WO2001033963A1 - A composition comprising solubilized repellent active component - Google Patents

A composition comprising solubilized repellent active component Download PDF

Info

Publication number
WO2001033963A1
WO2001033963A1 PCT/US1999/026581 US9926581W WO0133963A1 WO 2001033963 A1 WO2001033963 A1 WO 2001033963A1 US 9926581 W US9926581 W US 9926581W WO 0133963 A1 WO0133963 A1 WO 0133963A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
straight
saturated
oily component
active compound
Prior art date
Application number
PCT/US1999/026581
Other languages
French (fr)
Inventor
Li Sun
Victorio Tan Wee
Gong-Xiang Chen
Hsiang-Kuen Mao
Original Assignee
The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to AU18164/00A priority Critical patent/AU1816400A/en
Priority to PCT/US1999/026581 priority patent/WO2001033963A1/en
Publication of WO2001033963A1 publication Critical patent/WO2001033963A1/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier 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
    • A61Q17/02Barrier 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 containing insect repellants

Definitions

  • the present invention relates to a composition containing solubilized insect and dust mite repellent.
  • it relates to a solubility system of a natural insect and dust mite repellent and compositions thereof.
  • N,N-diethyl-m-toluamide is the most widely used insect repellent active sometimes referred to as "DEET.” See U.S. Patent 2,932,665, Wagner et al, issued on April 12, 1960, U.S. Patent 4,756,905, Melnik, issued July 12, 1988, U.S. Patent 4,416,881 , McGovern et al, and U.S. Patent 4,419,360, Smolanoff, disclosing DEET to protect an outdoorsman from insects and adequately cover the skin of the user.
  • d-8-ACA Another repellent active that has previously been proposed is d-8-ACA, disclosed in Chinese patent application No. 94100746, Hanzhi et al., filed on July 2. It is both natural and safe to the human and provides good repellent efficacy for insect and dust mites instead of killing them. This active is typically provided in a crystallized form. The liquid form of d-8-ACA is, however believed to be the much more efficacious for use in many personal care and home care products to give effective repellent benefits. d-8-ACA can be delivered to skin in a water and alcohol solution. Unfortunately, d-8-ACA is a water-insoluble material.
  • compositions having superior insect and dust mites repellent properties is proposed.
  • the composition contains:
  • R 1 and R2 are independently selected from saturated, straight or branched alkyl group of from 1 to about 10 carbons;
  • safety and effective amount means an amount of a compound or composition sufficient to significantly induce a positive benefit, preferably a positive skin appearance or feel benefit, including independently the benefits disclosed herein, but low enough to avoid serious side effects, e.g., to provide a reasonable benefit to risk ratio, within the scope of sound judgment of the skilled artisan.
  • All ingredients such as actives and other ingredients useful herein may be categorized or described by their cosmetic and/or therapeutic benefit or their postulated mode of action. However, it is to be understood that the active and other ingredients useful herein can, in some instances, provide more than one cosmetic and/or therapeutic benefit or operate via more than one mode of action. Therefore, classifications herein are made for the sake of convenience and are not intended to limit an ingredient to the particularly stated application or applications listed.
  • the topical composition of the present invention contains an active compound having the following formula (I) and a oily component for obtaining a liquid active solvent.
  • R 1 and R2 are independently selected from saturated, straight or branched alkyl group of from 1 to about 10 carbons.
  • the oily component for obtaining a liquid active solution having less than
  • composition provides superior insect repellent efficacy, especially prolonged repellent efficacy in liquid form.
  • composition of the present invention also provides desirable mites repellent in stead of killing them.
  • composition of the present invention contains a safe and effective amount of an active compound having the formula (I):
  • R1 and R2 are independently selected from saturated, straight or branched alkyl group of from 1 to about 10 carbons. * indicates active place.
  • R1 and R ⁇ are independently selected from saturated, straight alkyl groups of from 1 to about 3 carbons. More preferably, R " 1 and R2 are independently methyl, ethyl, or propyl.
  • the active component of the present invention has optical isomers; d-, I-, and a mixtures of d- and l-forms.
  • the active component provides as a mixture of higher levels of d-form with lower levels l-form. It is believed that d- form works effectively than l-form.
  • the active compound can be derived by a method described in Chinese patent application No. 94100746, Hanzhi et al., filed on July 26, 1995. Such compounds include d-8- acetoxycarvotanacetone (d-8-ACA).
  • the active compound of the present invention provides strong activity to repel insects such as mosquitoes and gnats and arachnid. These compounds are particularly effective in repelling insects instead of killing them when formulated in active repellent solution with a oily component.
  • This class of active compounds can also be effective to repel dust mites, which are members of the arachnid family and often are unaffected by traditional insect repellent compositions. It is well known that dust mites are a common source of allergens. As such, it is desirable to repel dust mites from areas that are used by people who are sensitive to allergens. It is also believed that the dead mites of the house dust variety float in the air, causing bronchial asthma, allergic rhinitis, allergic dermatitis, and various other disorders. These areas include households, automobiles, offices and other areas.
  • the active compounds can provide desirable mite repellency. Such repellancy and attractant of mites are important for the people having allergic dermatitis.
  • the active components of the present invention are effective against most of the house dust mites such as Dermatophagoides farinae and
  • the concentration of the formula (I) is from about 0.1 wt% to about 85 wt% of the active compound, more preferably from about 0.5 wt% to about 50 wt%.
  • compositions of the present invention may further comprise additional active components. It is especially preferred that the additional actives fall within the class of oily compounds. But it is understood that the additional active compounds can be any appropriate compound that is compatible with the other compounds in the present compositions. Especially preferred additional active compounds are those of the general structure:
  • R 3 is hydrogen or -(CH2) n CH3 and n is integer form about 0 to about
  • Such compounds include 3-n-butyl-n-acetyl aminopropionic acid and its ester. These compounds are sold by Merck Chemical Company under the trade name Merck 3535.
  • additional active compounds for use in the present invention include insect and moth controllingagents such as anti-aggregation pheromones, and other natural and/or synthetic ingredients.
  • Preferred additional active compounds useful in the composition of the present invention are perfume ingredients, such as citronellol, citronellal, citral, linalool, cedar extract, geranium oil, sandalwood oil, 2-(diethylphenoxy)ethanol, 1-dodecene, etc.
  • perfume ingredients such as citronellol, citronellal, citral, linalool, cedar extract, geranium oil, sandalwood oil, 2-(diethylphenoxy)ethanol, 1-dodecene, etc.
  • Other examples of additional active compounds useful in the composition of the present invention are disclosed in U.S. Patent No.
  • composition and the system of the present invention contains an oily component.
  • the active compounds identified above are most effective when in a liquid state. But when these compounds are dissolved in solvent containing alcohol with water and applied to a surface, the solvent evaporates and the active compound tends to crystallize, rendering it relatively ineffective as an insect or dust mite repellent.
  • the active compounds are preferably dissolved in an oily compound before they are incorporated into any product applications.
  • the oily component useful herein can be derived from animals, plants, or petroleum and may be natural or synthetic (i.e., man-made).
  • the oily component are substantially water-insoluble, more preferably essentially water-insoluble.
  • the oily components herein has about 50°C or less of a melting point under one atmosphere of pressure, and does not evaporate rapidly.
  • the oily component useful herein can has a viscosity of from about 0 to about 10,000 cps; preferably from about 20 to about 5,000 cps.
  • suitable oily components include those selected from the group consisting of mineral oil, petrolatum, straight and branched chain hydrocarbons having from about 7 to about 40 of carbon atoms, vegetable oils and hydrogenated vegetable oils, animal fats and oils, polyhydric alcohols, silicone oils, alcohol esters of carboxylic acids and of dicarboxylic acids, alkylene glycol esters, C-
  • Mineral oil which is also known as petrolatum liquid, is a mixture of liquid hydrocarbons obtained from petroleum. See The Merck Index, Tenth
  • Petrolatum which is also known as petroleum jelly, is a colloidal system of nonstraight-chain solid hydrocarbons and high-boiling liquid hydrocarbons, in which most of the liquid hydrocarbons are held inside the micelles. See The Merck Index, Tenth Edition, Entry 7047, p. 1033 (1983); Schindler, Drug. Cosmet. Ind.. 89, 36-37, 76, 78-80, 82 (1961 ); and International Cosmetic Ingredient Dictionary, Fifth Edition, vol. 1 , p. 537 (1993), which are incorporated by reference herein in their entirety.
  • (iii) Straight and branched chain hydrocarbons having from about 7 to about 40 carbon atoms.
  • these hydrocarbon materials include dodecane, isododecane, squalane, cholesterol, hydrogenated polyisobutylene, docosane (i.e. a C22 hydrocarbon), hexadecane, isohexadecane (a commercially available hydrocarbon sold as Permethyl® 101 A by Presperse, South Plainfield, NJ).
  • docosane i.e. a C22 hydrocarbon
  • hexadecane isohexadecane
  • C7-C40 isoparaffins which are C7-C40 branched hydrocarbons.
  • Vegetable oils and hydrogenated vegetable oils are C7-C40 branched hydrocarbons.
