EP1469817A1 - Fixative agents for hair - Google Patents

Fixative agents for hair

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Publication number
EP1469817A1
EP1469817A1 EP03729484A EP03729484A EP1469817A1 EP 1469817 A1 EP1469817 A1 EP 1469817A1 EP 03729484 A EP03729484 A EP 03729484A EP 03729484 A EP03729484 A EP 03729484A EP 1469817 A1 EP1469817 A1 EP 1469817A1
Authority
EP
European Patent Office
Prior art keywords
weight
polymer
acrylic acid
hair
vinylpyrrolidone
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.)
Withdrawn
Application number
EP03729484A
Other languages
German (de)
French (fr)
Inventor
Wilma M. Dausch
Bernd De Potzolli
Maximilian Angel
Jacqueline Engesser
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1469817A1 publication Critical patent/EP1469817A1/en
Withdrawn legal-status Critical Current

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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
    • A61K8/817—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
    • A61K8/8141—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
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8176—Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring

Definitions

  • the present invention relates to new hair fixatives which contain polymer mixtures as film formers.
  • Hair spray compositions which consist of a polyester and a water-soluble polymer, for example a copolymer of N-vinylcaprolactam and N-vinylpyrrolidone, are known from WO 93/17658.
  • EP 0 734 717 A2 describes hair fixatives containing
  • polymer B 0.5 to 20% by weight of a further film-forming polymer (polymer B), selected from the group of polyamides, polyurethanes, homopolymers and copolymers of monoolefinically unsaturated monomers.
  • the object was to develop hair fixatives which have good setting properties and good washability, without showing the sensitivity to moisture described above, and which are characterized by low stickiness.
  • Suitable polymers A are homopolymers of N-vinylcaprolactam which are known to the person skilled in the art and can be prepared, for example, according to the procedure described in US Pat. No. 3,145,147. These polymers are available under the trade name Luviskol Plus (BASF Aktiengesellschaft).
  • suitable polymers A are copolymers of N-vinylcaprolactam and other polymerizable monomers, the copolymers consisting of at least 70% by weight, preferably at least 85% by weight, of N-vinylcaprolactam.
  • Suitable further polymerizable monomers for the copolymers A are:
  • Monomers with an acid function such as acrylic acid, methacrylic acid, acrylamido-methylpropylsulfonic acid (AMPS), (meth) acrylic acid-3-sulfopropyl ester, optionally also in completely or partially neutralized form;
  • APMS acrylamido-methylpropylsulfonic acid
  • acrylic acid-3-sulfopropyl ester optionally also in completely or partially neutralized form
  • Ci-Cis alkyl (meth) acrylates such as tert. Butyl acrylate, ethyl acrylate, iso-butyl methacrylate, n-butyl methacrylate, methyl ethacrylate,
  • Vinyl esters of C 2 -C 10 fatty acids such as vinyl acetate, vinyl propionate and vinyl esters of longer-chain and / or branched fatty acids, for example versatic acid;
  • N-alkyl (meth) acrylamides such as methacrylamide, N, N-dimethyl-acrylamide, N-tert. Butylacrylamide and N-tert. octyl acrylamide;
  • N-vinyl pyrrolidone and N-vinyl piperidone are N-vinyl pyrrolidone and N-vinyl piperidone.
  • the other monomers can be used as a single compound or as a mixture for the copolymer A.
  • EP 455 081 describes copolymers of N-vinylpyrrolidone, N-vinylcaprolactam and N-vinylimidazole.
  • Copolymers of N-vinylpyrrolidone, N-vinylcaprolactam and dirnethylaminoethyl methacrylate are known from EP 74191.
  • Homopolymers of N-vinylcaprolactam are preferably used as polymers A for the hair setting agents according to the invention.
  • the hair fixatives according to the invention contain the polymers A in an amount of 0.5 to 20, preferably 1 to 10,% by weight, based on the finished composition.
  • Suitable polymers B are terpolymers obtainable by copolymerization
  • At least 50% of the carboxyl groups present in the terpolymer with a lower organic base are selected from triethanolamine, triisopropanolamine, 2-amino-2-methyl-propanol and 2-amino-2-methyl-1,3-propane diol neutralized.
  • the N-substituted acrylamides or methacrylamides which can be used as monomers (a) are substituted with alkyl radicals which contain 1 to 4 carbon atoms.
  • alkyl radicals which contain 1 to 4 carbon atoms.
  • examples of such usable acrylamides and methacrylamides are N-methyl acrylamide, N-ethyl acrylamide, N-propyl acrylamide, N-n-butyl acrylamide, N-isopropyl acrylamide, N-sec-butyl acrylamide, N-tert. -Butyl acrylamide and the corresponding methacrylamides.
  • Preferred are the acrylamides and in particular N-tert-butyl acrylamide.
  • alkyl esters of acrylic acid or methacrylic acid which can be used as monomers (b) are methyl, ethyl, propyl, isopropyl or n-butyl acrylate or methacrylate, the acrylates being preferred over the methacrylates.
  • Acrylic acid ethyl ester is particularly preferred.
