Classifications

• • 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
• • 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
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
• • 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
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
• • 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
  • A61K8/8141—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
  • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; 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
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring

Definitions

• This invention relates to compositions and methods for treating hair. More particularly, this invention concerns a cosmetically acceptable hair fixative composition containing an anionic polymer and a method of using the composition for setting hair.
• Natural hair tends to return to its initial shape or position so it does not hold a set well. Hair styling and fixative products help build the interactive forces between hair fibers, which give adherence to the adjacent hairs so they can keep a particular shape or configuration as the polymer dries. In the past, hairsprays have dominated the styling aid market because of easy use, good styling and simple application. Pump hair sprays, hydrocarbon aerosols and carbon dioxide aerosols are three major types of sprays. However, hairsprays have largely used propellants and alcohol as their major components which are considered Volatile Organic Compounds (VOC) .
• VOC Volatile Organic Compounds
• High molecular weight polymers have been used as hair fixatives since 1940 and they have played the key role of holding the hair in place during the styling process and in the fixing step.
• most of the hair fixative polymers were designed to be soluble in alcohol or propellants, and usually these polymers have poor solubility in water.
• their performance as a hair fixative is affected when water is incorporated into the formulation.
• Cationic polymers such as polyquaternium-11 and polyquaternium-4 are excellent film-forming polymers, but their high substantivities make them difficult to wash out. Consequently, anionic polymers are most frequently used.
• anionic hair fixative polymers are also considered hygroscopic materials that often show poor hair setting properties in high humidity environments. It is thus an object of this invention to develop polymers that have a better balance between the conflicting requirements of water-indifference (good curl retention at high humidity) and water-sensitivity (rapid and complete removal from the hair when rinsed with water) .
• this invention is directed to a cosmetically acceptable hair fixative composition
• a cosmetically acceptable hair fixative composition comprising from about 0.1 to about 10 weight percent, based on polymer solids, of an anionic polymer, wherein the anionic polymer is composed of from about 10 to about 80 mole percent of 2-acrylamido-2-methyl-l- propanesulfonic acid or a base addition salt thereof and from about 90 to about 20 mole percent of one or more anionic or nonionic monomers.
• this invention is directed to a method of setting hair comprising a) applying to the hair an effective setting amount of a cosmetically acceptable hair fixative composition comprising from about 0.1 to about 10 weight percent, based on polymer solids, of an anionic polymer, wherein the anionic polymer is composed of from about 10 to about 80 mole percent of 2-acrylamido-2-methyl-l- propanesulfonic acid or a base addition salt thereof and from about 90 to about 20 mole percent of one or more anionic or nonionic monomers; and b) placing the hair in the desired configuration.
• a cosmetically acceptable hair fixative composition comprising from about 0.1 to about 10 weight percent, based on polymer solids, of an anionic polymer, wherein the anionic polymer is composed of from about 10 to about 80 mole percent of 2-acrylamido-2-methyl-l- propanesulfonic acid or a base addition salt thereof and from about 90 to about 20 mole percent of one or more anionic or nonionic monomers
• An advantage of this invention is that the anionic polymer performs well under high humidity and is easily removed by water.
• anionic polymer has excellent compatibility with an anionic thickening system.
• anionic polymer gives a silky feeling after the hair is dried.
• anionic monomer means a monomer as defined herein which possesses a net negative charge above a certain pH value.
• Representative anionic monomers include base addition salts of acrylic acid, methacrylic acid, itaconic acid, 2-acrylamido-2-methyl-l-propanesulfonic acid, sulfopropyl acrylate or methacrylate or other water-soluble forms of these or other polymerizable carboxylic or sulfonic acids, sulphomethylated acrylamide, allyl sulphonate, styrene sulfonic acid, sodium vinyl sulphonate, and the like.
• Preferred anionic monomers are acrylic acid and 2-acrylamido-2-methyl-l- propanesulfonic acid.
