+

WO2014068102A2 - Procédé de coloration et de lissage des cheveux - Google Patents

Procédé de coloration et de lissage des cheveux Download PDF

Info

Publication number
WO2014068102A2
WO2014068102A2 PCT/EP2013/072906 EP2013072906W WO2014068102A2 WO 2014068102 A2 WO2014068102 A2 WO 2014068102A2 EP 2013072906 W EP2013072906 W EP 2013072906W WO 2014068102 A2 WO2014068102 A2 WO 2014068102A2
Authority
WO
WIPO (PCT)
Prior art keywords
hair
composition
straightening
process according
dye
Prior art date
Application number
PCT/EP2013/072906
Other languages
English (en)
Other versions
WO2014068102A3 (fr
Inventor
Burkhard Rose
Jonathan Wood
Original Assignee
Kao Corporation
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 Kao Corporation filed Critical Kao Corporation
Publication of WO2014068102A2 publication Critical patent/WO2014068102A2/fr
Publication of WO2014068102A3 publication Critical patent/WO2014068102A3/fr

Links

Classifications

    • 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
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61Q5/10—Preparations for permanently dyeing the hair
    • 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
    • A61K2800/88—Two- or multipart kits
    • A61K2800/884—Sequential application

Definitions

  • the present invention relates to a method for dyeing and semipermanent straightening of the hair in two steps.
  • the shape of the hair is largely determined by the disulfide bonds linking two cysteine moieties of the hair keratin.
  • known methods involve the cleavage of the disulfide bonds by the action of a sulfide- or thio group containing reducing agent.
  • new disulfide bonds are formed by applying an oxidizing agent such as hydrogen peroxide, thus fixing the shape of the hair.
  • reducing compositions comprising thioglycolates or thiolactates as reducing agents and fixing compositions comprising hydrogen peroxide as an oxidizing agent.
  • the reducing compositions may further comprise a salt of an acid such as glyoxylic acid as a buffering agent.
  • the disulfide bridges can be cleaved by the action of an alkaline agent such as sodium hydroxide at a pH of about 11 or higher.
  • the disulfide (or cystin) moiety can undergo a disproportionation reaction under the elimination of sulfur, and is cleaved into an alpha-beta-unsaturated dehydro-alanine moiety and a cysteine moiety.
  • the dehydro-alanin moieties and the cysteine moieties form thioether bonds and combine to lanthionine, stabilizing the straightened state of the hair. Since the disulfide or cysteine moieties are converted into lanthionine moieties, this type of hair straightening process using an alkaline agent is also called lanthionization .
  • lanthionization method rely on a cleavage of the disulfide bonds and the formation of new bonds among the hair proteins, leading to an irreversible change of the shape of the hair. This means that these processes can achieve a permanent straightening, wherein the treated portion of the hair maintains its shape, and the straightening effect only vanishes because of the growth of the hair.
  • carboxylic acids having a carbonyl group adjacent to the carboxy group such as
  • glyoxylic acid which are known as a buffering agent in cosmetic compositions, may have a semi-permanent
  • semi-permanent means that the hair maintains its straightened appearance for several washing cycles.
  • permanent straightening wherein the shape of the hair is modified irreversibly, as in the above-described methods based on the cleavage of the disulfide bonds, and in contrast to the transient straightening achieved with a straightening iron, which vanishes by the action of moisture.
  • WO 2011/104282 describes a process for semipermanent hair straightening, which involves applying a composition comprising an a-keto acid onto the hair, leaving the composition in contact with the hair for 15 to 120 minutes, drying the hair and straightening the hair with a straightening iron at a temperature of 200 ⁇ 50°C.
  • WO 2012/010351 describes a treatment for semipermanent straightening of curly, frizzy or wavy hair by applying a solution of glyoxylic acid in combination with mechanical straightening, using a straightening iron at a temperature of 200 ⁇ 30°C. After the treatment, the hair is said to retain its shape for at least six consecutive
  • Hair dyeing methods and agents may be categorized in
  • hair dyes are usually classified as “permanent”, “demi- permanent” , “semi-permanent” or “temporary”. Permanent and demi-permanent dyes are typically formed by oxidation dyes, while direct dyes are used for semi-permanent or temporary colouring . Oxidation dyes are formed from low molecular intermediates which are known as “precursors” and “couplers”, respectively. These molecules are small enough to penetrate into the hair.
  • the precursors are usually aromatic para compounds such as 1 , 4 -diaminobenzene , and are used alone or in combination with aromatic meta compounds such as 1, 3 -diaminobenzene as
  • the precursor is oxidized and reacts with the coupler, thus forming the dye molecule.
  • the oxidative dye composition comprises ammonia as an alkalizing agent, in order to achieve a swelling of the hair and thus enhances the penetration of the precursor and the coupler into the hair.
  • the oxidizing agent By the action of the oxidizing agent, the intermediates are coupled inside the hair. Since the size of the thus formed dye molecule is larger than the size of the intermediates, the dye molecule stays trapped inside the hair, so that a permanent colouring can be
  • direct dyes the actual dye molecule is applied to the hair and adheres to the hair surface because of, for example, electrostatic interactions.
