US3227615A - Process and composition for the permanent waving of hair - Google Patents

Process and composition for the permanent waving of hair Download PDF

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US3227615A
US3227615A US19842462A US3227615A US 3227615 A US3227615 A US 3227615A US 19842462 A US19842462 A US 19842462A US 3227615 A US3227615 A US 3227615A
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water
hair
soluble
amine groups
secondary amine
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Maria A Korden
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Hercules Inc
Hercules Powder Co
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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
    • A61K8/19Cosmetics or similar toilet preparations characterised by the composition containing inorganic ingredients
    • A61K8/23Sulfur; Selenium; Tellurium; Compounds thereof
    • 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

Description

United States Patent Ofilice 3,227,615 Patented Jan. 4, 1966 3,227,615 PROCESS AND COMPGSITION FOR THE PERMA- NENT WAVING OF HAIR Maria A. Korden, Wilmington, Del., assignor to Hercules Powder Company, Wilmington, Del., a corporation of Delaware N Drawing. Filed May 29, 1962, 59k. No. 193,424 11 Claims. (Cl. 16787.1)

This invention relates to a process for the cold waving of hair and to novel compositions useful for this purpose.

One of the better known commercial hair-waving treatments involves the use of ammonium thioglycolate and an oxidizing agent. The hair is usually wound on rollers and then saturated with an ammonium thioglycolate solution. After a period of time ranging from about 15 to about 30 minutes, the ammonium thioglycolate solution is washed out and the curls are set with an oxidizing agent, usually dilute hydrogen peroxide.

The use of the thioglycolate-peroxide treatment for the cold waving of hair has a number of disadvantages. Among these are (1) it produces a strong, pungent odor and (2) it cannot be used over an extended period of time due both to the odor of the thioglycolate and its tendency to damage the hair. In an effort to overcome these disadvantages, other agents and combinations of agents have been employed. However, these, in most cases, have likewise not been entirely satisfactory either because they are too severe in their action or because of other disadvantages, such as unpleasant odor, toxicity, and so on.

An object of the invention is the provision of a novel and improved process for the cold waving of hair which does not require the use of an oxidizing agent, which does not cause damage to the hair, and which does not cause undesirable odor.

A further object of the invention is the provision of a novel and improved composition for the cold waving of hair which can be used at room temperatures for extended periods of time without causing damage to the hair and without undesirable odor.

In accordance with the invention, it has now been found that the above and other objects can be accomplished by treating hair with a water-soluble bisulfite and a Water-soluble cationic polyamide-epichlorohydrin resin of the type hereinafter described. Several procedures can be used for applying these materials to the hair. In accordance with one procedure, the watersoluble bisulfite and the cationic resin, each in aqueous solution, are applied to the hair separately, the bisulfite being applied first followed by the cationic resin. In accordance with another procedure, the bisulfite and the resin are applied to the hair in the form of a mixture of the two in aqueous solution, mixtures of this type forming the novel and improved compositions to which reference is made hereinabove. Regardless of the procedure utilized, the combined use of these materials has been found to be more effective than the use of either material alone, thus indicating that there is a synergistic effect.

The water-soluble bisulfites contemplated for use in the compositions of the invention are sodium bisulfite, potassium bisulfite, ammonium bisulfite, an amine bisulfite, such as ethyl amine bisulfite, and so on. Also, any of the corresponding metabisulfites which hydrolyze in the presence of water to yield bisulfites are operable.

The water-soluble polyamide-epichlorohydrin resins contemplated for use herein comprise a water-soluble polymeric reaction product of epichlorohydrin and a polyamide derived from a polyalkylene polyamine and a C -C saturated aliphatic dicarboxylic acid. It has been found that resins of this type are uniquely effective for the purposes of the present invention.

In the preparation of these cationic thermosetting resins, the dicarboxylic acid is first reacted with the polyalkylene polyamine under conditions such as to produce a Water-soluble polyamide containing the recurring groups NH(C H HN) CORCO- where n and x are each 2 or more and R is the divalent hydrocarbon radical of the dicarboxylic acid. This water-soluble polyamide is then reacted with epichlorohydrin to form the water-soluble cationic thermosetting resin.

