Classifications

• • A—HUMAN NECESSITIES
  • A45—HAND OR TRAVELLING ARTICLES
  • A45D—HAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
  • A45D7/00—Processes of waving, straightening or curling hair
  • A45D7/06—Processes of waving, straightening or curling hair combined chemical and thermal
• • A—HUMAN NECESSITIES
  • A45—HAND OR TRAVELLING ARTICLES
  • A45D—HAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
  • A45D2/00—Hair-curling or hair-waving appliances ; Appliances for hair dressing treatment not otherwise provided for
  • A45D2/001—Hair straightening appliances
• • 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
  • A61K8/362—Polycarboxylic acids
• • 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
  • 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
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/73—Polysaccharides
• • 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
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
  • A61K2800/24—Thermal properties

Definitions

• the invention relates to a process for relaxing keratin fibres with a heating means and at least one ⁇ -hydroxy acid and/or keto acid derivative.
• the relaxing process according to the invention is performed without using any reducing agent or lanthionizing agent. It does not include any reducing or lanthionization step.
• keratin fibres means fibres of human or animal origin such as head hair, bodily 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 of Caucasian or African hair.
• heating means means 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 or sources of infrared radiation.
• 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 or straighten it out. However, it is mainly used for relaxing naturally curly hair.
• the reducing compositions generally used for the first step of a permanent-waving or hair-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 1 M 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 efficient at reducing the disulfide bonds of keratin at alkaline pH, especially in the form of ammonium thioglycolate, and constitutes the product most frequently used in permanent waving (“hair waving”). It has been found, however, that thioglycolic acid must be used in sufficiently basic medium (in practice at a pH of between 8.5 and 9.5) if curling of satisfactory intensity is to be obtained. Besides the drawback of releasing an unpleasant odour requiring the use of more or less efficient fragrances to mask the odours, the use of a thiol at alkaline pH also results in degradation of the fibre and most particularly in impairment of artificial colorations.
• Sulfites or bisulfites are mainly used for relaxing the hair. They have drawbacks similar to those of thiols, with lower 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 following by fixing is judged to be very much lower than that which may be obtained via the lanthionization technique.
• compositions generally used to perform lanthionization contain as base a hydroxide such as sodium hydroxide, guanidinium hydroxide or lithium hydroxide.
• lanthionization active agents which allow opening of the disulfide bonds via a beta-elimination mechanism, are generally used as a water-oil emulsion at concentrations of between 0.4 and 0.6 M, by leaving them to act generally for 10 to 15 minutes at room temperature.
• Sodium hydroxide remains the agent most frequently 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 the relaxing or uncurling of naturally curly hair.
• hydroxides also affects the state of the hair by firstly giving it a coarse feel and secondly making it much more brittle, this brittleness possibly going as far as crumbling or breaking or even dissolution of the hair if the treatment is prolonged. In certain cases, hydroxides also cause decoloration of the natural colour of the hair.
• Formulations containing sodium hydroxide are generally referred to as “lye relaxers” and those not containing it are referred as “no-lye relaxers”.
• guanidinium hydroxide Since guanidinium hydroxide is unstable, it is generated at the time of use by mixing guanidinium carbonate and a source of 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 mineral particles on the hair and the scalp, which give it a coarse feel and an unaesthetic appearance resembling dandruff.
• guanidinium hydroxide (“no-lye”) over sodium hydroxide (“lye”) appears to arise from better relaxing efficacy and better skin tolerance.
• these techniques using bases of the hydroxide family remain very aggressive to the hair and the scalp and require very strict control of the duration of application to avoid excessive irritation and impairment of the hair that may go as far as breakage.
