US3768490A - Permanently having and permanently setting of hair - Google Patents

Permanently having and permanently setting of hair Download PDF

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US3768490A
US3768490A US3768490DA US3768490A US 3768490 A US3768490 A US 3768490A US 3768490D A US3768490D A US 3768490DA US 3768490 A US3768490 A US 3768490A
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hair
composition
acid
thiol
disulfide
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G Kalopissis
P Roussopoulos
C Zviak
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L'Oreal SA
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L'Oreal SA
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/04Preparations for permanent waving or straightening the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing sulfur
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59Mixtures

Abstract

Process for permanently waving hair and permanently setting hair which inclides the steps of subjecting hair on rollers and applying a self neutralizing composition containing in mixture a thiol selected from the group consisting of: thioglycerol, thioglycolic acid, dimercapto-adipic acid, dimercapto-1,4 butanediol-2,3 and thiolactic acid, and a disulfide, aid disulfide being dithiodiglycerol, or dithiodiglycolic acid only when the thiol is thioglycolic acid, and wherein the amount of thiol is preferably about 2 - 5 percent weight of the composition and wherein the numerical ratio of the disulfide groups to thiol groups is greater than 1,5, or greater than 2 when the thiol is thioglycolic acid and the disulfide is dithiodiglycolic acid.

Description

United States Patent [1 1 Kalopissis et al.

[ 1 Oct. 30, 1973 PERMANENTLY WAVING AND PERMANENTLY SETTING OF HAIR [75] Inventors: Gregoire Kalopissis; Paul Roussopoulos, both of Paris; Charles Zviak, Franconville, all of France [73] Assigneei Societe Anonyme dite: L'Oreal, Paris, France [22] Filed: Jan. 31, 1972 [21] Appl. No.: 222,299

Related US. Application Data [63] Continuation-impart of Ser. No. 56,136, July 6, 1970, which is a continuation of Ser. No. 475,890, July 29, 1965, and a continuation-in-part of Ser. No. 14,757, Feb. 25, 1970, which is a continuation of Ser. No. 508,383, Nov. 17, 1965.

[52] US. Cl. 132/7, 424/72 [51] Int. Cl. A45d 7/00 [58] Field of Search 132/7; 424/72, 71

[56] References Cited UNITED STATES PATENTS 10/1955 Sanders 424/72 10/1955 Haefele 424/71 2,689,815 9/1954 Gershon 424/72 FOREIGN PATENTS OR APPLICATIONS 810,355 3/1959 Great Britain l67/87.l

1,336,311 7/1963 France l67/87.l

Primary Examiner-Louis G. Mancene Assistant Examiner-Gregory E. McNeil] Attorney-Mason, Mason & Albright 57 ABSTRACT composition and wherein the numerical ratio of the disulfide groups to thiol groups is greater than 1,5, or greater than 2 when the thiol is thioglycolic acid and the disulfide is dithiodiglycolic acid.

8 Claims, No Drawings PERMANENTLY WAVING AND PERMANENTLY SETTING OF HAIR CROSS REFERENCE TO RELATED APPLICATIONS This application is a continuation-in-part of Ser. No. 56,136 filed July 6, 1970, and Ser. No. 14,757 filed Feb. 25, 1970, which are continuations of applications Ser. Nos. 475,890 and 508,383 respectively filed July 29, 1965, and Nov. 17, 1965.

BACKGROUND OF THE INVENTION It is common knowledge that hair waving can be done in three ways, namely:

the process of permanent deformation of the hair;

the process of simple setting; and

the process of permanent setting.

A. Permanent Deformation of the Hair (Permanent waving) The permanent deformation of the hair conventionally includes the following steps:

1. Rolling the hair on permanent-wave rollers of relatively small diameter, for example 8 to 10 mm.

2. Saturating the hair with a so-called reduction agent, such as a thiol. It should be noted, however, that the saturation of the hair with the reduction agent can be done before rolling the hair on the permanent-wave rollers.

3. Rinsing the hair, still on rollers (Optional).

4. Saturating the hair, still on permanent-wave rollers, with a neutralizing or oxidizing agent, such as a solution of hydrogen peroxide.

5. Removing the permanent-wave rollers and rinsing the hair.

By this process of permanent deformation of the hair, stable and durable curls are produced called pennanent which are not affected by atmospheric humidity or even by shampooing.

B. Simple Setting.

The conventional process of simple setting includes the following steps:

1. Saturating the hair with a hair setting lotion which can be either natural water, or a water-based solution, or a resin-based hydroalcoholic solution.

2. Rolling the hair on rollers of to 30 mm. in diameter.

3. Drying the hair, still on rollers.

By this process a temporary wave is obtained which may last for a few days, but which is not designated by the term permanent wave," because shampooing washesaway the wave.

C. Permanent Setting.

The conventional process of permanent setting is, in fact, a compromise between the permanent deformation process and the simple setting process.

.The conventional process of permanent setting includes the following steps:

1. Rolling the hair on rollers of about 15 to mm. in diameter. I

2. Saturating the hair with a reducing" agent. As in the process of permanent deformation, the hair can be saturated before it is rolled on the rollers.

3. Rinsing (Optional).

4. Saturating the hair, still on rollers, with a neutralizing or oxidizing agent.

5. Rinsing the hair, still on rollers.

6. Drying the hair, still on rollers, after it has been eventually saturated with a setting solution, either a water-based solution or a resin-based hydroalcoholic solution.

By this process a permanent setting is obtained which, compared to process B, has the advantage of giving the hair a relatively stable wave which shampooing will not wash out, but which is less durable than the wave obtained in permanent waving.

