WO2013061477A1 - Coloration capillaire par transfert thermique - Google Patents

Coloration capillaire par transfert thermique Download PDF

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Publication number
WO2013061477A1
WO2013061477A1 PCT/JP2011/075238 JP2011075238W WO2013061477A1 WO 2013061477 A1 WO2013061477 A1 WO 2013061477A1 JP 2011075238 W JP2011075238 W JP 2011075238W WO 2013061477 A1 WO2013061477 A1 WO 2013061477A1
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WO
WIPO (PCT)
Prior art keywords
nhc
keratin materials
dry composition
och
seconds
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PCT/JP2011/075238
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English (en)
Inventor
Maxime De Boni
Hiroshi Takahashi
Fabrice OSOLIN
Gabin Vic
Original Assignee
L'oreal
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Publication date
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Priority to PCT/JP2011/075238 priority Critical patent/WO2013061477A1/fr
Publication of WO2013061477A1 publication Critical patent/WO2013061477A1/fr

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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
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216—Solid or semisolid forms
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/418—Amines containing nitro groups
    • 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
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95

Definitions

  • the present invention relates to a method for dyeing keratin materials, in particular human keratin materials, in which a dry composition comprising at least one specific nitro dye is used. It also relates to a laminated sheet comprising a film of said composition, and moreover, relates to a method for dyeing keratin materials, in particular human keratin materials, using said laminated sheet by thermal transfer technology.
  • these methods use products that are commonly prepared with liquid, gel, and/or cream formulations, which cause color transfer to scalp, clothes, and hairdressing accessories (combs, towels and so on) during and after the dyeing process.
  • the coloration time is generally long because of the relatively long leave-in time (typically approximately 30 minutes or more) and the shampoo after the dyeing process.
  • An objective of the present invention is to provide a new dyeing or coloring process for keratin materials, in particular human keratin materials, using the thermal transfer of specific nitro dyes, which makes it possible to rapidly and cleanly dye hair.
  • the above objective can be achieved by a method for dyeing keratin materials, in particular human keratin materials, comprising the steps of:
  • - R represents -NH 2 , -NHC 2 H 4 OH, -NHC 3 H 6 OH, -NHC 2 H 4 NH 2 , -OC 2 H40H, -NHCH 3 , or -OCH 2 CH(OH)CH 2 OH;
  • - R' represents -OH, -OCH 3 , -N(C 2 H 4 OH) 2 , -NH 2 , -NHC 2 H 4 OH, -OC 2 H 4 OH,
  • nitro dye for the present invention may correspond to the following formula (la), (lb), or (Ic):
  • - Rl represents -NH 2 , -NHC 2 H 4 OH, -NHC 3 H 6 OH, or -NHC 2 H 4 NH 2 ;
  • - R2 represents -OH, -N(C 2 H 4 OH) 2 , -NH 2 , -OC 2 H 4 OH, or -N(C 2 H 4 OH)(C 2 H 5 );
  • R3 represents a hydrogen atom or an alkyl radical
  • - R4 represents -OCH 3 , -OC 2 H 4 OH, -OCH 2 CH(OH)CH 2 OH, or -NHC 2 H40H;
  • - R5 represents -NHC 2 H 4 NH 2 , -NHCH 3 , or -NHC 2 H 4 OH;
  • R6 represents a hydrogen atom or a halogen atom
  • - R7 represents -OH or -NHC 2 H 4 OH
  • - R8 represents -NH 2 or -OCH 3
  • nitro dye used in the present invention may be selected from the group consisting of 4-amino-3-nitrophenol [610-81-1], 3-nitro-p ⁇ 2ra-hydroxyethyl aminophenol
  • the heating temperature be between 100 and 600°C, preferably, between 130 and 250°C, and more preferably between 140 and 220°C.
  • the heating time be between 0.01 and 30 seconds, preferably 0.1 and 10 seconds, and more preferably 0.1 to 5 seconds.
  • the dry composition comprising said at least one specific nitro dye be in the form of a film.
  • the dry composition may comprise at least one binder material.
  • binder material may be selected from the group consisting of film-forming polymers; celluloses;
  • plastics such as polyester, polystyrene, ketone resin, epoxy resin, terpene phenol resin, polyamide, polysulfone, polyethersulfone, polyvinyl butyral, acrylonitrile, styrene resin and polyacrylate; and waxes such as carnauba wax and paraffin wax.
  • the present invention also relates to a laminated sheet comprising:
  • - R represents -NH 2 , -NHC 2 H 4 OH, -NHC 3 H 6 OH, -NHC 2 H 4 NH 2 , -OC 2 H 4 OH, -NHCH 3 , or -OCH 2 CH(OH)CH 2 OH;
  • - R' represents -OH, -OCH 3 , -N(C 2 H 4 OH) 2 , -NH 2 , -NHC 2 H 4 OH, -OC 2 H 4 OH, -N(C 2 H 4 OH)(C 2 H 5 ), -OCH 2 CH(OH)CH 2 OH, or -NHCH 3 ;
  • R" represents a hydrogen atom, a halogen atom, or an alkyl radical
  • the support may comprise at least one material selected from the group consisting of an aluminum foil, a paper, and a synthetic material with a high glass transition temperature such as polyester, polycarbonate, polyamide, polyimide, and polyaramid.
