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WO 2015/198923 Al 30 December 2015 (30.12.2015) P O P C T

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WO 2015/198923 Al 30 December 2015 (30.12.2015) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2015/198923 Al 30 December 2015 (30.12.2015) P O P C T (51) International Patent Classification: (74) Agents: MURAYAMA, Yasuhiko et al; 1-9-2, Marunou- A61K 8/33 (2006.01) A61K 8/46 (2006.01) chi, Chiyoda-ku, Tokyo, 1006620 (JP). A61K 8/35 (2006.01) A61Q 5/06 (2006.01) (81) Designated States (unless otherwise indicated, for every A61K 8/37 (2006.01) kind of national protection available): AE, AG, AL, AM, (21) International Application Number: AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, PCT/JP2015/067380 BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IR, IS, KE, KG, KN, KP, KR, 10 June 2015 (10.06.2015) KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, (25) Filing Language: English MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, (26) Publication Language: English SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, (30) Priority Data: TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. 2014-128963 24 June 2014 (24.06.2014) JP (84) Designated States (unless otherwise indicated, for every (71) Applicant (for all designated States except AL): kind of regional protection available): ARIPO (BW, GH, L'OREAL [FR/FR]; 14 rue Royale, 75008 Paris (FR). GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, (72) Inventors; and TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, (71) Applicants (for AL only): MIYAKE, Shiho [JP/JP]; c/o DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, NIHON L'OREAL K.K., KSP R&D-A1 101, 3-2-1, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, Sakado, Takatsu-ku, Kawasaki-shi, Kanagawa, 2130012 SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, (JP). YAMADA, Hidetoshi [JP/JP]; c/o NIHON GW, KM, ML, MR, NE, SN, TD, TG). L'OREAL K.K., KSP R&D-A1 101, 3-2-1, Sakado, Takat su-ku, Kawasaki-shi, Kanagawa, 2130012 (JP). MISU, Published: Daisuke [JP/JP]; c/o NIHON L'OREAL K.K., KSP R&D- — with international search report (Art. 21(3)) A 1101, 3-2-1, Sakado, Takatsu-ku, Kawasaki-shi, Kanagawa, 2130012 (JP). (54) Title: COMPOSITION FOR KERATIN FIBERS (57) Abstract: The present invention relates to a composition for dyeing keratin fibers, comprising: (a) at least one direct dye; (b) at least one aprotic polar solvent; and (c) at least one sulfur-containing reducing agent. The composition according to the present in vention can prevent or reduce skin staining by the direct dye on the skin such as scalp, as well as the stiffness of the keratin fibers, while providing the keratin fibers with good cosmetic effects such as good coloring properties. DESCRIPTION COMPOSITION FOR KERATIN FIBERS TECHNICAL FIELD The present invention relates to a composition for keratin fibers, in particular for dyeing keratin fibers with at least one direct dye, as well as a process using the same. BACKGROUND ART It is known to dye keratin fibers and in particular human hair with dyeing compositions containing oxidative coloring precursors, generally called oxidative bases, such as ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds. These oxidative bases are generally combined with couplers. These bases and these couplers are colorless or weakly colored compounds which, combined with oxidizing products, can give rise to colored compounds through an oxidative condensation process. This type of coloring by oxidation makes it possible to get colors with very high visibility, coverage of white hair and in a wide variety of shades but it results in damage to the keratin fibers by the use of oxidizing agents (in particular by repeated application or by combination with other hair treatments). On the other hand, it is also known to dye keratin fibers and in particular human hair with dyeing compositions containing direct dyes. Conventional direct dyes are in particular the following: benzene nitrates, anthraquinones, nitropyridines, azos, xanthines, acridinies, azinies, and triarylmethane type or natural colorings. For example, JP-A-2000-186018, JP-A-2006-342159 and WO 2010/032034 (JP-T-2012-502896) disclose a composition for dyeing hair, including a direct dye. The hair coloration using direct dyes has advantages over the hair coloration using oxidative dyes: it has no allergic issue, no damage to the hair, and it gives vivid color visibility. DISCLOSURE OF INVENTION However, skin staining has been an inevitable drawback of the hair coloration performance using direct dyes. In addition