WO1991003229A1 - Hair care preparations - Google Patents
Hair care preparations Download PDFInfo
- Publication number
- WO1991003229A1 WO1991003229A1 PCT/EP1990/001444 EP9001444W WO9103229A1 WO 1991003229 A1 WO1991003229 A1 WO 1991003229A1 EP 9001444 W EP9001444 W EP 9001444W WO 9103229 A1 WO9103229 A1 WO 9103229A1
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- WO
- WIPO (PCT)
- Prior art keywords
- hair
- preparations according
- monomers
- group
- groups
- Prior art date
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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
Definitions
- the invention relates to preparations for hair treatment which contain zwitterionic polymers.
- Polymeric compounds are frequently used as active ingredients that improve hair properties.
- Cationic polymers such as, for example, the cellulose derivatives known from the American patents US 3,816,616 and US 3,472,840, can significantly improve wet combability, but only achieve unsatisfactory hair-setting and hair-stabilizing effects.
- zwitterionic polymers which contain anionic groups, usually carboxyl groups, and quaternary ammonium groups in the molecule in hair treatment compositions.
- DE-OS 21 50 557 describes the use of polymers of zwitterionic monomers in hair fixatives.
- DE-OS 28 17 369 also disclosed the use of copolymers of dimethylaminoethyl methacrylate, acrylic acid and methyl methacrylate in hair fixatives and shampoos.
- zwitterionic polymers known for hair treatment and hair setting agents have the disadvantage, in particular in formulations with anionic surfactants, that the hair-activating and hair-setting properties are gradually lost in the course of longer storage times. It was therefore proposed in DE-OS 37 08 451, zwitterionic polymers consisting of 30-70% monomers with quaternary ammonium groups, 10-30% monomeric olefinically unsaturated carboxylic acids, 10-30% monomeric olefinically unsaturated carboxylic acid esters and 0-40% monomers with tertiary amino groups to use. These polymers are well tolerated with anionic and cationic surfactants and show good hair-activating and hair-stabilizing properties.
- Suitable polymers are thus available to achieve the desired effects on the hair, but these are composed of at least 3 or 4 monomers. There is therefore still a need for polymers which, with comparable properties, have a less complex structure, ie can be prepared from a smaller number of different monomers.
- the invention thus relates to aqueous preparations for hair treatment containing zwitterionic polymers, characterized in that the zwitterionic polymers essentially consist of one another
- R 1 -CH CR 2 -CO-Z- (C n H 2n ) -N (+) R 3 R 4 R 5 A (-) (I) in which R 1 and R 2 independently of one another represent hydrogen or a Methyl group and R 3 , R 4 and R 5 independently of one another for alkyl groups with 1 to 4 carbon atoms, Z an NH group or an oxygen atom, n an integer from 2 to 5 and A (-) the anion of an organic or inorganic Acid is and
- R 6 -CH CR 7 -COOH (II) in which R 6 and R 7 are independently hydrogen or methyl groups.
- Suitable starting monomers are e.g. B. dimethylaminoethyl acrylamide, dimethylaminoethyl methacrylamide, dimethylaminopropyl acrylamide, dimethylaminopropyl methacrylamide and diethylaminoethyl acrylamide if Z represents an NH group or dimethylaminoethyl acrylate, dimethylaminoethyl methacrylate and diethylaminoethyl acrylate if Z is an oxygen atom.
- the monomers mentioned are prepared by known processes, such as those described in, for. B. in US-PS 3 878 247, DE-PS 28 19 735, DE-PS 28 36 520, DE-PS 34 02 599 or CH-PS 464 891 are described.
- the monomers containing a tertiary amino group are then quaternized in a known manner, methyl chloride, dimethyl sulfate or diethyl sulfate being particularly suitable as alkylating reagents.
- the quaternization reaction can be carried out in aqueous solution or in the solvent. Suitable methods are e.g. B. in DE-OS 3330326, DE-OS 2537378 or DE-OS 3244274 described.
- Monomers of the formula (I) which are derivatives of acrylamide or methacrylamide are advantageously used. Also preferred are those monomers which contain halide, methoxysulfate or ethoxysulfate ions as counterions. Monomers of the formula (I) in which R 3 , R 4 and R 5 are methyl groups are also preferred.
- Acrylamidopropyltrimethylammonium chloride is a very particularly preferred monomer of formula (I).
- Acrylic acid, methacrylic acid, crotonic acid and 2-methyl-crotonic acid are suitable as monomeric carboxylic acids of formula (II).
- the zwitterionic polymers according to the invention are prepared from monomers of the formulas (I) and (II) by polymerization processes known per se.
- the polymerization can take place in either an aqueous or aqueous-alcoholic solution. Alcohols with 1 to 4 carbon atoms, preferably isopropanol, are used as alcohols, which simultaneously serve as polymerization regulators. However, other components can also be added to the monomer solution as regulators, e.g. B. formic acid or mercaptans such as thioethanol and thioglycolic acid.