  • acrylates or methacrylates with hydroxyl groups such as, for example, hydroxyethyl acrylate, hydroxypropyl acrylate or hydroxyethyl methacrylate, can be used as component (b).
  • Particularly preferred component (c) is acrylic acid.
  • Particularly preferred polymer B) is a terpolymer made from acrylic acid / ethyl acrylate / N-tertiary-butylacrylamide.
  • Such copolymers are sold under the trade names Ultrahold ® 8, Ultrahold Strong ® (BASF Aktiengesellschaft).
  • Suitable polymers C) are homopolymers of N-vinylpyrrolidone, such as those sold by BASF Aktiengesellschaft under the name Luviskol, for example.
  • the copolymers are by polymerizing N-vinylpyrrolidone with vinyl acetate and / or
  • Vinyl propionate available in various weight ratios are:
  • Luviskol ® K17 Luviskol ® K30 Luviskol ® K60 Luviskol ® K80, Luviskol K90 polyvinyl pyrrolidones with a corresponding K value as powder or as a solution (aqueous or aqueous / alcoholic)).
  • Luviskol VA vinyl pyrrolidone / vinyl acetate copolyers, especially Luviskol ® VA 73, Luviskol ® VA 64, Luviskol ® VA 55, Luviskol ® VA 37 removed from the range.
  • the hair fixatives contain
  • the polymers A, B and C can be used in the acid form or partially or completely neutralized for the hair fixatives according to the invention.
  • Alkali metal hydroxides, ammonia, organic amines, in particular amino alcohols, are suitable for neutralization, 2-amino-2-methyl-l-propanol being very particularly preferred.
  • the polymers A, B and C are present in a solvent, water or alcohols or mixtures of water and lower alcohols preferably being used as solvents.
  • the proportion of solvent in the hair fixative is usually between 25 and 98% by weight.
  • the polymers A, B and C can be mixed together by dissolving A, B and C as a powder in a solvent, or by mixing the other polymer as a solid or likewise as a solution into a solution of a polymer.
  • the hair fixatives according to the invention contain the polymers B and C in an amount of 0.5 to 20.0, preferably 1 to 5% by weight, based on the finished composition.
  • the hair fixatives according to the invention can, depending on the intended use, other conventional hair cosmetic additives such as perfume oils, emulsifiers, preservatives, care substances such as panthenol, silicone, collagen, vitamins, protein hydrolyzates, stabilizers, pH regulators, dyes , UV filter and other common additives.
  • other conventional hair cosmetic additives such as perfume oils, emulsifiers, preservatives, care substances such as panthenol, silicone, collagen, vitamins, protein hydrolyzates, stabilizers, pH regulators, dyes , UV filter and other common additives.
  • a blowing agent is generally added.
  • Typical blowing agents are lower alkanes, for example propane or butane, methyl ether, nitrogen, nitrogen oxide or carbon dioxide or mixtures of these substances.
  • the hair fixatives according to the invention can also contain halogenated hydrocarbons as blowing agents.
  • the propellant can be omitted.
  • the hair fixatives according to the invention have excellent performance properties; they form clear films and have a low solution viscosity in aqueous / alcoholic solutions, so that they also have good spray properties even in higher concentrations. Surprisingly, they show a clear lent reduced stickiness to known hair fixatives, in particular consisting of vinyl caprolactam and / or vinyl pyrrolidone and / or PVP / VA copolymer.
  • the polyvinyl caprolactam solutions used in the examples below were 40% by weight solutions in ethanol.
  • the K value according to Fikentscher of the polymer was 40 (1% in ethanol).
  • PVP polyvinyl pyrrolidone
  • PVP polyvinylpyrrolidone
  • polyvinylcaprolactam solution 2.5% by weight Ultrahold 8 (BASF Aktiengesellschaft) 35 2.5% by weight Luviskol K30 (BASF Aktiengesellschaft) polyvinylpyrrolidone 90.0% by weight agua dest.
  • Luviskol K30 polyvinylpyrrolidone

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

The invention relates to fixative agents for hair containing: A) between 0.5 and 20 wt. % of a homopolymer of N-vinylcaprolactam or of an anionic or non-ionic copolymer consisting of at least 70 wt. % of N-vinylcaprolactam (polymer A); and B) between 0.5 and 20 wt. % of a terpolymer (polymer B), obtained by the copolymerisation of (a) at least one C1-C4 N-alkylacrylamide or a C1-C4 N-alkylmethacrylamide and (b) at least one C1-C4 hydroxyalkyl ester or a C1-C4 alkyl ester of acrylic acid or methacrylic acid and (c) acrylic acid and/or methacrylic acid, C) between 0.5 and 20 wt. % of a polymer, selected from the group of copolymers consisting of vinylpyrrolidone and a vinyl ester and homopolymers of vinylpyrrolidone.

Description

HAARFESTIGUNGSMITTEL HAIR STRENGTHENING MEANS
Beschreibungdescription
Die vorliegende Erfindung betrifft neue Haarfestigungsmittel, die Polymermischungen als Filmbildner enthalten.The present invention relates to new hair fixatives which contain polymer mixtures as film formers.
