CA1066449A - Hair treatment and conditioning compositions - Google Patents
Hair treatment and conditioning compositionsInfo
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- CA1066449A CA1066449A CA232,769A CA232769A CA1066449A CA 1066449 A CA1066449 A CA 1066449A CA 232769 A CA232769 A CA 232769A CA 1066449 A CA1066449 A CA 1066449A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- 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
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
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- Animal Behavior & Ethology (AREA)
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- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Composition cosmétique pour cheveux renfermant: (1) polymère cationique filmogène de bas poids moléculaire de formule- A - Z - (I bis) où A désigne le symbole B1 ou B'1 et il signifie au moins une fois le symbole B'1; B1 désigne un radical bivalent qui est un radical alkylène à chaîne droite ou ramifiée ayant jusqu'à 7 atomes de carbone dans la chaîne principale substitué par un groupement hydroxyle; B'1 est un radical bivalent qui est un radical alkylène à chaîne droite ou ramifiée ayant jusqu'à 7 atomes de carbone dans la chaîne principale, non substitué ou substitué par un ou plusieurs radicaux hydroxyle et interrrompu par un ou plusieurs atomes d'azote, l'atome d'azote étant substitué par une chaîne alkyle ayant avantageusement de 1 à 4 et de préférence 4 atomes de carbone, interrompue éventuellement par un atome d'oxygène et comportant oblisatoirement une ou plusieurs fonctions hydroxyle et/ou carboxyle;(2) un gel d'ammonium quaternaire d'un polymère de formule (I bis)(?) un produit d'oxydation d'un polymère de formule (I bis) Les polymères mentionnés sous (1), (2) et (3).Cosmetic composition for hair containing: (1) low molecular weight cationic film-forming polymer of formula- A - Z - (I bis) where A denotes the symbol B1 or B'1 and it signifies at least once the symbol B'1; B1 denotes a bivalent radical which is a straight chain or branched alkylene radical having up to 7 carbon atoms in the main chain substituted by a hydroxyl group; B'1 is a bivalent radical which is a straight or branched chain alkylene radical having up to 7 carbon atoms in the main chain, unsubstituted or substituted by one or more hydroxyl radicals and interrupted by one or more nitrogen atoms , the nitrogen atom being substituted by an alkyl chain advantageously having from 1 to 4 and preferably 4 carbon atoms, optionally interrupted by an oxygen atom and comprising obliquely one or more hydroxyl and / or carboxyl functions; (2 ) a quaternary ammonium gel of a polymer of formula (I bis) (?) an oxidation product of a polymer of formula (I bis) The polymers mentioned under (1), (2) and (3) .
Description
~0~6449 L'invention se rapporte à un polymère cationique filmo-gène ainsi qu'à des compositions le renfermant. Dans sa demande de brevet No 157,715 déposée au Canada le 28 novembre 1972, la demanderesse a revendiqué et décrit des compositions cosmétiques de traitement et de conditionnement de la chevelure contenant des polymères cationiques filmogènes de formule générale:
-A - Z - A - z - A - z - (I) dans laquelle A désigne un radical comportant deux fonctions amine et de préférence le radical _ N ~ N -et Z désigne le symbole B ou B'; B et B', identiques ou différents,désignent un radical bivalent qui est un radical alkylène à chaîne droite ou ramifiée, comportant jusqu'à 7 atomes de carbone dans la chaine principale, non substituée ou substituée par un ou plu-sieurs groupements hydroxyle et pouvant comporter en outre des atomes d'oxygène, d'azote, de soufre, 1 à 3 cycles aromatiques et/ou hétérocycles, les atomes d'oxygène, d'azote et de soufre étant présents sous forme de groupements éther, thioéther, sulfoxy-de, sulfone, sulfonium, amine, alkyl-amine, alkénylamine, benzyl-amine, oxyde d'amine, amide,imide, alcool, ester et/ou uréthane.
Ces compositions pouvaient également contenir les sels d'ammonium quaternaires ainsi que le produit d'oxydation d'un polymère répondant à la formule ci-dessus.
L'utilisation de ces polyme~permettait de limiter i ou de corriger les inconvénients résultant de l'état général ou de traitements sensibilisants tels que décolorations, permanentes ou teintures.
La demanderesse a découvert de nouvelles compositions contenant un nouveau polymère du type - A - Z - (I bis) où A désigne - N N -et Z désignele symbole Bl ou B '1 ~ et il signifie au moins une fois le symbole B'l; Bl d~signe un radical bivalent bel qu'un radical alkylène à chaîne droite ou ramifiée ayant jusqu'à 7 ato-mes de carbone dans la chaîneprincipale, substitué par un groupe-ment hydroxyle et de préférence le radical 2-hy~roxy propane 1,3-diyle, B'l est un radical bivalent tel qu'un radical alkylène à
chaine droite ou ramifiée, ayant jusqu'à 7 atomes de carbone dans la chaine principale, non substitué ou substitué par un ou plu-sieurs radicaux hydroxyle et interrompu par un ou plusieurs atomes d'azote, l'atome d'azote étant substitué par une chaine alkyle ayant avantageusement de 1 à 4 et de préférence 4 atomes de carbone, interrompue éventuellement par un atome d'oxygène et com-portant obligatoirement une ou plusieures fonctions hydroxyle et/
ou carboxyle. Ces polymères présentent, comme ceux de la demande de brevet no 157,715, des propriétés de traitement et de condition-nement de la chevelure. En dehors des avantages des condition-neurs tels que l'amélioration du démelage des cheveux humides, de la brillance, de la douceur et de la docilité de la coiffure, les polymères suivant la présente invention ont une compatibilité
améliorée vis-à-vis des tensio-actifs habituellement utilisés dans les compositions de traitement des cheveux et en particulier vis-à-vis des tensio-actifs anioniques.
La composition cocmétique pour cheveux peut également renfermer le produit d'oxydation d'un polymère de formule I bis obtenu de préférence par l'eau oxygénée ou par un peracide ou le sel d'ammonium quaternaire d'un polymère de formule I bis.
La demanderesse a en outre découvert que les compositions cosmétiques pour cheveux contenant un polymère de formule - A - Z - A - Z - A - Z - (I) ou du type - A - Z - (I bis) peuvent être améliorées en utilisant les sels d'ammonium - quaternaires desdits polymères obtenus par quaternisation des :
10~6449 groupements basiques avec l'aclde chloracétique ou un chloracétate~
par exemple le chloracétate de soude.
Elle a constaté en ef~et, que la compatibilité des poly-mères ainsi quaternisés était améliorée vis-à-vis des tensio-actifs anioniques habituellement utilisés dans lesdites compositions.
L'objet de la présente invention est donc des composi-tions cosmétiques de traitement et de conditionnement de la che-velure, contenant un polymère cationique de bas poids moléculaire de formule - A - Z - (I bis) dans laquelle A et Z ont la signification indiquée ci-dessus, ledit polymère cationique étant essentiellement caractérisé par le fait que Z signifie au moins une fois B'l, B'l représente un radical bivalent qui est un radical alkylène à chaine droite ou ramifiée ayant ;usqu~à 7 atomes de carbone dans la cha;ne principale substitué ou non pàrun ou plusieurs radicaux hydroxyle etin~ro~u -- par un ou plusieurs atomes d'azote, l'atome d'azote étant substitué
par une chaîne alkyle ayant avantageusement de 1 à 4 et de préfé-rence 4 atomes de carbone, interrompue éventuellement par un atome d'oxygène et comportant obligatoirement une ou plusieurs fonctions hydroxyle et/ou carboxyle.
,~ La demande a également pour objet des compositions cosmétiques contenant des composés résultant des r~actions d'oxydation ou de quaternisation des polymères de formule I bis.
Un autre objet de la présente invention est un polymère cationique filmogène de bas poids moléculaire de formule - A - Z - (I bis) où A d~siyne le radical N~
et Z désigne le symbole Bl ou B'l et signifie au moins une fois Bll, Bl est un radical bivalent tel qu'un radical alkylène à
chaine droite ou ramifiée ayant jusqu'à 7 atomes de carbone 10~6449 dans la chaîne principale, substltué par un groupement hydroxyle, et de préférence un ~roupment 2-hydroxy propane 1,3-diyle, B'l signi~ie un radical bivalent tel qu'un radical à chaine droite ou ramifiée, ayant jusqu'à 7 atomes de carbone dans la chaîne principale, non substitué ou substitué par un ou plusieurs radi-caux hydroxyle et comportant un ou plusieurs atomes diazote, l'atome d'azote étant substitué par une chaine alkyle ayant - avantageusement de 1 à 4 et de préférence 4 atomes de carbone, interrompue éventuellement par un a~ome d'oxygène et comportant obligatoirement une ou plusieurs fonctions hydroxyle et/ ou carbo-xyle, ainsi que les dérivés d'oxydation et de quaternisation de ces polymères.
Les polymères préférés suivant la présente invention sont en particulier des polymères de formule - A - Z - (I bis) où A signifie le radical - ~ N - ,Z signifie Bl et/ou s' Bl signifie hydroxyalkylène tel que le groupement 2-hydroxy propane 1,3 diyle, B'l signifie un radical polyhydroxyalkylène et de préférence dihydroxyalkylene, ayant de préférence 6 atomes de carbone, interrompu par un atome d'azote substitué par un groupement choisi parmi les groupements suivants: carboxyméthyle, ~ 0 ~ 6449 The invention relates to a cationic film-forming polymer.
gene as well as compositions containing it. In his request Patent No. 157,715 filed in Canada on November 28, 1972, the Applicant has claimed and described cosmetic compositions treatment and conditioning of hair containing film-forming cationic polymers of general formula:
-A - Z - A - z - A - z - (I) in which A denotes a radical comprising two functions amine and preferably the radical _ N ~ N -and Z denotes the symbol B or B '; B and B ', identical or different, denote a bivalent radical which is a chain alkylene radical straight or branched, having up to 7 carbon atoms in the main chain, unsubstituted or substituted by one or more their hydroxyl groups and which may also contain oxygen, nitrogen, sulfur atoms, 1 to 3 aromatic rings and / or heterocycles, the oxygen, nitrogen and sulfur atoms being present in the form of ether, thioether, sulfoxy-de, sulfone, sulfonium, amine, alkylamine, alkenylamine, benzyl-amine, amine oxide, amide, imide, alcohol, ester and / or urethane.
These compositions could also contain the salts of quaternary ammonium as well as the oxidation product of a polymer corresponding to the above formula.
The use of these polyme ~ made it possible to limit i or to correct the inconveniences resulting from the general condition or sensitizing treatments such as discoloration, permanent or dyes.
