US3242052A - Hair treatment with nu-acylcysteines - Google Patents

Hair treatment with nu-acylcysteines Download PDF

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Publication number
US3242052A
US3242052A US301843A US30184363A US3242052A US 3242052 A US3242052 A US 3242052A US 301843 A US301843 A US 301843A US 30184363 A US30184363 A US 30184363A US 3242052 A US3242052 A US 3242052A
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hair
cysteine
solution
carbon atoms
sodium
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Expired - Lifetime
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US301843A
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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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Priority to US301843A priority Critical patent/US3242052A/en
Priority to GB35105/63A priority patent/GB1002889A/en
Priority to FR947595A priority patent/FR1375958A/fr
Priority to DEM58257A priority patent/DE1208450B/de
Priority to CH753364A priority patent/CH462386A/de
Priority to NL6406777A priority patent/NL6406777A/xx
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Publication of US3242052A publication Critical patent/US3242052A/en
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    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
    • 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

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 sulfhydryl 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 and large excesses of the material are frequently required.
  • 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 therefore, has along its objects:
  • compositions for use in the above processes which have a diminished propensity to damage the hair when used therein.
  • the present invention relates to a process which includes contacting hair with a solution of N- alkanoylcysteine or N-aroylcysteine 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 lower N-alkanoylcysteine or an N-aroylcysteine having a pH within the range of about pH 7.0 to pH 9.5 and a concentration thereof of about 3% to about 20% by weight.
  • a suificient period of time of contact with the solution to result in permanent deformation of the hair is employed. This period ranges from about 10 min.
  • Preferred lower N-alkanoylcysteines include N-acetylcysteine, N-propionylcysteine, N-butyrylcysteine, N-valerylcysteine, N-caproylcysteine and N-heptanoylcysteine of either the D or L configuration or mixtures thereof.
  • Preferred N-aroylcysteines include N-benzoylcysteine, N-toluoylcysteine, N-(ethylbenzoy1)cysteine, and N-(propylbenzoyl)cysteine.
  • the preferred species of waving agent for use in the present process is N-acetyl-L-cysteine.
  • L-form is preferred on the basis of economic factors, L-cysteine from which it is made being commercially available from sources such as feathers, hoofs, etc.
  • N-acetyl-DLcysteine is equally effective and may be preferred where it can be obtained more cheaply, for instance, by total synthesis.
  • FIGURE 1 is a diagram of load elongation behavior of various hair samples treated according to the present invention and with a thioglycolate preparation as described in Example 9.
  • This diagram shows that hair treated with a 10% (0.6 molar) aqueous solution of N-acetyl-L-cysteine having a pH of 9.3, sample C, is not significantly damaged relative to sample A, the untretated control tress.
  • the sample treated with an 0.6 molar solution of thioglycolic acid having a pH 9.3 (sample B) was significantly damaged.
  • N-acetyl-L-cysteine has been shown to be essentially nontoxic on oral administration or by inhalation of an aerosol thereof. It is not harmful to the mucous membranes of the conjuctiva or the nasal passages, nor does it interfere with tracheal ciliary activity. It has been shown to lack sensitizing potential in both guinea pigs and human beings on repeated exposure thereto.
  • fixing means When the term fixing means is employed in describing the present invention, it is intended to refer to the step of exposing the hair which has been plasticized by means of contact with a solution of a lower N-alkanoylcysteine or N-aroylcysteine to conditions of oxidation, permitting regeneration of the cystine disulfide bonds of the keratin.
  • 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.
  • the described cysteine derivatives have an acid strength similar to that of acetic acid