• Base addition salt means the salt resulting from reaction of a carboyxlic acid (-C0 2 H) group with a suitable base such as the hydroxide, carbonate, or bicarbonate of a metal cation or tetraalkylammonium cation, or with ammonia, or an organic primary, secondary, or tertiary amine of sufficient basicity to form a salt with the carboxylic acid group.
• suitable base such as the hydroxide, carbonate, or bicarbonate of a metal cation or tetraalkylammonium cation, or with ammonia, or an organic primary, secondary, or tertiary amine of sufficient basicity to form a salt with the carboxylic acid group.
• Representative alkali or alkaline earth metal salts include sodium, lithium, potassium, calcium, magnesium, and the like.
• Representative organic amines useful for the formation of base addition salts include, ethylamine, diethylamine, ethylenediamine, ethanolamine, di
• “Monomer” means a polymerizable allylic, vinylic or acrylic compound.
• the monomer may be anionic, cationic or nonionic. Vinyl monomers are preferred, acrylic monomers are more preferred.
• Nonionic monomer means a monomer as defined herein which is electrically neutral.
• Representative non-ionic, water-soluble monomers include acrylamide, methacrylamide, N, N-dimethylacrylamide , N, N- diethylacrylamide, N-isopropylacrylamide , N- vinylformamide,
• N-vinylmethylacetamide N-vinyl pyrrolidone, hydroxyethyl methacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, N- t- butylacrylamide, N-methylolacrylamide , and the like.
• RSV Reduced Specific Viscosity
• the RSV is measured at a given polymer concentration and temperature and calculated as follows :
• ⁇ viscosity of polymer solution
• ⁇ Q viscosity of solvent at the same temperature
• c concentration of polymer in solution.
• the units of concentration "c" are (grams/100 ml or g/deciliter) . Therefore, the units of RSV are dL/g.
• a 1.0 molar sodium nitrate solution is used for measuring RSV, unless specified.
• the polymer concentration in this solvent is 0.045 g/dL.
• the RSV is measured at 30 °C.
• the viscosities ⁇ and ⁇ D are measured using a Cannon Ubbelohde semimicro dilution viscometer, size 75. The viscometer is mounted in a perfectly vertical position in a constant temperature bath adjusted to 30 ⁇ 0.02 °C. The error inherent in the calculation of RSV is about 2 dL/g.
• Solution polymer means a water soluble anionic polymer as described herein that is prepared by solution polymerization.
• the desired monomers are dissolved in water, generally at concentrations between 5 and 40%, along with any buffers, acid or caustic, chelants and chain transfer agents.
• the solution is purged with nitrogen and heated to the polymerization temperature. After the polymerization temperature is reached, one or more water soluble initiators is added.
• initiators may be either of the azo type or of the redox type. Then, depending on the desired polymer characteristics, the temperature is either allowed to rise uncontrolled (adiabatic) or is controlled with cooling to remove the heat generated (isothermal) . After the polymerization is complete, the solution of polymer can be removed from the reaction vessel, transferred to storage and characterized.
• the anionic or nonionic monomers are selected from the group consisting of acrylic acid, methacrylic acid, acrylamide, methacrylamide and styrene sulfonic acid.
• the anionic polymer has a molecular weight of from about 20,000 to about 5, 000, 000.
• the anionic polymer is methacrylic acid/2-acrylamido-2-methyl-1-propanesulfonic acid sodium salt copolymer or acrylamide/2-acrylamido-2- methyl-1-propanesulfonic acid sodium salt copolymer.
• the anionic polymers of this invention are used as compositions for treating hair by incorporating them in a cosmetically acceptable medium in amounts of from about 0.1 to about 10 percent, preferably from about 0.5 to about 5 percent by weight, based on polymer solids.
• compositions can be presented in various forms including hair spray, styling gel, styling glaze, spray foam, styling cream, styling wax, styling lotion, liquid foam and mousse.
• They can contain water and also any cosmetically acceptable solvent, in particular monoalcohols, such as alkanols having 1 to 8 carbon atoms, like ethanol, isopropanol, benzyl alcohol and phenylethyl alcohol, polyalcohols, such as alkylene glycols, like glycerins, ethylene glycol and propylene glycol, and glycol ethers, such as mono-, di- and tri- ethylene glycol monoalkyl ethers, for example ethylene glycol monomethyl ether, ethylene glycol monomethyl ether and diethylene glycol monomethyl ether, used singly or in a mixture.