  • the present invention also relates to a method for dyeing keratin materials, in particular human keratin materials, comprising the steps of:
  • the heating temperature be between 100 and 600°C, preferably between 130 and 250°C, and more preferably between 140 and 220°C. It is preferable that the heating time be between 0.01 and 30 seconds, preferably between 0.1 and 10 seconds, and more preferably between 0.1 and 5 seconds.
  • the inventors performed diligent research and developed a thermal transfer technology which can give (1) dry, (2) quick, and (3) clean coloration (no stain to scalp, clothes, and hairdressing accessories such as combs, towels, and the like) to keratin materials, in particular human keratin materials, and also be (4) environmentally friendly.
  • the present invention has the advantage of not requiring the use of a liquid dye product, which causes color transfer to scalp, clothes, and hairdressing accessories.
  • composition makes it possible to use dyes which are sparingly soluble or which are unstable in a liquid medium. This can contribute to further broadening the palette of colors possible.
  • the color on the keratin materials obtained by the present invention can be resistant to washing, shampooing, rinsing, perspiration, sebum, light and the like.
  • the present invention can rapidly and cleanly dye the keratin materials compared to conventional coloring methods. Finally, this method makes it possible to produce, in a simple manner, motifs on the materials treated, in particular on the hair.
  • a method for dyeing keratin materials using a dry composition comprises the steps of:
  • composition when it is specified that the composition is "dry”, that means that the variation in the dry extract of such a composition, measured before and after a thermal treatment in an oven for one hour at 100°C, varies by 20% by weight or less, preferably by 10% by weight or less.
  • the dry composition has a viscosity of more than 100 centipoises, preferably more than 1 ,000 centipoises.
  • a "dry composition” is free or substantially free from water or lower (CrC 6 ) alcohols.
  • such a composition comprises less than 10% by weight, preferably less than 5% by weight, and more preferably less than 1% by weight of water or lower alcohols.
  • Human keratin materials used herein mean substances made from keratin, in particular keratin fibers, such as hair or eyelashes.
  • the dry composition for the present invention comprises at least one specific nitro dye.
  • a single type or two or more types of nitro dyes in combination may be used.
  • the nitro dye may be represented by the following formula (I):
  • - R represents -NH 2 , -NHC 2 H 4 OH, -NHC 3 H 6 OH, -NHC 2 H 4 NH 2 , -OCa ⁇ OH, -NHCH 3 , or -OCH 2 CH(OH)CH 2 OH;
  • - R' represents -OH, -OCH 3 , -N(C 2 H 4 OH) 2 , -NH 2 , -NHC 2 H 4 OH, -OC 2 H 4 OH,
  • nitro dye may correspond to the following formula (la), (lb), or (Ic):
  • - Rl represents -NH 2 , -NHC2H4OH, -NHC 3 H 6 OH, or -NHC 2 H 4 NH 2 ;
  • - R2 represents -OH, -N(C 2 H 4 OH) 2 , -NH 2 , -OC 2 H 4 OH, or -N(C 2 H 4 0H)(C 2 H 5 );
  • R3 represents a hydrogen atom or an alkyl radical
  • - R4 represents -OCH 3 , -OCH 2 CH(OH)CH 2 OH, or -NHC 2 H 4 OH;
  • - R5 represents -NHC 2 H 4 NH 2 , -NHCH 3 , or -NHC 2 H 4 OH;
  • R6 represents a hydrogen atom or a halogen atom
  • - R7 represents -OH or -NHC 2 H 4 OH
  • - R8 represents -NH 2 or -OCH 3
  • R9 represents a hydrogen atom or a halogen atom.
  • alkyl refers to monovalent saturated aliphatic hydrocarbon groups, preferably having up to about 20 carbon atoms, preferably from 1 to 10 carbon atoms, and more preferably from 1 to 6 carbon atoms.
  • the hydrocarbon chain may be either straight-chained or branched. This term is exemplified by groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, tert-butyl, n-hexyl, n-octyl, tert-octyl and the like.
  • the alkyl radical is a methyl group.
  • halogen refers to an atom of chlorine, bromine, fluorine, or iodine.
  • the halogen atom is chlorine.
  • nitro dye may be selected from the group consisting of
  • the dry composition may comprise from 0.0001 to 100 % by weight, preferably 0.01 to 60% by weight, and more preferably 0.5 to 20% by weight of the nitro dye, relative to the total weight of the composition.
  • the dry composition may preferably be in the form of a film, because the handling of the composition is easy, and the nitro dye(s) in the dry composition can easily be transferred to keratin materials such as the hair.
  • the thickness of the film is not limited.
  • the thickness of the film may be between 0.01 mm and 2 mm, preferably between 0.02 mm and 2 mm, and more preferably between 0.05 mm and 1 mm.
  • the dry composition comprising at least one nitro dye mentioned above may further comprise at least one binder material.
  • binder material that may be used, alone or as a mixture, in the composition according to the invention, mention may be made of a film-forming polymer; celluloses; plastics such as polyester, polystyrene, ketone resin, epoxy resin, terpene phenol resin, polyamide, polysulfone, polyethersulfone, polyvinyl butyral, acrylonitrile, styrene resin and polyacrylate; and waxes such as carnauba wax and paraffin wax; and the like.
  • film-forming polymers reference may be made in particular to the manual International Cosmetic Ingredient Directory and Handbook 2000 edition, Volume 2, pages 1744 to 1747 which relates to film-forming compounds.