  • the penetration of the direct dyes into the hair is relatively poor because of the larger molecule size.
  • direct dyes can be washed out, so that the colouring is merely temporary.
  • Some direct dyes, in particular nitro dyes, may adhere more firmly to the hair and may penetrate deeper into the hair surface to some extent. Colouring compositions comprising these dyes are washed out less easily and thus are termed "semi -permanent" .
  • the present invention relates to a process for dyeing and straightening hair, which comprises the following steps performed in this order:
  • a composition comprising at least one hair dye, optionally at least one alkalizing agent and optionally at least one
  • composition having a pH of 4 or lower and comprising at least one carboxylic acid of the formula (I) and/or a hydrate thereof and/or a salt thereof onto the hair:
  • steps (i) to (i) are carried out directly after the steps (a) to (c) .
  • hair straightening may be divided into two main categories. The first is permanent straightening, wherein hair shape is irreversibly changed either by a two-step reduction and oxidation process or alternatively by treating hair with a strong alkaline composition having pH values 11.0 or above. The second is semi-permanent straightening wherein hair is straightened relatively reversibly and returns to its
  • the present invention relates to semi- permanent straightening, and does not involve the cleavage of disulfide bonds by sulfur-based reducing agents or alkali.
  • the present invention relates to a hair treatment kit comprising a straightening composition and a hair dye composition as described above, for use in the above-described process.
  • the dye composition and/or the straightening composition may suitably comprise further ingredients such as surfactants and/or conditioning components defined below, and may
  • disulfide-cleaving agents and/or the agents for forming new disulfide bonds Accordingly, the combination of conventional hair straightening directly after hair colouring was likely to cause severe hair damage, leading to a dull appearance and reduced colour stability, since the dye may be washed out through the formed cracks and fissures.
  • the present invention solves this problem by providing a method which achieves a coulouring and straightening of the hair in two steps in direct succession.
  • the method of the present invention uses a first composition (dye composition) comprising at least one hair dye, optionally at least one alkalizing agent and optionally at least one oxidizing agent, and a second composition (dye composition) comprising at least one hair dye, optionally at least one alkalizing agent and optionally at least one oxidizing agent, and a second composition (dye composition) comprising at least one hair dye, optionally at least one alkalizing agent and optionally at least one oxidizing agent, and a second composition (dye composition) comprising at least one hair dye, optionally at least one alkalizing agent and optionally at least one oxidizing agent, and a second composition (dye composition) comprising at least one hair dye, optionally at least one alkalizing agent and optionally at least one oxidizing agent, and a second composition (dye composition) comprising at least one hair dye, optionally at least one alkalizing agent and optionally at least one oxidizing agent, and a second composition (dye composition) comprising at
  • composition comprising at least one carboxylic acid of the Formula (I) below.
  • the hair is treated with the said compositions successively, so that the straightening treatment is performed directly after the colouring treatment.
  • time interval between the two treatments is not more than two or three hours, preferably not more than one hour, more
  • the dye composition used in the present invention contains at least one hair dye, optionally at least one alkalizing agent and optionally at least one oxidizing agent.
  • the at least one hair dye generally is at least one direct dye, at least one oxidation dye or a combination thereof. This means that the dye composition may be a direct dye composition or an
  • oxidation dye composition for instance, the oxidation dye compositions as described in EP 2 407 149 or the compositions as described in EP 2 329 809, which comprise a combination of an oxidation dye and a direct dye may be used.
  • the dye composition may suitably comprise further ingredients such as surfactants and/or conditioning component as defined below, and may suitably be in the form of a solution,
  • the dye composition may comprise a direct dye.
  • a direct dye there are no particular limitations as to the type of direct dye, and any direct dye suitable for hair colouring may be used.
  • Examples of the direct dye include an anionic dye, a nitro dye, a disperse dye, and a cationic dye and mixtures thereof.
  • Non- limiting examples of the cationic dyes are Basic Blue 6, Basic Blue 7, Basic Blue 9, Basic Blue 26, Basic Blue 41, Basic Blue 99, Basic Brown 4, Basic Brown 16, Basic Brown 17, Natural Brown 7, Basic Green 1, Basic Orange 31, Basic Red 2, Basic Red 12 Basic Red 22, Basic Red 51, Basic Red 76, Basic Violet 1, Basic Violet 2, Basic Violet 3, Basic Violet 10, Basic Violet 14, Basic Yellow 57 and Basic Yellow 87 and mixtures thereof. Particularly preferred are Basic Red 51, Basic Orange 31, Basic Yellow 87 and mixtures thereof.
  • Non- limiting examples of the anionic dyes are Acid Black 1, Acid Blue 1, Acid Blue 3, Food Blue 5, Acid Blue 7, Acid Blue 9, Acid Blue 74, Acid Orange 3, Acid Orange 6, Acid Orange 7, Acid Orange 10, Acid Red 1, Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 50, Acid Red 52, Acid Red 73, Acid Red 87, Acid Red 88, Acid Red 92, Acid Red 155, Acid Red 180, Acid Violet 9, Acid Violet 43, Acid Violet 49, Acid Yellow 1, Acid Yellow 23, Acid Yellow 3, Food Yellow No. 8, D&C Brown No. 1, D&C Green No. 5, D&C Green No. 8, D&C Orange No. 4, D&C
