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WO1991003229A1 - Hair care preparations - Google Patents

Hair care preparations Download PDF

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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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WIPO (PCT)
Prior art keywords
hair
preparations according
monomers
group
groups
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PCT/EP1990/001444
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German (de)
French (fr)
Inventor
Reinhard Müller
Klaus-Dieter Wisotzki
Karl Giede
Jutta Bernike
Horst Höffkes
Kurt Seidel
Iduna Matzik
Dieter Schrader
Adolf Klenk
Kurt Dahmen
Helmut Klimmek
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Henkel Kommanditgesellschaft Auf Aktien
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Publication of WO1991003229A1 publication Critical patent/WO1991003229A1/en

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    • 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.

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Abstract

Aqueous hair care preparations containing zwitterion polymerizates and composed essentially of A) monomers containing quaternary ammonium groups of general formula (I): R?1-CH=CR?2-CO-Z-(Cn?H2n?)-N?(+)R?3R?4R?5 A?(-), where R?1 and R?2 independently stand for hydrogen or a methyl group and R?3, R?4 and R?5 independently stand for alkyl groups with 1 to 4 carbon atoms, Z stands for an NH group or an oxygen atom, n is an integer from 2 to 5 and A?(-) is an anion of an organic or inorganic acid, and B) monomer carboxylic acids of general formula (II): R?6-CH=CR?7-COOH, where R?6 and R?7 independently stand for hydrogen or methyl groups, possess hair conditioning and hair setting properties. Wet hair treated with these preparations can be combed as easily as that treated with cationic rinses.

Description

"Haarpflegemittel"  "Hair care products"
Die Erfindung betrifft Zubereitungen zur Haarbehandlung, die zwitterionische Polymerisate enthalten. The invention relates to preparations for hair treatment which contain zwitterionic polymers.
Haare weisen nach dem Waschen, Färben oder Dauerwellen häufig eine unbefriedigende Naß- und Trockenkämmbarkeit auf und das Lockenhaltevermögen der trockenen Haare ist unzureichend. Um diesem Mißstand abzuhelfen, müssen entweder den Haarbehandlungsmitteln entsprechende Komponenten hinzugefügt oder die Haare anschließend einer separaten Behandlung mit diesen Substanzen, die dann üblicherweise in Form einer Spülung formuliert werden, unterzogen werden. Hair often has unsatisfactory wet and dry combability after washing, dyeing or perming and the curl retention capacity of dry hair is inadequate. In order to remedy this situation, appropriate components must either be added to the hair treatment compositions or the hair must then be subjected to a separate treatment with these substances, which are then usually formulated in the form of a rinse.
Als solche haareigenschaftsverbessernde Wirkstoffe werden häufig polymere Verbindungen eingesetzt. Polymeric compounds are frequently used as active ingredients that improve hair properties.
Kationische Polymere, wie beispielsweise die aus den amerikanischen Patenten US 3,816,616 und US 3,472,840 bekannten Cellulosederivate, können zwar die Naßkämmbarkeit deutlich verbessern, erzielen aber nur unbefriedigende haarfestigende und frisurstabilisierende Wirkungen. 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.
Ebenfalls bekannt ist die Verwendung von zwitterionischen Polymeren, die anionische Gruppen, meist Carboxylgruppen, und quartäre Ammoniumgruppen im Molekül enthalten, in Haarbehandlungsmitteln. Beispielsweise beschreibt die DE-OS 21 50 557 die Verwendung von Polymerisaten zwitterionischer Monomerer in Haarfestlegemitteln. Auch aus DE-OS 28 17 369 war die Verwendung von Copolymerisäten aus Dimethylaminoethylmethacrylat, Acrylsäure und Methylmethacrylat in Haarfestlegemitteln und Shampoos bekannt. It is also known to use zwitterionic polymers which contain anionic groups, usually carboxyl groups, and quaternary ammonium groups in the molecule in hair treatment compositions. For example, 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.
Diese für Haarbehandlungs- und Haarfestlegemitteln bekannten zwitterionischen Polymeren zeigen, insbesondere in Formulierungen mit anionischen Tensiden, den Nachteil, daß die haaravivierenden und haarfestigenden Eigenschaften im Verlaufe längerer Lagerzeit allmählich verlorengehen. Es wurde daher in der DE-OS 37 08 451 vorgeschlagen, zwitterionische Polymerisate, bestehend aus 30-70 % Monomeren mit quartären Ammoniumgruppen, 10-30 % monomeren olefinisch ungesättigten Carbonsäuren, 10-30 % monomeren olefinisch ungesättigten Carbonsäureestern und 0-40 % Monomeren mit tertiären Aminogruppen, zu verwenden. Diese Polymerisate sind gut verträglich mit anionischen und kationischen Tensiden und zeigen gute haaravivierende und frisurstabilisierende Eigenschaften. These 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.
Somit stehen zwar geeignete Polymerisate zur Verfügung, um die gewünschten Effekte auf dem Haar zu erzielen, doch sind diese aus mindestens 3 oder 4 Monomeren zusammengesetzt. Es besteht daher weiterhin ein Bedarf an Polymerisaten, die bei vergleichbaren Eigenschaften weniger komplex aufgebaut, das heißt aus einer geringeren Anzahl an unterschiedlichen Monomeren herstellbar sind. 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.
Überraschenderweise wurde nunmehr gefunden, daß bestimmte zwitterionische Polymerisate aus Monomeren mit quartären Ammoniumgruppen und monomeren Carbonsäuren naßkämmbarkeitsverbessernde, haaravivierende und frisurstabilisierende Eigenschaften aufweisen, die bisher nur bei Polymerisaten mit einer größeren Anzahl unterschiedlicher Monomerer bekannt waren. Weiterhin ist es mit diesen Polymerisaten möglich, Haarbehandlungsmittel auf der Basis von Anion- und/oder Amphotensiden zu formulieren, die von ihrer Wirkung auf die Naßkämmbarkeit von Haaren in ihrem Leistungsniveau den bekannt guten kationischen Spülungen entsprechen. Surprisingly, it has now been found that certain zwitterionic polymers made from monomers with quaternary ammonium groups and monomeric carboxylic acids have properties which improve wet combability, hair-activating and hairstyle-stabilizing properties, which have hitherto only been the case with polymers with a large number different monomers were known. Furthermore, it is possible with these polymers to formulate hair treatment compositions based on anionic and / or amphoteric surfactants which correspond in their performance level to the known good cationic conditioners in terms of their effect on the wet combability of hair.