  • vegetable oils and hydrogenated vegetable oils include safflower oil, castor oil, coconut oil, cottonseed oil, menhaden oil, palm kernel oil, palm oil, peanut oil, soybean oil, rapeseed oil, linseed oil, rice bran oil, pine oil, sesame oil, sunflower seed oil, hydrogenated safflower oil, hydrogenated castor oil, hydrogenated coconut oil, hydrogenated cottonseed oil, hydrogenated menhaden oil, hydrogenated palm kernel oil, hydrogenated palm oil, hydrogenated peanut oil, hydrogenated soybean oil, hydrogenated rapeseed oil, hydrogenated linseed oil, hydrogenated rice bran oil, hydrogenated sesame oil, hydrogenated sunflower seed oil, and mixtures thereof.
  • Animal fats and oils e.g., lanolin and derivatives thereof, cod liver oil.
  • Polvhvdric alcohols including, but are not limited to, polyalkylene glycols, more preferably alkylene polyols and their derivatives including glycerin, propylene glycol, dipropylene glycol, tripropylene glycol, polyethylene glycol and derivatives thereof, sorbitol, hydroxypropyl sorbitol, erythritol, threitol, pentaerythritol, xylitol, glucitol, mannitol, hexylene glycol, 1 ,3-butylene glycol, 1 ,2,6-hexanetriol, glycerol, ethoxylated glycerol, propoxylated glycerol, sodium 2- pyrrolidone-5-carboxylate, soluble collagen, gelatin, and mixtures thereof.
  • polyalkylene glycols more preferably alkylene polyols and their derivatives including glycerin, propy
  • Silicone oils including polyalkyl siloxanes such as polydimethyl siloxane, polydiethyl siloxane; polyaryl siloxanes; and polyalkylaryl siloxanes such as polymethylphenyl siloxanes; cyclic polyalkylsiloxanes; polyether siloxane copolymers; and polypropylene oxide modified polydimethylsiloxane.
  • polyalkyl siloxanes such as polydimethyl siloxane, polydiethyl siloxane
  • polyaryl siloxanes such as polymethylphenyl siloxanes
  • polyalkylaryl siloxanes such as polymethylphenyl siloxanes
  • cyclic polyalkylsiloxanes such as polyether siloxane copolymers
  • polypropylene oxide modified polydimethylsiloxane Nonlimiting examples of suitable silicones are disclosed in U.S. Patent No. 5,069,897, to Orr, issued December 3, 1991.
  • polyalkylsiloxanes include the polydimethylsiloxanes, known as dimethicones, examples of which include the Vicasil® series sold by General Electric Company and the Dow Corning® 200 series sold by Dow Corning Corporation.
  • dimethicones include those alkyl-substituted dimethicones include cetyl dimethicone and lauryl dimethicone.
  • Nonlimiting examples include diisopropyl sebacate, diisopropyl adipate, isopropyl myristate, isopropyl palmitate, methyl palmitate, myristyl propionate, 2-ethylhexyl palmitate, isodecyl neopentanoate, di-2-ethylhexyl maleate, cetyl palmitate, myristyl myristate, stearyl stearate, isopropyl stearate, methyl stearate, cetyl stearate, behenyl behenate, dioctyl maleate, dioctyl sebacate, diisopropyl adipate, cetyl octanoate, diisopropyl dilinoleate.
  • _3Q carboxylic acids e.g., ethylene glycol mono- and di- esters, and propylene glycol mono- and di- esters of CI _3Q carboxylic acids e.g., ethylene glycol distearate.
  • esters C-j-30 mono- and poly- esters of sugars and related materials. These esters are derived from a sugar or polyol moiety and one or more carboxylic acid moieties. Depending on the constituent acid and sugar, these esters can be in either liquid or solid form at room temperature.
  • liquid esters include: glucose tetraoleate, the glucose tetraesters of soybean oil fatty acids (unsaturated), the mannose tetraesters of mixed soybean oil fatty acids, the galactose tetraesters of oleic acid, the arabinose tetraesters of linoleic acid, xylose tetralinoleate, galactose pentaoleate, sorbitol tetraoleate, the sorbitol hexaesters of unsaturated soybean oil fatty acids, xylitol pentaoleate, sucrose tetraoleate, sucrose pentaoletate, sucrose hexaoleate, sucrose hepatoleate, sucrose octaoleate, and mixtures thereof.
  • solid esters include: sorbitol hexaester in which the carboxylic acid ester moieties are palmitoleate and arachidate in a 1 :2 molar ratio; the octaester of raffinose in which the carboxylic acid ester moieties are linoleate and behenate in a 1 :3 molar ratio; the heptaester of maltose wherein the esterifying carboxylic acid moieties are sunflower seed oil fatty acids and lignocerate in a 3:4 molar ratio; the octaester of sucrose wherein the esterifying carboxylic acid moieties are oleate and behenate in a 2:6 molar ratio; and the octaester of sucrose wherein the esterifying carboxylic acid moieties are laurate, linoleate and behenate in a 1 :3:4 molar ratio.
  • a preferred solid material is sucrose polyester in which the degree of esterification is 7-8, and in which the fatty acid moieties are C18 mono- and/or di- unsaturated and behenic, in a molar ratio of unsaturates:behenic of 1 :7 to 3:5.
  • a particularly preferred solid sugar polyester is the octaester of sucrose in which there are about 7 behenic fatty acid moieties and about 1 oleic acid moiety in the molecule.
  • Other materials include cottonseed oil or soybean oil fatty acid esters of sucrose. The ester materials are further described in, U.S. Patent 2,831 ,854 and U.S. Patent 4,005,196, Jandacek, issued January 25, 1977; U.S.
  • the fatty alcohols having straight or branched such as cetyl alcohol, stearyl alcohol, and behenyl alcohol; fatty acids having straight or branched, at least about 10 carbon atoms stearic acid, behenic acid, palmitic acid, archidonic acid and sebacic Acid.
  • These are available, for example, from Akzo with tradenames Noe-Fat, from Witco Corp. with tradenames Hystrene, or from Vevy with tradenames derma.
  • the composition of the present invention contains from about 1 wt% to about 99 wt%, preferably from about 10wt% to about 90 wt%, and more preferably from about 30 wt% to about 80 wt% by weight of the composition, of the oily component present, as related to the active compounds.
  • the oily component of the present invention may also include a material which may be classified in the group of surfactants or emulsifiers such as silicone copolymer (e.g., SilwetTM VS series and FZ series available from Unicar) and PEG copolymer described hereinafter in view of its structure or functionality.
  • surfactants or Emulsifiers such as silicone copolymer (e.g., SilwetTM VS series and FZ series available from Unicar) and PEG copolymer described hereinafter in view of its structure or functionality.
  • the non-aqueous composition of the present invention further include a surfactant or an emulsifier to emulsify the mixture of the oily compound and the active compound in the aqueous carrier.
  • a surfactant or an emulsifier to emulsify the mixture of the oily compound and the active compound in the aqueous carrier.
  • the surfactant or emulsifier is fully compatible with the active compound and the optional ingredients.
  • Some of surfactants in the present composition or system useful herein can also effective as an emulsifier to form emulsion.
  • a surfactant or emulsifier presents from about 0.05 wt% to about 50 wt%, more preferably from about 0.1 wt% to about 30 wt%, most preferably from about 0.2 wt% to about 20 wt%.
  • the surfactant or emulsifier used for the composition of the present invention can be selected depending on the type of product category and/or the form of products and also depending upon their compatibility with other ingredients.
  • the surfactant herein includes nonionic surfactants, cationic surfactants, anionic surfactants, zwitterionic surfactants, ampholytic surfactants, and mixtures thereof.
  • the surfactants preferred for applications are nonionic surfactants.
  • Water-soluble nonionic surfactants are used in the instant detergent compositions.
  • Such nonionic materials include compounds produced by the condensation of alkylene oxide groups (hydrophilic in nature) with an organic hydrophobic compound, which may be aliphatic or alkyl aromatic in nature.
  • the length of the polyoxyalkylene group which is condensed with any particular hydrophobic group can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elements.
  • Suitable nonionic surfactants include the polyethylene oxide condensates of alkyl phenols, e.g., the condensation products of alkyl phenols having an alkyl group containing from about 6 to 15 carbon atoms, in either a straight chain or branched chain configuration, with from about 3 to 80 moles of ethylene oxide per mole of alkyl phenol.
  • commercially available nonionic surfactants include IgepalTM CO-630, marketed by the GAF Corporation; and TritonTM X-45, X-114, X-100 and X-102, all marketed by the Rohm & Haas Company.
  • alkylphenol alkoxylates e.g., alkyl phenol ethoxylates
  • alkylphenol alkoxylates e.g., alkyl phenol ethoxylates
  • these are particularly used for detergent products. Included are the water-soluble and water-dispersible condensation products of aliphatic alcohols containing from 8 to 22 carbon atoms, in either straight chain or branched configuration, with from 1 to 25 moles, preferably from 3 to 12 moles, of ethylene oxide per mole of alcohol.
