US3917817A - Hair treating cosmetic compositions containing piperazine based cationic polymer - Google Patents

Hair treating cosmetic compositions containing piperazine based cationic polymer Download PDF

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US3917817A
US3917817A US31008872A US3917817A US 3917817 A US3917817 A US 3917817A US 31008872 A US31008872 A US 31008872A US 3917817 A US3917817 A US 3917817A
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hair
cationic polymer
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piperazine
water
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Guy Vanlerberghe
Henri Sebag
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LOreal SA
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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
    • A61Q5/02Preparations for cleaning 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
    • A61K8/72Cosmetics 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
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/12Preparations containing hair conditioners
    • 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
    • C08G73/0273Polyamines containing heterocyclic moieties in the main chain
    • 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
    • C08G73/06Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0633Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring
    • 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
    • Y10S424/01Aerosol hair preparation
    • 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
    • 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
    • Y10S424/04Dandruff

Abstract

Piperazine-based low molecular weight film-forming cationic polymer is employed in a cosmetic hair-conditioner composition comprising a solution of the polymer in amounts of about 0.1-5 weight percent of the composition in a solvent such as water, acidified water, or aqueous alcohol solution.

Description

United States Patent 1 Vanlerberghe et a1.

[45] Nov. 4, 1975 HAIR TREATING COSMETIC COMPOSITIONS CONTAINING PIPERAZINE BASED CATIONIC POLYMER [75] Inventors: Guy Vanlerberghe, Montjay-la-Tour par Claie-Souilly; Henri Sebag, Paris, both of France [73] Assignee: LOreal, Paris, France [22] Filed: Nov. 28, 1972 [21] Appl. No.: 310,088

[30] Foreign Application Priority Data Nov. 29, 1971 Luxembourg 064371 260/29.6 HN; 424/47, 70, 71, DIG. 1, DIG. 2

[56] References Cited UNITED STATES PATENTS 3,069,390 12/1962 Kline et a]. 424/47 X 3,250,682 5/1966 Wilmsmann et a1. 3,267,046 8/1966 Bonvicini 260/2 BP 3,274,312 9/1966 Compostella et al. 264/78 3,280,044 10/1966 Bonvicini et a1. 260/2 BP Primary ExaminerAlbert T. Meyers Assistant Examiner-Vera C. Clarke Attorney, Agent, or FirmCushman, Darby & Cushman [57] ABSTRACT Piperazine-based low molecular weight film-forming cationic polymer is employed in a cosmetic hairconditioner composition comprising a solution of the polymer in amounts of about 0.1-5 weight percent of the composition in a solvent such as water, acidified water, or aqueous alcohol solution.

7 Claims, No Drawings 1. HAIR TREATING COSMETIC COMPOSITIONS CONTAINING PIPERAZINE BAsEn-CATIoNIC POLYMER-- The present invention relates to compositions fo r treatingand conditioning the hair. More particularly, the prese n t invention i'elates to cosmetic compositions for the hair, containing a low m'olecu lar weight, filmforming cationic polymer. l i A Many people's hair because of itsgerieral state orlits sensitivity due tov relatively frequent periodic treatments such asbleaching, dyeingor permanent waving, often is difficultto comb out and to arrange e specially in the case of abundanthair. To varying degrees, such hair often is also dry, dull and rough or lacks vigor and life-Further, such hair is very sensitive to,hurnidity in theair, which explains why hair-sets do not hold for an acceptable length OftimeDC nsequently, the frequency of such treatments, as described above has tobe increased, which, in turn increases the above-mentioned disadvantages. n, j c

The present invention now makesit possible to substantially limit or avoid these, disadyantagesby applying to the hair as a conditioner therefor-a low molecular weight, film-forming cationic polymer that imparts to the .hair an appearance of vigorand radiance.-

This polymer can be used alone-o'r as. the maincomponent in ahair-dressing lotion, cream, gel, hairsetting lotion hair-setting 'reinforcer, or alternatively, as an adjuvant in a composition for shampooing, setting, in permanent waving the hair, in a hair dyeing composition, in a cream for treating-dry or greasy hair, in an antidandruff lotion or in similarcompositi'ons forapplication to the hair.

The application of the hair conditioner cosmetic composition of this invention results in improving the facility and ease of combing out wet hair and imparts thereto brilliancy, softness and manageability of dry hair. Hair treated with the,composition of this invention feels lighten while at the "same 'time appears thickerand more alive. I

The conditioner according to the 'inven'tion, which acts as a softener and emollient, producesafter application of the same to the hair in. a shampoo, for example, a more brilliant, more voluminous and more aerated hair without the appearance of static electricity. Further, the cationic polymer of the present invention, provides the additional advantage of avoiding a powdering phenomenon which is frequently observed with numerous conventionally employed polymers. Moreover, the inclusion of the hair conditioner of thepres- Zen't invention in cosmetic compositions for the hair,

which comositions also include other components or hair treating agents, does not entail any appreciable -re- 'duction of the properties or effectiveness of theseother components.

The cationic polymer of the present invention is i characterized by the fact that the cationic groups are part of the main polymer chain and that they are essentially derivedfrorn. bisecondary heterocyclic amines, preferably, piperazine. Structu rally', the 'low molecular weight, filmforming, cationic polymer of the present invention can be represented by the pattern 2 wherein A represents a radicalderived from a heterocycle containing two secondary amine functions and, preferably, the radical and. Z. -r.eprefsents the,symbol P orB' ,;each of whicl'rindependently represents a bivalentfradical selected from thegroup consistingof (i) hydroxypropylene, (.ii),alkylene having up to 5 carbon atoms inclusive and interrupted by l 2 members selected from the group consisting of -CONl-l and I 4 I -con' NCO and (iii) hydroxy alkyl ene wherein the alkylene moiety has up to 6 carbon atoms inclusive and is interrupted by "a member selected'from the group consisting of 'alkyla- 'rn'i ne wherein the alkyl moiety has 12m 16 carbon atoms, benzylamin'e,' ole'ylam'ine" and oxygen.

Often, polymers of the present invention-are those in which A has the meaning given above and B and B each independently represent a branched or straight chain radical selected from the group consisting of hydroxyalkyl 'ene having and, preferably, 3 carbon atoms, lower" alkyl-carbonamide lower alkyl-carbonamide-lower alkyl having 5 to 8 'and, preferably 6 m7 carbon atoms, hydroxypropyl-Oxyhydroxypropyl,"hydroxypropyl-alkylaminohydroxypropyl wherein the alkyl moiety has 12 to 16 carbon atoms, hydroxypropyl-alkenylamino-hydroxypropyl wherein the alk enyl moiety has 18 carbon atoms,hydroxypropylpiperazinylhydroxypropyl, propiOnyl-piperazinyl-propionyl and hydroxypropyl-benzylamino-hydroxypropyl.

The polymers of the present invention are more generally strictly alternated, -i.e. of the type wherein A and B have the meanings give n aboveQj These rigorously'alternated polymers, which can be used in the present invention, can be prepared byconventional processes such as by polyaddition or polycon- .densation of (a) piperazine or a derivative thereof such as, for example, N,Nbis(hydroxyethyl)piperazine,,on (b) abifunctional compound such as c I 1.; alkyl or'alkyl-aryl dihalides, such as ethylene chlo- -ride ethylene bromide or his chloromethyl, 1,4-benzene wherein the alkyl moiety has 1-4 carbon atoms, the aryl moiety is phenyl and the halide moiety is chloride or bromide;

2. more complex'dihalogen derivatives, such as bis (chloroacetyl) ethylene diamine;

3. bis halohydrins, such as,bis 3-chloro 2-hydroxy propylether, or otherbis chlorohydrins which can be obtained by'conventional procedures such as by the condensation of epichlorohydrin. on (i) a primary amine, optionally hydroxylated, (ii) on a bisecondary diamine such as'piperazine, 4,4'- dipiperidyl, bis 4,4 (N-methylaminophenyl) methane, N,N 'dimethylethy- 'lene; diamine Orpropylene diamine, (iii) on. a,w-dimercaptoalkane, (iv) on a diol such as ethylene glycol or (v) Ona bis phenol such as hydroquinone or his .phenOlA;' v 1' 4. bis epoxide such as diglycidyl ether or N,Nbis (epoxy-2,3 propyl)piperazine, eventually obtained from the corresponding bis halohydrin;

5. epihalohydrins, such as epichlorohydrin or epibromohydrin;

bisecondary bis unsaturated derivatives, such as divinyl sulfone, bis maleimide derived from ethylene diamine, or bis acrylamide such as methylene bis acrylamide or piperazine bis acrylamide derived from 'biprimary or bissecondary diamines;

, 7. unsaturated acids, such as acrylic or methacrylic acid or their methyl or ethyl esters;

- 8. diacids, such as succinic, adipic, 2,2,4-trimethyl or 2,4,4-trimethyl adipic or terephthalic acids, acid chlorides or the corresponding methyl or ethyl esters; and 9. diisocyanates, such as toluene diisocyanate or 2,2,4- or 2,4,4-trimethyl hexamethylene isocyanate.

The polyaddition or polycondensation reaction can be carried out at ambient pressure and at a temperature ranging fromabout to 100C, the molar ratio of (a) to (b), defined above being 0.85 l to 1.15 1.

1 Of course, the polymers of the present invention can in certain cases advantageously be prepared in essentially the same way by polycondensation or polyaddition of (a N,Nbis(3-chloro 2-hydroxy propyl) piperazine or N,N'bis (2,3-epoxy propyl) piperazine on (b') a bifunctional compound such as a bisecondary diamine, a dimercaptan, a diol, a diphenol, a diacid, and

a primary amine such as an alkylamine, alkenylamine,

aralkylamine, of which the two hydrogen atoms can be substituted and which behaves as a bifunctional compound,'the molar ratio of (a') to(b') ranging from 0.85

Further, the cationic polymers of the present inventi'oncan also, in certain cases, be of the pattern iLe. be made up of polymer chains in which A, representing a bisecondary heterocyclic amine group, for example, the piperazine group, is distributed regularly, the two B and B groups designated by Z in formula (I) beingdistributed statistically. This type of polymer is 1 obtained'when piperazine or one of its derivatives is condensed with a mixture of two bifunctional derivatives.

The polycondensates of type I, II or [II can then, in

accordance with conventional procedures, be oxidized propylene oxide, epichlorohydrin or glycidol.

In those polymers of this invention wherein Z or B and B groups do not comprise base nitrogen or thioether, only the A groups will be modified statistically or almost totally by quaternization or oxidation. Other- I wise, any group can be modified.

The oxidation reaction of the polycondensate of type i I, [1 or [II can be performed with the amount of oxidizing agent being present in amounts from 0 to 100 percent relative to the oxidizable groups, while the quaternization reaction of the polycondensate of type I, II or .111 can be performed with the amount of quaternization 7 agent being present in amounts of 0 to 50 percent.

The cationic polymers of the present invention are also characterized by the fact that they are all filmforming and are generally of relatively low molecular weight, i.e. less than 15,000 and generally about LOCO-15,000. They are water soluble in acid medium and a number of them are also soluble as such in water without addition of acid or in dilute alcohol medium such as ethanol or isopropanol. The alcohol, i.e. lower alkanol, can be present in amounts of about 0 to 50 percent by weight of said composition. Generally, when an aqueous acidic medium is employed as the solvent for the polymers of the present invention, the acid employed can be hydrochloric, acetic, lactic, or tartaric acid in amounts sufficient to solubilize the said poly mer. Generally, the acid will be present in amounts of about 0 to 5 percent by weight of the composition. These polymers are particularly effective for hair which has become sensitives as a result of such treatments as bleaching, permanent waving, or dyeing. They can, however, also advantageously be used for normal hair.

Thus, an object of the present invention is the provision of a cosmetic composition for conditioning the hair comprising a solution in a solvent selected from the group consisting of water and an aqueous solution of a lower alkanol, of a member selected from the group consisting of (l) a low molecular weight, film-forming cationic polymer of the formula in which A represents a radical derived from a heterocycle carrying two secondary amine functions and preferably the radical and Z represents the symbol B or B; B and B each independently representing a bivalent radical selected from the group consisting of (i) hydroxypropylene, (ii) alkylene having up to 5 carbon atoms inclusive and interrupted by l-2member selected from the group consisting of CONH and CON. NCO

and (iii) hydroxy alkylene wherein the alkylene moiety has up to 6 carbon atoms inclusive and interrupted by a member selected from the group consisting of alkylamine wherein the alkyl moiety has 12-16 carbon atoms, benzylamine, oleylamine and oxygen, or (2) quaternary ammonium salt of the cationic polymer in (l) or (3) the oxidation product of the cationic polymer in (1).

Many of the polymers of formula (1) are new compounds.

Among the preferred polymers are those in which A and B and B, each independently represent a branched or straight chain radical selected from the group consisting of hydroxyackylene having l-6 carbon atoms, preferably 3 carbon atoms, lower alkyl-carbonamidelower alkyl-carbonamide-lower alkyl having 5-8 and preferably 6-7 carbon atoms, hydroxypropyl-oxyhydroxypropyl, hydroxypropyl-alkylamino-hydroxypropyl wherein the alkyl moiety has 12-16 carbon atoms, hydroxypropyl-alkenylamino-hydroxypropyl wherein the alkenyl moiety has 18 carbon atoms, hydroxypropyl-piperizinyl-hydroxypropyl, propionylpiperizinylpropionyl and hydroxypropyl-benzylamino-hydroxypropyl.

The polymer can be present in amounts of about 0.1 to 5 percent and preferably 0.2 to 3 percent by weight in the various cosmetic compositions of the present invention. These compositions include hair-dressing lotions, creams or gels as the main constituent, shampoos, hair-setting compositions, permanent wave composition or hair dye compositions, etc. The polymers can also be employed as an adjuvant in the presence of other components such as anionic, cationic, non-ionic, amphoteric or zwitterionic surfactants, oxidizing agents, foam stabilizers or synergists, sequestrants, superfatting agents, thickeners, softeners, antiseptics, preservatives, dyes, perfumes, germicides or other anionic, cationic, amphoteric or non-ionic polymers.

The polymers can be used in different compositions whose pI-l varies from 3 to 11, or in the form of inorganic or organic acid salts, or in the form of free base or, alternatively, the quaternary ammonium salt thereof.

The cosmetic compositions for hair according to the present invention can be in the form of an aqueous solution, a dilute alcohol solution, a cream, a paste, a gel, or a powder. They can also contain a conventional aerosol propellant such as dichlorodifluoromethane, monochlorotrifluoromethane, mixtures thereof or other conventional aerosol propellants, and can be packaged in a conventional aerosol bomb under pressure.

