Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/43—Guanidines
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/42—Amides
• • 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
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
• • 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

Definitions

• the invention relates to a process for relaxing keratin fibres with heat and at least one denaturing agent.
• the first consists, in a first stage, in performing this opening of the disulfide bonds using a composition containing a reducing agent, and then after, preferably, having rinsed the hair, in reconstituting, in a second stage, the said disulfide bonds by applying to the hair, that has been placed under tension beforehand by means of rollers or the like or shaped or smoothed out by other means, an oxidizing composition also known as a fixer, so as to give the head of hair the desired shape.
• an oxidizing composition also known as a fixer
• the second consists in performing a “lanthionization” operation, using a composition containing a base belonging to the hydroxide family. It leads to the replacement of the disulfide bonds (—CH2-S—S—CH2-) with lanthionine bonds (—CH2-S—CH2-).
• This lanthionization operation involves two consecutive chemical reactions:
• the first reaction consists of a beta-elimination on cystine brought about by a hydroxide ion, leading to the cleavage of this bond and to the formation of dehydroalanine.
• the second reaction is a reaction of the dehydroalanine with a thiol group.
• the double bond of the dehydroalanine formed is a reactive double bond. It can react with the thiol group of the cysteine residue that has been released to form a new bond known as a lanthionine bridge or bond or residue.
• this lanthionization technique does not require a fixing step, since the formation of the lanthionine bridges is irreversible. It is thus performed in a single step and makes it possible either to make the hair wavy or to relax it, uncurl it or smooth it out. However, it is mainly used for relaxing naturally frizzy hair.
• the reducing compositions generally used for the first step of a permanent-waving or relaxing operation contain thiols, sulfites or bisulfites as reducing agent. These agents are generally used in essentially aqueous medium at concentrations of between 0.5 and 1M to obtain good opening of the disulfide bonds.
• thiols those commonly used are thioglycolic acid, cysteamine, glyceryl monothioglycolate, thiolactic acid and cysteine.
• Thioglycolic acid is particularly effective for reducing the disulfide bonds of keratin at alkaline pH, especially in the form of ammonium thioglycolate, and is the product most widely used in permanent-waving (“hair waving”).
• thioglycolic acid must be used in a sufficiently basic medium (in practice at a pH of between 8.5 and 9.5) if it is desired to obtain curliness of satisfactory intensity.
• a thiol at alkaline pH also leads to degradation of the fibre and most particularly to impairment of artificial colorations.
• Sulfites or bisulfites are mainly used for relaxing. They have similar drawbacks to thiols, with less efficacy.
• Thiols and sulfites also have the drawback of having poor stability in aqueous solution.
• the durability of the reshaping effects obtained with thiols and sulfites by reduction of disulfides followed by fixing is judged to be very much inferior to that which may be obtained via the lanthionization technique.
• compositions generally used to perform the lanthionization contain as base a hydroxide such as sodium hydroxide, guanidinium hydroxide or lithium hydroxide.
• a hydroxide such as sodium hydroxide, guanidinium hydroxide or lithium hydroxide.
• These lanthionization active agents which allow the disulfide bonds to be opened via a beta-elimination mechanism, are generally used as a water-oil emulsion at concentrations of between 0.4 and 0.6M, by leaving them to act generally for 10 to 15 minutes at room temperature.
• Sodium hydroxide remains the agent most widely used.
• Guanidinium hydroxide is now the preferred compound for many compositions. These two hydroxides, sodium hydroxide and guanidinium hydroxide, are the two main agents used for relaxing or uncurling naturally frizzy hair.
• hydroxides have the major drawback of being caustic. This causticity affects the scalp by causing irritation, which may occasionally be severe. This may partially be remedied by first applying to the scalp a fatty protective cream often referred to as a “base” or “base cream”, the word “base” in this instance not having the meaning of a basic agent in the chemical sense.