• This aggressiveness arising from the causticity of hydroxides is justification for not using these hair lanthionization compositions for permanent waving (hair waving), but solely for hair straightening or hair relaxing.
• hydroxides are known to be good agents for hydrolysing amide functions (cf. for example March's Advanced Organic Chemistry, 5th edition, Wiley Interscience, New York, “Hydrolysis of Amides” page 474 et seq.), which thus lead to cleavage of peptide bonds by direct nucleophilic attack. It is thus probable that the observed impairments of the hair and of keratin materials in the broad sense are largely due to partial hydrolysis of the amide bonds of keratin.
• thioglycolic acid in the form of ammonium thioglycolate remains both the reference compound and the compound most widely used in cosmetic formulations, not only for shaping but also for straightening the hair.
• hydroxides serving as lanthionization active agent
• additives generally serving to protect the hair. Mention will be made, for example, of:
• hair can be durably relaxed by combining the action of an ⁇ -hydroxy acid and/or keto acid derivative and of a means of heating to a temperature above 110° C. Excellent results in terms of relaxing, cosmetic properties of the hair and fibre integrity are thus obtained.
• the Applicant considers that there is a combined action, on the keratin fibres, of an ⁇ -hydroxy acid and/or keto acid derivative and of a heating means, which allows the fibres to be efficiently and durably relaxed.
• the invention relates to a process for relaxing keratin fibres, comprising:
• the temperature is raised using a heating means to a temperature of between 120° C. and 220° C. and more advantageously between 140° C. and 220° C.
• the said composition is applied to wet keratin fibres.
• a step intended to remove the excess composition may also be introduced between the step of applying the composition and the step of raising the temperature.
• R1 H, OH, NH2, CH2-COOH or a linear or branched C1-C4 alkyl
• R2 H, COOH, CHOH—COOH, CF3, CH ⁇ CH2, NHCONH2, a linear, branched or cyclic C1-C8 alkyl optionally substituted with a radical chosen from OH, Cl, NH2, COOH, CF3 and SCH3; a phenyl or benzyl optionally substituted with one OH or OCH3 radical; or alternatively the radical
• R1 and R2 may also together form an oxo radical ( ⁇ O) or a cyclopropyl, cyclobutyl, hydroxycyclobutyl, cyclopentyl or cyclohexyl ring with the carbon atom that bears them, or alternatively a radical
• glycolic acid oxalic acid lactic acid 1-hydroxy-1-cyclopropanecarboxylic acid 2-hydroxy-3-butenoic acid 2-hydroxyisobutyric acid 2-hydroxy-n-butyric acid isoserine glyceric acid 2-hydroxy-3-methylbutyric acid 2-hydroxy-2-methylbutyric acid 2-hydroxyvaleric acid 4-amino-2-hydroxybutyric acid 1-hydroxycyclohexanecarboxylic acid dihydroxyfumaric acid citramalic acid tartaric acid citric acid 2-hydroxy-4-(methylthio)butyric acid mandelic acid 2-hydroxy-3-methylvaleric acid glyoxylurea ⁇ -imidazolelactic acid 2-trifluoromethyl-2-hydroxypropionic acid hexahydromandelic acid 2-hydroxyoctanoic acid arabic acid 3-phenylactic acid hydroxyphenylglycine 3-hydroxymandelic acid 4-hydroxymandelic acid 2-hydroxynonanoic acid L-arginic acid 3-methoxymandelic acid 4-
• N-2-hydroxyethyllactamide and the stereoisomers, organic or mineral salts and solvates thereof.
• R5 COOH, a linear or branched C1-C6 alkyl optionally substituted with an OH, COOH or Br radical; a phenyl or benzyl optionally substituted with an OH or COOH radical; or an indolyl radical or
• N-2-hydroxyethylpyruvamide and the stereoisomers, organic or mineral salts and solvates thereof.
• the working molar concentration is advantageously between 2 and 8 M and more advantageously between 4 and 8M.
• the working pH is preferably less than or equal to 7.
• compositions according to the invention are 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 prepared in the form of “heavy” emulsions.
• compositions contain at least one ⁇ -hydroxy acid derivative of formula (I) and/or at least one keto acid derivative of formula (II) and/or mixtures thereof in all proportions.
• compositions of the invention contain the hydroxy acid and/or keto acid derivative as sole hair-relaxing active agent.
• composition used according to the invention may also comprise one or more additional cosmetic active agents.
• the said 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 in an amount of from 0.05 to 20 g and preferably from 0.1 to 10 g of composition per gram of dry keratin fibre.