  • TergitolTM 15-S-9 the condensation product of C-11-C15 linear alcohol with 9 moles ethylene oxide
  • TergitolTM 24-L-6 NMW the condensation product of C ⁇
  • NeodolTM 45-9 the condensation product of C14-C15 linear alcohol with 9 moles of ethylene oxide
  • NeodolTM 23-3 the condensation product of C12- 13 linear alcohol with 3.0 moles of ethylene oxide
  • Shell Chemical Company and Genapol LA O3O or 050 (the condensation product of C12- 14 alcohol with
  • Semi-polar nonionic surfactants include water-soluble amine oxides containing one alkyl moiety of from abut 10 to 18 carbon atoms and two moieties selected from the group of alkyl and hydroxyalkyl moieties of from about 1 to about 3 carbon atoms; water-soluble phosphine oxides containing one alkyl moiety of about 10 to 18 carbon atoms and two moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to 3 carbon atoms; and water-soluble sulfoxides containing one alkyl moiety of from about 10 to 18 carbon atoms and a moiety selected from the group consisting of alkyl and hydroxyalkyl moieties of from about 1 to 3 carbon atoms.
  • Preferred nonionic surfactants are of the formula R1 (0C2H4)0H, wherein
  • R1 is a C- ⁇ o-16 a ' group or a C8-12 alkyl phenyl group, and n is from 3 to about 80.
  • Particularly preferred are condensation products of alcohols with from about 5 to about 20 moles of ethylene oxide per mole of alcohol, e.g., C-
  • the nonionic surfactant is an ethoxylated surfactant derived from the reaction of a monohydroxy alcohol or alkylphenol containing from about 8 to about 20 carbon atoms, excluding cyclic carbon atoms, with from about 6 to about 15 moles of ethylene oxide per mole of alcohol or alkyl phenol on an average basis.
  • Preferred ethoxylated nonionic surfactant is derived from a straight chain fatty alcohol containing from about 16 to about 20 carbon atoms (C-
  • the ethoxylated nonionic surfactant so derived has a narrow ethoxylate distribution relative to the average.
  • the ethoxylated nonionic surfactant can optionally contain propylene oxide in an amount up to about 15 wt% by weight of the surfactant when the liquid active solution of the present invention is formulated in skin care composition.
  • Preferred surfactants can be prepared by the processes described in U.S. Patent 4,223,163, Builloty, issued September 16, 1980.
  • Suitable block polyoxyethylene-polyoxypropylene polymeric compounds include those based on ethylene glycol, propylene glycol, glycerol, trimethylolpropane and ethylenediamine as the initiator reactive hydrogen compound. Polymeric compounds made from a sequential ethoxylation and propoxylation of initiator compounds with a single reactive hydrogen atom, such as C-12-18 aliphatic alcohols, do not provide satisfactory suds control in the detergent compositions of the invention. Certain of the block polymer surfactant compounds designated PLURONIC and TETRONIC by the BASF-Wyandotte Corp., Wyandotte, Mich., are suitable in the surfactant compositions of the invention.
  • a particularly preferred embodiment contains from about 40 wt% to about 70 wt% of a polyoxypropylene, polyoxyethylene block polymer blend comprising about 75 wt%, by weight of the blend, of a reverse block co-polymer of polyoxyethylene and polyoxypropylene containing 17 moles of ethylene oxide and 44 moles of propylene oxide; and about 25 wt%, by weight of the blend, of a block co-polymer of polyoxyethylene and polyoxypropylene, initiated with tri- methylol propane, containing 99 moles of propylene oxide and 24 moles of ethylene oxide per mole of trimethylol propane.
  • the compounds are suitable for use in the surfactant compositions of the invention and have relatively low cloud points.
  • Cloud points of 1 wt% solutions in water are typically below about 32 degC and preferably from about 15 degC to about 30 degC for optimum control of sudsing throughout a full range of water temperatures and water hardnesses.
  • Non-ionic surfactant suitable for the composition of the present invention also include silicone surfactant/emulsifier.
  • silicone surfactants examples include clyclomethicone, dimethicone, methicone, phenyl dimethicone, and dimethicone copoplyol.
  • silicone surfactant/oils are available, for example, from Unicar, with trade names of Silwet series, VS series and FZ series.
  • nonionic surfactants required in the compositions of the invention herein, the compositions may also contain surfactants selected from the group of cationic surfactants, anionic surfactants, ampholytic, zwitterinoic, and mixtures thereof.
  • Cationic surfactants can also be included in the present compositions.
  • Cationic surfactants comprise a wide variety of compounds characterized by one or more organic hydrophobic groups in the cation and generally by a quaternary nitrogen associated with an acid radical.
  • Pentavalent nitrogen ring compounds are also considered quaternary nitrogen compounds. Halides, methyl sulfate and hydroxide are suitable. A more complete disclosure of these and other cationic surfactants useful herein can be found in U.S. Patent 4,228,044, Cambre, issued Oct. 14, 1980; U.S. Patent 3,936,537, Baskerville, Jr. et al., issued February 3, 1976; U.S. Patent 4,222,905, Cockrell, issued September 16, 1980; and U.S. Patent 4,239,659, Murphy, issued December 16, 1980. Water-soluble salts of the higher fatty acids, i.e., soaps, are useful anionic surfactants for the compositions.
  • Such salts include alkali metal soaps such as the sodium, potassium, ammonium, and alkylolammonium salts of higher fatty acids containing from about 8 to about 24 carbon atoms, and preferably from about 12 to about 18 carbon atoms. Soaps can be made by direct saponification of fats and oils or by the neutralization of free fatty acids. Particularly useful are the sodium and potassium salts of the mixtures of fatty acids derived from coconut oil and tallow, i.e., sodium or potassium tallow and coconut soap.
  • Useful anionic surfactants also include the water-soluble salts, preferably the alkali metal, ammonium and alkylolammonium salts, of organic sulfuric reaction products having in their molecular structure an alkyl group containing from about 10 to about 20 carbon atoms and a sulfonic acid or sulfuric acid ester group. (Included in the term "alkyl” is the alkyl portion of acyl groups.) See U.S.
  • Patent 2,220,099 and 2,477,383 discloses linear straight chain alkylbenzene sulfonates in which the average number of carbon atoms in the alkyl group is from about 11 to 14, abbreviated as C-
  • anionic surfactants useful herein are the sodium alkyl glyceryl ether sulfonates and water-soluble salts of esters of alpha-sulfonated fatty acids. Examples of these anionic surfactants are set forth in U.S. Patent 5,565,422, Del
  • Ampholytic surfactants include derivatives of aliphatic or aliphatic derivatives of heterocyclic secondary and tertiary amines in which the aliphatic moiety can be straight chain or branched and wherein one of the aliphatic substituents contains from about 8 to 18 carbon atoms and at least one aliphatic substituent contains an anionic water-solubilizing group. See U.S. Patent
  • Zwitterionic surfactants include derivatives of aliphatic, quaternary, ammonium, phosphonium, and sulfonium compounds in which one of the aliphatic substituents contains from about 8 to 18 carbon atoms.
  • the non-aqueous composition of the present invention may further contain an optional component.
  • the optional component useful herein depends on the type and use of products such as skin care and home care.
  • a skin care actives include, but are not limited to:
  • Vitamin A compound e.g., retinoid which are commercially available from a number of sources, for example, Sigma Chemical Company (St. Louis,
  • Vitamin B3 compound such as nicotinic acid esters, including non- vasodilating esters of nicotinic acid, nicotinyl amino acids, nicotinyl alcohol esters of carboxylic acids, nicotinic acid N-oxide and niacinamide N-oxide;
  • Anti-oxidants and radical scavengers such as tocopherol (vitamin E), tocopherol sorbate, tocopherol acetate, other esters of tocopherol, butylated hydroxy benzoic acids and their salts, 6-hydroxy-2,5,7,8-tetramethylchroman-2- carboxylic acid (commercially available under the tradename Trolox®), gallic acid and its alkyl esters, especially propyl gallate, uric acid and its salts and alkyl esters, sorbic acid and its salts, amines (i.e., N,N-diethylhydroxylamine, amino- guanidine), sulfhydryl compounds (i.e., glutathione), dihydroxy fumaric acid and its salts, lycine pidolate, arginine pilolate, nordihydroguaiaretic acid, bioflavonoids, lysine, methionine, proline, superoxide dismutas
  • Anti-inflammatory agents such as alpha bisabolol, aloe vera, Manjistha (extracted from plants in the genus Rubia, particularly Rubia Cordifolia), and Guggal (extracted from plants in the genus Commiphora, particularly Commiphora Mukul), kola extract, chamomile, and sea whip extract, disclosed in Anti-inflammatory and Anti-Rheumatic Drugs, K. D. Rainsford, Vol. Mil, CRC Press, Boca Raton, (1985), and Anti-inflammatory Agents, Chemistry and Pharmacology, 1 , R. A.
  • Antimicrobial agents such as benzoyl peroxide, erythromycin, tetracycline, clindamycin, azelaic acid, sulfur resorcinol, phenoxyethanol, and IrgasanTM DP 300 (Ciba Geigy Corp., U.S.A.);
  • pH adjuster refers to any component which is employed to increase or decrease the overall pH of the composition/emulsion to an optimum pH, thereby preventing undesirable skin feeling such as skin irritation.
