|Publication number||US3227615 A|
|Publication date||Jan 4, 1966|
|Filing date||May 29, 1962|
|Priority date||May 29, 1962|
|Publication number||US 3227615 A, US 3227615A, US-A-3227615, US3227615 A, US3227615A|
|Inventors||Korden Maria A|
|Original Assignee||Hercules Powder Co Ltd|
|Export Citation||BiBTeX, EndNote, RefMan|
|Patent Citations (5), Referenced by (171), Classifications (14) |
|External Links: USPTO, USPTO Assignment, Espacenet|
Process and composition for the permanent waving of hair
US 3227615 A
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.
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|US7204860||Apr 1, 2004||Apr 17, 2007||L'oreal||Using aliphatic diol; dyeing hair|
|US7208018||Apr 1, 2004||Apr 24, 2007||L'oreal||Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one associative polymer, process therefor and use thereof|
|US7211268||Nov 15, 2002||May 1, 2007||L'oreal S.A.||Preparation of polysaccharide betainate type compounds, compounds obtained, their use and compositions comprising them|
|US7217296||Sep 24, 2002||May 15, 2007||L'oreal S.A.||Dyeing composition with a lightening effect for human keratin materials comprising at least one fluorescent dye|
|US7217298||Jan 16, 2004||May 15, 2007||L'oreal S.A.||anhydrous bleaching paste and oxidizer; hydrogen peroxide in water in oil emulsion containing nonionic and, or anionic surfactant|
|US7220285||Apr 27, 2006||May 22, 2007||L'oreal S.A.||Pulverulent composition for bleaching human keratin fibers|
|US7220408||Nov 8, 2002||May 22, 2007||L'oreal, S.A.||Mixture of aminosilicone and thickener|
|US7223385||Nov 8, 2002||May 29, 2007||L'oreal S.A.||Cosmetic compositions containing a particular aminosilicone and a conditioner, and uses thereof|
|US7226486||Jan 15, 2004||Jun 5, 2007||L'oreal S.A||Ready-to-use bleaching compositions, preparation process and bleaching process|
|US7232561||Jun 2, 2003||Jun 19, 2007||L'oreal S.A.||Washing compositions comprising at least one amphiphilic block copolymer and at least one cationic or amphoteric polymer|
|US7250064||Apr 1, 2004||Jul 31, 2007||L'oreal S.A.||Using crosslinked acrylic polymer|
|US7258852||Sep 10, 2002||Aug 21, 2007||L'oreal S.A.||Cosmetic compositions containing a methacrylic acid copolymer and an oil, and uses thereof|
|US7261744||Dec 23, 2003||Aug 28, 2007||L'oreal S.A.||Method for dyeing or coloring human keratin materials with lightening effect using a composition comprising at least one fluorescent compound and at least one optical brightener|
|US7267696||Mar 25, 2004||Sep 11, 2007||L'oreal S.A.||Composition for dyeing keratinous fibers, comprising a hydroxycarboxylic acid or a salt, ready-to-use composition comprising it, implementation process and device|
|US7294152||Jan 7, 2005||Nov 13, 2007||L'oreal S.A.||Dyeing composition comprising at least one fluorindine compound for the dyeing of keratinic fibers, dyeing process comprising the composition and compound|
|US7303588||Mar 25, 2004||Dec 4, 2007||L'oreal S.A.||Composition for dyeing keratinous fibers, comprising at least one polycarboxylic acid or a salt, ready-to-use composition comprising it, implementation process and device|
|US7303589||Apr 1, 2004||Dec 4, 2007||L'oreal S.A.||Process for dyeing human keratin fibers, having a lightening effect, comprising at least one fluorescent compound and compositions of the same|
|US7323015||Oct 21, 2003||Jan 29, 2008||L'oreal S.A.||Dyeing human hair|
|US7326256||Dec 8, 2003||Feb 5, 2008||L'ORéAL S.A.||dyeing human hair; aqueous solution|
|US7329287||Dec 8, 2003||Feb 12, 2008||L'oreal S.A.||Oxidation dye composition for keratin fibers, comprising at least one oxidation dye, at least one associative polymer, at least one nonionic cellulose-based compound not comprising a C8-C30 fatty chain, and at least one cationic polymer with a charge density of greater than 1 meq/g and not comprising a C8-C30 fatty chain|
