DE3929973A1 - HAIR CARE - Google Patents
HAIR CAREInfo
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- DE3929973A1 DE3929973A1 DE19893929973 DE3929973A DE3929973A1 DE 3929973 A1 DE3929973 A1 DE 3929973A1 DE 19893929973 DE19893929973 DE 19893929973 DE 3929973 A DE3929973 A DE 3929973A DE 3929973 A1 DE3929973 A1 DE 3929973A1
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- hair
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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
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- 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
Abstract
Description
Die Erfindung betrifft Zubereitungen zur Haarbehandlung, die zwitterionische Polymerisate enthalten.The invention relates to preparations for hair treatment, the 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 after washing, dyeing or perming unsatisfactory wet and dry combability, and curling retention the dry hair is inadequate. To this To remedy maladministration, either the hair treatment must added appropriate components or the hair afterwards a separate treatment with these substances, which then usually be formulated in the form of a rinse subjected become.
Als solche haareigenschaftsverbessernde Wirkstoffe werden häufig polymere Verbindungen eingesetzt.As such hair property-improving agents are becoming common used polymeric compounds.
Kationische Polymere, wie beispielsweise die aus den amerikanischen Patenten US 38 16 616 und US 34 72 840 bekannten Cellulosederivate, können zwar die Naßkämmbarkeit deutlich verbessern, erzielen aber nur unbefriedigende haarfestigende und frisurstabilisierende Wirkungen.Cationic polymers, such as those from the American Patents US 38 16 616 and US 34 72 840 known cellulose derivatives, Although they can significantly improve wet combability, but only achieve unsatisfactory hair-firming and hairstabilizing 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 Haarfestigungsmitteln. Auch aus DE-OS 28 17 369 war die Verwendung von Copolymerisaten aus Dimethylaminoethylmethacrylat, Acrylsäure und Methylmethacrylat in Haarfestigungsmitteln und Shampoos bekannt.Also known is the use of zwitterionic polymers, the anionic groups, mostly carboxyl groups, and quaternary ones Containing ammonium groups in the molecule, in hair treatment agents. For example, DE-OS 21 50 557 describes the use of Polymers of zwitterionic monomers in hair fixatives. Also from DE-OS 28 17 369 was the use of copolymers from dimethylaminoethyl methacrylate, acrylic acid and methyl methacrylate known in hair fixatives and shampoos.
Diese für Haarbehandlungs- und Haarfestlegemittel 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 ungesättigen 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 known for hair treatment and hair fixative show zwitterionic polymers, especially in formulations with anionic surfactants, the disadvantage that the hair-rendering and hair fixative properties over extended storage periods gradually lost. It was therefore in DE-OS 37 08 451 proposed zwitterionic polymers consisting of 30-70% Monomers with quaternary ammonium groups, 10-30% monomeric olefinic unsaturated carboxylic acids, 10-30% monomeric olefinic 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-revitalizing and hairstabilizing 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 Polymerisation, die bei vergleichbaren Eigenschaften weniger komplex aufgebaut, das heißt aus einer geringeren Anzahl an unterschiedlichen Monomeren herstellbar sind.Thus, although suitable polymers are available to the to achieve desired effects on the hair, but these are out composed of at least 3 or 4 monomers. It therefore exists There is still a need for polymerization, with comparable properties less complex, that is, a smaller one Number of different monomers can be produced.
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 of monomers with quaternary ammonium groups and monomeric carboxylic acids wet combability improving, have hair-revitalizing and hairstabilizing properties, the previously only in polymers with a larger number different monomers were known. Furthermore, it is with these polymers possible, based on hair treatment agent formulate anionic and / or amphoteric surfactants derived from theirs Effect on the wet combability of hair in their performance level correspond to the known good cationic rinses.