  • the preferred anionic dyes are Acid Red 52, Acid Violet 2, Acid Red 33, Acid Orange 4, Acid Red 27 and Acid
  • HC Blue No.2 HC Blue No.4, HC Blue No .5 , HC Blue No.6, HC Blue No .7 , HC Blue No.8, HC Blue No.9, HC Blue No.10, HC Blue No.11, HC Blue No.12, HC Blue No.13, HC Brown No.l, HC Brown No .2 , HC Green No .1 , HC Orange No .1 , HC Orange No .2 , HC Orange No .3 , HC Orange No.5, HC Red BN, HC Red No.l, HC Red No .3 , HC Red No.7, HC Red No .8 , HC Red No.9, HC Red No.10, HC Red No.11, HC Red No.13,
  • the dye composition may suitably comprise only one direct dye or a combination of direct dyes.
  • the direct dyes of different ionic characters may also be comprised in the same composition.
  • the total amount of direct dye in the composition is within the range of 0.001 to 10 %, preferably 0.01 to 7.5 %, more preferably 0.05 to 5% by weight, based on the total weight of the dye composition.
  • the dye composition only comprises direct dyes
  • Oxidation Dye is not required for colouring the hair. In case lightening of the hair colour is desired, an oxidizing agent may be included into the composition. Oxidation Dye
  • the dye composition comprises an oxidation dye, it is typically of a two-component type, wherein the first
  • component comprises the oxidation dye intermediates
  • the second component comprises an oxidizing agent such as
  • the two components are typically stored separately and combined before application onto the hair.
  • any known precursors and couplers normally used in a hair dye product may suitably be used.
  • Non- limiting examples of the precursor include para- phenylenediamine, toluene-2 , 5-diamine, 2 -chloro-para- phenylenediamine , N-methoxyethyl-para-phenylenediamine, N,N- bis (2 -hydroxyethyl) -para-phenylenediamine , 2- (2- hydroxyethyl) -para-phenylenediamine , 2 , 6-dimethyl-para- phenylenediamine , 4 , 4 » -diaminodiphenylamine, 1, 3 -bis (N- (2- hydroxyethyl) -N- (4-aminophenyl) amino) -2-propanol, PEG-3 ,3,2'- para-phenylenediamine, para-aminophenol , para- methylaminophenol , 3 -methyl-4 -aminophenol , 2-aminomethyl-4- aminophenol, 2-
  • the coupler include meta- phenylenediamine , 2 , -diaminophenaxyethanol , 2-amino-4- (2- hydroxyethylamino) anisole , 2,4 -diamino- 5 -methylphenetole , 2 , -diamino- 5- ( 2 -hydroxyethoxy) toluene , 2 , 4 -dimethoxy- 1 , 3 - diaminobenzene, 2 , 6 -bis ( 2 -hydroxyethylamino) toluene , 2,4- diamino-5-fluorotoluene, 1, 3 -bis (2,4-diaminophenoxy)propane, meta-aminophenol , 2-methyl-5-aminophenol, 2 -methyl- 5- (2- hydraxyethylamino) phenol, 2 , 4 -dichloro-3 -aminophenol
  • the concentration of the dye precursors and couplers each is in the range of 0.001 to 10%, preferably 0.01 to 7.5%, more preferably 0.1 to 5% by weight based on the total weight of the dye composition.
  • the oxidation dye composition further comprises an alkalizing agent. Suitable non-limiting examples of the alkalizing agent include ammonia and a salt thereof; alkanolamine such as monoethanolamine , isopropanolamine , 2 -amino- 2 -methyl propanol, and 2 -aminobutanol , and a salt thereof;
  • alkanediamine such as 1 , 3 -propanediamine and a salt thereof
  • carbonate such as guanidine carbonate, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate and their mixtures.
  • concentration of the alkalizing agent is in the range of 0.1 to 15% preferably 0.5 to 10%, more preferably 1 to 7.5% by weight, based on the total weight of the dye composition.
  • the component comprising the oxidizing agent is stored separately and mixed with the dye component prior to application onto hair.
  • Suitable non- limiting examples of the oxidizing agent include hydrogen peroxide, urea peroxide, melamin peroxide and sodium bromate . Among these oxidizing agents, hydrogen peroxide is
  • the concentration of the at least one oxidizing agent, preferably hydrogen peroxide, is in the range of 1 to 20%, preferably 1 to 15%, more preferably 1 to 12% and even more preferably 2 to 9% by weight, based on the total weight of the dye composition.
  • the pH of the component comprising the oxidizing agent is preferably 2 to 6 , more preferably 2.5 to 4.
  • the pH may be adjusted by means of suitable buffering agents .
  • the pH of the dye composition is typically in the range of 6 to 11, preferably 6.5 to 10.5 and more preferably 6.8 to 10, measured at ambient temperature (25°C) .
  • the oxidation dye composition may additionally comprise at least one direct dye.
  • the direct dyes mentioned above are all suitable for this purpose. 2.
  • the straightening composition comprises at least one
  • glyoxylic acid pyruvic acid and 2- ketobutyric acid can be mentioned.
  • the carboxylic acid of Formula (I) may be comprised in the composition in its free acid form.
  • the carbonyl group may be comprised in the composition in its free acid form.
  • the hydrate of the acid of Formula (I) may be formed when providing the composition as an aqueous solution.
  • glyoxylic acid (H-CO-COOH) in aqueous solution is almost quantitatively present as the hydrate (H-C (OH) 2 -COOH) .
  • the hydrate may also condense to dimers .
  • a salt of the carboxylic acid of Formula (I) may also be used.
  • alkali metal salts such as the sodium or potassium salt and alkaline earth metal salts such as the magnesium salt or the calcium salt may be mentioned.
  • the concentration of the at least one carboxylic acid of the formula (I) and/or a hydrate thereof and/or salts thereof is in the range of 0.1 to 40%, preferably 0.5 to 30%, more preferably 1 to 25% and even more preferably 2.5 to 20% by weight, based on the total weight of the straightening composition.
