WO1994001079A1 - Produits pour le traitement des cheveux renfermant des copolymerisats servant d'agents filmogenes - Google Patents

Produits pour le traitement des cheveux renfermant des copolymerisats servant d'agents filmogenes Download PDF

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Publication number
WO1994001079A1
WO1994001079A1 PCT/EP1993/001719 EP9301719W WO9401079A1 WO 1994001079 A1 WO1994001079 A1 WO 1994001079A1 EP 9301719 W EP9301719 W EP 9301719W WO 9401079 A1 WO9401079 A1 WO 9401079A1
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WIPO (PCT)
Prior art keywords
mixtures
copolymers
weight
hair treatment
acrylic
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PCT/EP1993/001719
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German (de)
English (en)
Inventor
Rainer Blankenburg
Christian Schade
Axel Sanner
Original Assignee
Basf Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO1994001079A1 publication Critical patent/WO1994001079A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers

Definitions

  • the invention relates to hair treatment compositions which contain copolymers of (meth) acrylic acid esters, (meth) acrylic acid and vinyl lactams as film formers and the use of these copolymers in hair treatment compositions.
  • Neutralized terpolymers are known from US Pat. No. 3,405,084 which contain 25 to 75% by weight of N-vinylpyrrolidone, 20 to 70% by weight of a C 1 -C 8 -alkyl ester of acrylic acid or methacrylic acid and 3 to 25% by weight. -% acrylic acid or methacrylic acid copolymerized.
  • the neutralized copolymers are used in hair spray formulations.
  • the terpolymers are prepared by the solution polymerization process. According to the information in the examples, anhydrous alcohol is used as the solvent.
  • Terpolymers are known from EP-B-0 257 444, which by radical polymerization of 20 to 50 wt .-% vinyl pyrrolidone, 40 to 70 wt .-% tert-butyl acrylate or tert-butyl methacrylate and 2 to 15 wt .-% % Acrylic acid or methacrylic acid are available.
  • the terpolymers have scores of 10 to 60 (determined in a 2% strength by weight solution of the terpolymers in the acid form in ethanol at 25 ° C.). According to the information in the patent, the terpolymers are prepared by the solution polymerization process. They are used as film formers in hair treatment products.
  • terpolymers which, by radical polymerization of 10 to 24% by weight of N-vinylpyrrolidone, 46 to 74% by weight of tert-butyl acrylate or tert-butyl methacrylate and 16 to 30% by weight of acrylic acid or methacrylic acid are available.
  • the terpolymers In the acid form, the terpolymers have K values (determined according to Fikentscher in 1% by weight solution in ethanol at 25 ° C.) from 25 to 65. According to the information in the examples, the terpolymers are prepared by the solution polymerization process in ethanol .
  • the carboxyl groups of the terpolymers can optionally be partially or completely neutralized with organic amines, ammonia and / or alkali metal bases.
  • the terpolymers are used as film formers in hair fixatives.
  • Water-soluble terpolymers are known from US Pat. No. 4,595,737 which:
  • the terpolymers can be prepared either by the solution polymerization method or by the precipitation polymerization method.
  • the terpolymers are used as adhesive raw materials or in the form of aqueous solutions as an adhesive.
  • WO-A-91/00302 describes a process for the preparation of terpolymers
  • the polymerization is preferably carried out in alcohols, in particular in ethanol.
  • Acid-catalyzed addition of the alcohol to the double bond of N-vinylpyrrolidone leads to losses in yield during the copolymerization, change in the composition and thus the product properties of the copolymers.
  • the copolymers prepared in this way contain intolerably high proportions of low molecular weight impurities which can only be removed with great effort.
  • the object of the invention is to provide copolymers for use in hair treatment compositions which do not have the above-mentioned defects.
  • hair treatment compositions which contain copolymers as film formers which are obtained by copolymerizing
  • Methacrylic esters which, when copolymerized, give copolymers with a glass transition temperature of more than 20 ° C.
  • the K values in the form of the free carboxylic acid groups (determined according to H. Fikentscher in 2% strength by weight solution in ethanol at 25 ° C.) have from 10 to 80, if the copolymers prepared by the precipitation polymerization process.
  • Suitable monomers of group (a) are those acrylic acid esters or methacrylic acid esters which each have a glass transition temperature of more than 20 ° C. as a homopolymer or mixtures of acrylic acid esters and methacrylic acid esters which, when these monomers are only copolymerized, give copolymers with one Glass transition temperature of more than 20 ° C result.
  • the glass transition temperature Tg is determined by differential thermal analysis (DTA), cf. B. Vollmert, floor plan of the makromol. Chemie, E. Vollmert Verlag, Düsseldorf, 1979, volume 4, p. 150.