HaarSprayzusammensetzungen, die aus einem Polyester und einem wasserlöslichen Polymer, beispielsweise einem Copolymer aus N-Vinylcaprolactam und N-Vinylpyrrolidon bestehen, sind aus WO 93/17658 bekannt.Hair spray compositions which consist of a polyester and a water-soluble polymer, for example a copolymer of N-vinylcaprolactam and N-vinylpyrrolidone, are known from WO 93/17658.
Solche Haarsprays sind jedoch feuchtigkeitsempfindlich und daher in der Anwendung und Handhabung nur eingeschränkt verwendbar.However, such hair sprays are sensitive to moisture and can therefore only be used to a limited extent in use and handling.
EP 0 734 717 A2 beschreibt Haarfestigungsmittel, enthaltendEP 0 734 717 A2 describes hair fixatives containing
A) 0,5 bis 20 Gew.% eines Homo- oder Copolymeren aus mindestens 70 Gew.% N-Vinylcaprolactam (Polymer A) , undA) 0.5 to 20% by weight of a homo- or copolymer of at least 70% by weight of N-vinylcaprolactam (polymer A), and
B) 0,5 bis 20 Gew.% eines weiteren filmbildenden Polymeren (Polymer B) , ausgewählt aus der Gruppe von Polyamiden, Polyurethanen, Homo- und Copolymeren von monoolefinisch ungesättigten Monomeren.B) 0.5 to 20% by weight of a further film-forming polymer (polymer B), selected from the group of polyamides, polyurethanes, homopolymers and copolymers of monoolefinically unsaturated monomers.
Unbefriedigend an den Haarbehandlungsmitteln des Standes der Technik ist ihre Klebrigkeit.The stickiness of the prior art hair treatment compositions is unsatisfactory.
Es bestand die Aufgabe, Haarfestigungsmittel zu entwickeln, die gute Festigereigenschaften bei guter Auswaschbarkeit aufweisen, ohne dabei die oben beschriebene Feuchtigkeitsempfindlichkeit zu zeigen und die sich durch geringe Klebrigkeit auszeichnen.The object was to develop hair fixatives which have good setting properties and good washability, without showing the sensitivity to moisture described above, and which are characterized by low stickiness.
Demgemäß wurden Haarfestigungsmittel gefunden, enthaltendAccordingly, hair fixatives have been found containing
A) 0,5 bis 20 Gew.% eines Homopolymeren des N-Vinylcaprolactams oder eines anionischen oder nichtionischen Copolymeren aus mindestens 70 Gew.% N-Vinylcaprolactam (Polymer A) , undA) 0.5 to 20% by weight of a homopolymer of N-vinylcaprolactam or of an anionic or nonionic copolymer of at least 70% by weight of N-vinylcaprolactam (polymer A), and
B) 0,5 bis 20 Gew.% eines Terpolymers (Polymer B) , erhältlich durch CopolymerisationB) 0.5 to 20% by weight of a terpolymer (polymer B), obtainable by copolymerization
(a) mindestens eines C1-C4 N-Alkylacrylamides oder eines C1-C4 N-Alkylmethacrylamides und (b) mindestens eines C1-C4 Hydroxyalkylesters oder eines C1-C4 Alkylesters der Acrylsaure oder Methacrylsäure und(a) at least one C 1 -C 4 N-alkyl acrylamide or one C 1 -C 4 N-alkyl methacrylamide and (b) at least one C1-C4 hydroxyalkyl or a C 1 -C 4 alkyl ester of acrylic acid or methacrylic acid and
(c) Acrylsaure und/oder Methacrylsäure(c) Acrylic acid and / or methacrylic acid
C) 0,5 bis 20 Gew.-% eines Polymeren ausgewählt aus der Gruppe bestehend aus Copolymeren aus Vinylpyrrolidon und eines Vinylesters und aus Homopolymeren von Vinylpyrrolidon.C) 0.5 to 20 wt .-% of a polymer selected from the group consisting of copolymers of vinyl pyrrolidone and a vinyl ester and homopolymers of vinyl pyrrolidone.
Als Polymere A sind Homopoly ere des N-Vinylcaprolactams geeignet, die dem Fachmann bekannt sind und sich beispielsweise nach der in US 3 145 147 beschriebenen Vorschrift herstellen lassen. Diese Polymere sind unter dem Handelsnamen Luviskol Plus (BASF Aktiengesellschaft) erhältlich.Suitable polymers A are homopolymers of N-vinylcaprolactam which are known to the person skilled in the art and can be prepared, for example, according to the procedure described in US Pat. No. 3,145,147. These polymers are available under the trade name Luviskol Plus (BASF Aktiengesellschaft).
Weitere geeignete Polymere A sind Copolymere aus N-Vinylcaprolactam und weiteren polymerisierbaren Monomeren, wobei die Copolymere aus mindestens 70 Gew.%, bevorzugt mindestens 85 Gew.% N-Vinylcaprolactam bestehen.Other suitable polymers A are copolymers of N-vinylcaprolactam and other polymerizable monomers, the copolymers consisting of at least 70% by weight, preferably at least 85% by weight, of N-vinylcaprolactam.