  • neutralization of solutions thereof with a suitable base is preferably employed to adjust the pH to within the specified range for hair-waving action.
  • the bases employed for pH adjustment should be sufliciently strong to neutralize the cysteine derivative, and 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 acids having pK values in excess of 3.2.
  • the cosmetically acceptable organic amines having basicities comparable to or greater than that of ammonia are suitable and in fact preferred. The pK 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 9.0 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 composition 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 efiect on the hair. They should not react with the sulfhydryl group of either the lower N-alkanoylcysteine or N-aroylcysteine 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 are carboxymethyl cellulose, polyacrylates, polystyrene latex, emulsified oils, chlorinated hydrocarbons, pectins, gums, etc., can be employed.
  • use may made of cosmetically acceptable perfumes and dyes if desired to lend elegance.
  • wetting agents and swelling agents can be incorporated to advantage into the compositions 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, polyoxythylenes, 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 are 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 2 The following waving solutions were compared in an experiment employing identical tresses of human hair. The compositions of these solutions are listed below as percent by weight of final solution. A fixing solution of 4.2 g. of sodium perborate monohydrate and 1.0 g. of sodium hexametaphosphate dissolved in 475 ml. of water was employed.
  • Example 3 Cornparative experiments employing the Waving solutions listed below and identical tresses of virgin human hair 6 inches in length and weighing approximately 1 g. each were conducted.
  • Example 4 A waving solution containing 10% N-acetyl-L-cysteine and 0.1% ethylene oxide-propylene oxide polymer having molecular weight 1750 (Pluronic F68, Wyandotte Chemicals Corporation, Wyandotte, Michigan) was compared in effectiveness to a commercial waving lotion determined by analysis to contain 5.52% ammonium thioglycolate as waving agent and having pH 9.25. The experiment was conducted on separate tresses of virgin human hair as described in the preceding example, but using a processing time of 15 min. Curls of equivalent tightness were obtained in each instance but the tress curled by the N-acetylcysteine solution was softer and had a more natural texture.
  • N-aoetylcysteine solution containing the following wetting agents: 1% by weight of Pluronic F68, 0.1% sodium lauryl sulfate, or 0.5% of polysorbate 80, and 1% of sodium dodecylbenzene sulfonate.
  • Example 5 -A further experiment on individual hair tresses as described in Example 3 was conducted. In this experiment three waving solutions having the following composition but adjusted respectively to pH 7, pH 8, and pH 9 were compared.
  • Example 6 A waving lotion having the composition given below is prepared.
  • the mineral oil and liquid lanolin are included to provide a cream-like appearance for cosmetic elegance.
  • the polyoxyethylene ingredients are non-ionic wetting agents included to improve wavingefliciency and to assist in emulsification of the oils.
  • the silicone antifoa-m is for manufacturing convenience and the disodium ethylene-diaminetetraacetic acid is a chela-ting agent which increases storage stability of the finished composition.
  • N-acetyl-L-cysteine is the waving agent.
  • Monoethanolam'ine is selected for pH adjustment since it has been observed that compositions containing it provide better-textured waves.
  • Distilled Water is the vehicle.
  • a perfume ingredient may also be employed if desired.
  • Preparation of the composition includes the following steps. Solutions of .the oil soluble and water soluble ingredients, designated by A and B above are prepared and warmed to 70 C. They are then combined and the silicone antifoam agent added. The pH of the mixture is then further adjusted if necessary and diluted to volume with water as a final step.
  • Example 7 Permanent waves were applied to seven subjects in accordance with the usual technique involved in the use of permanent wave lotions including the steps of shampooing the hair, saturating with the waving solution, rolling the hair on curling rods, resaturating on the rods with waving solution, holding for a period of time which in the judgment of the operator is suflicient to impart a curl, rinsing, and neutralizing with a 1.5% hydrogen peroxide solution to serve as a fixing solution.
