Connect public, paid and private patent data with Google Patents Public Datasets

Hair fixing compositions containing N-alkyl acrylamide or methacrylamide interpolymer

Download PDF

Info

Publication number
US3927199A
US3927199A US38832573A US3927199A US 3927199 A US3927199 A US 3927199A US 38832573 A US38832573 A US 38832573A US 3927199 A US3927199 A US 3927199A
Authority
US
Grant status
Grant
Patent type
Prior art keywords
hair
fixing
aerosol
acid
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
Inventor
Albert L Micchelli
Gerard J Legato
Stuart H Ganslaw
Lawrence D Schuler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
National Starch and Chemical Corp
Original Assignee
National Starch and Chemical Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Grant date

Links

Images

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • 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
    • A61K8/81Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/52Amides or imides
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/52Amides or imides
    • C08F20/54Amides
    • 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
    • Y10S526/00Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S526/923Ethylenic monomers containing at least one salt group

Abstract

Hair fixing compositions such as aerosol hair sprays and hair setting lotions containing as the film forming resinous binder therein an interpolymer derived from (1) N-alkyl acrylamides or methacrylamides, (2) acidic film forming comonomers, and (3) at least one polymerizable comonomer.

Description

United States Patent Micchelli et a1.

National Starch and Chemical Corporation, Clifton, NJ.

Filed: Aug. 13, 1973 Appl. No.: 388,325

Related US. Application Data Continuation-impart of Ser. No. 244,264, April 14, 1972, abandoned.

Assignee:

US. Cl 424/47; 260/296 ME; 260/296 T; 260/296 TA; 260/33.4 R; 260/338 UA; 260/785 BB; 260/8013; 260/808; 424/DlG. 1; 424/DIG. 2; 424/71; 424/78; 424/81;

424/359 Int. Cl. A61K 7/11 Field of Search 424/DIG. 1, DIG. 2, 47,

424/71, 81, 78; 260/785 R, 80.73, 29.6 T, 29.6 TA, 29.6 ME, 33.8 UA, 33.4 R

[ Dec. 16, 1975 [56] References Cited UNITED STATES PATENTS 3,257,281 6/1966 Maeder 424/47 3,405,084 10/1968 Bohac et a1... 424/71 X 3,493,500 2/1970 Volk et a1. 260/8073 X 3,577,517 5/1971 Kubot et a1 424/47 3,577,518 5/1971 Shepherd et al. 424/47 3,726,288 4/1973 Nowak et a1 424/71 X 3,735,003 5/1973 Zimmer et al. 424/47 3,753,958 8/1973 Wingler et a1. 260/785 R FOREIGN PATENTS OR APPLICATIONS 1,141,255 1/1969 United Kingdom 424/71 1,814,115 7/1969 Germany 260/8073 2,047,655 4/1971 Germany 424/71 Primary ExaminerSam Rosen Assistant ExaminerVera C. Clarke [57] ABSTRACT 10 Claims, No Drawings HAIR FIXING COMPOSITIONS CONTAINING N-ALKYL ACRYLAMIDE OR METHACRYLAMIDE INTERPOLYMER This is a continuation-in-part application of our copending application Ser. No. 244,264 filed Apr. 14, 1972, now abandoned.

This invention relates to hair fixing compositions containing unique film forming polymeric binders therein.

In order to be highly effective in hair fixing compositions such as aerosol hair sprays and hair setting tions, the film forming polymeric binders utilized therein as well as the films derived therefrom must meet a rigid set of requirements. Thus, the binders used in such formulations should be soluble in anhydrous organic solvents, yet the films cast from such hair fixing formulations should, ordinarily, either be water soluble or water dispersible in order to facilitate their easy removal from the users hair. As is readily visualized, this is an unusual combination of properties which is further complicated by the requirement that the binder used in such formulations be completely compatible with the solvents and/or propellants ordinarily employed therein. Furthermore, the binders used should show little or no tendency to interact with the perfumes or other optional ingredients utilized in hair fixing formulations.

In addition, the films cast from either aqueous or organic solvent solutions of these binders should be flexible and should simultaneously exhibit sufficient strength and elasticity; they should exhibit good adhesion to hair so as to avoid the occurrence of dusting or flaking when the hair is subjected to varying stresses; they should readily allow the hair to be recombed; they should maintain a non-tacky state despite humid conditions; they should be clear, transparent and glossy and should possess good antistatic properties; and-they should be easily removable by the use of water and/or soap or shampoo.

Needless to say, many polymeric systems have been utilized in an attempt to meet these stringent requirements. Among these are included: polyvinylpyrrolidone, copolymers of N-vinyl pyrrolidone. with vinyl acetate, 5-5 '-dimethyl hydantoinformaldehyde resins, and copolymers of methyl vinyl ethers and maleic acid half esters, etc. Though each of the latter systems has met at least some of the above cited requirements, none has exhibited all of these requirements to an optimum degree.

It is the prime object of this invention to provide film forming polymers for use as binders in hair fixing formulations, said polymers exhibiting most or all of the above-described properties required in such binders.

It is a further object to prepare effective aerosol hair sprays, hair setting lotions and the like utilizing these polymeric binders.

Various other objects and advantages of this invention will become apparent from a reading of the disclosure which follows hereinafter.

We have now discovered that all of the previously described requirements for an effective hair fixing formulation are met by utilizing the novel class of polymers hereinafter described as the film forming binder component'of the hair fixing compositions of this invention. Particularly significant are the broadened solubility and compatibility characteristics exhibited by these binders. Thus. for example. they display a greater degree of solubility in the organic solvents typically used in aerosol hair sprays as well as in the aqueous solvent systems typically utilized in wave set lotions. In addition, they exhibit greater compatibility with the hydrocarbon propellants typically used in aerosol hair sprays. Furthermore, if neutralization of these resins is desired by the practitioner, the lower levels of neutralization that can be used insure the deposition, onto the hair, of films having a minimal degree of water sensitivity which, although they are readily removable by washing, provide a greater degree of holding power and thereby enable the thus treated hair to retain its shape and body.

The film forming polymers (i.e. interpolymers) utilizable as binders in the hair fixing compositions of this invention comprise polymers containing moieties derived from l) at least one comonomer which is an N-alkyl acrylamide or methacrylamide, (2) at least one acidic comonomer containing one or more available carboxyl groups, and (3) at least one comonomer selected from a group of copolymerizable comonomers.

The applicable N-substituted acrylamides or methacrylamides are substituted with alkyl radicals containing from 2-12 carbon atoms. Among the applicable acrylamides and methacrylamides are included N-ethyl acrylamide, N-tettiary-butyl acrylamide, N-n-octyl acrylamide, N-teltiary-octyl acrylamide, N-decyl acrylamide, N-dodecyl acrylamide, as well as the corresponding methacrylamides.

The following list of monomers are representative of the applicable acidic film forming comonomers which contain at least one available carboxylic acid group: acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid and the C -C alkyl half esters of maleic and fumaric acids such, for example, as methyl hydrogen maleate and butyl hydrogen fumarate as well as any other acidic monomers which are capable of being copolymerized with the particular interpolymer system whose use is desired by the practitioner. As is known to those skilled in the art, the acidic comonomer(s) must be so chosen as to be readily polymerizable with the selected interpolymer system.

The acidic comonomers make it possible for the. resultant copolymer to be neutralized by reaction with an appropriate base in order that it may ultimately exhibit the requisite water solubility. These acidic comonomers may be neutralized prior to their being incorporated into the ultimate hair fixing formulation thus permitting these formulations to be removed from the hair merely by rinsing with water. However, if such copolymers are not pre-neutralized in this manner. removal may still be readily effected by the application of an alkaline aqueous solution, for example, soap and water. It should be noted that for purposes of this invention the term water solubility is meant to include both water solubility in its usual meaning as well as water dispersibility wherein the resulting films are sufficiently hydrated and softened by contact with water so as to be easily removed from the hair by the application of water and either soap or shampoo.

In order to modify or enhance certain properties of I the polymeric binder, for example. adherance to the atoms such as methyl, ethyl, propyl, butyl, octyl and lauryl alcohols; hydroxyalkyl esters of acrylic and methacrylic acids such as hydroxypropyl acrylate and methacrylate, hydroxybutyl acrylate and methacrylate, hydroxystearyl acrylate and methacrylate and hydroxyethyl acrylate and methacrylate; alkyl (C -C amino alkyl (C -C esters of acrylic and methacrylic acids such as N, N diethylaminoethyl acrylate, N-tertbutylaminopropyl acrylate, N, N -dimethylaminoethyl methacrylate, N-tert.-butylaminoethyl methacrylate and the quatemization product of dimethylaminoethyl methacrylate and dimethyl sulfate, diethyl sulfate and the like; diacetone acrylamide; vinyl esters such as vinyl acetate and vinyl propionate; and styrene monomers such as styrene and alpha-methyl styrene.

In order to provide binders which will function particularly efficiently in the novel hair fixing compositions of this invention, the interpolymer will contain from about 30-60% of the N-substituted acrylamide or methacrylamide, from -20%, (and 12-18%, preferrably) of the acidic comonomer, and up to 55% of at least one copolymerizable comonomer; these percentages being based on the total weight of the interpolymer. The percentages given herein and in the claims are to be taken so that the comonomers of the interpolymer will total to 100%.

Applicants preferred composition (preferred because of its combination of excellent properties of curl retention, adherance to the hair, clari'ty, gloss, and the like) will contain from 35-45% of N-tert.-octyl acrylamide. from 12-18% of acrylic or methacrylic acid, from 32-38% of methyl methacrylate, from 2-10% of hydroxypropyl acrylate, and from 2-10% of an alkyl (C -C amino alkyl (C -C acrylate or methacrylate.