  • polymers capable of entering into the composition of the films comprising the nitro dye there may be mentioned, for example, polymers derived from
  • vinylpyrrolidone polyvinyl alcohol, polyurethanes, polymers derived from caprolactam, vinyllactam, vinyl acetate, polymers derived from acrylamide, polysaccharides capable of forming a film in the dry state such as cellulose derivatives, starches and derivatives, pullulan gum, gum arabic, pectins, alginates, carrageenans, galactomannans, agars, chitosans, chitins, polymers derived from hyaluronic acid, xanthan gum, karaya gum, proteins capable of forming a film in the dry state, such as gelatin, gluten, casein, zein, gliadin, hordein and their natural or synthetic derivatives, polymers derived from silicones, amphoteric or anionic polymers which are derived from monomers comprising at least one carboxylic, sulphonic or phosphoric functional group, acrylic copolymers of phosphorylcholine (lipidure), anion
  • suitable cationic film-forming polymers there may be mentioned more particularly the following polymers, having in general a number-average molecular mass of between 500 and about 5,000,000:
  • Ri and R 2 which are identical or different, each represent a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms;
  • R3 denotes a hydrogen atom or a CH 3 group
  • A is a linear or branched alkyl group of 1 to 6 carbon atoms, or a hydroxyalkyl group of 1 to 4 carbon atoms;
  • R t , Rs, 3 ⁇ 4, which are identical or different, represent an alkyl group having from 1 to 18 carbon atoms or a benzyl group;
  • X denotes a methosulphate anion or a halide such as chloride or bromide
  • the copolymers of the family (1) contain, in addition, one or more units derived from comonomers which may be chosen from the family of acrylamides, methacrylamides, diacetone acrylamides, acrylamides and methacrylamides substituted on the nitrogen with lower (C ) alkyls, groups derived from acrylic or methacrylic acids or esters thereof, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, and vinyl esters.
  • chitosan having a degree of deacetylation of 90% by weight
  • pyrrolidone-chitosan carboxylate sold under the name KYTAMER ® PC by the company AMERCHOL.
  • anionic film-forming polymers they generally comprise at least one group derived from a carboxylic, sulphonic or phosphoric acid and have a
  • carboxylic groups are more particularly provided by unsaturated mono- or dicarboxylic acid monomers such as those corresponding to the formula:
  • n is an integer from 0 to 10
  • Ai denotes a methylene group, optionally linked to the carbon atom of the unsaturated group or to the neighboring methylene group, when n is greater than 1 , through a heteroatom such as oxygen or sulphur
  • Ra denotes a hydrogen atom, or a phenyl or benzyl group
  • Rb denotes a hydrogen atom, a Ci-C 4 alkyl group, in particular methyl, ethyl or carboxyl
  • Rc denotes a hydrogen atom or a lower alkyl group, a group -CH 2 -COOH, or a phenyl or benzyl group.
  • the preferred anionic film-forming polymers with carboxylic groups are:
  • a monoethylene monomer such as ethylene, styrene, vinyl esters, acrylic or methacrylic acid esters, optionally grafted onto a polyalkylene glycol such as polyethylene glycol and optionally crosslinked.
  • Copolymers of this type contain in their chain an acrylamide unit optionally N-alkylated and/or hydroxyalkylated as described especially in Luxembourg Patent Applications 75370 and 75371.
  • copolymers of acrylic acid and C1-C4 alkyl methacrylate and the terpolymers of vinylpyrrolidone, acrylic acid and Ci-C2o alkyl for example lauryl, methacrylate such as that sold by the company ISP under the name ACRYLIDONE ® LM and the methacrylic acid/ethyl acrylate/tert-butyl acrylate terpolymers such as the product sold under the name LUVIMER ® 100 P by the company BASF.
  • copolymers derived from crotonic acid such as those containing in their chain vinyl propionate or acetate units and optionally other monomers such as methallyl or allyl esters, vinyl ether or vinyl ester of a linear or branched saturated carboxylic acid with a long hydrocarbon chain such as those containing at least 5 carbon atoms, it being possible for these polymers to be optionally grafted and crosslinked or alternatively another monomer which is a vinyl, allyl or methallyl ester of an a- or ⁇ -cyclic carboxylic acid.
  • copolymers comprising (i) one or more itaconic, fumaric or maleic acids or anhydrides and (ii) at least one monomer chosen from vinyl esters, vinyl ethers, vinyl halides, phenylvinyl derivatives, acrylic acid and its esters, the anhydride functions of these copolymers being optionally monoesterified or monoamidated.
  • Such polymers are described in particular in U.S. Patent Nos. 2,047,398, 2,723,248, 2,102,113 and GB Patent 839805. Marketed products are especially those sold under the names
  • copolymers comprising (i) one or more maleic, citraconic or itaconic anhydride units and (ii) one or more monomers chosen from allyl or methallyl esters optionally containing one or more acrylamide, methacrylamide or a-olefin groups, acrylic or methacrylic esters, acrylic or methacrylic acid or vinylpyrrolidone in their chain, the anhydride functions of these copolymers being optionally monoesterified or
  • the polyacrylamides containing carboxylate groups are polymers containing vinylsulpho ic, styrenesulphonic, naphthalenesulphonic or acrylamidoalkylsulphonic units.
