US2577710A - Permanent waving compositions and methods - Google Patents

Permanent waving compositions and methods Download PDF

Info

Publication number
US2577710A
US2577710A US398235A US39823541A US2577710A US 2577710 A US2577710 A US 2577710A US 398235 A US398235 A US 398235A US 39823541 A US39823541 A US 39823541A US 2577710 A US2577710 A US 2577710A
Authority
US
United States
Prior art keywords
hair
mercaptan
waving
concentration
solution
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
US398235A
Other languages
English (en)
Inventor
Everett G Mcdonough
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.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=23574560&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US2577710(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to BE461496D priority Critical patent/BE461496A/xx
Priority to NL65044D priority patent/NL65044C/xx
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to US398235A priority patent/US2577710A/en
Priority to GB7140/42A priority patent/GB589956A/en
Priority to CH241113D priority patent/CH241113A/fr
Priority to FR938334D priority patent/FR938334A/fr
Priority to DEP52508A priority patent/DE948186C/de
Priority to DES23916A priority patent/DE972424C/de
Publication of US2577710A publication Critical patent/US2577710A/en
Application granted granted Critical
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • 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
    • D06M13/244—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 sulfur or phosphorus
    • D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
    • D06M13/252—Mercaptans, thiophenols, sulfides or polysulfides, e.g. mercapto acetic acid; Sulfonium compounds