As for the actual preparation of these polymeric film forming binders, there may be employed any of the usual vinyl polymerization methods which are well known to those skilled in the art and which are particularly suited for the polymer whose preparation is desired. Thus, the polymers may be prepared by means of free radical initiated processes utilizing bulk, suspension, solution, or emulsion polymerization techniques. The polymers may, if desired, be converted into relatively large particles known as beads or pearls by disp'ersing the solution polymerized polymer in water and thereafter driving off the solvent followed by separating and drying the particles.

It should be noted that the polymer binders of this invention may be partially neutralized prior to their being incorporated into the ultimate hair fixing formulation thus permitting them to be removed from the hair merely by rinsing with water. This may be accomplished by reacting the polymer, in the form of a solution in an organic solvent, with or without added water, with a concentration of an alkaline reagent (neutralizing agent) which is equivalent on a molar basis to a minimum of about 50% of the available carboxyl groups present on the polymer. Applicable alkaline materials which may be utilized in this manner include: sodium and potassium hydroxide; ammonia; primary, secondary and tertiary amines; alkanolamines; and, hydroxyamines such as 2-amino-2-methyl-propanol and 2-amino-2-methyl-l,3-propanediol. However, if such polymers are not pre-neutralized in this manner, their eventual removal may still be readily effected by the application of weak alkaline aqueous solution. e.g., soap and water.

In utilizing the above-described polymeric binders in the preparation of aerosol hair sprays, the other essential ingredients which must be admixed therewith are a solvent and a propellant, although 'in some instances the propellant will serve both the latter functions. The preferred solvents are alcohols such as ethanol and isopropanol. In addition to their solubility properties, the prime advantages of these solvents are their ability to dry quickly, their minimal effect on the metal containers ordinarily utilized for these pressurized aerosol formulations and their accepted use in cosmetic applications. Other solvents which may be used include methylene chloride and l,l,l-trichloroethane, etc.

Various types of aerosol propellants are well known to those skilled in the art. Thus, the commonly used propellants include trichlorofluoromethane, dichlorodifluoromethane, isobutane and propane, etc., as well as mixtures of the latter propellants. These propellants are readily compatible with the binder-solvent solutions utilized in this invention.

In general, the method for preparing the hair spray formulations of this invention merely involves dissolving or diluting the polymer in the selected solvents, adding any modifying agents whose presence may be desired, and thereupon combining the resulting solution with the selected aerosol propellant.

Thus, it may be noted that the novel hair spray formulations of this invention will in all cases contain at least three essential components. The first of the latter components will be what may be termed as the active ingredient comprising one or more of the abovedescribed polymers which serves as the binder for the formulation. Secondly, there will be one or more solvents which serve as vehicles for the binder. And, finally, there is the propellant which serves to effect the discharge of the aforedescribed binder and vehicle from the container wherein the formulation is packaged. Water is not ordinarily present, but may be included in some formulations.

With regard to proportions, the final hair spray formulations typically contain the polymeric binder in a concentration ranging from about 0.25 to 7%, by weight; the solvent in a concentration ranging from about 8 to 90%, by weight; and, the propellant concentration ranging from 10 to by weight. The latter proportions should, however, be considered asbeing merely illustrative inasmuch as it may well be possible to prepare operable formulations having concentrations of components which fall outside the above suggested ranges.

In addition, it should be noted that the unique film forming polymers of this invention are equally effective when utilized in hair setting lotions, which usually consist of a solution (or dispersion) of the polymer in a suitable organic solvent, such as alcohol, together with water. Such lotions may be directly applied to the hair or they may be sprayed thereon utilizing conventional spray nozzles. The application of such lotions may take place prior to, during, or after the desired hair style has been achieved.

The latter hair lotions are prepared by merely admixing the film forming polymer with the selected solvent, such solvents usually comprising a mixture, with water. of an alcohol such as ethanol or isopropanol. With regard to proportions, the lotions typically contain from about 0.5 to 7%. by weight. of the polymeric binder. while any desired ratio of alcohol to water in the solvent system may be utilized therein. An all alcohol system may also be used in some cases.

Comonomers N-tert.-octyl methacrylamide N-tert.-octyl acrylamide N tert=butyl acrylamide Acrylic Acid Methacrylic Acid ltaconic Acid Methyl Methacrylate Methyl Acrylate Tert.Butyl 'Methacrylate Hydroxypropyl Methacrylate Hydroxypropyl Acrylate Tert.-butyl Aminoethyl Methacrylate Dimethyl Aminoethyl Methacrylate N.N'-Dieth vlaminoethyl Acrylate Vinyl Acetate Diacetone Acrylamide to prepare the respective polymers being set forth in the following table:

Parts Polymer (Example No.)

Azobisisobulyronitrile substituted for benzoyl peroxide as free radical initiator.

Optional additives may be incorporated into the hair fixing formulations of this invention in order to modify certain properties thereof. Among these additives may be included: plasticizers such as glycols, phthalate esters and glycerine; silicones; emollients, lubricants and penetrants such as lanolin compounds, protein hydrolyzates and other protein derivatives, ethylene oxide adducts, and polyoxyethylene cholesterol; U.V. absorbers; dyes and other colorants; and, perfumes. As previously noted, the polymeric binders of this invention show little or no tendency to chemically interact with such additives.

The resulting hair fixing formulations exhibit all of the characteristics required of such a product. Their films are transparent, glossy, flexible, and strong. They possess good antistatic properties, adhere well to hair, are easily removed by soapy water or shampoos, allow the hair to be readily recombed, do not yellow on aging, do not become tacky when exposed to high humiditie's, and have excellent curl retention under high humidity conditions.

In the following examples, which further illustrate the embodiment of this invention, all parts given are by weight unless otherwise indicated.

EXAMPLES l-l 1 methyl methacrylate, 1.0 part benzoyl peroxide and 100 parts of ethanol. The contents were heated to the reflux temperature of the system and held there for a period of 6 hours whereupon an additional 1.0 part of benzoyl peroxide was added thereto. The system was then held at reflux for an additional 4 hours whereafter the reaction was cooled to 30C and the polymer No.1 recovered.

Additional polymers applicable for use in the hair fixing formulations of this invention were also prepared by means of the above-described procedure; the reagents and the concentrations in which they were used EXAMPLES 12-17 vessel was charged with 25% of a monomer mix con-- taining 40 parts tertiary-octyl acrylamide, l5 parts acrylic acid, 35 parts methyl methacrylate, 5 parts hydroxpropyl acrylate and 5 parts tertiary-butyl aminoethyl methacrylate. The system was heated to its reflux temperature whereupon the remainder of the monomer mix was added over a period of 4 hours. Upon completion of the monomer addition, an additional 1.0 part of benzoyl peroxide was added and the reaction held at reflux for further 4 hours. The system was cooled and polymer No.12 recovered therefrom.

Additional copolymers applicable for use in the hair fixing formulations of this invention were also prepared by the above described procedure; the reagents and the concentrations in which they were used to prepare the respective polymers being set forth in the following table:

Parts Polymer (Example No.)

Comonome rs 'lgl llllllll llE EEI'JIIII" EXAMPLES 18-23 Parts These examples illustrate the preparation of aerosol Wave Set Lem) (Example N0.) hair spray formulations typ1cal of the novel products of 34 25 26 5 thls lnverltlon' Anhydrous ethanol 4625 9170 A solution of the desired polymer in anhydrous ethawater 99344 50,000 nol was prepared and subsequently introduced into an available cflrbfmylic 100 6U acid groups neutrahzed aerosol container wh1ch had been charged with the in polymer desired propellant to an internal pressure of 30 lbs. per square inch gauge. The various modifying agents were 10 added to the Polymer-alcohol Solutlens Prior to When utilized, each of these wave setting lotions mtteduetton Into the propellant-Charged aerosol deposited a clear, glossy, flexible film which was readily tametremoved from the hair by a thorough washing with The reagents and the concentrations utilized for prewater. paring the Venous aerosol hair p y are Set forth l5 Summarizing, it is seen that this invention provides the tollowmg table: for the preparation of novel hair fixing formulations Parts Aerosol Spray (Example No.) 1s 19 20 21 22 23 Polymer No. 1 (dried) 0.50 Polymer No. 2 (dried) 0 250 7.000 Polymer No. 3 (dried) 0.500 2.000 Polymer No. 12 (dried) 0 50 2amino-2 methyl propanol 0.042 1.750 2amino-2 methyl- 0.059 0.136 1.3-propanediol Perfume oil 0.10 0.10 0.10 0.10 0.10 0.10

Polymethylpolysiloxane 0.250 Ethoxylated lanolin oil 0.50 0.500 0.50 Propoxylated oleyl alcohol 0.400 Hydrolyzed protein 0.70 Anhydrous ethanol 63.9 49.358 63.826 37.330 10.450 63.90 A :60 propellant mixture of dichlorodifluoromethane and trichlorofluoromethane 50.0 80.00 A :45:10 propellant mixture of trichlorofluoromethane: dichlorodifluoromethane: isobutane 35.0 35.0 35.00

Methylene Chloride 15.00 Vinyl Chloride 15.00 lsobutane 10.00

Dichlorodifluoromethane 20.00 7r of available carboxylic acid groups neutralized in polymer 55 100 58 81 EXAMPLES 24-26 These examples illustrate the preparation of wave setting lotions typical of the products of this invention.

The lotions noted in the following table were prepared by charging the specified ingredients into a reaction vessel equipped with means for mechanical agitation.

