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
  • A61K8/8141—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

Definitions

• the present invention provides a moisture-resistant setting lotion in the form of an aqueous or aqueous-alcoholic solution for setting hair that has been laid in the damp state, the said solution containing an amount of 0.5 to 5% of a salt, which is at least soluble in an aqueous-alcoholic solution, of a weak inorganic or organic acid and a basic copolymer capable of forming films; the copolymer contains at least an amount of a basic mono meric compound containing a tertiary nitrogen atom sufficient to ensure that after the hair has been dried at a temperature ranging from 18 to C. a water-insoluble film is left on it.
• the present invention provides a method of making water waves of enhanced durability, more specially in a damp atmosphere, wherein damp hair is impregnated with an aqueous or aqueous alcoholic solution containing 0.5 to 5% of a salt, which is at least soluble in an aqueous-alcoholic solution, of a Weak inorganic or organic acid and a basic copolymer capable of forming films, the said copolymer containing a basic monomer with a tertiary nitrogen atom in an amount sufficient to ensure that after having been dried the hair is covered with a water-insoluble film, whereupon the impregnated hair is laid in the desired shape and dried at a temperature ranging from 20 to 60 C., preferably from 30 to 50C.
• the solubility of the salts in water must be such that they are soluble at 15 to 25 C. and at a concentration of up to 20% by weight in water or in an aqueous-alcoholic mixture of 2 parts by weight of ethanol and at least 8 parts of water. If the share of the salt-forming, basic component is too large, drying does not convert the films into the water-insoluble state; if it is too small, no watersoluble salts are formed. The expert will be able to ascertain by simple tests the maximum and minimum amounts of basic component required to ensure the desired solubility of the salts in water and their capability of forming a water-insoluble film.
• solubility of the salts in water and their capability of forming water-insoluble films depend also on the kind and amount of the non-basic comonomers.
• acrylamide or its N-substituted alkylacrylamides are used the share of the basic component maybe smaller than when esters of acrylic or methacrylic acid are used. Since the manufacture of copolymers having the desired properties depends on a number of factors that affect one another, it is not possible to lay down a rule applicable to all cases.
• the basic component used is an NzN- dialkylaminoalkyl acrylamide, it should as a rule be used in an amount not exceeding 30% by weight and not less than 5%.
• an NzN-dialkylaminoalkyl methacrylic acid ester is used, the less pronounced solubilizing properties require 50% by weight or even more to be used.
• acids capable of forming salts there come into consideration weak inorganic or organic acids, that is to say acids whose dissociation constant is below 10- There may be mentioned: Boric, carbonic, formic, acetic, propionic and lactic acid. It is of special advantage to use a readily volatile acid, such as carbonic, formic or acetic acid.
• aqueous solution of the salts is poured over a plate of glass and allowed to evaporate at 18 to 25 C.
• the film (film thickness about 201.1.) is then dried for 1 hour at 45 C.
• the film is then kept covered with water for 1 hour at 18 to 25 C., and its dissolution or stability respectively is ascertained.
• the setting lotions contain the salts described above in a concentration of 0.5 to 5%, preferably 0.75 to 2% by weight.
• the solvent used may be water or, more advantageously, it is a mixture of alcohol and water because the alcohol promotes the evaporation and drying.
• the aqueous preparation used as setting lotion may contain, apart from the solvent or solvents and the salt of the basic copolymer, the conventional additives such as perfume, softening agents, evaporation accelerators and the like.
• the copolymers are particularly advantageous to manufacture from the compounds of type (a), especially from the basic acides of polymerizable aliphatic otIB-UHSEIUI- rated monocarboxylic acids whose molecule contains a tertiary nitrogen atom in the amide constituent.
• basic amides and esters are derived from an one-unsaturated acid of the acrylic acid series, that is to say from homologues of acrylic acid, such as methacrylic or cro tonic acid, or from the corresponding dicarboxylic acids, such as fumaric, itaconic or citraconic acid.
• the basic amides and esters of monocarboxylic acids correspond preferably to the general formula where X represents ahydrogen atom or the methyl group, n and s each is 1 or 2, and R and R each stands for an a-lkyl radical with 1 to 4 carbon atoms. R and R may also be linked together to form a heterocycle.
• basic amides of the Formula 1 there may be mentioned:
• Acrylic acid-fi-dimethylaminoethyl ester Methacrylic acid-'y-diethylaminopropyl ester, and Acrylic acid-'y-di-n-butylaminopropyl ester.
• Compounds of the type (a) may also be basic amides or esters of aliphatic azB-unsaturated dicarboxylic acids, such as maleic acid-' -dimethylaminopropylamide, fumaric acid-di-[y-dimethylaminopropyl]-amide and fumaric aciddifl-diethylaminoethyl] -ester.