Gegenstand der Erfindung sind somit wäßrige, zwitterionische Polymerisate enthaltende Zubereitungen zur Haarbehandlung, dadurch gekennzeichnet, daß sich die zwitterionischen Polymerisate im wesentlichen zusammensetzen ausThe invention thus relates to aqueous, zwitterionic Polymers containing preparations for hair treatment, characterized characterized in that the zwitterionic polymers substantially composite out
- A) Monomeren mit quartären Ammoniumgruppen der allgemeinen Formel (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 undA) Monomers having quaternary ammonium groups of the general formula (I) R 1 -CH = CR 2 -CO-Z- (C n H 2n ) -N (+) R 3 R⁴R⁵ A (-) (I) in which R¹ and R² independently of one another represent Hydrogen or a methyl group and R³, R⁴ and R⁵ independently represent alkyl groups having 1 to 4 carbon atoms, Z is an NH group or an oxygen atom, n is 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) R⁶-CH=CR⁷-COOH (II)in denen R⁶ und R⁷ unabhängig voneinander Wasserstoff oder Methylgruppen sind.B) monomeric carboxylic acids of the general formula (II) R⁶-CH = CR⁷-COOH (II) in which R⁶ and R⁷ are independently hydrogen or Are methyl groups.
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.Suitable starting monomers are, for. Dimethylaminoethylacrylamide, Dimethylaminoethylmethacrylamide, dimethylaminopropylacrylamide, Dimethylaminopropylmethacrylamide and diethylaminoethylacrylamide, when Z is an NH group or dimethylaminoethyl acrylate, Dimethylaminoethyl methacrylate and diethylaminoethyl acrylate when Z is an oxygen atom.
Die Herstellung der genannten Monomeren erfolgt nach bekannten Verfahren, wie sie z. B. in US-PS 38 78 247, DE-PS 28 19 735, DE-PS 28 36 520, DE-PS 34 02 599 oder CH-PS 4 64 891 beschrieben sind.The preparation of the monomers mentioned is carried out according to known Procedures, such as. In US-PS 38 78 247, DE-PS 28 19 735, DE-PS 28 36 520, DE-PS 34 02 599 or CH-PS 4 64 891 described are.
Die eine tertiäre Aminogruppe enthaltenden Monomeren werden dann in bekannter Weise quaterniert, wobei als Alkylierungsreagenzien Methylchlorid, Dimethylsulfat oder Diethylsulfat besonders geeignet sind. Die Quaternierungsreaktion kann in wäßriger Lösung oder im Lösungsmittel erfolgen. Geeignete Verfahren sind z. B. in DE-OS 33 30 326, DE-OS 25 37 378 oder DE-OS 32 44 274 beschrieben.The tertiary amino group-containing monomers are then quaternized in a known manner, being used as Alkylierungsreagenzien Methyl chloride, dimethyl sulfate or diethyl sulfate particularly suitable are. The quaternization reaction can be carried out in aqueous solution or in the solvent. Suitable methods are for. In DE-OS 33 30 326, DE-OS 25 37 378 or DE-OS 32 44 274 described.
Vorteilhafterweise werden solche Monomeren 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.Advantageously, such monomers of the formula (I) are used, represent the derivatives of acrylamide or methacrylamide. Preference is furthermore given to those monomers which, as counterions, are halide, Methoxysulfat- or ethoxysulfate ions contain. Likewise preferred are those monomers of the formula (I) in which R³, R⁴ and R⁵ are methyl groups.
Das Acrylamidopropyl-trimethylammoniumchlorid ist ein ganz besonders bevorzugtes Monomer der Formel (I).The acrylamidopropyltrimethylammonium chloride is a very special one preferred monomer of the 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.Suitable monomeric carboxylic acids of the formula (II) are acrylic acid, Methacrylic acid, crotonic acid and 2-methyl crotonic acid. Prefers are acrylic or methacrylic acid, especially acrylic acid 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 of the invention are made Monomers of the formulas (I) and (II) according to known polymerization manufactured. The polymerization can either carried out in aqueous or aqueous-alcoholic solution. As alcohols are alcohols having 1 to 4 carbon atoms, preferably Isopropanol, used simultaneously as a polymerization regulator serve. The monomer solution can also be other components than Regulators are added, for. For example, formic acid or mercaptans, such as Thioethanol and thioglycolic acid. The initiation of the polymerization takes place with the help of radical-forming substances. For this may be redox systems and / or thermally decomposing radical formers the type of azo compounds, such as. Azoisobutyronitrile, Azo-bis (cyanopentanoic acid) or azo-bis (amidinopropane) dihydrochloride be used. As redox systems are z. 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. The polymerization can be isothermal or under adiabatic conditions be carried out, depending on the concentration ratios by the released heat of polymerization the temperature range for the course of the reaction between 20 and 200 ° C, and the reaction optionally under the must be carried out adjusting overpressure. preferably, the reaction temperature is between 20 and 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 pH during the copolymerization can be in a wide range vary. Advantageously, at low pH values polymerized; however, pH values above the Neutral point. After the polymerization is washed with an aqueous Base, e.g. As sodium hydroxide, potassium hydroxide or ammonia, to a pH Value between 5 and 10, preferably 6 to 8, set. details Information on the polymerization process can be taken from the examples become.