Parts Wave Set Lotion (Example N0.) 24 25 26 Polymer N0. 2 (dried) 0.500 3.000 7,000 2umino-2 methyl 0.156 0.750 1.300

propanol which are characterized by their excellent holding power as well as by their ready removability.

Variations may be made in preparations. procedures and materials without departing from the scope of the invention as defined by the following claims:

We claim: e

1. A hair fixing composition containing a solvent selected from the group consisting of 1,1, l-trichloroethane, methylene chloride, ethanol, isopropanol, and water, and from 0.25 to 7%, by weight, of an interpolymer of 1') 30-60% of a comonomer selected from the group consisting of N-alkyl acrylamide and N-alkyl methacrylamide wherein the alkyl group thereof contains from 2 to 12 carbon atoms, (2) 12-18% of an acidic copolymerizable comonomer selected from the group consisting of acrylic acid, methacrylic acid. crotonic acid, itaconic acid, maleic acid, fumaric acid, and the (C -C alkyl half esters of maleic and fumaric acids, and '(3) 20-55% of at lest one copolymerizable comonomer selected from the group consisting of (C -C alkyl acrylates. C1 'C12) alkyl methacrylates, (C -C hydroxyalkyl acrylates. hydroxystearyl acrylate. hydroxyalkyl methacrylates, hydroxystearyl methacrylate, (C -C alkyl (C -C amino alkyl acrylates. (C 4: alkyl (Cg-C aminoalkyl methacrylates. vinyl 9 acetate, vinyl propionate, diacetone acrylamide, styrene, and alpha-methyl styrene; said interpolymer being sufficiently neutralized with an alkaline reagent to effect its solubility in water.

2. The hair fixing composition of claim 1, wherein from 50 to 100% of the available carboxyl groups of the interpolymer are neutralized with an alkaline reagent.

3. The hair fixing composition of claim 1, containing an interpolymer of (1) 30-45% N-tert.octyl acrylamide, (2) 12-18% acrylic or methacrylic acid, (3)

5. The hair fixing composition of claim 1, wherein the composition is in an aerosol container and also contains an aerosol propellant therefor.

6. The hair fixing composition of claim 2, wherein the composition is in an aerosol container and also contains an aerosol propellant therefor.

7. The hair fixing composition of claim 3, wherein the composition is in an aerosol container and also contains an aerosol propellant therefor.

8. The hair fixing composition of claim 4, wherein the composition is in an aerosol container and also contains an aerosol propellant therefor.

9. A process for fixing hair comprising applying to the hair an effective amount of the hair fixing composition of claim 1.

10. A process for fixing hair comprising spraying upon the hair an effective amount of the hair fixing composition of claim 5.

Claims (10)

1. A HAIR FIXING COMPOSITION CONTAINING A SOLVENT SELECTED FROM THE GROUP CONSISTING OF 1,1,1-TRICHLOROETHANE, METHYLENE CHLORIDE, ETHANOL, ISOPROPANOL, AND WATER, AND FROM 0.25 TO 7%, BY WEIGHT, OF AN INTERPOLYMER OF (1) 30-60% OF A COMONOMER SELECTED FROM THE GROUP CONSISTING OF N-ALKYL ACRYLAMIDE AND N-ALKYL METHACRYLAMIDE WHEREIN THE ALKYL GROUP THEREOF CONTAINS FROM 2 TO 12 CARBON ATOMS, (2) 12-18% OF AN ACIDIC COPOLYMERIZABLE COMONOMER SELECTED FROM THE GROUP CONSISTING OF ACRYLIC ACID, METHACRYLIC ACID, CROTONIC ACID, ITACONIC ACID, MALEIC ACID, FUMARIC ACID, AND THE (C1-C4) ALKYL HALF ESTERS OF MALEIC AND FUMARIC ACIDS, AND (3) 20-55% OF AT LEST ONE COPOLYMERIZABLE COMONOMER SELECTED FROM THE GROUP CONSISTING OF (C1-C12) ALKYL ACRYLATES, (C1-C12) ALKYL METHACRYLATES, (C2-C4) HYDROXYALKYL ACRYLATES, HYDROXYSTEARYL ACRYLATE, HYDROXYALKYL METHACRYLATES, HYDROXYSTEARYL METHACRYLATE, (C1-C4) ALKYL (C2-C4) AMINO ALKYL ACRYLATES, (C1-C4) ALKYL (C2-C4) AMINOALKYL METHACRYLATES, VINYL ACETATE, VINYL PROPIONATE, DIACETONE ACRYLAMIDE, STYRENE, AND ALPHA-METHYL STYRENE; SAID INTERPOLYMER BEING SUFFICICNTLY NEUTRALIZED WITH AN ALKALINE REAGENT TO EFFECT ITS SOLUBILITY IN WATER.
2. The hair fixing composition of claim 1, wherein from 50 to 100% of the available carboxyl groups of the interpolymer are neutralized with an alkaline reagent.
3. The hair fixing composition of claim 1, containing an interpolymer of (1) 30-45% N-tert.octyl acrylamide, (2) 12-18% acrylic or methacrylic acid, (3) 32-38% methyl methacrylate, (4) 2-10% hydroxypropyl acrylate, and (5) 2-10% of a (C1-C4) alkyl (C2-C4) aminoalkyl acrylate or methacrylate.
4. The hair fixing composition of claim 3, wherein from 50 to 100% of the available carboxyl groups of the interpolymer are neutralized with an alkaline reagent.
5. THE HAIR FIXING COMPOSITION OF CLAIM 1, WHEREIN THE COMPOSITION IS IN AN AEROSOL CONTAINER AND ALSO CONTAINS AN AEROSOL PROPELLANT THEREFOR.
6. The hair fixing composition of claim 2, wherein the composition is in an aerosol container and also contains an aerosol propellant therefor.
7. The hair fixing composition of claim 3, wherein the composition is in an aerosol container and also contains an aerosol propellant therefor.
8. The hair fixing composition of claim 4, wherein the composition is in an aerosol container and also contains an aerosol propellant therefor.
9. A process for fixing hair comprising applying to the hair an effective amount of the hair fixing composition of claim 1.
10. A process for fixing hair comprising spraying upon the hair an effective amount of the hair fixing composition of claim 5.
US3927199A 1972-04-14 1973-08-13 Hair fixing compositions containing N-alkyl acrylamide or methacrylamide interpolymer Expired - Lifetime US3927199A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US24426472 true 1972-04-14 1972-04-14
US3927199A US3927199A (en) 1972-04-14 1973-08-13 Hair fixing compositions containing N-alkyl acrylamide or methacrylamide interpolymer

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US3927199A US3927199A (en) 1972-04-14 1973-08-13 Hair fixing compositions containing N-alkyl acrylamide or methacrylamide interpolymer

Publications (1)

Publication Number Publication Date
US3927199A true US3927199A (en) 1975-12-16

Family

ID=26936432

Family Applications (1)

Application Number Title Priority Date Filing Date
US3927199A Expired - Lifetime US3927199A (en) 1972-04-14 1973-08-13 Hair fixing compositions containing N-alkyl acrylamide or methacrylamide interpolymer

Country Status (1)

Country Link
US (1) US3927199A (en)

