US3560610A - Hair-setting composition - Google Patents

Hair-setting composition Download PDF

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US3560610A
US3560610A US3560610DA US3560610A US 3560610 A US3560610 A US 3560610A US 3560610D A US3560610D A US 3560610DA US 3560610 A US3560610 A US 3560610A
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hair
water
reaction
soluble
polyaminoureylene
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Maria A Korden
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Hercules Inc
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Hercules Inc
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    • 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
    • A61K8/72Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/88Polyamides
    • 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
    • A61K8/72Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02Polyamines
    • C08G73/0206Polyalkylene(poly)amines
    • C08G73/0213Preparatory process
    • C08G73/022Preparatory process from polyamines and epihalohydrins
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/02Polyureas
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00Drug, bio-affecting and body treating compositions
    • Y10S424/02Resin hair settings

Abstract

A HAIR-SETTING LOTION IS PROVIDED WHICH IS COMPRISED OF AN AQUEOUS SOLUTION OF A REACTION PRODUCT OF A WATERSOLUBLE POLYAMINOUREYLENE-EPICHLOROHYDRIN RESIN AND A WATER-SOLUBLE MATERIAL SUCH AS SODIUM SULFITE.

Description

Int. Cl. A61k 7/10 US. Cl. 424-72 7 Claims ABSTRACT OF THE DISCLOSURE A hair-setting lotion is provided which is comprised of an aqueous solution of a reaction product of a watersoluble polyaminoureylene-epichlorohydrin resin and a water-soluble material such as sodium sulfite.

This invention relates to novel hair-setting compositions or lotions and to their use in setting hair.

Two primary methods are employed in the art of hair dressing. In one of these, called permanent waving, the configuration of individual hair fibers is substantially permanently changed to impart a curl or wave to the hair. A permanent waving process involves the use of chemical agents which react with the material of the hair fibers to soften and/or change it chemically in order to achieve a desired permanently waved configuration. This process can be carried out either at approximately room temperature, the process then being called cold permanent waving, or at an elevated temperature.

The second process involved in hair dressing is that of setting the hair; that is, imparting to the hair a temporary set or temporarily changed configuration for the purpose of obtaining a particular hair style. This temporary set is changed whenever the hair style is changed. The hairsetting process can also be carried out either at room temperature or at elevated temperature, and in the past there have been employed certain water-soluble gums and resins for imparting a temporary set to hair.

In the case of permanently waved hair the curl or wave in the hair remains substantially unaltered for the remainder of the life of the hair under ordinarly conditions. A hair set, however, is not permanent but is generally removed by wetting the hair with water. Usually, the hair set is removed by shampooing the hair with mild shampoo.

The present invention is directed to a novel hair-setting composition for use in imparting a temporary set to hair.

In accordance with this invention there is provided a novel hair-setting composition comprised of an aqueous solution of a water-soluble resinous material. The hairsetting composition of this invention can be used to impart a highly satisfactory temporary set to hair which has good resistance to high humidity. The hair-setting composition is applied to water-damp hair, usually in the form of a fine spray, and the thus treated hair is set to a desired configuration usually by use of rollers. The treated hair is subsequently dried. The water-soluble resinous material deposited on the hair provides the desired set-holding characteristics until removed. The deposited resinous material is essentially tack free and remains so even when the hair is exposed to conditions of high humidity. The resinous material deposited on the hair can be easily and readily removed, despite its resistance to humid conditions, by washing with a mild shampoo whereby the hair-set is removed and the hair can be reset and restyled, if desired.

The water-soluble resinous material of this invention is the reaction product derived by reaction of (l) a watersoluble polyaminoureylene-epichlorohydrin resin, and (2) a water-soluble material selected from the group consisting of (a) water-soluble sulfites; (b) water-soluble United States Patent Patented Feb. 2, 1971 bisulfites; (c) water-soluble thiosulfates; (d) water-soluble thioglycolates; and (e) mixtures of two or more. The hair-setting compositions of this invention are essentially free of sulfite anions, bisulfite anions, thiosulfate anions, and thioglycolate anions.

