US2261094A - Treatment of keratins - Google Patents

Treatment of keratins Download PDF

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Publication number
US2261094A
US2261094A US53688A US5368835A US2261094A US 2261094 A US2261094 A US 2261094A US 53688 A US53688 A US 53688A US 5368835 A US5368835 A US 5368835A US 2261094 A US2261094 A US 2261094A
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Prior art keywords
hair
solution
fibres
treatment
keratin
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Expired - Lifetime
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US53688A
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English (en)
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Speakman John Bamber
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/23—Sulfur; Selenium; Tellurium; Compounds thereof
    • 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
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01C—CHEMICAL OR BIOLOGICAL TREATMENT OF NATURAL FILAMENTARY OR FIBROUS MATERIAL TO OBTAIN FILAMENTS OR FIBRES FOR SPINNING; CARBONISING RAGS TO RECOVER ANIMAL FIBRES
    • D01C3/00—Treatment of animal material, e.g. chemical scouring of wool

Definitions

  • keratin such as hair and wogiand is parpou containing two r m r r a ve ha o n ticularly concernedTitli tY'athients for the apatoms, w by to form in or between the fibres plication of permanent set to such substances .5' e D bonds Containing a metal or for the removal of stress from materials made erganicg p
  • the reatment with a reducfrom them, and for the treatment of keratininge m may e eff d a n m y r l containing materials in or before finishing opvatedtemp e e- Y rati 5
  • the disruption of the disulphide bond by re- Substances containing keratin are customarily duction in" this way relieves stress in the keratinsubjected to a-
  • fibres in a state such that further bonds may b proposed to treat wo l o hair wh i th caused to take place with the fibres in the destretched condition with boiling solutions of bi- O d d on by subsequent treatment with sulphite for the improvement of its appearance the metal Salvo! Organic p u 01 bon s and properties and subsequently to treat the wool e n S '-X-S- where X is a metal or oror hair with solutions of metal compounds such genie r ping-
  • the fibres are stabilised in the as basic alum or with oxidising agents.
  • Treatformation which they had during such treatment ment of wool or hair with boiling solutions of and-may t be caused to take on a P rmanent sulphites or bisulphites will cause disruption of g the disulphide bond tie-keratin and the formahebonds formed in the P e f the metal tion of S-NH bonds according to the following Or Organic compounds are resistant to steam n equations, where and 1391 hot water and consequently any set or formation resent the peptide and associated side chains of g en to -co taining fibres under treat- 1 mt ment wiilhbe retained subsequently by the fibres k I evenin e presence of hot water and steam.
  • the object of the invention is to provide a 40 bon'ds should precede as aseparate step the treatmethod of treatment of keratin containing subment with the polyvalent metal compound or stances for the removal of stress on the applica-' organic compound- If the reducing agent a tion of a set which maybe carried out at normal polyvalent metal compound or organic compound or raised temperatures and which will render are employed simultaneously, reaction may take the keratin containing substances resistant to place whereby the metal or 0rga,nic grouping deterioration by alkaline media and susceptible enters the disulphide bond, b t t reaction takes to dyeing without the use of mordants.
  • the invention consists in treating fibrous suband therefore without change in. the internal stance containing keratin, such as wool or hair, stress of the fibres or the formation of the fibres with a reducing agent at such concentration, pH 50.
  • keratin such as wool or hair
  • stress of the fibres or the formation of the fibres with a reducing agent at such concentration, pH 50.
  • This invention relates to improvements in the treatment of fibres or fibrous materials containand temperature as to effect reduction and disruption of the constituent disulphide or cystine bond of keratin with the formation of sulphydryl groups and thereafter treating the substance,
