US3914403A - Hair care preparations containing N-vinyl pyrrolidone homo- and copolymers and a quaternized copolymer of vinyl pyrrolidone - Google Patents
Hair care preparations containing N-vinyl pyrrolidone homo- and copolymers and a quaternized copolymer of vinyl pyrrolidone Download PDFInfo
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- US3914403A US3914403A US359325A US35932573A US3914403A US 3914403 A US3914403 A US 3914403A US 359325 A US359325 A US 359325A US 35932573 A US35932573 A US 35932573A US 3914403 A US3914403 A US 3914403A
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- vinyl pyrrolidone
- hair
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- copolymer
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/046—Aerosols; Foams
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/817—Compositions 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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
- A61K8/8176—Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/817—Compositions 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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
- A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/59—Mixtures
- A61K2800/594—Mixtures of polymers
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- Y—GENERAL 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/01—Aerosol hair preparation
-
- Y—GENERAL 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/02—Resin hair settings
Definitions
- compositions containing N-vinyl pyrrolidone polymers and the quaternized copolymer exhibit excellent adhesion and holding-power when employed for hair care preparations.
- the present invention is directed to certain novel cosmetic compositions, i.e., aerosol hair sprays,hair conditioners, and hair setting lotions, creams, etc., containing polymeric N-vinyl pyrrolidone homoand copolymers thereof, (i.e., with vinyl acetate), referred to as PVP and VP/VA, respectively; and a minor amount of a quaternary copolymer of vinyl pyrrolidone; more particularly, the present invention is directed to such cosmetic compositions containing PVP or vinyl pyrrolidone/vinyl acetate copolymers (VP/VA) admixed with quaternary copolymer of vinyl pyrrolidone and a further copo
- a number of synthetic polymers are presently used in hair sprays, hair wave set lotions, hair conditioners, etc.;, the function of such synthetic polymers being generally to contribute body and holding power to the hair-do sets.
- the holding phenomena of hair sprays and setting lotions are, however, not very well defined.
- a polymer globule holds several'keratin fibers together so as to produce the necessary holding of the hair in place.
- setting and conditioning lotions however, polymers are deposited over the surface of the hair and again several hair strands are adhered together.
- polymer adhesion to the hair is a very important factor which influences the usefulness of a particular synthetic polymer or resin in a hair preparation.
- many of the currently employed synthetic polymers or resins exhibit poor adhesion thereby causing poor holding of the hair and excessive flaking when the hair is combed or brushed.
- the principal synthetic polymers or resins employed in hair sprays, wave set lotions, and hair conditioners include polyvinyl pyrrolidone homopolymers and copolymers, half esters of polyvinyl ethers maleic anhydride, polyvinyl acetate crotonic acid and terpolymers, half esters of ethylene maleic anhydride and various others.
- compositions e.g., hair spray compositions, which contain PVP or VP/VA and a minor amount of a quaternary copolymer of vinyl pyrrolidone, which two component system contributes to the body and holding of the hair-do while eliminating the disadvantages of flaking and undue stiffness.
- It is still a further object of the present invention to providetsuch novel compositions comprising PVP or VP/VA polymers and a quaternary copolymer of a) N- vinyl pyrrolidone and a b) di-loweralkylaminoalkyl acryla'te or methacrylate and optionally a further mono vinyl monomer different from a and b and copolymericable therewith, in a suitable cosmetic vehicle, e.g., water, alcohol or water-alcohol mixtures.
- a suitable cosmetic vehicle e.g., water, alcohol or water-alcohol mixtures.
- Poly (N-vinyl pyrrolidone) utilized herein is represented by the following structural formula:
- n represents a number indicative of the extent of polymerization, and is usually at least 3 or 4.
- the poly (N-vinyl pyrrolidone) polymers will have molecular weights ranging from at least 400 up to 2,000,000 or more. Viscosity measurements are commonly used as an indication of the average molecular weight of polymeric compositions, the instant polymers being characterized by a chain of carbon atoms to which the lactam righs are attached through their nitrogen atoms:
- the K value (Fikentscher) of any particular mixture of polymer is calculated from viscosity data and is useful as an indication of the average molecular weight of such mixture. Its determination is fully described in Modern Plastics, 23, No. 3, 157-61, 212, 214, 216, 218 (1945), and is defined as 1,000 times k in the empirical relative viscosity equation:
- C is the concentration in grams per hundred cc. of polymer solution and n,,,, is the ratio of the viscosity of the solution to that of pure solvent.