The applicant has discovered new compositions containing a new polymer of the type - A - Z - (I bis) where A denotes - NN -and Z denotes the symbol Bl or B '1 ~ and it signifies at least one times the symbol B'l; Bl denotes a bivalent radical as beautiful as straight or branched chain alkylene radical having up to 7 ato-carbon mes in the main chain, substituted by a group-ment hydroxyl and preferably the radical 2-hy ~ roxy propane 1,3-diyl, B'l is a bivalent radical such as an alkylene radical with straight or branched chain, having up to 7 carbon atoms in the main chain, unsubstituted or substituted by one or more radicals hydroxyl and interrupted by one or more atoms of nitrogen, the nitrogen atom being substituted by an alkyl chain advantageously having from 1 to 4 and preferably 4 atoms of carbon, possibly interrupted by an oxygen atom and com-necessarily having one or more hydroxyl functions and /
or carboxyl. These polymers have, like those of the application No. 157,715, processing and conditioning properties hairstyle. Apart from the advantages of the conditions-such as improving the disentangling of damp hair, the shine, softness and docility of the hairstyle, the polymers according to the present invention have compatibility improved with respect to the surfactants usually used in hair treatment compositions and in particular vis-with respect to anionic surfactants.
The cosmetic composition for hair can also contain the oxidation product of a polymer of formula I bis preferably obtained by hydrogen peroxide or by a peracid or the quaternary ammonium salt of a polymer of formula I bis.
The Applicant has further discovered that the compositions hair cosmetics containing a polymer of formula - A - Z - A - Z - A - Z - (I) or of the type - A - Z - (I bis) can be improved using ammonium salts - quaternaries of said polymers obtained by quaternization of :
10 ~ 6449 basic groupings with chloracetic acid or a chloracetate ~
for example sodium chloracetate.
She noted in fact ~ and, that the compatibility of poly-mothers thus quaternized was improved vis-à-vis the tensio-anionic active agents usually used in said compositions.
The object of the present invention is therefore compounds cosmetic treatments and conditioning of the hair velvet, containing a low molecular weight cationic polymer of formula - A - Z - (I bis) in which A and Z have the meanings indicated above, said cationic polymer being essentially characterized by the fact that Z means at least once B'l, B'l represents a bivalent radical which is a straight chain alkylene radical or branched having; usqu ~ to 7 carbon atoms in the main chain substituted or unsubstituted by one or more hydroxyl radicals etin ~ ro ~ u - by one or more nitrogen atoms, the nitrogen atom being substituted by an alkyl chain advantageously having from 1 to 4 and preferably 4 carbon atoms, possibly interrupted by one atom oxygen and necessarily having one or more functions hydroxyl and / or carboxyl.
, ~ The request also relates to compositions cosmetics containing compounds resulting from reactions oxidation or quaternization of polymers of formula I bis.
Another object of the present invention is a polymer low molecular weight cationic film-forming formula - A - Z - (I bis) where A d ~ siyne the radical N ~
and Z denotes the symbol Bl or B'l and signifies at least once Bll, Bl is a bivalent radical such as an alkylene radical with straight or branched chain with up to 7 carbon atoms 10 ~ 6449 in the main chain, substituted by a hydroxyl group, and preferably a ~ roupment 2-hydroxy propane 1,3-diyl, B'l signi ~ ie a bivalent radical such as a straight chain radical or branched, having up to 7 carbon atoms in the chain main, unsubstituted or substituted by one or more radi-hydroxyl cals and containing one or more nitrogen atoms, the nitrogen atom being substituted by an alkyl chain having advantageously from 1 to 4 and preferably 4 carbon atoms, possibly interrupted by an oxygen atom and comprising one or more hydroxyl and / or carbon functions xyl, as well as the oxidation and quaternization derivatives of these polymers.
The preferred polymers according to the present invention are in particular polymers of formula - A - Z - (I bis) where A signifies the radical - ~ N -, Z signifies Bl and / or s' Bl signifies hydroxyalkylene such as the 2-hydroxy group 1,3 di propane, B'l signifies a polyhydroxyalkylene radical and preferably dihydroxyalkylene, preferably having 6 atoms of carbon, interrupted by a nitrogen atom substituted by a group chosen from the following groups: carboxymethyl,
2-~-hydroxyéthoxy éthyle, 1,3-dihydroxy 2-méthyl propyle-2, l-hydroxy 2-méthyl propyle-2.
La demande concerne, par ailleurs, les procédés de préparation desdits polymères et de leurs dérivés d'ammonium quaternaire.
Les polymères cationiques suivant la présente demande, ; peuvent être préparés par polycondensation directe ou indirecte.
La polycondensation directe consiste à faire réagir la pipérazine et une amine hydroxylée telle que la diglycolamine ou le 2-amino 2-méthyl propane-1,3-diol ou un aminoacide tel que le glycocolle avec une épihalohydrine telle que l'épichlorhydrine 10~:i64~9 ou 1'épibromhydrine, en milieu a~ueux, à additionner de la soude comme accepteur de l'hydracide libéré, puis à chauffer à tempéra-ture comprise entre 80 et 90c.
La polycondensation indirecte consiste à préparer tout d'abord, un dérivé intermédiaire X, résultant de la réaction de l'épihalohydrine avec soit la pipérazine, soit l'amine hydroxylée et/ou l'amino-acide. ce dérivé intermédiaire x est ensuite amené
à réagir avec une seconde amine. On additionne ensuite éventuel-lement de l'épihalohydrine et on ajoute une base telle que l'hydro-xyde de sodium et on chauffe à une température comprise entre 80 et 90C.
Les proportions utilisables de pipérazine, d'épihalo-hydrine et d'amine hydroxylée et/ou de l'amino-acide, sont ~onc-tion de l'alternance des motifs A, sl et s'l que l'on veut obtenir dans le polymère final.
L'épihalohydrine et le mélange pipérazine-amine hydroxy-lée et/ou aminoacide sont présents de préférence dans des proportions équimolaires. Quant au mélange pipérazine-amine hydro-xylée et/ou aminoacide, il comprend des proportions molaires comprises entre 90 et 50% pour la pipérazine et 10 à 50% pour l'amine hy~roxylée et/oul'aminoacide.
Les polymères ainsi obtenus peuvent, de fa,con connue comme indiqué dans la demande de bre~et no 157,715, être oxyd~s avec de l'eau oxygénée ou des peracides ou etre quaternisés avec des agents de quaternisation connus, tels que le bromure, le chlo-rure, iodure, sulfate, mésylate, ou tosylate d'alkyle inférieur, de préférence de méthyle ou d'éthyle, le chlorure ou bromure de benzyle.
Une quaternisation qui s'est révélée particulièrement avantageuse quant aux propriétés de compatibilité des polymères résultant avec les tensio-actifs anioniques, est la "bétainisation"
des composés de formules (I) et (I bis) consistant à quaterniser 10~6449 de O à 66% des groupements basiques quaternisables avec le chloracétate de sodium ou l'acide chloracétique. Le rendement de la réaction est généralement compris entre 60 et 100%.
Le taux de "bétainisation" peut etre défini comme le rapport entre le nombre d'équivalents d'azote quaternisés et - le nombre d'équivalents d'azote totaux quaternisables, multiplié par 100.
Le rendement de quaternisation de la réaction peut être défini par le rapport entre le nombre d'~quivalents d'azote réellement quaternisés et le nombre d'équivalents d'agent de quaternisation utilisé, multiplié par 100.
La demanderesse a constaté qu'un seul des deux atomes d'azote tertiaire du motif A était facilement quaternisable. On obtient par la bétaïnisation, des motifs répondant a la formule - A' - Z' ~ (II) dans laquelle A' est un mélange de groupements - - N N - et - N N -COO
Z' désigne Bl ou les motifs obtenus par bétaïnisation de B, B' ou B'l lorsque ceux-ci comportent un ou plusieurs atomes d'azote basique qui peuvent prendre la forme . - N
., I
- ~CH2 COO~
; La-présente demande a donc également pour objet un polymère de formule - A' - Z' - (II) où A désigne un mélange de radicaux .:
.
+~
- N N - et - N N -COO
et Z' désigne :
(1) ou bien s ou s' ou les motifs obtenus par béta-inisation de B ou s'lorsque ceux-ci comportent un ou plusieurs atomes d'azote basique, B et B', identiques ou différents, désignent un radical bivalent qui est un radical alkylène à chaine droite ou ramifiée, compor-~ ,i tant jusqu'à 7 atomes de carbone dans la chaine principale, nonsubstituée ou substituée par un ou plusieurs groupement~ hydroxy-le et pouvant comporter en outre des atomes d'oxygène, d'azote, de soufre, 1 à 3 cycles aromatiques et/ou hétérocycliques, les atomes d'oxygène, d'azote et de soufre étant présents sous forme de groupements éther, thioéther, sulfoxyde, sulfone, sulfonium, amine, alkylamine, alkénylamine, benzylamine, oxyde d'amine, amide, imide, alcool, ester et/ou uréthane;
(2) ou bien Z' signifie Bl ou B'l et les motifs obtenus - par bétainisation de Bl et il signifie au moins une fois s'l et les motifs dérivant de B'l, Bl désigne un radical bivalent qui est un radical alkylène à chaîne droite ou ramifiée ayant jùsqu'à 7 atomes de carbone dans la cha~ne prin-cipale, substitué par un groupement hydroxyle et de préférence un groupement 2-hydroxy propane 1,3-diyle, B'l est un radical bivalent qui est un radical alkylène à chaJne droite ou ramifiée ayant jusqu'à 7 atomes de carbone dans la chaîne principale, substitué par un ou plusieurs radicaux hydroxyle et interrompu par un ou plusieurs atomes d'azote, l'atome d'azote étant substitué par une chaîne alkyle ayant avantageusement de 1 à 4 et de préférence 4 atomes de carbone, interrompue éventuelle-ment par un atome d'oxygène et comportant obligatoirement une ou - 7 _ 10~6449 ` plusieurs fonctic~ns hydroxyle et/ou carboxyle.
La pr~sente demande a également pour objet une composi-tion cosmétique pour cheveux renfermant un polymère de formule - A~ _ z (II) où A' désigne un m~lange de radicaux ~
- N N - et - N N -~ CH
- COO
æ ~ désigne Bl ou B'l et/ou B ou B' et les motifs obtenus par la bétaïnisation de Bl et/ou de B et B' lorsque ceux-ci comportent ;un ou plusieurs atomes d'azote basique.
On constate que les polymères objet de la présente inyention et préparés suivant l'un quelconque des procédés cités ; ci-dessus, sont caractérisés par le fait qu'ils sont filmogènes et ont un poids moléculaire relativement bas, c'est-à-dire inférieur à 15.000.
Ils sont solubles dans-l'eau ou en milieu hydroalcooli-- que.
