WO2006013271A1 - Compositions cosmetiques contenant au moins un agent conditionneur et au moins un copolymere ethylenique a greffons polyethyleneglycol - Google Patents
Compositions cosmetiques contenant au moins un agent conditionneur et au moins un copolymere ethylenique a greffons polyethyleneglycol Download PDFInfo
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- WO2006013271A1 WO2006013271A1 PCT/FR2005/001702 FR2005001702W WO2006013271A1 WO 2006013271 A1 WO2006013271 A1 WO 2006013271A1 FR 2005001702 W FR2005001702 W FR 2005001702W WO 2006013271 A1 WO2006013271 A1 WO 2006013271A1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N C1CCCCC1 Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N CC1CCCC1 Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N CN1CCN(C)CC1 Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- A61K8/91—Graft copolymers
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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
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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
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
-
- 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
Definitions
- the present invention relates to compositions comprising at least one conditioning agent and at least one ethylene copolymer with polyethylene glycol grafts. BACKGROUND OF THE INVENTION The present invention relates to compositions comprising at least one conditioning agent and at least one ethylene copolymer with polyethylene glycol grafts.
- the object of the present invention is to provide cosmetic compositions comprising polymers capable of providing a real styling effect while retaining an acceptable cosmetic to the compositions, and in particular low viscosity polymers which only slightly modify the viscosity of the compositions comprising them. .
- polymers comprising, inter alia, monomers of the polyethylene glycol (meth) acrylate type as defined below, could make it possible to produce rinsed or non-rinsed styling compositions having adequate cosmetics.
- Polymers containing polyethylene glycol (meth) acrylate units (MPEG) are described in the prior art.
- copolymers based on MPEG and monomers (meth) acrylamides of C1-C8 alkyl which may comprise cationic monomers.
- these polymers comprise only a small proportion of cationic monomers, which does not allow them to generate adequate cosmetic effects, in particular a deposit on the hair which is sufficient to provide the desired properties.
- JP2002-322219 discloses polymers containing MPEG units in combination with hydrophobic monomers based on polypropylene glycol (PPO) or tetramethylene polyoxide, and cationic monomers.
- PPO polypropylene glycol
- tetramethylene polyoxide tetramethylene polyoxide
- compositions comprising cationic polymers in which the monomers of the PEG type are associated with monomers comprising quaternary amino units, whereas the presence of quaternary units can induce, as and when As the applica ⁇ tions, an additional deposit that can affect in some cases the cosmetic quality of the composition.
- these polymers contain a low cationic charge rate, of the order of 0.5 at 6%, which does not allow an optimal affinity for the hair.
- JP2000-302649 discloses a hair composition
- a hair composition comprising a polymer which comprises cationic or amphoteric monomers, monomers with a polyether group, in particular of the PEG or PPO type, as well as optional monomers which may be predominantly hydrophobic (for example, methacrylate). stearyl).
- hair compositions comprising a polymer which comprises MPEG-type monomers in as ⁇ sociation with ionic, cationic or amphoteric monomers, and additional monomers of the type (alkyl) alkyl (meth) acrylates in C1-C24, principally hydrophobic.
- hydrophobic comonomers for example of the butyl acrylate or stearyl type, does not make it possible to obtain adequate cosmetic properties, in particular do not make it possible to obtain a good disentangling of wet hair just after shampooing.
- the Applicant has demonstrated new polymers for applying a styling and conditioning effect to cosmetic hair products.
- the polymers according to the invention have interesting cosmetic properties, for example during application in a formulation of type after shampoo in combination with conditioning agents; it has indeed been found that the hair disentangles easily during rin ⁇ unitge, and they have softness; after drying, the compositions according to the invention also make it possible, once the hair is dried, a shaping of the hair that is particularly advantageous.
- the cosmetic compositions according to the invention are characterized in that they comprise:
- At least one conditioning agent chosen from syn ⁇ thesis oils, mineral oils, vegetable oils, fluorinated or perfluorinated oils, natural or synthetic waxes, silicones, cationic polymers whose cationic charge density is less than 5 meq / g, cationic proteins, cationic protein hydrolysates, ceramide-type compounds, cationic surfactants, fatty amines, fatty acids and their derivatives, as well as mixtures of these different compounds, and
- At least one ethylenic copolymer comprising, in% by weight relative to the total weight of the polymer
- cyclic radical will be understood to mean a monocyclic or polycyclic radical, which may itself be in the form of one or more rings, saturated and / or unsaturated, optionally substi ⁇ killed (for example cyclohexyl, cyclodecyl, benzyl or fluorenyl), but also a radical which comprises one or more of said rings (for example p-tertbutylcyclohexyl or 4-hydroxybenzyl).
- saturated and / or unsaturated radical means completely saturated radicals, totally unsaturated radicals, including aromatic radicals, as well as radicals comprising one or more double and / or triple bonds, the remainder of the bonds being single bonds.
- the ethylenic copolymer according to the invention therefore comprises at least one monomer of formula (I), which may be present alone or as a mixture,
- R 1 is a hydrogen atom or a linear or branched hydrocarbon radical of the type C p H 2 P + 1, with p being an integer between 1 and 12 inclusive;
- Z is a divalent group selected from -COO-, -CONH-, -CONCH 3 -, -OCO-, -O-, -SO 2 - -CO-O-CO- or -CO-CH 2 -CO-; - x is 0 or 1;
- R2 is a divalent carbon radical, saturated or unsaturated, optionally aroma ⁇ tick, linear, branched or cyclic, of 1 to 30 carbon atoms, com ⁇ take 1 to 18 heteroatoms selected from O, N, S, F, Si and P;
- n is an integer from 3 to 300 inclusive;
- R 3 is a hydrogen atom or a saturated or unsaturated, optionally aromatic, linear, branched or cyclic carbon radical, of 1 to 30 carbon atoms, which can comprise 1 to 20 heteroatoms chosen from O, N, S, F, Si and
- R 1 may represent a methyl, ethyl, propyl or butyl radical.
- R 1 represents hydrogen or a methyl radical.
- Z represents COO or CONH.
- x is 1.
- the heteroatom (s), when present, may be intercalated in the chain of said radical R2, or said radical R2 may be substituted by one or more groups including them, such as hydroxy or amino (NH 2, NHR 1 or NR 1 R "with R 'and R" identical or different representing a linear or branched C1-C22 alkyl, in particular methyl or ethyl).
- R2 may be: an alkylene radical such as methylene, ethylene, propylene, n-butylene, isobutylene, tert-butylene, n-hexylene, n-octylene, n-dodecylene, n-octadecylene, n-tetradecylene, n-docosanylene ;
- R'1 to R'4 identical or different, selected from H and a C1-C12 alkyl radical optionally comprising 1 to 8 heteroatoms selected from O, N, S, F, Si and P; in particular R 1 I to R ' 4 may be methyl and / or ethyl; a radical of formula -CH 2 -O-CO-O-, CH 2 -CH 2 -O-CO-O-, -CH 2 -CO-O-, -CH 2 -CH 2 -CO-O-, -CH 2 -O-CO-NH-, -CH 2 -CH 2 -O-CO-NH-; -CH 2 -NH-CO-NH-, -CH 2 - CH 2 -NH-CO-NH-, -CH 2 -CHOH-, -CH 2 -CH 2 -CHOH-, -CH 2 -CH 2 -CH (NH 2 ) -, -CH 2 --CH (NH 2 ) -, -CH 2
- n is between 5 and 200 inclusive, and even better between 7 and 100 inclusive, or even between 9 and 50 inclusive.
- R3 is a hydrogen atom; a benzyl or phenyl radical optionally substituted with a C1-C12 alkyl radical optionally comprising 1 to 8 heteroatoms chosen from O, N, S, F, Si and P; a C1-C30 alkyl radical, in particular C1-C22 or even C2-C16, optionally comprising 1 to 18 heteroatoms chosen from O, N, S, F, Si and P.
- benzyl, phenyl or alkyl radicals can comprise in particular a function chosen from the following functions:
- R6 and R7 independently of one another, selected from H or C1-C18 linear, branched or cyclic, especially methyl, optionally comprising 1 or more heteroatoms or bearing protective groups such as t-butyloxycarbonyl (also called BOC) or 9-fluorenylmethoxycarbonyl (also called FmoC).
- BOC t-butyloxycarbonyl
- FmoC 9-fluorenylmethoxycarbonyl
- R 3 radicals mention may be made of the methyl, ethyl, propyl, benzyl, ethylhexyl, lauryl, stearyl and behenyl (- (CH 2 ) 2 1 -CH 3 chains, and also the fluorinated alkyl chains such as, for example heptadecafluorooctyl sulfonyl amino ethyl CF 3 - (CF 2 ) T-SO 2 -N (C 2 HEJ) -CH 2 -CH 2 ; OR chains - CH 2 - CH 2 -CN, succinimido, maleimido, mesityl, tosyl, triethoxysilane or phtaiimide.
- the amine units and / or the anionic groups of the monomer of formula (I) may optionally be neutralized.
- the amine units of the monomer may optionally be neutralized.
- the salts mention may be made of the salts of mineral acids, such as sulfuric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid and boric acid. Mention may also be made of organic acid salts, which may comprise one or more carboxylic acid, sulfonic acid or phosphonic acid groups. It may be linear, branched or cyclic aliphatic acids or aromatic acids. These acids may furthermore comprise one or more heteroatoms chosen from O and N, for example in the form of hydroxyl groups. These include propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid.
- the neutralization of the anionic groups can be carried out by an inorganic base, such as LiOH, NaOH, KOH, Ca (OH) 2 , NH 4 OH, Mg (OH) 2 or Zn (OH) 2 ; or by an organic base such as a primary, secondary or tertiary alkylamine, especially triethylamine or butylamine.
- This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and / or oxygen atoms and may therefore comprise, for example, one or more alcohols; mention may especially be made of 2-amino-2-methyl-propanol, triethanolamine and dimethylamino-2-propanol. Mention may also be made of lysine or 3- (dimethylamino) propylamine.
- n is preferably between 3 and 100 inclusive, in particular 5 to 50 inclusive, or even 7 to 30 inclusive.
- the monomers of formula (I) that are most particularly preferred are chosen from poly (ethylene glycol) (meth) acrylates and methyl (poly) ethylene glycol (meth) acrylates, preferably those having a molecular weight between 350 and 15 000 g / mol, in particular between 500 and 8000 g / mol.
- poly (ethylene glycol) (meth) acrylates, and in particular those having a molecular weight of between 350 and 15,000 g / mol are preferred, especially between 500 and 8000 g / mol.
- CD 350 methoxy-poly (ethylene glycol 350) methacrylate
- CD 550 methoxy-poly (ethylene glycol 550) methacrylate
- M90G methoxy-poly (ethylene glycol methacrylate (9 repetition units)
- M230G methoxy-polyethylene glycol methacrylate (23 repeating units)) available from Shin-Nakamura Chemicals
- methoxy methacrylates poly (ethylene glycol) of average molecular weights 300, 475 or 1100, available from Sigma-Aldrich;
- methoxy-poly (ethylene glycol) methacrylates available from LAPORTE under the trade names: MPEG 350, MPEG 550,
- poly (ethylene glycol) phenyl ether acrylates of average molecular weights 236, 280 or 324 available from Aldrich;
- the monomer of formula (I) has a molecular weight of between 350 and 15000 g / mol, in particular between 500 and 8000 g / mol.
- the monomer of formula (I), alone or as a mixture, is present in a proportion of 10% inclusive of 60% by weight, relative to the weight of the final polymer, in particular from 20% to 55% inclusive by weight, preferably from 30% to 50% inclusive by weight.
- the ethylenic copolymer according to the invention also comprises at least one "essentially cationic" monomer, or one of its salts, chosen from: (i) one or more cationic monomers of formula (IIa), - (ii) one or more amphoteric monomers of formulas (IIc) and (IId), and
- the "essentially cationic" monomer is chosen from the cationic monomers of formula (IIa) and the amphoteric monomers of formula (Ile) or (Hd), preferably from cationic monomers of formula (IIa).
- cationic monomer means a monomer comprising units capable of possessing a cationic charge in the pH range comprised between 3 and 12. These units do not necessarily have a perma ⁇ nent charge whatever the pH. The cationic unit does not need to be protonated at each of these pH's.
- R1 is a hydrogen atom or a linear or branched hydrocarbon radical of the type CpHbp + 1, with p being an integer between 1 and 12, inclusive;
- R 1 may represent a methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl or tert-butyl radical.
- R 1 represents hydrogen or a methyl radical.
- Z 1 is a divalent group chosen from -COO-, -CONH-, -CONCH3-, -OCO- or -O-, -SO 2 - -CO-O-CO- or -CO-CH 2 -CO-;
- Z ' is selected from COO and CONH.
- x ' is 0 or 1, preferably 1.
- R'2 is a divalent carbon radical, saturated or unsaturated, optionally aroma ⁇ tick, linear, branched or cyclic, from 1 to 30 carbon atoms, com ⁇ take 1 to 18 heteroatoms selected from O, N, S, F , Si and P;
- the heteroatom (s) when they are present, may be inserted in the chain of said radical R'2, or said radical R'2 may be substituted by one or more groups including them, such as hydroxy or amino (NH 2, NHR 1 or NR'R "with R 'and R" identical or different representing a linear or branched C1-C22 alkyl, especially methyl or ethyl).