  • An optimum pH is subject to the selection of preventing skin irritation.
  • the optimum pH is around 5.0 to about 7.0.
  • Suitable pH adjusters herein include acetate, phosphate, citrate, triethanolamine and carbonate.
  • one of optional ingredients is bleaching agents such as hydrogen peroxide, PB1 , PB4 and percarbonate with a particle size of 400-800 microns.
  • bleaching agent components can include one or more oxygen bleaching agents and, depending upon the bleaching agent chosen, one or more bleach activators.
  • the bleaching agent can be any of the bleaching agents useful for cleaning compositions including oxygen bleaches as well as others known in the art.
  • the bleaching agent suitable for the present invention can be an activated or non-activated bleaching agent.
  • Patent 5,114,611 PCT application WO 95/07823, Hexter, issued Mrach 23, 1995; and WO 95/27772, WO 95/27773, WO 95/27774, and WO 95/27775, Pretty et al., issued October 19, 1995.
  • a builder system may further present.
  • Any conventional builder system is suitable for use, including aluminosilicate materials such as Zeolite A, Zeolite B, and Zeolite X, silicates, polycarboxylates, alkyl- or alkenyl- succinic acid and fatty acids, materials such as ethylenediamine tetraacetate, diethylene triamine pentamethyleneacetate, metal ion sequestrants such as aminopolyphosphonates, particularly ethylenediamine tetramethylene phosphonic acid and diethylene triamine pentamethylenephosphonic acid. See, for example, U.S.
  • Phosphate builders can also be used herein.
  • One another optional component cleaning detergent composition is one or more enzymes which provide cleaning performance, fabric care and/or sanitisation benefits.
  • Said enzymes include enzymes selected from cellulases, hemicellulases, peroxidases, proteases, gluco-amylases, amylases, xylanases, lipases, phospholipases, esterases, cutinases, pectinases, keratanases, reductases, oxidases, phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, ⁇ -glucanases, arabinosidases, hyaluronidase, chondroitinase, laccase or mixtures thereof.
  • a range of enzyme materials and means for their incorporation into synthetic detergent compositions is disclosed, for example, in PCT publication WO 93/07263 and WO 93/07260, Genencor International; WO 89/08694, Novo; U.S. Patent 3,553,139, McCarty et al.; U.S. Patent 4,101 ,457, Place et al.; and U.S. Patent 4,507,219, Hughes; U.S. Patent 4,261 ,868, Hora et al.; U.S. Patent 3,600,319, Gedge et al.; European publication A 199,405 and European publication A 200,586, Venegas; and Novo, PCT publication WO 94/01532.
  • malodor controlling agents include odor absorbing ingredients, such as various type of cyclodextrins, which trap the malodor molecules into the donuts structures of the cyclodextrins. Examples of cyclodextrins are such described in the U.S. Patent 5,714,137 and 5,714,445, Trinh et al., issued February 3, 1998.
  • Other malodor controlling agents are odor scavengers, odor aggregation agents, odor masking agents such as polyphenols, and natural extracts from tea and mushroom and their derivatives.
  • Suitable smectite clays for use herein are described in U.S. Patent 4,762,645, Tucker et al, issued August 9, 1988.
  • Suitable additional detergency builders for use herein are enumerated in U.S. Patent 3,936,537, Baskerville, Jr. et al., issued February 3, 1976, and in U.S. Patent 4,663,071 , Bush et al, issued May 5, 1987.
  • ingredients suitable for inclusion in a home care composition can be added to the present compositions. These include bleach activators, suds boosters or suds suppressors, anti-tarnish and anticorrosion agents, soil suspending agents, soil release agents, germicides, pH adjusting agents, non- builder alkalinity sources, and perfumes. Such ingredients are described in the Baskerville, Jr's U.S. Patent referred to the above.
  • Some skin care components which may be included herein, but are not limited to, can be preservatives and preservative enhancers such as water- soluble or solubilizable preservatives including Germall 115, methyl, ethyl, propyl and butyl esters of hydroxybenzoic acid, benzyl alcohol, EDTA, Bronopol (2- bromo-2-nitropropane-1 ,3-diol) and phenoxypropanol; skin lightening/evenness agents including kojic acid, arbutin, ascorbic acid and derivatives thereof and described in PCT Application number U.S.
  • preservative enhancers such as water- soluble or solubilizable preservatives including Germall 115, methyl, ethyl, propyl and butyl esters of hydroxybenzoic acid, benzyl alcohol, EDTA, Bronopol (2- bromo-2-nitropropane-1 ,3-diol) and phen
  • Patent 4,076,663 proteins and polypeptides and derivatives thereof; organic hydroxy acids; drug astringents; external analgesics; film formers; absorbents including oil absorbents such as clays and polymeric absorbents; abrasives; anticaking agents; antifoaming agents; binders; biological additives; bulking agents; coloring agents; perfumes, essential oils, and solubilizers thereof; natural extracts; compounds which stimulate collagen production.
  • a non-aqueous composition of the present invention is prepared by a method comprising the steps of mixing an active compound to a oily component for obtaining a liquid active solvent.
  • the active component has the following formula (I):
  • R ⁇ and R2 are independently selected from saturated, straight or branched alkyl group of from 1 to about 10 carbons; preferably independently from 1 to about 3 carbons.
  • the oily component has less than 50 °C of melting point.
  • compositions shown below can be prepared by any conventional method known in the art. Suitable methods and formulations are as follows: wt %
  • the composition comprising a solubilized composition of 8-ACA into oily compounds provides desirable repellent efficacy; better and long-lasting efficacy than water-base composition.
  • the present composition with a surfactant or an emulsifier, can easily apply to any application which is an aqueous base without lack of repellency and long-lasting efficacy.

Abstract

A non-aqueous composition comprising a safe and effective amount of an active compound and an oily component for obtaining a liquid active solution. The active component has formula (I) wherein R?1 and R2¿ are independently selected form saturated, straight or branched alkyl group of from 1 to about 10 carbons. The oily component for obtaining a liquid active solution, has less than 50°C of melting point.

Description

A COMPOSITION COMPRISING SOLUBILIZED REPELLENT ACTIVE COMPONENT
FIELD
The present invention relates to a composition containing solubilized insect and dust mite repellent. In particular, it relates to a solubility system of a natural insect and dust mite repellent and compositions thereof.
BACKGROUND
Consumers frequently use insect repellent products to protect themselves from insect bites including mosquitoes, alone or along with cosmetic products, during an outdoor activity such as hiking, camping, and hunting. These products, which come in the form of liquids, creams, pastes and gels, are rubbed, sprayed, or otherwise applied to the skin. Repellent products are also used in the home, for example to control dust mites, ants, wasps, and so on.
Many substances have been suggested through the years to be used in such repellence products as insect repellence actives including dimethyl phthalate and N,N-diethyl-m-toluamide. N,N-diethyl-m-toluamide is the most widely used insect repellent active sometimes referred to as "DEET." See U.S. Patent 2,932,665, Wagner et al, issued on April 12, 1960, U.S. Patent 4,756,905, Melnik, issued July 12, 1988, U.S. Patent 4,416,881 , McGovern et al, and U.S. Patent 4,419,360, Smolanoff, disclosing DEET to protect an outdoorsman from insects and adequately cover the skin of the user. Another repellent active that has previously been proposed is d-8-ACA, disclosed in Chinese patent application No. 94100746, Hanzhi et al., filed on July 2. It is both natural and safe to the human and provides good repellent efficacy for insect and dust mites instead of killing them. This active is typically provided in a crystallized form. The liquid form of d-8-ACA is, however believed to be the much more efficacious for use in many personal care and home care products to give effective repellent benefits. d-8-ACA can be delivered to skin in a water and alcohol solution. Unfortunately, d-8-ACA is a water-insoluble material. Therefore, when such aqueous solution containing d-8-ACA is applied to a surface, the d-8-ACA crystallizes when the solvent carrier evaporates. This creates a problem, because crystalline d-8-ACA is substantially less effective as a repellent than d- 8-ACA in the liquid form.
Based on the foregoing, there is a need for a solubilized composition for d- 8-ACA wherein a stable, non-volatile liquid form of the compound is obtained and the composition suitable for incorporation into a variety of conventional product forms e.g., liquids, creams, pastes and gels, and spray.
SUMMARY This need is met by the present invention wherein compositions having superior insect and dust mites repellent properties is proposed. The composition contains:
(1 ) an active compound having the following formula (I):
Figure imgf000003_0001
wherein R1 and R2 are independently selected from saturated, straight or branched alkyl group of from 1 to about 10 carbons; and
(2) a oily component for obtaining a liquid active solution, having less than 50°C of melting point.
These and other features, aspects, and advantages of the present invention will become better understood from a reading of the following description, and appended claims.
DETAILED DESCRIPTION
While the specification concludes with claims particularly pointing out and distinctly claiming the invention, it is believed that the present invention will be better understood from the following description.
All percentages and ratios used hereinafter are by weight of total composition, unless otherwise indicated. All measurements referred to herein are made at 25°C unless otherwise specified.
