US3847165A - Acidic permanent waving solution and process for its use - Google Patents

Acidic permanent waving solution and process for its use Download PDF

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Publication number
US3847165A
US3847165A US00388385A US38838573A US3847165A US 3847165 A US3847165 A US 3847165A US 00388385 A US00388385 A US 00388385A US 38838573 A US38838573 A US 38838573A US 3847165 A US3847165 A US 3847165A
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United States
Prior art keywords
stage
molar
solution
urea
water soluble
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Expired - Lifetime
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US00388385A
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English (en)
Inventor
K Patel
C Reiss
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Redken Laboratories Inc
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Redken Laboratories Inc
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Application filed by Redken Laboratories Inc filed Critical Redken Laboratories Inc
Priority to US00388385A priority Critical patent/US3847165A/en
Priority to DE2437084A priority patent/DE2437084A1/de
Priority to GB3475174A priority patent/GB1466896A/en
Priority to CA206,471A priority patent/CA1034502A/en
Priority to JP49092876A priority patent/JPS5042055A/ja
Application granted granted Critical
Publication of US3847165A publication Critical patent/US3847165A/en
Assigned to SECURITY PACIFIC NATIONAL BANK reassignment SECURITY PACIFIC NATIONAL BANK SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: REDKEN LABORATORIES, INC.
Anticipated expiration legal-status Critical
Assigned to REDKEN LABORATORIES, INC. reassignment REDKEN LABORATORIES, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BANK OF AMERICA NATIONAL TRUST AND SAVINGS ASSOCIATION, SUCCESSOR BY MERGER TO SECURITY PACIFIC NATIONAL BANK
Expired - Lifetime legal-status Critical Current

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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
    • A61K8/64Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/65Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
    • 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
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42Amides
    • 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
    • A61K8/64Proteins; Peptides; Derivatives or degradation products thereof
    • 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

