EP3386476A1 - Zusammensetzung mit einem polymer mit einen sulfonischen monomer und einem pyridinedicarboxylsäurederivat und verfahren zur kosmetischen behandlung - Google Patents

Zusammensetzung mit einem polymer mit einen sulfonischen monomer und einem pyridinedicarboxylsäurederivat und verfahren zur kosmetischen behandlung

Info

Publication number
EP3386476A1
EP3386476A1 EP16808628.8A EP16808628A EP3386476A1 EP 3386476 A1 EP3386476 A1 EP 3386476A1 EP 16808628 A EP16808628 A EP 16808628A EP 3386476 A1 EP3386476 A1 EP 3386476A1
Authority
EP
European Patent Office
Prior art keywords
weight
acrylamido
acid
composition
composition according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP16808628.8A
Other languages
English (en)
French (fr)
Inventor
Laurence Richet
Olivia ISARD
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP3386476A1 publication Critical patent/EP3386476A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00Preparations for affecting hair growth
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54Polymers characterized by specific structures/properties
    • A61K2800/542Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5424Polymers characterized by specific structures/properties characterized by the charge anionic

Definitions

  • composition comprising a polymer containing a sulfonic monomer and a pyridinedicarboxylic acid derivative, and cosmetic treatment method
  • the present invention relates to a composition, in particular a cosmetic composition, comprising a pyridinedicarboxylic acid derivative in combination with a particular thickening polymer, and also to a cosmetic treatment method using said composition, in particular in the field of haircare.
  • the growth of the hair and its renewal are mainly determined by the activity of the hair follicles and their matrix environment. Their activity is cyclical and essentially comprises three phases, namely the anagenic phase, the catagenic phase and the telogenic phase.
  • the head of hair is continuously renewed and, of the approximately 150 000 individual hairs which make up a head of hair, approximately 10% are at rest and will be replaced in the months to come.
  • the natural loss of the hair can be estimated, on average, at a few hundred hairs per day for a normal physiological state. This constant physical renewal process undergoes a natural change during the course of ageing; the hairs become finer and their cycles shorter. It is known, furthermore, that certain factors, such as hormonal imbalance, physiologi- cal stress or malnutrition, can accentuate the phenomenon. In addition, loss or impairment of the hair can be in connection with seasonal phenomena.
  • patent EP 1 352 629 it has thus in particular been proposed, by patent EP 1 352 629, to use pyridinedicarboxylic acid derivatives to induce and/or stimulate the growth of human keratin fibres, such as the hair or eyelashes, and/or to slow down their loss and/or to in- crease their density.
  • These derivatives are generally offered formulated in the form of an aqueous- alcoholic lotion to be applied to the scalp.
  • the formulation of these derivatives within a thickened composition especially provides slip, in particular on dry hair, which facilitates the massaging of the scalp, thus enabling a better distribution and a better availability of the active agents on the scalp and throughout the length of the hair.
  • composition is thickened, or even gelled, makes it possible to provide a more slippery feel than that obtained with a non thickened aqueous- alcoholic lotion.
  • the composition When the composition is thickened, the measuring out thereof is facilitated since it can be drawn off easily, it runs less between the fingers and ultimately there is less loss. In addition, it can be applied to and distributed over the hair or scalp more easily, without running onto the face or neck.
  • the thickened composition makes it possible to provide conditioning, volume and density to the head of hair during styling.
  • the hair is smooth and shiny.
  • composition has a better stability, whether this is with respect to temperature, to pH or over time.
  • the objective of the present invention is therefore to propose a composition that is advantageously in the form of a lotion, in particular hair lotion, which is thickened and stable even though it comprises a pyridinedicarboxylic acid derivative.
  • a subject of the present invention is a composition comprising:
  • Ri and F3 ⁇ 4 represent, independently of one another, a hydrogen atom, a saturated or unsaturated, linear or branched C1-C18 aliphatic hydrocarbon radical; or a C6-C18 aralkyl radical; said radicals optionally being substituted by one or more groups selected from OH, NH 2 , -OR, -OCOR and -NHR with R representing a C1-C18 alkyl group; at least one of the Ri and R2 groups being other than a hydrogen atom; and
  • composition comprising water in an amount ranging from 20% to 80% by weight, or even from 30% to 50% by weight, relative to the total weight of the composition.
  • Another subject of the invention is a method for the cosmetic treatment of keratin materials, in particular the hair and/or the skin, including the scalp, in which a cosmetic composition as defined above is applied to said keratin materials and said keratin materials are optionally rinsed.
  • compositions according to the invention result in a substantial provision of density and volume to the head of hair, during styling, and also a provision of body, the hair being stronger and more resistant.