~` Ils sont particulièrement efficaces pour les cheveux sensibilisés après des traitements comme des décolorations, les permanentes ou les teintures, mais peuvent également être avan-tageusement utilisés pour les cheveux normaux.
'~:
Ces polymères sont introduits dans des proportions de 0,1 ~ 5% et de préférence de 0,2 ~ 3% du poid total de la compo-sition dans différentes compositions cosmétiques comme des lotions des crèmes, ou des gels coiffants en tant que constituants princi-paux ou encore dans des shampooings, compositions de mise en plis, de fixateurs de permanentes, de teintures, etc..., en tant qu'adjuvants en présence d'autres composés tels que des tensio-actifs anioniques, cationiques, non-ioniques, amphoteres ou zwitterioniques, des oxydants, des synergistes, ou stabilisateurs de mousse, des séquestrants, des surgraissants, des épaississants .~ - 8 _ des a~oucissants, des antiseptiques, des conservateurs, des colo-rants, des parfums, des germicides, ils peuvent être utilisés en mélange avec d'autres polymeres anioniques, cationiques, am-photères ou non-ioniques.
Ils peuvent se trouver dans les différentes compositions soit sous forme de sels d'acides minéraux ou organiques, soit sous forme de bases libres ou encore de quaternaires, selon le pH
d'utilisation, celui-ci étant compris entre 3 et 11.
Les compositions cosmétiques pour cheveux selon l'invention peuvent également se présenter sous forme de solutions aqueuses, hydroalcooliques, de crèmes , de pâtes, de gels ou de pou~res. Elles peuvent également renfermer un propulseur et être conditiolmées en bombe aérosol.
Les compositions de shampooings pour cheveux selon l'in-vention sont caractérisées par le fait qu'elles renferment en plus un agent de surface anionique, cationique, non-ionique, amphotère et/ou zwitterionique, un ou plusieurs composés de formule I bis et/ou II, ainsi qu'éventuellement des synergistes stabilisat~urs de mousse, des séquestrants, des surgraissants, des épaississants, une ou plusieurs résines cosmétiques, des adou-cissants, des colorants, des parfums, des bactéricides, des con-servateurs, et tout autre adjuvant habituellement utilisé dans les compositions cosmétiques.
Les polymères suivant la pr~sente demande permettent également de préparer des lotions de mise en plis, des crèmes de traitement, des conditionneurs pour cheveux, des lotions anti-pelliculaires et d'autres compositions similaires, caractérisées par le fait qu'elles renferment un ou plusieurs polymères objet de la présente demande, ayant un poids moléculaire déterminé
par abaissement de la tension de vapeur compris entre 500 et 15.000.
Les exemples suivants sont destinés à illustrer l'invention sans toutefois la limiter. Les parties seront indiquées _ 9 _ ~06644~
en poids.
ler stade - Préparation d~ derivé intermédiaire-N,N-Bis[~-hydroxy,Y-chloro-propyl~ diglycolamine de ~ormule Cl CH2 - CHOH -- CH2 --N - CH - CHOH CH Cl .. CH2 appelé ci-après intermédiaire X.
A une solution de 420 g de diglycolamine (4 moles) ~` 10 dans 2700 y d'eau, on ajoute goutte à goutte et sous agitation, 740 g (8 moles) d'épichlorhydrine en 1 heure à 10-15C.
Après 4 heures d-'agitation du mélange réactionnel à
20C, les fonctions époxydes ont pratiquement disparu.
On obtient alors une solution limpide, très légèrement teintée en vert, à 30% d'extrait sec.
2eme stade - Préparation d'un polymère du type - - A _ z _ où A désiyne - N N - Z désigne Bl ou B' Bl désigne -CH2 - CHOH - CH2 -B 1 désigne - CH2 - CHOH - CH - N - CH CHOH CH
: CH2 CH2 - O - CH2 - C~I2OH
et dans lequel les proportions des motifs A/Bl/Bl sont 4/1/3 (les proportions molaires de pipérazine/diglycolamine/épichlorhy-drine sont de 4/1/5).
A 775 g de pipérazine hexahydratée (4 moles), on ajoute en maintenant la température à 20C, 965 g(l mole) de solution :~ de dérivé intermédiaire X préparé ci-dessus. On ajoute ensuite 277g (3 moles) d'épichlorhydrine toujours à la température de 20C.
On ajoute ensuite en 1 heure, 500 g (5 moles) de solution de soude 10~6~49 à 40%. On chauffe ensuite jusql1'à 80L90C et l'on maintient -cette température pendantl heure.
Par dilution avec 1130 g d'eau, on obtient une solution à 20% de matière active.
Préparation directe d'un polymère du type - A - Z -dans lequel les motifs A et Z ont la même signification que dans l'exemple 1, mais où la répartition de la pipérazine et de la digly-colamine est statistique.
La proportion des motifs A/B'l/Bl est de 4/1/3 comme ci-dessus.
On utilise les mêmes proportions molaires relatives de pipérazine, diglycolamine et épichlorhydrine que dans l'exemple 1, c'est-à-dire 4/1/5.
A 161 g de pipérazine hexahydratée (0,83 mole) et 21 g de diglycolamine (0,2 mole), dispersés dans 140 ml dieau, on ajoute en 1 heure et à 20C, 92,5 g d'épichlorhydrine (1 mole).
Une heure après l'addition, on ajoute goutte à goutte, toujours à 20C, 100 g d'hydroxyde de sodium à 40% (1 mole).
On chauffe ensuite jusqu'à la température de 80-90C, que l'on maintient pendant 1 heure.
On dilue ensuite le milieu réactionnle avec 227 ml d'eau pour obtenir une solution à 20% de matière active.
La solution ainsi obtenue est incolore et sa viscosité
mesurée à 25C est de 0,7 poise.
Préparation d'un polymère de type - A - Z - dans lequel .' r~
A désigne - N N - et Z désigne B' `' ` 1066449 B 1 désigne - cH2 - CHOH - CH2 - N - CH - CHOH CH
CH2 - O - CH2 - cH2OH
La proportion des moti~s A/B ' 1 est de 1/1.
Les proportions molaires pipérazine/diglycolamine/
épichlorhydrine sont de 1/1/2.
A une solution de 1 mole (194 g) de pipérazine hexahydratée dans 742 g d'eau, on ajoute, goutte à goutte, en 1 ~eure, à 20C, sous agitation et sous atmosphère d'azote, 1 mole d'intermédiaire X préparé à l'exemple 1, sous la forme d'une solution 30% (970 g).
Après la fin de l'addition, la masse réactionnelle est maintenue sous agitation à 20C, pendant 1 heure.
On ajoute ensuite, à la meme température et en 1 heure, 167,5 g de soude à 48% (2 moles).
L'agitation est maintenue encore 1 heure à cette température, puis on chauffe le mélange 2 heures à 80-90C.
Par addition de 1026,5 g d'eau, on obtient une solution limpide et pratiquement incolore de polyamine à 10% de ; 20 matière active.
ler stade - Préparation d'un prépolymère P auquel on attribue principalement la formule:
~,~ ~N ~
E OEl2 ~ NH
A une solution de 776 g (4 moles) de pipérazine hexa-hydratée dans 500 g d'eau, on ajoute en procédant comme dans l'exem-ple 3, 2 moles du composé intermédiaire X de l'exemple 1, sous ; 30 forme d'une solution à 30% (1935 g).
Après la fin de l'addition, la masse réactionnelle est maintenue sous agitation à 20C, pendant 1 heure.
- - .. ` :
106644~
On ajoute ensuite à la même température et en 1 : heure, 4 mo~es d'hydroxyde de sodium sous forme d'une solution à 48% (335 g). L'agitation est maintenue encore 1 heure à cette température, puis on chauffe le mélange 3 heures à 80-90C.
On obtient ainsi une solution limpide d'un prépolymère P de formule ci-dessus.
-, 2ème stade - Préparation d'un polymère du type - A - Z -.. ~
~ dans lequel A designe - N N -`'' / , Z désigne Bl ou B'l Bl désigne - CH2 - CHOH - CH2 -1 g 2 CHOH - CH2 - 7 - CH2 - cHOH - CH
CH
~ 1 2 :, CH2 - O - CH2 - CH20H
La proportion des motifs A/B'l/Bl est de 2/1/1.
Les proportions molaires pipérazine/diglycolamine/épi-; chlorhydrine sont de 2/1/3.
A la moitié de la solution de pré-polymère P ci-dessus préparée (1835 g) (correpondant à 2 équivalents d'amines secondaires), on ajoute, goutte à goutte et sous agitation, 92,5 g d'épichlorhydrine (1 mole).
Après la fin de l'addition, la masse réactionnelle est maintenue sous agitation à 20C, pendant 1 heure.
On ajoute ensuite à la même température, et en 1 heure, 83 g (1 mole) de soude à 48%.
L'agltation est maintenue encore 1 heure à cette tempé-rature, puis on chauffe le mélange 1 heure à 80-90C.
Par addition de 2625 g d'eau, on obtient une solution limpide et pratiquement incolore de polyamine à 10,~ de matière active.
` 10~64~9 - Préparation d'un polym~re du type - A - Z -.~ ~ ,.
.; ou A signifle - N N - Z signlfle Bl ou B
/
B 1 si~nigie - CH2 - CHOH - CH2 - N - CH2 - CHOH - CH2 -~ CH2 Bl signifie - CH2 - CHOH - CH2 -La proportion des motifs A/B'l/Bl est de 4/1/3.
La proportion molaire relative de pipérazine/digly-colamine/épihalohydrine est égale à 4/1/5.
A 394,5 g de solution de pré-polymère P décrit ci-- dessus et contenant 0,43 équivalent d'amine secondaire, on ajoute sous agitation, 51 g de 1,3-bis pipérazino propane-2-ol de formule '`' ~ /--\
~- HN N-CH2 - CHOH - CH2 - N NH
` contenant 0,43 équivalent d'amine secondaire, c'est-à-dire correspondant à 0,215 mole. Le 1,3-bis pipérazino 2-propane-2-o~
peut être préparé suivant la méthode décrite dans l'exemple 15 de la demande No 157,715.
- A cette solution on ajoute en 1 heure, et à 20 C, 39,7 g (0,43 mole) d'épichlorhydrine. Le mélange est agité 1 heure à cette température. On ajoute ensuite à 20C et en 1 heure, 35,8 g (0,43 mole) de soude à 48%.
~ ~-près 1 heure d'agitation à la même température , on - chauffe la masse réactionnelle pendant 1 heure à 80-90C.
Par addition de 1099 g d'eau, on obtient une solution lim-pid~ de polyamine à 10% de matière active.
