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Publication numberUS3840656 A
Publication typeGrant
Publication dateOct 8, 1974
Filing dateApr 7, 1970
Priority dateOct 5, 1965
Also published asDE1617702A1
Publication numberUS 3840656 A, US 3840656A, US-A-3840656, US3840656 A, US3840656A
InventorsG Kalopissis, P Roussopoulos, C Zviak
Original AssigneeOreal
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Process for improving the durability and quality of a hair set and new products for carrying out this process
US 3840656 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

United States Patent Int. Cl. A61k 7/00 U.S. Cl. 424-47 Claims ABSTRACT OF THE DISCLOSURE Compositions for treating hair to improve its mechanical properties containing at least a 1.5 molar concentration of thiol disulfide oxidizing agent to thiol reducing agent having an alkaline pH.

One of the important operations in hairstyling is the setting of the hair.

This operation consists essentially of rolling hair previously dampened with water or an aqueous solution on rollers whose diameters vary according to the desired effect, but which are generally of about to millimeters. Next the hair is dried and the rollers are removed. Then the coiffure is completed by combing it out.

It has long been known that styles resulting from simple sets, especially those in which the hair has been dampened with water only, do not last well and are highly sensitive to humidity.

To remedy these defects, water-alcohol or alcoholic solutions of natural or synthetic resins or polymers are used in the setting operation, though the results are not always completely satisfactory.

The applicants have just discovered that it is possible to notably improve the durability and quality of a set by giving the hair a chemical treatment while the hair is in its natural state, that is without using curling pins, rollers or any other device designed to give hair a particular shape. Sets carried out in the usual manner on hair so treated yield noticeably better results than sets on untreated hair.

The object of the present invention is to provide a new process for treating hair so that it may be more effectively set, this process being essentially characterized by the fact that after the hair has first been washed, it is impregnated with an alkaline solution consisting of a mixture of at least one reducing agent belonging to the thiol class and at least one oxidizing agent consisting of a thiol disulfide. This composition is left to act for a sufficient length of time, for example, from 1 to 15 minutes, then the hair is thoroughly rinsed.

Another object of the invention is to provide a new process for setting hair, this process being essentially characterized by the fact that the hair is first treated as described above, then set in the conventional manner using water or an aqueous or water-alcohol solution of a setting resin.

In one embodiment of the invention, the aforecited treatment is carried out while shampooing the hair.

In accordance with the invention, the composition containing the mixture of thiol and disulfide has a pH falling between about 9 and 10. The pH of the composition may be regulated using ammonia or any organic or mineral base which may be used in cosmetics such as monoethanolamine, diethanolamine, or morpholine.

In accordance with the invention, some of the thiols which may be used to carry out this process are: thioglycolic acid, thioglycerol, glycol thioglycolate, glycerol thioglycolate, glycol thiolactate, S-mercaptoethanol, N- carboxymethyl mercaptoacetamide, thiolactic acid, [3- mercaptopropionic acid, although this list is in no Way exhaustive.

Among the disulfides which may be used to carry out the invention are those which correspond to the above thiols.

The proportion of the molar concentration of the disulfide to that of the thiol may vary widely, though it may never be less than about 1.5. Generally the proportion may vary up to about 20, but it is usually of the order of 2.5 and 15.

For each thiol-disulfide mixture, it is desirable, remembering the above directions, to determine the disulfide/ thiol molar ratio which yields the best results.

According to the invention, a thiol may be used with its corresponding disulfide, but this is not essential. It is equally possible to use compositions containing mixtures of several thiols and several disulfides.

The thiol concentration in the compositions used to carry out this process according to the invention may vary widely, but it is usually between 0.01 and 0.5 mol/liter.

The process according to the invention has several advantages.

First, the process according to the invention results in sets which hold longer than conventional sets obtained using pure water or resin solutions.