Cited By (127)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4030512A (en) * 1974-12-30 1977-06-21 Societe Anonyme Dite: L'oreal Hair lacquer or setting lotion containing bi- or tri-sequenced copolymer
US4057624A (en) * 1975-03-29 1977-11-08 Henkel Kommanditgesellschaft Auf Aktien Cosmetic emulsions containing acrylamide copolymer
US4059688A (en) * 1976-06-29 1977-11-22 Clairol Incorporated Hair fixing compositions containing fluoroterpolymers and method
JPS5399338A (en) * 1977-02-09 1978-08-30 Sunstar Inc Set lotion and hair spray composition
US4128636A (en) * 1976-03-26 1978-12-05 Henkel Kommanditgesellschaft Auf Aktien Cosmetic emulsions containing copolymers of 2-hydroxy-3-hydroxyalkyl-aminopropyl(meth)acrylates and alkyl (meth)acrylates
US4128635A (en) * 1976-03-04 1978-12-05 Henkel Kommanditgesellschaft Auf Aktien Cosmetic emulsions containing copolymers of alkyl (meth) acrylates and mono- or polyhydroxyalkyl (meth) acrylates
US4128634A (en) * 1976-03-04 1978-12-05 Henkel Kommanditgesellschaft Auf Aktien Cosmetic emulsions containing copolymers of alkyl(meth)acrylates and mono-(N-hydroxyalkyl) or bis-(N-hydroxyalkyl) (meth)acrylamides
US4237253A (en) * 1977-04-21 1980-12-02 L'oreal Copolymers, their process of preparation, and cosmetic compounds containing them
US4275183A (en) * 1979-07-27 1981-06-23 Peter Kuzma Hydrophilic polymers and contact lenses therefrom
US4283525A (en) * 1980-02-19 1981-08-11 National Starch And Chemical Corporation Continuous process for increasing discrete particle size of solution carboxyl polymers
US4293635A (en) * 1980-05-27 1981-10-06 E. I. Du Pont De Nemours And Company Photopolymerizable composition with polymeric binder
EP0037378A2 (en) * 1980-03-27 1981-10-07 Ciba-Geigy Ag Acrylic terpolymers, process for the manufacture thereof and of hair fixing formulations for use as air-pump or aerosol sprays
US4319013A (en) * 1977-05-16 1982-03-09 Societe Francaise Hoechst Powdered cationic polyelectrolytes, based on acrylamide and quaternized or salified dimethyl-aminoethyl acrylate, process for producing them
US4325741A (en) * 1979-09-20 1982-04-20 Kanebo, Ltd. Fibroin-coated pigment and processes for producing same
EP0062002A2 (en) * 1981-03-25 1982-10-06 Ciba-Geigy Ag Composition for fixing the hair, its preparation and its use in aerosol sprays
US4402936A (en) * 1980-02-26 1983-09-06 Kao Soap Co., Ltd. Preshampoo-type hair-treating composition
US4431769A (en) * 1981-03-31 1984-02-14 Showa Denko Kabushiki Kaisha Binder composition for paper-coating materials
EP0121874A2 (en) 1983-04-08 1984-10-17 BASF Aktiengesellschaft Water soluble polymers with low hygroscopicity
US4543249A (en) * 1980-03-27 1985-09-24 American Cyanamid Co. Hair spray compositions containing methylmethacrylate-methacrylic acid copolymers
EP0202690A2 (en) 1981-06-08 1986-11-26 E.I. Du Pont De Nemours And Company Photoimaging compositions containing substituted cyclohexadienone compounds
US4683258A (en) * 1984-05-28 1987-07-28 Mitsui Toatsu Chemicals, Incorporated Agent for absorbing and releasing water vapor
US4762703A (en) * 1982-01-25 1988-08-09 Dow Corning Corp. Nitrocellulose free nail lacquer composition
US4842852A (en) * 1988-03-10 1989-06-27 National Starch And Chemical Corporation Hydrocarbon tolerant hair fixing compositions
EP0323715A2 (en) * 1987-12-11 1989-07-12 THE PROCTER & GAMBLE COMPANY Hair styling agents and compositions containing the same
US4874604A (en) * 1988-06-23 1989-10-17 S. C. Johnson & Son, Inc. Hairspray with improved adhesion/removability upon washing
US4923695A (en) * 1988-03-10 1990-05-08 National Starch And Chemical Corporation Hydrocarbon tolerant hair fixing compositions
US4933170A (en) * 1988-03-10 1990-06-12 National Starch And Chemical Investment Holding Corporation Hydrocarbon tolerant hair fixing compositions
USRE33355E (en) * 1983-10-22 1990-09-25 Mitsui Toatsu Chemicals, Incorporated Agent for absorbing and releasing water vapor
US4996045A (en) * 1988-11-16 1991-02-26 National Starch And Chemical Investment Holding Corporation Hair fixative compositions containing alpha-aminomethylene phosphonate betaines
US5021238A (en) * 1989-09-18 1991-06-04 National Starch And Chemical Investment Holding Corporation Water-based two-phase aerosol hairsprays
EP0442821A1 (en) * 1990-02-16 1991-08-21 L'oreal Aerosol hair laquer containing a tetrapolymer of acrylic acid, a N,N-dimethylacrylamide, a N-tertiobutylacrylamide and an ethyl methacrylate and a non-halogen propellant
US5094838A (en) * 1990-08-22 1992-03-10 Playtex Beauty Care, Inc. Aerosol hair spray composition
US5104642A (en) * 1990-04-06 1992-04-14 The Procter & Gamble Company Hair styling compositions containing particular hair styling polymers and non-aqueous solvents
US5120531A (en) * 1990-04-06 1992-06-09 The Procter & Gamble Company Hair styling conditioners
US5120532A (en) * 1990-04-06 1992-06-09 The Procter & Gamble Company Hair styling shampoos
EP0491629A1 (en) * 1990-12-19 1992-06-24 L'oreal Aerosol laquer for hair containing a tetrapolymers of acrylic acid, a n-vinylpyrrolidon, a n-tertiobutylacrylamide and an ethyl methacrylate
USRE34157E (en) * 1988-06-23 1993-01-05 S. C. Johnson & Son, Inc. Hairspray with improved adhesion/removability upon washing
US5196470A (en) * 1991-03-01 1993-03-23 H. B. Fuller Licensing & Financing Inc. Water soluble alcohol based nonwoven binder for water swellable, soluble or sensitive fibers
US5204092A (en) * 1981-07-03 1993-04-20 Societe Anonyme Dite: L'oreal Cosmetic compositions for the treatment of the hair and skin contain polymer constituted essentially by repeating units of the beta-alanine type
US5262244A (en) * 1990-07-21 1993-11-16 Hoechst Aktiengesellschaft Hydrophilic copolymers and their use in reprography
US5266308A (en) * 1991-12-20 1993-11-30 Chesebrough-Pond's Usa Co. Hair treatment composition
US5275811A (en) * 1991-01-25 1994-01-04 Isp Investments Inc. Hair spray resin composition
US5288493A (en) * 1991-05-17 1994-02-22 National Starch And Chemical Investment Holding Corporation Skin care compositions with improved rub-off resistance
US5441728A (en) * 1994-06-22 1995-08-15 Chesebrough-Pond's Usa Co., A Division Of Conopco, Inc. Hairspray compositions
WO1995035087A1 (en) * 1994-06-21 1995-12-28 Ppg Industries, Inc. Hair fixative amphoteric polymer composition
US5484610A (en) * 1991-01-02 1996-01-16 Macromed, Inc. pH and temperature sensitive terpolymers for oral drug delivery
EP0694565A2 (en) 1994-07-28 1996-01-31 National Starch and Chemical Investment Holding Corporation Solution polymerization of vinyl monomers with water soluble initiators in substantially non-aqueous media
JPH08501675A (en) * 1993-07-12 1996-02-20 フィリップス エレクトロニクス ネムローゼ フェン ノートシャップ Method and apparatus for the channel mapping according to related services confirmed
US5501851A (en) * 1992-07-16 1996-03-26 National Starch And Chemical Investment Holding Corporation Emulsion polymers for use in hair fixatives
US5599532A (en) * 1994-08-12 1997-02-04 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Sprayable hair treatment composition
EP0763356A1 (en) * 1995-09-13 1997-03-19 National Starch and Chemical Investment Holding Corporation Aqueous acrylic hair fixative and methods of making same
EP0781543A1 (en) 1995-12-29 1997-07-02 National Starch and Chemical Investment Holding Corporation Acrylic hair fixatives and methods of making same
US5652296A (en) * 1994-08-19 1997-07-29 Minnesota Mining And Manufacturing Company Water-based adhesives
US5672656A (en) * 1994-02-10 1997-09-30 Kohjin Co., Ltd. Temperature sensitive water absorbing and discharging polymer composition
US5693317A (en) * 1991-09-30 1997-12-02 Colgate-Palmolive Company Conditioning rinse compositions which facilitates setting of hair
US5753215A (en) * 1993-06-08 1998-05-19 L'oreal Cosmetic composition containing a pseudo-latex having remanence properties
DE19704038C1 (en) * 1997-02-04 1998-07-09 Goldwell Gmbh Low viscosity hair styling product
US5840292A (en) * 1991-12-20 1998-11-24 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Hair treatment composition
US6013733A (en) * 1996-02-16 2000-01-11 Ppg Industries Ohio, Inc. Coating of film-forming resin and functional flow control copolymer
US6139827A (en) * 1997-12-31 2000-10-31 L'oreal Wear cosmetic composition
US6159457A (en) * 1997-02-10 2000-12-12 L'oreal Cosmetic or dermatological compositions containing polymers exhibiting a critical temperature of the LCST type or of the USCT type of uses thereof
US6190681B1 (en) 1998-04-15 2001-02-20 Yoram Fishman Long lasting liquid color compositions
US6261576B1 (en) 1998-04-15 2001-07-17 Yoram Fishman Long-lasting liquid color formulations
US6262176B1 (en) 1998-05-14 2001-07-17 Basf Aktiengesellschaft Crosslinked water-soluble or water-dispersible polyurethanes
US6395263B1 (en) 1995-05-15 2002-05-28 Rosemarie Nichols Smear-resistant cosmetic
EP1239329A2 (en) 2001-03-06 2002-09-11 E.I. Du Pont De Nemours And Company A process for making a flexographic printing plate and a photosensitive element for use in the process
US6482393B1 (en) * 1993-04-30 2002-11-19 Basf Aktiengesellschaft Hairsetting compositions
FR2840210A1 (en) * 2002-05-31 2003-12-05 Oreal capillary pressurized composition, comprising at least one amphiphilic diblock copolymer linear
US20040013615A1 (en) * 2002-05-31 2004-01-22 L'oreal Pressurized hair treatment compositions comprising at least one amphiphilic linear diblock copolymer
US20040223933A1 (en) * 2001-09-13 2004-11-11 Mitsubishi Chemical Corporation Cosmetic polymer composition and cosmetic
WO2005058988A1 (en) * 2003-12-09 2005-06-30 Basf Aktiengesellschaft Ampholytic anionic copolymers
WO2005058989A1 (en) * 2003-12-09 2005-06-30 Basf Aktiengesellschaft Copolymers based on tert-butyl(meth)acrylate and use thereof
US20050158265A1 (en) * 2003-06-17 2005-07-21 Sabine Vrignaud Cosmetic hair composition comprising tridecyl trimellitate and at least one fixing polymer
EP1674133A1 (en) 2004-12-16 2006-06-28 KPSS-Kao Professional Salon Services GmbH Cleansing composition
USRE39218E1 (en) 1994-09-30 2006-08-01 L'oreal Anhydrous and water-resistant cosmetic compositions
WO2007017441A1 (en) * 2005-08-11 2007-02-15 Basf Se Cosmetically used cross-linked methyl methacrylate-copolymer
WO2007020203A1 (en) * 2005-08-19 2007-02-22 Basf Se Anionic, ampholytic copolymers for low-voc-compositions
EP1762224A1 (en) 2005-09-08 2007-03-14 KPSS-Kao Professional Salon Services GmbH Aerosol styling wax composition
EP1762225A1 (en) 2005-09-08 2007-03-14 KPSS-Kao Professional Salon Services GmbH Aerosol styling wax composition
US20080089853A1 (en) * 2004-10-22 2008-04-17 Basf Aktiengesellschaft Amphoteric Ethyl Methacrylate Copolymers and Use Thereof
EP1925288A1 (en) 2006-11-24 2008-05-28 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP1927346A1 (en) 2006-11-16 2008-06-04 KPSS-Kao Professional Salon Services GmbH Hair styling emulsion composition
EP2018843A1 (en) 2007-07-26 2009-01-28 KPSS Kao Professional Salon Services GmbH Conditioning and colouring composition for hair
EP2022474A1 (en) 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair comprising optical brightener
EP2022472A1 (en) 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
EP2025329A1 (en) 2007-08-07 2009-02-18 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
EP2025330A2 (en) 2007-08-07 2009-02-18 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP2025322A1 (en) 2007-08-07 2009-02-18 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
EP2025321A1 (en) 2007-08-07 2009-02-18 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
EP2044925A1 (en) 2007-07-26 2009-04-08 KPSS Kao Professional Salon Services GmbH Colour enhancing shampoo composition
US20090104136A1 (en) * 2007-10-22 2009-04-23 Daniel Griffith Anderson Hair care compositions and methods of treating hair using same
EP2090291A1 (en) 2008-02-14 2009-08-19 KPSS-Kao Professional Salon Services GmbH Composition for hair comprising PCA and PCA ester
EP2110117A1 (en) 2008-04-15 2009-10-21 KPSS-Kao Professional Salon Services GmbH Volume giving cleansing composition
EP2110119A1 (en) 2008-04-15 2009-10-21 KPSS-Kao Professional Salon Services GmbH Shear thickening cleaning composition
EP2161018A1 (en) 2008-09-05 2010-03-10 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP2161017A1 (en) 2008-09-05 2010-03-10 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP2161014A1 (en) 2008-09-05 2010-03-10 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
EP2161016A1 (en) 2008-09-05 2010-03-10 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
EP2161015A1 (en) 2008-09-05 2010-03-10 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
US20100068156A1 (en) * 1997-06-29 2010-03-18 Basf Se Ampholytic copolymer based on quaternized nitrogen-containing monomers
EP2184051A1 (en) 2008-11-11 2010-05-12 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP2184052A1 (en) 2008-11-11 2010-05-12 KPSS-Kao Professional Salon Services GmbH Composition for hair
EP2191814A1 (en) 2008-12-01 2010-06-02 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP2196178A1 (en) 2008-12-15 2010-06-16 KPSS-Kao Professional Salon Services GmbH Cosmetic composition for hair and scalp
EP2196186A1 (en) 2008-12-15 2010-06-16 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP2196192A1 (en) 2008-12-15 2010-06-16 KPSS-Kao Professional Salon Services GmbH Use of aminated organopolysiloxane compounds for protecting hair and hair colour
EP2246036A1 (en) 2009-04-27 2010-11-03 KPSS-Kao Professional Salon Services GmbH Aqueous cleansing composition
US20100278769A1 (en) * 2007-10-22 2010-11-04 Living Proof, Inc. Hair care compositions and methods of treating hair
EP2258337A1 (en) 2009-06-03 2010-12-08 KPSS-Kao Professional Salon Services GmbH Composition for hair
US20110073126A1 (en) * 2005-05-12 2011-03-31 Wellin Mu Long-Wearing Glossy Cosmetic Composition
EP2332518A1 (en) 2009-12-10 2011-06-15 KPSS-Kao Professional Salon Services GmbH Hair styling composition comprising dipeptide
EP2335680A1 (en) 2009-12-18 2011-06-22 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP2335674A1 (en) 2009-12-18 2011-06-22 KPSS-Kao Professional Salon Services GmbH Hair styling emulsion foam
EP2335679A1 (en) 2009-12-18 2011-06-22 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
EP2335673A1 (en) 2009-12-18 2011-06-22 KPSS-Kao Professional Salon Services GmbH Hair styling gel foam
EP2380555A1 (en) 2010-04-23 2011-10-26 KPSS-Kao Professional Salon Services GmbH Conditioning composition for keratin fibres and its use
EP2394631A1 (en) 2010-06-08 2011-12-14 KPSS-Kao Professional Salon Services GmbH Hair treatment composition
EP2471505A1 (en) 2010-12-28 2012-07-04 KPSS-Kao Professional Salon Services GmbH Cleansing composition especially for artificially coloured hair
CN102796221A (en) * 2011-05-27 2012-11-28 罗门哈斯电子材料有限公司 Surface active additive and photoresist composition comprising same
WO2012163406A1 (en) 2011-05-31 2012-12-06 Kpss-Kao Professional Salon Services Gmbh Hair treatment composition
EP2550953A1 (en) 2011-07-27 2013-01-30 KPSS-Kao Professional Salon Services GmbH Post-foaming gel composition
EP2868309A1 (en) 2013-10-31 2015-05-06 Kao Corporation Hair styling composition
EP2942083A1 (en) 2014-05-07 2015-11-11 Kao Germany GmbH Aqueous cosmetic powder composition
WO2016169957A1 (en) 2015-04-20 2016-10-27 Akzo Nobel Chemicals International B.V. Acrylic hair fixative copolymers and compositions
US9554972B2 (en) 2004-03-05 2017-01-31 Kao Germany Gmbh Hair treatment composition
WO2017083328A1 (en) 2015-11-09 2017-05-18 Merial, Inc. Pet care compositions
EP3187227A1 (en) 2015-12-28 2017-07-05 Kao Corporation Use of silicone copolymer for improving select hair properties and process thereof

