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    • 专利摘要:
    The present invention relates to a process for treating keratinous fibers, in particular hair, comprising: a) the application to said fibers of a composition having a pH greater than or equal to 8 at 25 ° C., and comprising at least one amino acid chosen from those of formula (I) and (II) below, as well as their betaines forms, their optical isomers, their solvates such as hydrates and their salts of bases or acids, organic or mineral: Formulas (I) and (II) in which: R represents a hydrogen atom, a linear or branched, preferably linear, C 1 -C 5 alkyl group, said alkyl group being optionally substituted by at least one group chosen from hydroxyl, -C ( O) -OH, -S (O) 2-OH, -C (O) -O-, M +, -S (O) 2-O-, M +, with M + representing a cationic counterion such as alkali metal, alkaline -terrous, or ammonium, - n is 0 or 1; b) followed by a step of smoothing / straightening the keratinous fibers by means of a smoothing iron at a temperature of at least 100 ° C.
    公开号:FR3030240A1
    申请号:FR1463221
    申请日:2014-12-23
    公开日:2016-06-24
    发明作者:Sebastien Voisin；Gregory Plos
    申请人:LOreal SA；
    IPC主号:
    专利说明:

    [0001] The present invention relates to a process for the treatment of keratinous fibers, in particular the hair, comprising the application of a composition comprising at least one particular amino acid and a step of smoothing / keratinous fibers. straightening by means of a smoothing iron. In the hair field, consumers want to have compositions to make a temporary change to their hair, and aiming for a good performance of the effect achieved. In general, it is desired that the change persists shampoos for at least 15 days, or more depending on the nature of the change. Heat treatments are generally used to change the shape of the hair, in a sustainable way. These treatments allow a visual modification of the appearance of the hairstyle, associating a decrease of the degree of curling, a reduction of the overall volume of the hairstyle, a decrease of the frizzotis, a gain in discipline, a smoother visual aspect, a substantial gain shine, resistance to moisture and heat for maintaining the hairstyle all day long. Moreover, this type of treatment has the advantage of facilitating the daily care of the hair, with the use of less care products, including rinsed care such as conditioners or masks, or care rinsed such as serums, skincare creams or balms, disciplinary foams. Hair drying is facilitated, with a greatly shortened brushing time and a reduction in the daily use of flat tongs, in both time and intensity. This thus makes it possible to limit the risks of damage to the hair by combined factors of mechanical and thermal stress. To these heat treatments, we associate several technologies. A first technology relies on the use of compositions based on thiol reducers. These technologies require a rigorous respect of the conditions of application recommended by the suppliers, in particular in terms of quantity and time of break. In addition, they may be contraindicated on hair too sensitized and not be compatible with the same day application of other treatments such as staining or discoloration. They are otherwise smelly. Another technology relies on the use of formalin (or formaldehyde) based compositions and its derivatives. These treatments have the particularity to be robust, perfectly compatible with all other conventional hair treatments, such as thiol smoothing mentioned above, alkaline straightening, coloring or discoloration of all types, made before or after. They give the hair an excellent discipline, a very strong shine and an ease of care in everyday life. However, in case of repetition of applications, new hair damage appears that can lead to hair breakage. In addition, for toxicological reasons, the use of some of these compounds is now prohibited and / or regulated. So we are looking more and more to avoid the use of such substances, which can be aggressive for the hair and other keratin materials. Another technology relies on the use of acid-based compositions, and particularly on the use of glyoxylic acid. It has thus been proposed, by the application WO2011 / 104282, a new method for semipermanently smoothing the hair, consisting in applying a solution of alphaketoacid on the hair for 15 to 120 minutes, then drying and finally smoothing with iron at a temperature of about 200 ° C, the hair. The alpha-ketoacid used is preferably glyoxylic acid. However, it has been found that glyoxylic acid may not be well tolerated, particularly when the scalp is sensitive and / or irritated. Its volatility, amplified by the use of iron heat, can also be a problem. Moreover, the compositions of the prior art can alter the hair and / or alter the color.
    [0002] It has also been proposed treatments using a composition comprising a base associated with a heat treatment to smooth the hair. Such treatments make it possible to obtain a good relaxation of the loops but can lead to alterations of the hair fiber. The document EP1837010 notably describes a smoothing / straightening process using a composition comprising sodium hydroxide and a heat treatment. WO2007 / 144707 discloses a smoothing / straightening process using a composition comprising a non-hydroxylated base such as monoethanolamine, ethylene diamine, associated with a heat treatment. WO2009 / 117344 also describes a smoothing / straightening method using a composition comprising a non-hydroxylated base and a protein denaturant associated with a heat treatment. To limit the alterations of the hair fibers, it has also been proposed to use compositions comprising weak acids at alkaline pH associated with a heat treatment. The document WO2010 / 049434 for example describes a smoothing / straightening process in which a composition comprising a dicarboxylic acid such as maleic acid and a heat treatment is applied.
    [0003] There is still a need to develop a method of hair treatment, including a smoothing / straightening method that allows smoothing / straightening and / or reducing hair curling effectively and sustainably by limiting hair degradation.
    [0004] The Applicant has now discovered that the use of a composition having a pH greater than or equal to 8 and comprising at least one particular amino acid associated with a smoothing step with a straightener at a temperature of at least 100 ° C. achieved the desired properties of sustainable smoothing. Thus, an object of the present invention is a process for treating keratinous fibers, in particular hair, comprising a) the application to the keratin fibers of a composition having a pH greater than or equal to 8 at 25 ° C. and comprising at least one amino acid chosen from those of formula (I) and (II) below, as well as their betaines forms, their optical isomers, their solvates such as hydrates and their salts, acid or base, organic or minerals: ## STR2 ## Formulas (I) and (II) in which: R represents a hydrogen atom, a linear or branched C1-C5 alkyl group; preferably linear, said alkyl group being optionally substituted with at least one group chosen from hydroxyl, -C (O) -OH, -S (O) 2 -OH, -C (O) -O-, M +, -S (0) 2-0-, M +, with M + representing a cationic counter ion such as alkali metal, alkaline earth metal, or ammonium, - n is 0 or 1; b) followed by a step of smoothing / straightening the keratinous fibers by means of a smoothing iron at a temperature of at least 100 ° C.