Moreover, the improvement in the holding quality of the sets obtained using the process according to the invention is noticeable not only in the first set thereafter, but also in later sets which may be carried out without again using the process according to the invention.

In addition, it is much simpler to use the process according to the invention than it is to use the permanent setting techniques which are known today. Since the composition according to the invention is applied to hair which has not yet been rolled on curling pins or rollers, the composition, in the form of a lotion of a fluid cream, may simply be brushed into the hair.

Finally, hair treated according to the invention is easier to manage and lends itself to a better coifIure.

Another object of the present invention is to provide the new industrial product consisting of a cosmetic composition for treating hair with a view to notably improving the quality of later sets. This composition is essentially characterized by the fact that it is alkaline and that it contains a mixture of at least one reducing agent belonging to the thiol class and at least one oxidizing agent consisting of a thiol disulfide compound. This composition may also have the diverse particulars cited above during the discussion of the process utilizing this composition.

The composition according to the invention may take the form of liquid solutions, creams or gels. It may also be packaged in the form of aerosols for use in the spray state or as a lasting. or temporary foam. the form of liquid solutions, creams or gels. It may also contain other cosmetic additives such as perfumes or dyes to make the composition more versatile, or cationic products to make it easier to untangle the hair and apply the composition, or swelling agents such as urea to make it easier for the composition to penetrate to the interior of the keratinic fiber, or sequestrant agents so that the composition may be stored for a longer time.

Another object of the present invention is to provide the new industrial product which consists of a composition for simultaneously washing hair and treating it so that it may be more effectively set later. This new composition is essentially characterized by the fact that it contains at least one detergent which may be used as a shampoo and a mixture of at least one reducing agent belonging to the thiol class and at least one oxidizing agent consisting of a thiol disulfide compound.

Conforming to the invention, the process described above may thus be carried out by simultaneously washing the hair and pretreating it so that it may be more effectively set later.

In accordance with the invention, the various types of compounds known for their use in shampoos may be used in the composition.

For example, noniouic shampoos such as those which contain ethylene oxides in their molecules may be used.

In such nonionic shampoos, the solubility may also be the result of OH functions fixed on the lipophile chain. Sugar esters belong to this category of shampoos.

Anionic shampoos such as lauryl sulfate or dodecyl benzene sulfonate or cationic shampoos such as quaternary arnmonias or salts of fatty amines may also be used.

Finally, ampholite or amphoteric shampoos may be used, these being the shampoos which carry both negative and positive charges, as is the case for example with the long-chain amino acids.

These compositions may contain for example from 2 to 10% detergent and from 0.5 to 10% thiol compounds, and from 3 to 50% thiol disulfide compounds.

Conforming to the invention, the composition just described may be used as a weekly or monthly shampoo so as to keep the hair in condition to undergo sets which will last longer and will be of better quality.

In order that the invention may be better understood, several examples will now be given by way of illustration, though they are in no way exhaustive.

EXAMPLE 1 At the moment of use, the following composition is prepared:

Thioglycolic acid g Dithioglycerol g 5.7 Ammonia, q.s.p. pH=9.5

Distilled water, q.s.p cc 100 The hair is washed in the usual manner and dried. Next enough of this lotion is applied to impregnate all the hair. The lotion is left for 15 minutes, then the hair is thoroughly rinsed and set without using other ingredients.

The hair is dried under a hood, unrolled, and combed out.

It is noted that the application of such a solution makes the hair easier to style and that the set holds notably longer than a conventional set carried out under the same conditions.

EXAMPLE 2 The following solution is prepared:

Thiolactic acid g 1 Dithiodilactic acid g 5 Monoethanolamine, q.s.p. pH=9.5

Perfume g 0.5 Distilled water, q.s.p. cc 100 4 EXAMPLE 3 The two following solutions are prepared and packaged separately:

Part A fi-Mercaptopropionic acid g 3 Monoethanolamine, q.s.p. pH=9.6 Water, q.s.p cc 10 Part B Dithiodiglycerol g 40 Distilled water, q.s.p. cc

At the moment of use, equal volumes of these two solutions are mixed. It is applied to the hair in the usual manner and the hair is then set.