  • Min. 3 subjects 15 1 subject 17 1 subject 20 1 subject 30 1 subject 60 After saturation of the hair on the curling rods with the fixing solution, it was let down, resaturated with fixing solution, rinsed, set on rollers, and allowed .to dry. On removing the rollers, waves were obtained which were considered satisfactory by the operator and each of the subjects.
  • Example 8 A waving lotion similar to that of Example 6 was compared in effectiveness to a commercial Waving lotion of the home permanent type having pH 9.25 which was determined by analysis to contain 5 52% ammonium thioglycolate as waving agent.
  • the half head technique in which the permanent wave is applied using one lotion on the left-hand portion of the head and a second lotion on the right-hand portion of the head was employed on five subjects.
  • the permanent Waves were applied manually by a licensed beauty operator according to the usual technique as outlined in Example 7. The most striking difference between the two products which was observed by the operator in all cases was the greater ease with which the hair which had been treated with the lotion of Example 6 could be combed. There was a striking absence of tangled hair ends as was encountered with the commercial product.
  • Example 9 -Individual tresses of virgin human hair, 6 inches in length and weighing approximately 1 g. each were separately immersed in loose uncurled condition each in one of the following compositions for 30 min. The waving composition was then rinsed from the hair and the tresses saturated with a 1.5% solution of hydrogen peroxide as fixing solution. The tresses were again rinsed and dried.
  • Example 10 Strain elongation work indices for the wet hair samples referred to in Example 9 were deter mined as a further measure of hair damage by the chemical treatment described. Approximately 10 filaments from each sample were subjected to load elongation studies in the apparatus referred to in Example 9 while immersed in water at 70 F. The same strain rates, 50% per minute, and gauge lengths, 4 in., were employed as in Example 9. An integrator was connected to the Instron testing dynamometer to automatically compute the area under the stress-strain diagram as a measure of the work done in straining each filament to strain levels of and 30%.
  • the work index (Speakman, Journal of the Textile Institute, vol. 37T, 102 (1947)) is the ratio of the work required to stretch the treated filament 8 to a given strain value to the work required to stretch the untreated material to the same strain value. The results obtained are tabulated in Table 2.
  • Example 11 After shampooing and while saill moist, an adult womans hair was wetted with a 7% aqueous solution of N-acetyl-L-cysteine having pH 7.0 (adjusted with sodium hydroxide), and put up in curlers. The hair on each curler was rem-oistened with the solution. This process was completed just before retiring and the curls remained moist during the night. The hair was then dried, the curlers removed, and the curls combed. The desired curly appearance was achieved and had a substantially greater degree of permanence than when water was used to wet the hair during the curling process. In addition, the hair appeared to have improved body and better sheen.
  • Example 14 The experiment described in Example 3 is repeated, substituting N-benzoyl-L-cysteine for the N-acetyl-L-cysteine specified in that example. Substantially the same results are observed.
  • a cosmetically acceptable aqueous solution containing from about 3% to about 20% by weight of a compound selected from the group consisting of a lower N-alkanoylcysteine having up to ten carbon atoms and N-aroylcysteine having up to twelve carbon atoms for a period of from about 10 minutes to about 12 hours; said solution having a pH of from about pH 7 to about pH 9.5.
  • a process for permenently changing the configuration of hair without substantial damage to the hair structure which includes the step of contacting the hair while in desired configuration with an aqueous solution containing from about 3% to about 20% by weight of a compound selected from the group consisting of a lower N-alkanoylcysteine having up to ten carbon atoms and FOREIGN PATENTS N-aroylcysteine having up 'to Twelve carbon-atoms for 1,035,855 8/1958 Germany a period of time suflicient to achieve plasticization thereof,