    [0005] The method of the invention makes it possible in particular to obtain a good relaxation of loops, durable, while limiting the degradation of the hair. Other features and advantages of the invention will appear more clearly on reading the description and examples which follow. In what follows the expression "at least one" is equivalent to the expression "one or more".
    [0006] As indicated above, the process for treating keratinous fibers according to the invention comprises a) a step of applying to the keratinous fibers a composition comprising at least one amino acid chosen from those of the following formulas (I) and (II) , as well as their betaines forms, their optical isomers, their solvates such as hydrates, and their salts, acid or base, organic or mineral: ## STR5 ## Formulas (I) and (II) in which: R represents a hydrogen atom, a linear or branched, preferably linear, C 1 -C 5 alkyl group, said alkyl group being optionally substituted by at least one group chosen from hydroxyl, -C (0) ) -0H, -S (O) 2-OH, -C (O) -O-, M +, -S (O) 2 -O-, M +, with M + representing a cationic counterion such as alkali metal, alkaline earthy, or ammonium, - n is 0 or 1. In the composition containing them, the amino acid or acids may be in their non-ionized form (I), (II) or in their ionized or betaine (I ') or (II') form: ## STR2 ## Formulas in which R represents an atom of hydrogen, a linear or branched C1-C5 alkyl group, optionally substituted by a hydroxyl group, or a carboxylate group, n is 0 or 1. The amino acid or acids of the invention are preferably chosen from the amino acids known as "Neutral" or so-called "acids". "Neutral amino acids" means amino acids which have a pH at room temperature (25 ° C) in water ranging from 5 to 7 inclusive. Acidic amino acids are amino acids which contain a pH at Preferably, the amino acids of the invention comprise a number of amino groups less than or equal to the number of acid groups. More preferably, the amino acid (s) is (are) chosen from among the amino acids of formula (1). The at least one amino acid (s) or their salt (s) is (are) preferentially chosen from glycine, alanine, serine, beta-alanine and taurine, glycinate. sodium, sodium alaninate, sodium serinate, lithium betaalaninate, sodium taurate, preferably glycine. The amino acid (s) is (are) present in the composition in a content ranging from 1.5 to 15% by weight, preferably from 2 to 10% by weight relative to the total weight. of the composition.
    [0007] The composition used in the process of the invention may comprise at least one basifying agent or an acidifying agent. The alkalinizing agent (s) may be selected from inorganic or organic alkaline agents. In particular, the alkalinizing agent (s) may be chosen from sodium hydroxide, potassium hydroxide, lithium hydroxide, calcium hydroxide, magnesium hydroxide and the conjugate bases of formula (Ib) and (Ib) of the amino acid of the following formula (1) or (11): ## STR2 ## Formulas (Ib) and (Ib) in which R, n and M + are as defined above.
    [0008] According to a particular embodiment, the alkalinizing agent (s) is (are) chosen from sodium hydroxide and potassium hydroxide, preferably sodium hydroxide. According to another particular embodiment, the alkalinizing agent (s) is (are) chosen from among the conjugate bases of formula (Ib) and (Ib) of the amino acid of formula (1) ) or (11).
    [0009] When they are present, the basifying agent (s) is (are) present in the composition in a content ranging from 1.5 to 15% by weight. preferably from 2 to 10% by weight relative to the total weight of the composition. The acidifying agent (s) may be chosen from inorganic or organic acids. The mineral acid can be chosen from hydrochloric acid, sulfuric acid and orthophosphoric acid. Preferably, the mineral acid may be selected from hydrochloric acid and orthophosphoric acid. The organic acid may be chosen from hydroxy acids, in particular from citric acid, lactic acid, glycolic acid, gluconic acid, tartaric acid and malic acid, and more preferably from lactic acid and glycolic acid. When (they) are (are) present, the acidifying agent (s) is (are) present in the composition in a content ranging from 1.5 to 15% by weight preferably from 2 to 10% by weight relative to the total weight of the composition.