  • the pH of the straightening composition is below or equal to 4.0, preferably in the range of 0.5 to 3, more preferably 1 to 2.5, as measured directly and at ambient temperature
  • the pH of the compositions may be adjusted using known alkaline solutions, preferably with sodium hydroxide solution .
  • shaping/straightening techniques are based on the reorganization of the disulfide bridges and involve a cleavage of the disulfide bonds either by using a sulfur-based
  • the present invention does not utilize cleavage of the disulfide bonds and fixing the bonds in the new shape. Therefore, the straightening composition of the present invention does not require the presence of sulfur- based reducing agents. However, up to 2% by weight calculated to the total of the composition sulfur based reducing agents does not disturb the straightening performance of the
  • the straightening composition has less than 2% by weight of sulfur-based reducing agents, and preferably is free of sulfur-based reducing agents.
  • the straightening composition may suitably comprise further ingredients such as surfactants and/or conditioning component as defined below, and may suitably be in the form of a solution, emulsion, cream, paste and mousse. 3.
  • the dye composition and the straightening composition may comprise a surfactant.
  • a surfactant any of a cationic surfactant, a nonionic surfactant, an amphoteric surfactant and an anionic surfactant can be used. It is also possible to use two or more types of surfactants in combination.
  • the cationic surfactant is preferably a mono- long chain alkyl quaternary ammonium salt, having a C 8 -C 2 4 alkyl residue and three Ci - C 4 alkyl residues.
  • Preferably at least one mono alkyl quaternary ammonium surfactant is selected from the compounds with the general formula
  • R 1 1 wherein R 8 is a saturated or unsaturated, branched or
  • n is an integer of 1 - 4, or
  • R 9 , R 10 and Rii are independent from each other an alkyl group with 1 to 4 carbon atoms, hydroxyl alky chain with 1 to 4 carbon atoms, or ethoxy or propoxy group with a number of ethoxy or propoxy groups varying in the range of 1 to 4 , and X is chloride, bromide, methosulfate or ethosulfate.
  • Suitable cationic surfactants are, for example, long-chain quaternary ammonium compounds which can be used alone or in admixture with one another, such as cetyl trimethyl ammonium chloride, myristyl trimethyl ammonium chloride,
  • behentrimonium chloride trimethyl cetyl ammonium bromide, stearyl trimethyl ammonium chloride, stearyl trimonium chloride and stearamidopropyltrimonium chloride.
  • nonionic surfactant examples include polyoxy-Ci- 4 - alkylene C 8 - 24 -alkyl ether, polyoxy-Ci_ 4 -alkylene C 8 - 24 -alkylene alkenyl ether, higher (Ci 2 -C 24 ) fatty acid sucrose ester, polyglycerin C 8 - 2 4-fatty acid ester, higher (Ci 2 -C 24 ) fatty acid mono- or diethanolamide, polyoxyethylene hardened castor oil, polyoxyethylene sorbitan C 8 - 24 -fatty acid ester,
  • polyoxyethylene sorbit C 8 _ 24 -fatty acid ester polyoxyethylene sorbit C 8 _ 24 -fatty acid ester, C 8 - 2 4-alkyl saccharide surfactant, C 8 - 24 -alkylamine oxide, and C 8-24 - alkylamidoamine oxide .
  • amphoteric surfactant examples include an imidazoline- based surfactant, a carbobetaine-based surfactant, an
  • amidobetaine-based surfactant a sulfobetaine-based surfactant
  • surfactant a hydroxysulfobetaine-based surfactant and an amidosulfobetaine-based surfactant.
  • anionic surfactant examples include:
  • alkylbenzenesulfonate alkyl or alkenyl ether sulfate, alkyl or alkenyl sulfate, olefin sulfonate, alkanesulfonate , saturated or unsaturated fatty acid salts, alkyl or alkenyl ether carboxylate, a- sulfo fatty acid salts, N-acylamino acid type surfactants, phosphoric acid mono- or diester type surfactants, and sulfosuccinate .
  • alkyl ether sulfate include polyoxyethylene alkyl ether sulfate. Examples of the counterion for the anionic residues of these
  • surfactants include an alkalimetal ion such as sodium ion or potassium ion; an alkaline earth metal ion such as calcium ion or magnesium ion; an ammonium ion; and an alkanolamine having 1 to 3 alkanol groups each having 2 or 3 carbon atoms (for example, monoethanolamine , diethanolamine ,
  • the surfactant can be used singly or in combination of two or more kinds.
  • the content thereof usually is 0.05 to 10% wt.%, more preferably 0.1 to 5 wt.%, based on the total weight of the dye composition and the straightening composition, respectively.
  • the dye composition and the straightening composition may optionally comprise a conditioning component suitable for application to the hair.
  • the conditioning component is an oil or polymer which adheres to the hair and improves the feel and the manageability.
  • the total amount thereof is preferably 0.01 to 30 wt.%, more preferably 0.05 to 20 wt.%, and even more preferably 0.1% to 10 wt.%, based on the total weight of the dye composition and the
  • conditioning component generally include silicones, higher alcohols, and organic conditioning oils (for example, hydrocarbon oil, polyolefin and fatty acid ester) .
  • the composition may comprise a single type of
  • conditioning component or two or more in combination.
  • the dye composition and/or the straightening composition preferably contains a silicone.
  • the silicone include
  • modified silicone for example, amino-modified silicone, fluorine-modified silicone, alcohol- modified silicone, polyether-modified silicone, epoxy- modified silicone, or alkyl-modified silicone
  • dimethylpolysiloxane polyether-modified silicone and amino- modified silicone are preferred.