Definitions

  • the present invention is concerned with the chemical medium which provides the chemical or softening force above referred to, this being identified hereinafter for descriptive purposes only as the waving solution, and comprising an aqueous solution containing the waving agent or agents.
  • a waving agent for such solutions which is an al kaline material, for example, bor-ax, various carbonates and phosphates of alkaline materials, ammonia and ammonium salts, such as the carbonates.
  • soluble sulfites of alkalies and ammonia have been utilized for the waving agent, and sulfides have also been provided for this purpose.
  • the sulfides do not require as long a time nor need quite as great a concentration as the sulfites and a satisfactory solution may be made therefrom for most types of hair and even fine hair under some conditions, but many disadvantages appear when using sulfides, the first of which is the characteristic odor of rotten eggs possessed by such sulfides resulting from generation and liberation of free hydrogen sulfide by hydrolysis. All attempts to mask this odor result in failure and the use of heavy perfumes only serves to minimize the objectionable odor. Secondly, these sulfides have a tendency to cause tarnishing and blackening on metal, particularly jewelry, silverware, and the like, which is a further objection to their use in the waving lotion.
  • the disgusting odor which accompanies the use of such hydrogen sulfide salts is toxic to breathe and although normally the amount of hydrogen sulfide produced thereby is not dangerous, when in a confined booth or room such as a beauty shop cubicle often used in hair waving establishments, the concentration of the gas may become so high as to seriously affect both operator and patron, unless expensive ventilating equipment is installed and maintained to remove this gas.
  • ammonium hydrogen sulfide but, despite its relatively greater waving power, the use thereof is limited by liberation of hydro en sulfide gas, together with ammonia gas. These evolved gases make this compound very objectionable and perhaps dangerous, unless special precautions to remove the vapors, for instance, by suction ventilators.
  • ammonium hydrogen sulfide and other sulfides are undesirable to use in spite of repeated rinsings even when using a chemical setting solution. The result is a malodor to the hair, particularly on each re-wetting. More important, however, is the fact that this retention by the hair of the sulfide affords a continuous "relaxing" effect on the permanent wave with the result that the wave becomes less tight with each re-wetting.
  • I can obtain these objects by providing as a waving agent a mercaptan, or a mixture of mercaptans, whether the fixing of the new form for the hairbe by cooling subsequent to heating, or by using .chemical rinses or by any other method, and, further, that an effective waving solution can be obtained by proper formulation including a mercaptan in water.
  • the mercaptans are represented by the formula R-SH where R is an organic group such .as the ethyl group in H H Ethyl mercaptan or the benzyl group in Benzyl mercaptan Such simple mercaptans will function adequately .as waving agents, butthey still have the disadvantage of sulfides, such as ammonium hydrogen sulfide as far as bad odor isconcerned. I .have discovered that bad odor, and other dis,-
  • vadvantages can. be entirely obviated by having ,the molecule contain other groups which are carefully selected,,as hereinafter set forth, to give 'of polar acidic substituted mercaptans are: mercaptans containing the carboxylic groups, as, for
  • mercapto-acetic acid thioglycollic
  • mercaptans containing sulfonic groups as, for example, mercapto-ethyl sulfonic.
  • Other acidic groups are nitro, chloro, or other halogenated groups, sulfonic, sulfate.
  • any homologues could be used and that cyclic, or benzenoid groups may be included-also derivatives of these compounds, such as salts, esters, amides, and the like.
  • polar alkaline substituted mercaptans are: Mercaptan containing amino groups, which may be.
  • alkaline groups are imines and nitrogen heterocyclic compounds. It is to be noted that any homologues could be used and that cyclic, or benzenoid groups may be included-also de rivatives of these compounds,'such as salts, nitrogen derivatives, amides, and the like.'
  • the molecule may contain non-polar groups.
  • An example of a mercaptan containing the non-polar hydroxyl group is the simple mercapto-carbinol compound, c-mercaptoethyl alcohol.
  • An example of mercaptans containing non-polar aldehyde groups is the simple mercapto-carbinol, mercapto acetaldehyde'.
  • mercaptan containing non-polar ketone groups is the simple mercapto-carbonyl, mercapto-di-methyl ketone.
  • An example of mer captan containing ester groups is the simple mercapto-ester, mercapto ethyl acetate.
  • As an example of mercaptan containing ether groups is the simple mercapto-ether, c-mercapto di-ethyl ether. Homologues, cyclic or benzenoid and other derivatives of these compounds could be used.
  • mercaptan compounds could be included under the groups above and the following lists are given to show the wide variety of mercaptans which ma be used and to show that mercaptans having poly mercaptoand'poly sub stituted groups may be used: 1. Thioglycerol, mono, di-, or polythio-polyhydric alcohols, e. g., trithio hexitols, monoand polythio-polyoxyethylene glycols (e; g., tetra glycol dimercaptan) 2. mercapto-ethylhydroxy ethylamine, triomercapto-ethyl amine; 3.
  • This pH range is particularly critical when the waving agent is used for that type of waving employing a chemical setting agent, as in the socalled "cold waving method, since in that system the necessary requirement of speed without hair destruction demands a high concentration of the waving agent in the waving solution. If the pH value is not high enough slow waving action will result and if too high the hair will be destroyed or badly damaged. While with sulfite a shorter waving time may require a pH of or above, with these more powerful waving agents, the use of pHs higher than 9.5 must be watched very carefully for with pH of 10 or above, hair destruction or injury may occur before a satisfactory wave is obtained.
  • organic sulfides and disulfldes are not effective waving agents.
  • mercaptans containing polar groups are difhcult to remove from the hair and whenever the hair becomes damp, for instance, in bathing, shampooing, or at sports such as skiing, the residual odor tends to offend. This is most observable with mercaptans containing polar alkaline groups such as 8- amino ethyl mercaptan.