• basic amides or esters of aliphatic azB-unsaturated dicarboxylic acids such as maleic acid-' -dimethylaminopropylamide, fumaric acid-di-[y-dimethylaminopropyl]-amide and fumaric aciddifl-diethylaminoethyl] -ester.
• vinyl ethers containing a tertiary nitrogen atom andup to 12 carbon atoms specifically the following: ,B-diethylaminoethyl vinyl ether, fl-di-n-butylaminoethyl vinyl ether, fi-morpholinoethyl vinyl ether and 4-dimethylaminophenyl-(1)-methylvinyl ether.
• the polymerization may be conducted in solution or in emulsion, using the measure conventionally employed in the polymerization technique. Preferably, the polymerization is performed in solution.
• the basic copolymers may be manufactured by the processes described in the Brtish patent application No. 871,295, granted October 18, 1961, by A. Maeder, and British patent application No.
• the polymer solution is concentrated by evaporating the solvent, whereupon advantageously the calculated amount of acid is added and the whole is diluted with water.
• the salt to be manufactured is the carbonate
• the solution is freed from the solvent and diluted with water and carbon dioxide is injected into it while cooling with ice.
• non-basic compounds which likewise contain a carbon-to-carbon double bond, more especially an H C:C group
• vinyl esters of organic acids for example vinyl acetate, formate, butyrate or benzoate
• vinylaryl compounds such as styrene or substituted styrenes
• compounds of the acrylic acid series such as esters of acrylic acid and alcohols or phenols that contain 1 to 12 carbon atoms and no tertiary amino group, for example ethyl acrylate, butyl acrylate and dodecyl acrylate, acrylonitrile or acrylamide and its derivatives substituted on the amide nitrogen, such as, NzN-diethyl acrylamide, NzN-dihyroxyethyl acrylamide, N-n-propyl acrylamide, N-tertiary butyl acrylamide, NzN- di-n-butyl-acryl
• polymerizable vinyl ethers such as vinylethyl ether.
• Preferred use is made of derivatives of acrylic and methacrylic acid (said derivatives being .free from basic nitrogen atoms) and among them above all the esters with aliphatic alcohols, or the N-monosubstituted amides in which an aliphatic substituent is linked to the amide nitrogen atom through a secondary or tertiary carbon atom.
• ternary copolymers that contain as the film-forming component 30 to 50% of an ester of acrylic or methacrylic acid and an alkanol with 1 to 4 carbon atoms; as setting and sheenforming component 30 to 50% of an N-monoalkyl-substituted or N:N-dialkyl-substituted acrylamide whose substituents contain 2 to 4 carbon atoms each, and as saltforming component 5 to 20% of an N:Ndi-(C C alkylamino- (C -C alkylacrylamide.
• Example 1 160 parts of ethyl acrylate, 200 parts of N-tertiary butyl acrylamide and 40 parts of NzN-diethylaminopropyl acrylamide are dissolved at room temperature in 320 parts of absolute ethanol in a 2-filter flask equipped with stirrer, reflux condenser and thermometer. The flask is then scavenged with nitrogen and the batch is heated to the boiling point of ethanol. 0.4 part of azo diisobutyronitrile is then added, and this addition is repeated four times at intervals of 1 hour each. The polymerization is slightly exothermic. 1 hour after the last addition of catalyst the mixture iscooled to room temperature.
• Example 2 Setting lotions are prepared with the use of the undermentioned salts, having the following composition:
• the salts concerned are the following products:
• Acetate salt of the copolymer from 80% of ethyl acrylate, 10% of N-teritary butyl acrylamide and 10% of NzN-diethylaminopropyl acrylamide.
• Lactate salt of the copolymer from 30% of ethyl acrylate, 10% of lauryl acrylate, 40% of NzN-diethyl acrylamide and of N:N-diethylaminoethyl acrylamide.
• the hair is thoroughly washed and then dried with a towel only so much as to leave it damp. 10 to ml. of setting lotion are then applied so as to leave the hair thoroughly damp.
• the hair is then given the desired style (preferably by curling) and dried in air heated up to C. In all 14 cases there are obtained water waves which display a coating that is resistant to moist air.
• the hair can be styled again in the damp state and without additional treatment, and the resulting hairstyle is permanent.
• a composition for setting hair that has been shaped in the damp state comprising a solvent selected from the class consisting of water and a mixture of water and alcohol, and, in an amount of 0.5 to 5 percent, calculated on the total of the solution, a salt which is soluble in said solvent, of a weak acid selected from the group consisting of boric acid, carbonic acid, formic acid, acetic acid, propionic acid and lactic acid and a basic, filmforming copolymer, said copolymer consisting of (1) 30 to percent by weight of units of an alkyl ester of an acid selected from the group consisting of acrylic and methacrylic acid, wherein the alkyl has 1 to 4 carbon atoms, (2) 30 to 50 percent by weight of units of a substituted acrylamide selected from the group consisting of N-mono-alkyl-substituted and NzN-dialkyl-substituted acrylamide, the substituents containing 2 to 4 carbon atoms each, and (3) 5 to 20 percent by weight of units of