The dicarboxylic acids contemplated for use in preparing these resins are the saturated aliphatic dicarboxylic acids preferably containing from 3 to 8 carbon atoms such as malonic, succinic, glutaric, adipic, and so on, together with diglycoiic acid. Of these, diglycolic acid and the saturated dicarboxylic acids having from 4 to 6 carbon atoms in the molecule, namely, succinic, glutaric and adipic, are most preferred. Blends of two or more of these dicarboxylic acids can also be used, as well as blends of one or more of these with higher saturated aliphatic dicarboxylic acids, such as azelaic and sebacic, as long as the resulting long-chain polyamide is water soluble or at least water dispersible.

A variety of polyalkylene polyamines including polyethylene polyamines, polypropylene polyamines, polybutylene polyamines, and so on may be employed of which the polyethylene polyamines represent an economically preferred class. More specifically, the polyalkylene polyamines contemplated for use are polyamines containing two primary amine groups and at least one secondary amine group in which the nitrogen atoms are linked together by groups of the formula C H where n is a small integer greater than unity and the number of such groups in the molecule ranges from two up to about eight, and preferably up to about four. The nitrogen atoms may be attached to adjacent carbon atoms in the group C H or to carbon atoms further apart, but not to the same carbon atom. This invention contemplates not only the use of such polyamines as diethylenetriamine, triethylenetetramine, tetraethylenepentamine, dipropylenetriamine, and the like, which can be obtained in reasonably pure form, but also mixtures and various crude polyamine materials. For example, the mixture of polyethylene polyamines obtained by the reaction of ammonia and ethylene dichloride, refined only to the extent of removal of chlorides, water, excess ammonia and ethylenediamine, is a very satisfactory starting material. Most preferred are the polyethylene poly amines containing from two to four ethylene groups, two primary amine groups, and irom one to three secondary amine groups.

The term polyalkylene polyamine employed in the claims, therefore, refers to and includes any of the polyalkylene polyamines referred to above or to a mixture of such polyalkylenc polyamines.

It is desirable, in some cases, to increase the spacing of secondary amine groups on the polyamide molecule in order to change the reactivity of the polyamideepichlorohydrin complex. This can be accomplished by substituting an aliphatic diamine such as ethylenediamine, propylenediamine, hexamethylenediamine, or a heterocyciic diamine such as piperazine or the like for a portion of the polyalkylene polyamine. For this purpose, up to about 60% of the polyalkylene polyamine may be replaced by a molecularly equivalent amount of the di amine. Usually, a replacement of about 30% or less will serve the purpose.

The temperatures employed for carrying out the reaction between the dicarboxylic acid and the polyalkylene polyamine can vary from about C. to about 250 C.

or higher at atmospheric pressure. For most purposes, however, temperatures between about 160 C. and 210 C. have been found satisfactory and are preferred. Where reduced pressures are employed, somewhat lower temperatures may be utilized. The time of reaction depends on the temperatures and pressures utilized and will ordinarily vary from about /2 to 2 hours, although shorter or longer reaction times may be utilized depending on reaction conditions. In any event, the reaction is desirably continued to substantial completion for best results.

In carrying out the reaction, it is preferred to use an amount of dicarboxylic acid sufficient to react substantially completely with the primary amine groups of the poiyalkylene polyamine but insufficient to react with the secondary amine groups to any substantial extent. This will usually require a mole ratio of polyalltylene polyamine to dicarboxylic acid of from about 0.9:1 to about 1.2:1. However, mole ratios of from about 0.821 to about 1.4:1 may be used with quite satisfactory results. Mole ratios outside of these ranges are generally unsatisfactory. Thus, mole ratios below about 0.8:1 result in a gelled product or one having a pronounced tendency to gel, while mole ratios above 1.411 result in low molecular weight polyamides. Such products, when reacted with epichlorohydrin, do not produce resins having the desired efiiciency for use herein.

