Classifications

• • 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
  • A61K8/18—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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F20/00—Homopolymers 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
  • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
  • C08F20/52—Amides or imides
  • C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
• • 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 adapted for use as an aerosol spray and containing a tetrapolymer of (A) N-t-butyl acrylamide or N-isopropyl acrylamide, (B) acrylamide or methacrylamide, (C) N-vinyl pyrrolidone and (D) acrylic or methacrylic acid, and hair spray compositions per se, are disclosed.
• my tetrapolymer offers the commercial formulator great latitude to vary the degree of neutralization so that the water-solubility can be optimized with re- 3,634,368 Patented Jan. 11, 1972 gard to washability. These unique properties are achieved by a balanced blend of the polymer component monomers.
• the characteristics of my novel tetrapolymer are a direct function of a hydrophobichydrophilic balance and the number of carboxyl groups therein. They are further related to the carboxyl groups in such a fashion that the water solubility can be varied over a wide range according to the degree of neutralization which is controlled, as is known in the art, by the amount of solubilizing base added to the final formulation.
• my novel polymeric material is a tetrapolymer of ('1) N-t-butyl acrylamide or N-isopropyl acrylamide, (2) acrylamide or methylacrylamide, (3) N-vinyl pyrrolidone and (4) acrylic or methacrylic acid.
• the unique characteristics of this novel tetrapolymer are achieved by varying the amounts of each monomeric component over a relatively narrow and critical range.
• the N-t-butyl acrylamide or N-isopropyl acrylamide should be present in an amount ranging from about -80%, by weight, the acrylamide or methacrylamide in an amount ranging from about 5-15%, by Weight, the N-vinyl pyrrolidone in an amount ranging from about 5-15%, by weight, and the acrylic or methacrylic acid in an amount ranging from about 110%, by weight, said weights being based on the total Weight of the polymer and totaling
• the method or manner by which the tetrapolymer is produced is not critical and therefore forms no part of the instant invention. Any known polymerization technique can be utilized ie the monomers may be polymerized via bulk, solution, emulsion, etc. processes without detracting from the essential characteristics of the resultant polymer.
• vinyl polymerization may be inhibited or retarded by oxygen, it is desirable to free the reactants from dissolved oxygen and to maintain an inert atmosphere throughout the course of the polymerization, conveniently by a continuous purge with an inert gas stream such as nitrogen or argon.
• an inert gas stream such as nitrogen or argon.
• the reaction can be initiated by any of a number of systems preferably with a ready source of free radicals such as a,a-azodiisobutyronitrile or organic peroxy compounds, for example, lauroyl peroxide and benzoyl peroxide or the various redox systems comprising, commonly, as the oxidizing component, the inorganic peroxides or persulfates and as the reducing component sulfur dioxide, a bisulfite, hydrosulfite or thiosulfate, or an organic hydroperoxide and activator. In some instances, a combination of systems will be most desirable. Furthermore, it is possible to initiate the polymerization thermally or by radiation over a wide range of energy levels. The reaction may be modified by the addition of chain transfer agents to control the molecular Weight below its maximum value and by accelerators to increase the rate of reaction.
• a ready source of free radicals such as a,a-azodiisobutyronitrile or organic peroxy compounds, for example, lauroyl peroxid
• any number of solvents alone or in combination will be found useful.
• the choice is not limited to solvents in which a homogeneous mixture can be maintained.
• An acetone- Water-mixture in which all the reactants and the product are soluble is particularly advantageous and permits the employment of a simple inorganic redox system such as ammonium persulfate-sodium meta-bisulfite with ferrous sulfate as an accelerator.
• a simple inorganic redox system such as ammonium persulfate-sodium meta-bisulfite with ferrous sulfate as an accelerator.
• solution polymerization is the preferred method.
• the rate and extent of polymerization can be controlled through the choice of catalysts and additives and the amount and time intervals at which they are introduced, the level of monomer concentration, the temperature maintained and the solvent used.
• the preferred temperatures range from 40 C. to 80 C., particularly from 40 to 60 C.
• the molecular weight of my tetrapolymer be controlled so as to give intrinsic viscosities of not higher than about 0.55 dl./g.
• the tetrapolymer described in this disclosure and prepared from the four monomers in the proportions specified above is formulated into hair spray compositions as described in the above-cited U.S. patents, hereby incorporated herein by reference.
• the tetrapolymer may be formulated, in concentrations ranging from 0.5 to 4.0%, by weight, into such an aerosol composition.
• the aerosol will contain ordinarily from about 3565% by weight of propellant, more particularly from about 4555%, and from about 35-65% by weight of a lower alcohol, more particularly from about 4555%, the preferred alcohols being ethanol and isopropanol or mixtures of these with small amounts of n-propanol.
• a neutralizing agent in amounts suflicient to neutralize from 50-100% of the carboxyl groups present in the resin must be added to form the final composition. If desired, small amounts of other ingredients commonly added to hair sprays, such as plasticizers, perfumes, oils and lanolin etc. may also be incorporated into the composition.
