US3672375A

US3672375A - Treatment of damaged hair with methylol compounds

Info

Publication number: US3672375A
Application number: US851473A
Authority: US
Inventors: Gregoire Kalopissis; Henri Philippe De Beaulieu; Jean-Louis Abegg; Giuliana Ghilardi
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 1968-08-26
Filing date: 1969-08-19
Publication date: 1972-06-27
Anticipated expiration: 1989-06-27
Also published as: DE1942671B2; DE1942671A1; LU56768A1; FR2017178A1; BE737932A; CH510439A; GB1264690A; DE1942671C3; IT1043802B

Abstract

Cosmetic composition for use in treating damaged hair. The composition comprises, as the active component a methylol compound of the formula:

IN A SUITABLE COSMETIC CARRIER, IN WHICH FORMULA: X represents either an oxygen atom or a sulfur atom or an NH group; R and R'' are identical or different and represent either a hydrogen atom or a lower alkyl radical; and R1 and R2 represent either a methyl hydroxy group or a methyl alkoxy group, e.g. methyl alkoxy wherein the alkoxy contains up to five carbon atoms or more. Typically the methylol compound is N,N''-dihydroxymethyl glyoxalurea or N,N''-dihydroxymethyl glyoxalthiourea. The composition is applied at an acid pH and is advantageously made up in solid form for mixing with water or water-and-alcohol solutions when used. The compositions are used by impregnating the hair with a mixture thereof and water or water-and-alcohol solution followed by drying with heat.

Description

United States Patent Kalopissis et al.

[451 June 27, 1972 [54] TREATMENT OF DAMAGED HAIR WITH METHYLOL COMPOUNDS Inventors: Gregoire Kalopissis; Henri Philippe De Beaulieu, both of Paris; Jean-Louis Abegg, Le Perreux; Giuliana Ghllardi, Paris, all of France [73]. Assignee: Societe anonyme dite:

France Filed: Aug. 19, 1969 Appl. No.2 851,473

LOreal, Paris,

Foreign Application Priority Data Aug. 26, 1968 Luxembourg ..56768 U.S. Cl ..l32/7, 8/ 1 27.5 1 424/47, 424/70, 424/71 Int. Cl ..A6lk 7/06, A45d 7/04 Field of Search ..424/47, 70, 71;8/127.6, 127.5], 8/1 16.2; 132/7 [56] References Cited UNITED STATES PATENTS 3,209,010 9/1965 Gagliardi et al ..8/1l6.2 X 3,350,162 10/1967 Beck ....8/1 16.2 X 3,442,905 5/1969 Primary Examiner-Albert T. Meyers Assistant Examiner-Vera C. Clarke Attorney-Cushman, Darby & Cushman l-lerbes et al. ..8/1 16.2 X

[5 7] ABSTRACT Cosmetic composition for use in treating damaged hair. The composition comprises, as the active component a methylol compound of the formula:

Typically the methylol compound is N,N'-dihydroxymethyl glyoxalurea or N,N'-dihydroxymethyl glyoxalthiourea.

The composition is applied at an acid pH and is advantageously made up in solid form for mixing with water or water-and-alcohol solutions when used. The compositions are used by impregnating the hair with a mixture thereof and water or water-and-alcohol solution followed by drying with heat.

5 Claims, No Drawings The present invention relates to a new .cosmeticcomposition intended for restoration of human hair which has previously been more or less severely damaged.

it is .known that there are numerous factors which tend to degrade the keratin of the hair. Thus atmospheric agents such as sun and sea water, or chemical treatments accompanying perrnanents and bleaching operations involve a certain breakdown of .the hair keratin. This degredation most often causes a significant loss of brilliance and of the aesthetic qualities of the hair. Damaged hair also becomes brittle and breaks easily, which can cause a rapid reduction of the total bulk of the hair.

, Treatment of the hair to increase mechanical resistance and elasticity has already been suggested, namely with use of compositions which contain polycondensable. N-methylol nitro compounds. These compounds have the characteristic of being able, when acted upon by acid catalysts and heat, to polymerize within the keratin, giving rise to a resin that can strengthen the hair. In addition, these compounds can be fixed to the keratin by their methylol function and thus create new cross linkages of the keratin fiber,- which also reinforces the hair.

It has been shown, however, that most of the known and used methylol compounds have the disadvantage of being relatively difficult to dissolve in water, which complicates their use in aqueous cosmetic compositions that are to be utilized as hair impregnants.