to the skin staining, hair stiffness caused by the acidic condition for direct dyes is also an issue for the hair coloration with direct dyes. An objective of the present invention is to provide a composition for keratin fibers, in particular for dyeing keratin fibers, which uses a direct dye, but can prevent or reduce skin staining by the direct dye on the skin such as scalp, preferably as well as the stiffness of the keratin fibers, while providing the keratin fibers with good cosmetic effects such as good coloring properties. The above objective can be achieved by a composition for dyeing keratin fibers, comprising: (a) at least one direct dye; (b) at least one aprotic polar solvent; and (c) at least one sulfur-containing reducing agent. The (a) direct dye may be selected from the group consisting of acidic direct dyes, basic direct dyes and neutral direct dyes. The (a) direct dye may be selected from the group consisting of: the diaryl anionic azo dyes of formula (II) or (IT): in which formulae (II) and (IT): R , R , R9, R10, R'7, R's, R'9 and R' o which may be identical or different, represent a hydrogen atom or a group chosen from: - alkyl; alkoxy, alkylthio; hydroxyl, mercapto; nitro; R°-C(X)-X'-, R°-X'-C(X)-, R°-X'-C(X)-X"- with R° representing a hydrogen atom or an alkyl or aryl group; X, X' and X", which may be identical or different, representing an oxygen or sulfur atom, or NR with R representing a hydrogen atom or an alkyl group; (0) 2S(0 )-, X with X representing an organic or mineral cationic counter ion; - R"-S(0) 2-, with R" representing a hydrogen atom or an alkyl, aryl, (di)(alkyl)amino or aryl(alkyl)amino group; preferably a phenylamino or phenyl group; R"'-S(0) 2-X'- with R'" representing an alkyl or optionally substituted aryl group; (di)(alkyl)arnino; aryl(alkyl)amino optionally substituted with one or more groups chosen from i) nitro; ii) + nitroso; iii) (0) 2S(0 )-, X and iv) alkoxy with X ; optionally substituted heteroaryl; preferably a benzothiazolyl group; cycloalkyl; especially cyclohexyl, - Ar-N=N- with Ar representing an optionally substituted aryl group, preferably a phenyl 4 optionally substituted with one or more alkyl, (0) 2S(0 )-, X or phenylamino groups; or alternatively two contiguous groups R7 with R or ¾ with R 9 or R 9 with Rio together form a fused benzo group A'; and R ' with R'g or R' with R'9 or R'9 with R'io together form a fused benzo group B'; with A' and B' optionally substituted with one or more groups chosen from i) nitro; ii) nitroso; iii) (0) 2S(0 )-, X*; iv) hydroxyl; v) mercapto; vi) (di)(alkyl)amino; vii) R°-C(X)-X'-; viii) R°-X'-C(X)-; ix) R°-X'-C(X)-X"-; x) Ar-N=N- and xi) optionally substituted aryl(alkyl)amino; W represents a sigma bond σ, an oxygen or sulfur atom, or a divalent radical i) -NR-, or ii) methylene -C(Ra)(Rb)- with Ra and R b, which may be identical or different, representing a hydrogen atom or an aryl group, or alternatively Ra and R form, together with the carbon atom that bears them, a spiro cycloalkyl; preferably W represents a sulfur atom or Ra and R b together form a cyclohexyl; wherein formulae (II) and (ΙΓ ) comprise at least one sulfonate (0 )2S(0 )-, X or phosphonate + (0)P(0 2 ) 2X or carboxylate (0)C(0>, X* radical on one of the rings A, A', B, B' or C; and the anthraquinone dyes of formulae (III) and (III'): in which formulae (III) and (ΠΓ ) : R22, R23, R24, R25, R26 and R27, which may be identical or different, represent a hydrogen or halogen atom or a group chosen from: alkyl; hydroxyl, mercapto; alkoxy, alkylthio; - aryloxy or arylthio optionally substituted, preferably substituted with one or more groups chosen from alkyl and (0) 2S(0 )-, X with X representing an organic or mineral cationic counter ion; aryl(alkyl)amino optionally substituted with one or more groups chosen from alkyl and (di)(alkyl)amino; (di)(¾ydroxyalkyl)amino; - (O S O X Z ' represents a hydrogen atom or a group NR2 R29 vvith R2 and R2 , which may be identical or different, representing a hydrogen atom or a group chosen from: alkyl; polyhydroxyalkyl such as hydroxyethyl; - aryl optionally substituted with one or more groups, particularly i) alkyl such as methyl, -dodecyl, n-butyl; ii) (0) 2S(0 )-, * iii) R°-C(X)-X'-, R°-X'-C(X)-, R°-X'-C(X)-X"-, preferably R° represents an alkyl group; cycloakyl; especially cyclohexyl; Z represents a group chosen from hydroxyl and NR' 2 R'29 with R'28 and R'29, which may be identical or different, representing the same atoms or groups as R and R ; ΠΙ ΙΙΓ wherein formulae ( ) and ( ) comprise at least one sulfonate group (0) 2S(0 )-, X*.
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