|US7364594||Nov 22, 2001||Apr 29, 2008||L'oreal S.A.||E.g., a quaternized polyetherurethane copolymer and an acrylamide/ dimethyldiallylammonium chloride/acrylic acid terpolymer.|
|US7402180||Jul 11, 2006||Jul 22, 2008||L'ORéAL S.A.||Composition for the oxidation dyeing of keratin fibres, comprising at least one fatty alcohol chosen from mono- and polyglycerolated fatty alcohols and a particular polyol|
|US7429275||Dec 23, 2005||Sep 30, 2008||L'oreal S.A.||Use of at least one compound chosen from porphyrin compounds and phthalocyanin compounds for dyeing human keratin materials, compositions comprising them, a dyeing process, and compounds therefor|
|US7431740||Nov 22, 2001||Oct 7, 2008||L'oreal, S.A.||Oxidation dyeing composition for keratinous fibers comprising an associative polymer and a pearling agent|
|US7442214||Mar 31, 2006||Oct 28, 2008||L'oreal S.A.||Dye composition comprising at least one non-ionic associative polymer and process for dyeing keratin fibers using same|
|US7485289||Feb 15, 2007||Feb 3, 2009||L'oreal, S.A.||Cosmetic compositions containing a particular aminosilicone and a conditioner, and uses thereof|
|US7498022||Mar 28, 2003||Mar 3, 2009||L'oreal S.A.||One amphiphilic polymer chosen from branched block copolymers comprising at least one nonionic unit derived from at least one monomer chosen from C1-20 alkyl (meth)acrylates, N-mono-(C2-12 alkyl)- meth)acrylamides and N,N-di-(C2-12|
|US7504094||Feb 15, 2007||Mar 17, 2009||L'oreal, S.A.||Hair conditioners; alkoxy-capped copolymer with dimethylsiloxy units and 3-(2-aminoethyl)aminopropyl)methyl- (or alkoxy-)siloxy units; for improving the lightness, softness, sheen and/or disentangling, and/or facilitating styling of hair|
|US7510705||Sep 21, 2006||Mar 31, 2009||L'oreal, S.A.||Process for permanently reshaping the hair using particular aminosilicones|
|US7550015||Mar 31, 2006||Jun 23, 2009||L'oreal S.A.||hair dyes comprising oxidation dye precursors and direct dyes, nonionic surfactants or anionic surfactants, hydroxyethylcellulose, cationic polymer; and one fatty substance; fatty acid esters of polyethylene glycol; multi-compartment kit for store the dyes|
|US7569078||Mar 31, 2006||Aug 4, 2009||L'oreal S.A.||Dye composition comprising at least one cellulose and process for dyeing keratin fibers using the dye composition|
|US7575605||Mar 31, 2006||Aug 18, 2009||L'oreal S.A.||Dye composition comprising at least one glycerol ester and a process for dyeing keratin fibers using the composition|
|US7578854||Mar 31, 2006||Aug 25, 2009||L'oreal S.A.||Applying to wet or dry keratin fibers a formulation containing oxidation dye precursor such as phenolamines, a direct dye ( azo dye, methine dye etc.), a fatty alchol, a fatty alcohol ester of polyglycerol, a oxyalkylenated or glycerolated nonionic surfactant, a cationic polymer|
|US7608115||Apr 30, 2004||Oct 27, 2009||L'oreal S.A.||Via applying direct dye, oxidation base, coupler, and oxidizing agent, then heating; oxidation color dyes; hair conditioners; cosmetics|
|US7651533||Mar 31, 2006||Jan 26, 2010||Oreal||Dye composition with a reduced content of starting materials, process for dyeing keratin fibers using the same and device therefor|
|US7708981||Mar 10, 2004||May 4, 2010||L'oreal S.A.||Cosmetic compositions comprising at least one crosslinked copolymer, at least one insoluble mineral particle and at least one polymer, and uses thereof|
|US7736465||Feb 6, 2004||Jun 15, 2010||Kemira Oyj||Controlling the wet to dry tensile strength ratio of paper by increasing the ratio the ratio by 10% by treating the pulp with a crosslinked anionicacrylic polymer and a cationic surfactant; increased softness fot towel and tissue products; papermaking|
|US7736631||Apr 1, 2004||Jun 15, 2010||L'oreal S.A.||Organic pigment colors and a modified polydimethylsiloxane homopolymer or copolymers for lightening hair or skin; multi-compartment kit for dyeing|
|US7771491||Dec 21, 2007||Aug 10, 2010||L'oreal S.A.||Hair dye; environmentally friendly, due to use of nonionic cellulose; good shampoo fastness|
