US20050238599A1 - Process for permanently reshaping the hair using particular aminosilicones - Google Patents

Process for permanently reshaping the hair using particular aminosilicones Download PDF

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US20050238599A1
US20050238599A1 US11/158,014 US15801405A US2005238599A1 US 20050238599 A1 US20050238599 A1 US 20050238599A1 US 15801405 A US15801405 A US 15801405A US 2005238599 A1 US2005238599 A1 US 2005238599A1
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Prior art keywords
treatment
composition
post
hair
aminosilicone
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US11/158,014
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Priscille Devin-Baudoin
Anne Sabbagh
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LOreal SA
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LOreal SA
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/896Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/04Preparations for permanent waving or straightening the hair
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/22Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups

Definitions

  • the present disclosure relates to a process for permanently reshaping keratin fibres, for example, hair.
  • This process may be used, for example, in professional hairstyling salons, or privately via the marketing of kits.
  • the expression “permanent reshaping process” means any long-lasting process for shaping, curling, straightening or relaxing the hair.
  • keratin fibres means, for example, hair, eyelashes and eyebrows.
  • One technique for obtaining a permanent reshaping of the hair comprises, in a first stage, opening the keratin —S—S— disulphide (cystine) bonds using a reducing composition comprising a reducing agent (reduction), followed, for example, after having rinsed the hair thus treated, by reconstituting, in a second stage, the disulphide bonds by applying to the hair, which has been placed under tension beforehand (for example, with curlers and the like), an oxidizing composition (oxidizing, also known as fixing) so as to finally give the hair the desired shape.
  • This technique thus can make it equally possible either to make the hair wavy or to straighten or relax it.
  • the new shape given to the hair by a chemical treatment such as above can be long-lasting and may, for example, withstand the action of washing with water and/or shampoos, as opposed to other techniques for temporary reshaping, such as hairsetting.
  • the reducing composition that may be used to carry out the reduction of a permanent-waving process may comprise, as reducing agents, sulphites, bisulphites or thiols.
  • thiols that may be mentioned are cysteine and its various derivatives, cysteamine and its derivatives, thiolactic acid, thioglycolic acid and its esters, such as glyceryl monothioglycolate, and thioglycerol.
  • compositions based on aqueous hydrogen peroxide solution or alkali metal bromates may be used.
  • One disadvantage of the permanent-waving techniques known to date is that applying them repeatedly to the hair may induce in the long term a gradual deterioration in the quality of the hair, for example, a gradual and pronounced deterioration in the sheen and the cosmetic properties of the hair, such as the softness of the fibres, which may have a tendency to become more and more coarse, and also as regards their disentangling, the hair may become more and more difficult to disentangle. This deterioration may be pronounced when the fixing of the permanent-waving process is carried out using a bromate.
  • the present disclosure addresses at least one of these disadvantages by providing a process for permanently reshaping keratin fibres, such as hair, which can reduce the degree of mechanical and/or cosmetic degradation of the hair, while at the same time providing a satisfactory degree, quality and liveliness of curls.
  • the inventors have discovered, surprisingly and unexpectedly, that by applying to the hair, before applying the reducing composition and/or after having applied the oxidizing composition, at least one pre-treatment and/or post-treatment cosmetic composition comprising at least one aminosilicone as defined below, it is possible to solve at least one of these problems.
  • One new embodiment is a process for permanently reshaping keratin fibres, such as hair, comprising the following:
  • kits for permanently reshaping keratin fibres comprising at least one compartment comprising a pre-treatment and/or post-treatment cosmetic composition comprising at least one aminosilicone comprising at least one aminoethylimino(C 4 -C 8 )alkyl group.
  • the at least one aminosilicone is of the following formula: in which:
  • the viscosity of the at least one aminosilicone may be, for example, greater than 25 000 mm 2 /s at 25° C.
  • this viscosity may range from 30 000 to 200 000 mm 2 /s at 25° C., such as from 30 000 to 150 000 mm 2 /s at 25° C.
  • the viscosity is measured at 25 ° C. according to ASTM standard 445, Appendix C.
  • the at least one aminosilicone has a weight-average molecular mass ranging, for example, from 2 000 to 1 000 000, and further, for example, from 3 500 to 200 000.
  • the weight-average molecular mass of the at least one aminosilicone is measured by Gel Permeation Chromatography (GPC) at room temperature as polystyrene equivalent.
  • the columns used are ⁇ styragel columns.
  • the eluent is THF, the flow rate is 1 ml/min. 200 ⁇ l of a solution containing 0.5% by weight of silicone in THF are injected. The detection is made by refractometry and UVmetry.
  • the at least one aminosilicone may be used as is or in the form of emulsions.
  • the emulsion may comprise at least one surfactant.
  • the at least one surfactant may be of any type, such as cationic and/or nonionic.
  • the mean particle size of the at least one aminosilicone in the emulsion ranges, for example, from 3 nm to 500 nm, further, for example, from 70 nm to 500 nm, and even further, for example, from 150 to 275 nm.
  • One of ordinary skill in the art can measure such particle sizes by known techniques. Such particle sizes are measured with a laser granulometer.
  • aminosilicone corresponding to this formula is DC2-8299® from Dow Corning.
  • the concentration of the at least one aminosilicone comprising at least one aminoethylimino(C 4 -C 8 )alkyl group in the pre-treatment and/or post-treatment composition ranges, for example, from 0.05 to 10% by weight relative to the total weight of the composition, such as from 0.1 to 7% by weight relative to the total weight of the composition.
  • the pre-treatment and/or post-treatment composition comprising at least one aminosilicone as defined above may further comprise at least one active agent chosen from water-soluble and liposoluble active agents, having cosmetic and/or dermopharmaceutical activity.
  • active agents include vitamins and derivatives thereof such as vitamin E, vitamin E acetate, vitamin C and its esters, the B vitamins, vitamin A alcohol and retinol, vitamin A acid and retinoic acid and its derivatives, provitamins such as panthenol, vitamin A palmitate, niacinamide, ergocalciferol, antioxidants, essential oils, wetting agents, silicone and non-silicone sunscreens, preserving agents, sequestering agents, pearlescent agents, pigments, moisturizers, antidandruff agents, anti-seborrhoeic agents, plasticizers, hydroxy acids, electrolytes, solvents and fragrances.
  • compositions may also comprise at least one solvent such as C1-C8 lower alcohols such as ethanol.
  • the pH of the pre-treatment and/or post-treatment composition comprising at least one aminosilicone as defined above ranges, for example, from 2 to 10, such as from 3 to 9.
  • the pre-treatment composition comprising at least one aminosilicone as defined above is applied to the hair to be treated, which may optionally have been moistened beforehand.
  • This application may be performed after the usual procedure of placing the hair under tension in a shape corresponding to the desired final shape of the hair (for example, curls).
  • This procedure itself can possibly be carried out by any implements, such as a mechanical implement, that is suitable and known per se for maintaining hair under tension, such as, rollers, curlers and the like.
  • the pre-treatment and/or post-treatment composition comprising at least one aminosilicone as defined above is left to act on the hair, at room temperature or under heat, for a period of time ranging from, for example, 1 to 60 minutes, such as from 3 to 30 minutes.
  • the hair impregnated with the pre-treatment composition comprising at least one aminosilicone as defined above can be rinsed, wherein the rinsing may be carried out using water.
  • a reducing composition is applied to the hair, wherein the reducing composition may comprise at least one thiol.
  • the thiol in the reducing composition may be chosen from thiols known as reducing agents such as thioglycolic acid, glyceryl and glycol monothioglycolate, cysteamine and its C 1 -C 4 acyl derivatives such as N-acetylcysteamine or N-propionyl-cysteamine, cysteine, N-acetylcysteine, sugar N-mercaptoalkylamides such as N-(2-mercaptoethyl)gluconamide, 3-mercaptopropionic acid and its derivatives, thiolactic acid and its esters such as glyceryl monothiolactate, thiomalic acid, pantethine, thioglycerol, alkali metal and alkaline-earth metal sulphites and bisulphites, the N-(mercaptoalkyl)- ⁇ -hydroxyalkylamides described in patent application EP-A-354 835 and the N-mono- or N,
  • thioglycolic acid, thiolactic acid and 3-mercaptopropionic acid are chosen for use.
  • the reducing agents may be present in a concentration that may range, for example, from 1% to 20% by weight relative to the total weight of the reducing composition.
  • the pH of the reducing composition may range, for example, from 6 to 10, and further, for example, from 7 to 9.
  • the pH values of the reducing compositions may be conventionally adjusted by adding at least one basifying agent.
  • basifying agents include, for example, aqueous ammonia, monoethanolamine, diethanolamine, triethanolamine, isopropanolamine, 1,3-propanediamine, ammonium and alkali metal carbonates and bicarbonates, primary, secondary and tertiary amine carbonates and bicarbonates and organic carbonates such as guanidine carbonate.
  • the reducing composition may be in the form of a thickened or unthickened lotion, a cream, a gel, or any other suitable form, and may comprise additives known for their use in reducing compositions for permanently reshaping the hair.
  • the reducing composition may also be of the exothermic type, i.e., the type causing a certain level of heating during application to the hair, affording a pleasant sensation to the person on whom the permanent-waving or straightening process is being performed.
  • the reducing composition may also comprise a solvent such as, ethanol, propanol, isopropanol and glycerol, in a maximum concentration of 20% by weight relative to the total weight of the composition.
  • a solvent such as, ethanol, propanol, isopropanol and glycerol
  • the reducing composition may be, for example, 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, for example based on glyceryl stearate, glycol stearate, self-emulsifiable waxes, fatty alcohols, etc.
  • liquids or gels containing thickeners such as carboxyvinyl polymers or copolymers, which can “stick” the hairs together and keep them in the smooth position during the exposure time.
  • compositions may also be in a “self-neutralizing” or “self-regulated” form and, in this case, the reducing agents used may be combined with at least one disulphide known for its use in a reducing composition for self-neutralizing permanent waving.
  • the hair onto which the reducing composition has been applied is left to rest for a few minutes, such as ranging from 2 to 40 minutes, and further such as from 5 to 30 minutes, so as to allow the reducing agent sufficient time to act correctly on the hair.
  • This waiting stage may be carried out by leaving the treated hair to rest in the open air (at room temperature or with heating). During this waiting stage, care may be taken to ensure that the hair does not dry out completely but instead remains humid.
  • the hair impregnated with the reducing composition can then be carefully rinsed, for example, with water.
  • a heating at high temperature for a few seconds may be carried out.
  • An oxidizing composition can then be applied to the hair thus rinsed, with the aim of fixing the new shape given to the hair. It may also be envisaged to leave the hair to be oxidized by the air.
  • the oxidizing composition comprises an oxidizing agent that may be chosen from aqueous hydrogen peroxide solution, alkali metal bromates, persalts and polythionates.
  • an oxidizing agent that may be chosen from aqueous hydrogen peroxide solution, alkali metal bromates, persalts and polythionates.
  • the bromate concentration in the oxidizing composition ranges, for example, from 0.1 to2 M.
  • the pH of the oxidizing composition may range, for example, from 2 to 10.
  • the hair onto which the oxidizing composition has been applied is then left for a standing or waiting stage that may last a few minutes, for example, ranging from 3 to 30 minutes and further, for example, from 5 to 15 minutes.
  • the post-treatment composition comprising at least one aminosilicone as defined above is, for example, applied, after rinsing out the oxidizing composition, to wet or dry hair.
  • the hair that has undergone the post-treatment may optionally be dried and/or heated and/or rinsed, before being styled.
  • the composition may be applied while the hair is maintained by a mechanical device, for example, hairsetting rollers or curlers.
  • the hair impregnated with the oxidizing composition is rinsed carefully, such as with water.
  • the keratin fibres may be separated from the implement used for placing the keratin fibres under tension.
  • the hair finally obtained can have good cosmetic properties: the hair can be shinier, softer and easier to disentangle or to style.
  • the pre-treatment and/or post-treatment composition comprising at least one aminosilicone as defined above is applied according to at least one of the following variants:
  • a straightening agent such as a thiol agent or an alkaline agent.
  • the process may be carried out, for example, by applying the pre-treatment and/or post-treatment composition comprising at least one aminosilicone as defined above according to at least one of the following variants:
  • the process may be carried out, for example, by applying the pre-treatment and/or post-treatment composition comprising at least one aminosilicone as defined above to wet hair, after rinsing out neutralizing shampoo, by rinsing before drying the hair.
  • the process may give lively curls, and the hair may be at least one of supple, light, silky and well separated.
  • the process may afford control of the body of the hair, may make the hair smooth from the root to the tip, and may give a more natural feel.
  • composition described in 1) may be used for the care of recently straightened or permanently-waved hair. This composition was applied to wet hair after rinsing out the neutralizing shampoo, or after rinsing out the fixing agent in the case of permanent waving. This composition can make the hair smooth and soft.