In converting the polyamide, formed as above described, to a cationic thermosetting resin, it is reacted with epichlorohydrin at a temperature from about 45 C. to about 100 C., and preferably from about 45 C. to about 70 C., until the viscosity of a 25% solids solution at 25 C. has reached at least B, and preferably at least D, on the Garduer-Holdt scale. This reaction is preferably carried out in aqueous solution to moderate the reaction. pH adjustment is usually not necessary. However, since the pi-l decreases during the polymerization phase of the reaction, it may be desirable, in some cases, to add alkali to combine with at least some of the acid formed.

When the desired viscosity is reached, sufficient water is then added to adjust the solids content of the resin solution to the desired amount, the product cooled to about 25 C. and then stabilized by adding sufiicient acid to reduce the pH at least to about 6, and preferably to about 4 or lower, e.g., from about 2-4. Any suitable acid such as hydrochloric, sulfuric, nitric, formic, phosphoric, and acetic acid, or various combinations of these, can be used to stabilize the product.

In the polyamide-epichlorohydrin reaction, it is preferred to use sufficient epichlorohydrin to convert all secondary amine groups to tertiary amine groups. However, more or less can be added to moderate or increase reaction rates. In general, satisfactory results can be obtained utilizing from about 0.5 mole to about 1.8 moles of epichlorohydrin for each secondary amine group of the polyarnide. It is preferred to utilize from about 0.9 mole to about 1.5 moles of epichlorohydrin for each secondary amine group of the polyainide.

In the cold waviri of hair, for example, human hair, in accordance with the invention, the hair, after the usual shampoo, can be wound on curlers and then treated successively with aoueous solutions of the bisulfite and the cationic resin or simultaneously with a mixture of the two. The pH to be utilized in the treatment will desirably be from about 6.0 to about 7.2, and preferably from about 6.5 to about 6.8. The desired pH of treatment can be obtained by adjusting the pH of the aqueous treating comopsitions to a value somewhat above that desired during the treatment, e.g., within the range from about 6.5 to about 7.2, since the hair reduces the pH somewhat.

Aqueous mixtures of the bisulfite and resin will desirably contain from about 2% to about by wel ht, based on the weight of the compositions, of the bisultite from about 2% to about 10% by weight, based on the weight of the composition, of resin solids. Where the two are utilized separately, corresponding proportions can be used.

In an alternative method, the hair can be shampooed, treated with the bisulfite and resin, wound on curlers and again treated with the bisulfite and resin. Application to the hair can be accomplished in any suitable manner, as by spraying, absorbent wad, or the like.

The time of treatment will vary depending on a number of factors including the type of treatment, the type of hair, and so on, but will generally be from about 30 iinutes to about 60 minutes at ordinary room temperatures and for somewhat shorter periods at higher temperatures. Temperatures higher than room temperatures, e.g., up to about 38 C., can be attained by placing a plastic cap over the hair. Following the treatment with the bisulfite and resin, the hair can then be washed and subjected to any of the usual treatments commonly utilized in the cold waving of hair.

The following examples are given to illustrate specific embodiments of the invention. In these examples wetcurl retention was determined utilizing the apparatus and procedures described in U.S. 2,836,543.

Example 1 A cationic polyamide-epichlorohydrin resin 0f the type herein described was prepared as follows:

Two hundred twenty-five parts of diethylenetriamine and 108 parts of water were placed in a reaction vessel and agitated. To this was added 327 parts of adipic acid. After the acid had dissolved in the amine, the solution was heated to 165-170" C. and held there until the reaction was completed. Then 503 parts of water was added. The resulting polyamide solution contained 50.0%52.0% solids and had an intrinsic viscosity at 25 C. from about (3.115 to about 0.125.

To parts of this poiyamide solution was added 395 parts of water. This solution was heated to 50 C., and 25.5 parts of epichlorohydrin was added. The mixture was then heated at about 76 C. until it had attained a Gardner viscosity of DE. Then 181.8 parts of water was added to the product, it was cooled to 25 C.30 C., and sufficient 10% l-lCl added to adjust the pH to about 5.0. The product contained about 16% solids and had a Gardner viscosity of CD.

