US3218234A - Treatment of proteinaceous materials with pyruvic acid or glyoxylic acid to remove peroxides - Google Patents

Treatment of proteinaceous materials with pyruvic acid or glyoxylic acid to remove peroxides Download PDF

Info

Publication number
US3218234A
US3218234A US280107A US28010763A US3218234A US 3218234 A US3218234 A US 3218234A US 280107 A US280107 A US 280107A US 28010763 A US28010763 A US 28010763A US 3218234 A US3218234 A US 3218234A
Authority
US
United States
Prior art keywords
peroxide
acid
fibers
proteinaceous
treatment
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.)
Expired - Lifetime
Application number
US280107A
Other languages
English (en)
Inventor
Wilmsmann Hermann
Konrad Eugen
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.)
WILMSMANN
Original Assignee
WILMSMANN
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
Application filed by WILMSMANN filed Critical WILMSMANN
Application granted granted Critical
Publication of US3218234A publication Critical patent/US3218234A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts
    • D06P3/305—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts with oxidation dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/08—Preparations for bleaching the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
    • D06L4/15—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen using organic agents
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/207—Substituted carboxylic acids, e.g. by hydroxy or keto groups; Anhydrides, halides or salts thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00—Drug, bio-affecting and body treating compositions
    • Y10S424/02—Resin hair settings
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00—Drug, bio-affecting and body treating compositions
    • Y10S424/03—Hair bleach