    [0010] According to one particular embodiment, the composition used in the method of the invention comprises: an amino acid chosen from the amino acids of formula (1) and (11), and the conjugate base of formula (Ib) or I lb) of said amino acid. According to a preferred embodiment, the amino acid molar ratio of formula (1) or (11) on its conjugate base (Ib) or (Ib) ranges from 1 to 100, preferably from 1 to 10. Preferably, the composition comprises an amino acid of formula (1) and its conjugate base of formula (Ib). According to a particularly preferred embodiment, the composition comprises glycine and sodium glycinate, preferably in a glycine / glycinate molar ratio ranging from 1 to 100, preferably from 1 to 10. The composition used in the process according to The invention may also include one or more amino denaturing agents. By "denaturing agent" is meant an organic or inorganic compound having both at least one electron donor site of basic or nucleophilic character and at least one electron acceptor site of acidic or electrophilic nature, interacting with the weak bonds keratin. According to the invention, a denaturing agent is a compound capable of reducing the rotatory power of a model protein such as, for example, bovine serum albumin by at least 7 ° and / or 5 ° at 579 nm, the measurements being carried out after 3 hours of incubation at 37 ° C., using a polarimeter, as described in Biochemistry 2 (1), 47-57, 1963: either in a 0.05M TRIS buffer pH 7.6 or in a 5.45M urea solution when the solubility of the compound is insufficient in 0.05M TRIS buffer pH 7.6. The compound is considered to be a denaturing agent according to the invention if the decrease in the rotatory power is at least 7 ° in the 0.05 M TRIS buffer pH 7.6 and / or at least 5 ° in the solution of 5.45 M urea. Preferably, the aminated denaturant agent is chosen from ureas and / or urea derivatives and guanidines. The term "urea derivative" means any compound other than urea CO (NH 2) 2 itself, comprising in its chemical formula a carbonyl group covalently bound by two single bonds 6 to two nitrogen atoms, that is to say a unit NV CO Preferably, the denaturing agent is chosen from compounds of formula (III) or (IV), their salts or their hydrates: R3 R5-N, N-R6 NNAII R4 R2 (III) (IV) in which: - R1, R2, R3, R4 represent, independently: (i) a hydrogen atom or (ii) a linear or branched, cyclic C 1 -C 5 alkyl or lower alkenyl radical or acyclic, a C 1 -C 5 alkoxy radical, a C 6 -C 18 aryl radical, a 5- to 8-membered heterocyclic radical; these radicals being optionally substituted with a radical chosen from the radicals: hydroxyl, (C 1 -C 4) alkyl, (di) (C 1 -C 4) (alkyl) amino such as dimethylamino, carboxyl, halogen, aryl, 06-018, carboxamide and N-methylcarboxamide; ; it being understood that when R1, R2 and R3 represent a hydrogen atom, R4 may denote a carboxamide, methoxy, ethoxy, 1,2,4-triazolyl, cyclopentyl or (ClC6) alkylcarbonyl radical, such as acetyl, (C1-C6) alkoxycarbonyl such as methoxycarbonyl or ethoxycarbonyl, -C (O) -CH = CH-C (O) -OH, phenyl optionally substituted by a chlorine atom or a hydroxyl, benzyl or 2,5-dioxo-4-imidazolidinyl radical; when R 1 and R 3 represent a hydrogen atom, R 2 may represent a hydrogen atom, a methyl or ethyl radical and R 4 an acetyl radical; when R 1 = R 2 = H, R 3 and R 4 may form, with the nitrogen atom which bears them, a piperidine, 3-methylpyrazole or 3,5-dimethylpyrazole or maleimide ring; - R1 and R2 as well as R3 and R4 can form, with the nitrogen atom which carries them, an imidazole ring; - R5 and R6 represent, independently of one another, (iii) a hydrogen atom or (iv) an alkyl, acyl, or lower alkenyl radical C-05, linear or branched, cyclic or acyclic a radical C1-5 alkoxy, a 6-018 aryl radical, a 5- to 8-membered heterocyclic radical; these radicals being optionally substituted with a radical chosen from the radicals: hydroxyl, amino, dimethylamino, carboxyl, halogen, aryl 06-018, carboxamide and N-methylcarboxamide; - A is a radical chosen from the radicals: CH2-CH2, CH = CH, CH2-C (O), O (O) -NH, CH = N, C (O) -C (O), CH (OH) -CH (OH), (HO (O) C) CH-CH, CH (OH) -C (O), OH 2 -H 2 OH, 0H 2 -NH-C (O), CH = C (OH) -C (O) ), NH-C (O) -NH, OH-OH2-C (O), OH-N (OH) -OH, NH-OH-NH, C (O) -CH (OH) -OH, C (O) ) -0H2-C (O), C (O) -NH-C (O), C (O) -CH (C (O) OH) -CH2, C (O) -CH = C (C (O) 0H), C (O) -CH = C (OH), C (O) -C (NH2) = CH, C (O) -C (OH3) = N, C (O) -CH = CH, C ( 0) -CH = N and C (O) -N = CH. Among the compounds of formula (III) that are particularly preferred according to the invention, mention may be made of: - urea - methylurea - ethylurea - propylurea - n-butylurea - sec-butylurea - isobutylurea - tert-butylurea -butylurea - cyclopentylurea - ethoxyurea - hydroxyethylurea - N- (2-hydroxypropyl) urea - N- (3-hydroxypropyl) urea - N- (2-dimethylaminopropyl) urea - N- (3- dimethylaminopropyl) urea - 1- (3-hydroxyphenyl) urea - benzylurea - N-carbamoyl maleamide - N-carbamoyl maleamic acid - piperidinecarboxamide - 1,2,4-triazol-4-yl-urea hydantoic acid - methyl allophanate - ethyl allophanate - acetylurea - hydroxyethyleneurea - 2- (hydroxyethyl) ethyleneurea - diallylurea - chloroethylurea - N, N-dimethylurea - N, N -diethylurea - N, N-dipropylurea - cyclopentyl-1-methylurea - 1,3-dimethylurea - 1,3-diethylurea - 1,3-bis (2-hydroxyethyl) urea - 1,3-bis (2-hydroxypropyl) urea - 1,3-bis (3-hydroxypropyl) urea - 1,3-dipropylurea - ethyl-3-propylurea - sec-butyl-3-methylurea - isobutyl-3- methylurea - cyclopentyl-3-methylurea - N-acetyl-N'-methylurea - trimethylurea - butyl-3,3-dimethylurea - tetramethylurea and - benzylurea. Among the compounds