All percentages, ratios, and levels of ingredients referred to herein are based on the actual amount of the ingredient, and do not include solvents, fillers, or other materials with which the ingredient may be combined as a commercially available product, unless otherwise indicated.
All publications, patent applications, and issued patents mentioned herein are hereby incorporated in their entirety by reference. Citation of any reference is not an admission regarding any determination as to its availability as prior art to the claimed invention.
Herein, "comprising" means that other steps and other ingredients which do not affect the end result can be added. This term encompasses the terms "consisting of and "consisting essentially of.
Herein, "safe and effective amount," means an amount of a compound or composition sufficient to significantly induce a positive benefit, preferably a positive skin appearance or feel benefit, including independently the benefits disclosed herein, but low enough to avoid serious side effects, e.g., to provide a reasonable benefit to risk ratio, within the scope of sound judgment of the skilled artisan. All ingredients such as actives and other ingredients useful herein may be categorized or described by their cosmetic and/or therapeutic benefit or their postulated mode of action. However, it is to be understood that the active and other ingredients useful herein can, in some instances, provide more than one cosmetic and/or therapeutic benefit or operate via more than one mode of action. Therefore, classifications herein are made for the sake of convenience and are not intended to limit an ingredient to the particularly stated application or applications listed.
The topical composition of the present invention contains an active compound having the following formula (I) and a oily component for obtaining a liquid active solvent.
Figure imgf000004_0001
wherein R1 and R2 are independently selected from saturated, straight or branched alkyl group of from 1 to about 10 carbons. The oily component for obtaining a liquid active solution, having less than
50°C of melting point. The composition provides superior insect repellent efficacy, especially prolonged repellent efficacy in liquid form. The composition of the present invention also provides desirable mites repellent in stead of killing them.
A. Active compound
The composition of the present invention contains a safe and effective amount of an active compound having the formula (I):
Figure imgf000005_0001
wherein R1 and R2 are independently selected from saturated, straight or branched alkyl group of from 1 to about 10 carbons. * indicates active place. In the above formula (I), preferably R1 and R^ are independently selected from saturated, straight alkyl groups of from 1 to about 3 carbons. More preferably, R"1 and R2 are independently methyl, ethyl, or propyl.
The active component of the present invention has optical isomers; d-, I-, and a mixtures of d- and l-forms. In general, the active component provides as a mixture of higher levels of d-form with lower levels l-form. It is believed that d- form works effectively than l-form. In one embodiment, the active compound can be derived by a method described in Chinese patent application No. 94100746, Hanzhi et al., filed on July 26, 1995. Such compounds include d-8- acetoxycarvotanacetone (d-8-ACA).
The active compound of the present invention provides strong activity to repel insects such as mosquitoes and gnats and arachnid. These compounds are particularly effective in repelling insects instead of killing them when formulated in active repellent solution with a oily component.
This class of active compounds can also be effective to repel dust mites, which are members of the arachnid family and often are unaffected by traditional insect repellent compositions. It is well known that dust mites are a common source of allergens. As such, it is desirable to repel dust mites from areas that are used by people who are sensitive to allergens. It is also believed that the dead mites of the house dust variety float in the air, causing bronchial asthma, allergic rhinitis, allergic dermatitis, and various other disorders. These areas include households, automobiles, offices and other areas.
The active compounds can provide desirable mite repellency. Such repellancy and attractant of mites are important for the people having allergic dermatitis. The active components of the present invention are effective against most of the house dust mites such as Dermatophagoides farinae and
Tyrophagus pytrescentiae.
Preferably the concentration of the formula (I) is from about 0.1 wt% to about 85 wt% of the active compound, more preferably from about 0.5 wt% to about 50 wt%.
The compositions of the present invention may further comprise additional active components. It is especially preferred that the additional actives fall within the class of oily compounds. But it is understood that the additional active compounds can be any appropriate compound that is compatible with the other compounds in the present compositions. Especially preferred additional active compounds are those of the general structure:
Figure imgf000006_0001
Wherein R3 is hydrogen or -(CH2)nCH3 and n is integer form about 0 to about
10. Such compounds include 3-n-butyl-n-acetyl aminopropionic acid and its ester. These compounds are sold by Merck Chemical Company under the trade name Merck 3535.
Other additional active compounds for use in the present invention include insect and moth controllingagents such as anti-aggregation pheromones, and other natural and/or synthetic ingredients. Preferred additional active compounds useful in the composition of the present invention are perfume ingredients, such as citronellol, citronellal, citral, linalool, cedar extract, geranium oil, sandalwood oil, 2-(diethylphenoxy)ethanol, 1-dodecene, etc. Other examples of additional active compounds useful in the composition of the present invention are disclosed in U.S. Patent No. 4,449,987, 4,693,890, 4,696,676, 4,933,371 , 5,030,660, 5,196,200, and in "Semio Activity of Flavor and Fragrance Molecules on Various Insect Species", B.D. Mookherjee et al., published in Bioactive Volatile Compounds from Plants. ASC Symposium Series 525, R. Teranishi, R.G. Buttery, and H. Sugisawa, 1993, pp. 35-48, all of said patents and publications being incorporated herein by reference.
It is recognized that some of these active compounds can have properties as oily components, surfactants and emulsifiers and can alternatively be classified as such. However, a given classification is not intended to be a limitation on that particular compound, but is done so for convenience of classification and nomenclature.
B. Oily component The composition and the system of the present invention contains an oily component. The active compounds identified above are most effective when in a liquid state. But when these compounds are dissolved in solvent containing alcohol with water and applied to a surface, the solvent evaporates and the active compound tends to crystallize, rendering it relatively ineffective as an insect or dust mite repellent. Thus, the active compounds are preferably dissolved in an oily compound before they are incorporated into any product applications.
The oily component useful herein can be derived from animals, plants, or petroleum and may be natural or synthetic (i.e., man-made). The oily component are substantially water-insoluble, more preferably essentially water-insoluble. Preferably, the oily components herein has about 50°C or less of a melting point under one atmosphere of pressure, and does not evaporate rapidly.
In a preferred embodiment, the oily component useful herein can has a viscosity of from about 0 to about 10,000 cps; preferably from about 20 to about 5,000 cps.
A wide variety of suitable oily components are known and may be used herein and numerous examples can be found in McCUTOCHEON'S Functional Materials, North American Edition, International Edition Cosmetics, 1999 Anuals. Nonlimiting examples of suitable oily component include those selected from the group consisting of mineral oil, petrolatum, straight and branched chain hydrocarbons having from about 7 to about 40 of carbon atoms, vegetable oils and hydrogenated vegetable oils, animal fats and oils, polyhydric alcohols, silicone oils, alcohol esters of carboxylic acids and of dicarboxylic acids, alkylene glycol esters, C-|_3o mono- and poly- esters of sugars and related materials, and fatty alcohols, fatty acids, fatty acid derivatives or fatty alcohol derivatives. (i) Mineral oil, which is also known as petrolatum liquid, is a mixture of liquid hydrocarbons obtained from petroleum. See The Merck Index, Tenth
Edition, Entry 7048, p. 1033 (1983) and International Cosmetic Ingredient
Dictionary, Fifth Edition, vol. 1 , p.415-417 (1993), which are incorporated by reference herein in their entirety.
(ii) Petrolatum, which is also known as petroleum jelly, is a colloidal system of nonstraight-chain solid hydrocarbons and high-boiling liquid hydrocarbons, in which most of the liquid hydrocarbons are held inside the micelles. See The Merck Index, Tenth Edition, Entry 7047, p. 1033 (1983); Schindler, Drug. Cosmet. Ind.. 89, 36-37, 76, 78-80, 82 (1961 ); and International Cosmetic Ingredient Dictionary, Fifth Edition, vol. 1 , p. 537 (1993), which are incorporated by reference herein in their entirety.
(iii) Straight and branched chain hydrocarbons having from about 7 to about 40 carbon atoms. Nonlimiting examples of these hydrocarbon materials include dodecane, isododecane, squalane, cholesterol, hydrogenated polyisobutylene, docosane (i.e. a C22 hydrocarbon), hexadecane, isohexadecane (a commercially available hydrocarbon sold as Permethyl® 101 A by Presperse, South Plainfield, NJ). Also useful are the C7-C40 isoparaffins, which are C7-C40 branched hydrocarbons. (iv) Vegetable oils and hydrogenated vegetable oils. Examples of vegetable oils and hydrogenated vegetable oils include safflower oil, castor oil, coconut oil, cottonseed oil, menhaden oil, palm kernel oil, palm oil, peanut oil, soybean oil, rapeseed oil, linseed oil, rice bran oil, pine oil, sesame oil, sunflower seed oil, hydrogenated safflower oil, hydrogenated castor oil, hydrogenated coconut oil, hydrogenated cottonseed oil, hydrogenated menhaden oil, hydrogenated palm kernel oil, hydrogenated palm oil, hydrogenated peanut oil, hydrogenated soybean oil, hydrogenated rapeseed oil, hydrogenated linseed oil, hydrogenated rice bran oil, hydrogenated sesame oil, hydrogenated sunflower seed oil, and mixtures thereof. (v) Animal fats and oils, e.g., lanolin and derivatives thereof, cod liver oil.