The hair shampoo compositions according to the invention are characterized by the fact that they contain, in addition to an anionic, cationic, non-ionic, amphoteric and/or switterionic surfactant, one or more compounds of formula I and optionally foam stabilizers or synergists, sequestrants, superfatting agents, thickeners, one or more other cosmetic resins, softeners, dyes, perfumes, antiseptics, preservatives and any other adjuvant usually used in cosmetic compositions.

The polymers of formula I also make it possible to prepare hair-setting lotions, hair-setting reinforcers,

'treatment creams, hair conditioners, anti-dandruff lotions and other similar compositions characterized by the fact that they contain one or more polymers of formula I having a molecular weight, determined by lowering of the vapor tension, between 1,000 and 15,000, or the quaternary ammonium salt or amine oxide of these polymers, possibly mixed with other cosmetic resins.

EXAMPLES OF PREPARATION OF THE POLYMER Example 1 Polycondensation of piperazine and epichlorohydrin. To a solution of 97 g (0.5 mole) of piperazine hexahydrate in 125 g of water, there are added, drop by 6 drop, over a period of l hour, 46.3 g (0.5 mole) of epichlorohydrin, with stirring, while maintaining the temperature at 20C. Stirring is continued for 1 hour at 20C. The reaction mass is then heated at 95C for 2 hours. Over a period of one hour, 0.5 mole of sodium hydroxide is then added in the form of a 40 percent (50 g) NaOH solution. A cloud then appears in the solution. The temperature is maintained at the 9095C level for 15 minutes more, and the reaction mixture is then cooled with stirring while adding 182 g of water to bring the concentration to 20 percent of dry extract (14.5 percent active material and a 5.5 percent NaCl).

A limpid and almost colorless solution is thus obtained, having a viscosity of 2.5 poises, measured at 25C.

On evaporation of a dilute solution of the polymer thus prepared, there is obtained a wrinkled film, opaque because of the presence of the sodium chloride, but hard and not sticky.

Example 2 Polycondensation of N,N'bis-(2,3-epoxy propyl) piperazine and piperazine.

A polymer similar to that of Example 1, but free of sodium chloride, is prepared by olycondensation of piperazine and N,N' bis(2,3-epoxy propyl) piperazine in an aqueous medium and in stoichiometric proportions. The N,Nbis-(2,3-epoxy propyl) piperazine can be prepared in the following way:

To 86 g (1 mole) of anhydrous piperazine, dissolved in 540 g of isopropanol, there are added, over a 30 minute period at a temperature of l0l5C, 185 g of epichlorohydrin (2 moles). This temperature is maintained at this level while the reaction mixture is stirred for 7 hours.

The resulting dichlorohydrin, derived from piperazine, is filtered and dried. It is a white crystallized product having a melting point of l08l 10C.

50.7 g (0.18 mole) of the dichlorohydrin thus obtained are dispersed in ml of benzene. The suspension is cooled to 10C. There are then added by fractions, over a 30 minute period, 15.5 g (0.37 mole) of ground sodium hydroxide. This temperature is maintained for 2 1% hours. The sodium chloride precipitate is filtered and rinsed with three times 100 ml of benzene.

After elimination of the benzene, under partial vacuum, there are collected 26 g of white solid corresponding, according to functional analyses, to N,N'bis- (2,3-epoxy propyl) piperazine.

25 g (0.125 mole) of product thus prepared are heated with reflux with 10.8 g (0.125 mole) of anhydrous piperazine in 60 g of isopropanol for 3 9% hours. The cationic polymer is then partially precipitated. The solvent is eliminated under partial vacuum and an almost white powder is thus obtained which is soluble in water and which exhibits a melting point of 190C. The molecular weight of this polymer, measured in chloroform by the method of lowering the vapor tension, is 2460.

Example 3 Quaternization of the piperazine and 'epichlorohydrin polycondensate.

To 200 g of solution obtained according to Example 1 which contains 0.4 equivalent of base nitrogen, there are added g of absolute ethyl alcohol and then 25 .3 g (0.2 mole) of benzyl chloride. The reaction mixture is heated at 80C for 1% hours. The ethanol is then elimi- '7 nated under partial vacuum, while re-adding water, to obtain a 10 percent solution of dry extract.

Example 4 mole) of 200 volume hydrogen peroxide. The tempera- 1O ture is maintained at this level for hours.

The polymer solution obtained is perfectly limpid and yields, on evaporation, films comparable to those of Example 1.

Example 5 Polycondensation of piperazine, benzylamine and epichlorohydrin.

To a solution of 97 g (0.5 mole) of hexahydrated piperazine, in 384 g of isopropyl alcohol, there are added, drop by drop at C, 92.5 g (1 mole) of epichlorohydrin. The resulting solution is maintained, with stirring, at 15C for 2 hours. Thereafter it is heated to 70C, and over a 15 minute period, 54 g (0.5 mole) of benzylamine are added. The resulting mixture is heated with reflux for an hour. There are then added, drop by drop, 160 g of methanol solution of sodium methylate (0.98 mole). Heating is continued for 1 hour.

After cooling, the formed sodium chloride is filtered and the isopropanol is eliminated under partial vacuum. After drying under vacuum and in the presence of phosphoric anhydride, a hard, brittle, colorless solid is obtained, having a softening point of 65C and a molecular weight, measured in absolute ethanol of 1600.

The compound thus obtained is soluble in water in an acid medium and in a dilute alcohol medium. It yields beautiful, hard and very brilliant films, after evaporation of its dilute alcohol solvent.

Example 6 Polycondensation of N,N-bis(2,3-epoxy propyl) piperazine and cetylamine.

'24 g (0.1 mole) of cetylamine and g (0.1 mole) of N,N'-bis(2,3-epoxy propyl) piperazine prepared according to Example 2, are heated with reflux in 45 g of isopropanol for 15 hours. The resin obtained is soluble in water in an acid medium, such as hydrochloric acid.

Example 7 Quaternization of the product obtained in Example To 68 g of the above isopropanol solution (0.23 equivalent in base nitrogen) there are added, drop by drop at 30C, 14.6 (0.11 mole) of dimethyl sulfate. Stirring is continued for 2 hours. The solvent is then eliminated under partial vacuum, with water being added to produce a final aqueous solution that is 10 percent by weight.

The film obtained by evaporation of the dilute solution is rather hard and not sticky.

Example 8 Polycondensation of N,N'bis(2,3-epoxy propyl) piperazine and dodecylamine.

18.5 g (0.1 mole) of dodecylamine and 20 g (0.1 mole) of N,N'bis(2,3-epoxy propyl)piperazine, prepared according to Example 2, are dissolved in 90 g of isopropyl alcohol. After 10 hours of heating at reflux,

the solvent is eliminated under partial vacuum. There is thus obtained a soft, colorless, transparent resin, soluble in water in the presence of hydrochloric acid and also in alcohol such as ethanol or isopropanol.

The molecular weight of this resin, measured in absolute ethanol, is 2900.

By evaporation of dilute solutions, soft, slightly sticky films are obtained.

Example 9 Quaternization of the N,N'-bis(2,3-epoxy propyl) piperazine and dodecylamine polycondensate.

To 30 g of resin obtained according to Example 7 (0.21 equivalent in base nitrogen), dissolved in 40 g of isopropanol, there are added, drop by drop at 30C, 13.5 g (0.1 mole) of dimethyl sulfate. Stirring is kept up for 2 hours at the same temperature. Then the solvent is eliminated under partial vacuum, with water being added to obtain the resin in the form ofa 10 weight percent solution in water.

On evaporation of the dilute aqueous solutions, films are obtained which are always soft but which are no longer sticky.

Example 10 Polycondensation of piperazine and N,N-bis(- chloroacetyl)ethylene diamine.

To a solution of 10.6 g (0.05 mole) of N,N'-bis chloroacetyl ethylene diamine in 125 g of water, there are added 9.7 g (0.05 mole) of hexahydrated piperazine. The mixture is heated for 3 hours at C. While the heating is continued, the acid formed is neutralized by addition, in several fractions, of 0.1 mole of sodium hydroxide in the form of a 40 percent (10 g) NaOI-l solution.

A colloidal solution having good film-forming properties is thus obtained.

Example 1 1 Polycondensation of N,N-bis(2,3-epoxy propyl) piperazine, oleyamine and piperazine.

To a solution of 20 g (0.1 mole) of N,N-bis(2,3- epoxy propyl) piperazine in 47 g of isopropanol, there are added 10.7 g (0.04 mole) of oleylamine and 5.16 g (0.06 mole) of anhydrous piperazine. After 4 hours of heating at reflux, the solvent is eliminated under reduced pressure. There is then obtained a white solid having a softening point of around 100C, the product being insoluble in neutral water, but soluble in ethanol and in water in an acid medium such as HCl.

Films obtained by evaporation of the dilute solution are transparent, not sticky and slightly hard.

Example 12 Polycondensation of piperazine and diglycidyl ether.

To 6.63 g (0.077 mole) of anhydrous piperazine in 11 g of isopropanol there are added over a 15 minute period at 30C, 10 g (0.077 mole) of diglycidyl ether. The mixture is heated at reflux for 4% hours. Then the solvent is eliminated, at reduced pressure, while water is added to obtain a colloidal solution of 5 weight percent active material, i.e. polymer.

Films obtained by evaporation of the dilute solution are opalescent, hard and not sticky.

The diglycidyl ether is prepared by reacting at 1520C a stoichiometric amount of sodium hydroxide on bis(3-chloro 2-hydroxy propyl) ether. The diglycidyl ether is isolated by distillation under reduced pres- 9 sure. The boiling point is 8085C/0.05 mm Hg,

Example 13 Polycondensation of piperazine and methylene bisacrylamide.

To 15.4 g (0.1 mole) of methylene bisacrylamide provided in paste form with 18.6 g of water, there are By evaporating the dilute aqueous solution, there is obtained very hard transparent and non-sticky films.

Example 14 Polycondensation of piperazine and piperazine bisacrylamide.

To a solution of 19.4 g (0.l mole) of piperazine bi- To 688 g (8 moles) of anhydrous piperazine dissolved in 1500 g of isopropanol, there are added 92.5 g (1 mole) of epichlorohydrin over a period of 1 hour at a temperature of C. The resulting reaction mixture is then heated for a period of 1.5 hours at 80C throughout said period. There are then added over a period of one-half hour 250 g of sodium methylate. The reaction mixture is then cooled and filtered to remove sodium chloride formed during the reaction. The remaining reaction mixture is then concentrated under a partial vacuum thereby eliminating the greatest part of the excess piperazine. The desired compound is isolated bydistillation. It is awhite solid having a melting point of 78C and a boiling point of 147l52C/0.07 mm Hg. Method 2 To a solution of 116.4 g (0.6 mole) of piperazine hexahydrate in 353 g of water, there are added in small sacrylamide in 35 g of water, there are added with agi- Example 15 Polycondensation of 1,3-bis piperazine-Z-propanol and methylene bisacrylamide. Method 1 To 15.4 g (0.1 mole) of. methylene bisacrylamide provided in paste form with-23.1 g of water there are added with agitation at a temperature between 0 and 5C under a nitrogen atmosphere, 152.5 g of a standardized aqueous solution containing 22.8 g (0.1 mole) of 1,3-bis piperazine-2-propanol. The mixture is left standing for 30 hours at C.

The polymer is precipitated in accordance with the procedure outlined in Example 14.

There is thus obtained a white solid exhibiting a softening point of 176C and a melting point of 200-2l0C.

By evaporating the dilute aqueous solution, there is obtained very hard, transparent and non-sticky films.

The l,3-bis-piperazine-2-propanol, utilized above, can be prepared as follows:

Structural Pattern Example No.

portions a total of 46 .2 g (0.3 mole) of solid methylene bisacrylamide, with agitation at a temperature between 0 to 5C and under a nitrogen atmosphere. The resulting reaction mixture is left to stand for 24 hours at 25C. There are then added, little by little, 27.75 g (0.3 mole) of epichlorohydrin over a period of 1 hour while maintaining the temperature of the reaction mixture at 20C.

The reaction mixture is stirred again for a period of 1 hour at a temperature of 20C. Then there are added at this temperature over a 1 hour period, 30 g (0.3 mole) of a 40 percent NaOH solution.

After an additional 1 hour period of stirring the reaction mixture at 20C, the reaction mixture is heated for 1 hour at C. There is thus obtained a 20 percent solution of the polymer exhibiting a very light opalescence and being nearly'colorless. By evaporating the dilute aqueous solution there is obtained a very hard, transparent and non-sticky film.

Example 16 Polycondensation of 1,3-bis piperazine-2-propanol and piperazine bisacrylamide.

To a solution of. 19.4 g (0.1 mole) of piperazine bisacrylamide in 39.1 g of water there are added with stirring at a temperature between 0 to 5C and under a nitrogen atmosphere 152.5 g of a standardized aqueous solution containing 22.8 g (0.1 mole) of 1,3-bis piperazine 2-propanol. The resulting reaction mixture is left to stand for 30 hours at 25C. The polymer is precipitated from the reaction mixture in accordance with the procedure outlined in Example 14 thereby yielding a white solid having a melting point of about 205210C. By evaporating the dilute aqueous solution there is obtained a hard, transparent and nonsticky film.

The following Table summarizes the reactions of Examples 1-16.

TAB"

- A B J- A B' A B A B Reaction Formula of RepeatingUnits l 1 1 Condensation of v 1 N N- CH CH.-CH piperazine and epil I chlor'ohydrin OH Citric acid, q.s.p. pH 6 Water, q.s.p.