of formula (IV) which are particularly preferred according to the invention, mention may be made of: parabanic acid - 1,2-dihydro-3H-1,2,4-triazol-2-one - barbituric acid - uracil - 1-methyl uracil - 3-methyl uracil - 5-methyl uracil - 1,3-dimethyl uracil - 5-aza uracil - 6-aza uracil - 5-fluoro uracil - the 6-fluoro uracil - 1,3-dimethyl-5-fluoro uracil - 5-amino uracil - 6-amino uracil - 6-amino-1-methyl uracil - 6-amino-1,3-dimethyl-uracil 4-chloro uracil-5-chloro uracil-5,6-dihydro-uracil-5,6-dihydro-5-methyl-uracil-2-imidazolidone-1-methyl-2-imidazolidinone-1, 3-dimethyl-2-imidazolidinone - 4,5-dihydroxy-imidazolidin-2-one - 1- (2-hydroxyethyl) -2-imidazolidinone - 1- (2-hydroxypropyl) -2-imidazolidinone (3-hydroxypropyl) -2-imidazolidinone - 4,5-dihydroxy-1,3-dimethyl-imidazolidin-2-one - 1,3-bis (2-hydroxyethyl) -2-imidazolidinone - 2- acid imida 4-Methyl-1,2,4-triazoline-3,5-dione-2,4-dihydroxy-6-methylpyrimidine 1-amino-4,5-dihydro-1H-tetrazol-5-one - hydantoin - 1-methylhydantoin - 5-methylhydantoin - 5,5-dimethylhydantoin - 5-ethylhydantoin - 5-n-propylhydantoin 5-ethyl-5-methylhydantoin - 5-hydroxy-5-methylhydantoin - 5-hydroxymethylhydantoin - 1-allylhydantdine - 1-aminohydantoin - hydantdine 5-acetic acid - 4-amino-1,2 , 4-triazolone-3,5-dione - hexahydro-1,2,4,5-tetrazine-3,6-dione - 5-methyl-1,3,5-triazinon-2-one - 1 methyl-tetrahydro-pyrimidin-2-one - 2,4-dioxohexahydro-1,3,5-triazine - urazole - 4-methylurazole - orotic acid - dihydroxyorotic acid - 2,4 5-trihydroxypyrimidine - 2-hydroxy-4-methylpyrimidine - 4,5-diamino-2,6-dihydroxypyrimidine - barbituric acid - 1,3-dimethylbarbituric acid - cyanuric acid - 1-met hyl-hexahydropyrimidine-2,4-dione - 1,3-dimethyl-3,4,5,6-tetrahydro-2-1H-pyrimidinone - 5- (hydroxymethyl-2,4- (1H, 3H) -pyrimidinedione 2,4-dihydroxypyrimidine-5-carboxylic acid; 6-azathymine; 5-methyl-1,3,5-triazinan-2-one; N-carbamoyl maleamic acid; and alloxane monohydrate. Preferably, said denaturing agent (s) are chosen from urea, alkylurea, hydroxyalkylurea, especially hydroxyethylurea, more preferably from urea and hydroxyethylurea. By "guanidine" is meant any derivative comprising in its chemical formula at least one carbon atom doubly bound to a nitrogen atom and simply bonded to two other nitrogen atoms. These guanidines are more particularly selected from the compounds of general formula (V) below, and their organic or inorganic salts: ## STR1 ## in which: R 1, R 2, R 3, R 4 and R 5 represent, independently, (i) a hydrogen atom or (ii) a linear or branched C 1 -C 4 alkyl or alkenyl radical, optionally substituted by one or 2 radicals chosen from: hydroxyl, amino, dimethylamino, methoxy, ethoxy, carboxyl, carboxamide, N-methylcarboxamide or SO3H. When R 1, R 2 and R 3 and R 4 represent a hydrogen atom, R 5 can also denote an acetyl radical; chloroacetyl; carboxamide; methoxy; ethoxy; 1,2,4-triazoly1; cyclopentyl; methoxycarbonyl; ethoxycarbonyl; C (O) -CH = CH-C (O) OH; phenyl optionally substituted with a chlorine atom or a hydroxyl radical; benzyl; thiazolidone; benzimidazole; benzoxazole; benzothiazole; or C (= NH) -NR6R7 in which R6 and R7 denote, independently of one another, a hydrogen atom or a lower alkyl radical C1-04, linear or branched, optionally substituted with one or two radicals selected from: hydroxyl, amino, (V) dimethylamino, carboxyl or carboxamide; or N-methylcarboxamide; or a phenyl radical. When R 1 = R 2 = R 3 = H, R 4 and R 5 may also form, with the nitrogen atom which carries them, a pyrrolidine, piperidine, pyrazole or 1,2,4-triazole ring optionally substituted with 1 or 2 chosen radicals hydroxyl, amino or carboxyl. When R1 = R2 = H, and R4 = H or methyl, R3 and R5 may also together form a 5-membered ring optionally containing an oxo group. Among the compounds of formula (V), mention may especially be made of the following preferred compounds: guanidine, hydrochloride, guanidine, acetate, guanidine, sulphate, guanidine, carbonate, guanidine, bicarbonate, guanidine, phosphate, guanidine, sulfamate - aminoguanidine - aminoguanidine, hydrochloride - aminoguanidine, sulfate - aminoguanidine, bicarbonate - 1,3-diaminoguanidine, hydrochloride - 1-acetylguanidine - chloroacetylguanidine, hydrochloride - guanylurea - guanylurea , phosphate - phenylguanidine, carbonate - phenylguanidine, bicarbonate - 1-methylguanidine, hydrochloride - 1,1-dimethylguanidine, hydrochloride - 1-ethylguanidine, hydrochloride - 1,1-diethylguanidine, hydrochloride - creatine - creatine , monohydrate - creatinine, hydrochloride - agmatine - agmatine, sulfate - guanidinoacetic acid - guanidinosuccinic acid - 3-guanidinopropionic acid - 4-guanidinobutyric acid e - 5-guanidinovaleric acid - beta-N-methylguanidinopropionic acid - N-methylguanidinopropionic acid - N- (2-hydroxyethyl) guanidine - N- (3-hydroxypropyl) guanidine - biguanide, hydrochloride - N-methyl biguanide, hydrochloride - N-ethyl biguanide, hydrochloride - N-propyl biguanide, hydrochloride - N-butylbiguanide, hydrochloride - 1,1-dimethylbiguanide, hydrochloride - 1-phenylbiguanide - 1,1, 3,3-tetramethylguanidine hydrochloride - 2-tert-butyl-1,1,1,3,3-tetramethylguanidine, hydrochloride - L-arginine - D-arginine - DL-arginine - arginic acid - N- amidino-N- (2,3-dihydroxypropyl) glycine - N-amidinotaurine - 2-imino-1-imidazolidineacetic acid - 1- (2,2-diethoxyethyl) guanidine - 1H-pyrazole-1-carboxamidine, hydrochloride - 5-hydroxy-3-methyl-1H-pyrazole-1-carboximidamide - 3,5-diamino-1H-1,2,4-triazole-1-carboximidamide hydrochloride - 2-guanidone-4-thiazolidone 2-guanidinobenzimidazole - the 2-guanidinobenzoxazole - 2-guanidinobenzothiazole - pyrrolidinoformamidine