US2201929A - Treatment of fibers or fibrous materials containing keratin - Google Patents

Treatment of fibers or fibrous materials containing keratin Download PDF

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US2201929A
US2201929A US53687A US5368735A US2201929A US 2201929 A US2201929 A US 2201929A US 53687 A US53687 A US 53687A US 5368735 A US5368735 A US 5368735A US 2201929 A US2201929 A US 2201929A
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hair
treatment
solution
reducing agent
keratin
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US53687A
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Speakman John Bamber
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    • 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

  • This invention relates to improvements in the treatment of substances containing keratin, such as hair and wool, and is particularly concerned with treatments for the application of a permameat set to such substances or for the removal of stress from materials made from keratins such as wool and with the treatment of keratin materials in or before finishing operations.
  • Keratin-containing fibers are customarily sub- 9 jected to steaming or hot water treatment in the presence of compounds which may include reducing agents at or only slightly below the boiling point for the release of strain and the application of a permanent set.
  • the object of the present invention is to pro- 43 vide a treatment whereby release of strain and permanent set are obtained over a much larger range of temperatures below the customary tem peratures and especially down through temperatures to as low as room temperatures where de- 45 sired.
  • the invention consists in treating fibrous substance containing keratin, such as wool or hair, with a solution of a reducing agent in alkaline solution to efiect reduction and disruption of the an constituent disulphide or cystine bond of keratin with the formation of sulphydryl groups, and then, while maintaining the substance in a tormation which it is desired to render permanent, causing the formation of further disulphide bonds as in or between the fiber molecules by subjecting (Ci.
  • Suitable reducing agents which may be employed according to the invention are sodium sulphide, sodium hydrosulphide, cysteine hydrochloride, sodium hypophosphite, sodium thiosulphate, sodium hydrosulphite, sodium dithionate. lutions whose concentrations may be varied in accordance with the natureof the reducing agent and its mode of use.
  • the reducing agent may be formed in situ, for example if keratin containing fibers are moistened with alkali, e. g., baryta, hydrosulphide is formed by reaction with the fiber molecules, which may be caused to attain the required concentration by maintaining the total volume of solution low.
  • Reducing agents as a whole, in alkaline solution 5 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 disruption of the disulphide bond by reduction according to the invention may be employed to relieve stress in the fibers, which stress may have been caused. for example, by deforming the fibers in giving them a desired configuration, and leaves them in such a state that formation of further bonds may take place whereby the fibers will retain permanently any set or configuration which may have been given them.
  • reducing agent may be of any desired alkalinity, it is found in certain cases that for the application of permanent sets They may be employed in the form of so- 25 or waves to keratin fibers, conditions are most favourable to the permanence and efiiciency of the set when the reducing solution actually in contact with the hair is at or above pH 10, preferably pH 11.
  • reducing agents are effective, since alkalies are able to attack unstrained as well as strained disulphide bonds, sulphydryl and sulphenic acid groups being produced by hydrolysis, which latter groups are reduced by the reducing agent to sulphydryl groups. Disulphide bonds may be formed from the suphydryl groups by the subsequent action of an oxidising agent.
  • Example I The hair after a preliminary shampoo is treated with a 6 per cent, sodium hydrosulphide solution brought to pH I! by addition of sodium carbonate or sodium metasilicate.
  • the hair may be treated with the solution before or after winding on a curler or the solution may be circulated about the hair wound on a curler.
  • the solution is maintained in contact with the hair for about 15 minutes at room temperature or above, after which a solution of an oxidising agent may be applied, for example a 10 volume hydrogen peroxide solution or 10 per cent. ammonium persulphate solution.
  • the hair may then be subjected to the usual finishing operations of permanent waving.
  • Example II In this case, a solution of a reducing agent as specified in Example I, is employed, but instead of winding the hair on curlers it is formed into waves or curls on the head after being moistened with the solution.
  • a thickening agent may be added to the solution of reducing agent, for instance agaragar or kieselguhr. in sufiicient amount to give the consistency of a paste. Suitable wetting agents may also be added.
  • the solution is allowed to remain in contact with the hair for about 15 minutes at about room temperature or above. The formation of further bonds to give permanence to the waves or curls can then be brought about by treatment with an oxidising agent.
  • An alternative manner of carrying out the treatment of the invention according to this example is to form the hair intowaves or curls on the head and treat it with the reducing agent, the subsequent procedure being as set out above.
  • the reagents may be applied by spraying or any other suitable means.
  • the usual crabbing and blowing operations for the removal or equalising of stress in the fabrics may be replaced by a reduction treatment in cold or warm alkaline solutions of reducing agents, for example a 0.6 per cent. solution of sodium sulphide.
  • the fabrics may then be treated for the removal of the reducing agent, for example by washing, or by treatment in a solution of an oxidising agent such as a l0-volume hydrogen peroxide solution. Removal of reducing agents generally may be effected by treatment with an oxidising agent.
  • the invention may also be applied to the removal of distortion in knitted fabrics of wool arising from uneven stress in the yarn, by treatment of the fabric with an alkaline solution of a reducing agent and subsequent removal of the reducing agent as by treatment with an oxidising agent.
  • Yarns for the manufacture of curl fabrics or artificial astrakhan and Persian lamb fabrics may have a permanent set given to them by treatment of the deformed yarn with a reducing agent followed by removal of the reducing agent as by treatment with an oxidising agent.
  • a method of giving a desired permanent form to fibrous substances containing keratin which comprises treating the substance with an alkaline solution of a reducing agent free from sulphite at a pH of at least 10 and a temperature appreciably below the boiling point whereby to effect reduction and disruption of the constitutent disulphide or cystine bond of keratin with the formation of sulphydryl groups, and then, 'while maintaining the substance in a form which it is desired to render permanent, causing the formation of further cystine bonds through interaction of the sulphydryl groups by subjecting the fibers to the action of an oxidising agent comprising a per-compound.
  • a method of permanently waving hair which comprises treating the hair with an alkaline solution of a reducing agent free from sulphite at apI-I of at least 10 and a temperature appreciably below the boiling point whereby to effect reduction and disruption of the constituent disulphide or cystine bond of keratin of the hair with the formation of sulphydryl groups and then, while maintaining the hair in a curled or waved condition, causing the formation of further cystine bonds in the hair molecules by interaction of the sulphydryl groups by subjecting the hair to the action of an oxidising agent comprising a per-compound.
  • the reducing agent employed is an alkali metal sulphide, cysteine hydrochloride, sodium hypophosphite, sodium thiosulphate, sodium hydo-sulphite and sodium dithionate.
  • a method as claimed in claim 3 wherein the per-compound is ammonium persulphate.
  • a method of permanently waving hair which comprises treating the hair with a solution of an alkaline reducing agent free from sulphite at a pH of at least 10 and a temperature appreciably below the boiling point whereby to effect reduction and disruption of the constituent disulphide'or cystine bond of keratin of the hair with the formation of sulphydryl groups and then, while maintaining the hair in a curled or waved condition, causing the formation of further cystine bonds in the hair molecules by interaction of the sulphydryl groups by subjecting the hair to the action of a solution of a peroxide.
  • a method of permanentlywaving hair which comprises treating the hair with a solution of an alkaline reducing'agent free from sulphite at a pH of at least 10 and a temperature appreciably below the boiling point whereby to efl'ect reduction and disruption of the constituent disulphide or cystine bond of keratin of the hair with the formation of sulphydryl groups and then, while maintaining the hair in a curled or waved condition, causing the formation of further cystinebonds in the hair molecules by interaction of the sulphydryl groups by subjecting the hair to the action of a solution of a per-salt.