EXEMPLE ~
.i Préparation d'un polymère du type - A - Z - dans - 10~;64~9 .,, ~
le~uel A d~3signe - N N - Z désigne sl ou B ' 1 B'l désigne - CH2 - CH2 - CHOH - CH2 - 7 CH2 CHOH 2 Bl désigne - CH2 - CHOH - CH2 -La proportion des motifs A/B'l/Bl est de 1/0,42/0,56, les motifs Bl et B'l étant répartis statistiquement.
ce polymère est préparé selon le procédé direct de l'exemple 2, à partir de pipérazine (1,07 mole), 2-amino 2-méthyl propane 1,3-diol (0,45 mole3 et épichlorhydrine (1,5 mole).
; On mélange 209 g de pipérazine hexahydratée (1,07 mole) et ~-7,2 g de 2-amino 2-méthyl propane L3-diol dans 250 ml d'eau. On ajoute en l'espace d'une heure à 20C, 139 g (1,5 mole) d'épichlorhydrine. On ajoute encore 150 g d'hydroxyde de sodium à 40% (1,5 mole) et on chauffe à 80-90C, température que l'on maintient pendant 1 heure.
s En fin de réaction on dilue avec 760 ml d'eau et on obtient ainsi une solution limpide à 20% d'extrait sec.
Préparation d'un polymère du type - A - Z - dans lequel A désigne - N N - Z désigne Bl ou B 1 \
B 1 dé~igne - CH2 CHOH - C~l2 - N - CH2 - CHOH - CH
Bl désigne - CH2 - CHOH - CH2 -.
La proportion des motifs A/B'l/Bl est de 1,2/0,8/0,4 les motifs Bl et B'l étant répartis statistiquement.
Les proportions molaires relatives de pipérazine/glyco-colle/épichlorhydrine sont de 1,2/0,8/2.
60 g (0,8 mole) de gly~ocolle de formule H2N-CH2-COOH, dispersés dans 218 g d'eau sont neutralisés par 80 g de soude - à 40% (0,8 mole).
A la solution ci-dessus, on ajoute 233 g (1,3 mole) de pipérazine hexahydratée. On ajoute ensuite, sous agitation, en 1 heure, et à 15-20 C, 185 g (2 moles) d'épichlorhydrine.
Après 1 heure d'agitation à cette température, on ajoute, - toujours à la même température , 200 g (2 moles) de soude à 40%.
On poursuit encore l'agitation 1 heure à 20C, puis 1 heure à 80C. La solution est refroidie et ramenée à 25% de matière active par addition de 124 g d'eau.
On obtient ainsi une solution limpide très légèrement colorée en jaune.
Par évaporation d'une solution diluée, on obtient un film dur et peu collant.
Préparation d'un polymère béta~nisé du type - A'- Z' -où A désigne un mélange de radicaux ~ ~ +~
- N N - et - N N -, ~ COO
et Z' désigne B et B désigne - CH2-CHOH-CH2-.
A 500 g d'une solution aqueuse de polymère du type - A - Z - ou Z désigne B, A désigne - N 11 - et B désigne -CH2 - CHOH - CH2 - , à 14,2% de matière active, obtenu par conden-sation en solution aqueuse de 100 g de pipérazine hexahydratée (0,51 mole), 47,7 g d'épichlorhydrine (0,51 mole) et 20,2g d'hydroxyde de - sodium (0,51 mole), contenant l'équivalent d'azote quaternisable et ayant une viscosité de 320 cps à 20C, on ajoute 58,25 g - ` 106649~9 (0,51 mole) de monochloracétate de sodium et on chauffe la masse à 90C pendant 5 heur~s. Après refroidissement, les analyses ef-fectuées sur la solution montrent un rendement de quaternisation de 83,4%. Le taux de bétainisation est de 41,7%. La viscosité
de la solution après quaternisation est de 130 cps.
Le taux de bétaïnisation de 41,7% indique que 83,4% des motifs A' désignent A
- N N -IH~J
COO
A 812 g de solution aqueuse de polymère cationique à
14,2% de matière active décrite ci-dessus et contenant 1,6 équiva-lent d'azote quaternisable, on ajoute 46,7 g (0,4 mole) de mono-chloracétate de sodium et on chauffe à 90C pendant 5 heures. le rendement de quaternisation est de 85%. Le taux de bétaïnisation ; est de 21%.
: Dans ce polymère bétaïnisé, 42% des motifs A désignent :: + ~
- N N -COO
Préparation d'un polymère bétaïnisé du type - A' - Z' ~
où A' désigne un mélange de radicaux ~ +~
- N ~ - et C ~ N - et Z' désigne: Bl c'est-à-dire - CH2 - CHOH - CH2 - , et les motifs obtenus par bétaïnisation de B'l c'est-à-dire un mélange de radicaux ~066449 - CH2 - CHOH - CH2 - N - CH - (`I~OH - CH
cH2 - CH2 ~ c~2 2 ~t - CH2 - CHOH - CH -+N- CH - CHOH CH
On bétaïnise un polymère obtenu par condensation en solution de 483 g (2,49 moles) de pipérazine hexahydratée, de `- 63 g ~0,6 mole) de diglycolamine, de 277,5 g (3 moles) d'épichlor-hydrine et de 120 g (3 moles) de soude (hydroxyde de sodium).
La solution a une viscosité de 75 cps à 25 C.
Ce polymère de départ est du type - A - Z -, où A dési-- gne - N / _ Z désigne Bl ou s'l `.; ~
~ B désigne - CH2 - CHOH - CH2 I C 2 2 ~ - CH2 - CH2OH
Bl désigne - CH2 - CHOH - CH2 -La proportion des motifs A/B'l/Bl est de 2,4/0,6/1,8.
-~ On ajoute à 1005 g dudit polymère à 20% de matière active contenant 2,5 équivalents d'azote totaux, 157,4 g (1,34 mole) de monochloracétate de sodium et on chauffe à 95C pendant 5 heures.
Le rendement de quaternisation est de 70-71% et la vis-cosité du composé résultant est de 67 cps à 25C. Le taux bétaini-sation est de 37,5%, c'est-à-dire que 37,5% des atomes d'azote ~CH - COO
` basique sont sous la forme ~b~ 2 A 1005 g de polymère cationique à 20% de matière active, utilisé dans l'exemple 10, contenant 2,5 équivalents d'azote totaux, on ajoute 78,8 g (0,67 mole) de monochloracétate de sodium et on chauffe à 85-100 C pendant 5 à 6 heures. Le rendement de - 30 quaternisation est de 71% et la viscosité après réaction de 60 cps 106~449 à 25C. Le taux de bétaïnisation est de 19%.
Le polymère bétaïnisé est du même type que celui préparé
dans l'exemple 10 et en diffère seulement par le fait que 19% des atomes d'azote basique sont sous la forme - N -Quaternisation par du sulfate de diméthyle du composé de l'exemple 2 dans lequel:
A désigne - N N - Z désigne Bl ou B' ~, ; lO Bldésigne - CH2 - CHOH - CH2 -B 1 dési~ne - CH2 - CHOH - CH2 - N - CH2 - CHOH - CH2-Le polymère quaternisé est essentiellement constitué
par les deux motifs suivants dans la proportion de 80/20.
f ~ c 2 2 : f 3 SO4CH3 . _ - I - CH2 - CHOH - CH2 - _ .
, ., ICH2 A 1082 g de solution aqueuse à 27% de poly~ère préparé
selon l'exemple 2, dont le chlorure de sodium a été éliminé à 80%
par dialyse, et contenant 3,37 équivalents d~z~e on ajoute, sous agi-tation et à une température inférieure à 30C, 254 g (2,02 moles) de sulfate de diméthyle. Après 3 heures d'agitation à cette tem-p~rature on ramène la solution à 30% de matière active par addition de 485 g d'eau.
Le film obtenu p~r évaporation d'une solution aqueuse est :~066449 dur et lé~èrement collant.
EXE~IPLE 1 3 Préparation d'un polymere quaternisé par du sulfate de diméthyle et constitué par les deux motifs suivants:
C ~ 1 3 4 3 - 1 3 SO4CH3 ~ ~ N+- CH2 ~ CH - CH - - N - CH2 - CHOH - CH2 - -_ _ CH2 - O - CH2 - CH2 OH
dans la proportion d'environ 80/20.
Au mélange de 141 g (1,64 mole) de pipérazine et 42 g (0,4 mole) de diglycolamine solubilisés dans 300 cc de méthanol, on ajoute sous agitation, en une heure et à 20C, 185 g (2 moles) d'épichlorhydrine puis on chuaffe le mélange réactionnel 30 minutes à reflux de solvant.
On ajoute alors en 2 heures en chauffant toujours à
reflux de méthanol, 3~0 g (2 moles) de solution de méthylate de -sodium à 30% dans le méthanol. Le chlorure de sodium est éliminé
par filtration.
261 g de la solution ci-dessus contenant 0,942é~iv~ent d'azote sont chauffés sous pression réduite pour éliminer le méthanol. On ajoute 200 cc de diméthylformamide.
A cette nouvelle solution on ajoute 119 g (0,942 mole) de sulfate de méthyle puis on chauffe le mélange réactionnel sous agitation 4 heures à 90C.
Par addition goutte à goutte de cette solution dans un grand excès d'acétone on isole le polymère sous forme de poudre très hygroscopique.
Le film obtenu par évaporation d'une solution aqueuse est transparent, dur et non collant.
.
EX~MPLE D'APPLlCATION
Shampooing anionique:
; Composé selon l'exemple 3......................... 1 g Lauryl sulfate de triéthanolamine................. 15 g Diéthanolamide de coprah.......................... 3 g Acide lactique a.s.p. PH 7,4 Eau q.s.p......................................... 100 g Shampooing anionique:
Composé selon l'exemple 4......................... 1,2 g Semi-ester sulfosuccinate disodique d'alcanol amide modifié........................................... 10 g Lauryl éther sulfate de sodium condensé avec 2,2 moles d'oxyde d'éthylene...................... 15 g Diéthanolamide de coprah.......~........................................... 4 yEau q.s.p................................................................ 100 g le pH est de 7.