- K values are reported as 1000 times the calculated viscosity coefficient in order to avoid the use of decimals.
- polymeric N-vinyl lactams having a K value of about to 200, preferably of 30 to 100 because of their viscosity at lower concentrations.
- Intrinsic viscosity and K are intended to be independent of concentration.
- n The number of recurring polymer units enclosed by brackets in the foregoing general structural formula, indicated by n, or the extent of degree of polymerization corresponds to a chain of roughly 4 to 20,000 monomer units or more. In actual practice, a mixture of polymeric molecules, each containing a different number (n) of monomer units, is always produced.
- the polymers are readily prepared by the procedural steps given in US. Pat. Nos. 2,265,450, 2,317,804 and 2,335,454 and in which working examples of all the species characterized by the above formula are given and all of which are incorporated herein by reference thereto.
- N-vinyl pyrrolidone is employed as a comonomer, to form vinyl pyrrolidone/vinyl acetate copolymers
- operable ranges are 1:99 to 99: l preferably 90:10 to 1090, most preferably 20:70 vinyl pyrrolidone to 30:80 vinyl acetate.
- Also operative are 90:10 percent of a homopolymer of N-vinyl pyrrolidone admixed with said quaternized copolymer.
- These copolymers may be prepared in accordance with procedures known in the art.
- the quaternary copolymers employed in the novel compositions of the present invention are those which have the following formula:
- U- CH X is Cl, Br, I, S0 H CH OSO and M is a monomeric unit resulting from the heteropolymerization employing an optional mono vinyl new hydroxl containing monomer different from and copolymerizable with the n and m units.
- such quaternary copolymers are prepared by the copolymerization of N-vinyl pyrrolidone and di-loweralkylaminoalkyl acrylate or methacrylate, and optionally a further mono vinyl monomer different from and copolymerizable with n and m.
- the monomers are copolymerized in ac-.
- cordance with the present invention so that based upon 100 mole percent, the vinyl pyrrolidone units are presc. 0 50 mole percent of a vinyl monomer different from and copolymerizable with A and B.
- Such copolymers are conveniently prepared by subjecting a solution of vinyl pyrrolidone and the amino acrylate or amino methacrylate monomer with or without an optional copolymerizable vinyl monomer to conditions conducive to vinyl polymerization through the double bond.
- polymerization may suitably be initiated by the action of free radicals, the polymerization proceeding exothermically once initiated.
- Suitable free radical catalysts conveniently employed and suitably utilized in accordance with the production of the copolymers include organic and inor- 1 ganic peroxides, e.g., hydrogen peroxide, t-butyl peroxthe quaternary copolymers of the present invention inelude such materials as:
- the optional monovinyl or vinylidene monomer represented by M in the above structural formula can comprise any conventional vinyl monomer copolymerizable with N-vinyl pyrrolidone.
- suitable conventional vinyl monomers include the alkyl vinyl ethers, e.g. methyl vinyl ether, ethyl vinyl ether, octyl vinyl ethers, e.g. acrylic and methacrylic acid and esters thereof, e.g.
- vinyl aromatic monomers e.g., styrene, a-methyl styrene, etc.
- vinyl acetate vinyl alcohol
- vinylidene chloride acrylonitrile and substituted derivatives thereof
- methacrylonitrile and substituted derivatives thereof acrylamide and methacrylamide and N- substituted derivatives thereof
- vinyl chloride crotonic acid and esters thereof; etc.
- optional copolymerizable vinyl monomer can comprise any conventional vinyl monomer copolymerizable with N-vinyl pyrrolidone and said acrylate or methacrylate.
- B. 5 40 mole percent percent of a diloweralkylaminoalkyl acrylate or methacrylate present invention can be characterized as'having a reide, etc. aliphatic azo compounds, e.g., azobisisobutyronitrile as well as other free radical forming catalysts well known in the polymerization art.