Abstract

A process for permanently reshaping keratin fibres, comprising the application to the keratin fibres, before reducing and/or after fixing, of a pre-treatment and/or post-treatment cosmetic composition comprising, in a cosmetically acceptable medium, at least one aminosilicone comprising at least one aminoethylimino(C4-C8)alkyl group.

Description

  • The present disclosure relates to a process for permanently reshaping keratin fibres, for example, hair. This process may be used, for example, in professional hairstyling salons, or privately via the marketing of kits.
  • The expression “permanent reshaping process” means any long-lasting process for shaping, curling, straightening or relaxing the hair.
  • The expression “keratin fibres” means, for example, hair, eyelashes and eyebrows.
  • One technique for obtaining a permanent reshaping of the hair comprises, in a first stage, opening the keratin —S—S— disulphide (cystine) bonds using a reducing composition comprising a reducing agent (reduction), followed, for example, after having rinsed the hair thus treated, by reconstituting, in a second stage, the disulphide bonds by applying to the hair, which has been placed under tension beforehand (for example, with curlers and the like), an oxidizing composition (oxidizing, also known as fixing) so as to finally give the hair the desired shape. This technique thus can make it equally possible either to make the hair wavy or to straighten or relax it. The new shape given to the hair by a chemical treatment such as above can be long-lasting and may, for example, withstand the action of washing with water and/or shampoos, as opposed to other techniques for temporary reshaping, such as hairsetting.
  • The reducing composition that may be used to carry out the reduction of a permanent-waving process may comprise, as reducing agents, sulphites, bisulphites or thiols. Among the thiols that may be mentioned are cysteine and its various derivatives, cysteamine and its derivatives, thiolactic acid, thioglycolic acid and its esters, such as glyceryl monothioglycolate, and thioglycerol.
  • As to the oxidizing composition used to carry out the fixing, compositions based on aqueous hydrogen peroxide solution or alkali metal bromates may be used.
  • One disadvantage of the permanent-waving techniques known to date is that applying them repeatedly to the hair may induce in the long term a gradual deterioration in the quality of the hair, for example, a gradual and pronounced deterioration in the sheen and the cosmetic properties of the hair, such as the softness of the fibres, which may have a tendency to become more and more coarse, and also as regards their disentangling, the hair may become more and more difficult to disentangle. This deterioration may be pronounced when the fixing of the permanent-waving process is carried out using a bromate.
  • To limit this deterioration of the hair, it has already been proposed to introduce conditioners directly into the reducing composition. For example, Japanese patent applications H2-250814 and H9-151120 describe reducing compositions containing aminosilicones, which may optionally be in the form of a microemulsion.
  • However, processes for permanently reshaping the hair using such compositions are not entirely satisfactory, since the degree, the quality and liveliness of the curls may be insufficient and short-lived, for example, if the conditioner, such as amino-silicones, directly combined with the reducing agent to block the activity of the reducing agent.
  • The present disclosure addresses at least one of these disadvantages by providing a process for permanently reshaping keratin fibres, such as hair, which can reduce the degree of mechanical and/or cosmetic degradation of the hair, while at the same time providing a satisfactory degree, quality and liveliness of curls.
  • The inventors have discovered, surprisingly and unexpectedly, that by applying to the hair, before applying the reducing composition and/or after having applied the oxidizing composition, at least one pre-treatment and/or post-treatment cosmetic composition comprising at least one aminosilicone as defined below, it is possible to solve at least one of these problems.
  • One new embodiment is a process for permanently reshaping keratin fibres, such as hair, comprising the following:
      • (i) applying a reducing composition to the keratin fibres; and
      • (ii) oxidizing the keratin fibres,
        wherein the process also comprises applying to the keratin fibres, before (i) and/or after (ii), a pre-treatment and/or post-treatment cosmetic composition comprising, in a cosmetically acceptable medium, at least one aminosilicone comprising at least one aminoethylimino(C4-C8)alkyl group. Another embodiment relates to a pre-treatment and/or post-treatment cosmetic composition for pre-treatment and/or post-treatment in permanent reshaping of keratin fibres comprising, in a cosmetically acceptable medium in said composition, at least one aminosilicone comprising at least one aminoethylimino(C4-C8)alkyl group.
  • Another new embodiment relates to a kit for permanently reshaping keratin fibres, comprising at least one compartment comprising a pre-treatment and/or post-treatment cosmetic composition comprising at least one aminosilicone comprising at least one aminoethylimino(C4-C8)alkyl group.
  • In one new embodiment, the at least one aminosilicone is of the following formula:
    Figure US20050238599A1-20051027-C00001