Gegenstand der Erfindung sind somit wäßrige, zwitterionische Polymerisate enthaltende Zubereitungen zur Haarbehandlung, dadurch gekennzeichnet, daß sich die zwitterionischen Polymerisate im wesentlichen zusammensetzen aus The invention thus relates to aqueous preparations for hair treatment containing zwitterionic polymers, characterized in that the zwitterionic polymers essentially consist of one another
A) Monomeren mit quartären Ammoniumgruppen der allgemeinen Formel (I), A) monomers with quaternary ammonium groups of the general formula (I),
R1-CH=CR2-CO-Z-(CnH2n)-N(+)R3R4R5 A(-) (I) in der R1 und R2 unabhängig voneinander stehen für Wasserstoff oder eine Methylgruppe und R3, R4 und R5 unabhängig voneinander für Alkylgruppen mit 1 bis 4 Kohlenstoff-Atomen, Z eine NH- Gruppe oder ein Sauerstoffatom, n eine ganze Zahl von 2 bis 5 und A(-) das Anion einer organischen oder anorganischen Säure ist und 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
B) monomeren Carbonsäuren der allgemeinen Formel (II), B) monomeric carboxylic acids of the general formula (II),
R6-CH=CR7-COOH (II) in denen R6 und R 7 unabhängig voneinander Wasserstoff oder Methylgruppen sind. Geeignete Ausgangsmonomere sind z. B. Dimethylaminoethylacrylamid, Dimethylaminoethylmethacrylamid, Dimethylaminopropylacrylamid, Dimethylaminopropylmethacrylamid und Diethylaminoethylacrylamid, wenn Z eine NH-Gruppe bedeutet oder Dimethylaminoethylacrylat, Dimethylaminoethylmethacrylat und Diethylaminoethylacrylat, wenn Z ein Sauerstoffatom ist. 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.
Die Herstellung der genannten Monomeren erfolgt nach bekannten Verfahren, wie sie z. B. in US-PS 3 878 247, DE-PS 28 19 735, DE-PS 28 36 520, DE-PS 34 02 599 oder CH-PS 464 891 beschrieben sind. 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.
Die eine tertiäre Aminogruppe enthaltenden Monomeren werden dann in bekannter Weise quarterniert, wobei als Alkylierungsreagenzien Methylchlorid, Dimethylsulfat oder Diethylsulfat besonders geeignet sind. Die Quaternisierungsreaktion kann in wäßriger Lösung oder im Lösungsmittel erfolgen. Geeignete Verfahren sind z. B. in DE-OS 3330326, DE-OS 2537378 oder DE-OS 3244274 beschrieben. 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.
Vorteilhafterweise werden solche Monomere der Formel (I) verwendet, die Derivate des Acrylamids oder Methacrylamids darstellen. Weiterhin bevorzugt sind solche Monomeren, die als Gegenionen Halogenid-, Methoxysulfat- oder Ethoxysulfat-Ionen enthalten. Ebenfalls bevorzugt sind solche Monomeren der Formel (I), bei denen R3, R4 und R5 Methylgruppen sind. 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.
Das Acrylamidopropyl-trimethylammoniumchlorid ist ein ganz besonders bevorzugtes Monomer der Formel (I). Acrylamidopropyltrimethylammonium chloride is a very particularly preferred monomer of formula (I).
Als monomere Carbonsäuren der Formel (II) eignen sich Acrylsäure, Methacrylsäure, Crotonsäure und 2-Methyl-crotonsäure. Bevorzugt werden Acryl- oder Methacrylsäure, insbesondere Acrylsäure, eingesetzt. Acrylic acid, methacrylic acid, crotonic acid and 2-methyl-crotonic acid are suitable as monomeric carboxylic acids of formula (II). Prefers acrylic or methacrylic acid, especially acrylic acid, are used.
Die erfindungsgemäßen zwitterionischen Polymerisate werden aus Monomeren der Formeln (I) und (II) nach an sich bekannten Polymerisationsverfahren hergestellt. Die Polymerisation kann entweder in wäßriger oder wäßrig-alkoholischer Lösung erfolgen. Als Alkohole werden Alkohole mit 1 bis 4 Kohlenstoffatomen, vorzugsweise Isopropanol, verwendet, die gleichzeitig als Polymerisationsregler dienen. Der Monomerlösung können aber auch andere Komponenten als Regler zugesetzt werden, z. B. Ameisensäure oder Mercaptane, wie Thioethanol und Thioglykolsäure. Die Initiierung der Polymerisation erfolgt mit Hilfe von radikalbildenden Substanzen. Hierzu können Redoxsysteme und/oder thermisch zerfallende Radikalbildner vom Typ der Azoverbindungen, wie z. B. Azoisobuttersäurenitril, Azo-bis-(cyanopentansäure) oder Azo-bis-(amidinopropan)dihydrochlorid verwendet werden. Als Redoxsysteme eignen sich z. B. Kombinationen aus Wasserstoffperoxid, Kalium- oder Ammoniumperoxodisulfat sowie tertiäres Butylhydroperoxid mit Natriumsulfit, Natriumdithionit oder Hydroxylaminhydrochlorid als Reduktionskomponente. 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. As redox systems such. B. combinations of hydrogen peroxide, potassium or ammonium peroxodisulfate and tertiary butyl hydroperoxide with sodium sulfite, sodium dithionite or hydroxylamine hydrochloride as a reduction component.