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3257281A (en) * 1962-07-05 1966-06-21 Ciba Ltd Aerosol preparations for the treatment of the hair comprising hydrophilic salts of basic amides and esters
US3405084A (en) * 1965-06-30 1968-10-08 Barr Company G Neutralized terpolymeric resin of vinyl pyrrolidone, alkyl acrylate or methacrylate,and unsaturated monocarboxylic acid
US3493500A (en) * 1966-10-20 1970-02-03 Dow Chemical Co Acrylic acid polymers
US3577518A (en) * 1969-07-18 1971-05-04 Nat Patent Dev Corp Hydrophilic hairspray and hair setting preparations
US3577517A (en) * 1965-03-26 1971-05-04 Mitsubishi Rayon Co Acrylic or methacrylic acid copolymer in resinous aerosol hair preparations
US3726288A (en) * 1971-08-04 1973-04-10 Nat Starch Chem Corp Process for setting hair using a preparation comprising a single fixative-thickener
US3735003A (en) * 1969-12-15 1973-05-22 Aerosol hair setting composition com- prising an interpolymer of an n-j-oxo- alkylamide and a,/j-unsaturated ali- phatic acid
US3753958A (en) * 1969-12-31 1973-08-21 Bayer Ag Pulverisable acrylate resins

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3257281A (en) * 1962-07-05 1966-06-21 Ciba Ltd Aerosol preparations for the treatment of the hair comprising hydrophilic salts of basic amides and esters
US3577517A (en) * 1965-03-26 1971-05-04 Mitsubishi Rayon Co Acrylic or methacrylic acid copolymer in resinous aerosol hair preparations
US3405084A (en) * 1965-06-30 1968-10-08 Barr Company G Neutralized terpolymeric resin of vinyl pyrrolidone, alkyl acrylate or methacrylate,and unsaturated monocarboxylic acid
US3493500A (en) * 1966-10-20 1970-02-03 Dow Chemical Co Acrylic acid polymers
US3577518A (en) * 1969-07-18 1971-05-04 Nat Patent Dev Corp Hydrophilic hairspray and hair setting preparations
US3735003A (en) * 1969-12-15 1973-05-22 Aerosol hair setting composition com- prising an interpolymer of an n-j-oxo- alkylamide and a,/j-unsaturated ali- phatic acid
US3753958A (en) * 1969-12-31 1973-08-21 Bayer Ag Pulverisable acrylate resins
US3726288A (en) * 1971-08-04 1973-04-10 Nat Starch Chem Corp Process for setting hair using a preparation comprising a single fixative-thickener