• a composition for setting hair that has been shaped in the damp state comprising a solvent selected from the class consisting of water and a mixture of water and alcohol, and, in an amount of 0.5 to 5 percent, calculated on the total of the solution, a salt Which is soluble in said solvent, of acetic acid and a basic, film-forming copolymer, said copolymer consisting of 30 to 50 percent by weight of units of ethyl-acrylate, 30 to 50 percent by weight of units of N-tertiary butyl-acrylamide, and 5 to 20 percent by weight of units of NzN-diethylaminopropyl-acrylamide.
• a composition for setting hair that has been shaped in the damp state comprising a solvent selected from the class consisting of water and a mixture of water and alcohol, and, in an amount of 0.5 to 5 percent, calculated on the total of the solution, a salt which is soluble in said solvent, of acetic acid and a basic, film-forming copolymer, said copolymer consisting of 40% of ethyl acrylate, 30% of N-tertiary butyl acrylamide and 30% of NzN-diethylaminoethyl vinyl ether.
• a composition for setting hair that has been shaped in the damp state comprising a solvent selected from the class consisting of water and a mixture of water and alcohol, and, in an amount of 0.5 to 5 percent, calculated on the total of the solution, a salt which is soluble in said solvent, of acetic acid and a basic, filmforming copolymer, said copolymer consisting of 30% of ethyl acrylate, 20% of N-tertiary butyl acrylamide and 50% of NzN-diethylaminoethyl methacrylate.
• a composition for setting hair that has been shaped in the damp state comprising a solvent selected from the class consisting of water and a mixture of water and alcohol, and, in an amount of 0.5 to 5 percent, calculated on the total of the solution, a salt which is soluble in said solvent, of acetic acid and a basic, film-forming copolymer, said copolymer consisting of 75% of ethyl acrylate and 25% of di-(N:N-dimethylaminopropyl)- fumaric acid amide.
• a method for making water waves of enhanced durability in a damp atmosphere wherein the damp hair is impregnated with a composition as claimed in claim 1, the impregnated hair is laid in the desired shape and dried at. a temperature ranging from 20 to 60 C.
• a method for making water waves of enhanced durability in a damp atmosphere wherein the damp hair is impregnated with a composition as claimed in claim 2, the impregnated hair is laid in the desired shape and dried at a temperature ranging from 20 to 60 C.
• a method for making water waves of enhanced durability in a damp atmosphere wherein the damp hair is impregnated with a composition as claimed in claim 4, the impregnated hair is laid in the desired shape and dried at a temperature ranging from 20 to 60 C.
• a method for making water waves of enhanced durability in a damp atmosphere wherein the damp hair is impregnated with a composition as claimed in claim 5, the impregnated hair is laid in the desired shape and dried at a temperature ranging from 20 to 60 C.
• a composition for setting hair that has been shaped in the damp state comprising a solvent selected from the class consisting of water and a mixture of water and alcohol and, in an amount of 0.5 to 5 percent, calculated on the total of the solution, a salt which is soluble in said solvent, of lactic acid and a basic, film-forming copolymer, said copolymer consisting of 30 to 50 percent 7 by Weight of units of ethyl-acrylate, 30 to 50 percent by Weight of units of N-tertiary butyl-acrylarnide, and 5 to 20 percent by Weight of units of units of NzN-diethylaminopropyl-acrylamide.
• a composition for setting hair that has been shaped in the damp state comprising a solvent selected from the class consisting of Water and a mixture of water and alcohol and, in an amount of 0.5 to 5 percent, calculated on the total of the solution, a salt which is soluble in said solvent, of formic acid and a basic, film-forming copolymer, said copolymer consisting of 30 to 50 percent by weight of units of ethyl-acrylate, 30 to 50 percent by weight of units of N-tertiary butyl-acrylarnide, and 5 to 20 percent by weight of units of NzN-diethylaminopropyl-acrylamide.

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Cited By (4)

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Citations (3)

• 0
  • NL NL294872D patent/NL294872A/xx unknown
  • NL NL135734D patent/NL135734C/xx active
  • BE BE634447D patent/BE634447A/xx unknown
• 1962
  • 1962-07-04 CH CH802862A patent/CH439592A/de unknown
• 1963
  • 1963-06-28 DK DK310463AA patent/DK107769C/da active
  • 1963-07-03 DE DE1467818A patent/DE1467818C3/de not_active Expired
  • 1963-07-03 US US292756A patent/US3206362A/en not_active Expired - Lifetime
  • 1963-07-03 FI FI631326A patent/FI42987C/fi active
  • 1963-07-03 AT AT530463A patent/AT249878B/de active
  • 1963-07-03 SE SE07405/63A patent/SE326255B/xx unknown
  • 1963-07-04 GB GB26629/63A patent/GB1031540A/en not_active Expired
  • 1963-10-02 IT IT13490/63A patent/IT951503B/it active
• 1964
  • 1964-12-31 OA OA51365A patent/OA01184A/xx unknown

Patent Citations (3)

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