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.As particularly effective, such polymers have been found in which the monomers of the formula (I) with respect to the monomers of Formula (II) in excess. It is therefore according to the invention preferred to use those polymers which consist of monomers of Formula (I) and the monomers of the formula (II) in a molar ratio from 60:40 to 95: 5, especially 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 in the inventive Preparations preferably in amounts of 0.1 to 10 Wt .-%, based on the total preparation. The wet combability improving Effect of the polymers is already at low concentrations very large; the hair-vivifying and Hair-setting effects, in contrast, in most cases observed only at concentrations above about 1 wt .-%. It is therefore particularly preferred, the polymers in amounts of about 1 to 5 wt .-% use.
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 nichtionische Tenside bevorzugt. The zwitterionic polymers of the invention are preferred in aqueous preparations containing surfactants Used connections. As surface-active compounds while anionic, zwitterionic, amphoteric and / or nonionic Surfactants are preferred.
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 Phosphat- Gruppe 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, vonAs anionic surfactants are suitable in hair treatment compositions according to the invention all for use on the human body suitable anionic surfactants. These are marked by a water-solubilizing, anionic group such as As a carboxylate, sulfate, sulfonate or phosphate Group and a lipophilic alkyl group having about 10 to 22 carbon atoms. In addition, glycol or polyglycol ether groups, Ester, ether and amide groups and hydroxyl groups his. Examples of suitable anionic surfactants are the sodium, Potassium and ammonium as well as the mono-, di- and trialkanolammonium salts with 2 or 3 C atoms in the alkanol group, of
- - 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,- Ethercarbonsäuren the formula RO- (CH₂-CH₂O) x -CH₂-COOH, in which R is a linear alkyl group having 10 to 22 carbon atoms and x = 0 or 1 to 10,
- - Acylsarcosiden mit 10 bis 18 C-Atomen in der Acylgruppe,Acylsarcosides having 10 to 18 C atoms in the acyl group,
- - Acyltauriden mit 10 bis 18 C-Atomen in der Acylgruppe,Acyltaurides having 10 to 18 C atoms in the acyl group,
- - Acylisethionaten mit 10 bis 18 C-Atomen in der Acylgruppe,Acyl isethionates having 10 to 18 C 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 having 8 to 18 C Atoms in the alkyl group and sulfosuccinic acid mono-alkylpolyoxyethyl esters with 8 to 18 C atoms in the alkyl group and 1 to 6 oxyethyl groups,
- - linearen Alkansulfonaten mit 12 bis 18 C-Atomen,- linear alkanesulfonates having 12 to 18 C atoms,
- - linearen Alpha-Olefinsulfonaten mit 12 bis 18 C-Atomen,Linear alpha-olefin sulfonates having 12 to 18 C atoms,
- - Alpha-Sulfofettsäuremethylestern von Fettsäuren mit 12 bis 18 C-Atomen,Alpha-sulfofatty acid methyl esters of fatty acids with 12 to 18 C-atoms,
- - Alkylsulfaten und Alkylpolyglykolethersulfaten der Formel 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,- Alkylsulfaten and Alkylpolyglykolethersulfaten the formula RO (CH₂-CH₂O) x -OSO₃H, in which R is a preferably linear alkyl group having 10 to 18 carbon atoms and x = 0 or 1 to 12,
- - Gemische oberflächenaktiver Hydroxysulfonate gemäß DE-OS 37 25 030, - Mixtures of surface-active hydroxysulfonates according to DE-OS 37 25 030,
- - sulfatierte Hydroxyalkylpolyethylen- und/oder Hydroxyalkylenpropylenglykolether gemäß DE-OS 37 23 254,- Sulfated Hydroxyalkylpolyethylen- and / or Hydroxyalkylenpropylenglykolether according to DE-OS 37 23 254,
- - Ester der Weinsäure und Zitronensäure mit Alkoholen, die Anlagerungsprodukte von etwa 2-15 Molekülen Ethylenoxid und/oder Propylenoxid an Fettalkohole mit 8 bis 22 C-Atomen darstellen.- esters of tartaric acid and citric acid with alcohols, the Addition products of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols having 8 to 22 carbon atoms represent.