hydrochloride Among the compounds of formula (V), there may especially be mentioned the following particularly preferred compounds: guanidine, hydrochloride - guanidine, acetate - guanidine, sulfate - guanidine , carbonate - guanidine, bicarbonate - guanidine, phosphate - guanidine, sulfamate - aminoguanidine, hydrochloride - aminoguanidine, sulfate - aminoguanidine, bicarbonate - 1,3-diaminoguanidine, hydrochloride - guanylurea, phosphate - 1-methylguanidine, hydrochloride - 1,1-dimethylguanidine, hydrochloride - 1-ethylguanidine, hydrochloride - creatine, monohydrate - creatinine, hydrochloride - agmatine - agmatine, sulfate - guanidinoacetic acid - the guanidinosuccinic acid - 3-guanidinopropionic acid - beta-N-methylguanidinopropionic acid - N-methylguanidinopropionic acid - N- (2-hydroxyethyl) guanidine - N- (3-hydroxypropyl) l) guanidine - biguanide, hydrochloride - N-methyl biguanide, hydrochloride - N-ethyl biguanide, hydrochloride - 1,1-dimethylbiguanide, hydrochloride - 1,1,3,3-tetramethylguanidine, hydrochloride - 2- tert-butyl-1,1,3,3-tetramethylguanidine, hydrochloride - L-arginine - DL-arginine - arginic acid - N-amidino-N- (2,3-dihydroxypropyl) glycine - N- amidinotaurine - 2-imino-1-imidazolidineacetic acid - 1H-pyrazole-1-carboxamidine, hydrochloride - 3,5-diamino-1H-1,2,4-triazole-1-carboximidamide, hydrochloride - 2- guanidone-4-thiazolidone. Preferably, the composition comprises an aminated denaturant selected from guanidine, urea, alkylurea, hydroxyalkylurea, especially hydroxyethylurea, more preferably urea and hydroxyethylurea. When present, the denaturating agent (s) is (are) present in an amount ranging from 1 to 30% by weight, preferably from 2 to 25% by weight. , relative to the total weight of the composition. The composition according to the invention may also further comprise one or more thickeners. For the purposes of the present invention, the term "thickening agent" is understood to mean an agent which, by virtue of its presence in the composition, makes it possible to increase the viscosity of said composition by at least 10 cPs, preferably by at least 200 cPs, at 25 ° C and at a shear rate of 1s-1. This viscosity can be measured using a cone / plane viscometer (Haake R600 Rheometer or the like). The thickening agent (s) may be chosen from fatty acid amides obtained from C 10 -C 30 carboxylic acid (monoisopropanol-, diethanol- or monoethanolamide of coconut acids, monoethanolamide of alkyl ether acid). carboxylic oxyethylenated), polymeric thickeners and in particular polysaccharides, especially cellulosic polymers as described below, gum arabic, gums of microbial origin (scleroglucan gum), crosslinked or non-crosslinked homo- and copolymers based on acrylic acid, methacrylic acid or acrylamidopropanesulfonic acid, associative polymers as described below, and mixtures thereof. The term "cellulosic" polymer is understood to mean, according to the invention, any polysaccharide compound having in its structure chains of glucose residues linked by f3-1,4 bonds; in addition to unsubstituted celluloses, the cellulose derivatives may be anionic, cationic, amphoteric or nonionic.
    [0011] Thus, the cellulosic polymers of the invention may be selected from unsubstituted celluloses including microcrystalline form and cellulose ethers. Among these cellulosic polymers, there are cellulose ethers, cellulose esters and cellulose ether esters. Among the cellulose ethers, there are (C1 -6) alkylcelluloses and in particular methyl hydroxyethylcelluloses. Among the cellulose esters, there are inorganic esters of cellulose (cellulose nitrates, sulphates or phosphates, etc.), cellulose organic esters (cellulose monoacetates, triacetates, amidopropionates, acetatebutyrates, acetatepropionates or acetatetrimellitates, etc.). and mixed organic / inorganic cellulose esters such as cellulose acetate and acetate sulphates and cellulose acetate propionates. Among the cellulose ether esters, mention may be made of hydroxypropyl methylcellulose phthalates and ethylcellulose sulphates. Preferably, the cellulosic polymer is chosen from (C1-06) alkylcelluloses and in particular methyl hydroxyethylcelluloses.
    [0012] The associative polymer or polymers that may be used according to the invention are water-soluble polymers capable, in an aqueous medium, of reversibly associating with each other or with other molecules. Their chemical structure comprises hydrophilic zones, and hydrophobic zones characterized by at least one fatty chain preferably comprising from 10 to 30 carbon atoms. The associative polymer or polymers that may be used according to the invention may be of the anionic, cationic, amphoteric or nonionic type, such as the polymers sold under the names Pemulen TR1 or TR2 by the company Goodrich (INCI: Acrylates / C10-30 Alkyl Acrylate Crosspolymer ), SALCARE SC90 by the company CIBA, ACULYN 22, 28, 33, 44 or 46 by the company ROHM & HAAS and ELFACOS T210 and T212 by the company AKZO. Among all the thickening agents mentioned, the thickening agent (s) is (are) preferably chosen from polymers, better still from polysaccharides, and even more preferably from cellulosic polymers, in particular from (C1-C6) alkylcelluloses and in particular methyl hydroxyethylcelluloses. When they are present, the thickening agents are (are) present in an amount ranging from 0.01 to 10% by weight, preferably from 0.1 to 5% by weight, preferably from 0.2 to 3% by weight. % by weight, relative to the total weight of the composition. The composition used in the process according to the invention may also comprise one or more silicones, and in particular one or more amino silicones.