Als weitere polymerisierbare Monomere für die Copolymere A sind geeignet :Suitable further polymerizable monomers for the copolymers A are:
Monomere mit einer Säurefunktion wie Acrylsaure, Methacrylsäure, Acrylamido-methylpropylsulfonsäure (AMPS) , (Meth) acrylsäure- 3-sulfopropylester, gegebenenfalls auch in komplett oder teilweise neutralisierter Form;Monomers with an acid function such as acrylic acid, methacrylic acid, acrylamido-methylpropylsulfonic acid (AMPS), (meth) acrylic acid-3-sulfopropyl ester, optionally also in completely or partially neutralized form;
Ci-Cis Alkyl (meth) acrylate, wie tert. Butylacrylat , Ethylacrylat, iso-Butylmethacrylat, n-Butylmethacrylat , Methyl ethacrylat,Ci-Cis alkyl (meth) acrylates, such as tert. Butyl acrylate, ethyl acrylate, iso-butyl methacrylate, n-butyl methacrylate, methyl ethacrylate,
Ethyl ethacrylat und Hydroxy-alkyl (meth) acrylsäureester;Ethyl ethacrylate and hydroxy-alkyl (meth) acrylic acid esters;
Vinylester der C2-Cιo Fettsäuren wie Vinylacetat, Vinylpropionat und Vinylester längerkettiger und/oder verzweigter Fettsäuren, beispielsweise Versatiesäure;Vinyl esters of C 2 -C 10 fatty acids such as vinyl acetate, vinyl propionate and vinyl esters of longer-chain and / or branched fatty acids, for example versatic acid;
C3-C8 N-Alkyl (meth)acrylamide, wie Methacrylamid, N,N-Dimethyl- acrylamid, N-tert. Butylacrylamid und N-tert. Octylacrylamid;C 3 -C 8 N-alkyl (meth) acrylamides, such as methacrylamide, N, N-dimethyl-acrylamide, N-tert. Butylacrylamide and N-tert. octyl acrylamide;
N-Vinylpyrrolidon und N-Vinylpiperidon.N-vinyl pyrrolidone and N-vinyl piperidone.
Die weiteren Monomeren können als einzelne Verbindung oder als Gemisch für das Copolymer A verwendet werden.The other monomers can be used as a single compound or as a mixture for the copolymer A.
Solche Copolymere sind bekannt oder lassen sich durch übliche Polymerisationsverfahren herstellen. Beispielsweise werden in EP 455 081 Copolymere aus N-Vinylpyrrolidon, N-Vinylcaprolactam und N-Vinylimidazol beschrieben. Aus EP 74191 sind Copolymere aus N-Vinylpyrrolidon,N-Vinylcaprolactam und Dirnethylaminoethyl-methacrylat bekannt.Such copolymers are known or can be produced by customary polymerization processes. For example, EP 455 081 describes copolymers of N-vinylpyrrolidone, N-vinylcaprolactam and N-vinylimidazole. Copolymers of N-vinylpyrrolidone, N-vinylcaprolactam and dirnethylaminoethyl methacrylate are known from EP 74191.
Bevorzugt werden für die erfindungsgemäßen Haarfestiger Homopoly- mere des N-Vinylcaprolactam als Polymere A verwendet.Homopolymers of N-vinylcaprolactam are preferably used as polymers A for the hair setting agents according to the invention.
Die erfindungsgemäßen Haarfestigungsmittel enthalten die Poly- mere A in einer Menge von 0,5 bis 20, bevorzugt von 1 bis 10 Gew.-%, bezogen auf das fertige Mittel.The hair fixatives according to the invention contain the polymers A in an amount of 0.5 to 20, preferably 1 to 10,% by weight, based on the finished composition.
Als Polymere B sind geeignet Terpolymere, erhältlich durch CopolymerisationSuitable polymers B are terpolymers obtainable by copolymerization
(a) mindestens eines C1-C4 N-Alkylacrylamides oder eines C1-C4 N-Alkylmethacrylamides und(a) at least one C 1 -C 4 N-alkyl acrylamide or a C1-C 4 N-alkyl methacrylamide and
(b) mindestens eines C1-C4 Hydroxyalkylesters oder eines C1-C4 Alkylesters der Acrylsaure oder Methacrylsäure und(b) at least one C 1 -C 4 hydroxyalkyl ester or one C 1 -C 4 alkyl ester of acrylic acid or methacrylic acid and
(c) Acrylsaure und/oder Methacrylsäure(c) Acrylic acid and / or methacrylic acid
In einer bevorzugten Ausführungsform sind mindestens 50 % der im Terpolymer vorhandenen Carboxylgruppen mit einer niederen organischen Base ausgewählt aus Triethanolamin, Triisopropanol- amin, 2-Amino-2-methyl-propanol und 2-Amino-2-methyl-l,3-propan- diol neutralisiert.In a preferred embodiment, at least 50% of the carboxyl groups present in the terpolymer with a lower organic base are selected from triethanolamine, triisopropanolamine, 2-amino-2-methyl-propanol and 2-amino-2-methyl-1,3-propane diol neutralized.