-continued 15 Condensation of 1,3-

bis-piperazine-2- propanol and methylene bisacrylamide I y I I I N N' CH -CHOH-CH N ir cH -cri -corm-cfl -NHco-c1i,,--cH

k L- I 1 i J I I I l l A B i B 16 Condensation of 1,3-

bis-piperazine-E- propanol and piperazine bisacrylamide I I I I II I 1 N N CH CHOH-CH N N CH -CH CN NC-CH -CH l l I I l 4 I I I I EXAMPLES OF APPLICATION Example l7 Setting lotion for very dry hair Compound prepared according to Example 1 l g Propyl para-hydroxybenzoate 0.4 g Neolane pink dye, C.l. 18810 0.005 g Perfume 0.2 g Water, q.s.p. 100 g Example 18 Setting reinforcer for damaged hair Compound prepared according to Example l l g Polyvinyl pyrrolidone/vinyl acetate 60/40 copolymer (m.W. 50,000 to 70,000) 05 g Trimethyl cetyl ammonium bromide 0.2 g Perfume 0.1 g Methyl para-hydroxybenzoate 0.l g Water, q.s.p. 100 g Example 19 Setting reinforcer for normal hair Compound prepared according to Example 1 l g Vinyl acetate/crotonic acid copolymer (M.W. 20.000) 1 8 Trimethyl cetyl ammonium bromide 0.1 g Methyl violet dye, CI. 42535 0.002 g Perfume 0.1 g Ethyl alcohol, q.s.p. 50 Water, q.s.p. 100 g Example 20 Anionic shampoo R(OCH,CH,),OSO;Na wherein R alkyl C -C in proportions of 70/30 10 g Diethanolamide of copra fatty acids 3 g Water, q.s.p. I00 g pH 7 Example 21 Anionic shampoo Compound prepared according to Example 1 0.75 g Triethanolamine alkyl sulfate wherein alkyl C /C 70/30 15 g Monoethanolamide of copra fatty acid 4 g Sodium N-lauryl sarcosinate 3 g Acetylated lanolin 3 g Water, q.slp. 100 g pH 7.5 Example 22 Non-ionic shampoo Compound prepared according to Example I 2.5 g

R- OCH,iH OH wherein R alkyl C I-[, 15 g H OH Alkoxylated anhydrous lanolin sold under the trademark Lantrol AWS" by Malstrom Chemical Corporation, New Jersey 1.5 Hydroxypropyl methyl cellulose 0.3

-continued EXAMPLES OF APPLICATION Example 17 Setting lotion for very dry hair Compound prepared according to Example I Example 23 Cationic shampoo Compound prepared according to Example 8 Bromide of dodecyl, tetradecyl and hexadecyl trimethylammonium sold under the tradename Cetavlon" Lauryl alcohol oxyethylenated with 12 moles of ethylene oxide Lauryl diethanolamide Ethyl cellulose Lactic acid, q.s.p. pH 4 Water, q.s.p.

Example 24 Amphoteric shampoo Compound prepared according to Example I CH sold under the name Miranol "CZM" by Miranol Chemical Corporation, lrvington. New Jersey Dimethyl alkylamine oxide prepared from copra fatty acids Lauryl diethanolamide Lauryl alcohol, oxyethylenated with 12 moles of ethylene oxide Lactic acid, q.s.p. pH 6 Water, q.s.p. Example 25 Amphoteric shampoo Compound prepared according to Example l Sodium salt of N,N(diethylamino propyl)N'- dodecyl asparagin R OCH,il-l OH wherein R alkyl, C I-l H OH 4 Lactic acid, q.s.p. pH 5 Water, q.s.p. Example 26 Anionic shampoo Compound prepared according to Example 9 Sodium alkyl sulfate (alkyl C C Sodium N-lauryl sarcosinate Lauryl monoethanolamide Glycol distearate Water, q.s.p. pH 7 Example 27 Anionic shampoo Compound prepared according to Example 9 RO(CHCH2)2OSO3N3 wherein R C ll Sodium salt of N,N(diethylamino propyl)-N- dodecyl asparagin Diethylanolamide of copra fatty acids Hydroxypropyl cellulose Water, q.s.p. pH 6.5 Example 28 Cream for treating dry hair Compound prepared according to Example 1, q.s.p. Cetyl alcohol Stearyl alcohol Cetyl-stearyl alcohol oxyethylenated with 15 moles of ethylene oxide Hydroxyethylcellulose Perfume Water, q.s.p.

Application of this cream is followed by rinsing of the hair. Example 29 Conditioner for dry hair Compound prepared according to Example I, q.s.p. Polyvinylpyrrolidone/vinyl acetate copolymer 70/30 (M.W. 40,000) Perfume Water, q.s.p.

This conditioner is to be used after shampooing and before setting, without intermediate rinsing. Example 30 Anti-dandruff lotion for daily use -continued EXAMPLES OF APPLICATION Example 17 Setting lotion for very dry hair Anionic shampoo in the form of a clear solution Ammonium alkylsulfate (alkyl derived from copra) Sodium alkyl ether sulfate'iavherein the alkyl moiety is derived from copra fatty acids and oxyethylenated with 2 moles of ethylene oxide i Compound prepared according -to Example 4' Lauryl diethanolamide Mixture of monoand di-gly'cerides of fatty acids, sold under the tradename "ARLACEL 186" by Atlas Lactic acid, q.s.p. pH 7.5

Water, q.s.p.

Example 32 Anionic shampoo Sodium alkyl ether sulfate wherein the alkyl moiety is derived from copra fatty acids and oxyethylenated with 2 moles of ethylene oxide Copra diethanolamide Compound prepared according to Example 13 Sodium monolauryl sulfosuccinate Lactic acid, q.s.p. pH 7.5

Water, q.s.p.

ts -q mourn Hair treated with the above composition is easy to comb, exhibits good volume, is shiny and lively.

Example 33 Anionic shampoo The composition of Example 32 is repeated except that the compound prepared according to Example 13 is replaced with an essentially equivalent amount of the compound prepared according to Example 14. Essentially similar effective and advantageous results are achieved with this composition.

This solution imparts to hair a lively and shiny appearance.

Further in Examples 17-22, 24, and 28-30, the compound prepared in accordance with Example 1 is replaced with the compound prepared in accordance with Example 15 and 16 in essentially equivalent amounts to provide equally effective hair treating compositions.

In all of the Examples of Application given above, the weight of the polymer is expressed as the active material therein.

What is claimed is:

1. Cosmetic composition for conditioning the hair comprising a solution in a solvent selected from the group consisting of water and water-lower alkanol, of a member selected from the group consisting of l. a film-forming cationic polymer having a molecular weight of about 1,000 to 15,000 and having the formula wherein A represents and Z represents B andIB' wherein B and B each independently represent a bivalent radical selected from the group consisting of (i) hydroxypropylene, (ii) alkylene having up to 5 carbon atoms inclusive and interrupted by l-2 members selected from the group consisting of -CONH and (iii) hydroxy alkylene wherein the alkylene moiety has up to 6 carbon atoms inclusive and interrupted by a member selected from the group consisting of alkylamine wherein the alkyl moiety has 12-16 carbon atoms, benzylamine, oleylamine and oxygen, and (iv) hydroxy propyl-piperazinyl-hydroxypropyl,

2. quaternary ammonium salt of the cationic polymer in l) and 3. the oxidation product of the cationic polymer in said member being present in an amount of about 0.1 to 5 percent by weight of said composition. 2. The composition according to claim 1, characterized by the fact that it is in the form of a cream.

wherein A represents and Z represents B and B wherein B and B each independently represent a bivalent radical selected from the group consisting of (i) hydroxypropylene, (ii) alkylene having up to carbon atoms inclusive and interrupted by 1-2 members selected from the group consisting of -CONH and -CON NCO- (iii) hydroxy alkylene wherein the alkylene moiety has up to 6 carbon atoms inclusive and interrupted by a member selected from the group consisting of alkylamine wherein the alkyl moiety has 12-16 carbon atoms, benzylamine, oleylamine and oxygen and (iv) hydroxy propyl-piperazinyl-hydroxypropyl,

2. quaternary ammonium salt of the cationic polymer in (l) and v 3. the oxidation product of the cationic polymer in said member being present in an amount of about 0.1 to 5 percent by weight of said composition. 5. The composition of claim 4 which also includes an anionic, cationic, non-ionic or amphoteric surfactant.

6. The composition according toclaim 4 having a pH between 3 and 11.

7. The composition according to claim 4 wherein said cationic polymer has a molecular weight less than 15,000. i

Claims (14)

1. COSMETIC COMPOSITION FOR CONDITIONING THE HAIR COMPRISING SOLUTION IN A SOLVENT SELECTED FROM THE GROUP CONSISTING OF WATER AND WATER-LOWER ALKANOL, OF A MEMBER SELECTED FROM THE GROUP CONSISTING OF
1. A FILM-FORMING CATIONIC POLYMER HAVING A MOLECULAR WEIGHT OF ABOUT 1,000 TO 15,000 AND HAVING THE FORMULA
2. QUATERNARY AMMONIUM SALT OF THE CATIONIC POLYMER IN (1) AND
2. quaternary ammonium salt of the cationic polymer in (1) and
2. The composition according to claim 1, characterized by the fact that it is in the form of a cream.
2. quaternary ammonium salt of the cationic polymer in (1) and
3. the oxidation product of the cationic polymer in (1), said member being present in an amount of about 0.1 to 5 percent by weight of said composition.
3. A method of conditioning the hair comprising applying to said hair an effective amount of the composition of claim 1.
3. the oxidation product of the cationic polymer in (1), said member being present in an amount of about 0.1 to 5 percent by weight of said composition.
3. THE OXIDATION PRODUCT OF THE CATIONIC POLYMER IN (I). SAID MEMBER BEING PRESENT IN AN AMOUNT OF ABOUT 0.1 TO 5 PERCENT BY WEIGHT OF SAID COMPOSITION.
4. A cosmetic composition for conditioning the hair comprising a solution in water-ethanol of a member selected from the group consisting of
5. The composition of claim 4 which also includes an anionic, cationic, non-ionic or amphoteric surfactant.
6. The composition according to claim 4 having a pH between 3 and 11.
7. The composition according to claim 4 wherein said cationic polymer has a molecular weight less than 15,000.
US05310088 1971-11-29 1972-11-28 Hair treating cosmetic compositions containing piperazine based cationic polymer Expired - Lifetime US3917817A (en)