Cited By (194)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4030512A (en) * 1974-12-30 1977-06-21 Societe Anonyme Dite: L'oreal Hair lacquer or setting lotion containing bi- or tri-sequenced copolymer
US4057624A (en) * 1975-03-29 1977-11-08 Henkel Kommanditgesellschaft Auf Aktien Cosmetic emulsions containing acrylamide copolymer
US4128635A (en) * 1976-03-04 1978-12-05 Henkel Kommanditgesellschaft Auf Aktien Cosmetic emulsions containing copolymers of alkyl (meth) acrylates and mono- or polyhydroxyalkyl (meth) acrylates
US4128634A (en) * 1976-03-04 1978-12-05 Henkel Kommanditgesellschaft Auf Aktien Cosmetic emulsions containing copolymers of alkyl(meth)acrylates and mono-(N-hydroxyalkyl) or bis-(N-hydroxyalkyl) (meth)acrylamides
US4128636A (en) * 1976-03-26 1978-12-05 Henkel Kommanditgesellschaft Auf Aktien Cosmetic emulsions containing copolymers of 2-hydroxy-3-hydroxyalkyl-aminopropyl(meth)acrylates and alkyl (meth)acrylates
US4059688A (en) * 1976-06-29 1977-11-22 Clairol Incorporated Hair fixing compositions containing fluoroterpolymers and method
JPS5399338A (en) * 1977-02-09 1978-08-30 Sunstar Inc Set lotion and hair spray composition
JPS6150923B2 (en) * 1977-02-09 1986-11-06 Sunstar Kk
US4237253A (en) * 1977-04-21 1980-12-02 L'oreal Copolymers, their process of preparation, and cosmetic compounds containing them
US4319013A (en) * 1977-05-16 1982-03-09 Societe Francaise Hoechst Powdered cationic polyelectrolytes, based on acrylamide and quaternized or salified dimethyl-aminoethyl acrylate, process for producing them
US4275183A (en) * 1979-07-27 1981-06-23 Peter Kuzma Hydrophilic polymers and contact lenses therefrom
US4325741A (en) * 1979-09-20 1982-04-20 Kanebo, Ltd. Fibroin-coated pigment and processes for producing same
US4283525A (en) * 1980-02-19 1981-08-11 National Starch And Chemical Corporation Continuous process for increasing discrete particle size of solution carboxyl polymers
US4402936A (en) * 1980-02-26 1983-09-06 Kao Soap Co., Ltd. Preshampoo-type hair-treating composition
EP0037378A2 (en) * 1980-03-27 1981-10-07 Ciba-Geigy Ag Acrylic terpolymers, process for the manufacture thereof and of hair fixing formulations for use as air-pump or aerosol sprays
EP0037378A3 (en) * 1980-03-27 1982-04-14 Ciba-Geigy Ag Acrylic terpolymers, process for the manufacture thereof and of hair fixing formulations for use as air-pump or aerosol sprays
JPS56149412A (en) * 1980-03-27 1981-11-19 Ciba Geigy Ag Acryl terpolymer, its manufacture and hair treatment composition available for air pump or aerosol spray
JPH0261494B2 (en) * 1980-03-27 1990-12-20 Basf Ag
US4543249A (en) * 1980-03-27 1985-09-24 American Cyanamid Co. Hair spray compositions containing methylmethacrylate-methacrylic acid copolymers
US4293635A (en) * 1980-05-27 1981-10-06 E. I. Du Pont De Nemours And Company Photopolymerizable composition with polymeric binder
EP0062002A2 (en) * 1981-03-25 1982-10-06 Ciba-Geigy Ag Composition for fixing the hair, its preparation and its use in aerosol sprays
US5110582A (en) * 1981-03-25 1992-05-05 Basf Aktiengesellschaft Hair-setting preparation
EP0062002A3 (en) * 1981-03-25 1983-06-22 Ciba-Geigy Ag Composition for fixing the hair, its preparation and its use in aerosol sprays
US4431769A (en) * 1981-03-31 1984-02-14 Showa Denko Kabushiki Kaisha Binder composition for paper-coating materials
EP0202690A2 (en) 1981-06-08 1986-11-26 E.I. Du Pont De Nemours And Company Photoimaging compositions containing substituted cyclohexadienone compounds
US5204092A (en) * 1981-07-03 1993-04-20 Societe Anonyme Dite: L'oreal Cosmetic compositions for the treatment of the hair and skin contain polymer constituted essentially by repeating units of the beta-alanine type
US5389362A (en) * 1981-07-03 1995-02-14 Societe Anonyme Dite: L'oreal Cosmetic compositions for the treatment of the hair and skin contain polymer constituted essentially by repeating units of the β-alanine type
US4762703A (en) * 1982-01-25 1988-08-09 Dow Corning Corp. Nitrocellulose free nail lacquer composition
EP0121874A2 (en) 1983-04-08 1984-10-17 BASF Aktiengesellschaft Water soluble polymers with low hygroscopicity
US4551512A (en) * 1983-04-08 1985-11-05 Basf Aktiengesellschaft Water-soluble polymers having a low hygroscopicity
USRE33355E (en) * 1983-10-22 1990-09-25 Mitsui Toatsu Chemicals, Incorporated Agent for absorbing and releasing water vapor
US4683258A (en) * 1984-05-28 1987-07-28 Mitsui Toatsu Chemicals, Incorporated Agent for absorbing and releasing water vapor
JP2716486B2 (en) * 1987-12-11 1998-02-18 ザ、プロクター、エンド、ギャンブル、カンパニー Styling agents and compositions containing the same
JPH01301613A (en) * 1987-12-11 1989-12-05 Procter & Gamble Co:The Styling agent and composition comprising the same
EP0323715A2 (en) * 1987-12-11 1989-07-12 THE PROCTER & GAMBLE COMPANY Hair styling agents and compositions containing the same
EP0323715A3 (en) * 1987-12-11 1990-05-16 The Procter & Gamble Company Hair styling agents and compositions containing the same
US4923695A (en) * 1988-03-10 1990-05-08 National Starch And Chemical Corporation Hydrocarbon tolerant hair fixing compositions
US4842852A (en) * 1988-03-10 1989-06-27 National Starch And Chemical Corporation Hydrocarbon tolerant hair fixing compositions
US4933170A (en) * 1988-03-10 1990-06-12 National Starch And Chemical Investment Holding Corporation Hydrocarbon tolerant hair fixing compositions
US4859455A (en) * 1988-03-10 1989-08-22 National Starch And Chemical Corporation Hydrocarbon tolerant hair fixing compositions
US4874604A (en) * 1988-06-23 1989-10-17 S. C. Johnson & Son, Inc. Hairspray with improved adhesion/removability upon washing
USRE34157E (en) * 1988-06-23 1993-01-05 S. C. Johnson & Son, Inc. Hairspray with improved adhesion/removability upon washing
US4996045A (en) * 1988-11-16 1991-02-26 National Starch And Chemical Investment Holding Corporation Hair fixative compositions containing alpha-aminomethylene phosphonate betaines
US5021238A (en) * 1989-09-18 1991-06-04 National Starch And Chemical Investment Holding Corporation Water-based two-phase aerosol hairsprays
FR2658417A1 (en) * 1990-02-16 1991-08-23 Oreal Capillary aerosol lacquer containing a tetrapolymer of acrylic acid, N, N-dimethylacrylamide, n-butylacrylamide and ethyl methacrylate and a nonhalogenated propellent gas.
US5116601A (en) * 1990-02-16 1992-05-26 L'oreal Aerosol hair spray containing a tetrapolymer of acrylic acid, n,n-dimethylacrylamide, n-tert-butylacrylamide, and ethyl methacrylate and a non-halogenated propellant gas
EP0442821A1 (en) * 1990-02-16 1991-08-21 L'oreal Aerosol hair laquer containing a tetrapolymer of acrylic acid, a N,N-dimethylacrylamide, a N-tertiobutylacrylamide and an ethyl methacrylate and a non-halogen propellant
US5120532A (en) * 1990-04-06 1992-06-09 The Procter & Gamble Company Hair styling shampoos
US5120531A (en) * 1990-04-06 1992-06-09 The Procter & Gamble Company Hair styling conditioners
US5104642A (en) * 1990-04-06 1992-04-14 The Procter & Gamble Company Hair styling compositions containing particular hair styling polymers and non-aqueous solvents
US5262244A (en) * 1990-07-21 1993-11-16 Hoechst Aktiengesellschaft Hydrophilic copolymers and their use in reprography
US5094838A (en) * 1990-08-22 1992-03-10 Playtex Beauty Care, Inc. Aerosol hair spray composition
EP0491629A1 (en) * 1990-12-19 1992-06-24 L'oreal Aerosol laquer for hair containing a tetrapolymers of acrylic acid, a n-vinylpyrrolidon, a n-tertiobutylacrylamide and an ethyl methacrylate
FR2670671A1 (en) * 1990-12-19 1992-06-26 Oreal Aerosol lacquer for setting hair containing a tetrapolymer of acrylic acid, n-vinylpyrrolidone, n-butylacrylamide and ethylmethacrylate.
US5484610A (en) * 1991-01-02 1996-01-16 Macromed, Inc. pH and temperature sensitive terpolymers for oral drug delivery
US5275811A (en) * 1991-01-25 1994-01-04 Isp Investments Inc. Hair spray resin composition
US5196470A (en) * 1991-03-01 1993-03-23 H. B. Fuller Licensing & Financing Inc. Water soluble alcohol based nonwoven binder for water swellable, soluble or sensitive fibers
US5288493A (en) * 1991-05-17 1994-02-22 National Starch And Chemical Investment Holding Corporation Skin care compositions with improved rub-off resistance
US5693317A (en) * 1991-09-30 1997-12-02 Colgate-Palmolive Company Conditioning rinse compositions which facilitates setting of hair
US5266308A (en) * 1991-12-20 1993-11-30 Chesebrough-Pond's Usa Co. Hair treatment composition
US5840292A (en) * 1991-12-20 1998-11-24 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Hair treatment composition
US5501851A (en) * 1992-07-16 1996-03-26 National Starch And Chemical Investment Holding Corporation Emulsion polymers for use in hair fixatives
US6482393B1 (en) * 1993-04-30 2002-11-19 Basf Aktiengesellschaft Hairsetting compositions
US5753215A (en) * 1993-06-08 1998-05-19 L'oreal Cosmetic composition containing a pseudo-latex having remanence properties
JPH08501675A (en) * 1993-07-12 1996-02-20 フィリップス エレクトロニクス ネムローゼ フェン ノートシャップ Method and apparatus for the channel mapping according to related services confirmed
US5672656A (en) * 1994-02-10 1997-09-30 Kohjin Co., Ltd. Temperature sensitive water absorbing and discharging polymer composition
WO1995035087A1 (en) * 1994-06-21 1995-12-28 Ppg Industries, Inc. Hair fixative amphoteric polymer composition
US5948396A (en) * 1994-06-21 1999-09-07 Ppg Industries Ohio, Inc. Hair fixative amphoteric polymer composition
EP0688557A2 (en) 1994-06-22 1995-12-27 Unilever Plc Hairspray compositions
US5441728A (en) * 1994-06-22 1995-08-15 Chesebrough-Pond's Usa Co., A Division Of Conopco, Inc. Hairspray compositions
EP0694565A2 (en) 1994-07-28 1996-01-31 National Starch and Chemical Investment Holding Corporation Solution polymerization of vinyl monomers with water soluble initiators in substantially non-aqueous media
US5576403A (en) * 1994-07-28 1996-11-19 National Starch And Chemical Investment Holding Corporation Solution polymerization of vinyl monomers with water soluble initiators in substantially non-aqueous media
EP0694565A3 (en) * 1994-07-28 1996-05-22 Nat Starch Chem Invest Solution polymerization of vinyl monomers with water soluble initiators in substantially non-aqueous media
US5632976A (en) * 1994-07-28 1997-05-27 National Starch And Chemical Investment Holding Corporation Solution polymerization of vinyl monomers with water soluble initiators in substantially non-aqueous media
US5599532A (en) * 1994-08-12 1997-02-04 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Sprayable hair treatment composition
US5723113A (en) * 1994-08-12 1998-03-03 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Sprayable hair treatment composition
US5652296A (en) * 1994-08-19 1997-07-29 Minnesota Mining And Manufacturing Company Water-based adhesives
USRE39218E1 (en) 1994-09-30 2006-08-01 L'oreal Anhydrous and water-resistant cosmetic compositions
US6509009B2 (en) 1995-05-15 2003-01-21 Rosemarie Nichols Smear-resistant cosmetic
US6395263B1 (en) 1995-05-15 2002-05-28 Rosemarie Nichols Smear-resistant cosmetic
EP0763356A1 (en) * 1995-09-13 1997-03-19 National Starch and Chemical Investment Holding Corporation Aqueous acrylic hair fixative and methods of making same
US5620683A (en) * 1995-09-13 1997-04-15 National Starch And Chemical Investment Holding Corporation Aqueous, acrylic hair fixatives and methods of making same
US5686062A (en) * 1995-12-29 1997-11-11 National Starch And Chemical Investment Holding Corporation Acrylic hair fixatives and methods of making same
EP0781543A1 (en) 1995-12-29 1997-07-02 National Starch and Chemical Investment Holding Corporation Acrylic hair fixatives and methods of making same
US6313224B1 (en) 1996-02-16 2001-11-06 Ppg Industrial Ohio, Inc. Coating of film-forming resin and functional flow control copolymer
US6013733A (en) * 1996-02-16 2000-01-11 Ppg Industries Ohio, Inc. Coating of film-forming resin and functional flow control copolymer
DE19704038C1 (en) * 1997-02-04 1998-07-09 Goldwell Gmbh Low viscosity hair styling product