Die als Monomere (a) verwendbaren N-substituierten Acrylamide oder Methacrylamide sind mit Alkylresten substituiert, welche 1 bis 4 Kohlenstoffatome enthalten. Beispiele für derartige anwendbare Acrylamide und Methacrylamide sind N-Methylacrylamid, N-Ethylacrylamid, N-Propylacrylamid, N-n-Butylacrylamid, N-Iso- propylacrylamid, N-sek.-Butylacrylamid, N-tert . -Butylacrylamid sowie die entsprechenden Methacrylamide, Bevorzugt sind die Acrylamide und insbesondere N-tert .-Butylacrylamid.The N-substituted acrylamides or methacrylamides which can be used as monomers (a) are substituted with alkyl radicals which contain 1 to 4 carbon atoms. Examples of such usable acrylamides and methacrylamides are N-methyl acrylamide, N-ethyl acrylamide, N-propyl acrylamide, N-n-butyl acrylamide, N-isopropyl acrylamide, N-sec-butyl acrylamide, N-tert. -Butyl acrylamide and the corresponding methacrylamides. Preferred are the acrylamides and in particular N-tert-butyl acrylamide.
Beispiele von als Monomeren (b) verwendbaren Alkylester der Acrylsaure oder Methacrylsäure sind Methyl-, Ethyl-, Propyl-, Isopropyl- oder n-Butylacrylat oder -methacrylat , wobei die Acrylate gegenüber den Methacrylaten bevorzugt sind. Dabei ist Acrylsäureethylester besonders bevorzugt. Des weiteren können Acrylate oder Methacrylate mit Hydroxylgruppen, wie z.B. Hydroxy- ethylacrylat, Hydroxypropylacrylat oder Hydroxyethylmethacrylat als Komponente (b) verwendet werden. Besonders bevorzugte Komponente (c) ist Acrylsaure.Examples of alkyl esters of acrylic acid or methacrylic acid which can be used as monomers (b) are methyl, ethyl, propyl, isopropyl or n-butyl acrylate or methacrylate, the acrylates being preferred over the methacrylates. Acrylic acid ethyl ester is particularly preferred. Furthermore, acrylates or methacrylates with hydroxyl groups, such as, for example, hydroxyethyl acrylate, hydroxypropyl acrylate or hydroxyethyl methacrylate, can be used as component (b). Particularly preferred component (c) is acrylic acid.
Bevorzugt sind Polymere B) , die erhältlich sind ausPolymers B) which are obtainable from are preferred
40 bis 60 Gew.-% (a)40 to 60% by weight (a)
35 bis 50 Gew.-% (b) und 3 bis 11 Gew.-% (c)35 to 50% by weight (b) and 3 to 11% by weight (c)
- bezogen auf das Gesamtgewicht des Monomerengemisch.es - mit der Maßgabe, daß sich die Anteile zu 100 % addieren.- Based on the total weight of the monomer mixture - with the proviso that the proportions add up to 100%.
Besonders bevorzugtes Polymer B) ist ein Terpolymer aus Acryl- säure/Ethylacrylat/N-tertiär-Butylacrylamid. Solche Copolymere werden unter dem Handelsnamen Ultrahold® 8 , Ultrahold Strong® (BASF Aktiengesellschaft) vertrieben.Particularly preferred polymer B) is a terpolymer made from acrylic acid / ethyl acrylate / N-tertiary-butylacrylamide. Such copolymers are sold under the trade names Ultrahold ® 8, Ultrahold Strong ® (BASF Aktiengesellschaft).
Als Polymer C) sind geeignet Homopolymere des N-Vinylpyrrolidons , wie sie beispielsweise unter dem Namen Luviskol von der BASF Aktiengesellschaft vertrieben werden. Die Copolymere sind durch Polymerisation von N-Vinylpyrrolidon mit Vinylacetat und/oderSuitable polymers C) are homopolymers of N-vinylpyrrolidone, such as those sold by BASF Aktiengesellschaft under the name Luviskol, for example. The copolymers are by polymerizing N-vinylpyrrolidone with vinyl acetate and / or
Vinylpropionat in verschiedenen Gewichtsverhältnissen erhältlich. Beispiele für solche Polymere sind:Vinyl propionate available in various weight ratios. Examples of such polymers are:
Luviskol® K17 Luviskol® K30 Luviskol® K60 Luviskol® K80, Luviskol K90 (Polyvinylpyrrolidone mit entsprechendem K-Wert als Pulver oder als Lösung (wäßrig oder wäßrig/alkoholisch) ) .Luviskol ® K17 Luviskol ® K30 Luviskol ® K60 Luviskol ® K80, Luviskol K90 (polyvinyl pyrrolidones with a corresponding K value as powder or as a solution (aqueous or aqueous / alcoholic)).
