US3093146A - Process for permanent setting of living hair by surface active compounds - Google Patents

Process for permanent setting of living hair by surface active compounds Download PDF

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US3093146A
US3093146A US798805A US79880559A US3093146A US 3093146 A US3093146 A US 3093146A US 798805 A US798805 A US 798805A US 79880559 A US79880559 A US 79880559A US 3093146 A US3093146 A US 3093146A
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hair
setting
surface active
active compounds
permanent waving
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US798805A
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Kalopissis Gregoire
Viout Andre
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LOreal SA
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LOreal SA
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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
    • A61K8/30—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

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  • the hairdressers final purpose is in effect to realize by a hair disposition a style of hair-dressing adapted to the up to date taste and to the treated hair; such disposition is socalled a setting in the art.
  • the hairdresser arranges Wet hair, previously curled by the permanent waving, in locks which he rolls at his will and dries when the whole of the operation is completed.
  • the present invention aims to simplify and facilitate the hairdressers work for such hair setting which constitutes the essential part of his art, owing to the fact that it makes unnecessary the previous permanent waving proper of the hair and that it makes it possible to accomplish the hair setting in a single opera-tion while giving to the hair a better lasting which extends the duration of the hair-dressing in a noticeable manner.
  • This invention has for a primary object a hair setting process eliminating any previous permanent waving, charaoterized by the fact that the hair is impregnated with an aqueous solution of a compound having a reducing effect analogous to that of mercaptans, so as to impart to the hair the desired plasticity, and having moreover the characteristics of a cation-active detergent which cleans the hair and comprises a fatty chain susceptible of adhering to the cleaned hair while giving the same a brightness and a suppleness which facilitate the hair setting, that such hair setting is performed after rinsing of the hair and that the hair is air dried so as to permit an oxidation which gives again to the set hair its natural elasticity.
  • the present invention has for another object to provide a cation aotive addition salt of an amine, comprising a thiol group reducing the keratin disulphide bridges to put into practice the aforementioned hair setting process, said salt being characterized by the fact that it belongs to the general formula:
  • R is a hydrogen atom or a lower alkyl radical comprising not more than 6 carbon atoms
  • R" is a lower alkyl radical, any either of substituents 'R, R' being selected from hydrogen and a lower alkyl radical and the other being a water repelling fatty radical having from 8 to 24 carbon atoms and X being an acid anion harmless to the live hair and to the scalp.
  • the compound according to this invention may be used advantageously in the state of an addition salt obtained by reacting this compound with an inorganic or organic acid.
  • one object of the present invention is to provide a process for making a cation-active compound of the aforementioned Formula (I), characterized by the fact that it consists in bringing into reaction equimolecular amount of a mercaptan having the general formula:
  • the reduced bridges SS- in a relatively low number by the application of these reducing surfaceactive products, may be rebuilt by the sole action of the oxygen of air during the conventional operations of drying in a draught, under a helmet, without using an oxidizing solution as in the case of a permanent waving.
  • foaming cationic detergent properties allow them to be applied as a shampoo as it is applied in a conventional manner previously to the purely manual operation of hair-setting; so as to avoid, in particular, when first applied, any excessive dilution by water, after which the hair is rinsed and the hair-setting and drying operations are elfected according to the usual practice.
  • the efiiciency of the amide formation may be increased by reacting under the same conditions as those mentioned above new amounts of ethyl thioglycolate, once or twice, taking into consideration the amount of non reacted amine.
  • the product may be purified by using its insoluble cadmium salt (by reacting cadmium acetate) which can be separated and decomposed later by hydrogen sulphide.
  • the practically pure product is thus obtained in the form of an aqueous solution.
  • This product having an 85% purity was directly treated with lactic acid. There was obtained a gel, which was dissolved in water at a 30% to 35% concentration. This solution is used as a shampoo.
  • An improved process for setting living hair without submitting the hair to a previous permanent waving which comprises, impregnating the hair with an aqueous solution of an addition salt of a member of the group consisting of the organic and inorganic acid salts of a compound having a general formula wherein R is a member of the group consisting of a hydrogen atom and a lower alkyl radical having not more than 6 carbon atoms, R" is a lower alkyl radical, and one of the substituents R and R is selected from the group consisting of a hydrogen atom and a lower alkyl radical, the other being a water repelling fatty acid radical having from 8 to 24 carbon atoms, the organic and inorganic acids being harmless to the live hair and to the scalp, said addition salt having a reducing action analogous to that of mercaptans, so as to impart to the hair the desired plasticity and having moreover the characteristics of a cation-active detergent which cleans the hair and com prises a fatty chain susceptible to adhere to the cleaned hair
  • An improved process for setting live hair without submitting the hair to previous permanent waving which comprises, impregnating the hair with an aqueous solution of an addition salt of lactic acid, with a compound having a general formula wherein R is a member of the group consisting of a hydrogen atom and a lower alkyl radical having not more than 6 carbon atoms, R is a lower alkyl radical, and one of the substituents R and R, is selected from the group consisting of a hydrogen atom and a lower alkyl radical, the other being a water repelling fatty acid radical having from 8 to 24 carbon atoms, rinsing the hair so impregnated, separating the hair into individual locks, setting the hair in the form desired and allowing the hair to dry so as to permit oxidation to impart to the hair in a set condition its natural elasticity.
  • An improved process for setting hair without submitting the hair to previous permanent waving which comprises impregnating the hair with an aqueous solution containing an addition salt of lactic acid with mercapto- N-lauryl-N-(Z-diethylaminoethyl) acetamide, rinsing the so impregnated hair, separating the hair into individual locks, setting the hair in the form desired and air drying the same to permit oxidation to impart to the hair in a set condition its natural elasticity.
  • An improved process for setting hair without submitting the hair to previous permanent waving which comprises, impregnating the hair with an aqueous solution containing an addition salt of lactic acid with mercapto N (2 methyl,2 lauryl,aminoethyl) acetamide, rinsing the so impregnated hair, separating the hair into individual locks, setting the hair in the form desired and allowing the hair to dry so as to permit oxidation to impart to the hair in a set condition its natural elasticity.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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  • Cosmetics (AREA)