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US301843A 1962-09-21 1963-08-13 Hair treatment with nu-acylcysteines Expired - Lifetime US3242052A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US301843A US3242052A (en) 1963-08-13 1963-08-13 Hair treatment with nu-acylcysteines
GB35105/63A GB1002889A (en) 1962-09-21 1963-09-05 Hair waving composition
FR947595A FR1375958A (fr) 1963-08-13 1963-09-16 Nouvelles compositions d'ondulation de la chevelure
DEM58257A DE1208450B (de) 1963-08-13 1963-09-19 Mittel zur Verformung von menschlichem Haar
CH753364A CH462386A (de) 1963-08-13 1964-06-09 Haarverformungsmittel
NL6406777A NL6406777A (de) 1963-08-13 1964-06-15

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US301843A US3242052A (en) 1963-08-13 1963-08-13 Hair treatment with nu-acylcysteines

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CH (1) CH462386A (de)
DE (1) DE1208450B (de)
FR (1) FR1375958A (de)
GB (1) GB1002889A (de)
NL (1) NL6406777A (de)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3470887A (en) * 1965-10-21 1969-10-07 Natcon Chem Co Inc Method for straightening hair and composition of matter for use therewith
US4139610A (en) * 1976-04-19 1979-02-13 Kyowa Hakko Kogyo Kabushiki Kaisha Permanent waving composition
US4153681A (en) * 1976-08-19 1979-05-08 Yamanouchi Pharmaceutical Co., Ltd. Composition for permanent waving
US4272517A (en) * 1978-12-25 1981-06-09 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Permanent waving compositions
US4314572A (en) * 1977-06-09 1982-02-09 Carson Products Company Method and composition for hair treatment
US4322401A (en) * 1979-12-29 1982-03-30 Morio Harada Permanent-wave solution
US4635654A (en) * 1985-11-04 1987-01-13 Redken Laboratories, Inc. Method for evaluating efficacy of a hair styling product
US4992267A (en) * 1988-04-28 1991-02-12 Johnson Products Co., Inc. Hair straightening composition and system
US5296500A (en) * 1991-08-30 1994-03-22 The Procter & Gamble Company Use of N-acetyl-cysteine and derivatives for regulating skin wrinkles and/or skin atrophy
US5451405A (en) * 1994-04-25 1995-09-19 Chesebrough-Pond's Usa Co. Skin treatment composition
WO1997022329A1 (en) * 1995-12-16 1997-06-26 Unilever Plc Cosmetic hair treatment method
US5645825A (en) * 1995-06-07 1997-07-08 The Procter & Gamble Company Depilatory compositions comprising sulfhydryl 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
US20020189027A1 (en) * 2001-04-20 2002-12-19 Cannell David W. Composition and methods for lanthionizing keratin fibers using at least one organic nucleophile and at least one hydroxide ion generator
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
US20030102004A1 (en) * 2000-01-19 2003-06-05 Yoshihiro Hirata Hair styling method
WO2012038114A3 (de) * 2010-09-20 2012-10-18 Henkel Ag & Co. Kgaa Farberhalt durch reduktionsmittelhaltige konditioniermittel
WO2019051182A1 (en) 2017-09-07 2019-03-14 The Children's Hospital Of Philadelphia COMPOSITIONS AND METHODS FOR THE TREATMENT OF CYSTATIN C-HISTORY AMYLOID ANGIOPATHY (HCCAA) AND OTHER NEURODEGENERATIVE DISORDERS ASSOCIATED WITH ABERRANT AMYLOID DEPOTS
WO2019164841A1 (en) * 2018-02-20 2019-08-29 Living Proof, Inc. Covalent treatment with thiols of keratin-containing materials

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU58042A1 (de) * 1969-02-19 1970-09-09 Oreal
LU58634A1 (de) * 1969-05-12 1971-03-09 Oreal
US4301820A (en) * 1980-02-04 1981-11-24 Redken Laboratories, Inc. Permanent waving compositions containing fatty acid lactylates and glycolates and their method of use
SE463674B (sv) * 1987-01-15 1991-01-07 Lejus Medical Ab Foerfarande foer behandling i fluidiserad baedd av amfotaera aminosyror och amfotaera derivat av aminosyror
SE8704542D0 (sv) * 1987-11-19 1987-11-19 Draco Ab New derivatives of cysteine
US5350767A (en) * 1987-11-19 1994-09-27 Aktiebolaget Draco Derivatives of cysteine
SE8901570D0 (sv) * 1989-05-02 1989-05-02 Draco Ab Organic salts of cysteine derivatives
WO2015018596A1 (en) * 2013-08-05 2015-02-12 Unilever N.V. A method and a kit for colouring keratinous fibers

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2405166A (en) * 1942-02-11 1946-08-06 Raymond Lab Inc Process for waving hair
DE1035855B (de) * 1957-06-29 1958-08-07 Hans Schwarzkopf Chem Fab Haut- und Haarpflegemittel
US3091569A (en) * 1960-08-26 1963-05-28 Mead Johnson & Co Mucolytic-nu-acylated sulfhydryl compositions and process for treating animal mucus

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2405166A (en) * 1942-02-11 1946-08-06 Raymond Lab Inc Process for waving hair
DE1035855B (de) * 1957-06-29 1958-08-07 Hans Schwarzkopf Chem Fab Haut- und Haarpflegemittel
US3091569A (en) * 1960-08-26 1963-05-28 Mead Johnson & Co Mucolytic-nu-acylated sulfhydryl compositions and process for treating animal mucus

