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WO 2016/097248 Al 23 June 2016 (23.06.2016) W P O P C T

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WO 2016/097248 Al 23 June 2016 (23.06.2016) W 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 2016/097248 Al 23 June 2016 (23.06.2016) W P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A61Q 5/06 (2006.01) A61K 36/00 (2006.01) kind of national protection available): AE, AG, AL, AM, A61K 8/97 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, (21) Number: International Application DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, PCT/EP20 15/080403 HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, (22) International Filing Date: KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, 18 December 2015 (18. 12.2015) 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, (25) Filing Language: English SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, (26) Publication Language: English TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 1462873 19 December 2014 (19. 12.2014) FR kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, (71) Applicant: L'OREAL [FR/FR]; 14, rue Royale, 75008 TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, Paris (FR). TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (72) Inventors: CHOISY, Patrick; 6, quai Albert Baillet, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, 37270 Montlouis-sur-Loire (FR). GUENAULT, Emilie; 1, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, rue de la Baratterie, 37390 Saint-Roch (FR). GABANT, GW, KM, ML, MR, NE, SN, TD, TG). Marion; 1, ave Eugene Schueller, BP 22, 93601 Aul- nay-sous-Bois (FR). Published: (74) Agent: KUHLMANN, Sonia; L'Oreal, D.I.P.I., 25-29, — with international search report (Art. 21(3)) quai Aulagnier, 92665 Asnieres-sur-Seine Cedex (FR). 00 l © (54) Title: PROCESS FOR DYEING KERATIN FIBRES USING PRE-HYDROLYSED AND DECONTAMINATED HENNA ¾ (57) Abstract: The subject of the invention is i) a process for preparing an aqueous composition comprising pre-hydrolysed and de - contaminated henna, ii) the aqueous composition prepared according to the process, iii) a process for dyeing keratin fibres, in partic - ular human keratin fibres, such as the hair, which uses the composition comprising pre-hydrolysed and decontaminated henna op - tionally extemporaneously with indigo, and iv) the use of the composition comprising the pre-hydrolysed and decontaminated henna, for dyeing keratin fibres. PROCESS FOR DYEING KERATIN FIBRES USING PRE-HYDROLYSED AND DECONTAMINATED HENNA The subject of the invention is i) a process for preparing an aqueous composition comprising pre-hydrolysed and decontaminated henna, ii) the aqueous composition prepared according to the process, iii) a process for dyeing keratin fibres, in particular human keratin fibres, such as the hair, which uses the composition comprising pre-hydrolysed and decontaminated henna optionally extemporaneously with indigo, iv) the use of the composition comprising the prehydrolysed and decontaminated henna and optionally indigo prepared extemporaneously, for dyeing keratin fibres in a single action. Two major methods for dyeing human keratin fibres, and in particular the hair, are known. The first, known as oxidation dyeing or permanent dyeing, consists in using one or more oxidation dye precursors, more particularly one or more oxidation bases optionally combined with one or more couplers. Oxidation bases are usually chosen from ortho- or para-phenylenediamines, ortho- or para-aminophenols, and heterocyclic compounds. These oxidation bases are colourless or weakly coloured compounds, which, when combined with oxidizing products, can give rise via a process of oxidative condensation to coloured species, which remain trapped within the fibre. The shades obtained with these oxidation bases are often varied by combining them with one or more couplers, these couplers being chosen in particular from aromatic meta- diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds, such as indole compounds. The variety of the molecules used as oxidation bases and couplers allows a wide range of colours to be obtained. The second dyeing method, known as direct dyeing or semi-permanent dyeing, comprises the application of direct dyes, which are coloured and colouring molecules that have affinity for fibres. Given the nature of the molecules used, they tend rather to remain on the surface of the fibre and penetrate relatively little into the fibre, when compared with the small molecules of oxidation dye precursors. The main advantages of this type of dyeing are that it does not require any oxidizing agent, which limits the degradation of