    in which:
      • A is chosen from linear and branched C4-C8 alkylene radicals, for example, linear and branched C4 alkylene radicals;
      • m and n are numbers such that the sum (n+m) may range from 1 to 2 000, such as from 50 to 150; n is a number, for example, ranging from 0 to 1 999, further for example, from 49 to 149; and m is a number, for example, ranging from 1 to 2 000, further for example, from 1 to 10.
  • The viscosity of the at least one aminosilicone may be, for example, greater than 25 000 mm2/s at 25° C.
  • Further, for example, this viscosity may range from 30 000 to 200 000 mm2/s at 25° C., such as from 30 000 to 150 000 mm2/s at 25° C.
  • The viscosity is measured at 25 ° C. according to ASTM standard 445, Appendix C.
  • The at least one aminosilicone has a weight-average molecular mass ranging, for example, from 2 000 to 1 000 000, and further, for example, from 3 500 to 200 000.
  • The weight-average molecular mass of the at least one aminosilicone is measured by Gel Permeation Chromatography (GPC) at room temperature as polystyrene equivalent. The columns used are μ styragel columns. The eluent is THF, the flow rate is 1 ml/min. 200 μl of a solution containing 0.5% by weight of silicone in THF are injected. The detection is made by refractometry and UVmetry.
  • The at least one aminosilicone may be used as is or in the form of emulsions. The emulsion may comprise at least one surfactant. The at least one surfactant may be of any type, such as cationic and/or nonionic. The mean particle size of the at least one aminosilicone in the emulsion ranges, for example, from 3 nm to 500 nm, further, for example, from 70 nm to 500 nm, and even further, for example, from 150 to 275 nm. One of ordinary skill in the art can measure such particle sizes by known techniques. Such particle sizes are measured with a laser granulometer.
  • An example of the aminosilicone corresponding to this formula is DC2-8299® from Dow Corning.
  • In one embodiment, the concentration of the at least one aminosilicone comprising at least one aminoethylimino(C4-C8)alkyl group in the pre-treatment and/or post-treatment composition ranges, for example, from 0.05 to 10% by weight relative to the total weight of the composition, such as from 0.1 to 7% by weight relative to the total weight of the composition.
  • The pre-treatment and/or post-treatment composition comprising at least one aminosilicone as defined above may further comprise at least one active agent chosen from water-soluble and liposoluble active agents, having cosmetic and/or dermopharmaceutical activity. Non-limiting examples of those active agents include vitamins and derivatives thereof such as vitamin E, vitamin E acetate, vitamin C and its esters, the B vitamins, vitamin A alcohol and retinol, vitamin A acid and retinoic acid and its derivatives, provitamins such as panthenol, vitamin A palmitate, niacinamide, ergocalciferol, antioxidants, essential oils, wetting agents, silicone and non-silicone sunscreens, preserving agents, sequestering agents, pearlescent agents, pigments, moisturizers, antidandruff agents, anti-seborrhoeic agents, plasticizers, hydroxy acids, electrolytes, solvents and fragrances.
  • The compositions may also comprise at least one solvent such as C1-C8 lower alcohols such as ethanol.
  • The pH of the pre-treatment and/or post-treatment composition comprising at least one aminosilicone as defined above ranges, for example, from 2 to 10, such as from 3 to 9.
  • In one embodiment, the pre-treatment composition comprising at least one aminosilicone as defined above is applied to the hair to be treated, which may optionally have been moistened beforehand. This application may be performed after the usual procedure of placing the hair under tension in a shape corresponding to the desired final shape of the hair (for example, curls). This procedure itself can possibly be carried out by any implements, such as a mechanical implement, that is suitable and known per se for maintaining hair under tension, such as, rollers, curlers and the like.
  • In another embodiment, the pre-treatment and/or post-treatment composition comprising at least one aminosilicone as defined above is left to act on the hair, at room temperature or under heat, for a period of time ranging from, for example, 1 to 60 minutes, such as from 3 to 30 minutes.
  • According to an option in the process, the hair impregnated with the pre-treatment composition comprising at least one aminosilicone as defined above can be rinsed, wherein the rinsing may be carried out using water.
  • In the process, a reducing composition is applied to the hair, wherein the reducing composition may comprise at least one thiol.
  • The thiol in the reducing composition may be chosen from thiols known as reducing agents such as thioglycolic acid, glyceryl and glycol monothioglycolate, cysteamine and its C1-C4 acyl derivatives such as N-acetylcysteamine or N-propionyl-cysteamine, cysteine, N-acetylcysteine, sugar N-mercaptoalkylamides such as N-(2-mercaptoethyl)gluconamide, 3-mercaptopropionic acid and its derivatives, thiolactic acid and its esters such as glyceryl monothiolactate, thiomalic acid, pantethine, thioglycerol, alkali metal and alkaline-earth metal sulphites and bisulphites, the N-(mercaptoalkyl)-ω-hydroxyalkylamides described in patent application EP-A-354 835 and the N-mono- or N,N-dialkylmercapto-4-butyramides described in patent application EP-A-368 763, the aminomercaptoalkylamides described in patent application EP-A432 000, the N-(mercaptoalkyl)succinamic acid and N-(mercaptoalkyl)succinimide derivatives described in patent application EP-A465 342, the alkylaminomercaptoalkylamides described in patent application EP-A-514 282, and the mixture of 2-hydroxypropyl thioglycolate and of 2-hydroxy-1-methylethyl thioglycolate described in patent application FR-A-2 679 448.
  • In one embodiment, thioglycolic acid, thiolactic acid and 3-mercaptopropionic acid are chosen for use.
  • The reducing agents may be present in a concentration that may range, for example, from 1% to 20% by weight relative to the total weight of the reducing composition.
  • The pH of the reducing composition may range, for example, from 6 to 10, and further, for example, from 7 to 9.
  • The pH values of the reducing compositions may be conventionally adjusted by adding at least one basifying agent. Non-limiting examples of such basifying agents include, for example, aqueous ammonia, monoethanolamine, diethanolamine, triethanolamine, isopropanolamine, 1,3-propanediamine, ammonium and alkali metal carbonates and bicarbonates, primary, secondary and tertiary amine carbonates and bicarbonates and organic carbonates such as guanidine carbonate.
  • The reducing composition may be in the form of a thickened or unthickened lotion, a cream, a gel, or any other suitable form, and may comprise additives known for their use in reducing compositions for permanently reshaping the hair.
  • The reducing composition may also be of the exothermic type, i.e., the type causing a certain level of heating during application to the hair, affording a pleasant sensation to the person on whom the permanent-waving or straightening process is being performed.
  • The reducing composition may also comprise a solvent such as, ethanol, propanol, isopropanol and glycerol, in a maximum concentration of 20% by weight relative to the total weight of the composition.
  • When the compositions are intended for a hair straightening or relaxing process, the reducing composition may be, for example, 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, for example based on glyceryl stearate, glycol stearate, self-emulsifiable waxes, fatty alcohols, etc.
  • It is also possible to use liquids or gels containing thickeners such as carboxyvinyl polymers or copolymers, which can “stick” the hairs together and keep them in the smooth position during the exposure time.
  • The compositions may also be in a “self-neutralizing” or “self-regulated” form and, in this case, the reducing agents used may be combined with at least one disulphide known for its use in a reducing composition for self-neutralizing permanent waving.
  • In one non-limiting example, the hair onto which the reducing composition has been applied is left to rest for a few minutes, such as ranging from 2 to 40 minutes, and further such as from 5 to 30 minutes, so as to allow the reducing agent sufficient time to act correctly on the hair. This waiting stage may be carried out by leaving the treated hair to rest in the open air (at room temperature or with heating). During this waiting stage, care may be taken to ensure that the hair does not dry out completely but instead remains humid.
  • The hair impregnated with the reducing composition can then be carefully rinsed, for example, with water. Optionally, after rinsing, a heating at high temperature for a few seconds may be carried out.
  • An oxidizing composition can then be applied to the hair thus rinsed, with the aim of fixing the new shape given to the hair. It may also be envisaged to leave the hair to be oxidized by the air.
  • The oxidizing composition comprises an oxidizing agent that may be chosen from aqueous hydrogen peroxide solution, alkali metal bromates, persalts and polythionates. As mentioned previously, one of the advantages of an embodiment of the process disclosed is that it can be entirely suitable in the case of bromate-based oxidizing compositions. The bromate concentration in the oxidizing composition ranges, for example, from 0.1 to2 M.
  • The pH of the oxidizing composition may range, for example, from 2 to 10.
  • As in the case of the application of the reducing composition, the hair onto which the oxidizing composition has been applied is then left for a standing or waiting stage that may last a few minutes, for example, ranging from 3 to 30 minutes and further, for example, from 5 to 15 minutes.
  • The post-treatment composition comprising at least one aminosilicone as defined above is, for example, applied, after rinsing out the oxidizing composition, to wet or dry hair. The hair that has undergone the post-treatment may optionally be dried and/or heated and/or rinsed, before being styled. Where appropriate, the composition may be applied while the hair is maintained by a mechanical device, for example, hairsetting rollers or curlers.
  • Usually, the hair impregnated with the oxidizing composition is rinsed carefully, such as with water. Before or after rinsing, the keratin fibres may be separated from the implement used for placing the keratin fibres under tension.
  • The hair finally obtained can have good cosmetic properties: the hair can be shinier, softer and easier to disentangle or to style.
  • In one embodiment, the pre-treatment and/or post-treatment composition comprising at least one aminosilicone as defined above is applied according to at least one of the following variants:
      • to clean, wet hair, before using the implement for placing the hair under tension, without rinsing the hair before applying the reducing agent; and
      • to wet hair after rinsing out the fixing agent, the hair being subsequently either rinsed and/or dried.
  • When the process for permanently reshaping the hair is a straightening process, it is possible, in a manner that is known per se, to use a straightening agent, such as a thiol agent or an alkaline agent.
  • In the case of a thiol straightening agent, the process may be carried out, for example, by applying the pre-treatment and/or post-treatment composition comprising at least one aminosilicone as defined above according to at least one of the following variants:
      • to clean, wet hair, without rinsing before applying the reducing agent; and
      • to clean, wet hair, after rinsing out the fixing agent, by rinsing before drying the hair.
  • In the case of an alkaline straightening agent, the process may be carried out, for example, by applying the pre-treatment and/or post-treatment composition comprising at least one aminosilicone as defined above to wet hair, after rinsing out neutralizing shampoo, by rinsing before drying the hair.
  • In the case of a hair curling process, the process may give lively curls, and the hair may be at least one of supple, light, silky and well separated.
  • In the case of a hair straightening process, the process, for example, may afford control of the body of the hair, may make the hair smooth from the root to the tip, and may give a more natural feel.
  • The present disclosure may be understood more clearly with the aid of the non-limiting examples which follow, which constitute various embodiments of the process.
  • In the examples, the term “am” means active material.
  • EXAMPLES
  • 1) Protective Care Composition Before Permanent-Waving
    Ingredients % am
    cetylstearyl alcohol/sodium lauryl 12
    sulphate/cetyl myristate/myristyl
    alcohol (62/20/8/10)
    oxyethylenated oleyl alcohol (20 EO) 0.1
    glycerine 0.5
    PDMS containing aminoethylaminobutyl-α,ω-disilanol in 2
    cationic emulsion
    (DC2-8299 from Dow Corning)
    demineralized water qs 100 g