  • a solution of a polyvalent metal compound or with an organic comfibres by the method ofthe invention may be employed for attachment or those dye moleculesvwhich ordinarily require the use of a mordant.
  • suitable reducing agents which may be employed are sodium, ammonium or potassium bisulphite, sodium sulphide, sodium hydrosulphide, titanous chloride, cysteine hydrochloride, sodium hypophosphite, sodium thiosulphate, sulphurous acid, sodium hydrosulphite, ammonium, sodium or potassium sulphite, sodium dithionate and potassium metabisulphite, which may be used either alone or in combination with one another or with suitable media.
  • the reducing agent may be formed in situ as f by moistening the fibres with a small quantity of a solution of an alkali such as baryta which reacts with the fibre molecules to form a hydrosulphide, the concentration of which may be kept sufficiently high if the amount of solution employed is small.
  • Reducing agents as a whole with the exception of those yielding S03 ions disrupt the disulphide bond of keratin with the formation of sulphydryl groups, although the quantity of disulphide bonds disrupted in any keratin-containing substance varies not only from one reducing agent to another, but also with the conditions of concentration, pH and temperature at which a-reducing agent is employed.
  • the reducing agents yielding S03 ions as exemplified by sulphites, bisulphites and metabisulphites, efiect disruption of the disulphide bond of keratin by formation of RSNa and R-'SSO3H groupings at the boiling point, and acidsulphite solutions at pH 6 at temperatures as low as 50 C. effect the same disruption, but the formation of the groupings is immediately followed by the spontaneous formation of SNH bonds in these cases.
  • boiling solutions of reducing agents yielding S03 ions and acid sulphite solutions at pH 6 at 50 C. or above cannot be employed according to the invention. At temperatures appreciably below the boiling point and as low as 37 0.
  • solutions of bisulphites and 1 meta-bisulphites can be employed to form sulphydryl groups from the disulphide bonds of keratin. Under such temperature conditions the disruption of the disulphide bond is attended initially by the formation of R.SNa and R SSOsH- groupings as in the case of the boiling solution but the formation of S-NH bonds does not take place. Removal of the bisulp'hite or meta-bisulphite from the fibres by treatment with alkali, aqueous acetone or by simple washing results in the conversion of the R-SNa and RSSO3H groupings into RSI-I and RP-SCH groups. Sufficient reducing agent is present to reduce the R-SOH groups to RSH groups. 4
  • the reducing agents are emcient because alkalies are able to attack disulphide bonds readily whether strained or unstrained, sulphydryl and sulphonic acid groups being produced by hydrolysis, and the latter groups are reduced by the reducing agent to sulphydryl groups.
  • the sulphydryl groups are available for combination with the metal salt or organic compound.
  • the metal salts employed according to the invention may be the salts of metals other than the alkali metals, examples being salts of calcium, barium, zinc, copper or nickel.
  • the salts may be oxidizing agents, for example, nitrates, or they may be used mixed with oxidizing agents, in order that formation of disulphide bonds from sulphydryl groups may proceed at the same time as the formation of SXS bonds, X being metal or an organic grouping, and thus reduce the time of treatment. Any desired concentration of the salt solutions may be employed, but 5% is a convenient concentration.
  • the solutions of metal salts are desirably slightly acid in reaction, so that not only is the formation of further bonds in the fibre molecules assisted by the reduction of alkalinity in thefibres, but the probability of metal hydroxides or basic salts separating in reduced.
  • a solution of the reducing agent is applied to the keratin-containing :fibres as by immersion of the fibres, and then after sufficient time has been allowed for reaction with the fibres, for example about 15 minutes, the solution may be removed and the fibres may be washed, or the reducing agent completely removed by the use of an agent adapted to combine withit or otherwise render it inactive, or eliminate it; for example Where bisulphites are employed as reducing agents a 60% aqueous acetone solution may be employed to remove the agent.