Definitions

  • the hair is neutralized in a conventional manner and styled.
  • Swelling is as important as the reduction process itself. Rate of reaction increases with pH and temperature and has been reported to depend on the extent of ionization of the mercaptan group of the thiol acid, such as ammonium thioglycolate.
  • a two stage acidic hair waving system for use in commercial hair waving and styling operations and a process for using the solutions.
  • the first stage at least consists of urea and/or its alkyl inclusion derivatives and is normally dry.
  • the second stage is a solution containing water, a water soluble thiol, such as ammonium thioglycolate, and a water soluble hair protein.
  • bicarbonate compound and/or borax may be present in the first and/or second stage a bicarbonate compound and/or borax.
  • urea or its derivative Prior to use, urea or its derivative is dissolved to form an aqueous acidic waving solution.
  • the solution contains urea or its derivatives in a concentration from about I to about 4 molar, a water soluble thiol, preferably ammonium thioglycolate, in a concentration from about 0.8 to about 1.4 molar, a bicarbonate compound in a concentration of from to about 0.6 molar, borax in a concentration from O to about 0.007 molar, protein in an amount from about 2 to about 5 percent by weight based on the total weight of the solution, the solution having the pH from about 6 to about 6.8.
  • the reforming solution is applied to the hair which is processed at a temperature from about 1 10 to 130F for a period of from about 5 to 30 minutes.
  • the reforming solutions of this invention are unique as to prior art solutions in that the rate of reaction with hair may be better controlled because the igni ation of the mercaptan group of the thiol is dependent solely on heat and not pH.
  • ammonia is not evolved as an irritant, and therefore there is less irritation to skin and eyes.
  • urea is used to swell the hair sufficiently to permit penetration of the thiol which acts as the bond breaker for sulfur in the hair.
  • Borax when present provides a better curl pattern and also serves as a buffer in conjunction with bicarbonate compound to control pH.
  • DESCRlPTlON According to the present invention, there is provided a novel acidic waving solution and process for its use in the styling of hair.
  • the waving solution is a two stage system, first stage of which comprises urea and its inclusion monoalkyl derivatives, such as methyl urea and ethyl urea preferably in a dry form or, if desired, in an aqueous solution.
  • first stage of which comprises urea and its inclusion monoalkyl derivatives, such as methyl urea and ethyl urea preferably in a dry form or, if desired, in an aqueous solution.
  • the second stage of the solution consists of an aqueous solution of a thiol compound, and a conventional water soluble hair protein.
  • a bicarbonate compound and borax is present, either being provided from the first or second stage, preferably from the first stage.
  • urea and/or its derivatives and any of the contained additions is mixed to form a resultant aqueous solution to what may be termed a reforming solution, in which urea and/or its inclusion derivatives concentration is from about l to about 4 molar, a thiol, such as ammonium thioglycolate is present in a concentration fromabout 0.8 to about 1.4 molar, abicarbonate compound in a concentration from 0 to about 06 molar, borax in a concentration from 0 to about 0.007 molar, hair protein in an amount from about 2 to about 5 percent by weight based on the total weight of the solution, the net solution having a pH from about 6 to about 6.8.
  • a reforming solution in which urea and/or its inclusion derivatives concentration is from about l to about 4 molar
  • a thiol such as ammonium thioglycolate is present in a concentration fromabout 0.8 to about 1.4 molar
  • abicarbonate compound
  • the urea or its functional derivatives and any additional ingredients present are added at the time of use and dissolved in the aqueous solution containing the remaining constituents to provide the net composition set forth above.
  • thiol is intended to include a water soluble compound containing a sulfhydryl or mercaptan group as the hair reducing agent.
  • Conventional thiols are those comprising strong polar groups, such as ammonium thioglycolate, sodium thioglycolate, sodium and ammonium salts of mercaptoethylenesulfonic acid and 3-mercapto-2- hydroxypropanesulfonic acid and the like.
  • the preferred thiol is ammonium thioglycolate.
  • urea or its inclusion derivatives there is meant urea and low molecular weight monoalkyl derivatives of urea, such as methyl and ethyl urea.
  • hair protein there is meant, in general, conventional hydrolysis derivatives of collagen which has been reduced in molecular weight to render the protein water soluble.
  • the urea or urea inclusion derivatives, the thiol and the proteins are those conventionally used in hair waving solutions, whether hot or cold.
  • urea or its inclusion derivatives serve as a swelling agent for hair to facilitate reduction of the sulfur bonds by the thiol under hair dryer techniques employed.
  • Borax when present, improves curl patterns and also acts as a buffer in conjunction with the bicarbonate compound consisting of ammonium bicarbonate, an alkali metal bicarbonate such as sodium or potassium bicarbonate as well as mixtures thereof which, when present, maintains the solution at the desired pH.
  • the reforming solution because it is employed at a pH below 7, and hair is subsequently oxidized at a pH of about 6.1, there is continuity of pH with no material shift in hydrogen bonds and salt linkages.
  • the protein reforming solution of this invention is prepared by the addition of urea and/or its derivatives alone or with other constituents, if present, as solid crystals or in solution to provide the activated solution of the nature described above.
  • the resultant acidic reforming solution may be applied to all types of hair, with normal precautions and where the beauty aid patronss scalp is void of abrasions and the like.
  • agitation is normally required where the urea and/or its derivatives is provided as a solid. Mere shaking of the mixture is sufficient to achieve solution.