  • the bad odor and other disadvantages of the simple mercaptans can be obviated by having the organic group R of the mercaptan molecule contain either polar or nonpolar groups.
  • vapor-pressure-depressing substituent in the organic group R" of the mercaptan formula R-SH is meant a substituted mercaptan which contains in its organic group R either a polar (ionizing) group or a nonpolar (non-ionizing) group of the type above described.
  • these compounds in cold waving are far more desirable and effective than ammonium hydrogen sulfide, which has heretofore been utilized particularly for cold waving.
  • these non-polar mercaptans give better waving results and lackv bad odor but also they are easier to remove from the hair and can be completely removed by shampooing or by thoroughly rinsing with water, no malodor being detected on the hair. More important, is that their easy removal allows practically no retention by the hair to effect a relaxation or loosening of the permanent wave with each succeeding wetting of the hair.
  • Example 2 did, however, tend to retain an odor noticeable upon wetting the hair While with the solution of Example 2 not a trace of bad odor was present even when the waved hair was re-wetted.
  • additional groups such as hydroxyl present.
  • Particularly effective as such a compound is 2-hydroxy 3-amino propyl mercaptan.
  • mercaptans containing polar and non-polar groups may be used. It has been brought out hereinbefore that either polar or non-polar groups are within the spirit and scope of this invention. Polar groups differ from non-polar in that in water solution they may ionize.
  • the concentration of the waving agent may be materially decreased, approximately to one-third or one-fifth of the concentration given in the examples.
  • EXAMPLE 1 Polar typ -Acidic Mercapto-acetic, about 2 gms. to 3.3 gms.
  • EXAMPLE 3 Polar type-Basic Mercapto ethylamine, about 1 gm. to 1.66 gms.
  • a purpose is to provide a waving agent for use in a solution, the concentration of the waving agent being much lower than heretofore effective commensurate with the desired effect of waving the hair.
  • the following procedure, or one similar thereto, may be employed in giving a permanent wave:
  • the head of hair is blocked off into secunder the same conditions of procedure can be tions and each of the sectioned strands is then well soaked in the waving solution.
  • each section of hair is wound on a mandrel to the form desired and heat is then applied, as by a chemical heating pad arranged over the wound section or by an electrical heating unit, the temperature being raised to about 212 F.. and the hair, upon cooling, sets into its new configuration.
  • EXAMPLE 1 PoZar-type-Acidic Mercapto-acetic, about 6 gms. to 10 gms.
  • EXAMPLE 3 Polar type-Basic Mercapto ethylamine, about 3 gms. to 5 gms. to
  • the concentration of my novel waving agent in the waving solution that the desired time of actual treatment becomes feasible, ranging from a low concentration with longer time of application as is desired in some methods of cold waving, or a low concentration in continuous intimate contact with shorter time of application, or a low concentration with shorter time using heat, to higher concentrations with decrease in time whether the fix ation is by chemical, or by cooling subsequent to heating.
  • the time of waving is greater with lower concentrations and less with higher concentrations of mercaptans and since, as described above, the time of waving is greater with a lower pH value and less with a higher pH value, it fol lows'that the concentration of "the mercaptan and the pH of the solution can be adjusted withinthe ranges given above to obtain a permanent change in the'configuration of human hair during 9, given time of application without damage to the hair structure by having the concentration of mercaptan in the higher portion of the concentration range for a lower pH and having the concentration of mercaptan in the lower portion of said concentration range for a higher pH. But I do not under any conditions use concentrations higher than heretofore used. On the contrary, comparing the time-concentration factors of my novel waving agent with waving agents of the prior art for equivalent purposes, it will be found that under all analogous conditions I provide a distinct reduction in concentration while attaining optimum results in the final waving.
  • the waving solution according to this invention may be applied to the hair at any desired time, either before or after winding or otherwise mechanically placing the hair in its reformed desired shape or form and by any desired means, such assoaking, spraying, continuous circulation or the like, and the'claims are to be so construed.
  • any desired means such assoaking, spraying, continuous circulation or the like, and the'claims are to be so construed.
  • a permanent waving composition comprising a mercaptan having a molecular weight less than 121 and having the general formula R-SH, where the organic group R contains a carbon atom attached to the sulfur atom, said mercaptan having a vapor-pressure-depressing substituent in the organic group R, in a solution containing an alkaline material having a dissociation constant less than 10- said solution having a pH higher than pH 7 and not higher than pH 9.5, the concentration of said mercaptan in terms of weight per volume ranging between about 1% and about 10%, the concentration of mercaptan and the pH of the solution being adjusted within said ranges to obtain a permanent change in the configuration of human hair during a given time of application without damage to the hair structure by having the concentration of mercaptan in the higher portion of said concentration range for a lower pH and having the concentration of mercaptan in the lower portion of said concentration range for a higher pH within the stated pH range.
  • a permanent waving composition comprising a solution having a concentration in terms of weight per volume of 3% to less than about 8% of a mercaptan having a molecular weight less than 121 and having the general formula R-SH, where the organic group R contains .a carbon atom attached to the sulfur atom, said mercaptan having a vapor-pressure-depressing substituent in the organic group R, and a voltatile base having a dissociation constant less than 5 x 19- said solution having a pH ranging from about 9.2 to not higher than 9.5, the concentration of mercaptan and the pH of the solution being adjusted within said ranges to obtain a permanent change in the configuration of human hair during a given time of application at temperaturestolerable to the human body without damage to the hair structure.
