US3406238A - Emollient preparations containing alkylated polymers of heterocyclic n-vinyl monomers - Google Patents

Emollient preparations containing alkylated polymers of heterocyclic n-vinyl monomers Download PDF

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US3406238A
US3406238A US423603A US42360365A US3406238A US 3406238 A US3406238 A US 3406238A US 423603 A US423603 A US 423603A US 42360365 A US42360365 A US 42360365A US 3406238 A US3406238 A US 3406238A
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vinyl
alkylated
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heterocyclic
mole
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Harlan B Freyermuth
Wilmer E Van Horn
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GAF Corp
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Priority to FR44808A priority patent/FR1462808A/fr
Priority to SE110/66A priority patent/SE312197B/xx
Priority to NL6600037A priority patent/NL127700C/xx
Priority to CH11366A priority patent/CH490853A/de
Priority to DE19661617484 priority patent/DE1617484A1/de
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    • 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
    • C08F26/00—Homopolymers and 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
    • C08F26/06—Homopolymers and 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 by a heterocyclic ring 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
    • A61K8/72—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
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; 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)
    • 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
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/12—Face or body powders for grooming, adorning or absorbing
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/002—Aftershave preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A61Q3/04—Nail coating removers
    • 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
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/02—Shaving preparations

Definitions

  • compositions contain as an essential component from 0.1 to about 50% by Weight thereof of an alkylated polymer of an N-vinyl heterocyclic monomer wherein on an average at least of the N-vinyl heterocyclic monomer units in said polymer are alkylated with an alkyl group of from 10 to 42 carbon atoms.
  • This invention relates to emollient preparations containing alkylated polymers of heterocyclic N-vinyl monomers which impart a much smoother texture to the preparation together with a softening and soothing effect when applied to the skin and the appendages of the skin.
  • emollients and cosmetics for the skin and hair include all preparations for conditioning or embellishment such as cleansing creams, quick-liquefying creams, emollient creams, cleansing lotions, cream and paste rouges, lipsticks, anti-perspirants, facial masks, massage oils, hair .oils and creams, hair removers (epilating Waxcompositions), eye shadow, sunburn preventives, etc.
  • preparations other than normal soap bars, contain petroleum hydrocarbons in one form or another, such as mineral oil, petroleum (solid or liquid), and paraffin wax or a mixture of two or all of such hydrocarbons.
  • the cosmetic industry has and is expending considerable amounts of money in research and development of a product or products which, when incorporated into toiletry preparations, will impart a much smoother texture as well as a softening and soothing effect on the skin and the appendages of the skin.
  • the problems involved are manifold.
  • the cosmetic chemist must consider the nature of the skin, i.e., whether normally dry or oily to which the preparation is to be applied. He must also consider the nature or character of the developed product, its compatibility with other components constituting the preparation and the effect ;when applied ot the skin or the appendages thereof.
  • toiletry preparations i.e., emollients, cosmetics, and soaps, which are smooth in texture and which impart a softening and soothing elfect to the skin and the appendages of the skin.
  • Another object is to provide cosmetic preparations for the conditioning of nails of the toes and fingers.
  • a further object isto provide cosmetic preparations for the conditioning and grooming of hair which will leave the hair soft, lustrous, alive-looking and manageable.
  • products obtained by the alkylation of polymers of heterocyclic N-vinyl monomers or by the simultaneous polymerization and alkyl-ation of heterocyclic N-vinyl monomers and co-monomers thereof are excellent additives to soaps and cosmetic preparations of the cleansing, conditioning, and embellishing type which will impart a smooth texture as Well as a softening and soothing effect to the skin and skin appendages.
  • the additives range from viscous oils to soft and relatively hard waxes. They can be used in place of, and in addition to, petroleum hydrocarbons, i.e., mineral oils, petrolatums and paraffin waxes.
  • the toiletry preparation contains any one or all of these petroleum hydrocarbons, vegetable oils', lanolin, and/or other unctuous components, or is free from such components, etc., the presence of the additive in such preparation imparts a much smoother texture to it with the attendant softening and soothing effect when applied to the skin and a softening effect when applied to skin appendages.
  • the additive displays dye-binding properties as well as softening and soothing effects. It also retards drying out of the lipstick.
  • soaps and synthetic soap bars the presence of the additive imparts a soft and pliable effect on skin and scalp and a soft effect on hair after rinsing with water. The same effect is felt after several rinses with water.
  • Toiletry preparations especially skin cosmetics, containing the additive and applied to the skin, resist the penetration of oils and of fine dust and other dirt particles which imbed themselves in the skin pores.
  • the unusual properties of the additive are not-clearlystearate, glycerine, the currently used emollients, hair- 3 oils and creams, etc., may be due to both the hydrophilic character of the component of the N-heterocyclic ring and the hydrophobic character of the alkyl chain or chains in said ring of the polymer molecule.
  • the hydrophobic character imparts the solubility and compatibility in oils, fats, waxes, and other unctuous materials, as well as smoothness; Whereas the hydrophilic character may contribute to the softening and soothing eiiects.
  • the additives employed in accordance with the present invention are prepared by reacting one mole of a monomer or polymer of a (homopolymer or copolymer) of a a heterocyclic N-vinyl monomer with 0.5 to 4, preferably 1 to 3, moles of an a-olefin of from 10 to 42 carbon atoms in solution of an organic solvent common to the monomer and its polymer (homopolymer or copolymer) in the presence of 0.025 to 0.30 mole of an organic peroxide catalyst per mole of iii-olefin at a temperature ranging from 100 to 200 C. for a period of time ranging from 3 to 60 hours.