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Cited By (158)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4018721A (en) * 1974-03-07 1977-04-19 Union Carbide Corporation Cross-linked, water insoluble poly(N-glycidyl-piperazine)
US4061602A (en) * 1976-08-03 1977-12-06 American Cyanamid Company Conditioning shampoo composition containing a cationic derivative of a natural gum (such as guar) as the active conditioning ingredient
US4080310A (en) * 1975-06-12 1978-03-21 Beecham Group Limited Amphoteric conditioning shampoo
US4101456A (en) * 1975-04-18 1978-07-18 Colgate-Palmolive Company Light duty liquid detergent
US4201766A (en) * 1977-03-02 1980-05-06 L'oreal Hair conditioning composition and method of using the same
US4240450A (en) * 1977-03-15 1980-12-23 L'oreal Composition and process for the treatment of keratin materials with polymers
US4271053A (en) * 1979-06-29 1981-06-02 Union Carbide Corporation Quaternary ammonium graft copolymers for use as flocculants and method of preparing same
US4305829A (en) * 1979-06-29 1981-12-15 Union Carbide Corporation Process for flocculating an aqueous suspension of particles with quaternary ammonium graft copolymers
US4314807A (en) * 1975-11-13 1982-02-09 L'oreal Hair dye composition containing a hair dye formulation packaged in two parts
US4349532A (en) * 1977-09-20 1982-09-14 Guy Vanlerberghe Cosmetic compositions based on poly-(quaternary ammonium) polymers
US4465802A (en) * 1982-10-26 1984-08-14 Union Carbide Corporation Process for treating furred animal pelts and/or fur
US4470982A (en) * 1980-12-22 1984-09-11 The Procter & Gamble Company Shampoo compositions
US4488879A (en) * 1982-07-10 1984-12-18 Basf Aktiengesellschaft Process for dyeing textile materials of polyacrylonitrile: quaternized piperazine copolymer as basic dye retarder
US4647379A (en) * 1985-11-13 1987-03-03 The Dow Chemical Company Nitrogen-containing water-soluble polymer flocculants
US4656245A (en) * 1985-03-08 1987-04-07 Sumitomo Electric Industries, Ltd. Functional elastomer
EP0168719A3 (en) * 1984-07-20 1987-05-20 Revlon, Inc. Low ph hair conditioner compositions containing amine oxides
US4761273A (en) * 1981-05-08 1988-08-02 L'oreal Composition in the form of an aerosol foam, based on a cationic polymer and an anionic polymer
US4806345A (en) * 1985-11-21 1989-02-21 Nalco Chemical Company Cross-linked cationic polymers for use in personal care products
US4851532A (en) * 1985-05-20 1989-07-25 Buckman Laboratories, Inc. Ionene polymeric compositions, their preparation and use
US4867966A (en) * 1986-09-19 1989-09-19 L'oreal Cosmetic compositions based on cationic polymers and alkyloxazoline polymers
US5130056A (en) * 1989-01-27 1992-07-14 Deutsche Solvay-Werke Gmbh Cleaning agent and process for its preparation
US5236996A (en) * 1991-07-24 1993-08-17 Union Camp Corporation Stable polyamide resin dispersions containing piperasine and methods for the manufacture thereof
WO1999014300A1 (en) * 1997-09-15 1999-03-25 The Procter & Gamble Company Laundry detergent compositions with cyclic amine based polymers to provide appearance and integrity benefits to fabrics laundered therewith
US6228828B1 (en) 1997-09-15 2001-05-08 The Procter & Gamble Company Laundry detergent compositions with anionically modified, cyclic amine based polymers
WO2001032816A1 (en) * 1999-10-29 2001-05-10 The Procter & Gamble Company Laundry detergent compositions with fabric care
US6251846B1 (en) * 1997-09-15 2001-06-26 The Procter & Gamble Company Laundry detergent compositions with cyclic amine based polymers to provide appearance and integrity benefits to fabrics laundered therewith
US6260556B1 (en) 1999-01-29 2001-07-17 L'oreal Anhydrous composition for bleaching keratin fibers
US6262011B1 (en) * 1996-10-21 2001-07-17 Basf Aktiengesellschaft Polycationic condensates as color transfer inhibiting and color release reducing additive to detergents and fabric conditioners
US6379401B1 (en) 1999-01-29 2002-04-30 L'oreal, S.A. Anhydrous composition for bleaching keratin fibers comprising a combination of a water-soluble thickening polymer and a nonionic amphiphilic polymer comprising at least one fatty chain
US6436151B2 (en) 1999-12-30 2002-08-20 L'oreal S.A. Compositions for oxidation dyeing keratin fibers comprising at least one oxidation dye, at least one thickening polymer comprising at least one fatty chain, and at least one fatty alcohol comprising more than twenty carbon atoms and uses thereof
US6444197B2 (en) 1999-12-13 2002-09-03 L'oreal S.A. Bleaching composition for keratin fibers, comprising a combination of two polyurethane polyethers
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
US6472364B1 (en) 1998-10-13 2002-10-29 The Procter & Gamble Company Detergent compositions or components
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
US20030023782A1 (en) * 2001-07-26 2003-01-30 International Business Machines Corp. Microprocessor system bus protocol providing a fully pipelined input/output DMA write mechanism
US6534047B1 (en) 1999-06-30 2003-03-18 L'oreal S.A. Mascara containing film-forming polymers
US20030074747A1 (en) * 2001-07-27 2003-04-24 Patricia Vuarier 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
US20030103929A1 (en) * 2001-09-11 2003-06-05 Mireille Maubru Cosmetic compositions containing a methacrylic acid copolymer, a silicone and a cationic polymer, and uses thereof
US20030103926A1 (en) * 2001-09-11 2003-06-05 Mireille Maubru Cosmetic compositions containing a methacrylic acid copolymer, a dimethicone, a nacreous agent and a cationic polymer, and uses thereof
US20030108503A1 (en) * 2001-09-11 2003-06-12 Mireille Maubru Cosmetic compositions containing a methacrylic acid copolymer, a silicone and a cationic polymer, and uses thereof
US6589519B1 (en) 1997-08-25 2003-07-08 L'oreal S.A. Cosmetic compositions containing a polyoxyalkylenated aminosilicone block copolymer and a conditioner, and uses thereof
US20030140429A1 (en) * 2001-11-08 2003-07-31 Frederic Legrand Keratin fibre dyeing composition comprising a particular aminosilicone
US6602303B2 (en) 2000-08-11 2003-08-05 L'oreal S.A. Composition for the oxidation dyeing of keratinous fibers comprising at least one oxidation dye and at least one cationic amphiphilic polymer, and dyeing methods
US20030147818A1 (en) * 2001-11-15 2003-08-07 Claude Dubief Preparation of polysaccharide betainate type compounds, compounds obtained, their use and compositions comprising them
US20030147842A1 (en) * 2001-11-08 2003-08-07 Serge Restle Cosmetic compositions containing a particular aminosilicone and a conditioner, and uses thereof
US6635262B2 (en) 2000-03-14 2003-10-21 L'oreal S.A. Roll-on applicator comprising a hair composition
US20030223948A1 (en) * 2002-03-28 2003-12-04 Mireille Maubru Cosmetic composition comprising at least one anionic surfactant, at least one cationic polymer and at least one amphiphilic, branched block acrylic copolymer and method for treating hair using such a composition
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US20040025266A1 (en) * 2000-11-08 2004-02-12 Francois Cottard Oxidation dyeing composition for karatinous fibres comprising a cationic associative polyurethane
US6695887B2 (en) 1999-12-30 2004-02-24 L'oreal S.A. Compositions for oxidation dyeing keratin fibers comprising at least one fatty alcohol having more than twenty carbon atoms and at least one oxyalkylenated nonionic surfactant with an hlb greater than 5
US20040034946A1 (en) * 2000-11-08 2004-02-26 Frederic Legrand Composition for bleaching or permanent waving of keratinous fibers comprising a cationic associative polyurethane
US20040037796A1 (en) * 2000-11-20 2004-02-26 Francois Cottard Composition for treating keratinous materials comprising a cationic associative polyurethane polymer and a protecting or conditioning agent
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US20040034944A1 (en) * 2000-08-21 2004-02-26 Frederic Legrand Bleaching composition for dyed keratinous fibers
US20040039101A1 (en) * 2002-05-31 2004-02-26 Claude Dubief Washing compositions comprising at least one amphiphilic block copolymer and at least one cationic or amphoteric polymer
US20040049861A1 (en) * 2000-12-04 2004-03-18 Francois Cottard Oxidation dyeing composition for keratinous fibres comprising an associative polymer and a pearling agent
US20040060126A1 (en) * 2000-12-04 2004-04-01 Francois Cottard Dyeing composition for keratinous fibres comprising an associative polymer and a polymer with acrylamide units, dialkyldiallylammonium halide, and vinylic carboxylic acid
US20040077510A1 (en) * 2002-07-08 2004-04-22 Pascale Lazzeri Detergent cosmetic compositions comprising an anionic surfactant, an amphoteric, cationic, and/or nonionic surfactant, and a polysacchardie, and use thereof
US20040115156A1 (en) * 2001-01-26 2004-06-17 De La Mettrie Roland Cosmetic composition comprising a fixing polymer and a cationic poly(vinyllactam)
US20040122807A1 (en) * 2002-12-24 2004-06-24 Hamilton Darin E. Methods and systems for performing search interpretation
US20040133995A1 (en) * 2002-10-21 2004-07-15 Francois Cottard Oxidation dyeing composition for keratin fibers comprising a cationic poly(vinyllactam) and at least one C10-C14 fatty acid, methods and devices for oxidation dyeing
US20040133994A1 (en) * 2002-10-21 2004-07-15 Francois Cottard Oxidation dyeing composition for keratin fibers comprising a cationic poly(vinyllactam) and at least One C10-C14 fatty alcohol, methods and devices for oxidation dyeing
US20040163186A1 (en) * 2002-12-06 2004-08-26 Frederic Simonet 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
US20040180030A1 (en) * 2002-12-19 2004-09-16 Mireille Maubru Cosmetic compositions comprising at least one alkylamphohydroxyalkylsulphonate amphoteric surfactant and at least one nacreous agent and/or opacifier, and uses thereof
US6800098B1 (en) 1999-12-08 2004-10-05 L'oreal, S.A. Oxidation dye composition for keratinic fibres containing a thickening polymer with an ether plastic skeleton
US6800096B1 (en) 1999-12-08 2004-10-05 L'oreal S.A. Composition, process and kit for bleaching keratin fibers comprising at least one thickening polymer with an aminoplast-ether skeleton
US20040208843A1 (en) * 2002-09-24 2004-10-21 Gabin Vic Cosmetic composition comprising an exogenous ligand-receptor system adsorbed or covalently attached to keratin materials, and hair treatment using this composition or constituent elements thereof
US20040205902A1 (en) * 2002-12-06 2004-10-21 Francois Cottard Composition for the oxidation dyeing of keratin fibers, comprising at least one non-oxyalkenylated fatty alcohol, at least one oxidation dye, at least one associative polymer, and at least one amide of an alkanolamine and a C14-C30 fatty acid
US20040221401A1 (en) * 2003-03-25 2004-11-11 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
US20040226110A1 (en) * 2003-01-16 2004-11-18 Frederic Legrand Ready-to-use bleaching compositions, preparation process and bleaching process
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US20040237217A1 (en) * 2003-03-25 2004-12-02 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
US20050011017A1 (en) * 2003-03-25 2005-01-20 L'oreal S.A. Oxidizing composition comprising hydroxycarboxylic acids and salts thereof as complexing agents for dyeing, bleaching or permanently reshaping keratin fibres
US20050036970A1 (en) * 2003-03-25 2005-02-17 L'oreal S.A. Reducing compositions for bleaching or permanently reshaping keratin fibres comprising polycarboxylic acids and salts thereof as complexing agents
US20050039270A1 (en) * 2003-03-25 2005-02-24 L'oreal S.A. Use of polycarboxylic acids and salts thereof as complexing agents in oxidizing compositions for dyeing, bleaching or permanently reshaping keratin fibres
US20050125912A1 (en) * 2001-12-21 2005-06-16 Patricia Desenne Dyeing composition for keratinous fibers comprising an oxyethylene rapeseed fatty acid amide