|US7771492||Feb 23, 2009||Aug 10, 2010||L'oreal S.A.||Hair dyes; anionic thickener has hydrophilic olefinic unsaturated carboxylic acid and a C10-C30 alkyl unsaturated carboxylate; nonionic thickeners are celluloses modified by fatty chain or polyoxyethylenated polyurethanes; cationic thickener is quaternized cellulose with fatty acid chain; resists running|
|US7799093||Oct 25, 2007||Sep 21, 2010||L'ORéAL S.A.||Coloring composition of keratinous fibers comprising at least one polysiloxane/polyurea block copolymer|
|US7867969||Oct 30, 2006||Jan 11, 2011||L'oreal S.A.||Composition for washing keratin materials comprising a magnesium salt anionic surfactant|
|US7914775||Nov 6, 2001||Mar 29, 2011||L'oreal S.A.||Treating keratinous fibres, in particular human keratinous fibres such as hair, comprising in a physiologically acceptable medium, at least a protecting or conditioning agent, and further at least a cationic associative|
|US7928087||Jan 11, 2002||Apr 19, 2011||L'oreal||provides a flow texture to cosmetic compositions and are easily rinsed; Hair treated with the composition has a soft feel free of residue; used for washing and/or conditioning keratinous matter such as hair or skin|
|US7976831||Apr 4, 2005||Jul 12, 2011||L'oreal S.A.||Method for treating hair fibers|
|US7998464||Sep 28, 2006||Aug 16, 2011||L'oreal S.A.||Process for the photoprotective treatment of artificially dyed keratin fibers by application of a liquid water/steam mixture|
|US8070914||Apr 9, 2010||Dec 6, 2011||Kemira Oyj||Anionic functional promoter and charge control agent with improved wet to dry tensile strength ratio|
|US8349363||Nov 7, 2008||Jan 8, 2013||Kimberly-Clark Worldwide, Inc.||Temperature responsive delivery systems|
|US8425724||Oct 18, 2011||Apr 23, 2013||Kemira Oyj||Anionic functional promoter and charge control agent with improved wet to dry tensile strength ratio|
|US8557226||Jan 18, 2010||Oct 15, 2013||Isp Investments Inc.||Performance-boosting UV-absorbing compounds|
|US8586014||Oct 30, 2006||Nov 19, 2013||L'oreal||Composition for the care of keratin material and cosmetic treatment process using said composition|
|US8673272||Jul 22, 2010||Mar 18, 2014||Isp Investments Inc.||Ultraviolet-absorbing compounds|
|US8703109||Mar 28, 2008||Apr 22, 2014||L'oreal||Protection of keratinous fibers using ceramides and/or glycoceramides|
|US8784506||Oct 28, 2011||Jul 22, 2014||L'oreal||Dye composition having a low content of ammonia|
|US8790623||Jan 18, 2006||Jul 29, 2014||Il'Oreal||Composition for treating keratin fibers, comprising at least one aromatic alcohol, at least one aromatic carboxylic acid, and at least one protecting agent|
|US8802066||Dec 20, 2011||Aug 12, 2014||L'oreal||Cosmetic composition comprising a particular zinc salt and an amino silicone|
|US8828368||Dec 20, 2011||Sep 9, 2014||L'oreal||Cosmetic composition comprising a particular zinc salt and a starch|
|DE202013011676U1||Nov 8, 2013||Feb 14, 2014||L'oreal||Zusammensetzung, die eine Dicarbonylverbindung enthält|
|EP0011511A2 *||Nov 20, 1979||May 28, 1980||Lamaur Inc.||A method and compositions for relaxing natural curls and kinks in human hair and a package for these compositions|
|EP0723772A1||Jan 10, 1996||Jul 31, 1996||L'oreal||Reducing composition bared on a basic amino acid and a cationic polymer|
|EP1920755A1||Nov 9, 2007||May 14, 2008||L'Oréal||Method for permanently deforming keratinous fibres comprising a step of applying an intermediate rinsing component comprising a monovalent metal cation salt or an ammonia salt and an organic acid|
|EP2011473A1||Jun 26, 2008||Jan 7, 2009||L'Oreal||Anhydrous composition in paste form for bleaching keratinous fibres.|
|EP2065023A2||Nov 28, 2008||Jun 3, 2009||L'Oreal||Hairstyling composition comprising at least one (meth)acrylic copolymer and at least one pearlescent agent|
|EP2065024A2||Nov 28, 2008||Jun 3, 2009||L'Oreal||Hairstyling composition comprising (meth)acrylic copolymers and at least one oil|