A sample of human hair was bent around the pegs of a curling device of the type shown in U.S. 2,836,543 and held in place by an elastic band. The hair was then saturated with an aqueous solution containing 5% sodium bisulfite and 4% (resin solids) of the cationic resin prepared as above described and adjusted to pH 6.5 with sodium hydroxide. The assembly was placed in an oven at 38 C. for 30 minutes after which it was placed in rinsing vater for 5 minutes at 28 C. The wetcurl retention, measured immediately after the rinse, was 29.1%.

Example 2 A sample of human hair was treated in the same manner as in Example 1 except that a solution containing 10% sodium bisulfite and 4% resin solids, adjusted to pH 6.5, was used. Wet-curl retention was 29.1%.

Example 3 A sample of human hair was bent around the curling device as before. It was saturated with a 2% solution of sodium bisulfite, and the assembly was placed in an oven at 38 C. for 20 minutes. The hair was then wet with a 2% solution of the resin of Example 1, and the assembly was returned to the oven for 15 minutes at 38 C. The hair was then rinsed with water at 27 C. for 5 minutes. Wet-curl retention was 18%.

Example 4 The procedure of Example 3 was followed except that the pH of both solutions was adjusted to 6.5 with sodium hydroxide. The wet-curl retention was 29%.

Example 5 The hair assembly was prepared as before and the hair saturated with a solution of 5% sodium bisulfite and 4% of the resin (solids basis) described in Example 1 and adjusted to a pH of 6.5. The assembly was placed in the oven at 38 C. for 45 minutes and the hair then rinsed for 5 minutes wtih 27 C. water. The curl retention was 37.5%.

Example 6 The procedure of Example 5 was followed except that the solution contained sodium bisulfite. Wet-curl retention was 50%.

Example 7 The procedure of Example 5 was followed except that the pH of the bisulfite-resin solution was adjusted to 7 .2 with sodium hydroxide. Wet-curl retention was 24%.

Example 8 Hair was treated with a solution of 10% sodium bisulfite and 4% of the resin (solids basis) described in Example 1 and adjusted to a pH of 6.5. The assembly was placed in the oven at 38 C. for 60 minutes, then rinsed with 27 C. water for 10 minutes. Curl retention was 50%.

It will thus be seen that the present invention provides a novel and effective process and composition for the cold waving of hair which does not give 011 odor and which does not require neutralization of the hair with oxidizing agents. While preferred embodiments of the invention have been described, the invention is not to be construed as limited to the details thereof except as they may be included in the accompanying claims.

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

1. The method of cold waving hair which comprises treating the same with a water-soluble bisulfite and a water-soluble cationic thermosetting resin obtained by reacting a polyalkylene polyamine having two primary amine groups and at least one secondary amine group with a dicarboxylic acid selected from the group consisting of diglycolic acid and C -C saturated aliphatic dicarboxylic acids to form a water-soluble, long-chain polyamide containing secondary amine groups, the mole ratio of polyalkylene polyamine to dicarboxylic acid being from about 0.8:1 to about 1.4:1, and then reacting the polyamide in aqueous solution with epichlorohydrin in a mole ratio of epichlorohydrin to secondary amine groups of said polyamide of from about 0.5:1 to about 1.8: l.

2. The method of claim 1 wherein the hair is treated first with the water-soluble bisulfite and then with the water-soluble cationic thermosetting resin.

3. The method of claim 1 wherein the water-soluble bisulfite and the Water-soluble cationic thermosetting resin are applied to the hair in admixture in an aqueous solution.

4. The method of cold Waving hair which comprises (1) adjusting said hair to the desired configuration, (2) contacting said hair at a pH from about 6.0 to about 7.2 with a water-soluble bisulfite and a water-soluble cationic thermosetting resin obtained by reacting a polyalkylene polyamine having two primary amine groups and at least one secondary amine group with a dicarboxylic acid selected from the group consisting of diglycolic acid and C -C saturated aliphatic dicarboxylic acids to form a water-soluble, long-chain polyamide containing secondary amine groups, the mole ratio of polyalkylene polyamine to dicarboxylic acid being from about 0.8:1 to about 1.4: l, and then reacting the polyamide in aqueous solution with epichlorohydrin in a mole ratio of epichlorohydrin to secondary amine groups of said polyamide of from about 0.5 :1 to about 1.8:1, washing said hair with water, and drying said hair.