• These solvents can be present in proportions of up to as much as 99.5 percent by weight, relative to the weight of the total composition.
• compositions of this invention can also contain any other ingredient normally used in cosmetics, such as perfumes, dyestuffs which can serve to color the composition itself or the fibres of the hair, preservatives, sequestering agents, thickeners, silicones, softeners, foam synergistic agents, foam stabilizers, sun filters, peptising agents and also anionic, non-ionic, cationic or amphoteric surface-active agents or mixtures thereof.
• the hair fixative composition of this invention is applied to wet or dry hair by spraying or by rubbing onto the hair manually.
• the treated hair is then mechanically fixed in the desired configuration using, for example, any of a variety of rollers or curlers .
• the hair is then dried using ambient air, electric or hot air drying using, for example, a blow dryer.
• the hair is then combed to provide the desired hairstyle.
• the hair fixative composition is selected from the group consisting of gels, glazes and creams.
• a hair styling gel is firm gel that thins upon application of shear such that it spreads very thin when applied to hair.
• Hair styling gels are typically applied by manually rubbing the gel onto wet or damp hair. The hair is then placed in the desired configuration, for example by wrapping the hair tightly around curlers or a finger and set by drying as described above.
• Hair styling glazes are easy to spread, clear flowable gels that are particularly useful for the wet look or blow dry styling methods.
• Hair styling creams are easy to spread, flowable lotions .
• the hair styling gel or glaze contains about 0.05 to about 15 percent by weight of a thickener.
• the thickener should be compatible with the anionic polymer and should not adversely affect the stability or efficacy of the hair styling gel.
• Representative thickeners include polyacrylic acid, polyacrylic acid crosslinked with allyl ethers of pentaerythrol or allyl ethers of sucrose (available from BF Goodrich, Brecksville, OH under the tradename Carbopol®) , sodium acrylates copolymer (available from Ciba Specialty Chemicals Corporation, High Point, NC under the tradename Salcare®) , xanthan gums, sodium alginates, gum arable and cellulose derivatives. It is also possible to achieve thickening by means of a mixture of polyethylene glycol stearates or distearates or by means of a mixture of a phosphoric acid ester and an amide .
• optional ingredients also can be incorporated into the hair styling gel or glaze.
• the identity of the optional ingredients is not limited as long as the optional ingredients do not adversely affect the aesthetics or efficacy of the hair styling gel.
• Such optional ingredients are well known to those skilled in the art and include emulsifiers such as anionic or nonionic surfactants; preservatives such as benzyl alcohol, methyl paraben, propyl paraben, or imidazolidinylurea; cationic conditioners such as cetyl trimethyl ammonium chloride, methyldibromoglutaronitrile (available from ONDEO Nalco, Naperville, IL under the tradename Merguard®) , stearyl dimethyl benzyl ammonium chloride, and di (partially hydrogenated tallow) dimethyl ammonium chloride; coloring agents such as any of the FD&C or D&C dyes; perfume oils; and chelating agents such as ethylenediaminetetraacetic acid.
• the hair fixative composition of this invention may also contain conventional hair care adjuvants including plasticizers such as glycols, phthalate esters and glycerine, silicones, emollients, lubricants, and penetrants such as various lanolin compounds, protein hydrolysates and other protein derivatives, ethylene adducts and polyoxyethylene cholesterol .
• plasticizers such as glycols, phthalate esters and glycerine
• silicones such as silicones, emollients, lubricants, and penetrants
• penetrants such as various lanolin compounds, protein hydrolysates and other protein derivatives, ethylene adducts and polyoxyethylene cholesterol .