    [0013] By aminosilicone is meant any silicone comprising at least one primary, secondary, tertiary amine or a quaternary ammonium group. Amino silicones that can be used in the context of the invention include polysiloxanes, trimethylsilylamodimethicone, amino silicones proposed by the company VVACKER under the name BELSIL® ADM 652 or under the name Fluid VVR 1300®. It is also possible to use amino silicones in the form of an oil-in-water emulsion, such as the amino silicone microemulsions proposed under the names FINISH CT 96 E® or SLM 28020® (BELSIL ADM LOG 10) by the company VVACKER. Mention may also be made of Dow Corning's DC2-8566 Amino Fluid, or alternatively quaternary ammonium silicones and polyoxyalkylenated multiblock amino silicones, such as those sold under the names Silsoft A-843 or Silsoft A + by Momentive. When they are present, the amino silicone (s) is (are) present in an amount ranging from 0.01% to 10% by weight, preferably from 0.1% to 5% by weight. 15% by weight, preferably 0.2 to 3% by weight, relative to the total weight of the composition. The pH of the composition used in the process of the invention is greater than or equal to 8. Preferably, the pH of the composition ranges from 8 to 12 and more preferably from 9 to 11. Preferably, the pH of the composition composition is less than two units of the pKa relating to the equilibrium of the amino acid of formula (I) or (11) with its base (Ib) or (11b). The composition used in the process of the invention may be aqueous or anhydrous. It is preferably aqueous and then comprises water at a concentration ranging from 10 to 99%, more preferably from 30 to 99%, more preferably from 50 to 98% by weight relative to the total weight of the composition. The composition may especially comprise one or more organic solvents, especially water-soluble solvents such as C 1 -C 7 alcohols; mention may be made especially of C 1 -C 7 aliphatic monoalcohols, for example ethanol, or C6-C7 aromatics, which may be used alone or in admixture with water. The composition used in the process of the invention may further comprise at least one usual cosmetic ingredient, especially chosen from propellants; the oils; solid fatty substances and especially C8-C40 esters, C8-C40 acids; C8-C40 alcohols, sunscreens; moisturizing agents; antidandruff agents; antioxidants; chelating agents; pearlescent and opacifying agents; plasticizing or coalescing agents; the charges; thickeners or gelling agents, polymeric or not other than the cellulosic polymers already mentioned; emulsifiers; polymers in particular conditioning or styling; the perfumes; silanes; crosslinking agents. The composition may of course include several cosmetic ingredients listed above. Depending on their nature and the purpose of the composition, the usual cosmetic ingredients may be present in customary amounts, easily determinable by those skilled in the art, and which may be included, for each ingredient, between 0.01 to 80% by weight . Those skilled in the art will take care to choose the ingredients in the composition, as well as their amounts, so that they do not adversely affect the properties of the compositions of the present invention. The compositions used in the process according to the invention may be in any of the galenical forms conventionally used, and in particular in the form of an aqueous, alcoholic or aqueous-alcoholic solution or suspension, or an oily solution; a solution or dispersion of the lotion or serum type; an emulsion, in particular of liquid or semi-liquid consistency, of the HIE, W / O or multiple type; a suspension or emulsion of soft consistency of cream (O / W) or (W / O) type; an aqueous or anhydrous gel, or any other cosmetic form. These compositions may be packaged in pump bottles or in aerosol containers, in order to ensure application of the composition in vaporized form (lacquer) or in the form of foam. Such forms of packaging are indicated, for example, when it is desired to obtain a spray or a mousse, for the treatment of hair. In these cases, the composition preferably comprises at least one propellant.
    [0014] The composition which has just been described can be applied to dry or wet hair, preferably on dry hair. The bath ratio of the applied composition can vary from 0.1 to 10, more particularly from 0.2 to 5, and preferably from 0.5 to 3. Relative bath ratio is the ratio of the total weight of the composition applied and the total weight of keratinous fibers to be treated. As indicated above, the step of applying the composition which has just been described is followed by a step of smoothing / straightening the keratinous fibers by means of a smoothing iron also called flat tongs. The smoothing iron is used at a temperature of at least 100 ° C, preferably at a temperature between, inclusive, 100 ° C and 300 ° C, preferably between 120 ° C and 280 ° C, preferably still between 150 ° C and 250 ° C, and even better, between 200 and 250 ° C. The method of the invention may comprise other intermediate steps aimed at improving the smoothing of keratin fibers.
    [0015] In particular, the application stage of the composition may be followed by a laying time The exposure time, namely the contact time of the composition on the hair, is preferably at least 5 minutes, preferably between 10 and 60 minutes, preferably between 15 and 45 minutes, a rinsing of the hair may optionally be provided after the application of the composition and possibly the exposure time, the hair may then be dewatered or not, preferably dried A drying step in the hair dryer, associated or not with brush straightening (brushing) may be provided before the smoothing step with a smoothing iron.
    [0016] According to one particular embodiment, smoothing with the iron to be smoothed is carried out in several passages on the hair, in general 3 to 10 passes. According to a particular embodiment, the method of the invention comprising the steps of applying the composition according to the invention to the hair, then of smoothing with iron is carried out one or more times, spaced (s) or not by a or several cosmetic treatments, preferably a shampoo, until the desired form or intensity of shape is obtained. The following examples serve to illustrate the invention without being limiting in nature.
    [0017] EXAMPLES The following compositions were made from the ingredients indicated in the tables below, all the amounts being indicated in percent by weight of material as is with respect to the total weight of the composition. 1 2 3 A (control) Glycine 10.0 5.0 2.0 (1.33M) (0.66M) (0.27M) Sodium Glycinate 10.0 5.0 2.0 (1.03M) ( 0.51M) (0.2M) Monoethanolamine 1.67 (0.27M) Hydrochloric acid qs pH Water Qsp 100 Qsp 100 Qsp 100 Qsp 100 pH 9.9 9.9 9.9 9.9 Relaxation after 10 +++ + ++++ +++ - shampoos very strong relaxation +: a little relaxation +++: strong relaxation -: very little relaxation ++: average relaxation -: no relaxation The compositions 1 to 3 according to the The invention and the control composition A were applied to locks of natural dry curly Caucasian hair, 2.7 g and 20 cm long with 5-7 loops. After 30 minutes, the hair was dried in the hair dryer (blow dry) and then smoothed by the passage of flat tongs brought to 210 ° C (10 passes per wick). They were then subjected to 10 shampoos. For each wick, the loop relaxation was measured, namely the wick length difference before and after treatment (including shampoos). It can be seen that with the process of the invention in which the compositions 1, 2 or 3 have been applied, a strong or very strong relaxation of the loops after shampooing is obtained, whereas by using the control composition A, do not get relaxed. In addition, the treated locks retain good integrity since no breakage was observed with the compositions 2, 3 and a slight breakage, after combing, with the composition 1. The method according to the invention thus allows to obtain a good relaxation of curls, durable, while limiting the degradation of the hair.
