US3252866A - 2-hydrocarbon substituted-amido mercaptopropionamides in hair waving compositions and processes - Google Patents

2-hydrocarbon substituted-amido mercaptopropionamides in hair waving compositions and processes Download PDF

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Publication number
US3252866A
US3252866A US467673A US46767365A US3252866A US 3252866 A US3252866 A US 3252866A US 467673 A US467673 A US 467673A US 46767365 A US46767365 A US 46767365A US 3252866 A US3252866 A US 3252866A
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United States
Prior art keywords
hair
processes
waving
employed
mercaptopropionamides
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Expired - Lifetime
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US467673A
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English (en)
Inventor
Sheffner Aaron Leonard
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Mead Johnson and Co LLC
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Mead Johnson and Co LLC
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Filing date
Publication date
Application filed by Mead Johnson and Co LLC filed Critical Mead Johnson and Co LLC
Priority to US467674A priority Critical patent/US3340147A/en
Priority to US467673A priority patent/US3252866A/en
Application granted granted Critical
Publication of US3252866A publication Critical patent/US3252866A/en
Priority to GB24965/66A priority patent/GB1144308A/en
Priority to GB25192/66A priority patent/GB1114369A/en
Priority to NL6608251A priority patent/NL6608251A/xx
Priority to NL6608252A priority patent/NL6608252A/xx
Priority to NO163503A priority patent/NO119638B/no
Priority to ES0328087A priority patent/ES328087A1/es
Priority to CH901366A priority patent/CH472890A/de
Priority to SE8610/66A priority patent/SE344409B/xx
Priority to FI661688A priority patent/FI48344C/fi
Priority to SE08609/66A priority patent/SE363095B/xx
Priority to DE19661543766 priority patent/DE1543766A1/de
Priority to FR66985A priority patent/FR5630M/fr
Priority to DK330866AA priority patent/DK115145B/da
Priority to DK330966AA priority patent/DK121762B/da
Priority to FR67129A priority patent/FR1484964A/fr
Priority to BR180766/66A priority patent/BR6680766D0/pt
Priority to BE683280D priority patent/BE683280A/xx
Priority to AT03654/68A priority patent/AT278735B/de
Priority to BE683281D priority patent/BE683281A/xx
Priority to CH934266A priority patent/CH503698A/de
Priority to CH1480169A priority patent/CH506502A/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur

Definitions

  • This invention relates to processes and compositions for the permanent deformation of human hair which have substantial and unexpected advantages over currently available methods. These processes and compositions relate to the so-called permanent waving of hair as well as to the corollary processes and compositions of straightening naturally or artificially curled hair.
  • the most common processes now in use for the permanent waving of hair by chemical methods comprise a first step in which the hair is impregnated with an aqueous solution containing one or more sulfhydryl compounds as a reducing agent for the disulfide linkages of the keratin, in order to impart plasticity to the hair and permit reshaping.
  • the sulfiiydryl compound thioglycolic acid is the only member of the class that has achieved any substantial degree of practical application. It has come to the fore because of its low cost and because the undesirable properties of the thiols as a class are exhibited to a minimum extent by this compound.
  • thioglycolate based waving lotions which results in hair damage reflected in loss in tensile strength thereof is to an extent an inherent characteristic of the thioglycolate ingredient. Furthermore, such lotions are unstable on exposure to the air.
  • One of the reasons for the inapplicability of certain other thiol compounds having the desired inherent activity is that undesirable deposits are left thereby on treated hair or the hair otherwise acquires an undesirable appearance or odor.
  • the present invention has among its objects:
  • compositions for use in the above processes which have a diminished propensity to damage the hair when used therein.
  • R and R are hydrogen atom or lower alkyl groups having up to about 4 carbon atoms.
  • R and R are each hydrogen atoms, the products are derivatives of the amino acid cysteine.
  • R and R are methyl groups, the products are derivatives of the amino acid penicillaminc.
  • R represents a hydrogen atom or the organic residue of the N-acyl group, in which event it is either an alkyl group, an aryl group, or an aralkyl group having up to 9 carbon atoms.
  • R and R are hydrogen atoms in the case of the simple amides which constitute preferred embodiments of the present invention. In other embodiments they represent the organic residues of N-substituted amides. More specifically, R is either a hydrogen atom, an alkyl, alkenyl, cycloalkyl, or cycloalkenyl group of up to 5 carbon atoms. To name a few representative residues, the following may be mentioned: methyl, ethyl, propyl, allyl, pentyl, butyl, tbutyl, cyclopentyl, cyclopentenyl, etc. R is either a hydrogen atom or a lower alkyl group of up to 4 carbon atoms.
  • R and R may be substituted by from 1 to 2 hydroxyl groups.
  • R and R may be connected to form together with the nitrogen atom a heterocyclic group such as piperidino, pyrrolidino, N- R -piperazino (in which R has the aforesaid meaning), morpholino, thiamorpholino, hexamethyleneimino, etc.
  • the cosmetic elegance of hair preparations containing compounds of Formula I combined with the physiologically acceptable nature and enhanced keratin reducing capacity thereof at near neutral pHs particularly adapts them for use in hair treatment processes.
  • the compounds of Formula I have remarkably little propensity to damage the hair or to cause it to be dry or brittle when used in permanent waving processes.
  • the present invention relates to a process which includes contacting hair with a solution of a compound of Formula I in order to form the hair into a predetermined configuration.
  • the present invention involves contacting clean human hair while confining it in the desired predetermined configuration with an aqueous solution of a compound of Formula I having a pH within the range of about pH 7.0 to pH 9.5 and a concentration thereof of from about 0.5% by weight up to a saturated solution, or up to about 20% by weight.
  • a sufficient period of time of contact with the solution to result in permanent deformation of the hair is employed. This period ranges from about 10' minutes to about 12 hours, depending upon the characteristics of the hair being treated, the temperature, the pH of the solution, and the concentration and species of compound of Formula I employed. It is Within the province of the 3 skilled operator to ascertain the optimum time period in any given situation.
  • Preferred compounds for use in accordance with the present invention include 2-acetamido-3-mercaptopropionamide, Z-acetamido 3 mercapto N methylpropionamide, and 2-propionamido-3-mercaptopropiffnide.
  • L-' 2-acetamido-3-rnercaptopropionamide has been shown to be a very non-toxic substance. In mice the LD' value is 2820 mg./kg. (intravenous administration). In rabbits after instillation of a 20% solution thereof into the eye, no ocular reaction whatever is evident employing the Draize method (Food, Drugs & Cosmetics 4951 (1959)) for determining toxicity to the eye mucosa.
  • Oxidizing agents that have been employed and which are suitable in the present process include hydrogen peroxide, the alkali metal bromates and iodates, the alkali metal perborates, etc.
  • Adjustment of the pH to within the specified range for hair-waving action can be accomplished, when necessary, by neutralization with a suitable base.
  • the bases employed for pH adjustment should be cosmetically acceptable. Sodium hydroxide, ammonia or ammonium hydroxide meet both of these standards. Other materials that are applicable include the sodium, potassium, and ammonium salts of cosmetically acceptable weak acids.
  • the cosmetically acceptable organic amineshaving basicities comparable to or greater than that of ammonia are suitable and in fact preferred. The pKb values of such amines are less than 5.0.