5. The method of claim 4 wherein the hair is treated 6 first with the water-soluble bisulfite and then with the water-soluble cationic thermosetting resin.

6. The method of claim 4 wherein the water-soluble bisulfite and the water-soluble cationic thermosetting resin are applied to the hair in admixture in an aqueous solution.

7. The method of claim 6 wherein the bisulfite is present in said mixture in an amount from about 2% to about 10% by weight of the solution, and said cationic thermosetting resin is likewise present in said mixture in an amount from about 2% to about 10% by weight resin solids, based on the Weight of the solution.

8. A composition for the cold waving of hair comprising an aqueous solution of a mixture of water-soluble bisulfite and water-soluble cationic thermosetting resin obtained by reacting a polyalkylene polyamine having two primary amine groups and at least one secondary amine group with a dicarboxylic acid selected from the group consisting of diglycolic acid and C C saturated aliphatic dicarboxylic acids to form a water-soluble, longchain polyamide containing secondary amine groups, the mole ratio of polyalkylene polyamine to a dicarboxylic acid being from about 0.8:1 to about 1.4:1, and then reacting the polyamide in aqueous solution with epichlorohydrin in a mole ratio of epichlorohydrin to secondary amine groups of said polyamide of from about 0.5:1 to about 1.8:1, said bisulfite being present in an amount from about 2% to about 10% by Weight of the solution, and said cationic thermosetting resin being present in an amount from about 2% to about 10% by weight resin solids, based on the weight of the solution, said solution having a pH from about 6.5 to about 7.2.

9. A composition in accordance with claim 8 wherein said bisulfite is sodium bisulfite.

10. A composition in accordance with claim 8 wherein said bisulfite is ammonium bisulfite.

11. The method of preparing a composition for the cold waving of hair which comprises forming an aqueous solution of a water-soluble bisulfite and a water-soluble cationic resin obtained by reacting a polyalkylene polyamine having two primary amine groups and at least one secondary amine group with a dicarboxylic acid selected from the group consisting of diglycolic acid and C C saturated aliphatic dicarboxylic acids to form a watersoluble, long-chain polyamide containing secondary amine groups, the mole ratio of polyalkylene polyamine to dicarboxylic acid being from about 0.821 to about 1.421, and then reacting the polyamide in aqueous solution with epichlorohydrin in a mole ratio of epichlorohydrin to secondary amine groups of said polyamide of from about 0.5:1 to about 1.8: 1, said bisulfite being present in an amount from about 2% to about 10% by weight of the solution, and said cationic thermosetting resin being present in an amount from about 2% to about 10% by weight resin solids, based on the weight of the solution, and adjusting the pH of the solution to from about 6.5 to about 7.2.

References Cited by the Examiner UNITED STATES PATENTS 2,400,377 5/1946 Speakman 16787.1 2,836,543 5/1958 Watson 167-87.1 2,882,185 4/1959 Valko et al 117-161 2,926,154 2/1960 Keim 117161 2,948,656 8/1960 Tousignant et al. 167-87.1

OTHER REFERENCES Sagarin: Cosmetics: Science and Technology published by Interscience Publishers, Inc., New York, 1957, pages 531-533 relied upon (copy available in Patent Office Scientific Library).

LEWIS GOTTS, Primary Examiner. FRANK CACCIAPAGLIA, 111., Examiner.

