Search Images Maps Play YouTube News Gmail Drive More »
Sign in
Screen reader users: click this link for accessible mode. Accessible mode has the same essential features but works better with your reader.

Patents

  1. Advanced Patent Search
Publication numberUS3093146 A
Publication typeGrant
Publication dateJun 11, 1963
Filing dateMar 12, 1959
Priority dateMar 14, 1958
Also published asDE1150491B
Publication numberUS 3093146 A, US 3093146A, US-A-3093146, US3093146 A, US3093146A
InventorsAndre Viout, Gregoire Kalopissis
Original AssigneeOreal
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Process for permanent setting of living hair by surface active compounds
US 3093146 A
Abstract  available in
Images(2)
Previous page
Next page
Claims  available in
Description  (OCR text may contain errors)

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

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2577710 *Jun 16, 1941Dec 4, 1951Procter & GamblePermanent waving compositions and methods
US2714119 *Aug 7, 1953Jul 26, 1955Sterling Drug IncProcess for preparing amides of alphamercapto lower fatty acids
US2792307 *Jul 20, 1953May 14, 1957Universal Oil Prod CoStabilization of organic compounds
US2817342 *Dec 17, 1953Dec 24, 1957Colgate Palmolive CoMethod of permanently reshaping a keratin-containing substance
US2869559 *Oct 7, 1957Jan 20, 1959Procter & GambleNon-volatile mercaptan and hydroxyamine impregnated end wrap and method of use
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4098811 *Dec 2, 1976Jul 4, 1978Ciba-Geigy CorporationPerfluoroalkylthioamido amine and ammonium compounds
US4567198 *Feb 6, 1984Jan 28, 1986Roussel UclafEthanethioates and mercaptoamides and use thereof as analgesic and enkephalinase inhibitory compounds
US4973475 *Oct 7, 1988Nov 27, 1990Revlon, Inc.Hair treatment and conditioning agents
US5071441 *Sep 6, 1990Dec 10, 1991Revlon, Inc.Hair treatment and conditioning agents
US5091573 *Aug 27, 1990Feb 25, 1992Rohm And Haas CompanyThiol-terminated hydroxyamides
US5116608 *Sep 25, 1989May 26, 1992Seiwa Kasei Co., Ltd.Permanent waving composition
US5247125 *Feb 28, 1991Sep 21, 1993Rohm And Haas CompanyThiol-terminated hydroxyamides
US20070225611 *Feb 6, 2007Sep 27, 2007Kumar Uday NNon-invasive cardiac monitor and methods of using continuously recorded cardiac data
EP0361391A2 *Sep 26, 1989Apr 4, 1990Seiwa Kasei Co., Ltd.Permanent waving composition
EP0361391A3 *Sep 26, 1989Dec 27, 1990Nippon Shokubai Kagaku Kogyo Co. Ltd.Permanent waving composition
EP0577473A1 *Jun 23, 1993Jan 5, 1994L'orealReducing cosmetic composition for the permanent deformation of hair based on a mercaptoalkylamino-amide and process for the permanent deformation of hair
EP0712633A1 *Nov 18, 1994May 22, 1996Izhak BlankPharmaceutical compositions for topical application
Classifications
U.S. Classification132/203, 510/492, 564/192, 510/119, 510/126, 252/188.2, 562/589, 424/70.2
International ClassificationC07C, A45D7/00, A45D7/04, C07C233/00, A61K8/46, A61K8/30, A61Q5/04
Cooperative ClassificationA61Q5/04, A61K8/46
European ClassificationA61K8/46, A61Q5/04