- the polymerization is preferably carried out in solution at temperatures varying from about 50C to 100C or more; however, to avoid run away conditions and to obtain a copolymer of a desirable molecular weight it is sometimes preferred to carry out the copolymerization at a temperature of from about to about C.
- the copolymerization reaction is preferably carried out in the absence of free oxygen, conveniently under a blanket of an inert gas, such as, nitrogen, argon or the like, or at atmospheric pressure.
- the copolymers are in the form of their quaternary salts. Accordingly, after completion of the polymerization reaction the polymer is submitted to a treatment conducive to quaternization of the tertiary amino group, utilizing a conventional quaternizing agent.
- suitable quaternizing agents include, such as, dialkyl sulfates, e.g., dimethyl sulfate, diethyl sulfate, etc.; alkyl sulfonic acid, e.g., methyl sulfonic acid, ethyl sulfonic acid, etc.; benzyl halides, e.g., benzyl chloride, benzyl bromide, benzyl iodide, etc.; alkyl halide, etc.
- any conventional quaternizing agent can be advantageously employed in the production of the quaternary N-vinyl pyrrolidone copolymers used in the cosmetic compositions of the present invention.
- the above quaternary copolymers employed in the compositions of the present invention can be prepared over a wide range of molecular weights. Generally, however, the molecular weight of the copolymer employed in the novel composition of the present invention is within the range of 10,000 to 1,000,000, the molecular weight being chosen somewhat with respect to the utility of the cosmetic composition.
- the quaternary copolymers of the present invention are soluble in both water and alcohol as is the PVP and VP/VA polymers and, thus, the combination can be employed in hair spray and similar cosmetic compositions containing an alcoholic, aqueous, or mixed alcoholic-aqueous base.
- the high molecular weight quaternary polymers act as their own thickeners in aqueous or alcoholic solutions, such solutions displaying a slippery feel and an ease of application to the hair. Accordingly, the use thereof of such higher molecular weight quaternary copolymers, i.e., quaternary copolymers within the molecular weight range of 50,000 to 500,000 is particularly applicable to the preparation of hair setting lotions, creams, etc.
- a further advantage of the use of pVP or VP/VA pol- -ymers and the quaternary copolymers in the hair setting and similar cosmetic preparations is that hair sprayed or otherwise treated with a hair setting composition containing same is easy to comb and easy to roll on rollers.
- setting and conditioning lotions prepared utilizing same give a firm and stiff curl yet allow easy combing without comb drag.
- both polymeric materials employed in the novel compositions of the present invention are soluble in both alcohols and water, this makes them eminently suitable in hair spray and similar compositions which conventionally have an alcoholic, aqueous, or mixed aqueous-alcoholic base.
- they may be employed in the same manner as heretofore employed conventional film-forming resins, said mixture providing improvements as set forth above by their inclusion within I the hair spray, setting lotion, or similar cosmetic preparation.
- the filmforming polymers PVP or VP/VA with the quaternary copolymer of N-vinyl pyrrolidone is generally employed in an amount of from about 0.1 to 45.0 percent by weight, the precise amount depending somewhat on the end desired utility for the composition.
- the ratio of PVP or VP/VA to quaternary copolymer being in the range of to 90 percent, preferably 50 to 50 percent.
- the base can either be aqueous, alcoholic, or a mixture of alcohols and water.
- the alcohol which is used as the alcoholic base or portion of the water-alcohol solvent system is generally a lower monohydric aliphatic alcohol, preferably, a monohydric aliphatic alcohol having from 2 to 3 carbon atoms, e.g., ethanol, isopropanol, or n-propanol, ethanol being preferred.
- the alcoholic solvent can comprise the commercially and industrially available ethyl alcohols or any one of the denatured alcohol formulas which are permitted by law for use in hair care preparations, e. c.
- the hair spray or similar composition may contain minor amounts of other ingredients for their usual purposes.