- R'2 can be: an alkylene radical such as methylene, ethylene, propylene, n-butylene, isobutylene, tert-butylene, n-hexylene, n-octylene, n-dodecylene, n-octadecylene, n-tetradecylene, n-docosanylene;
- - X is a group of formula -N (R 6) (R 7) or -P (Re) (R?) Or - P + R 6 R 7 Re, with R6, R7 and R8 representing , independently of one another, either (i) a hydrogen atom, or (ii) a linear, branched or cyclic, saturated or unsaturated, optionally aromatic, alkyl group comprising from 1 to 18 carbon atoms, which may be comprise 1 to 10 heteroatoms selected from O, N, S, F, Si and P; or (iii) R6 and R7 may form with the nitrogen or phosphorus atom, a first cycle, saturated or unsaturated, optionally aromatic, comprising in total 5, 6, 7 or 8 atoms, and in particular 4, 5 or 6 carbon atoms and / or 2 to 4 heteroatoms selected from O, S and N; said first cycle being fusible with one or more other rings, saturated or unsaturated, optionally aromatic, each comprising 5, 6 or 7 atoms,
- R6 and R7 can be chosen from hydrogen, a methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl, isobutyl, octyl, lauryl or stearyl group.
- R6 and R7 are independently selected from H, CH3 and C2H5.
- X may represent a group -R'6-N-R'7- in which R'6 and R'7 form with the nitrogen atom a ring, saturated or unsaturated, possibly aromatic , comprising in total 5, 6, 7 or 8 atoms, and in particular 4, 5 or 6 carbon atoms and / or 2 to 4 heteroatoms chosen from O, S and N; said cycle being fusible with one or more other rings, saturated or unsaturated, optionally aromatic, each comprising 5, 6 or 7 atoms, and especially 4, 5, 6, 7 or 8 carbon atoms and / or 2 to 4 heteroatoms selected ⁇ if among O, S and N.
- X may constitute an aromatic or non-aromatic ring comprising a tertiary amine group or may represent an aromatic or non-aromatic heterocycle containing a tertiary nitrogen.
- X include pyridine, indole, isoindolinyl, imidazolyl, imidazolinyl, piperidinyl, pyrazolynyl, pyrazolyl, quinoline, pyrazolinyl, pyridinyl, piperazinyl, pyrrolidinyl, quinidinyl, thiazolinyl, morpholine, guanidino, amidino radicals. , phosphonium, and mixtures thereof.
- the guanidino and amidino groups are respectively of formula:
- the monomers of formula (IIa) can be neutralized by neu ⁇ tralisants agents of different chemical nature.
- the neutralizing agent may be chosen from inorganic or organic acids in the Bronsted sense and preferably from organic acids.
- it may be chosen from neutralizing agents having a log P of less than or equal to 2, for example between -8 and 2, preferably between -6 and 1, in particular between -6 and 0.
- the log P values are known and are determined according to a standard test which determines the concentration of the neutralizing agent in octanol-1 and water.
- the mineral acids that can be used include sulfuric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid and boric acid.
- the neutralizing agents of the organic acid type may be chosen from linear, branched or cyclic aliphatic acids and / or unsaturated or aromatic acids, and may especially comprise 1 to 1000 carbon atoms, especially 2 to 500 carbon atoms. They have at least one Bronsted acid function, and in particular one or more carboxylic acid, sulphonic acid and / or phosphonic acid groups. They may also comprise one or more heteroatoms chosen from O, N, Si, F and P, for example in the form of hydroxyl groups.
- fatty acids having 6 to 32 carbon atoms, in particular 8 to 28, linear, branched or cyclic, saturated or unsaturated, optionally aromatic, and comprising at least one COOH or sulphonic acid function (- SO 3 H).
- hydroxy acids in particular alpha-hydroxy acids, having 6 to 32 carbon atoms, in particular 8 to 28 linear atoms.
- alkylbenzenesulphonic acids in which the alkyl group may comprise from 4 to 30, in particular from 6 to 24, carbon atoms.
- amphoteric neutralizing agents in particular of the alkylbetaine or alkylamidopropylbetaine type, in which the alkyl group may comprise 4 to 30, especially 6 to 24, carbon atoms; cocoamidopropylbetaine may be mentioned in particular.
- alpha-hydroxyethanoic acid alpha-hydroxyoctanoic acid, alpha-hydroxycaprylic acid, ascorbic acid, acetic acid, benzoic acid, behenic acid, capric acid, citric acid, caproic acid, caprylic acid, dodecylbenzene sulfonic acid, 2-ethylcaproic acid, folic acid, fumaric acid, galactaric acid, gluconic acid, glycolic acid, 2-hexadecyl eicosanoic acid, hydroxycaproic acid, 12-hydroxystearic acid, isolauric acid (or 2-butyl octanoic acid), isomyristic acid (or 2-hexyl octanoic acid) , isoarachidic acid (or 2-octyl dodecanoic acid), isoloinoceric acid (or 2-decyltetradecanoic acid), lactic acid, lauric acid, mal
- the neutralizing agent used may be caproic acid, 2-ethylcaproic acid, oleic acid, behenic acid, stearic acid, acetic acid, citric acid, acid and the like.
- neutralization is meant the action of an organic acid according to the invention and comprising at least one Bronsted acid function, on all or part of the monomers and / or polymer mentioned above, comprising at least one less a basic function in the sense of Bronsted.
- the neutralizing agent alone or as a mixture, may be added in an amount of 0.01 to 3 molar equivalents, in particular 0.05 to 2.5 or even 0.1 to 2 molar equivalents, relative to the amine functions. total of the polymer or monomers.
- the neutralizing agent can be present in an amount necessary to neutralize 1 to 99%, in particular 5 to 90%, or even 10 to 80%, of the total amino functions of the polymer or monomers; which means that it is present in an amount of 0.01 to 0.99 molar equivalents, in particular 0.05 to 0.9 or even 0.1 to 0.8 molar equivalents.
- the neutralizing agent may be present in an amount necessary to neutralize 101 to 300%, especially 120 to 250%, or even 150 to 200% total amine functions of the polymer or monomers; this may be the case when it is desired to provide the polymer with a pH range and / or a suitable ionic strength vis-à-vis the intended formulations. It may therefore be present in an amount of 1.0 to 3 molar equivalents, in particular 1, 2 to 2.5 or even 1.5 to 2 molar equivalents, relative to the total amine functions of the polymer or monomers.
- the neutralizing agent alone or as a mixture, is present in a stoichiometric amount relative to the total amine functional groups of the polymer or monomers; it is therefore present in an amount necessary to neutralize 100% of the amine units of the polymer or monomers, ie 1 molar equivalent.
- the nature and amount of neutralizing agent may be determined by those skilled in the art so as ultimately to obtain a water soluble or dispersible polymer.
- Y is a group chosen from -COOH, -SO 3 H, -SOO 3 H, -PO 3 H 2 and -OPO 3 H 2 .
- the neutralization of the anionic groups can be carried out by an inorganic base, such as LiOH, NaOH, KOH, Ca (OH) 2 , NH 4 OH, Mg (OH) 2 or Zn (OH) 2 ; or by an organic base such as a primary, secondary or tertiary alkylamine, especially triethylamine or butylamine.
- This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and / or oxygen atoms and may therefore comprise, for example, one or more alcohols; mention may especially be made of 2-amino-2-methyl-propanol, triethanolamine and dimethylamino-2-propanol. Mention may also be made of lysine or 3- (dimethylamino) propylamine. It is understood that according to the state of the art, the groups SO 4 H 2 and PO 4 H 2 are linked to R '2 by the oxygen atom while the groups SO 3 H and PO 3 H are linked at R'2 respectively via the S and P atoms.
- X 1+ is a divalent group of formula -N + (Ro) (Ry) - with R6 and R7 representing, independently of each other, either (i) a hydrogen atom or (ii) ) a linear, branched or cyclic, optionally aromatic, alkyl group comprising from 1 to 25 carbon atoms, which can comprise 1 to 20 heteroatoms chosen from O, N, S and P; or (iii) R6 and R7 can form with the nitrogen atom a first ring, saturated or unsaturated, optionally aromatic, comprising in total 5, 6, 7 or 8 atoms, and in particular 4, 5, 6 or 7 carbon atoms and / or 2 to 3 heteroatoms selected from O, S and N; said first cycle being fusible with one or more other rings, saturated or unsaturated, optionally aromatic, each comprising 5, 6, 7 or 8 atoms, and in particular 4, 5, 6 or 7 carbon atoms and / or 2 to 3 heteroatoms selected from O, S and N.
- Preferred X 1+ radicals include pyridine, indolyl, isoindolinyl, imidazolyl, imidazolinyl, piperidinyl, pyrazolynyl, pyrazolyl, quinoline, pyrazolinyl, pyridinyl, piperazinyl, pyrrolidinyl, quinidinyl and thiazolinyl radicals. , morpholine, guanidino, amidino, and mixtures thereof.
- Y ' " is a group chosen from -COO ' , -SO 3 " 1 -OSO 3 " , -PO 3 2" and -OPO 3 2 " .
- - R'3 is a divalent carbon radical, saturated or unsaturated, optionally aroma ⁇ tick, linear, branched or cyclic, from 1 to 30 carbon atoms, com ⁇ take 1 to 18 heteroatoms selected from O, N, S, F, Si and P.
- radical R'3 the or heteroatoms, when they are present, may be intercalated in the chain of said radical R'3, or said radical R'3 may be substituted by one or more groups including them such as hydroxy or amino (NH 2 , NHR 'or NR 1 R "with R 1 and R" same or different representative
- C 1 -C 12 alkyl radical optionally comprising 1 to 5 heteroatoms selected from O, N, S, F, Si and P;
- - n 1 is between 1 and 100, preferably 1 and 5 inclusive.
- X " + is a group of formula -N + ReRyRs with R6, R7 and R8 representing, independently of one another, either (i) a hydrogen atom or ( ii) a linear, branched or cyclic, optionally aromatic, alkyl group comprising from 1 to 18 carbon atoms, which can comprise 1 to 5 heteroatoms chosen from O, N, S and P, or (iii) R 6 and R 7 can form with nitrogen atom a first ring, saturated or unsaturated, optionally aromatic, comprising in total 5, 6 or 7 atoms, and in particular 4, 5 or 6 carbon atoms and / or 2 to 3 heteroatoms chosen from O, S and N, said first cycle being fusible with one or more other rings, saturated or unsaturated, optionally aromatic, each comprising 5, 6 or 7 atoms, and in particular 4, 5, 6 or 7 carbon atoms and / or 2 with 3 heteroatoms selected from O, S and N.
- R6, R7 and R8 may be chosen from hydrogen, a methyl group, ethyl, propyl, isopropyl, n-butyl, t-butyl, isobutyl, octyl, lauryl or stearyl.
- Preferred X " + radicals include trimethylammonium, triethylammonium, N, N-dimethyl, N-octylammonium, N, N-dimethyl, N-laurylammonium, monomers of the formula (IIc) or (IId).
- N, N-dimethyl-N- (2-methacryloyloxyethyl) -N- (3-sulfopropyl) ammonium betaine especially SPE from Raschig
- N, N-dimethyl-N (3- (3-methacrylamidopropyl) -N- (3-sulfopropyl) ammonium betaine
- Raschig SPP (3- (3-methacrylamidopropyl) -N- (3-sulfopropyl) ammonium betaine
- Raschig SPV 1- (3-sulfopropyl) -2-vinylpyridinium betaine
- the 'essentially cationic' monomer is chosen from the melan ⁇ cation of cationic and / or amphoteric monomers with anionic monomers
- said anionic monomers are preferably present in a proportion of 5 to 40% by weight, relative to the weight of the cationic and / or amphoteric res + anionic ", especially from 10 to 30% by weight, preferably from 15 to 25% by weight.
- the essentially cationic monomer 1 is present in a proportion of 40 to 90% by weight relative to the weight of the final polymer, in particular 45 to 80% by weight, preferably 50 to 70% by weight.
- the polymer according to the invention comprises the monomers of formula (I) and the ionic monomers (the cationic monomers + the possible amphoteric and anionic monomers) in a weight ratio ranging from 60/40 to 40/60, with a preference for a 50/50 ratio.
- the ethylenic copolymer according to the invention may comprise op ⁇ tionally other monomers than those mentioned above. These additional monomers are therefore nonionic.
- hydrophilic monomer monomers having a logarithm value of the octanol-1 / water apparent partition coefficient, also called log P, less than or equal to 2, for example between -8 and 2, preferably less than or equal to 1, 5, in particular less than or equal to 1, and in particular com ⁇ between -7 and 1, or between -6 and 0.
- the log P values are known and are determined according to a standard test which determines the concentration of the monomer in octanol-1 and water.
- the values can be calculated using the software Advan ⁇ ced Chemistry Development Software solaris V4.67; they can also be obtained from Exploring QSAR: hydrophobic, electronic and steric constants (ACS professional reference book, 1995).
