-05-19 | Henkel Ag & Co. Kgaa | Foamy colorants |
| WO2011061144A2 (en) | 2009-11-20 | 2011-05-26 | Basf Se | The present invention relates to the use of beta-(1, 3)- beta-(1, 4) glucan with an average molecular weight of from 5.000 to 150.000 da for the increase of synthesis of collagen |
| DE102010002558A1 (en) | 2009-11-20 | 2011-06-01 | Symrise Ag | Use of physiological cooling agents and agents containing such agents |
| DE102009054833A1 (en) | 2009-12-17 | 2011-06-22 | Henkel AG & Co. KGaA, 40589 | Antibacterial and bleaching oral and dental care and cleaning products II |
| KR20130036188A (en) | 2010-03-02 | 2013-04-11 | 바스프 에스이 | Block copolymers and their use |
| DE102010029976A1 (en) | 2010-06-11 | 2011-12-15 | Henkel Ag & Co. Kgaa | Substantially ammonia-free corrugating agent |
| DE102010063518A1 (en) | 2010-12-20 | 2012-06-21 | Henkel Ag & Co. Kgaa | Methods and compositions for smoothing keratin-containing fibers |
| DE102010055817A1 (en) | 2010-12-23 | 2012-06-28 | Henkel Ag & Co. Kgaa | Foaming agent-containing foamable cosmetic composition for skin and body care |
| JP6049684B2 (en) | 2011-03-23 | 2016-12-21 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Compositions containing polymeric ionic compounds containing imidazolium groups |
| DE102011076852A1 (en) | 2011-06-01 | 2012-12-06 | Henkel Kgaa | Substantially ammonia-free corrugating agent with cysteine |
| DE102011079664A1 (en) | 2011-07-22 | 2012-04-26 | Henkel Kgaa | Composition useful e.g. for treating skin and keratin fibers, caring and conditioning of skin and/or keratin fibers and restructuring keratin fibers, comprises oil obtained from seeds of cape chestnut, surfactants and aqueous carrier |
| EP2758041B1 (en) | 2011-09-20 | 2021-01-13 | Basf Se | Low-molecular modulators of the cold-menthol receptor trpm8 and use of same |
| DE102011087624A1 (en) | 2011-12-02 | 2013-06-06 | Henkel Ag & Co. Kgaa | "Hair treatment composition with 4-morpholinomethyl-substituted silicone (s) and conditioning agent (s)" |
| CN104487139B (en) * | 2012-02-13 | 2017-02-22 | 赫尔克里士公司 | Conditioning composition additive for providing immediate and long lasting benefits to keratin substrates |
| JP6377052B2 (en) | 2012-04-03 | 2018-08-22 | ビーエイエスエフ・ソシエタス・エウロパエアＢａｓｆ Ｓｅ | Hair cosmetic composition containing plant lecithin |
| DE102012206949A1 (en) | 2012-04-26 | 2013-10-31 | Henkel Ag & Co. Kgaa | Hair treatment agent with hydroxy-terminated organopolysiloxane (s) and conditioning agent (s) |
| EP2810640A1 (en) | 2013-06-03 | 2014-12-10 | Basf Se | Esters of oligohydroxy carboxylic acids and their use |
| EP2810935B1 (en) | 2013-06-03 | 2016-05-25 | Basf Se | Sulfated esters of oligohydroxy carboxylic acids and their use |
| WO2015059084A1 (en) | 2013-10-21 | 2015-04-30 | Basf Se | Precipitation polymerization in the presence of a tertiary amine and of an anhydride |
| EP2899214A1 (en) | 2014-01-27 | 2015-07-29 | Basf Se | Ethylenically unsaturated polysaccharides, method for their production and their use |
| EP2899213A1 (en) | 2014-01-27 | 2015-07-29 | Basf Se | Modified polysaccharides, method for their production and their use |
| DE102015221460B4 (en) | 2015-11-03 | 2022-11-10 | Henkel Ag & Co. Kgaa | Permanent waving process with improved care performance and waving effect |
| DE102015222215A1 (en) | 2015-11-11 | 2017-05-11 | Henkel Ag & Co. Kgaa | Improved discoloration of dyed keratin fibers |
| DE102015222214A1 (en) | 2015-11-11 | 2017-05-11 | Henkel Ag & Co. Kgaa | Improved discoloration of dyed keratin fibers |
| DE102015222976A1 (en) | 2015-11-20 | 2017-05-24 | Henkel Ag & Co. Kgaa | Hair care compositions containing casein hydrolyzate for improving the hair structure |
| US20200086616A1 (en) | 2016-12-16 | 2020-03-19 | Basf Se | Multi-layered film , method for the production and use thereof |
| DE102016225377B4 (en) | 2016-12-19 | 2022-04-28 | Henkel Ag & Co. Kgaa | Creamy hair dye II |
| DE102016225473A1 (en) | 2016-12-19 | 2017-08-24 | Henkel Ag & Co. Kgaa | Hair dyes with improved dyeing properties |
| DE102016225476B4 (en) | 2016-12-19 | 2022-04-28 | Henkel Ag & Co. Kgaa | Oxidative hair treatment with after-treatment to improve wash fastness |