  • the percent of a-olefin reacted is determined by the percent of the a-olefin consumed and may range from about 50% to 100% of the a-olefin charged.
  • Alkylated polymers of heterocyclic N-vinyl monomers with emollient properties are obtained in which a minimum of 25% to a maximum of 400% of the monomeric units in the polymer are alkylated. In other words, alkylated homopolymers are obtained containing an average of 0.25 to 4 alkyl groups of 10 carbon atoms per monomer unit.
  • alkylated copolymers with emollient properties are obtained in which a minimum of 30% to a maximum of 240% of the heterocyclic N-vinyl units in the copolymer are alkylated, i.e., containing at least 0.25 alkyl groups of 10 carbon atoms per monomeric unit in the copolymer.
  • alkylating such copolymers it is preferred that 1-3 moles of a-Olefin be reacted with one mole of copolymer to yield an alkylate in which at least 30% of the heterocyclic N-vinyl units in the copolymer are alkylated.
  • the resulting solution of the alkylated polymer is subjected to vacuum distillation to remove the organic solvent.
  • the residue, alkylated polymer ranges from a viscous oil to a soft and substantially hard wax.
  • the homopolymers of heterocyclic N-vinyl monomers which are alkylated with an a-olefin of from 8 to 42 carbon atoms and employed as additives, include homopolymers of N-vinyl suecinimide, N-vinyl diglycolylimide, N- vinyl glutarimide, N-vinyl-3-morpholinone, N-vinyl-- methyl-B-morpholinone, N-vinyl-5-ethyl-3-morpholinone, and N-vinyl lactams having the following formulae:
  • R represents an alkylene bridge, i.e.,
  • N-vinyl thiolactams and these can be used in the alkylation process.
  • R, R and R have the same values as above, in is an integer of from one to four, and n is an integer of from one to four when m has a value of one and from two to four when m has a value greater than one.
  • Illustrative compounds are N-acryloxy-methyl-pyrrolidone, -piperidone and -caprolactam; N-methacryloxyethoxy-ethyl-pyrrolidone, -piperidone and -caprolactam; N methacryloxy propyl pyrrolidone, -piperidone and -caprolactam; N-methacryloxy-ethyl-pyrrolidone, -piperidone, and -caprolactam; N-methacryloxy-methyl-S-methyl-pyrrolidone, -6-methylpiperidoue and -7-methy1-caprolactam, including amidoalkyl lactams of the structure:
  • J H:,NR:i-COCR; CH: wherein R, R and R have the same value as above, R represents hydrogen, alkyl group of from 1 to 12 carbon atoms or phenyl, and Y represents an integer of from 2 to 3.
  • Illustrative compounds of this type are N-methacrylamidomethyl-, N-methacrylamidoethyl-, N-methacrylamidopropyl and N (N phenylacrylamidopropyl) pyrrolidones, -piperidones and -caprolactams, which are readily prepared by reacting acryloyl or methacryloyl chloride or bromide with an N-(aminoalkyD-lactam, wherein the alkyl is from 1 to 12 carbon atoms, in the presence of any conventional base to take up the hydrogen halide.
  • the individual homopolymers of the foregoing heterocyclic N-vinyl monomers may be alkylated as such or in admixture.
  • the proportions constituting the mixture are immaterial since such mixture of homopolymers is readily alkylated and yields a product with emollient properties.
  • the comonomer mixture contain at least 60% by weight, i.e., from 60% to by weight of any one of the foregoing heterocyclic N-vinyl monomers with up to 40% by Weight, i.e., from 5 to 40% by weight of a non-heterocyclic monomer.
  • non-heterocyclic monomers containing a polymerizable vinyl group which are copolymerized with any one of the foregoing heterocyclic N-vinyl monomers, prior to alkylation, including vinyl ester monomers such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl isobutyrate, vinyl lactate, vinyl caproate, vinyl caprylate, vinyl oleate, and vinyl stearate; vinyl chloride; vinylidene chloride; acrylonitrile; styrene; acrylic acid; 'acrylate ester monomers of the formula CH CHCOOR wherein R represents either a straight or branched alkyl of from 1 to 18 carbon atoms or an alkoxyalkyl in which the total number .of carbon atoms in the alkyl groups range from 3 to 6.
  • acrylate esters examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, Z-methyl-l-butyl, 3- methyl-l-butyl, Z-ethyl-l-butyl, amyl, 3-pentyl, 2-methyll-pent'yl, 4-methyl-2-pentyl, hexyl, Z-ethylhexyl, heptyl, 2-heptyl, octyl, 2-octyl, nonyl, 5-ethyl-2-nonyl, decyl, 2- methyl-7 ethyl-4-undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 2-methoxyethyl, 2-ethoxyethyl and 2-butoxyethyl
  • non-heterocyclic polymerizable monomers are immaterial so long as such monomers are capable of copolymerization in the aforestated proportions with the heterocyclic N-vinyl monomers and yield copolymers which can be alkylated.
  • any a-olefin having a molecular weight from about 140 to about 588 may be employed in the alkylation reaction.
  • alpha-olefins straight chain or branched
  • linear a-olefins are preferred because of their. commercial availability, numerous isomers of a-olefins ranging from l-pentene to l-pentacosene as well as polybutenes may also be employed in the alkylation reaction. The only precaution required in such case is that the isomer contain an ethylenic unsaturation in the a-position thereof.
  • a mixture of commercially available linear a-OlCfiHS produced by cracking petroleum wax orby polymerizing lower olefins may also be used as the alkylating agent.