  • Preferred monomers of group (a) are tert-butyl acrylate, isobutyl methacrylate, n-butyl methacrylate, ethyl methacrylate and / or t-butyl methacrylate, if appropriate in a mixture with ethyl acrylate, n-butyl acrylate, stearyl acrylate, methyl methacrylate, stearyl methacrylate and lauryl methacrylate.
  • the monomers of group (a) are contained in the monomer mixture which is subjected to the copolymerization in an amount of 30 to 80, preferably 50 to 80% by weight.
  • Acrylic acid, methacrylic acid or mixtures of acrylic acid and methacrylic acid are used as monomers of group (b).
  • the monomers of group (b) are 5 to 25, preferably 10 to Contain 20 wt .-% in the mixture to be polymerized. They can also be used in the copolymerization in partially or completely neutralized form with alkali metal bases, ammonia or ammonium bases, provided that the neutralized monomer is still soluble in the solvent used for the precipitation polymerization.
  • Suitable monomers of group (c) are N-vinylpyrrolidone, N-vinylcaprolactam or mixtures of N-vinylpyrrolidone and N-vinylcaprolactam in any mixing ratio.
  • the monomers of group (c) are present in the mixture to be polymerized in an amount of 10 to 45, preferably 15 to 30,% by weight.
  • the monomer mixtures are copolymerized in the presence of free radical polymerization initiators.
  • All initiators that are also used in the known solution polymerization can be used for this, e.g. Azo or peroxo compounds.
  • Suitable initiators are, for example, diacyl peroxides such as dilauroyl peroxide, didecanoyl peroxide and dictanoyl peroxide or peresters such as tert-butyl perpivalate, tert-amyl perpivalate or tert-butyl perneodecanoate and azo compounds such as dimethyl-2,2'-azobis (isobutyrate) '-Azo-bis (isobutyronitrile), 2,2'-azobis (2-methyl-butyronitrile) or 2,2'-azobis (2,4-dimethylvaleronitrile).
  • the initiators are used in conventional amounts, e.g. 0.1 to 5 wt .-%
  • copolymers are used in hair treatment compositions which can be obtained by copolymerizing the abovementioned monomers from groups (a) to (c) by the precipitation polymerization process.
  • the monomers are largely soluble, and the polymer is insoluble or only slightly soluble in the solvent system used.
  • the copolymers formed during the polymerization are obtained in the form of fine powders in the course of the polymerization.
  • the precipitation polymerization can be carried out in aromatic hydrocarbons, saturated aliphatic hydrocarbons having 5 to 12 carbon atoms in the molecule, halogenated saturated aliphatic hydrocarbons, ethers, C - to C ⁇ -alkyl esters of formic acid or acetic acid or in mixtures of the solvents mentioned perform medium.
  • aromatic hydrocarbons are, for example, toluene or xylene.
  • Suitable halogenated saturated aliphatic hydrocarbons are, for example, 1,1,1-trichloroethane or methylene chloride.
  • Suitable ethers are, for example, tert-butyl methyl ether or isobutyl methyl ether.
  • the alkyl esters of formic acid or acetic acid are derived from saturated alcohols with 2 to 6 carbon atoms, for example ethyl formate, methyl acetate or ethyl acetate.
  • Aliphatic hydrocarbons having 5 to 12 carbon atoms in the molecule are preferably used as solvents or diluents in the precipitation polymerization. Particularly preferred are hydrocarbons with 5 to 8 carbon atoms in the molecule, which can be straight-chain or branched, cyclic or dicyclic.
  • Cyclohexane is particularly preferably used as the solvent.
  • the amount of solvent is chosen so that the reaction mixture remains stirrable during the polymerization.
  • the solids content of the mixture after the polymerization is preferably in the range from 10 to 40% by weight.
  • the polymerization mixture may contain water, alcohols, ketones, protective colloids, emulsifiers or larger amounts of a base, e.g. Potassium carbonate can be added.
  • a base e.g. Potassium carbonate
  • the molecular weight of the copolymers can be reduced by adding regulators to the polymerization mixture. Suitable regulators are, for example, mercapto compounds such as dodecyl mercaptan, thioethanol or thioglycolic acid. If regulators are also used, the amount used is 0.1 to 5% by weight.
  • Protective colloids are, for example, polyalkyl vinyl ethers having 1 to 12 carbon atoms in the alkyl radical.
  • the K values of the polyalkyl vinyl ethers are 10 to 200, preferably 20 to 100 (measured in 1% strength by weight solution in cyclohexanone at 25 ° C.).
  • Suitable polyvinyl alkyl ethers are, for example, polymethyl vinyl ether, polyethyl vinyl ether, polypropyl vinyl ether, polyisopropyl vinyl ether, poly-n-butyl vinyl ether and polyisobutyl vinyl ether.
  • Other suitable protective colloids are homo- and copolymers of N-vinylpyrrolidone, e.g.
  • the protective colloids are used in amounts of 0.05 to 4, preferably 0.1 to 2% by weight, based on the monomers to be polymerized.
  • the polymerization is usually carried out under an inert gas atmosphere.