    2) Care Composition for Straightened and Permanent-Waved Hair
  • The composition described in 1) may be used for the care of recently straightened or permanently-waved hair. This composition was applied to wet hair after rinsing out the neutralizing shampoo, or after rinsing out the fixing agent in the case of permanent waving. This composition can make the hair smooth and soft.

Claims (14)

1. A process for permanently reshaping keratin fibres, comprising:
(i) applying a reducing composition to the keratin fibres; and
(ii) oxidizing the keratin fibres,
wherein the process comprises applying to the keratin fibres, before(i) and/or after (ii), a pre-treatment and/or post-treatment cosmetic composition comprising, in a cosmetically acceptable medium, at least one aminosilicone comprising at least one aminoethylimino(C4-C8)alkyl group.
2.-9. (canceled)
10. The process according to claim 1, wherein the at least one aminosilicone has a weight-average molecular mass ranging from 2 000 to 1 000 000.
11. The process according to claim 10, wherein the at least one aminosilicone has a weight-average molecular mass ranging from 3 500 to 200 000.
12. The process according to claim 1, wherein the pH of the pre-treatment and/or post-treatment composition ranges from 2 to 10.
13. The process according to claim 12, wherein the pH of the pre-treatment and/or post-treatment composition ranges from 3 to 9.
14. The process according to claim 1, wherein the concentration of the at least one aminosilicone comprising at least one aminoethylimino(C4-C8)alkyl group in the pre-treatment and/or post-treatment composition ranges from 0.05 to 10% by weight relative to the total weight of the composition.
15. The process according to claim 14, wherein the concentration of the at least one aminosilicone comprising at least one aminoethylimino(C4-C8)alkyl group in the pre-treatment and/or post-treatment composition ranges from 0.1 to 7% by weight relative to the total weight of the composition.
16. The process according to claim 1, wherein the pre-treatment and/or post-treatment composition is left to act on the keratin fibres for a period of time ranging from 1 to 60 minutes.
17. The process according to claim 16, wherein the pre-treatment and/or post-treatment composition is left to act on the keratin fibres for a period of time ranging from 3 to 30 minutes.
18. The process according to claim 1, wherein the pre-treatment and/or post-treatment composition further comprises at least one additive chosen from vitamins and derivatives thereof, provitamins,antioxidants, essential oils, wetting agents, silicone and non-silicone sunscreens, preserving agents, sequestering agents, pearlescent agents, pigments, moisturizers, antidandruff agents, anti-seborrhoeic agents, plasticizers, hydroxy acids, electrolytes, solvents and fragrances.
19-21. (canceled)
22. A kit for permanently reshaping keratin fibres, comprising at least one compartment comprising a pre-treatment and/or post-treatment cosmetic composition comprising at least one aminosilicone comprising at least one aminoethylimino(C4-C8)alkyl group.
23. A pre-treatment and/or post-treatment cosmetic composition for pre-treatment and/or post-treatment in permanent reshaping of keratin fibres comprising, in a cosmetically acceptable medium in said composition, at least one aminosilicone comprising at least one aminoethylimino(C4-C8)alkyl group.
US11/158,014 2001-11-08 2005-06-22 Process for permanently reshaping the hair using particular aminosilicones Abandoned US20050238599A1 (en)

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FR0114479A FR2831805B1 (en) 2001-11-08 2001-11-08 PROCESS FOR PERMANENT DEFORMATION OF HAIR USING PARTICULAR AMINO SILICONES
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013528191A (en) * 2010-06-11 2013-07-08 ユニリーバー・ナームローゼ・ベンノートシヤープ Hair styling composition
US9005593B2 (en) 2009-04-15 2015-04-14 L'oreal Method for shaping the hair using at least one reducing composition, at least one care composition, and heating