  • the washing operation or removal of the reducing agent is, however, unnecessary where the metal salt does not react with the reducing agent to form undesirable compounds, such as metal sulphides, which would stain or otherwise spoil the fibres.
  • the fibres are then treated with the metal salt care being taken to ensure that the solution reaches all the fibres.
  • the fibres may afterwards be washed.
  • an organic compound such as phosgene may be employed to react with the reduced-fibres, when disulphide linkages containing an organic grouping will be formed.
  • the fibres may be treated with a solution containing a reducing agent and a metal salt, e. g. sodium sulphite and zinc sulphate.
  • a metal salt e. g. sodium sulphite and zinc sulphate.
  • the hair In carrying the invention into eiliect according toone method as applied by Way of example to the permanent waving of human hair, the hair, after the usual shampoo, is treated With a solutionxof the reducing agent, e. g. sodium bisulphi'te, preferably of from 5 to 20 per cent. concentration, which may contain alcohol in suitable concentration, say 10%, to minimise oxidation of the bisulphite on exposure .to air, and which may be warmed upto about 40 'C. to assistpenetrationof the hair.
  • the hair is wound on a curler and the .b-isulphi'te solution again applied, for example'by admitting it into atube surrounding the curler orby circulating it'inisome convenient zmanner about the curler.
  • the solution is kept in contact with the hair 'for a: period of about fifteen minutes andthen withdrawn;
  • the hair is thenztreated .withasolutionotanretal salt, e. g 5% copper water. containing 5 alcohol is prepared; the proportions of the two conipo'unds' being adjusted: to givepI-I "6;” ,
  • The. solution is circulated about the hair;lwoun'd on a curler, by any convenient means for about minutes, being'maintained at from toz50lC.
  • thehair-and'the pH value becomes about. 6'; ;
  • the hair; and the solution in. contact therewith are preferably maintained at 359-to C. or higher for'about fifteencminutes, as by applying the necessaryzheat to the curlersior by heating the hair by' a stream of hot. air-from a dryin'g apparatus, -evaporation or the solution be-x ing'prevented inthe latter; case by. covering the curlers or thewhole headzxvith a Water-impermeable'coven. 1:1 j HTreatmeritof thehair with a' metal isal'tithen follotvs as described above. A solution of; 5%.
  • calcium or barium nitrate may beemp'loyed-as the. salt. solution .wherebyl both-1 disulphide bonds are formed bylr'oxidation of Z sulphydrylz groupsand .'1 Sf-BaS+. Tor ".-"-.S+'C a-Sfi. bonds :by combinationof such groupsywiththe metal. i
  • sulphide solution brought to pI-I 10 is employed.
  • the solution is applied to the hair before'or. after win'dingbn-a; curler and in addition may be. cir-z culated about (the-hair on the curler; "A solution of an alkali, for. example a ,baryta solution at the specified pH; may also be employedfbeing'applied' to the hair in small: quantity. :1: The alkaliireacts with. the hair molecules andiiforms a hydrosulphide. Treatment is complete in about fifteen minutes at 30 C.
  • the hair may then be subjected to; the finishing treatment usual info-permanent wavingo'perationsi .1 mSuccessful treatment offibre's andfibrous ma terials may-also beeffected at pH valuesyother thanipI-I' 6 and; pHlO-ll.
  • the configuration given to the hair is then made permanent by treatment witlr'a 5% solution of a metal salt suchas copper sulphate, .or'a solutioh'of .an organic compound;"with'or without an'oxidi'zing agent.
  • the usual crabbing and blowing operations for the removal or equalisingof stress in the fabrics may be dispensed with and a reduction treatment in the cold or warm solutions of reducing agents, such am as a 5 to 20% solution of alkali bisulphites, or a 0.6% solution of sodium sulphide'give'n in their place.
  • reducing agents such as a 5 to 20% solution of alkali bisulphites, or a 0.6% solution of sodium sulphide'give'n in their place.
  • the reducing agent by disrupting the disulphide bond in the wool molecule relieves stress inthe fibres.
  • the fibres arestabilised by a sub-- sequent treatment with a 5% or other dilute somoval of distortion in knitted fabrics .of Wool arising from uneven strain on the yarn, by treatment of the fabric with a solution of a reducing agent,and. subsequent stabilising'by treatment with a metal salt solution or an. organic compound with or without an oxidizing agent.