  • the following list includes a sampling of suitable bases for pH adjustment of waving solutions employed in the present process: sodium hydroxide, potassium hydroxide, ammonia, methylamine, ethylamine, propylamine, butylamine, dimethylamine, diethylamine, monoethanolamine, ethylenediamine, piperazine, tetramethylenediamine, and sodium, potassium, or ammonium salts of the following acids: lactic acid, acetic acid, carbonic acid, citric acid, etc. Monoethanolamine is the preferred base for pH adjustment. The preferred pH range is pH 8.0 to 9.5. It will be noted that most of the bases listed above are water-soluble materials indicative of the preference herein for bases of that type.
  • cosmetically acceptable as applied to ingredients of the present compostion is intended to refer to certain functional characteristics thereof.
  • cosmetically acceptable amines and salts are materials which are non-corrosive in the concentrations employed, which have low toxicities, and which lack irritating or sensitizing propensity.
  • such ingredients should not have undue or irreversible softening effect on the hair. They should not react With the sulfhydryl group of the compounds of Formula I under conditions of storage and use in an irreversible or destructive fashion as by oxidation, condensation, or precipitation. Furthermore, they should not evoke undesirable color reactions to the detriment of the appearance of the composition as a whole or the hair treated therewith.
  • Auxiliary materials of the sort employed in the hairwaving art are also suitable for use in the present processes. These include opacifiers and thickeners to impart a milky or creamy lotion-like consistency to the otherwise transparent solution of the described cysteine derivative.
  • opacifiers and thickeners to impart a milky or creamy lotion-like consistency to the otherwise transparent solution of the described cysteine derivative.
  • such ingredients as carboxymethyl cellulose, polyacrylates, polystyrene latex, emulsified oils, chlorinated hydrocarbons, pectins, gums, etc., can be employed.
  • use may be made of cosmetically acceptable perfumes and dyes if desired to lend elegance.
  • Additives of a functional nature can also be included, and in this regard it has been found that wetting agents and swelling agents can be incorporated to advantage into the com-positions employed in the present process.
  • Suitable wetting agents include the ionic and nonionic synthetic wetting agents and particularly detergents such as the sodium and potassium salts of the alkylsulfuric, alkylsulfonic, and aralkylsulfonic acids having at least 12 carbon atoms, polyoxyethylenes, polyoxypropylenes, and the ethers and esters thereof.
  • Wetting agents are employed in concentrations of from about 0.1% to 1.0% by weight.
  • urea As materials which are known to swell the hair sheath on contact therewith in water, urea, thiourea, methylurea, ethylurea, and the mineral acid salts of guanidine may be mentioned. Such materials can be included in the compositions in an amount of from about 1% to about 15% by weight of the waving solution as directed by properties affecting both function and elegance of the final product.
  • adjuvants that can be employed include agents to prevent overprocessing of the hair.
  • Materials which are known in the art to be applicable for this purpose include ammonium chloride, ammonium sulfate, ammonium phosphate, .and various other salts of weak bases and strong acids.
  • Example 1 A hair waving lotion is prepared from the following ingredients by preparing separate solutions of the ingredients shown in lists A and B.
  • List A contains the oil-soluble ingredients, and List B the water-soluble ingredients. The two solutions are warmed to C. before combining. After they are combined, a silicone antifoam agent, 0.01 g., is added thereto, the solution adjusted to pH 9.3 with monoethanolamine or ammonium hydroxide, and diluted to ml. with water.
  • This solution is employed according to the usual technique for applying a home permanent, including the steps of shampooing the hair, saturating the hair with the waving lotion, rolling the hair on curling rods, resaturating the rolled tresses with waving lotion, holding for a period of time suflicient in the judgment or" the operator for plasticity to develop, rinsing, and neutralizing with a 1.5% hydrogen peroxide solution. It is then rinsed, allowed to dry, and the curling rods removed.
  • Examples 2 and 3.Hair waving compositions are pre pared and used as described in Example 1 by substituting 5 g. of L-2-acetamido3-mercapto-N-methylpropionamide (Example 2) or g. of L-2-propionamido-3-mercaptopropionamide (Example 3) for the amount of L-Z-acetamido-3-mercaptopropionamide specified in Example 1.
  • a hair waving composition comprising a cosmetically acceptable aqueous solution having a pH between about pH 7 and pH 9.5 and containing from about 0.5% to about 20% by weight of a compound having the following formula:
  • R 0 ONH wherein R and R are hydrogen or alkyl of up to 4 carbon atoms;
  • R is hydrogen, alkyl, aralkyl, or aryl, each of up to 9 carbon atoms;
  • R is hydrogen, alkyl, alkenyl, cycloalkyl, or cycloalkenyl each of up to 5 carbon atoms and is unsubstituted or substituted by up to 2 hydroxyl groups;
  • R is hydrogen or lower alkyl of up to 4 carbon atoms and is unsubstituted or substituted by up to 2 hydroxyl groups.
  • the hair waving composition or" claim 1 wherein said composed is 2-acetarnido-3-mercapto-N-methylpropionamide.
  • composition of claim 1 wherein the concentration of said compound is from about 3% to about 10% by weight' 6.
  • concentration of said compound is from about 3% to about 10% by weight' 6.
  • pH is within the range of pH 8 to pH 9.5.
  • a process for permanently changing the configuration of hair without damage to the hair structure which includes the step of contacting the hair while in the desired configuration with a composition as claimed in claim 1.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Portable Nailing Machines And Staplers (AREA)
  • Pyrrole Compounds (AREA)
US467673A 1965-06-28 1965-06-28 2-hydrocarbon substituted-amido mercaptopropionamides in hair waving compositions and processes Expired - Lifetime US3252866A (en)