(vi) Polvhvdric alcohols, including, but are not limited to, polyalkylene glycols, more preferably alkylene polyols and their derivatives including glycerin, propylene glycol, dipropylene glycol, tripropylene glycol, polyethylene glycol and derivatives thereof, sorbitol, hydroxypropyl sorbitol, erythritol, threitol, pentaerythritol, xylitol, glucitol, mannitol, hexylene glycol, 1 ,3-butylene glycol, 1 ,2,6-hexanetriol, glycerol, ethoxylated glycerol, propoxylated glycerol, sodium 2- pyrrolidone-5-carboxylate, soluble collagen, gelatin, and mixtures thereof.
(vii) Silicone oils, including polyalkyl siloxanes such as polydimethyl siloxane, polydiethyl siloxane; polyaryl siloxanes; and polyalkylaryl siloxanes such as polymethylphenyl siloxanes; cyclic polyalkylsiloxanes; polyether siloxane copolymers; and polypropylene oxide modified polydimethylsiloxane. Nonlimiting examples of suitable silicones are disclosed in U.S. Patent No. 5,069,897, to Orr, issued December 3, 1991. Commercially available polyalkylsiloxanes include the polydimethylsiloxanes, known as dimethicones, examples of which include the Vicasil® series sold by General Electric Company and the Dow Corning® 200 series sold by Dow Corning Corporation. Suitable dimethicones include those alkyl-substituted dimethicones include cetyl dimethicone and lauryl dimethicone.
(viϋ) CI _3Q alcohol esters of Ci_3Q carboxylic acids and of C2-30 dicarboxylic acids, including straight and branched chain materials as well as aromatic derivatives (as used herein in reference to the hydrophobic component, mono- and poly- carboxylic acids include straight chain, branched chain and aryl carboxylic acids). Nonlimiting examples include diisopropyl sebacate, diisopropyl adipate, isopropyl myristate, isopropyl palmitate, methyl palmitate, myristyl propionate, 2-ethylhexyl palmitate, isodecyl neopentanoate, di-2-ethylhexyl maleate, cetyl palmitate, myristyl myristate, stearyl stearate, isopropyl stearate, methyl stearate, cetyl stearate, behenyl behenate, dioctyl maleate, dioctyl sebacate, diisopropyl adipate, cetyl octanoate, diisopropyl dilinoleate.
(vii) Alkylene glycol esters of C-| _3Q carboxylic acids, e.g., ethylene glycol mono- and di- esters, and propylene glycol mono- and di- esters of CI _3Q carboxylic acids e.g., ethylene glycol distearate.
0X) C-j-30 mono- and poly- esters of sugars and related materials. These esters are derived from a sugar or polyol moiety and one or more carboxylic acid moieties. Depending on the constituent acid and sugar, these esters can be in either liquid or solid form at room temperature. Examples of liquid esters include: glucose tetraoleate, the glucose tetraesters of soybean oil fatty acids (unsaturated), the mannose tetraesters of mixed soybean oil fatty acids, the galactose tetraesters of oleic acid, the arabinose tetraesters of linoleic acid, xylose tetralinoleate, galactose pentaoleate, sorbitol tetraoleate, the sorbitol hexaesters of unsaturated soybean oil fatty acids, xylitol pentaoleate, sucrose tetraoleate, sucrose pentaoletate, sucrose hexaoleate, sucrose hepatoleate, sucrose octaoleate, and mixtures thereof. Examples of solid esters include: sorbitol hexaester in which the carboxylic acid ester moieties are palmitoleate and arachidate in a 1 :2 molar ratio; the octaester of raffinose in which the carboxylic acid ester moieties are linoleate and behenate in a 1 :3 molar ratio; the heptaester of maltose wherein the esterifying carboxylic acid moieties are sunflower seed oil fatty acids and lignocerate in a 3:4 molar ratio; the octaester of sucrose wherein the esterifying carboxylic acid moieties are oleate and behenate in a 2:6 molar ratio; and the octaester of sucrose wherein the esterifying carboxylic acid moieties are laurate, linoleate and behenate in a 1 :3:4 molar ratio. A preferred solid material is sucrose polyester in which the degree of esterification is 7-8, and in which the fatty acid moieties are C18 mono- and/or di- unsaturated and behenic, in a molar ratio of unsaturates:behenic of 1 :7 to 3:5. A particularly preferred solid sugar polyester is the octaester of sucrose in which there are about 7 behenic fatty acid moieties and about 1 oleic acid moiety in the molecule. Other materials include cottonseed oil or soybean oil fatty acid esters of sucrose. The ester materials are further described in, U.S. Patent 2,831 ,854 and U.S. Patent 4,005,196, Jandacek, issued January 25, 1977; U.S. Patent 4,005,195, Jandacek, issued January 25, 1977; U.S. Patent 5,306,516, Letton et al., issued April 26, 1994; U.S. Patent 5,306,515, and U.S. Patent 5,305,514, Letton et al., issued April 26, 1994; U.S. Patent No. 4,797,300, Jandacek et al., issued January 10, 1989; U.S. Patent 3,963,699, Rizzi et al, issued June 15, 1976; U.S. Patent 4,518,772, Volpenhein, issued May 21 , 1985; and U.S. Patent 4,517,360, Volpenhein, issued May 21 , 1985; all of which are incorporated by reference herein in their entirety. (x) Fatty alcohols, fatty acids, fatty acid derivatives or fatty alcohol derivatives. The fatty alcohols having straight or branched such as cetyl alcohol, stearyl alcohol, and behenyl alcohol; fatty acids having straight or branched, at least about 10 carbon atoms stearic acid, behenic acid, palmitic acid, archidonic acid and sebacic Acid. These are available, for example, from Akzo with tradenames Noe-Fat, from Witco Corp. with tradenames Hystrene, or from Vevy with tradenames derma.
The composition of the present invention contains from about 1 wt% to about 99 wt%, preferably from about 10wt% to about 90 wt%, and more preferably from about 30 wt% to about 80 wt% by weight of the composition, of the oily component present, as related to the active compounds. The oily component of the present invention may also include a material which may be classified in the group of surfactants or emulsifiers such as silicone copolymer (e.g., Silwet™ VS series and FZ series available from Unicar) and PEG copolymer described hereinafter in view of its structure or functionality. C. Surfactant or Emulsifier
The non-aqueous composition of the present invention further include a surfactant or an emulsifier to emulsify the mixture of the oily compound and the active compound in the aqueous carrier. Preferably, the surfactant or emulsifier is fully compatible with the active compound and the optional ingredients. Some of surfactants in the present composition or system useful herein can also effective as an emulsifier to form emulsion.
A surfactant or emulsifier presents from about 0.05 wt% to about 50 wt%, more preferably from about 0.1 wt% to about 30 wt%, most preferably from about 0.2 wt% to about 20 wt%. The surfactant or emulsifier used for the composition of the present invention can be selected depending on the type of product category and/or the form of products and also depending upon their compatibility with other ingredients. The surfactant herein includes nonionic surfactants, cationic surfactants, anionic surfactants, zwitterionic surfactants, ampholytic surfactants, and mixtures thereof.
In one embodiment, the surfactants preferred for applications are nonionic surfactants. Water-soluble nonionic surfactants are used in the instant detergent compositions. Such nonionic materials include compounds produced by the condensation of alkylene oxide groups (hydrophilic in nature) with an organic hydrophobic compound, which may be aliphatic or alkyl aromatic in nature. The length of the polyoxyalkylene group which is condensed with any particular hydrophobic group can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elements. Suitable nonionic surfactants include the polyethylene oxide condensates of alkyl phenols, e.g., the condensation products of alkyl phenols having an alkyl group containing from about 6 to 15 carbon atoms, in either a straight chain or branched chain configuration, with from about 3 to 80 moles of ethylene oxide per mole of alkyl phenol. In one embodiemnt, commercially available nonionic surfactants include Igepal™ CO-630, marketed by the GAF Corporation; and Triton™ X-45, X-114, X-100 and X-102, all marketed by the Rohm & Haas Company. These surfactants are commonly referred to as alkylphenol alkoxylates (e.g., alkyl phenol ethoxylates). These are particularly used for detergent products. Included are the water-soluble and water-dispersible condensation products of aliphatic alcohols containing from 8 to 22 carbon atoms, in either straight chain or branched configuration, with from 1 to 25 moles, preferably from 3 to 12 moles, of ethylene oxide per mole of alcohol. Examples of commercially available include Tergitol™ 15-S-9 (the condensation product of C-11-C15 linear alcohol with 9 moles ethylene oxide), Tergitol™ 24-L-6 NMW (the condensation product of C<|2-Ci4 primary alcohol with 6 moles ethylene oxide with a narrow molecular weight distribution), both marketed by Union Carbide Corporation; Neodol™ 45-9 (the condensation product of C14-C15 linear alcohol with 9 moles of ethylene oxide), Neodol™ 23-3 (the condensation product of C12- 13 linear alcohol with 3.0 moles of ethylene oxide), marketed by Shell Chemical Company, and Genapol LA O3O or 050 (the condensation product of C12- 14 alcohol with
3 or 5 moles of ethylene oxide) marketed by Hoechst. These are particularly used for detergent products.