• the hair fixative composition of this invention can also contain electrolytes, such as aluminum chlorhydrate, alkali metal salts, e.g., sodium, potassium or lithium salts, these salts preferably being halides, such as the chloride or bromide, and the sulphate, or salts with organic acids, such as the acetates or lactates, and also alkaline earth metal salts, preferably the carbonates, silicates, nitrates, acetates, gluconates, pantothenates and lactates of calcium, magnesium and strontium.
• electrolytes such as aluminum chlorhydrate, alkali metal salts, e.g., sodium, potassium or lithium salts, these salts preferably being halides, such as the chloride or bromide, and the sulphate, or salts with organic acids, such as the acetates or lactates, and also alkaline earth metal salts, preferably the carbonates, silicates, nitrates, acetates, glucon
• the hair fixative composition of this invention may also contain one or more additional hair fixative polymers.
• the additional hair fixative polymers are present in a total amount of from about 0.25 to about 5 percent by weight .
• Representative hair fixative polymers compatible with anionic and nonionic hair fixative polymers include acrylic/acrylate copolymer, allyl stearate/vinyl acetate (VA) copolymer, AMP acrylate/diacetoneacrylamide copolymer, butyl ester of ethylene/maleic anhydride (MA) copolymer, butyl ester of PVM/MA copolymer, isopropyl ester of PVM/MA copolymer, octylacrylamide/acrylate/butylaminoethyl methacrylate copolymer, phthalic anhydride/glycerin/glycidyl decanoate copolymer, polybutylene terephthalate, polyethylacrylate, polyethylene, polyviny
• the hair styling gels of the present invention are prepared by dissolving the anionic polymer in water or a water/alcohol mixture, with heating if necessary. An aqueous solution of the viscosity enhancer and any optional ingredients are then added and the mixture is stirred to provide the gel or glaze.
• the hair fixative composition When the hair fixative composition is in the form of a hair spray or mousse, it additionally contains up to 50 weight percent of one or more propellants.
• propellants include ethers, compressed gases, halogenated hydrocarbons and hydrocarbons including, dimethyl ether, carbon dioxide, nitrogen, nitrous oxide and volatile hydrocarbons, such as butane, isobutane, propane, and the like.
• Polymerization begins within 5 minutes and after 10 minutes, the solution becomes viscous and the temperature of the reaction rises to 80 °C. The reaction is continued for a total of 16 hours at 78-82 °C.
• the resulting 10% polymer solution has a Brookfield viscosity of 1000 cps at 25 °C and contains a 60/40 w/w copolymer of acrylic acid/AMPS with an intrinsic viscosity of 2.8 dL/g in 1.0 molar NaN0 3 .
• the reaction is continued for 18 hours at 48-52 °C.
• the reaction mixture is then heated to 80 °C and maintained at 78-82 °C for 24 hours .
• the resulting polymer solution has a Brookfield viscosity of 43200 cps at 25 °C and contains 15% of a
• the beaker is rinsed with 600g of deionized water and the rinse is added to the reactor.
• the reaction mixture is stirred and heated to 45 °C.
• 1.13g of a 10% wt solution of 2, 2 ' -azobis [2- (2- imidazolin-2-yl) propane] dihydrochloride (VA-044, Wako Chemicals USA, Inc., Richmond, VA) initiator 500 ppm based on monomer
• VA-044, Wako Chemicals USA, Inc., Richmond, VA Wako Chemicals USA, Inc., Richmond, VA
• the reaction mixture is purged with nitrogen at approximately lL/min. After several minutes the reaction mixture becomes viscous. After approximately eight hours, the reaction mixture is cooled to room temperature and the contents are discharged.
• the polymer has an IV of about 2.5 dL/g and a Brookfield viscosity of about 5700 cps (15% polymer solution) .
• a representative hair styling gel formulation is shown in Table 3.
• the gel is prepared by dispersing carbomer resin
• the glaze is prepared by agitating a solution of hydroxyethylcellulose (Natrosol HHR, Hercules Inc., Wilmington, DE) in one half of the volume of water with agitation for 4 hours. Alkylquat (Incroquot 26, Croda Inc., Parsippany, NJ) is added to the solution followed by a solution of the anionic polymer in the remaining water. The pH of the glaze is adjusted to about 6.5 with citric acid or sodium hydroxide.