  • the commercial product composition contains a mixture of linear olefins ranging from 11 to 15 carbon atoms, and as high as 15 to 22 carbon atoms.
  • alkylated polymers of heterocyclic N-vinyl monomers suitable for the purpose of the present invention are also obtained by alkylating the polymer (homoand co-polymer) with at least 5 moles to as high as 16 moles of ethylene for each mole of polymer to yield an alkylate wherein the ethylene propagates itself to a minimum average chain length of 10 carbon atoms.
  • a minimum average chain length of 10 carbons is also obtained by alkylation with l-p-ropene, l-butene, l-pentene, l-hexene, l-heptene, l-octene or l-nonene.
  • the required number of moles of such oz-Olefin, i.e., from 2 to 9 carbon atoms to obtain the minimum average chain length of 10 carbon atoms the following formula may be used:
  • M represents the number of moles of the -olefin and C represents the number of carbon atoms in the a-olefin.
  • chlorinated and/or fluor'inated a-olefins such as, for example, dichlorovinylidene fluoride, chlorovinylidene fluoride, chlorotrifluoroethylene, tetrafluoroethylene, vinylidene fluoride and the like may be used.
  • an organic solvent is employed which is common to the polymer and alpha-olefin(s).
  • solvents various alcohols such as methanol, ethanol, propanol, isopropanol, butanol, sec-butanol, amyl alcohol, hexanol, 2-ethyl-1ahexanol, ethylene glycol, 1,2-butanediol, 4-butanediol, etc. may be employed.
  • Other solvents such as d-iacetone alcohol, diethylene glycol, ethylene glycol monomethyl ether acetate, methylene chloride and the like may also be employed. It is to be noted that the nature or character of the organic solvent is immaterial so long as it is a liquid, forms a solution with the polymer and alkylating a-olefin(s), and is not susceptible to alkylation.
  • organic solvent employed is not critical. Any amount which will yield a solution of the polymeric material and a-olefin(s) will suflice. However, for purposes of expediency, for every part by weight of solid homopolymer or.copolymer of N-vinyl lactam, from 2 to 10 parts of organic solvent, either by volume or by weight, are sufficient to yield a workable solution.
  • any one of the known tertiary-alkyl organic peroxides such as, for example, t-butyl hydro-peroxide, di-t-butyl peroxide, t-butyl perbenzoate, di-ti-butyl peroxide, t-butyl perbenzoate, di-ti-butyl perphthalate, t-butyl-pentamethylethyl peroxide, tbutyl-triphenylmethyl peroxide, di-t-amyl peroxide, bis-(triethylmethyl) peroxide, bis-(triphenylmethyl) peroxide, 2,5dimethylhexyl-2,S-dihydro-peroxide, 2,5 dimethyl-2,5-di(t-butyl peroxy) hexane, 2,5-dimethy1- hexyl-2,5-di(peroxy be
  • the alkylation of the polymers or the simultaneous polymerization and alkylation reaction of the monomer(s) is preferably conducted in the presence of hexanol. As the latter is being removed during vacuum distillation, it is replaced with a refined mineral oil and the resulting solution of the alkylated polymer employed as the additive. Any refined mineral oil used by the pharmaceutical and cosmetic trade is ideally suited as a replacement during the removal of the hexanol by vacuum distillation.
  • the flask was purged thoroughly with nitrogen and heated. The contents were maintained at reflux (120 C. pot) for 30 hours and then cooled and analyzed. The analyses showed the presence of only 3.05% of a-octadecene in the solution, corresponding to 18 grams unreacted olefin.
  • the flask was then purged thoroughly with nitrogen, heated and maintained at 125-135 C. for 24 hours.
  • the contents when analyzed showed the presence of only 4.54% of u-octene, corresponding to about 21 grams of the unreacted olefin.
  • the solvent was stripped in vacuum and about 210 grams of a clear, oily gel was obtained.
  • the flask was purged thoroughly with nitrogen and heated. The contents were maintained at reflux for 24 hours and then cooled and analyzed. The analysis showed the presence of 7.75% of the C a-olefin in the solution corresponding to 37.5 grams of unreacted olefin.
  • EXAMPLE VI An /20 (by weight) copolymer of N-vinyl-e-capro lactam and ethyl acrylate weighing grams was dissolved in 200 grams of normal amyl alcohol and after the addition of 252 grams (1.5 mole) of u-dodecene and 22 grams (0.15 mole) of di-t-butyl peroxide, the solution was heated and maintained at 140 C. for 10 hours. The reaction mixture was then cooled and analyzed. It was found to contain 4.2% of unreacted a-dodecene, corresponding to 90.5% alkylation based on the dodecene used. The product is a soft waxy substance.
  • the flask was purged thoroughly with nitrogen and heated. The contents were maintained at reflux for 30 hours and then cooled and analyzed. The analysis showed the presence of only 4.97% of u-octene in the solution corresponding to 28 grams of unreacted olefin.
  • Example I was repeated with the exception 1 mole of aeicosene was replaced by 1 mole of a commercial mixture of oc-OlefinS in the C -C carbon range.
  • the product is a waxy substance.
  • Total peroxide 22 grams or 0.24 mole.
  • total peroxide 22 grams or 0.24 mole.
  • alkylated polymers of heterocyclic N-vinyl monomers prepared as above described, and in accordance with the foregoing illustrative examples, are soluble in all of the unctuous materials used in toiletry preparations such as vegetable and mineral oils, fatty acids, fatty acid esters, waxes, polyoxyalkylene glycols, higher alcohols of from 6 carbon atoms and up, including compounds having similar boiling points of the type employed in the alkylation reaction. They are also partially soluble in hot lower alcohols such as ethanol and propanol.