  • the head of hair is well-behaved, and easy to style. Moreover, the usage and sensory qualities are improved.
  • compositions according to the invention are furthermore stable, in particular during storage and/or with respect to temperature variations.
  • the expression “at least one” is equivalent to the ex- pression “one or more” and can be substituted therefor, and the expression “between ... and " is equivalent to the expression “ranging from ... to ! and can be substituted therefor; in these two expressions, the limits are included.
  • the composition according to the invention thus comprises at least one pyridinedicarboxylic acid ester.
  • the ester can be a monoester or a diester, preferably a diester. It can also be a salt of such an ester.
  • Said compounds correspond to the general formula (I), or a salt thereof:
  • Ri and R2 represent, independently of one another, a hydrogen atom, a saturated or unsaturated, linear or branched C1-C18 aliphatic hydrocarbon radical, in particular alkyl radical; or a C6-C18 aryl radical; said aliphatic or aryl hydrocarbon radicals optionally being substituted by one or more groups selected from OH, NH 2 , -OR, -OCOR and -NHR with R representing a C1-C18 alkyl group;
  • At least one of the Ri and R2 groups is other than a hydrogen atom.
  • the COOR1 and COOR2 substituents are respectively in the 2 and 3 positions, or in the 2 and 4 positions of the pyridine ring. Preferably, they are in the 2 and 4 positions.
  • the compounds correspond to the formula (la), or a salt thereof:
  • Ri and R2 represent, independently of one another, a hydrogen atom, a saturated or unsaturated, linear or branched C1-C18 aliphatic hydrocarbon radical, in particular alkyl radical; or a C6-C18 aryl radical; said aliphatic or aryl hydrocarbon radicals optionally being substituted by one or more groups selected from OH, NH 2 , -OR, -OCOR and -NHR with R representing a C1-C18 alkyl group; at least one of the Ri and R2 groups being other than a hydrogen atom.
  • the C1-C18 aliphatic hydrocarbon radical in particular alkyl radical, is a C1-C10, in particular C1-C6, aliphatic hydrocarbon radi- cal, in particular alkyl radical, such as methyl, ethyl, tert-butyl, isopropyl or hexyl.
  • the aryl radical can represent the phenyl or naphthyl radical.
  • Ri and R 2 represent, independently of one another, a hydrogen atom or a saturated, linear or branched, C1 -C18, better still C1 -C10, indeed even C1 -C6, aliphatic hydrocarbon radical, in particular alkyl radical, which is optionally substituted by an alkoxy or acyloxy group (OR or OCOR with R denoting a C1-C18 alkyl radical), at least one of the Ri and R 2 groups being other than a hydrogen atom.
  • Ri and R 2 are identical.
  • Ri and R 2 are identical and represent a saturated linear C1-C18, preferably C1 -C10 and better still C1 -C6 alkyl radical and very particularly an ethyl radical.
  • the composition comprises, as compound of formula (I) or (la), diethyl pyridine-2,4-dicarboxylate.
  • Salts of the compounds of formula (I) is understood to mean, according to the invention, the organic or inorganic salts of a compound of formula (I), these salts being physiologically acceptable. Mention may be made, as inorganic salts, of the sodium or potassium salts and also the zinc (Zn 2+ ), calcium (Ca 2+ ), copper (Cu 2+ ), iron (Fe 2+ ), strontium (Sr 2+ ), magnesium (Mg 2+ ) or manganese (Mn 2+ ) salts; the hydroxides, the carbonates and the chlorides.
  • the composition according to the invention comprises the compound(s) of formula (I) in an amount greater than or equal to 0.5% by weight, in particular between 0.5% and 20% by weight, in particular ranging from 3% to 15% by weight and better still ranging from 4% to 10% by weight, relative to the total weight of the composition.
  • composition according to the invention also comprises one or more polymers comprising at least one monomer containing a sulfonic group.
  • the polymers comprising at least one monomer containing a sulfonic group are preferably water-soluble or water-dispersible. They may be homopolymers or copolymers and can be obtained from at least one ethylenically unsaturated monomer containing a sulfonic group, which may be in free form or partially or totally neutralized form. These polymers may optionally comprise at least one hydrophobic group and then constitute an amphiphilic polymer (or hydrophobic modified polymer).
  • the polymers in accordance with the invention may be partially or totally neutralized with an inorganic base (sodium hydroxide, potassium hydroxide or aqueous ammonia) or an organic base such as monoethanolamine, diethanolamine or triethanolamine, an aminomethylpropanediol, N- methylglucamine, basic amino acids, for instance arginine and lysine, and mixtures of these compounds. They are generally neutralized.
  • an inorganic base sodium hydroxide, potassium hydroxide or aqueous ammonia
  • organic base such as monoethanolamine, diethanolamine or triethanolamine, an aminomethylpropanediol, N- methylglucamine, basic amino acids, for instance arginine and lysine, and mixtures of these compounds.
  • neutralized is intended to mean polymers that are totally or virtually totally neutralized, i.e. at least 90% neutralized.
  • the polymers used in the composition of the invention generally have a number- average molecular weight (Mn) ranging from 1000 to 20 000 000 g/mol, preferably ranging from 20 000 to 5 000 000 g/mol and more preferentially still from 100 000 to 1 500 000 g/mol.
  • Mn number- average molecular weight