  • the copolymerization can be controlled in different ways. For example, all components can be initially introduced at the start of the reaction. However, some or all of the components can also be metered in partially or completely in the course of the implementation under different circumstances under different circumstances.
  • the temperature of the reaction mixture during the polymerization is generally 40 to 160, preferably 50 to 120 ° C. The temperature can be controlled differently during the reaction according to a program.
  • the Pressure in the reaction vessel is usually set to values from 0.8 to 5 bar.
  • the polymerization process is preferably controlled so that the polymer is obtained in the form of a finely divided powder.
  • the powder obtained in the copolymerization is separated from the other constituents of the reaction mixture, for example filtered off or centrifuged off.
  • the powder obtained in this way can optionally be subjected to further suitable separation, washing, drying or grinding processes. If necessary, the powder can also be processed into granules.
  • the copolymers obtained by precipitation polymerization are preferably used in a form partially or completely neutralized by organic amines, ammonia and / or by alkali metal bases as film formers in hair treatment compositions.
  • the carboxyl groups are 5 to 100, preferably 70 to
  • alkanolamines from the series of the mono-, di- or trialkanolamines having 2 to 5 carbon atoms in the alkanol radical are preferably used panolamine or 2-amino-2-methylpropanol or alkanediolamines having 2 to 4 carbon atoms in the alkanediol radical, such as 2-amino-2-methyl-l, 3-propanediol or 2-amino-2-ethyl-l, 3- propanediol, which, like 2-amino-2-methylpropanol and triisopropanolamine, is preferably used for neutralization.
  • the neutralization of the carboxyl groups of the copolymers described above can also be carried out with the aid of ammonia or basic alkali metal compounds such as alkali metal hydroxides, for example lithium hydroxide or in particular sodium and potassium hydroxide, alkali metal carbonates, for example sodium or potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or alkali metal alcoholates, Sodium methylate or sodium ethylate.
  • alkali metal hydroxides for example lithium hydroxide or in particular sodium and potassium hydroxide
  • alkali metal carbonates for example sodium or potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or alkali metal alcoholates, Sodium methylate or sodium ethylate.
  • Mixtures of organic amines, ammonia and basic alkali metal compounds can also be used.
  • the at least partially neutralized copolymers are used as film formers in hair treatment agents.
  • Hair treatment agents are, for example, hair setting solutions, hair foams, hair gels or hair styling agents such as spray preparations.
  • the hair setting agents can contain the copolymers obtainable by precipitation polymerization in amounts of 1 to 15, preferably 2 to 10% by weight.
  • Further constituents of hair fixatives are solvents from the group of water, acetone, ethanol, n-propanol, n-butanol, isopropanol and 1-methoxypropanol or mixtures of the solvents mentioned.
  • the use of water, ethanol and isopropanol is particularly cheap.
  • the solvents are usually present in amounts of 10 to 99% by weight in hair agents included.
  • the hair treatment compositions can contain a blowing agent from the group consisting of propane, n-butane, isobutane, 2,2-dimethylpropane, isopentane and dimethyl ether and mixtures of the compounds mentioned.
  • the amounts of blowing agent contained in the hair treatment composition can be up to 90% by weight.
  • the hair treatment compositions can also contain other customary additives, such as perfume, preservatives, etc., in the amounts customary for this.
  • the copolymers which can be used according to the invention by the precipitation polymerization process and are to be used in hair treatment compositions have a higher purity than the copolymers which can be obtained by the solution polymerization process.
  • the yield was approximately 95%.
  • the polymer obtained was a fine, light, odorless powder with a K value of 60 and a residual monomer content of less than 100 ppm. It is used as a film former in hair sprays.
  • the terpolymers were prepared by the process described in Example 1 with 1.1% tert-butyl perpivalate as the initiator and 0.7% mercaptoethanol as the regulator. From the table below the composition of the monomer mixture, the K value of the terpolymers and the yield can be seen.
  • VP N-vinylpyrrolidone t-BA: tert-butyl acrylate
  • MAS methacrylic acid
  • n-BMA n-butyl methacrylate
  • VCap N-vinyl caprolactam
  • Samples 1-6 had a propane / butane tolerance of at least 70%.
  • the value for the hydrocarbon compatibility with a propane / n-butane mixture in a weight ratio of 40:60 indicates how many% by weight of this propellant gas mixture is a spray preparation which, in addition to ethanol as solvent, has 3% by weight of the neutralized copolymer, may contain a maximum without becoming cloudy at 0 ° C.