  • the ethanol contains about 0.1% of alkylated polymer
  • the propanol contains about 0.3% of the alkylated polymer.
  • Their partial solubility in such alcohols provides an excellent means for incorporation into non-unctuous materials.
  • the alkylated polymers are added at any suitable stage of conventional toiletry manufacture. In other words, if the toiletry preparation comprises an unctuous base the alkylated polymer is dissolved in such base by gentle heating and stirring until solution is attained.
  • unctuous material is a liquid such as mineral oil, myristyl alcohol, etc.
  • the alkylated polymer is dissolved therein'at room temperature with or without gentle heating and stirring.
  • unctuous components are solids such as solid petrolactams, paraflin wax, natural and synthetic waxes, fatty acid, fatty acid esters, lanolin, etc.
  • they are first heated to the liquid state and the alkylated polymer dissolved therein with stirring.
  • the temperature of heating may vary from 50 to C., depending upon the nature or character of the unctuous material.
  • a water phase is included in such preparation such as triethanolamine, borax, sodium or potassium hydroxide, and any other water soluble components, the oil phase is added slowly to the water phase or vice versa with good agitation.
  • the amount of alkylated polymer that is employed to effect the desired results ranges from about 0.1% to about 50% by weight based on the total weight of the completed toiletry preparation.
  • the alkylated polymers are added at any stage of manufacture of cold creams, cleansing creams, emollient creams, finishing creams, skin-softening lotions, hand cleaners, lubricating creams, overnight creams, iabsorption-base creams, hand creams and lotions, foot creams, baby creams, baby skin oils; special creams, such as astringent creams, bleaching creams, acne creams, protective creams (industrial creams), vanishing creams, foundation creams, brushless shaving creams, shaving preparations, after-shave lotions and sprays, medicated creams, deodorants and anti-perspirants, such as deodorant creams and lotions, roll-on deodorants, sunburn preventives, suntan preparations, paste or lotion rouges, cream rouges,
  • the alkylated polymers are effective pigment dispersers and act as color receptors.
  • the presence of the alkylated polymer improves the softness, water repellency and manageability of the hair.
  • the alkylated polymers may be added to creams, foams or gels and the resulting preparations pressurized with nitrogen, argon, or the usual liquefied fluorochloro-hydrocarbons.
  • borax sodium tetraborate
  • EXAMPLE XV Hand lotion (liquid) grams of boric acid was dissolved in 30 grams glycerine by heating the mixture in a 100 ml. beaker to 105 C. with an electromagnetic-type electrically heated stirrer. 30 grams of lanolin and 10.5 grams of the alkylated polymer of Example I were dissolved in 40 grams of white mineral oil in a 250 ml. beaker by heating to 60 C. on a steam bath while stirring with a small stainless steel stirrer. After rninutes stirring at 60 C., and
  • the glycerine solution of boric acid was slowly added in a thin stream to the solution of lanolin, additive and mineral with rapid agitation.
  • EXAMPLE XVI Vanishing cream EXAMPLE XVII Cleansing cream 10 grams of petrolatum, 27.5 grams of white mineral oil, 12.5 grams of parafiin wax and 5 grams of the alkylated polymer of Example I were melted together in a 100 ml. beaker while stirring and heating on a steam bath to 12 72 C. The melted solution was poured into a glass jar and allowed to cool undisturbed overnight.
  • EXAMPLE XVIII Hand lotion (salve) 2 grams of boric acid were dissolved in 12 grams of glycerine by heating to'105 C. with stirring in a 30 ml. beaker. 16 grams of petrolatum, 12 grams of lanolin and 42 grams of the alkylated polymer of Example I were melted and dissolved in each other by heating to 70 C. while stirring in a 100 ml. beaker. The boric acid-glycerine solution was added slowly to the petrolatum-lanolin-addirive-solution with continual stirring with a stainless steel agitator. The hot C.) molten salve was poured into a jar and allowed to cool undisturbed to room temperature.
  • Emollient cream This cream was prepared from the following ingredients in percent by weight: Y
  • Example II 7 7 Grams Beeswax 8 Cetyl alcohol 2 Cocoa butter 2 Lanolin (anhydrous) 10 Olive oil 50 Lecithin 1 Alkylated polymer of Example II 7 were dissolved in admixture by heating to 87 C. The resulting solution was allowed to reach room temperature to which was added 1 gram of rose perfume. Sufiicient distilled water was added with agitation to make 100 parts by weight of finished emollient cream.
  • EXAMPLE XXIV Synthetic soap bar 30% by weight of stearic acid and 10% by weight of the alkylated polymer of Example I were melted and emulsified with 8% by weight of water. To the emulsion were added, with agitation, 30% by weight of myristic sodium isethionate, 5% by weight of ethoxylated nonyl phenolcontaining 80% by weight of ethylene oxide and by weight of sodium tallowate. The resulting mixture was cooled and subjected to soap bar formation by the conventional injection molding.
  • EXAMPLE XXV Total sunscreen lotion Percent by weight Mineral oil 40.0 Beeswax 1 6.0 Oil solution of alkylated polymer of Example X 19.5 Water 33.5 2,2, 4,4'-tetrahydroxy-benzophenone 0.5 Sodium hydroxide 0.5
  • the oil phase and alkylated polymer were heated to 70 -C. and the water phase, including the sunscreen agent and sodium hydroxide to the same temperature.
  • the oil phase was added slowly to the'water phase with good agitation. A'creamy emulsion resulted.