  • These polymers may be especially chosen from:
  • film-forming anionic polymers of the grafted silicone type comprising a polysiloxane portion and a portion consisting of a nonsilicone organic chain, one of the two portions constituting the principal chain of the polymer, the other being grafted onto the said principal chain.
  • 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 U.S. Patent Nos.
  • Such polymers are, for example, the copolymers which can be obtained by free-radical polymerization starting with a mixture of monomers, consisting of:
  • C3 ⁇ 4 C— C— O— (C3 ⁇ 4) 3 — Si-O- ⁇ Si-O Si-(C3 ⁇ 4) 3 -
  • v being a number ranging from 5 to 700; the percentages by weight being calculated relative to the total weight of the monomers.
  • grafted silicone polymers include in particular
  • polydimethylsiloxanes onto which are grafted, via a chain link of thiopropylene type, mixed polymer units of poly(meth)acrylic acid type or of poly(alkyl(meth)acrylate) type, and polydimethylsiloxanes (PDMS) onto which are grafted, via a chain link of thiopropylene type, polymer units of
  • polyurethanes particularly sought by the present invention are those described in the patents EP 0 751 162, EP 0 637 600, FR 2 743 297 and EP 0 648 485 and the patents EP 0 656 021 or WO 94/03510 and EP 0 619 111.
  • the anionic film-forming polymers are preferably chosen from the acrylic acid copolymers such as the acrylic acid/ethyl acrylate/
  • N-tert-butylacrylamide terpolymers sold under the name ULTRAHOLD ® STRONG by the company BASF the copolymers derived from crotonic acid such as the vinyl acetate/vinyl tert-butylbenzoate/crotonic acid terpolymers and the crotonic acid/vinyl acetate/vinyl neododecanoate terpolymers sold in particular under the name Resine 28-29-30 by the company NATIONAL STARCH
  • LUVIMER ® MAEX or MAE by the company BASF and the vinyl acetate/crotonic acid copolymers and the vinyl acetate/crotonic acid copolymers grafted with polyethylene glycol sold under the name ARISTOFLEX ® A by the company BASF and the polyurethane Luviset PUR ® sold by the company BASF.
  • the anionic film-forming polymers which are most particularly preferred are those chosen from the monoesterified maleic anhydride/methyl vinyl ether copolymers sold under the name GANTREZ ® ES 425 by the company ISP, the acrylic acid ethyl acrylate/N-tert-butylacrylarnide terpolymers sold under the name ULTRAHOLD STRONG by the company BASF, the copolymers of methacrylic acid and of methyl methacrylate sold under the name EUDRAGIT ® L by the company ROHM PHARMA, the vinyl acetate/vinyl tert-butylbenzoate/crotonic acid terpolymers and the crotonic acid/vinyl acetate/vinyl neododecanoate terpolymers sold under the name Resine 28-29-30 by the company NATIONAL STARCH, the copolymers of methacrylic acid and ethyl acrylate sold under the name LUVIMER ® MA
  • amphoteric film-forming polymers which can be used, there may be mentioned those containing B and C units distributed randomly in the polymer chain where B denotes a unit which is derived from a monomer containing at least one basic nitrogen atom and C denotes a unit which is derived from an acidic monomer containing one or more carboxylic or sulphonic groups or alternatively B and C may denote groups which are derived from zwitterionic monomers of carboxybetaines or of sulphobetaines; B and C may also denote a cationic polymer chain containing primary, secondary, tertiary or quaternary amine groups, in which at least one of the amine groups carries a carboxylic or sulphonic group linked via a hydrocarbon group or alternatively B and C form part of a chain of a polymer with an a-dicarboxylic ethylene unit in which one of the carboxylic groups has been caused to react with a polyamine containing one or more primary or secondary amine
  • amphoteric film-forming 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 diethyldiallyl ammonium chloride.
  • the copolymers of acrylic acid and the latter monomer are offered under the names MERQUAT 280, MERQUAT 295 and MERQUAT PLUS 3330 by the company CALGON.
  • N-substituted acrylamides or methacrylamides more particularly preferred are compounds whose alkyl groups contain from 2 to 12 carbon atoms, and more
  • the acidic comonomers are chosen more particularly from acrylic, methacrylic, crotonic, itaconic, maleic and fumaric acids as well as the alkyl monoesters having 1 to 4 carbon atoms of maleic or fumaric anhydrides or acids.
  • the basic comonomers preferred are methacrylates of aminoethyl, butylaminoethyl, ⁇ , ⁇ '-dimethylaminoethyl, N-tert-butylaminoethyl.
  • octylacrylamide/acrylates/butylaminoethyl methacrylate copolymer such as the products sold under the name AMPHOMER ® or LOVOCRYL ® 47 by the company NATIONAL STARCH.
  • R 10 represents a divalent group derived from a saturated dicarboxylic acid, a mono- or dicarboxylic aliphatic acid with an ethylenic double bond, an ester of a lower alkanol having 1 to 6 carbon atoms of these acids or a group which is derived from the addition of any one of the said acids with a bis-primary or bis-secondary amine, and Z denotes a group which is derived from a bis-primary, mono- or bis-secondary
  • polyalkylene-polyamine and preferably represents:
  • the saturated carboxylic acids are preferably chosen from the acids having 6 to 10 carbon atoms such as adipic, 2,2,4-trimethyladipic and 2,4,4-trimethyladipic acids, terephthalic acid, and the acids with an ethylene double bond such as acrylic, methacrylic and itaconic acids.