Abstract

Produits pour le traitement des cheveux renfermant, comme agents filmogènes, des copolymérisats obtenus par copolymérisation de: a) 30 à 80 % en poids d'un ester d'acide acrylique ou méthacrylique présentant, comme homopolymérisat, une température de transition vitreuse de plus de 20 °C, ou de mélanges d'esters acryliques et méthacryliques produisant, par copolymérisation, des copolymérisats ayant une température de transition vitreuse de plus de 20 °C; b) 5 à 25 % en poids d'acide acrylique, d'acide méthacrylique ou de mélanges de ces acides, et c) 10 à 45 % en poids de N-vinylpyrrolidone, de N-vinylcaprolactame ou de mélanges de ces produits, en présence d'initiateurs radicalaires de polymérisation, selon le procédé de polymérisation par précipitation. L'invention concerne également l'utilisation des copolymérisats ainsi obtenus, comme agents filmogènes dans des produits pour le traitement des cheveux.
PCT/EP1993/001719 1992-07-14 1993-07-03 Produits pour le traitement des cheveux renfermant des copolymerisats servant d'agents filmogenes WO1994001079A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19924223066 DE4223066A1 (de) 1992-07-14 1992-07-14 Haarbehandlungsmittel, die als Filmbildner Copolymerisate enthalten
DEP4223066.7 1992-07-14

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995028909A1 (fr) * 1994-04-26 1995-11-02 Henkel Kommanditgesellschaft Auf Aktien Agents de traitement capillaire
WO1995028908A1 (fr) * 1994-04-26 1995-11-02 Henkel Kommanditgesellschaft Auf Aktien Agents de traitement capillaire
US8084561B2 (en) 2006-03-31 2011-12-27 Basf Se Process for preparing acrylate copolymers

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10243038A1 (de) * 2002-09-17 2004-03-25 Henkel Kgaa Haarbehandlungsmittel mit konditionierenden Eigenschaften
DE102004051648A1 (de) 2004-10-22 2006-04-27 Basf Ag Anionische Ethylmethacrylat-Copolymere und deren Verwendung
DE102004051647A1 (de) * 2004-10-22 2006-07-06 Basf Ag Kosmetische Zubereitungen enthaltend Ethylmethacrylat-Copolymere
DE102004051541A1 (de) 2004-10-22 2006-05-04 Basf Ag Amphotere Ethylmethacrylat-Copolymere und deren Verwendung
CN101405304A (zh) * 2006-01-23 2009-04-08 巴斯夫欧洲公司 在含水溶剂中制备聚合物的方法
EP2051780A1 (fr) 2006-08-11 2009-04-29 Basf Se Utilisation de copolymères cationiques à base d'acrylates aminés et de sels de n-vinylimidazole dans des préparations cosmétiques capillaires
US8247507B2 (en) 2006-09-21 2012-08-21 Basf Se Cationic polymers as thickeners for aqueous and alcoholic compositions