Die Polymerisation kann isotherm oder unter adiabatischen Bedingungen durchgeführt werden, wobei in Abhängigkeit von den Konzentrationsverhältnissen durch die freiwerdende Polymerisationswärme der Temperaturbereich für den Ablauf der Reaktion zwischen 20 und 200 °C schwanken kann, und die Reaktion gegebenenfalls unter dem sich einstellenden Überdruck durchgeführt werden muß. Bevorzugterweise liegt die Reaktionstemperatur zwischen 20 und 100 °C. Der pH-Wert während der Copolymerisation kann in einem weiten Bereich schwanken. Vorteilhafterweise wird bei niedrigen pH-Werten polymerisiert; möglich sind jedoch auch pH-Werte oberhalb des Neutralpunktes. Nach der Polymerisation wird mit einer wäßrigen Base, z. B. Natronlauge, Kalilauge oder Ammoniak, auf einen pH-Wert zwischen 5 und 10, vorzugsweise 6 bis 8, eingestellt. Nähere Angaben zum Polymerisationsverfahren können den Beispielen entnommen werden. 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. After the polymerization, 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.
Als besonders wirksam haben sich solche Polymerisate erwiesen, bei denen die Monomeren der Formel (I) gegenüber den Monomeren der Formel (II) im Überschuß vorlagen. Es ist daher erfindungsgemäß bevorzugt, solche Polymerisate zu verwenden, die aus Monomeren der Formel (I) und die Monomeren der Formel (II) in einem Molverhältnis von 60:40 bis 95:5, insbesondere von 75:25 bis 95:5, bestehen. 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 .
Die genannten zwitterionischen Polymerisate sind in den erfindungsgemäßen Zubereitungen vorzugsweise in Mengen von 0,1 bis 10 Gew.-%, bezogen auf die gesamte Zubereitung, enthalten. Die naßkämmbarkeitsverbessernde Wirkung der Polymerisate ist bereits bei niedrigen Konzentrationen sehr groß; die haaravivierenden und haarfestigenden Wirkungen werden dagegen in den meisten Fällen erst bei Konzentrationen oberhalb von etwa 1 Gew.-% beobachtet. Es ist daher besonders bevorzugt, die Polymerisate in Mengen von etwa 1 bis 5 Gew.-% einzusetzen. 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.
Die erfindungsgemäßen zwitterionischen Polymeren werden bevorzugt in wäßrigen Zubereitungen mit einem Gehalt an oberflächenaktiven Verbindungen verwendet. Als oberflächenaktive Verbindungen werden dabei anionische, zwitterionische, amphotere und/oder nichtionischen Tenside bevorzugt. Als anionische Tenside eignen sich in erfindungsgemäßen Haarbehandlungsmitteln alle für die Verwendung am menschlichen Körper geeigneten anionischen oberflächenaktiven Stoffe. Diese sind gekennzeichnet durch eine wasserlöslich machende, anionische Gruppe wie z. B. eine Carboxylat-, Sulfat-, Sulfonat- oder PhosphatGruppe und eine lipophile Alkylgruppe mit etwa 10 bis 22 C-Atomen. Zusätzlich können im Molekül Glykol- oder Polyglykolether-Gruppen, Ester-, Ether- und Amidgruppen sowie Hydroxylgruppen enthalten sein. Beispiele für geeignete anionische Tenside sind die Natrium-, Kalium- und Ammonium- sowie die Mono-, Di- und Trialkanolammoniumsalze mit 2 oder 3 C-Atomen in der Alkanolgruppe, vonThe 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. In addition, the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups. Examples of 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
- linearen Fettsäuren mit 10 bis 22 C-Atomen (Seifen), - linear fatty acids with 10 to 22 carbon atoms (soaps),
- Ethercarbonsäuren der Formel R-O-(CH2-CH2O)x-CH2-COOH, in der R eine lineare Alkylgruppe mit 10 bis 22 C-Atomen und x = 0 oder 1 bis 10 ist, Ether carboxylic acids of the formula RO- (CH 2 -CH 2 O) x -CH 2 -COOH, in which R is a linear alkyl group with 10 to 22 C atoms and x = 0 or 1 to 10,
- Acylsarcosiden mit 10 bis 18 C-Atomen in der Acylgruppe,  Acyl sarcosides with 10 to 18 carbon atoms in the acyl group,
- Acyltauriden mit 10 bis 18 C-Atomen in der Acylgruppe,  Acyl taurides with 10 to 18 carbon atoms in the acyl group,
- Acylisethionaten mit 10 bis 18 C-Atomen in der Acylgruppe, Acyl isethionates with 10 to 18 carbon atoms in the acyl group,
- Sulfobernsteinsäuremono- und dialkylestern mit 8 bis 18 C- Atomen in der Alkylgruppe und Sulfobernsteinsäuremono-alkylpolyoxyethylestern mit 8 bis 18 C-Atomen in der Alkylgruppe und 1 bis 6 Oxyethylgruppen, Sulfosuccinic acid mono- and dialkyl esters with 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid mono-alkyl polyoxyethyl esters with 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups,
- linearen Alkansulfonaten mit 12 bis 18 C-Atomen,  linear alkanesulfonates with 12 to 18 carbon atoms,
- linearen Alpha-Olefinsulfonaten mit 12 bis 18 C-Atomen,  linear alpha olefin sulfonates with 12 to 18 carbon atoms,
- Alpha-Sulfofettsäuremethylestern von Fettsäuren mit 12 bis 18 C-Atomen,  - Alpha-sulfofatty acid methyl esters of fatty acids with 12 to 18 carbon atoms,
- Alkylsulfaten und Alkylpolyglykolethersulfaten der Formel  - Alkyl sulfates and alkyl polyglycol ether sulfates of the formula
R-O(CH2-CH2O)x-OSO3H, in der R eine bevorzugt lineare Alkylgruppe mit 10 bis 18 C-Atomen und x = 0 oder 1 bis 12 ist,RO (CH 2 -CH 2 O) x -OSO 3 H, in which R is a preferably linear alkyl group with 10 to 18 carbon atoms and x = 0 or 1 to 12,
- Gemische oberflächenaktiver Hydroxysulfonate gemäß DE-OS - Mixtures of surface active hydroxysulfonates according to DE-OS
3725030 - sulfatierte Hydroxyalkylpolyethylen- und/oder Hydroxyalkylenpropylenglykolether gemäß DE-OS 3723254. 3725030 - Sulphated hydroxyalkyl polyethylene and / or hydroxyalkylene propylene glycol ethers according to DE-OS 3723254.