  • a permanent waving composition comprising a solution having a concentration in'terms of weight per volume of 3% to less than about 8% of a mercaptan having a molecular weight less than 121 and having the general formula R,SH.
  • the organic group R contains a carbon atom attached to the sulfur atom, said mercaptan having a vapor-pressure-depressing substituent in the organic group R, and an alkaline material having a dissbciation constant less than 5 lO said solution l aving a pH of about 9.2 to not higher than 9.5,the concentration of mercaptan and the pH of the solution being adjusted within said ranges to obtain a permanent change in the configuration of human hair during a given time of application at temperatures tolerable to the human body without damage to the hair structure.
  • the method of permanently changing the configuration of human hair without damage to the hair structure including the steps of imparting the vdesired configuration to the hair and treating of the hair for a length of time with a permanent waving solution comprising an alkaline material having a dissociation constant less than 5 10- and a mercaptan of the general formula R-SH where the organic group R contains a carbon atom attached to the sulfur atom, said mercaptan having a vapor-pressure-depressing substituent in the organic group R and having a molecular weight less than 121, said solution having a pH higher than pH 7 and not higher than pH 9.5, the concentration of the mercaptan in terms of weight per volume ranging between about 1% and about 10%, the concentration of mercaptan and the pH of the solution being adjusted within said ranges to obtain a permanent change in the configuration of human hair during a given time of application without damage to the hair structure by having the concentration of mercaptan in thehigher portion of said concentration range for a lower pH and having the
  • the method of permanently changing the configuration of human hair without damage to the hair structure including the steps of imparting the desired configuration to the hair and treating of the hair with a permanent waving solution comprising about 1% to about 10% in terms of weight per volume of a mercaptan of the general formula R-SH where the organic group R contains a carbon atom attached to the sulfur atom, said mercaptan having a non-ionizing vapor-pressure-depressing substituent in the organic group R, and an alkaline material having a dissociation constant less than 5 10- said solution having a pH higher than pH 7 and not higher than pH 9.5; the concentration of mercaptan and the pH of the solution being adjusted within said ranges to obtain a permanent change in the configuration of human hair during a given time of application without damage to the hair structure by having .the concentration of mercaptan in the higher portion 01' said concentration range for a lower pH and having the concentration of mercaptan in the lower portion of said concentration range for a higher pH within the stated pH range; and
  • composition as specified in claim 1 wherein the vapor-pressure-depressing substituent is an ionizing group.
  • composition as specified in claim 1 wherein the vapor-pressure-depressing substituent is an acidic group.
  • composition as specified in claim 1 wherein the vapor-pressure-depressing substituent is a non-ionizing group.
  • composition as specified in claim 1 wherein the vapor-pressure-depressing substituent is an ether group.
  • a composition as specified in claim 1 wherein the dissociation constant of the alkaline material is about 10- 11.
  • a composition as specified in claim 3 wherein the dissociation constant of the alkaline material is about 12.
  • a composition as specified in claim 3 wherein the concentration of mercaptan is about 6%.
  • composition as specified in claim 3 wherein the vapor-pressure-depressing substituent is an ionizing group.
  • composition as specified in claim 3 wherein the vapor-pressure-depressing substituent is an acidic group.
  • composition as specified in claim 3 wherein the vapor-pressure-depressing substituent is a non-ionizing group.
  • composition as specified in claim 3 wherein the vapor-pressure-depressing substituent is an ether group.
  • a permanent waving composition comprising a solution having a concentration in terms of weight per volume of about 1% to about 10% of a mercaptan having a molecular weight less than 121 and having the general formula RSH, I
  • the organic group R contains a carbon atom attached to the sulfur atom, said mercaptan having a vapor-pressure-depressing substituent in the organic group R, and an alkaline material having a dissociation constant less than 5x10- said solution having a pH of about 9.2. the concentration of mercaptan being adjusted with respect to said pH to obtain a permanent change in the configuration of human hair during a given time of application at temperatures tolerable to the human body without damage to the hair structure.
  • a permanent waving composition comprising a mercaptan having a molecular weight less than 121 and having the general formula R-SH, where the organic group R contains a carbon atom attached to the sulfur atom, said mercaptan having a vapor-pressure-depressing substituent in the organic group R, in asolution containing an alkaline material having a dissociation constant less than 5x10 said solution having a pH higher than pH 7 and not higher than pH 9.5, the concentration of said mercaptan in terms of weight per volume being about 6%, and the pH of the solution being adjusted within said ranges to obtain a permanent change in the configuration of human hair during a given time of application without damage to the hair structure.
  • Pillemer et al. The Specificity of Keratins, Journal of Experimental Medicine, 1939, pp. 191- 197.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US398235A 1941-06-16 1941-06-16 Permanent waving compositions and methods Expired - Lifetime US2577710A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
BE461496D BE461496A (fr) 1941-06-16
NL65044D NL65044C (fr) 1941-06-16
US398235A US2577710A (en) 1941-06-16 1941-06-16 Permanent waving compositions and methods
GB7140/42A GB589956A (en) 1941-06-16 1942-05-26 Improvements in or relating to permanent hair waving
CH241113D CH241113A (fr) 1941-06-16 1942-06-16 Préparation pour le traitement de fibres contenant de la kératine.
FR938334D FR938334A (fr) 1941-06-16 1946-01-07 Perfectionnements à l'ondulation permanente des cheveux
DEP52508A DE948186C (de) 1941-06-16 1949-08-20 Mittel zur dauernden Formveraenderung von Haaren am lebenden Koerper (Dauerwellen)
DES23916A DE972424C (de) 1941-06-16 1949-08-20 Verfahren zur dauernden Verformung, insbesondere zum Dauerwellen, von Keratinfasern, vorzugsweise von Haaren am lebenden menschlichen Koerper