US6916344B1 (en) 1999-12-08 2005-07-12 L'oreal S.A. Direct dyeing composition for keratinic fibers containing a thickening polymer with an ether plastic skeleton
US6919073B2 (en) 2001-05-16 2005-07-19 L'oreal S.A. Pulverulent composition for bleaching human keratin fibers
US20050158262A1 (en) * 2003-12-19 2005-07-21 Eric Parris Cosmetic composition comprising a cationic agent, a polymer comprising a hetero atom and an oil, and cosmetic treatment process
US20050169873A1 (en) * 2003-12-19 2005-08-04 Isabelle Rollat Styling composition comprising, in a predominantly aqueous medium, an elastic cationic polyurethane, processes using it and uses thereof
US20050175569A1 (en) * 2004-01-07 2005-08-11 Geraldine Fack Cosmetic compositions comprising a cation, a drawing polymer and a thickener, and cosmetic treatment processes
US20050186151A1 (en) * 2003-08-11 2005-08-25 Franck Giroud Cosmetic composition comprising stabilized and optionally coated metal particles
US20050188475A1 (en) * 2004-01-07 2005-09-01 Alain Lagrange Dyeing composition comprising at least one fluorindine compound for the dyeing of keratinic fibers, dyeing process comprising the composition and compound
US20050208005A1 (en) * 2003-08-11 2005-09-22 Franck Giroud Cosmetic composition comprising particles having a core-shell structure
US6956017B1 (en) 1999-10-29 2005-10-18 The Procter & Gamble Company Laundry detergent compositions with fabric care
US20050232884A1 (en) * 2004-04-02 2005-10-20 Thomas Fondin Method for treating hair fibers
US20050232883A1 (en) * 2004-04-02 2005-10-20 Thomas Fondin Method for treating hair fibers
US20050232885A1 (en) * 2004-01-07 2005-10-20 L'oreal Detergent cosmetic compositions comprising at least one surfactant, at least one drawing polymer and at least one nonsilicone conditioner, and use thereof
US20060025318A1 (en) * 2004-04-22 2006-02-02 Mireille Maubru Composition for washing and conditioning keratin materials, comprising a carboxyalkyl starch, and process for the use thereof
US20060057096A1 (en) * 2004-09-08 2006-03-16 Pascale Lazzeri Cosmetic composition comprising at least one cationic surfactant, at least one aminated silicone, at least one fatty alcohol, and at least one diol
US7128902B2 (en) 2001-11-08 2006-10-31 L'oreal, Sa Reducing composition for treating keratin fibres, comprising a particular aminosilicone
US7135167B2 (en) 2001-11-08 2006-11-14 L'oreal, Sa Oxidizing composition for treating keratin fibers, comprising a particular aminosilicone
US20060257339A1 (en) * 2005-05-13 2006-11-16 L'oreal Use of conductive polymer nanofibers for treating keratinous surfaces
US7138109B2 (en) 2001-11-08 2006-11-21 L'oreal, Sa Use of particular aminosilicones as a pre-or post-treatment of processes for bleaching keratin fibres
US20060265817A1 (en) * 2005-03-31 2006-11-30 Frederic Legrand Dye composition comprising at least one non-ionic associative polymer and process for dyeing keratin fibers using same
US7147673B2 (en) 2003-04-01 2006-12-12 L'oreal S.A. Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one insoluble polyorganosiloxane conditioning polymer, process therefor and use thereof
US7150764B2 (en) 2003-04-01 2006-12-19 L'oreal S.A. Composition for dyeing a human keratin material, comprising at least one fluorescent dye and at least one insoluble conditioning agent, process thereof, use thereof, and devices thereof
US7186278B2 (en) 2003-04-01 2007-03-06 L'oreal S.A. Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one compound comprising an acid functional group and processes therefor
US7192454B2 (en) 2003-04-01 2007-03-20 L'oreal S.A. Composition for dyeing human keratin materials, comprising a fluorescent dye and a particular sequestering agent, process therefor and use thereof
US7195651B2 (en) 2003-04-01 2007-03-27 L'oreal S.A. Cosmetic composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one cationic polymer, and a dyeing process therefor
US7195650B2 (en) 2003-04-01 2007-03-27 L'oreal S.A. Process for dyeing, with a lightening effect, human keratin fibers that have been permanently reshaped, using at least one composition comprising at least one fluorescent dye
US7198650B2 (en) 2003-04-01 2007-04-03 L'oreal S.A. Method of dyeing human keratin materials with a lightening effect with compositions comprising at least one fluorescent dye and at least one amphoteric or nonionic surfactant, composition thereof, process thereof, and device therefor
US20070074356A1 (en) * 2005-09-29 2007-04-05 Boris Lalleman Process for the photoprotective treatment of artificially dyed keratin fibers by application of a liquid water/steam mixture
US7204860B2 (en) 2003-04-01 2007-04-17 L'oreal Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one polyol, process therefor and use thereof
US7208018B2 (en) 2003-04-01 2007-04-24 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
US20070104747A1 (en) * 2005-10-28 2007-05-10 Virginie Masse Cosmetic composition comprising at least one anti-dandruff agent and also oxyethylenated sorbitan monolaurate, and cosmetic treatment process using said composition
US20070104668A1 (en) * 2005-10-28 2007-05-10 Virginie Masse Composition for the care of keratin material and cosmetic treatment process using said composition
US20070105734A1 (en) * 2005-10-28 2007-05-10 Sandrine Decoster Composition for washing keratin materials and cosmetic treatment process using said composition
US7217296B2 (en) 2001-09-28 2007-05-15 L'oreal S.A. Dyeing composition with a lightening effect for human keratin materials comprising at least one fluorescent dye
US7220408B2 (en) 2001-11-08 2007-05-22 L'oreal, S.A. Cosmetic compositions containing a particular aminosilicone and a thickener, and uses thereof
US7223385B2 (en) 2001-11-08 2007-05-29 L'oreal S.A. Cosmetic compositions containing a particular aminosilicone and a conditioner, and uses thereof
US20070141006A1 (en) * 2004-03-17 2007-06-21 Aude Livoreil Cosmetic compositions containing modified polyamines and the uses thereof
US7250064B2 (en) 2003-04-01 2007-07-31 L'oreal S.A. Dye composition comprising at least one fluorescent dye and a non-associative thickening polymer for human keratin materials, process therefor, and method thereof
US20070174974A1 (en) * 2003-05-09 2007-08-02 De La Mettrie Roland Process for treating keratin fibres by applying heat
US7258852B2 (en) 2001-09-11 2007-08-21 L'oreal S.A. Cosmetic compositions containing a methacrylic acid copolymer and an oil, and uses thereof
US7261744B2 (en) 2002-12-24 2007-08-28 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
US20070237733A1 (en) * 2004-01-05 2007-10-11 Frederic Simonet Cosmetic Composition of Water-in-Water Emulsion type Based on Surfactants and Cationic Polymers
US20070251026A1 (en) * 2006-04-12 2007-11-01 Boris Lalleman Unsaturated fatty substances for protecting the color of artificially dyed keratin fibers with respect to washing; and dyeing processes
US7303589B2 (en) 2003-04-01 2007-12-04 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
US20080119554A1 (en) * 2004-11-26 2008-05-22 Rajiv Jalan Compositions Comprising Ornithine And Phenylacetate Or Phenylbutyrate For Treating Hepatic Encephalopathy
US20090068124A1 (en) * 2006-03-03 2009-03-12 Raphael Beumer Novel heterocyclic substituted condensation polymers
US20090081148A1 (en) * 2000-08-25 2009-03-26 L'oreal S.A. Protection of keratinous fibers using ceramides and/or glycoceramides
US7510705B2 (en) 2001-11-08 2009-03-31 L'oreal, S.A. Process for permanently reshaping the hair using particular aminosilicones
US7550015B2 (en) 2005-03-31 2009-06-23 L'oreal S.A. Dye composition with a reduced content of starting materials, and process for dyeing keratin fibers using the same
US7569078B2 (en) 2005-03-31 2009-08-04 L'oreal S.A. Dye composition comprising at least one cellulose and process for dyeing keratin fibers using the dye composition
US7575605B2 (en) 2005-03-31 2009-08-18 L'oreal S.A. Dye composition comprising at least one glycerol ester and a process for dyeing keratin fibers using the composition
US7578854B2 (en) 2005-03-31 2009-08-25 L'oreal S.A. Dye composition comprising at least one fatty acid ester and process for dyeing keratin fibers using the same
US7651533B2 (en) 2005-03-31 2010-01-26 Oreal Dye composition with a reduced content of starting materials, process for dyeing keratin fibers using the same and device therefor
US7736631B2 (en) 2003-04-01 2010-06-15 L'oreal S.A. Cosmetic dye composition with a lightening effect for human keratin materials, comprising at least one fluorescent dye and at least one aminosilicone, and process of dyeing
US7771492B2 (en) 1999-12-30 2010-08-10 L'oreal S.A. Compositions for oxidation dyeing keratin fibers comprising at least one thickening polymer comprising at least one fatty chain and at least one fatty alcohol chosen from monoglycerolated fatty alcohols and polyglycerolated fatty alcohols
US7799093B2 (en) 2006-10-25 2010-09-21 L'ORéAL S.A. Coloring composition of keratinous fibers comprising at least one polysiloxane/polyurea block copolymer
US20110155163A1 (en) * 2009-12-23 2011-06-30 Viravau Valerie Cosmetic composition comprising at least one organosilicon compound, at least one anionic surfactant and at least one nonionic thickener, and process using the composition
US20110158927A1 (en) * 2009-12-23 2011-06-30 Viravau Valerie Cosmetic composition comprising at least one organosilicon compound, at least one anionic surfactant and at least one cationic polymer
US20110182842A1 (en) * 2009-12-23 2011-07-28 Carine Aires Cosmetic composition comprising at least one organosilicon compound, at least two anionic surfactants and at least one amphoteric surfactant
US8784506B2 (en) 2010-11-02 2014-07-22 L'oreal Dye composition having a low content of ammonia
US8790623B2 (en) 2005-01-18 2014-07-29 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
US8802066B2 (en) 2010-12-21 2014-08-12 L'oreal Cosmetic composition comprising a particular zinc salt and an amino silicone
US8828368B2 (en) 2010-12-21 2014-09-09 L'oreal Cosmetic composition comprising a particular zinc salt and a starch
US9044412B2 (en) 2011-07-05 2015-06-02 L'oreal Dye composition using a long-chain ether of an alkoxylated fatty alcohol and a cationic polymer, processes and devices using the same
EP2438906A3 (en) * 2010-08-17 2015-06-03 Henkel AG & Co. KGaA Matting additive for blonding agents
US9060944B2 (en) 2011-07-05 2015-06-23 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
US9066890B2 (en) 2011-07-05 2015-06-30 L'oreal Dye composition comprising an alkoxylated fatty alcohol ether and a fatty alcohol
US9180086B2 (en) 2011-06-01 2015-11-10 L'oreal Process for treating straightened keratin fibres
US9198851B2 (en) 2012-01-23 2015-12-01 L'oreal Composition comprising at least one specific alkoxysilane polymer
US9375393B2 (en) 2010-12-21 2016-06-28 L'oreal Composition comprising a non-nitrogenous zinc salt and a particular cationic surfactant
US9493475B2 (en) 2012-09-18 2016-11-15 Devan Chemicals Nv Textile treatment compounds and compositions
US9776020B2 (en) 2011-05-27 2017-10-03 L'oreal Composition comprising an alkoxysilane and a modified starch, and cosmetic use thereof
US9827185B2 (en) 2012-08-02 2017-11-28 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
US9974725B1 (en) 2017-05-24 2018-05-22 L'oreal Methods for treating chemically relaxed hair
US10058494B2 (en) 2015-11-24 2018-08-28 L'oreal Compositions for altering the color of hair
US10137063B2 (en) 2012-08-02 2018-11-27 L'oreal Dye composition comprising nonionic guar gum or a nonionic derivative thereof, process and device for the same
US10201483B2 (en) 2012-08-02 2019-02-12 L'oreal Dye composition in cream form comprising at least one oil and little or no solid fatty alcohol, dyeing process and suitable device
US10226411B2 (en) 2012-08-02 2019-03-12 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
US10231915B2 (en) 2015-05-01 2019-03-19 L'oreal Compositions for altering the color of hair