  • rics or artificial astrackan and Persian lamb fab-r rics may have a permanent set given to them by treatment of the deformed yarn with'a; reducing agent in the cold or warm state, followed by treatment witha solution of a' metal salt with or without an oxidizing agent, to: give permanence to the set.
  • the invention may be applied toimproving the resistance of fibres or fibrous materials containing keratin, such as fabrics or yarns, to deterioration by alkalies and alkali sulphide solutions, apart altogether from the application of a permanent set to the'fibre or relief of. stress in the fabric, by treatment with a reducing agent,
  • a metal atom or other grouping into the disulphide linkages of keratin may serve for the fixing ofdyes to the keratin molecules, keratin fibres or keratin-containing materials which have been treated with a solution of a reducing agent and then with a solution of a metal salt in the manner which has been described above in connection with the applica tion of a permanent set, the release of stress or.
  • the increasing of resistance of the keratin to deterioration by alkalies may be subjected to dyeing without the need for a preliminary mordanting operation.
  • lpMethod of permanently waving hair which comprises treating the hair for a period not ex ceeding 30'minutes with a solution of a reducing agent at a temperature appreciably below the boiling point and in the absence of amphoteric metals to effect reduction and "disruption of the disulphide or cystine bond of keratin of the hair with the formation of sulphydrylgroups and thereafter treating the hair while maintaining it in a curled or waved condition with a solution of at least one polyvalent metal compound whereby to form. sulphur bonds containing-a polyvalent metal in thehair'molecules while the hair is in the curled or waved condition;
  • Method of permanently waving hair which comprises treating the hair for a period not exceeding 30 minutes with an alkaline solution of a reducing agent at a pH of'at least and a temperature appreciably below thexboiling point and, in the absence of amphoteric metals to efiect reduction and disruption of the constituent di-- sulphide or cystine bond of keratin with the formation of-sulphydryl groups, and then while maintaining the hair ina curled or waved conditiontreating.
  • a 'solutionof at least one polyvalent metal compound whereby to form sulphur-bonds containing a polyvalent metal in the hair molecules while the hair is in the, curled or waved condition. :2
  • Method of permanently wavingv hair which comprises treating the hair for a period not exceedingj30 minutes with a solution of at least one compound of the group, consisting of acid sulphites of monovalentmetalsand radicals at a pH of about 4 and at a'temperature substantially below the :boiling pointof water-to reflect disruption ofthe constituentdisulphide or cystine bond .of keratinofthe hair with the formation of sulphy-dryl and sesulphonic acid groups, andthen while maintaining the hair in a curledor waved condition treating. it with a, solution of: at least one polyvalent metal compound, whereby to form sulphur bonds containing a polyvalent metal in the hairifmole'cules .while the hair isin the curled or waved condition.
  • Method 7 Metal-d of permanently waving hair which comprises treating the hair with an alkaline solution 'of an organic hydrosulphide, in the absence of amphoteric metals; to effect disruption of the disulphide bond of keratin of the hair and then while maintaining the hair in a curled or waved condition treating" it with a solution of at least one polyvalent metal salt whereby to form sulphur bonds containing a polyvalent metal in the hair molecules while the hair is in the curled or waved condition.
  • Method of permanently waving hair which comprises treating the hair for a period'not exceeding BOminutes with'an alkaline solution of a hydro-sulphide of an alkali metal, including ammonium, at a pH of at least 10 and at a temperature appreciably below the boil, in the absence of amphoteric .metals,'to effect disruptionof the disulphide bond of the keratin of the hair and then while maintaining the hair in a curled or waved condition treating it with a solution of at least one polyvalent metal salt whereby to form sulphur bonds containing a polyvalent metal in the hair molecules while the hair is in the curled or waved condition.
  • a hydro-sulphide of an alkali metal including ammonium