The process of permanent setting makes use of compounds similar to those employed for permanent deformation of the hair, but generally less concentrated; moreover, the diameter of the rollers used is greater than that of the rollers used in permanent waving; and, finally, as in the process for simply setting, the hair, still on rollers, is allowed to dry.

As can be readily observed, the process of permanent deformation of the hair, as well as the process of permanent setting, comprises a number of steps which present numerous inconveniences.

Indeed, the fact that two different solutions must be applied one after the other, each having been left to stand from 15 to 20 minutes, notwithstanding the necessity of separate rinsings, constitutes operational complications.

Moreover, the step called neutralization or oxidation is a particularly difficult one, because the oxidizing agent penetrates the hair only with difficulty. Care must be taken not to use too much of this liquid which is slightly corrosive, lest it touch the scalp and damage the persons skin.

It must be noted, however, that certain attempts have been made to accomplish the so-called neutralization or oxidation step by restoring to the mere oxidizing action of the oxygen in the air.

By resorting to this modified process, however, a period of 5 to 8 hours is necessary if satisfactory results are to be obtained. The hair, constrained in the style that one wishes to obtain, needs that long exposure to the oxygen of the air in order to obtain the desired effect.

In order to simplify these operations, the applicants have sought to develop a process whereby the application of one and only one solution would produce simultaneously the results of the step called reduction and that called neutralization or oxidation.

A priori, such a simplification would appear difficult to realize; the process of permanent reduction of the hair is based on the opening of the cystine bridges by means of a reducer followed by the reconstituting of the same by means of an oxidizing agent. In order to produce deformation in a single step, it is therefore necessary to mix two substances -'one a reducer, the other an oxidizer which tend naturally to react on each other and which, at first, would seem to cancel out each others action on the hair.

The applicants realized, however, that during the first step it was notnecessary to open all the SS--- bridges before proceeding to close them, after having provoked the relative displacement of the keratinic chains. It would suffice to provoke a continual opening and closing of a certain number of keratinic bridges, during which time the hair would be kept in a sufficient state of deformation to provoke the slipping of the keratinic chains along with the opening of their -S-S- bridges.

The present invention is therefore as relevant to a new process of permanent deformation of the hair as it is to a process of permanent setting, both of these processes being effected in a single step.

According to the invention, in order to effect these two processes, one would utilize one and only one composition containing a mixture of certain thiols and certain disulfides in well determined proportions, so that a genuine self-neutralizing composition is obtained which makes possible in one operation the permanent deformation as well as the permanent setting of the hair, a process which until now required two steps, namely, the so-called reduction step and the so-called neutralization or oxidation step.

Compositions based on thiols and disulfides of various kinds have already been described in US. Pat. Nos. 2,719,813 and 2,719,814.

It should be noted, however, that in both of these patents, the use of such compositions is recommended in the first step only of the permanent deformation of hair, the presence of the disulfide being justified by the fact that the latter compounded with the thiol diminishes the harsh effects of the thiol.'

In fact, it is known that thiols have certain secondary effects causing damage to hair keratin.

To offset the harmful action of the thiols, it is recommended in the American patents to use thiol along with a disulfide in a numerical ratio of the disulfide groups to thethiol groups contained between 0.1 to 1.5. In these numerical ratios, the disulfides mitigate the harsh effects of the thiols without removing the reducing power of the latter.

According to these patents, it is specified, moreover, that a numerical ratio of the disulfide groups to the thiol groups in excess of 1.5 precludes curls of superior quality, whatever the duration of the application.

Consequently, for the first step in permanent waving it is recommended to contain the numerical ratios of the disulfide groups to the thiol groups between 0.25 and 0.75.

Finally, it is importantto specify that, according to the two patents, the second step called neutralization or oxidation is effected either by means of an oxidizing compound or by simple exposure of the hair to the oxygen to the atmospheric air.

These two patents contribute progress to the conventional process of permanent deformation, since they permit elimination of the harshness of the thiols, but they give'neither solution nor insights into the problem caused by the permanent deformation of the hair in one step by means of a self-neutralizing composition.

SUMMARY OF THE INVENTION As has been explained above, the present invention offers a solution to the problem causing the steps of permanent deformation and permanent setting of the hair, because it allows completion of these two processes in only one step.

The object of the present invention is to provide a new process toeffect the permanent deformation of the hair in a single step, said process being characterized by the following:

the hair subjected to a sufficient mechanical deformation is treated by means of a composition containing in mixture from 2 to 5 percent of a thiol taken in the group constituted by thioglycerol, thioglycolic acid, dimercapto-adipic acid, dimercapto-1,4 butanediol-2,3

and thiolactic acid, and a disulfide which is dithiodiglycerol. The numerical ratio of the disulfide groups to the thiol groups is greater than 1,5 and the said composition has a pH between 8,5 and 10.;

the composition mentioned above is permitted to take effect during a period of time from 5 to 30 minutes;

the hair is rinsed; and

the means affording the mechanical deformation is then removed.

According to a variation of the present invention, the permanent deformation of the hair can also be accomplished in one step, as indicated above, by using a selfneutralizing composition, a composition containing a mixture of 2 to 5 percent of thioglycolic acid for thiol and dithiodiglycolic acid for disulfide, the numerical ratio of the disulfide groups to the thiol groups being greater than 2, and the composition having a pH contained between 8.5 and 10.

