US3687606A

US3687606A - Permanent hair waving by artificially shaping with an epoxy-organo-silane

Info

Publication number: US3687606A
Application number: US75258A
Authority: US
Inventors: Walter Simmler; Hans-Horst Steinbach
Original assignee: Bayer AG
Current assignee: Bayer AG
Priority date: 1969-10-04
Filing date: 1970-09-24
Publication date: 1972-08-29
Anticipated expiration: 1989-08-29

Abstract

AGENTS FOR IMPROVING THE USUAL METHOD OF WAVING THE HUMAN HAIR HAVE THE GENERAL FORMULA

(R-O)A-SI(-CH3)(3-A)-CH2-(C2H4-O)B-CH2-CH<(-O-CH2-)

EXAMPLES OF MOST SUITABLE COMPOUNDS ARE 3-(METHYLDIISOPROPOXY-SILYL)-PROPYL-(1)-GLYCIDYL ETHER OF THE FORMULA

CH3-(O-C2H4)(1,2,OR3)-

AND THE 3-(TRIETHOXY-SILYL)-PROPYL-(1)-GLYCIDYL ETHER OF THE FORMULA

(C3H7-O)2-SI(-CH3)-(CH2)3-O-CH<(-O-CH2-)

PREFERABLY DISSOLVED IN ETHANOL OR ISOPROPANOL. IN A PREFERRED PROCESS OF APPLYING THESE AGENTS THE HAIR IS FIRST SHAPED, IN THE USUAL WAY, WITH THE AID OF A REDUCING AGENT WHICH SPLITS DISULPHIDE BRIDGES IN THE KERATIN IN THE HAIR, THEN, ACCORDING TO THE INVENTION , A SOLUTION OF ONE OF THE EPOXY-ORGANO-SILANES MENTIONED ABOVE IN ETHANOL OR ISOPROPANOL IS APPLIED TO THE HAIR. THEREAFTER, THE REDUCTION IS REVERSED IN KNOWN MANNER BY MEANS OF AN AQUEOUS HYDROGEN PEROXIDE SOLUTION.

Description

United States Patent 3 687 606 PERMANENT HAIR vvAvlNcr BY ARTIFICIALLY SHAPING WITH AN EPOXY-ORGANO-SILANE Walter Simmler, Odenthal-Gloebusch, and Hans-Horst Steinbach, Schildgen, Germany, assignors t0 Farbenfabriken Bayer Aktiengesellschaft, Leverkusen, Germany No Drawing. Filed Sept. 24, 1970, Ser. No. 75,258 Claims priority, application Germany, Oct. 4, 1969, P 19 50 098.2 Int. Cl. A61k 7/10 US. Cl. 8127.51 3 Claims ABSTRACT OF THE DISCLOSURE Agents for improving the usual method of waving the human hair have the general formula (a is 2 or 3, b is 0 or 1, R is C to C alkyl or f CHO CH 2 4 /l.2or3 3) Examples of most suitable compounds are 3-(methyl diisopropoxy-silyl)-propyl-(l)-glycidyl ether of the formula and the 3-(triethoxy-silyl)-propyl-(1)-glycidyl ether of the formula preferably dissolved in ethanol or isopropanol.

In a preferred process of applying these agents the hair is first shaped, in the usual way, with the aid of a reducing agent which splits disulphide bridges in the keratin in the hair, then, according to the invention, a solution of one of the epoxy-organo-silanes mentioned above in ethanol or isopropanol is applied to the hair. Thereafter, the reduction is reversed in known manner by means of an aqueous hydrogen peroxide solution.

The invention relates to certain new compounds and to their use for the permanent waving of hair.

It has been found that hair which has been artificially waved (that is, shaped in waves or curls) with the aid of known agents by a wet method may retain its shape for a prolonged time, even in humid air, when treated with the present compounds.

It is known to use various sprays containing synthetic resins, for example polyacetals, to assist in maintaining the shape of artificially waved hair. These resins cover the hair externally. It has been proposed to use agents which combine chemically with the substance of the hair, for example epoxyalkyl-siloxanes according to US. patent specification No. 3,248,296.