• base fatty protective cream
• base cream When the protective cream is combined with hydroxide in a single composition, it is generally known as a “no-base” cream, as opposed to the above name. This “no-base” technology is preferred.
• hydroxides also affects the condition of the hair by firstly giving it a coarse feel and secondly making it much more fragile, this fragility possibly going as far as flaking or even breaking, or even the dissolution of the hair if the treatment is prolonged. In certain cases, hydroxides also cause decolorization of the natural colour of the hair.
• Formulations containing sodium hydroxide are generally known as “lye relaxers” and those not containing it are known as “no-lye relaxers”.
• guanidinium hydroxide Since guanidinium hydroxide is unstable, it is generated extemporaneously by mixing guanidine carbonate and a source of very sparingly soluble hydroxide such as calcium hydroxide. The reaction between these two compounds leads to the formation of guanidinium hydroxide and calcium carbonate, which precipitates in the composition. The presence of this precipitate makes the final rinsing of the hair much more difficult and leaves on the hair and the scalp mineral particles that give it a coarse feel and an unattractive appearance resembling dandruff.
• guanidinium hydroxide in the face of sodium hydroxide (“lye”) appears to arise from better relaxing efficacy and better skin tolerance.
• these technologies using bases of the hydroxide family remain very aggressive for the hair and the scalp and require very strict control of the application time to avoid excessive irritation and impairment of the hair, which may go as far as breaking of the hair.
• This aggressiveness arising from the causticity of hydroxides is just reason for these hair lanthionization compositions not being used for permanent-waving (“hair waving”), but being reserved for relaxing (“hair straightening” or “hair relaxing”).
• hydroxides are known to be good agents for hydrolysing amide functions (cf. for example March's Advanced Organic Chemistry, 5 ed., Wiley Interscience, New York, “Hydrolysis of Amides” pages 474 et seq.), which thus lead to cleavage of the peptide bonds via direct nucleophilic attack. It is thus probable that the impairments observed on the hair and keratin materials in the broad sense are largely due to partial hydrolysis of the amide bonds of keratin.
• thioglycolic acid in its ammonium thioglycolate form remains both the compound of reference and the compound most widely used in cosmetic formulations, both for shaping and for straightening.
• patent application CA 1315204 which describes a composition containing ammonium thioglycolate (5.5-11.5%) and urea or a monoalkylurea (1-3%) for shaping the hair,
• patent application NL 6 410 355 which describes a composition containing a sulfite (0.8-1.5M) and urea (0.6-3.0M) for shaping and relaxing the hair,
• patent application JP 2000/229 819 which describes a composition containing a sulfite or bisulfite (0.5-15%), urea (0.5-15%) and an alcohol (ethanol and/or isopropanol, 1-30%) for shaping and relaxing the hair.
• hydroxides serving as lanthionization active agent
• additives generally serving to protect the hair. Mention will be made, for example, of:
• patent application WO 02/085 317 which describes a composition containing organic nucleophiles, which react during the second step with the dehydroalanine formed with hydroxides, to give new bridges.
• the hair can be durably relaxed by combining the action of a denaturing agent and by heating to a temperature above 110° C. Excellent results in terms of relaxing, hair cosmetic properties and fibre integrity are thus obtained.
• keratin fibres means fibres of human or animal origin such as head hair, body hair, the eyelashes, wool, angora, cashmere or fur. Although the invention is not limited to particular keratin fibres, reference will nevertheless be made more particularly to head hair.
• the term “relaxing” covers the relaxing, straightening or uncurling, and includes such effects on, e.g., Caucasian and African hair.
• the term “to relax” means to relax, to straighten or to uncurl.
• denaturing agent includes those compounds specifically identified as such herein and means an organic or mineral compound containing both at least one electron-donating site of basic or nucleophilic nature and at least one electron-withdrawing site of acidic or electrophilic nature, which interact with the weak bonds of keratin.