Shampooing:
Composé selon l'exemple 5............................................... 0,75 g Alcool laurique polyéthoxylé avec 12 moles d'oxyde dléthylène................................................................ 12 g Diéthanolamide de coprah................................................... 4 gBromure de triméthyl cétyl ammonium............... 0,5 g Acide citrique q.s.p. pH 4 Eau q.s.p. ....................................... 100 g Shampooing:
Composé selon l'exemple 3......................... 1 g Lauryl éther sulfate de sodium condensé avec 2,2 moles d'oxyde d'éthylène ................................... 10 g 1C~66449 Alkyl imidazoine de ~o~mule I / CH2 ~OO Na N CH2 CH2 ~ C~2 ~ - CH2COONa vendu sous la marque de commerce "Miranol C2M"...... 2 g Monoéthanolamide de coprah~......................... 1,5 g Acide lactique q.s.p. pH 7,5 Eau q.s.p........................................... 100 g Shampooing:
Composé selon l'exemple 4........................... 1,5 g Alcool laurique polyéthoxylé avec 12 moles d'oxyde d'éthylène.......................................... 8 g Sel de sodiwn de N-(N',N'-diéthylamino propyl) N -dodécyl asparagine.................................. 4 g Diéthanolamide de coprah.........n............................ 2 g Acide lactique q.s.ppH 5 Eau q.s.p........................................ ........... 100 g EXEMPLE A
Shampooing anionique:
Composé selon l'exemple 2........................... 1 g Lauryl sulfate de triéthanolamine.................. 10 g Lauryléther sulfate de sodium oxyéthyléné avec 2,2 moles d'oxyde d'~thylène....................... 10 g Diéthanolamide de coprah............................ 3 g Eau q.s.p......................................... 100 g pH 8 Shampooing anionique:
Composé de l'exemple 10............................. 1 g Lauryl sul~ate de triéthanolamine.................. 10 g ~066449 Lauryl éther sul~ate sw aosium ozyéthyléné avec 2,2 moles d'oxyde d'éthylène....................... 10 ~
Diéthanolamide de coprah............................ 3 g Eau q.s.p......................................... 100 g pH 7, 5 Shampooing anionique:
Composé de l'exemple 10.......................... O,75 g Lauryl éther sulfate de sodium oxyéthyléné avec -~ 10 2,2 moles d'oxyde d'éthylène....................... 10 g Oxyde de lauryl diméthyl amine (vendu sous la marque de commerce "Ammonyx L0")........................... 2 g Diéthanolamide de coprah.......................... 2,5 g Eau ~.s.p......................................... 100 g pH 7,5 Shampooing cationique:
- Composé de l'exemple 2............................ 1,2 g Alcool laurique polyéthoxylé avec 12 moles d'oxyde d'éthylene .................... . .... ........... 12 g Bromure de triméthyl cétyl ammonium (vendu sous la marque de commerce "Cetavlon")................... 1 g Diéthanolamide de coprah............................ 2 g Acide lactique q.s.p. pH 5 Eau q.s.p......................................... 100 g Shampooing:
Composé selon l'exemple 7..................-................ 1,5 g Composé de formule C12H25O~ C2H3O(CH2OH)~4 -H 6 g Composé de formule R-CHOH-CH2O[CH2-CHOH-CH2O~3 5 H
où R signifie alkyle en Cg-Cl2........................ 5 g Oxyde de lauryl diméthylamine (commercialisé sous la marque de commerce "Ammonyx LO")...................... 2 g Acide lactique q.s.p. pH 4 - Eau q.s.p......................................... 100 g Shampooing:
Composé de l'exemple 7............................ 1 g -~ Lauryl sul~ate de triéthanolamine................. 15 g Diéthanolamide laurique........................... 3 g Eau q.s.p..............................~......... 100 y pH 7,5 . .
Shampooing:
Composé de l'exemple 8............................ 2 g Lauryl éther sulfate de soude polyoxyéthyléné avec 2,2 moles d'oxyde d'éthylène...................... 12 g Ethanolamide de coprah............................ 2,5 g Carboxyméthyl cellulose........................... 0,5 g ~ - Eau q.s.p......................................... 100 g - ~ pH 7,3 Shampooing:
Composé de l'exemple 8............................ 1,5 g Composé de formule R.CHOH-CH20LCH2-CHOH-CH2O ~5H 1,5 g où R signifie alkyle en Cg-Cl2.................... ~ g Alcool laurique polyéthoxylé avec 12 moles d'oxyde d'éthylène........................................ 5 g Acide lactique q.s.p.pH 5 Eau q.s.p......................................... 100 g ShampGoing anionique:
Cornposé de l'exemple 12.......................... 1,5 g Lauryl myristyléther sulfate de monoéthanolamine oxyéthyléné avec 2,2 moles d'oxyde d'éthylène. 12 g Diéthanolamide de coprah......................... 2,5 g Eau q.s.p............................ ~........... 100 g pH = 8 Shampooing anionique Composé de l'exemple 12............................. 1 g Oxyde de lauryl diméthylamine de formule f~3 12 25 1 > ..................................... 1,5 g ~H3 Diéthanolamides d'acides gras de coprah........... 2 g Lauryl myristyléther sulfate de sodium oxy-éthyléné avec 2,2 moles d'oxyde d'éthylène........ 8,5 g Eau q.s.p....... ................................. 100 g pH = 7,5 -- Shampooing cationique Composé de l'exemple 12........................... 2 g Alcool laurlque oxyéthyléné avec 12 moles d'oxyde d'éthylène................................ 10 g Diéthanolamides d'acides gras de coprah........... 3 g Oxyde de lauryl diméthylamine..................... 2,5 g Eau q.s.p......................................... 100 g pH = 5 : .~
-2- ~ -hydroxyethoxy ethyl, 1,3-dihydroxy 2-methyl propyl-2, 1-hydroxy 2-methyl propyl-2.
The request also relates to the methods of preparation of said polymers and their ammonium derivatives quaternary.
The cationic polymers according to the present application, ; can be prepared by direct or indirect polycondensation.
Direct polycondensation consists in reacting piperazine and a hydroxylated amine such as diglycolamine or 2-amino 2-methyl propane-1,3-diol or an amino acid such as glycocolle with an epihalohydrin such as epichlorohydrin 10 ~: i64 ~ 9 or 1'epibromhydrine, in a ~ ueux medium, to add soda as an acceptor of the released hydracid, then to heat to temperature ture between 80 and 90c.
Indirect polycondensation consists in preparing everything first, an intermediate derivative X, resulting from the reaction of epihalohydrin with either piperazine or the hydroxylated amine and / or the amino acid. this intermediate derivative x is then brought to react with a second amine. Then, if necessary, epihalohydrin and a base such as hydro-sodium xyde and heated to a temperature between 80 and 90C.
The usable proportions of piperazine, epihalo-hydrine and hydroxylated amine and / or amino acid, are ~ onc-tion of the alternation of the patterns A, sl and s'l that we want to obtain in the final polymer.
Epihalohydrin and the piperazine-hydroxy amine mixture lée and / or amino acid are preferably present in equimolar proportions. As for the piperazine-amine hydro-xylated and / or amino acid, it includes molar proportions between 90 and 50% for piperazine and 10 to 50% for the amine hy ~ roxylated and / or the amino acid.
The polymers thus obtained can, in known fashion, be known.
as indicated in the application for bre ~ and no 157,715, be oxidized ~ s with hydrogen peroxide or peracids or be quaternized with known quaternizing agents, such as bromide, chloro rure, iodide, sulfate, mesylate, or lower alkyl tosylate, preferably methyl or ethyl, chloride or bromide benzyl.
A quaternization which has proved particularly advantageous as regards the compatibility properties of polymers resulting with anionic surfactants, is "betainization"
compounds of formulas (I) and (I bis) consisting in quaternizing 10 ~ 6449 from O to 66% of the basic quaternizable groups with the sodium chloracetate or chloroacetic acid. The yield of the reaction is generally between 60 and 100%.
The rate of "betainisation" can be defined as the ratio between the number of quaternized nitrogen equivalents and - the number of quaternizable total nitrogen equivalents, multiplied by 100.
The quaternization yield of the reaction can be defined by the ratio between the number of nitrogen equivalents actually quaternized and the number of agent equivalents quaternization used, multiplied by 100.
The Applicant has found that only one of the two atoms tertiary nitrogen of motif A was easily quaternizable. We obtained by betainization, patterns corresponding to the formula - A '- Z' ~ (II) in which A 'is a mixture of groups - - NN - and - NN -COO
Z 'denotes B1 or the patterns obtained by betainization of B, B' or B'l when these have one or more nitrogen atoms basic that can take the form . - NOT
., I
- ~ CH2 COO ~
; The present application therefore also relates to a formula polymer - A '- Z' - (II) where A denotes a mixture of radicals .:
.
+ ~
- NN - and - NN -COO
and Z 'denotes:
(1) either s or s or the patterns obtained by beta-inization of B or if these have one or more nitrogen atoms basic, B and B ', identical or different, denote a bivalent radical which is a straight or branched chain alkylene radical, comprising ~, i both up to 7 carbon atoms in the main chain, unsubstituted or substituted by one or more ~ hydroxy- group the and which may also contain oxygen, nitrogen atoms, of sulfur, 1 to 3 aromatic and / or heterocyclic rings, the oxygen, nitrogen and sulfur atoms being present in the form of ether, thioether, sulfoxide, sulfone, sulfonium groups, amine, alkylamine, alkenylamine, benzylamine, amine oxide, amide, imide, alcohol, ester and / or urethane;
(2) or Z 'means Bl or B'l and the patterns obtained - by betainization of Bl and it means at least once s'l and the motifs deriving from B'l, Bl denotes a bivalent radical which is a straight chain alkylene radical or branched having jùsqu'à 7 carbon atoms in the chain ~ ne prin-cipal, substituted by a hydroxyl group and preferably a 2-hydroxy propane 1,3-diyl group, B'l is a bivalent radical which is a chain alkylene radical straight or branched having up to 7 carbon atoms in the main chain, substituted by one or more hydroxyl radicals and interrupted by one or more nitrogen atoms, the nitrogen atom being substituted by an alkyl chain advantageously having 1 with 4 and preferably 4 carbon atoms, possibly interrupted-ment by an oxygen atom and necessarily including one or - 7 _ 10 ~ 6449 `several hydroxyl and / or carboxyl functions.
The present application also relates to a composition cosmetic hair treatment containing a polymer of formula - A ~ _ z (II) where A 'denotes a mixture of radicals ~
- NN - and - NN -~ CH
- COO
æ ~ denotes Bl or B'l and / or B or B 'and the patterns obtained by the betainization of Bl and / or B and B 'when these include one or more basic nitrogen atoms.
It is found that the polymers object of the present inyention and prepared according to any of the methods cited ; above, are characterized by the fact that they are film-forming and have a relatively low molecular weight, i.e. lower to 15,000.
They are soluble in water or in a hydroalcoholic medium.
- than.
~ `They are particularly effective for hair sensitized after treatments such as discoloration, perms or dyes, but can also be taggedly used for normal hair.
'~:
These polymers are introduced in proportions of 0.1 ~ 5% and preferably 0.2 ~ 3% of the total weight of the compound sition in different cosmetic compositions like lotions creams, or styling gels as main constituents pale or in shampoos, conditioning compositions pleats, permanent fixers, dyes, etc., as as adjuvants in the presence of other compounds such as surfactants anionic, cationic, nonionic, amphoteric or zwitterionics, oxidants, synergists, or stabilizers foam, sequestering agents, superfats, thickeners . ~ - 8 _ a ~ oucissant, antiseptics, preservatives, colo-rants, perfumes, germicides, they can be used mixed with other anionic, cationic, am-photers or non-ionic.