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 sulfates and alkyl polyglycol ether sulfates with 10 to 18 C atoms in the alkyl group and up to 12 glycol ether groups in the molecule.
Als zwitterionische Tenside werden solche oberflächenaktive 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-glycine, beispielsweise das Kokosalkyl-N,N-dimethylammonium-glycinat, N- Acyl-aminopropyl-N,N-dimethylammoniumglycinate, beispielsweise das Kokosacylaminopropyl-N,N-dimethylammoniumglycinat, und 2-Alkyl- 3-carboxylmethyl-3-hydroxyethyl-imidazoline mit jeweils 8 bis 18 C-Atomen in der Alkyl- oder Acylgruppe sowie das Kokosacylaminoethylhydroxyethylcarboxymethylglycinat.Zwitterionic surfactants are those surface-active compounds which carry in the molecule at least one quaternary ammonium group and at least one -COO (-) or -SO₃ (-) group. Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium-glycines, for example the cocoalkyl-N, N-dimethylammonium-glycinate, N-acyl-aminopropyl-N, N-dimethylammoniumglycinate, for example the Kokosacylaminopropyl- N, N-dimethylammonium glycinate, and 2-alkyl-3-carboxylmethyl-3-hydroxyethyl-imidazolines having in each case 8 to 18 C atoms in the alkyl or acyl group, and 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-Alkylaminopropionsäuren und Alkylaminoessigsäuren mit jeweils etwa 8 bis 18 C-Atomen in der Alkylgruppe.Among amphoteric surfactants are such surface-active compounds understood that except a C₈-C₁₈ alkyl or acyl group in the molecule at least one free amino group and at least one -COOH or -SO₃H group and to form internal Salts are capable. Examples of suitable amphoteric surfactants are N-alkylglycines, N-alkylaminopropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyl taurines, N-alkyl sarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each having about 8 to 18 C 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, Alkylaminoxid- Tenside und Fettsäurealkanolamide.Nonionic surfactants are mainly the addition products of 2 to 20 moles of ethylene oxide with preferably linear alcohols having 12 to 18 C atoms, to alkylphenols having 8 to 15 C atoms in the alkyl group, fatty acids with 12 to 18 carbon atoms, fatty acid partial glycerides, on fatty acid sorbitan partial esters, on fatty acid alkanolamides and methylglucoside 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 34 42 175 bekannt.Cationic surfactants can also be used in the preparations according to the invention contained when mixed with the other components, e.g. B. anionic surfactants. Such cationic surfactants are z. B. from DE-OS 34 42 175 known.
Vorzugsweise enthalten die erfindungsgemäßen Zubereitungen oberflächenaktive Verbindungen in Mengen von 0,1 bis 40 Gew.-%, bezogen auf die gesamte Zubereitung.Preferably, the preparations of the invention contain surface-active Compounds in amounts of 0.1 to 40 wt .-%, based on the whole 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, Haar- Fönwellmittel sowie wäßrige Färbemittel, Dauerwellmittel oder Dauerwell-Fixiermittel sein. Because of their good hair-soothing and hair-firming properties and their compatibility with the usual, in hair treatment products used substances are the inventive zwitterionic polymers as strengthening and hair-preserving component in all common aqueous preparations for cleaning and care of the hair. Such preparations can z. Hair shampoos, hair conditioners, hair fixatives, hair Fönwellmittel and aqueous colorants, permanent wave or Perming permanent fixer.