Priority Applications (23)

Application Number Priority Date Filing Date Title
US467674A US3340147A (en) 1965-06-28 1965-06-28 Amides of n-acylated cysteines
US467673A US3252866A (en) 1965-06-28 1965-06-28 2-hydrocarbon substituted-amido mercaptopropionamides in hair waving compositions and processes
GB24965/66A GB1144308A (en) 1965-06-28 1966-06-03 Hair waving composition and process
GB25192/66A GB1114369A (en) 1965-06-28 1966-06-06 Amides of n-acyl cysteines
NL6608251A NL6608251A (enrdf_load_stackoverflow) 1965-06-28 1966-06-14
NL6608252A NL6608252A (enrdf_load_stackoverflow) 1965-06-28 1966-06-14
NO163503A NO119638B (enrdf_load_stackoverflow) 1965-06-28 1966-06-17
ES0328087A ES328087A1 (es) 1965-06-28 1966-06-18 Un metodo de hacer una composicion para ondular el cabello.
CH901366A CH472890A (de) 1965-06-28 1966-06-22 Mittel zur bleibenden Verformung des Haares und dessen Verwendung
SE8610/66A SE344409B (enrdf_load_stackoverflow) 1965-06-28 1966-06-23
FI661688A FI48344C (fi) 1965-06-28 1966-06-23 Menetelmä limaa hajoittavien N-asyyli-kysteiiniamidien valmistamiseksi .
SE08609/66A SE363095B (enrdf_load_stackoverflow) 1965-06-28 1966-06-23
DE19661543766 DE1543766A1 (de) 1965-06-28 1966-06-24 Verfahren zur Herstellung von Amiden von N-Acylcysteinen
BR180766/66A BR6680766D0 (pt) 1965-06-28 1966-06-27 Processo para a preparacao de amidas de cisteinas n-a-ciladas
FR66985A FR5630M (enrdf_load_stackoverflow) 1965-06-28 1966-06-27
DK330866AA DK115145B (da) 1965-06-28 1966-06-27 Middel til bølgning eller udglatning af hår.
DK330966AA DK121762B (da) 1965-06-28 1966-06-27 Analogifremgangsmåde til fremstilling af N-acylerede cysteinforbindelser.
FR67129A FR1484964A (fr) 1965-06-28 1966-06-27 Cystéines nu-acylées et procédé de préparation de leurs amides ainsi que de compositions utilisées pour l'ondulation des cheveux et contenant ces amides
BE683280D BE683280A (enrdf_load_stackoverflow) 1965-06-28 1966-06-28
AT03654/68A AT278735B (de) 1965-06-28 1966-06-28 Verfahren zur herstellung von neuen amiden von n-acylcysteinen
BE683281D BE683281A (enrdf_load_stackoverflow) 1965-06-28 1966-06-28
CH934266A CH503698A (de) 1965-06-28 1966-07-28 Verfahren zur Herstellung von Amiden von N-Acylcysteinen
CH1480169A CH506502A (de) 1965-06-28 1966-07-28 Verfahren zur Herstellung von Amiden von N-Acyl-cysteinen

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US467673A US3252866A (en) 1965-06-28 1965-06-28 2-hydrocarbon substituted-amido mercaptopropionamides in hair waving compositions and processes
US467674A US3340147A (en) 1965-06-28 1965-06-28 Amides of n-acylated cysteines

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US3252866A true US3252866A (en) 1966-05-24