  • the alkanesultones used in the acylation are preferably propane- or butanesultone, and the salts of the acylating agents are preferably the sodium or potassium salts.
  • Rn denotes a polymerizable unsaturated group such as an acrylate, methacrylate, acrylamide or methacrylamide group
  • y and z represent an integer from 1 to 3
  • Ri 2 and R 13 represent a hydrogen atom or a methyl, ethyl or propyl group
  • R 14 and R 15 represent a hydrogen atom or an alkyl group such that the sum of the carbon atoms in R H and R 15 does not exceed 10.
  • the polymers comprising such units may also comprise units derived from
  • nonzwitterionic monomers such as dimethyl- or diethylaminoethyl acrylate or methacrylate or alkyl acrylates or methacrylates, acrylamides or methacrylamides or vinyl acetate.
  • R 16 represents a group of formula:
  • the polymers corresponding to the general formula (IV) are described for example in French Patent 1 400 366 and comprise the repeating unit below:
  • R20 represents a hydrogen atom, a CH 3 0, CH3CH2O or phenyl group
  • R21 denotes a hydrogen atom or a lower alkyl group such as methyl or ethyl
  • R22 denotes a hydrogen atom or a C ⁇ lower alkyl group such as methyl or ethyl
  • R 23 denotes a C C 6 lower alkyl group such as methyl or ethyl or a group corresponding to the formula: -R24-N(R 22 )2, R24 representing a group -CH 2 -CH 2 -, -CH 2 -CH 2 -CH 2 - or -CH 2 -CH(CH 3 )-, R22 having the meanings mentioned above.
  • N-carboxymethyl chitosan or N-carboxybutyl chitosan are N-carboxymethyl chitosan or N-carboxybutyl chitosan.
  • amphoteric polymers of the -D-X-D-X- type chosen from:
  • unsubstituted or substituted with hydroxyl groups and which may contain, in addition, oxygen, nitrogen or sulphur atoms, 1 to 3 aromatic and/or heterocyclic rings; the oxygen, nitrogen and sulphur atoms being present in the form of ether, thioether, sulphoxide, sulphone, sulphonium, alkylamine or alkenylamine groups, or hydroxyl, benzylamine, amine oxide, quaternary ammonium, amide, imide, alcohol, ester and/or urethane groups.
  • D denotes a group N / ⁇ — and X denotes the symbol E or E' and, at least once, E';
  • E having the meaning indicated above and E' is a bivalent group which is an alkylene group with a linear or branched chain having up to 7 carbon atoms in the principal chain, which is unsubstituted or substituted with one or more hydroxyl groups and containing one or more nitrogen atoms, the nitrogen atoms being substituted with an alkyl chain optionally interrupted by an oxygen atom and necessarily containing one or more carboxyl functional groups or one or more hydroxyl functional groups and betainized by reaction with chloroacetic acid or sodium chloroacetate.
  • copolymers may also contain other vinyl
  • the preferred amphoteric film-forming polymers are those of the family (3) such as the copolymers whose CTFA name is Octylacrylamide/acrylates/butylaminoethyl methacrylate copolymer such as the products sold under the names AMPHOMER , AMPHOMER ® LV 71 or LOVOCRYL ® 47 by the company NATIONAL STARCH and those of the family (4) such as the butyl methacrylate/ N,N-dimethylcarboxyaminoethyl methacrylate copolymers.
  • nonionic film-forming polymers which can be used according to the present invention may be chosen for example from:
  • the copolymers of acrylic esters such as for example the copolymers of alkyl acrylates and alkyl methacrylates such as the products offered by the company ROHM & HAAS under the names PRIMAL ® AC-261 K and EUDRAGIT ® NE 30 D, by the company BASF under the name 8845, by the company HOECHST under the name APPRETAN ® N9212;
  • the copolymers of styrene and alkyl(meth)acrylate such as the products MOWILITH LDM 6911, MOWILITH ® DM 611 and MOWILITH ® LDM 6070 offered by the company HOECHST, the products RHODOPAS ® SD 215 and RHODOPAS ® DS 910 offered by the company RHODIA CHIMIE;
  • the alkyl groups of the nonionic polymers mentioned above preferably have from 1 to 6 carbon atoms.
  • the film-forming polymers are preferably nonionic polymers, and better still nonionic polymers with vinyllactam units. They are described in particular in United States Patents 3 770 683, 3 929 735, 4 521 504, 5 158 762, 5 506 315 and in Patent Applications WO 94/121148, WO 96/06592, and WO 96/10593. They may be provided in pulverulent form or in the form of a solution or a suspension.
  • the homopolymers or copolymers with vinyllactam units comprise units of formula:
  • n is independently 3, 4 or 5.
  • the number-average molecular mass of the polymers with vinyllactam units is generally greater than about 5,000, preferably between approximately 10,000 and 1,000,000, and more preferably approximately between 10,000 and 100,000.