| DE102016225378A1 (en) | 2016-12-19 | 2018-06-21 | Henkel Ag & Co. Kgaa | Creamy hair dye III |
| KR20200002947A (en) | 2017-04-28 | 2020-01-08 | 시므라이즈 아게 | Yarrow Fresh-Plant Squeezed Juice Concentrates, Production, and Uses |
| KR20200020886A (en) | 2017-06-26 | 2020-02-26 | 바스프 에스이 | Alkoxylation of Hydroxy Acids |
| DE102018209891A1 (en) | 2018-06-19 | 2019-12-19 | Henkel Ag & Co. Kgaa | Oxidative hair lightening or hair dye from cold production for level 2 colorations |
| DE102018209894A1 (en) | 2018-06-19 | 2019-12-19 | Henkel Ag & Co. Kgaa | Oxidative hair lightening or hair dye with improved application properties |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH645653A5 (en) * | 1980-08-01 | 1984-10-15 | Ciba Geigy Ag | QUATERNAERE, COPOLYMERE, HIGH MOLECULAR AMMONIUM SALTS ON ACRYLIC BASE, THE PRODUCTION AND USE THEREOF AS ACTIVE COMPONENTS IN COSMETIC AGENTS. |
| EP0047714B1 (en) * | 1980-09-05 | 1985-10-30 | Ciba-Geigy Ag | Mixtures of polymeric high-molecular acrylic quaternary ammonium salts and detergents, their preparation and use in cosmetic formulations |
| JPS5813700A (en) * | 1981-07-17 | 1983-01-26 | 花王株式会社 | Detergent composition |
| EP0217274A3 (en) * | 1985-09-30 | 1988-06-29 | Kao Corporation | Hair cosmetic composition |
| DE3708451A1 (en) * | 1987-03-16 | 1988-10-06 | Henkel Kgaa | ZWITTERIONIC POLYMERS AND THEIR USE IN HAIR TREATMENT AGENTS |
-
1989
- 1989-09-08 DE DE19893929973 patent/DE3929973A1/en not_active Withdrawn
-
1990
- 1990-08-30 JP JP51324290A patent/JPH05500220A/en active Pending
- 1990-08-30 EP EP19900914143 patent/EP0490982A1/en active Pending
- 1990-08-30 CA CA 2066226 patent/CA2066226A1/en not_active Abandoned
- 1990-08-30 WO PCT/EP1990/001444 patent/WO1991003229A1/en not_active Application Discontinuation
- 1990-09-07 DD DD34392990A patent/DD297554A5/en not_active IP Right Cessation
Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6365697B1 (en) | 1995-11-06 | 2002-04-02 | Basf Aktiengesellschaft | Water-soluble or water-dispersible polyurethanes with terminal acid groups, the production and the use thereof |
| US6277386B1 (en) | 1998-02-25 | 2001-08-21 | Basf Aktiengesellschaft | Cosmetic |
| US6932964B1 (en) | 1998-08-26 | 2005-08-23 | Basf Aktiengesellschaft | Cosmetic composition with water-soluble or water-dispersible polymers |
| US6410004B1 (en) | 1999-03-12 | 2002-06-25 | Basf Aktiengesellschaft | Polyureas and water-soluble or water-dispersible polymeric salts |
| US6800276B2 (en) | 1999-03-12 | 2004-10-05 | Basf Aktiengesellschaft | Polyureas and water-soluble or water-dispersible polymeric salts |
| US6871652B1 (en) | 1999-07-03 | 2005-03-29 | Hans Schwarzkopf Gmbh & Co. Kg | Method for permanently shaping keratin fibers, and agents |
| US6828443B1 (en) | 1999-07-06 | 2004-12-07 | Henkel Kommanditgesellschaft Auf Aktien | Dyes and colorants |
| US6541032B1 (en) | 1999-10-13 | 2003-04-01 | Basf Aktiengesellschaft | Use of finely divided dye-containing polymers PD as color-imparting constituent in cosmetic compositions |
| US7098178B2 (en) | 2000-03-16 | 2006-08-29 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Silicic acid ester mixtures |
| US7169193B2 (en) | 2000-04-28 | 2007-01-30 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Use of sugar surfactants and fatty acid partial glycerides |
| US6858216B2 (en) | 2000-05-06 | 2005-02-22 | Henkel Kommanditgesellschaft Auf Aktien | Cosmetic agent containing 2-furanone derivatives |
| US7417019B2 (en) | 2000-07-14 | 2008-08-26 | Henkel Kommanditgesellschaft Auf Aktien | Hollow body with a compartment, containing a portion of a washing, cleaning or rinsing agent |
| US7601679B2 (en) | 2000-07-14 | 2009-10-13 | Henkel Ag & Co. Kgaa | Process for producing a hollow body with a compartment, containing a portion of a washing, cleaning or rinsing agent |
| US6812200B2 (en) | 2000-12-23 | 2004-11-02 | Henkel Kommanditgesellschaft Auf Aktien | Process for coating detergent tablets |
| US6736862B2 (en) | 2001-01-10 | 2004-05-18 | Henkel Kommanditgesellschaft Auf Aktien | Indole/indoline based hybrid dyes and indole/indoline based hybrid dye intermediate products |