Very satisfactory results are obtained. The holding quality of the coiffure is notably improved for 5 to 6 weeks.

EXAMPLE 4 The two following solutions are prepared and packaged separately:

The pH of this part B is about 3.

When parts A and B are mixed at the moment of use, the resin Carbopol 934 contained in part B is neutralized by the excess alkali in part A. The mixture gels and the result is a thick paste whose pH equals 9.5 and which is extremely easy to apply.

The gel thus obtained is applied to the hair in the usual manner and excellent results are obtained both from the point of view of ease of application due to the form of the product and of the holding quality of the set.

The high holding quality of the coitfure lasts from 2 to 3 weeks.

EXAMPLE 5 At the moment of use, a composition having the following formula is prepared:

Thioglycerol g 1 Dithiodiglycerol g 20 Lauryl ammonia sulfate g 25- Monoethanolamine, q.s.p. pH=9.5

Water, q.s.p. cc 100 10 cm. of this composition are used for the first washing of natural hair, then the hair is rinsed and 10 cm. more of this composition are applied.

The scalp is massaged for several moments while the composition is being emulsified, then there is a 10 minute wait.

The hair is then rinsed and immediately set using, if desired, a conventional setting lotion which may consis of a water-alcohol resin solution. 1

The hair is rolled on rollers and dried. Then the rollers are removed and the hair is combed out.

It is noted that the hair falls into place easily and that it is both supple and strong.

The set holds much longer than if it had been carried out without the pre-treatment according to the invention.

After a week the hair may be washed again with a conventional shampoo and set. The holding quality of this set also will be notably improved.

Experiments have shown that the particular qualities of these sets hold true for all sets carried out for a month after the pre-treatment according to the invention.

After this time another pre-treatment using the abovedescribed shampoo is necessary.

EXAMPLE 6 At the moment of use, a composition having the following formula is obtained:

Thioglycerol 0.4

Dithiodiglycerol g 1.3

Lauric sulfate neutralized with soda plus 2 molecules of ethylene oxide g 25 Monoethanolamine, q.s.p. pH=9.5

Water, q.s.p cc 100 This composition is used regularly in place of a conventional shampoo.

Sets obtained this way hold for up to about 10 days.

The results are excellent, whether the solution is applied to natural or to lightly sensitized hair.

EXAMPLE 7 A shampoo powder is made by preparing dry the following mixture:

Laurie sulfate with 50% active matter, neutralized with soda g 3 Potassium thioglycolate g 0.5 Powdered dithiodiglycerol g 5 Kaolin g 1 Sodium carbonate q.s.p. pH=9.5

For an aerosol shampoo, the following mixture is first prepared:

Laurie sulfate neutralized with soda plus 2 molecules of ethylene oxide g 50 Diethanolamide of fatty acid of copra g 2 Dithiodiglycerol g 40 Thioglycerol g 2 Monoethanolamine q.s.p. pH=9.5 Water, q.s.p. cc 100 This mixture is packaged in an aerosol bomb with the following composition:

The above-described liquid 69 Fluoric hydrocarbon sold under the trademark Freon 12 CCI F B.Pt. (-21.6 F.) 3

Butane 3 To use this shampoo, 10 to 15 grams of it are sprayed on dampened hair in the usual manner.

Again a notable improvement in the quality of later sets is obtained.

It will of course be appreciated that the foregoing examples have been given purely by way of illustration and could be modified as to detail without thereby departing from the basic principles of the invention.