The numerical ratios of the disulfide groups to the thiol groups which in the first case must be greater than 1.5 and in the second greater than 2, are critical ratios, that is to say, below these limits no deformation is obtained, or only a deformation of inferior quality which in no case can be considered permanent according to the criteria generally accepted. Among these criteria the index of fixation, If, is particularly selective, and it is generally accepted that permanent waving is produced when this index is equal to or less than 0.1. By Index of Fixation is meant the following ratio:

extension The calculation of the Index of Fixation consists therefore in measuring the force T corresponding to the area of plasticity of the hair, hence the minimum force allowing the hair to be subjected to a deformation greater than 2 percent. This force is measured:

before the treatment, and this gives the value T,;

after the treatment, with the help of a selfneutralizing composition, and this gives the value T and finally;

after the total fixation, that is to say, after the reconstruction of the ensemble of bridges -SS- of the hair keratin, by means of the hydrogen peroxide, and this gives the value T The thiol concentrate is not exactly critical, but it has been established that such a concentrate from 2 to 5 percent brings about compositions possessing the required fluidity. In fact, some concentrates stronger in thiol would produce strong disulfide concentrates ally recommended for capillary compositions so that there is no incompatibility between the scalp and the composition.

According to the invention, in the process of permanent deformation of the hair, deformation results either in waves or in straightening. To obtain a permanent wave, the mechanical device used is the permanent wave roller having a diameter of about 8 to 10 mm.

On the other hand, to obtain straightening, mechanical deformation is obtained by combing and by the application of a composition having a cream-like consistency, and this makes it possible to keep the hair in the desired configuration.

According to the invention, and as in the classical procedure for permanent deformation of the hair, the self-neutralizing compositions such as they are defined above, must be applied either before or after using the mechanical device which brings about the mechanical deformation. After the waiting time of 5 to 30 minutes, as indicated above, the mechanical device is removed and the hair is rinsed.

By this process, according to the invention of permanent deformation of the hair, curls of excellent quality are obtained which resist atmospheric humidity and subsequent shampoos.

PREFERRED EMBODIMENTS The object of the present invention also includes a process of permanent setting characterized by the fact that:

the hair, subjected to a slight mechanical deformation by means of to mm. rollers, is treated with a composition containing a mixture of 2 to 5 percent thiol taken from the group consisting of thioglycerol, thioglycolic acid, dimercaptoadipic acid, dimercapto- 1,4 butanediol 2,3 and thiolactic acid, and a disulfide, the disulfide being dithiodiglycerol. The numerical ratio of the disulfide groups to the thiol groups is greater than 1.5 and the aforesaid composition has a pH between 8,5 and 10.;

the aforementioned composition isleft to react during a 5 to 30 minute period of time;

the hair is eventually rinsed; and

the hair, still on rollers, is dried by heat externally provided.

As in the process of permanent deformation of the hair, it is also possible, according to the invention, to utilize a composition containing a mixture of 2 to 5 percent thioglycolic acid (for thiol) and of dithiodiglycolic acid (for disulfide), the'numerical ratio of the disulfide groups to the thiol groups being greater than 2 and the composition having a pH between 8,5 and 10.

According to this permanent setting process, beautiful waves are produced, identical to those obtained by the classical process involving two steps.

As can be ascertained, the self-neutralizing compositions used in the process producing permanent deformation of the hair and the process of permanent setting are of the same kind and therefore are judged by the same criteria.

In a variation of the permanent setting process, it is possible, after rinsing the hair, to apply to it a waterbased or a resin-based hydroalcoholic setting lotion.

Compositions producing simultaneously permanent deformation and permanent setting of the hair can appear in various forms. It is preferable, however, to utilize water-based or hydroalcoholic solutions (ethanol water, for example) which can contain other ingredients, such as perfumes, swelling agents, etc. To obtain straightening of the hair, it is preferable to use creamytextured compositions which allow the hair to be held in the desired configuration.

Finally, it should be noted that when, in the processes of the invention, compositions are used that are formed by pairing the following thiol/disulfide: thioglycerol/dithiodiglycerol, and thioglycolic acid/dithiodiglycolic acid, the required quantity of disulfide can be obtained at the precise moment of application by obtaining the oxidation of a predetermined quantity of surplus thiol in such a way as to obtain in the first case a ratio of the disulfide groups to the thiol groups greater than 1,5, and in the second case, a ratio greater than 2.

Among the oxidizing agents that produce in situ the disulfides starting from corresponding thiols, the following can be mentioned: oxidized water (hydrogen peroxide), sodium iodate, sodium periodate, sodium bromate, etc.

In order to make the invention more readily understandable, several examples of the two processes according to the invention are described below by way of illustration.

Example 1 To obtain a permanent deformation of hair, a solution composed of the following ingredients is prepared at the time of application:

thioglycerol 5 g dithiodiglycerol 15,85 g ammonia, qsp pH 9,5

urea 4 g mono-oleate of polyoxyethylenatcd sorbitan 0,4 g water qsp lOO g Each strand of hair is saturated with this solution and set on rollers of 8 to 10 mm. in diameter. When all the hair has been set on rollers, it is again saturated with the same solution. The head is covered with a cap, and a period of 20 to 25 minutes is allowed to elapse.

The hair, still on rollers, is then abundantly and carefully rinsed with lukewarm water; the rollers are taken off and the hair is rinsed again. I

The curl thus obtained is well set and soft; it lends itself to pleasant styling, and the condition of the hair remains good. After 6 weeks, no loss of curl is apparent. Example 2 In order to obtain a permanent deformation of hair, a solution containing the following ingredients is prepared at the time of application:

thioglycerol 4 g dithiodiglycerol 17 g mono-ethanolamine, qsp pH 9,2 urea 4 g mono-oleate of polyoxyethylenated sorbitan 0,4 g or Tween (d=l,06l,l0, viscosity 230-430 centistokes) water qsp Example 3 To obtain the straightening of naturally frizzy hair,

the following composition is prepared, in a creamy texture, by mixing the following ingredients:

Wax 7 g (made of a mixture of 30 percent cetylic alcohol and 70 percent stearylic alcohol, this mixture being oxyethylenated by 30 moles of ethylene oxide per mole of alcohol in the mixture) thioglycerol 2 g bromide of trimethyl cetyl ammonium 0,2 g dithiodiglycerol 6,35 g ammonia, qsp pH 9,5 perfume 0,3 g water qsp 100 g The cream thus obtained is applied to the hair to be straightened strand by strand. Care should be taken to mix the cream well into each strand, so that it be well saturated.

The hair is then combed backward for a few moments, so that the consistency of the cream will keep the hair well saturated while the action of the composition is allowed to take place.

After about 15 minutes the hair is carefully rinsed so as to eliminate the cream while keeping the hair as much as possible in a stretched position.

The hair which, before the treatment, was tightly curled and frizzy has become smooth without being stiff.

The hair, however, now has a soft wide wave, while its texture has remained in excellent condition.

The ends have remained in good condition, and no cracking has been noted in the area of the roots. Example 4 To obtain a permanent deformation of the hair, a solution composed of the following ingredients is prepared at the time of the application:

thioglycolic acid 3,5 g dithiodiglycerol 16 g ammonia, qsp pH 9,5

urea 4 g mono-oleate of polyoxyethylenated sorbitan 0,4 g water qsp 100 g The hair is saturated with the aforementioned solution, and it is set on rollers of about 8 to 10 mm. in diameter.

To complete saturation of the hair, the rolled strands of hair are saturated again with the same solution, and the hair is covered with a cap.

After waiting for about minutes, the rollers are removed, the hair is rinsed very rapidly with water and sponged with a towel.

The result is a very beautiful curl, soft to the touch. The curl is durable and no change is'observed in the wave even after a lapse of 4 to 5 weeks.

Example 5 To obtain a permanent deformation of the hair, a solution composed of the following ingredients is prepared at the time of application:

thioglycolic acid 2 g dithiodiglycerol 23,2 g mono-ethanolamine, qsp pH 9,0

diethylene triamino pentacetic acid 0,] g ethanol 5 g water qsp 100 g After shampooing and sponging the hair, strand by strand the hair is saturated with the aformentioned solution and set on rollers of about 8 to 10 mm. in diameter.

After the rollers are all in, the rolled strands of hair are saturated once more with the same solution, and the head is covered with a cap. A waiting period of 20 to 25 minutes is allowed to take place.

The hair is then thoroughly rinsed with tepid water, and the rollers are removed. The hair is rinsed one more time.

The curl thus obtained is well set and soft; the styling is pleasant and the condition of the hair has remained good.

After a lapse of 6 weeks, no loss of curl is noted. Example 6 To obtain a permanent deformation in ordinary hair, a solution composed of the following ingredients is prepared at the time of application:

dimercapto-adipic acid 4 g dithiodiglycerol 12 g ammonia, qsp pH l0 urea l0 g water qsp l00 g This solution is applied as indicated in Example 5, with the difference that the time of application is reduced to about 15 to 20 minutes. A good permanent wave of the hair is thus obtained.

Example 7 To obtain a permanent deformation in bleached hair, a solution containing the following ingredients is pre pared at the time of application:

dimercapto-adipic acid 3 g dithiodiglycerol 15 g mono-ethanolamine, qsp pH 9,0

urea 4 g monoleate of polyoxyethylenated sorbitan 0,4 g water qsp 100 g By following the same operational mode as that described in Example 2, it is obtained after the last rinsing shiny hair and pleasant to the touch.

The curl thus obtained is deep, has beautiful styling and does not alter for several weeks.

Example 8 To obtain, according to the invention, a straightening of naturally frizzy hair, a creamy composition is prepared from the following ingredients:

thioglycolic acid 3 g dithiodiglycolic acid 18 g mono-ethanolamine, qsp pH 9,0 wax 7 g (made of a mixture of 30 percent cetylic alcohol and percent of stearylic alcohol; this mixture is oxyethylenated by means of 33 moles of ethylene oxide per mole of alcohol in the mixture) bromide of trimethylcetylammonium 0,2 g perfume 0,3 g water g This cream is applied in the same operational mode described in Example 3. Excellent results are likewise obtained, and the hair is left with a very wide wave. Example 9 To obtain, according to the invention, a permanent deformation of the hair, a solution is prepared at the moment of the application containing the following ingredients:

dimercapto-1,4 butanediol-2,3 2,5 g dithiodiglycerol 5 g ammonia, qsp pH 9,7

urea 10 g water qsp I00 g This solution is applied in the same operational mode as that described in Example 1. Excellent results are likewise obtained, and the hair presents a well set and soft curl even after a lapse of 6 weeks.

Example 10 To obtain a permanent deformation of the hair, at the moment of application a solution is prepared containing the following ingredients:

thiolactic acid 3 g dithiodiglycerol 15,2 g ammonia, qsp pH 9,4

urea 10 g water qsp 100 g After shampooing and sponging the hair, the operator saturates each strand of hair with the prementioned solution and sets it on roller of 8 to 10 mm. in diameter.

When all the rollers are on, the hair is saturated once more with the same solution. The head is covered with a cap, and a period of 20 to 25 minutes is allowed to elapse.

The hair is then rinsed carefully and thoroughly with lukewarm water; the curlers are removed, and the hair is rinsed again.

The curl thus obtained is well set and soft; it presents pleasant styling, and the condition of the hair remains good.

After a lapse of to 6 weeks, no loss of curl is noted. Example 11 To obtain a permanent deformation of the hair, a solution is prepared at the time of application. The following ingredients are included:

thiolactic acid 5 g dithiodiglycerol 30 g mono-ethanolamine, qsp pH 8,7

diethylene triamino pentacetic acid 0,1 g ethanol 5 g water qsp 100 g thioglycolic acid 5 g dithiodiglycolic acid 25 g ammonia, qsp pH 9,3

urea g water qsp 100 g This solution is applied as indicated in Example 4, and a good permanent wave is obtained.

Example 13 To obtain, according to the invention, the straightening of naturally frizzy hair, a cream compounded as follows is prepared:

thioglycerol dithiodiglycerol l monoethanolamine qsp pH 9.5 wax composed of a mixture of:

30 percent cetylic alcohol and 70 percent stearylic alcohol, this mixture being oxyethylenated by 33 moles of ethylene oxide per mole of alcohol in the mixture ammonium cetyl trimethyl bromide perfume water qsp n-nop SUNQ (BROOM This cream, applied in the same conditions as in Example 3, produces an excellent straightening of frizzy hair. The hair now appears with a slight wave. Example 14 To obtain a permanent setting according to the invention, a solution containing the following ingredients must be prepared:

thioglycerol 5 g dithiodiglycerol 16,85 g ammonia, qsp pH 9,5

urea 10 g water qsp I00 g The hair is then saturated and set on rollers of about 15 to 20 mm. in diameter. The solution is left to react during 15 to 20 minutes. The hair, still on rollers, is then rinsed and dried by heat externally produced. After the rollers are removed and the hair is combed out, a very satisfactory coiffure is obtained.

Example 15 To obtain a permanent setting according to the invention, a composition is first prepared by mixing the following ingredients:

thioglycerol 5 g dithiodiglycerol 40 g monoethanolamine qsp pH 8,5

diethylene triamino pentacetic acid 0,] g

ethanol 5 g water qsp g The hair is saturated with the solution thus obtained,

then set on rollers of about 15 to 20 mm. in diameter. After a setting period of about 15 to 20 minutes, the hair is carefully rinsed and then dried by means of heat externally produced.

After the rollers have been removed and the hair has been combed out, an excellent coiffure is obtained. Example 16 To obtain a permanent setting, a composition is first prepared by mixing the following ingredients:

thioglycolic acid 2 g dithiodiglycolic acid 20 g ammonia, qsp pH 10 urea 10 g water qsp 100 g thioglycolic acid 5 g dithiodiglycerol 35 g monoethanolamine, qsp-pH 8,5 triamino diethylene pentacetic acid 0,1 g ethanol 5 g water qsp 100 g The hair is saturated, strand by strand, and is set on rollers of about 15 to 20 mm. in diameter. Setting on the rollers takes place immediately after each strand is saturated with the solution.

After a period of setting of about 15 to 20 minutes, the hair is rinsed very carefully. The next step is drying, heat being produced externally.

After the hair is thoroughly dried, the rollers are removed, and the hair is combed out. Excellent resiliency of the strands is obtained. The styling effect produced at this time lasts, and the hair is pleasant to behold and to touch.

Example 18 To obtain a permanent setting according to the invention, a composition is prepared by mixing the following ingredients:

dimercaptoadipic acid 4 g dithiodiglycerol 12 g ammonia, qsp pH urea 10 g water qsp 100 g By proceeding as indicated in the preceding Example, a permanent setting of very good appearance is obtained.

Example 19 To obtain a permanent setting according to the invention, a composition is prepared by mixing the following ingredientsi dimercapto-l,4 butanediol-2,3 2,5 g dithiodiglycerol g ammonia, qsp pH 9,7

urea 10 g water qsp 100 g By operating as in Example 17, an excellent permanent setting is obtained whereby the hair appears with a very good wave.

Example 20 To obtain a permanent setting according to the invention, a composition is prepared by mixing the following ingredients:

thiolactic acid 2 g dithiodiglycerol 20 g ammonia, qsp pH 10 triamino diethylene pentacetic acid 0,] g ethanol 5 g water qsp 100 g Composition A thioglycolic acid 28,25 g monoethanolamine qsp pH 9,6 perfume 0,4 g water qsp 100 g Composition B aqueous solution of hydrogen peroxide 17,2 volumes.

At the time of use compositions A and B are mixed volume to volume. After one minute the internal temperature was about 70C and after 10 minutes about 43C.

After the 10 minutes laps, analysis of the mixture give the following figures:

thioglycolic acid dithiodiglycolic acid By using this composition as described in example 10 an excellent curl is obtained which does not loose even after 6 weeks. Example 22 To obtain a permanent deformation of hair according to the invention the two following compositions are prepared: Composition A thioglycolic acid 20 g ammonia, qsp to neutralize monoethanolamine, qsp pH 9,5

perfume 0,3 g water qsp 8 Composition B aqueous solution of hydrogen peroxide 10 volumes. At the time of use composition A and B are mixed volume to volume. From time 0 to 10 minutes the internal temperature figures are:

time 0 21C 30 sec 41C 10 mn 32C After the 10 minutes laps, analysis of the mixture give the following figures:

thioglycolic acid dithiodiglycolic acid pH 9,4

By using this composition according to Example 1 a perfect permanent wave is obtained.

What is claimed is: v

1. A process which produces a permanent deformation of the hair wherein:

the hair is subjected to mechanical deformation and treated with a sufiicient amount of self-neutralizing composition containing in aqueous or hydroalcoholic solution, a mixture of: thiol with a concentration of 2 to 5 percent, said thiol being selected from the group consisting of: thioglycerol, thioglycolic acid, dimercapto-adipic acid, dimercapto-l ,4 buta'nediol-2,3, and thiolactic acid; and disulfide, said disulfide being dithiodiglycerol, the numerical ratio of the disulfide groups to the thiol groups being greater than 1,5 and said composition having a pH contained between 8,5 and l0;

the composition is left to set for a period of time be- 13 14 I the composition is left to react during a period of tion having a pH between 8,5 and 10;

time contained between S and 30 minutes; the composition is left to react during a period of mechanical deformation is relieved; and time contained between and 30 minutes;

the hair i rin dthe hair, still on rollers, is rinsed; and

A Process accordmg to clalm 2, Where"! the hall 5 the hair is dried by heat externally provided. is saturated with the composition before it is subjected process which produces permanent setting of to mechanical deformation. the hair wherein;

Pmcess f q to clam wherein the the hair is rolled on curlers of about 15 to 20 mm. in chamfial fieformatlon produced by rollers of 8 to 10 diameter, and treated with a sufficient amount of m d'ameter' m a self-neutralizing composition containing in aque- 5. A process according to claim 2, wherein mechani- (ms or hydroalcoholic Solution a mixture of cal deformation is produced by combing and the com- 2 5 f I d osition is applied in the form of a cream. P i 0 10 an p dithlodiglycolic acid with a numerical ratio of the 6. A process which produces permanent setting of disulfide groups to the thiol groups being greater the hair wherein:

the hair is set on rollers of 15 to mm. in diameter,

and treated with a sufiicient amount of a selfneutralizing composition containing, in aqueous or hydroalcoholic solution, a mixture of: a thiol having a concentration between 2 and 5 per- 20 cent, said thiol being selected from the group consisting of: thioglycerol, thioglycolic acid, dimercapthan 2, and the said composition having a pH between 8,5 and 10.; the composition is left to react during a period of time contained between 5 and minutes; the hair, still on rollers, is rinsed; and the hair is dried by heat externally provided. 8. A process according to claim 7, wherein:

to-adipic acid, dimercapto-l,4 butanediol-2,3, a d the hair is rinsed after the standing period of 5 to 30 thiolactic acid, and minutes; and

a disulfide, said disulfide being dithiodiglycerol, the 5 the hair is saturated by an aqueous, or hydroalcoholic numerical ratio of the disulfide groups to the thiol solution containing a resin.

groups being greater than 1,5, and said composic UNITED STATES PATENT OFFICE CERTIFICATE -O-F CORRECTION Patent No. 3,768,490 'Dated October 30 1973 v h GREGOIRE KALOPISSIS ET AL It is certified that error appears in the aboveddentified patent andthat said Letters Patent are hereby corrected as shown below:

On the cover sheet, insert [30] Foreign Appli'cation, Priority Data France 983,968 August 3, 1964 France 995,597 November 19,. 1964 France. 5,818 February- 16, 1965 France 5,819 February 16, 1965 Signed and sealed this 6th day of August 1974.

(SEAL) Attes t MCCOY M. GIBSON, JR. c. MARSHALL DANN Atte sting Officer Commissioner of Patents FORM po'wso "$59) US'COMM-DC 00376-P69 9 .5, GOVERNMENT PR'NT'NG OFFICE Z IQ, O366-334.

Claims (7)

  1. 2. A process which produces a permanent deformation of the hair wherein: the hair is subjected to mechanical deformation and treated with a sufficient amount of a self-neutralizing composition containing in aqueous or hydroalcoholic solution, a mixture of: 2 to 5 percent of thioglycolic acid, and dithiodiglycolic acid, the numerical ratio of the disulfide groups to the thiol groups being greater than 2 and said composition having a pH of 8,5 and 10; the composition is left to react during a period of time contained between 5 and 30 minutes; mechanical deformation is relieved; and the hair is rinsed.
  2. 3. A process according to claim 2, wherein the hair is saturated with the composition before it is subjected to mechanical deformation.
  3. 4. A process according to claim 2, wherein the mechanical deformation is produced by rollers of 8 to 10 mm. in diameter.
  4. 5. A process according to claim 2, wherein mechanical deformation is produced by combing and the composition is applied in the form of a cream.
  5. 6. A process which produces permanent setting of the hair wherein: the hair is set on rollers of 15 to 20 mm. in diameter, and treated with a sufficient amount of a self-neutralizing composition containing, in aqueous or hydroalcoholic solution, a mixture of: a thiol having a concentration between 2 and 5 percent, said thiol being selected from the group consisting of: thioglycerol, thioglycolic acid, dimercapto-adipic acid, dimercapto-1,4 butanediol-2,3, and thiolactic acid, and a disulfide, said disulfide being dithiodiglycerol, the numerical ratio of the disulfide groups to the thiol groups being greater than 1,5, and said composition having a pH between 8,5 and 10; the composition is left to react during a period of time contained between 5 and 30 minutes; the hair, still on rollers, is rinsed; and the hair is dried by heat externally provided.
  6. 7. A process which produces permanent setting of the hair wherein: the hair is rolled on curlers of about 15 to 20 mm. in diameter, and treated with a sufficient amount of a self-neutralizing composition containing in aqueous or hydroalcoholic solution a mixture of: 2 to 5 percent of thioglycolic acid, and dithiodiglycolic acid with a numerical ratio of the disulfide groups to the thiol groups being greater than 2, and the said composition having a pH between 8,5 anD 10.; the composition is left to react during a period of time contained between 5 and 30 minutes; the hair, still on rollers, is rinsed; and the hair is dried by heat externally provided.
  7. 8. A process according to claim 7, wherein: the hair is rinsed after the standing period of 5 to 30 minutes; and the hair is saturated by an aqueous, or hydroalcoholic solution containing a resin.
US3768490A 1972-01-31 1972-01-31 Permanently having and permanently setting of hair Expired - Lifetime US3768490A (en)