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.The aqueous preparations according to the invention for the purification and Hair care can therefore be in addition to the obligatory zwitterionic Polymers all customary for the particular application Auxiliaries and additives included.
Für Haarnachspülmittel sind dies z. B. kationische Tenside, insbesondere oberflächenaktive quartäre Ammoniumsalze, Fettalkohole mit 12 bis 22 C-Atomen, Fettsäurepartialglyceride, kosmetische Öl- und 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 conditioner this z. As cationic surfactants, in particular surface-active quaternary ammonium salts, fatty alcohols with 12 to 22 carbon atoms, fatty acid partial glycerides, cosmetic oil and fat component and water-soluble polymers with thickening Effect. For hair fixatives and Fönwellmittel these are z. B. also cationic surfactants, cationic, nonionic or anionic Polymers and lower alcohols. Hair dyes contain direct dyes or oxidation dye precursors, anionic or nonionic surfactants, ammonia or alkanolamines and possibly antioxidants. Permanent wave fixatives include Oxidizing agent, e.g. B. H₂O₂, H₂O₂ 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 from 4 to 10, especially from 5 to 9, on.
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 limiting it to it.
In einem Reaktor mit Impellerrührer, Heizung, Kühlung, Rückflußkühlung sowie einer Temperaturmeßvorrichtung wurdenIn a reactor with impeller stirrer, heating, cooling, reflux cooling and a temperature measuring device
201,17 kg Wasser,
89,59 kg einer 60gew.-%igen wäßrigen Lösung von Acrylamidpropyltrimethylammoniumchlorid und
6,25 kg Acrylsäure201.17 kg of water,
89.59 kg of a 60 wt .-% aqueous solution of acrylamidepropyltrimethylammonium chloride and
6.25 kg of acrylic acid
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 aussubmitted. It turned a pH of 3.4. The solution was purged with nitrogen and then heated to 60 ° C. Then, successively, the solutions were made
0,06 kg Azo-bis-(amidinopropan)dihydrochlorid in 1,00 kg Wasser,
0,024 kg Kaliumperoxodisulfat in 1,000 kg Wasser und
0,012 kg Natriumsulfit in 1,000 kg Wasser0.06 kg of azo-bis- (amidinopropane) dihydrochloride in 1.00 kg of water,
0.024 kg of potassium peroxodisulfate in 1,000 kg of water and
0.012 kg of sodium sulphite in 1.000 kg of water
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. added to the mixture while stirring. Here was only a slight Warming instead. The reaction mixture was heated to 80-85 ° C and held at this temperature for 4 hours. To At this time, the polymerization was completed. The viscous solution was cooled to 30-40 ° C and with 5,000 kg of 45% aqueous Sodium hydroxide solution neutralized.
Die klare, farblose Polymerlösung zeigte folgende Kenndaten:The clear, colorless polymer solution showed the following characteristics:
pH-Wert: 6,9
Trockensubstanz: 20%
Produktviskosität: 13 800 mPa · s
Grenzviskosität: 220 ml/g
(in 10% NaCl-Lösung)pH value: 6.9
Dry substance: 20%
Product viscosity: 13,800 mPa · s
Intrinsic viscosity: 220 ml / g
(in 10% NaCl solution)
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. The rinse is in the form of a cloudy solution. The wet combability hair treated with this conditioner was very good; a hair load or static charge of the hair was not observed.
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 hair treated with this conditioner was very good.
Die Naßkämmbarkeit von mit dieser Spülung behandelten Haaren war gut bis sehr gut.The wet combability of hair treated with this conditioner was good to very good.
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 hair treated with this conditioner was very Well.
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.To prepare this hair conditioner was the mixture of surfactants and polymerizate are added to the molten fat phase and emulsified. The wet combability of treated with this conditioner Hair was excellent.
Die Naßkämmbarkeit der mit dieser Zubereitung shampoonierten Haare war hervorragend.The wet combability of the hair shampooed with this preparation was excellent.
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. When treating the hair with this shampoo, these were not just freed from dirt and grease, but rather received the moist Hair has a pronounced softening and dry hair fullness and Volume.