    [0018] The following compositions 4 to 7 according to the invention and the control composition B were also applied according to the protocol described above and the same measurements were carried out as previously. B (control) Glycine 3.5 2.5 (0.33M) 5.0 (0.67M) 2.0 (0.27M) (0.47M) 30% Sodium MA 3.5 ( 0.26M) 1.5 5.0 (0.51M) 2.0 (0.15M) 2.0 (0.15M) (0.11M) Ethanol 10.0 Methyl hydroxyethylcellulose (STRUCTURE CEL 8000M from Akzo Nobel) 1.0 1.0 Amodimethicone (and) Trideceth-5 (and) Trideceth-10 (BELSIL ADM LOG 1 from VVacker) 2.0 Water Qsp 100 Qsp 100 Qsp 100 Qsp 100 Qsp 100 pH 9.9 9.6 9.9 9.9 13.1 Relaxation after 10 shampoos + ++ +++ +++ + It can be seen that with the process of the invention in which the composition 4 was applied, a little relaxation is obtained and with the compositions 5 to 7, a relaxation of the medium to strong loops is obtained. It is also contested that, at an equivalent molar content of sodium hydroxide, a strong loosening of the loops is obtained with the composition 7, which comprises glycine, whereas little relaxation is obtained with the control composition B which does not comprise glycine. .
    [0019] The following composition 8 according to the invention and the comparative composition C were also applied according to the protocol described previously and the same measurements were carried out as previously. 8 C (comparative) Glycine 8.8 (1.18M) Lysine 10.0 (0.68M) 30% Soda MA 8.8 (0.68M) 5.0 (0.52M) Hydrochloride 5.0 ( 0.52M) guanidine Water Qsp 100 Qsp 100 pH 10.1 10.2 Relaxation after 10 shampoos ++++ + It can be seen that with the process of the invention in which it has been applied composition 8, a significantly greater expansion is obtained than with the composition C with identical basic content. The following compositions 9 and 10 according to the invention and comparative composition D were also applied according to the protocol described previously and the same measurements were carried out as previously. 9 10 D (Comparative) Alanine 4.5 (0.5M) Serine 4.3 (0.5M) Lysine 7.3 (0.5M) Soda at 30% my 4.0 (0.3M) 4.5 ( 0.33M) 3.0 (0.22M) Water Qsp 100 Qsp 100 Qsp 100 pH 10.1 10.0 11.1 Relaxation after 10 shampoos + ++ It can be seen that with the process of the invention in which one applied the compositions 9 and 10, a significantly greater expansion is obtained than with the composition D, equivalent molar content amino acid.
    [0020] Finally, the following compositions 11 to 15 according to the invention and the comparative composition E were also applied, according to the protocol described previously, and the same measurements were carried out as previously.
    [0021] E (comparative) Glycine 3.5 (0.47M) 3.5 (0.47M) 3.5 (0.47M) 3.5% (0.47M) 2.1 (0) , 28M) 30% Soda MA 3.5 (0.26M) 3.5 (0.26M) 3.5 (0.26M) 3.5% (0.26M) 2.1 (0.16M) Monoethanolamine 1.0 (0.16M) Ethanol 10 10.0 10% Urea 5.0 (0.83M) 10.0 (1.66M) 15.0 (2.58M) 15.0 (2.58M) Hydroxyethylurea 21.8 (0.83M) 6.3 (0.24M) Amodimethicone (and) Trideceth-5 (and) Trideceth-10 (BELSIL ADM LOG 1 from VVacker) 2.0 2.0 2.0 2.0 Methyl 1.0 1.0 1.0 1.0 hydroxyethylcellulose (Akzo Nobel structure 8000 M CEL) Water Qsp 100 Qsp Qsp Qsp 100 Qsp 100 Qsp 100 100 100 pH 9.9 9.9 9.9 9.9 10 11.9 Relaxation after 10 +++ +++ ++++ ++++ ++++ ++ shampoos It can be seen that with the process of the invention in which the compositions 11 to 15 a relaxation of the strong to very strong loops is obtained. It can also be seen that with the composition 15, a significantly greater expansion is achieved than with the composition E, with identical basic content, and with a lower pH of the composition according to the invention than that of the comparative composition. E.
    权利要求:
    Claims (17)
    [0001]
    REVENDICATIONS1. A method of treating keratinous fibers, in particular hair, comprising: a) applying to said keratin fibers a composition having a pH greater than or equal to 8 at 25 ° C and comprising at least one amino acid selected from those of formula (I) and (II) below, as well as their betaines forms, their optical isomers, their solvates such as hydrates and their salts of bases or acids, organic or mineral: ## STR1 ## I1) Formulas (I) and (II) in which: R represents a hydrogen atom or a linear or branched, preferably linear, C1-C5 alkyl group, said alkyl group being optionally substituted by at least one chosen group; from hydroxyl, -C (O) -OH, -S (O) 2 -OH, -C (O) -O-, M +, - S (O) 2-O-, M +, with M + representing a cationic counterion such as alkali metal, alkaline earth metal, or ammonium, - n is 0 or 1; b) followed by a step of smoothing / straightening the keratinous fibers by means of a smoothing iron at a temperature of at least 100 ° C.
