US20170095408A9 - Method for treating hair fibers - Google Patents

Method for treating hair fibers Download PDF

Info

Publication number
US20170095408A9
US20170095408A9 US13/541,117 US201213541117A US2017095408A9 US 20170095408 A9 US20170095408 A9 US 20170095408A9 US 201213541117 A US201213541117 A US 201213541117A US 2017095408 A9 US2017095408 A9 US 2017095408A9
Authority
US
United States
Prior art keywords
reducing composition
hair fibers
reducing
hair
chosen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
US13/541,117
Other versions
US9675822B2 (en
US20130000661A1 (en
Inventor
Thomas Fondin
Anne Sabbagh
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=35096497&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US20170095408(A9) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by LOreal SA filed Critical LOreal SA
Priority to US13/541,117 priority Critical patent/US9675822B2/en
Publication of US20130000661A1 publication Critical patent/US20130000661A1/en
Publication of US20170095408A9 publication Critical patent/US20170095408A9/en
Priority to US15/584,472 priority patent/US10702464B2/en
Application granted granted Critical
Publication of US9675822B2 publication Critical patent/US9675822B2/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • 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
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • AHUMAN NECESSITIES
    • A45HAND OR TRAVELLING ARTICLES
    • A45DHAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
    • A45D1/00Curling-tongs, i.e. tongs for use when hot; Curling-irons, i.e. irons for use when hot; Accessories therefor
    • A45D1/02Curling-tongs, i.e. tongs for use when hot; Curling-irons, i.e. irons for use when hot; Accessories therefor with means for internal heating, e.g. by liquid fuel
    • A45D1/04Curling-tongs, i.e. tongs for use when hot; Curling-irons, i.e. irons for use when hot; Accessories therefor with means for internal heating, e.g. by liquid fuel by electricity
    • AHUMAN NECESSITIES
    • A45HAND OR TRAVELLING ARTICLES
    • A45DHAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
    • A45D7/00Processes of waving, straightening or curling hair
    • A45D7/02Processes of waving, straightening or curling hair thermal
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/12Preparations containing hair conditioners

Definitions

  • Disclosed herein is a method for treating hair fibers by applying a reducing composition and then heating the hair with a heating iron.
  • the usual practice to permanently reshape hair comprises first opening the keratin disulfide bonds (cystine) with a composition comprising a reducing agent.
  • the disulfide bonds are then re-formed, optionally after rinsing the hair, by applying to the hair, which has been straightened or placed beforehand under tension with suitable means such as curlers or the equivalent, an oxidizing composition also called a fixing solution, so as to give the desired form to the hair.
  • an oxidizing composition also called a fixing solution
  • Reducing compositions that can be used to carry out the first step of this method generally comprise compounds comprising a thiol group, such as thioglycolic acid, cysteine, cysteamine, thiolactic acid, and glycerol monothioglycolate.
  • a thiol group such as thioglycolic acid, cysteine, cysteamine, thiolactic acid, and glycerol monothioglycolate.
  • the reducing agent concentration may be very high, often up to 15% by weight, relative to the total weight of the reducing composition.
  • Patent Application No. JP 2000 256 146 describes a process to permanently reshape the hair, comprising the application of a cosmetic composition comprising from 2 to 11% reducing agents and from 0.2 to 4% diammonium dithiodiglycolate. After the reducing composition is applied, a heating iron is used at a temperature from 60 to 220° C.
  • the resulting shape is irreversible.
  • the difference between the parts of the hair that have been treated and the hair roots is very noticeable as the hair regrows.
  • a hair fiber treating method that compensates for at least one of the drawbacks of the prior art.
  • Such a method would also ideally preserve the natural aspect of the hair so as to limit the so-called ‘root effect’, that is to say the contrast between the parts which have been treated and the roots, and also ideally reduce the hair fiber treating time and obtain long-lasting results.
  • the present inventors have found that it is possible to counteract at least one of the drawbacks of the prior art and to achieve at least one of the desirable results listed above, by carrying out a hair fiber treating method without fixing the hair, comprising applying to the hair fibers at least one reducing composition comprising at least one reducing agent chosen from compounds comprising at least one thiol group, wherein the at least one reducing agent is present in an amount of less than 3% by weight, relative to the total weight of the at least one reducing composition, and wherein the at least one reducing composition does not comprise an aminothiol compound or if the composition does comprise at least one aminothiol compound, it is present in an amount of less than 5% by weight, relative to the total weight of the at least one reducing composition, and raising the temperature of the hair fiber using a heating iron at a temperature of at least 60° C., wherein the temperature of the hair fiber is raised before or after the hair fibers are optionally rinsed.
  • a method of treating hair fibers without fixing the hair comprising:
  • ‘without fixing the hair’ or ‘without a hair-fixing step’ means without any additional application of a composition comprising a chemical oxidizing agent, such as hydrogen peroxide or a bromate.
  • a chemical oxidizing agent such as hydrogen peroxide or a bromate.
  • the at least one reducing composition may have a pH of less than or equal to 9, provided that the at least one reducing composition does not comprise an aminothiol compound.
  • the at least one reducing composition does not comprise dithiodiglycolic acid or any salt thereof.
  • the at least one reducing composition may, for example, be applied onto wet and clean hair fibers.
  • aminothiol compound means a thiol comprising at least one NH moiety.
  • the thiols used as the at least one reducing agent may, for example, be chosen from aminothiols, such as cysteine and derivatives thereof, i.e., N-acetylcysteine, cysteamine and derivatives thereof, C 1 -C 4 acylated derivatives thereof, such as N-acetyl cysteamine and N-propionyl cysteamine, and non-aminated thiols, such as thiolactic acid and esters thereof, such as glycerol monothiolactate, thioglycolic acid and esters thereof, such as glycerol and glycol monothioglycolate, and thioglycerol.
  • aminothiols such as cysteine and derivatives thereof, i.e., N-acetylcysteine, cysteamine and derivatives thereof, C 1 -C 4 acylated derivatives thereof, such as N-acetyl cysteamine and N-propionyl cysteamine
  • the thiol may be provided, if needed, in the form of at least one salt thereof, such as alkali metal or ammonium salts. In one embodiment, ammonium thioglycolate may be used.
  • the thiol may be provided, if needed, in the form of at least one salt thereof, such as aminothiol halogenides.
  • L-cysteine hydrochloride may be used.
  • aminothiols examples include sugar N-mercapto-alkyl amides, such as N-(mercapto-2-ethyl)-gluconamide, pantheteine, and N-(mercaptoalkyl)- ⁇ -hydroxyalkyl amides such as those described in Patent Application No. EP-A-354 835 and N-mono- and N,N-dialkylmercapto 4-butyramides, such as those described Patent Application No. EP-A-368 763, aminomercaptoalkyl amides, such as those described Patent Application No. EP-A-432 000 and alkylaminomercaptoalkyl amides such as those described in Patent Application No. EP-A-514 282.
  • sugar N-mercapto-alkyl amides such as N-(mercapto-2-ethyl)-gluconamide, pantheteine
  • N-(mercaptoalkyl)- ⁇ -hydroxyalkyl amides such as those described in Patent Application No. EP-A-3
  • non-aminated thiols examples include a mixture of hydroxy-2-propyl thioglycolate (2/3) and hydroxy-2 methyl-1 ethyl thioglycolate (67/33) described in Patent Application No. FR-A-2 679 448, ⁇ -mercaptopropionic acid and derivatives thereof, and thiomalic acid.
  • the total concentration of thiols in the at least one reducing composition is as follows:
  • the total concentration of thiols is less than 5% by weight, such as from 0.1 to 5% by weight, or further from 0.5 to 4% by weight, relative to the total weight of the at least one reducing composition, or
  • the total concentration of thiols is less than 3% by weight, such as from 0.1% to 3% by weight and, further, for example, from 0.5% to 3% by weight relative to the total weight of the at least one reducing composition
  • the pH of the at least one reducing composition may be adjusted by means of at least one agent chosen from alkaline agents and acidifying agents.
  • the alkaline agents may, for example, be chosen from ammonia; organic amines, such as monoethanolamine, diethanolamine, triethanolamine, 1,3-propanediamine, and 2-amino-2-methyl-1-propanol; alkaline and ammonium carbonate or bicarbonate; organic carbonate, such as guanidine carbonate; alkaline hydroxide, such as soda.
  • the acidifying agents may, for example, be chosen from hydrochloric acid, acetic acid, lactic acid, oxalic acid. and boric acid.
  • the at least one reducing composition may, for example, comprise at least one cosmetically acceptable solvent chosen, for example, from water, C 1 -C 6 alcohols, for example, alkanols such as ethanol, propanol, and isopropanol; polyhydric alcohols, such as propyleneglycol, pentanediol and glycerine; benzyl alcohol; polyol ethers; C 2 -C 6 esters; N-methylpyrrolidone (NMP); and C 3 -C 6 cetones.
  • C 1 -C 6 alcohols for example, alkanols such as ethanol, propanol, and isopropanol
  • polyhydric alcohols such as propyleneglycol, pentanediol and glycerine
  • benzyl alcohol polyol ethers
  • C 2 -C 6 esters such as N-methylpyrrolidone (NMP); and C 3 -C 6 cetones.
  • the at least one reducing composition may also comprise at least one cosmetic additive.
  • the at least one cosmetic additive may, for example, be chosen from volatile and non volatile, linear and cyclic silicones; cationic, non ionic, anionic and amphoteric polymers; peptides and derivatives thereof; protein hydrolyzates; waxes; swelling agents and penetrating agents; agents that are able to increase the efficiency of the at least one reducing agent, such as a SiO 2 /polydimethylsiloxane mixture, dimethylisosorbitol, urea and derivatives thereof; anionic, cationic, non ionic, amphoteric, and zwitterionic surfactants; active agents for combating hair loss; anti-dandruff agents; natural and synthetic, associative and unassociative thickeners; suspension agents; sequestering agents; opacifying agents; dyes; sunscreen agents; vitamins and provitamins; fatty acids; fatty alcohols; mineral, vegetable, and synthetic oils; and fragrances and preserving agents.
  • cationic polymer means any polymer comprising cationic moieties and/or moieties that are ionizable to cationic moieties.
  • cationic polymers examples include polyamine, polyaminoamide and quaternary polyammonium type-polymers, which are known products.
  • Polyamine, polyaminoamide and quaternary polyammonium type-polymers suitable for use in the at least one reducing composition are those, for example, described in French Patent Nos. FR 2 505 348 and FR 2 542 997. These polymers may be chosen from at least one of the following:
  • cationic polymers that can be used include cationic proteins or cationic protein hydrolyzates, polyalkyleneimines, for example, polyethylene imines, polymers with vinyl pyridine or vinyl pyridinium moieties, polyamine and epichlorhydrine condensation products, quatemary polyureylenes, and chitin derivatives.
  • polyalkyleneimines for example, polyethylene imines, polymers with vinyl pyridine or vinyl pyridinium moieties, polyamine and epichlorhydrine condensation products, quatemary polyureylenes, and chitin derivatives.
  • the cationic polymers may be chosen from hexadimethrine chloride and dimethyldiallylammonium chloride homopolymers and copolymers.
  • the at least one cosmetic additive may also be chosen from silicones.
  • Silicones that are suitable for use as the at least one cosmetic additive include polydimethylsiloxanes; quatemized polyorganosiloxanes, such as those described in French Patent Application No. FR 2 535 730; polyorganosiloxanes comprising alkoxycarbonylalkyl moieties modified with aminoalkyl moieties, such as those described in U.S. Pat. No.
  • polyorganosiloxanes such as polydimethylsiloxane-polyoxyalkyl copolymer of dimethicone copolyol; a polydimethylsiloxane with stearoxy (stearoxy dimethicone) end groups; a polydimethylsiloxane-dialkylammonium acetate copolymer and a polydimethyl-siloxane polyalkylbetaine copolymer described in British Patent No. GB 2,197,352; and organo polysiloxanes modified by mercapto or mercaptoalkyl moieties such as those described in French Patent No. FR 1 530 369 and in European Patent Application No. EP 295 780.
  • the at least one cosmetic additive may also be chosen from fatty acids and fatty alcohols.
  • the fatty acids may, for example, be chosen from C 8 -C 30 carboxylic acids, such as palmitic acid, oleic acid, linoleic acid, myristic acid, stearic acid, lauric acid, and mixtures thereof.
  • the fatty alcohols may, for example, be chosen from C 8 -C 30 alcohols, such as palmityl, oleyl, linoleyl, myristyl, stearyl, and lauryl alcohols.
  • the at least one reducing composition used in the method disclosed herein may be provided in a form chosen from an optionally thickened lotion, a cream, a gel, and a foam.
  • the method disclosed herein comprises applying the at least one reducing composition as defined above to hair fibers. Once the at least one reducing composition has been applied, it can be left on the hair fibers, optionally under a drying helmet, for a time period ranging from 5 to 60 minutes, for example, from 5 to 30 minutes.
  • the method further comprises, after applying the reducing composition, optionally rinsing the hair fibers, then raising the temperature of the hair fibers, with a heating iron at a temperature of at least 60° C.
  • iron means any heating device which functions by contacting the hair fibers.
  • the end of the iron coming into contact with the hair may have various forms. It may, for example, have a plane surface, such as a flat iron. It may also have a rounded surface, such as a round iron.
  • the iron may be applied proceeding by successive separated touches for a few seconds or by gradually moving or sliding along hair locks.
  • the hair fiber temperature may be raised at a temperature ranging from 60° C. to 250° C., such as from 120° C. to 220° C.
  • the hair fibers are not rinsed out before heat is applied in the form of the heating iron for raising the temperature of the hair fibers.
  • the method disclosed herein may also include partially pre-drying the hair fibers before raising the temperature of the hair fibers, so as to prevent any substantial steam development that might bum the hands of the hair stylist and the scalp of the user.
  • This pre-drying may be done, for example, by using a hair drier, a hood, or it is also possible to let the hair dry naturally.
  • the hair fiber treating method disclosed herein was carried out using a reducing composition.
  • a reducing composition such as previously described was applied onto the hair and left on for 5 minutes.
  • the hair was then partially pre-dried using a hair drier before being treated using a flat iron heated to 180° C.
  • the hair fiber showed a good texture, a well controlled volume, a good respect of the color and a long term durability of the effects.