Luviskol VA = Vinylpyrrolidon/Vinylacetat-Copolyere, insbesondere Luviskol® VA 73, Luviskol® VA 64, Luviskol® VA 55, Luviskol® VA 37 aus Sortiment gestrichen.Luviskol VA = vinyl pyrrolidone / vinyl acetate copolyers, especially Luviskol ® VA 73, Luviskol ® VA 64, Luviskol ® VA 55, Luviskol ® VA 37 removed from the range.
In einer besonders bevorzugten Ausführungsform enthalten die HaarfestigungsmittelIn a particularly preferred embodiment, the hair fixatives contain
A) 0,5 bis 20 Gew.-%, insbesondere 1 bis 5 Gew.-% bezogen auf Feststoff eines Homopolymerisates des N-VinylcaprolactamsA) 0.5 to 20 wt .-%, in particular 1 to 5 wt .-% based on the solid of a homopolymer of N-vinylcaprolactam
B) 0,5 bis 20 Gew.-%, insbesondere 1 bis 5 Gew.-% eines Ter- polymers aus N-tert. -Butylacrylamid, Ethylacrylat und Acryl- säureB) 0.5 to 20 wt .-%, in particular 1 to 5 wt .-% of a terpolymer made of N-tert. -Butyl acrylamide, ethyl acrylate and acrylic acid
C) 0,5 bis 20 Gew.-%, insbesondere 1 bis 5 Gew.-% bezogen auf Feststoff eines Homopoly ers aus N-Vinylpyrrolidon und/oder eines Copolymers aus N-Vinylpyrrolidon und Vinylacetat . Die Polymere A, B und C können, falls sie aus säuregruppen- haltigen Monomeren aufgebaut sind, in der Säureform oder teilweise oder komplett neutralisiert für die erfindungsgemäßen Haarfestigungsmittel verwendet werden. Zur Neutralisierung eignen sich Alkalihydroxide, Ammoniak, organische Amine, insbesondere Aminoalkohole, wobei 2-Amino-2-methyl-l-propanol ganz besonders bevorzugt wird.C) 0.5 to 20 wt .-%, in particular 1 to 5 wt .-% based on the solids of a homopoly ers from N-vinylpyrrolidone and / or a copolymer of N-vinylpyrrolidone and vinyl acetate. If they are composed of monomers containing acid groups, the polymers A, B and C can be used in the acid form or partially or completely neutralized for the hair fixatives according to the invention. Alkali metal hydroxides, ammonia, organic amines, in particular amino alcohols, are suitable for neutralization, 2-amino-2-methyl-l-propanol being very particularly preferred.
Die Polymere A, B und C liegen in einem Lösungsmittel vor, wobei als Lösungsmittel bevorzugt Wasser oder Alkohole oder Mischungen aus Wasser und niederen Alkoholen eingesetzt werden. Der Lösungsmittelanteil im Haarfestigungsmittel beträgt üblicherweise zwischen 25 bis 98 Gew.-%.The polymers A, B and C are present in a solvent, water or alcohols or mixtures of water and lower alcohols preferably being used as solvents. The proportion of solvent in the hair fixative is usually between 25 and 98% by weight.
Das Zusammenmischen der Polymere A, B und C kann erfolgen, indem A, B und C als Pulver in einem Lösungsmittel aufgelöst werden, oder indem in eine Lösung eines Polymeren das jeweils andere Polymer als Feststoff oder ebenfalls als Lösung zugemischt wird.The polymers A, B and C can be mixed together by dissolving A, B and C as a powder in a solvent, or by mixing the other polymer as a solid or likewise as a solution into a solution of a polymer.
Die erfindungsgemäßen Haarfestigungsmittel enthalten die Polymere B und C in einer Menge von 0,5 bis 20,0 bevorzugt von 1 bis 5 Gew.-%, bezogen auf das fertige Mittel.The hair fixatives according to the invention contain the polymers B and C in an amount of 0.5 to 20.0, preferably 1 to 5% by weight, based on the finished composition.
Neben den Polymeren A, B und C sowie einem Lösungsmittel können die erfindungsgemäßen Haarfestigungsmittel je nach Verwendungszweck weitere übliche haarkosmetische Zusätze wie Parfümöle, Emulgatoren, Konservierungsmittel, Pflegestoffe wie Panthenol, Silikon, Collagen, Vitamine, Eiweißhydrolysate, Stabilisatoren, pH-Wert-Regulatoren, Farbstoffe, UV-Filter und weitere übliche Additive enthalten.In addition to the polymers A, B and C and a solvent, the hair fixatives according to the invention can, depending on the intended use, other conventional hair cosmetic additives such as perfume oils, emulsifiers, preservatives, care substances such as panthenol, silicone, collagen, vitamins, protein hydrolyzates, stabilizers, pH regulators, dyes , UV filter and other common additives.