• a denaturing agent is a compound capable of reducing the optical rotation of a model protein, for instance bovine serum albumin, by at least 70 and/or 50 at 579 nm, the measurements being taken after 3 hours of incubation at 37° C., using a polarimeter, as described in Biochemistry 2 (1), 47-57, 1963:
• the compound is considered as being a denaturing agent according to the invention if the reduction in the optical rotation is at least 70 in 0.05M pH 7.6 TRIS buffer and/or at least 5° in 5.45M urea solution.
• weak bonds of keratin means all of the non-covalent bonds, such as:
• heating means is a term invoking 35 U.S.C. 112, paragraph 6, and is defined as any means for heating keratin fibres to a temperature of at least 110° C., such as heating irons, for example flat or round irons, microwave generators, sources of infrared radiation, etc.
• heating irons for example flat or round irons, microwave generators, sources of infrared radiation, etc.
• heteroters include all of these examples but are not terms implicating 35 U.S.C. 112, paragraph 6.
• the inventor believes that there is a combined action, on the keratin fibres, of a denaturing agent and of the action of a heater or a heating means, which allows the fibres to be effectively and durably relaxed.
• a relaxing composition comprising at least one denaturing agent preferably having a molecular mass (weight) of greater than 18.1 g/mol, present in a molar concentration of between 1M and 8M in said composition, and
• a molar concentration of between 1M and 8M generally corresponds to a weight concentration of between about 6% and about 80% relative to the total weight of the composition.
• one subject of the invention is a process for relaxing keratin fibres comprising:
• a relaxing composition comprising at least one denaturing agent with a molecular mass of greater than 18.1 g/mol, present in a molar concentration of between 1M and 8M,
• the hair can be dried to some extent after treatment with the relaxing composition prior to application of heat to raise the temperature of the keratin fibres, for example by wiping with a towel, etc.
• the hair have remaining thereon at least some denaturing agent when heat is applied so as to obtain the benefits of the present invention.
• the relaxing composition comprises between 2M and 8M of the said denaturing agent; this corresponds to a weight concentration of between about 12% and about 80%, relative to the total weight of the composition, of the said denaturing agent.
• the temperature is raised using a heater or by heating means to a temperature of between 120° C. and 220° C. and more advantageously between 140° C. and 220° C.
• the molar mass of the denaturing agent is between 40 and 600 g/mol.
• the relaxing composition is applied to wet keratin fibres.
• the removal of excess relaxing composition may advantageously be inserted between the act of applying the relaxing composition and the act of raising the temperature.
• the denaturing agent is chosen from protein-denaturing agents such as ureas, guanidines, amidines, urethanes, aromatic monohydroxylated, dihydroxylated, trihydroxylated or polyhydroxylated derivatives, nitrogen heterocycles of the imidazole or triazole family, carboxylic acids and amide and thioamide derivatives thereof, thioureas, amino acids, alcohols, polyols, amine oxides, surfactants containing sugar, choline, deoxycholine or polyethylene glycol units, metal salts and sulfamides.
• protein-denaturing agents such as ureas, guanidines, amidines, urethanes, aromatic monohydroxylated, dihydroxylated, trihydroxylated or polyhydroxylated derivatives, nitrogen heterocycles of the imidazole or triazole family, carboxylic acids and amide and thioamide derivatives thereof, thioureas, amino acids, alcohols, polyols, amine oxides
• the denaturing agent is advantageously a urea or a guanidine.
• urea that may be used as relaxing active agent, this term refers to any derivative comprising in its chemical formula a carbonyl group simply bonded to 2 nitrogen atoms. These ureas are more particularly selected from the compounds of general formulae (I) and (II) below:
• R1, R2, R3 and R4 represent, independently:
• R4 may also denote a radical chosen from the following: carboxamide; methoxy; ethoxy; 1,2,4-triazolyl; cyclopentyl; methoxycarbonyl; ethoxycarbonyl; CO—CH ⁇ CH—COOH; phenyl optionally substituted with a chlorine atom or a hydroxyl radical; benzyl; or 2,5-dioxo-4-imidazolidinyl.