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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)

Description

@atented May 21, 1940 UNITED SKATES TREATMENT OF FEERS R FIBROUS MA- TERIALS CQNTAINENG KERA'EIIN John Bamber Speakman, Far Headingley, Leeds,
-" England No Drawing. Application Becember 9, 1935; Se-
rial No. 53,687. In Great Britain December M Claims.
This invention relates to improvements in the treatment of substances containing keratin, such as hair and wool, and is particularly concerned with treatments for the application of a permameat set to such substances or for the removal of stress from materials made from keratins such as wool and with the treatment of keratin materials in or before finishing operations.
I Keratin-containing fibers are customarily sub- 9 jected to steaming or hot water treatment in the presence of compounds which may include reducing agents at or only slightly below the boiling point for the release of strain and the application of a permanent set.
It has been proposed to treat wool or hair with a boiling bisulphite solution uhile tensioning the wool or hair. Such treatment at the boiling point will result in disruption of the disulphide bonds of keratin and the immediate formation 2t) oi S-NH bonds as indicated by the following equations where R-S-S-R and R'--NH2 represent the peptide and associated side chains of keratin. gm The reactions take place with such readiness that the maximum possible number of linkages result. Bisulphite solutions, however, have the disadvantage that at theboiling point of water they are capable of serious destructive attack on hair 5 and at lower temperatures the rate of formation of linkages as represented by equation 2 above, is negligibly small and therefore proceeds far too slowly to be commercially useful.
The object of the present invention is to pro- 43 vide a treatment whereby release of strain and permanent set are obtained over a much larger range of temperatures below the customary tem peratures and especially down through temperatures to as low as room temperatures where de- 45 sired.
The invention consists in treating fibrous substance containing keratin, such as wool or hair, with a solution of a reducing agent in alkaline solution to efiect reduction and disruption of the an constituent disulphide or cystine bond of keratin with the formation of sulphydryl groups, and then, while maintaining the substance in a tormation which it is desired to render permanent, causing the formation of further disulphide bonds as in or between the fiber molecules by subjecting (Ci. Mil-8'33) R,SS-R+reducing agent=RSH+RSH and permanent set or form is given-to the relaxed fibers according to the invention, not by the formation of SNH- bonds by interaction of sulphonic groups with amino groups as in the 15 prior treatment referred to, but solely by direct union of sulphydryl groups themselves to form cystine bonds, brought about by the action of the oxidising agent.
Suitable reducing agents which may be employed according to the invention are sodium sulphide, sodium hydrosulphide, cysteine hydrochloride, sodium hypophosphite, sodium thiosulphate, sodium hydrosulphite, sodium dithionate. lutions whose concentrations may be varied in accordance with the natureof the reducing agent and its mode of use. The reducing agent may be formed in situ, for example if keratin containing fibers are moistened with alkali, e. g., baryta, hydrosulphide is formed by reaction with the fiber molecules, which may be caused to attain the required concentration by maintaining the total volume of solution low.
Reducing agents as a whole, in alkaline solution 5 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 disruption of the disulphide bond by reduction according to the invention may be employed to relieve stress in the fibers, which stress may have been caused. for example, by deforming the fibers in giving them a desired configuration, and leaves them in such a state that formation of further bonds may take place whereby the fibers will retain permanently any set or configuration which may have been given them.
Although the solution of reducing agent may be of any desired alkalinity, it is found in certain cases that for the application of permanent sets They may be employed in the form of so- 25 or waves to keratin fibers, conditions are most favourable to the permanence and efiiciency of the set when the reducing solution actually in contact with the hair is at or above pH 10, preferably pH 11.
At or above pH 10 reducing agents are effective, since alkalies are able to attack unstrained as well as strained disulphide bonds, sulphydryl and sulphenic acid groups being produced by hydrolysis, which latter groups are reduced by the reducing agent to sulphydryl groups. Disulphide bonds may be formed from the suphydryl groups by the subsequent action of an oxidising agent.
The following are examples of convenient ways of carrying the invention into effect as applied by way of example to the permanent waving of hair.
Example I The hair after a preliminary shampoo is treated with a 6 per cent, sodium hydrosulphide solution brought to pH I!) by addition of sodium carbonate or sodium metasilicate. The hair may be treated with the solution before or after winding on a curler or the solution may be circulated about the hair wound on a curler. The solution is maintained in contact with the hair for about 15 minutes at room temperature or above, after which a solution of an oxidising agent may be applied, for example a 10 volume hydrogen peroxide solution or 10 per cent. ammonium persulphate solution.
The hair may then be subjected to the usual finishing operations of permanent waving.