  • the dimethylpolysiloxane may be any cyclic or non-cyclic dimethylsiloxane polymer, and examples thereof include SH200 series, BY22-019, BY22-020, BY11-026, B22-029, BY22-034, BY22-050A, BY22-055, BY22-060, BY22-083, FZ-4188 (all by Dow Corning Toray Co., Ltd.), KF-9008, KM-900 series, MK-15H, and MK-88 (all by Shin-Etsu Chemical Co., Ltd.).
  • the polyether-modified silicone may be any silicone having a polyoxyalkylene group, and the group constituting the
  • polyoxyalkylene group may be an oxyethylene group or an oxypropylene group. More specific examples include KF-6015, KF-945A, KF-6005, KF-6009, KF-6013, KF-6019, KF-6029, KF- 6017, KF-6043, F-353A, KF-354A, KF-355A (all by Shin-Etsu Chemical Co., Ltd.), FZ-2404, SS-2805, FZ-2411, FZ-2412, SH3771M, SH3772M, SH3773M, SH3775M, SH3749, SS-280X series, BY22-008 M, BY11-030, and BY25-337 (all by Dow Corning Toray Co. , Ltd. ) .
  • the amino-modified silicone may be any silicone having an amino group or an ammonium group, and examples thereof include an amino-modified silicone oil having all or a part of the terminal hydroxy1 groups capped with a methyl group or the like, and an amodimethicone which does not have the terminals capped.
  • a preferred example of the amino-modified silicone may be a compound represented by the following formula :
  • R ' represents a hydroxyl group, a hydrogen atom or R x ;
  • R x represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms;
  • D represents R x , R"- (NHCH 2 CH 2 ) m NH 2 , OR x , or a hydroxyl group;
  • R" represents a divalent hydrocarbon group having 1 to 8 carbon atoms;
  • m represents a number from 0 to 3;
  • p and q represent numbers, the sum of which is, as a number average, equal to or greater than 10 and less than 20,000, preferably equal to or greater than 20 and less than 3000, more preferably equal to or greater than 30 and less than 1000, and even more preferably equal to or greater than 40 and less than 800.
  • silicone oils such as SF8452C, SS-3551 (all by Dow Corning Toray Co., Ltd.), KF-8004, KF-867S, and KF-8015 (all by Shin- Etsu Chemical Co. , Ltd.); and amodimethicone emulsions such as SM8704C, SM8904, BY22-079, FZ-4671, and FZ-4672 (all by Dow corning Toray Co., Ltd.) .
  • the total content of these silicones in the compositions of the present invention is usually 0.1 to 20 wt.%, preferably 0.2% to 10 wt.% and more preferably 0.5 to 5 wt.%, based on the total weight of the dye composition and the straightening composition, respectively.
  • the dye composition and/or the straightening composition may also include an organic conditioning oil.
  • the organic conditioning oil that is suitably used as a conditioning component is preferably a low-viscosity and water-insoluble liquid, and is selected from a hydrocarbon oil having at least 10 carbon atoms, a polyolefin, a fatty acid ester, a fatty acid amide, a
  • the viscosity of such an organic conditioning oil as measured at 40°C is preferably 1 to 200 mPa-s, more preferably 1 to 100 mPa-s, and even more preferably 2 to 50 mPa-s.
  • a capillary viscometer may be used for the determination of the viscosity.
  • hydrocarbon oil examples include a cyclic hydrocarbon, a linear aliphatic hydrocarbon (saturated or unsaturated) , and a branched aliphatic hydrocarbon (saturated or
  • the linear hydrocarbon oil preferably has 12 to 19 carbon atoms.
  • the branched hydrocarbon oil includes
  • hydrocarbon polymers and preferably has more than 19 carbon atoms .
  • the polyolefin is a liquid polyolefin, more preferably a liquid poly-cc-olefin, and even more preferably a
  • the polyolefin used herein is prepared by polymerizing an olefin monomer having 4 to 14 carbon atoms, and preferably 6 to 12 carbon atoms.
  • the fatty acid ester may be, for example, a fatty acid ester having at least 10 carbon atoms.
  • Examples of such a fatty acid ester include esters having a hydrocarbon chain derived from a fatty acid and an alcohol (for example, monoesters, polyhydric alcohol esters, or di- and tricarboxylic acid esters ⁇ .
  • the hydrocarbon group of these fatty acid esters may have another compatible functional group such as an amide group or an alkoxy group as a substituent, or the hydrocarbon group may be covalently bonded to those functional groups.
  • an alkyl and alkenyl ester of a fatty acid having a fatty acid chain having 10 to 22 carbon atoms a carboxylic acid ester of an aliphatic alcohol having an aliphatic chain derived from an alkyl and/or alkenyl alcohol having 10 to 22 carbon atoms, and a mixture thereof are suitably used.
  • these preferred fatty acid esters include isopropyl isostearate, hexyl laurate, isohexyl laurate, isohexyl palmitate, isopropyl palmitate, decyl oleate, isodecyl oleate, hexadecyl stearate, decyl stearate, dihexadecyl adipate, lauryl lactate, myristyl lactate, cetyl lactate, oleyl stearate, oleyl oleate, oleyl myristate, lauryl acetate, cetyl propionate and dioleyl adipate .
  • Further suitable oil components are natural oils such as paraffin oil and natural triglycerides.
  • Suitable natural triglycerides are argan oil, shea butter oil, karite oil, olive oil, almond oil, avocado oil, ricinus oil, coconut oil, palm oil, sesame oil, peanut oil, sunflower oil, peach kernel oil, wheat germ oil, macadamia nut oil, macadamia oil, night primrose oil, jojoba oil, castor oil, soya oil, lanolin, passiflora oil, black cumin oil, borage oils, grapeseed oil, hempseed oil, kukui nut oil, and rosehip oil .
  • the organic conditioning oil may be used in combination of two or more kinds, and the total concentration is typically in the range of 0.1 to 20 wt.%, preferably 0.2 to 10 wt.%, more preferably 0.5 to 5 wt.%, based on the total weight of the dye composition and the straightening composition, respectively.