Landscapes

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

Abstract

A hair fiber treating method not containing a fixing step, comprising, applying to the hair fibers at least one reducing composition, free of ceramide, comprising at least one reducing agent; and raising the temperature of the hair fibers using a heating iron at temperature of at least 60° C., wherein the temperature of the hair fibers are raised before or after the hair fiber are optionally rinsed.

Description

  • This application claims benefit of U.S. Provisional Application No. 60/571,922, filed May 18, 2004, and French Patent Application No. 04 50667, filed Apr. 2, 2004, both of which are hereby incorporated by reference.
  • Disclosed herein is a method for treating hair fibers by applying a reducing composition and then heating the hair with a heating iron.
  • The usual practice to permanently reshape hair comprises first opening the keratin disulfide bonds (cystine) with a composition comprising a reducing agent. The disulfide bonds are then re-formed, optionally after rinsing the hair, by applying to the hair, which has been straightened or placed beforehand under tension with suitable means such as curlers or the equivalent, an oxidizing composition also called a fixing solution, so as to give the desired form to the hair. This method results in the waving of the hair, the uncurling of the hair, the backcombing of the hair, or the straightening of the hair.
  • Reducing compositions that can be used to carry out the first step of this method generally comprise compounds comprising a thiol group, such as thioglycolic acid, cysteine, cysteamine, thiolactic acid, and glycerol monothioglycolate.
  • The reducing agent concentration may be very high, often up to 15% by weight, relative to the total weight of the reducing composition.
  • Nevertheless, such a method may not be fully satisfactory. While it is very efficient to reshape the hair, it may cause great damage to the hair fibers.
  • Moreover, it has been suggested to raise the hair temperature between the reducing step and the fixing step by means of a heating iron.
  • For example, Patent Application No. JP 2000 256 146 describes a process to permanently reshape the hair, comprising the application of a cosmetic composition comprising from 2 to 11% reducing agents and from 0.2 to 4% diammonium dithiodiglycolate. After the reducing composition is applied, a heating iron is used at a temperature from 60 to 220° C.
  • Such a process nevertheless implies a post-iron fixing step as well, which increases the treatment time.
  • Moreover, the resulting shape is irreversible. The difference between the parts of the hair that have been treated and the hair roots is very noticeable as the hair regrows.
  • Finally, if the treatment is conducted on colored hair, it frequently causes the hair color to fade as a result of the treatment.
  • Thus, it would be desirable to provide a hair fiber treating method that compensates for at least one of the drawbacks of the prior art. For example, it would be desirable to provide a method that changes the hair fiber behavior while limiting the damage caused to the hair, controls the hair volume, and enhances at least one of the cosmetic benefits provided to the hair, for example, softness, shine and ease of combing, while also better preserving colored hair shades. Such a method would also ideally preserve the natural aspect of the hair so as to limit the so-called ‘root effect’, that is to say the contrast between the parts which have been treated and the roots, and also ideally reduce the hair fiber treating time and obtain long-lasting results.
  • The present inventors have found that it is possible to counteract at least one of the drawbacks of the prior art and to achieve at least one of the desirable results listed above, by carrying out a hair fiber treating method without fixing the hair, comprising applying to the hair fibers at least one reducing composition comprising at least one reducing agent chosen from compounds comprising at least one thiol group, wherein the at least one reducing agent is present in an amount of less than 3% by weight, relative to the total weight of the at least one reducing composition, and wherein the at least one reducing composition does not comprise an aminothiol compound or if the composition does comprise at least one aminothiol compound, it is present in an amount of less than 5% by weight, relative to the total weight of the at least one reducing composition, and raising the temperature of the hair fiber using a heating iron at a temperature of at least 60° C., wherein the temperature of the hair fiber is raised before or after the hair fibers are optionally rinsed.
  • Thus, disclosed herein is a method of treating hair fibers without fixing the hair, comprising:
      • applying to the hair fibers at least one reducing composition, free of ceramide, comprising at least one reducing agent chosen from thiols, wherein the at least one reducing agent is present in an amount of less than 3% by weight, relative to the total weight of the at least one reducing composition, provided that the at least one reducing composition does not comprise an aminothiol compound or if the at least one reducing composition does comprise at least one aminothiol compound, it is present in an amount of less than 5% by weight, relative to the total weight of the at least one reducing composition and
      • applying to the hair fibers a heating iron at a temperature of at least 60° C. to raise the temperature of the fibers, wherein the temperature of the hair fiber is raised before or after the hair fibers are optionally rinsed.
  • As used herein, ‘without fixing the hair’ or ‘without a hair-fixing step’ means without any additional application of a composition comprising a chemical oxidizing agent, such as hydrogen peroxide or a bromate.
  • The at least one reducing composition may have a pH of less than or equal to 9, provided that the at least one reducing composition does not comprise an aminothiol compound.
  • In one embodiment, the at least one reducing composition does not comprise dithiodiglycolic acid or any salt thereof.
  • The at least one reducing composition may, for example, be applied onto wet and clean hair fibers.
  • As used herein, ‘aminothiol compound’ means a thiol comprising at least one NH moiety.
  • The thiols used as the at least one reducing agent may, for example, be chosen from aminothiols, such as cysteine and derivatives thereof, i.e., N-acetylcysteine, cysteamine and derivatives thereof, C1-C4 acylated derivatives thereof, such as N-acetyl cysteamine and N-propionyl cysteamine, and non-aminated thiols, such as thiolactic acid and esters thereof, such as glycerol monothiolactate, thioglycolic acid and esters thereof, such as glycerol and glycol monothioglycolate, and thioglycerol.
  • When the thiol comprises at least one carboxylic acid functional group, the thiol may be provided, if needed, in the form of at least one salt thereof, such as alkali metal or ammonium salts. In one embodiment, ammonium thioglycolate may be used. When the thiol has an amine moiety, the thiol may be provided, if needed, in the form of at least one salt thereof, such as aminothiol halogenides. In one embodiment, L-cysteine hydrochloride may be used.
  • Examples of aminothiols that may be used in the at least one reducing composition include sugar N-mercapto-alkyl amides, such as N-(mercapto-2-ethyl)-gluconamide, pantheteine, and N-(mercaptoalkyl)-Ω-hydroxyalkyl amides such as those described in Patent Application No. EP-A-354 835 and N-mono- and N,N-dialkylmercapto 4-butyramides, such as those described Patent Application No. EP-A-368 763, aminomercaptoalkyl amides, such as those described Patent Application No. EP-A-432 000 and alkylaminomercaptoalkyl amides such as those described in Patent Application No. EP-A-514 282. Examples of non-aminated thiols that may be used include a mixture of hydroxy-2-propyl thioglycolate (2/3) and hydroxy-2 methyl-1 ethyl thioglycolate (67/33) described in Patent Application No. FR-A-2 679 448, β-mercaptopropionic acid and derivatives thereof, and thiomalic acid.
  • The total concentration of thiols in the at least one reducing composition is as follows:
  • when the at least one reducing composition comprises at least one aminothiol compound, the total concentration of thiols is less than 5% by weight, such as from 0.1 to 5% by weight, or further from 0.5 to 4% by weight, relative to the total weight of the at least one reducing composition, or
  • when the at least one reducing composition does not comprise at least one aminothiol compound, the total concentration of thiols is less than 3% by weight, such as from 0.1% to 3% by weight and, further, for example, from 0.5% to 3% by weight relative to the total weight of the at least one reducing composition
  • The pH of the at least one reducing composition may be adjusted by means of at least one agent chosen from alkaline agents and acidifying agents. The alkaline agents may, for example, be chosen from ammonia; organic amines, such as monoethanolamine, diethanolamine, triethanolamine, 1,3-propanediamine, and 2-amino-2-methyl-1-propanol; alkaline and ammonium carbonate or bicarbonate; organic carbonate, such as guanidine carbonate; alkaline hydroxide, such as soda. The acidifying agents may, for example, be chosen from hydrochloric acid, acetic acid, lactic acid, oxalic acid. and boric acid.
  • The at least one reducing composition may, for example, comprise at least one cosmetically acceptable solvent chosen, for example, from water, C1-C6 alcohols, for example, alkanols such as ethanol, propanol, and isopropanol; polyhydric alcohols, such as propyleneglycol, pentanediol and glycerine; benzyl alcohol; polyol ethers; C2-C6 esters; N-methylpyrrolidone (NMP); and C3-C6cetones.
  • In order to improve at least some of the cosmetic properties of the present hair compositions, the at least one reducing composition may also comprise at least one cosmetic additive.
  • The at least one cosmetic additive may, for example, be chosen from volatile and non volatile, linear and cyclic silicones; cationic, non ionic, anionic and amphoteric polymers; peptides and derivatives thereof; protein hydrolyzates; waxes; swelling agents and penetrating agents; agents that are able to increase the efficiency of the at least one reducing agent, such as a SiO2/polydimethylsiloxane mixture, dimethylisosorbitol, urea and derivatives thereof; anionic, cationic, non ionic, amphoteric, and zwitterionic surfactants; active agents for combating hair loss; anti-dandruff agents; natural and synthetic, associative and unassociative thickeners; suspension agents; sequestering agents; opacifying agents; dyes; sunscreen agents; vitamins and provitamins; fatty acids; fatty alcohols; mineral, vegetable, and synthetic oils; and fragrances and preserving agents.