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2831804B1 (en) * 2001-11-08 2004-07-30 Oreal PROCESS FOR PERMANENT DEFORMATION OF HAIR USING PARTICULAR AMINO SILICONES
FR2831809B1 (en) * 2001-11-08 2004-07-23 Oreal OXIDIZING COMPOSITION FOR THE TREATMENT OF KERATINIC FIBERS COMPRISING A PARTICULAR AMINO SILICONE
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FR2831805B1 (en) * 2001-11-08 2004-08-06 Oreal PROCESS FOR PERMANENT DEFORMATION OF HAIR USING PARTICULAR AMINO SILICONES
FR2831811B1 (en) * 2001-11-08 2004-07-23 Oreal USE OF PARTICULAR AMINO SILICONES AS A POST TREATMENT OF DIRECT DYES OR OF OXIDATION OF KERATIN FIBERS
FR2831817B1 (en) * 2001-11-08 2003-12-19 Oreal REDUCING COMPOSITION FOR THE TREATMENT OF KERATINIC FIBERS COMPRISING A PARTICULAR AMINO SILICONE
AU2002301803B2 (en) * 2001-11-08 2004-09-09 L'oreal Cosmetic compositions containing an aminosilicone and a conditioner, and uses thereof
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EP1591102A1 (en) * 2004-04-30 2005-11-02 The Procter & Gamble Company Process and kit-of-parts for improved hair conditioning after coloring, bleaching or perming
EP1754517A1 (en) 2005-08-17 2007-02-21 The Procter and Gamble Company A fiber and hair fiber conditioning treatment composition
JP5020761B2 (en) * 2007-03-15 2012-09-05 三洋化成工業株式会社 Cleaning agent for clothing
DE102009027965A1 (en) * 2009-07-23 2011-01-27 Henkel Ag & Co. Kgaa Hair conditioning agents containing selected cationic silicones and a B-series vitamin
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JP5738143B2 (en) * 2011-09-26 2015-06-17 株式会社サニープレイス Hair treatment agent and hair treatment method
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Citations (97)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2047398A (en) * 1930-06-26 1936-07-14 Ig Farbenindustrie Ag Artificial resins and process of making them
US2261002A (en) * 1941-06-17 1941-10-28 Du Pont Organic nitrogen compounds
US2271378A (en) * 1939-08-30 1942-01-27 Du Pont Pest control
US2273780A (en) * 1939-12-30 1942-02-17 Du Pont Wax acryalte ester blends
US2375853A (en) * 1942-10-07 1945-05-15 Du Pont Diamine derivatives
US2528378A (en) * 1947-09-20 1950-10-31 John J Mccabe Jr Metal salts of substituted quaternary hydroxy cycloimidinic acid metal alcoholates and process for preparation of same
US2781354A (en) * 1956-03-26 1957-02-12 John J Mccabe Jr Imidazoline derivatives and process
US2798053A (en) * 1952-09-03 1957-07-02 Goodrich Co B F Carboxylic polymers
US2923692A (en) * 1954-01-25 1960-02-02 Goodrich Co B F Mucilaginous composition comprising salt of crosslinked carboxylic polymer and method of preparing same
US3206462A (en) * 1962-10-31 1965-09-14 Dow Chemical Co Quaternary poly(oxyalkylene)alkylbis(diethylenetriamine) compounds
US3227615A (en) * 1962-05-29 1966-01-04 Hercules Powder Co Ltd Process and composition for the permanent waving of hair
US3472840A (en) * 1965-09-14 1969-10-14 Union Carbide Corp Quaternary nitrogen-containing cellulose ethers
US3632559A (en) * 1967-09-28 1972-01-04 Sandoz Ltd Cationically active water soluble polyamides
US3810977A (en) * 1967-03-23 1974-05-14 Nat Starch Chem Corp Hair fixing composition and process containing a solid terpolymer
US3836537A (en) * 1970-10-07 1974-09-17 Minnesota Mining & Mfg Zwitterionic polymer hairsetting compositions and method of using same
US3874870A (en) * 1973-12-18 1975-04-01 Mill Master Onyx Corp Microbiocidal polymeric quarternary ammonium compounds
US3910862A (en) * 1970-01-30 1975-10-07 Gaf Corp Copolymers of vinyl pyrrolidone containing quarternary ammonium groups
US3912808A (en) * 1970-02-25 1975-10-14 Gillette Co Hair waving and straightening process and composition containing water-soluble amino and quaternary ammonium polymers
US3915921A (en) * 1974-07-02 1975-10-28 Goodrich Co B F Unsaturated carboxylic acid-long chain alkyl ester copolymers and tri-polymers water thickening agents and emulsifiers
US3966904A (en) * 1974-10-03 1976-06-29 Millmaster Onyx Corporation Quaternary ammonium co-polymers for controlling the proliferation of bacteria
US4001432A (en) * 1974-10-29 1977-01-04 Millmaster Onyx Corporation Method of inhibiting the growth of bacteria by the application thereto of capped polymers
US4005193A (en) * 1974-08-07 1977-01-25 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
US4013787A (en) * 1971-11-29 1977-03-22 Societe Anonyme Dite: L'oreal Piperazine based polymer and hair treating composition containing the same
US4025617A (en) * 1974-10-03 1977-05-24 Millmaster Onyx Corporation Anti-microbial quaternary ammonium co-polymers
US4025627A (en) * 1973-12-18 1977-05-24 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
US4025653A (en) * 1975-04-07 1977-05-24 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
US4026945A (en) * 1974-10-03 1977-05-31 Millmaster Onyx Corporation Anti-microbial quaternary ammonium co-polymers
US4027020A (en) * 1974-10-29 1977-05-31 Millmaster Onyx Corporation Randomly terminated capped polymers
US4027008A (en) * 1975-05-14 1977-05-31 The Gillette Company Hair bleaching composition containing water-soluble amino and quaternary ammonium polymers
US4031307A (en) * 1976-05-03 1977-06-21 Celanese Corporation Cationic polygalactomannan compositions
US4070533A (en) * 1974-04-01 1978-01-24 L'oreal Terpolymer of (a) crotonic acid (b) vinyl acetate and (c) allyl or methallyl esters
US4075136A (en) * 1974-01-25 1978-02-21 Calgon Corporation Functional ionene compositions and their use
US4076912A (en) * 1974-04-01 1978-02-28 L'oreal Tetrapolymers comprising (a) unsaturated acids (b) vinyl esters (c) branched allyl or methallyl esters and (d) vinyl ether or vinyl fatty ester or linear allyl or methallyl esters
US4137208A (en) * 1976-05-06 1979-01-30 Berger, Jenson & Nicholson Limited Coating composition
US4157388A (en) * 1977-06-23 1979-06-05 The Miranol Chemical Company, Inc. Hair and fabric conditioning compositions containing polymeric ionenes
US4165367A (en) * 1977-06-10 1979-08-21 Gaf Corporation Hair preparations containing vinyl pyrrolidone copolymer
US4172887A (en) * 1973-11-30 1979-10-30 L'oreal Hair conditioning compositions containing crosslinked polyaminopolyamides
US4217914A (en) * 1974-05-16 1980-08-19 L'oreal Quaternized polymer for use as a cosmetic agent in cosmetic compositions for the hair and skin
US4223009A (en) * 1977-06-10 1980-09-16 Gaf Corporation Hair preparation containing vinyl pyrrolidone copolymer
US4277581A (en) * 1973-11-30 1981-07-07 L'oreal Polyamino-polyamide crosslinked with crosslinking agent
US4282203A (en) * 1978-10-27 1981-08-04 L'oreal Hair lacquer and hair lotion compositions containing a copolymer having units of a vinyl allyl or methally ester of an α- or β-cyclic carboxylic acid
US4349532A (en) * 1977-09-20 1982-09-14 Guy Vanlerberghe Cosmetic compositions based on poly-(quaternary ammonium) polymers
US4509949A (en) * 1983-06-13 1985-04-09 The B. F. Goodrich Company Water thickening agents consisting of copolymers of crosslinked acrylic acids and esters
US4591610A (en) * 1983-03-23 1986-05-27 L'oreal Thickened or gelled composition for conditioning hair
US4608250A (en) * 1975-07-04 1986-08-26 Societe Anonyme Dite: L'oreal Quaternized polymers; process for preparing the same; and cosmetic compositions containing the same
US4673568A (en) * 1984-04-13 1987-06-16 L'oreal Hair-care composition and hair treatment process
US4693935A (en) * 1986-05-19 1987-09-15 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer pressure sensitive adhesive composition and sheet materials coated therewith