| US7375070B2 (en) | 2002-08-14 | 2008-05-20 | Henkel Kommanditgesellschaft Auf Aktien | Portioned detergent composition |
| US8034888B2 (en) | 2004-10-22 | 2011-10-11 | Basf Se | Amphoteric ethyl methacrylate copolymers and use thereof |
| US8821841B2 (en) | 2005-08-11 | 2014-09-02 | Basf Se | Copolymers for cosmetic applications |
| US8753408B2 (en) | 2007-08-23 | 2014-06-17 | Henkel Ag & Co. Kgaa | Reductive decoloration of keratin-containing fibers |
| US8268015B2 (en) | 2008-12-16 | 2012-09-18 | Henkel Ag & Co. Kgaa | Method for decolorizing keratin-containing fibers |
| US8673275B2 (en) | 2010-03-02 | 2014-03-18 | Basf Se | Block copolymers and their use |
| US10323215B2 (en) | 2013-07-03 | 2019-06-18 | Basf Se | Solid polymer composition obtained by polymerization of an acid group containing monomer in the presence of a polyether compound |
| US10344249B2 (en) | 2013-07-03 | 2019-07-09 | Basf Se | Gel-like polymer composition obtained by polymerizing a monomer containing acid groups in the presence of a polyether compound |
| US10655088B2 (en) | 2013-07-03 | 2020-05-19 | Basf Se | Solid polymer composition obtained by polymerization of an acid group-containing monomer in the presence of a polyether compound |
| DE102015218077A1 (en) | 2015-09-21 | 2017-03-23 | Henkel Ag & Co. Kgaa | Hair-friendly oxidation dye or bleaching agent and gentle hair dyeing or bleaching method |
| FR3041257A1 (en) | 2015-09-21 | 2017-03-24 | Henkel Ag & Co Kgaa | |
| US10143646B2 (en) | 2015-09-21 | 2018-12-04 | Henkel Ag & Co. Kgaa | Oxidative coloring or blonding agent gentle on hair, and gentle hair coloring or blonding method |
| US11434220B2 (en) | 2017-08-31 | 2022-09-06 | Basf Se | Use of physiological cooling active ingredients, and compositions comprising such active ingredients |
Also Published As
| Publication number | Publication date |
|---|---|
| DD297554A5 (en) | 1992-01-16 |
| JPH05500220A (en) | 1993-01-21 |
| DE3929973A1 (en) | 1991-03-14 |
| WO1991003229A1 (en) | 1991-03-21 |
| EP0490982A1 (en) | 1992-06-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2066226A1 (en) | Hair care preparations | |
| ES2297883T3 (en) | ANPHOLIT POLYMERS FOR USE IN PRODUCTS FOR PERSONAL CARE. | |
| US5609862A (en) | Ampholyte teropolymers providing superior conditioning properties in shampoos and other hair care products | |
| US5275809A (en) | Ampholyte terpolymers providing superior conditioning properties in shampoos and other hair care products | |
| EP0522755B1 (en) | Ampholyte terpolymers providing superior conditioning properties in shampoos and other hair care products | |
| CA1091160A (en) | Hair preparation containing vinyl pyrrolidone copolymer | |
| US4165367A (en) | Hair preparations containing vinyl pyrrolidone copolymer | |
| EP0744936B1 (en) | Hair care products | |
| US5338541A (en) | Dual cationic terpolymers providing superior conditioning properties in hair, skin and nail care products | |
| WO2005099654A1 (en) | Water soluble polymer complexes with surfactants | |
| WO1997002006A1 (en) | Preparation for treating keratin fibres | |
| AU2004308108B2 (en) | Cosmetic composition comprising an ampholyte copolymer | |
| CA2139495A1 (en) | Hair treatment preparation | |
| JP6689680B2 (en) | Cleaning composition | |
| US5747014A (en) | Cosmetics compositions containing at least one anionic suracant of alkylgalactoside uronate type and at least one amphoteric polymer | |
| ES2235509T3 (en) | CATIONIC POLYMERS AND ITS USE. | |
| US5609857A (en) | Methods of conditioning hair which utilize polymeric N-vinyl formamide | |
| EP1302191A2 (en) | Foamable composition for hair care | |
| GB2177916A (en) | Cosmetic composition | |
| WO2009122844A1 (en) | Cosmetic preparation | |
| EP2391339A2 (en) | Color-preserving hair treatment agents | |
| CA2145861A1 (en) | Hair treatment preparations | |
| JP2024108920A (en) | Cleaning composition | |
| KR100940442B1 (en) | Personal cleansing composition comprising self emulsified silicone copolymer | |
| MXPA99008974A (en) | Ampholyte polymers for use in personal care products |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |