US 3628544 A
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United States Patent Inventors Appl. No. Filed Patented Assignee Priority Gregoire Kalopissis Paris;
Jean-Louis Abegg, le Perreux, both of France Feb. 28, 1968 Dec. 21 1971 Societe Anonyme Dite: LOreal Mar. 3, 1967 France PERMANENT WAVE-FIXING COMPOSITION AND PROCESS 5 Claims, No Drawings US. Cl 132/7, 424/71, 424/72 A6lk 7/10 llnt. Cl
Primary ExaminerAlbert T. Meyers Assistant Examiner-Doris J. Funderburk Attorney--Holcombe, Wetherill & Brisebois ABSTRACT: Process of treating the hair comprising first permanently waving the hair with a thio reducing agent and thereafter applying to the hair an aqueous solution containing a neutralizing agent and a water-soluble diimide compound.
PERMANENT WAVE-FIXING COMPOSITION AND PROCESS In conventional permanent waving processes the first step is to apply-to the hair a suitable reducing agent to rupture the 8-8 bonds of the keratin in the hair, after which the desired shape is imparted to the hair. An oxidizing composition is then applied, which serves to reconstitute the broken S-S bonds.
This last step is commonly called the neutralizing or oxidizing" step.
This invention relates to a new neutralizing composition which has the remarkable property of effectively restoring to its original state hair which has been damaged by the first step in permanent waving, or by bleaching.
It is an object of the present invention to provide a new composition for fixing" or neutralizing" permanent waves, which is essentially characterized by the fact that it comprises in combination at least one oxidizing agent and at least one carbodiimide.
The oxidizing agents may be selected from the group consisting of hydrogen peroxide, the bromates and iodates of alkaline metals, the alkaline perborates, urea peroxide, chlorates, and polythionates such as sodium tetrathionate. The concentrations of those oxidizing agents are those normally used to neutralize permanent waves.
The carbodiimides of the composition according to the invention are compositions which respond to the general formula:
R and R may be identical or different, and represent lower aliphatic or cycloaliphatic alkyl radicals containing one to six carbon atoms, aromatic radicals such as phenyl and tolyl or aralkyl radicals such as benzyl.
In a preferred embodiment of the invention the carbodiimides are soluble in the composition.
In this preferred embodiment of the invention, the neutralizing composition is an aqueous solution containing at least one carbodiimide responding to the formula:
R, has the significance indicated under formula l,
R and R are identical or different lower alkyls containing one to four carbon atoms such as CH or Cal l5. R, and R may also form part of a heterocyclic remainder, such as, for example, morpholine or piperidine,
n is a hole number between 2 and 6 inclusive.
In one particular embodiment of the composition according to the invention, the tertiary amine function of the carbodiimide according to formula ll may be quaternized in a conventional manner by means of a lower alkyl halide, such as methyl iodide, or by an alkyl sulfate or sulfonate, such as methyl sulfate or methyl paratoluene sulfonate.
Among the carbodiimides which may be used in the composition according to the invention are, for example:
the monocarbodiimides, such as:
[l-ethyl-3-(3'-trimethylammonium) propyl carbodiimide] iodide responding to'the formula:
[l-cyclohexyl-3-(2'-methyl morpho linium) ethyl carbodiimide] paratoluene sulfonate responding to the formula:
[l-ethyl-3-(2'-methyl morpholinium) ethyl carbodiimide] paratoluene sulfonate responding to the formula:
[l-cyclohexyl-3-(2'-diethyl methylammonium) ethyl carbodiimide] paratoluene sulfonate responding to the forl -ethyl-3-( 3 '-trimethylammonium)propyl carbodiimide] paratoluene sulfonate responding to the formula:
and [l,l'bis (3"-trimethylammonium propyl) 3,3-hexamethylene dicarbodiimide] diiodide responding to the The above carbodiimides have been listed purely by way of example, and may be used singly or in mixtures containing two or more of them.
In accordance with the invention the concentration of carbodiimides in the composition may range from bout 0.1 to 10 percent and preferably from 2 to 6 percent.
The pH value of the composition according to the invention may vary within broad limits, but it is in general determined by the nature of the oxidizing agents used for neutralization, and is preferably between 4 and 8.
The composition according to the invention may also take the form of an emulsion, gel or cream, and may contain any of the additives conventionally included in cosmetic compositions for used for carrying out the neutralizing step in permanent waving processes.
It is also an object of the present invention to provide a new method of carrying out this neutralization, which method is characterized by the fact that a composition having a carbodiimide base and oxidizing compounds are applied to the hair and left in contact therewith for at least 5 minutes and generally about 15 to 60 minutes, at a temperature between 25 and 50 C., for example.
The concentration of the oxidizing compounds is, for instance, 5 to 20 percent for compounds like potassium bromate or sodium bromate and l to 5 percent in weight for hydrogen superoxide, the concentration of the carbodiimide being between 0.1 and percent. 7
Thus when the hair has first been bleached, the composition according to the invention is applied in exactly the same way as those used in the conventional neutralization of a permanent wave, that is to say, for about minutes, at the ambient temperature.
On the other hand, when hair which has not been bleached is neutralized, neutralization with the product according to the invention is fully efficacious only at higher temperature, for example, of the order of 50 C. and when applied for a longer time, of the order of minutes, for example.