- the compositions may include plasticizing agents i.e., ethoxylated and acetylated lanolin alcohols; polyoxyethylene sorbitan derivatives such as polyoxyethylene sorbitan monopalmitate, polyoxyethylene monostearate, polyoxyethylene sorbitan trioleate; glycol esters such as diethylene glycol, propylene glycol; dimethyl phthalates; isopropyl myristate and isopropyl palmitate; long chain fatty alcohols such as oleyl, isostearyl, cetyl alcohols, etc., conditioning agents such as .water soluble and insoluble silicones;
- a setting and'conditionhydralyzed polypeptide solutions and quaternary compounds such as stearyl dimethyl be nzyl ammonium chloride.
- cetyl dimethyl benzyl ammonime chloride preservative agents such as sorbic acid; 6-acetoxy 2,4 diemthyl m-dioxan e; 2-bromo -2- nitropropane -1, 3- diol and others. All in amounts up to 5 percent by weight, preferably 0.1 to 2 percent.
- the usual aerosol type container and equipment and usual aerosol type propellant may be effectively utilized to propel the compositions to the hair, such propellants being liquified lower hydrocarbons such as propane, n-butane, and isobutane and the low boiling chlorofluoro hydrocarbons identified broadly as Freons.”
- propellants being liquified lower hydrocarbons such as propane, n-butane, and isobutane and the low boiling chlorofluoro hydrocarbons identified broadly as Freons.”
- Freons liquified lower hydrocarbons
- Preferred propellants may be F11 and F12 and F12 and F1 14. All propellants are used in a pressurizing amount.
- the propellant in an aerosol type hair spray composition in accordance with the present invention, is generally employed in an amount of from about 25 percent to about 65 percent by weight based on the total composition.
- the film-forming two component polymer system constitutes from about 0.1 percent to about 5 percent by weight, preferably, between 0.1 and 2.5 percent with the remainderconstituting the alcohol, water, or water-alcohol mixture.
- the hair spray composition can contain minor amounts, i.e., up to about 5 percent by weight of a surfactant or plasticizer and still lesser amounts of perfumes, i.e., up to about 0.5 percent by weight and similar agents.
- the sprayable hair composition is generally formed as an alcoholic or mixed aqueousalcoholic solvent system. Accordingly, suitable amounts of the various components in such composition are as follows:
- ком ⁇ онент polymeric system in an aqueous or mixed aqueous and alcoholic system may comprise the following components:
- the setting and conditioning lotions may contain minor amounts of other conventional optional materials. These include such materials as perfumes, preservatives, additional organic solvents, lanolin and lanolin derivatives, silicone lubricity agents, etc.
- optional components are conventional and employed in 'minor amounts, i.e., less than about 2 percent by weight.
- An optional surfactant or plasticizer for the film-forming copolymer can also be employed in an amount up to about 5 percent by weight:
- compositions can be prepared in the form of wig conditioners, hair coloring preparations, hand lotions, protective creams,
- the film-forming two component polymeric system is soluble in both the alcoholic and aqueous systems utilized in the preparation of the above and similar cosmetic and relatedpreparations. Accordingly, in order to produce such formulations, it is merely necessary to dissolve the same in the suitable solvent with previous, simultaneous or subsequent-addition of the other optional components. Solution of the same in the solvent system may be facilitated by mixing.
- EXAMPLE 1 Production of film-forming quaternary copolymer A copolymer was produced utilizing polymerization apparatus comprising a 5 liter kettle equipped with me chanical stirrer, reflux condenser, thermometer, and gas inlet tube. Some 1,225 parts of ethanol as a solvent were charged into the kettle and 800 parts of vinyl pyrrolidone and 200 parts of dimethylaminoethyl methacrylate were added and agitation was started. To the system was added one part of azobisisobutyronitrile and the system was purged thoroughly with nitrogen. The temperature of the system was raised to gentle reflux at about C.
- the polymerization reaction was promoted with further additions of catalysts (one part each) until the amount of residual monomer was below 0.6 percent.
- the system was thereafter cooled to 25 C and the speed of the agitation was increased.
- the aerosol hair spray formulation was prepared by dissolving the film-forming two component polymeric admixture in the ethanol solvent and thereafter adding the plasticizer with vigorous mixing. After such mixing, the perfume oil, lubricity agents and the like may be added and the composition filtered and transferred to an aerosol can where it is crimped and charged with the necessary propellants.
- Such a hair spray composition was found to be easily applied to .the hair, the same providing a natural look yet offering excellent holding power.