  • Myristic acid 2 90% of the above concentrate maybe pressurized with a 60/ 40 mixture of propellents 114/ 12 at 10% concentration. If desired, a small amount from about 0.2 to 0.5%
  • polyvinyl pyrrolidone by weight may be incorporated in the shampoo so that in addition to functioning as a shampoo, it will also serve as a grooming agent by permitting curl retention.
  • EXAMPLE XXIX Bath talc One gram of alkylated polymer of Example -I was dissolved in 250 grams of hot ethanol. While maintaining the ethanol solution hot, 50 grams of talcum powder were added slowly with constant agitation. After the addition of the talc was complete, the slurry was permitted to cool to room temperature, a few drops of perfume added wit-h mixing, and the slurry filtered, dried and the small lumpy particles broken by milling in a hammer mill. The dried fine powder was passed through the customary talc sieve and stored in a container. The a1- cohol may also be removed by vacuum distillation of th slurry while maintaining good agitation.
  • EXAMPLE XXX After-shave lotion Percent by weight The ethanol was heated to about the boil and the alkylated polymer added slowly until dissolved. The'homo genous cloudy solution was allowed to cool with agitation and the perfume added when the solution reached room temperature. 60% by weight of the resulting concentrate was charged in the conventional manner with 40 parts by weight of a mixture consisting of 30% by weight of propellent 12 and 10% by weight of propellent 114. The aerosol preparation was clear in view of the higher solubility of the alkylated polymer in the propellent mixture.
  • the components were heated to the boil of ethanol, 5 grams of polyvinylpyrrolidone K-30 added with stirring, quickly cooled to room temperature, perfume added and 30% by weight of the cooled solution pressurized in the conventional manner with 70% by weight of a mixture 15 of propellents containing 35% by weight of propellent 12 and 65% by weight of propellent 11.
  • the alkylated polymer also functions as plasticizer for the polyvinylpyrrolidone (or copolymers thereof with vinyl acetate) and as water repellent for the film. It imparts softness and lubricity to the hair. It also reduces the tack when the polymeric film former concentration is around by weight or higher in the hair spray composition.
  • This cleaner is useful for removing heavily embedded grime, oil, grease and stains.
  • the calcium carbonate was mixed with the water and glycerine to yield a uniform suspension.
  • To the suspension was added in sufficient quantity the customary gum and peppermint fiavor to yield a paste.
  • the alkylated polymer was mixed with the sodium lauryl sulfoacetate and incorporated into the paste with thorough mixing.
  • the alkylated polymers may be employed in the preparation of pharmaceutical salves, ointments and suppositories. Such preparations may contain the usual antiseptic, germicidal and medicinal agents.
  • the alkylated polymers display their desirable emollient effects in all types of ointments, salves, lotions, antiseptics, disinfectants, and other medicinal preparations for external use.
  • the alkylated polymers are especially adaptable in the preparation of non-irritating detergent emulsions as skin cleansers for removing grease and oils from the skin. They manifest their softening and soothing effects when incorporated in hemorrhoidal preparations. They can be incorporated into unctuous materials and employed as lubricants to aid the passage of cathethers or enema tubes. They can be incorporated into salves and ointments used in the treatment of burns. Due to the water insolubility of the alkylated polymers, a continued softening (emollient) effect is noted even after several washings of the skin with soap and water.
  • alkylated polymers of heterocyclic' N-vinyl monomers in cosmetics and soaps
  • alkylated polymers homoand co-polymers
  • other heterocyclic N-vinyl monomers containing a a o I II group in the ring may be employed as additives in accordance with the present invention.
  • Such monomers include the N-vinyl monomers of alkyl substituted derivatives of lactams such as, for example, 4,4-dimethyl-2- pyrrolidone, 3,3-dimethyl-2-pyrrolidone, 3-ethyl-2-pyrrolidone, 3,5-dimethyl-2-pyrrolidone, 3-ethyl-2-pyrrolidone, 4-acryl-2-pyrrolidone, 5-ethyl-2-pyrrolidone, 3- methyl-Z-pyrrolidone, 4-methyl-2-pyrrolidone, 3,3,5-trimethyl 2 pyrrolidone, 5,5-diethyl-2-piperidone, 5,6-dimethyl-Z-piperidone, 4-ethyl 2 piperidone, 6-ethyl-3- methyl-Z-piperidone, 3-methyl-2-piperidone, 4-methyl-2- piperidone, 5-methyl-2-piperidone, 3,6-dimethyl-2-caprolactarn, 4,6-dimethyl
  • Patent 2,905,660 and US. Patent 3,097,087) 5-ethyl-2-oxazinidinone, 5-phenyl- 2-oxazinidinone, 4,5-dimethyl 2 oxazinidinone, 5,5-dimethyl-Z-oxazinidinone, 2,S-diphenyl-2-oxazinidinone, 2- pheny1-4-oxothiazolidone, 2,2-diphenyl 4 oxothiazolidone, 2,2-dimethyl 4 oxothiazolidone, 2-oxazolidinone (US.
  • Patent 2,905,690 and US Patent 2,891,058) 5- methyl-2-oxazolidinone, 4-methyl 2 oxazolidinone, 5- ethyl 2 oxazolidinone, 4,5-dimethyl 2 oxazolidinone, 2-phenyl-2-oxazolidinone, 5-butyl-2-oxazolidinone, S-propyl-2-oxazolidinone, 4,5-diethyl-2-oxazolidinone, Z-piperazonone (JACS 62, 1202 (1940), 3,3-dimethyl-2-ketopiperazine and 3-methyl-2-ketopiperazine, 4-thiazolidone (JACS 76, 578 (1954), Z-thiazolidone (J.