Description

United States Patent 3,093,146 PROCESS FOR PERMANENT SETTING 0F LIVING HAIR BY SURFACE ACTIVE COMPOUNDS Gregoire Kalopissis and Andre Viout, Paris, France, assignors to LOreal, a corporation of France No Drawing. Filed Mar. 12, 1959, Ser. No. 798,805 Claims priority, application France Mar. 14, 1958 4 Claims. (Cl. 1327) Permanent waving of living hair is generally obtained in a known manner by two successive operations viz. a first operation in which the hair is impregnated with a reducing solution so as to insure a more or less complete breakdown of the disulphide bridges of the keratin, While imparting to the hair a sufficient plasticity to lead itself to the curled form which is given thereto on haircurlers, and a second operation during which the hairdresser impregnates the hair with a neutralizing solution, most often of an oxidizing character, intended to give again to the hair in the new form thereof the mechanical properties which it has lost during the first operation, said properties resulting most often from the rebuilding of the aforementioned disulphide bridges.
However, permanent waving of the hair so effected is only a preliminary step in hair-dressing art. The hairdressers final purpose is in effect to realize by a hair disposition a style of hair-dressing adapted to the up to date taste and to the treated hair; such disposition is socalled a setting in the art. During said setting, the hairdresser arranges Wet hair, previously curled by the permanent waving, in locks which he rolls at his will and dries when the whole of the operation is completed.
Various attempts have been made to improve the lasting of such setting (and consequently the hair-dressing duration) by pretreating the hair with different natural or synthetic resin compositions, or surface active compounds, the application being effected by using a lotion, a rinsing or a spraying, for example in aerosol form. However, such products do not insure a durable result, since the action thereof on hair is only superficial.
The present invention aims to simplify and facilitate the hairdressers work for such hair setting which constitutes the essential part of his art, owing to the fact that it makes unnecessary the previous permanent waving proper of the hair and that it makes it possible to accomplish the hair setting in a single opera-tion while giving to the hair a better lasting which extends the duration of the hair-dressing in a noticeable manner.
This invention has for a primary object a hair setting process eliminating any previous permanent waving, charaoterized by the fact that the hair is impregnated with an aqueous solution of a compound having a reducing effect analogous to that of mercaptans, so as to impart to the hair the desired plasticity, and having moreover the characteristics of a cation-active detergent which cleans the hair and comprises a fatty chain susceptible of adhering to the cleaned hair while giving the same a brightness and a suppleness which facilitate the hair setting, that such hair setting is performed after rinsing of the hair and that the hair is air dried so as to permit an oxidation which gives again to the set hair its natural elasticity.
The present invention has for another object to provide a cation aotive addition salt of an amine, comprising a thiol group reducing the keratin disulphide bridges to put into practice the aforementioned hair setting process, said salt being characterized by the fact that it belongs to the general formula:
Patented June 11, 1963 in which R is a hydrogen atom or a lower alkyl radical comprising not more than 6 carbon atoms, R" is a lower alkyl radical, any either of substituents 'R, R' being selected from hydrogen and a lower alkyl radical and the other being a water repelling fatty radical having from 8 to 24 carbon atoms and X being an acid anion harmless to the live hair and to the scalp.
The compound according to this invention may be used advantageously in the state of an addition salt obtained by reacting this compound with an inorganic or organic acid.
Further, one object of the present invention is to provide a process for making a cation-active compound of the aforementioned Formula (I), characterized by the fact that it consists in bringing into reaction equimolecular amount of a mercaptan having the general formula:
(II) HS-CHR'COOR in which R, is a lower alkyl radical and of an alkylene diamine having the general formula:
(III) NHR NRIIR!!! R, R, R" and R' having the significations recited for the Formula ('I).
It may be expected that the compounds of Formula ('1), owing to their chemical constitution, resulting from this reaction have a moderate reducing activity on the hair keratin. On the contrary, said reducing activity, which would not be suflicient for the permanent waving, is appropriate especially for the operation of so-called hair setting.
The reduced bridges SS-, in a relatively low number by the application of these reducing surfaceactive products, may be rebuilt by the sole action of the oxygen of air during the conventional operations of drying in a draught, under a helmet, without using an oxidizing solution as in the case of a permanent waving.
When one or more compounds of Formula (I) are used according to the present invention to effect a hair setting, their foaming cationic detergent properties allow them to be applied as a shampoo as it is applied in a conventional manner previously to the purely manual operation of hair-setting; so as to avoid, in particular, when first applied, any excessive dilution by water, after which the hair is rinsed and the hair-setting and drying operations are elfected according to the usual practice.