- the stiff look associated with the use of half esters of polyvinyl ethers, maleic anhydride or polyvinyl acetate, crotonic acid co'and terpolymer hair setting resins was not present and improved mixture resistance no flaking associated with the employment of the hair spray composition containing the film-forming two component polymeric admixture.
- EXAMPLE 3 In a manner similar to Example 2, an aerosol hair spray particularly adapted for men was prepared in an alcohol-aqueous solvent system. Utilizing a mixing procedure. as in Example 2.7 the following composition was prepared:
- the hair spray composition was found to have improved moisture resistance and excellent holding properties providing a natural look to the hair.
- the use of the two component polymeric admixture was seen to be superior to PVP alone or VP/VA systems alone in that no flaking and no undue stiffness of the hair resulted.
- EXAMPLE 4 A composition as in Example 3 was prepared except that the film-forming quaternized copolymer component of N-vinyl pyrrolidone and diethylaminoethyl methacrylate was replaced with a substantially equivalent amount of a quaternized copolymer of N-vinyl pyrrolidone and the following monomers:
- EXAMPLE 5 A hair spray composition as set forth in Example 2 was produced except that the quaternized copolymer of N-vinyl pyrrolidone was prepared by employing the following comonomers in the following amounts:
- EXAMPLE 6 A hair spray composition as set forth in Example 2 was again produced except that the quaternized copolymer component of N-vinyl pyrrolidone was one produced by the copolymerization system of Example 1 including the following further copolymerizable vinyl monomers:
- EXAMPLE 7 An anhydrous aerosol hair spray was produced through a procedure such as set forth in Example 2 by combining the following components:
- composition containing no water was also" found to be extremely suitable for hair spray purposes.
- the composition exhibited excellent adhesion and holding power when employed as an aerosol hair spray, particularly adapted for men.
- EXAMPLE 8 A concentrated setting and conditioning lotion for womens hair was produced as follows. A copolymer of vinyl pyrrolidone and dimethylaminoethyl methacrylate (80:20) quaternized with diethyl sulfate was thereafter dissolved in water and alcohol so as to provide a 2.0 percent solids content. After mixing the system well, a plasticizer, silicone lubricity agent, and perfume oil were added with additional mixing. Stirring was stopped and the system was allowed to rest for about 20 minutes so as to allow the escape of air bubbles. Such a formulation designed for use on damp or towel dried hair can then be packed in a plunger or tube type dispenser. The composition produced as above had the following formulation:
- the hair sprays of the present invention are seen to provide excellent adhesion and holding power without the disadvantages of previously employed compositions.
- a hair care composition comprising a solvent selected from the group consisting of water, a C monohydric aliphatic alcohol and mixtures of each of these. said solvent containing a polymeric component approximately 0.1 to about 45 percent by weight of said composition, said polymeric component consisting essentially of.
- n 40-90 percent, m is 5-40 mole percent,-p is 0-50 mole percent, and n+m+p 100;
- R is H or Ch ;
- 'R is CH Ch CH or C,H where x 2-18;
- R is CH or C H R, is CH C H or X is Cl, Br, I, SO.,, or CH OSO and
- M is a vinyl monomeric unit having no hydroxyl groups and different I 3.
- component l is a copolymer of vinyl pyrrolidone and vinyl acetate.
- composition of claim 3 wherein said copolymer is composed of about (10:90) parts vinyl pyrrolidone and (:10) parts vinyl/acetate.
- composition of claim 1 wherein unit m is dimethylaminoethyl methacrylate.
- composition of claim 5 wherein said quaternized copolymer is composed of vinyl pyrrolidone and dimethylaminoethyl methacrylate.
- An aerosol hair spray containing a pressurizing amount of an aerosol propellant and the composition as defined inclaim l.
- An aerosol hair spray composition comprising:
- composition of claim 8 wherein unit m is dimethylaminoethyl methacrylate.
- a hair setting and conditioning lotion comprising:
- unit m is dimethylaminoethyl methacrylate.
- component 2 is a quaternized copolymer of vinyl pyrrolidone and dimethylaminoethyl methacrylate.
- component 2 has a molecular weight within the range 1 is a co-polymer of vinyl pyrrolidone and vinyl acetate.