- the additional hydrophilic monomers may especially be chosen from those of formula (III), alone or as a mixture,
- R'i is hydrogen or -CH 3 ;
- Z " is a divalent group chosen from -COO-, -CONH-, -CONCH 3 -, -OCO-, -SO 2 , -CO-O-CO-, -CO-CH 2 -CO- or -O- preferably COO and CONH;
- R is a saturated or unsaturated, optionally aromatic, linear, branched or cyclic, carbon radical of 1 to 30 carbon atoms, which may comprise
- heteroatoms selected from O, N, S, F, Si and P;
- the heteroatom (s), when they are present, can be inserted in the chain of said radical or said radical can be substi ⁇ killed by one or more groups including them such as hydroxy, ester, amide, urethane or urea.
- R may be methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, benzyl, or a radical of formula -CH 2 - CH 2 -CH 2 OH, -CH 2 -CH 2 - OH, -CH 2 -CH 2 -CH 2 OH or furfuryl
- the additional hydrophilic nonionic monomers are especially chosen from the following monomers: methyl methacrylate, methyl acrylate, ethyl methacrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, tetrahydrofurfuryl methacrylate, tetrahydrofurfuryl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, methacrylate and the like.
- the additional monomer may not be present in the polymer according to the invention (0%), or may be present in an amount of up to 50% by weight, relative to the weight of the polymer. final; in particular it may be present in an amount of 0.1 to 35% by weight, preferably 1 to 25% by weight, for example 3 to 15% by weight, or even 5 to 9.5% by weight by weight, based on the total weight of the polymer.
- this additional monomer was chosen from methyl acrylate, methyl methacrylate and isopropyl acrylate, these monomers could not be present in a greater amount or equal to 10% by weight.
- the copolymer according to the invention does not comprise monomers other than those of formulas (I), (IIa), (Ub), (IIc) and (Hd).
- the copolymer according to the invention comprises only monomers of formulas (I) and (IIa).
- the polymer which can be used according to the invention comprises the monomers of formula (I) and the "essentially cationic" monomers in a weight ratio that can range from 60/40 to 40/60, with a preference for a 50/50 ratio.
- the polymer consists essentially of monomer of formula (I), alone or as a mixture, and of monomers of formula (IIa), alone or as a mixture.
- the monomer of formula (I), alone or as a mixture is present in a proportion of 10 to 60% by weight, relative to the weight of the final polymer, in particular from 20 to 60% by weight, preferably from 30 to 50% by weight, and is chosen from, alone or as a mixture, poly (ethylene glycol) (meth) acrylates, preferably those having a molecular weight of between 350 and 13000 g / mol, in particular between 500 and 8000 g / mol . and
- the substantially cationic monomer 1 is present in a proportion of 40 to 90% by weight relative to the weight of the final polymer, in particular from 40 to 80% by weight, preferably from 50 to 70% by weight, and is chosen from alone or in a mixture, dimethylaminopropyl (meth) acrylamide, dimethylaminoethyl (meth) acrylamide, diethylaminoethyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, vinylimidazole, vinylpyridine, (meth) morpholinoethyl acrylate; and
- the polymer being preferably neutralized with an organic acid neutralizing agent, especially chosen from 2-ethylcaproic acid, oleic acid, behenic acid, stearic acid, acetic acid and citric acid, tartaric acid, betaine hydrochloride and / or gluconic acid, and preferably behenic acid and / or betaine hydrochloride.
- organic acid neutralizing agent especially chosen from 2-ethylcaproic acid, oleic acid, behenic acid, stearic acid, acetic acid and citric acid, tartaric acid, betaine hydrochloride and / or gluconic acid, and preferably behenic acid and / or betaine hydrochloride.
- the monomer of formula (I), alone or as a mixture is present in a proportion of 10 to 60% by weight, relative to the weight of the final polymer, in particular from 20 to 60% by weight, preferably from 30 to 50% by weight, and is chosen from, alone or as a mixture, the (meth) acrylates of poly (ethylene glycol), preferably those having a molecular weight of between 350 and 13000 g / mol, in particular between 500 and 8000 g / mol; and
- the substantially cationic monomer 1 is present in a proportion of 40 to 90% by weight relative to the weight of the final polymer, in particular from 40 to 80% by weight, preferably from 50 to 70% by weight, and is chosen from alone or in a mixture, dimethylaminopropyl (meth) acrylamide, and
- polymers according to the invention can be prepared according to the conventional methods of conventional radical polymerization, which are well known to those skilled in the art, and as described, for example, in the work "Chemistry and physico ⁇ chemistry of polymers" by Gnanou et al. . (Dunod edition).
- these polymers may be prepared by: direct polymerization in solution in water with or without pre-neutralization of the cationic unit and / or anionic unit;
- polymerization in an organic solvent such as ethanol or methyl ethyl ketone, with or without pre-neutralization of the cationic unit and / or of the anionic unit, followed by a solution or dispersion step in the water with evaporation of the solvent.
- organic solvent such as ethanol or methyl ethyl ketone
- These polymerizations may be carried out in the presence of a radical initiator, especially of the peroxide (Trigonox 21 S: tert-Butyl peroxy-2-ethylhexanoate) or azo (AIBN V 50: 2,2'-azo-bis (2-amidinopropane) type. dihydrochloride), which may be present in a proportion of 0.3 to 5% by weight relative to the total weight of the monomers.
- a radical initiator especially of the peroxide (Trigonox 21 S: tert-Butyl peroxy-2-ethylhexanoate) or azo (AIBN V 50: 2,2'-azo-bis (2-amidinopropane) type. dihydrochloride), which may be present in a proportion of 0.3 to 5% by weight relative to the total weight of the monomers.
- the polymers according to the invention are uncrosslinked. They are in the form of random ethylenic copolymers, preferably film-forming copolymers, of one or more ethylenic monomers containing PEG groups (the PEG groups are pendent along the backbone) and of one or more ethylene-ethylenic monomers comprising cationic functions. (Neutralized and non-quaternary amines) and / or betaines and, optionally, one or more other nonionic hydrophilic ethylenic comonomers, monovalent.
- ethylenic polymer is meant a polymer obtained by polymerization of monomers comprising ethylenic unsaturation.
- film-forming polymer is meant a polymer capable of forming on its own or in the presence of an auxiliary film-forming agent, a continuous and adherent film on a support, in particular on keratin materials. They have a weight average molecular weight (Mw) which is preferably between 500 and 5,000,000, in particular between 1,000 and 3,000,000 and more preferably between 2,000 and 2,000,000, or even 4,000 and 500 000, among others 7000 and 250 000, even better 8 000 and 100 000.
- Mw weight average molecular weight
- the weight average molecular weights (Mw) are determined by gel permeation chromatography or by light scattering, depending on the accessibility of the the method (solubility of the polymers considered).
- the polymers that may be used according to the invention are preferably transportable in an aqueous medium, that is to say that they are preferably water-soluble or water-dispersible.
- water-soluble it is meant that it is soluble in water, at least 5% by weight, at 25 ° C, and forms a clear solution.
- hydrodispersible is meant that it forms in water, at a concentration of 5% by weight, at 25 0 C, a stable dispersion of fine particles, generally spherical.
- the average particle size constituting said dispersion is less than 1 ⁇ m and, more generally, varies between 5 and 400 nm, preferably from 10 to 250 nm. These particle sizes are measured by light diffusion.
- the dissolution or dispersion in water can be carried out by direct solubilization of the polymer if it is soluble, or by neutralization of the amino units and / or acidic units so as to render the polymer soluble or dissolved. persible in the water.
- the dissolution or aqueous dispersion can also be carried out via an intermediate step of solubilization in an organic solvent followed by the addition of water before evaporation of the organic solvent.
- the polymers which can be used according to the invention advantageously have a viscosity in water that is adequate with the applications envisaged, which can be, for example, between 1 and 1000 mPa.s, preferably between 1, 5 and 750 mPa.s, and even more preferably between 2 and 500 mPa.s.
- the viscosity is measured using a BROOKFIELD viscometer, for a solution at 15% by weight of polymer in water or methyl ethyl ketone (solvent chosen as a function of the solubility of the polymer and / or the method of polyméri ⁇ sation), at 25 ° C, with a needle-type mobile (spindle) selected from the models numbers 00 to 07 Brookfield, preferably the mobile No. 1; for a measuring time of 5 minutes, at a speed of between 0.1 and 6 rpm.
- the viscosity is measured after complete dissolution of the polymer in water or methyl ethyl ketone.
- the polymers that may be used according to the invention may preferably have a glass transition temperature (Tg) of between -15 ° C. and 20 ° C., in particular -120 ° C. and 10 ° C., better still between -100 ° C. C and 0 ° C; the Tg is measured according to the method given before the examples.
- the polymers that may be used according to the invention may preferably have a melting temperature (Tf) of between -100 ° C. and 80 ° C., especially between -80 ° C. and 50 ° C., better still between -70 ° C. and 45 ° C. , even -1O 0 C and 25 0 C.
- the polymers that can be used according to the invention preferably have a water uptake of between 3% and 150% by weight, preferably between 4% and 100% by weight, and especially between 5% and 50% by weight, at 75% by weight. % relative humidity (75% RH); the water uptake is measured according to the method given before the examples. They can also have a water uptake of between 3% and 200% by weight, preferably between 2.5% and 150% by weight, in particular between 3% and 100% by weight, at 85% relative humidity (85%). % RH).
- the polymers may be present in the composition in solubilized form, for example in water or an organic solvent, or in the form of an aqueous or organic dispersion.
- compositions according to the invention can be used in the cosmetic compositions according to the invention in a proportion of 0.01 to 30% by weight of dry matter, in particular from 0.1 to 20% by weight, or even from 0.1 to 10% by weight, still better from 0.5 to 3% by weight, relative to the total weight of the composition.
- conditioning agent is understood to mean any agent whose function is to improve the cosmetic properties of the hair, in particular the softness, the gloss, the disentangling, the touch, the smoothing, the static electricity. .
- the conditioning agents may be in liquid, semi-solid or solid form such as, for example, oils, waxes or gums.
- the conditioning agents may be chosen from synthetic oils such as polyolefins, mineral oils, vegetable oils, fluorinated or perfluorinated oils, natural or synthetic waxes, silicones, cationic polymers, cationic proteins, cationic protein hydrolyzates, ceramide compounds, cationic surfactants, fatty amines, fatty acids and their derivatives as well as mixtures of these various compounds.
- synthetic oils such as polyolefins, mineral oils, vegetable oils, fluorinated or perfluorinated oils, natural or synthetic waxes, silicones, cationic polymers, cationic proteins, cationic protein hydrolyzates, ceramide compounds, cationic surfactants, fatty amines, fatty acids and their derivatives as well as mixtures of these various compounds.
- the preferred conditioning agents according to the invention are cationic polymers, cationic surfactants, silicones and mixtures of these compounds.
- the synthetic oils are in particular polyolefins, in particular poly- ⁇ -olefins and more particularly:
- Isobutylene oligomers with a molecular weight of less than 1000 are preferably used and their mixtures with polyisobutylenes with a molecular weight greater than 1000 and preferably between 1000 and 15000.
- mineral oils that can be used in the compositions of the invention are preferably chosen from the group formed by:
- hydrocarbons such as hexadecane and paraffin oil
- the animal or vegetable oils are chosen in particular from triglycerides of fatty acid C8-C30 and preferably from sweet almond oil, avocado oil, castor oil, olive oil, jojoba oil, sunflower oil, wheat germ oil, sesame oil, peanut oil, grapeseed oil, soybean oil, oil sesame oil, rapeseed oil, safflower oil, coconut oil, corn oil, hazelnut oil, shea butter, palm oil, kernel oil apricot, calophyllum oil, fish oils, tricaprocaprylate of glycerol, or vegetable or animal oils of formula R9COOR 10 in which Rg CO represents an acyl radical having from 8 to 30 carbon atoms and R 10 represents a linear or branched hydrocarbon chain containing from 3 to 30 carbon atoms, in particular alkyl or alkenyl, for example, purcellin oil or liquid jojoba wax; .
- Waxes are natural (animal or vegetable) or synthetic substances that are solid at room temperature (20 ° -25 ° C). They are insoluble in water, soluble in oils and are capable of forming a water-repellent film.
- waxes for example, D.D. Dorgan, Drug and Cosmetic Industry, December 1983, pp. 30-33.
- the wax or the waxes are chosen in particular from Carnauba wax, Candelila wax, and Alfa wax, paraffin wax, ozokerite, vegetable waxes such as olive wax, rice wax , hydrogenated jojoba wax or absolute waxes of flowers such as the essential wax of blackcurrant sold by the company BERTIN (France), animal waxes such as beeswax, or modified beeswax (cerabellina) ; other waxes or waxy raw materials that can be used according to the invention are, in particular, marine waxes, such as the one sold by SOPHIM under the reference M82, and polyethylene or polyolefin waxes in general.
- the cationic polymers that may be used according to the invention have a cationic charge density of less than 5 meq / g, preferably ranging from 0.1 to 4 meq / g and more particularly from 0.2 to 3 meq / g and even more especially from 0.3 to 2 meq / g.
- the charge density can be determined by the Kjeldahl method. It is generally measured at a pH of the order of 3 to 9.