In the following examples, given in an illustrative and by no means limitative way, there is described the preparation of some compounds of the aforementioned Formula (I):
Example I Mercapto-N-lauryl-N-(Z-diethylaminoethyl) acetamide. Such compound has for its formula:
Preparatiom-There was prepared a hydro-alcoholic solution containing 1 mol of N-lauryl, N-diethylethylene diamine and 1 mol+10% of ethyl thioglycolate; this solution was heated under reflux during 10 hours under a stream of N after vacuum concentration, there was obtained a residue containing 62% of active product.
The efiiciency of the amide formation may be increased by reacting under the same conditions as those mentioned above new amounts of ethyl thioglycolate, once or twice, taking into consideration the amount of non reacted amine.
It is thus possible to obtain finally the desired amide in the form of a waxy body having a purity. The
efficiency of the condensation amounts to 85% of the amine used. The corresponding salt of lactic acid is obtained from this raw product, because purification is rather difiicult.
The product may be purified by using its insoluble cadmium salt (by reacting cadmium acetate) which can be separated and decomposed later by hydrogen sulphide. The practically pure product is thus obtained in the form of an aqueous solution.
Example II Mercapto-N(2-methyl,2-lauryl,aminoethyl) acetamide. This compound has the following formula:
CH; HS-GH:C ONH-CHzOHzN There was added 1 mol a excess) of ethyl thioglycolate in an alcoholic solution to 1 mol of N-lauryl-N- methyl-ethylene-diamine. This solution was heated under reflux during 4 hours and concentrated under vacuum. The resulting residue contained 85 of amide. After a period of 48 hours, it set partly. There were obtained crystals melting at 30 C.-32 C. The yield of the condensation was 75% based on the amine used.
This product having an 85% purity was directly treated with lactic acid. There was obtained a gel, which was dissolved in water at a 30% to 35% concentration. This solution is used as a shampoo.
It is to be understood that the foregoing examples are only illustrative and by no way limitative of the scope of the invention as defined in the appended claims.
What we claim is:
1. An improved process for setting living hair without submitting the hair to a previous permanent waving which comprises, impregnating the hair with an aqueous solution of an addition salt of a member of the group consisting of the organic and inorganic acid salts of a compound having a general formula wherein R is a member of the group consisting of a hydrogen atom and a lower alkyl radical having not more than 6 carbon atoms, R" is a lower alkyl radical, and one of the substituents R and R is selected from the group consisting of a hydrogen atom and a lower alkyl radical, the other being a water repelling fatty acid radical having from 8 to 24 carbon atoms, the organic and inorganic acids being harmless to the live hair and to the scalp, said addition salt having a reducing action analogous to that of mercaptans, so as to impart to the hair the desired plasticity and having moreover the characteristics of a cation-active detergent which cleans the hair and com prises a fatty chain susceptible to adhere to the cleaned hair, while giving to the latter a brightness and a suppleness which facilitates hair setting, rinsing the so impregnated hair, separating the hair into individual locks, setting the hair in the form desired and allowing the hair to dry so as to permit oxidation to impart to the hair in a set condition its natural elasticity.
2. An improved process for setting live hair without submitting the hair to previous permanent waving, which comprises, impregnating the hair with an aqueous solution of an addition salt of lactic acid, with a compound having a general formula wherein R is a member of the group consisting of a hydrogen atom and a lower alkyl radical having not more than 6 carbon atoms, R is a lower alkyl radical, and one of the substituents R and R, is selected from the group consisting of a hydrogen atom and a lower alkyl radical, the other being a water repelling fatty acid radical having from 8 to 24 carbon atoms, rinsing the hair so impregnated, separating the hair into individual locks, setting the hair in the form desired and allowing the hair to dry so as to permit oxidation to impart to the hair in a set condition its natural elasticity.
3. An improved process for setting hair without submitting the hair to previous permanent waving, which comprises impregnating the hair with an aqueous solution containing an addition salt of lactic acid with mercapto- N-lauryl-N-(Z-diethylaminoethyl) acetamide, rinsing the so impregnated hair, separating the hair into individual locks, setting the hair in the form desired and air drying the same to permit oxidation to impart to the hair in a set condition its natural elasticity.
4. An improved process for setting hair without submitting the hair to previous permanent waving, which comprises, impregnating the hair with an aqueous solution containing an addition salt of lactic acid with mercapto N (2 methyl,2 lauryl,aminoethyl) acetamide, rinsing the so impregnated hair, separating the hair into individual locks, setting the hair in the form desired and allowing the hair to dry so as to permit oxidation to impart to the hair in a set condition its natural elasticity.
References Cited in the file of this patent UNITED STATES PATENTS 2,577,710 McDonough Dec. 4, 1951 2,714,119 Crounse July 26, 1955 2,792,307 Chenicek May 14, 1957 2,817,342 Henkin Dec. 24, 1957 2,869,559 Moore Jan. 20, 1959