  • polyvinylpyrrolidones such as those marketed under the name Luviskol ® K30 by the company BASF; polyvinylcaprolactams such as those marketed under the name Luviskol ® PLUS by the company BASF; poly(vinylpyrrolidone/vinyl acetate) copolymers such as those marketed under the name PVPVA S630L by the company ISP, Luviskol ® VA 73, VA 64, VA 55, VA 37 and VA 28 by the company BASF; and poly(vinylpyrrolidone/vinyl acetate/vinyl propionate) terpolymers such as those marketed under the name Luviskol ® YAP 343 by the company BASF.
  • the dry composition may comprise from 0.0001 to 80% by weight, preferably 0.01 to 40% by weight, and more preferably 0.1 to 20% by weight of the binder material, relative to the total weight of the composition.
  • the dry composition useful in the present invention may comprise at least one additive. One or more additives may be used.
  • the dry composition may comprise at least one plasticizer.
  • the plasticizers that are conventionally used in the field of the invention may be used in the dry composition.
  • urea glycerine
  • sorbitol mono- and/or disaccharides
  • dipropylene glycol butylene glycol
  • pentylene glycol or polyethylene glycol
  • benzyl alcohol or mixtures thereof.
  • the dry composition may comprise at least one formulation adjuvant and/or cosmetic active agent chosen for example from dispersing agents such as alkali metal lignosulphonates, antioxidants, pH-regulating agents, perfumes, silicones, and ceramides.
  • dispersing agents such as alkali metal lignosulphonates, antioxidants, pH-regulating agents, perfumes, silicones, and ceramides.
  • the content of the additive(s) in the dry composition may represent, for each, from 0.01 to 80% by weight, preferably 0.1 to 50% by weight, and more preferably 1 to 20% by weight; the total content of additives, if they are present, should not exceed 80% by weight of the dry composition.
  • the dry composition can be prepared by simply mixing at least one nitro dye or dyes as well as other ingredients such as at least one binder or binders. Any mixing means may be used for preparing the dry composition.
  • the dry composition in the form of a film may be prepared by:
  • the solvent preferably has a boiling point less than the vaporization or sublimation temperature of the nitro dye.
  • the boiling point of the solvent is less than or equal to 110°C.
  • the solvent entering into the mixture is preferably chosen from the compounds which solubilize or disperse at least the binder material.
  • the binder materials are in the form of dispersions of solid or liquid particles of polymer (latex or pseudolatex).
  • the solvent furthermore has a boiling point less than the sublimation temperature of the dye and less than the degradation temperature of the binder material.
  • said mixture may comprise from 5 to 99.9% by weight of solvent.
  • the mixture may be deposited on an appropriate heating plate.
  • the heating plate any plate with a heating device may be used.
  • a non-rough and horizontal heating plate can preferably used.
  • the mixture may be deposited in a conventional manner.
  • the mixture is deposited with an apparatus which makes it possible to obtain a substantially uniform film thickness.
  • the thickness of the mixture deposited is preferable for the thickness of the mixture deposited to be relatively uniform.
  • the thickness of the mixture deposited is such that a film is obtained, preferably after the evaporation of solvent, which can be handled at room temperature.
  • the thickness of the mixture deposited varies in general from 0.01 to 2 mm, preferably from 0.02 to 2 mm, and more preferably from 0.05 to 1 mm.
  • the dry composition as described above is applied to keratin materials, in particular human keratin materials.
  • a single type or two or more types of dry composition in combination may be used.
  • the manner of the application is not limited, and any conventional manner of applying can be used.
  • the dry composition may be applied to the keratin materials by using a hair brush, a comb, a glove, or a hand.
  • the dry composition may be placed on a support such as a film or sheet, and then the support is placed on the keratin materials such that the dry composition directly contacts with the keratin materials.
  • the composition and/or the keratin material is heated.
  • the manner of the heating is not limited, and any conventional manner of heating can be used.
  • a source of heat is brought into contact with the dry composition and/or the keratin materials to be treated. It is preferable to apply a source of heat to the dry composition and/or the keratin material to be treated to cause the vaporization or sublimation of the nitro dye(s) comprised in the above-mentioned dry composition.
  • the source of heat may be provided in a conventional manner.
  • a hair iron, hot air, hot steam, high frequency induction heating, microwave, infrared-light irradiation, UV light, visible light, ultrasonic wave, laser heating, and flash lamp irradiation, and the like examples of such source of heat which can be used for the purpose of the present invention.
  • the period for which the heat source is applied is such that the keratin material is not substantially degraded. More particularly, the physical and physicochemical properties of the keratin material are not substantially impaired. There is furthermore no substantial modification of their natural colour, or modification of their mechanical resistance properties.
  • the heating temperature to cause the sublimation of the nitro dye according to the present invention may be between 100 and 600°C, preferably between 130 and 250°C, and more preferably between 140 and 220°C.
  • the heating time to cause the sublimation of the nitro dye according to the present invention may be between 0.01 and 30 seconds, preferably between 0.1 and 10 seconds, and more preferably between 0.1 and 5 seconds.
  • Another embodiment of the present invention is a dry composition for thermal transfer process, which is used for dyeing keratin materials, in particular human keratin materials.
  • thermo transfer is understood to mean, for the purposes of the present invention, the nitro dye(s) transfers from the dry composition to the keratin materials under heat.
  • the nitro dye(s) enters a gaseous state thereof from the solid state thereof in the dry composition under heat without passing through the liquid state thereof, and the gaseous nitro dye(s) adhere(s) to or penetrate(s) into the keratin materials.