Definitions

  • hydroperoxides are for-med in proteinaceous fibers upon exposure to ultraviolet radiation or in moist condition. It is also known that after an intentional treatment of such fibers with hydrogen-peroxide, residual hydroperoxide remains in the proteinaceous fiber and this peroxide residue will not be removed even upon intensive rinsing. The hydroperoxides which thus remain in the proteinaceous fibers will cause a certain degree of bleaching of the fibers as well as damage to the fiber structure. The unfavorable effect of residual hydroperoxide on proteinaceous fibers becomes apparent, for instance by bleaching human hair in accordance with the method disclosed in US. Patent 1,750,657. Upon subsequent dyeing of the thus-bleached hair with oxidation dyestuffs or nitroa-minobenzenes, it is generally not possible to achieve uniform dyeing of the hair.
  • Thiosulfate, dithionite, hypophosphites, and ascorbic acid are effective only in an alkaline .pH range.
  • the treating agent is supposed not only to remove hydrogen peroxide residue but also alkaline residues. This is important, for instance, when the removal of peroxide residue is to be carried out as aftertreatment subsequent to permanent waving, bleaching or hair dyeing.
  • An after-treatment which would lead to the destruction of hydrogen peroxide only in an alkaline pH range would then require a further after-treatment with an acidic agent in order to eliminate alkali residues, and this would considerably prolong the total treating time and make the treatment more expensive.
  • thiourea Of the peroxide destroying agents mentioned so far, only thiourea will also be effective in an acidic pH range and does not have the disadvantages which are characteristic for catalase. For this reason, thiourea is presently extensively used in the treatment of human hair. However, the use of thiourea is frequently unpleasant due to the odor given thereby to the treated hair, as well as due to the unpleasant change in the odor of the thiourea-containing hair treating agent, which is observed not only during treatment but also upon prolonged storage of the treating agent. The cause of this unpleasant odor, i.e.
  • the present invention includes a method of treating peroxide-containing proteinaceous material, comprising the step of contacting the material with a substance selected from the group consisting of alpha-carbonyl-monocarboxylic acids of the general formula RCOCOOH, wherein R is selected from the group consisting of hydrogen and alkyls having up to 5 carbon atoms, and salts thereof.
  • pyruvic acid and glyoxylic acid is well as the wateror alcohol-soluble salts thereof.
  • the following salts thereof may be advantageously used: sodium, potassium, ammonium, calcium, magnesium, aluminum salts, as well as organic amines such as monoethanolamine, diethanolamine, triethanolamine, butylamine, isopropanolamine, and trishydroxymethyl-aminomethane salts.
  • organic amines such as monoethanolamine, diethanolamine, triethanolamine, butylamine, isopropanolamine, and trishydroxymethyl-aminomethane salts.
  • the salts of the heavy metals as well as of barium and strontium are to be excluded.
  • the reactants described above will be applied distributed in suitable carriers, for instance dissolved in water or aqueous alcohol, or in the form of a suitable cream or paste, whereby the concentration of the alpha-monocarboxylic acid or salt preferably will be between 0.5 and 4% by weight, and in most cases between about 1 and 2%. If the free acid is used, then best results will be frequently obtained with a concentration of about 1%, While the salts are preferably used in a concentration of about 2%, whereby all percentage figures are intended to indicate percent by weight.
  • reaction products obtained by the reaction of the above-mentioned acids or salts with the peroxide of the proteinaceous fibers are completely harmless substances which, in addition, will cause a desirable acidification of the fibers.
  • the alpha-carbonyl-monocarboxylic acids and their salts which may be used according to the present invention are also capable to react by means of their reactive carbonyl group with SI-I, NHzor peptide groups of the proteinaceous fibers and thereby to cause cross linking or blocking of active groups which in turn will improve the structure and reduce the reactivity of the proteinaceous fibers.
  • the alpha-carbonyl-monocarboxylic acids and their soluble salts may be distributed in a carrier substance which after being in contact with the hair or the like for a limited period of time is again removed, preferably by rinsing, or the reactants according to the present invention may also be incorporated in carrier substances which after being applied to, for instance, human hair are not removed therefrom, such as setting agents.
  • alpha-carbonyl-monocarboxylic acids and their salts which are used according to the present invention may be incorporated in all conventional types of hair treating agents such as aqueous, alcoholic or aqueousalcoholic solutions, emulsions and the like.
  • EXAMPLE I A permanent Wave is applied to living human hair by means of a conventional solution of thioglycolate, fixed in conventional manner with hydrogen peroxide and thereafter the hair is treated for about five minutes with one of the following solutions:
  • Solution B 2.0 g. of the sodium, potassium, ammonium, calcium,
  • EXAMPLE III EXAMPLE IV Human hair is bleached in conventional manner with potassium persulfate in accordance with the method disclosed in the US. Patent 1,750,657, and thereafter treated with any one of the solutions of Examples I and II.
  • the thus treated hair may now be dyed with a solution of 0.12% 2-nitro-l,4-phenylenediamine and 1% of an aqueous 25% ammonia solution, the balance, i.e. 98.98% being water, and thereby the desired uniform coloration of the dyed hair will be achieved, while similarly bleached hair which has not been subjected to the intermediate treatment according to the present invention, upon dyeing in the above described manner, will be of spotty appearance.
  • EXAMPLE VI Raw wool is bleached as described in Example VI, rinsed with water for a short period of time and then treated for several minutes with a 4% aqueous solution of glyoxylic acid. No residual peroxide can be found in the thus-treated wool which is of acidic pH.
  • EXAMPLE VIII Human hair is wetted with a setting agent as described in Example V, in which the 1.0 g. of the sodium salt of pyruvic acid is replaced by 0.5 g. of pyruvic acid. The hair is then set in the desired shape and dried. After wetting the thus treated hair and even upon exposure to ultra violet rays, it is not possible to determine the presence of hydroperoxide therein.
  • a method of treating peroxide-containing proteinaceous fibers selected from the group consisting of human hair and wool for the removal of peroxide therefrom comprising the step of contacting said peroxide-containing fibers with a substance selected from the group consisting of pyruvic acid, glyoxylic acid, and their sodium potassium, ammonium, calcium, magnesium, aluminum and organic amine salts.
  • a method of treating peroxide-containing proteinaceous fibers selected from the group consisting of human hair and wool for the removal of peroxide therefrom comprising the step of contacting said peroxide-containing fibers in an acidic medium with a substance selected a from the group consisting of pyruvic acid, glyoxylic acid, and their sodium, potassium, ammonium, calcium, magnesium, aluminum and organic amine salts.
  • a method of treating peroxide-containing proteinaceous fibers selected from the group consisting of human hair and wool for the removal of peroxide therefrom comprising the step of contacting said peroxide-containing fibers in an acidic medium with a carrier substance compatible with said fibers and having distributed therethrough between about 0.5 and 4% of a substance selected from the group consisting of pyruvic acid, glyoxylic acid, and their sodium, potassium, ammonium, calcium, magnesium, aluminum and organic amine salts.
  • a method of treating peroxide-containing proteinaceous fibers selected from the group consisting of human hair and wool for the removal of peroxide therefrom comprising the step of contacting said peroxide-containing fibers in an acidic medium with an aqueous solution compatible with said fibers and having distributed therethrough between about 0.5 and 4% of a substance selected from the group consisting of pyruvic acid, glyoxylic acid, and their sodium, potassium, ammonium, calcium, magnesium, aluminum and organic amine salts.
  • a method of treating peroxide-containing proteinaceous fibers selected from the group consisting of human hair and wool for the removal of peroxide therefrom comprising the step of contacting said peroxide-containing fibers in an acidic medium with a carrier substance compatible with said fibers and having distributed therethrough between about 1 and 2% of a substance selected from the group consisting of pyruvic acid, glyoxylic acid, and their sodium, potassium, ammonium, calcium, magnesium, aluminum and organic amine salts.
  • a method of treating peroxide-containing proteinaceous fibers selected from the group consisting of human hair and wool for the removal of peroxide therefrom comprising the step of contacting said peroxide-containing fibers in an acidic medium with a carrier substance compatible with said fibers and having distributed therethrough about 1% by weight of a substance selected from the group consisting of pyruvic acid and glyoxylic acid.
  • a method of treating peroxide-containing proteinaceous fibers selected from the group consisting of human hair and wool for the removal of peroxide therefrom comprising the step of contacting said peroxide-containing fibers with a carrier substance compatible therewith and having distributed therethrough between about 0.5 and 4% by weight of pyruvic acid.
  • a method of treating peroxide-containing proteinaceous fibers selected from the group consisting of human hair and wool for the removal of peroxide therefrom comprising the step of contacting said peroxide-containing fibers with a carrier substance compatible therewith and having distributed therethrough between about 0.5 and 4% by weight of glyoxylic acid.
  • a method of treating peroxide-containing proteinaceous fibers selected from the group consisting of human hair and wool for the removal of peroxide therefrom comprising the step of contacting said peroxide-containing fibers in an acidic medium with a carrier substance compatible with said fibers and having distributed therethrough about 2% by weight of a substance selected from the group consisting of alkali metal, ammonium, calcium, magnesium, aluminum and organic amino salts of pyruvic acid and glyoxylic acid.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
US280107A 1962-05-17 1963-05-13 Treatment of proteinaceous materials with pyruvic acid or glyoxylic acid to remove peroxides Expired - Lifetime US3218234A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEW32278A DE1158213B (de) 1962-05-17 1962-05-17 Haarbehandlungsmittel