  • As used herein, ‘cationic polymer’ means any polymer comprising cationic moieties and/or moieties that are ionizable to cationic moieties.
  • Examples of cationic polymers include polyamine, polyaminoamide and quaternary polyammonium type-polymers, which are known products.
  • Polyamine, polyaminoamide and quaternary polyammonium type-polymers suitable for use in the at least one reducing composition are those, for example, described in French Patent Nos. FR 2 505 348 and FR 2 542 997. These polymers may be chosen from at least one of the following:
      • (1) homopolymers or copolymers derived from acrylic or methacrylic acid esters or amides;
      • (2) cellulose ether derivatives comprising quaternary ammonium moieties described in French Patent No. FR 1 492 597;
      • (3) cationic cellulose derivatives, such as cellulose copolymers or cellulose derivatives grafted onto a water-soluble quaternary ammonium monomer, and described, for example, in U.S. Pat. No. 4,131,576, such as hydroxyalkylcelluloses, i.e. hydroxymethyl-, hydroxyethyl- and hydroxypropyl-cellulose, for example, grafted onto a methacryloylethyl-trimethylammonium salt, a methacrylamidopropyl-trimethylammonium salt or a dimethyldiallylammonium salt; for example, polyquatemium 10 (INCl denomination);
      • (4) other cationic polysaccharides described, for example, in U.S. Pat. Nos. 3,589,578 and 4,031,307, such as guar gums comprising trialkylammonium cationic moieties;
      • (5) polymers comprising piperazinyl moieties and linear or branched chain alkylene or hydroxyalkylene divalent groups, wherein the chains are optionally interrupted by at least one atom chosen from oxygen, sulphur, and nitrogen atoms or by aromatic or heterocyclic rings, as well as oxidation and/or quatemization products of these polymers. Such polymers are described, for example, in French Patent Nos. FR 2 162 025 and FR 2 280 361;
      • (6) water-soluble polyaminoamides, such as those, for example, described in French Patent Nos. FR 2 252 840 and FR 2 368 508;
      • (7) polyaminoamide derivatives, such as adipic acid/dialkylaminohydroxyalkyl dialkylene-triamine polymers, wherein the alkyl group comprises from 1 to 4 carbon atoms and is chosen, for example, from methyl, ethyl, and propyl groups, wherein the alkylene group comprises from 1 to 4 carbon atoms and may, for example, be an ethylene group. Such polymers are described, for example, in French Patent No. FR 1 583 363.
      • (8) polymers resulting from the reaction of a polyalkylene-polyamine comprising two primary amine moieties and at least one secondary amine moiety, with a dicarboxylic acid chosen from diglycolic acid and saturated aliphatic dicarboxylic acids comprising from 3 to 8 carbon atoms. The molar ratio between polyalkylene-polyamine and dicarboxylic acid ranging from 0.8:1 and 1.4:1; wherein the polyaminoamide resulting from such reaction is reacted with epichlorhydrine in a molar ratio of epichlorhydrine to secondary amine moiety of the polyaminoamide ranging from 0.5:1 to 1.8: 1. Such polymers are described, for example, in U.S. Pat. Nos. 3,227,615 and N° 2,961,347;
      • (9) alkyldiallylamine and dialkyldiallylammonium cyclopolymers, such as dimethyldiallylammonium chloride homopolymer and diallyldimethylammonium chloride and acrylamide copolymers;
      • (10) quaternary diammonium polymers having a number average molecular weight typically ranging from 1000 to 100000, such as those described, for example, in French Patent Nos. FR 2 320 330, 2 270 846, 2 316 271, 2 336 434, and 2 413 907 and in U.S. Pat. Nos. 2,273,780, 2,375,853, 2,388,614, 2,454,547, 3,206,462, 2,261,002, 2,271,378, 3,874,870, 4,001,432, 3,929,990, 3,966,904, 4,005,193, 4,025,617, 4,025,627, 4,025,653, 4,026,945 and 4,027,020; hexadimethrine chloride (INCI denomination) commercially marketed by CHIMEX under the trade name MEXOMERE PO is another example;
      • (11) quaternary polyammonium polymers, such as those described in Patent Application No. EP-A-122 324;
      • (12) vinylpyrrolidone and vinylimidazole quaternary polymers, such as products commercially marketed under the trade names Luviquat® FC 905, FC 550 and FC 370 by B.A.S.F;
      • (13) polyamines such as Polyquart® H commercially marketed by HENKEL, registered under the name ‘POLYETHYLENEGLYCOL (15) TALLOW POLYAMINE’ in the CTFA dictionary; and
      • (14) methacryloyloxyalkyl(C1-C4) trialkyl(C1-C4)ammonium salt branched polymers, such as those commercially marketed under the trade names SALCARE® SC 92, SALCARE® SC 95 and SALCARE® SC 96 by ALLIED COLLOIDS.
  • Other cationic polymers that can be used include cationic proteins or cationic protein hydrolyzates, polyalkyleneimines, for example, polyethylene imines, polymers with vinyl pyridine or vinyl pyridinium moieties, polyamine and epichlorhydrine condensation products, quatemary polyureylenes, and chitin derivatives.
  • In one embodiment, the cationic polymers may be chosen from hexadimethrine chloride and dimethyldiallylammonium chloride homopolymers and copolymers.
  • As explained above, the at least one cosmetic additive may also be chosen from silicones.
  • Silicones that are suitable for use as the at least one cosmetic additive include polydimethylsiloxanes; quatemized polyorganosiloxanes, such as those described in French Patent Application No. FR 2 535 730; polyorganosiloxanes comprising alkoxycarbonylalkyl moieties modified with aminoalkyl moieties, such as those described in U.S. Pat. No. 4,749,732; polyorganosiloxanes, such as polydimethylsiloxane-polyoxyalkyl copolymer of dimethicone copolyol; a polydimethylsiloxane with stearoxy (stearoxy dimethicone) end groups; a polydimethylsiloxane-dialkylammonium acetate copolymer and a polydimethyl-siloxane polyalkylbetaine copolymer described in British Patent No. GB 2,197,352; and organo polysiloxanes modified by mercapto or mercaptoalkyl moieties such as those described in French Patent No. FR 1 530 369 and in European Patent Application No. EP 295 780.
  • Moreover, the at least one cosmetic additive may also be chosen from fatty acids and fatty alcohols.
  • The fatty acids may, for example, be chosen from C8-C30 carboxylic acids, such as palmitic acid, oleic acid, linoleic acid, myristic acid, stearic acid, lauric acid, and mixtures thereof.
  • The fatty alcohols may, for example, be chosen from C8-C30 alcohols, such as palmityl, oleyl, linoleyl, myristyl, stearyl, and lauryl alcohols.
  • The at least one reducing composition used in the method disclosed herein may be provided in a form chosen from an optionally thickened lotion, a cream, a gel, and a foam.
  • The method disclosed herein comprises applying the at least one reducing composition as defined above to hair fibers. Once the at least one reducing composition has been applied, it can be left on the hair fibers, optionally under a drying helmet, for a time period ranging from 5 to 60 minutes, for example, from 5 to 30 minutes.
  • As explained above, the method further comprises, after applying the reducing composition, optionally rinsing the hair fibers, then raising the temperature of the hair fibers, with a heating iron at a temperature of at least 60° C.
  • As used herein, ‘iron’ means any heating device which functions by contacting the hair fibers.
  • The end of the iron coming into contact with the hair may have various forms. It may, for example, have a plane surface, such as a flat iron. It may also have a rounded surface, such as a round iron.
  • The iron may be applied proceeding by successive separated touches for a few seconds or by gradually moving or sliding along hair locks.
  • All types of flat or round irons may be given as non limitative examples of suitable irons for use in the method disclosed herein, for example, those described in U.S. Pat. Nos. 4,103,145; 4,308,878; 5,983,903; 5,957,140; 5,494,058; and 5,046,516.
  • The hair fiber temperature may be raised at a temperature ranging from 60° C. to 250° C., such as from 120° C. to 220° C.
  • According to one embodiment, the hair fibers are not rinsed out before heat is applied in the form of the heating iron for raising the temperature of the hair fibers.
  • The method disclosed herein may also include partially pre-drying the hair fibers before raising the temperature of the hair fibers, so as to prevent any substantial steam development that might bum the hands of the hair stylist and the scalp of the user. This pre-drying may be done, for example, by using a hair drier, a hood, or it is also possible to let the hair dry naturally.
  • Further disclosed herein is a method as described herein to durably change the hair shape without excessively altering the hair color and/or without excessively damaging the hair fibers.
  • Other than in the operating examples, or where otherwise indicated, all numbers expressing quantities of ingredients, reaction conditions, and so forth used in the specification and claims are to be understood as being modified in all instances by the term “about.” Accordingly, unless indicated to the contrary, the numerical parameters set forth in the specification and attached claims are approximations that may vary depending upon the desired properties sought to be obtained by the present invention. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, each numerical parameter should be construed in light of the number of significant digits and ordinary rounding approaches.
  • Notwithstanding that the numerical ranges and parameters setting forth the broad scope of the invention are approximations, the numerical values set forth in the specific example are reported as precisely as possible. Any numerical value, however, inherently contains certain errors necessarily resulting from the standard deviation found in their respective testing measurements.
  • The following examples are intended to illustrate the invention in a non-limiting manner.
  • EXAMPLES
  • The hair fiber treating method disclosed herein was carried out using a reducing composition.
  • Tested reducing compositions were as follows:
  • Reducing Composition 1
  • L-Cysteine 1.4 g
    MEXOMERE PO 2.5 g
    2-amino-2-methyl-1-propanol qs pH 9
    Demineralized water qs 100 g
  • Reducing Composition 2
  • Thioglycolic acid 1.1 g
    MEXOMERE PO 2.5 g
    2-amino-2-methyl-1-propanol qs pH 9
    Demineralized water qs 100 g
  • Reducing Composition 3
  • L-Cysteine 1.4 g
    Thioglycolic acid 0.3 g
    MEXOMERE PO 2.5 g
    2-amino-2-methyl-1-propanol qs pH 9
    Demineralized water qs 100 g
  • Reducing Composition 4
  • L-Cysteine 1.4 g
    2-amino-2-methyl-1-propanol qs pH 9
    Demineralized water qs 100 g
  • Tests were conducted on colored, naturally curling hair.
  • A reducing composition such as previously described was applied onto the hair and left on for 5 minutes.
  • The hair was then partially pre-dried using a hair drier before being treated using a flat iron heated to 180° C.
  • As a result, the hair fiber showed a good texture, a well controlled volume, a good respect of the color and a long term durability of the effects.