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2026004A (en) * 1978-06-23 1980-01-30 Oreal Cosmetic compositions for treating hair
EP0168684A2 (fr) * 1984-06-26 1986-01-22 BASF Aktiengesellschaft Terpolymères solubles dans l'eau, leur procédé de préparation et leur utilisation comme adhésifs
EP0257444A2 (fr) * 1986-08-18 1988-03-02 BASF Aktiengesellschaft Tercopolymères, leur utilisation dans des compositions pour le traitement des cheveux, et compositions de traitement des cheveux les contenant
EP0315021A2 (fr) * 1987-10-31 1989-05-10 BASF Aktiengesellschaft Procédé de préparation de copolymères d'anhydrydes d'acides dicarboxyliques à insaturation éthylénique et d'éthers alkylvinyliques
EP0379082A2 (fr) * 1989-01-18 1990-07-25 BASF Aktiengesellschaft Agent fixateur des cheveux
WO1990012041A1 (fr) * 1989-04-07 1990-10-18 Gaf Chemicals Corporation Polymerisation par precipitation de copolymeres d'un lactame de vinyl et d'un acide carboxylique polymerisable dans un solvant d'hydrocarbure aliphatique
WO1991000302A1 (fr) * 1989-06-26 1991-01-10 Gaf Chemicals Corporation Polymerisation par precipitation de terpolymeres de lactame vinylique
EP0480280A1 (fr) * 1990-10-08 1992-04-15 BASF Aktiengesellschaft Terpolymères, leur utilisation dans des agents fixateur des cheveux avec fixation améliorée et agents fixateur des cheveux les contenants
WO1992007011A1 (fr) * 1990-10-18 1992-04-30 Isp Investments Inc. Polyvinylpyrrolidone reticulee pouvant gonfler et compositions a usage cosmetique preparees a partir de celle-ci

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2026004A (en) * 1978-06-23 1980-01-30 Oreal Cosmetic compositions for treating hair
EP0168684A2 (fr) * 1984-06-26 1986-01-22 BASF Aktiengesellschaft Terpolymères solubles dans l'eau, leur procédé de préparation et leur utilisation comme adhésifs
EP0257444A2 (fr) * 1986-08-18 1988-03-02 BASF Aktiengesellschaft Tercopolymères, leur utilisation dans des compositions pour le traitement des cheveux, et compositions de traitement des cheveux les contenant
EP0315021A2 (fr) * 1987-10-31 1989-05-10 BASF Aktiengesellschaft Procédé de préparation de copolymères d'anhydrydes d'acides dicarboxyliques à insaturation éthylénique et d'éthers alkylvinyliques
EP0379082A2 (fr) * 1989-01-18 1990-07-25 BASF Aktiengesellschaft Agent fixateur des cheveux
WO1990012041A1 (fr) * 1989-04-07 1990-10-18 Gaf Chemicals Corporation Polymerisation par precipitation de copolymeres d'un lactame de vinyl et d'un acide carboxylique polymerisable dans un solvant d'hydrocarbure aliphatique
WO1991000302A1 (fr) * 1989-06-26 1991-01-10 Gaf Chemicals Corporation Polymerisation par precipitation de terpolymeres de lactame vinylique
EP0480280A1 (fr) * 1990-10-08 1992-04-15 BASF Aktiengesellschaft Terpolymères, leur utilisation dans des agents fixateur des cheveux avec fixation améliorée et agents fixateur des cheveux les contenants
WO1992007011A1 (fr) * 1990-10-18 1992-04-30 Isp Investments Inc. Polyvinylpyrrolidone reticulee pouvant gonfler et compositions a usage cosmetique preparees a partir de celle-ci

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995028909A1 (fr) * 1994-04-26 1995-11-02 Henkel Kommanditgesellschaft Auf Aktien Agents de traitement capillaire
WO1995028908A1 (fr) * 1994-04-26 1995-11-02 Henkel Kommanditgesellschaft Auf Aktien Agents de traitement capillaire
US6126921A (en) * 1994-04-26 2000-10-03 Henkel Kommanditgesellschaft Auf Aktien Hair treatment formulations containing a water-insoluble polymer having a glass transition temperature of -20° C. to 70° C.
US8084561B2 (en) 2006-03-31 2011-12-27 Basf Se Process for preparing acrylate copolymers

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