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3470887A (en) * 1965-10-21 1969-10-07 Natcon Chem Co Inc Method for straightening hair and composition of matter for use therewith
US4139610A (en) * 1976-04-19 1979-02-13 Kyowa Hakko Kogyo Kabushiki Kaisha Permanent waving composition
US4153681A (en) * 1976-08-19 1979-05-08 Yamanouchi Pharmaceutical Co., Ltd. Composition for permanent waving
US4314572A (en) * 1977-06-09 1982-02-09 Carson Products Company Method and composition for hair treatment
US4272517A (en) * 1978-12-25 1981-06-09 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Permanent waving compositions
US4322401A (en) * 1979-12-29 1982-03-30 Morio Harada Permanent-wave solution
US4635654A (en) * 1985-11-04 1987-01-13 Redken Laboratories, Inc. Method for evaluating efficacy of a hair styling product
AU590808B2 (en) * 1985-11-04 1989-11-16 Redken Laboratories, Inc. Method for evaluating efficacy of a hair styling product
EP0269771B1 (de) * 1985-11-04 1992-02-26 Redken Laboratories Inc. Verfahren zur Evaluierung der Wirksamkeit eines Haarversorgungsproduktes
US4992267A (en) * 1988-04-28 1991-02-12 Johnson Products Co., Inc. Hair straightening composition and system
US5296500A (en) * 1991-08-30 1994-03-22 The Procter & Gamble Company Use of N-acetyl-cysteine and derivatives for regulating skin wrinkles and/or skin atrophy
US5451405A (en) * 1994-04-25 1995-09-19 Chesebrough-Pond's Usa Co. Skin treatment composition
US5897857A (en) * 1995-06-07 1999-04-27 The Procter & Gamble Company Depilatory compositions comprising sulfhydryl compounds
US5645825A (en) * 1995-06-07 1997-07-08 The Procter & Gamble Company Depilatory compositions comprising sulfhydryl compounds
WO1997022329A1 (en) * 1995-12-16 1997-06-26 Unilever Plc Cosmetic hair treatment method
US20030102004A1 (en) * 2000-01-19 2003-06-05 Yoshihiro Hirata Hair styling method
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
US20020189027A1 (en) * 2001-04-20 2002-12-19 Cannell David W. Composition and methods for lanthionizing keratin fibers using at least one organic nucleophile and at least one hydroxide ion generator
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
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
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
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
WO2012038114A3 (de) * 2010-09-20 2012-10-18 Henkel Ag & Co. Kgaa Farberhalt durch reduktionsmittelhaltige konditioniermittel
WO2019051182A1 (en) 2017-09-07 2019-03-14 The Children's Hospital Of Philadelphia COMPOSITIONS AND METHODS FOR THE TREATMENT OF CYSTATIN C-HISTORY AMYLOID ANGIOPATHY (HCCAA) AND OTHER NEURODEGENERATIVE DISORDERS ASSOCIATED WITH ABERRANT AMYLOID DEPOTS
EP4379376A2 (de) 2017-09-07 2024-06-05 The Children's Hospital Of Philadelphia Zusammensetzungen und verfahren zur behandlung von hereditärer cystatin-c-amyloidangiopathie (hccaa) und anderen neurodegenerativen erkrankungen im zusammenhang mit aberranter amyloidablagerungen
WO2019164841A1 (en) * 2018-02-20 2019-08-29 Living Proof, Inc. Covalent treatment with thiols of keratin-containing materials
US10993903B2 (en) 2018-02-20 2021-05-04 Living Proof, Inc. Covalent treatment with thiols of keratin-containing materials
US11723857B2 (en) 2018-02-20 2023-08-15 Living Proof, Inc. Covalent treatment with thiols of keratin-containing materials

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DE1208450B (de) 1966-01-05
CH462386A (de) 1968-09-15
NL6406777A (de) 1965-12-16
FR1375958A (fr) 1964-10-23
GB1002889A (en) 1965-09-02

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