Claims (24)

1-25. (canceled)
26. A method for treating hair fibers comprising,
applying to the hair fibers at least one reducing composition, free of ceramide, comprising at least one reducing agent, wherein the at least one reducing agent is chosen from thiols and wherein
when the at least one reducing composition does not comprise at least one aminothiol compound, the at least one reducing agent is present in an amount of less than 3% by weight, relative to the total weight of the at least one reducing composition,
when the at least one reducing composition does comprise at least one aminothiol compound, the at least one reducing agent is present in an amount of less than 5% by weight, relative to the total weight of the at least one reducing composition, and
applying a heating iron to the hair fibers to raise the temperature of said hair fibers, wherein said heating iron has a temperature ranging from 120° C. to 220° C., and wherein the heating iron is applied before or after the hair fibers are optionally rinsed, and
wherein the method does not include a fixing step.
27. The method according to claim 26, wherein, when the at least one reducing composition does not comprise at least one aminothiol compound, said at least one reducing composition has a pH of less than or equal to 9.
28. The method according to claim 26, wherein the at least one reducing composition does not comprise dithiodiglycolic acid or any salt thereof.
29. The method according to claim 26, wherein when the at least one reducing composition does not comprise at least one aminothiol, the at least one reducing agent is present in an amount ranging from 0.1% to 3% by weight, relative to the total weight of the at least one reducing composition.
30. The method according to claim 29, wherein the at least one reducing agent is present in an amount ranging from 0.5% to 3% by weight relative to the total weight of the at least one reducing composition.
31. The method according to claim 26, wherein when the at least one reducing composition comprises at least one aminothiol compound, the at least one reducing agent is present in an amount ranging from 0.1 to 5% by weight, relative to the total weight of the at least one reducing composition.
32. The method according to claim 31, wherein the at least one reducing agent is present in an amount ranging from 0.5 to 4% by weight, relative to the total weight of the at least one reducing composition.
33. The method according to claim 26, further comprising leaving the at least one reducing composition on the hair fibers for a time period ranging from 5 to 60 minutes before heating.
34. The method according to claim 33, further comprising leaving the at least one reducing composition on the hair fibers for a time period ranging from 5 to 30 minutes before heating.
35. The method according to claim 26, further comprising not rinsing the hair fibers before heating the hair fibers.
36. The method according to claim 26, further comprising partially pre-drying the hair fibers before heating the hair fibers.
37. The method according to claim 26, wherein the thiols are chosen from aminothiols and non-aminated thiols.
38. The method according to claim 37, wherein the aminothiols are chosen from cysteine and derivatives thereof and cysteamine and derivatives thereof.
39. The method according to claim 37, wherein the non-aminated thiols are chosen from thiolactic acid and esters thereof, thioglycolic acid and esters thereof, and thioglycerol.
40. The method according to claim 37, wherein the thiols are in salts form.
41. The method according to claim 26, wherein the at least one reducing composition comprises at least one solvent chosen from water, C1-C6 alcohols, polyhydric alcohols, benzyl alcohol, polyol ethers, C2-C6 esters, N-methylpyrrolidone (NMP), and C3-C6cetones.
42. The method according to claim 41, wherein the C1-C6 alcohols are alkanols chosen from ethanol, propanol, and isopropanol.
43. The method according to claim 42, wherein polyhydric alcohols are chosen from propyleneglycol, pentanediol, and glycerine.
44. The method according to claim 26, wherein the at least one reducing composition comprises at least one cosmetic additive chosen from volatile and non volatile, linear and cyclic silicones; cationic, non ionic, anionic, and amphoteric polymers; peptides and derivatives thereof; protein hydrolyzates; waxes; swelling agents and penetrating agents; agents that are able to increase the efficiency of the at least one reducing agent; anionic, cationic, non ionic, amphoteric, and zwitterionic surfactants; active agents combating hair loss; anti-dandruff agents; natural and synthetic, associative and unassociative thickeners; suspension agents; sequestering agents; opacifying agents; dyes; sunscreen agents; vitamins and provitamins; fatty acids; fatty alcohols; mineral, vegetable and synthetic oils; and fragrances and preserving agents.
45. The method according to claim 44, wherein the cationic polymers are chosen from hexadimethrine chloride and dimethyldiallylammonium chloride homopolymers and copolymers.
46. The method according to claim 26, wherein the at least one reducing composition is provided in a form chosen from an optionally thickened lotion, a cream, a gel, and a foam.
47. A method for treating hair fibers to change the shape of the hair fibers without excessively altering the hair color and/or without excessively damaging the hair fibers, said method comprising:
applying to the hair fibers at least one reducing composition, free of ceramide, comprising at least one reducing agent, wherein the at least one reducing agent is chosen from thiols and wherein
when the at least one reducing composition does not comprise at least one aminothiol compound, the at least one reducing agent is present in an amount of less than 3% by weight, relative to the total weight of the at least one reducing composition,
when the at least one reducing composition does comprise at least one aminothiol compound, the at least one reducing agent is present in an amount of less than 5% by weight, relative to the total weight of the at least one reducing composition, and
applying a heating iron to the hair fibers to raise the temperature of said hair fibers, wherein said heating iron has a temperature ranging from 120° C. to 220° C., and wherein the heating iron is applied before or after the hair fibers are optionally rinsed, and
thus changing the shape of the hair fibers without excessive alteration of the hair color and/or without excessive damage to the hair fibers, and without a fixing step.
48. The method according to claim 26, wherein:
when the at least one reducing composition does not comprise at least one aminothiol compound, the at least one reducing agent is present in an amount of 1.1% or less by weight, relative to the total weight of the at least one reducing composition; and
when the at least one reducing composition comprises at least one aminothiol compound, the at least one reducing agent is present in an amount of 1.4% or less by weight, relative to the total weight of the at least one reducing composition.
US13/541,117 2004-04-02 2012-07-03 Method for treating hair fibers Active US9675822B2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US13/541,117 US9675822B2 (en) 2004-04-02 2012-07-03 Method for treating hair fibers
US15/584,472 US10702464B2 (en) 2004-04-02 2017-05-02 Method for treating hair fibers

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
FR0450667A FR2868305B1 (en) 2004-04-02 2004-04-02 CAPILLARY TREATMENT PROCESS AND USE THEREOF
FR0450667 2004-04-02
US57192204P 2004-05-18 2004-05-18
US11/097,167 US20050232883A1 (en) 2004-04-02 2005-04-04 Method for treating hair fibers
US13/541,117 US9675822B2 (en) 2004-04-02 2012-07-03 Method for treating hair fibers

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US11/097,167 Continuation US20050232883A1 (en) 2004-04-02 2005-04-04 Method for treating hair fibers

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US15/584,472 Division US10702464B2 (en) 2004-04-02 2017-05-02 Method for treating hair fibers

Publications (3)