  • polymers according to the invention may be crosslinked or non-crossl inked.
  • the monomers containing a sulfonic group of the polymer used in the composition of the invention are in particular chosen from vinylsulfonic acid, styrenesulfonic acid, (meth)acrylamido(Ci-C22)alkylsulfonic acids, N-(Ci-
  • C22)alkyl(meth)acrylamido(Ci-C22)alkylsulfonic acids such as undecylacrylamidomethanesulfonic acid, and also partially or totally neutralized forms thereof, and mixtures thereof.
  • the monomers containing a sulfonic group are chosen from (meth)acrylamido(Ci-C22)alkylsulfonic acids, for instance acrylamidomethanesulfonic acid, acrylamidoethanesulfonic acid, acrylamidopropanesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, 2- methacrylannido-2-nnethylpropanesulfonic acid, 2-acrylannido-n-butanesulfonic acid, 2-acrylamido-2,4,4-thnnethylpentanesulfonic acid, 2-methacrylamidododecyl sulfonic acid and 2-acrylamido-2,6-dimethyl-3-heptanesulfonic acid, and also the partially or totally neutralized forms thereof, and mixtures thereof.
  • (meth)acrylamido(Ci-C22)alkylsulfonic acids for instance acrylamidomethane
  • a polymer comprising at least one monomer of 2- acrylamido-2-methylpropanesulfonic acid type, and also the partially or totally neutralized forms thereof.
  • the crosslinking agents may be chosen from the polyolefinically unsaturated compounds commonly used for crosslinking polymers obtained by radical polymerization.
  • crosslinking agents examples include divinylbenzene, diallyl ether, dipropylene glycol diallyl ether, polyglycol diallyl ethers, triethylene glycol divinyl ether, hydroquinone diallyl ether, ethylene glycol or tetraethylene glycol di(meth)acrylate, trimethylolpropane triacrylate, methylenebisacrylamide, methylenebismethacrylamide, triallylamine, triallyl cyanurate, diallyl maleate, tetraallylethylenediamine, tetraallyloxyethane, trimethylolpropane diallyl ether, allyl (meth)acrylate, allylic ethers of alcohols of the sugar series, or other allyl or vinyl ethers of polyfunctional alcohols, and also the allylic esters of phosphoric and/or vinylphosphonic acid derivatives, or mixtures of these compounds.
  • the crosslinking agent is chosen from methylenebisacrylamide, allyl methacrylate and trimethylolpropane triacrylate (TMPTA).
  • TMPTA trimethylolpropane triacrylate
  • the degree of crosslinking generally ranges from 0.01 mol% to 10 mol% and more particularly from 0.2 mol% to 2 mol% relative to the polymer.
  • the polymers used are homopolymers, they only comprise monomers containing a sulfonic group and, if they are crosslinked, one or more crosslinking agents. These homopolymers are generally crosslinked and neutralized, and they may be obtained according to the preparation process comprising the following steps:
  • the monomer solution or dispersion obtained in (a) is neutralized with one or more mineral or organic bases, preferably aqueous ammonia NH 3 , in an amount making it possible to obtain a degree of neutralization of the sulfonic acid functions of the polymer ranging from 90% to 100%;
  • a standard free-radical polymerization is performed in the presence of free- radical initiators at a temperature ranging from 10 to 150°C; the polymer precipitating in the tert-butanol-based solution or dispersion.
  • the composition may comprise at least one 2-acrylamido-2- methylpropanesulfonic acid homopolymer comprising, randomly distributed:
  • X + denotes a proton, an alkali metal cation, an alkaline-earth metal cation or the ammonium ion, not more than 10 mol% of the cations X + possibly being protons H + ; b) from 0.01 % to 10% by weight of crosslinking units originating from at least one monomer containing at least two olefinic double bonds; the weight proportions being defined relative to the total weight of the polymer.
  • the homopolymers according to the invention that are more particularly preferred comprise from 98% to 99.5% by weight of units of formula (II) and from 0.2% to 2% by weight of crosslinking units.
  • a polymer of this type that may especially be mentioned is the crosslinked and neutralized 2-acrylamido-2-methylpropanesulfonic acid homopolymer sold by Clariant under the trade name Hostacerin AMPS (CTFA name: ammonium polyacryldimethyltauramide).
  • the polymer may also be an amphiphilic homopolymer (or hydrophobic modified homopolymer) selected from random amphiphilic 2-acrylamido-2- methylpropanesulfonic acid polymers modified by reaction with a C6-C22 n- monoalkylamine or di-n-alkylamine, such as those described in document WO 00/31 154, which are grafted homopolymers.
  • an amphiphilic homopolymer or hydrophobic modified homopolymer selected from random amphiphilic 2-acrylamido-2- methylpropanesulfonic acid polymers modified by reaction with a C6-C22 n- monoalkylamine or di-n-alkylamine, such as those described in document WO 00/31 154, which are grafted homopolymers.
  • the polymers used are copolymers they may be obtained by polymerization using ethylenically unsaturated monomers containing a sulfonic group and additional ethylenically unsaturated monomers, i.e. ethylenically unsaturated monomers without a sulfonic group.
  • additional ethylenically unsaturated monomers i.e. ethylenically unsaturated monomers without a sulfonic group.
  • the ethylenically unsaturated monomers containing a sulfonic group are chosen from those described above.
  • the ethylenically unsaturated monomers without a sulfonic group may be chosen from ethylenically unsaturated hydrophilic monomers, ethylenically unsaturated hydrophobic monomers and mixtures thereof.