Example II In this case, a solution of a reducing agent as specified in Example I, is employed, but instead of winding the hair on curlers it is formed into waves or curls on the head after being moistened with the solution. To facilitate manipulation of the hair, a thickening agent may be added to the solution of reducing agent, for instance agaragar or kieselguhr. in sufiicient amount to give the consistency of a paste. Suitable wetting agents may also be added. The solution is allowed to remain in contact with the hair for about 15 minutes at about room temperature or above. The formation of further bonds to give permanence to the waves or curls can then be brought about by treatment with an oxidising agent.
An alternative manner of carrying out the treatment of the invention according to this example, is to form the hair intowaves or curls on the head and treat it with the reducing agent, the subsequent procedure being as set out above.
The reagents may be applied by spraying or any other suitable means.
In the application of the invention to fabrics made of keratins such as wool, the usual crabbing and blowing operations for the removal or equalising of stress in the fabrics may be replaced by a reduction treatment in cold or warm alkaline solutions of reducing agents, for example a 0.6 per cent. solution of sodium sulphide. The fabrics may then be treated for the removal of the reducing agent, for example by washing, or by treatment in a solution of an oxidising agent such as a l0-volume hydrogen peroxide solution. Removal of reducing agents generally may be effected by treatment with an oxidising agent.
The invention may also be applied to the removal of distortion in knitted fabrics of wool arising from uneven stress in the yarn, by treatment of the fabric with an alkaline solution of a reducing agent and subsequent removal of the reducing agent as by treatment with an oxidising agent.
Yarns for the manufacture of curl fabrics or artificial astrakhan and Persian lamb fabrics may have a permanent set given to them by treatment of the deformed yarn with a reducing agent followed by removal of the reducing agent as by treatment with an oxidising agent.
I claim:
1. A method of giving a desired permanent form to fibrous substances containing keratin, which comprises treating the substance with an alkaline solution of a reducing agent free from sulphite at a pH of at least 10 and a temperature appreciably below the boiling point whereby to effect reduction and disruption of the constitutent disulphide or cystine bond of keratin with the formation of sulphydryl groups, and then, 'while maintaining the substance in a form which it is desired to render permanent, causing the formation of further cystine bonds through interaction of the sulphydryl groups by subjecting the fibers to the action of an oxidising agent comprising a per-compound.
2. A method as claimed in claim 1, wherein the reducing agent is removed from the substance prior to treatment with the oxidising agent.
3. A method of permanently waving hair which comprises treating the hair with an alkaline solution of a reducing agent free from sulphite at apI-I of at least 10 and a temperature appreciably below the boiling point whereby to effect reduction and disruption of the constituent disulphide or cystine bond of keratin of the hair with the formation of sulphydryl groups and then, while maintaining the hair in a curled or waved condition, causing the formation of further cystine bonds in the hair molecules by interaction of the sulphydryl groups by subjecting the hair to the action of an oxidising agent comprising a per-compound.
4. A method as claimed in claim 3 wherein the hair in the form of strands is wound on curlers after treatment with the reducing agent and is treated with the oxidising agent while it is on the curlers.
5. A method as claimed in claim 3 wherein the reducing agent employed is an alkali metal sulphide, cysteine hydrochloride, sodium hypophosphite, sodium thiosulphate, sodium hydo-sulphite and sodium dithionate.
6. A method as claimed in claim 3 wherein the reducing agent employed is an alkali metal hydrosulphide.
7. A method as claimed in claim 3 wherein the reducing agent employed is cysteine hydrochloride.
8. A method as claimed in claim 1 wherein the per-compound is hydrogen peroxide.
9. A method as claimed in claim 1 wherein the per-compound is ammonium persulphate.
10. A method as claimed in claim 3 wherein the per-compound is hydrogen peroxide.
11. A method as claimed in claim 3 wherein the per-compound is ammonium persulphate.
12. A method as claimed in claim 3, wherein reducing agent is removed from the hair prior to treatment with the oxidising agent.
13. A method of permanently waving hair which comprises treating the hair with a solution of an alkaline reducing agent free from sulphite at a pH of at least 10 and a temperature appreciably below the boiling point whereby to effect reduction and disruption of the constituent disulphide'or cystine bond of keratin of the hair with the formation of sulphydryl groups and then, while maintaining the hair in a curled or waved condition, causing the formation of further cystine bonds in the hair molecules by interaction of the sulphydryl groups by subjecting the hair to the action of a solution of a peroxide.
14. A method of permanentlywaving hairwhich comprises treating the hair with a solution of an alkaline reducing'agent free from sulphite at a pH of at least 10 and a temperature appreciably below the boiling point whereby to efl'ect reduction and disruption of the constituent disulphide or cystine bond of keratin of the hair with the formation of sulphydryl groups and then, while maintaining the hair in a curled or waved condition, causing the formation of further cystinebonds in the hair molecules by interaction of the sulphydryl groups by subjecting the hair to the action of a solution of a per-salt.
US53687A 1934-12-10 1935-12-09 Treatment of fibers or fibrous materials containing keratin Expired - Lifetime US2201929A (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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US53688A Expired - Lifetime US2261094A (en) 1934-12-10 1935-12-09 Treatment of keratins