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Animal Husbandry (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Textile Engineering (AREA)
  • Cosmetics (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
US53688A 1934-12-10 1935-12-09 Treatment of keratins Expired - Lifetime US2261094A (en)

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GB35495/34A GB453700A (en) 1934-12-10 1934-12-10 Improvements in and relating to the treatment of fibres or fibrous materials containing keratin

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US53687A Expired - Lifetime US2201929A (en) 1934-12-10 1935-12-09 Treatment of fibers or fibrous materials containing keratin

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BE (1) BE417226A (enrdf_load_stackoverflow)
FR (1) FR815582A (enrdf_load_stackoverflow)
GB (3) GB453700A (enrdf_load_stackoverflow)
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Cited By (35)

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US2418664A (en) * 1946-06-10 1947-04-08 Harry R Ramsey Hair treating cream
US2418940A (en) * 1944-01-19 1947-04-15 Du Pont Sulfur-containing polymeric compounds
US2434562A (en) * 1941-10-17 1948-01-13 Textile Foundation Process of treating animal fibers and product thereof
US2464280A (en) * 1945-03-07 1949-03-15 Raymond Lab Inc Cream hair treating preparations
US2464281A (en) * 1945-03-07 1949-03-15 Raymond Lab Inc Cream hair treating preparations
US2466963A (en) * 1945-06-16 1949-04-12 Thiokol Corp Polysulfide polymer
US2501184A (en) * 1944-04-06 1950-03-21 Lawrence Richard Bruce Inc Method of dyeing keratinous fibers
US2508714A (en) * 1946-10-07 1950-05-23 Harris Res Lab Process of treating keratinous materials
US2508713A (en) * 1946-10-07 1950-05-23 Harris Res Lab Treatment of keratinous material
US2540494A (en) * 1949-09-03 1951-02-06 Milton H Schwarz Permanent hair waving
US2540980A (en) * 1946-10-16 1951-02-06 Raymond Lab Inc Process and composition for treating keratinous material
US2577710A (en) * 1941-06-16 1951-12-04 Procter & Gamble Permanent waving compositions and methods
US2610941A (en) * 1946-12-14 1952-09-16 L Oreal Soc Hair-dye compositions
US2623039A (en) * 1949-05-02 1952-12-23 Rochester Button Co Thermosetting keratinoid compositions and method of making the same
US2642332A (en) * 1948-10-01 1953-06-16 Monsanto Chemicals Method of treating keratinous yarns and compositions therefor
US2691378A (en) * 1953-07-23 1954-10-12 Oliva David Permanent wave lotion
US2719104A (en) * 1951-07-11 1955-09-27 Carl G Westerberg Dyeing composition and process for keratinaceous material
US2736323A (en) * 1949-08-13 1956-02-28 Tide Water Patent Dev Company Permanent waving solutions and method
US2739033A (en) * 1951-03-19 1956-03-20 Du Pont Treatment of reduced keratinous materials with alpha,alpha'-dihalodicarboxylic acid
US2742909A (en) * 1951-08-14 1956-04-24 Turner Hall Corp Respiratory pigments of blood in setting permanent waves
US2806762A (en) * 1951-10-24 1957-09-17 Armour & Co Method of chemically curling animal hair with sulfur dioxide in aqueous solution
US2914374A (en) * 1954-03-24 1959-11-24 Harris Res Lab Inc Bleaching of keratinous fibrous material
US2926061A (en) * 1957-04-23 1960-02-23 Varsenig Z Pasternak Method of increasing the curl, filling power, etc., of land fowl feathers with zirconium sulfate and product produced thereby
US2928713A (en) * 1957-04-23 1960-03-15 Varsenig Z Pasternak Chromic acid treatment of feathers
US3178877A (en) * 1962-05-29 1965-04-20 Deering Milliken Res Corp Method for making elastic yarn containing keratinous fibers
US3464825A (en) * 1967-02-28 1969-09-02 Gen Mills Inc Keratin protein product and process of preparing same
US4304244A (en) * 1977-06-09 1981-12-08 Carson Products Company Hair straightening process and hair curling process and compositions therefor
US4324263A (en) * 1977-06-09 1982-04-13 Carson Products Company Hair straightening process and hair curling process and compositions therefor
US4605018A (en) * 1981-02-19 1986-08-12 Carson Products Company Method of treating hair and anhydrous composition related thereto
US4840791A (en) * 1984-02-06 1989-06-20 Redken Laboratories, Inc. Hair-waving process
US5047233A (en) * 1984-02-06 1991-09-10 Redken Laboratories, Inc. Hair-waving process
US5061483A (en) * 1990-05-01 1991-10-29 Chesebrough-Pond's Inc. Permanent wave hair compositions containing transition metal oxide compounds
US6269412B1 (en) 1997-05-13 2001-07-31 Micron Technology, Inc. Apparatus for recording information system events
US20050255070A1 (en) * 2004-05-14 2005-11-17 Jennifer Albano Nutritive/restorative yogurt based probiotic hair care composition
US20090211593A1 (en) * 2007-10-05 2009-08-27 Peter Coppola Reactive Keratin Protein Formulations and Methods of Using for Revitalizing Hair