Claims (2)

1. THE METHOD OF COLD WAVING HAIR WHICH COMPRISES TREATING THE SAME WITH A WATER-SOLUBLE BISULFATE AND A WATER-SOLUBLE CATIONIC THERMOSETTING RESIN OBTAINED BY REACTING A POLYALKYLEENE PLYAMINE HAVING TWO PRIMARY AMINE GROUPS AND AT LEAST ONE SECONDARY AMINE GROUP WITH A DICARBOXYLIC ACID SELECTED FROM THE GROUP CONSISTING OF DIGLYCOLIC ACID AND C3-C8 SATURATED ALIPHATIC DICARBOXYLIC ACIDS TO FORM A WATER-SOLUBLE, LONG-CHAIN POLYAMIDE CONTAINING SECONDARY AMINE GROUPS, THE MOLE RATIO OF POLYALKYLENE POLAMINE TO DICARBOXYLIC ACID BEING FROM ABOUT 0.8:1 TO ABOUT 1.4:1, AND THEN REACTING THE POLYAMIDE IN AQUEOUS SOLUTION WITH EPICHLOROHYDRIN IN A MOLE RATIO OF EPICHLOROHYDRIN TO SECONDARY AMINE GROUPS OF SAID POLYAMIDE OF FROM ABOUT 0.5:1 TO ABOUT 1.8:1.
8. A COMPOSITION FOR THE COLD WAVING OF HAIR COMPRISING AN AQUEOUS SOLUTION OF A MIXTURE OF WATER-SOLUBLE BISULFITE AND WATER-SOLUBLE CATIONIC THERMOSETTING RESIN OBTAINED BY REACTING A POLYALKYLENE POLYAMINE HAVING TWO PRIMARY AMINE GROUPS AND AT LEAST ONE SECONDARY AMINE GROUP WITH A DICARBOXYLIC ACID SELECTED FROM THE GROUP CONSISTING OF DIGLYCOLIC ACID SELECTED FROM THE GROUP CONSISTING OF DIGLYCOLIC ACID AND C3-C8 SATURATED ALIPHATIC DICARBOXYLIC ACIDS TO FORM A WATER-SOLUBLE, LONGCHAIN POLYAMIDE CONTAINING SECONDARY AMINE GROUPS, THE MOLE RATIO OF POLYALKYLENE POLYAMINE TO A DICARBOXYLIC ACID BEING FROM ABOUT 0.8:1 TO ABOUT 1.4:1, AND THEN REACTING THE PLYAMIDE IN AQUEOUS SOLUTION WITH EPICHLOROHYDRIN IN A MOLE RATIO OF EPICHLOROHYDRIN TO SECONDARY AMINE GROUPS OF SAID POLYAMIDE OF FROM ABOUT 0.5:1 TO ABOUT 1.8:1, SAID BISULFITE BEING PRESENT IN AN AMOUNT FROM ABOUT 2% TO ABOUT 10% BY WEIGHT OF THE SOLUTION, AND SAID CATIONIC THERMOSETTING RESIN BEING PRESENT IN AN AMOUNT FROM ABOUT 2% TO ABOUT 10% BY WEIGHT RESIN SOLIDS, BASED ON THE WEIGHT OF THE SOLUTION, SAID SOLUTION HAVING A PH FROM ABOUT 6.5 TO ABOUT 7.2.
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US4842851A (en) * 1986-06-02 1989-06-27 L'oreal Polyamino amides for protecting hair against atmospheric attack, and in particular against light, and process for protecting hair employing such polyaminoamides
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US5071641A (en) * 1988-06-10 1991-12-10 University Of Leeds Industrial Services Limited Method of setting hair
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US6451298B1 (en) 1999-10-20 2002-09-17 L'oreal, S.A. Cosmetic compositions comprising at least one silicone copolymer and at least one cationic polymer, and uses thereof
US6471953B1 (en) 1999-06-28 2002-10-29 L'oreal S.A. Permanent-waving process comprising the preliminary application of a composition comprising at least one anionic polymer
US20020157193A1 (en) * 2001-02-02 2002-10-31 Frederic Legrand Pulverulent composition for bleaching human keratin fibers
US6482400B1 (en) 1999-06-30 2002-11-19 L'Oréal S.R. Mascara containing film-forming polymers
US20020193265A1 (en) * 2001-03-30 2002-12-19 Beatrice Perron Detergent cosmetic compositions containing an anionic surfactant derived from amino acids and salts thereof and a soluble conditioning agent and uses thereof
US6506372B1 (en) 1999-06-25 2003-01-14 L'oreal S.A. Cosmetic compositions containing an amphoteric polymer and a fixing/conditioner polymer, and their uses
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