  • the hair dye composition and/or the straightening composition may also contain a higher alcohol having 8 carbon atoms or more.
  • the higher alcohol has 8 to 22 carbon atoms, and preferably 16 to 22 carbon atoms. Specific examples thereof include cetyl alcohol, stearyl alcohol, behenyl alcohol, and mixtures thereof.
  • the higher alcohol may be used in combination of two or more kinds, and the content thereof is typically 0.1 to 20 wt.%, preferably 0.2 to 10 wt.%, more preferably 0.5 to 5 wt.%, based on the total weight of the dye composition and the straightening composition, respectively.
  • polyols may suitably be comprised in the
  • compositions examples include polyethylene glycol and polypropylene glycol, and a mixture of the two may be used, or a copolymer of ethylene oxide and propylene oxide may also be used.
  • the dye composition may comprise further ingredients conventionally used in the field of cosmetics, such as preservatives, chelating agents, stabilizers, oxidation inhibitors, plant extracts, ultraviolet absorbers, vitamins, dyes, and fragrances.
  • the hair treatment process of the present invention involves two stages, namely the colouring treatment (steps (a) to (c) ) and the straightening treatment (steps (d) to (i) ) .
  • composition is applied to the hair (step (a) ) and left on the hair for 5 to 45 minutes, preferably 5 to 30 minutes, and is rinsed off with water(step (b) ) .
  • the hair may be shampooed .
  • the application ratio of hair to composition by weight is preferably 0.5:2 to 2:0.5, more preferably 0.5:1 to 1:0.5, even more preferably about 1:1.
  • the hair may be dried after the colouring step, in order to reduce the water content of the hair.
  • a hair dryer may be used for this purpose (step c) .
  • step (a) to (c) After completion of the colouring treatment (steps (a) to (c) ) , the hair is subjected to the straightening treatment in accordance with steps (d) to (i) .
  • the straightening treatment achieves a semi-permanent
  • the straightening effect is not achieved by cleaving the disulfide bonds by reduction or the action of strong alkali. Accordingly, the usage of a reducing composition or an alkaline relaxer
  • step (d) the straightening composition is applied to the hair.
  • the application ratio of hair to composition by weight is preferably 0.5:2 to 2:0.5, more preferably 0.5:1 to 1:0.5, even more preferably about 1:1.
  • composition is left on the hair for 1 to 120 minutes
  • step (e) preferably 5 to 90 minutes, more preferably 10 to 60 minutes, and in particular 15 to 45 minutes at a temperature range of 20 to 45°C and preferably at ambient temperature.
  • the time the composition is left on the hair depends on the type of the hair, whether the hair is damaged or resistant.
  • the hair may optionally be rinsed off with water.
  • the hair is dried in order to avoid an excessive steam generation in the subsequent step of treating the hair with the iron (steps (f ) and (g) ) .
  • a hair dryer is used for this purpose. It is preferable to dry the hair under continuous combing in order to prevent
  • the hair is treated with an iron (step (h) ) .
  • a usual straightening iron may be used for this purpose.
  • the surface temperature of the iron is 250°C or lower, preferably 230°C or lower, more preferably 200°C or lower.
  • the temperature of the iron is 130°C or higher, preferably 150°C or higher, more preferably 170° or higher.
  • the iron may preferably have a surface temperature of 180 ⁇ 50°C, more preferably 170 to 200°C.
  • the hair may be rinsed off with water after treating the hair with the iron and dried with a hair drier (step (i) ) .
  • the hair is dyed with the direct dye composition and rinsed off with water. Subsequently, the straightening composition is applied to the pre-shampooed hair at a ratio of about 1:1, rubbed into the hair and left on the hair for about 30 minutes. Then, the hair is dried with a hair drier.
  • straightening iron having a temperature of about 200°C is used for the subsequent straightening.
  • the oxidative hair dye composition is mixed with a 6% H 2 0 2 solution at a weight ratio of 1:1 before application onto the hair.
  • the straightening composition described in Example 1 is used as the straightening composition.
  • the demi-permanent dye composition is mixed with a 6% H202 solution at a weight ratio of 1:1 before application onto the hair.
  • the straightening composition described in Example 1 is used as the straightening composition.
  • the hair dyed and straightened with the compositions of the above Examples 1-3 showed long lasting colour and the hair was straight for a long period of time.
  • composition was mixed with an aqueous 6% hydrogen
  • the mixed oxidative dye composition was applied to the permed samples at a ratio of dry hair to colour of 1:3, uniformly distributed with a brush and processed on the hair for 20 minutes at a temperature of 40°C. Then, the samples were rinsed off with water (2 1, for 30 sec. at 37°C) and allowed to dry for four hours at ambient temperature .
  • the remaining streaks were treated with an aqueous solution of 10 wt . % glyoxylic acid having a pH of 1.5 (adjusted with NaOH) as the straightening composition in a ratio of dry hair to straightening composition of 1:1.5.
  • the straightening composition was uniformly distributed with a comb and
  • the colour of the straightened, dyed streaks and of the non- straightened, dyed reference streaks was measured in terms of L*a*b values.
  • each streak was immersed in 100 ml of a 5% sodium lauryl ether sulfate solution and treated in a shaking bath for 30 minutes at 40°C and an agitation rate of 100 min "1 .
  • the colour of the streaks was measured in terms of the L*a*b values. Then, the colour difference ( ⁇ value) was determined.