- Ester der Weinsäure und Zitronensäure mit Alkoholen, die  - esters of tartaric acid and citric acid with alcohols
Anlagerungsprodukte von etwa 2-15 Molekülen Ethylenoxid und/oder Propylenoxid an Fettalkohole mit 8 bis 22 C-Atomen darstellen.  Represent addition products of about 2-15 molecules of ethylene oxide and / or propylene oxide on fatty alcohols with 8 to 22 carbon atoms.
Bevorzugte anionische Tenside sind Alkylsulfate- und Alkylpolyglykolethersulfate mit 10 bis 18 C-Atomen in der Alkylgruppe und bis zu 12 Glykolethergruppen im Molekül. 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.
Als zwitterionische Tenside werden solche oberflächenaktiven Verbindungen bezeichnet, die im Molekül mindestens eine quartäre Ammoniumgruppe und mindestens eine -COO(-)- oder -SO3(-)-Gruppe tragen. Besonders geeignete zwitterionische Tenside sind die sogenannten Betaine wie die N-Alkyl-N,N-dimethylammonium-glycinate, beispielsweise das Kokosalkyl-N,N-dimethylammonium-glycinat, N-Acyl-aminopropyl-N,N-dimethylammoniumglycinate, beispielsweise das Kokosacylaminopropyl-N,N-dimethylammoniumglycinat, und 2-Alkyl3-carboxylmethyl-3-hydroxyethyl-imidazoline mit jeweils 8 bis 18 C-Atomen in der Alkyl- oder Acylgruppe sowie das Kokosacylaminoethylhydroxyethylcarboxymethylglycinat. 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.
Unter amphoteren Tensiden werden solche oberflächenaktiven Verbindungen verstanden, die außer einer C8-C18-Alkyl- oder -Acylgruppe im Molekül mindestens eine freie Aminogruppe und mindestens eine - -COOH- oder -SO3H-Gruppe enthalten und zur Ausbildung innerer Salze befähigt sind. Beispiele für geeignete amphotere Tenside sind N-Alkylglycine, N-Alkylaminopropionsäuren, N-Alkylaminobuttersäuren, N-Alkyliminodipropionsäuren, N-Hydroxyethyl-N-alkylamidopropylglycine, N-Alkyltaurine, N-Alkylsarkosine, 2-Alkyl aminopropionsäuren und Alkylaminoessigsäuren mit jeweils etwa 8 bis 18 C-Atomen in der Alkylgruppe. 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. Examples of suitable 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.
Nichtionische Tenside sind vor allem die Anlagerungsprodukte von 2 bis 20 Mol Ethylenoxid an bevorzugt lineare Alkohole mit 12 bis 18 C-Atomen, an Alkylphenole mit 8 bis 15 C-Atomen in der Alkylgruppe, an Fettsäuren mit 12 bis 18 C-Atomen, an Fettsäurepartialglyceride, an Fettsäure-sorbitan-partialester, an Fettsäurealkanolamide und an Methylglucosid-Fettsäureester. Weitere geeignete nichtionogene Tenside sind Alkyl(oligo)-glucoside, AlkylaminoxidTenside und Fettsäurealkanolamide. 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.
Auch kationische Tenside können in den erfindungsgemäßen Zubereitungen enthalten sein, wenn sie mit den anderen Komponenten, z.B. anionischen Tensiden, verträglich sind. Solche kationischen Tenside sind z. B. aus DE-OS 3442175 bekannt. 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.
Vorzugsweise enthalten die erfindungsgemäßen Zubereitungen oberflächenaktiven Verbindungen in Mengen von 0,1 bis 40 Gew.-%, bezogen auf die gesamte Zubereitung. 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.
Aufgrund ihrer guten haaravivierenden und haarfestigenden Eigenschaften sowie ihrer Verträglichkeit mit den üblichen, in Haarbehandlungsmitteln verwendeten Stoffen eignen sich die erfindungsgemäßen zwitterionischen Polymerisate als festigende und haaravivierende Komponente in allen gängigen wäßrigen Zubereitungen zur Reinigung und Pflege der Haare. Solche Zubereitungen können z. B. Haarshampoos, Haarnachspülmittel, Haarfestiger, HaarFönwellmittel sowie wäßrige Färbemittel, Dauerwellmittel oder Dauerwell-Fixiermittel sein. Die erfindungsgemäßen wäßrigen Zubereitungen zur Reinigung und Pflege der Haare können daher neben den obligatorischen zwitterionischen Polymeren alle für den jeweiligen Anwendungszweck üblichen Hilfs- und Zusatzmittel enthalten. Because of their good hair-activating and hair-fixing properties and their compatibility with the usual substances used in hair treatment compositions, 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.
Für Haarnachspülmittel sind dies z. B. kationische Tenside, insbesondere oberflächenaktive quartäre Ammoniumsalze, Fettalkohole mit 12 bis 22 C-Atomen, Fettsäurepartialglyceride, kosmetische Ölund Fettkomponente und wasserlösliche Polymere mit verdickender Wirkung. Für Haarfestiger und Fönwellmittel sind dies z. B. ebenfalls kationische Tenside, kationische, nichtionogene oder anionische Polymere und niedere Alkohole. Haarfärbemittel enthalten direktziehende Farbstoffe oder Oxidationsfarbstoffvorprodukte, anionische oder nichtionogene Tenside, Ammoniak oder Alkanolamine sowie ggf. Antioxidantien. Dauerwellfixiermittel enthalten ein Oxidationsmittel, z. B. H2O2, H2O2-Anlagerungsverbindungen oder Kaliumbromat, sowie anionische oder nichtionogene Tenside. For hair rinsing agents, these are e.g. B. 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. For 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 surfactants.
Die erfindungsgemäßen Zubereitungen weisen bevorzugt einen pH-Wert von 4 bis 10, insbesondere von 5 bis 9, auf. The preparations according to the invention preferably have a pH of 4 to 10, in particular 5 to 9.