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US398235A US2577710A (en) 1941-06-16 1941-06-16 Permanent waving compositions and methods

Publications (1)

Publication Number Publication Date
US2577710A true US2577710A (en) 1951-12-04

Family

ID=23574560

Family Applications (1)

Application Number Title Priority Date Filing Date
US398235A Expired - Lifetime US2577710A (en) 1941-06-16 1941-06-16 Permanent waving compositions and methods

Country Status (7)

Country Link
US (1) US2577710A (fr)
BE (1) BE461496A (fr)
CH (1) CH241113A (fr)
DE (2) DE972424C (fr)
FR (1) FR938334A (fr)
GB (1) GB589956A (fr)
NL (1) NL65044C (fr)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2688972A (en) * 1951-11-20 1954-09-14 Gillette Co Process for permanently waving human hair
DE948186C (de) * 1941-06-16 1956-08-30 Sales Affiliates Inc Mittel zur dauernden Formveraenderung von Haaren am lebenden Koerper (Dauerwellen)
US2776668A (en) * 1951-06-28 1957-01-08 Rubinstein Inc H Method and preparations for the permanent dyeing of keratinous material
US2809643A (en) * 1954-04-30 1957-10-15 Freeman Rose Hair curler
US2865811A (en) * 1952-05-02 1958-12-23 Irval Cosmetics Inc Hair straightener containing a kerating reducing agent, anionic wetting agent and water-soluble soap and method of using same
US2889833A (en) * 1951-12-03 1959-06-09 Sales Affiliates Inc Glyceryl monomercaptan composition and method of cold waving
US2976216A (en) * 1959-11-04 1961-03-21 Gillette Co Permanent waving agent
US3025218A (en) * 1958-11-06 1962-03-13 Turner Hall Corp Permanent waving of hair on the human head
US3066077A (en) * 1961-05-08 1962-11-27 Gillette Co Alpha, alpha'-dimercaptoadipic hair waving compositions
US3071515A (en) * 1958-12-31 1963-01-01 Procter & Gamble Hair waving compositions
US3093146A (en) * 1958-03-14 1963-06-11 Oreal Process for permanent setting of living hair by surface active compounds
US3459198A (en) * 1966-03-10 1969-08-05 Collaborative Res Inc Waving and straightening human hair with 1,4-dimercapto-2,3-butane diol and substituted products thereof
JPS63145219A (ja) * 1986-12-09 1988-06-17 Kao Corp 加温式毛髪変形処理剤
US4786493A (en) * 1985-11-22 1988-11-22 Estee Lauder Inc. Hair protection composition
US4935230A (en) * 1986-03-03 1990-06-19 Kao Corporation Hair waving agent
US5362487A (en) * 1992-01-10 1994-11-08 Helene Curtis, Inc. Cysteamine permanent wave composition and method
US5456907A (en) * 1992-01-10 1995-10-10 Helene Curtis, Inc. Cysteamine permanent wave composition and method
WO2006121214A2 (fr) * 2005-05-12 2006-11-16 Showa Denko K.K. Agent d'ondulation permanent
US20080085251A1 (en) * 2004-12-20 2008-04-10 Akira Shibuya Hair Processing Agent And Method For Permanent Waving Hair