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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2434688A (en) * 1942-11-03 1948-01-20 Ralph L Evans Regenerated keratin
US2442461A (en) * 1944-03-09 1948-06-01 Hoffmann La Roche Stable solutions of calcium ascorbate
US2535684A (en) * 1950-12-26 Recovery of protein from
US2540494A (en) * 1949-09-03 1951-02-06 Milton H Schwarz Permanent hair waving
US2564722A (en) * 1945-06-04 1951-08-21 Raymond Lab Inc Process for treating hair to impart a permanent set thereto
US2577710A (en) * 1941-06-16 1951-12-04 Procter & Gamble Permanent waving compositions and methods
US2600624A (en) * 1950-03-15 1952-06-17 Alice Parker Hair-waving composition
US2624347A (en) * 1945-11-09 1953-01-06 Rose E Melaro Method of waving hair
US2642332A (en) * 1948-10-01 1953-06-16 Monsanto Chemicals Method of treating keratinous yarns and compositions therefor
US2708940A (en) * 1949-06-22 1955-05-24 Gillette Co Composition and method of cold waving
US2736323A (en) * 1949-08-13 1956-02-28 Tide Water Patent Dev Company Permanent waving solutions and method
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
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
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
US3464825A (en) * 1967-02-28 1969-09-02 Gen Mills Inc Keratin protein product and process of preparing same
US5071641A (en) * 1988-06-10 1991-12-10 University Of Leeds Industrial Services Limited 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 (en) 2010-08-27 2012-03-01 Henkel Ag & Co. Kgaa Bleaching with reductive pretreatment