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Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4470423A (en) * 1981-05-16 1984-09-11 Wella Aktiengesellschaft Process for permanently shaping hair
US4572220A (en) * 1981-02-19 1986-02-25 Helene Curtis Industries, Inc. Composition for altering the configuration of hair
US4600028A (en) * 1983-08-29 1986-07-15 Zotos International Inc. Saturated end wrap construction and composition
DE3707415A1 (en) * 1987-03-07 1988-09-15 Wella Ag Means and methods for permanent hair deformation
EP0354835A1 (en) * 1988-08-04 1990-02-14 L'oreal N-(mercaptoalkyl)-omega-hydroxyalkyl amides and their use as reducing agents in a process for the permanent setting of hair
FR2654617A1 (en) * 1989-11-20 1991-05-24 Oreal Cosmetic composition for permanent reductive containing, as reducing agent, the aletheine or a salt thereof, and its use in a process for permanently reshaping the hair.
US5154918A (en) * 1990-07-02 1992-10-13 L'oreal Cosmetic composition for use in permanent deformation of hair contains as a reducing agent a derivative of n-(mercapto alkyl) succinamic acid or of n-(mercapto alkyl) succinimide
US5316025A (en) * 1991-01-28 1994-05-31 Sahm Juergen E Method of set shaping hair
US5350572A (en) * 1993-02-18 1994-09-27 Shiseido Co., Ltd. Permanent waving composition
US5378454A (en) * 1992-01-09 1995-01-03 John Paul Mitchell Systems Composition and process for permanent waving
US5378813A (en) * 1992-05-29 1995-01-03 President And Fellows Of Harvard College Meso-2,5-dimercapto-N,N,N'N'-tetramethyladipamide
EP0689827A1 (en) 1994-06-30 1996-01-03 L'oreal Process for permanent hair waving
WO1996008179A1 (en) * 1994-09-14 1996-03-21 Shiseido Co., Ltd. Reducing agents for permanent waving of hair
US5584308A (en) * 1995-04-21 1996-12-17 Maekawa; Seiji Permanent wave method and apparatus
US5833966A (en) * 1993-07-28 1998-11-10 L'oreal Hydrogen peroxide-based compositions used as fixers for permanent-waving/straightening
US5988180A (en) * 1994-12-22 1999-11-23 Zotos International, Inc. Leave-on oxidizing solution for permanent waving of hair and a process for permanent waving of hair
US6173717B1 (en) * 1997-12-19 2001-01-16 Wella Aktiengesellschaft Hair shaping method using acidic aqueous intermediate rinse to prevent overcurling
US6302119B1 (en) 1999-12-06 2001-10-16 Bristol-Myers Squibb Company Low odor permanent waving compositions containing a disulfide
US20040194230A1 (en) * 2002-12-24 2004-10-07 Luc Nicolas-Morgantini Oxidation dye composition comprising at least one mesomorphic phase, process for preparing it and ready-to-use composition for dyeing keratin materials
FR2854568A1 (en) * 2003-05-06 2004-11-12 Oreal Use of water-soluble dithiols in a reducing composition for deformation of keratinic fibers, especially hair, at a defined pH
EP1501470A1 (en) * 2002-01-18 2005-02-02 Park, Junghyun One step permanent cosmetic composition
US20050042190A1 (en) * 2002-12-24 2005-02-24 Luc Nicolas-Morgantini Reducing composition for permanently reshaping or straightening the hair, containing a certain amount of mesomorphic phase, process for preparing it and process for permanently reshaping or straightening the hair
US20060002882A1 (en) * 2004-07-01 2006-01-05 Isabelle Rollat-Corvol Rinse-out cosmetic composition comprising elastomeric film-forming polymers, use thereof for conditioning keratin materials
US20060000485A1 (en) * 2004-07-01 2006-01-05 Henri Samain Pressurized hair composition comprising at least one elastomeric film-forming polymer
US20060002877A1 (en) * 2004-07-01 2006-01-05 Isabelle Rollat-Corvol Compositions and methods for permanently reshaping hair using elastomeric film-forming polymers
US20060005326A1 (en) * 2004-07-01 2006-01-12 Isabelle Rollat-Corvol Dyeing composition comprising at least one elastomeric film-forming polymer and at least one dyestuff
US20060005325A1 (en) * 2004-07-01 2006-01-12 Henri Samain Leave-in cosmetic composition comprising at least one elastomeric film-forming polymer and use thereof for conditioning keratin materials
FR2923713A1 (en) * 2007-11-15 2009-05-22 Oreal Reductive thickened composition.

Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4572220A (en) * 1981-02-19 1986-02-25 Helene Curtis Industries, Inc. Composition for altering the configuration of hair
US4470423A (en) * 1981-05-16 1984-09-11 Wella Aktiengesellschaft Process for permanently shaping hair
US4600028A (en) * 1983-08-29 1986-07-15 Zotos International Inc. Saturated end wrap construction and composition
DE3707415A1 (en) * 1987-03-07 1988-09-15 Wella Ag Means and methods for permanent hair deformation
EP0354835A1 (en) * 1988-08-04 1990-02-14 L'oreal N-(mercaptoalkyl)-omega-hydroxyalkyl amides and their use as reducing agents in a process for the permanent setting of hair
FR2654617A1 (en) * 1989-11-20 1991-05-24 Oreal Cosmetic composition for permanent reductive containing, as reducing agent, the aletheine or a salt thereof, and its use in a process for permanently reshaping the hair.
US5085860A (en) * 1989-11-20 1992-02-04 L'oreal Reducing composition for the permanent deformation of hair containing as a reducing agent, an amino mercaptoalkylamide or a salt thereof
EP0432000A1 (en) * 1989-11-20 1991-06-12 L'oreal Reducing composition for permanent hairwaving, comprising as reducing agent an amino-mercaptoalkylamide or one of its salts, and its use in a process for permanent hairwaving
US5154918A (en) * 1990-07-02 1992-10-13 L'oreal Cosmetic composition for use in permanent deformation of hair contains as a reducing agent a derivative of n-(mercapto alkyl) succinamic acid or of n-(mercapto alkyl) succinimide
US5316025A (en) * 1991-01-28 1994-05-31 Sahm Juergen E Method of set shaping hair
US5378454A (en) * 1992-01-09 1995-01-03 John Paul Mitchell Systems Composition and process for permanent waving
US5378813A (en) * 1992-05-29 1995-01-03 President And Fellows Of Harvard College Meso-2,5-dimercapto-N,N,N'N'-tetramethyladipamide
US5350572A (en) * 1993-02-18 1994-09-27 Shiseido Co., Ltd. Permanent waving composition
US5833966A (en) * 1993-07-28 1998-11-10 L'oreal Hydrogen peroxide-based compositions used as fixers for permanent-waving/straightening
EP0689827A1 (en) 1994-06-30 1996-01-03 L'oreal Process for permanent hair waving
WO1996008179A1 (en) * 1994-09-14 1996-03-21 Shiseido Co., Ltd. Reducing agents for permanent waving of hair
US5617883A (en) * 1994-09-14 1997-04-08 Shiseido Co., Ltd. Reducing agents for permanent waving of hair
US5988180A (en) * 1994-12-22 1999-11-23 Zotos International, Inc. Leave-on oxidizing solution for permanent waving of hair and a process for permanent waving of hair
US5584308A (en) * 1995-04-21 1996-12-17 Maekawa; Seiji Permanent wave method and apparatus
US6173717B1 (en) * 1997-12-19 2001-01-16 Wella Aktiengesellschaft Hair shaping method using acidic aqueous intermediate rinse to prevent overcurling
US6302119B1 (en) 1999-12-06 2001-10-16 Bristol-Myers Squibb Company Low odor permanent waving compositions containing a disulfide
EP1501470A1 (en) * 2002-01-18 2005-02-02 Park, Junghyun One step permanent cosmetic composition
EP1501470A4 (en) * 2002-01-18 2005-05-25 Park Junghyun One step permanent cosmetic composition
US7867478B2 (en) 2002-12-24 2011-01-11 L'oreal S.A. Reducing composition for permanently reshaping or straightening the hair, containing a certain amount of mesomorphic phase, process for preparing it and process for permanently reshaping or straightening the hair
US20050042190A1 (en) * 2002-12-24 2005-02-24 Luc Nicolas-Morgantini Reducing composition for permanently reshaping or straightening the hair, containing a certain amount of mesomorphic phase, process for preparing it and process for permanently reshaping or straightening the hair
US20040194230A1 (en) * 2002-12-24 2004-10-07 Luc Nicolas-Morgantini Oxidation dye composition comprising at least one mesomorphic phase, process for preparing it and ready-to-use composition for dyeing keratin materials
US7608116B2 (en) 2002-12-24 2009-10-27 L'oreal S.A. Oxidation dye composition comprising at least one mesomorphic phase, process for preparing it and ready-to-use composition for dyeing keratin materials
WO2004098488A3 (en) * 2003-05-06 2004-12-29 Gilles Genain Use of dithiols in a hair-perming composition
FR2854568A1 (en) * 2003-05-06 2004-11-12 Oreal Use of water-soluble dithiols in a reducing composition for deformation of keratinic fibers, especially hair, at a defined pH
WO2004098488A2 (en) * 2003-05-06 2004-11-18 L'oreal Use of dithiols in a hair-perming composition
US20060000485A1 (en) * 2004-07-01 2006-01-05 Henri Samain Pressurized hair composition comprising at least one elastomeric film-forming polymer
US20060005326A1 (en) * 2004-07-01 2006-01-12 Isabelle Rollat-Corvol Dyeing composition comprising at least one elastomeric film-forming polymer and at least one dyestuff
US20060005325A1 (en) * 2004-07-01 2006-01-12 Henri Samain Leave-in cosmetic composition comprising at least one elastomeric film-forming polymer and use thereof for conditioning keratin materials
US20060002882A1 (en) * 2004-07-01 2006-01-05 Isabelle Rollat-Corvol Rinse-out cosmetic composition comprising elastomeric film-forming polymers, use thereof for conditioning keratin materials
US20060002877A1 (en) * 2004-07-01 2006-01-05 Isabelle Rollat-Corvol Compositions and methods for permanently reshaping hair using elastomeric film-forming polymers
FR2923713A1 (en) * 2007-11-15 2009-05-22 Oreal Reductive thickened composition.
WO2009063042A1 (en) * 2007-11-15 2009-05-22 L'oreal Thickened reducing composition

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