Soll das erfindungsgemäße Haarfestigungsmittel als Haarspray verwendet werden, so wird in der Regel ein Treibmittel zugesetzt. Übliche Treibmittel sind niedere Alkane, beispielsweise Propan oder Butan, Dirnethylether, Stickstoff, Stickoxydul oder Kohlendioxid oder Gemische aus diesen Substanzen. Die erfindungsgemäßen Haarfestigungsmittel können auch halogenhaltige Kohlenwasserstoffe als Treibmittel enthalten.If the hair fixative according to the invention is to be used as a hair spray, a blowing agent is generally added. Typical blowing agents are lower alkanes, for example propane or butane, methyl ether, nitrogen, nitrogen oxide or carbon dioxide or mixtures of these substances. The hair fixatives according to the invention can also contain halogenated hydrocarbons as blowing agents.
Bei Verwendung in mechanischen Sprühvorrichtungen, beispielsweise Sprühpumpen, kann das Treibmittel entfallen.When used in mechanical spray devices, for example spray pumps, the propellant can be omitted.
Die erfindungsgemäßen Haarfestigungsmittel besitzen hervorragende anwendungstechnische Eigenschaften; sie bilden klare Filme und besitzen in wäßrig/alkoholischen Lösungen eine niedrige Lösungsviskosität, so daß sie auch höherkonzentriert noch gute Sprüheigenschaften besitzen. Überraschenderweise zeigen sie eine deut- lieh erniedrigte Klebrigkeit gegenüber bekannten Haarfestigungsmitteln, insbesondere bestehend aus Vinylcaprolactam und/oder Vinylpyrrolidon und/oder PVP/VA-Copolymer.The hair fixatives according to the invention have excellent performance properties; they form clear films and have a low solution viscosity in aqueous / alcoholic solutions, so that they also have good spray properties even in higher concentrations. Surprisingly, they show a clear lent reduced stickiness to known hair fixatives, in particular consisting of vinyl caprolactam and / or vinyl pyrrolidone and / or PVP / VA copolymer.
5 Die in den nachstehenden Beispielen verwendeten Polyvinylcapro- lactam-Lösungen waren 40 gew.-%ige Lösungen in Ethanol. Der K- Wert nach Fikentscher des Polymeren lag bei 40 (1 % in Ethanol) .5 The polyvinyl caprolactam solutions used in the examples below were 40% by weight solutions in ethanol. The K value according to Fikentscher of the polymer was 40 (1% in ethanol).
Beispiel 1example 1
1010
7,5 Gew.-% Polyvinylcaprolactam-Lösung7.5% by weight of polyvinyl caprolactam solution
2,0 Gew.-% Ultrahold Strong (BASF Aktiengesellschaft)2.0% by weight of Ultrahold Strong (BASF Aktiengesellschaft)
1,5 Gew.-% Polyvinylpyrrolidon (PVP)1.5% by weight polyvinyl pyrrolidone (PVP)
89,0 Gew.-% agua dest.89.0% by weight of agua dest.
1515
Beispiel 2Example 2
7,5 Gew.-% Polyvinylcaprolactam-Lösung7.5% by weight of polyvinyl caprolactam solution
2,0 Gew.-% Ultrahold Strong (BASF Aktiengesellschaft)2.0% by weight of Ultrahold Strong (BASF Aktiengesellschaft)
20 1,5 Gew.-% Polyvinylpyrrolidon (PVP)20 1.5% by weight polyvinylpyrrolidone (PVP)
65,0 Gew.-% Ethanol abs .65.0 wt .-% ethanol abs.
24,0 Gew.-% agua dest.24.0% by weight of agua dest.
Beispiel 3 25Example 3 25
5 Gew.-% Polyvinylcaprolactam-Lösung 2,5 Gew.-% Ultrahold 8 (BASF Aktiengesellschaft) 2,5 Gew.-% Luviskol K30 (BASF Aktiengesellschaft) Polyvinyl- pyrrolidon5% by weight polyvinylcaprolactam solution 2.5% by weight Ultrahold 8 (BASF Aktiengesellschaft) 2.5% by weight Luviskol K30 (BASF Aktiengesellschaft) polyvinylpyrrolidone
30 90,0 Gew.-% Ethanol abs. Beispiel 430 90.0 wt .-% ethanol abs. Example 4
5 Gew.-% Polyvinylcaprolactam-Lösung 2,5 Gew.-% Ultrahold 8 (BASF Aktiengesellschaft) 35 2,5 Gew.-% Luviskol K30 (BASF Aktiengesellschaft) Polyvinyl- pyrrolidon 90,0 Gew.-% agua dest.5% by weight polyvinylcaprolactam solution 2.5% by weight Ultrahold 8 (BASF Aktiengesellschaft) 35 2.5% by weight Luviskol K30 (BASF Aktiengesellschaft) polyvinylpyrrolidone 90.0% by weight agua dest.