Abstract
Description
Claims (21)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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US359325A US3914403A (en) | 1973-05-11 | 1973-05-11 | Hair care preparations containing N-vinyl pyrrolidone homo- and copolymers and a quaternized copolymer of vinyl pyrrolidone |
CA198,692A CA1022850A (en) | 1973-05-11 | 1974-05-02 | Hair care preparations containing n-vinyl pyrrolidone homo-and copolymers and a quaternized copolymer of vinyl pyrrolidone |
Applications Claiming Priority (1)
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US359325A US3914403A (en) | 1973-05-11 | 1973-05-11 | Hair care preparations containing N-vinyl pyrrolidone homo- and copolymers and a quaternized copolymer of vinyl pyrrolidone |
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US3914403A true US3914403A (en) | 1975-10-21 |
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US359325A Expired - Lifetime US3914403A (en) | 1973-05-11 | 1973-05-11 | Hair care preparations containing N-vinyl pyrrolidone homo- and copolymers and a quaternized copolymer of vinyl pyrrolidone |
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CA (1) | CA1022850A (en) |
Cited By (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2326177A1 (en) * | 1975-10-01 | 1977-04-29 | Langheim Peter | HAIR FIXING AGENT |
DE2651749A1 (en) * | 1975-11-13 | 1977-05-26 | Oreal | HAIR DYE PRODUCTS AND HAIR DYE PROCESSES |
US4035478A (en) * | 1976-03-08 | 1977-07-12 | American Cyanamid Company | Clear, water-white hair conditioning composition |
US4057623A (en) * | 1975-03-29 | 1977-11-08 | Henkel Kommanditgesellschaft Auf Aktien | Cosmetic emulsions containing N-vinylpyrrolidone-alkyl acrylate copolymers |
US4165367A (en) * | 1977-06-10 | 1979-08-21 | Gaf Corporation | Hair preparations containing vinyl pyrrolidone copolymer |
US4192862A (en) * | 1977-07-28 | 1980-03-11 | Lever Brothers Company | Hairspray containing a hairspray resin and a drag reducing agent |
US4223009A (en) * | 1977-06-10 | 1980-09-16 | Gaf Corporation | Hair preparation containing vinyl pyrrolidone copolymer |
US4237253A (en) * | 1977-04-21 | 1980-12-02 | L'oreal | Copolymers, their process of preparation, and cosmetic compounds containing them |
US4265778A (en) * | 1977-08-17 | 1981-05-05 | Colgate-Palmolive Company | Soap bar |
US4273760A (en) * | 1979-02-05 | 1981-06-16 | National Starch And Chemical Corporation | Shampoo compositions |
US4507280A (en) * | 1979-07-02 | 1985-03-26 | Clairol Incorporated | Hair conditioning composition and method for use |
US4529586A (en) * | 1980-07-11 | 1985-07-16 | Clairol Incorporated | Hair conditioning composition and process |
US4663158A (en) * | 1979-07-02 | 1987-05-05 | Clairol Incorporated | Hair conditioning composition containing cationic polymer and amphoteric surfactant and method for use |
US4673569A (en) * | 1985-02-12 | 1987-06-16 | Faberge Incorporated | Mousse hair composition |
WO1988003017A1 (en) * | 1986-10-24 | 1988-05-05 | Gaf Corporation | Composition used in permanent alteration of hair color |
WO1988002985A1 (en) * | 1986-10-24 | 1988-05-05 | Gaf Corporation | Quaternized nitrogen containing compounds |
WO1988002997A1 (en) * | 1986-10-24 | 1988-05-05 | Gaf Corporation | Compositions used in permanent structure altering of hair |
US4814101A (en) * | 1987-03-16 | 1989-03-21 | Henkel Kommanditgesellschaft Auf Aktien | Zwitterionic polymers and their use in hair treatment preparations |
WO1990001920A1 (en) | 1988-08-25 | 1990-03-08 | Gaf Chemicals Corporation | Hydrolysis resistant vinyl lactam amino acrylamide polymers |