  • skin in general, which is the external covering or integument of the body and includes the scalp which isan integument of the upper part of the head. Since hair is the natural covering of the head growing from the skin and since nails (modified epidermis,
  • a composition for application to a member of the group consisting of skin and appendages of theskin containing as an essential component in a toiletry carrier from 0.1 to about 50% by weight of said carrier of an alkylated polymer of an N.-vinyl heterocyclic monomer wherein on an average of at least 25% of the N-vinyl heterocyclic monomer units in said polymer are alkylated with an alkyl chain of from-10 to 42 carbon atoms, said alkylated polymer being selected from the class consisting of polymers prepared by (a) the simultaneous polymerization and alkylation of one mole of a monomer selected from the group consisting of at least one N-vinyl heterocyclic monomer and a mixture of monomers containing from 60 to 95% by weight of said N-vinyl heterocyclic monomer and from to 40% by weight of a non-heterocyclic polymerizable monoethylenically unsaturated monomer, and v (b) by the alkylation of one mole of a poly
  • R represents an alkylene bridge of from 2 to 4 carbon atoms to complete a 5-, 6- and 7-membered heterocyclic ring system
  • R represents a member selected from the class consisting of hydrogen, methyl and ethyl
  • R represents a member selected from the class consisting of hydrogen and methyl
  • R represents a member selected from the class consisting of hydrogen, alkyl of from 1 to 12 carbon atoms and phenyl
  • m is an integer of from 1 to 4
  • n is an integer of from 1 to 4 when m has a value of 1
  • from 2 to 4 when m has a value greater than
  • y is an integer of from 2 to 3
  • the said non-heterocyclic polymerizable monoethylenically unsaturated monomer is selected from the class consisting 18- of vinyl esters, vinyl chloride, vinylidene' chloride, acrylonitrile, styrene, acrylic acid, acrylate esters, methacrylic acid
  • a composition for application to a member of the group consisting of skin and appendages of the skin containing as an essential component in a toiletry carrier from 0.1 to about 50% by weight of said carrier of an alkylated poly-mer of an N-vinyl lactam monomer Wherein on an average ofat least 25% of the N-vinyl lactam monomer units in said polymer are alkylated with an alkyl chain of from 10 to 42 carbon atoms, said alkylated polymer being selected.
  • N-vinyl lactam monomer is selected from the class consisting of monomers of the fol lowing formulae:
  • R represents an alkylene bridge of from 2 to 4 carbon atoms to complete a 5-, 6- and 7-mem-bered-heterocyclic ring system
  • R represents a member selected from the class consisting of hydrogen, methyl and ethyl
  • R represents a member selected from the class consisting of hydrogen and methyl
  • R represents a member selected from the class consisting of hydrogen, alkyl of from 1 to 12 carbon atoms and phenyl
  • m is an integer of from 1 to 4
  • n is an integer of from 1 to 4 when m has a value of l, and from 2 to 4 when m has a value greater than 1
  • y is an integer of from 2 to 3
  • the said non-heterocyclic polymerizable monoethylenically unsaturated monomer is selected from the class consisting of vinyl esters, vinyl chloride, vinylidene chloride, acrylonitrile, styrene, acrylic acid, acryl
  • methacrylic acid methacrylate esters, methacrylonitrile
  • a lotion for-conditioning and softening the skin containing as an essential component in a dermatologically acceptable carrier vfrom 0.1% to about 50% by weight of said carrier of an alkylated polymer of an N- vinyl heterocyclic monomer prepared by the process defined in claim 1.
  • a cuticle softener for conditioning and softening the cuticles of the nails of fingers and toes containing as an essential component in a dermatologically acceptable carrier from 0.1% to about 50% ,by weight of said cartier of an alkylated polymer of an N-vinyl heterocyclic monomer, prepared by the process defined in claim 1. 7.
  • a toiletry preparation for application to a member selected from the group consisting of skin and appendages of the skin containing as an essential component in a toiletry carrier from 0.1% to about 50% by weight of said carrier of an alkylated homopolymer of N-vinyl-2- pyrrolidone, wherein on the average of at least 50% of the N-vinyl-2-pyrrolidone units in said homopolymer are alkylated with an alkyl group of from 10 to 42 carbon atoms, prepared by the alkylation of one mole of the homopolymer of N-vinyl-2-pyrrolidone with 0.5 to 4 moles of an u-olefin of from 10 to 42 carbon atoms in solution of an organic solvent common to said homoof an organic peroxide catalyst per mole of said a-olefin at a temperature ranging from 100 to 200 C.