Die folgenden Beispiele sollen den Erfindungsgegenstand näher erläutern, ohne ihn hierauf zu beschränken. The following examples are intended to explain the subject matter of the invention in more detail without restricting it thereto.
Beispiele Examples
1. Herstellung eines Polymerisats aus Acrylamidopropyltrimethylammoniumchlorid und Acrylsäure im Molverhältnis 3 : 1 (Polymerisat P1). 1. Preparation of a polymer from acrylamidopropyltrimethylammonium chloride and acrylic acid in a molar ratio of 3: 1 (polymer P1).
In einem Reaktor mit Impellerrührer, Heizung, Kühlung, Rückflußkühlung sowie einer Temperaturmessvorrichtung wurden In a reactor with impeller stirrer, heating, cooling, reflux cooling and a temperature measuring device
201,17 kg Wasser 201.17 kg of water
89,59 kg einer 60 Gew.-%igen wäßrigen Lösung von Acrylamidpropyltrimethylammoniumchlorid und  89.59 kg of a 60 wt .-% aqueous solution of Acrylamidpropyltrimethylammoniumchlorid and
6,25 kg Acrylsäure vorgelegt. Es stellte sich ein pH-Wert von 3,4 ein. Die Lösung wurde mit Stickstoff gespült und anschließend auf 60 °C aufgeheizt. Dann wurden nacheinander die Lösungen aus  6.25 kg of acrylic acid submitted. A pH of 3.4 was established. The solution was flushed with nitrogen and then heated to 60 ° C. Then the solutions were chosen one after the other
0,06 kg Azo-bis-(amidinopropan)dihydrochlorid in 1,00 kg Wasser, 0.06 kg azo-bis- (amidinopropane) dihydrochloride in 1.00 kg water,
0,024 kg Kaliumperoxodisulfat in 1,000 kg Wasser und 0.024 kg potassium peroxodisulfate in 1,000 kg water and
0,012 kg Natriumdisulfit in 1,000 kg Wasser dem Ansatz unter Rühren hinzugefügt. Hierbei fand nur eine leichte Erwärmung statt. Das Reaktionsgemisch wurde auf 80 - 85 °C aufgeheizt und während 4 Stunden bei dieser Temperatur gehalten. Nach dieser Zeit war die Polymerisation beendet. Die viskose Lösung wurde auf 30 - 40 °C abgekühlt und mit 5,000 kg 45 %iger wäßriger Natronlauge neutral gestellt. Die klare, farblose Polymerlösung zeigte folgende Kenndaten: pH-Wert: 6,9 0.012 kg of sodium disulfite in 1,000 kg of water were added to the batch with stirring. Only slight warming took place here. The reaction mixture was heated to 80-85 ° C. and kept at this temperature for 4 hours. After this time the polymerization was complete. The viscous solution was cooled to 30-40 ° C. and neutralized with 5,000 kg of 45% aqueous sodium hydroxide solution. The clear, colorless polymer solution had the following characteristics: pH: 6.9
Trockensubstanz: 20 % Dry matter: 20%
Produktviskosität: 13800 mPa*s Product viscosity: 13800 mPa * s
Grenzviskosität : 220 ml/g Intrinsic viscosity: 220 ml / g
(in 10 % NaCl-Lösung) (in 10% NaCl solution)
2. Anwendungsbeispiele 2. Examples of use
2.1. Haarspülung No.1 2.1. Hair conditioner No.1
Komponenten Gew.-% Components weight%
Fettalkohol (C12-14)poly(3 E0)glykolether-sulfat, Fatty alcohol (C 12-14 ) poly (3 E0) glycol ether sulfate,
Na-Salz, 28 %ige wäßrige Lösung 5,0  Na salt, 28% aqueous solution 5.0
Kokosacyl(C12-C18)-aminopropyl-dimethylglycin, Cocoacyl (C 12 -C 18 ) aminopropyl dimethylglycine,
30 %ige wäßrige Lösung 1,0  30% aqueous solution 1.0
Polymerisat P1 (20 % Aktivsubstanz in Wasser) 2,5  Polymer P1 (20% active substance in water) 2.5
Wasser ad 100  Water ad 100
Die Spülung liegt in Form einer trüben Lösung vor. Die Naßkämmbarkeit von mit dieser Spülung behandelten Haaren war sehr gut; eine Haarbelastung oder statische Aufladung der Haare wurde nicht beobachtet. 2.2. Haarspülung No.2 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
Komponenten Gew.-% Components weight%
Fettalkohol (C12-14)poly(3 EO)glykolether-sulfat, Fatty alcohol (C 12-14 ) poly (3 EO) glycol ether sulfate,
Na-Salz, 28 %ige wäßrige Lösung 5,0Na salt, 28% aqueous solution 5.0
Dehyton(R) AB 301 1,0Dehyton (R) AB 30 1 1.0
Polymerisat P1 (20 % Aktivsubstanz in Wasser) 2,5Polymer P1 (20% active substance in water) 2.5
Wasser ad 100 Water ad 100
1 Fettamin-Derivat mit Betainstruktur, ca. 30 % Aktivsubstanz in Wasser, CTFA-Bezeichnung: Coco-Betaine (HENKEL) 1 fatty amine derivative with betaine structure, approx. 30% active substance in water, CTFA name: Coco-Betaine (HENKEL)
Die Spülung liegt in Form einer trüben Lösung vor. Die Naßkämmbarkeit von mit dieser Spülung behandelten Haaren war sehr gut. The rinse is in the form of a cloudy solution. The wet combability of hair treated with this conditioner was very good.