- the cationic polymers other than the PEG-bonded polymers that can be used in accordance with the present invention can be chosen from all those already known per se as improving the cosmetic properties of the hair, namely in particular those described in the patent application EP-A-0. 337,354 and in the French patent applications FR-A-2,270,846, 2,383,660, 2,598,611, 2,470,596 and 2,519,863 and having a cationic charge density as defined above.
- the expression "cationic polymer” denotes any polymer containing cationic groups and / or ionizable groups in cationic groups.
- the preferred cationic polymers are chosen from those containing units containing primary, secondary, tertiary and / or quaternary amine groups that may either be part of the main polymer chain or may be carried by a lateral substituent directly connected thereto.
- the cationic polymers used generally have an average molecular weight in number or in weight of between about 500 and 5 ⁇ 10 6 , and preferably between 10 3 and 3 ⁇ 10 6 approximately.
- cationic polymers mention may be made more particularly of the polymers of the polyamine, polyaminoamide and quaternary polyammonium type. These are known products.
- polymers of the polyamine, polyamidoamide or quaternary polyammonium type, usable in accordance with the present invention are those described in French Pat. Nos. 2,505,348 or 2,542,997. Among these polymers, it is possible to to quote :
- R3 which may be identical or different, denote a hydrogen atom or a CH3 radical
- A which may be identical or different, represent a linear or branched alkyl group of 1 to 6 carbon atoms, preferably 2 or 3 carbon atoms or a hydroxyalkyl group of 1 to 4 carbon atoms;
- R4, R5, RQ identical or different, represent an alkyl group having 1 to 18 carbon atoms or a benzyl radical and preferably an alkyl group having 1 to 6 carbon atoms;
- R 1 and R 2 which are identical or different, represent hydrogen or an alkyl group having from 1 to 6 carbon atoms and preferably methyl or ethyl;
- X denotes an anion derived from a mineral or organic acid such as a methosulphate anion or a halide such as chloride or bromide.
- the copolymers of the family (1) may also contain one or more units derived from comonomers which may be chosen from the family of acrylamides, methacrylamides, diacetones acrylamides, acrylamides and methacrylamides substituted on the nitrogen by lower alkyls ( C1-C4), acrylic or methacrylic acids or their esters, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, vinyl esters.
- comonomers which may be chosen from the family of acrylamides, methacrylamides, diacetones acrylamides, acrylamides and methacrylamides substituted on the nitrogen by lower alkyls ( C1-C4), acrylic or methacrylic acids or their esters, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, vinyl esters.
- copolymers of acrylamide and of dimethylaminoethyl methacrylate quaternized with dimethyl sulphate or with a dimethyl halide such as that sold under the name HERCOFLOC by the company HERCULES
- copolymers of acrylamide and of methacryloyloxyethyltrimethylammonium chloride for example described in the patent application EP-A-080976 and sold under the name BINA QUAT P 100 by the company CIBA GEIGY
- vinylpyrrolidone / dialkylaminoalkyl acrylate or methacrylate copolymers which may or may not be quaternized. These polymers are described in detail in French Patents 2,077,143 and 2,393,573. dimethylaminoethyl methacrylate / vinylcaprolactam / vinylpyrrolidone terpolymers,
- vinylpyrrolidone / methacrylamidopropyl dimethylamine copolymers and the vinylpyrrolidone / quaternized dimethylaminopropyl methacrylamide copolymers.
- cationic polysaccharides in particular cationic celluloses and cationic galactomannan gums.
- cationic polysaccharides mention may be made more particularly of cellulose ether derivatives containing quaternary ammonium groups, cationic cellulose copolymers or cellulose derivatives grafted with a quaternary ammonium water-soluble monomer, and cationic galactomannan gums.
- cellulose ether derivatives comprising quaternary ammo ⁇ nium groups described in French Patent 1,492,597. These polymers are also defined in the CTFA dictionary as qua ⁇ ternary ammoniums of hydroxyethylcellulose reacted with a group-substituted epoxide. trimethyl.
- Cationic cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer are described in particular in US Pat. No. 4 131 576, such as hydroxyalkyl celluloses, such as hydroxymethyl, hydroxyethyl or hydroxypropyl celluloses grafted in particular with a salt of methacryloylethyltrimethylammonium, methacrylmidopropyltrimethylammonium, dimethyldiallylammonium.
- cationic galactomannan gums are described more particularly in US Pat. Nos. 3,589,578 and 4,031,307, in particular guar gums containing cationic trialkylammonium groups.
- guar gums modified with a salt (eg chloride) of 2,3-epoxypropyltrimethylammonium are used.
- polymers consisting of piperazinyl units and straight or branched chain alkylene or hydroxyalkylene divalent radicals, optionally interrupted by oxygen, sulfur or nitrogen atoms or by aromatic or heterocyclic rings, as well as oxidation and / or quaternization products of these polymers.
- Such polymers are in particular described in French Patents 2,162,025 and 2,280,361;
- water-soluble polyaminoamides prepared in particular by polycondensation of an acidic compound with a polyamine; these polyaminoamines can be crosslinked by an epihalohydrin, a diepoxide, a dianhydride, an unsaturated dianhydride, a bis-unsaturated derivative, a bis-halohydrin, a bis-azetidinium, a bis-haloacyldiamine, a bis-alkyl halide. or alternatively by an oligomer resulting from the reaction of a bifunctional compound which is reactive with a bis-halohydrin, a bis-azetidinium, a bis-haloacyldiamine or a bis-halogenide.
- Such polymers are described in French patents 2 252 840 and 2 368 508;
- polyamino amide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation with difunctional agents Mention may be made, for example, of the adipic acid-diacoylaminohydroxyalkyldialoylene triamine polymers in which the alkyl radical contains from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl. Such polymers are described in particular in French Patent 1,583,363.
- adipic acid / dimethylaminohydroxypropyl / diethylene triamine polymers sold under the name "CARTARETINE F, F4 or F8" by SANDOZ.
- the molar ratio between the polyalkylene polylamine and the dicarboxylic acid being between 0.8: 1 and 1.4: 1; the polyamino amide being reacted being reacted with epichlorohydrin in a molar ratio of epichlorohydrin relative to the secondary amine group of the polyaminoamide of between 0.5: 1 and 1, 8: 1.
- Such polymers are especially described in US Patents 3,227,615 and 2,961,347.
- Polymers of this type are in particular marketed under the name "HERCOSETT 57" by the company Hercules Inc. by the company HERCULES in the case of the adipic acid / epoxypropyl / diethylene-triamine copolymer.
- alkyl diallyl amine or dialkyl diallyl ammonium co-cyclopolymers such as copolymers comprising as main constituent of the chain of units corresponding to formulas (I) or (I 1 ):
- R-J2 denotes a hydrogen atom or a methyl radical
- R-10 and Ru independently of each other, denote an alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group in which the alkyl group preferably has 1 to 5 carbon atoms, a lower amidoalkyl group.
- Q and R 1 -j may designate, together with the nitrogen atom to which they are attached, heterocyclic groups, such as piperidinyl or morpholinyl;
- Y " is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulphate, bisulphite, sulphate, phosphate
- R-10 and R 1 independently of one another, preferably denote an alkyl group having from 1 to 4 carbon atoms.
- Rj 3, Rj 4, Rj 5 and R-j ⁇ which may be identical or different, represent aliphatic, alicyclic or arylaliphatic radicals containing from 1 to 20 carbon atoms or lower hydroxyalkylaliphatic radicals, or else Rj 3, Rj 4, Rj 5 and R-j, together or separately, together with the nitrogen atoms to which they are attached, constitute heterocycles optionally containing a second heteroatom other than nitrogen or R-J3, R-14, R15 and R- jre represent a linear or branched C1-C6 alkyl radical substituted with a group nitrile, ester, acyl, amide or -CO-OR> J 7 -D or -CO-NH-R 17 -D wherein R 17 is alkylene and D is a quaternary ammonium group;
- A1 and B1 represent polymethylene groups containing 2 to 20 carbon atoms which may be linear or branched, saturated or unsaturated, and may contain, bound to or intercalated in the main chain, one or more aromatic rings, or one or more oxygen, sulfur or sulfoxide, sulfone, disulfide, amino, alkylamino, hydroxyl, quaternary ammonium, ureido, amide or ester, and X " refers to an anion derived from a mineral or organic acid;
- A1, R13 and R15 can form with the two nitrogen atoms to which they are attached a piperazine ring; furthermore, if A1 denotes a linear or branched, saturated or unsaturated alkylene or hydroxyalkylene radi ⁇ cal, B1 may also denote a (CH2) n -CO-D-OC- (CH2) n- group in which D denotes: a) a glycol residue of formula: -OZO-, where Z denotes a linear or branched hydrocarbon radical or a group corresponding to one of the following formulas: - (CH2-CH2-O) x-CH2-CH2-
- x and y denote an integer of 1 to 4, representing a defined and unique degree of polymerization or any number of 1 to 4 representative ⁇ an average degree of polymerization; b) a bis-secondary diamine residue such as a piperazine derivative; c) a bis-primary diamine residue of formula: -NH-Y-NH-, where Y de ⁇ sign a linear or branched hydrocarbon radical, or the divalent radical
- X " is an anion such as chloride or bromide.
- These polymers have an average molecular weight in number genera ⁇ ment between 1000 and 100000.
- R 1, R 2, R 3 and R 3 which are identical or different, denote an alkyl or hydroxyalkyl radical having from 1 to about 4 carbon atoms, n and p are integers ranging from about 2 to about 20 and X " is an anion derived from a mineral or organic acid.
- 9, R 20 and ⁇ 21> identical or different represent a hydrogen atom or a methyl, ethyl, propyl, ⁇ -hydroxyethyl, ⁇ - hydroxypropyl or -CH ⁇ Ch ⁇ OCh ⁇ Ch ⁇ pOH, where p is equal to 0 or to an integer between 1 and 6, with the proviso that R 8 > R 19 > R 20 and R 21 do not simultaneously represent a hydrogen atom, r and s, which may be identical or different, are integers included in 1 and 6, q is equal to 0 or to an integer between 1 and 34, X "denotes an anion such as a halogenide,
- A denotes a radical of a dihalide or is preferably -CH2-CH2-O-CH2-CH2-.
- Quaternary polymers of vinylpyrrolidone and of vinylimidazole such as, for example, the products sold under the names Luviquat® FC 905, FC 550 and FC 370 by the company B.A.S.F.
- Crosslinked polymers of methacryloyloxyalkyl (C1-C4) trialkyl (C1-C4) ammonium salts such as polymers obtained by homopolymerization of dimethylaminoethyl methacrylate quaternized with methyl chloride, or by copolymerization of acrylamide with dimethylaminoethyl methacrylate - Quaternized by methyl chloride, the homo or copolymerization being followed by crosslinking with an olefinically unsaturated compound, in particular methylenebisacrylamide.
- cationic polymers which may be used in the context of the invention are cationic proteins or hydrolysates of cationic proteins, polyalkyleneimines, in particular polyethyleneimines, polymers containing vinylpyridine or vinylpyridinium units, condensates of polyamines and epichlorohydrin, quaternary polyureylenes and chitin derivatives, especially chitosans or their salts; the salts which can be used are, in particular, chitosan acetate, lactate, glutamate, gluconate or pyrrolidonecarboxylate. These compounds include the chitosan having a rate of de- sacétylation 90% by weight, the keted pyrrolidonecarboxylate chitosan com ⁇ under the name KYTAMER ® PC by Amerchol.
- cationic polymers which may be used in the context of the present invention, it is preferred to use cationic cyclopolymers, in particular homopolymers or copolymers of dimethyldiallylammonium chloride, sold under the names "Merquat 100", “ MERQUAT 550 “and” MERQUAT S “by NALCO, quaternary polymers of vinylpyrrolidone and vinylimidazole, homopolymers or crosslinked copolymers of methacryloyloxyalkyl (C 1 -C 4) trialkyl (C 1 -C 4) salts ammonium, chitosan pyrrolidone carboxylate sold under the name KYTAMER ® PC by Amerchol and produce ⁇ diapers.
- cationic cyclopolymers in particular homopolymers or copolymers of dimethyldiallylammonium chloride, sold under the names "Merquat 100", “ MERQUAT 550 “and” MERQUAT S “by NALCO,
- K denotes a unit derived from a monomer comprising at least one nitrogen atom.
- M denotes a unit derived from an acidic monomer having one or more carboxylic or sulfonic groups, or K and M may denote groups derived from zwitterionic monomers of carboxybetaines or sulfobetaines;
- K and M may also denote a cationic polymer chain comprising primary, secondary, tertiary or quaternary amine groups, in which at least one of the amine groups carries a carboxylic or sulphonic group connected via a hydrocarbon radical, or K and M are part of a chain of an ⁇ , ⁇ -dicarboxylic ethylene unit polymer, one of whose carboxylic groups has been reacted with a polyamine containing one or more primary amine groups. or secondary.
- the amphoteric polymers corresponding to the definition given above, which are more particularly preferred, are chosen from the following polymers:
- the vinyl compound may also be a dialkyldiallylammonium salt such as dimethyldiallylammonium salt (eg chloride).
- dialkyldiallylammonium salt such as dimethyldiallylammonium salt (eg chloride).