Beispiel 5 40Example 5 40
5,0 Gew.-% Polyvinylcaprolactam-Lösung 2,0 Gew.-% Ultrahold 8 (BASF Aktiengesellschaft) 2,5 Gew.-% Luviskol VA 64P, pulverförmiges Copolymer aus5.0% by weight of polyvinylcaprolactam solution 2.0% by weight of Ultrahold 8 (BASF Aktiengesellschaft) 2.5% by weight of Luviskol VA 64P, powdery copolymer
N-Vinylpyrrolidon/VinylacetatN-vinylpyrrolidone / vinyl acetate
45 52,5 Gew.-% Ethanol abs . 35,0 Gew.-% aqua dest. Beispiel 645 52.5 wt .-% ethanol abs. 35.0% by weight aqua dest. Example 6
5 Gew.-% Polyvinylcaprolactam-Lösung5% by weight polyvinyl caprolactam solution
2,5 Gew.-% Ultrahold, pulverförmiges Terpolymer aus N-tertiär- Butylacrylamid, Ethylacrylat, Acrylsaure2.5% by weight ultrahold, powdered terpolymer of N-tertiary butyl acrylamide, ethyl acrylate, acrylic acid
1,5 Gew.-% Luviskol K30 (BASF Aktiengesellschaft): Polyvinylpyrrolidon1.5% by weight Luviskol K30 (BASF Aktiengesellschaft): polyvinylpyrrolidone
0,23 Gew.-% AMP0.23 wt% AMP
53,50 Gew.-% Ethanol abs. 37,27 Gew.-% agua dest. 53.50 wt .-% ethanol abs. 37.27% by weight of agua dest.

Claims

Patentansprüche Patent claims
1. Haarfestigungsmittel, enthaltend1. Hair setting agent containing
A) 0,5 bis 20 Gew.% eines Homopolymeren des N-Vinylcaprolactams oder eines anionischen oder nichtionischen Copolymeren aus mindestens 70 Gew.% N-Vinylcaprolactam (Polymer A) , undA) 0.5 to 20% by weight of a homopolymer of N-vinyl caprolactam or an anionic or nonionic copolymer of at least 70% by weight of N-vinyl caprolactam (polymer A), and
B) 0,5 bis 20 Gew.-% eines Terpolymers (Polymer B) , erhältlich durch CopolymerisationB) 0.5 to 20% by weight of a terpolymer (polymer B), obtainable by copolymerization
(a) mindestens eines C1-C4 N-Alkylacrylamides oder eines C1-C4 N-Alkylmethacrylamides und(a) at least one C 1 -C 4 N-alkylacrylamide or one C 1 -C 4 N-alkylmethacrylamide and
(b) mindestens eines C1-C4 Hydroxyalkylesters oder eines C1-C4 Alkylesters der Acrylsaure oder Methacrylsäure und(b) at least one C 1 -C 4 hydroxyalkyl ester or a C 1 -C 4 alkyl ester of acrylic acid or methacrylic acid and
(c) Acrylsaure und/oder Methacrylsäure(c) acrylic acid and/or methacrylic acid
C) 0,5 bis 20 Gew.-% eines Polymeren ausgewählt aus der Gruppe bestehend aus Copolymeren aus Vinylpyrrolidon und eines Vinylesters und aus Homopolymeren von Vinylpyrrolidon. . Haarfestigungsmittel nach Anspruch 1, dadurch gekennzeichnet, daß als Polymer A ein Homopolymer aus N-Vinylcaprolactam ein- gesetzt wird. . Haarfestigungsmittel nach Anspruch 1, dadurch gekennzeichnet, daß als Polymer B ein Terpolymer aus N-tert. -Butylacrylamid, Ethylacrylat und Acrylsaure eingesetzt wird.C) 0.5 to 20% by weight of a polymer selected from the group consisting of copolymers of vinylpyrrolidone and a vinyl ester and of homopolymers of vinylpyrrolidone. . Hair setting agent according to claim 1, characterized in that a homopolymer of N-vinylcaprolactam is used as polymer A. . Hair setting agent according to claim 1, characterized in that the polymer B is a terpolymer of N-tert. -Butylacrylamide, ethyl acrylate and acrylic acid are used.
. Haarfestigungsmittel nach einem der Ansprüche 1 bis 3 , dadurch gekennzeichnet, daß es einen Alkohol und niedere Alkane enthält . . Hair setting agent according to one of claims 1 to 3, characterized in that it contains an alcohol and lower alkanes.
EP03729484A 2002-01-21 2003-01-20 Fixative agents for hair Withdrawn EP1469817A1 (en)

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DE10202253 2002-01-21
DE10202253A DE10202253A1 (en) 2002-01-21 2002-01-21 New hair fixatives
PCT/EP2003/000490 WO2003059301A1 (en) 2002-01-21 2003-01-20 Fixative agents for hair

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US3145147A (en) * 1961-02-20 1964-08-18 Gen Aniline & Film Corp Film forming composition of copolymers of nu-vinyl-epsilon-caprolactam
US5637296A (en) * 1994-08-31 1997-06-10 Isp Investments Inc. Low VOC hair spray resin composition of improved spray properties
DE19510474A1 (en) * 1995-03-27 1996-10-02 Basf Ag New hair fixatives
WO2001013884A2 (en) * 1999-08-26 2001-03-01 Basf Aktiengesellschaft Cosmetic and/or pharmaceutical preparations with polymers containing polysiloxanes and the uses thereof

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