The amount of water-soluble material (2) used in carrying out the reaction to provide the water-soluble resinous material of this invention will be that which will provide from about 0.2 mole to 1.0 mole, and preferably from about 0.5 mole to 0.9 mole, of sulfite anion, bisulfite anion, thiosulfate anion, or thioglycolate anion per mole of epichlorohydrin moiety of the water-soluble polyaminoureylene-epichlorohydrin resin (1). Reaction is carried out in aqueous media at a pH of about 4.5 to about 11, preferably at a pH of from about 6 to about 8.5, and at a temperature of from about 25 C. to about C. for a period of time of from about /z hour to 2 weeks, or longer if required. Preferred temperature range is from about 25 C. to about 80 C. Reaction time varies inversely with temperature. Reaction is carried out until essentially all bisulfite anion, sulfite anion, thiosulfate anion, and/or thioglycolate anion has reacted and there is less than about 0.15% anion present in the solution. After reaction, the solution is adjusted to a desired solids concentration and to a pH- of from about 6 to about 7.5.

Examples of suitable water-soluble sulfites for use herein include sodium sulfite, potassium sulfite, and ammonium sulfite. Examples of suitable water-soluble bisulfites for use in this invention include sodium bisulfite, potassium bisulfite, ammonium bisulfite, sodium metabisulfite, potassium metabisulfite, and ammonium metabisulfite. Examples of water-soluble thiosulfates include sodium thiosulfate, potassium thiosulfate, and ammonium thiosulfate. Examples of water-soluble thioglycolates include sodium thioglycolate, potassium thioglycolate, and ammonium thioglycolate. Mixtures of two or more of the above can be used if desired.

Water-soluble polyaminoureylene-epichlorohydrin resins (1) employed herein are water-soluble polymeric reaction products of epichlorohydrin and a water-soluble polyaminoureylene containing tertiary amino nitrogens.

The polyaminoureylene is water-soluble and is derived by reaction of urea and a polyalkylene polyamine containing at least three amine groups, at least one of which is a tertiary amine group in a mole ratio of polyalkylene polyamine to urea of from about 0.7:1 to about 1.521. The reaction can, if desired, be carried out in a suitable organic diluent such as xylene. The reaction is carried out preferably in aqueous media.

The polyalkylenepolyamine reactant will have at least three amine groups, at least one of which is a tertiary amine group. Examples of suitable polyalkylene polyamines include methyl bis(3 aminopropyl)amine, methyl bis(2 aminoethyl)amine, 4,7 dimethyltriethylenetetramine and the like. Mixtures of two or more can be employed if desired.

Temperature employed in carrying out reaction between urea and polyalkylene polyamine can vary from about C. to about 250 C. at atmospheric pressure. Temperatures between about C. and about 225 C. are preferred. The time of reaction will vary depending upon temperature, but will usually be from about /2 hour to about 4 hours. Reaction time varies inversely with temperature. In any event, reaction is continued to substantial completion.

In carrying out reaction between urea and polyalkylene polyamine, it is preferred to use a mole ratio of polyalkylenepolyamine to urea of about 1:1. However, as above set forth, mole ratios from about 0.7:1 to about 1521 can be used.

Reaction of the polyaminoureylene with epichlorohydrin is carried out at a temperature of from about 25 C. to about 80 C., and preferably at a temperature of from about 35 C. to about 50 C., until the viscosity of a 25% solids solution in water at 25 C. has reached about B or higher on the Gardner-Holdt scale. This reaction is preferably carried out in aqueous solution at solids concentrations from about to about 50% to moderate the reaction. The reaction can also be moderated by decreasing the pH of the aqueous polyaminoureylene solution with acid prior to addition of epichlorohydrin or immediately after the addition of epichlorohydrin. This adjustment is usually made to pH 85-95 but may be made to as low as pH 7.5 in some cases with quite satisfactory results. When the desired viscosity is reached, the product is cooled to about C.