Publication Number Publication Date
US20130000661A1 US20130000661A1 (en) 2013-01-03
US20170095408A9 true US20170095408A9 (en) 2017-04-06
US9675822B2 US9675822B2 (en) 2017-06-13

Family

ID=35096497

Family Applications (3)

Application Number Title Priority Date Filing Date
US11/097,167 Abandoned US20050232883A1 (en) 2004-04-02 2005-04-04 Method for treating hair fibers
US13/541,117 Active US9675822B2 (en) 2004-04-02 2012-07-03 Method for treating hair fibers
US15/584,472 Active 2026-08-01 US10702464B2 (en) 2004-04-02 2017-05-02 Method for treating hair fibers

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US11/097,167 Abandoned US20050232883A1 (en) 2004-04-02 2005-04-04 Method for treating hair fibers

Family Applications After (1)

Application Number Title Priority Date Filing Date
US15/584,472 Active 2026-08-01 US10702464B2 (en) 2004-04-02 2017-05-02 Method for treating hair fibers

Country Status (8)

Country Link
US (3) US20050232883A1 (en)
EP (1) EP1584329B2 (en)
JP (1) JP2005290003A (en)
KR (1) KR20060045454A (en)
CN (1) CN100574741C (en)
BR (1) BRPI0501718A (en)
FR (1) FR2868305B1 (en)
MX (1) MXPA05003491A (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2868305B1 (en) * 2004-04-02 2006-06-30 Oreal CAPILLARY TREATMENT PROCESS AND USE THEREOF
JP5089053B2 (en) * 2006-01-31 2012-12-05 株式会社ミルボン Decontamination composition
FR2911272B1 (en) * 2007-01-12 2009-03-06 Oreal REDUCING COMPOSITION INTENDED FOR USE IN A PROCESS FOR PERMANENTLY DEFORMING KERATIN FIBERS COMPRISING CYSTEINE AND THIOLACTIC ACID OR ONE OF THEIR SALTS
FR2944438B1 (en) 2009-04-15 2011-06-17 Oreal METHOD OF FORMING HAIR BY MEANS OF REDUCING COMPOSITION AND HEATING.
FR2965481B1 (en) 2010-10-01 2013-04-19 Oreal PROCESS FOR TREATING KERATIN FIBERS USING AT LEAST ONE SULFUR REDUCER, AT LEAST ONE CATIONIC POLYMER AND AT LEAST ONE MERCAPTOSILOXANE
US8607803B2 (en) 2011-09-29 2013-12-17 The Procter & Gamble Company Hair treatment process providing dispersed colors by light diffraction
DE102011084188A1 (en) * 2011-10-10 2013-04-11 BSH Bosch und Siemens Hausgeräte GmbH Hair styling and / or hair straightening agent with traction enhancing agent
MX2015005778A (en) 2013-03-28 2015-09-23 Procter & Gamble Hair treatment process providing dispersed colors by light diffraction.
FR3039374B1 (en) * 2015-07-29 2019-12-20 L'oreal PROCESS FOR TREATING HAIR FIBERS
US20190240130A1 (en) * 2016-09-30 2019-08-08 L'creal Hair cosmetic composition comprising thiol-based compounds
JP7353754B2 (en) * 2018-12-14 2023-10-02 ロレアル Keratin fiber straightening method