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE958764C (de) * 1948-10-02 1957-02-21 Schwarzkopf Fa Hans Mittel zur dauerhaften Formveraenderung von menschlichem Haar bei Temperaturen von 20 bis 200íÒ
DE958501C (de) * 1949-04-14 1957-02-21 Schwarzkopf Fa Hans Mittel zur dauerhaften Formveraenderung des menschlichen Haares bei Temperaturen zwischen 20 und 200íÒ
DE958696C (de) * 1949-04-14 1957-02-21 Schwarzkopf Fa Hans Dauerwellmittel fuer menschliches Haar
DE899703C (de) * 1949-04-15 1953-12-14 Henkel & Cie Gmbh Verfahren zur AEnderung der Struktur von schwefelhaltigen Skleroproteinen
DE879756C (de) * 1949-07-09 1953-06-18 Henkel & Cie Gmbh Mittel zur AEnderung der Struktur von schwefelhaltigen Skleroproteinen
DE971559C (de) * 1949-11-07 1959-02-19 Haarfarben Mittel zum Herstellen von Kaltdauerwellen
DE968630C (de) * 1950-09-02 1958-03-13 Wella Ag Reagenzpapier zum Nachweis von Thioglykolsaeure bzw. Thioglykolat
DE1034820B (de) * 1952-03-05 1958-07-24 Wella Ag Verfahren zur verformenden Behandlung von Keratinfasern
DE950678C (de) * 1953-12-06 1956-10-11 Basf Ag Haarpflegemittel
DE1000567B (de) * 1953-12-07 1957-01-10 Hans Fasching Erben K G Verfahren zur Erhaltung der pilzabtoetenden Wirkung von antimykotischen Substanzen bei Zugabe derselben zu nagelkeratin-aufweichenden Verbindungen (Thioglykolaten)
DE1009765B (de) * 1955-04-18 1957-06-06 F Schwaiger Dipl Ing Mittel zur Haarverformung im sauren Medium
DE1067566B (de) * 1955-07-12 1959-10-22 Johannes Saphir Verfahren zur Herstellung haltbarer Frisuren
DE1126839C2 (de) * 1961-02-16 1973-05-03 Therachemie Chem Therapeut Mittel zur Behandlung schwefelhaltiger Skleroproteine
EP0095916A3 (fr) * 1982-06-01 1984-08-08 THE PROCTER & GAMBLE COMPANY Compositions dépilatoires
JPH0296512A (ja) * 1988-09-29 1990-04-09 Seiwa Kasei:Kk パーマネントウェーブ用第一剤
DE19608581A1 (de) * 1996-03-06 1997-09-11 Wella Ag Mittel und Verfahren zur dauerhaften Haarverformung
DE19618445A1 (de) * 1996-05-08 1997-11-13 Wella Ag Mittel und Verfahren zur dauerhaften Haarverformung auf Basis von Mercaptoacetamiden sowie Verfahren zu deren Herstellung
US6116250A (en) * 1996-07-20 2000-09-12 Wella Aktiengesellschaft Process of permanent hair shaping
US6153180A (en) * 1997-01-11 2000-11-28 Wella Aktiengesellschaft Agent and method for permanently shaping the hair, based on n-branched-chain alkyl-substituted mercapto acetamides and process for their preparation
EP0868900A1 (fr) * 1997-03-14 1998-10-07 Wella Aktiengesellschaft Composition et méthode pour l'ondulation permanente des cheveux
DE19732079C1 (de) * 1997-07-25 1999-02-04 Wella Ag Gesättigte, alkylsubstituierte N-Mercaptoacetyl-Heterocyclen, Mittel und Verfahren zur dauerhaften Haarverformung auf deren Basis
DE59810341D1 (de) 1997-07-31 2004-01-15 Wella Ag Mittel und verfahren zur dauerhaften haarverformung und verfahren zur herstellung von n-alkylmercaptoacetamiden
DE19733952C2 (de) 1997-08-06 1999-12-23 Wella Ag Mittel zur dauerhaften Haarverformung auf Basis von N,N-disubstituierten Mercaptoacetamiden sowie Verfahren zur Herstellung dieser Mercaptoacetamide
CN110044670B (zh) * 2019-03-27 2022-08-09 广州金域司法鉴定技术有限公司 毛发中毒品提取试剂盒、提取方法和检测方法

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1780449A (en) * 1929-07-01 1930-11-04 Snell Foster Dee Hair waving
US1973130A (en) * 1933-07-21 1934-09-11 Rohm & Haas Process of unhairing hides or skins
GB435213A (en) * 1933-06-13 1935-09-17 Frederic Maeder Improvements in or relating to permanent hair-waving
GB453701A (en) * 1934-12-10 1936-09-10 John Bamber Speakman Improvements in and relating to the treatment of fibres or fibrous materials containing keratin
US2154925A (en) * 1937-06-02 1939-04-18 Carbide & Carbon Chem Corp Hair waving
US2183894A (en) * 1937-07-26 1939-12-19 David J Pye Cold permanent waving of hair
US2194517A (en) * 1937-10-26 1940-03-26 Du Pont Contact insecticide
US2238672A (en) * 1940-04-09 1941-04-15 Du Pont Textile treatment
US2266719A (en) * 1941-01-11 1941-12-16 Nat Oil Prod Co Process of refining fat-soluble vitamin-containing materials
US2352524A (en) * 1938-06-20 1944-06-27 Sales Affiliates Inc Depilatory