- the copolymers of acrylic acid and of the latter monomer are sold under the names MERQU AT 280 and MERQUAT 295 by the company NALCO.
- (2) polymers comprising units derived from: a) at least one monomer chosen from acrylamides or methacrylamides substituted on the nitrogen with an alkyl radical, b) with at least one acidic comonomer containing one or more carboxylic groups reagents, and c) at least one basic comonomer such as primary, secondary, tertiary and quaternary amine substituted esters of acrylic and methacrylic acids and the quaternization product of dimethylaminoethyl methacrylate with dimethyl or diethyl sulfate.
- N-substituted acrylamides or methacrylamides which are more particularly preferred according to the invention are the groups in which the alkyl radicals contain from 2 to 12 carbon atoms and more particularly N-ethylacrylamide, N-tert-butyl-acrylamide and N-tert-octyl.
- the acidic comonomers are chosen more particularly from acrylic, methacrylic, crotonic, itaconic, maleic and fumaric acids as well as alkyl monoesters having 1 to 4 carbon atoms of maleic or fumaric acids or anhydrides.
- Preferred basic comonomers are aminoethyl, butylaminoethyl, N, N'-dimethylaminoethyl, N-tert-butylaminoethyl methacrylates.
- copolymers whose CTFA name (4th Ed., 1991) is octylacrylamide / acrylates / butylaminoethyl methacrylate copolymer are particularly used.
- R 4 represents a divalent radical derived from a saturated dicarboxylic acid, a mono or dicarboxylic aliphatic acid having an ethylenic double bond, an ester of a lower alkanol having 1 to 6 carbon atoms of these acids or of a radical deriving from the addition of any one of said acids with a primary bis or secondary bis amine
- Z denotes a radical of a bis-primary, mono or bis-secondary polyalkylene polyamine and preferably represents: a) in the proportions of 60 to 100 mol%, the radical
- the saturated carboxylic acids are preferably chosen from acids having 6 to 10 carbon atoms, such as adipic acid, trimethyl-2,2,4-adipic acid and trimethyl-2,4,4-adipic acid, terephthalic acid, ethylenic double bond such as acrylic acid, methacrylic acid, itaconic acid.
- the alkanesultones used in the alkylation are preferably propane or butane sultone
- the salts of the alkylating agents are preferably the sodium or potassium salts.
- R5 denotes a polymerizable unsaturated group such as an acrylate, methacrylate, acrylamide or methacrylamide group
- y and z represent an integer from 1 to 3
- RQ and R7 represent a hydrogen, methyl, ethyl or propyl atom
- RQ and Rg represent a hydrogen atom or an alkyl radical such that the sum of the carbon atoms in Rs and Rg does not exceed 10.
- Polymers comprising such units may also comprise units derived from non-zwitterionic monomers such as dimethyl or diethylaminoethyl acrylate or methacrylate or alkyl acrylates or methacrylates, acrylamides or methacrylamides or vinyl acetate.
- R 10 represents a radical of formula:
- amphoteric polymers of the type -D-X-D-X- selected from: a) the polymers obtained by the action of chloroacetic acid or sodium chloroacetate on compounds comprising at least one unit of formula
- X denotes the symbol E or E 1 , E or E 'which are identical or different and denote a divalent radical which is a straight or branched chain alkylene radical having up to 7 carbon atoms in the unsubstituted main chain or substituted with hydroxyl groups and which may comprise in o or atoms of oxygen, nitrogen, sulfur, 1 to 3 aromatic and / or heterocyclic rings; the oxygen, nitrogen and sulfur atoms being present in the form of ether, thioether, sulphoxide, sulphone, sulphonium, alkylamine, alkenylamine, hydroxyl groups, benzylamine, amine oxide, quaternary ammonium, amide groups, imide, alcohol, ester and / or urethane; b) polymers of formula:
- E denotes a radical and X denotes the symbol E or E 'and at least once E'; E having the meaning indicated above and E 'is a divalent radical which is a straight or branched chain alkylene radical having up to 7 carbon atoms in the main chain, substituted or unsubstituted by one or more hydroxyl radicals and comprising one or more nitrogen atoms, the nitrogen atom being substituted by an optionally interrupted alkyl chain by an oxygen atom and necessarily containing one or more carboxyl functions or one or more hydroxyl functional groups and betaineized by reaction with chloroacetic acid or sodium chloroacetate.
- (9) (C 1 -C 5) alkyl vinyl ether / maleic anhydride copolymers partially modified by semiamidation with N, N-dialkylaminoalkylamine such as N, N-dimethylaminopropylamine or by semi-esterification with N, N-dialkanolamine.
- These copolymers may also include other vinyl comonomers such as vinylcaprolactam.
- amphoteric polymers that are particularly preferred according to the invention are those of the family (1).
- the silicones that can be used in accordance with the invention are, in particular, polyorganosiloxanes that are insoluble in the composition and can be in the form of oils, waxes, resins or gums.
- Organopolysiloxanes are further defined in Walter Noll's "Chemistry and Technology of Silicones” (1968) Academy Press. They can be volatile or nonvolatile.
- the silicones are more particularly chosen from those having a boiling point between 60 ° C. and 260 ° C., and more particularly from:
- cyclic silicones comprising from 3 to 7 silicon atoms and preferably from 4 to 5. It is, for example, octamethylcyclotetrasiloxane marketed in particular under the name "VOLATILE SILICONE 7207" by UNION CARBIDE or "SILBIONE 70045 V 2" by RHODIA CHIMIE, decamethylcyclopentasiloxane marketed under the name "VOLATILE SILICONE 7158" by UNION CARBIDE, "SILBIONE 70045 V 5" by RHODIA CHIMIE, and mixtures thereof.
- linear volatile silicones having 2 to 9 silicon atoms and having a viscosity less than or equal to 5 ⁇ 10 -6 m 2 / s at 25 ° C. It is, for example, decamethyltetrasiloxane marketed in particular under the name " SH 200 "by TORAY SILICONE Silicones in this class are also described in the article published in Cosmetics and toiletries, Vol 91, Jan.
- Non-volatile silicones and more particularly polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, gums and resins of silicones, polyorganosiloxanes modified with organofunctional groups and mixtures thereof, are preferably used.
- chosen from among the polyalkylsiloxanes, among which may be mentioned mainly polydimethylsiloxanes with terminal trimethylsilyl ayan groups t is a viscosity of 5.10 -6 to 2.5 m / s at 25 ° C and preferably 1.10 -5 to 1 m 2 / s.
- the viscosity of the silicones is, for example, measured at 25 ° C. according to ASTM 445 Appendix C.
- SILBIONE oils of the 47 and 70 047 series or the MIRASIL oils marketed by RHODIA CHIMIE such as, for example, the 70 047 V 500 000 oil; oils of the MIRASIL series marketed by RHODIA CHIMIE;
- oils of the 200 series of the Dow Corning Company such as, more particularly, the DC200 with a viscosity of 60 000 Cst;
- polyalkylsiloxanes In this class of polyalkylsiloxanes, mention may also be made of the products sold under the names "ABIL WAX 9800 and 9801" by the company GOLDSCHMIDT, which are polyalkyl (C 1 -C 20 ) siloxanes.
- the polyalkylarylsiloxanes are particularly chosen from polydimethylmethylphenylsiloxanes and linear and / or ramified polydimethyl diphenylsiloxanes with a viscosity of from 1 ⁇ 10 -5 to 5 ⁇ 10 -2 m.sup.2 at 25 ° C.
- the products sold can be exemplified by way of example.
- the SILBIONE oils of the 70 641 series of RHODIA CHIMIE the oils of the RHODORSIL 70 633 and 763 series of RHODIA CHIMIE, the DOW CORNING DOW CORNING 556 COSMETIC GRAD FLUID oil, the silicones of the PK series of BAYER as the product PK20;
- silicones of the PN and PH series from BAYER such as the PN1000 and PH 1000 products
- oils of the SF series of GENERAL ELECTRIC such as SF 1023, SF 1154, SF 1250, SF 1265.
- the silicone gums that can be used in accordance with the invention are in particular polydiorganesiloxanes having high average molecular weights between 200,000 and 1,000,000 used alone or in a mixture in a solvent.
- This solvent may be chosen from volatile silicones, polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffins, polyisobutylenes, methylene chloride, pentane, dodecane, tridecanes or their mixtures.
- PDMS polydimethylsiloxane
- PPMS polyphenylmethylsiloxane
- isoparaffins polyisobutylenes
- methylene chloride pentane
- dodecane dodecane
- tridecanes tridecanes or their mixtures.
- polydimethylsiloxane / phenylmethylsiloxane polydimethylsiloxane / diphenylsiloxane / methylvinylsiloxane.
- More particularly useful products according to the invention are mixtures such as:
- mixtures formed from a hydroxylated polydimethylsiloxane at the end of the chain (called dimethiconol according to the CTFA code nomenclature) and a cyclic poly-dimethylsiloxane (called cyclomethicone according to the CTFA dictionary name), such as the product Q2 1401 marketed by the company Dow Corning; .
- mixtures formed from a polydimethylsiloxane gum with a cyclic silicon such as the product SF 1214 Silicone Fluid from GENERAL ELECTRIC, this product is a SF 30 gum corresponding to a dimethicone, having a number average molecular weight of 500,000 solubilized in oil SF 1202 Silicone Fluid corresponding to decamethylcyclopentasiloxane; . mixtures of two PDMSs of different viscosities, and more particularly of a PDMS gum and a PDMS oil, such as the product SF 1236 of the so ⁇ cicie GENERAL ELECTRIC.
- the product SF 1236 is the mixture of an SE 30 gum defined above having a viscosity of 20 m 2 / s and an SF 96 oil having a viscosity of 5 ⁇ 10 -6 m 2 / s. preferably 15% SE gum and 85% of an SF 96 oil.
- Organopolysiloxane resins usable according to the invention are crosslinked siloxane systems containing the units: R 2 Si0 2/2, RsSiOi / 2, RSiO 3/2 and SiO 4/2 in which R represents a hydrocarbon ment having Malawi ⁇ 1 to 16 carbon atoms or a phenyl group.
- R denotes a lower alkyl radical Ci-C 4 , more particularly methyl, or a phenyl radical.
- organomodified silicones that may be used in accordance with the invention are silicones as defined above and comprising in their structure one or more organofunctional groups attached via a hydrocarbon-based radiocarbon.
- organomodified silicones comprising: polyethyleneoxy and / or polypropyleneoxy groups optionally comprising C 6 -C 24 alkyl groups, such as the products known as dimethicone copolyol sold by the company Dow Corning under the name DC 1248 or SILWET oils L 722, L 7500, L 77, L 711 from the company UNION CARBIDE and the alkyl (Ci 2 ) meticone copolyol marketed by the company Dow Corning under the name Q2 5200;
- polyorganosiloxanes comprising: polyethyleneoxy and / or polypropyleneoxy groups optionally comprising C 6 -C 24 alkyl groups, such as the products known as dimethicone copolyol sold by the company Dow Corning under the name DC 1248 or SILWET oils L 722, L 7500, L 77, L 711 from the company UNION CARBIDE and the alkyl (Ci 2 ) meticone copolyol marketed by the company Dow Corning
- substituted or unsubstituted amine groups such as the products sold under the name GP 4 Silicone Fluid and GP 7100 by the company Genesee or the products sold under the names Q2 8220 and Dow Corning 929 or 939 by the company Dow Corning.
- the substituted amine groups are aminoalkyl groups Ci-C 4;
- thiol groups such as the products marketed under the terms “GP 72 A” and “GP 71” from GENESEE;
- alkoxylated groups such as the product sold under the name "Silicone Copolymer F-755" by SWS Silicones and Abil Wax 2428, 2434 and 2440 by the company GOLDSCHMIDT;
- hydroxyl groups such as the hydroxyalkyl-functional polyorganosiloxanes described in the French patent application FR-A-85 16334, which corresponds to the formula (Xl): R 3 - - R, (Xl)
- radicals R 3 which are identical or different are chosen from methyl and phenyl radicals; at least 60 mol% of the radicals R 3 denoting methyl; the radical R ' 3 is a divalent C 2 -C 18 hydrocarbon alkylene chain; p is between 1 and 30 inclusive; q is from 1 to 150 inclusive;
- acyloxyalkyl groups such as, for example, the polyorganosiloxanes described in US Pat. No. 4,957,732 and corresponding to formula (XII):
- R 4 denotes a methyl, phenyl, -OCOR 5 , hydroxyl group, only one of the radicals R 4 per silicon atom may be OH;
- R ' 4 is methyl, phenyl; at least 60% in molar proportion of all the R 4 radicals and R ' 4 denoting methyl;
- R 5 denotes alkyl or alkenyl, C2-C8 0;
- anionic groups of the carboxylic type for example in the products described in the patent EP 186 507 of the company Chisso Corporation, or of the alkylcarboxylic type, such as those present in the product X-22-3701E from the company Shin-Etsu; 2-hydroxyalkylsulfonate; 2-hydroxyalkylthiosulfate such as the products sold by GOLDSCHMIDT under the names "ABIL S201" and "ABIL S255".
- hydroxyacylamino groups such as the polyorganosiloxanes described in patent application EP 342 834. Mention may be made, for example, of the product Q2- 8413 from the company Dow Corning.