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US467673A Expired - Lifetime US3252866A (en) 1965-06-28 1965-06-28 2-hydrocarbon substituted-amido mercaptopropionamides in hair waving compositions and processes
US467674A Expired - Lifetime US3340147A (en) 1965-06-28 1965-06-28 Amides of n-acylated cysteines

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US467674A Expired - Lifetime US3340147A (en) 1965-06-28 1965-06-28 Amides of n-acylated cysteines

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US (2) US3252866A (enrdf_load_stackoverflow)
AT (1) AT278735B (enrdf_load_stackoverflow)
BE (2) BE683281A (enrdf_load_stackoverflow)
BR (1) BR6680766D0 (enrdf_load_stackoverflow)
CH (2) CH472890A (enrdf_load_stackoverflow)
DE (1) DE1543766A1 (enrdf_load_stackoverflow)
DK (2) DK115145B (enrdf_load_stackoverflow)
FI (1) FI48344C (enrdf_load_stackoverflow)
FR (1) FR5630M (enrdf_load_stackoverflow)
GB (2) GB1144308A (enrdf_load_stackoverflow)
NL (2) NL6608251A (enrdf_load_stackoverflow)
NO (1) NO119638B (enrdf_load_stackoverflow)
SE (2) SE363095B (enrdf_load_stackoverflow)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3340147A (en) * 1965-06-28 1967-09-05 Mead Johnson & Co Amides of n-acylated cysteines
US3975515A (en) * 1973-09-29 1976-08-17 Wella Ag Reducing the alkali concentration in hair treating compositions
US4992267A (en) * 1988-04-28 1991-02-12 Johnson Products Co., Inc. Hair straightening composition and system
US20020107176A1 (en) * 1997-12-23 2002-08-08 Daphne Atlas Brain targeted low molecular weight hydrophobic anti oxidant compounds
US20020159962A1 (en) * 2001-02-22 2002-10-31 Cannell David W. Hair relaxer compositions comprising at least one hydroxide compound and at least one activating agent, and methods of using the same
US20030033677A1 (en) * 2001-08-20 2003-02-20 Nguyen Nghi Van Compositions comprising at least one hydroxide compound and at least one reducing agent, and methods for relaxing hair
US20030037384A1 (en) * 2001-08-20 2003-02-27 Nguyen Nghi Van Compositions comprising at least one hydroxide compound and at least one oxidizing agent, and methods to straighten curly hair

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4061634A (en) * 1976-11-01 1977-12-06 The United States Of America As Represented By The Secretary Of Agriculture Sulfur-containing antimicrobial ester-amides
US4440788A (en) * 1980-05-13 1984-04-03 Mitsubishi Chemical Industries, Limited Cysteine derivatives
US5378729A (en) * 1985-02-15 1995-01-03 Research Corporation Technologies, Inc. Amino acid derivative anticonvulsant
US5654301A (en) * 1985-02-15 1997-08-05 Research Corporation Technologies, Inc. Amino acid derivative anticonvulsant
US5165427A (en) * 1991-07-16 1992-11-24 Helene Curtis, Inc. Cysteinamide--containing permanent wave composition and method
US5874468A (en) * 1996-12-26 1999-02-23 Yissum Brain targeted low molecular weight hydrophobic antioxidant compounds
CN1261878A (zh) * 1997-05-07 2000-08-02 柏林马克斯普朗克科学促进协会 新的半胱氨酸衍生物,它们的制备方法和含有它们的药物
CA2346700A1 (en) * 1998-10-09 2000-04-20 Ajinomoto Co., Inc. Cysteine derivatives
FR2878435B1 (fr) * 2004-11-26 2009-04-03 Oreal Procede de defrisage des fibres keratiniques avec un moyen de chauffage et un agent denaturant
WO2016077467A1 (en) 2014-11-11 2016-05-19 The Johns Hopkins University Biomarkers useful in the treatment of subjects having diseases of the eye
CN111386255B (zh) 2017-09-20 2021-11-23 纳崔泰制药有限公司 用于制备n-乙酰基半胱氨酸酰胺及其衍生物的方法
US11091433B2 (en) 2017-09-20 2021-08-17 Nacuity Pharmaceutials, Inc. Method for preparation of N-acetyl cysteine amide and derivatives thereof
US11548851B2 (en) 2017-09-20 2023-01-10 Nacuity Pharmaceuticals, Inc. Method for preparation of n-acetyl cysteine amide and derivatives thereof
US20190135741A1 (en) 2017-11-09 2019-05-09 Nacuity Pharmaceuticals, Inc. Methods of Making Deuterium-Enriched N-acetylcysteine Amide (D-NACA) and (2R, 2R')-3,3'-Disulfanediyl BIS(2-Acetamidopropanamide) (DINACA) and Using D-NACA and DINACA to Treat Diseases Involving Oxidative Stress
WO2020146674A1 (en) 2019-01-11 2020-07-16 Nacuity Pharmaceuticals, Inc. Treatment of age-related macular degeneration, glaucoma, and diabetic retinopathy with n-acetylicysteine amide (naca) or 2r,2r')-3-3'-disulfanediyl bis (2-acetamidopropanamide) (dinaca)
WO2020146660A1 (en) 2019-01-11 2020-07-16 Nacuity Pharmaceuticals, Inc. N-acetylcysteine amide (naca) and (2r,2r')-3-3'-disulfanediyl bis (2-acetamidopropanamide) (dinaca) for prevention and treatment of radiation pneumonitis and treatment of pulmonary function in cystic fibrosis