  • the ethylenically unsaturated hydrophilic monomers may be selected for example from (meth)acrylic acids, ⁇ -substituted alkyl derivatives thereof or esters thereof obtained with monoalcohols or monoalkylene or polyalkylene glycols, (meth)acrylamides, vinylpyrrolidone, vinylformamide, maleic anhydride, itaconic acid, maleic acid or mixtures of these compounds.
  • the polymer comprising at least one monomer containing a sulfonic group according to the invention is a copolymer that can be obtained from ethylenically unsaturated monomers containing a sulfonic group and ethylenically unsaturated hydrophilic monomers, said polymer may be selected from:
  • said polymer comprising at least one monomer containing a sulfonic group is selected from those from the families (1 ) to (3) above.
  • said polymer comprising at least one monomer containing a sulfonic group is selected from non-associative polymers.
  • the polymer comprising at least one monomer containing a sulfonic group according to the invention is a copolymer that can be obtained from ethylenically unsaturated monomers containing a sulfonic group and ethylenically unsaturated hydrophobic monomers, that is to say comprising a C6-C50 fatty chain
  • said polymer is amphiphilic, that is to say that it comprises both a hydrophilic portion and a hydrophobic portion.
  • Such polymers are also referred to as hydrophobic modified polymers.
  • hydrophobic modified polymers may also contain one or more monomers comprising neither a sulfonic group nor a fatty chain, such as (meth)acrylic acids, ⁇ -substituted alkyl derivatives thereof or esters thereof obtained with monoalcohols or monoalkylene or polyalkylene glycols, (meth)acrylamides, vinylpyrrolidone, vinylformamide, maleic anhydride, itaconic acid or maleic acid, or mixtures of these compounds.
  • monomers comprising neither a sulfonic group nor a fatty chain, such as (meth)acrylic acids, ⁇ -substituted alkyl derivatives thereof or esters thereof obtained with monoalcohols or monoalkylene or polyalkylene glycols, (meth)acrylamides, vinylpyrrolidone, vinylformamide, maleic anhydride, itaconic acid or maleic acid, or mixtures of these compounds.
  • the ethylenically unsaturated hydrophobic monomers may be selected from those of formula (III) below:
  • Ri and R3 which may be identical or different, denote a hydrogen atom or a linear or branched C1-C6 alkyl radical, preferably methyl;
  • Y denotes O or NH;
  • R 2 denotes a hydrocarbon radical comprising from 6 to 50 carbon atoms, preferentially from 6 to 22 carbon atoms, better still from 6 to 18 carbon atoms and more particularly from 12 to 18 carbon atoms; and
  • x varies from 0 to 100.
  • the R2 radical is preferably selected from linear C6-C18 alkyl radicals (for example n-hexyl, n-octyl, n-decyl, n-hexadecyl, n-dodecyl or lauryl, or n-octadecyl or stearyl radicals); branched or cyclic C6-C18 alkyl radicals (for example cyclododecane (C12) or adamantane (C10) radicals); C6-C18 alkylperfluoro radicals (for example the group of formula -(CH 2 )2-(CF 2 )9-CF 3 ); the cholesteryl (C27) radical or a cholesterol ester residue, such as the cholesteryl oxyhexanoate group; or polycyclic aromatic groups, such as naphthalene or pyrene.
  • linear C6-C18 alkyl radicals for example n-hexy
  • radicals the ones that are more particularly preferred are substantially linear alkyl radicals and more particularly the n-dodecyl, n-hexadecyl or n-octadecyl radical, and mixtures thereof.
  • the monomer of formula (III) comprises at least one alkylene oxide unit (x > 1 ) and preferably several alkylene oxide units (x > 1 ) forming a polyoxyalkylene chain.
  • the number of oxyalkylene units (or number of moles of alkylene oxide) generally ranges from 3 to 100, more preferentially from 3 to 50 and better still from 7 to 25.
  • copolymers which may or may not be crosslinked and which may or may not be neutralized, comprising from 15% to 60% by weight of 2-acrylamido-2- methylpropanesulfonic acid units and from 40% to 85% by weight of (Cs- Ci6)alkyl(meth)acrylamide units or of (Cs-Ci6)alkyl (meth)acrylate units relative to the polymer, such as those described in document EP-A-750 899;
  • - terpolymers comprising from 10 mol% to 90 mol% of acrylamide units, from 0.1 ⁇ / ⁇ to 10 ⁇ / ⁇ of 2-acrylamido-2-methylpropanesulfonic acid units and from 5 ⁇ / ⁇ to 80 ⁇ / ⁇ of n-(C6-Ci8)alkylacrylamide units relative to the polymer, such as those described in document US-A-5 089 578;
  • copolymers constituted of (i) 2- acrylamido-2-methylpropanesulfonic acid units of formula (II) indicated above, in which X + is a proton, an alkali metal cation, an alkaline-earth metal cation or the ammonium ion, and (ii) units of formula (IV) below: in which x denotes an integer ranging from 3 to 100, preferably from 3 to 50, and preferentially from 7 to 25; Ri has the same meaning as that indicated above in formula (III) and R 4 denotes a linear or branched alkyl radical comprising from 6 to 22 carbon atoms and preferably from 10 to 22 carbon atoms.
  • Ri denotes methyl and R 4 represents n-hexadecyl (Ci6), n-octadecyl (Cis), or n- dodecyl (C12), or mixtures thereof.
  • the polymers for which X + denotes sodium or ammonium are more particularly preferred.
  • the polymers capable of being used in the composition in accordance with the invention may be obtained according to conventional free-radical polymerization processes in the presence of one or more initiators, for instance azobisisobutyronitrile (AIBN), azobisdimethylvaleronitrile, 2,2-azobis[2- amidinopropane] hydrochloride (ABAH), organic peroxides such as dilauryl peroxide, benzoyl peroxide, tert-butyl hydroperoxide; mineral peroxide compounds such as potassium persulfate or ammonium persulfate, or H2O2 optionally in the presence of reducing agents.