- silicones comprising a polysiloxane por ⁇ tion and a portion consisting of a non-silicone organic chain, one of the two portions constituting the main chain of the polymer, the other being grafted on the said main channel.
- These polymers are for example described in patent applications EP-A-412 704, EP-A-412 707, EP-A-640 105 and WO 95/00578, EP-A-582 152 and WO 93/23009 and the US Patents 4,693,935, US 4,728,571 and US 4,972,037.
- These polymers are preferably anionic or nonionic.
- Such polymers are, for example, copolymers which can be obtained by radical polymerization from the monomer mixture consisting of: a) 50 to 90% by weight of tert-butyl acrylate; b) 0 to 40% by weight of acrylic acid; c) 5 to 40% by weight of silicone macromer of formula:
- v being a number from 5 to 700; the percentages by weight being cal ⁇ culated with respect to the total weight of the monomers.
- grafted silicone polymers include polydimethylsiloxanes (PDMS) on which are grafted, via a thiopropylene type connecting member, mixed polymeric units of the poly (meth) acrylic acid type and the poly (meth) acrylate type and polydimethylsiloxanes (PDMS) on which are grafted, via a thiopropylene type connecting member, polymer units of the poly (meth) acrylate isobutyl type.
- PDMS polydimethylsiloxanes
- PDMS polydimethylsiloxanes
- silicones can also be used in the form of emulsions, nanoemulsions or microemulsions.
- the polyorganosiloxanes that are particularly preferred according to the invention are:
- non-volatile silicones chosen from the family of polyalkylsiloxanes containing trimethylsilyl end groups, such as oils having a viscosity of between 0.2 and 2.5 m 2 / s at 25 ° C., such as the oils of the DC200 series of Dow Corning in particular that of 60 000 Cst viscosity, the SILBIONE 70047 and 47 series and more particularly the 70 047 V 500 000 oil marketed by RHODIA CHIMIE, the polyalkylsiloxanes containing dimethylsilanol end groups such as dimethiconol or polyalkylarylsi loxanes, such as the SILBIONE 70641 V 200 oil marketed by Rhodia Chimie; the organopolysiloxane resin sold under the name Dow Corning 593;
- polysiloxanes containing amino groups such as amodimethicones or trimethylsilylamodimethicone
- the cationic proteins or hydrolysates of cationic proteins are in particular chemically modified polypeptides carrying at the end of the chain, or grafted onto it, quaternary ammonium groups.
- Their mo ⁇ lecular mass may vary for example from 1 500 to 10 000, and in particular from 2 000 to 5 000 approximately.
- hydrolysates of collagen carrying triethylammonium groups such as the products sold under the name "Quat-Pro E” by the company MAYBROOK and referred to in the CTFA dictionary "Triethonium Hydrolyzed Collagen Ethosulfate”
- collagen hydrolysates carrying trimethylammonium chloride and trimethylstearylammonium groups sold under the name "Quat-Pro S” by the company MAYBROOOK and referred to in the CTFA dictionary “Steartrimonium Hydrolyzed Collagen”
- animal protein hydrolysates bearing trimethylbenzylammonium groups such as the products sold under the name Crotein BTA by the company CRODA and referred to in the CTFA dictionary as "Benzyltrimonium hydrolyzed animal protein”
- proteins or quaternized hydrolysates are, for example, those corresponding to formula (XIV):
- X " is an anion of an organic or inorganic acid
- A denotes a protein residue derived from collagen protein hydrolysates
- R 5 denotes a lipophilic group having up to 30 carbon atoms
- R 6 represents a grouping alkylene having 1 to 6 carbon atoms, for example the products sold by the company Inolex under the name “Loexin QX 3000", referred to in the CTFA dictionary "Cocotrimonium Collagent Hydrolysate".
- quaternized vegetable proteins such as proteins of wheat, corn or soya: as quaternized wheat proteins, mention may be made of those marketed by Croda under the names “Hytrotriticum WQ or QM", in the CTFA dictionary "Cocodimonium
- CTFA "Laurdimonium hydrolysed wheat protein", or "Hydrotriticum QS", called in the CTFA dictionary "Steardimonium hydrolysed wheat protein".
- the ceramide-type compounds are in particular ceramides and / or glycoceramides and / or pseudoceramides and / or neoceramides, natural or synthetic.
- Ceramide-type compounds are for example described in patent applications DE4424530, DE4424533, DE4402929, DE4420736, WO95 / 23807, WO94 / 07844, EP-A-0646572, WO95 / 16665, FR-2,673,179, EP-A- 0227994 and WO 94/07844, WO94 / 24097, WO94 / 10131, the teachings of which are hereby incorporated by reference.
- Particularly preferred ceramide-type compounds according to the invention are, for example:
- cationic surfactants among which may be mentioned in particular: salts of primary, secondary or tertiary fatty amines, optionally polyoxyalkylenated; quaternary ammonium salts; imidazoline derivatives; or oxides of amines with a cationic character.
- the quaternary ammonium salts are, for example:
- radicals R 1 to R 4 which may be identical or different, represent a linear or branched aliphatic radical containing from 1 to 30 carbon atoms, or an aromatic radical such as aryl or alkylaryl.
- the aliphatic radicals can comprise heteroatoms such as in particular oxygen, nitrogen, sulfur, halogens.
- the aliphatic radicals are for example chosen from alkyl, alkoxy, polyoxy (C 2 -C 6) alkylene, alkylamide, (C 2 -C 22) alkyl amido (C2-Ce), (C 1 2-C2 2) acetate hydroxyalkyl having from about 1 to about 30 carbon atoms;
- X is an anion chosen from the group of halides, phosphates, acetates, lactates, alkyl (C 2 -C 6 ) sulphates, alkyl-or-alkylarylsulphonates, preferably R 1 and R 2 denotes C1-C4 alkyl or C 1 -C 4 hydroxyalkyl; .
- tetraalkylammonium chlorides for example dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl radical has from about 12 to 22 carbon atoms, are preferred.
- carbon in particular behenyltrimethylammonium, distearyldimethylammonium, cetyltrimethylammonium, benzyldimethylstearylammonium chlorides or, on the other hand, palmitylamidopropyltrimethylammonium chloride or stearamidopropyldimethyl (myristyl acetate) ammonium chloride;
- R 5 represents an alkenyl or alkyl radical containing from 8 to 30 carbon atoms, for example derived from coconut fatty acids
- R 6 represents a hydrogen atom, a C 1 -C 4 alkyl radical or an alkenyl or alkyl radical; having from 8 to 30 carbon atoms
- R 7 represents an alkyl radical in C 1 -C 4 alkyl
- Rs represents a hydrogen atom
- X is an anion chosen from the group of halides, phosphates , acetates, lactates, alkylsulfates, alkyl-or-alkylarylsulfonates.
- R 5 and RB denote a mixture of alkenyl or alkyl radicals containing from 12 to 21 carbon atoms, for example derived from tallow fatty acids, R 7 denotes methyl and R 8 denotes hydrogen.
- R 5 and RB denote a mixture of alkenyl or alkyl radicals containing from 12 to 21 carbon atoms, for example derived from tallow fatty acids
- R 7 denotes methyl
- R 8 denotes hydrogen.
- Such a product is for example marketed under the name "REWOQUAT W 75" by the company Degussa,
- Rg is an aliphatic radical having about 16 to 30 carbon atoms
- R13 and R14 identical or different are chosen from hydrogen or an alkyl radical containing from 1 to 4 carbon atoms
- X is an anion chosen from the group of halides, acetates, phosphates, nitrates and methylsulphates.
- diammonium quaternary salts include in particular propane dichloride diammonium.
- quaternary ammonium salts containing at least one ester function that can be used according to the invention are, for example, those of formula (XVIII) below:
- R 5 is chosen from C 1 -C 4 alkyl radicals and C 1 -C 4 hydroxyalkyl or dihydroxyalkyl radicals;
- Q is selected from:
- R 1 is selected from:
- R 1 and R 21 which are identical or different, are chosen from linear or branched, saturated or unsaturated C 7 -C 21 hydrocarbon radicals;
- n, p and r which may be identical or different, are integers ranging from 2 to 6;
- y is an integer from 1 to 10;
- x and z are integers ranging from 0 to 10;
- - X ⁇ is a simple or complex anion, organic or inorganic; with the proviso that the sum x + y + z is from 1 to 15, that when x is 0, then R-IQ is R20 and that when z is 0 then R-) 8 is R22-
- the alkyl radicals R15 may be linear or branched and more particularly linear.
- R 5 denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl radical and more particularly a methyl or ethyl radical.
- the sum x + y + z is from 1 to 10.
- R-j ⁇ is a hydrocarbon radical R20, it can be long and have from 12 to 22 carbon atoms or short and have from 1 to 3 carbon atoms.
- R 1 is a hydrocarbon radical R 22, it preferably has 1 to 3 carbon atoms.
- R 1, R 2 and R 21, which are identical or different, are chosen from linear or branched, saturated or unsaturated C 1 -C 21 hydrocarbon radicals, and more particularly from alkyl and alkenyl radicals.
- Ci 1-C21 linear or branched, saturated or unsaturated.
- x and z are 0 or 1.
- y is equal to 1.
- n, p and r are 2 or 3 and even more particularly are equal to 2.
- the anion is preferably a halide (chloride, bromide or iodide) or an alkyl sulphate more particularly methyl sulphate.
- a halide chloride, bromide or iodide
- an alkyl sulphate more particularly methyl sulphate.
- methanesulphonate, phosphate, nitrate, tosylate an anion derived from an organic acid such as acetate or lactate or any other anion compatible with ammonium with an ester function.
- the anion X ⁇ is even more particularly chloride or methylsulfate.
- R15 denotes a methyl or ethyl radical
- z is 0 or 1; n, p and r are 2;
- Ri 6 is chosen from:
- Ri s is chosen from:
- ⁇ 17 » ⁇ 19 * ⁇ ⁇ 21> identical or different, are chosen from hydrocarbon radicals in C13-C17 linear or branched, saturated or unsaturated and preferably from alkyl and alkenyl radicals, C ⁇ -C-jy linear or branched, saturated or unsaturated.
- the hydrocarbon radicals are linear.
- the compounds of formula (XVI) such as the salts (especially chloride or methylsulfate) of diacyloxyethyl dimethyl ammonium, diacyloxyethyl hydroxyethyl methyl ammonium, monoacyloxyethyl dihydroxyethyl methyl ammonium, triacyloxyethyl methyl ammonium, monoacyloxyethyl hydroxyethyl dimethyl ammonium and mixtures thereof.
- the acyl radicals preferably have from 14 to 18 carbon atoms and come more particularly from a vegetable oil such as palm oil or sunflower oil. When the compound contains more than one acyl radical, the latter may be identical or different.
- These products are obtained for example by direct esterification of triethanolamine, triisopropanolamine, alkyldiethanolamine or alkyldiisopropanolamine optionally oxyalkylenated on fatty acids or mixtures of fatty acids of plant or animal origin or by transesterification of their esters methyl.
- This esterification is followed by a quaternization using an alkylating agent such as an alkyl halide (preferably methyl or ethyl), a dialkyl sulphate (preferably methyl or ethyl), methyl methanesulphonate, methyl paratoluenesulfonate, glycol or glycerol chlorohydrin.
- an alkylating agent such as an alkyl halide (preferably methyl or ethyl), a dialkyl sulphate (preferably methyl or ethyl), methyl methanesulphonate, methyl paratoluenesulfonate,
- Such compounds are, for example, sold under the names DEHYQUART by the company COGNIS, STEPANQUAT by the company STEPAN, NOXAMIUM by the company CECA, REWOQUAT WE 18 by the company DEGUSSA.
- ammonium salts containing at least one ester function described in US-A-4874554 and US-A-4137180.
- tetraalkylammonium chlorides for example dialkyldimethylammonium or alkyltrimethylammonium chlorides, in which the alkyl radical contains approximately from 12 to 22 carbon atoms, are preferred.
- dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl radical contains approximately from 12 to 22 carbon atoms.
- the fatty acids are chosen more particularly from myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, linolenic acid and isostearic acid.
- fatty acids are in particular esters of carboxylic acids, in particular mono, di, tri or tetracarboxylic esters.
- the monocarboxylic acid esters include monoesters of saturated aliphatic acids or unsaturated, linear or branched Ci-C 26 and saturated or unsaturated aliphatic alcohols, linear or branched C 1 -C 26 Is the total number of carbon esters being greater than or equal to 10.
- diethyl sebacate diisopropyl sebacate; diisopropyl adipate; di-propyl adipate; dioctyl adipate; diisostearyl adipate; dioctyl maleate; glyceryl undecylenate; octyldodecyl stearoyl stearate; pentaerythrityl monoricinoleate; pentaerythrityl tetraisononate; pentaerythrityl tetrapelargonate; pentaerythrityl tetraisostearate; pentaerythrityl tetraoctanoate; dicaprylate propylene glycol dicaprate; tridecyl erucate; triisopropyl citrate; triisotearyl citrate; glyceryl trilactate; glyceryl trioctanoate; trio
- esters mentioned above it is preferred to use ethyl and isopropyl palmitates, ethyl-2-hexyl palmitate, 2-octyldecyl palmitate and alkyl myristates such as myristate.