Semi-polar nonionic surfactants include water-soluble amine oxides containing one alkyl moiety of from abut 10 to 18 carbon atoms and two moieties selected from the group of alkyl and hydroxyalkyl moieties of from about 1 to about 3 carbon atoms; water-soluble phosphine oxides containing one alkyl moiety of about 10 to 18 carbon atoms and two moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to 3 carbon atoms; and water-soluble sulfoxides containing one alkyl moiety of from about 10 to 18 carbon atoms and a moiety selected from the group consisting of alkyl and hydroxyalkyl moieties of from about 1 to 3 carbon atoms.
Preferred nonionic surfactants are of the formula R1 (0C2H4)0H, wherein
R1 is a C-ιo-16 a' group or a C8-12 alkyl phenyl group, and n is from 3 to about 80. Particularly preferred are condensation products of alcohols with from about 5 to about 20 moles of ethylene oxide per mole of alcohol, e.g., C-|2-13 alcohol condensed with about 6.5 moles of ethylene oxide per mole of alcohol.
In a preferred embodiment, the nonionic surfactant is an ethoxylated surfactant derived from the reaction of a monohydroxy alcohol or alkylphenol containing from about 8 to about 20 carbon atoms, excluding cyclic carbon atoms, with from about 6 to about 15 moles of ethylene oxide per mole of alcohol or alkyl phenol on an average basis. Preferred ethoxylated nonionic surfactant is derived from a straight chain fatty alcohol containing from about 16 to about 20 carbon atoms (C-|β-20 alcohol), preferably a Cιs alcohol, condensed with an average of from about 6 to about 15 moles, preferably from about 7 to about 12 moles, and most preferably from about 7 to about 9 moles of ethylene oxide per mole of alcohol. Preferably the ethoxylated nonionic surfactant so derived has a narrow ethoxylate distribution relative to the average.
The ethoxylated nonionic surfactant can optionally contain propylene oxide in an amount up to about 15 wt% by weight of the surfactant when the liquid active solution of the present invention is formulated in skin care composition. Preferred surfactants can be prepared by the processes described in U.S. Patent 4,223,163, Builloty, issued September 16, 1980.
Suitable block polyoxyethylene-polyoxypropylene polymeric compounds include those based on ethylene glycol, propylene glycol, glycerol, trimethylolpropane and ethylenediamine as the initiator reactive hydrogen compound. Polymeric compounds made from a sequential ethoxylation and propoxylation of initiator compounds with a single reactive hydrogen atom, such as C-12-18 aliphatic alcohols, do not provide satisfactory suds control in the detergent compositions of the invention. Certain of the block polymer surfactant compounds designated PLURONIC and TETRONIC by the BASF-Wyandotte Corp., Wyandotte, Mich., are suitable in the surfactant compositions of the invention.
A particularly preferred embodiment contains from about 40 wt% to about 70 wt% of a polyoxypropylene, polyoxyethylene block polymer blend comprising about 75 wt%, by weight of the blend, of a reverse block co-polymer of polyoxyethylene and polyoxypropylene containing 17 moles of ethylene oxide and 44 moles of propylene oxide; and about 25 wt%, by weight of the blend, of a block co-polymer of polyoxyethylene and polyoxypropylene, initiated with tri- methylol propane, containing 99 moles of propylene oxide and 24 moles of ethylene oxide per mole of trimethylol propane.
Because of the relatively high polyoxypropylene content, e.g., up to about 90 wt% of the block polyoxyethylene-polyoxypropylene polymeric compounds of the invention and particularly when the polyoxypropylene chains are in the terminal position, the compounds are suitable for use in the surfactant compositions of the invention and have relatively low cloud points. Cloud points of 1 wt% solutions in water are typically below about 32 degC and preferably from about 15 degC to about 30 degC for optimum control of sudsing throughout a full range of water temperatures and water hardnesses. Non-ionic surfactant suitable for the composition of the present invention also include silicone surfactant/emulsifier. Examples of such silicone surfactants are clyclomethicone, dimethicone, methicone, phenyl dimethicone, and dimethicone copoplyol. Such silicone surfactant/oils are available, for example, from Unicar, with trade names of Silwet series, VS series and FZ series. In addition, the nonionic surfactants required in the compositions of the invention herein, the compositions may also contain surfactants selected from the group of cationic surfactants, anionic surfactants, ampholytic, zwitterinoic, and mixtures thereof.
Cationic surfactants can also be included in the present compositions. Cationic surfactants comprise a wide variety of compounds characterized by one or more organic hydrophobic groups in the cation and generally by a quaternary nitrogen associated with an acid radical.
Pentavalent nitrogen ring compounds are also considered quaternary nitrogen compounds. Halides, methyl sulfate and hydroxide are suitable. A more complete disclosure of these and other cationic surfactants useful herein can be found in U.S. Patent 4,228,044, Cambre, issued Oct. 14, 1980; U.S. Patent 3,936,537, Baskerville, Jr. et al., issued February 3, 1976; U.S. Patent 4,222,905, Cockrell, issued September 16, 1980; and U.S. Patent 4,239,659, Murphy, issued December 16, 1980. Water-soluble salts of the higher fatty acids, i.e., soaps, are useful anionic surfactants for the compositions. Such salts include alkali metal soaps such as the sodium, potassium, ammonium, and alkylolammonium salts of higher fatty acids containing from about 8 to about 24 carbon atoms, and preferably from about 12 to about 18 carbon atoms. Soaps can be made by direct saponification of fats and oils or by the neutralization of free fatty acids. Particularly useful are the sodium and potassium salts of the mixtures of fatty acids derived from coconut oil and tallow, i.e., sodium or potassium tallow and coconut soap.
Useful anionic surfactants also include the water-soluble salts, preferably the alkali metal, ammonium and alkylolammonium salts, of organic sulfuric reaction products having in their molecular structure an alkyl group containing from about 10 to about 20 carbon atoms and a sulfonic acid or sulfuric acid ester group. (Included in the term "alkyl" is the alkyl portion of acyl groups.) See U.S.
Patent 2,220,099 and 2,477,383, discloses linear straight chain alkylbenzene sulfonates in which the average number of carbon atoms in the alkyl group is from about 11 to 14, abbreviated as C-| ι_-|4 LAS. Preferred are mixtures of C-| •]_
16 (preferably C-j η-13) linear alkylbenzene sulfonates and C12-I8 (preferably 14-I6) alkyl sulfates. Sodium salts of the above are preferred.
Other anionic surfactants useful herein are the sodium alkyl glyceryl ether sulfonates and water-soluble salts of esters of alpha-sulfonated fatty acids. Examples of these anionic surfactants are set forth in U.S. Patent 5,565,422, Del
Greco, issued October 15, 1996.
Ampholytic surfactants include derivatives of aliphatic or aliphatic derivatives of heterocyclic secondary and tertiary amines in which the aliphatic moiety can be straight chain or branched and wherein one of the aliphatic substituents contains from about 8 to 18 carbon atoms and at least one aliphatic substituent contains an anionic water-solubilizing group. See U.S. Patent
3,929,678, Laughlin et al., issued December 30, 1975 at column 19, lines 18-35, for examples of ampholytic surfactants.
Zwitterionic surfactants include derivatives of aliphatic, quaternary, ammonium, phosphonium, and sulfonium compounds in which one of the aliphatic substituents contains from about 8 to 18 carbon atoms.
D. Optional component
The non-aqueous composition of the present invention may further contain an optional component. The optional component useful herein depends on the type and use of products such as skin care and home care.