US6159457A (en) * 1997-02-10 2000-12-12 L'oreal Cosmetic or dermatological compositions containing polymers exhibiting a critical temperature of the LCST type or of the USCT type of uses thereof
US20100068156A1 (en) * 1997-06-29 2010-03-18 Basf Se Ampholytic copolymer based on quaternized nitrogen-containing monomers
US6139827A (en) * 1997-12-31 2000-10-31 L'oreal Wear cosmetic composition
US6190681B1 (en) 1998-04-15 2001-02-20 Yoram Fishman Long lasting liquid color compositions
US6428797B2 (en) 1998-04-15 2002-08-06 Yoram Fishman Long-lasting liquid color compositions
US6261576B1 (en) 1998-04-15 2001-07-17 Yoram Fishman Long-lasting liquid color formulations
USRE41615E1 (en) 1998-05-14 2010-08-31 Basf Se Crosslinked, water-soluble or water-dispersible polyurethanes
USRE39936E1 (en) 1998-05-14 2007-12-04 Basf Aktiengesellschaft Crosslinked, water-soluble or water-dispersible polyurethanes
US6262176B1 (en) 1998-05-14 2001-07-17 Basf Aktiengesellschaft Crosslinked water-soluble or water-dispersible polyurethanes
US6489397B2 (en) 1998-05-14 2002-12-03 Basf Aktiengesellschaft Crosslinked, water-soluble or water-dispersible polyurethanes
EP1239329A2 (en) 2001-03-06 2002-09-11 E.I. Du Pont De Nemours And Company A process for making a flexographic printing plate and a photosensitive element for use in the process
US20040223933A1 (en) * 2001-09-13 2004-11-11 Mitsubishi Chemical Corporation Cosmetic polymer composition and cosmetic
US20070166250A1 (en) * 2001-09-13 2007-07-19 Mitsubishi Chemical Corporation Cosmetic polymer composition and cosmetic
FR2840210A1 (en) * 2002-05-31 2003-12-05 Oreal capillary pressurized composition, comprising at least one amphiphilic diblock copolymer linear
US20040013615A1 (en) * 2002-05-31 2004-01-22 L'oreal Pressurized hair treatment compositions comprising at least one amphiphilic linear diblock copolymer
US20050158265A1 (en) * 2003-06-17 2005-07-21 Sabine Vrignaud Cosmetic hair composition comprising tridecyl trimellitate and at least one fixing polymer
US7858076B2 (en) 2003-12-09 2010-12-28 Basf Se Copolymers based on tert-butyl(meth) acrylate and use thereof
US7829070B2 (en) 2003-12-09 2010-11-09 Basf Se Ampholytic anionic copolymers
WO2005058989A1 (en) * 2003-12-09 2005-06-30 Basf Aktiengesellschaft Copolymers based on tert-butyl(meth)acrylate and use thereof
US20070116660A1 (en) * 2003-12-09 2007-05-24 Basf Aktiengesellschaft Copolymers based on tertbutyl(meth) acrylate and use thereof
US20070141013A1 (en) * 2003-12-09 2007-06-21 Basf Aktiengesellschaft Ampholytic anionic copolymers
WO2005058988A1 (en) * 2003-12-09 2005-06-30 Basf Aktiengesellschaft Ampholytic anionic copolymers
US9554972B2 (en) 2004-03-05 2017-01-31 Kao Germany Gmbh Hair treatment composition
US20080089853A1 (en) * 2004-10-22 2008-04-17 Basf Aktiengesellschaft Amphoteric Ethyl Methacrylate Copolymers and Use Thereof
US8034888B2 (en) 2004-10-22 2011-10-11 Basf Se Amphoteric ethyl methacrylate copolymers and use thereof
EP1674133A1 (en) 2004-12-16 2006-06-28 KPSS-Kao Professional Salon Services GmbH Cleansing composition
US20110073126A1 (en) * 2005-05-12 2011-03-31 Wellin Mu Long-Wearing Glossy Cosmetic Composition
US8932570B2 (en) 2005-05-12 2015-01-13 Elc Management Llc Long-wearing glossy cosmetic composition
US20100135917A1 (en) * 2005-08-11 2010-06-03 Basf Aktiengesellschaft Cosmetically used cross-linked methyl methacrylate-copolymer
WO2007017441A1 (en) * 2005-08-11 2007-02-15 Basf Se Cosmetically used cross-linked methyl methacrylate-copolymer
WO2007020203A1 (en) * 2005-08-19 2007-02-22 Basf Se Anionic, ampholytic copolymers for low-voc-compositions
US20080219934A1 (en) * 2005-08-19 2008-09-11 Basf Aktiengesellschaft Anionic, Ampholytic Copolymers for Low-Voc-Compositions
EP1762225A1 (en) 2005-09-08 2007-03-14 KPSS-Kao Professional Salon Services GmbH Aerosol styling wax composition
EP1762224A1 (en) 2005-09-08 2007-03-14 KPSS-Kao Professional Salon Services GmbH Aerosol styling wax composition
CN101516934B (en) 2006-09-15 2012-07-18 巴斯夫欧洲公司 Ampholytic copolymer based on quaternized nitrogen-containing monomers
US8303943B2 (en) 2006-09-15 2012-11-06 Basf Se Ampholytic copolymer based on quaternized nitrogen-containing monomers
EP1927346A1 (en) 2006-11-16 2008-06-04 KPSS-Kao Professional Salon Services GmbH Hair styling emulsion composition
EP1925288A1 (en) 2006-11-24 2008-05-28 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP2044925A1 (en) 2007-07-26 2009-04-08 KPSS Kao Professional Salon Services GmbH Colour enhancing shampoo composition
EP2018843A1 (en) 2007-07-26 2009-01-28 KPSS Kao Professional Salon Services GmbH Conditioning and colouring composition for hair
EP2022472A1 (en) 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
EP2022474A1 (en) 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair comprising optical brightener
EP2025321A1 (en) 2007-08-07 2009-02-18 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
EP2025330A2 (en) 2007-08-07 2009-02-18 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP2025329A1 (en) 2007-08-07 2009-02-18 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
EP2025322A1 (en) 2007-08-07 2009-02-18 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
US8318138B2 (en) 2007-10-22 2012-11-27 Living Proof, Inc. Hair care compositions and methods of treating hair using same
US8226934B2 (en) 2007-10-22 2012-07-24 Living Proof, Inc. Hair care compositions and methods of treating hair using same
US8545818B2 (en) 2007-10-22 2013-10-01 Living Proof, Inc. Hair care compositions and methods of treating hair using same
US8551463B2 (en) 2007-10-22 2013-10-08 Living Proof, Inc. Hair care compositions and methods of treating hair
US8557223B2 (en) 2007-10-22 2013-10-15 Living Proof, Inc. Hair care compositions and methods of treating hair using same
US9770399B2 (en) 2007-10-22 2017-09-26 Living Proof, Inc. Hair care compositions and methods of treating hair
US9192553B2 (en) 2007-10-22 2015-11-24 Living Proof, Inc. Hair care compositions and methods of treating hair using same
US20100284953A1 (en) * 2007-10-22 2010-11-11 Living Proof, Inc. Hair care compositions and methods of treating hair using same
US20090191141A1 (en) * 2007-10-22 2009-07-30 Living Proof, Inc. Hair care compositions and methods of treating hair using same
US7785575B2 (en) 2007-10-22 2010-08-31 Living Proof, Inc. Hair care compositions and methods of treating hair using same
US20090104136A1 (en) * 2007-10-22 2009-04-23 Daniel Griffith Anderson Hair care compositions and methods of treating hair using same
US20100284939A1 (en) * 2007-10-22 2010-11-11 Living Proof, Inc. Hair care compositions and methods of treating hair using same
US20100278769A1 (en) * 2007-10-22 2010-11-04 Living Proof, Inc. Hair care compositions and methods of treating hair
US7763240B2 (en) 2007-10-22 2010-07-27 Living Proof, Inc. Hair care compositions and methods of treating hair using same
EP2090291A1 (en) 2008-02-14 2009-08-19 KPSS-Kao Professional Salon Services GmbH Composition for hair comprising PCA and PCA ester
EP2130529A2 (en) 2008-04-15 2009-12-09 KPSS-Kao Professional Salon Services GmbH Volume giving cleansing composition
EP2110117A1 (en) 2008-04-15 2009-10-21 KPSS-Kao Professional Salon Services GmbH Volume giving cleansing composition
EP2110119A1 (en) 2008-04-15 2009-10-21 KPSS-Kao Professional Salon Services GmbH Shear thickening cleaning composition
EP2161018A1 (en) 2008-09-05 2010-03-10 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP2161016A1 (en) 2008-09-05 2010-03-10 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
EP2161014A1 (en) 2008-09-05 2010-03-10 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
EP2161015A1 (en) 2008-09-05 2010-03-10 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
EP2161017A1 (en) 2008-09-05 2010-03-10 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP2184051A1 (en) 2008-11-11 2010-05-12 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP2184052A1 (en) 2008-11-11 2010-05-12 KPSS-Kao Professional Salon Services GmbH Composition for hair
EP2191814A1 (en) 2008-12-01 2010-06-02 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP2196186A1 (en) 2008-12-15 2010-06-16 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP2196178A1 (en) 2008-12-15 2010-06-16 KPSS-Kao Professional Salon Services GmbH Cosmetic composition for hair and scalp
EP2196192A1 (en) 2008-12-15 2010-06-16 KPSS-Kao Professional Salon Services GmbH Use of aminated organopolysiloxane compounds for protecting hair and hair colour
EP2246036A1 (en) 2009-04-27 2010-11-03 KPSS-Kao Professional Salon Services GmbH Aqueous cleansing composition
EP2258337A1 (en) 2009-06-03 2010-12-08 KPSS-Kao Professional Salon Services GmbH Composition for hair
WO2011069618A2 (en) 2009-12-10 2011-06-16 Kpss-Kao Professional Salon Services Gmbh Hair styling composition
EP2332518A1 (en) 2009-12-10 2011-06-15 KPSS-Kao Professional Salon Services GmbH Hair styling composition comprising dipeptide
EP2335679A1 (en) 2009-12-18 2011-06-22 KPSS-Kao Professional Salon Services GmbH Conditioning composition for hair
EP2335680A1 (en) 2009-12-18 2011-06-22 KPSS-Kao Professional Salon Services GmbH Cleansing composition
EP2335674A1 (en) 2009-12-18 2011-06-22 KPSS-Kao Professional Salon Services GmbH Hair styling emulsion foam
WO2011072857A1 (en) 2009-12-18 2011-06-23 Kpss-Kao Professional Salon Services Gmbh Hair styling gel foam
WO2011072856A1 (en) 2009-12-18 2011-06-23 Kpss-Kao Professional Salon Services Gmbh Hair styling emulsion foam
WO2011072855A1 (en) 2009-12-18 2011-06-23 Kpss-Kao Professional Salon Services Gmbh Cleansing composition
EP2335673A1 (en) 2009-12-18 2011-06-22 KPSS-Kao Professional Salon Services GmbH Hair styling gel foam
WO2011072853A2 (en) 2009-12-18 2011-06-23 Kpss-Kao Professional Salon Services Gmbh Conditioning composition for hair
WO2011131687A1 (en) 2010-04-23 2011-10-27 Kpss-Kao Professional Salon Services Gmbh Conditioning composition for keratin fibres and its use
EP2380555A1 (en) 2010-04-23 2011-10-26 KPSS-Kao Professional Salon Services GmbH Conditioning composition for keratin fibres and its use
US9511008B2 (en) 2010-04-23 2016-12-06 Kao Germany Gmbh Conditioning composition for keratin fibres and its use
EP2394631A1 (en) 2010-06-08 2011-12-14 KPSS-Kao Professional Salon Services GmbH Hair treatment composition
WO2012089719A2 (en) 2010-12-28 2012-07-05 Kpss-Kao Professional Salon Services Gmbh Cleansing composition especially for artificially coloured hair
EP2471505A1 (en) 2010-12-28 2012-07-04 KPSS-Kao Professional Salon Services GmbH Cleansing composition especially for artificially coloured hair
US8722825B2 (en) 2011-05-27 2014-05-13 Rohm And Haas Electronic Materials Llc Surface active additive and photoresist composition comprising same
CN102796221B (en) 2011-05-27 2014-08-27 罗门哈斯电子材料有限公司 Surface active additive and photoresist composition comprising same
EP2527377A1 (en) * 2011-05-27 2012-11-28 Rohm and Haas Electronic Materials LLC Surface active additive and photoresist composition comprising same
US9012128B2 (en) 2011-05-27 2015-04-21 Rohm And Haas Electronic Materials Llc Photoresist and coated substrate comprising same
CN102796221A (en) * 2011-05-27 2012-11-28 罗门哈斯电子材料有限公司 Surface active additive and photoresist composition comprising same
WO2012163406A1 (en) 2011-05-31 2012-12-06 Kpss-Kao Professional Salon Services Gmbh Hair treatment composition
EP2550953A1 (en) 2011-07-27 2013-01-30 KPSS-Kao Professional Salon Services GmbH Post-foaming gel composition
WO2013014139A2 (en) 2011-07-27 2013-01-31 Kao Germany Gmbh Post-foaming gel composition
EP2868309A1 (en) 2013-10-31 2015-05-06 Kao Corporation Hair styling composition
EP2942083A1 (en) 2014-05-07 2015-11-11 Kao Germany GmbH Aqueous cosmetic powder composition
WO2016169957A1 (en) 2015-04-20 2016-10-27 Akzo Nobel Chemicals International B.V. Acrylic hair fixative copolymers and compositions
WO2017083328A1 (en) 2015-11-09 2017-05-18 Merial, Inc. Pet care compositions
WO2017083326A1 (en) 2015-11-09 2017-05-18 Merial, Inc. Pet care cleansing composition
EP3187227A1 (en) 2015-12-28 2017-07-05 Kao Corporation Use of silicone copolymer for improving select hair properties and process thereof