|EP2072033A2||Sep 12, 2008||Jun 24, 2009||L'Oreal||Cosmetic composition comprising at least one specific cationic polymer and at least one fatty acid ester in C8-C24 and oxyethylenated sorbitan comprising 2 to 10 oxyethylene patterns, and cosmetic treatment method using said composition|
|EP2198929A1||Dec 18, 2009||Jun 23, 2010||L'oreal||Hair dye or lightening composition comprising a fatty substance and a cationic polymer, and use thereof|
|EP2301630A2||Dec 18, 2009||Mar 30, 2011||L'Oréal||Oxidizing composition for the treatment of keratin fibres comprising a cationic polymer, a fatty amide and an anti-oxygen agent|
|EP2343040A2||Dec 17, 2010||Jul 13, 2011||L'Oréal||Cosmetic composition containing at least one organic silicon compound, at least one anionic surface-active agent and at least one amine silicone as well as a method implementing said composition|
|WO2010070140A1||Dec 21, 2009||Jun 24, 2010||L'oreal||Antiperspirant composition containing at least one complex formed by combining at least one anionic species and at least one cationic species, and process for treating human perspiration|
|WO2011074140A1||Dec 18, 2009||Jun 23, 2011||L'oreal||Process for treating keratin fibers|
|WO2011107432A2||Feb 28, 2011||Sep 9, 2011||L'oreal||Composition comprising ellagic acid and a particular cationic surfactant, and cosmetic use thereof|
|WO2011107433A2||Feb 28, 2011||Sep 9, 2011||L'oreal||Cosmetic composition based on ellagic acid or a derivative thereof and a bacterial extract|
|WO2011107467A2||Mar 1, 2011||Sep 9, 2011||L'oreal||Cosmetic composition based on ellagic acid or a derivative thereof and on a particular mixture of surfactants|
|WO2011107468A2||Mar 1, 2011||Sep 9, 2011||L'oreal||Cosmetic antidandruff composition based on ellagic acid or a derivative thereof and a second, different active compound in a specific weight ratio|
|WO2011107469A1||Mar 1, 2011||Sep 9, 2011||L'oreal||Use of ellagic acid as an anti-dandruff agent|
|WO2012032055A1||Sep 6, 2011||Mar 15, 2012||L'oreal||Cosmetic composition comprising at least one cationic polymer and at least two cationic surfactants|
|WO2012032673A1||Sep 8, 2010||Mar 15, 2012||L'oreal||Cosmetic composition for keratin fibers|
|WO2012038536A2||Sep 23, 2011||Mar 29, 2012||L'oreal||Cosmetic composition comprising at least one hygroscopic salt, at least one aromatic polyol ether and at least one diol, and cosmetic treatment process|
|WO2012042019A2||Sep 30, 2011||Apr 5, 2012||L'oreal||Process for treating keratin fibres using at least one sulfureous reducing agent, at least one cationic polymer and at least one mercaptosiloxane.|
|WO2012049145A1||Oct 11, 2011||Apr 19, 2012||L'oreal||Cosmetic composition comprising a particular silicon derivative and one or more acrylic thickening polymers|
|WO2012055807A1||Oct 24, 2011||May 3, 2012||L'oreal||Cosmetic composition comprising a fatty-chain alkoxysilane and a cationic polymer|
|WO2012055812A1||Oct 24, 2011||May 3, 2012||L'oreal||Cosmetic composition comprising a fatty-chain alkoxysilane and an antidandruff agent.|
|WO2012059410A1||Oct 28, 2011||May 10, 2012||L'oreal||Dye composition having a low content of ammonia|
|WO2012072765A1||Dec 1, 2011||Jun 7, 2012||L'oreal||Cosmetic composition containing a non-amino silicone, a liquid fatty ester and an amino silicone, process and use|
|WO2012084863A1||Dec 19, 2011||Jun 28, 2012||L'oreal||Cosmetic composition comprising a zinc salt and 1,2-octanediol|
|WO2012084866A1||Dec 19, 2011||Jun 28, 2012||L'oreal||Composition comprising a non-nitrogenous zinc salt and a particular cationic surfactant|
|WO2012084867A1||Dec 19, 2011||Jun 28, 2012||L'oreal||Cosmetic composition comprising a zinc salt, a cationic polymer and a propellant|
|WO2012084901A1||Dec 20, 2011||Jun 28, 2012||L'oreal||Cosmetic composition comprising a zinc salt and a solid fatty ester|