Families Citing this family (133)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2280361B2 (en) * 1974-08-02 1981-11-13 Oreal
FR2417981B2 (en) * 1978-02-27 1987-04-30 Oreal New cosmetic compositions for hair and application process
CA1144691A (en) * 1977-08-19 1983-04-12 David H. Dumas Sizing accelerator
US4298494A (en) * 1979-03-27 1981-11-03 Lever Brothers Company Shampoo
FR2460133B1 (en) * 1979-07-02 1986-11-07 Bristol Myers Co A composition for hair care and its application method
LU83020A1 (en) * 1980-12-19 1982-07-07 Oreal oily composition for treating keratin materials and skin
DE3417239A1 (en) * 1984-05-10 1985-11-14 Basf Ag A process for preparing antifelting equipped, optionally dyed wool
DE3417240A1 (en) * 1984-05-10 1985-11-14 Basf Ag A process for the aftertreatment of dyed textile materials composed of natural or synthetic polyamides
GB8429273D0 (en) * 1984-11-20 1984-12-27 Dow Chemical Nederland Producing nitrogen containing prepolymer
DE4241118A1 (en) * 1992-12-07 1994-06-09 Basf Ag Use of cationic polyurethanes and polyureas as auxiliaries in cosmetic and pharmaceutical preparations
FR2718960B1 (en) * 1994-04-22 1996-06-07 Oreal Compositions for the treatment and protection of hair, ceramide and cationic groups to polymers.
FR2718961B1 (en) * 1994-04-22 1996-06-21 Oreal Compositions for washing and treating the hair and skin ceramide and cationic groups to polymers.
FR2729852B1 (en) 1995-01-30 1997-03-07
FR2749506B1 (en) 1996-06-07 1998-08-07 Oreal Detergent cosmetic compositions and use capillary use
FR2749507B1 (en) * 1996-06-07 1998-08-07 Oreal Detergent cosmetic compositions and use
FR2751532B1 (en) * 1996-07-23 1998-08-28 Oreal washing compositions and conditioning silicone-based and dialkyl
FR2773069B1 (en) 1997-12-29 2001-02-02 Oreal cosmetic composition comprising at least one surfactant amidoethercarboxylique acid and at least one combination of an anionic polymer and a cationic polymer
FR2785799B1 (en) 1998-11-12 2002-11-29 Oreal Cosmetic conditioning and detergent composition comprising a carboxylic acid surfactant, a silicone and a cationic polymer, use and method.
FR2788975B1 (en) 1999-01-29 2002-08-09 Oreal aqueous composition for keratin fibers discoloration ready to use comprising a combination of a water-soluble solvent and a nonionic or anionic amphiphilic polymer comprising at least one fatty chain
FR2788972B1 (en) 1999-02-03 2001-04-13 Oreal hair composition comprising a cleansing base, a cationic polymer and an anionic polyurethane and use
FR2788973B1 (en) 1999-02-03 2002-04-05 Oreal Cosmetic composition comprising an anionic surfactant, an amphoteric surfactant, polyolefin type of an oil, a cationic polymer and a salt or a water soluble alcohol, use and method
FR2819404B1 (en) 2001-01-12 2004-11-05 Oreal Cosmetic compositions containing a fructan and a cationic polymer and uses thereof
FR2848102B1 (en) 2002-12-06 2007-08-03 Oreal oxidation dye composition comprising an oxidation dye, an associative polymer, a nonionic cellulose compound and a cationic polymer
FR2848105B1 (en) 2002-12-06 2006-11-17 Oreal Oxidation dye composition for keratin fibers comprising a fatty alcohol, an oxidation dye, an associative polymer and an alkyl sulfate c14-c30.
US7217298B2 (en) 2003-01-16 2007-05-15 L'oreal S.A. Ready-to-use bleaching compositions, preparation process and bleaching process
FR2874820B1 (en) 2004-09-08 2007-06-22 Oreal Cosmetic composition based on a cationic surfactant, a fatty alcohol and a diol
FR2880801B1 (en) 2005-01-18 2008-12-19 Oreal keratinous fiber treatment composition comprising an aromatic alcohol, an aromatic carboxylic acid and a protective agent
FR2881954B1 (en) 2005-02-11 2007-03-30 Oreal Cosmetic composition comprising a cation, a cationic polymer, a solid compound and starch and cosmetic treatment process
FR2883738B1 (en) 2005-03-31 2007-05-18 Oreal A dye composition comprising a nonionic associative polymer, fibers of the keratin dyeing process employing
FR2883736B1 (en) 2005-03-31 2007-05-25 Oreal A dye composition comprising a fatty acid ester and keratin fiber dyeing method embodying the
FR2883737B1 (en) 2005-03-31 2009-06-12 Oreal A dye composition comprising a glyceryl ester and fiber dyeing method embodying the keratin
FR2883735B1 (en) 2005-03-31 2009-06-12 Oreal The coloring composition has decreased content of raw materials, keratin fiber dyeing process using the execution device and
FR2883734B1 (en) 2005-03-31 2007-09-07 Oreal The coloring composition has decreased content of raw materials and keratin fiber dyeing method embodying the
FR2883746B1 (en) 2005-03-31 2007-05-25 Oreal A dye composition comprising a cellulose fiber and process for coloring keratin the implementing
FR2908305B1 (en) 2006-11-10 2009-02-27 Oreal Process for permanently reshaping keratin fibers, comprising a step of applying a composition comprising intermediate rinse a monovalent metal cation salt or an ammonium salt and an organic acid
FR2910274B1 (en) 2006-12-22 2009-04-03 Oreal Process for permanently reshaping keratin fibers, comprising a step of applying a low concentration reducing composition and an intermediate drying step
FR2911272B1 (en) 2007-01-12 2009-03-06 Oreal Reductive composition intended to be used in a permanent deformation of keratinous fibers comprising cysteine ​​and thiolactic acid or a salt thereof
FR2915376B1 (en) 2007-04-30 2011-06-24 Oreal Use of a multi-carbo multi-sites moieties coupling agent to protect the color vis-a-vis the washing keratin fibers artificially dyed; staining methods
FR2917972B1 (en) 2007-06-29 2009-10-16 Oreal An anhydrous composition in the form of paste for bleaching keratin fibers
DE102007030642A1 (en) 2007-07-02 2009-01-08 Momentive Performance Materials Gmbh A process for the preparation of polyorganosiloxanes having (C6-C60) -Alkylmethylsiloxygruppen and dimethylsiloxy
FR2920977B1 (en) 2007-09-14 2012-07-27 Oreal cosmetic compositions containing a cationic copolymer and a particular triglyceride and their uses.
FR2920976B1 (en) 2007-09-14 2009-12-04 Oreal cosmetic composition comprising a cationic copolymer and an anionic associative polymer and cosmetic treatment process.
FR2920971B1 (en) 2007-09-14 2014-03-28 Oreal cosmetic composition comprising at least one specific cationic polymer, at least one surfactant, at least one cationic or amphoteric polymer and at least one mineral particle, and cosmetic treatment process.
FR2920978B1 (en) 2007-09-14 2012-04-27 Oreal cosmetic composition comprising a cationic copolymer and a starch and cosmetic treatment process.
FR2920972B1 (en) 2007-09-14 2009-12-04 Oreal cosmetic composition comprising a specific cationic polymer and at least one fatty acid ester of C 8 -C 24 and of oxyethylenated sorbitan comprising 2 to 10 oxyethylene units, and cosmetic treatment process.
FR2924338B1 (en) 2007-11-30 2010-09-03 Oreal A hair styling composition comprising at least a (meth) acrylic acid and at least one pearlescent agent.
FR2924336A1 (en) 2007-11-30 2009-06-05 Oreal A hair styling composition comprising (meth) acrylic acid and at least one oil.
FR2924337A1 (en) 2007-11-30 2009-06-05 Oreal repositionable styling composition comprising at least a (meth) acrylic acid and at least one silicone.
FR2930436B1 (en) 2008-04-28 2010-06-11 Oreal cosmetic composition comprising an emulsion obtained by a method pit
FR2930442B1 (en) 2008-04-28 2010-06-11 Oreal cosmetic composition comprising an emulsion obtained by pit METHOD
FR2940067B1 (en) 2008-12-19 2011-02-25 Oreal oxidizing composition for treating keratin fibers, comprising a cationic polymer, a fatty amide and an agent-oxygen
FR2940063B1 (en) 2008-12-19 2011-02-11 Oreal antiperspirant compositions containing at least one complex form by the combination of at least one anionic species and at least one cationic species and method of treating human perspiration.
FR2940078B1 (en) 2008-12-19 2011-05-13 Oreal Composition comprising a fatty substance and a cationic polymer, dyeing process using the implemented systems
EP2198850A1 (en) 2008-12-22 2010-06-23 L'oreal Cosmetic composition containing four types of surfactants and one non-silicone fatty derivative
FR2940094B1 (en) 2008-12-22 2011-02-25 Oreal Cosmetic composition comprising detergente four surfactants, a cationic polymer and a zinc salt
FR2943895B1 (en) 2009-04-03 2011-05-06 Oreal Hair processing method with the help of steam.
FR2944438B1 (en) 2009-04-15 2011-06-17 Oreal shaping of the hair by means of a reducing composition and heating.
FR2949970B1 (en) 2009-09-15 2011-09-02 Oreal Use of a drying oil to protect the color vis-a-vis the washing keratin fibers artificially dyed; staining methods
FR2954114B1 (en) 2009-12-17 2013-10-11 Oreal Cosmetic composition comprising a surfactant, a liquid fatty alcohol and fatty alcohol ether and oxyethylene cosmetic treatment process
FR2954149B1 (en) 2009-12-17 2014-10-24 Oreal Cosmetic composition comprising a surfactant, a liquid fatty alcohol and a nonionic associative polymer and cosmetic treatment process
WO2011074140A1 (en) 2009-12-18 2011-06-23 L'oreal Process for treating keratin fibers
FR2954135B1 (en) 2009-12-23 2012-02-24 Oreal cosmetic composition comprising at least one organic compound of silicon, at least one anionic surfactant and at least one aminosilicone and a method using said composition
FR2954139B1 (en) 2009-12-23 2012-05-11 Oreal cosmetic composition comprising at least one volatile linear alkane and at least one non-protein cationic polymer
FR2954108B1 (en) 2009-12-23 2012-03-09 Oreal Use of a cosmetic composition containing a volatile linear alkane and a nonionic associative polymer for conditioning the hair
FR2956811B1 (en) 2010-03-01 2012-05-25 Oreal Antidandruff composition based cosmetics ellagic or its derivatives acid and a second compound different active in a particular ponderal ratio.
FR2956808B1 (en) 2010-03-01 2012-05-25 Oreal Use of ellagic acid as an anti-dandruff agent.
WO2011107467A2 (en) 2010-03-01 2011-09-09 L'oreal Cosmetic composition based on ellagic acid or a derivative thereof and on a particular mixture of surfactants
FR2956812B1 (en) 2010-03-01 2013-03-08 Oreal Cosmetic composition ellagic acid base or a derivative thereof and an extract of bacteria.
FR2956809B1 (en) 2010-03-01 2014-09-26 Oreal Composition comprising ellagic acid and a specific cationic surfactant and its use in cosmetic
FR2959666B1 (en) 2010-05-07 2012-07-20 Oreal foaming cosmetic composition of ellagic acid base or its derivatives and essential oil.
FR2964319B1 (en) 2010-09-06 2017-01-13 Oreal cosmetic composition comprising at least one cationic polymer and at least two surfactants
WO2012032673A1 (en) 2010-09-08 2012-03-15 L'oreal Cosmetic composition for keratin fibers
FR2965174B1 (en) 2010-09-24 2013-04-12 Oreal cosmetic composition comprising at least one hygroscopic salt and at least one aromatic ether of polyol and at least one diol, cosmetic treatment process
FR2965481B1 (en) 2010-10-01 2013-04-19 Oreal fibers of keratin processing method using at least one reducing sulfur, at least one cationic polymer and at least one mercaptosiloxane
WO2012049145A1 (en) 2010-10-12 2012-04-19 L'oreal Cosmetic composition comprising a particular silicon derivative and one or more acrylic thickening polymers
FR2966352B1 (en) 2010-10-26 2016-03-25 Oreal Cosmetic composition comprising an alkoxysilane containing a fatty chain and a cationic polymer
FR2966357A1 (en) 2010-10-26 2012-04-27 Oreal Cosmetic composition comprising a fatty chain and alkoxysilane has an antidandruff agent
FR2968209B1 (en) 2010-12-03 2013-07-12 Oreal Cosmetic compositions containing a non-amino silicone, a liquid fatty ester and an aminosilicone, processes and uses
FR2968939B1 (en) 2010-12-21 2014-03-14 Oreal Cosmetic composition comprising a particular zinc salt and a fatty ester
FR2968942B1 (en) 2010-12-21 2016-02-12 Oreal Cosmetic composition comprising a zinc salt and 1,2-octanediol
FR2968943B1 (en) 2010-12-21 2013-07-05 Oreal Cosmetic composition comprising a zinc salt, a cationic polymer and a propellant
WO2012110608A2 (en) 2011-02-17 2012-08-23 L'oreal Process for treating keratin fibres using a silicone elastomer in combination with heat
FR2973661A1 (en) 2011-04-08 2012-10-12 Oreal Hair processing method.
WO2012149617A1 (en) 2011-05-04 2012-11-08 L'oreal S.A. Detergent cosmetic compositions comprising four surfactants, a cationic polymer and a silicone, and use thereof
FR2975594B1 (en) 2011-05-27 2013-05-10 Oreal Composition comprising an alkoxysilane, a fatty ester and silicone and its use in cosmetic
FR2976483B1 (en) 2011-06-17 2013-07-26 Oreal Cosmetic composition comprising an anionic surfactant, a nonionic surfactant or amphoteric surfactant and a solid fatty alcohol and cosmetic treatment process
CN103813778B (en) 2011-09-22 2016-11-09 莱雅公司 Cosmetic composition
FR2984159B1 (en) 2011-12-19 2014-01-31 Oreal Cosmetic composition comprising a hydrophobically modified cellulose, an anionic sulfate or sulfonate, and a branched fatty alcohol.
FR2984156B1 (en) 2011-12-19 2016-08-26 Oreal Cosmetic composition comprising a hydrophobically modified cellulose and an anionic surfactant has group (s) carboxylate (s)
EP2793831B1 (en) 2011-12-20 2018-10-03 L'Oréal Cosmetic composition comprising an anionic surfactant, a solid fatty alcohol and a solid fatty ester, and cosmetic treatment process
FR2988602B1 (en) 2012-03-27 2014-09-05 Oreal Method of cosmetic care and / or making up keratin materials
WO2014002290A1 (en) 2012-06-29 2014-01-03 L'oreal Cosmetic composition for keratin fibers
WO2014056962A2 (en) 2012-10-11 2014-04-17 L'oreal Cosmetic composition comprising a bacterial lysate, a thickener and a particular surfactant system, and cosmetic treatment process
WO2014068795A1 (en) 2012-10-31 2014-05-08 L'oreal Use of triazine derivatives for permanent deformation of keratin fibers
FR2997848B1 (en) 2012-11-09 2015-01-16 Oreal Composition comprising a dicarbonyl derivative and hair straightening process from this composition
FR2997845B1 (en) 2012-11-09 2015-03-06 Oreal hair straightening process from a composition containing glyoxylic acid and / or its derivatives
FR2999077A1 (en) 2012-12-11 2014-06-13 Oreal cosmetic composition comprising a nonionic surfactant, a cationic surfactant, a liquid fatty ester and a particular silicone, and pro-cede of cosmetic treatment
FR2999078B1 (en) 2012-12-11 2015-08-07 Oreal Cosmetic composition comprising the combination of nonionic and cationic surfactants, and cosmetic treatment process
FR3001149B1 (en) 2013-01-18 2015-01-16 Oreal shaping of the hair which comprises applying a particular styling composition that is rinsed
FR3001147B1 (en) 2013-01-18 2015-07-17 Oreal soft solid cosmetic composition comprising anio lunches surfactants and solid particles, and cosmetic treatment process
FR3001145B1 (en) 2013-01-18 2015-07-17 Oreal soft solid cosmetic composition comprising anio lunches surfactants and polyols, and cosmetic treatment process
FR3010900B1 (en) 2013-09-24 2017-02-17 Oreal cosmetic composition comprising a combination of surfactants of the carboxylate type, acyl isethionate, and alkyl (poly) glycoside.
WO2015063122A1 (en) 2013-10-30 2015-05-07 L'oreal Expanded dyeing composition comprising an inert gas, an oxidation dye and an oxyalkylenated nonionic surfactant
FR3015273B1 (en) 2013-12-19 2015-12-25 Oreal rich in fats dyeing composition comprising a mixture of ethoxylated surfactants
FR3015272B1 (en) 2013-12-19 2016-01-08 Oreal Process for coloring implementing compositions rich in fats
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3069390A (en) * 1959-07-17 1962-12-18 Borden Co Polymeric amides from polymeric acrylic acid esters and n-aminoalkyl alkanol amines and reaction products therefrom
US3250682A (en) * 1961-02-22 1966-05-10 Wella Ag Method of setting hair with epoxy resin compositions
US3267046A (en) * 1961-12-19 1966-08-16 Montedison Spa Process for regulating the molecular weight of basic nitrogen polycondensates
US3274312A (en) * 1961-12-21 1966-09-20 Montedison Spa Process for preparing dye-receptive shaped articles
US3280044A (en) * 1962-02-02 1966-10-18 Montedison Spa Metal salts of epichlorohydrin-piperazine-amine polycondensates