Publications (1)

Publication Number Publication Date
US3218234A true US3218234A (en) 1965-11-16

Family

ID=7599991

Family Applications (1)

Application Number Title Priority Date Filing Date
US280107A Expired - Lifetime US3218234A (en) 1962-05-17 1963-05-13 Treatment of proteinaceous materials with pyruvic acid or glyoxylic acid to remove peroxides

Country Status (5)

Country Link
US (1) US3218234A (d)
BE (1) BE631957A (d)
DE (1) DE1158213B (d)
GB (1) GB1006195A (d)
NL (1) NL292754A (d)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3649159A (en) * 1968-06-03 1972-03-14 Fmc Corp Hair coloring method using a peroxydiphosphate oxidant
US3793210A (en) * 1969-06-20 1974-02-19 Colgate Palmolive Co Keto acid containing compositions
US3906091A (en) * 1969-12-24 1975-09-16 Oreal Hair-setting lotion containing a reducing agent
US3988110A (en) * 1969-12-24 1976-10-26 Societe Anonyme Dite: L'oreal Hair coloring and hair-setting lotion containing a direct dye, a reducing agent and a solar filter
JPS55130908A (en) * 1979-03-29 1980-10-11 Wella Ag Hair permanent wave posttreating agent
US4294852A (en) * 1973-11-01 1981-10-13 Johnson & Johnson Skin treating compositions
US4786493A (en) * 1985-11-22 1988-11-22 Estee Lauder Inc. Hair protection composition
US6106579A (en) * 1998-03-12 2000-08-22 Wella Aktiengesellschaft Compositions and methods for dyeing and safe decolorizing of fibers, especially hair, and multi-part kit for repeatedly changing dyed fiber color
WO2014067703A3 (en) * 2012-11-05 2014-07-17 Kao Corporation Process for straightening and bleaching hair
WO2014068101A3 (en) * 2012-11-05 2014-07-17 Kao Corporation Process for bleaching and straightening hair
WO2014068102A3 (en) * 2012-11-05 2014-07-17 Kao Corporation Process for dyeing and straightening hair
EP3141284B1 (fr) 2006-05-24 2019-08-28 L'Oréal Procede de defrisage des fibres keratiniques avec un moyen de chauffage et un derive d'acide

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5254336A (en) * 1992-09-24 1993-10-19 Helene Curtis, Inc. Method of increasing hair shine and repairing alkaline-damaged hair
CN109183177A (zh) * 2018-08-08 2019-01-11 内蒙古石墨烯材料研究院 一种高强高模的对位芳纶纤维及制备方法和应用
CN109972390B (zh) * 2019-03-15 2020-02-07 江南大学 一种利用蛋白酶k对羊毛织物进行防毡缩整理的方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1210394A (en) * 1914-12-10 1917-01-02 Roessler & Hasslacher Chemical Process of finishing animal filaments, fibers, or threads.
US2892756A (en) * 1955-10-06 1959-06-30 Flesch Peter Method for protecting, dyeing, and waving peroxide bleach-damaged keratin