Family Cites Families (153)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB339805A (en) 1929-12-21 1930-12-18 Sunsaloon Bodies Ltd Improvements in or relating to removable heads and roofs for motor vehicles
BE380814A (en) * 1930-06-26
US1970066A (en) * 1934-02-14 1934-08-14 Torigiani Orlando Time controlled switch
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
US2388614A (en) * 1942-05-05 1945-11-06 Du Pont Disinfectant compositions
US2375853A (en) * 1942-10-07 1945-05-15 Du Pont Diamine derivatives
US2463264A (en) * 1942-12-23 1949-03-01 Ciba Ltd Derivatives of cyclic amidines and process of making same
US2454547A (en) * 1946-10-15 1948-11-23 Rohm & Haas Polymeric quaternary ammonium salts
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
CA714031A (en) 1953-06-10 1965-07-20 Northwestern Research Corp. Method of treating hair
US2723248A (en) 1954-10-01 1955-11-08 Gen Aniline & Film Corp Film-forming compositions
CH353491A (en) 1955-06-29 1961-04-15 Oreal Process for the permanent deformation of hair and composition obtained allowing waving or stripping
US2781354A (en) * 1956-03-26 1957-02-12 John J Mccabe Jr Imidazoline derivatives and process
GB839805A (en) 1957-06-10 1960-06-29 Monsanto Chemicals Sprayable compositions
US2961347A (en) * 1957-11-13 1960-11-22 Hercules Powder Co Ltd Process for preventing shrinkage and felting of wool
FR1222944A (en) 1958-04-15 1960-06-14 Hoechst Ag Graft polymers and their preparation 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
FR1400366A (en) 1963-05-15 1965-05-28 Oreal New compounds which can be used in particular for the treatment of hair
US3256154A (en) * 1963-10-18 1966-06-14 Gillette Co Hair waving composition and method
US4192863A (en) * 1964-06-12 1980-03-11 Tokuzo Kondo Completely one-step permanent wave solution and a method for using the same
US3327615A (en) * 1965-01-04 1967-06-27 William S Swan Coffee dispenser with built-in grinder
LU54202A1 (en) 1967-07-28 1969-03-24 Oreal Process for the preparation of new copolymers and cosmetic compositions containing these copolymers
FR1517743A (en) * 1966-08-03 1968-03-22 Oreal New copolymers and cosmetic compositions containing these copolymers
US3472840A (en) * 1965-09-14 1969-10-14 Union Carbide Corp Quaternary nitrogen-containing cellulose ethers
FR1492597A (en) 1965-09-14 1967-08-18 Union Carbide Corp New cellulose ethers containing quaternary nitrogen
US3472243A (en) * 1965-09-27 1969-10-14 Clairol Inc Treating damaged living human hair with water soluble polymerizable vinyl monomers
NL6702986A (en) 1966-07-07 1968-01-08
FR1530369A (en) 1966-07-07 1968-06-21 Dow Corning Hair treatment compositions
NL136457C (en) 1967-03-23
US3810977A (en) * 1967-03-23 1974-05-14 Nat Starch Chem Corp Hair fixing composition and process containing a solid terpolymer
CH491153A (en) * 1967-09-28 1970-05-31 Sandoz Ag Process for the production of new cation-active, water-soluble polyamides
US3836537A (en) * 1970-10-07 1974-09-17 Minnesota Mining & Mfg Zwitterionic polymer hairsetting compositions and method of using same
FR2280361A2 (en) 1974-08-02 1976-02-27 Oreal HAIR TREATMENT AND CONDITIONING COMPOSITIONS
LU64371A1 (en) * 1971-11-29 1973-06-21
US4013787A (en) * 1971-11-29 1977-03-22 Societe Anonyme Dite: L'oreal Piperazine based polymer and hair treating composition containing the same
LU65552A1 (en) 1972-06-20 1973-12-27
CA981746A (en) * 1973-09-24 1976-01-13 Alfred M. Hase Battery charging circuit
US4189468A (en) * 1973-11-30 1980-02-19 L'oreal Crosslinked polyamino-polyamide in hair conditioning compositions
LU68901A1 (en) 1973-11-30 1975-08-20
FR2368508A2 (en) 1977-03-02 1978-05-19 Oreal HAIR CONDITIONING COMPOSITION
US4277581A (en) 1973-11-30 1981-07-07 L'oreal Polyamino-polyamide crosslinked with crosslinking agent
US4172887A (en) * 1973-11-30 1979-10-30 L'oreal Hair conditioning compositions containing crosslinked polyaminopolyamides
US3929990A (en) * 1973-12-18 1975-12-30 Millmaster Onyx Corp Microbiocidal polymeric quaternary ammonium compounds
US3874870A (en) * 1973-12-18 1975-04-01 Mill Master Onyx Corp Microbiocidal polymeric quarternary ammonium compounds
US4025627A (en) * 1973-12-18 1977-05-24 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
US4166894A (en) * 1974-01-25 1979-09-04 Calgon Corporation Functional ionene compositions and their use
DK659674A (en) 1974-01-25 1975-09-29 Calgon Corp
LU69759A1 (en) 1974-04-01 1976-03-17
LU69760A1 (en) * 1974-04-01 1976-03-17
US4422853A (en) * 1974-05-16 1983-12-27 L'oreal Hair dyeing compositions containing quaternized polymer
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
IT1050562B (en) 1974-05-16 1981-03-20 Oreal COSMETIC AGENT BASED ON QUATERNIZED POLYMERS
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
US4948579A (en) * 1974-05-16 1990-08-14 Societe Anonyme Dite: L'oreal Quaternized polymer for use as a cosmetic agent in cosmetic compositions for the hair and skin
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
US4026945A (en) * 1974-10-03 1977-05-31 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
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
US4197865A (en) * 1975-07-04 1980-04-15 L'oreal Treating hair with quaternized polymers
AT365448B (en) * 1975-07-04 1982-01-11 Oreal COSMETIC PREPARATION
US4103145A (en) * 1975-07-24 1978-07-25 Oliveri Joseph T Hair curling iron and oven
CH1669775A4 (en) 1975-12-23 1977-06-30
AT364706B (en) 1976-04-06 1981-11-10 Oreal COSMETIC AGENT FOR TREATING THE HAIR
LU75370A1 (en) 1976-07-12 1978-02-08
GB1572555A (en) * 1976-04-06 1980-07-30 Oreal Copolymers on n-alkyl-or n-alkoxyalkyl-acrylamides or-methacrylamides process for their preparation and their use in cosmetics
LU75371A1 (en) 1976-07-12 1978-02-08
US4031307A (en) * 1976-05-03 1977-06-21 Celanese Corporation Cationic polygalactomannan compositions
GB1572837A (en) 1976-05-06 1980-08-06 Berger Jenson & Nicholson Ltd Coating composition
JPS52154529A (en) 1976-06-15 1977-12-22 Matsushita Electric Works Ltd Hair conditioning lotion composition
JPS52154259A (en) 1976-06-15 1977-12-21 Hideaki Itagaki Sewage treating apparatus
FR2357241A2 (en) 1976-07-08 1978-02-03 Oreal Partially esterified or amidated unsaturated anhydride copolymer - for hair lacquer made from copolymer of unsaturated anhydride, allyl or methallyl ester and acrylamide or methacrylamide cpd.
US4128631A (en) * 1977-02-16 1978-12-05 General Mills Chemicals, Inc. Method of imparting lubricity to keratinous substrates and mucous membranes
CH614878A5 (en) 1977-03-11 1979-12-28 Charmilles Sa Ateliers
LU78153A1 (en) * 1977-09-20 1979-05-25 Oreal COSMETIC COMPOSITIONS BASED ON QUATERNARY POLYAMMONIUM POLYMERS AND PREPARATION PROCESS
US4131576A (en) * 1977-12-15 1978-12-26 National Starch And Chemical Corporation Process for the preparation of graft copolymers of a water soluble monomer and polysaccharide employing a two-phase reaction system
US4970066A (en) 1978-06-15 1990-11-13 L'oreal Hair dye or bleach supports of quaternized polymers
US4348202A (en) 1978-06-15 1982-09-07 L'oreal Hair dye or bleach supports
FR2439798A1 (en) 1978-10-27 1980-05-23 Oreal NEW COPOLYMERS FOR USE IN COSMETICS, IN PARTICULAR IN HAIR LACQUERS AND LOTIONS
US4308878A (en) * 1979-11-29 1982-01-05 Silva Wilbur W Curling iron holder
LU83349A1 (en) 1981-05-08 1983-03-24 Oreal AEROSOL FOAM COMPOSITION BASED ON CATIONIC POLYMER AND ANIONIC POLYMER
LU83703A1 (en) 1981-10-20 1983-06-08 Oreal NOVEL COSMETIC COMPOSITION AND ITS APPLICATION TO PERMANENT DEFORMATION OF HAIR