  • Such dry composition comprises at least one specific nitro dye as mentioned above. It is preferable that the nitro dye(s) is/are in a dispersed in the composition.
  • the dry composition for thermal transfer process according to the present invention may comprise at least one binder as mentioned above.
  • An another embodiment of the present invention is a laminated sheet, for a thermal transfer process, which can be used for dyeing keratin materials, in particular human keratin materials.
  • the laminated sheet according to the present invention comprises:
  • the dry composition used in this embodiment is as explained above. A single type or two or more types of the dry compositions in combination may be used.
  • the support must be resistant to heat stimulus and be flexible to allow easy use for the coloration process.
  • the support may advantageously be chosen from compounds which are not degraded under the conditions for carrying out the method.
  • a single type or two or more types of supports in combination may be used.
  • the support may be chosen from compounds which do not become solubilized under the conditions for preparing said film. Thus, the support is not soluble in an aqueous medium.
  • the support may be chosen from compounds which conduct electricity or from compounds which are electrical insulators.
  • the water-soluble or water insoluble support may thus be made of a material chosen from polyurethanes, thermoplastic elastomers of the type including
  • styrene-butadiene-styrene styrene-ethylene-butadiene-styrene
  • ethylene- vinyl acetate or coether ester
  • polyethylenes polypropylenes, or silicones.
  • Such supports are sold in particular under the trade marks: BAYDUR ® , DALTOFLEX ® , UROFLEX ® , HYPERLAST ® , INSPIRE ® , DESMOPAN ® , ESTANE ® , LASTANE ® , TEXIN ® , CARIFLEX ® , KRATON ® , SOLPRENE ® , ELVAX ® , ESCORENE ® ,
  • the material for the support may also be chosen from a paper, and a synthetic material with a high glass transition temperature such as polyester, polycarbonate, polyamide, polyimide, and poly ar amid. A single type or two or more types of materials in combination may be used.
  • an inorganic compound such as aluminum foil.
  • the thickness of the support on which the dry composition is deposited preferably has a thickness which allows easy use for dyeing the keratin materials (easy folding, sufficient solidity to allow several applications with several foldings and unfoldings).
  • the thickness of the support may be between 0.001 mm and 2 mm, preferably 0.005 mm and 2 mm, and more preferably between 0.01 mm and 1 mm.
  • the laminated sheet according to the present invention can be prepared by:
  • At least one nitro dye, at least one binder material, at least one solvent, and at least one optional additive to be included in the mixture can be chosen appropriately from those specifically described above.
  • the mixture is deposited on an appropriate support, such as a non-rough and horizontal support of the heating or non-heating bed or marble type.
  • an appropriate support such as a non-rough and horizontal support of the heating or non-heating bed or marble type.
  • the mixture is deposited directly on the support with which the mixture is intended to be used for dyeing, if such a variant is chosen.
  • the mixture may be deposited on the support in a conventional manner.
  • the mixture can be deposited with an apparatus which makes it possible to obtain a substantially uniform film thickness.
  • the thickness of the mixture deposited is such that a film of the dry composition can be obtained, preferably after evaporation of the solvent, which can be handled at room temperature (more particularly between 15 and 30°C).
  • the thickness of the mixture deposited on the support is between 0.01 mm and 2 mm, preferably between 0.02 mm and 1 mm, and more preferably between 0.05 mm and 0.5 mm.
  • the solvent is evaporated in a conventional manner to prepare a film comprising the dry composition.
  • the method for dyeing keratin materials, in particular human keratin materials, using said laminated sheet comprises the steps of:
  • the keratin materials are sandwiched by the laminated sheet.
  • the laminated sheet can be then heated preferably by a source of heat so that the nitro dye comprised in the laminated sheet vaporizes or sublimes.
  • the heating may be performed in a conventional manner.
  • a source of heat may be applied to the laminated sheet and/or the keratin materials.
  • the heating temperature to cause the sublimation of the nitro dye according to the present invention may be between 100 and 600°C, preferably between 130 and 250°C, and more preferably between 140 and 220°C.
  • the heating time to cause the vaporization or sublimation of the nitro dye according to the present invention is between 0.01 and 30 seconds, preferably between 0.1 and 10 seconds, and more preferably between 0.1 and 5 seconds.
  • the dye used was as follows.
  • the film obtained above was applied to a dry natural grey hair lock which is 90% white.
  • the hair lock was then covered with an aluminum foil.
  • the hair lock was thermally pressed by a hair iron with the condition of 220°C for 10 seconds. After this process, the hair lock was dyed and no rinsing was necessary.
  • the above hair dyeing process was performed in only a short period of time such as 10 seconds, and no solvent such as water or alcohol was used. Therefore, the above hair dyeing process was a quick and dry process. Further, since only the hair lock was dyed and no color transfer to other objects such as the hands was observed, the above hair dyeing process can realize clean coloring. Furthermore, since no rinsing is necessary, the above hair dyeing process was environmentally friendly.
  • spectrocolorimeter (illuminant D65, angle 10°, SCI values) for the L*, a*, b* colorimetric measurements.
  • L* represents the intensity of the color
  • a* indicates the green/red color axis
  • b* indicates the blue/yellow color axis.
  • AE* /(L * -L 0 * ) 2 + (a * -a 0 * ) + (b* - b 0 *) 2
  • L*, a* and b* represent the values measured after dyeing the natural hair lock comprising 90% of white hairs and Lo*, ao*, and bo* represent the values measured for the untreated natural hair lock.