In the polyaminoureylene-epichlorohydrin reaction, it is preferred to use a mole ratio of epichlorohydrin to free amine groups in the polyaminoureylene of from about 1.021 to about 1.7:1. Satisfactory results can be obtained employing from about 0.8 mole to about 2.0 moles of epichlorohydrin for each free amine group of the polyaminoureylene.

The following examples are illustrative of the invention. All parts and percentages are by Weight unless otherwise specified.

EXAMPLE 1 To a resin kettle are charged 217.5 parts of methyl bis(3-aminopropyl)amine and 90 parts of urea. The resulting mixture is heated at about 180 C. for about 45 minutes, and is then diluted with about 300 parts water and cooled. The resulting polyaminoureylene has an intrinsic viscosity of about 0.20 and a total solids content of about 40%. 212 parts of the above polyaminoureylene solution containing 85.5 parts solids is diluted with 233 parts of water and acidified with 14.1 parts of concentrated hydrochloric acid. The resulting solution is then treated with 69.4 parts of epichlorohydrin and heated to 4055 C. until the Gardner-Holdt viscosity reaches K. The resulting solution is acidified to a pH of about 2 with concentrated HCl and heated to about 65 C. for about 1.5 hours while maintaining the pH of about 2 by periodic additions of concentrated HCl. The resulting solution after cooling contains about 28% total solids. To 50 parts of the above resin solution are added about 150 parts of water and 3.48 parts of sodium metabisulfite. The pH is adjusted to about 8.2 with sodium hydroxide solution and water is added to a total weight of mixture about 400 parts to provide a hair-setting lotion.

EXAMPLE 2 A strand or tress of hair, 10 inches long and weighing 1 gram, is dampened with water. It is then sprayed with the hair-setting lotion of Example 1. The treated tress is rolled up on rollers, dried with a home-type hair dryer and combed out. The curl length is about 3.41 inches. The curled tress is hung in a high humidity chamber (75 F., 75% R.H.). After two hours exposure, the length of the curled tress is about 6.7 inches.

EXAMPLE 3 To 212 parts of an aqueous solution of polyaminoureylene (40.3% solids) is added 233 parts water. The pH of the solution is adjusted to 9.6 by addition of concentrated HCl. The polyaminoureylene is the condensation product of about 1 mole of urea and about 1 mole of methyl bis(3-aminopropyl)amine. To the resulting mixture there is added 69.4 parts of epichlorohydrin. This mixture is then heated at 40 C. for about 2% hours and then at 50 C. for about /2 hour. At the end of this time the reaction mass has a Gardner-Holdt viscosity of L and a pH of 8.5. The reaction mass is cooled to about 40 C. and the pH thereof is adjusted to 8.25 by addition of HCl. A solution of 40.2 parts of sodium metabisulfite dissolved in 100 parts water is added followed by addition of parts water. The temperature of this reaction mass increases to about 50 C. in about /2 hour and then decreases to about 40 C. in about hour. The 40 C. temperature is maintained for an additional 2% hours. At the end of this period the sulfite anion concentration, calculated as NaHSO is less than 0.1%. The reaction mass is diluted with 3,312 parts water to provide a solution having a solids content of about 4.3% and a pH of about 7.1.

EXAMPLE 4 The solution of Example 3 is tested as a hair-set lotion in accordance with the procedure of Example 2. Curled tress length after treatment and combing is 4.2 inches and 6.6 inches after being subjected to 75 F., 75% R.H. for 2 hours. Water treatment, used as a control, gives a curled tress of 4.8 inches after combing and a tress having a length of 7.8 inches after being subjected to 75 F., 75% R.H. for 2 hours.

EXAMPLE 5 Example 3 is repeated using ammonium thioglycolate instead of sodium metabisulfite to provide an equally satisfactory hair-set lotion.

EXAMPLE 6 Example 3 is repeated using sodium thiosulfate pentahydrate instead of sodium metabisulfite to provide an equally satisfactory hair-set lotion.

Thus, in accordance with this invention, there is provided a novel hair-setting composition that can be employed to impart a temporary set to hair which has good set-holding properties when exposed to conditions of high humidity.