• a representative hair styling cream formulation is shown in Table 5.
• the tresses are prepared for testing by cutting 1/8" width of hair from the pretabbed hair tress (0.4 g for each tress) .
• the hair tress is wetted with water and then 0.3 g of sodium laureth sulfate is massaged onto the hair tress from top to bottom for 1 minute.
• the hair tress is then rinsed under 40 ⁇ 2 °C tap water for 1 minute.
• the washed hair tresses are soaked in deionized water overnight .
• Curl retention using an aqueous anionic polymer solution Curl retention using an aqueous anionic polymer solution. Clean hair tresses, prepared as in Example 7, are immersed in a 0.5 weight percent aqueous polymer solution for 2 minutes. The excess solution is squeezed from the tress with gloved fingers. Each tress is combed to detangle with the wide end of Sally Styling Combs, then the hair is rolled onto a roller (11/16" in diameter) .
• the hair rolls are placed in a 50% relative humidity room overnight. The next day, the hair is unwound from each roller and the curled hair is placed in a 90% relative humidity chamber. The length of the curl (fall-out) is measured every 15 minutes for 2 hours and curl retention is calculated by the following equation:
• Lt length of hair tress at time of measurement
• Curl retention for styling gel containing a representative anionic polymer Curl retention for styling gel containing a representative anionic polymer.
• Example 7 To a 2 g washed hair tress is evenly applied 0.5 gram of the styling gel formulation of Example 4. The hair tress is dried using a hair dryer at 65 °C for 5 minutes. The hair is rolled onto a roller and the hair roller is placed in a 50% humidity room for 2 hours. The hair is then unrolled from the roller and the curl retention is measured as in Example 8. The results are summarized in Table 7. Table 7
• a styling gel composition according to this invention has substantial holding power .
• Example 10 Curl retention for styling glaze containing a representative anionic polymer.
• Example 7 To a 2 g washed hair tress is evenly applied 0.5 g of the styling glaze formulation of Example 5. The hair tress is dried using a hair dryer at 65 °C for 5 minutes. The hair is rolled onto a roller and the hair roller is placed in a 50% humidity room for 2 hours. The hair is then unrolled from the roller and the curl retention is measured as in Example 6. The results are summarized in Table 7. Table 8
• a hair styling glaze containing the anionic polymer of this invention exhibits also exhibits substantial curl retention.
• Curl memory for styling cream containing a representative anionic polymer containing a representative anionic polymer.
• a 2 g, 6 inch washed hair tress is combed 10 times (Sally comb, large tooth part) to detangle, and 1 g of styling cream is applied to the hair tress.
• the hair tress is dried for 1.5 hours at room temperature at 30 % relative humidity.
• a curling iron (Conair Instant Heat) at setting 20, 1 inch barrel is then used to curl each tress. After counting to 30, the curl is released and allowed to cool for five minutes at 50% relative humidity. The fall-out length is recorded after 5 and 30 minutes. The shorter the fall-out length of hair curl the better the curl memory.
• Duplicate hair tresses are tested. The results are summarized in Table 9. Table 9
• a hair styling cream containing the anionic polymer of this invention exhibits high curl memory.
• the ease of removal of the hair fixative composition of this invention from hair is evaluated using blind wash off panel testing.
• the test is subjective because the results reflect the opinions and perceptions of the panelists.
• the results do, however, provide an excellent way of determining how a consumer will perceive the properties of a product on the hair.
• the results of the panel test indicate that the hair fixative compositions of this invention are easily washed from the hair, and further impart a feeling of wet slip, silkiness and enhanced dry combability to the hair.
• the anionic polymer of this invention is compatible with most commonly used hair fixatives.
• the following tables show styling aid formulations having a combination of anionic polymer with poly (vinylpyrrolidone) and poly (vinylpyrrolidone/vinyl acetate) copolymer.
• the formulations described in Tables 11 and 12 are prepared as described in Examples 4 and 6, respectively.
• the styling gel and cream show no separation after 2 weeks.

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