US4702906A (en) * 1979-12-21 1987-10-27 Societe Anonyme Dite: L'oreal Cosmetic agents based on polycationic polymers, and their use in cosmetic compositions
US4719282A (en) * 1986-04-22 1988-01-12 Miranol Inc. Polycationic block copolymer
US4719099A (en) * 1977-03-15 1988-01-12 L'oreal Composition and process for the treatment of keratin materials with polymers
US4728571A (en) * 1985-07-19 1988-03-01 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer release coating sheets and adhesive tapes
US4761273A (en) * 1981-05-08 1988-08-02 L'oreal Composition in the form of an aerosol foam, based on a cationic polymer and an anionic polymer
US4770873A (en) * 1983-06-15 1988-09-13 Clairol, Incorporated Neutralizing composition and method for hair waving and straightening
US4839166A (en) * 1986-05-16 1989-06-13 L'oreal Cosmestic compositions containing a cationic polymer and an anionic polymer as thickening agent
US4957732A (en) * 1988-12-29 1990-09-18 L'oreal Shaving composition for the skin based on polyorgano-siloxanes containing an acyloxyalkyl group and process for use
US4996059A (en) * 1979-11-28 1991-02-26 L'oreal Composition for the treatment of keratin fibers, based on amphoteric polymer and cationic polymer
US5057311A (en) * 1988-04-12 1991-10-15 Kao Corporation Low-irritation detergent composition
US5061289A (en) * 1988-12-24 1991-10-29 Wella Aktiengesellschaft Oxidation hair dye composition containinng diaminopyrazol derivatives and new diaminopyrazol derivatives
US5085860A (en) * 1989-11-20 1992-02-04 L'oreal Reducing composition for the permanent deformation of hair containing as a reducing agent, an amino mercaptoalkylamide or a salt thereof
US5089252A (en) * 1982-01-15 1992-02-18 L'oreal Cosmetic composition for treating keratin fibres, and process for treating the latter
US5106612A (en) * 1988-08-04 1992-04-21 Societe Anonyme Dite: L'oreal N-(mercaptoalkyl)ω-hydroxyalkylamides and their use as a reducing agent in a process for permanently deforming hair
US5139037A (en) * 1982-01-15 1992-08-18 L'oreal Cosmetic composition for treating keratin fibres, and process for treating the latter
US5196189A (en) * 1974-05-16 1993-03-23 Societe Anonyme Dite: L'oreal Quaternized polymer for use as a cosmetic agent in cosmetic compositions for the hair and skin
US5210324A (en) * 1985-08-12 1993-05-11 Allied Colloids Limited Monomer production
US5340367A (en) * 1993-02-11 1994-08-23 Shiseido Co. Ltd. Permanent waving and color enhancing composition and method
US5344464A (en) * 1988-09-08 1994-09-06 L'oreal Oxidation dye composition containing at least one double base in combination with at least one single base and dyeing process making use of it
US5380340A (en) * 1991-10-14 1995-01-10 Wella Aktiengesellschaft Hair dye containing aminopyrazole derivatives as well as pyrazole derivatives
US5534267A (en) * 1992-10-16 1996-07-09 Wella Aktiengesellschaft Composition for the oxidative dyeing of hair containing 4,5-diaminopyrazole derivatives as well as new 4,5-diaminopyrazole derivatives and process for their synthesis
US5538717A (en) * 1993-10-15 1996-07-23 L'oreal Aqueous nail polish containing as film-forming substance particles of polyester-polyurethane which are anionic in dispersion
US5626840A (en) * 1993-04-06 1997-05-06 National Starch And Chemical Investment Holding Corporation Use of polyurethanes with carboxylate functionality for hair fixative applications
US5663366A (en) * 1992-10-16 1997-09-02 Wella Aktiengesellschat Process for the synthesis of 4,5-diaminopyrazole derivatives useful for dyeing hair
US5708151A (en) * 1994-11-03 1998-01-13 Ciba Specialty Chemicals Corporation Cationic imidazole azo dyes
US5741337A (en) * 1994-05-09 1998-04-21 L'oreal Process for the oxidative dyeing of keratinous fibres with a composition which contains an oxidation dye precursor, a coupler, and an oxidant at an acidic pH
US5756076A (en) * 1995-09-07 1998-05-26 L'oreal Conditioning composition and detergent for use on hair
US5766576A (en) * 1995-11-25 1998-06-16 Wella Aktiengesellschaft Oxidation hair dye compositions containing 3,4,5-triaminopyrazole derivatives and 3,4,5-triaminopyrazole derivatives
US5773611A (en) * 1991-02-21 1998-06-30 L'oreal Ceramides, process for their preparation and their applications in the cosmetic and dermopharmaceutical fields
US5925341A (en) * 1997-03-18 1999-07-20 L'oreal Nanoemulsion based on nonionic amphiphilic lipids and aminated silicones and uses
US6010541A (en) * 1996-07-23 2000-01-04 L'oreal Oxidation dye composition for keratin fibers comprising a nonionic amphiphilic polymer
US6071504A (en) * 1997-07-09 2000-06-06 Kao Corporation Hair treatment composition comprising alkalizing agent
US6099592A (en) * 1995-05-05 2000-08-08 L'oreal Composition for dyeing keratin fibers which contain at least one diaminopyrazole, dyeing process, novel diaminopyrazoles and process for their preparation
US6099593A (en) * 1996-06-21 2000-08-08 L'oreal Compositions for dyeing keratin fibers containing pyrazolo(1,5-a)pyrimidine derivatives and dyeing processes
US6177090B1 (en) * 1995-09-29 2001-01-23 L'oreal Topical composition containing a silicone-grafted polymer and an amine silicone and/or a silicone gum or resin
US6179881B1 (en) * 1997-11-21 2001-01-30 L'oreal Compositions and processes for dyeing keratin fibers with azo compounds
US6214326B1 (en) * 1998-06-15 2001-04-10 L'oreal Cosmetic composition containing a cationic polymer and an acrylic terpolymer, and use of this composition for the treatment of keratinous material
US6254646B1 (en) * 1997-10-03 2001-07-03 L'oreal S.A. Oxidizing composition and uses for dyeing, permanently setting or bleaching keratin fibres
US6260556B1 (en) * 1999-01-29 2001-07-17 L'oreal Anhydrous composition for bleaching keratin fibers
US6284003B1 (en) * 1994-11-17 2001-09-04 Henkel Kommanditgesellschaft Auf Aktien Oxidation colorants comprising 2-(2,5-diaminophenyl)-ethanol compounds and 2-chloro-6-methyl-3-aminophenol compounds
US20020006389A1 (en) * 1998-07-23 2002-01-17 Serge Restle Detergent cosmetic compositions and use
US6372876B1 (en) * 1992-07-29 2002-04-16 Basf Aktiengesellschaft Use of polyurethanes which are soluble or dispersible in water as aids in cosmetic and pharmaceutical compositions, and polyurethanes which contain polylactic acid polyols as copolymerized units
US6395265B1 (en) * 1996-01-05 2002-05-28 L'oreal Cosmetic compositions containing multi-block ionizable polysiloxane/polyurethane and/or polyurea polycondensates in solution, and uses thereof
US6506373B1 (en) * 1998-11-14 2003-01-14 Wella Aktiengesellschaft Agent and method for permanent waving
US6511669B1 (en) * 1999-02-16 2003-01-28 L'oreal S.A. Cosmetic compositions containing an anionic hydroxyalkyl ether surfactant and a cationic polymer, and uses thereof
US6582477B1 (en) * 1999-04-07 2003-06-24 L'oreal S.A. Oxidation dyeing process using a ketose as reducing agent and a laccase as oxidizing agent
US6613313B2 (en) * 1997-11-28 2003-09-02 Fuji Photo Film Co., Ltd. Aniline compound-containing hair dye composition and method of dyeing hair
US6770271B2 (en) * 1993-08-04 2004-08-03 L'oreal Polyester polyurethanes, process for preparing them, pseudolatices produced from the said polyester polyurethanes and their use in cosmetic compositions
US6846333B2 (en) * 2001-11-08 2005-01-25 L'oreal, S.A. Keratin fiber dyeing composition comprising a particular aminosilicone
US6916467B2 (en) * 2001-11-08 2005-07-12 L'oreal S.A. Process for permanently reshaping the hair using particular aminosilicones