The amount of resinous material in the hair-setting composition is from about 0.5% to 10%, by weight of the total weight of the composition, and preferably from about 1 /2% to about 5 /2% by weight. Lower concentrations can be employed; however, they are not so desirable because excessively large quantities of the composition must be applied to the hair in order to obtain an adequate application of resinous material. Higher concentrations are undesirable because of the tendency to apply more resinous material to the hair than is needed. The pH of the hairsetting compositions preferably will be from about 6 to about 7.5. Required pH adjustments in this invention can be made by use of either dilute sulfuric acid or dilute sodium hydroxide.

The hair-setting composition of this invention can be applied to the hair in any convenient manner such as, for example, by means of a spray pump.

Additives often used in hair-setting compositions can also be incorporated into the compositions of this invention, if desired. Thus, for example, glycerine and/ or watersoluble lanolin derivatives, such as ethoxylated lanolin, can be added to improve sheen or luster of treated hair. Water-soluble dyes can be added as well as perfumes and the like.

It is to be understood that the above description and examples are illustrative of this invention and not in limitation thereof.

What I claim and desire to protect by Letters Patent is:

1. A hair-setting lotion comprising an aqueous solution containing, by weight, from about 0.5% to about 10% of a reaction product of (1) a Water-soluble polyaminoureylene-epichlorohydrin resin derived by reacting epichlorohydrin and a water-soluble polyaminoureylene containing tertiary amino nitrogens in a mole ratio of epichlorohydrin to free amine groups in the polyaminoureylene of from about 1.0:1 to about 1.7:1, and polyaminoureylene being derived by reaction of urea and a polyalkylene polyamine containing at least three amine groups, at least one of which is a tertiary amine group, in a mole ratio of polyalkylene polyamine to urea of from about 0.7:1 to about 1.5:1, said polyalkylene polyamine being selected from the group consisting of methyl bis(3- aminopropyDamine, methyl bis(2-aminoethyl)amine, 4,7- dimethyltriethylenetetramine, and mixtures thereof and (2) a water-soluble material selected from the group consisting of sodium, potassium, and ammonium sulfites, bisulfites, thiosulfates, and thioglycolates and mixtures thereof, the amount of water-soluble material (2) used to prepare the reaction product being that which will provide from about 0.2 mole to 1.0 mole of sulfite anion, bisulfite anion, thiosulfate anion, thioglycolate anion, or mixtures thereof per mole of epichlorohydrin moiety of the water soluble polyaminoureylene epichlorohydrin resin, said reaction product being derived by reaction of the water soluble polyaminoureylene epichlorohydrin resin (1) and fwater-soluble material (2) in aqueous media at a pH of about 4.5 to about 11 and at a temperature of from about 25 C. to about 100 C. until essentially all bisulfite anion, sulfite anion, thiosulfate anion, thioglycolate anion, or mixtures thereof has reacted and there is less than 0.15% anion present. I

2. The hair-setting lotion of claim 1 wherein the pH of the aqueous solution is from about 6 to about 7.5.

3. The hair-setting lotion of claim 1 wherein the polyaminoureylene is derived by reaction of urea and methyl bis( 3 -aminopropyl) amine.

4. The hair-setting lotion of claim 1 wherein the amount of water-soluble material (2) used is that which will provide from about 0.5 mole to about 0.9 mole of the anion of the water-soluble material per mole of epichlorohydrin moiety.

5. The hair-setting lotion of claim 4 wherein the pH of the aqueous solution is from about 6 to about 7.5.

6. The hair-setting lotion of claim 4 wherein the polyarninoureylene is derived by reaction of urea and methyl bis(3-aminopropyl)amine.

7. In the method of providing a temporary wave set to hair wherein there is applied to water-damp hair a hair-setting lotion, the thus treated hair being subsequently styled to a desired configuration, the improvement wherein the hair-setting lotion employed is the hair-setting lotion of claim 1.