• the film-forming tetrapolymer is, however, the essential part of the invention.
• Halogenated propellants such as those described in the above-cited patents are preferred because of their nonfiammable characteristics.
• the film-forming resin composition of the present invention is also useful as a temporary coating in many other applications where it is desirable that the film be removed easily by washing.
• the composition may be used in the automobile industry, glassware industry, etc. as temporary coatings.
• the neutralizing agent may be used at a lower level or omitted entirely in order to increase the resistance of the film to water.
• 2-amino-2-methyl-1,3-propandiol (AMPD) and 2- amino-2-methyl-propanol (AMP) are preferred neutralizers.
• other neutralizers such as 2-aminobutanol may also be used.
• Example 1 33.3 parts of N-tertiary butyl acrylamide in 300 parts of acetone, 2.7 parts of acrylic acid in 40 parts of acetone, 0.6 part of sodium hydroxide in 30 parts of water, 4.5 parts of acrylamide in 15 parts of water, 4.5 parts of N- vinyl pyrrolidone and 0.100 part of sodium meta-bisulfite in parts of water are charged to a suitable reaction vessel in the order given and with continuous stirring.
• the vessel is equipped with a variable speed stirrer, cooling condenser, nitrogen inlet tube and thermometer.
• the mixture is heated under continuous nitrogen gas purge and with stirring to 50 C. by means of a water bath.
• the following reagents are then added in the order given: 0.003 part of thioglycerol in 1.5 parts of acetone, 0.090 part of ammonium persulfate in 10 parts of Water and .020 part of FeSO -7H O in 20 parts of water. Additional thioglycerol, .045 part in 22.5 parts of acetone is introduced over the course of the next 2% hours.
• the temperature is maintained at 50 C., and the nitrogen purge and stirring are continued to termination at 3 hours.
• the reaction vessel is then opened to air.
• the polymerization mixture is filtered, acidified with 0.5 N HCl in 20% excess and placed into a large volume of water with continuous agitation. The product is collected, washed with water and dried. A 74% yield of the tetrapolymer with a carboxyl content of 3.4% is obtained.
• the intrinsic viscosity in absolute ethanol at 30 C. is 0.47 dl./g.
• Example 2 The procedure of Example 1 is again followed except that an equivalent amount of N-isopropyl acrylamide is substituted for the N-t-butyl acrylamide therein. Similar results are achieved.
• Example 3 Following the procedure of Example 1 except that methacrylamide is substituted in equal amounts, for the acrylamide therein, a similar tetrapolymer is recovered.
• Example 4 The substitution of methacrylic acid for the acrylic acid in Example 1, in an equivalent amount, all other conditions remaining equal, results in a tetrapolymer of properties similar to that of said Example 1.
• Example 5 2.0 percent of the tetrapolymer of Example 1 and 52.85 percent of ethanol are charged to a suitable mixing vessel. The contents are agitated until the tetrapolymer dissolves and 0.05 percent of aminomethylpropanediol, as neutralizer, and 0.1 percent of polyethylene glycol (molecular weight 600), as plasticizer, are then added with agitation. The resultant material is placed into an aerosol bomb which is then charged with 45.0 percent of a mixture of trichloromonofluoromethane and dichlorodifluoromethane (60/ 40) as propellant. The resultant solution is sprayed onto hair. The hair is effectively held in its styled form and has a smooth appearance even at relative humidity. The hair is not tacky and no flaking results during combing. The hair may be completely cleaned by Washing with dilute solutions of customary soaps and shampoos.
• a composition adapted for use as an aerosol spray said composition containing a tetrapolymer comprising from about 7080% of N-t-butyl acrylamide or N-isopropyl acrylamide, from about 515% of acrylamide or methacrylamide, from about 5l5% of N-vinyl pyrrolidone and from about 1-10% of acrylic acid or methacrylic acid, said percentages being by weight, based on the total Weight of said tetrapolymer.
• composition according to claim 1 wherein said tetrapolymer comprises N-t-butyl acrylarnide, acrylamide, N-vinyl pyrrolidone and methacrylic acid.
• a composition according to claim 1 wherein said tetrapolymer comprises N-t-butyl acrylamide, acrylamide, N- vinyl pyrrolidone and methacrylic acid.
• composition according to claim 1 wherein said tetrapolymer comprises N-isopropyl acrylamide, acrylamide, N-vinyl pyrrolidone and acrylic acid.
• composition according to claim 1 wherein said tetrapolymer comprises N-t-butyl acrylamide, methacryl amide, N-vinyl pyrrolidone and acrylic acid.

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• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• General Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Epidemiology (AREA)
• Birds (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Cosmetics (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Compositions Of Macromolecular Compounds (AREA)

Applications Claiming Priority (1)

Publications (1)

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Family Applications (1)

Country Status (10)

Cited By (6)

Families Citing this family (5)

• 1969
  • 1969-09-29 US US862044A patent/US3634368A/en not_active Expired - Lifetime
• 1970
  • 1970-06-02 ZA ZA703718A patent/ZA703718B/xx unknown
  • 1970-06-08 AU AU16054/70A patent/AU1605470A/en not_active Expired
  • 1970-06-08 GB GB27651/70A patent/GB1283131A/en not_active Expired
  • 1970-06-23 NL NL7009195A patent/NL7009195A/xx unknown
  • 1970-07-22 DK DK380870AA patent/DK125520B/da unknown
  • 1970-07-31 ES ES382360A patent/ES382360A1/es not_active Expired
  • 1970-09-28 DE DE19702047655 patent/DE2047655A1/de active Pending
  • 1970-09-29 JP JP45085816A patent/JPS4821495B1/ja active Pending
  • 1970-09-29 FR FR7035243A patent/FR2062801A5/fr not_active Expired

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