2.3. Haarspülung No.3 2.3. Hair conditioner No.3
Komponenten Gew. -% Components weight%
Sulfobernsteinsäurehalbester auf Basis eines C12-14-Alkylpoly(3 EO)glykolethers, Dinatriumsalz (40 % Semi- sulfosuccinic acid based on a C 12-14 alkyl poly (3 EO) glycol ether, disodium salt (40%
Aktivsubstanz in Wasser), CTFA-Bezeichnung: Disodium Active substance in water), CTFA name: Disodium
laurethsulfosuccinate 0,9laureth sulfosuccinate 0.9
Texapon(R) K14 S spez.2 1,2Texapon (R) K14 S spec. 2 1.2
Dehyton(R) AB 30 1,0Dehyton (R) AB 30 1.0
Polymerisat P1 (20 % Aktivsubstanz in Wasser) 2,5 Wasser ad 100 Polymer P1 (20% active substance in water) 2.5 water ad 100
2 Natriumlaurylmyristylethersulfat, ca. 30 % Aktivsubstanz in 2 sodium lauryl myristyl ether sulfate, approx. 30% active ingredient in
Wasser (HENKEL)  Water (HENKEL)
Die Naßkämmbarkeit von mit dieser Spülung behandelten Haaren war gut bis sehr gut. 2.4. Haarspülung No.4 The wet combability of hair treated with this conditioner was good to very good. 2.4. Hair conditioner No.4
Komponenten Gew.-% Components weight%
Sulfobernsteinsäurehalbester auf Basis eines C12-14-Alkylpoly(3 EO)glykolethers, Dinatriumsalz (40 % Semi- sulfosuccinic acid based on a C 12-14 alkyl poly (3 EO) glycol ether, disodium salt (40%
Aktivsubstanz in Wasser), CTFA-Bezeichnung: Disodium Active substance in water), CTFA name: Disodium
laurethsulfosuccinate 1,0laureth sulfosuccinate 1.0
Dehyton(R) AB 30 7,5Dehyton (R) AB 30 7.5
Polymerisat P1 (20 % Aktivsubstanz in Wasser) 2,5 Wasser ad 100 Polymer P1 (20% active substance in water) 2.5 water ad 100
Die Spülung liegt in Form einer fast klaren Lösung vor. Die Naßkämmbarkeit von mit dieser Spülung behandelten Haaren war sehr gut. The rinse is in the form of an almost clear solution. The wet combability of hair treated with this conditioner was very good.
2.5. Haarspülung No.5 2.5. Hair conditioner No.5
Komponenten Gew.-% Components weight%
C16-18-Fettalkohol 3,0C 16-18 fatty alcohol 3.0
Kokosacyl(C12-C18)-aminopropyl-dimethylglycin, Cocoacyl (C 12 -C 18 ) aminopropyl dimethylglycine,
30 %ige wäßrige Lösung 8,0 30% aqueous solution 8.0
Fettalkohol (C12-14)poly(3 E0)glykolether-sulfat, Fatty alcohol (C 12-14 ) poly (3 E0) glycol ether sulfate,
Na-Salz, 28 %ige wäßrige Lösung 5,0 Na salt, 28% aqueous solution 5.0
Polymerisat P1 (20 % Aktivsubstanz in Wasser) 2,5Polymer P1 (20% active substance in water) 2.5
Wasser ad 100 Water ad 100
Zur Herstellung dieser Haarspülung wurde die Mischung aus Tensiden und Polymerisat in die geschmolzene Fettphase gegeben und emulgiert. Die Naßkämmbarkeit von mit dieser Spülung behandelten Haaren war hervorragend. 2.6. Haarshampoo No.1 To produce this hair conditioner, the mixture of surfactants and polymer was added to the melted fat phase and emulsified. The wet combability of hair treated with this conditioner was excellent. 2.6. Hair shampoo No.1
Komponenten Gew.-% Components weight%
Fettalkohol (C12-14)poly(3 EO)glykolether-sulfat, Fatty alcohol (C 12-14 ) poly (3 EO) glycol ether sulfate,
Na-Salz, 28 %ige wäßrige Lösung 50,0 Na salt, 28% aqueous solution 50.0
Kokosacyl(C12-C18)-aminopropyl-dimethylglycin, Cocoacyl (C 12 -C 18 ) aminopropyl dimethylglycine,
30 %ige wäßrige Lösung 10,0 30% aqueous solution 10.0
Polymerisat P1 (20 % Aktivsubstanz in Wasser) 5,0Polymer P1 (20% active substance in water) 5.0
Wasser ad 100 Water ad 100
Die Naßkämmbarkeit der mit dieser Zubereitung Shampoon ierten Haare war hervorragend. The wet combability of the hair shampooed with this preparation was excellent.
2.7. Haarshampoo No.2 2.7. Hair shampoo No.2
Komponenten Gew.-% Components weight%
Fettalkohol(C12-14)poly(3 EO)glykolether-sulfat, Fatty alcohol (C 12-14 ) poly (3 EO) glycol ether sulfate,
Na-Salz, 28 %ige wäßrige Lösung 45,0 Na salt, 28% aqueous solution 45.0
Kokosacyl(C12-C18)-aminopropyl-dimethylglycin, Cocoacyl (C 12 -C 18 ) aminopropyl dimethylglycine,
30 %ige wäßrige Lösung 15,0 30% aqueous solution 15.0
Akypo(R) RLM 100 NV3 5,0Akypo (R) RLM 100 NV 3 5.0
Polymerisat P1 (20 % Aktivsubstanz in Wasser) 5,0Polymer P1 (20% active substance in water) 5.0
Wasser ad 100 Water ad 100
3 Wäßrige Lösung von C12-14-Alkyl-O-(CH2-CH2-O)10-CH2-COONa, 3 Aqueous solution of C 12-14 alkyl-O- (CH 2 -CH 2 -O) 10 -CH 2 -COONa,
22 % Aktivsubstanz (CHEM-Y)  22% active substance (CHEM-Y)
Bei Behandlung der Haare mit diesem Shampoo wurden diese nicht nur von Schmutz und Fett befreit, vielmehr erhielten die feuchten Haare eine ausgeprägte Avivage und die trockenen Haare Fülle und Volumen. Zur Quantifizierung des durch das Polymerisat erzielten Effektes wurde eine 15 cm lange Haarsträhne (2 g) auf ein Glasrohr mit einem Außendurchmesser von 1,7 cm gewickelt, fixiert und mit 0,2 g des Shampoos behandelt. Anschließend wurde die Haarsträhne mit Wasser gespült und getrocknet. Ein Maß für die Stabilität der nach dem Herausziehen des Glasstabes erhaltenen Locke ist der Curl-Retention-Wert. Der Curl-Retention-Wert ist definiert alsWhen the hair was treated with this shampoo, it not only freed it of dirt and grease, it also gave the moist hair a pronounced finish and the dry hair fullness and volume. To quantify the effect achieved by the polymer, a 15 cm strand of hair (2 g) was wound on a glass tube with an outside diameter of 1.7 cm, fixed and treated with 0.2 g of the shampoo. The lock of hair was then rinsed with water and dried. A measure of the stability of the curl obtained after pulling out the glass rod is the curl retention value. The curl retention value is defined as