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US423603A 1965-01-05 1965-01-05 Emollient preparations containing alkylated polymers of heterocyclic n-vinyl monomers Expired - Lifetime US3406238A (en)

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US423603A US3406238A (en) 1965-01-05 1965-01-05 Emollient preparations containing alkylated polymers of heterocyclic n-vinyl monomers
GB55215/65A GB1130144A (en) 1965-01-05 1965-12-30 Toiletry compositions
FR44808A FR1462808A (fr) 1965-01-05 1966-01-04 Nouvelles compositions cosmétiques contenant un polymère alkylé préparé à partir de monomères n-vinyl hétérocycliques
SE110/66A SE312197B (enrdf_load_stackoverflow) 1965-01-05 1966-01-04
NL6600037A NL127700C (enrdf_load_stackoverflow) 1965-01-05 1966-01-04
CH11366A CH490853A (de) 1965-01-05 1966-01-05 Als Kosmetikum oder Salbengrundlage bestimmtes Mittel
DE19661617484 DE1617484A1 (de) 1965-01-05 1966-01-05 Toilettenpraeparate

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Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3479417A (en) * 1966-11-16 1969-11-18 Gaf Corp Graft copolymers of alpha-olefins and preformed,water-insoluble,homopolymer of n-vinyl-2-pyrrolidone
US3878135A (en) * 1973-10-15 1975-04-15 Warner Lambert Co Denture adhesive preparation containing an anionic protein material
US3906091A (en) * 1969-12-24 1975-09-16 Oreal Hair-setting lotion containing a reducing agent
US3911105A (en) * 1973-06-08 1975-10-07 Oreal Fatty compositions for use in cosmetic makeup compositions and said cosmetic makeup compositions
US3926870A (en) * 1973-10-15 1975-12-16 Warner Lambert Co Denture adhesive preparation containing an anionic protein material
US3937811A (en) * 1973-06-08 1976-02-10 Societe Anonyme Dite: L'oreal Fatty compositions for use in cosmetic makeup compositions and said cosmetic makeup compositions
US3988110A (en) * 1969-12-24 1976-10-26 Societe Anonyme Dite: L'oreal Hair coloring and hair-setting lotion containing a direct dye, a reducing agent and a solar filter
US4075131A (en) * 1976-09-17 1978-02-21 Minnesota Mining And Manufacturing Company Conditioning shampoo
USRE29871E (en) * 1973-06-08 1978-12-26 L'oreal Fatty compositions for use in cosmetic makeup compositions and said cosmetic makeup compositions
US4172122A (en) * 1977-07-29 1979-10-23 Minnesota Mining And Manufacturing Company Substantive sunscreening compositions
US4268499A (en) * 1979-06-07 1981-05-19 Dow Corning Corporation Antiperspirant emulsion compositions
US4507280A (en) * 1979-07-02 1985-03-26 Clairol Incorporated Hair conditioning composition and method for use
US4701322A (en) * 1980-04-21 1987-10-20 The Procter & Gamble Company Conditioning shampoo
US5004598A (en) * 1986-11-10 1991-04-02 The B. F. Goodrich Company Stable and quick-breaking topical skin compositions
US5011681A (en) * 1989-10-11 1991-04-30 Richardson-Vicks, Inc. Facial cleansing compositions
US5026540A (en) * 1987-06-04 1991-06-25 Chesebrough-Pond's Usa Co. Sunscreen composition
AU640533B2 (en) * 1991-08-26 1993-08-26 Isp Investments Inc. Copolymer of vinyl pyrrolidone and a c30 alpha-olefin in flake or powder form, process for making same, and personal care compositions therewith
US5304317A (en) * 1991-03-28 1994-04-19 Fospur Limited Froth flotation of fine particles
US5690918A (en) * 1995-12-19 1997-11-25 Maybelline, Inc. Solvent-based non-drying lipstick
WO2002032382A1 (fr) * 2000-10-19 2002-04-25 L"Oreal Pate pigmentaire anhydre et son utilisation en cosmetique
US20050249686A1 (en) * 2004-04-27 2005-11-10 Francoise Pataut Cosmetic composition free of water comprising fatty acid esters, petrolatum oil and non-ionic polymers
US20090036551A1 (en) * 2007-08-03 2009-02-05 Basf Se Copolymers based on n-vinyl lactams and olefins as their use as solubilizers for slightly water-soluble compounds
WO2013156385A3 (en) * 2012-04-17 2014-01-16 L'oreal Water resistant compositions containing a heterocyclic compound and a compound having at least one functional group chosen from an amino group and a hydroxyl group
US9028804B2 (en) 2012-04-17 2015-05-12 L'oreal Water resistant compositions containing a lactone compound and an amine compound chosen from amino alcohol compounds and alkoxylated amine compounds

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE758280A (fr) * 1969-10-31 1971-04-30 Dow Chemical Co Lotions cosmetiques non graisseuses
FR2168202A1 (en) * 1972-01-20 1973-08-31 Fabre Sa Pierre Accelerator for depilation - contg n vinyl lactam copolymer with unsatd carboxylic semi ester
EP0019970B1 (en) * 1979-05-23 1983-10-19 THE PROCTER & GAMBLE COMPANY Conditioning shampoo
EP0191128A1 (en) * 1985-02-14 1986-08-20 TERAD International, Inc. Topical preparations for human skin irratations
FR2631825B1 (fr) * 1988-05-26 1990-09-07 Serho Francois K Nouvelles compositions de cires a depiler jetables, arrachables, auto-detachables, et leur procede de preparation
DE4243119A1 (de) * 1992-12-22 1994-06-23 Henkel Kgaa Wasserabweisende Babycreme

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DE850328C (de) * 1944-08-10 1952-09-22 Basf Ag Geformte Wasch- und Reinigungsmittel
US2723248A (en) * 1954-10-01 1955-11-08 Gen Aniline & Film Corp Film-forming compositions
CA519669A (en) * 1955-12-20 Manno F. Nelson, Jr. Dentifrice containing polyvinylpyrrolidone