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA365290A (fr) * 1937-04-06 Bamber Speakman John Traitement de la keratine
US1899707A (en) * 1933-02-28 mcxee
CH189507A (de) * 1933-06-13 1937-02-28 Maeder Frederic Verfahren zur Herstellung eines Mittels zur Erzeugung von Dauerwellen in Haaren.
DE655845C (de) * 1934-08-05 1938-01-25 Coriolan Ges M B H Neuheiten V Mittel zur Herstellung von Dauerwellen
US2180380A (en) * 1934-12-10 1939-11-21 Arnold F Willat Permanent waving of hair
FR784404A (fr) * 1934-12-15 1935-07-22 Produit hygiénique et cosmétique
DE697634C (de) * 1935-07-19 1940-10-18 Phil Friedrich Keil Dr Mittel zum Strecken und Glaetten krausen Haares
US2123214A (en) * 1935-11-02 1938-07-12 William B Stoddard Stabilized soluble stannite depilatory
FR824804A (fr) * 1936-07-27 1938-02-17 Préparation épilatoire
GB484467A (en) * 1936-07-27 1938-04-27 Maurice Edmond Joseph Gheury D Toilet depilatory preparations
GB472745A (en) * 1937-02-24 1937-09-29 Norman Victor Sydney Knibbs Improvements in and relating to solutions for curling and waving hair
US2190380A (en) * 1937-06-02 1940-02-13 Hoe & Co R Plate clamping mechanism
CH224067A (fr) * 1937-10-08 1942-10-31 Liggett Evans Ralph Dépilatoire pour le corps humain.
DE885746C (de) * 1939-08-12 1953-08-06 Siemens Ag Verfahren zum Verleimen von Brettern aus Holz oder anderen Werkstoffen mittels elektrischer Hochfrequenzfelder
CH221067A (de) * 1939-10-14 1942-05-15 Hermes Patentverwertungs Gmbh Verfahren zum Verleimen von Brettern und ähnlichen langen Gegenständen.
CH220349A (de) * 1939-12-18 1942-03-31 Wiechowski Siegfried Dr Prof Verfahren zur Herstellung eines Haar- und Hautpflegemittels.
DE719542C (de) * 1940-07-03 1942-04-10 Deutsche Hydrierwerke Ag Kosmetische Praeparate
NL56529C (fr) * 1940-12-24 1944-06-15
US2350178A (en) * 1941-03-13 1944-05-30 Martin Lab Inc Hair waving
NL65044C (fr) * 1941-06-16
US2405166A (en) * 1942-02-11 1946-08-06 Raymond Lab Inc Process for waving hair
US2389755A (en) * 1942-12-21 1945-11-27 George S Baker Permanent wave solutions
US2418664A (en) * 1946-06-10 1947-04-08 Harry R Ramsey Hair treating cream

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1780449A (en) * 1929-07-01 1930-11-04 Snell Foster Dee Hair waving
GB435213A (en) * 1933-06-13 1935-09-17 Frederic Maeder Improvements in or relating to permanent hair-waving
US1973130A (en) * 1933-07-21 1934-09-11 Rohm & Haas Process of unhairing hides or skins
GB453701A (en) * 1934-12-10 1936-09-10 John Bamber Speakman Improvements in and relating to the treatment of fibres or fibrous materials containing keratin
US2201929A (en) * 1934-12-10 1940-05-21 Speakman John Bamber Treatment of fibers or fibrous materials containing keratin
US2261094A (en) * 1934-12-10 1941-10-28 Speakman John Bamber Treatment of keratins
US2154925A (en) * 1937-06-02 1939-04-18 Carbide & Carbon Chem Corp Hair waving
US2183894A (en) * 1937-07-26 1939-12-19 David J Pye Cold permanent waving of hair
US2194517A (en) * 1937-10-26 1940-03-26 Du Pont Contact insecticide
US2352524A (en) * 1938-06-20 1944-06-27 Sales Affiliates Inc Depilatory
US2238672A (en) * 1940-04-09 1941-04-15 Du Pont Textile treatment
US2266719A (en) * 1941-01-11 1941-12-16 Nat Oil Prod Co Process of refining fat-soluble vitamin-containing materials