[0-1x)/(1-1o)] * 100 %, wobei 1 die Länge der Haarsträhne (15 cm), 10 die Länge der Haarlocke unmittelbar nach dem Trocknen und 1x die Länge der Haarlocke nach 48 h Lagerung in einem Trockenschrank bei konstanten Bedingungen (30 °C, 40 % relative Luftfeuchtigkeit) ist. Die mit dem erfindungsgemäßen Shampoo behandelte Locken wiesen einen Curl-Retention-Wert von 94,7 % auf, während Locken, die mit einem gleichartigen Shampoo behandelt wurden, dem das Polymerisat P1 nicht zugesetzt worden war, nur einen Curl-Retention-Wert von 87,1 % zeigten. [0-1 x ) / (1-1 o )] * 100%, 1 being the length of the strand of hair (15 cm), 1 0 the length of the lock of hair immediately after drying and 1 x the length of the lock of hair after 48 h of storage in a drying cabinet at constant conditions (30 ° C, 40% relative humidity). The curls treated with the shampoo according to the invention had a curl retention value of 94.7%, while curls treated with a similar shampoo to which the polymer P1 had not been added had only a curl retention value of 87 , 1% showed.
2.8. Haarshampoo No. 3 2.8. Hair shampoo No. 3
Komponenten Gew.-% Components weight%
Texapon(R) K14 S spez. 15,0 Sulfobernsteinsäurehalbester auf Basis eines C12-14- Alkylpolyglykol(3 EO)ethers, Dinatriumsalz (40 % 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%
Aktivsubstanz in Wasser), CTFA-Bezeichnung: Disodium Active substance in water), CTFA name: Disodium
laurethsulfosuccinate 12,0 ethoxilierte (9 E0) Palmkernölfettsäure 1,0laureth sulfosuccinate 12.0 ethoxylated (9 E0) palm kernel oil fatty acid 1.0
Alkylglucosid APG-600 4,0Alkyl glucoside APG-600 4.0
Dehyton(R) CB5 9,7Dehyton (R) CB 5 9.7
Polymerisat P1 (20 % Aktivsubstanz in Wasser) 5,0Polymer P1 (20% active substance in water) 5.0
Wasser ad 100 Water ad 100
4 Wäßrige Lösung von RO(Z)x mit Z=Glucose, x=1,4 und R= 4 Aqueous solution of RO (Z) x with Z = glucose, x = 1.4 and R =
n-Alkyl(C12-14), (50 % Aktivsubstanz) (HORIZON) n-alkyl (C 12-14 ), (50% active substance) (HORIZON)
5 Wäßrige Lösung eines Fettamin-Derivates mit Betainstruktur, CTFA-Bezeichnung: Coco-Betaine (ca. 31 % Aktivsubstanz, ca. 6 , 5 % NaCl ) (HENKEL) 5 Aqueous solution of a fatty amine derivative with betaine structure, CTFA name: Coco-Betaine (approx. 31% active substance, approx. 6.5% NaCl) (HENKEL)
Das Shampoo ist klar und farblos. Bei Behandlung der Haare mit diesem Shampoo erhielten diese eine ausgezeichnete Avivage. The shampoo is clear and colorless. When the hair was treated with this shampoo, it received an excellent finish.
2.9. Haarshampoo No.4 2.9. Hair shampoo No.4
Komponenten Gew.-% Components weight%
Sulfobernsteinsäurehalbester auf Basis eines C12-14-Alkylpolyglykol(3 EO)ethers, Dinatriumsalz (40 % Sulfosuccinic acid semiesters based on a C 12-14 alkyl polyglycol (3 EO) ether, disodium salt (40%
Aktivsubstanz in Wasser), CTFA-Bezeichnung: Disodium Active substance in water), CTFA name: Disodium
laurethsulfosuccinate 12,0 ethoxilierte (9 E0) Palmkernölfettsäure 1,0laureth sulfosuccinate 12.0 ethoxylated (9 E0) palm kernel oil fatty acid 1.0
Dehyton(R) CB 10,0Dehyton (R) CB 10.0
Eucarol(R) TA6 20,0Eucarol (R) TA 6 20.0
Polymerisat P1 (20 % Aktivsubstanz in Wasser) 1,2Polymer P1 (20% active substance in water) 1.2
Wasser ad 100 Water ad 100
6 Wäßrige Lösung von Natriumlaureth-7-tartrat, 25 6 Aqueous solution of sodium laureth-7-tartrate, 25
Aktivsubstanz (ROL)  Active substance (ROL)
Dieses klare Shampoo zeichnete sich bei guter Reinigungsleistung insbesonders durch einen ausgezeichneten Konditionierungseffekt aus. This clear shampoo was particularly characterized by an excellent conditioning effect with good cleaning performance.
2.10. Haarshampoo No.5 2.10. Hair shampoo No.5
Komponenten Gew.-% Components weight%
Sulfobernsteinsäurehalbester auf Basis eines C12-14-Alkylpolyglykol(3 EO)ethers, Dinatriumsalz (40 % Sulfosuccinic acid semiesters based on a C 12-14 alkyl polyglycol (3 EO) ether, disodium salt (40%
Aktivsubstanz in Wasser), CTFA-Bezeichnung: Disodium Active substance in water), CTFA name: Disodium
laurethsulfosuccinate 15,0 Dehyton(R) CB 12,0laureth sulfosuccinate 15.0 Dehyton (R) CB 12.0
Alkylglucosid APG-600 4,0Alkyl glucoside APG-600 4.0
Polymerisat P1 (20 % Aktivsubstanz in Wasser) 1 ,2 Wasser ad 100 Polymer P1 (20% active substance in water) 1, 2 water ad 100
Dieses klare Shampoo verlieh den shampoonierten Haaren eine sehr gute Naßkämmbarkeit. This clear shampoo gave the shampooed hair very good wet combability.