US5011493A (en) * | 1983-04-14 | 1991-04-30 | Belykh Sergei I | Material for connecting members for inner soft tissues and organs |
US5110585A (en) * | 1986-10-24 | 1992-05-05 | Isp Investments Inc. | Quaternized nitrogen containing polycyclic compounds |
US5830440A (en) * | 1991-11-21 | 1998-11-03 | L'oreal | Aqueous aerosol hair spray |
US6410005B1 (en) | 2000-06-15 | 2002-06-25 | Pmd Holdings Corp. | Branched/block copolymers for treatment of keratinous substrates |
US6423101B1 (en) * | 1998-01-23 | 2002-07-23 | Eugene Perma | Ammonia-free composition for dyeing keratinous fibres |
US6436380B1 (en) * | 1992-12-31 | 2002-08-20 | Advantage Partners Llc | Baldness cosmetic and method of application |
US20030147929A1 (en) * | 2000-02-23 | 2003-08-07 | Kim Son Nguyen | Cosmetic agent |
US6814957B1 (en) * | 1992-12-31 | 2004-11-09 | Kenneth Pond | Baldness cosmetic and method of application |
US20050101740A1 (en) * | 2003-09-01 | 2005-05-12 | Nathalie Mougin | Block ethylenic copolymers comprising a vinyllactam block, cosmetic compositions containing them and cosmetic use of these copolymers |
US20050106117A1 (en) * | 2002-03-12 | 2005-05-19 | Gerald Adams | Triblock copolymers for cosmetic or personal care compositions |
US20050238594A1 (en) * | 2003-09-15 | 2005-10-27 | Nathalie Mougin | Block ethylenic copolymers comprising a vinyllactam block, cosmetic or pharmaceutical compositions comprising them and cosmetic use of these copolymers |
US20050255067A1 (en) * | 2004-05-17 | 2005-11-17 | Leighton John C | Hair fixative film |
US20060088487A1 (en) * | 2003-09-15 | 2006-04-27 | Nathalie Mougin | Block ethylenic copolymers comprising a vinyllactam block, cosmetic or pharmaceutical compositions containing them and cosmetic use of these copolymers |
US20060263317A1 (en) * | 2003-04-01 | 2006-11-23 | Gerald Adams | Aba block copolymers for hair styling composition |
WO2011154457A1 (en) | 2010-06-09 | 2011-12-15 | L'oreal | 2-pyrrolidone derivatives functionalized with an ester, acid or amide radical, cosmetic composition comprising them and use thereof for conditioning keratin materials |
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Cited By (37)
Publication number | Priority date | Publication date | Assignee | Title |
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US4057623A (en) * | 1975-03-29 | 1977-11-08 | Henkel Kommanditgesellschaft Auf Aktien | Cosmetic emulsions containing N-vinylpyrrolidone-alkyl acrylate copolymers |
FR2326177A1 (en) * | 1975-10-01 | 1977-04-29 | Langheim Peter | HAIR FIXING AGENT |
DE2651749A1 (en) * | 1975-11-13 | 1977-05-26 | Oreal | HAIR DYE PRODUCTS AND HAIR DYE PROCESSES |
US4035478A (en) * | 1976-03-08 | 1977-07-12 | American Cyanamid Company | Clear, water-white hair conditioning composition |
US4237253A (en) * | 1977-04-21 | 1980-12-02 | L'oreal | Copolymers, their process of preparation, and cosmetic compounds containing them |
US4165367A (en) * | 1977-06-10 | 1979-08-21 | Gaf Corporation | Hair preparations containing vinyl pyrrolidone copolymer |
US4223009A (en) * | 1977-06-10 | 1980-09-16 | Gaf Corporation | Hair preparation containing vinyl pyrrolidone copolymer |
US4192862A (en) * | 1977-07-28 | 1980-03-11 | Lever Brothers Company | Hairspray containing a hairspray resin and a drag reducing agent |
US4265778A (en) * | 1977-08-17 | 1981-05-05 | Colgate-Palmolive Company | Soap bar |
US4273760A (en) * | 1979-02-05 | 1981-06-16 | National Starch And Chemical Corporation | Shampoo compositions |