Claims (1)

1. AN IMPROVED PROCESS FOR SETTING LIVING HAIR WITHOUT SUBMITTING THE HAIR TO A PERVIOUS PERMANENT WAVING WHICH COMPRISES, IMPREGNATING THE HAIR WITH AN AQUEOUS SOLUTION OF AN ADDITION SALT OF A MEMBER OF THE GROUP CONSISTING OF THE ORGANIC AND INORGANIC ACID SALTS OF A COMPOUND HAVING A GENERAL FORMULA
US798805A 1958-03-14 1959-03-12 Process for permanent setting of living hair by surface active compounds Expired - Lifetime US3093146A (en)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4098811A (en) * 1976-12-02 1978-07-04 Ciba-Geigy Corporation Perfluoroalkylthioamido amine and ammonium compounds
US4567198A (en) * 1983-02-07 1986-01-28 Roussel Uclaf Ethanethioates and mercaptoamides and use thereof as analgesic and enkephalinase inhibitory compounds
FR2636841A1 (en) * 1988-09-29 1990-03-30 Seiwa Kasei Co Ltd COMPOSITION FOR PERMANENT HAIR WAVING
US4973475A (en) * 1988-10-07 1990-11-27 Revlon, Inc. Hair treatment and conditioning agents
US5091573A (en) * 1990-08-11 1992-02-25 Rohm And Haas Company Thiol-terminated hydroxyamides
US5247125A (en) * 1990-08-11 1993-09-21 Rohm And Haas Company Thiol-terminated hydroxyamides
FR2692481A1 (en) * 1992-06-23 1993-12-24 Oreal Reductive cosmetic composition for the permanent deformation of hair based on a mercaptoalkylamino amide and permanent hair deformation process.
EP0712633A1 (en) * 1994-11-18 1996-05-22 Izhak Blank Pharmaceutical compositions for topical application
US20070225611A1 (en) * 2006-02-06 2007-09-27 Kumar Uday N Non-invasive cardiac monitor and methods of using continuously recorded cardiac data