Similar Documents

Publication Publication Date Title
US3577518A (en) Hydrophilic hairspray and hair setting preparations
US3577517A (en) Acrylic or methacrylic acid copolymer in resinous aerosol hair preparations
US3405084A (en) Neutralized terpolymeric resin of vinyl pyrrolidone, alkyl acrylate or methacrylate,and unsaturated monocarboxylic acid
US3485915A (en) Thickened hydroxypropyl cellulose compositions
US3579629A (en) Salts of copolymers of vinyl acetate/crotonic acid/vinylic or allylic or methallyic esters in hair cosmetics
US3445566A (en) Hair spray compositions containing an ultraviolet absorbing film forming copolymer
US6329472B1 (en) Water-soluble or water-dispersible graft copolymers based on a polyvinyllactam, their preparation and use
US5391368A (en) Hair styling shampoos
US5019377A (en) Low glass transistion temperature adhesive copolymers for use in hair styling products
US4009256A (en) Novel shampoo composition containing a water-soluble cationic polymer
US3728447A (en) Fatty acid lactylates and glycolates for conditioning hair
US4664835A (en) Washing and foaming composition based on surface-active agents and anionic polymers
US5824296A (en) Solid hair composition containing a particular structuring agent
US4764363A (en) Hair styling mousse
US3964500A (en) Lusterizing shampoo containing a polysiloxane and a hair-bodying agent
US4283384A (en) Cosmetic compositions containing polymers produced in the presence of cerium ions
US4080310A (en) Amphoteric conditioning shampoo
US5077042A (en) Conditioning hair relaxer system with conditioning activator
US6410005B1 (en) Branched/block copolymers for treatment of keratinous substrates
US4348380A (en) Cosmetic compositions for the hair and skin based on copolymers having tertiary amine and/or quaternary ammonium functions
US5039519A (en) Hair cosmetic composition
US5620684A (en) Cosmetic compositions for maintaining hairstyle possessing improved fixing power
US5478553A (en) Hair fixative compositions containing polymeric N-vinyl formamide
US20020061319A1 (en) Film-forming cosmetic composition
US5686067A (en) Low voc hair spray compositions