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1470819A (en) * 1965-03-15 1967-02-24 Eastman Kodak Co New linear condensation polymers, process for their preparation and their applications, particularly in photography
US3560609A (en) * 1967-10-13 1971-02-02 Hercules Inc Hair-setting composition

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3069390A (en) * 1959-07-17 1962-12-18 Borden Co Polymeric amides from polymeric acrylic acid esters and n-aminoalkyl alkanol amines and reaction products therefrom
US3250682A (en) * 1961-02-22 1966-05-10 Wella Ag Method of setting hair with epoxy resin compositions
US3267046A (en) * 1961-12-19 1966-08-16 Montedison Spa Process for regulating the molecular weight of basic nitrogen polycondensates
US3274312A (en) * 1961-12-21 1966-09-20 Montedison Spa Process for preparing dye-receptive shaped articles
US3280044A (en) * 1962-02-02 1966-10-18 Montedison Spa Metal salts of epichlorohydrin-piperazine-amine polycondensates

Cited By (214)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4018721A (en) * 1974-03-07 1977-04-19 Union Carbide Corporation Cross-linked, water insoluble poly(N-glycidyl-piperazine)
US4101456A (en) * 1975-04-18 1978-07-18 Colgate-Palmolive Company Light duty liquid detergent
US4080310A (en) * 1975-06-12 1978-03-21 Beecham Group Limited Amphoteric conditioning shampoo
US4362528A (en) * 1975-11-13 1982-12-07 Societe Anonyme Dite: L'oreal Cosmetic composition for dyeing hair and process for using the same
US4314807A (en) * 1975-11-13 1982-02-09 L'oreal Hair dye composition containing a hair dye formulation packaged in two parts
US4061602A (en) * 1976-08-03 1977-12-06 American Cyanamid Company Conditioning shampoo composition containing a cationic derivative of a natural gum (such as guar) as the active conditioning ingredient
US4201766A (en) * 1977-03-02 1980-05-06 L'oreal Hair conditioning composition and method of using the same
US4240450A (en) * 1977-03-15 1980-12-23 L'oreal Composition and process for the treatment of keratin materials with polymers
US4719099A (en) * 1977-03-15 1988-01-12 L'oreal Composition and process for the treatment of keratin materials with polymers
US4349532A (en) * 1977-09-20 1982-09-14 Guy Vanlerberghe Cosmetic compositions based on poly-(quaternary ammonium) polymers
US4305829A (en) * 1979-06-29 1981-12-15 Union Carbide Corporation Process for flocculating an aqueous suspension of particles with quaternary ammonium graft copolymers
US4271053A (en) * 1979-06-29 1981-06-02 Union Carbide Corporation Quaternary ammonium graft copolymers for use as flocculants and method of preparing same
US4470982A (en) * 1980-12-22 1984-09-11 The Procter & Gamble Company Shampoo compositions
US4761273A (en) * 1981-05-08 1988-08-02 L'oreal Composition in the form of an aerosol foam, based on a cationic polymer and an anionic polymer
US4488879A (en) * 1982-07-10 1984-12-18 Basf Aktiengesellschaft Process for dyeing textile materials of polyacrylonitrile: quaternized piperazine copolymer as basic dye retarder
US4465802A (en) * 1982-10-26 1984-08-14 Union Carbide Corporation Process for treating furred animal pelts and/or fur
EP0168719A3 (en) * 1984-07-20 1987-05-20 Revlon, Inc. Low ph hair conditioner compositions containing amine oxides
US4656245A (en) * 1985-03-08 1987-04-07 Sumitomo Electric Industries, Ltd. Functional elastomer
US4851532A (en) * 1985-05-20 1989-07-25 Buckman Laboratories, Inc. Ionene polymeric compositions, their preparation and use
US4647379A (en) * 1985-11-13 1987-03-03 The Dow Chemical Company Nitrogen-containing water-soluble polymer flocculants
US4806345A (en) * 1985-11-21 1989-02-21 Nalco Chemical Company Cross-linked cationic polymers for use in personal care products
US4867966A (en) * 1986-09-19 1989-09-19 L'oreal Cosmetic compositions based on cationic polymers and alkyloxazoline polymers
US5130056A (en) * 1989-01-27 1992-07-14 Deutsche Solvay-Werke Gmbh Cleaning agent and process for its preparation
US5236996A (en) * 1991-07-24 1993-08-17 Union Camp Corporation Stable polyamide resin dispersions containing piperasine and methods for the manufacture thereof
US6262011B1 (en) * 1996-10-21 2001-07-17 Basf Aktiengesellschaft Polycationic condensates as color transfer inhibiting and color release reducing additive to detergents and fabric conditioners
US6589519B1 (en) 1997-08-25 2003-07-08 L'oreal S.A. Cosmetic compositions containing a polyoxyalkylenated aminosilicone block copolymer and a conditioner, and uses thereof
US6482787B1 (en) 1997-09-15 2002-11-19 The Procter & Gamble Company Laundry detergent and fabric conditioning compositions with oxidized cyclic amine based polymers
WO1999014300A1 (en) * 1997-09-15 1999-03-25 The Procter & Gamble Company Laundry detergent compositions with cyclic amine based polymers to provide appearance and integrity benefits to fabrics laundered therewith
US6228828B1 (en) 1997-09-15 2001-05-08 The Procter & Gamble Company Laundry detergent compositions with anionically modified, cyclic amine based polymers
US6251846B1 (en) * 1997-09-15 2001-06-26 The Procter & Gamble Company Laundry detergent compositions with cyclic amine based polymers to provide appearance and integrity benefits to fabrics laundered therewith
WO1999014299A1 (en) * 1997-09-15 1999-03-25 The Procter & Gamble Company Laundry detergent compositions with anionically modified, cyclic amine based polymers
WO1999014301A1 (en) * 1997-09-15 1999-03-25 The Procter & Gamble Company Laundry detergent and fabric conditioning compositions with oxidized cyclic amine based polymers
CZ300454B6 (en) * 1997-09-15 2009-05-20 The Procter & Gamble Company Washing detergent agent for providing better appearance and integrity of fabrics and textiles, washed in washing solutions comprising this agent
AU740415B2 (en) * 1997-09-15 2001-11-01 Procter & Gamble Company, The Laundry detergent compositions with cyclic amine based polymers to provide appearance and integrity benefits to fabrics laundered therewith
US6472364B1 (en) 1998-10-13 2002-10-29 The Procter & Gamble Company Detergent compositions or components
US6379401B1 (en) 1999-01-29 2002-04-30 L'oreal, S.A. Anhydrous composition for bleaching keratin fibers comprising a combination of a water-soluble thickening polymer and a nonionic amphiphilic polymer comprising at least one fatty chain
US6260556B1 (en) 1999-01-29 2001-07-17 L'oreal Anhydrous composition for bleaching keratin fibers
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
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
US6482400B1 (en) 1999-06-30 2002-11-19 L'Oréal S.R. Mascara containing film-forming polymers
US6534047B1 (en) 1999-06-30 2003-03-18 L'oreal S.A. Mascara containing film-forming polymers
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
US6956017B1 (en) 1999-10-29 2005-10-18 The Procter & Gamble Company Laundry detergent compositions with fabric care
WO2001032815A1 (en) * 1999-10-29 2001-05-10 The Procter & Gamble Company Laundry detergent compositions with fabric care
WO2001032816A1 (en) * 1999-10-29 2001-05-10 The Procter & Gamble Company Laundry detergent compositions with fabric care
US6916344B1 (en) 1999-12-08 2005-07-12 L'oreal S.A. Direct dyeing composition for keratinic fibers containing a thickening polymer with an ether plastic skeleton
US6800098B1 (en) 1999-12-08 2004-10-05 L'oreal, S.A. Oxidation dye composition for keratinic fibres containing a thickening polymer with an ether plastic skeleton
US6800096B1 (en) 1999-12-08 2004-10-05 L'oreal S.A. Composition, process and kit for bleaching keratin fibers comprising at least one thickening polymer with an aminoplast-ether skeleton
US6444197B2 (en) 1999-12-13 2002-09-03 L'oreal S.A. Bleaching composition for keratin fibers, comprising a combination of two polyurethane polyethers
US7771492B2 (en) 1999-12-30 2010-08-10 L'oreal S.A. Compositions for oxidation dyeing keratin fibers comprising at least one thickening polymer comprising at least one fatty chain and at least one fatty alcohol chosen from monoglycerolated fatty alcohols and polyglycerolated fatty alcohols
US6436151B2 (en) 1999-12-30 2002-08-20 L'oreal S.A. Compositions for oxidation dyeing keratin fibers comprising at least one oxidation dye, at least one thickening polymer comprising at least one fatty chain, and at least one fatty alcohol comprising more than twenty carbon atoms and uses thereof
US6695887B2 (en) 1999-12-30 2004-02-24 L'oreal S.A. Compositions for oxidation dyeing keratin fibers comprising at least one fatty alcohol having more than twenty carbon atoms and at least one oxyalkylenated nonionic surfactant with an hlb greater than 5
US6635262B2 (en) 2000-03-14 2003-10-21 L'oreal S.A. Roll-on applicator comprising a hair composition
US6602303B2 (en) 2000-08-11 2003-08-05 L'oreal S.A. Composition for the oxidation dyeing of keratinous fibers comprising at least one oxidation dye and at least one cationic amphiphilic polymer, and dyeing methods
US20040034944A1 (en) * 2000-08-21 2004-02-26 Frederic Legrand Bleaching composition for dyed keratinous fibers
US20050132505A9 (en) * 2000-08-21 2005-06-23 Frederic Legrand Bleaching composition for dyed keratinous fibers
US8703109B2 (en) 2000-08-25 2014-04-22 L'oreal Protection of keratinous fibers using ceramides and/or glycoceramides
US20090081148A1 (en) * 2000-08-25 2009-03-26 L'oreal S.A. Protection of keratinous fibers using ceramides and/or glycoceramides
US7077869B2 (en) 2000-11-08 2006-07-18 L'oreal S.A. Composition for bleaching or permanent waving of keratinous fibers comprising a cationic associative polyurethane
US20040019981A1 (en) * 2000-11-08 2004-02-05 Francois Cottard Direct dyeing composition for keratinous fibres comprising a cationic associative polyurethane
US20040025266A1 (en) * 2000-11-08 2004-02-12 Francois Cottard Oxidation dyeing composition for karatinous fibres comprising a cationic associative polyurethane
US7108726B2 (en) 2000-11-08 2006-09-19 L'oreal S.A. Direct dyeing composition for keratinous fibres comprising a cationic associative polyurethane
US20040034946A1 (en) * 2000-11-08 2004-02-26 Frederic Legrand Composition for bleaching or permanent waving of keratinous fibers comprising a cationic associative polyurethane
US7101405B2 (en) 2000-11-08 2006-09-05 L'oreal S.A. Oxidation dyeing composition for karatinous fibers comprising a cationic associative polyurethane
US20040034947A1 (en) * 2000-11-08 2004-02-26 Frederic Legrand Bleachng composition for keratinous fibres comprising an associate polyurethane
US7066965B2 (en) 2000-11-08 2006-06-27 L'oreal S.A. Bleaching composition for keratinous fibers comprising an associate polyurethane
US20040037796A1 (en) * 2000-11-20 2004-02-26 Francois Cottard Composition for treating keratinous materials comprising a cationic associative polyurethane polymer and a protecting or conditioning agent
US7914775B2 (en) 2000-11-20 2011-03-29 L'oreal S.A. Composition for treating keratinous materials comprising a cationic associative polyurethane polymer and a protecting or conditioning agent
US7431740B2 (en) 2000-12-04 2008-10-07 L'oreal, S.A. Oxidation dyeing composition for keratinous fibers comprising an associative polymer and a pearling agent
US20040049861A1 (en) * 2000-12-04 2004-03-18 Francois Cottard Oxidation dyeing composition for keratinous fibres comprising an associative polymer and a pearling agent
US20040060126A1 (en) * 2000-12-04 2004-04-01 Francois Cottard Dyeing composition for keratinous fibres comprising an associative polymer and a polymer with acrylamide units, dialkyldiallylammonium halide, and vinylic carboxylic acid
US7364594B2 (en) 2000-12-04 2008-04-29 L'oreal S.A. Dyeing composition for keratinous fibres comprising an associative polymer and a polymer with acrylamide units, dialkyldiallylammonium halide, and vinylic carboxylic acid
US20040115156A1 (en) * 2001-01-26 2004-06-17 De La Mettrie Roland Cosmetic composition comprising a fixing polymer and a cationic poly(vinyllactam)
US7220285B2 (en) 2001-02-02 2007-05-22 L'oreal S.A. Pulverulent composition for bleaching human keratin fibers
US20020157193A1 (en) * 2001-02-02 2002-10-31 Frederic Legrand Pulverulent composition for bleaching human keratin fibers
US20060191081A1 (en) * 2001-02-02 2006-08-31 L'oreal, S.A. Pulverulent composition for bleaching human keratin fibers
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
US6919073B2 (en) 2001-05-16 2005-07-19 L'oreal S.A. Pulverulent composition for bleaching human keratin fibers
US20050201960A1 (en) * 2001-05-16 2005-09-15 L'oreal S.A. Pulverulent composition for bleaching human keratin fibers
US20030023782A1 (en) * 2001-07-26 2003-01-30 International Business Machines Corp. Microprocessor system bus protocol providing a fully pipelined input/output DMA write mechanism
US7402180B2 (en) 2001-07-27 2008-07-22 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
US20060248664A1 (en) * 2001-07-27 2006-11-09 Patricia Vuarier 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
US20030074747A1 (en) * 2001-07-27 2003-04-24 Patricia Vuarier 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
US7258852B2 (en) 2001-09-11 2007-08-21 L'oreal S.A. Cosmetic compositions containing a methacrylic acid copolymer and an oil, and uses thereof
US20040001796A9 (en) * 2001-09-11 2004-01-01 Mireille Maubru Cosmetic compositions containing a methacrylic acid copolymer, a dimethicone, a nacreous agent and a cationic polymer, and uses thereof
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US7217296B2 (en) 2001-09-28 2007-05-15 L'oreal S.A. Dyeing composition with a lightening effect for human keratin materials comprising at least one fluorescent dye
US20030140429A1 (en) * 2001-11-08 2003-07-31 Frederic Legrand Keratin fibre dyeing composition comprising a particular aminosilicone
US7220408B2 (en) 2001-11-08 2007-05-22 L'oreal, S.A. Cosmetic compositions containing a particular aminosilicone and a thickener, and uses thereof
US6846333B2 (en) 2001-11-08 2005-01-25 L'oreal, S.A. Keratin fiber dyeing composition comprising a particular aminosilicone
US7485289B2 (en) 2001-11-08 2009-02-03 L'oreal, S.A. Cosmetic compositions containing a particular aminosilicone and a conditioner, and uses thereof
US7510705B2 (en) 2001-11-08 2009-03-31 L'oreal, S.A. Process for permanently reshaping the hair using particular aminosilicones
US20030147842A1 (en) * 2001-11-08 2003-08-07 Serge Restle Cosmetic compositions containing a particular aminosilicone and a conditioner, and uses thereof
US7504094B2 (en) 2001-11-08 2009-03-17 L'oreal, S.A. Cosmetic compositions containing a particular aminosilicone and a thickener, and uses thereof
US7128902B2 (en) 2001-11-08 2006-10-31 L'oreal, Sa Reducing composition for treating keratin fibres, comprising a particular aminosilicone
US7223385B2 (en) 2001-11-08 2007-05-29 L'oreal S.A. Cosmetic compositions containing a particular aminosilicone and a conditioner, and uses thereof
US7135167B2 (en) 2001-11-08 2006-11-14 L'oreal, Sa Oxidizing composition for treating keratin fibers, comprising a particular aminosilicone
US7138109B2 (en) 2001-11-08 2006-11-21 L'oreal, Sa Use of particular aminosilicones as a pre-or post-treatment of processes for bleaching keratin fibres
US7211268B2 (en) 2001-11-15 2007-05-01 L'oreal S.A. Preparation of polysaccharide betainate type compounds, compounds obtained, their use and compositions comprising them
US20030147818A1 (en) * 2001-11-15 2003-08-07 Claude Dubief Preparation of polysaccharide betainate type compounds, compounds obtained, their use and compositions comprising them
US20070160557A1 (en) * 2001-11-15 2007-07-12 L'oreal S.A. Preparation of polysaccharide betainate type compounds, compounds obtained, their use and compositions comprising them
US20050125912A1 (en) * 2001-12-21 2005-06-16 Patricia Desenne Dyeing composition for keratinous fibers comprising an oxyethylene rapeseed fatty acid amide
US7153331B2 (en) 2001-12-21 2006-12-26 L'oreal S.A. Dyeing composition for keratinous fibers comprising an oxyethylene rapeseed fatty acid amide
US7498022B2 (en) 2002-03-28 2009-03-03 L'oreal S.A. Cosmetic composition comprising at least one anionic surfactant, at least one cationic polymer and at least one amphiphilic, branched block acrylic copolymer and method for treating hair using such a composition
US20030223948A1 (en) * 2002-03-28 2003-12-04 Mireille Maubru Cosmetic composition comprising at least one anionic surfactant, at least one cationic polymer and at least one amphiphilic, branched block acrylic copolymer and method for treating hair using such a composition
US7232561B2 (en) 2002-05-31 2007-06-19 L'oreal S.A. Washing compositions comprising at least one amphiphilic block copolymer and at least one cationic or amphoteric polymer
US20040039101A1 (en) * 2002-05-31 2004-02-26 Claude Dubief Washing compositions comprising at least one amphiphilic block copolymer and at least one cationic or amphoteric polymer