They can be found in different compositions either in the form of salts of mineral or organic acids, or in form of free bases or quaternaries, depending on the pH
of use, this being between 3 and 11.
Cosmetic compositions for hair according to the invention can also be presented in the form of solutions aqueous, hydroalcoholic, creams, pastes, gels or for ~ res. They may also contain a propellant and be put in an aerosol can.
The shampoo compositions for hair according to the vention are characterized by the fact that they contain in plus an anionic, cationic, non-ionic surfactant, amphoteric and / or zwitterionic, one or more compounds of formula I bis and / or II, as well as possibly synergists stabilization of foam, sequestrants, superfats, thickeners, one or more cosmetic resins, softeners polishers, dyes, perfumes, bactericides, con-servants, and any other adjuvant usually used in cosmetic compositions.
The polymers according to the present request allow also to prepare styling lotions, creams treatment, hair conditioners, anti lotions dandruff and other similar compositions, characterized by the fact that they contain one or more object polymers of the present application, having a determined molecular weight by lowering the vapor pressure between 500 and 15,000.
The following examples are intended to illustrate the invention without however limiting it. The parties will be indicated _ 9 _ ~ 06644 ~
in weight.
1st stage - Preparation of ~ intermediate derivative -N, N-Bis [~ -hydroxy, Y-chloro-propyl ~ diglycolamine de ~ ormule Cl CH2 - CHOH - CH2 --N - CH - CHOH CH Cl .. CH2 hereinafter called intermediary X.
To a solution of 420 g of diglycolamine (4 moles) ~ `10 in 2700 y of water, added dropwise and with stirring, 740 g (8 moles) of epichlorohydrin in 1 hour at 10-15C.
After 4 hours of stirring the reaction mixture at 20C, the epoxy functions have practically disappeared.
We then obtain a clear solution, very slightly tinted green, 30% dry extract.
2nd stage - Preparation of a polymer of the type - - A _ z _ where A désiyne - NN - Z denotes Bl or B ' Bl denotes -CH2 - CHOH - CH2 -B 1 denotes - CH2 - CHOH - CH - N - CH CHOH CH
: CH2 CH2 - O - CH2 - C ~ I2OH
and in which the proportions of the patterns A / Bl / Bl are 4/1/3 (the molar proportions of piperazine / diglycolamine / epichlorhy-drine are 4/1/5).
To 775 g of piperazine hexahydrate (4 moles) is added maintaining the temperature at 20C, 965 g (l mole) of solution : ~ of intermediate derivative X prepared above. Then added 277 g (3 moles) of epichlorohydrin always at a temperature of 20C.
500 g (5 moles) of sodium hydroxide solution are then added over 1 hour 10 ~ 6 ~ 49 at 40%. Then heated up to 80L90C and maintained -this temperature for 1 hour.
By dilution with 1130 g of water, a solution is obtained 20% active ingredient.
Direct preparation of a polymer of the type - A - Z -in which the motifs A and Z have the same meaning as in example 1, but where the distribution of piperazine and digly-colamine is statistical.
The proportion of patterns A / B'l / Bl is 4/1/3 as above.
We use the same relative molar proportions piperazine, diglycolamine and epichlorohydrin only in Example 1, i.e. 4/1/5.
A 161 g of piperazine hexahydrate (0.83 mole) and 21 g of diglycolamine (0.2 mole), dispersed in 140 ml of water, add in 1 hour and at 20C, 92.5 g of epichlorohydrin (1 mole).
One hour after the addition, add dropwise, always at 20C, 100 g of 40% sodium hydroxide (1 mole).
It is then heated to the temperature of 80-90C, which we hold for 1 hour.
The reaction medium is then diluted with 227 ml of water to obtain a 20% solution of active material.
The solution thus obtained is colorless and its viscosity measured at 25C is 0.7 poise.
Preparation of a polymer of type - A - Z - in which . ' r ~
A denotes - NN - and Z denotes B ' '' `1066449 B 1 denotes - cH2 - CHOH - CH2 - N - CH - CHOH CH
CH2 - O - CH2 - cH2OH
The proportion of moti ~ s A / B '1 is 1/1.
The piperazine / diglycolamine / molar proportions epichlorohydrin are 1/1/2.
To a solution of 1 mole (194 g) of piperazine hexahydrate in 742 g of water, added dropwise to 1 ~ eure, at 20C, with stirring and under a nitrogen atmosphere, 1 mole of intermediate X prepared in Example 1, in the form of a 30% solution (970 g).
After the addition is complete, the reaction mass is stirred at 20C for 1 hour.
Then, at the same temperature and in 1 hour, 167.5 g 48% sodium hydroxide (2 moles).
Agitation is continued for another 1 hour at this time.
temperature, then the mixture is heated for 2 hours at 80-90C.
By adding 1026.5 g of water, a clear and practically colorless solution of 10% polyamine ; 20 active ingredient.
1st stage - Preparation of a prepolymer P to which we attribute mainly the formula:
~, ~ ~ N ~
E OEl2 ~ NH
To a solution of 776 g (4 moles) of piperazine hexa-hydrated in 500 g of water, adding as in the example-ple 3, 2 moles of intermediate compound X of Example 1, under ; 30 as a 30% solution (1935 g).
After the addition is complete, the reaction mass is maintained under stirring at 20C, for 1 hour.
- - .. `:
106,644 ~
Then added at the same temperature and in 1 : hour, 4 mo ~ es of sodium hydroxide in the form of a solution 48% (335 g). Agitation is continued for another 1 hour at this time.
temperature, then the mixture is heated for 3 hours at 80-90C.
This gives a clear solution of a prepolymer P of formula above.
-, 2nd stage - Preparation of a polymer of the type - A - Z -.. ~
~ in which A designates - NN -`` '', Z denotes Bl or B'l Bl denotes - CH2 - CHOH - CH2 -1 g 2 CHOH - CH2 - 7 - CH2 - cHOH - CH
CH
~ 1 2 :, CH2 - O - CH2 - CH20H
The proportion of the patterns A / B'l / Bl is 2/1/1.
The piperazine / diglycolamine / epi- molar proportions ; hydrochlorine are 2/1/3.
Half of the prepolymer solution P above prepared (1835 g) (corresponding to 2 equivalents of amines secondary), added dropwise and with stirring, 92.5 g epichlorohydrin (1 mole).
After the addition is complete, the reaction mass is maintained under stirring at 20C, for 1 hour.
Then added at the same temperature, and in 1 hour, 83 g (1 mole) 48% sodium hydroxide.
Aglation is maintained for another 1 hour at this temperature.
erase, then the mixture is heated for 1 hour at 80-90C.
By adding 2625 g of water, a solution is obtained clear and practically colorless of polyamine at 10 ~ material active.
`10 ~ 64 ~ 9 - Preparation of a polym ~ re of the type - A - Z -. ~ ~,.
. or A means - NN - Z means Bl or B
/
B 1 if ~ nigie - CH2 - CHOH - CH2 - N - CH2 - CHOH - CH2 -~ CH2 Bl means - CH2 - CHOH - CH2 -The proportion of patterns A / B'l / Bl is 4/1/3.
The relative molar proportion of piperazine / digly-colamine / epihalohydrin is 4/1/5.
A 394.5 g of prepolymer solution P described above - above and containing 0.43 equivalent of secondary amine, add with stirring, 51 g of 1,3-bis piperazino propan-2-ol of formula '''~ / - \
~ - HN N-CH2 - CHOH - CH2 - N NH
`containing 0.43 equivalent of secondary amine, i.e.
corresponding to 0.215 mole. 1,3-bis piperazino 2-propane-2-o ~
can be prepared according to the method described in Example 15 of Application No. 157,715.
- To this solution is added in 1 hour, and at 20 C, 39.7 g (0.43 mole) of epichlorohydrin. The mixture is stirred 1 hour at this temperature. Then add to 20C and 1 hour, 35.8 g (0.43 mole) 48% sodium hydroxide.
~ ~ - after 1 hour of stirring at the same temperature, - heats the reaction mass for 1 hour at 80-90C.
By adding 1099 g of water, a lim-pid ~ of polyamine at 10% active material.
EXAMPLE ~
.i Preparation of a polymer of the type - A - Z - in - 10 ~; 64 ~ 9 . ,, ~
the ~ uel A d ~ 3 sign - NN - Z denotes sl or B '1 B'l denotes - CH2 - CH2 - CHOH - CH2 - 7 CH2 CHOH 2 Bl denotes - CH2 - CHOH - CH2 -The proportion of units A / B'l / Bl is 1 / 0.42 / 0.56, the patterns Bl and B'l being distributed statistically.
this polymer is prepared according to the direct process of Example 2, starting from piperazine (1.07 mole), 2-amino 2-methyl propane 1,3-diol (0.45 mole3 and epichlorohydrin (1.5 mole).
; 209 g of piperazine hexahydrate (1.07) are mixed mole) and ~ -7.2 g of 2-amino 2-methyl propane L3-diol in 250 ml of water. 139 g (1.5 mole) are added over the course of an hour at 20 ° C.
epichlorohydrin. Another 150 g of sodium hydroxide are added.
at 40% (1.5 mole) and heated to 80-90C, temperature that it is maintained for 1 hour.
s At the end of the reaction, dilute with 760 ml of water and thus obtains a clear solution with 20% of dry extract.
Preparation of a polymer of the type - A - Z - in which A designates - NN - Z designates Bl or B 1 \
B 1 designates - CH2 CHOH - C ~ l2 - N - CH2 - CHOH - CH
Bl denotes - CH2 - CHOH - CH2 -.
The proportion of patterns A / B'l / Bl is 1.2 / 0.8 / 0.4 the patterns Bl and B'l being distributed statistically.
The relative molar proportions of piperazine / glyco-glue / epichlorohydrin are 1.2 / 0.8 / 2.
60 g (0.8 mole) of gly ~ glue of formula H2N-CH2-COOH, dispersed in 218 g of water are neutralized with 80 g of soda - at 40% (0.8 mole).
To the above solution, 233 g (1.3 mole) are added piperazine hexahydrate. Then, with stirring, 1 hour, and at 15-20 C, 185 g (2 moles) of epichlorohydrin.
After 1 hour of stirring at this temperature, the following is added, - always at the same temperature, 200 g (2 moles) of 40% sodium hydroxide.
Stirring is continued for 1 hour at 20C, then 1 hour at 80C. The solution is cooled and brought to 25% of active ingredient by addition of 124 g of water.