Claims

Patentansprüche Claims
1. Wäßrige, zwitterionische Polymerisate enthaltende Zubereitungen zur Haarbehandlung, dadurch gekennzeichnet, daß sich die zwitterionischen Polymerisate im wesentlichen zusammensetzen aus 1. Aqueous preparations containing zwitterionic polymers for hair treatment, characterized in that the zwitterionic polymers consist essentially of one another
A) Monomeren mit quartären Ammoniumgruppen der allgemeinen Formel (I), A) monomers with quaternary ammonium groups of the general formula (I),
R1-CH=CR2-CO-Z-(CnH2n)-N(+)R3R4R5 A(-) (I) in der R1 und R2 unabhängig voneinander stehen für Wasserstoff oder eine Methylgruppe und R3, R4 und R5 unabhängig voneinander für Alkylgruppen mit 1 bis 4 Kohlenstoff-Atomen, Z eine NH-Gruppe oder ein R 1 -CH = CR 2 -CO-Z- (C n H 2 n) -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 having 1 to 4 carbon atoms, Z an NH group or a
Sauerstoffatom, n eine ganze Zahl von 2 bis 5 und A(-) das Anion einer organischen oder anorganischen Säure ist und Oxygen atom, n is an integer from 2 to 5 and A (-) is the anion of an organic or inorganic acid and
B) monomeren Carbonsäuren der allgemeinen Formel (II), B) monomeric carboxylic acids of the general formula (II),
R6-CH=CR7-COOH (II) in denen R6 und R7 unabhängig voneinander Wasserstoff oder Methylgruppen sind R 6 -CH = CR 7 -COOH (II) in which R 6 and R 7 are independently hydrogen or methyl groups
2. Zubereitungen nach Anspruch 1, dadurch gekennzeichnet, daß die zwitterionischen Polymerisate aus Monomeren des Typs (A) und Monomeren des Typs (B) in einem Molverhältnis von 60:40 bis 95:5, insbesondere von 75:25 bis 95:5, bestehen. 2. Preparations according to claim 1, characterized in that the zwitterionic polymers from monomers of type (A) and Monomers of type (B) in a molar ratio of 60:40 to 95: 5, in particular from 75:25 to 95: 5, exist.
3. Zubereitungen nach einem der Ansprüche 1 oder 2, dadurch gekennzeichnet, daß bei den Monomeren des Typs (A) R3, R4 und R3 Methylgruppen sind, Z eine NH-Gruppe und A(-) ein Halogenid-, Methoxysulfat- oder Ethoxysulfat-Ion ist. 3. Preparations according to one of claims 1 or 2, characterized in that in the monomers of type (A) R 3 , R 4 and R 3 are methyl groups, Z is an NH group and A (-) is a halide, methoxysulfate. or ethoxysulfate ion.
4. Zubereitungen nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß das Monomere des Typs (A) Acrylamidopropyltrimethyl-ammoniumchlorid ist. 4. Preparations according to one of claims 1 to 3, characterized in that the monomer of type (A) is acrylamidopropyltrimethylammonium chloride.
5. Zubereitungen nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß das Monomere des Typs (B) Acrylsäure ist. 5. Preparations according to one of claims 1 to 4, characterized in that the monomer of type (B) is acrylic acid.
6. Zubereitungen nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß sie die zwitterionischen Polymerisate in Mengen von 0,1 bis 10 Gew.-%, insbesondere von 1 bis 5 Gew.-%, bezogen auf die gesamte Zubereitung, enthalten. 6. Preparations according to one of claims 1 to 5, characterized in that they contain the zwitterionic polymers in amounts of 0.1 to 10 wt .-%, in particular from 1 to 5 wt .-%, based on the entire preparation.
7. Zubereitungen nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, daß sie mindestens eine oberflächenaktive Verbindung, ausgewählt aus der Gruppe der anionischen, zwitterionischen, amphoteren und nichtionischen Tenside, enthalten. 7. Preparations according to one of claims 1 to 6, characterized in that they contain at least one surface-active compound selected from the group of anionic, zwitterionic, amphoteric and nonionic surfactants.
8. Zubereitungen nach Anspruch 7, dadurch gekennzeichnet, daß sie die oberflächenaktiven Verbindungen in Mengen von 0,1 bis 40 Gew.-%, bezogen auf die gesamte Zubereitung, enthalten. 8. Preparations according to claim 7, characterized in that they contain the surface-active compounds in amounts of 0.1 to 40 wt .-%, based on the entire preparation.
9. Zubereitungen nach einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, daß sie einen pH-Wert von 4 bis 10, insbesondere von 5 bis 9, aufweisen. 9. Preparations according to one of claims 1 to 8, characterized in that they have a pH of 4 to 10, in particular 5 to 9.
10. Zubereitungen nach einem der Ansprüche 1 bis 9, dadurch gekennzeichnet, daß sie als Haarshampoo oder Haarspülung formuliert sind. 10. Preparations according to one of claims 1 to 9, characterized in that they are formulated as a hair shampoo or hair conditioner.
11. Verwendung von Zubereitungen nach einem der Ansprüche 1 bis 10 zur Haarbehandlung. 11. Use of preparations according to one of claims 1 to 10 for hair treatment.
PCT/EP1990/001444 1989-09-08 1990-08-30 Hair care preparations WO1991003229A1 (en)

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DE19893929973 DE3929973A1 (en) 1989-09-08 1989-09-08 HAIR CARE

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US6555101B1 (en) * 1992-09-29 2003-04-29 Henkel Kommanditgesellschaft Auf Aktien Hair aftertreatment preparations
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CA2066226A1 (en) 1991-03-09
EP0490982A1 (en) 1992-06-24

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