  • the hair is first shampooed, towel dried and predampened with the reforming solution and conventional styling wrapping procedures followed, using selected proper sized rods for the desired curl configuration.
  • the patron is then placed under the preheated dryer making sure that the heat provided reaches all areas of the hair including the nape. Care should be taken to test curls aproxima tely every 5 minutes for normal hair and about every 2 to 3 minutes for tinted hair.
  • the hair When the hair forms the desired pattern which may range over a time period from about 5 to about 30 minutes, the hair is rinsed with warm water for a period of about 3 to about 5 minutes.
  • an acidic protein bonding or neutralizing solution (pH about 6.1) which are typically aqueous solutions containing oxidizing agents such as hydrogen peroxide, potassium bromate, alkali metai perborates, such as sodium and potassium perborate, and the like, as well as mixture thereof, which neutralizes the redox effect of the reforming solution. That is to curb reduction of the hair while the reforming solution is oxidized. This also constitutes a rebonding operation to assure rebonding of the hair ends.
  • oxidizing agents such as hydrogen peroxide, potassium bromate, alkali metai perborates, such as sodium and potassium perborate, and the like
  • the neutralizing solution is allowed to remain in the hair for at least 5 minutes for complete bonding an conditioning.
  • the rods are then removed and the neutralizing solution thoroughly worked through the hair to insure rebonding of the hair ends.
  • the hair is then thoroughly rinsed withtepid water and styled in the usual manner to the desired end result.
  • the presently preferred reforming solution of this invention have the following composition:
  • EXAMPLES l to 6 are representative compositions found useful as acidic waving solutions found useful in combination with neutralizing solutions for hair styling. Each component is listed in the typical concentration employed, the balance of the solution being water. The formations are shown in Table I.
  • a two stage acidic composition for use in waving operations which comprises:
  • a first stage comprising a urea compound selected from the group consisting of urea, methyl urea, ethyl urea and mixtures thereof;
  • a second stage comprising water, a water soluble thiol and a water soluble protein
  • said net solution having a pH between about 6.0 and about 6.8, said net solution having a urea compound concentration of from about 1 to about 4 molar; a water soluble thiol concentration of from about 0.8 to about 1.4 molar and a water soluble protein content of from about 2 to 5 percent by weight based on the total weight of the net solution.
  • a two stage acidic composition as claimed in claim 1 in which a bicarbonate compound selected from the group consisting of ammonium bicarbonate, an alkali metal bicarbonate and mixtures thereof is present in the net solution in an amount up to about 0.6 molar.
  • a two stage acidic composition as claimed in claim 2 in which a bicarbonate compound selected from the group consisting of ammonium bicarbonate, an alkali metal bicarbonate and mixtures thereo is present in the net solution in an amount up to about 0.6 molar.
  • a two stage acidic composition as claimed in claim 3 in which borax is present in the net solution in an amount up to about 0.007 molar.
  • a two stage acidic composition for use in hair waving operations which comprises:
  • a first comprising a urea compound selected from the group consisting of urea. methyl urea. ethyl urea and mixtures thereof, a bicarbonate compound selected from the group consisting of ammonium bicarbonate, an alkali metal bicarbonate and mixtures thereof and borax;
  • a second stage comprising water, a'water soluble thiol, and a water soluble protein
  • said net solution having a pH between about 6.0 and about 6.8, said net solution having a urea compound concentration of from about 1 to about 4 molar, a water soluble thiol concentration of from about 0.8 to about 1.4 molar, a bicarbonate compound concentration up to about 0.6 molar, borax in a concentation up to about 0.007 molar and a water soluble protein content of from about 2 to about 5 weight percent by weight based on the total weight of the net solution.
  • a two stage acidic composition for use in hair waving operations which comprises;
  • a first stage comprising a urea compound selected from the group consisting of urea, methylurea, ethyl urea and mixtures thereof;
  • a second stage comprising an aqueous solution of a water soluble thiol, a bicarbonate compound selected from the group consisting of ammonium bicaronate, an alkali metal bicarbonate and mixtures thereof; borax, and a water soluble protein;
  • said net solution having a urea concentration of from about 1 to about 4 molar; an ammonium thioglycolate concentration of from about 1 to about 4 molar; an ammonium thioglycolate concentration of from about 0.8 to about 1.4 molar, ammonium bicarbonate in a concentration of from 0 to about 0.6 molar, borax in a concentration of from 0 to about 0.007 molar and a water soluble protein content of from about 2 to about 5 percent by weight 7 based on the total weight of the net solution.
  • a process for conditioning hair for styling which comprises:
  • rinsing the hair to remove at least a substantial portion of the reforming solution; d. applying to the hair a neutralizing solution contain ing at least one oxidizing agent; e. rinsing the hair with water and setting the hair. 21.
  • the urea compound in the aqueous acidic reforming solu- 'tion is urea and the thiol i'sm'rhohium thioglycolate.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
US00388385A 1973-08-15 1973-08-15 Acidic permanent waving solution and process for its use Expired - Lifetime US3847165A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US00388385A US3847165A (en) 1973-08-15 1973-08-15 Acidic permanent waving solution and process for its use
DE2437084A DE2437084A1 (de) 1973-08-15 1974-08-01 Saures dauerwellenwasser und seine verwendung
GB3475174A GB1466896A (en) 1973-08-15 1974-08-07 Hair waving
CA206,471A CA1034502A (en) 1973-08-15 1974-08-07 Acidic permanent waving solution and process for its use
JP49092876A JPS5042055A (enrdf_load_stackoverflow) 1973-08-15 1974-08-15