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3252866A (en) * 1965-06-28 1966-05-24 Mead Johnson & Co 2-hydrocarbon substituted-amido mercaptopropionamides in hair waving compositions and processes

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3340147A (en) * 1965-06-28 1967-09-05 Mead Johnson & Co Amides of n-acylated cysteines
US3975515A (en) * 1973-09-29 1976-08-17 Wella Ag Reducing the alkali concentration in hair treating compositions
US4992267A (en) * 1988-04-28 1991-02-12 Johnson Products Co., Inc. Hair straightening composition and system
US20020107176A1 (en) * 1997-12-23 2002-08-08 Daphne Atlas Brain targeted low molecular weight hydrophobic anti oxidant compounds
US20020159962A1 (en) * 2001-02-22 2002-10-31 Cannell David W. Hair relaxer compositions comprising at least one hydroxide compound and at least one activating agent, and methods of using the same
US7118736B2 (en) 2001-02-22 2006-10-10 L'oreal Hair relaxer compositions comprising at least one hydroxide compound and at least one activating agent, and methods of using the same
US20030033677A1 (en) * 2001-08-20 2003-02-20 Nguyen Nghi Van Compositions comprising at least one hydroxide compound and at least one reducing agent, and methods for relaxing hair
US20030037384A1 (en) * 2001-08-20 2003-02-27 Nguyen Nghi Van Compositions comprising at least one hydroxide compound and at least one oxidizing agent, and methods to straighten curly hair
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
US7468180B2 (en) 2001-08-20 2008-12-23 L'oreal, S.A. Compositions comprising at least one hydroxide compound and at least one oxidizing agent, and methods to straighten curly hair

Also Published As

Publication number Publication date
NO119638B (enrdf_load_stackoverflow) 1970-06-15
FR5630M (enrdf_load_stackoverflow) 1967-12-18
SE344409B (enrdf_load_stackoverflow) 1972-04-17
DK115145B (da) 1969-09-08
DK121762B (da) 1971-11-29
NL6608252A (enrdf_load_stackoverflow) 1966-12-29
BE683281A (enrdf_load_stackoverflow) 1966-12-28
BR6680766D0 (pt) 1973-12-26
CH503698A (de) 1971-02-28
GB1144308A (en) 1969-03-05
NL6608251A (enrdf_load_stackoverflow) 1966-12-29
FI48344B (enrdf_load_stackoverflow) 1974-05-31
BE683280A (enrdf_load_stackoverflow) 1966-12-28
US3340147A (en) 1967-09-05
SE363095B (enrdf_load_stackoverflow) 1974-01-07
CH472890A (de) 1969-05-31
GB1114369A (en) 1968-05-22
FI48344C (fi) 1974-09-10
DE1543766A1 (de) 1970-01-02
AT278735B (de) 1970-02-10

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