After the reaction of their epoxide groups, the last- Inentioned compounds adhere to the hair more persistentlv than a mere film and they impart to the hair the known water-repellent effect of the organo-polysiloxane moiety. However, it is a disadvantage of this treatment that the hair acquires an unnatural and therefore undesirable oily gloss. Another disadvantage is that these siloxanes are not soluble in water. This fact is important for the following reason:

In the shaping process at present most commonly in which a is 2 or 3;

b is 0 or 1; and

R is an alkyl radical with 1 to 6 carbon atoms or an ether radical of the formula in which n is 1, 2 or 3.

It is known that Si-bound alkoxyl radicals are hydrolytically eliminated upon the access of water thereby forming the corresponding alcohols ROH; for reasons of health or odor, the ethyl and isopropyl radicals are therefore to be preferred for R. Accordingly, the treatment agents according to the invention are also preferably used dissolved in ethanol or isopropanol.

The invention also provides a process for the permanent waving of hair which comprises artificially shaping the hair with the aid of a reducing agent which splits disulphide bridges in the keratin of the hair applying an epoxy-organo-silane according to the invention to the hair, and thereafter applying an oxidizing agent to reverse the reduction.

The reducing and oxidizing agents may for example be any of those conventionally used for the purpose.

In accordance with conventional practice, the reducing agent is usually applied in aqueous medium.

It is preferred that the polyorganosilane be applied in alcoholic or aqueous-alcoholic solution to the wet hair. This gives the advantages mentioned above, in that the treating agent is readily dispersed in the hair to 'which an aqueous reducing agent has been applied and the hair is particularly rich in reactive groups capable of entering into chemical bonds with the treating agent.

In a preferred method of carrying out the process of the invention (which is particularly conducive to the durability of the desired effect), the washed hair is first shaped in the moist state by a conventional-method and subjected to the effect of a suitable reducing liquid, for example an aqueous thioglycollic acid solution, at a temperature between 20 and 50 C. A solution of 2 to 20 percent by weight of one of the epoxy-organo-silanes mentioned above in ethanol or isopropanol is then applied to the hair while it is still moist. Finally, the reduction is reversed in the usual way by means of an aqueous hydrogen peroxide solution, the hair is dried in a warm air current, and the shaping devices are removed. The hair then has only a slight gloss and can easily be combed.

The reactions taking place in the course of this treatment have not yet been eluciated in detail. In any case, the effect achieved according to the invention is substantially diiferent from that of the epoxy-alkyl-siloxane treatment mentioned above, although it may be that in the end of the alkoxyor methoxy-ethoxy-silanes used in the present case are condensed to organosiloxanes. It can be assumed that here the silicon compounds are temporarily diifused in the form of water-soluble hydrolysis products to the surface of the moist hair and that only there the siloxane condensation takes place simultaneously with the reaction between the epoxide groups and the hair substance.

The epoxy-organo-silanes to be used according to the invention can be obtained by various methods of known type: for example, al-kenyl-silicon compounds can be oxidized with peracetic acid to form epoxy-alkyl-silicon compounds, or partially substituted silane derivatives can be added with the HSi groups on to the double bonds of olefinic epoxides, for example, epoxy-butene or allyl glycidyl ether; in this way, there are obtained, for example, silicon-bound organic radicals of the formulae For the treatment of hair according to the invention the 3- (methyl diisopropoxy silyl)-propyl-(1)-glycidyl ether of the formula and the 3-*(triethoxy-silyl)-propyl-(1)-glycidyl ether of the formula have proved particularly satisfactory; strands of hair shaped in curls and treated with these agents showed no appreciable change of shape after more than one year in an indoor atmosphere.

Another valuable specific compound is 3-(methyl-diethoxy-silyl -propyl-( 1 -glycidyl ether.

The invention is illustrated by the following examples.