- fluorinated oils are for example perfluoropolyethers described in particular in the patent application EP-A-486135 and the fluorohydrocarbon compounds described in particular in the patent application WO 93/11103.
- fluorohydrocarbon compounds refers to compounds whose chemical structure comprises a carbon skeleton of which certain hydrogen atoms have been substituted by fluorine atoms.
- Fluorinated oils may also be fluorocarbons such as fluoroamines, for example perfluorotributylamine, fluorinated hydrocarbons, for example perfluorodecahydronaphthalene, fluoroesters and fluoro-thers; Perfluoropolyethers are for example sold under the trade names FOMBLIN by the company MONTEFLUOS and KRYTOX by the company DU PONT.
- fluorohydrocarbon compounds mention may also be made of fluorinated fatty acid esters such as the products sold under the name NOFABLE FO by the company Nippon Oil.
- the conditioning agent (s) may represent from 0.001% to 20% by weight, preferably from 0.01% to 10% by weight and more particularly from 0.1% to 3% by weight relative to total weight of the final composition.
- the composition may comprise a hydrophilic medium comprising water or a mixture of water and hydrophilic organic solvent (s) such as alcohols and especially linear or branched C1-C6 monoalcohols.
- s such as alcohols and especially linear or branched C1-C6 monoalcohols.
- alcohols such as ethanol, tert-butanol, n-butanol, isopropanol or n-propanol
- polyols such as glycerine, diglycerine, propylene glycol, sorbitol, pentylene glycol, and the like. polyethylene glycols, or alternatively the glycols ethers, in particular C-2.
- the water or the mixture of water and hydrophilic organic solvents may be present in the composition according to the invention in a content ranging from 30% to 99% by weight, relative to the total weight of the composition, and from preferably from 40% to 80% by weight.
- the composition may further comprise an additional polymer such as a film-forming polymer.
- film-forming polymer means a polymer capable of forming on its own or in the presence of an auxiliary film-forming agent, a continuous and adherent film on a support, in particular on keratin materials.
- film-forming polymers that may be used in the composition of the present invention, mention may be made of synthetic polymers, of radical type or of polycondensate type, polymers of natural origin and their mixtures, in particular acrylic polymers, polyurethanes , polyesters, polyamides, polyureas, cellulosic polymers such as nitrocellulose.
- compositions of the invention advantageously also contain at least one surfactant which is generally present in an amount of between 0.1% and 60% by weight, preferably between 1% and 40% and even more preferably between 5% and 30%, based on the total weight of the composition.
- This surfactant may be chosen from anionic, amphoteric and nonionic surfactants, or mixtures thereof.
- Surfactants suitable for the implementation of the present invention are in particular the following: (0) Anionic surfactant (s):
- anionic surfactants which may be used, alone or as mixtures, in the context of the present invention, mention may be made in particular (non-limiting list) of the salts (in particular alkaline salts, in particular sodium salts, sodium salts, and the like).
- alkylsulfates alkylethersulfates, alkylamidoethersulfates, alkylarylpolyethersulfates, monoglycerides sulfates; alkylsulfonates, alkylphosphates, alkylamidesulfonates, alkylarylsulfonates, ⁇ -olefin-sulfonates, paraffin-sulfonates; alkylsulfosuccinates, alkylethersulfosuccinates, alkylamidesulfosuccinates; alkylsulfosuccinamates; alkylsulfoacetates; alkyl ether phosphates; acylsarcosinates; acylisethionates and N-acyltaurates, the alkyl or acyl radical of all these various compounds preferably containing from
- anionic surfactants that can still be used, mention may also be made of fatty acid salts such as the salts of oleic, ricinoleic, palmitic and stearic acids, coconut oil acid or hydrogenated coconut oil acid; acyl lactylates whose acyl radical has 8 to 20 carbon atoms. It is also possible to use weakly anionic surfactants, such as the alkyl D galactoside uronic acids and their salts, as well as the polyoxyalkylenated (C 6 -C 2 4) alkyl carboxylic acids, the C 6 alkyl acids.
- weakly anionic surfactants such as the alkyl D galactoside uronic acids and their salts, as well as the polyoxyalkylenated (C 6 -C 2 4) alkyl carboxylic acids, the C 6 alkyl acids.
- polyoxyalkylenated aryl ether carboxylic acids polyoxyalkylenated (C 6 -C 24 ) alkyl amido ether carboxylic acids and their salts, in particular those containing from 2 to 50 ethylene oxide groups, and mixtures thereof.
- the alkyl sulphate and alkyl ether sulfate salts and their mixtures are preferred to use, according to the invention.
- Nonionic surfactants are also well-known compounds per se (see in particular in this regard "Handbook of Surfactants” by MR PORTER, Blackie & Son editions (Glasgow and London), 1991, pp 116-178) and their nature does not, in the context of the present invention, be of a critical nature.
- alcohols alpha-diols, alkylphenols or polyethoxylated, polypropoxylated or polyglycerolated fatty acids, having a fatty chain comprising, for example, 8 to 18 carbon atoms, the a number of ethylene oxide or propylene oxide groups that can range from 2 to 50 and the number of glycerol groups that can range from 2 to 30.
- amphoteric surfactant (s) may be in particular (non-limiting list) derivatives of secondary or tertiary aliphatic amines, wherein the aliphatic radical is a straight or branched chain having 8 to 22 carbon atoms and containing at least one water-soluble anionic group (eg carboxylate, sulfonate, sulfate, phosphate or phosphonate); mention may also be made of alkyl (Cs-C 20 ) betaines, sulphobetaines, alkyl (C 8 -C 20 ) amidoalkyl (C 1 -C 6 ) betaines or alkyl (C 8 -C 2 o) amidoalkyl (CrC 6 ) sulfobetaines.
- the amine derivatives mention may be made of the products sold under the name MI
- R 2 -CONHCH 2 CH 2 -N (R 3 ) (R 4 ) (CH 2 COO-) (2) in which: R 2 denotes an alkyl radical derived from an acid R 2 -COOH present in the oil of hydrolyzed coco, a heptyl, nonyl or undecyl radical, R 3 denotes a beta-hydroxyethyl group and R 4 a carboxymethyl group; and
- B represents -CH 2 CH 2 OX '
- X 1 denotes the group -CH 2 CH 2 -COOH or a hydrogen atom
- Y 'de notes -COOH or the radical -CH 2 - CHOH - SO3H
- R 5 denotes an alkyl radical of an Rg -COOH acid present in coconut oil or in hydrolysed linseed oil, an alkyl radical, especially a C 7 , Cg radical,
- compositions according to the invention use is preferably made of surfactant mixtures and in particular mixtures of anionic surfactants and mixtures of anionic surfactants and amphoteric or nonionic surfactants.
- a particularly preferred mixture is a mixture of at least one anionic surfactant and at least one amphoteric surfactant.
- an amphoteric surfactant such as the amine derivatives known as di-sodium cocoamphodipropionate or sodium cocoamphopropionate marketed in particular by the company Rhodia Chimie under the trade name "MIRANOL C2M CONC" in aqueous solution containing 38% active ingredient or the name MIRANOL C32;
- amphoteric surfactant of the zwitterionic type such as alkylbetaines, in particular cocobetaine sold under the name "Dehyton AB 30" in aqueous solution containing 32% of MA by the company Cognis.
- mixtures of surfactants and in particular mixtures of anionic surfactants, mixtures of anionic surfactants and amphoteric, cationic or non-cationic surfactants are possible to use mixtures of surfactants and in particular mixtures of anionic surfactants, mixtures of anionic surfactants and amphoteric, cationic or non-cationic surfactants.
- ionic mixtures of cationic tensides with nonionic or amphoteric surfactants is a mixture comprising at least one anionic surfactant and at least one amphoteric surfactant.
- the amount of anionic surfactants is preferably from 3% to 40% by weight, based on the total weight of the cosmetic composition. It is preferably between 5% and 35% by weight and more preferably between 8% and 25% by weight.
- the amount of amphoteric and / or nonionic surfactants, when they are present, is preferably from 0.5 to 20% by weight, and in particular from 1 to 15% by weight and more particularly from 2 to 10% by weight relative to the total weight of the composition.
- composition according to the invention may also comprise ingredients commonly used in cosmetics, such as vitamins, perfumes, pearlescent agents, thickeners, gelling agents, trace elements, sweeteners, sequestering agents, perfumes, alkalinizing or acidifying agents, preservatives, sunscreens, antioxidants, anti-hair loss agents, anti-dandruff agents, anti-grease agents, anti-free radicals, or mixtures thereof.
- ingredients commonly used in cosmetics such as vitamins, perfumes, pearlescent agents, thickeners, gelling agents, trace elements, sweeteners, sequestering agents, perfumes, alkalinizing or acidifying agents, preservatives, sunscreens, antioxidants, anti-hair loss agents, anti-dandruff agents, anti-grease agents, anti-free radicals, or mixtures thereof.
- ingredients commonly used in cosmetics such as vitamins, perfumes, pearlescent agents, thickeners, gelling agents, trace elements, sweeteners, sequestering agents, perfumes, alkalinizing or acidifying agents, preservative
- the pH of the composition of the present invention is chosen in the range from 2 to 11 and preferably from 3 to 10.
- alkalinizing agents well known from the state of the art of the compositions applied to keratin materials.
- alkalinizing agents mention may be made, for example, of ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines and their derivatives, hydroxyalkylamines and ethylene diamines which are oxyethylenated and / or oxypropylenes, hydroxides of sodium or potassium and the compounds of formula (XX) below:
- R39 ⁇ ⁇ 4i R wherein R is a propylene residue optionally substituted with a hydroxyl ment grou ⁇ or an alkyl radical in C 1 -C 4 alkyl; 8 R3, R3 9, R 40 and R 41, identical or different, represent a hydrogen atom, an alkyl radical in C 1 -C 4 hydroxyalkyl or C 1 -C 4.
- the acidifying agents are conventionally, by way of example, mineral or organic acids such as hydrochloric acid, orthophosphoric acid, carboxylic acids such as tartaric acid, citric acid, lactic acid, or sulfonic acids.
- the composition according to the invention may comprise a propellant.
- the propellant is included among the compressed or liquefied gases usually used for the preparation of aerosol compositions and their mixtures. Air, carbon dioxide, compressed nitrogen or a soluble gas such as dimethyl ether, halogenated hydrocarbons (particularly fluorinated) or not, and mixtures thereof, are preferably used.
- the compositions particularly find an application of particular interest in the hair field, in particular for maintaining the hairstyle or shaping the hair.
- the hair compositions are preferably shampoos, after shampoos, gels, styling lotions, blow-drying lotions, fixing and styling compositions such as lacquers or spray.
- the lotions may be packaged in various forms, in particular in vaporizers, pump-bottles or in aerosol containers in order to ensure application of the composition in vaporized form or in the form of foam.
- compositions according to the invention may be used for the washing or treatment of keratinic materials such as hair, skin, eyelashes, eyebrows, nails, lei ⁇ vres, the scalp and more particularly the hair.
- compositions according to the invention are detergent compositions such as shampoos, shower gels and bubble baths.
- the compositions comprise one or more surfactants that can be indifferently chosen, alone or in mixtures, within the anionic, amphoteric, nonionic surfactants as defined above.
- the quantity and the quality of the surfactants are those sufficient to give the final composition satisfactory foaming and / or detergent power.
- the surfactants can represent from 4% to 50% by weight, preferably from 6% to 35% by weight, and even more preferably from 8% to 25% by weight, of the total weight of the composition. final.
- the composition comprises at least 3% by weight of anionic surfactant, more particularly from 4 to 30% by weight relative to the total weight of the composition.
- the invention therefore also relates to a method for treating ké-ratinic materials such as the skin or the hair, characterized in that it consists in applying to the keratin materials a cosmetic composition as defined above, then to be carried out optionally a rinse with water.
- this method according to the invention allows the maintenance of the hairstyle, treatment ⁇ ment, care or washing or removing make-up of the skin, hair or any other keratin material.
- the subject of the invention is also the use of the composition for maintaining or shaping keratin materials, in particular the hair.
- compositions of the invention may be in the form of a conditioner to be rinsed or not, or in the form of compositions to be rinsed, to be applied before or after any treatment.
- capillary action including coloring, discoloration, permanent or straightening, or between the two stages of a perm or de-waxing.
- composition when in the form of an optionally rinsing conditioner, it advantageously contains at least one cationic surfactant, for example in a concentration generally of between 0.1 and 10% by weight and preferably of 0.5. 5% by weight relative to the total weight of the composition.
- compositions according to the invention may also be in the form of aqueous or aqueous-alcoholic lotions for the care of the skin and / or the hair.
- the composition according to the invention after application to human hair and scalp can be rinsed or not rinsed after any treatment. It may be in any form conventionally used in the field concerned and for example in the form of a more or less thickened lotion, gel, cream, spray or mousse.
- This composition can be monophasic or multiphasic.
- the present invention also relates to a cosmetic treatment process keratin materials which consists in applying an effective amount of a composition as described above, on keratin materials, optionally to perform a rinse after a possible exposure time.
- the composition can be used as a shampoo.