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US2535684A (en) * 1950-12-26 Recovery of protein from
US2876781A (en) * 1942-04-04 1959-03-10 Permanent Hair Waving Corp Hair waving lotion of alkali metal and ammonium salts of an aliphatic mercaptan carboxylic acid
US2434688A (en) * 1942-11-03 1948-01-20 Ralph L Evans Regenerated keratin
US2437965A (en) * 1944-01-18 1948-03-16 Lawrence Richard Bruce Inc Method for relaxing keratinous fibres
US2442461A (en) * 1944-03-09 1948-06-01 Hoffmann La Roche Stable solutions of calcium ascorbate
US2479542A (en) * 1944-08-26 1949-08-16 Thiokol Corp Preparation of mercaptans
US2564722A (en) * 1945-06-04 1951-08-21 Raymond Lab Inc Process for treating hair to impart a permanent set thereto
US2624347A (en) * 1945-11-09 1953-01-06 Rose E Melaro Method of waving hair
DE958764C (de) * 1948-10-02 1957-02-21 Schwarzkopf Fa Hans Mittel zur dauerhaften Formveraenderung von menschlichem Haar bei Temperaturen von 20 bis 200íÒ
DE905193C (de) * 1949-03-22 1954-02-25 Henkel & Cie Gmbh Verfahren zur Kraeuselung oder Entkraeuselung von menschlichen oder tierischen Haaren od. dgl.
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
US2708940A (en) * 1949-06-22 1955-05-24 Gillette Co Composition and method of cold waving
US2600624A (en) * 1950-03-15 1952-06-17 Alice Parker Hair-waving composition
BE504346A (enrdf_load_stackoverflow) * 1950-06-30
DE972419C (de) * 1950-08-11 1959-07-16 Procter & Gamble Verfahren zur AEnderung der Eigenschaften von keratinhaltigen Stoffen
DE968630C (de) * 1950-09-02 1958-03-13 Wella Ag Reagenzpapier zum Nachweis von Thioglykolsaeure bzw. Thioglykolat
US2615828A (en) * 1951-02-15 1952-10-28 Procter & Gamble Compositions for treating keratin-containing materials
US2776668A (en) * 1951-06-28 1957-01-08 Rubinstein Inc H Method and preparations for the permanent dyeing of keratinous material
DE1034820B (de) * 1952-03-05 1958-07-24 Wella Ag Verfahren zur verformenden Behandlung von Keratinfasern
US2857237A (en) * 1953-03-20 1958-10-21 Edward R Frederick Method of enhancing filling power, etc., of landfowl feathers with hydrosulfide compounds and products produced thereby
US2817342A (en) * 1953-12-17 1957-12-24 Colgate Palmolive Co Method of permanently reshaping a keratin-containing substance
DE1021979B (de) * 1954-01-29 1958-01-02 Gillette Co Verfahren und Mittel zur dauernden Formaenderung von menschlichem Haar
US2809643A (en) * 1954-04-30 1957-10-15 Freeman Rose Hair curler
US2774355A (en) * 1955-03-23 1956-12-18 Du Pont Permanent hair waving neutralization by monopersulfate
DE3443327C1 (de) * 1984-11-28 1985-09-05 Rosorius, Gerhard, 2085 Quickborn Verfahren zur Verbesserung der Eigenschaften von Textilien,die aus nativen pflanzlichen oder tierischen Fasern bestehen oder diese enthalten
EP0346151A3 (en) * 1988-06-10 1990-02-21 University of Leeds Industrial Services Ltd. Method of setting hair
US5378813A (en) * 1992-05-29 1995-01-03 President And Fellows Of Harvard College Meso-2,5-dimercapto-N,N,N'N'-tetramethyladipamide
DE102010039878A1 (de) 2010-08-27 2012-03-01 Henkel Ag & Co. Kgaa Blondierung mit reduktiver Vorbehandlung
FR3045347B1 (fr) * 2015-12-18 2019-12-27 L'oreal Composition comprenant au moins un sulfite avec un ph inferieur a 5,0
IT202100012569A1 (it) * 2021-05-14 2022-11-14 Lanificio Luigi Colombo S P A Procedimento per la realizzazione di un tessuto comprendente disegni in rilevo realizzati con intrecci di fili

Cited By (39)

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Also Published As

Publication number Publication date
FR815582A (fr) 1937-07-16
US2201929A (en) 1940-05-21
BE417226A (enrdf_load_stackoverflow)
GB456336A (en) 1936-10-23
GB453700A (en) 1936-09-10
NL47270C (enrdf_load_stackoverflow) 1900-01-01
GB453701A (en) 1936-09-10

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