This gives a very slightly clear solution colored yellow.
By evaporation of a dilute solution, a hard and slightly sticky film.
Preparation of a beta polymerized type - A'- Z '-where A denotes a mixture of radicals ~ ~ + ~
- NN - and - NN -, ~ COO
and Z 'denotes B and B denotes - CH2-CHOH-CH2-.
500 g of an aqueous solution of polymer of the type - A - Z - or Z denotes B, A denotes - N 11 - and B denotes -CH2 - CHOH - CH2 -, with 14.2% of active material, obtained by conden-sation in aqueous solution of 100 g of piperazine hexahydrate (0.51 mole), 47.7 g of epichlorohydrin (0.51 mole) and 20.2 g of hydroxide - sodium (0.51 mole), containing the equivalent of quaternizable nitrogen and having a viscosity of 320 cps at 20C, 58.25 g is added - `106649 ~ 9 (0.51 mole) of sodium monochloroacetate and the mass is heated at 90C for 5 hours. After cooling, the analyzes ef-performed on the solution show a quaternization yield 83.4%. The betainization rate is 41.7%. The viscosity of the solution after quaternization is 130 cps.
The betainization rate of 41.7% indicates that 83.4% of reasons A 'denote A
- NN -IH ~ J
COO
A 812 g of aqueous solution of cationic polymer to 14.2% of active ingredient described above and containing 1.6 equiva-slow quaternizable nitrogen, 46.7 g (0.4 mole) of mono-sodium chloracetate and heated to 90C for 5 hours. the quaternization yield is 85%. Betainization rate ; is 21%.
: In this betainized polymer, 42% of the units A denote :: + ~
- NN -COO
Preparation of a betainized polymer of the type - A '- Z' ~
where A 'denotes a mixture of radicals ~ + ~
- N ~ - and C ~ N - and Z 'denotes: B1 that is to say - CH2 - CHOH - CH2 -, and the patterns obtained by betainization of B'l, that is to say a mixture of radicals ~ 066449 - CH2 - CHOH - CH2 - N - CH - (`I ~ OH - CH
cH2 - CH2 ~ c ~ 2 2 ~ t - CH2 - CHOH - CH - + N- CH - CHOH CH
A polymer obtained by condensation is betainized solution of 483 g (2.49 moles) of piperazine hexahydrate, `- 63 g ~ 0.6 mole) of diglycolamine, 277.5 g (3 moles) of epichlor-hydrin and 120 g (3 moles) soda (sodium hydroxide).
The solution has a viscosity of 75 cps at 25 C.
This starting polymer is of the type - A - Z -, where A desi-- gne - N / _ Z indicates Bl or s'l `.; ~
~ B denotes - CH2 - CHOH - CH2 IC 2 2 ~ - CH2 - CH2OH
Bl denotes - CH2 - CHOH - CH2 -The proportion of units A / B'l / Bl is 2.4 / 0.6 / 1.8.
- ~ 1005 g of said polymer containing 20% of active material are added containing 2.5 total nitrogen equivalents, 157.4 g (1.34 mole) sodium monochloroacetate and heated to 95C for 5 hours.
The quaternization yield is 70-71% and the screw cosity of the resulting compound is 67 cps at 25C. The betaini- rate sation is 37.5%, i.e. 37.5% of the nitrogen atoms ~ CH - COO
`basic are in the form ~ b ~ 2 A 1005 g of cationic polymer with 20% active material, used in Example 10, containing 2.5 equivalents of total nitrogen, 78.8 g (0.67 mole) of sodium monochloroacetate are added and heats to 85-100 C for 5 to 6 hours. The yield of - 30 quaternization is 71% and the viscosity after reaction of 60 cps 106 ~ 449 at 25C. The betainization rate is 19%.
The betainized polymer is of the same type as that prepared in example 10 and only differs from it by the fact that 19% of basic nitrogen atoms are in the form - N -Quaternization with dimethyl sulfate of the compound of Example 2 in which:
A denotes - NN - Z denotes Bl or B ' ~, ; lO Bldesign - CH2 - CHOH - CH2 -B 1 desi ~ ne - CH2 - CHOH - CH2 - N - CH2 - CHOH - CH2-The quaternized polymer consists essentially of by the following two reasons in the proportion of 80/20.
f ~ c 2 2 : f 3 SO4CH3 . _ - I - CH2 - CHOH - CH2 - _.
,., ICH2 A 1082 g of aqueous solution at 27% of poly ~ era prepared according to Example 2, 80% of which sodium chloride has been removed by dialysis, and containing 3.37 equivalents of ~ z ~ e is added, under agi-at a temperature below 30C, 254 g (2.02 moles) dimethyl sulfate. After 3 hours of agitation at this time p ~ rature the solution is reduced to 30% of active material by addition 485 g of water.
The film obtained p ~ r evaporation of an aqueous solution is : ~ 066449 hard and slightly sticky.
EXE ~ IPLE 1 3 Preparation of a polymer quaternized with sulphate dimethyl and consisting of the following two units:
C ~ 1 3 4 3 - 1 3 SO4CH3 ~ ~ N + - CH2 ~ CH - CH - - N - CH2 - CHOH - CH2 - -_ _ CH2 - O - CH2 - CH2 OH
in the proportion of about 80/20.
In the mixture of 141 g (1.64 mole) of piperazine and 42 g (0.4 mole) of diglycolamine dissolved in 300 cc of methanol, 185 g (2 moles) are added with stirring, in one hour and at 20C
epichlorohydrin and then the reaction mixture is heated for 30 minutes at solvent reflux.
We then add in 2 hours, always heating to methanol reflux, 3 ~ 0 g (2 moles) of methylate solution from -30% sodium in methanol. Sodium chloride is removed by filtration.
261 g of the above solution containing 0.942é ~ iv ~ ent nitrogen are heated under reduced pressure to remove the methanol. 200 cc of dimethylformamide are added.
To this new solution is added 119 g (0.942 mole) of methyl sulfate and then the reaction mixture is heated with stirring 4 hours at 90C.
By dropwise addition of this solution to a large excess of acetone the polymer is isolated in powder form very hygroscopic.
The film obtained by evaporation of an aqueous solution is transparent, hard and not sticky.
.
EX ~ MPLE OF APPLICATION
Anionic shampoo:
; Compound according to Example 3 ......................... 1 g Triethanolamine lauryl sulfate ................. 15 g Coconut diethanolamide .......................... 3 g Lactic acid asp PH 7.4 Water qs ........................................ 100 g Anionic shampoo:
Compound according to Example 4 ......................... 1.2 g Alkanol amide disodium sulfosuccinate semi-ester modified ........................................... 10 g Lauryl ether sodium sulfate condensed with 2.2 moles of ethylene oxide ...................... 15 g Coconut diethanolamide ....... ~ ....................................... .... 4 water qs ........................................... .................... 100 g the pH is 7.
Shampoo:
Compound according to Example 5 ............................................ ... 0.75 g Polyethoxylated lauryl alcohol with 12 moles of oxide ethylene ................................................. ............... 12 g Coconut diethanolamide ............................................... .... 4 g Trimethyl cetyl ammonium bromide ............... 0.5 g Citric acid qs pH 4 Water qs ....................................... 100 g Shampoo:
Compound according to Example 3 ......................... 1 g Lauryl ether sodium sulfate condensed with 2.2 moles of ethylene oxide ................................... 10 g 1C ~ 66449 Alkyl imidazoine of ~ o ~ mule I / CH2 ~ OO Na N CH2 CH2 ~ C ~ 2 ~ - CH2COONa sold under the trademark "Miranol C2M" ...... 2 g Coconut monoethanolamide ~ ......................... 1.5 g Lactic acid qs pH 7.5 Water qs .......................................... 100 g Shampoo:
Compound according to Example 4 ........................... 1.5 g Polyethoxylated lauryl alcohol with 12 moles of oxide ethylene .......................................... 8 g Sodiwn salt of N- (N ', N'-diethylamino propyl) N -dodecyl asparagine .................................. 4 g Coconut diethanolamide ......... n ............................ 2 g Lactic acid qsppH 5 Water qs ....................................... ......... .. 100 g EXAMPLE A
Anionic shampoo:
Compound according to Example 2 ........................... 1 g Triethanolamine lauryl sulfate .................. 10 g Oxyethylenated sodium lauryl ether sulfate with 2.2 moles of ~ thylene oxide ....................... 10 g Coconut diethanolamide ............................ 3 g Water qs ........................................ 100 g pH 8 Anionic shampoo:
Compound of example 10 ............................. 1 g Lauryl sul ~ aet of triethanolamine .................. 10 g ~ 066449 Lauryl ether sul ~ ate sw aosium ozyethylenated with 2.2 moles of ethylene oxide ....................... 10 ~
Coconut diethanolamide ............................ 3 g Water qs ........................................ 100 g pH 7.5 Anionic shampoo:
Compound of Example 10 .......................... O, 75 g Lauryl ether oxyethylenated sodium sulfate with - ~ 10 2.2 moles of ethylene oxide ....................... 10 g Lauryl dimethylamine oxide (sold under the brand "Ammonyx L0") ........................... 2 g Coconut diethanolamide .......................... 2.5 g Water ~ .sp ........................................ 100 g pH 7.5 Cationic shampoo:
- Compound of Example 2 ............................ 1.2 g Polyethoxylated lauryl alcohol with 12 moles of oxide ethylene ..................... .... ........... 12 g Trimethyl cetyl ammonium bromide (sold under the trademark "Cetavlon") ................... 1 g Coconut diethanolamide ............................ 2 g Lactic acid qs pH 5 Water qs ........................................ 100 g Shampoo:
Compound according to Example 7 ..................-................ 1.5 g Compound of formula C12H25O ~ C2H3O (CH2OH) ~ 4 -H 6 g Compound of formula R-CHOH-CH2O [CH2-CHOH-CH2O ~ 3 5 H
where R means Cg-Cl2 alkyl ........................ 5 g Lauryl dimethylamine oxide (sold under the trademark "Ammonyx LO") ...................... 2 g Lactic acid qs pH 4 - Water qs ........................................ 100 g Shampoo:
Compound of Example 7 ............................ 1 g - ~ Lauryl sul ~ triethanolamine ate ................. 15 g Diethanolamide lauric ........................... 3 g Water qs ............................. ~ ......... 100 y pH 7.5 . .