  • AIBN azobisisobutyronitrile
  • ABAH 2,2-azobis[2- amidinopropane] hydrochloride
  • organic peroxides such as dilauryl peroxide, benzoyl peroxide, tert-butyl hydroperoxide
  • mineral peroxide compounds such as potassium persulfate or ammoni
  • hydrophobic modified polymers may be obtained especially by free-radical polymerization in a tert-butanol medium, in which they precipitate.
  • precipitation polymerization in tert-butanol it is possible to obtain a size distribution of the polymer particles that is particularly favourable for its uses.
  • the reaction may be performed at a temperature of between 0 and 150°C and preferably between 10 and 100°C, either at atmospheric pressure or under reduced pressure. It may also be performed under inert atmosphere and preferably under nitrogen.
  • hydrophobic modified polymers are in particular those described in document EP 1 069 142, and especially those obtained by polymerization of 2- acrylamido-2-methylpropanesulfonic acid or a sodium or ammonium salt thereof with a (meth)acrylic acid ester and
  • the molar percentage concentration of units of formula (II) and of units of formula (IV) in the polymers according to the invention varies as a function of the desired cosmetic application and of the rheological properties sought for the formulation. It can range between 0.1 and 99.9 mol%.
  • the molar proportion of units of formula (II) or (IV) ranges from 50.1 % to 99.9%, more particularly from 70% to 95% and more particularly still from 80% to 90%.
  • the molar proportion of units of formula (II) or (IV) ranges from 0.1 % to 50%, more particularly from 5% to 25% and more particularly still from 10% to 20%.
  • composition according to the invention may comprise the polymer or polymers comprising at least one monomer containing a sulfonic group in an amount ranging from 0.01 % to 10% by weight, preferably from 0.05% to 5% by weight, better still from 0.1 % to 3% by weight and preferentially from 0.2% to 2% by weight, relative to the total weight of the composition.
  • composition according to the invention may be for cosmetic or pharmaceutical use.
  • the composition according to the invention is for cosmetic use.
  • Cosmetic is understood to mean, within the meaning of the invention, a composition of pleasant appearance, odour and feel.
  • the composition is for topical application to the skin and keratin fibres and more especially to the scalp, hair and eyelashes.
  • composition according to the invention may be in the form of an aqueous, alcoholic, aqueous-alcoholic or oily solution or suspension, of an emulsion, of liquid or semi-liquid consistency, obtained by dispersing a fatty phase in of an aqueous phase (O/W) or vice versa (W/O), or of an aqueous, alcoholic, aqueous-alcoholic or oily (anhydrous) gel.
  • an aqueous, alcoholic, aqueous-alcoholic or oily solution or suspension of an emulsion, of liquid or semi-liquid consistency, obtained by dispersing a fatty phase in of an aqueous phase (O/W) or vice versa (W/O), or of an aqueous, alcoholic, aqueous-alcoholic or oily (anhydrous) gel.
  • the composition according to the invention is in the form of an aqueous, alcoholic or aqueous-alcoholic, preferably aqueous-alcoholic, generally thickened, solution or lotion.
  • the composition according to the invention comprises water in an amount ranging from 20% to 80% by weight, or even from 30% to 50% by weight, relative to the total weight of the composition.
  • the composition according to the invention comprises one or more C2-C 4 monoalcohols such as ethanol and isopropanol, especially in an amount ranging from 10% to 90% by weight, in particular ranging from 20% to 80% by weight, or even from 30% to 70% by weight, better still ranging from 40% to 60% by weight, relative to the total weight of the composition.
  • composition according to the invention may also comprise one or more additional organic solvents, other than C2-C 4 monoalcohols, for example selected from polyols, especially those containing from 2 to 6 carbon atoms, for instance glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol or diethylene glycol; and polyol ethers such as 2-butoxyethanol, propylene glycol monomethyl ether, and diethylene glycol monoethyl ether and monomethyl ether; and mixtures thereof.
  • additional organic solvents other than C2-C 4 monoalcohols
  • composition according to the invention may also comprise one or more addi- tional thickeners, other than polymers comprising at least one monomer containing a sulfonic group above, in particular selected from carboxyvinyl polymers (car- bomers), acrylic copolymers, such as acrylate/alkyl acrylate copolymers, poly- acrylamides, polysaccharides, such as hydroxypropyl cellulose, natural gums and clays, and mention may be made, as lipophilic gelling agents, of modified clays, such as bentones, metal salts of fatty acids, such as aluminium stearates, hydrophobic treated silica, ethyl cellulose and mixtures thereof.
  • addi- tional thickeners other than polymers comprising at least one monomer containing a sulfonic group above, in particular selected from carboxyvinyl polymers (car- bomers), acrylic copolymers, such as acrylate/alkyl acrylate copolymers, poly-