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US2434562A (en) * 1941-10-17 1948-01-13 Textile Foundation Process of treating animal fibers and product thereof
US2437965A (en) * 1944-01-18 1948-03-16 Lawrence Richard Bruce Inc Method for relaxing keratinous fibres
US2418940A (en) * 1944-01-19 1947-04-15 Du Pont Sulfur-containing polymeric compounds
US2501184A (en) * 1944-04-06 1950-03-21 Lawrence Richard Bruce Inc Method of dyeing keratinous fibers
US2479542A (en) * 1944-08-26 1949-08-16 Thiokol Corp Preparation of mercaptans
US2464281A (en) * 1945-03-07 1949-03-15 Raymond Lab Inc Cream hair treating preparations
US2464280A (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
US2418664A (en) * 1946-06-10 1947-04-08 Harry R Ramsey Hair treating cream
US2508713A (en) * 1946-10-07 1950-05-23 Harris Res Lab Treatment of keratinous material
US2508714A (en) * 1946-10-07 1950-05-23 Harris Res Lab Process of treating keratinous materials
US2540980A (en) * 1946-10-16 1951-02-06 Raymond Lab Inc Process and composition for treating keratinous material
NL69995C (en) * 1946-12-14
DE958764C (en) * 1948-10-02 1957-02-21 Schwarzkopf Fa Hans Means for permanently changing the shape of human hair at temperatures from 20 to 200 Ò
DE905193C (en) * 1949-03-22 1954-02-25 Henkel & Cie Gmbh Process for curling or uncrimping human or animal hair or the like.
DE958501C (en) * 1949-04-14 1957-02-21 Schwarzkopf Fa Hans Means for permanently changing the shape of human hair at temperatures between 20 and 200
DE958696C (en) * 1949-04-14 1957-02-21 Schwarzkopf Fa Hans Permanent wave agent for human hair
US2623039A (en) * 1949-05-02 1952-12-23 Rochester Button Co Thermosetting keratinoid compositions and method of making the same
BE504346A (en) * 1950-06-30
DE972419C (en) * 1950-08-11 1959-07-16 Procter & Gamble Process for changing the properties of substances containing keratin
DE968630C (en) * 1950-09-02 1958-03-13 Wella Ag Reagent paper for the detection of thioglycolic acid or thioglycolate
US2615828A (en) * 1951-02-15 1952-10-28 Procter & Gamble Compositions for treating keratin-containing materials
US2739033A (en) * 1951-03-19 1956-03-20 Du Pont Treatment of reduced keratinous materials with alpha,alpha'-dihalodicarboxylic acid
US2719104A (en) * 1951-07-11 1955-09-27 Carl G Westerberg Dyeing composition and process for keratinaceous material
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
DE1034820B (en) * 1952-03-05 1958-07-24 Wella Ag Process for the deforming treatment of keratin fibers
US2691378A (en) * 1953-07-23 1954-10-12 Oliva David Permanent wave lotion
US2817342A (en) * 1953-12-17 1957-12-24 Colgate Palmolive Co Method of permanently reshaping a keratin-containing substance
DE1021979B (en) * 1954-01-29 1958-01-02 Gillette Co Method and means for permanently changing the shape of human hair
US2914374A (en) * 1954-03-24 1959-11-24 Harris Res Lab Inc Bleaching of keratinous fibrous material
US2774355A (en) * 1955-03-23 1956-12-18 Du Pont Permanent hair waving neutralization by monopersulfate
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
BE632929A (en) * 1962-05-29
US4324263A (en) * 1977-06-09 1982-04-13 Carson Products Company Hair straightening process and hair curling process and compositions therefor
US4304244A (en) * 1977-06-09 1981-12-08 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
DE3443327C1 (en) * 1984-11-28 1985-09-05 Rosorius, Gerhard, 2085 Quickborn Process for improving the properties of textiles consisting of or containing native vegetable or animal fibers
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
US7374750B2 (en) * 2004-05-14 2008-05-20 Jennifer Albano Probiotic containing anhydrous hair care composition
US8785370B2 (en) * 2007-10-05 2014-07-22 Keratin Complex Holdings, Inc. Reactive keratin protein formulations and methods of using for revitalizing hair
FR3045347B1 (en) * 2015-12-18 2019-12-27 L'oreal COMPOSITION COMPRISING AT LEAST ONE SULPHITE WITH A PH LESS THAN 5.0
IT202100012569A1 (en) * 2021-05-14 2022-11-14 Lanificio Luigi Colombo S P A PROCEDURE FOR CREATING A FABRIC INCLUDING EMBOSSED DESIGNS MADE WITH INTERLAYING THREADS