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1229305A (en) * 1983-06-15 1987-11-17 Leszek J. Wolfram Neutralizing composition and method for hair waving and straightening
LU87378A1 (en) 1988-11-09 1990-06-12 Oreal MERCAPTO-4 BUTYRAMIDES N-MONO OR N, N-DISUBSTITUTED BY A MONO OR POLYHYDROXYALKYL RADICAL, AND THEIR USE AS REDUCING AGENTS IN A PERMANENT HAIR DEFORMATION PROCESS
FR2663845B1 (en) 1990-07-02 1994-01-07 Oreal REDUCING COSMETIC COMPOSITION FOR PERMANENT CONTAINING N- (MERCAPTO ALKYL) SUCCINAMIC ACID OR N- (MERCAPTO ALKYL) SUCCINIMIDE DERIVATIVE, AND ITS USE IN A PERMANENT HAIR DEFORMATION PROCESS.
JP2925705B2 (en) 1990-10-15 1999-07-28 株式会社成和化成 1st agent for permanent wave
FR2676441B1 (en) 1991-05-17 1994-10-28 Oreal NOVEL ALKYLAMINO-MERCAPTOALKYLAMIDES OR ONE OF THEIR COSMETICALLY ACCEPTABLE SALTS, AND THEIR USE AS REDUCING AGENTS, IN A PROCESS OF PERMANENT HAIR DEFORMATION.
FR2679558B1 (en) 1991-07-25 1993-09-24 Rhone Poulenc Rorer Sa PROCESS FOR THE PREPARATION OF CINNAMOYL-13ALPHA BACCATIN III OR DESACETYL-10 BACCATIN III.
JP3446980B2 (en) 1994-12-08 2003-09-16 株式会社成和化成 Hair cosmetics
JPH09151120A (en) * 1995-11-30 1997-06-10 Toshiba Silicone Co Ltd Permanent waving agent
JP3926063B2 (en) 1999-06-29 2007-06-06 ホーユー株式会社 Permanent wave pretreatment composition and method of using the same
FR2823110B1 (en) 2001-04-06 2004-03-05 Oreal PROCESS FOR PERMANENT DEFORMATION OF HAIR USING AMINO SILICONES
FR2829383B1 (en) * 2001-09-11 2005-09-23 Oreal COSMETIC COMPOSITIONS CONTAINING A METHACRYLIC ACID COPOLYMER, A SILICONE AND A CATIONIC POLYMER AND USES THEREOF