US4452261A (en) * 1982-01-29 1984-06-05 The Gillette Company Hair setting composition and method
LU84463A1 (en) * 1982-11-10 1984-06-13 Oreal POLYQUATERNARY POLYSILOXANE POLYMERS
LU84708A1 (en) * 1983-03-23 1984-11-14 Oreal THICKENED OR GELLIED HAIR CONDITIONING COMPOSITION CONTAINING AT LEAST ONE CATIONIC POLYMER, AT LEAST ONE ANIONIC POLYMER AND AT LEAST ONE XANTHANE GUM
DE3375135D1 (en) 1983-04-15 1988-02-11 Miranol Inc Polyquaternary ammonium compounds and cosmetic compositions containing them
US4812307A (en) 1983-07-06 1989-03-14 Chesebrough-Pond's Inc. Crosslinking of hair thiols using glutathione disulfide
JPS60199833A (en) * 1984-03-26 1985-10-09 Meiji Milk Prod Co Ltd Preparation of w/o/w-type composite emulsion for pharmaceutical, cosmetic, etc.
JPS6259205A (en) * 1985-09-10 1987-03-14 Tokuzo Kondo Permanent wave agent
US4798722A (en) 1986-11-12 1989-01-17 Zotos International, Inc. Permanent waving composition
EP0269107A3 (en) * 1986-11-28 1989-10-11 Kao Corporation Composition for hair treatment agent
US4749732A (en) * 1987-01-02 1988-06-07 Dow Corning Corporation Hair care composition containing modified aminoalkyl substituted polydiorganosiloxane
GB8713879D0 (en) 1987-06-13 1987-07-15 Dow Corning Ltd Treating hair
US4795629A (en) 1987-07-06 1989-01-03 Chesebrough-Pond's Inc. Crosslinking of hair thiols using cystamine
EP0299764B1 (en) 1987-07-16 1992-05-27 Unilever Plc Hair treatment product
LU87310A1 (en) * 1988-08-04 1990-03-13 Oreal N- (MERCAPTOALKYL) OMEGA-HYDROXYALKYLAMIDES AND THEIR USE AS REDUCING AGENTS, IN A PERMANENT HAIR DEFORMATION PROCESS
US5046516A (en) * 1988-10-31 1991-09-10 George Barradas Hair curling iron
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
FR2654617B1 (en) 1989-11-20 1993-10-08 Oreal COSMETIC REDUCING COMPOSITION FOR PERMANENT CONTAINING, AS REDUCING AGENT, ALETHEINE OR ONE OF ITS SALTS, AND ITS USE IN A PROCESS OF PERMANENT DEFORMATION OF HAIR.
US5237071A (en) * 1991-01-22 1993-08-17 Fairmount Chemical Company, Inc. Process for preparing 2,2'-methylene-bis(6-(2H-benzotriazol-2-yl)-4-hydrocarbyl phenols)
US5166355A (en) * 1991-02-04 1992-11-24 Fairmount Chemical Co., Inc. Process for preparing substituted 2,2'-methylene-bis-[6-(2H-benzotriazol-2-yl)-4-hydrocarbyl-phenols]
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.
IT1247973B (en) 1991-06-04 1995-01-05 Sigma Prod Chim 1,3,5-TRIAZINE DERIVATIVES, THEIR PREPARATION AND USE AS SOLAR FILTERS
FR2677543B1 (en) 1991-06-13 1993-09-24 Oreal COSMETIC FILTERING COMPOSITION BASED ON BENZENE 1,4-DI ACID (3-METHYLIDENE-10-CAMPHOSULFONIC) AND NANOPIGMENTS OF METAL OXIDES.
FR2677544B1 (en) 1991-06-14 1993-09-24 Oreal COSMETIC COMPOSITION CONTAINING A MIXTURE OF NANOPIGMENTS OF METAL OXIDES AND MELANIC PIGMENTS.
FR2679448B1 (en) 1991-07-23 1993-10-15 Oreal AZETROPE MIXTURE OF 2-HYDROXY-2-PROPYL THIOGLYCOLATE AND 2-HYDROXY-2-METHYL-ETHYL THIOGLYCOLATE, PROCESS FOR THE PRODUCTION THEREOF, AND USE THEREOF IN A PERMANENT HAIR DEFORMATION PROCESS.
JP3187521B2 (en) * 1992-03-24 2001-07-11 カネボウ株式会社 Permanent wave agent 1st agent
IT1255729B (en) * 1992-05-19 1995-11-15 Giuseppe Raspanti s-triazine derivatives as photostabilising agents
US5279818A (en) * 1992-10-13 1994-01-18 Dow Corning Corporation Permanent waving with silicones
JPH06192051A (en) * 1992-12-24 1994-07-12 Hoyu Co Ltd 1st agent for flatiron perm
TW311089B (en) 1993-07-05 1997-07-21 Ciba Sc Holding Ag
TW325998B (en) 1993-11-30 1998-02-01 Ciba Sc Holding Ag Dyeing keratin-containing fibers
US6013249A (en) * 1994-02-09 2000-01-11 Helene Curtis, Inc. Hair manageability and styling composition and method
GB2286772B (en) * 1994-02-10 1997-11-19 China Pacific Trade Ltd Hair curling iron
ES2157268T5 (en) 1994-02-24 2004-12-01 SYMRISE GMBH & CO KG COSMETIC AND DERMATOLOGICAL PREPARATIONS CONTAINING PHENYLENE-1,4-BISBENCIMIDAZOLSULFONIC ACIDS.
FR2718351B1 (en) 1994-04-11 1996-05-31 Oreal Process for the permanent deformation of keratin materials.
ES2215944T3 (en) 1994-11-03 2004-10-16 Ciba Specialty Chemicals Holding Inc. CATIONIC IMIDAZOLAZOIC COLORS.
US5637297A (en) 1994-12-08 1997-06-10 Shiseido Co., Ltd. Reducing agents for permanent waving of hair
GB9515048D0 (en) 1995-07-22 1995-09-20 Ciba Geigy Ag Sunscreen compositions
JPH09132515A (en) * 1995-11-09 1997-05-20 Seiji Maekawa Curly hair straightening
DE19543730A1 (en) * 1995-11-23 1997-05-28 Ciba Geigy Ag Until resorcinyl-triazines
IT1283295B1 (en) 1996-03-22 1998-04-16 3V Sigma Spa SOLAR FILTERS
US5749379A (en) 1996-04-25 1998-05-12 Golden Supreme, Inc. Non-numeric temperature indicating method for a hair styling iron
JPH10113212A (en) * 1996-10-15 1998-05-06 Matsushita Electric Works Ltd Hair iron
EP0863145B1 (en) 1997-03-03 2003-10-01 F. Hoffmann-La Roche Ag Sunscreen compositions
US5976512A (en) * 1997-03-03 1999-11-02 Roche Vitamins Inc. Symetrical hydroxyphenyl-s-triazine compositions
TW432055B (en) * 1997-05-16 2001-05-01 Ciba Sc Holding Ag Resorcinyl-triazines, their preparation process and a cosmetic composition containing them
EP0878469B1 (en) 1997-05-16 2004-10-27 Ciba SC Holding AG Resorcinyl-triazines
DE19726184A1 (en) 1997-06-20 1998-12-24 Beiersdorf Ag Oil-in-water or multiple emulsion with high concentration of suspended UVB filter
GB9715751D0 (en) 1997-07-26 1997-10-01 Ciba Geigy Ag Formulations
EP0933376B1 (en) 1998-01-02 2003-08-20 F. Hoffmann-La Roche Ag Silanyl-triazines as light screening compositions
JP2000143452A (en) * 1998-11-02 2000-05-23 C T C Japan:Kk Hair treatment composition and treatment of hair
JP4204021B2 (en) 1998-11-05 2009-01-07 パナソニック電工株式会社 Hair setting method
US5957140A (en) * 1998-11-19 1999-09-28 Mcgee; Robert J. Hair styling iron for straightening and curling
DE19855649A1 (en) 1998-12-03 2000-06-08 Basf Ag Dimeric alpha-alkyl-styrene derivatives as photostable UV filters in cosmetic and pharmaceutical preparations
JP3522572B2 (en) * 1999-03-15 2004-04-26 株式会社ミルボン First agent for heated permanent wave and method for applying heated straight perm to curly hair using the same
JP2001213741A (en) * 2000-02-01 2001-08-07 Hoyu Co Ltd Method for hair treatment
DE10103494A1 (en) 2001-01-26 2002-08-14 Goldwell Gmbh Means for permanent deformation of human hair
JP2002356408A (en) 2001-05-30 2002-12-13 Milbon Co Ltd Hair treatment and method for hair treatment using the same
JP2002356410A (en) * 2001-05-30 2002-12-13 Milbon Co Ltd First agent for permanent wave and method for permanent wave treatment using the same
US7195755B2 (en) 2001-08-20 2007-03-27 L'oreal S.A. Compositions comprising at least one hydroxide compound and at least one reducing agent, and methods for relaxing hair
JP2004026770A (en) 2002-06-28 2004-01-29 Milbon Co Ltd First agent for correcting curly hair and method for correcting treatment of curly hair using the same
JP2004035473A (en) * 2002-07-03 2004-02-05 Tokyo Aerosol Kagaku Kk Foam aerosol composition for hair treatment, and hair treatment method
JP2004002459A (en) * 2003-07-15 2004-01-08 Milbon Co Ltd Primary agent for permanent wave and method of treatment for straight permanent wave to curly hair by using the same
US20050025736A1 (en) * 2003-07-30 2005-02-03 Janusz Jachowicz Hair and skin altering and protecting compositions
US7976831B2 (en) * 2004-04-02 2011-07-12 L'oreal S.A. Method for treating hair fibers
FR2868305B1 (en) * 2004-04-02 2006-06-30 Oreal CAPILLARY TREATMENT PROCESS AND USE THEREOF
US20110083695A1 (en) * 2009-10-12 2011-04-14 Bahereh Abbasi Hair Straightening Apparatus