  • composition according to the invention may also comprise one or more stand- ard cosmetic additives, in particular selected from nonionic, anionic, cationic and amphoteric surfactants, vitamins, sunscreens, fillers, colourants, nacreous agents, opacifiers, film-forming polymers, conditioners, liquid or solid fatty substances, antioxidants, fragrances and preservatives.
  • stand- ard cosmetic additives in particular selected from nonionic, anionic, cationic and amphoteric surfactants, vitamins, sunscreens, fillers, colourants, nacreous agents, opacifiers, film-forming polymers, conditioners, liquid or solid fatty substances, antioxidants, fragrances and preservatives.
  • the composition may also comprise one or more fixing polymers selected from nonionic, anionic, cationic or amphoteric fixing polymers, preferably from anionic or cationic fixing polymers.
  • the composition according to the invention may comprise at least one vitamin B and/or an analogue or derivative thereof.
  • the vitamin B capable of being employed in the context of the invention is chosen from vitamin B3, vitamin B5, vitamin B6 and vitamin B8 or an analogue or derivative thereof, and in particular calcium pantothenate, panthenol, panthenyl ethyl ether, panthenyl ethyl ether acetate and panthenyl triacetate, and also mixtures thereof.
  • the composition according to the invention preferably comprises the vitamin or vitamins B, analogue(s) and/or derivative(s) in an amount of between 0.001 % and 5% by weight, in particular 0.005% and 2% by weight and better still between 0.01 % and 1 % by weight, relative to the total weight of the composition.
  • the composition may comprise active agents that favour the regrowth of human keratin fibres and/or that limit the loss thereof, other than the pyridinedicarboxylic acid esters according to the invention, and which may be selected from aminexil, 6-O-[(9Z,12Z)-octadeca-9,12- dienoyl]hexapyranose, pyrimidine derivatives, such as 2,4-diamino-6- piperidinopyrimidine 3-oxide; antiseborrheic agents and/or antidandruff agents such as octopirox or zinc pyrithione.
  • active agents that favour the regrowth of human keratin fibres and/or that limit the loss thereof, other than the pyridinedicarboxylic acid esters according to the invention, and which may be selected from aminexil, 6-O-[(9Z,12Z)-octadeca-9,12- dienoyl]hexapyranose, pyrimidine derivative
  • the composition according to the invention is a hair composition, capable of being applied to the scalp and/or the hair, and may be in the form of a hair care lotion, for example for daily or twice-weekly application, of a shampoo or of a hair conditioner, in particular for twice-weekly or weekly application, of a liquid or solid soap for cleaning the scalp for daily application, of a treatment mask, of a cream or of a foaming gel for cleaning the hair. It may also be in the form of a hair dye or mascara to be applied with a brush or comb.
  • composition according to the invention in particular the cosmetic composition, may be applied to the alopecic areas of the scalp and/or to the hair, optionally left in contact for several hours and/or optionally rinsed out.
  • composition according to the invention in the evening, to keep the latter in contact overnight and optionally to shampoo in the morning.
  • These applications can be repeated daily for one or more months, according to the individuals.
  • Another subject of the present invention is a method for the cosmetic treatment of human keratin materials, in particular hair and/or skin, including the scalp, in which a cosmetic composition as defined above is applied to said keratin materials, it being possible for said application to optionally be followed by a step of rinsing said keratin materials.
  • said method is a method for the cosmetic treatment, in particular for the care, of the hair and/or scalp, for the purpose of improving their condition and/or their appearance.
  • This treatment method indeed exhibits the characteristics of a cosmetic method in so far as it makes it possible to improve the attractiveness of keratin materials, in particular hair, by giving them greater vigour, an improved appearance (provision of conditioning) and greater ease of handling (spreading, distribution) and of styling.
  • composition (% by weight, AM active material):
  • This gelled lotion is clear and stable over time (at least 2 months, at 25°C or 45°C). Applied line by line to the scalp, this lotion exhibits good qualities of use, promoting the delivery and the distribution of the active principles over the scalp.
  • the hair is silky and light and the head of hair is well-behaved and easy to style.
  • This gelled lotion is clear and stable over time (at least 2 months, at 25°C or 45°C). Applied line by line to the scalp, this lotion exhibits good qualities of use, promoting the delivery and the distribution of the active principles over the scalp. It also exhibits a good cosmetic performance. It provides hold, body and volume to the head of hair.
EP16808628.8A 2015-12-08 2016-12-07 Zusammensetzung mit einem polymer mit einen sulfonischen monomer und einem pyridinedicarboxylsäurederivat und verfahren zur kosmetischen behandlung Withdrawn EP3386476A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1561958A FR3044548B1 (fr) 2015-12-08 2015-12-08 Composition comprenant un polymere a monomere sulfonique et un derive d'acide pyridine-dicarboxylique, et procede de traitement cosmetique
PCT/EP2016/080119 WO2017097849A1 (en) 2015-12-08 2016-12-07 Composition comprising a polymer containing a sulfonic monomer and a pyridinedicarboxylic acid derivative, and cosmetic treatment method