Patent Citations (99)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2047398A (en) * 1930-06-26 1936-07-14 Ig Farbenindustrie Ag Artificial resins and process of making them
US2271378A (en) * 1939-08-30 1942-01-27 Du Pont Pest control
US2273780A (en) * 1939-12-30 1942-02-17 Du Pont Wax acryalte ester blends
US2261002A (en) * 1941-06-17 1941-10-28 Du Pont Organic nitrogen compounds
US2375853A (en) * 1942-10-07 1945-05-15 Du Pont Diamine derivatives
US2528378A (en) * 1947-09-20 1950-10-31 John J Mccabe Jr Metal salts of substituted quaternary hydroxy cycloimidinic acid metal alcoholates and process for preparation of same
US2798053A (en) * 1952-09-03 1957-07-02 Goodrich Co B F Carboxylic polymers
US2923692A (en) * 1954-01-25 1960-02-02 Goodrich Co B F Mucilaginous composition comprising salt of crosslinked carboxylic polymer and method of preparing same
US2781354A (en) * 1956-03-26 1957-02-12 John J Mccabe Jr Imidazoline derivatives and process
US3227615A (en) * 1962-05-29 1966-01-04 Hercules Powder Co Ltd Process and composition for the permanent waving of hair
US3206462A (en) * 1962-10-31 1965-09-14 Dow Chemical Co Quaternary poly(oxyalkylene)alkylbis(diethylenetriamine) compounds
US3472840A (en) * 1965-09-14 1969-10-14 Union Carbide Corp Quaternary nitrogen-containing cellulose ethers
US3810977A (en) * 1967-03-23 1974-05-14 Nat Starch Chem Corp Hair fixing composition and process containing a solid terpolymer
US3632559A (en) * 1967-09-28 1972-01-04 Sandoz Ltd Cationically active water soluble polyamides
US3910862A (en) * 1970-01-30 1975-10-07 Gaf Corp Copolymers of vinyl pyrrolidone containing quarternary ammonium groups
US3912808A (en) * 1970-02-25 1975-10-14 Gillette Co Hair waving and straightening process and composition containing water-soluble amino and quaternary ammonium polymers
US3836537A (en) * 1970-10-07 1974-09-17 Minnesota Mining & Mfg Zwitterionic polymer hairsetting compositions and method of using same
US4013787A (en) * 1971-11-29 1977-03-22 Societe Anonyme Dite: L'oreal Piperazine based polymer and hair treating composition containing the same
US4172887A (en) * 1973-11-30 1979-10-30 L'oreal Hair conditioning compositions containing crosslinked polyaminopolyamides
US4277581A (en) * 1973-11-30 1981-07-07 L'oreal Polyamino-polyamide crosslinked with crosslinking agent
US4025627A (en) * 1973-12-18 1977-05-24 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
US3874870A (en) * 1973-12-18 1975-04-01 Mill Master Onyx Corp Microbiocidal polymeric quarternary ammonium compounds
US4075136A (en) * 1974-01-25 1978-02-21 Calgon Corporation Functional ionene compositions and their use
US4070533A (en) * 1974-04-01 1978-01-24 L'oreal Terpolymer of (a) crotonic acid (b) vinyl acetate and (c) allyl or methallyl esters
US4076912A (en) * 1974-04-01 1978-02-28 L'oreal Tetrapolymers comprising (a) unsaturated acids (b) vinyl esters (c) branched allyl or methallyl esters and (d) vinyl ether or vinyl fatty ester or linear allyl or methallyl esters
US4217914A (en) * 1974-05-16 1980-08-19 L'oreal Quaternized polymer for use as a cosmetic agent in cosmetic compositions for the hair and skin
US5196189A (en) * 1974-05-16 1993-03-23 Societe Anonyme Dite: L'oreal Quaternized polymer for use as a cosmetic agent in cosmetic compositions for the hair and skin
US3915921A (en) * 1974-07-02 1975-10-28 Goodrich Co B F Unsaturated carboxylic acid-long chain alkyl ester copolymers and tri-polymers water thickening agents and emulsifiers
US4005193A (en) * 1974-08-07 1977-01-25 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
US4025617A (en) * 1974-10-03 1977-05-24 Millmaster Onyx Corporation Anti-microbial quaternary ammonium co-polymers
US3966904A (en) * 1974-10-03 1976-06-29 Millmaster Onyx Corporation Quaternary ammonium co-polymers for controlling the proliferation of bacteria
US4026945A (en) * 1974-10-03 1977-05-31 Millmaster Onyx Corporation Anti-microbial quaternary ammonium co-polymers
US4027020A (en) * 1974-10-29 1977-05-31 Millmaster Onyx Corporation Randomly terminated capped polymers
US4001432A (en) * 1974-10-29 1977-01-04 Millmaster Onyx Corporation Method of inhibiting the growth of bacteria by the application thereto of capped polymers
US4025653A (en) * 1975-04-07 1977-05-24 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
US4027008A (en) * 1975-05-14 1977-05-31 The Gillette Company Hair bleaching composition containing water-soluble amino and quaternary ammonium polymers
US4608250A (en) * 1975-07-04 1986-08-26 Societe Anonyme Dite: L'oreal Quaternized polymers; process for preparing the same; and cosmetic compositions containing the same
US4031307A (en) * 1976-05-03 1977-06-21 Celanese Corporation Cationic polygalactomannan compositions
US4137208A (en) * 1976-05-06 1979-01-30 Berger, Jenson & Nicholson Limited Coating composition
US4719099A (en) * 1977-03-15 1988-01-12 L'oreal Composition and process for the treatment of keratin materials with polymers
US5009880A (en) * 1977-03-15 1991-04-23 L'oreal Composition and process for the treatment of keratin materials with polymers
US4223009A (en) * 1977-06-10 1980-09-16 Gaf Corporation Hair preparation containing vinyl pyrrolidone copolymer
US4165367A (en) * 1977-06-10 1979-08-21 Gaf Corporation Hair preparations containing vinyl pyrrolidone copolymer
US4157388A (en) * 1977-06-23 1979-06-05 The Miranol Chemical Company, Inc. Hair and fabric conditioning compositions containing polymeric ionenes
US4349532A (en) * 1977-09-20 1982-09-14 Guy Vanlerberghe Cosmetic compositions based on poly-(quaternary ammonium) polymers
US4282203A (en) * 1978-10-27 1981-08-04 L'oreal Hair lacquer and hair lotion compositions containing a copolymer having units of a vinyl allyl or methally ester of an α- or β-cyclic carboxylic acid
US5958392A (en) * 1979-11-28 1999-09-28 L'oreal Composition for the treatment of keratin fibers, based on amphoteric polymers and cationic polymers
US4996059A (en) * 1979-11-28 1991-02-26 L'oreal Composition for the treatment of keratin fibers, based on amphoteric polymer and cationic polymer
US4702906A (en) * 1979-12-21 1987-10-27 Societe Anonyme Dite: L'oreal Cosmetic agents based on polycationic polymers, and their use in cosmetic compositions
US4761273A (en) * 1981-05-08 1988-08-02 L'oreal Composition in the form of an aerosol foam, based on a cationic polymer and an anionic polymer
US5139037A (en) * 1982-01-15 1992-08-18 L'oreal Cosmetic composition for treating keratin fibres, and process for treating the latter
US5089252A (en) * 1982-01-15 1992-02-18 L'oreal Cosmetic composition for treating keratin fibres, and process for treating the latter
US4591610A (en) * 1983-03-23 1986-05-27 L'oreal Thickened or gelled composition for conditioning hair
US4509949A (en) * 1983-06-13 1985-04-09 The B. F. Goodrich Company Water thickening agents consisting of copolymers of crosslinked acrylic acids and esters
US4770873A (en) * 1983-06-15 1988-09-13 Clairol, Incorporated Neutralizing composition and method for hair waving and straightening
US4673568A (en) * 1984-04-13 1987-06-16 L'oreal Hair-care composition and hair treatment process
US4728571A (en) * 1985-07-19 1988-03-01 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer release coating sheets and adhesive tapes
US5210324A (en) * 1985-08-12 1993-05-11 Allied Colloids Limited Monomer production
US4719282A (en) * 1986-04-22 1988-01-12 Miranol Inc. Polycationic block copolymer
US4839166A (en) * 1986-05-16 1989-06-13 L'oreal Cosmestic compositions containing a cationic polymer and an anionic polymer as thickening agent
US4693935A (en) * 1986-05-19 1987-09-15 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer pressure sensitive adhesive composition and sheet materials coated therewith
US5057311A (en) * 1988-04-12 1991-10-15 Kao Corporation Low-irritation detergent composition
US5106612A (en) * 1988-08-04 1992-04-21 Societe Anonyme Dite: L'oreal N-(mercaptoalkyl)ω-hydroxyalkylamides and their use as a reducing agent in a process for permanently deforming hair
US5344464A (en) * 1988-09-08 1994-09-06 L'oreal Oxidation dye composition containing at least one double base in combination with at least one single base and dyeing process making use of it
US5061289A (en) * 1988-12-24 1991-10-29 Wella Aktiengesellschaft Oxidation hair dye composition containinng diaminopyrazol derivatives and new diaminopyrazol derivatives
US4957732A (en) * 1988-12-29 1990-09-18 L'oreal Shaving composition for the skin based on polyorgano-siloxanes containing an acyloxyalkyl group and process for use
US5085860A (en) * 1989-11-20 1992-02-04 L'oreal Reducing composition for the permanent deformation of hair containing as a reducing agent, an amino mercaptoalkylamide or a salt thereof
US5773611A (en) * 1991-02-21 1998-06-30 L'oreal Ceramides, process for their preparation and their applications in the cosmetic and dermopharmaceutical fields
US5380340A (en) * 1991-10-14 1995-01-10 Wella Aktiengesellschaft Hair dye containing aminopyrazole derivatives as well as pyrazole derivatives
US6372876B1 (en) * 1992-07-29 2002-04-16 Basf Aktiengesellschaft Use of polyurethanes which are soluble or dispersible in water as aids in cosmetic and pharmaceutical compositions, and polyurethanes which contain polylactic acid polyols as copolymerized units
US5534267A (en) * 1992-10-16 1996-07-09 Wella Aktiengesellschaft Composition for the oxidative dyeing of hair containing 4,5-diaminopyrazole derivatives as well as new 4,5-diaminopyrazole derivatives and process for their synthesis
US5663366A (en) * 1992-10-16 1997-09-02 Wella Aktiengesellschat Process for the synthesis of 4,5-diaminopyrazole derivatives useful for dyeing hair
US5340367A (en) * 1993-02-11 1994-08-23 Shiseido Co. Ltd. Permanent waving and color enhancing composition and method
US5626840A (en) * 1993-04-06 1997-05-06 National Starch And Chemical Investment Holding Corporation Use of polyurethanes with carboxylate functionality for hair fixative applications
US6770271B2 (en) * 1993-08-04 2004-08-03 L'oreal Polyester polyurethanes, process for preparing them, pseudolatices produced from the said polyester polyurethanes and their use in cosmetic compositions
US5538717A (en) * 1993-10-15 1996-07-23 L'oreal Aqueous nail polish containing as film-forming substance particles of polyester-polyurethane which are anionic in dispersion
US5741337A (en) * 1994-05-09 1998-04-21 L'oreal Process for the oxidative dyeing of keratinous fibres with a composition which contains an oxidation dye precursor, a coupler, and an oxidant at an acidic pH
US5708151A (en) * 1994-11-03 1998-01-13 Ciba Specialty Chemicals Corporation Cationic imidazole azo dyes
US6284003B1 (en) * 1994-11-17 2001-09-04 Henkel Kommanditgesellschaft Auf Aktien Oxidation colorants comprising 2-(2,5-diaminophenyl)-ethanol compounds and 2-chloro-6-methyl-3-aminophenol compounds
US6099592A (en) * 1995-05-05 2000-08-08 L'oreal Composition for dyeing keratin fibers which contain at least one diaminopyrazole, dyeing process, novel diaminopyrazoles and process for their preparation
US5756076A (en) * 1995-09-07 1998-05-26 L'oreal Conditioning composition and detergent for use on hair
US6177090B1 (en) * 1995-09-29 2001-01-23 L'oreal Topical composition containing a silicone-grafted polymer and an amine silicone and/or a silicone gum or resin
US5766576A (en) * 1995-11-25 1998-06-16 Wella Aktiengesellschaft Oxidation hair dye compositions containing 3,4,5-triaminopyrazole derivatives and 3,4,5-triaminopyrazole derivatives
US6395265B1 (en) * 1996-01-05 2002-05-28 L'oreal Cosmetic compositions containing multi-block ionizable polysiloxane/polyurethane and/or polyurea polycondensates in solution, and uses thereof
US6099593A (en) * 1996-06-21 2000-08-08 L'oreal Compositions for dyeing keratin fibers containing pyrazolo(1,5-a)pyrimidine derivatives and dyeing processes
US6010541A (en) * 1996-07-23 2000-01-04 L'oreal Oxidation dye composition for keratin fibers comprising a nonionic amphiphilic polymer
US5925341A (en) * 1997-03-18 1999-07-20 L'oreal Nanoemulsion based on nonionic amphiphilic lipids and aminated silicones and uses
US6071504A (en) * 1997-07-09 2000-06-06 Kao Corporation Hair treatment composition comprising alkalizing agent
US6254646B1 (en) * 1997-10-03 2001-07-03 L'oreal S.A. Oxidizing composition and uses for dyeing, permanently setting or bleaching keratin fibres
US6179881B1 (en) * 1997-11-21 2001-01-30 L'oreal Compositions and processes for dyeing keratin fibers with azo compounds
US6613313B2 (en) * 1997-11-28 2003-09-02 Fuji Photo Film Co., Ltd. Aniline compound-containing hair dye composition and method of dyeing hair
US6214326B1 (en) * 1998-06-15 2001-04-10 L'oreal Cosmetic composition containing a cationic polymer and an acrylic terpolymer, and use of this composition for the treatment of keratinous material
US20020006389A1 (en) * 1998-07-23 2002-01-17 Serge Restle Detergent cosmetic compositions and use
US6506373B1 (en) * 1998-11-14 2003-01-14 Wella Aktiengesellschaft Agent and method for permanent waving
US6260556B1 (en) * 1999-01-29 2001-07-17 L'oreal Anhydrous composition for bleaching keratin fibers
US6511669B1 (en) * 1999-02-16 2003-01-28 L'oreal S.A. Cosmetic compositions containing an anionic hydroxyalkyl ether surfactant and a cationic polymer, and uses thereof
US6582477B1 (en) * 1999-04-07 2003-06-24 L'oreal S.A. Oxidation dyeing process using a ketose as reducing agent and a laccase as oxidizing agent
US6846333B2 (en) * 2001-11-08 2005-01-25 L'oreal, S.A. Keratin fiber dyeing composition comprising a particular aminosilicone
US6916467B2 (en) * 2001-11-08 2005-07-12 L'oreal S.A. Process for permanently reshaping the hair using particular aminosilicones

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9005593B2 (en) 2009-04-15 2015-04-14 L'oreal Method for shaping the hair using at least one reducing composition, at least one care composition, and heating
JP2013528191A (en) * 2010-06-11 2013-07-08 ユニリーバー・ナームローゼ・ベンノートシヤープ Hair styling composition

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