Landscapes

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

Abstract

La présente invention concerne un procédé de coloration et de lissage semi-permanent des cheveux en deux étapes, qui sont effectuées l'une après l'autre dans une seule visite au salon de coiffure. Le procédé utilise une première composition (composition de coloration) comprenant au moins un colorant capillaire, facultativement au moins un agent alcalinisant et facultativement au moins un agent oxydant, et une seconde composition (composition de lissage) comprenant au moins un acide carboxylique de formule (I) : R-CO-COOH. Les cheveux sont traités avec lesdites compositions successivement, de sorte que le traitement de lissage soit effectué directement après le traitement de coloration.
PCT/EP2013/072906 2012-11-05 2013-11-04 Procédé de coloration et de lissage des cheveux WO2014068102A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP12191329 2012-11-05
EP12191329.7 2012-11-05

Publications (2)

Publication Number Publication Date
WO2014068102A2 true WO2014068102A2 (fr) 2014-05-08
WO2014068102A3 WO2014068102A3 (fr) 2014-07-17

Family

ID=47146223

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2013/072906 WO2014068102A2 (fr) 2012-11-05 2013-11-04 Procédé de coloration et de lissage des cheveux

Country Status (2)

Country Link
DE (1) DE202013011967U1 (fr)
WO (1) WO2014068102A2 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015036051A1 (fr) * 2013-09-16 2015-03-19 Kao Corporation Procédé de traitement des cheveux
WO2015086230A1 (fr) * 2013-12-13 2015-06-18 Henkel Ag & Co. Kgaa Lissage des cheveux à l'acide glyoxylique
FR3024646A1 (fr) * 2014-08-05 2016-02-12 Concept Procede de coloration et de lissage de cheveu et kit dedie
WO2017041904A1 (fr) * 2015-09-08 2017-03-16 Kao Germany Gmbh Procédé de lissage semi-permanent et de coloration des cheveux
EP3225229A1 (fr) * 2016-03-29 2017-10-04 Kao Germany GmbH Procédé pour traiter les cheveux
WO2017207767A1 (fr) * 2016-06-03 2017-12-07 Kao Corporation Composition cosmétique capillaire
WO2017207768A1 (fr) * 2016-06-03 2017-12-07 Kao Corporation Procédé de traitement des cheveux
WO2017207799A1 (fr) * 2016-06-03 2017-12-07 Kao Corporation Composition cosmétique capillaire
EP3463265A1 (fr) * 2016-06-03 2019-04-10 Kao Corporation Composition cosmétique capillaire
WO2019147304A1 (fr) * 2017-01-25 2019-08-01 Iuveni Llc Solution de réparation de complexe de membrane chimique et son procédé d'utilisation
CN111372561A (zh) * 2017-11-20 2020-07-03 花王株式会社 毛发处理方法
US10842725B2 (en) 2018-07-31 2020-11-24 L'oreal Express hair coloring using heat
US20210338556A1 (en) * 2018-10-23 2021-11-04 Kao Germany Gmbh Shine enhancing spray composition

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210059336A1 (en) * 2018-02-15 2021-03-04 Kao Corporation Human hair fiber treatment agent

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1416564A (en) 1972-03-21 1975-12-03 Wella Ag Permanent deformation of human hair
EP2329809A1 (fr) 2008-08-19 2011-06-08 Kao Corporation Composition de teinture capillaire
WO2011104282A2 (fr) 2010-02-24 2011-09-01 Alderan S.A.S. Di D'ottavi Adele & C. Procédé de lissage semi-permanent de cheveux frisés, ondulés ou bouclés
EP2407149A1 (fr) 2009-03-11 2012-01-18 Kao Corporation Produit de colorant capillaire du type à deux composants
WO2012010351A2 (fr) 2010-07-20 2012-01-26 Alderan S.A.S. Di D'ottavi Adele & C. Procédé de lissage semi-permanent de cheveux frisés, crépus ou ondulés

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE631957A (fr) * 1962-05-17
US4148329A (en) * 1977-08-17 1979-04-10 Jaskowski Michael C Process and composition for treating hair
US20020192175A1 (en) * 2001-04-18 2002-12-19 Manilal Patel Hair relaxer and coloring system
DE102004054055A1 (de) * 2004-11-05 2006-05-18 Wella Ag Verfahren zum Färben und dauerhaften Verformung von Haaren
EP1880706A1 (fr) * 2006-07-21 2008-01-23 Wella Aktiengesellschaft Méthode et agent pour la déformation permanente de cheveux
EP2191865B1 (fr) * 2008-11-26 2013-10-23 Kao Germany GmbH Procédé pour colorer et lisser des fibres de kératine