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2654617B1 (en) * 1989-11-20 1993-10-08 Oreal COSMETIC REDUCING COMPOSITION FOR PERMANENT CONTAINING, AS REDUCING AGENT, ALETHEINE OR ONE OF ITS SALTS, AND ITS USE IN A PROCESS OF PERMANENT DEFORMATION OF HAIR.
DE19732079C1 (en) * 1997-07-25 1999-02-04 Wella Ag Saturated, alkyl-substituted N-mercaptoacetyl heterocycles, compositions and methods of permanent hair styling based thereon

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2577710A (en) * 1941-06-16 1951-12-04 Procter & Gamble Permanent waving compositions and methods
US2714119A (en) * 1953-08-07 1955-07-26 Sterling Drug Inc Process for preparing amides of alphamercapto lower fatty acids
US2792307A (en) * 1953-07-20 1957-05-14 Universal Oil Prod Co Stabilization of organic compounds
US2817342A (en) * 1953-12-17 1957-12-24 Colgate Palmolive Co Method of permanently reshaping a keratin-containing substance
US2869559A (en) * 1957-10-07 1959-01-20 Procter & Gamble Non-volatile mercaptan and hydroxyamine impregnated end wrap and method of use

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2577710A (en) * 1941-06-16 1951-12-04 Procter & Gamble Permanent waving compositions and methods
US2792307A (en) * 1953-07-20 1957-05-14 Universal Oil Prod Co Stabilization of organic compounds
US2714119A (en) * 1953-08-07 1955-07-26 Sterling Drug Inc Process for preparing amides of alphamercapto lower fatty acids
US2817342A (en) * 1953-12-17 1957-12-24 Colgate Palmolive Co Method of permanently reshaping a keratin-containing substance
US2869559A (en) * 1957-10-07 1959-01-20 Procter & Gamble Non-volatile mercaptan and hydroxyamine impregnated end wrap and method of use

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4098811A (en) * 1976-12-02 1978-07-04 Ciba-Geigy Corporation Perfluoroalkylthioamido amine and ammonium compounds
US4567198A (en) * 1983-02-07 1986-01-28 Roussel Uclaf Ethanethioates and mercaptoamides and use thereof as analgesic and enkephalinase inhibitory compounds
FR2636841A1 (en) * 1988-09-29 1990-03-30 Seiwa Kasei Co Ltd COMPOSITION FOR PERMANENT HAIR WAVING
EP0361391A2 (en) * 1988-09-29 1990-04-04 Seiwa Kasei Co., Ltd. Permanent waving composition
US5116608A (en) * 1988-09-29 1992-05-26 Seiwa Kasei Co., Ltd. Permanent waving composition
EP0361391A3 (en) * 1988-09-29 1990-12-27 Seiwa Kasei Co., Ltd. Permanent waving composition
US5071441A (en) * 1988-10-07 1991-12-10 Revlon, Inc. Hair treatment and conditioning agents
US4973475A (en) * 1988-10-07 1990-11-27 Revlon, Inc. Hair treatment and conditioning agents
US5091573A (en) * 1990-08-11 1992-02-25 Rohm And Haas Company Thiol-terminated hydroxyamides
US5247125A (en) * 1990-08-11 1993-09-21 Rohm And Haas Company Thiol-terminated hydroxyamides
FR2692481A1 (en) * 1992-06-23 1993-12-24 Oreal Reductive cosmetic composition for the permanent deformation of hair based on a mercaptoalkylamino amide and permanent hair deformation process.
EP0577473A1 (en) * 1992-06-23 1994-01-05 L'oreal Reducing cosmetic composition for the permanent deformation of hair based on a mercaptoalkylamino-amide and process for the permanent deformation of hair
EP0712633A1 (en) * 1994-11-18 1996-05-22 Izhak Blank Pharmaceutical compositions for topical application
US20070225611A1 (en) * 2006-02-06 2007-09-27 Kumar Uday N Non-invasive cardiac monitor and methods of using continuously recorded cardiac data

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NL111194C (en) 1965-05-17
CH401083A (en) 1965-10-31
FR1193289A (en) 1959-11-02
BE576566A (en) 1959-09-11
GB891600A (en) 1962-03-14
DE1150491B (en) 1963-06-20
CH387229A (en) 1965-01-31

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