• R1 and R3 represent a hydrogen atom
• R2 may also represent a hydrogen atom or a methyl or ethyl radical and R4 an acetyl radical.
• R3 and R4 may also form, with the nitrogen atom that bears them, a piperidine or 3-methylpyrazole or 3,5-dimethylpyrazole or maleimide ring.
• R1 and R2, and also R3 and R4, may also form, with the nitrogen atom that bears them, an imidazole ring.
• R5 and R6 represent, independently of each other:
• A represents the radicals: CH2-CH2 or CH ⁇ CH or CH2-CO or CO—NH or CH ⁇ N or CO—CO or CHOH—CHOH or (HOOC)CH—CH or CHOH—CO or CH2-CH2-CH2 or CH2-NH—CO or CH ⁇ C(CH3)—CO or NH—CO—NH or CH2-CH2-CO or CH2-N(CH3)—CH2 or NH—CH2-NH or CO—CH(CH3)—CH2 or CO—CH2-CO or CO—NH—CO or CO—CH(COOH)—CH2 or CO—CH ⁇ C(COOH) or CO—CH ⁇ C(CH3) or CO—C(NH2) ⁇ CH or CO—C(CH3) ⁇ N or CO—CH ⁇ CH or CO—CH ⁇ N or CO—N ⁇ CH.
• guanidine that may be used as relaxing active agent, this term means any derivative comprising in its chemical formula at least one carbon atom doubly bonded to a nitrogen atom and singly bonded to two other nitrogen atoms. These guanidines are more particularly selected from the compounds of general formula (III) below:
• R1, R2, R3, R4 and R5 represent, independently:
• R5 may also denote a radical chosen from the following: acetyl; chloroacetyl; carboxamide; methoxy; ethoxy; 1,2,4-triazolyl; cyclopentyl; methoxycarbonyl; ethoxycarbonyl; CO—CH ⁇ CH—COOH; 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 each other, a hydrogen atom or a linear or branched C1-C4 lower alkyl radical, optionally substituted with one or two radicals chosen from: hydroxyl, amino, dimethylamino, carboxyl and carboxamide; or N-methylcarboxamide; or alternatively a phenyl radical.
• R6 and R7 denote, independently of each other, a hydrogen atom
• R4 and R5 may also form, with the nitrogen atom that bears them, a pyrrolidine, piperidine, pyrazole or 1,2,4-triazole ring, optionally substituted with one or two radicals chosen from: hydroxyl, amino and carboxyl.
• R3 and R5 may also together form a 5-membered ring optionally containing an oxo group
• the urea of formula (I) or (II) or the guanidine of formula (III) is advantageously present in a molar concentration of between 1M and 8M and more advantageously at a concentration of between 2M and 8M.
• any combination of two or more active agents can be used in combination herein.
• the pH of the compositions according to the invention is preferably between 3 and 10 and more particularly between 5 and 9.
• the urea of formula (I) or (II) or the guanidine of formula (III) is the sole relaxing active agent.
• compositions according to the invention are preferably either in the form of an aqueous solution or in the form of a thickened cream so as to keep the hair as straight as possible.
• These creams are preferably made in the form of “heavy” emulsions.
• composition used according to the invention may also comprise one or more additional cosmetic active agents.
• the additional cosmetic active agent(s) represent(s) from 0.01% to 30% and preferably from 0.1% to 10% by weight relative to the total weight of the cosmetic composition.
• the composition applied to the keratin fibres is applied at a rate of from 0.05 to 20 g and preferably from 0.1 to 10 g of composition per gram of dry keratin fibre.
• the composition after applying the composition, and before raising the temperature of the keratin fibres using a heater or heating means, the composition may be left to stand on the fibres, generally for between 30 seconds and 60 minutes and preferably 5 to 45 minutes.