Shampoo:
Compound of example 8 ............................ 2 g Lauryl ether sodium hydroxide polyoxyethylenated with 2.2 moles of ethylene oxide ...................... 12 g Coconut ethanolamide ............................ 2.5 g Carboxymethyl cellulose ........................... 0.5 g ~ - Water qs ........................................ 100 g - ~ pH 7.3 Shampoo:
Compound of Example 8 ............................ 1.5 g Compound of formula R.CHOH-CH20LCH2-CHOH-CH2O ~ 5H 1.5 g where R means Cg-Cl2 alkyl .................... ~ g Polyethoxylated lauryl alcohol with 12 moles of oxide ethylene ........................................ 5 g Lactic acid qsppH 5 Water qs ........................................ 100 g Anionic Shampoo:
Example 12 .......................... 1.5 g Lauryl myristylether monoethanolamine sulfate oxyethylenated with 2.2 moles of ethylene oxide. 12 g Coconut diethanolamide ......................... 2.5 g Water qs ........................... ~ ........... 100 g pH = 8 Anionic shampoo Compound of example 12 ............................. 1 g Lauryl dimethylamine oxide of formula f ~ 3 12 25 1> ..................................... 1.5 g ~ H3 Coconut fatty acid diethanolamides ........... 2 g Lauryl myristylether oxy sodium sulfate ethylene with 2.2 moles of ethylene oxide ........ 8.5 g Water qs ...... ................................. 100 g pH = 7.5 - Cationic shampoo Compound of example 12 ........................... 2 g Lauryl alcohol oxyethylenated with 12 moles ethylene oxide ................................ 10 g Coconut fatty acid diethanolamides ........... 3 g Lauryl dimethylamine oxide ..................... 2.5 g Water qs ........................................ 100 g pH = 5 :. ~
-
Claims (26)
(1) un polymère cationique filmogène de bas poids molécu-laire de formule - A - Z - (I bis) où A désigne , et Z désigne le symbole B1 ou B'1 et il signifie au moins une fois le symbole B'1;
B1 désigne un radical bivalent qui est un radical alkylène à chaîne droite ou ramifiée ayant jusqu'à 7 atomes de carbone dans la chaîne principale substitué par un groupement hydroxyle;
B'1 est un radical bivalent qui est un radical alkylène à chaîne droite ou ramifiée ayant jusqu'à 7 atomes de carbone dans la chaîne principale, non substitué ou substitué par un ou plusieurs radicaux hydroxyle et interrompu par un ou plusieurs atomes d'azote, l'atome d'azote étant substitué par une chaîne alkyle ayant avantageusement de 1 à 4 et de préférence 4 atomes de carbone, interrompue éventuellement par un atome d'oxygène et comportant obligatoirement une ou plusieurs fonctions hydroxyle et/ou carboxyle;
(2) un sel d'ammonium quaternaire d'un polymère de formule (I bis);
(3) un produit d'oxydation d'un polymère de formule (I bis). 1. Cosmetic composition for hair containing in a vehicle at least one of the following compounds:
(1) a low molecular weight film-forming cationic polymer formula formula - A - Z - (I bis) where A denotes , and Z denotes the symbol B1 or B'1 and it means the symbol B'1 at least once;
B1 denotes a bivalent radical which is a radical straight or branched chain alkylene having up to 7 atoms carbon in the main chain substituted by a group hydroxyl;
B'1 is a bivalent radical which is an alkylene radical straight or branched chain having up to 7 carbon atoms in the main chain, unsubstituted or substituted by one or several hydroxyl radicals and interrupted by one or more nitrogen atoms, the nitrogen atom being substituted by a chain alkyl advantageously having from 1 to 4 and preferably 4 atoms carbon, possibly interrupted by an oxygen atom and necessarily having one or more hydroxyl functions and / or carboxyl;
(2) a quaternary ammonium salt of a polymer of formula (I bis);
(3) an oxidation product of a polymer of formula (I bis).
B1 désigne un radical bivalent qui est un radical alkylène à chaîne droite ou ramifiée ayant jusqu'à 7 atomes de carbone dans la chaîne principale substitué par un groupement hydroxyle, B'1 est un radical bivalent qui est un radical alkylène à chaîne droite ou ramifiée ayant jusqu'à 7 atomes de carbone dans la chaîne principale, non substitué ou substitué par un ou plusieurs radicaux hydroxyle et interrompu par un ou plusieurs atomes d'azote, l'atome d'azote étant substitué par une chaîne alkyle ayant éventuellement de 1 à 4 et de préférence 4 atomes de carbone, interrompue éventuellement par un atome d'oxygène et comportant obligatoirement une ou plusieurs fonctions hydroxyle et/ou carboxyle. 14. Low molecular weight film-forming cationic polymer of formula - A - Z - (I bis) where A denotes and Z denotes the symbol B1 or B'1 and it signifies at least one times the symbol B'1;
B1 denotes a bivalent radical which is a radical straight or branched chain alkylene having up to 7 atoms carbon in the main chain substituted by a group hydroxyl, B'1 is a bivalent radical which is a radical straight or branched chain alkylene having up to 7 atoms carbon in the main chain, unsubstituted or substituted by one or more hydroxyl radicals and interrupted by one or several nitrogen atoms, the nitrogen atom being substituted by an alkyl chain optionally having from 1 to 4 and preferably 4 carbon atoms, possibly interrupted by one atom oxygen and necessarily having one or more functions hydroxyl and / or carboxyl.
B'1 est un radical bivalent qui est un radical alkylène à chaîne droite ou ramifiée ayant jusqu'à 7 atomes de carbone dans la chaîne principale, non substitué ou substitué par un ou plusieurs radicaux hydroxyle et interrompu par un ou plusieurs atomes d'azote, l'atome d'azote étant substitué par un chaîne alkyle ayant avantageusement de 1 à 4 et de préférence 4 atomes de carbone, interrompue éventuellement par un atome d'oxygène et comportant obligatoirement une ou plusieurs fonctions hydroxyle et/ou carboxyle. 23. Polymer according to claim 22, of formula - A '-Z '- (II) in which A' denotes a mixture of radicals and and Z 'denotes B1 or B'1 and the patterns obtained by betaïnisa-tion of B'1 and it means at least once B'1 and the patterns deriving from B'1, B1 denotes a bivalent radical which is a straight or branched chain alkylene radical having up to 7 carbon atoms in the main chain substituted by a hydroxyl group and preferably a 2-hydroxy group propane-1,3-diyl;
B'1 is a bivalent radical which is a radical straight or branched chain alkylene having up to 7 atoms carbon in the main chain, unsubstituted or substituted by one or more hydroxyl radicals and interrupted by one or several nitrogen atoms, the nitrogen atom being substituted by a alkyl chain advantageously having from 1 to 4 and preferably 4 carbon atoms, possibly interrupted by an atom oxygen and necessarily having one or more functions hydroxyl and / or carboxyl.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7427030A FR2280361A2 (en) | 1974-08-02 | 1974-08-02 | HAIR TREATMENT AND CONDITIONING COMPOSITIONS |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1066449A true CA1066449A (en) | 1979-11-13 |
Family
ID=9142077
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA232,769A Expired CA1066449A (en) | 1974-08-02 | 1975-08-01 | Hair treatment and conditioning compositions |
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JP (3) | JPS5151528A (en) |
AT (1) | AT355727B (en) |
BE (1) | BE832063R (en) |
BR (1) | BR7504935A (en) |
CA (1) | CA1066449A (en) |
CH (1) | CH579909A5 (en) |
DE (2) | DE2534514C2 (en) |
DK (1) | DK163478C (en) |
FR (1) | FR2280361A2 (en) |
GB (2) | GB1510488A (en) |
IT (1) | IT1050594B (en) |
NL (1) | NL177730C (en) |
Families Citing this family (251)
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FR2460133B1 (en) * | 1979-07-02 | 1986-11-07 | Bristol Myers Co | COMPOSITION FOR HAIR CARE AND METHOD OF APPLICATION |
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LU83020A1 (en) * | 1980-12-19 | 1982-07-07 | Oreal | OIL COMPOSITION FOR THE TREATMENT OF KERATINIC MATERIALS AND THE SKIN |
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WO2024097256A1 (en) | 2022-10-31 | 2024-05-10 | L'oreal | Systems and methods for stabilizing compositions, and compositions comprising the systems |
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Family Cites Families (3)
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BE791128A (en) * | 1971-11-12 | 1973-05-09 | Bayer Ag | POLYAMINES CONTAINING ACID GROUPS AND THEIR PREPARATION PROCESS |
FR2280361A2 (en) * | 1974-08-02 | 1976-02-27 | Oreal | HAIR TREATMENT AND CONDITIONING COMPOSITIONS |
LU64371A1 (en) * | 1971-11-29 | 1973-06-21 |
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1974
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1975
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- 1975-08-01 CH CH1010375A patent/CH579909A5/xx not_active IP Right Cessation
- 1975-08-01 BE BE158890A patent/BE832063R/en not_active IP Right Cessation
- 1975-08-01 GB GB3228575A patent/GB1510488A/en not_active Expired
- 1975-08-01 DE DE19752534514 patent/DE2534514C2/en not_active Expired
- 1975-08-01 CA CA232,769A patent/CA1066449A/en not_active Expired
- 1975-08-01 DK DK350875A patent/DK163478C/en active
- 1975-08-01 BR BR7504935A patent/BR7504935A/en unknown
- 1975-08-01 DE DE19752560488 patent/DE2560488C2/de not_active Expired
- 1975-08-01 NL NL7509188A patent/NL177730C/en active Search and Examination
- 1975-08-01 GB GB42977A patent/GB1510489A/en not_active Expired
- 1975-08-01 AT AT598575A patent/AT355727B/en not_active IP Right Cessation
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1984
- 1984-11-09 JP JP23538684A patent/JPS60142910A/en active Granted
- 1984-12-10 JP JP26060984A patent/JPS60142909A/en active Granted
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DE2560488C2 (en) | 1987-12-03 |
JPS6335608B2 (en) | 1988-07-15 |
BE832063R (en) | 1976-02-02 |
JPS6335607B2 (en) | 1988-07-15 |
NL7509188A (en) | 1976-02-04 |
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DK163478C (en) | 1992-07-27 |
AU8359675A (en) | 1977-02-03 |
JPS60142910A (en) | 1985-07-29 |
ATA598575A (en) | 1979-08-15 |
DK163478B (en) | 1992-03-09 |
NL177730B (en) | 1985-06-17 |
BR7504935A (en) | 1976-07-27 |
DK350875A (en) | 1976-02-03 |
NL177730C (en) | 1985-11-18 |
DE2534514A1 (en) | 1976-02-12 |
JPS60142909A (en) | 1985-07-29 |
DE2534514C2 (en) | 1988-12-22 |
AT355727B (en) | 1980-03-25 |
FR2280361B2 (en) | 1981-11-13 |
GB1510489A (en) | 1978-05-10 |
JPS5151528A (en) | 1976-05-07 |
CH579909A5 (en) | 1976-09-30 |
FR2280361A2 (en) | 1976-02-27 |
IT1050594B (en) | 1981-03-20 |
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