US7157413B2 (en) 2002-07-08 2007-01-02 L'oreal Detergent cosmetic compositions comprising an anionic surfactant, an amphoteric, cationic, and/or nonionic surfactant, and a polysacchardie, and use thereof
US20040077510A1 (en) * 2002-07-08 2004-04-22 Pascale Lazzeri Detergent cosmetic compositions comprising an anionic surfactant, an amphoteric, cationic, and/or nonionic surfactant, and a polysacchardie, and use thereof
US20050101499A9 (en) * 2002-07-08 2005-05-12 Pascale Lazzeri Detergent cosmetic compositions comprising an anionic surfactant, an amphoteric, cationic, and/or nonionic surfactant, and a polysacchardie, and use thereof
US20040208843A1 (en) * 2002-09-24 2004-10-21 Gabin Vic Cosmetic composition comprising an exogenous ligand-receptor system adsorbed or covalently attached to keratin materials, and hair treatment using this composition or constituent elements thereof
US20040133995A1 (en) * 2002-10-21 2004-07-15 Francois Cottard Oxidation dyeing composition for keratin fibers comprising a cationic poly(vinyllactam) and at least one C10-C14 fatty acid, methods and devices for oxidation dyeing
US7323015B2 (en) 2002-10-21 2008-01-29 L'oreal S.A. Oxidation dyeing composition for keratin fibers comprising a cationic poly(vinyllactam) and at least One C10-C14 fatty alcohol, methods and devices for oxidation dyeing
US7147672B2 (en) 2002-10-21 2006-12-12 L'oreal S.A. Oxidation dyeing composition for keratin fibers comprising a cationic poly(vinyllactam) and at least one C10-C14 fatty acid, methods and devices for oxidation dyeing
US20040133994A1 (en) * 2002-10-21 2004-07-15 Francois Cottard Oxidation dyeing composition for keratin fibers comprising a cationic poly(vinyllactam) and at least One C10-C14 fatty alcohol, methods and devices for oxidation dyeing
US7329287B2 (en) 2002-12-06 2008-02-12 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
US20080104775A1 (en) * 2002-12-06 2008-05-08 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
US7771491B2 (en) 2002-12-06 2010-08-10 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
US20040163186A1 (en) * 2002-12-06 2004-08-26 Frederic Simonet 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
US7326256B2 (en) 2002-12-06 2008-02-05 L'ORéAL S.A. Composition for the oxidation dyeing of keratin fibers, comprising at least one non-oxyalkenylated fatty alcohol, at least one oxidation dye, at least one associative polymer, and at least one amide of an alkanolamine and a C14-C30 fatty acid
US20040205902A1 (en) * 2002-12-06 2004-10-21 Francois Cottard Composition for the oxidation dyeing of keratin fibers, comprising at least one non-oxyalkenylated fatty alcohol, at least one oxidation dye, at least one associative polymer, and at least one amide of an alkanolamine and a C14-C30 fatty acid
US20040180030A1 (en) * 2002-12-19 2004-09-16 Mireille Maubru Cosmetic compositions comprising at least one alkylamphohydroxyalkylsulphonate amphoteric surfactant and at least one nacreous agent and/or opacifier, and uses thereof
US7261744B2 (en) 2002-12-24 2007-08-28 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
US20040122807A1 (en) * 2002-12-24 2004-06-24 Hamilton Darin E. Methods and systems for performing search interpretation
US7226486B2 (en) 2003-01-16 2007-06-05 L'oreal S.A Ready-to-use bleaching compositions, preparation process and bleaching process
US20040226110A1 (en) * 2003-01-16 2004-11-18 Frederic Legrand Ready-to-use bleaching compositions, preparation process and bleaching process
US20040234485A1 (en) * 2003-03-11 2004-11-25 Mireille Maubru Cosmetic compositions comprising at least one crosslinked copolymer, at least one insoluble mineral particle and at least one polymer, and uses thereof
US7708981B2 (en) 2003-03-11 2010-05-04 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
US7267696B2 (en) 2003-03-25 2007-09-11 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
US20040221401A1 (en) * 2003-03-25 2004-11-11 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
US20050011017A1 (en) * 2003-03-25 2005-01-20 L'oreal S.A. Oxidizing composition comprising hydroxycarboxylic acids and salts thereof as complexing agents for dyeing, bleaching or permanently reshaping keratin fibres
US20050036970A1 (en) * 2003-03-25 2005-02-17 L'oreal S.A. Reducing compositions for bleaching or permanently reshaping keratin fibres comprising polycarboxylic acids and salts thereof as complexing agents
US7303588B2 (en) 2003-03-25 2007-12-04 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
US20050039270A1 (en) * 2003-03-25 2005-02-24 L'oreal S.A. Use of polycarboxylic acids and salts thereof as complexing agents in oxidizing compositions for dyeing, bleaching or permanently reshaping keratin fibres
US20040237217A1 (en) * 2003-03-25 2004-12-02 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
US7186278B2 (en) 2003-04-01 2007-03-06 L'oreal S.A. Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one compound comprising an acid functional group and processes therefor
US7192454B2 (en) 2003-04-01 2007-03-20 L'oreal S.A. Composition for dyeing human keratin materials, comprising a fluorescent dye and a particular sequestering agent, process therefor and use thereof
US7150764B2 (en) 2003-04-01 2006-12-19 L'oreal S.A. Composition for dyeing a human keratin material, comprising at least one fluorescent dye and at least one insoluble conditioning agent, process thereof, use thereof, and devices thereof
US7736631B2 (en) 2003-04-01 2010-06-15 L'oreal S.A. Cosmetic dye composition with a lightening effect for human keratin materials, comprising at least one fluorescent dye and at least one aminosilicone, and process of dyeing
US7147673B2 (en) 2003-04-01 2006-12-12 L'oreal S.A. Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one insoluble polyorganosiloxane conditioning polymer, process therefor and use thereof
US7195651B2 (en) 2003-04-01 2007-03-27 L'oreal S.A. Cosmetic composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one cationic polymer, and a dyeing process therefor
US7204860B2 (en) 2003-04-01 2007-04-17 L'oreal Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one polyol, process therefor and use thereof
US7195650B2 (en) 2003-04-01 2007-03-27 L'oreal S.A. Process for dyeing, with a lightening effect, human keratin fibers that have been permanently reshaped, using at least one composition comprising at least one fluorescent dye
US7198650B2 (en) 2003-04-01 2007-04-03 L'oreal S.A. Method of dyeing human keratin materials with a lightening effect with compositions comprising at least one fluorescent dye and at least one amphoteric or nonionic surfactant, composition thereof, process thereof, and device therefor
US7208018B2 (en) 2003-04-01 2007-04-24 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
US7303589B2 (en) 2003-04-01 2007-12-04 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
US7250064B2 (en) 2003-04-01 2007-07-31 L'oreal S.A. Dye composition comprising at least one fluorescent dye and a non-associative thickening polymer for human keratin materials, process therefor, and method thereof
US20100005600A1 (en) * 2003-05-09 2010-01-14 L'oreal S.A. Process for treating keratin fibres by applying heat
US7608115B2 (en) 2003-05-09 2009-10-27 L'oreal S.A. Process for treating keratin fibres by applying heat
US20070174974A1 (en) * 2003-05-09 2007-08-02 De La Mettrie Roland Process for treating keratin fibres by applying heat
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US20050208005A1 (en) * 2003-08-11 2005-09-22 Franck Giroud Cosmetic composition comprising particles having a core-shell structure
US20050158262A1 (en) * 2003-12-19 2005-07-21 Eric Parris Cosmetic composition comprising a cationic agent, a polymer comprising a hetero atom and an oil, and cosmetic treatment process
US20050169873A1 (en) * 2003-12-19 2005-08-04 Isabelle Rollat Styling composition comprising, in a predominantly aqueous medium, an elastic cationic polyurethane, processes using it and uses thereof
US20070237733A1 (en) * 2004-01-05 2007-10-11 Frederic Simonet Cosmetic Composition of Water-in-Water Emulsion type Based on Surfactants and Cationic Polymers
US20050232885A1 (en) * 2004-01-07 2005-10-20 L'oreal Detergent cosmetic compositions comprising at least one surfactant, at least one drawing polymer and at least one nonsilicone conditioner, and use thereof
US20050175569A1 (en) * 2004-01-07 2005-08-11 Geraldine Fack Cosmetic compositions comprising a cation, a drawing polymer and a thickener, and cosmetic treatment processes
US20050188475A1 (en) * 2004-01-07 2005-09-01 Alain Lagrange Dyeing composition comprising at least one fluorindine compound for the dyeing of keratinic fibers, dyeing process comprising the composition and compound
US7294152B2 (en) 2004-01-07 2007-11-13 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
US20070141006A1 (en) * 2004-03-17 2007-06-21 Aude Livoreil Cosmetic compositions containing modified polyamines and the uses thereof
US7976831B2 (en) 2004-04-02 2011-07-12 L'oreal S.A. Method for treating hair fibers
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US20050232884A1 (en) * 2004-04-02 2005-10-20 Thomas Fondin Method for treating hair fibers
US20050232883A1 (en) * 2004-04-02 2005-10-20 Thomas Fondin Method for treating hair fibers
US20060025318A1 (en) * 2004-04-22 2006-02-02 Mireille Maubru Composition for washing and conditioning keratin materials, comprising a carboxyalkyl starch, and process for the use thereof
US20060057096A1 (en) * 2004-09-08 2006-03-16 Pascale Lazzeri Cosmetic composition comprising at least one cationic surfactant, at least one aminated silicone, at least one fatty alcohol, and at least one diol
US20080119554A1 (en) * 2004-11-26 2008-05-22 Rajiv Jalan Compositions Comprising Ornithine And Phenylacetate Or Phenylbutyrate For Treating Hepatic Encephalopathy
US8790623B2 (en) 2005-01-18 2014-07-29 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
US7550015B2 (en) 2005-03-31 2009-06-23 L'oreal S.A. Dye composition with a reduced content of starting materials, and process for dyeing keratin fibers using the same
US7575605B2 (en) 2005-03-31 2009-08-18 L'oreal S.A. Dye composition comprising at least one glycerol ester and a process for dyeing keratin fibers using the composition
US20060265817A1 (en) * 2005-03-31 2006-11-30 Frederic Legrand Dye composition comprising at least one non-ionic associative polymer and process for dyeing keratin fibers using same
US7442214B2 (en) 2005-03-31 2008-10-28 L'oreal S.A. Dye composition comprising at least one non-ionic associative polymer and process for dyeing keratin fibers using same
US7651533B2 (en) 2005-03-31 2010-01-26 Oreal Dye composition with a reduced content of starting materials, process for dyeing keratin fibers using the same and device therefor
US7569078B2 (en) 2005-03-31 2009-08-04 L'oreal S.A. Dye composition comprising at least one cellulose and process for dyeing keratin fibers using the dye composition
US7578854B2 (en) 2005-03-31 2009-08-25 L'oreal S.A. Dye composition comprising at least one fatty acid ester and process for dyeing keratin fibers using the same
US20060257339A1 (en) * 2005-05-13 2006-11-16 L'oreal Use of conductive polymer nanofibers for treating keratinous surfaces
US20070074356A1 (en) * 2005-09-29 2007-04-05 Boris Lalleman Process for the photoprotective treatment of artificially dyed keratin fibers by application of a liquid water/steam mixture
US7998464B2 (en) 2005-09-29 2011-08-16 L'oreal S.A. Process for the photoprotective treatment of artificially dyed keratin fibers by application of a liquid water/steam mixture
US20070105734A1 (en) * 2005-10-28 2007-05-10 Sandrine Decoster Composition for washing keratin materials and cosmetic treatment process using said composition
US20070104668A1 (en) * 2005-10-28 2007-05-10 Virginie Masse Composition for the care of keratin material and cosmetic treatment process using said composition
US20070104747A1 (en) * 2005-10-28 2007-05-10 Virginie Masse Cosmetic composition comprising at least one anti-dandruff agent and also oxyethylenated sorbitan monolaurate, and cosmetic treatment process using said composition
US8586014B2 (en) 2005-10-28 2013-11-19 L'oreal Composition for the care of keratin material and cosmetic treatment process using said composition
US7867969B2 (en) 2005-10-28 2011-01-11 L'oreal S.A. Composition for washing keratin materials comprising a magnesium salt anionic surfactant
US20090068124A1 (en) * 2006-03-03 2009-03-12 Raphael Beumer Novel heterocyclic substituted condensation polymers
US8951509B2 (en) * 2006-03-03 2015-02-10 Dsm Ip Assets B.V. Heterocyclic substituted condensation polymers
US20070251026A1 (en) * 2006-04-12 2007-11-01 Boris Lalleman Unsaturated fatty substances for protecting the color of artificially dyed keratin fibers with respect to washing; and dyeing processes
US20100047201A1 (en) * 2006-04-12 2010-02-25 L'oreal, S.A. Unsaturated fatty substances for protecting the color of artificially dyed keratin fibers with respect to washing; and dyeing processes
US7799093B2 (en) 2006-10-25 2010-09-21 L'ORéAL S.A. Coloring composition of keratinous fibers comprising at least one polysiloxane/polyurea block copolymer
US20110182842A1 (en) * 2009-12-23 2011-07-28 Carine Aires Cosmetic composition comprising at least one organosilicon compound, at least two anionic surfactants and at least one amphoteric surfactant
US20110155163A1 (en) * 2009-12-23 2011-06-30 Viravau Valerie Cosmetic composition comprising at least one organosilicon compound, at least one anionic surfactant and at least one nonionic thickener, and process using the composition
US20110158927A1 (en) * 2009-12-23 2011-06-30 Viravau Valerie Cosmetic composition comprising at least one organosilicon compound, at least one anionic surfactant and at least one cationic polymer
US9248083B2 (en) 2009-12-23 2016-02-02 L'oreal Cosmetic composition comprising at least one organosilicon compound, at least two anionic surfactants and at least one amphoteric surfactant
EP2438906A3 (en) * 2010-08-17 2015-06-03 Henkel AG & Co. KGaA Matting additive for blonding agents
US8784506B2 (en) 2010-11-02 2014-07-22 L'oreal Dye composition having a low content of ammonia
US8802066B2 (en) 2010-12-21 2014-08-12 L'oreal Cosmetic composition comprising a particular zinc salt and an amino silicone
US9375393B2 (en) 2010-12-21 2016-06-28 L'oreal Composition comprising a non-nitrogenous zinc salt and a particular cationic surfactant
US8828368B2 (en) 2010-12-21 2014-09-09 L'oreal Cosmetic composition comprising a particular zinc salt and a starch
US9776020B2 (en) 2011-05-27 2017-10-03 L'oreal Composition comprising an alkoxysilane and a modified starch, and cosmetic use thereof
US9610241B2 (en) 2011-06-01 2017-04-04 L'oreal Process for treating straightened keratin fibres
US9180086B2 (en) 2011-06-01 2015-11-10 L'oreal Process for treating straightened keratin fibres
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US9060944B2 (en) 2011-07-05 2015-06-23 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
US9066890B2 (en) 2011-07-05 2015-06-30 L'oreal Dye composition comprising an alkoxylated fatty alcohol ether and a fatty alcohol
US9198851B2 (en) 2012-01-23 2015-12-01 L'oreal Composition comprising at least one specific alkoxysilane polymer
US10201483B2 (en) 2012-08-02 2019-02-12 L'oreal Dye composition in cream form comprising at least one oil and little or no solid fatty alcohol, dyeing process and suitable device
US10137063B2 (en) 2012-08-02 2018-11-27 L'oreal Dye composition comprising nonionic guar gum or a nonionic derivative thereof, process and device for the same
US10226411B2 (en) 2012-08-02 2019-03-12 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
US9827185B2 (en) 2012-08-02 2017-11-28 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
US9493475B2 (en) 2012-09-18 2016-11-15 Devan Chemicals Nv Textile treatment compounds and compositions
US10231915B2 (en) 2015-05-01 2019-03-19 L'oreal Compositions for altering the color of hair
US10058494B2 (en) 2015-11-24 2018-08-28 L'oreal Compositions for altering the color of hair
US9974725B1 (en) 2017-05-24 2018-05-22 L'oreal Methods for treating chemically relaxed hair

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NL176223C (en) 1985-03-18
DK134141B (en) 1976-09-20
DE2258222B2 (en) 1982-02-04
BE792004A1 (en)
GB1416454A (en) 1975-12-03
ATA1010472A (en) 1975-12-15
IT1050457B (en) 1981-03-10
AU4934972A (en) 1974-05-30
FR2162025B1 (en) 1976-01-30
CH559038A5 (en) 1975-02-28
FR2162025A1 (en) 1973-07-13
DE2258222C3 (en) 1982-09-23
LU64371A1 (en) 1973-06-21
JPS4875732A (en) 1973-10-12
ES437446A1 (en) 1977-05-01
CA1026039A (en) 1978-02-07
NL176223B (en) 1984-10-16
DK134141C (en) 1977-02-21
DE2258222A1 (en) 1973-06-14
BR7208360D0 (en) 1973-08-30
AT331990B (en) 1976-09-10
BE792004A (en) 1973-05-28
CA1026039A1 (en)
JPS6025410B2 (en) 1985-06-18
ES409075A1 (en) 1976-03-01
NL7216145A (en) 1973-06-01
AR213060A1 (en) 1978-12-15

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