EXAMPLE 1 A standard brown-grey mottled strand of human head hair of 100 mm. length was moistened with Water, wound on a commercial curler of mm. diameter, dipped for 15 minutes into a solution of 12 g. thioglycollic acid and 8 g. fi-aminoethanol in 1 80 g. of water, which had been heated to 50 C., and then thoroughly rinsed with water.

According to the invention, this was followed by an immersion treatment of 15 minutes duration with a solution of 2 g. 3-(methyl-diisopropoxy-silyl)-propy1-(1)- glycidyl ether and 94 g. ethanol in 104 g. of Water, which had been heated to 30 C. After thorough rinsing with water, there followed a third immersion treatment of 5 minutes duration with an aqueous solution of 3 percent by weight of hydrogen peroxide at C. After final rinsing with water, the curler was removed and the hair was allowed to dry at room temperature, suspended on the cord of the test strand. The length of the freely suspended curl amounted to 28 mm. after 24 hours.

EXAMPLE 2 (In analogy with Example 1, a hair strand of the same composition was treated, the ditference being that a solution of 2 g. 3-(triethoxy-silyl)-propyl-(1)-glycidyl ether and 88 g. ethanol in 110 g. of water was used for the second immersion treatment according to the invention. All other steps were the same. The length of the dried curl amounted to 35 mm. after 24 hours.

EXAMPLE 3 Treatment of a further strand of hair was carried out in analogy with the preceding examples, but with the use of a solution of 2 g. 3- (trimethoxy-silyl)-propyl-(1)- glycidyl ether and 56 g. ethanol in 142 g. of water for the second immersion threatment. The length of the curl was found to be 30 mm.

EXAMPLE 4 In a process otherwise identical with that described in Examples 1 to 3, a solution of 2 g. 3-(methyl-diethoxysilyD-propyl-(l)-glycidyl ether and g. ethanol in 104 g. of Water was used for the second immersion treatment. The dried curl had a length of 55 mm.

In a comparative experiment, the solutions for the second immersion treatment according to the invention were replaced with a solution of 2 g. of an organo-polysiloxane as described in detail in US. patent specification No. 3,248,296 in 198 g. ethanol. This linear siloxane consists, on average, of 18 dimethyl-siloxane units, 18 methyl- (epoxy-propoxy-propyl)-siloxane units and 2 terminal trimethyl-siloxane units. The test strand was otherwise treated in the same Way as were the strands in the preceding Examples 1 to 4, but after drying the curl had uncurled to a length of 70 mm.

What we claim is:

1. A composition for use in the permanent waving of hair, consisting of from 2 to 20 percent by weight of an epoxy-organo-silane of the general formula in which a is one of the numbers 2 and 3; b is one of the numbers 0 and l; and R is a substituent selected from the group consisting of alkyl radicals having 1 to 6 carbon atoms, and ether radicals of the formula in which n is one of the numbers 1, 2 and 3; and from '98 to 80 percent by weight of a solvent selected from the group consisting of ethanol and isopropanol.

2. A composition according to claim 1, in which R is selected from the group consisting of ethyl and isopropyl. G. In a process for the permanent waving of hair, which comprises artificially shaping the hair with the aid of a reducing agent which splits disulphide bridges in the keratin of the hair and thereafter applying an oxidizing agent to reverse the reduction, the improvement which comprises applying an epoxy-organo-silane according to claim 1 to the hair after treating the hair with said reducing agent and before applying said oxidizing agent.

References Cited UNITED STATES PATENTS 3,248,296 4/ 1966 Steinbach et al. 8127.51

FOREIGN PATENTS 1,036,083 7/ 1966 Great Britain 260-34=8 OTHER REFERENCES Sadykh-Zade et al.: Doldady Akad. Nauk S.S.S.R., vol. 1l8, 1958, pp. 723-6 (see Abstracts, Chem. 1958, vol. 52, p. 11805f).

GEORGE F. LESMES, Primary Examiner P. C. IVES, Assistant Examiner US. Cl. X.R. 260-348 SC