GB797992A (en) * 1955-10-06 1958-07-09 British Oxygen Co Ltd Protective substances
US3250680A (en) * 1960-07-19 1966-05-10 Gillette Co Heat-generating cosmetic composition
US3309365A (en) * 1964-10-09 1967-03-14 Gen Aniline & Film Corp Alkylated cyclic imides and processes for their production

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Publication number Priority date Publication date Assignee Title
CA519669A (en) * 1955-12-20 Manno F. Nelson, Jr. Dentifrice containing polyvinylpyrrolidone
DE850328C (de) * 1944-08-10 1952-09-22 Basf Ag Geformte Wasch- und Reinigungsmittel
US2723248A (en) * 1954-10-01 1955-11-08 Gen Aniline & Film Corp Film-forming compositions
GB797992A (en) * 1955-10-06 1958-07-09 British Oxygen Co Ltd Protective substances
US3250680A (en) * 1960-07-19 1966-05-10 Gillette Co Heat-generating cosmetic composition
US3309365A (en) * 1964-10-09 1967-03-14 Gen Aniline & Film Corp Alkylated cyclic imides and processes for their production

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3479417A (en) * 1966-11-16 1969-11-18 Gaf Corp Graft copolymers of alpha-olefins and preformed,water-insoluble,homopolymer of n-vinyl-2-pyrrolidone
US3988110A (en) * 1969-12-24 1976-10-26 Societe Anonyme Dite: L'oreal Hair coloring and hair-setting lotion containing a direct dye, a reducing agent and a solar filter
US3906091A (en) * 1969-12-24 1975-09-16 Oreal Hair-setting lotion containing a reducing agent
US3911105A (en) * 1973-06-08 1975-10-07 Oreal Fatty compositions for use in cosmetic makeup compositions and said cosmetic makeup compositions
US3937811A (en) * 1973-06-08 1976-02-10 Societe Anonyme Dite: L'oreal Fatty compositions for use in cosmetic makeup compositions and said cosmetic makeup compositions
USRE29871E (en) * 1973-06-08 1978-12-26 L'oreal Fatty compositions for use in cosmetic makeup compositions and said cosmetic makeup compositions
US3926870A (en) * 1973-10-15 1975-12-16 Warner Lambert Co Denture adhesive preparation containing an anionic protein material
US3878135A (en) * 1973-10-15 1975-04-15 Warner Lambert Co Denture adhesive preparation containing an anionic protein material
US4075131A (en) * 1976-09-17 1978-02-21 Minnesota Mining And Manufacturing Company Conditioning shampoo
US4172122A (en) * 1977-07-29 1979-10-23 Minnesota Mining And Manufacturing Company Substantive sunscreening compositions
US4268499A (en) * 1979-06-07 1981-05-19 Dow Corning Corporation Antiperspirant emulsion compositions
US4507280A (en) * 1979-07-02 1985-03-26 Clairol Incorporated Hair conditioning composition and method for use
US4701322A (en) * 1980-04-21 1987-10-20 The Procter & Gamble Company Conditioning shampoo
US5004598A (en) * 1986-11-10 1991-04-02 The B. F. Goodrich Company Stable and quick-breaking topical skin compositions
US5026540A (en) * 1987-06-04 1991-06-25 Chesebrough-Pond's Usa Co. Sunscreen composition
US5011681A (en) * 1989-10-11 1991-04-30 Richardson-Vicks, Inc. Facial cleansing compositions
US5304317A (en) * 1991-03-28 1994-04-19 Fospur Limited Froth flotation of fine particles
AU640533B2 (en) * 1991-08-26 1993-08-26 Isp Investments Inc. Copolymer of vinyl pyrrolidone and a c30 alpha-olefin in flake or powder form, process for making same, and personal care compositions therewith
USRE38441E1 (en) * 1995-12-19 2004-02-24 Maybelline, Inc. Solvent-based non-drying lipstick
US5690918A (en) * 1995-12-19 1997-11-25 Maybelline, Inc. Solvent-based non-drying lipstick
WO2002032382A1 (fr) * 2000-10-19 2002-04-25 L"Oreal Pate pigmentaire anhydre et son utilisation en cosmetique
US20030053969A1 (en) * 2000-10-19 2003-03-20 Florence Tournilhac Anhydrous pigment paste and its use in cosmetics
FR2815537A1 (fr) * 2000-10-19 2002-04-26 Oreal Pate pigmentaire anhydre et son utilisation en cosmetique
US6740316B2 (en) 2000-10-19 2004-05-25 L'oreal Anhydrous pigment paste and its use in cosmetics
US20050249686A1 (en) * 2004-04-27 2005-11-10 Francoise Pataut Cosmetic composition free of water comprising fatty acid esters, petrolatum oil and non-ionic polymers
US20090036551A1 (en) * 2007-08-03 2009-02-05 Basf Se Copolymers based on n-vinyl lactams and olefins as their use as solubilizers for slightly water-soluble compounds
EP2022805A2 (en) 2007-08-03 2009-02-11 Basf Se Copolymers based on N-vinyllactams and olefins as their use as solubilizers for slightly water-soluble compounds
EP2022805A3 (en) * 2007-08-03 2009-02-25 Basf Se Copolymers based on N-vinyllactams and olefins as their use as solubilizers for slightly water-soluble compounds
WO2013156385A3 (en) * 2012-04-17 2014-01-16 L'oreal Water resistant compositions containing a heterocyclic compound and a compound having at least one functional group chosen from an amino group and a hydroxyl group
US9028804B2 (en) 2012-04-17 2015-05-12 L'oreal Water resistant compositions containing a lactone compound and an amine compound chosen from amino alcohol compounds and alkoxylated amine compounds

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NL127700C (enrdf_load_stackoverflow) 1969-07-15
GB1130144A (en) 1968-10-09
FR1462808A (fr) 1966-12-16
NL6600037A (enrdf_load_stackoverflow) 1966-07-06
CH490853A (de) 1970-05-31
DE1617484A1 (de) 1971-05-27
SE312197B (enrdf_load_stackoverflow) 1969-07-07

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