The present invention relates to cosmetic compositions containing one or more polycondensable methylol compounds as the base or essential component, which reinforce the keratin and moreover present the advantage of being much more soluble in water and in water-and-alcohol solutions than are the methylol compounds which have been previously described for use in this field of application.

The present invention relates to a cosmetic composition characterized in that it contains at least one compound of the formula:

in a suitable cosmetic carrier, in which formula X represents either an oxygen atom or a sulfur atom or an NH group;

R and R are identical or different and represent either a hydrogen atom or a lower alkyl radical; and

R and R represent either a methyl hydroxy group or a methyl alkoxy group, e.g., methyl alkoxy wherein the alkoxy contains up to five carbon atoms or more.

In a preferred embodiment of the invention, the cosmetic carrier of the composition is a solid carrier which offers good solubility in water and in water-and-alcohol solutions. The preparation of the composition as a solid is made possible by the substantial solubility of the active compounds which permits them to be very readily dissolved by the user at the time of application. The solid form of the composition is advantageous, because the composition can be stored in this way to avoid the risk of degradation of the active compounds which could occur in the course of extended storage of these compounds in aqueous solution.

In another embodiment, the composition of the invention is prepared as an aqueous or water-and-alcohol solution (e.g., water/ ethanol or water/isopropanol) of the methylol compound described above, in a concentration ranging between 0.5 and 12 percent by weight of the active component or components. The composition of the invention can also be prepared as a cream, a gel or an aerosol.

According to a specific embodiment, the composition may also contain an acid-reacting compound which allows its pH to be brought to a value between 1.5 and 5.

Among the active compounds that can be utilized according to the invention, there may be mentioned N,N -dihydroxymethyl glyoxalurea of the formula:

and N,N-dihydroxymethyl glyoxalthiourea of the formula:

The composition of the invention may also contain conventional ingredients such as swelling agents, surfactants, penetration agents, or dyes, perfumes, and cosmetic resins.

The present invention is also concerned with a process for treating the hair, characterized in that the hair is impregnated with a composition such as described above, in liquid or fluid form, the hair also being impregnated with an acid solution if the composition itself does not have an acid pH, followed by drying the hair with the application of heat, the hair being optionally rinsed before drying.

To facilitate the effecting of the treatment described above, it is possible,- for example, to formulate the cosmetic composition in liquid or fluid form at the moment of application to the hair. Thus, a solid composition according to the invention and comprising the methylol compound and solid carrier can be mixed with water or a water-and-alcohol solution with acid pH to make a lotion or the like which is applied to the hair directly after mixing.

ln a preferred embodiment of the invention, the treatment process described above is effected along with a hair-curling operation, the hair being rolled up after impregnation with the composition on curler rolls and dried by the application of heat.

The advantages of using the compositions of the invention in the manner described herein are that, even in the case of hair that has been substantially damaged, there is attained a curl that is of excellent quality, the hair regaining its original softness, sheen and liveliness.

For a better understanding of the invention, the following examples of compositions according to the invention and methods of using the same are presented, it being understood that these are given for purposes of illustration and are not intended to be in any way limiting:

EXAMPLE I Oleic alcohol l0 moles 0.5. (Brij 96) 23 g Paraffin oil 22 g N,N'-dihydroxymethyl glyoxalthiourea 0.2 g Perfume 0.2 g Water 55 g EXAMPLE 2 A gel having the following composition is which has been bleached, just before setting it:

applied to hair Oleic acid 10 moles 0.5. 27 g Paraffin oil 23 g N.N'-dihydroxymethyl glyoxalurea 0.5 g Pure acetic acid q.s.p. pH 3.5 Water 50 cc with the application of heat.

2. The process of claim 1 wherein the acid in said aqueous acid solution is selected from the group consisting of acetic, citric and phosphoric acid.

3. The process of claim 1 wherein said damaged hair is impregnated with an aqueous acid solution having a pH of 1.5-5 prior to impregnating said hair with said composition.

4. The process of claim 1 which also includes rolling up said hair impregnated with said composition on curlers prior to drying said hair.

5. The process of claim 1 which also includes rinsing said hair subsequent to impregnating the same with said composition and prior to drying said hair.

Claims

2. The process of claim 1 wherein the acid in said aqueous acid solution is selected from the group consisting of acetic, citric and phosphoric acid.
3. The process of claim 1 wherein said damaged hair is impregnated with an aqueous acid solution having a pH of 1.5-5 prior to impregnating said hair with said composition.
4. The process of claim 1 which also includes rolling up said hair impregnated with said composition on curlers prior to drying said hair.
5. The process of claim 1 which also includes rinsing said hair subsequent to impregnating the same with said composition and prior to drying said hair.