The neutralizing process according to the invention makes it possible to substantially improve the cosmetic properties of hair treated therewith, which presents a more attractive appearance, is softer to the touch, fluffier, and takes subsequent sets better than hair which has not been treated in accordance with the invention.
It should moreover be noted that treatment with the compositions according to the invention makes it possible to obtain a reduction of about 30 to 40 percent in alkaline solubility of the hair at the end of the permanent in the case of bleached hair which has been treated in accordance with the invention, as compared with hair waved in a conventional manner.
lt will be recalled that the tenn alkaline solubility" is defined as the relative decrease in the weight of hair treated with N/ 10 sodium hydroxide under the conditions specified in the international standards set forth in the l.W.T.O. report.
In order that the invention may be better understood, several examples will now be described, purely by way of illus' tration, without suggesting that the scope of the invention is limited to the details thereof.
EXAMPLE I Hair which has first been bleached with a conventional oxidizing agent is permanently waved in a conventional manner, using a 4 percent solution of ammonium thioglycollate, the pH value of which has been adjusted to 8.2 with ammonia or a suitable buffering agent. After completion of the first permanent waving step in a conventional manner, the following solution is applied to the hair:
Sodium bromate 5 g. l-cyclohexyl-3-(2'-methylmorpholinium) ethyl carbodiimide] paratoluene lulfonate 2 g. Water q.s.p. 100 cc.
The pH value of this solution is 7.5.
This solution is felt on thehair for 15 minutes at the ambient temperature. The hair is then rinsed with water and set in a conventional manner.
The hair is easier to arrange, more resilient, and more attractive in appearance.
EXAMPLE II The procedure is the same as in example I, except that the following solution according to the invention is used:
Sodium tetrathionate l5 g. Sodium bicarbonate l g. I-cyclohexyl-3-(2-methylomorpholinium) ethyl carbodiimide] par-toluene lull'onate 5 g. Water q.l.p. I00 cc.
Equally good results are obtained.
EXAMPLE Ill The procedure is the same as in example I, using as the reducing agent in the first step of the permanent waving process:
Thioglycerol 3 g. Ammonia q.s.p. pH Water q.|.p. cc.
Then the permanent is neutralized with the following oxidizing agent:
reducing agent the following solution:
Thiolactic acid 5 g.
Monoethanolamine, q.l.p. pH=9.2
Water q.|.p cc.
The permanent is then neutralized with a composition according to the invention, consisting of the following solution:
Sodium bromate 7 g. l-ethyl,3-(T-trimethylarnmonium) propyl carbodiimide] paratoluene lulfonate 2 g. Water q.s.p. 100 cc.
The pH value of this solution is 7.5 Equally good results are obtained.
EXAMPLE V The procedure is the same as in example I, using as the reducing agent the following solution:
Ammonium thioglycolate 4 g. Ammonia q.a.p. pH=9.3 Water q.|.p. X00 cc.
and as the composition according to the invention, for neutralizing the permanent, the following solution:
Sodium tetratluionate l5 g. Sodium bicarbonate l g. [l,l'-bia (3"-trimethylammonium propyl)-3,3'-
hear-ethylene dicarbondiimide] diparatoluene sulfonate 4 g. Water q.s.p. 100 cc.
Equally good results are obtained.
ral head of hair, in a conventional manner, by applying as the reducing agent the following composition:
Ammonium thioglycolate g. NlLOi-l qsp. pl l=9.3 Water q.s.p. 100 cc.
The hair is rinsed with hot water, and the oxidizing agent of example 11, which has first been warmed, is then applied.
The hair is then covered with a cap until neutralization is complete, that is, for about 15 minutes, and the temperature brought to about 4045 C. by heating it under a drier.
Equally good results are obtained.
It will be appreciated that the foregoing examples have been given purely by way of illustration, and may be modified as to detail without thereby departing from the basic principles of the invention.
1. A process for treating hair comprising the steps of first permanently waving the hair with a thioreducing agent to rupture the S--S bonds of the keratin, and thereafter applying to the hair an aqueous solution having a pH 4-8 and containing 1-20 percent by weight of a neutralizing agent and 0.1- percent by weight of a water soluble diimide compound selected from the group consisting of:
v and in which R represents a radical selected from the group consisting of lower alkyl having one to six carbon atoms and cyclohexyl R, is selected from the group consistingof:
CH1) nN A" CH R4 and in which R, and R represent a radical selected from the group consisting of methyl and ethyl,
n is a whole number 2 to 3 inclusive and A is an ion selected from the group consisting of sulfate,
paratoluene sulfonate and iodide, and permitting the solution to remain in contact with the hair for about 5-60 minutes. a
2. The process of claim I wherein the hair is bleached hair and the aqueous solution is left in contact with the hair for about fifteen minutes at ambient temperature.
3. The process of claim 1, wherein the hair is unbleached hair and the solution is left in contact with the hair for 15-60 minutes.
4. The process of claim 1, wherein the solution contains 2-6 percent of the carbodiimide.
5. The process of claim 4, wherein the neutralizing agent is selected from the group consisting of hydrogen peroxide, urea peroxide, alkali metal bi om ates ang so dium tetrathionate.