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1210394A (en) * 1914-12-10 1917-01-02 Roessler & Hasslacher Chemical Process of finishing animal filaments, fibers, or threads.
US2892756A (en) * 1955-10-06 1959-06-30 Flesch Peter Method for protecting, dyeing, and waving peroxide bleach-damaged keratin

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3649159A (en) * 1968-06-03 1972-03-14 Fmc Corp Hair coloring method using a peroxydiphosphate oxidant
US3793210A (en) * 1969-06-20 1974-02-19 Colgate Palmolive Co Keto acid containing compositions
US3906091A (en) * 1969-12-24 1975-09-16 Oreal Hair-setting lotion containing a reducing agent
US3988110A (en) * 1969-12-24 1976-10-26 Societe Anonyme Dite: L'oreal Hair coloring and hair-setting lotion containing a direct dye, a reducing agent and a solar filter
US4294852A (en) * 1973-11-01 1981-10-13 Johnson & Johnson Skin treating compositions
JPS55130908A (en) * 1979-03-29 1980-10-11 Wella Ag Hair permanent wave posttreating agent
US4786493A (en) * 1985-11-22 1988-11-22 Estee Lauder Inc. Hair protection composition
US6106579A (en) * 1998-03-12 2000-08-22 Wella Aktiengesellschaft Compositions and methods for dyeing and safe decolorizing of fibers, especially hair, and multi-part kit for repeatedly changing dyed fiber color
EP3141284B1 (fr) 2006-05-24 2019-08-28 L'Oréal Procede de defrisage des fibres keratiniques avec un moyen de chauffage et un derive d'acide
WO2014067703A3 (en) * 2012-11-05 2014-07-17 Kao Corporation Process for straightening and bleaching hair
WO2014068101A3 (en) * 2012-11-05 2014-07-17 Kao Corporation Process for bleaching and straightening hair
WO2014068102A3 (en) * 2012-11-05 2014-07-17 Kao Corporation Process for dyeing and straightening hair

Also Published As

Publication number Publication date
BE631957A (d)
DE1158213B (de) 1963-11-28
NL292754A (d)
GB1006195A (en) 1965-09-29

Similar Documents

Publication Publication Date Title
US3218234A (en) Treatment of proteinaceous materials with pyruvic acid or glyoxylic acid to remove peroxides
US3892845A (en) Hair shade adjuster
US3194734A (en) Processes and compositions for dyeing hair and similar fibres
DE3886867T2 (de) Haarpflegemittel.
US3973574A (en) Waving and straightening hair by producing metal chelates in the keratin of the hair
US5332570A (en) Reducing solution for permanent wave
JPS5939402B2 (ja) アルカリ反応性化粧品の活性濃度の減下方法
ES2078129T3 (es) Agente para teñir y enrubiar cabellos humanos y procedimiento para su preparacion.
US4459284A (en) Permanent waving composition comprising amino acids
EP0113418A1 (en) Hair cosmetic composition
RU2669345C2 (ru) Состав для обесцвечивания волос
GB1426450A (en) Self-heated compositions for carrying out the second stage of permanent waving of hair two compartment packs for the pro duction thereof and processes for permanently waving hair using the compositions
US2875769A (en) Keratinaceous fiber dye of hydroquinone and either dihydroxyphenylalanine or dihydroxyphenylglycine and method of its use
US3190803A (en) Pvp-formamidine sulfinic acid color stripping medium
US5103522A (en) Sequential oxidative and reductive bleaching in a multicomponent single liquor system
US2564722A (en) Process for treating hair to impart a permanent set thereto
US3649159A (en) Hair coloring method using a peroxydiphosphate oxidant
US3651209A (en) Hydrogen peroxide-persulfate hair bleaching enhanced by ammonium or an alkali metal peroxydiphosphate
US4322401A (en) Permanent-wave solution
US3676546A (en) Neutralizing compositions for permanent wave operation
JPH01254617A (ja) Ｎ―置換された―５，６―ジヒドロキシインド―ルの毛髪着色剤としての使用法
JPH01501003A (ja) 毛髪の色を永久的に変えるのに使用する組成物
JP2927526B2 (ja) 毛髪セット加工用前処理剤
US3143476A (en) Cold wave neutralizing composition and process
US3063908A (en) Process for permanent deformation of hair