Applications Claiming Priority (1)

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US00388385A US3847165A (en) 1973-08-15 1973-08-15 Acidic permanent waving solution and process for its use

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US3847165A true US3847165A (en) 1974-11-12

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US (1) US3847165A (enrdf_load_stackoverflow)
JP (1) JPS5042055A (enrdf_load_stackoverflow)
CA (1) CA1034502A (enrdf_load_stackoverflow)
DE (1) DE2437084A1 (enrdf_load_stackoverflow)
GB (1) GB1466896A (enrdf_load_stackoverflow)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4044782A (en) * 1976-03-26 1977-08-30 The Procter & Gamble Company Acid treated polyester polyurethane foam end wrap
US4054722A (en) * 1975-06-23 1977-10-18 Fuji Photo Film Co., Ltd. Acyloxy substituted acrylate timing layers for color diffusion transfer
US4105038A (en) * 1976-03-26 1978-08-08 The Procter & Gamble Company Acid treated polyether polyurethane foam end wrap
US4134411A (en) * 1975-09-05 1979-01-16 Ikue Yamazaki Acidic two-bath type composition for permanent waving of hair and for treatment of hair and scalp
US4228810A (en) * 1978-11-20 1980-10-21 La Maur Inc. Care and treatment of curly human hair
US4313933A (en) * 1975-05-09 1982-02-02 Ikue Yamazaki Acidic two-bath type composition for permanent waving of hair and for treatment of hair and scalp
EP0102495A3 (en) * 1982-07-30 1985-05-15 Helene Curtis Industries, Inc. Hair waving system and lotion, and method of waving hair
EP0101887A3 (en) * 1982-07-30 1985-05-15 Helene Curtis Industries, Inc. Cosmetic compositions comprising an aqueous solution of an urea compound, hair treatment, skin moisturizer, hair waving system, retardation of alkali production, and hair and skin treatment methods
FR2601975A1 (fr) * 1986-07-24 1988-01-29 Shigesaburo Mizushima Procede pour produire une laine et des poils d'animaux memorisant la forme.
EP0628301A1 (de) * 1993-05-27 1994-12-14 Wella Aktiengesellschaft Mittel und Verfahren zur dauerhaften Haarverformung
FR2855045A1 (fr) * 2003-05-19 2004-11-26 Oreal Composition reductrice pour la deformation permanente des fibres keratiniques et procede de deformation permanente.
US8906352B2 (en) 2006-05-24 2014-12-09 L'oreal Method for straightening human hair fibers using heating means and an α-hydroxy acid derivative
EP2826461A1 (fr) 2004-11-26 2015-01-21 L'Oréal Procédé de défrisage des fibres kératiniques avec un moyen de chauffage et un agent dénaturant
US11044978B2 (en) 2006-05-24 2021-06-29 L'oreal Method for straightening keratinous fibers using heating means and an aromatic compound

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6061516A (ja) * 1983-09-14 1985-04-09 Sansho Seiyaku Kk パ−マネントウエ−ブ用第1液

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2708940A (en) * 1949-06-22 1955-05-24 Gillette Co Composition and method of cold waving
US2836185A (en) * 1954-05-27 1958-05-27 Little Inc A Process of permanently setting hair with a hair-swelling solution of a bisulfite and a nitrogen-containing component
US2836543A (en) * 1954-05-27 1958-05-27 Little Inc A Sulfite hair waving composition comprising a nitrogen-containing compound and a substituted aromatic compound as additive, and method of use
US2847351A (en) * 1955-11-08 1958-08-12 Gillette Co Hair waving composition comprising a disulfide and either a non-corresponding mercaptan or thiourea dioxide
US3109778A (en) * 1961-03-16 1963-11-05 Turner Hall Corp Permanent waving compositions comprising 2, 2, 2-trichloro-1, 1-ethanediol