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 als [(l-lx)/(l-l₀)] * 100%, wobei l die Länge der Haarsträhne (15 cm), l₀ die Länge der Haarlocke unmittelbar nach dem Trocknen und lx 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 behandelten 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.To quantify the effect achieved by the polymer, a 15 cm long strand of hair (2 g) was wound on a glass tube having an outer diameter of 1.7 cm, fixed and treated with 0.2 g of the shampoo. The hair strand was then rinsed with water and dried. A measure of the stability of the curl obtained after pulling out the glass rod is the curl retention value. The curl retention value is defined as [(ll x ) / (l-l₀)] * 100%, where l is the length of the hair strand (15 cm), l₀ the length of the hair curl immediately after drying and l x the length the lock of hair after 48 hours of storage in a drying oven at constant conditions (30 ° C, 40% relative humidity) is. 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 only had a curl retention value of 87 , 1% showed.
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 treating the hair with This shampoo received an excellent finish.
Dieses klare Shampoo zeichnete sich bei guter Reinigungsleistung insbesondere durch einen ausgezeichneten Konditionierungseffekt aus.This clear shampoo stood out with good cleaning performance in particular by an excellent conditioning effect out.
Dieses klare Shampoo verlieh den shampoonierten Haaren eine sehr gute Naßkämmbarkeit.This clear shampoo gave the shampooed hair a great deal good wet combability.
Claims (11)
- A) Monomeren mit quartären Ammoniumgruppen der allgemeinen Formel (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
- B) monomeren Carbonsäuren der allgemeinen Formel (II) R⁶-CH=CR⁷-COOH (II)in denen R⁶ und R⁷ unabhängig voneinander Wasserstoff oder Methylgruppe sind.
- A) Monomers having quaternary ammonium groups of the general formula (I) R 1 -CH = CR 2 -CO-Z- (C n H 2n ) -N (+) R 3 R⁴R⁵ A (-) (I) in which R¹ and R² independently of one another represent Hydrogen or a methyl group and R³, R⁴ and R⁵ independently represent alkyl groups having 1 to 4 carbon atoms, Z is an NH group or an oxygen atom, n is an integer from 2 to 5 and A (-) the anion of an organic or inorganic Acid is and
- B) monomeric carboxylic acids of the general formula (II) R⁶-CH = CR⁷-COOH (II) in which R⁶ and R⁷ are independently hydrogen or methyl group.
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19893929973 DE3929973A1 (en) | 1989-09-08 | 1989-09-08 | HAIR CARE |
JP51324290A JPH05500220A (en) | 1989-09-08 | 1990-08-30 | hair care preparations |
CA 2066226 CA2066226A1 (en) | 1989-09-08 | 1990-08-30 | Hair care preparations |
EP19900914143 EP0490982A1 (en) | 1989-09-08 | 1990-08-30 | Hair care preparations |
PCT/EP1990/001444 WO1991003229A1 (en) | 1989-09-08 | 1990-08-30 | Hair care preparations |
DD34392990A DD297554A5 (en) | 1989-09-08 | 1990-09-07 | HAIR CARE PRODUCTS |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19893929973 DE3929973A1 (en) | 1989-09-08 | 1989-09-08 | HAIR CARE |
Publications (1)
Publication Number | Publication Date |
---|---|
DE3929973A1 true DE3929973A1 (en) | 1991-03-14 |
Family
ID=6388972
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19893929973 Withdrawn DE3929973A1 (en) | 1989-09-08 | 1989-09-08 | HAIR CARE |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0490982A1 (en) |
JP (1) | JPH05500220A (en) |
CA (1) | CA2066226A1 (en) |
DD (1) | DD297554A5 (en) |
DE (1) | DE3929973A1 (en) |
WO (1) | WO1991003229A1 (en) |
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Also Published As
Publication number | Publication date |
---|---|
JPH05500220A (en) | 1993-01-21 |
DD297554A5 (en) | 1992-01-16 |
EP0490982A1 (en) | 1992-06-24 |
WO1991003229A1 (en) | 1991-03-21 |
CA2066226A1 (en) | 1991-03-09 |
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