Publications (1)

Publication Number Publication Date
EP3386476A1 true EP3386476A1 (de) 2018-10-17

Family

ID=55862876

Family Applications (1)

Application Number Title Priority Date Filing Date
EP16808628.8A Withdrawn EP3386476A1 (de) 2015-12-08 2016-12-07 Zusammensetzung mit einem polymer mit einen sulfonischen monomer und einem pyridinedicarboxylsäurederivat und verfahren zur kosmetischen behandlung

Country Status (4)

Country Link
EP (1) EP3386476A1 (de)
JP (1) JP6991971B2 (de)
FR (1) FR3044548B1 (de)
WO (1) WO2017097849A1 (de)

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5089578A (en) 1986-03-28 1992-02-18 Exxon Research And Engineering Company Hydrophobically associating terpolymers containing sulfonate functionality
EP0750899A3 (de) 1995-06-30 1998-05-20 Shiseido Company Limited Ein aus einem wasserlöslichen amphiphilen Polyelektrolyten bestehender Emulgator oder Lösungsvermittler und eine diesen enthaltende emulgierte oder solubilisierte Zusammensetzung und ein diesen enthaltendes emulgiertes oder solubilisiertes Kosmetikum
FR2750330B1 (fr) * 1996-06-28 1998-07-31 Oreal Composition se presentant notamment sous la forme d'emulsion, de gel ou de solution aqueuse, et comprenant un polymere poly(acide 2 -acrylamido 2 -methylpropane sulfonique) reticule
FR2750325B1 (fr) * 1996-06-28 1998-07-31 Oreal Utilisation en cosmetique d'un poly(acide 2-acrylamido 2- methylpropane sulfonique) reticule et neutralise a au moins 90 % et compositions topiques les contenant
WO2000031154A1 (fr) 1998-11-23 2000-06-02 Sofitech N.V. Emulsions inversables stabilisees par des polymeres amphiphiles. application a des fluides de forage
DE50015912D1 (de) 1999-07-15 2010-06-10 Clariant Produkte Deutschland Wasserlösliche Polymere und ihre Verwendung in kosmetischen und pharmazeutischen Mitteln
FR2838336B1 (fr) 2002-04-11 2005-06-03 Utilisation d'un derive pyridine-dicarboxylate ou de l'un de ses sels pour stimuler ou induire la pousse des cheveux et/ou stopper leur chute
US7455848B2 (en) * 2002-12-18 2008-11-25 Nalco Company Skin care composition containing an anionic polymer
JP4584543B2 (ja) 2003-04-02 2010-11-24 株式会社資生堂 水中油型乳化組成物
FR2856923A1 (fr) * 2003-07-02 2005-01-07 Oreal Composition pour application topique contenant un polymere hydrosoluble
FR2880536B1 (fr) * 2005-01-13 2009-02-27 Oreal Composition cosmetique en aerosol comprenant au moins un polymere fixant anionique ou non ionique, au moins un polymere sulfone, au moins un polyol et un agent propulseur
KR20070099038A (ko) 2005-01-28 2007-10-08 바스프 악티엔게젤샤프트 화장품 제제를 위한 증점제 형태의 수-중-수 에멀젼중합체의 용도
FR2912907B1 (fr) * 2007-02-23 2011-04-22 Oreal Composition de coloration comprenant au moins un colorant azoique cationique a motif julolidine et au moins un polymere epaississant non cellulolique et procede de coloration
FR2927252B1 (fr) * 2008-02-12 2010-04-23 Oreal Emulsion huile-dans-eau contenant un polyere amphiphile
FR2953716B1 (fr) 2009-12-16 2015-03-27 Oreal Kit de formulation d'un produit cosmetique
US11110121B2 (en) * 2010-07-27 2021-09-07 Clariant International Ltd. Compositions comprising hydrogen peroxide or hydrogen peroxide donor substances
DE102011013341A1 (de) 2011-03-08 2011-12-08 Clariant International Ltd. Polymere auf Basis von Sulfonsäuren, Amiden und speziellen Vernetzern
DE102011013342A1 (de) 2011-03-08 2011-09-15 Clariant International Ltd. Vernetzte Polymere
FR2991875B1 (fr) 2012-06-15 2015-10-02 Oreal Composition comprenant un ester d'acide pyridine dicarboxylique et un polymere fixant, procede et utilisation