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1416564A (en) 1972-03-21 1975-12-03 Wella Ag Permanent deformation of human hair
EP2329809A1 (fr) 2008-08-19 2011-06-08 Kao Corporation Composition de teinture capillaire
EP2407149A1 (fr) 2009-03-11 2012-01-18 Kao Corporation Produit de colorant capillaire du type à deux composants
WO2011104282A2 (fr) 2010-02-24 2011-09-01 Alderan S.A.S. Di D'ottavi Adele & C. Procédé de lissage semi-permanent de cheveux frisés, ondulés ou bouclés
WO2012010351A2 (fr) 2010-07-20 2012-01-26 Alderan S.A.S. Di D'ottavi Adele & C. Procédé de lissage semi-permanent de cheveux frisés, crépus ou ondulés

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015036051A1 (fr) * 2013-09-16 2015-03-19 Kao Corporation Procédé de traitement des cheveux
US10449132B2 (en) 2013-09-16 2019-10-22 Kao Corporation Process for treating hair
WO2015086230A1 (fr) * 2013-12-13 2015-06-18 Henkel Ag & Co. Kgaa Lissage des cheveux à l'acide glyoxylique
FR3024646A1 (fr) * 2014-08-05 2016-02-12 Concept Procede de coloration et de lissage de cheveu et kit dedie
WO2017041904A1 (fr) * 2015-09-08 2017-03-16 Kao Germany Gmbh Procédé de lissage semi-permanent et de coloration des cheveux
AU2016319036B2 (en) * 2015-09-08 2019-08-08 Kao Germany Gmbh Process for semipermanent straightening and dyeing hair
EP3225229A1 (fr) * 2016-03-29 2017-10-04 Kao Germany GmbH Procédé pour traiter les cheveux
WO2017167596A1 (fr) * 2016-03-29 2017-10-05 Kao Germany Gmbh Procédé de traitement capillaire
EP3463265A1 (fr) * 2016-06-03 2019-04-10 Kao Corporation Composition cosmétique capillaire
CN109562033A (zh) * 2016-06-03 2019-04-02 花王株式会社 毛发化妆组合物
WO2017207799A1 (fr) * 2016-06-03 2017-12-07 Kao Corporation Composition cosmétique capillaire
WO2017207768A1 (fr) * 2016-06-03 2017-12-07 Kao Corporation Procédé de traitement des cheveux
WO2017207767A1 (fr) * 2016-06-03 2017-12-07 Kao Corporation Composition cosmétique capillaire
US10959925B2 (en) 2016-06-03 2021-03-30 Kao Corporation Hair cosmetic composition
US11045402B2 (en) 2016-06-03 2021-06-29 Kao Corporation Hair cosmetic composition
WO2019147304A1 (fr) * 2017-01-25 2019-08-01 Iuveni Llc Solution de réparation de complexe de membrane chimique et son procédé d'utilisation
CN111372561A (zh) * 2017-11-20 2020-07-03 花王株式会社 毛发处理方法
EP3714866A4 (fr) * 2017-11-20 2021-09-08 Kao Corporation Procédé de traitement capillaire
US11534380B2 (en) 2017-11-20 2022-12-27 Kao Corporation Hair treatment method
US10842725B2 (en) 2018-07-31 2020-11-24 L'oreal Express hair coloring using heat
US20210338556A1 (en) * 2018-10-23 2021-11-04 Kao Germany Gmbh Shine enhancing spray composition

Also Published As

Publication number Publication date
DE202013011967U1 (de) 2015-02-09
WO2014068102A3 (fr) 2014-07-17

Similar Documents

Publication Publication Date Title
EP2914346B1 (fr) Procédé pour défriser et teindre les cheveux
WO2014068102A2 (fr) Procédé de coloration et de lissage des cheveux
US10874185B2 (en) Process for one-step colouring and straightening hair
JP4564711B2 (ja) 毛髪用脱色又は染色処理剤組成物
BR112017023380B1 (pt) Sistema, composição cosmética e método para tratamento de substratos queratinosos
EP2961376B1 (fr) Procédé et composition pour le lissage semi-permanent de cheveux
BR112016005741B1 (pt) processo e kit de tratamento de cabelo para alisamento semipermanente de cabelo e pós-tratamento, e uso de uma composição de limpeza e/ou uma composição de condicionamento para o tratamento de cabelo depois de um tratamento de alisamento de cabelo
WO2014068101A2 (fr) Procédé de décoloration et de lissage des cheveux
EP2914237B1 (fr) Procédé permettant de lisser et de décolorer des cheveux
JP2008290953A (ja) 酸化染毛剤又は脱色剤組成物
US20150059794A1 (en) Process for straightening the hair
JP4116938B2 (ja) 酸化染毛剤又は脱色剤組成物
FR2984738A1 (fr) Composition oxydante pour le traitement des fibres keratiniques comprenant un sel mineral d' acide phosphorique, et procedes
JP4162585B2 (ja) 酸化染毛又は脱色用第１剤組成物
JP2008290952A (ja) 毛髪脱色用又は染色用第１剤組成物
JP4648188B2 (ja) 染毛剤組成物
TW202448408A (zh) 毛髮之處理方法
JP2008290954A (ja) 酸化染毛剤又は脱色剤組成物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 13786462

Country of ref document: EP

Kind code of ref document: A2

122 Ep: pct application non-entry in european phase

Ref document number: 13786462

Country of ref document: EP

Kind code of ref document: A2

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载