• the process according to the invention comprises, preferably after applying the composition, raising the temperature of the keratin fibres to a temperature of between 110° C. and 250° C.
• an iron is used as a heater or heating means.
• iron means a device for heating keratin fibres by placing the fibres and the heating device in contact.
• the end of the iron that comes into contact with the hair generally has two flat surfaces. These two flat surfaces may be metallic. They may be smooth or notched.
• irons that may be used in the process according to the invention, mention may preferably be made of any type of flat iron and in particular, in a non-limiting manner, those described in U.S. Pat. No. 5,957,140 and U.S. Pat. No. 5,046,516.
• the application of the iron may be performed by successive touches separated by a few seconds, or by gradual moving or sliding along locks, etc.
• the application of the iron in the process according to the invention is performed by continuous movement from the root to the end, in one or more passes.
• the process according to the invention may also comprise partial predrying of the keratin fibres before raising the temperature, so as to avoid substantial release of steam that might burn the hands of the hairstylist and the individual's scalp.
• This predrying step may be performed, for example, using a hairdryer, a drying hood or by free drying.
• a simplified relaxing composition containing urea, at a concentration of 8M in water, as relaxing active agent is prepared.
• the pH of the composition is 8.06. This composition is applied to naturally frizzy African hair for 15 minutes at a temperature of 40° C. and the hair is then rapidly wiped with a towel.
• the hair is then straightened lock by lock using a flat iron heated to 180° C. for 5 to 10 seconds.
• the hair is efficiently relaxed and feels soft.
• a simplified relaxing composition containing urea, at a concentration of 4M in water, as relaxing active agent is prepared.
• the pH of the composition is 7.7. This composition is applied to naturally frizzy African hair for 25 minutes at a temperature of 40° C. and the hair is then rapidly wiped with a towel.
• the hair is then straightened lock by lock using a flat iron heated to 180° C., for 5 to 10 seconds.
• the hair is efficiently relaxed and feels soft.
• a simplified relaxing composition containing guanidine hydrochloride, at a concentration of 8M in water, as relaxing active agent is prepared.
• the pH of the composition is 5.46. This composition is applied to naturally frizzy African hair for 15 minutes, at a temperature of 40° C. and the hair is then rapidly wiped with a towel.
• the hair is then straightened lock by lock using a flat iron heated to 180° C., for 5 to 10 seconds.
• the hair is efficiently relaxed and feels soft.
• the invention process for relaxing keratin fibres includes hair relaxing, uncurling and straightening, etc. While the invention can be thought of as involving distinct acts, such as
• keratin fibres it can also be thought of as a method comprising raising the temperature of keratin fibres, using a heater or heating means, to a temperature of between 110 and 250° C. wherein said keratin fibres comprise on at least a part of a surface thereof at least one denaturing agent with a molecular mass of greater than 18.1 g/mol.
• a relaxing composition comprising, consisting essentially of, or consisting of, at least one denaturing agent with a molecular mass of greater than 18.1 g/mol, present in a molar concentration of between 1M and 8M, and
• phrases “selected from the group consisting of,” “chosen from,” and the like include mixtures of the specified materials.

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• 2004
  • 2004-11-26 FR FR0452775A patent/FR2878435B1/fr not_active Expired - Fee Related
• 2005
  • 2005-11-14 EP EP14180383.3A patent/EP2826461B1/fr active Active
  • 2005-11-14 ES ES05292406.5T patent/ES2517817T3/es active Active
  • 2005-11-14 ES ES14180383.3T patent/ES2588538T3/es active Active
  • 2005-11-14 EP EP05292406.5A patent/EP1661551B1/fr active Active
  • 2005-11-24 BR BRPI0505222-0A patent/BRPI0505222A/pt active IP Right Grant
  • 2005-11-28 US US11/287,292 patent/US20060127337A1/en not_active Abandoned
• 2010
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