- the polymerization is initiated with the help of radical-forming substances. For this purpose, redox systems and / or thermally decomposing radical formers of the type of azo compounds, such as.
- B azoisobutyronitrile, azo-bis (cyanopentanoic acid) or azo-bis (amidinopropane) dihydrochloride can be used.
- redox systems such.
- the polymerization can be carried out isothermally or under adiabatic conditions, the temperature range for the course of the reaction being able to fluctuate between 20 and 200 ° C. depending on the concentration ratios as a result of the heat of polymerization being released, and the reaction may have to be carried out under the excess pressure which arises.
- the reaction temperature is preferably between 20 and 100.degree.
- the pH during the copolymerization can vary within a wide range. Polymerization is advantageously carried out at low pH values; however, pH values above the neutral point are also possible.
- an aqueous base e.g. As sodium hydroxide solution, potassium hydroxide solution or ammonia, adjusted to a pH between 5 and 10, preferably 6 to 8. Further information on the polymerization process can be found in the examples.
- Polymers in which the monomers of the formula (I) were in excess of the monomers of the formula (II) have proven to be particularly effective. It is therefore preferred according to the invention to use those polymers which consist of monomers of the formula (I) and the monomers of the formula (II) in a molar ratio of from 60:40 to 95: 5, in particular from 75:25 to 95: 5 .
- the zwitterionic polymers mentioned are preferably present in the preparations according to the invention in amounts of 0.1 to 10% by weight, based on the entire preparation.
- the wet combability-improving effect of the polymers is very great even at low concentrations; the hair-activating and hair-setting effects, in contrast, are observed in most cases only at concentrations above about 1% by weight. It is therefore particularly preferred to use the polymers in amounts of about 1 to 5% by weight.
- the zwitterionic polymers according to the invention are preferably used in aqueous preparations containing surface-active compounds.
- Anionic, zwitterionic, amphoteric and / or nonionic surfactants are preferred as surface-active compounds.
- Suitable anionic surfactants in hair treatment compositions according to the invention are all anionic surface-active substances suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
- the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
- suitable anionic surfactants are the sodium, potassium and ammonium and the mono-, di- and trialkanolammonium salts with 2 or 3 carbon atoms in the alkanol group, from
- Preferred anionic surfactants are alkyl sulfate and alkyl polyglycol ether sulfates with 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 that contain at least one quaternary ammonium group and at least one -COO (-) - or -SO 3 (-) - group in the molecule.
- Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the coconut alkyl-N, N-dimethylammonium glycinate, N-acyl-aminopropyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyl N, N-dimethylammonium glycinate, and 2-alkyl3-carboxylmethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group, as well as the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
- Amphoteric surfactants are surface-active compounds which, in addition to a C 8 -C 18 alkyl or acyl group, contain at least one free amino group and at least one --COOH or -SO 3 H group in the molecule and are capable of forming internal salts are.
- amphoteric surfactants are N-alkylglycine, N-alkylaminopropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkyl aminopropionic acids and alkylaminoacetic acids each having about 8 to 18 carbon atoms in the alkyl group.
- Nonionic surfactants are, above all, the addition products of 2 to 20 moles of ethylene oxide with preferably linear alcohols with 12 to 18 C atoms, with alkylphenols with 8 to 15 C atoms in the alkyl group, with fatty acids with 12 to 18 C atoms, with fatty acid partial glycerides , on fatty acid sorbitan partial esters, on fatty acid alkanolamides and on methyl glucoside fatty acid esters.
- Other suitable nonionic surfactants are alkyl (oligo) glucosides, alkylamine oxide surfactants and fatty acid alkanolamides.
- Cationic surfactants can also be present in the preparations according to the invention if they are combined with the other components, e.g. anionic surfactants are compatible.
- Such cationic surfactants are e.g. B. from DE-OS 3442175 known.
- the preparations according to the invention preferably contain surface-active compounds in amounts of 0.1 to 40% by weight, based on the entire preparation.
- the zwitterionic polymers according to the invention are suitable as a setting and hair-activating component in all common aqueous preparations for cleaning and care of the hair.
- Such preparations can e.g. B. hair shampoos, hair rinsing agents, hair setting agents, hair blow agents and aqueous colorants, permanent waving agents or permanent wave fixing agents.
- the aqueous preparations for cleaning and maintaining the hair according to the invention can therefore contain, in addition to the obligatory zwitterionic polymers, all auxiliaries and additives customary for the particular application.
- cationic surfactants especially surface-active quaternary ammonium salts, fatty alcohols with 12 to 22 carbon atoms, fatty acid partial glycerides, cosmetic oil and fat components and water-soluble polymers with thickening effect.
- cationic surfactants especially surface-active quaternary ammonium salts, fatty alcohols with 12 to 22 carbon atoms, fatty acid partial glycerides, cosmetic oil and fat components and water-soluble polymers with thickening effect.