Also Published As

Publication number Publication date
FR3044548B1 (fr) 2019-10-25
JP2018536673A (ja) 2018-12-13
WO2017097849A1 (en) 2017-06-15
JP6991971B2 (ja) 2022-01-13
FR3044548A1 (fr) 2017-06-09

Similar Documents

Publication Publication Date Title
JP5674621B2 (ja) 水溶性ポリマーおよびそれの用途
US7862803B2 (en) Oxidizing composition for treating keratin materials based on amphiphilic polymers of at least one ethylenically unsaturated monomer with a sulphonic group and comprising a hydrophobic portion
JP5377812B2 (ja) 酸性の化粧用、医薬用及び皮膚用剤
US20080003191A1 (en) Composition combining a C-glycoside derivative and an emulsifying polymer
JP2002201111A (ja) 界面活性剤不含化粧用、皮膚用及び医薬用剤
JP2004517133A (ja) 両親媒性ポリマーを含有するクレンジング組成物
US10952953B2 (en) Skin cleansing composition
US20030108577A1 (en) Cosmetic and/or dermatological acid composition containing an amphiphilic polymer
JP5743406B2 (ja) レチノイド、アデノシンに基づく非ホスフェート化化合物および半結晶性ポリマーを含有する化粧料組成物または皮膚科学的組成物
US20040047821A1 (en) Cosmetic composition comprising an anionic latex, an ether having two fatty chains and a mixture of fatty alcohols
CN111818905A (zh) 局部组合物
ES2276917T3 (es) Una composicion que contiene al menos una silicona y al menos un polimero anfifilo.
US5747014A (en) Cosmetics compositions containing at least one anionic suracant of alkylgalactoside uronate type and at least one amphoteric polymer
EP3386476A1 (de) Zusammensetzung mit einem polymer mit einen sulfonischen monomer und einem pyridinedicarboxylsäurederivat und verfahren zur kosmetischen behandlung
JP2001058918A (ja) 化粧品に使用される架橋又は分枝状の両性コポリマー及びそれを使用した組成物
EP3600560B1 (de) Antimikrobielle körperreinigungszusammensetzungen
US20040141930A1 (en) Oil-in-water oxidizing cream emulsion for treating human keratin fibers
WO2015028461A1 (en) Cosmetic composition comprising at least one acrylic and/or methacrylic thickening polymer, at least one fixing polymer and at least one anti-seborrhoeic agent
WO2018195792A1 (en) Composition comprising hydrophobic polymer for removing makeup on skin
JP7446861B2 (ja) 保湿剤
WO2018103066A1 (en) Skin care composition
ES2278011T3 (es) Composicion que contiene al menos un compuesto insoluble en agua particular y al menos un polimero anfifilo.
EP2478891A1 (de) Zusammensetzung zur chemischen Modifizierung des Innenabschnitts eines Haares
US20070104670A1 (en) Cosmetic composition comprising at least one specific fixative polymer and at least one sulphonated polymer
FR2823111A1 (fr) Composition antitranspirante anhydre a base de polymeres a motif sulfonique

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: UNKNOWN

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20180709

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

17Q First examination report despatched

Effective date: 20200302

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20200915