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2535684A (en) * 1950-12-26 Recovery of protein from
US2577710A (en) * 1941-06-16 1951-12-04 Procter & Gamble Permanent waving compositions and methods
DE972424C (en) * 1941-06-16 1959-07-16 Sales Affiliates Patentverwert Process for the permanent deformation, in particular for permanent waving, of keratin fibers, preferably of hair on the living human body
DE948186C (en) * 1941-06-16 1956-08-30 Sales Affiliates Inc Means for the permanent shape change of hair on the living body (permanent waves)
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
US2442461A (en) * 1944-03-09 1948-06-01 Hoffmann La Roche Stable solutions of calcium ascorbate
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
US2642332A (en) * 1948-10-01 1953-06-16 Monsanto Chemicals Method of treating keratinous yarns and compositions therefor
US2708940A (en) * 1949-06-22 1955-05-24 Gillette Co Composition and method of cold waving
US2736323A (en) * 1949-08-13 1956-02-28 Tide Water Patent Dev Company Permanent waving solutions and method
US2540494A (en) * 1949-09-03 1951-02-06 Milton H Schwarz Permanent hair waving
US2600624A (en) * 1950-03-15 1952-06-17 Alice Parker Hair-waving composition
US2776668A (en) * 1951-06-28 1957-01-08 Rubinstein Inc H Method and preparations for the permanent dyeing of keratinous material
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
US2809643A (en) * 1954-04-30 1957-10-15 Freeman Rose Hair curler
US3464825A (en) * 1967-02-28 1969-09-02 Gen Mills Inc Keratin protein product and process of preparing same
US5071641A (en) * 1988-06-10 1991-12-10 University Of Leeds Industrial Services Limited 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 (en) 2010-08-27 2012-03-01 Henkel Ag & Co. Kgaa Bleaching with reductive pretreatment
WO2012025269A2 (en) 2010-08-27 2012-03-01 Henkel Ag & Co. Kgaa Bleaching with reductive pre-treatment

Also Published As

Publication number Publication date
GB453701A (en) 1936-09-10
BE417226A (en)
FR815582A (en) 1937-07-16
NL47270C (en) 1900-01-01
GB453700A (en) 1936-09-10
GB456336A (en) 1936-10-23
US2261094A (en) 1941-10-28

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