- hair fixers and blow dryers these are e.g. B. also cationic surfactants, cationic, nonionic or anionic polymers and lower alcohols.
- Hair dyes contain direct dyes or oxidation dye precursors, anionic or non-ionic surfactants, ammonia or alkanolamines and possibly antioxidants.
- Permanent wave fixatives contain an oxidizing agent, e.g. B. H 2 O 2 , H 2 O 2 addition compounds or potassium bromate, and anionic or nonionic sur
- the preparations according to the invention preferably have a pH of 4 to 10, in particular 5 to 9.
- the rinse is in the form of a cloudy solution.
- the wet combability of hair treated with this conditioner was very good; hair stress or static electricity was not observed. 2.2. Hair conditioner No.2
- the rinse is in the form of a cloudy solution.
- the wet combability of hair treated with this conditioner was very good.
- the rinse is in the form of an almost clear solution.
- the wet combability of hair treated with this conditioner was very good.
- the wet combability of the hair shampooed with this preparation was excellent.
- Texapon (R) K14 S spec. 15.0 sulfosuccinic acid half- esters based on a C 12-14 alkyl polyglycol (3 EO) ether, disodium salt (40%
- n-alkyl (C 12-14 ), (50% active substance) (HORIZON)
- the shampoo is clear and colorless. When the hair was treated with this shampoo, it received an excellent finish.
- This clear shampoo was particularly characterized by an excellent conditioning effect with good cleaning performance.
Abstract
Description
Claims
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 |
---|---|
WO1991003229A1 true WO1991003229A1 (en) | 1991-03-21 |
Family
ID=6388972
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1990/001444 WO1991003229A1 (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 (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993005756A1 (en) * | 1991-09-25 | 1993-04-01 | Henkel Kommanditgesellschaft Auf Aktien | Hair-treatment preparations |
WO1994001077A1 (en) * | 1992-07-03 | 1994-01-20 | Henkel Kommanditgesellschaft Auf Aktien | Hair-treatment agents |
WO1994001076A1 (en) * | 1992-07-03 | 1994-01-20 | Henkel Kommanditgesellschaft Auf Aktien | Hair conditioner |
US5631003A (en) * | 1991-09-25 | 1997-05-20 | Henkel Kommanditgesellschaft Auf Aktien | Hair treatment prepartation |
US6555101B1 (en) * | 1992-09-29 | 2003-04-29 | Henkel Kommanditgesellschaft Auf Aktien | Hair aftertreatment preparations |
US6555100B1 (en) | 1997-12-31 | 2003-04-29 | L'ORéAL S.A. | Compositions for treating keratinous materials containing a combination of a zwitterion polymer and a water insoluble non-volatile silicon |
US7553338B2 (en) | 2004-09-16 | 2009-06-30 | Henkel Kgaa | Color-modifying compositions containing a moringa plant seed protein and methods of treating keratin fibers therewith |
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- 1990-08-30 CA CA 2066226 patent/CA2066226A1/en not_active Abandoned
- 1990-08-30 EP EP19900914143 patent/EP0490982A1/en active Pending
- 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
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Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993005756A1 (en) * | 1991-09-25 | 1993-04-01 | Henkel Kommanditgesellschaft Auf Aktien | Hair-treatment preparations |
EP0535447A1 (en) * | 1991-09-25 | 1993-04-07 | Henkel KGaA | Hair treatment compositions |
US5631003A (en) * | 1991-09-25 | 1997-05-20 | Henkel Kommanditgesellschaft Auf Aktien | Hair treatment prepartation |
WO1994001077A1 (en) * | 1992-07-03 | 1994-01-20 | Henkel Kommanditgesellschaft Auf Aktien | Hair-treatment agents |
WO1994001076A1 (en) * | 1992-07-03 | 1994-01-20 | Henkel Kommanditgesellschaft Auf Aktien | Hair conditioner |
US6555101B1 (en) * | 1992-09-29 | 2003-04-29 | Henkel Kommanditgesellschaft Auf Aktien | Hair aftertreatment preparations |
US6555100B1 (en) | 1997-12-31 | 2003-04-29 | L'ORéAL S.A. | Compositions for treating keratinous materials containing a combination of a zwitterion polymer and a water insoluble non-volatile silicon |
EP0966248B2 (en) † | 1997-12-31 | 2008-04-02 | L'oreal | Compositions for treating keratinous materials containing a combination of a zwitterion polymer and a water insoluble non-volatile silicon |
US7553338B2 (en) | 2004-09-16 | 2009-06-30 | Henkel Kgaa | Color-modifying compositions containing a moringa plant seed protein and methods of treating keratin fibers therewith |
Also Published As
Publication number | Publication date |
---|---|
JPH05500220A (en) | 1993-01-21 |
EP0490982A1 (en) | 1992-06-24 |
CA2066226A1 (en) | 1991-03-09 |
DD297554A5 (en) | 1992-01-16 |
DE3929973A1 (en) | 1991-03-14 |
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