US4507280A (en) * | 1979-07-02 | 1985-03-26 | Clairol Incorporated | Hair conditioning composition and method for use |
US4663158A (en) * | 1979-07-02 | 1987-05-05 | Clairol Incorporated | Hair conditioning composition containing cationic polymer and amphoteric surfactant and method for use |
US4529586A (en) * | 1980-07-11 | 1985-07-16 | Clairol Incorporated | Hair conditioning composition and process |
US5011493A (en) * | 1983-04-14 | 1991-04-30 | Belykh Sergei I | Material for connecting members for inner soft tissues and organs |
US4673569A (en) * | 1985-02-12 | 1987-06-16 | Faberge Incorporated | Mousse hair composition |
WO1988003017A1 (en) * | 1986-10-24 | 1988-05-05 | Gaf Corporation | Composition used in permanent alteration of hair color |
WO1988002985A1 (en) * | 1986-10-24 | 1988-05-05 | Gaf Corporation | Quaternized nitrogen containing compounds |
WO1988002997A1 (en) * | 1986-10-24 | 1988-05-05 | Gaf Corporation | Compositions used in permanent structure altering of hair |
US5110585A (en) * | 1986-10-24 | 1992-05-05 | Isp Investments Inc. | Quaternized nitrogen containing polycyclic compounds |
US4814101A (en) * | 1987-03-16 | 1989-03-21 | Henkel Kommanditgesellschaft Auf Aktien | Zwitterionic polymers and their use in hair treatment preparations |
WO1990001920A1 (en) | 1988-08-25 | 1990-03-08 | Gaf Chemicals Corporation | Hydrolysis resistant vinyl lactam amino acrylamide polymers |
US4923694A (en) * | 1988-08-25 | 1990-05-08 | Gaf Chemicals Corporation | Hydrolysis resistant vinyl lactam amino acrylamide polymers |
US5830440A (en) * | 1991-11-21 | 1998-11-03 | L'oreal | Aqueous aerosol hair spray |
US6436380B1 (en) * | 1992-12-31 | 2002-08-20 | Advantage Partners Llc | Baldness cosmetic and method of application |
US6814957B1 (en) * | 1992-12-31 | 2004-11-09 | Kenneth Pond | Baldness cosmetic and method of application |
US6423101B1 (en) * | 1998-01-23 | 2002-07-23 | Eugene Perma | Ammonia-free composition for dyeing keratinous fibres |
US20030147929A1 (en) * | 2000-02-23 | 2003-08-07 | Kim Son Nguyen | Cosmetic agent |
US8398963B2 (en) | 2000-02-23 | 2013-03-19 | Basf Se | Cosmetic agent |
US6410005B1 (en) | 2000-06-15 | 2002-06-25 | Pmd Holdings Corp. | Branched/block copolymers for treatment of keratinous substrates |
US20050106117A1 (en) * | 2002-03-12 | 2005-05-19 | Gerald Adams | Triblock copolymers for cosmetic or personal care compositions |
US20060263317A1 (en) * | 2003-04-01 | 2006-11-23 | Gerald Adams | Aba block copolymers for hair styling composition |
US20050101740A1 (en) * | 2003-09-01 | 2005-05-12 | Nathalie Mougin | Block ethylenic copolymers comprising a vinyllactam block, cosmetic compositions containing them and cosmetic use of these copolymers |
US20050238594A1 (en) * | 2003-09-15 | 2005-10-27 | Nathalie Mougin | Block ethylenic copolymers comprising a vinyllactam block, cosmetic or pharmaceutical compositions comprising them and cosmetic use of these copolymers |
US20060088487A1 (en) * | 2003-09-15 | 2006-04-27 | Nathalie Mougin | Block ethylenic copolymers comprising a vinyllactam block, cosmetic or pharmaceutical compositions containing them and cosmetic use of these copolymers |
US20050255067A1 (en) * | 2004-05-17 | 2005-11-17 | Leighton John C | Hair fixative film |
US7972589B2 (en) * | 2004-05-17 | 2011-07-05 | Akzo Nobel N.V. | Hair fixative film |
WO2011154457A1 (en) | 2010-06-09 | 2011-12-15 | L'oreal | 2-pyrrolidone derivatives functionalized with an ester, acid or amide radical, cosmetic composition comprising them and use thereof for conditioning keratin materials |
Also Published As
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