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE948186C (de) * 1941-06-16 1956-08-30 Sales Affiliates Inc Mittel zur dauernden Formveraenderung von Haaren am lebenden Koerper (Dauerwellen)
US2776668A (en) * 1951-06-28 1957-01-08 Rubinstein Inc H Method and preparations for the permanent dyeing of keratinous material
US2688972A (en) * 1951-11-20 1954-09-14 Gillette Co Process for permanently waving human hair
US2889833A (en) * 1951-12-03 1959-06-09 Sales Affiliates Inc Glyceryl monomercaptan composition and method of cold waving
US2865811A (en) * 1952-05-02 1958-12-23 Irval Cosmetics Inc Hair straightener containing a kerating reducing agent, anionic wetting agent and water-soluble soap and method of using same
US2809643A (en) * 1954-04-30 1957-10-15 Freeman Rose Hair curler
US3093146A (en) * 1958-03-14 1963-06-11 Oreal Process for permanent setting of living hair by surface active compounds
US3025218A (en) * 1958-11-06 1962-03-13 Turner Hall Corp Permanent waving of hair on the human head
US3071515A (en) * 1958-12-31 1963-01-01 Procter & Gamble Hair waving compositions
US2976216A (en) * 1959-11-04 1961-03-21 Gillette Co Permanent waving agent
US3066077A (en) * 1961-05-08 1962-11-27 Gillette Co Alpha, alpha'-dimercaptoadipic hair waving compositions
US3459198A (en) * 1966-03-10 1969-08-05 Collaborative Res Inc Waving and straightening human hair with 1,4-dimercapto-2,3-butane diol and substituted products thereof
US4786493A (en) * 1985-11-22 1988-11-22 Estee Lauder Inc. Hair protection composition
US4935230A (en) * 1986-03-03 1990-06-19 Kao Corporation Hair waving agent
US4935229A (en) * 1986-03-03 1990-06-19 Kao Corporation Hair waving agent
JPS63145219A (ja) * 1986-12-09 1988-06-17 Kao Corp 加温式毛髪変形処理剤
US5362487A (en) * 1992-01-10 1994-11-08 Helene Curtis, Inc. Cysteamine permanent wave composition and method
US5382426A (en) * 1992-01-10 1995-01-17 Helene Curtis, Inc. Cysteamine permament wave composition and method
US5439675A (en) * 1992-01-10 1995-08-08 Helene Curtis, Inc. Cysteamine permanent wave composition and method
US5456907A (en) * 1992-01-10 1995-10-10 Helene Curtis, Inc. Cysteamine permanent wave composition and method
US5460809A (en) * 1992-01-10 1995-10-24 Helene Curtis, Inc. Cysteamine permanent wave composition and method
US5601813A (en) * 1992-01-10 1997-02-11 Helene Curtis, Inc. Cysteamine permanent wave composition and method
CN101669887B (zh) * 2004-12-20 2012-12-05 昭和电工株式会社 毛发处理剂和烫发方法
US8961946B2 (en) * 2004-12-20 2015-02-24 Showa Denko K.K. Hair processing agent and method for permanent waving hair
US20080085251A1 (en) * 2004-12-20 2008-04-10 Akira Shibuya Hair Processing Agent And Method For Permanent Waving Hair
WO2006121214A2 (fr) * 2005-05-12 2006-11-16 Showa Denko K.K. Agent d'ondulation permanent
KR100970136B1 (ko) 2005-05-12 2010-07-14 쇼와 덴코 가부시키가이샤 퍼머넌트 웨이브 약제
CN101175535B (zh) * 2005-05-12 2011-05-04 昭和电工株式会社 烫发剂
US20090081147A1 (en) * 2005-05-12 2009-03-26 Showa Denko K.K. Permanent waving agent
WO2006121214A3 (fr) * 2005-05-12 2007-11-22 Showa Denko Kk Agent d'ondulation permanent

Also Published As

Publication number Publication date
NL65044C (fr)
DE948186C (de) 1956-08-30
DE972424C (de) 1959-07-16
CH241113A (fr) 1946-02-15
GB589956A (en) 1947-07-04
FR938334A (fr) 1948-09-10
BE461496A (fr)

Similar Documents

Publication Publication Date Title
US2577710A (en) Permanent waving compositions and methods
US3966903A (en) Sulfite or bisulfite hair-waving composition containing a wave accelerating agent
CA1338799C (fr) Solution a permanente
US4192863A (en) Completely one-step permanent wave solution and a method for using the same
US4459284A (en) Permanent waving composition comprising amino acids
JPS61183214A (ja) パーマネントウエーブ中和剤組成物およびその製造法
IE59238B1 (en) Peroxide-containing conditioning shampoo
JP3053650B2 (ja) 新規な酸化組成物および新規な髪のパーマネント変形またはブリーチ方法
US4504466A (en) Permanent hair-waving
US5116608A (en) Permanent waving composition
US5747015A (en) Acylated silk proteins for hair care
JPH01503297A (ja) 毛髪のパーマネント構造変形に使用する組成物
US2577711A (en) Permanent waving compositions and methods
US5271926A (en) Two-pack hair treatment composition and process for treating hair
KR20080023330A (ko) 최소한 하나의 디카르복시디티올을 포함하는 퍼머형 모발의재형상용 조성물
US2736323A (en) Permanent waving solutions and method
US3256154A (en) Hair waving composition and method
KR102046790B1 (ko) 열 재성형 방법
US5415856A (en) Hair treatment compositions containing disaccharides
EP0658338B1 (fr) Utilisation des compositions contenant des substances réductrices de la kératine et des alcools pour défriser les cheveux
US2889833A (en) Glyceryl monomercaptan composition and method of cold waving
WO2001082881A1 (fr) Compositions de frisage et methode de frisage utilisant ces compositions
US3331743A (en) Cyclohexylcyclohexanone in mercaptoacetate hair-treating compositions
CN112236127B (zh) 使角蛋白纤维定型和/或成波浪形的方法和组合物
CA1111769A (fr) Produits pour ondulations capillaires, a base d'acide thioglycolique, d'ammoniac et de carbonate