References Cited UNITED STATES PATENTS ALBERT T. MEYERS, Primary Examiner F. E. WADDELL, Assistant Examiner

US3560610D 1967-10-13 1967-10-13 Hair-setting composition Expired - Lifetime US3560610A (en)

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3805809A (en) * 1972-10-02 1974-04-23 Procter & Gamble Hair setting process
US4157388A (en) * 1977-06-23 1979-06-05 The Miranol Chemical Company, Inc. Hair and fabric conditioning compositions containing polymeric ionenes
US4172887A (en) * 1973-11-30 1979-10-30 L'oreal Hair conditioning compositions containing crosslinked polyaminopolyamides
US4189468A (en) * 1973-11-30 1980-02-19 L'oreal Crosslinked polyamino-polyamide in hair conditioning compositions
US4196741A (en) * 1977-07-18 1980-04-08 Minghenelli Santo M Product and process for highlighting and streaking hair
US4201766A (en) * 1977-03-02 1980-05-06 L'oreal Hair conditioning composition and method of using the same
US4213960A (en) * 1977-03-02 1980-07-22 L'oreal Cosmetic compositions for treating the hair
US4277581A (en) * 1973-11-30 1981-07-07 L'oreal Polyamino-polyamide crosslinked with crosslinking agent
US4579732A (en) * 1978-06-15 1986-04-01 L'oreal Hair dye or bleach supports
US5071641A (en) * 1988-06-10 1991-12-10 University Of Leeds Industrial Services Limited Method of setting hair
US20030143175A1 (en) * 2001-12-18 2003-07-31 Henri Samain Cosmetic compositions comprising polymers comprising complementary chemical functional groups
US20030157136A1 (en) * 2001-12-18 2003-08-21 Henri Samain Cosmetic composition forming a tackifying coating comprising a polymer with a non-silicone skeleton and reactive functional groups
US20030185781A1 (en) * 2001-12-18 2003-10-02 Henri Samain Cosmetic composition forming a soft coating comprising a polymer having a non-silicone backbone and reactive functional groups

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3805809A (en) * 1972-10-02 1974-04-23 Procter & Gamble Hair setting process
US4189468A (en) * 1973-11-30 1980-02-19 L'oreal Crosslinked polyamino-polyamide in hair conditioning compositions
US4172887A (en) * 1973-11-30 1979-10-30 L'oreal Hair conditioning compositions containing crosslinked polyaminopolyamides
US4277581A (en) * 1973-11-30 1981-07-07 L'oreal Polyamino-polyamide crosslinked with crosslinking agent
US4201766A (en) * 1977-03-02 1980-05-06 L'oreal Hair conditioning composition and method of using the same
US4213960A (en) * 1977-03-02 1980-07-22 L'oreal Cosmetic compositions for treating the hair
US4157388A (en) * 1977-06-23 1979-06-05 The Miranol Chemical Company, Inc. Hair and fabric conditioning compositions containing polymeric ionenes
US4196741A (en) * 1977-07-18 1980-04-08 Minghenelli Santo M Product and process for highlighting and streaking hair
US4579732A (en) * 1978-06-15 1986-04-01 L'oreal Hair dye or bleach supports
US4777040A (en) * 1978-06-15 1988-10-11 L'oreal Process and composition for protecting the hair from the degradation effects of a permanent wave
US5071641A (en) * 1988-06-10 1991-12-10 University Of Leeds Industrial Services Limited Method of setting hair
US20030143175A1 (en) * 2001-12-18 2003-07-31 Henri Samain Cosmetic compositions comprising polymers comprising complementary chemical functional groups
US20030157136A1 (en) * 2001-12-18 2003-08-21 Henri Samain Cosmetic composition forming a tackifying coating comprising a polymer with a non-silicone skeleton and reactive functional groups
US20030185781A1 (en) * 2001-12-18 2003-10-02 Henri Samain Cosmetic composition forming a soft coating comprising a polymer having a non-silicone backbone and reactive functional groups
US20080014161A1 (en) * 2001-12-18 2008-01-17 L'oreal S.A. Cosmetic compositions comprising polymers comprising complementary chemical functional groups

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