- the compositions in accordance with the invention are simply applied to wet cheeks, and then the composition is then removed, after a possible pause time, by rinsing with water. operation that can be repeated one or more times.
- compositions of the invention are further illustrated in the following examples. Tg measurement
- a film is produced from an aqueous solution containing 6% by weight of polymer and dried for 48 hours in a controlled atmosphere at 50% relative humidity and 25 ° C.
- the films thus obtained have a thickness of between 10 and 20%. .mu.m.
- the measuring device is a DSC (TA instruments).
- the sample from the film is deposited in an airtight crucible and is heated according to the following protocol:
- heating 1 increase in temperature, at a rate of + 10 ° C./min up to final temperature: Tf ( 0 C); - isothermal for 1 minute;
- heating 2 increase of the temperature at a rate of + 10 ° C./min up to Tf ( 0 C);
- a solution 1 comprising the monomers: 50 g of polyethylene glycol methacrylate (MPEG 550), 50 g of dimethylaminopropylmethacrylamide (DMAPMA) and the initiator: 0.5 g of (Trigonox 21S).
- a solution 2 comprising 75 ml of methyl ethyl ketone and 0.5 g of initiator (Trigonox 21S) is also prepared.
- Solution 1 is poured dropwise in 1 hour and solution 2 in two hours. res, in the quadricol reactor. The resulting mixture is maintained at 80 ° C. for 5 hours. The yellow-orange solution obtained is cooled. 95 g of polymer are obtained.
- the polymer has a Brookfield viscosity at 15% in the MEK at 25 ° C. measured with a spindle number 1 at a speed of 0.1 rpm of: 7.5 mPa.s .
- the polymer can then be neutralized in the following manner: 290 ml of 1N HCl are added with stirring to 95 g of polymer and 200 ml of distilled water. Then the solvent is evaporated (MEC). The neutralized polymer is soluble in water (at least up to 50% by weight). Its Tg is -60 ° C. The neutralized polymer has a water recovery at 85% RH of 51%.
- a reactor (quadricol) surmounted by two ampoules of addition, a refri ⁇ manager and provided with a mechanical stirrer, is introduced 100 ml of water which is brought to 80 0 C.
- a solution 1 comprising 50 g of MPEG 550 monomer, 1 g of initiator (potassium persulfate KPS) and 50 ml of water is prepared.
- a solution 2 comprising 50 g of DMAPMA monomer neutralized to 100% with betaine hydrochloride and 50 g of water is also prepared. Solutions 1 and 2 are cast in 1 hour in the quadricol. After one hour at 80 ° C., a mixture of 1 g of KPS in 50 ml of water is introduced dropwise over 15 minutes.
- the polymer has a Brookfield viscosity at 15% in water, at 25 ° C., measured with a spindle number 1, at a speed of 6 rpm, of: 164 mPa.s.
- the polymer is soluble in water (at least up to 50% by weight). Its Tg is -60 ° C.
- the neutralized polymer has a water recovery at 85% RH of 90%.
- Example 1 solvent process
- Example 2 process in water
- the following polymers which are according to the invention or comparative:
- TMEACL 2- (dimethylamino) ethyl acrylate, quaternized with methyl chloride
- the invention may be exemplified by the following non-exhaustive compositions.
- the compositions described below are not limiting. Percentages are expressed as a percentage by weight of active ingredient.
- composition described above is applied to 10 hairs (European chestnut hair approximately 20 cm long) at the rate of 12 gram ⁇ my composition by hair. After a 2 minute break, the disentangling on damp hair is evaluated by a panel of 10 experts then the hair is rinsed. They are then dried in a helmet (50 ° C./30 minutes).
- a score of 10 corresponds to:
- a good disentangling of the hair average level obtained with the formula after the shampoo "Mask Intense” marketed by the L'Oréal society applied at a rate of 12 grams per hair (European hair chestnut about 20 cm long ). After 2 minutes of break, disentangling on wet hair is evaluated by the panel of experts.
- a low styling level Average level obtained on a hair having just been rinsed and then dried with the helmet (50 ° C./30 minutes).
- compositions of the invention (A 1 B, C) gives a much higher level of styling than that obtained with the compositions containing the cationic cationic polymers (D , E).
- compositions of the invention (A 1 B 1 C) gives a higher level of styling than that obtained with the composition containing PEG graft polymers, making not part of the invention (F 1 G 1 H).
- compositions of the invention (A 1 B 1 C) gives a disentangling of the damp hair similar to that obtained with the compositions containing the cationic conditioning polymers ( D 1 E).
- compositions of the invention (A 1 B 1 C) gives a disentangling of the hair much higher than that obtained with the composition containing the PEG graft polymer not part of the invention (F 1 G 1 H).
- compositions of the invention make it possible to obtain both a good styling level while having a good level of disentangling on wet hair, unlike the comparative compositions (D 1 E 1 F 1 G 1 H).
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Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05786095A EP1768645A1 (fr) | 2004-07-02 | 2005-07-01 | Compositions cosmetiques contenant au moins un agent conditionneur et au moins un copolymere ethylenique a greffons polyethyleneglycol |
US11/631,118 US20080286218A1 (en) | 2004-07-02 | 2005-07-01 | Cosmetic Compositions Containing at Least One Conditioning Agent and at Least One Ethylene Polymer with Polyethylene Glycol Grafts |
BRPI0512444-1A BRPI0512444A (pt) | 2004-07-02 | 2005-07-01 | composição cosmética, processo cosmético de tratamento das matérias queratìnicas e usos de uma composição |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0451410A FR2872423B1 (fr) | 2004-07-02 | 2004-07-02 | Compositions cosmetiques contenant au moins un agent conditionneur et au moins un copolymere ethylenique a greffons polyethyleneglycol |
FR0451410 | 2004-07-02 | ||
US58672804P | 2004-07-12 | 2004-07-12 | |
US60/586,728 | 2004-07-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006013271A1 true WO2006013271A1 (fr) | 2006-02-09 |
Family
ID=34946252
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2005/001702 WO2006013271A1 (fr) | 2004-07-02 | 2005-07-01 | Compositions cosmetiques contenant au moins un agent conditionneur et au moins un copolymere ethylenique a greffons polyethyleneglycol |
Country Status (6)
Country | Link |
---|---|
US (1) | US20080286218A1 (fr) |
EP (1) | EP1768645A1 (fr) |
CN (1) | CN1980633A (fr) |
BR (1) | BRPI0512444A (fr) |
FR (1) | FR2872423B1 (fr) |
WO (1) | WO2006013271A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2514504A1 (fr) | 2007-02-02 | 2012-10-24 | Donaldson Company, Inc. | Paquet de matériaux filtrants |
WO2014118465A1 (fr) | 2013-01-31 | 2014-08-07 | S.P.C.M. Sa | Nouveaux polymeres peignes utilisables en cosmétique et detergence |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008520614A (ja) * | 2004-11-24 | 2008-06-19 | ザ プロクター アンド ギャンブル カンパニー | 毛髪トリートメント剤 |
TWI400254B (zh) * | 2005-06-23 | 2013-07-01 | Shiseido Co Ltd | 聚合物及化粧料 |
FR2934155B1 (fr) * | 2008-07-24 | 2014-07-25 | Oreal | Polymeres sequences, compositions cosmetiques les comprenant et procede de traitement cosmetique. |
FR2957791A1 (fr) * | 2010-03-26 | 2011-09-30 | Oreal | Composition cosmetique comprenant une dispersion aqueuse de polymere et procede de traitement cosmetique |
JP5998445B2 (ja) | 2010-10-22 | 2016-09-28 | 三菱化学株式会社 | 毛髪化粧料 |
MX352279B (es) * | 2012-03-30 | 2017-11-16 | Procter & Gamble | Composicion acondicionadora para el cabello que comprende un surfactante cationico y un polimero de deposito. |
MX352277B (es) * | 2012-03-30 | 2017-11-16 | Procter & Gamble | Composicion acondicionadora para el cabello que comprende un sistema surfactante cationico de monoalquilamina, un polimero de deposito, y silicona. |
EP2981246B1 (fr) * | 2013-04-05 | 2023-04-26 | The Procter & Gamble Company | Composition de soin capillaire comprenant une formulation pre-emulsifiee |
WO2015047826A1 (fr) * | 2013-09-30 | 2015-04-02 | The Procter & Gamble Company | Composition de soins capillaires à plus forte teneur en tensioactif cationique et en polymère de dépôt |
KR20180058727A (ko) * | 2015-09-30 | 2018-06-01 | 가부시키가이샤 시세이도 | 수중유중 분체형 조성물 |
AR108797A1 (es) * | 2016-06-29 | 2018-09-26 | Dow Brasil Sudeste Ind Ltda | Sistema concentrado para el cuidado del cabello |
CN109715133B (zh) * | 2016-09-27 | 2022-05-17 | 株式会社资生堂 | 使用了核-壳型微粒的化妆品原料和水包油型乳化化妆品 |
CN109485802A (zh) * | 2018-11-06 | 2019-03-19 | 广州天赐高新材料股份有限公司 | 一种发用定型聚合物及其制备方法 |
WO2021165493A1 (fr) * | 2020-02-21 | 2021-08-26 | Basf Se | Polyamines alcoxylées à biodégradabilité améliorée |
KR20230073178A (ko) | 2020-07-21 | 2023-05-25 | 켐보 엘엘씨 | 디에스테르 미용 제제 및 그의 용도 |
CN117126403B (zh) * | 2023-10-26 | 2024-01-02 | 山东富源新材料股份有限公司 | 一种甲基mq硅树脂的合成方法 |
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EP0372546A2 (fr) * | 1988-12-09 | 1990-06-13 | Kao Corporation | Résine formant un film et compositions d'entretien des cheveux contenant cette résine |
EP0728778A1 (fr) * | 1995-02-21 | 1996-08-28 | Kao Corporation | Résine formant un film et composition cosmétique pour les soins des cheveux contenant cette résine |
EP1270624A1 (fr) * | 2000-10-13 | 2003-01-02 | Kansai Paint Co., Ltd. | Resine pour dispersion de pigment |
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JP2651918B2 (ja) * | 1988-02-23 | 1997-09-10 | 三菱化学株式会社 | ゲル状整髪剤組成物 |
CA2057442C (fr) * | 1990-12-13 | 2001-10-23 | Anthony D. Gough | Composition de fixatif pour les cheveux |
US20030147825A1 (en) * | 2001-06-08 | 2003-08-07 | Chiarelli Joseph A. | Personal care compostions containing inverse emulsion polymers |
US20050025736A1 (en) * | 2003-07-30 | 2005-02-03 | Janusz Jachowicz | Hair and skin altering and protecting compositions |
-
2004
- 2004-07-02 FR FR0451410A patent/FR2872423B1/fr not_active Expired - Fee Related
-
2005
- 2005-07-01 CN CNA2005800225767A patent/CN1980633A/zh active Pending
- 2005-07-01 EP EP05786095A patent/EP1768645A1/fr not_active Withdrawn
- 2005-07-01 WO PCT/FR2005/001702 patent/WO2006013271A1/fr active Application Filing
- 2005-07-01 US US11/631,118 patent/US20080286218A1/en not_active Abandoned
- 2005-07-01 BR BRPI0512444-1A patent/BRPI0512444A/pt not_active IP Right Cessation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0372546A2 (fr) * | 1988-12-09 | 1990-06-13 | Kao Corporation | Résine formant un film et compositions d'entretien des cheveux contenant cette résine |
EP0728778A1 (fr) * | 1995-02-21 | 1996-08-28 | Kao Corporation | Résine formant un film et composition cosmétique pour les soins des cheveux contenant cette résine |
EP1270624A1 (fr) * | 2000-10-13 | 2003-01-02 | Kansai Paint Co., Ltd. | Resine pour dispersion de pigment |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2514504A1 (fr) | 2007-02-02 | 2012-10-24 | Donaldson Company, Inc. | Paquet de matériaux filtrants |
EP2514505A1 (fr) | 2007-02-02 | 2012-10-24 | Donaldson Company, Inc. | Paquet de matériaux filtrants et élément filtrante |
EP2514506A1 (fr) | 2007-02-02 | 2012-10-24 | Donaldson Company, Inc. | Ensemble de supports de filtration d'air, élément filtrant, supports de filtration d'air et procédés |
EP3597285A1 (fr) | 2007-02-02 | 2020-01-22 | Donaldson Company, Inc. | Ensemble de filtration d'air |
WO2014118465A1 (fr) | 2013-01-31 | 2014-08-07 | S.P.C.M. Sa | Nouveaux polymeres peignes utilisables en cosmétique et detergence |
US9150675B2 (en) | 2013-01-31 | 2015-10-06 | S.P.C.M. Sa | Comb polymers which can be used in cosmetics and detergents |
US9499648B2 (en) | 2013-01-31 | 2016-11-22 | S.P.C.M. Sa | Comb polymers which can be used in cosmetics and detergents |
Also Published As
Publication number | Publication date |
---|---|
BRPI0512444A (pt) | 2008-03-04 |
FR2872423A1 (fr) | 2006-01-06 |
CN1980633A (zh) | 2007-06-13 |
EP1768645A1 (fr) | 2007-04-04 |
FR2872423B1 (fr) | 2006-09-22 |
US20080286218A1 (en) | 2008-11-20 |
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