Also Published As

Publication number Publication date
US9675822B2 (en) 2017-06-13
CN100574741C (en) 2009-12-30
MXPA05003491A (en) 2005-10-06
JP2005290003A (en) 2005-10-20
US20130000661A1 (en) 2013-01-03
CN1698569A (en) 2005-11-23
EP1584329B1 (en) 2014-11-05
EP1584329B2 (en) 2021-05-19
US20050232883A1 (en) 2005-10-20
US20170231887A1 (en) 2017-08-17
BRPI0501718A (en) 2006-04-18
FR2868305B1 (en) 2006-06-30
KR20060045454A (en) 2006-05-17
US10702464B2 (en) 2020-07-07
EP1584329A1 (en) 2005-10-12
FR2868305A1 (en) 2005-10-07

Similar Documents

Publication Publication Date Title
US10702464B2 (en) Method for treating hair fibers
US5932201A (en) Reducing composition comprising a basic amino acid and a cationic polymer
US20080185014A1 (en) Method for permanently reshaping keratin fibers comprising applying a poorly concentrated reducing composition and intermediate drying
US20050232882A1 (en) Silicone composition-based hair fiber treating method
AU2004201433B2 (en) Hair treatment process and use of the process for smoothing the hair
US6187302B1 (en) Multi-component reducing agent and process for permanently reshaping the hair using this agent
JP6797515B2 (en) Permanent remolding method using a heating mechanical tensioning device
US5989534A (en) Process for the permanent deformation of keratinous matter
US5570708A (en) Process for the permanent reshaping of keratinous material
JPH0539211A (en) Reducing agent and cosmetic for human hair
US8313737B2 (en) Hair treatment process for smoothing the hair
US20050229336A1 (en) Method of treating hair fibers
US6238658B1 (en) Oxidizing agent containing several components and process for permanently reshaping the hair using this agent
US6623726B2 (en) Process for permanent reshaping of hair
JP2015508387A (en) How to treat keratin fibers
KR0162526B1 (en) Method for treating for permanent deformation of keratin substance
JP2000319143A (en) Permanent wave agent composition
ES2527035T5 (en) Hair treatment procedure and use of said procedure
JPH04295413A (en) Agent and method for permanent wave
JP2017105713A (en) Use of oleuropein or olea europaea l. leaf extract in cosmetics for permanent transformation of keratin fibers
EP4382172A1 (en) Composition for permanent shaping of human hair
JPH04154714A (en) Hair reducing agent and hair cosmetic

Legal Events

Date Code Title Description
FEPP Fee payment procedure

Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

STCF Information on status: patent grant

Free format text: PATENTED CASE

MAFP Maintenance fee payment

Free format text: PAYMENT OF MAINTENANCE FEE, 4TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1551); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

Year of fee payment: 4