|WO2012084903A1||Dec 20, 2011||Jun 28, 2012||L'oreal||Cosmetic composition comprising a particular zinc salt and an amino silicone|
|WO2012084904A1||Dec 20, 2011||Jun 28, 2012||L'oreal||Cosmetic composition comprising a particular zinc salt and a starch|
|WO2012137165A2||Apr 5, 2012||Oct 11, 2012||L'oreal||A hair treatment method|
|WO2012149617A1||May 4, 2011||Nov 8, 2012||L'oreal S.A.||Detergent cosmetic compositions comprising four surfactants, a cationic polymer and a silicone, and use thereof|
|WO2012163868A2||May 28, 2012||Dec 6, 2012||L'oreal||Composition comprising an alkoxysilane, a fatty ester and a silicone, and cosmetic use thereof|
|WO2012163869A2||May 28, 2012||Dec 6, 2012||L'oreal||Composition comprising an alkoxysilane and a modified starch, and cosmetic use thereof|
|WO2012164065A2||Jun 1, 2012||Dec 6, 2012||L'oreal||Process for treating straightened keratin fibres|
|WO2012171850A2||Jun 8, 2012||Dec 20, 2012||L'oreal||Cosmetic composition comprising an anionic surfactant, a nonionic or amphoteric surfactant and a solid fatty alcohol, and cosmetic treatment process|
|WO2013004773A2||Jul 5, 2012||Jan 10, 2013||L'oreal||Cosmetic composition rich in fatty substances comprising a polyoxyalkylenated fatty alcohol ether and a direct dye and/or an oxidation dye, the dyeing method and the device|
|WO2013042274A1||Sep 22, 2011||Mar 28, 2013||L'oreal||Cosmetic cleansing composition|
|WO2013092608A2||Dec 18, 2012||Jun 27, 2013||L'oreal||Cosmetic composition comprising a hydrophobically modified cellulose, a sulfated or sulfonated anionic surfactant and a branched fatty alcohol|
|WO2013092722A1||Dec 19, 2012||Jun 27, 2013||L'oreal||Cosmetic composition comprising a hydrophobically modified cellulose and an anionic surfactant comprising one or more carboxylate group(s)|
|WO2013110653A1||Jan 23, 2013||Aug 1, 2013||L'oreal||Composition comprising at least one specific alkoxysilane polymer|
|WO2013144871A1||Mar 27, 2013||Oct 3, 2013||L'oreal||Cosmetic process for caring for and/or making up keratin materials|
|WO2014002290A1||Jun 29, 2012||Jan 3, 2014||L'oreal||Cosmetic composition for keratin fibers|
|WO2014020146A2||Aug 2, 2013||Feb 6, 2014||L'oreal||Dyeing composition comprising at least one fatty substance, at least one oxidizing agent and at least one non-ionic, anionic and amphoteric surfactant|
|WO2014020147A2||Aug 2, 2013||Feb 6, 2014||L'oreal||Dyeing composition comprising a fatty substance, a non-ionic guar gum, an amphoteric surfactant and a non-ionic or anionic surfactant, and an oxidizing agent, dyeing process and suitable device|
|WO2014056962A2||Oct 9, 2013||Apr 17, 2014||L'oreal||Cosmetic composition comprising a bacterial lysate, a thickener and a particular surfactant system, and cosmetic treatment process|
|WO2014068795A1||Oct 31, 2012||May 8, 2014||L'oreal||Use of triazine derivatives for permanent deformation of keratin fibers|
|WO2014091111A2||Nov 27, 2013||Jun 19, 2014||L'oreal||Cosmetic composition comprising the association of nonionic and cationic surfactants, and cosmetic treatment method|
|WO2014091125A2||Dec 6, 2013||Jun 19, 2014||L'oreal||Cosmetic composition comprising a nonionic surfactant, a cationic surfactant, a liquid fatty ester and a particular silicone, and cosmetic treatment method|
|WO2014111579A2||Jan 20, 2014||Jul 24, 2014||L'oreal||Hair shaping process in which is applied a particular styling composition, which is rinsed out|
|WO2014111668A2||Jan 20, 2014||Jul 24, 2014||L'oreal||Flexible solid cosmetic composition comprising anionic surfactants and polyols, and cosmetic treatment method|
|WO2014111669A2||Jan 20, 2014||Jul 24, 2014||L'oreal||Flexible solid cosmetic composition comprising anionic surfactants and solid particles, and cosmetic treatment process|
| || |
|U.S. Classification||132/204, 528/342, 8/127.51|
|International Classification||A61K8/72, A61K8/19, A61K8/23, A61Q5/04, A61K8/88|
|Cooperative Classification||A61Q5/04, A61K8/88, A61K8/23|
|European Classification||A61Q5/04, A61K8/88, A61K8/23|