What is claimed is:

1. A method of treating unconstrained hair in a hair treating process to improve and prolong its setting properties without imparting any permanent deformation to the same comprising the steps of first applying to the unconstrained hair an effective amount of a composition containing, in aqueous media, a thiol reducing agent selected from the group consisting of thioglycolic acid, thioglycerol, glycol thioglycolate, glycerol thioglycolate, glycol thiolactate, B-mercapto-ethanol, N-carboxymethylmercapto-acetamide, thiolactic acid and ,B-mercaptopropionic acid and an oxidizing agent selected from the group consisting of the disulfides of the following thiols: thioglycolic acid, thioglycerol, glycol thioglycolate, glycerol thioglycolate, glycol thiolactate, fi-mercapto-ethanol, N-carboxymethyl-rnercapto-acetamide, thiolactic acid and B-mercaptopropionic acid, the molar ratio of the oxidizing agent to said reducing agent being at least 1.5 :1 and up to 20:1, with the amount of reducing agent in the composition being about 0.01-05 mole per liter and the amount of oxidizing agent being about 0.015-10 mole per liter, said composition having a pH of about 9-10, allowing the composition to remain in contact with the unconstrained hair for about 1 to 15 minutes and thereafter rinsing and drying the hair.

2. The method of claim 1, in which the composition containing the reducing agent and the oxidizing agent also contains 2 to 10% by weight of a shampoo detergent.

3. The method of claim 1 in which the hair is initially washed before being impregnated with the composition containing the reducing agent and the oxidizing agent.

4. The method of claim 1 in which the amount of reducing agent is between 0.5 and 10% and the amount of oxidizing agent between 3 and 50% by weight of said composition.

5. The method of claim 1, wherein the composition is sprayed on the hair with a propellant to initially form a light transient foam.

References Cited UNITED STATES PATENTS 2,719,813 10/1955 Haefele (I) 424-72 2,719,814 10/ 1955 Haefele (II) 42472 2,719,815 10/1955 Sanders 424-72 3,103,468 9/1963 Shepard et al 424-47 X 3,144,391 8/1964 Goff 424-47 X FOREIGN PATENTS 1,336,311 7/1963 France.

ALBERT T. MEYERS, Primary Examiner F. E. WADDELL, Assistant Examiner US. Cl. X.R. 424-72

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4134412 *Nov 18, 1976Jan 16, 1979Wella AktiengesellschaftWater soluble film-forming salt
US4956175 *Aug 2, 1989Sep 11, 1990Societe Anonyme Dite: L'orealN-(mercaptoalkyl)omega-hydroxyalkylamides and their use as a reducing agent in a process for permanently deforming hair
US5350572 *Feb 18, 1993Sep 27, 1994Shiseido Co., Ltd.Permanent waving composition
US5617883 *Sep 14, 1994Apr 8, 1997Shiseido Co., Ltd.Reducing agents for permanent waving of hair
US5720944 *Mar 21, 1996Feb 24, 1998Kao CorporationPolyglycol monothio(glycolate or lactate) as reducing agents
US6652842Nov 13, 2001Nov 25, 2003Noville, Inc.Clarity; stronger, longer duration fragrance; improved skin feel; reduced irritation
US6723304Oct 8, 2002Apr 20, 2004Noville, Inc.Oral care compositions comprising diglycerol
US6770264Jan 8, 2003Aug 3, 2004Noville, Inc.Chewing gum compositions comprising diglycerol
DE3707415A1 *Mar 7, 1987Sep 15, 1988Wella AgMittel und verfahren zur dauerhaften haarverformung
EP0286774A1 *Jan 7, 1988Oct 19, 1988Wella AktiengesellschaftComposition and process for permanently waving the hair
EP0884998A1 *Feb 21, 1997Dec 23, 1998L'orealNovel method for perming keratinous materials
Classifications
U.S. Classification424/47, 424/70.5
International ClassificationA45D7/04, A61K8/46, A61Q5/04
Cooperative ClassificationA61K2800/59, A61Q5/04, A61K8/46
European ClassificationA61K8/46, A61Q5/04