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2708940A (en) * 1949-06-22 1955-05-24 Gillette Co Composition and method of cold waving
US2836185A (en) * 1954-05-27 1958-05-27 Little Inc A Process of permanently setting hair with a hair-swelling solution of a bisulfite and a nitrogen-containing component
US2836543A (en) * 1954-05-27 1958-05-27 Little Inc A Sulfite hair waving composition comprising a nitrogen-containing compound and a substituted aromatic compound as additive, and method of use
US2847351A (en) * 1955-11-08 1958-08-12 Gillette Co Hair waving composition comprising a disulfide and either a non-corresponding mercaptan or thiourea dioxide
US3109778A (en) * 1961-03-16 1963-11-05 Turner Hall Corp Permanent waving compositions comprising 2, 2, 2-trichloro-1, 1-ethanediol

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4313933A (en) * 1975-05-09 1982-02-02 Ikue Yamazaki Acidic two-bath type composition for permanent waving of hair and for treatment of hair and scalp
US4054722A (en) * 1975-06-23 1977-10-18 Fuji Photo Film Co., Ltd. Acyloxy substituted acrylate timing layers for color diffusion transfer
US4134411A (en) * 1975-09-05 1979-01-16 Ikue Yamazaki Acidic two-bath type composition for permanent waving of hair and for treatment of hair and scalp
US4044782A (en) * 1976-03-26 1977-08-30 The Procter & Gamble Company Acid treated polyester polyurethane foam end wrap
US4105038A (en) * 1976-03-26 1978-08-08 The Procter & Gamble Company Acid treated polyether polyurethane foam end wrap
US4228810A (en) * 1978-11-20 1980-10-21 La Maur Inc. Care and treatment of curly human hair
EP0102495A3 (en) * 1982-07-30 1985-05-15 Helene Curtis Industries, Inc. Hair waving system and lotion, and method of waving hair
EP0101887A3 (en) * 1982-07-30 1985-05-15 Helene Curtis Industries, Inc. Cosmetic compositions comprising an aqueous solution of an urea compound, hair treatment, skin moisturizer, hair waving system, retardation of alkali production, and hair and skin treatment methods
FR2601975A1 (fr) * 1986-07-24 1988-01-29 Shigesaburo Mizushima Procede pour produire une laine et des poils d'animaux memorisant la forme.
EP0628301A1 (de) * 1993-05-27 1994-12-14 Wella Aktiengesellschaft Mittel und Verfahren zur dauerhaften Haarverformung
FR2855045A1 (fr) * 2003-05-19 2004-11-26 Oreal Composition reductrice pour la deformation permanente des fibres keratiniques et procede de deformation permanente.
US20050112076A1 (en) * 2003-05-19 2005-05-26 Thomas Fondin Reducing composition for permanently reshaping keratin fibers and permanent-reshaping process
US7754193B2 (en) 2003-05-19 2010-07-13 L'oreal S.A. Reducing composition for permanently reshaping keratin fibers and permanent-reshaping process
EP2826461A1 (fr) 2004-11-26 2015-01-21 L'Oréal Procédé de défrisage des fibres kératiniques avec un moyen de chauffage et un agent dénaturant
US8906352B2 (en) 2006-05-24 2014-12-09 L'oreal Method for straightening human hair fibers using heating means and an α-hydroxy acid derivative
EP3141284A1 (fr) 2006-05-24 2017-03-15 L'Oréal Procede de defrisage des fibres keratiniques avec un moyen de chauffage et un derive d'acide
US9743736B2 (en) 2006-05-24 2017-08-29 L'oreal Method for straightening human hair fibers using heating means and malic acid
US10561216B2 (en) 2006-05-24 2020-02-18 L'oreal Method for straightening human hair fibers using heating means and an a-keto acid derivative
US11013306B2 (en) 2006-05-24 2021-05-25 L'oreal Method for straightening keratinous fibers using heating means and malic acid
US11044978B2 (en) 2006-05-24 2021-06-29 L'oreal Method for straightening keratinous fibers using heating means and an aromatic compound

Also Published As

Publication number Publication date
CA1034502A (en) 1978-07-11
JPS5042055A (enrdf_load_stackoverflow) 1975-04-16
DE2437084A1 (de) 1975-02-27
GB1466896A (en) 1977-03-09

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Effective date: 19880913

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Effective date: 19930621