the fibres, and that it does not use any dyes that have particular reactivity, resulting in limitation of the intolerance risks. The first hair dyes were semi-permanent. One of the most well known natural dyes is that derived from the henna plant. Henna continues to be used in feminine beauty enhancement for colouring the hair or the nails, or for dyeing leather, silk and wool, etc. It is also used traditionally for various important events, celebrations and beliefs. Red henna is constituted of leaves of shrubs of the genus Lawsonia from the family Lythraceae, which is based on the principle of dyeing with the active agent lawsone: 2- hydroxy-1 ,4-naphthoquinone. Lawsone [83-72-7] (CI Natural Orange 6 ; C I 75420), also known as isojuglone, may be found in henna shrubs (Lawsonia alba, Lawsonia inermis) ("Dyes, Natural", Kirk-Othmer Encyclopedia of Chemical Technology, "Henna " Encyclopedia Britannica). This dye affords an orange-red colouration on grey hair, and a "warm" i.e. coppery to red colour on chestnut-brown hair. The dyeing process using henna is difficult to perform. A kind of "paste" (often referred to as a "poultice") is first made from ground or powdered henna leaves, which is then diluted at the time of use with warm water, and said paste is then applied to the keratin fibres. However, this process using said paste has drawbacks. During the preparation and application of the composition to keratin fibres, it is not always possible to obtain satisfactory impregnation due to the poor consistency of the composition obtained from the ground powder. Furthermore, it is very difficult to hope to reproduce the shades exactly, since the lawsone content very often varies from one batch to another and between different ground materials. The henna leaf in reality contains only a very small amount of lawsone, but contains its glycosylated precursor (NGP), enzymes and β-glucosidases. In the presence of water, said enzymes hydrolyse glucose and release a naphthohydroquinone which is rapidly oxidized in atmospheric oxygen to lawsone. Since the amount of β-glucosidases is small, approximately 1.8 U β-glucosidase/g of leaf, the reaction is slow. It is known practice to use exogenous enzymes of β-glucosidase type with henna (DE 1020500); nevertheless, the provision of exogenous enzymes can bring about type I allergies, the effectiveness of said enzymes is also significantly decreased by, in particular, problems of diffusion, added to this is the potential problem of storage of a composition comprising enzymes, and the excess cost generated is considerable. Moreover, henna powder generally contains between 105 and 106 bacteria per gram of leaves. In point of fact, it is preferable to have a henna powder quality with a very low bacterial content. In order to ensure a suitable microbiological quality, it is necessary to decontaminate, in particular by applying an ionizing treatment to the henna. The problem is that this treatment decreases the amount of β-glucosidases, and subsequently the capacity of the henna to suitably dye the keratin fibres. Another very well-known natural dye is indigo (see Ullmann's Encyclopedia of Industrial Chemistry, Hair preparation, point 5.2.3, 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim; 10.1002/1 4356007.a 12 57 1.pub2). Indigo continues to be used for feminine beauty enhancement by dyeing the hair or the nails, or for dyeing fabrics (jeans), leather, silk, wool, etc. Indigo [482-89-3] is a natural dye, originating in particular from the indigo plant, and having the empirical formula: C H N and having the structure: 6 0 2O2; Indigo is derived from indican and may be prepared from various plants known as indigo-producing plants such as Indigofera tinctoria, Indigo suffruticosa, Isatis tinctoria, etc. (see Kirk-Othmer Encyclopedia of Chemical Technology, updated on 17/04/2009, DOI: 10.1002/0471238961 .0425051903150618.a01 .pub2). The indigo-producing plants are generally chopped and soaked in hot water, heated, fermented and oxidized in the open air to liberate the purple-blue coloured indigo (see Chem. Rev. 201 1, 1 1 1, 2537-2561 , p. 2537- 2561). Indigo is the result of the fermentation, in the presence of β-glucosidases, and then oxidization of indican (glycosyl precursor). The indigo molecule is insoluble in water. The current colourations with henna and derived from indigo-producing plant(s) are applied in the form of a poultice for a long leave-on time on the hair and are then rinsed out, and the hair is dried, generally in the open air without final shampooing, so as to allow the colouration to become oxidized in the course of the following hours or even days.
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