• the said composition After applying the composition, and before raising the temperature of the keratin fibres using a heating means, the said composition may be left to act, generally for 30 seconds to 60 minutes and preferably 5 to 45 minutes.
• the process according to the invention includes, after the step of applying the composition, a step of raising the temperature of the keratin fibres, using a heating means, to a temperature of between 110° C. and 250° C.
• an iron is used as heating means.
• iron means a device for heating keratin fibres that places the said 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 crinkled.
• irons that may be used in the process according to the invention, mention may be made of flat irons of any type, 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 iron may be applied by successive separate touches of a few seconds, or by gradually moving or sliding it along the locks.
• the iron is applied by continuous movement from the root to the end, in one or more passes.
• the process according to the invention may also include an additional step of partial predrying of the keratin fibres before the step of raising the temperature, so as to avoid substantial evolution of steam that might burn the stylist's hands and the individual's scalp.
• This predrying step may take place, for example, using a hairdryer, a hood or alternatively by drying in the open air.
• the invention also relates to a kit comprising at least:
• the hair-relaxing composition contains at least one ⁇ -hydroxy acid derivative of formula (I) and/or at least one keto acid derivative of formula (II) and/or mixtures thereof in all proportions as defined above.
• a simplified hair-relaxing composition is prepared, containing DL-lactic acid at a concentration of 8 M in water, as hair-relaxing active agent. This composition is applied to naturally curly African hair for 15 minutes at a temperature of 40° C., and the hair is then rapidly towel-dried.
• Lock-by-lock straightening of the head of hair is then performed using a flat iron heated to 180° C., for 10 to 15 seconds.
• the hair is efficiently relaxed and feels soft.
• a simplified hair-relaxing composition is prepared, containing pyruvic acid at a concentration of 8 M in water, as hair-relaxing active agent. This composition is applied to naturally curly African hair for 15 minutes at a temperature of 40° C., and the hair is then rapidly towel-dried.
• Lock-by-lock straightening of the head of hair is then performed using a flat iron heated to 180° C., for 10 to 15 seconds.
• the hair is efficiently relaxed and feels soft.
• a simplified hair-relaxing composition is prepared, containing pyruvic acid at a concentration of 4 M in water, as hair-relaxing active agent. This composition is applied to naturally curly African hair for 25 minutes at a temperature of 40° C., and the hair is then rapidly towel-dried.
• Lock-by-lock straightening of the head of hair is then performed using a flat iron heated to 180° C., for 10 to 15 seconds.
• the hair is efficiently relaxed and feels soft.
• a simplified hair-relaxing composition is prepared, containing L-lactic acid at a concentration of 4 M in water, as hair-relaxing active agent. This composition is applied to naturally curly African hair for 25 minutes at a temperature of 40° C., and the hair is then rapidly towel-dried.
• Lock-by-lock straightening of the head of hair is then performed using a flat iron heated to 180° C., for 10 to 15 seconds.
• the hair is efficiently relaxed and feels soft.

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• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
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• Epidemiology (AREA)
• Emergency Medicine (AREA)
• Physics & Mathematics (AREA)
• Thermal Sciences (AREA)
• Cosmetics (AREA)

Priority Applications (5)

Applications Claiming Priority (5)

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Cited By (24)

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Citations (6)

Family Cites Families (39)

• 2006
  • 2006-05-24 FR FR0651909A patent/FR2901471B1/fr active Active
• 2007
  • 2007-05-23 EP EP07765948.0A patent/EP2029237B1/fr active Active
  • 2007-05-23 ES ES16166906T patent/ES2757380T3/es active Active
  • 2007-05-23 BR BRPI0711197A patent/BRPI0711197B1/pt active IP Right Grant
  • 2007-05-23 WO PCT/FR2007/000872 patent/WO2007135299A1/fr active Application Filing
  • 2007-05-23 EP EP16166906.4A patent/EP3141284B1/fr active Active
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