  • ⁇ * the greater the difference in color between the undyed lock and the dyed lock.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention porte sur un procédé qui permet de teinter des matières kératiniques, en particulier des matières kératiniques humaines. Ledit procédé consiste à appliquer au moins une composition sèche comprenant au moins un colorant nitré sur les matières kératiniques, et à chauffer la composition et/ou les matières kératiniques afin d'entraîner le transfert thermique du ou des colorants. Le procédé de teinture par transfert thermique selon l'invention permet une coloration améliorée des matières kératiniques, au moyen d'une technique sèche, rapide, propre et respectueuse de l'environnement.
PCT/JP2011/075238 2011-10-26 2011-10-26 Coloration capillaire par transfert thermique WO2013061477A1 (fr)

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GB839805A (en) 1957-06-10 1960-06-29 Monsanto Chemicals Sprayable compositions
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FR2265781A1 (fr) 1974-04-01 1975-10-24 Oreal
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EP0412704A2 (fr) 1989-08-07 1991-02-13 The Procter & Gamble Company Compositions pour traiter et fixer la chevelure
EP0412707A1 (fr) 1989-08-07 1991-02-13 The Procter & Gamble Company Compositions pour le conditionnement et la mise en forme des cheveux
US4972037A (en) 1989-08-07 1990-11-20 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer topical binder composition with novel fluorochemical comonomer and method of coating therewith
US5158762A (en) 1992-03-09 1992-10-27 Isp Investments Inc. Water-based hair spray compositions containing multiple polymers
US5506315A (en) 1992-03-12 1996-04-09 Basf Aktiengesellschaft Preparation of copolymers of monoethylenically unsaturated monomers containing acid groups and N-vinyllactams
WO1993023009A1 (fr) 1992-05-12 1993-11-25 Minnesota Mining And Manufacturing Company Polymeres utilises dans des compositions cosmetiques et des produits de soins
EP0640105A1 (fr) 1992-05-15 1995-03-01 The Procter & Gamble Company Agents adhesifs contenant un polymere a greffe polysiloxane et leur compositions cosmetiques
EP0582152A2 (fr) 1992-07-28 1994-02-09 Mitsubishi Chemical Corporation Composition cosmétique pour les cheveux
WO1994003510A1 (fr) 1992-07-29 1994-02-17 Basf Aktiengesellschaft Utilisation de polyurethannes solubles dans l'eau ou dispersibles dans l'eau comme adjuvants dans des preparations cosmetiques et pharmaceutiques, et polyurethannes renfermant des polyolpolylactiques incorpores par polymerisation
EP0656021A1 (fr) 1992-07-29 1995-06-07 Basf Ag Utilisation de polyurethannes solubles dans l'eau ou dispersibles dans l'eau comme adjuvants dans des preparations cosmetiques et pharmaceutiques, et polyurethannes renfermant des polyolpolylactiques incorpores par polymerisation.
WO1994012148A1 (fr) 1992-11-30 1994-06-09 Eastman Chemical Company Formules de spray capillaire a aerosol
EP0619111A1 (fr) 1993-04-06 1994-10-12 National Starch and Chemical Investment Holding Corporation Utilisation des polyuréthanes avec des groupes carboxyliques fonctionelle comme agent fixateur des cheveux
WO1995000578A1 (fr) 1993-06-24 1995-01-05 The Procter & Gamble Company Copolymeres de polyolefine modifies au siloxane
EP0637600A1 (fr) 1993-08-04 1995-02-08 L'oreal Nouveaux polyester-polyuréthannes, leur procédé de préparation, pseudo-latex réalisés à partir desdits polyester-polyuréthannes et leur utilisation dans des compositions cosmétiques
EP0648485A1 (fr) 1993-10-15 1995-04-19 L'oreal Vernis à ongles aqueux, contenant des particules de polyester-polyuréthanne anionique à l'état dispersé
EP0659398A1 (fr) * 1993-12-22 1995-06-28 L'oreal Procédé de coloration directe des fibres kératiniques humaines à l'aide de colorants sulfoniques et de vapeur d'eau
FR2713925A1 (fr) * 1993-12-22 1995-06-23 Oreal Procédé de coloration directe des fibres kératiniques humaines à l'aide de colorants naturels et de vapeur d'eau.
WO1996006592A1 (fr) 1994-08-31 1996-03-07 Isp Investments Inc. Composition de resine pour laque en aerosol a faible teneur en composes organiques volatils aux proprietes de pulverisation ameliorees
WO1996010593A1 (fr) 1994-09-30 1996-04-11 Basf Aktiengesellschaft PROCEDE DE PREPARATION DE SOLUTIONS AQUEUSES DE POLY(N-VINYL-ε-CAPROLACTAME) ET LEUR UTILISATION
EP0751162A1 (fr) 1995-06-27 1997-01-02 L'oreal Utilisation dans et pour la fabrication de compositions cosmétiques ou dermatologiques de polycondensats séquencés polyuréthanes et/ou polyurées à greffons siliconés
FR2743297A1 (fr) 1996-01-05 1997-07-11 Oreal Composition cosmetiques a base de polycondensats ionisables multisequences polysiloxane/polyurethane et/ou polyuree en solution et utilisation
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