    [0002]
    2. Method according to claim 1, characterized in that the composition comprises at least one basifying agent or at least one acidifying agent.
    [0003]
    3. Process according to claim 2, characterized in that the basifying agent is chosen from sodium hydroxide, potassium hydroxide, lithium hydroxide, calcium hydroxide, magnesium hydroxide, sodium hydroxide preferably, sodium hydroxide and potassium hydroxide, preferably sodium hydroxide. o n HO, S n NH2
    [0004]
    4. Method according to claim 2, characterized in that the basifying agent is selected from the conjugate bases of formula (Ib) and (II b) of the amino acid of formula (1) or (11) below: NH 2 Mn NH 2 (11b) Formulas (Ib) and (11b) wherein R, n and M + are as defined in claim 1.
    [0005]
    5. Method according to claim 2, characterized in that the acidifying agent is selected from a mineral acid, preferably selected from hydrochloric acid, orthophosphoric acid, sulfuric acid, and an organic acid, preferably chosen among the hydroxy acids, in particular from citric acid, lactic acid, glycolic acid, gluconic acid, tartaric acid, malic acid, and more preferably from lactic acid and glycolic acid; .
    [0006]
    6. Process according to any one of the preceding claims, characterized in that the amino acid is chosen from the amino acids of formula (1) as well as their betaines forms, their optical isomers, their solvates such as hydrates and their salts. bases or acids, organic or mineral.
    [0007]
    7. Process according to any one of the preceding claims, characterized in that the composition comprises: an amino acid chosen from the amino acids of formula (1) and (11) as defined in claim 1 or 6, and the conjugate base of formula (Ib) or (Ib) of said amino acid as defined in claim 4, preferably an amino acid of formula (1) and its conjugate base of formula (Ib).
    [0008]
    8. Method according to the preceding claim characterized in that the amino acid molar ratio of formula (1) or (11) on its conjugate base (Ib) or (11b) ranges from 1 to 100, preferably from 1 to 10.
    [0009]
    9. Process according to any one of the preceding claims, characterized in that the amino acid is neutral or acidic.
    [0010]
    10. Method according to any one of the preceding claims, characterized in that the amino acid is selected from glycine, alanine, serine, beta alanine, taurine, and their salts, especially sodium glycinate, sodium alanilate, sodium serinate, lithium betaalaninate, sodium taurate, in particular chosen from glycine, alanine and serine, and preferably the amino acid is glycine.
    [0011]
    11. Process according to any one of the preceding claims, characterized in that the amino acid is present in the composition in a content ranging from 1.5 to 15% by weight, preferably from 2 to 10% by weight relative to to the total weight of the composition.
    [0012]
    12. Process according to any one of the preceding claims, characterized in that the pH of the composition is less than two units of the pKa of the equilibrium of the amino acid of formula (1) or (11) with its base ( lb) or (11b). preferably less than one unit
    [0013]
    13. Process according to any one of the preceding claims, characterized in that the pH of the composition ranges from 8 to 12, preferably from 9 to 11.
    [0014]
    14. Process according to any one of the preceding claims, characterized in that the composition comprises at least one denaturing amine agent, preferably chosen from urea and / or urea derivatives, in particular from urea, alkylurea, hydroxyethylurea; guanidine salts.
    [0015]
    15. Process according to any one of the preceding claims, characterized in that the composition comprises at least one thickening agent, preferably chosen from polymers, better still from polysaccharides, and even better from cellulose polymers, in particular from (C1 -06) alkylcelluloses and especially methyl hydroxyethylcelluloses. 35
    [0016]
    16. Process according to any one of the preceding claims, characterized in that the composition comprises at least one or more ingredients chosen from nonionic surfactants, preferably polyethoxylated, and preferably amino silicones.
    [0017]
    17. Method according to any one of the preceding claims, characterized in that the smoothing / straightening step is performed by means of a smoothing iron at a temperature between, inclusive limits, 100 ° C and 300 ° C, preferably between 120 ° C and 280 ° C, more preferably between 150 ° C and 250 ° C.
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    同族专利:
    公开号 | 公开日
    JP6746584B2|2020-08-26|
    JP2018500347A|2018-01-11|
    US10449134B2|2019-10-22|
    FR3030240B1|2017-07-28|
    US20180042831A1|2018-02-15|
    EP3259030A1|2017-12-27|
    WO2016102543A1|2016-06-30|
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    法律状态:
    2015-11-10| PLFP| Fee payment|Year of fee payment: 2 |
    2016-06-24| PLSC| Publication of the preliminary search report|Effective date: 20160624 |
    2016-11-11| PLFP| Fee payment|Year of fee payment: 3 |
    2017-11-13| PLFP| Fee payment|Year of fee payment: 4 |
    2019-11-15| PLFP| Fee payment|Year of fee payment: 6 |
    2020-11-12| PLFP| Fee payment|Year of fee payment: 7 |
    2021-11-15| PLFP| Fee payment|Year of fee payment: 8 |
    优先权:
    申请号 | 申请日 | 专利标题
    FR1463221A|FR3030240B1|2014-12-23|2014-12-23|PROCESS FOR TREATING KERATIN FIBERS WITH A COMPOSITION COMPRISING AN AMINO ACID|FR1463221A| FR3030240B1|2014-12-23|2014-12-23|PROCESS FOR TREATING KERATIN FIBERS WITH A COMPOSITION COMPRISING AN AMINO ACID|
    JP2017533782A| JP6746584B2|2014-12-23|2015-12-22|Method for treating keratin fibers with a composition containing amino acids|
    US15/537,958| US10449134B2|2014-12-23|2015-12-22|Process for treating keratin fibres with a composition comprising an amino acid|
    EP15813869.3A| EP3259030A1|2014-12-23|2015-12-22|Process for treating keratin fibres with a composition comprising an amino acid|
    PCT/EP2015/080936| WO2016102543A1|2014-12-23|2015-12-22|Process for treating keratin fibres with a composition comprising an amino acid|
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