One of the optional component useful herein, particularly when the composition or the system of the present invention is applied to a skin care composition, is a skin care actives. Examples of such actives include, but are not limited to:
(1 ) Skin care actives
(i) Vitamin A compound (e.g., retinoid which are commercially available from a number of sources, for example, Sigma Chemical Company (St. Louis,
MO), and Boerhinger Mannheim (Indianapolis, IN) and described in U.S. Patent 4,677,120, Parish et al., issued June 30, 1987; U.S. Patent 4,885,311 , Parish et al., issued December 5, 1989; U.S. Patent 5,049,584, Purcell et al., issued
September 17, 1991 ; U.S. Patent 5,124,356, Purcell et al., issued June 23, 1992; and Reissue Patent 34,075, Purcell et al., issued September 22, 1992;
(ii) Vitamin B3 compound such as nicotinic acid esters, including non- vasodilating esters of nicotinic acid, nicotinyl amino acids, nicotinyl alcohol esters of carboxylic acids, nicotinic acid N-oxide and niacinamide N-oxide;
(iii) Anti-oxidants and radical scavengers such as tocopherol (vitamin E), tocopherol sorbate, tocopherol acetate, other esters of tocopherol, butylated hydroxy benzoic acids and their salts, 6-hydroxy-2,5,7,8-tetramethylchroman-2- carboxylic acid (commercially available under the tradename Trolox®), gallic acid and its alkyl esters, especially propyl gallate, uric acid and its salts and alkyl esters, sorbic acid and its salts, amines (i.e., N,N-diethylhydroxylamine, amino- guanidine), sulfhydryl compounds (i.e., glutathione), dihydroxy fumaric acid and its salts, lycine pidolate, arginine pilolate, nordihydroguaiaretic acid, bioflavonoids, lysine, methionine, proline, superoxide dismutase, silymarin, tea extracts, grape skin/seed extracts, melanin, and rosemary extracts, described in U.S. Patent 4,847,071 , Bissett et al, issued July 1 1 , 1989;
(iv) Anti-inflammatory agents such as alpha bisabolol, aloe vera, Manjistha (extracted from plants in the genus Rubia, particularly Rubia Cordifolia), and Guggal (extracted from plants in the genus Commiphora, particularly Commiphora Mukul), kola extract, chamomile, and sea whip extract, disclosed in Anti-inflammatory and Anti-Rheumatic Drugs, K. D. Rainsford, Vol. Mil, CRC Press, Boca Raton, (1985), and Anti-inflammatory Agents, Chemistry and Pharmacology, 1 , R. A. Scherrer, et al., Academic Press, New York (1974); (v) Antimicrobial agents such as benzoyl peroxide, erythromycin, tetracycline, clindamycin, azelaic acid, sulfur resorcinol, phenoxyethanol, and Irgasan™ DP 300 (Ciba Geigy Corp., U.S.A.);
(vi) Sunscreens and sunblocks such as PARSOL MCX, Eusolex™ 6300, Parsol 1789, disclosed in U.S. Patent 5,087,445, Haffey et al, issued February 1 1 , 1992; U.S. Patent 5,073,372, Turner et al, issued December 17, 1991 ; U.S. Patent 5,073,371 , Turner et al., issued December 17, 1991 ; and Segarin, et al, at Chapter VIII, pages 189 et seq., of Cosmetics Science and Technology (1972); and (vii) Chelators such as furildioxime and derivatives thereof, disclosed in U.S. Patent 5,487,884, Bissett et al., issued January 30, 1996; PCT application 91/16035 and 91/16034, Bush et al, published October 31 , 1995.
(2) pH adjuster The optional component can be a pH adjuster. Herein, "pH adjuster" refers to any component which is employed to increase or decrease the overall pH of the composition/emulsion to an optimum pH, thereby preventing undesirable skin feeling such as skin irritation. An optimum pH is subject to the selection of preventing skin irritation. Preferably, the optimum pH is around 5.0 to about 7.0. Suitable pH adjusters herein include acetate, phosphate, citrate, triethanolamine and carbonate.
(3) Bleaching agent
When the composition or the system of the present invention is applied to cleaning composition, one of optional ingredients is bleaching agents such as hydrogen peroxide, PB1 , PB4 and percarbonate with a particle size of 400-800 microns. These bleaching agent components can include one or more oxygen bleaching agents and, depending upon the bleaching agent chosen, one or more bleach activators. The bleaching agent can be any of the bleaching agents useful for cleaning compositions including oxygen bleaches as well as others known in the art. The bleaching agent suitable for the present invention can be an activated or non-activated bleaching agent. See, for example, European publication A 549 271 , Hage et al., issued June 30, 1993; , European publication A 549 272, Hage, issued June 30, 1993; , European publication A 458 397, Hage et al., November 27, 1991 ; U.S. Patent 5,246,621 , Harriott et al., issued March 16, 1996; , European publication A 458 398, Hage et al., November 27, 1991; U.S. Patent 5,194,416 and U.S. Patent 5,114,611 ; PCT application WO 95/07823, Hexter, issued Mrach 23, 1995; and WO 95/27772, WO 95/27773, WO 95/27774, and WO 95/27775, Pretty et al., issued October 19, 1995.
(4) Builder system When the composition or the system of the present invention is applied to cleaning composition, a builder system may further present. Any conventional builder system is suitable for use, including aluminosilicate materials such as Zeolite A, Zeolite B, and Zeolite X, silicates, polycarboxylates, alkyl- or alkenyl- succinic acid and fatty acids, materials such as ethylenediamine tetraacetate, diethylene triamine pentamethyleneacetate, metal ion sequestrants such as aminopolyphosphonates, particularly ethylenediamine tetramethylene phosphonic acid and diethylene triamine pentamethylenephosphonic acid. See, for example, U.S. Patent 3,985,669, Krummel et al., issued October 12, 1976; U.S. Patent 3,308,067, Diehl; U.S. Patent 4,144,226, issued March 13, 1979, and U.S. Patent 4,246,495, Crutchfield et al., issued March 27, 1979. Phosphate builders can also be used herein.
(5) Detergent enzyme
One another optional component cleaning detergent composition is one or more enzymes which provide cleaning performance, fabric care and/or sanitisation benefits. Said enzymes include enzymes selected from cellulases, hemicellulases, peroxidases, proteases, gluco-amylases, amylases, xylanases, lipases, phospholipases, esterases, cutinases, pectinases, keratanases, reductases, oxidases, phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, β-glucanases, arabinosidases, hyaluronidase, chondroitinase, laccase or mixtures thereof.
A range of enzyme materials and means for their incorporation into synthetic detergent compositions is disclosed, for example, in PCT publication WO 93/07263 and WO 93/07260, Genencor International; WO 89/08694, Novo; U.S. Patent 3,553,139, McCarty et al.; U.S. Patent 4,101 ,457, Place et al.; and U.S. Patent 4,507,219, Hughes; U.S. Patent 4,261 ,868, Hora et al.; U.S. Patent 3,600,319, Gedge et al.; European publication A 199,405 and European publication A 200,586, Venegas; and Novo, PCT publication WO 94/01532.
(6) Malodor controlling and/or removing agents
When the composition of the present invention to be applied for home care, for example malodor control products, one of the optional ingredients are malodor controlling agents. Malodor controlling agents include odor absorbing ingredients, such as various type of cyclodextrins, which trap the malodor molecules into the donuts structures of the cyclodextrins. Examples of cyclodextrins are such described in the U.S. Patent 5,714,137 and 5,714,445, Trinh et al., issued February 3, 1998. Other malodor controlling agents are odor scavengers, odor aggregation agents, odor masking agents such as polyphenols, and natural extracts from tea and mushroom and their derivatives.
(7) Other Ingredients
Some activators additionally useful herein are described in U.S. Patent 4,412,934, Chung et al., issued November 1 , 1983; U.S. Patent 4,483,781 , Hartman, issued November 20, 1984; U.S. Patent 4,634,551 , Burns et al, issued January 6, 1987; and U.S. Patent 4,909,953, Sadlowski et al, issued March 20, 1990. Chelating agents are described in U.S. Patent 4,663,071 , Bush et al. Suds modifiers are also optional ingredients and are described in U.S. Patent 3,933,672, Bartoletta et al., issued January 20, 1976; and U.S. Patent 4,136,045, Gault et al., issued January 23, 1979. Suitable smectite clays for use herein are described in U.S. Patent 4,762,645, Tucker et al, issued August 9, 1988. Suitable additional detergency builders for use herein are enumerated in U.S. Patent 3,936,537, Baskerville, Jr. et al., issued February 3, 1976, and in U.S. Patent 4,663,071 , Bush et al, issued May 5, 1987.
Other ingredients suitable for inclusion in a home care composition can be added to the present compositions. These include bleach activators, suds boosters or suds suppressors, anti-tarnish and anticorrosion agents, soil suspending agents, soil release agents, germicides, pH adjusting agents, non- builder alkalinity sources, and perfumes. Such ingredients are described in the Baskerville, Jr's U.S. Patent referred to the above.
Some skin care components which may be included herein, but are not limited to, can be preservatives and preservative enhancers such as water- soluble or solubilizable preservatives including Germall 115, methyl, ethyl, propyl and butyl esters of hydroxybenzoic acid, benzyl alcohol, EDTA, Bronopol (2- bromo-2-nitropropane-1 ,3-diol) and phenoxypropanol; skin lightening/evenness agents including kojic acid, arbutin, ascorbic acid and derivatives thereof and described in PCT Application number U.S. 95/07432, Hillebrand, filed on June 12, 1995; WO95/23780, Kvalnes et al, published September 8, 1995; skin- conditioning agents; skin penetration enhancing agents; skin protectants; skin soothing agents; skin healing agents; ultraviolet light absorbers or scattering agents; sequestrants; anti-acne agents; anti-androgens; depilation agents; keratolytic agents/ desquamation agents/ exfoliants such as salicylic acid; panthenol moisturizer such as D-panthenol; soluble or colloidally-soluble moisturizing agents such as hyaluronic acid and starch-grafted sodium polyacrylates such as Sanwet™ IM-1000, IM-1500 and IM-2500 available from Celanese Superabsorbent Materials, Portsmith, VA, U.S.A and described in U.S. Patent 4,076,663; proteins and polypeptides and derivatives thereof; organic hydroxy acids; drug astringents; external analgesics; film formers; absorbents including oil absorbents such as clays and polymeric absorbents; abrasives; anticaking agents; antifoaming agents; binders; biological additives; bulking agents; coloring agents; perfumes, essential oils, and solubilizers thereof; natural extracts; compounds which stimulate collagen production.
E. Method for Making Composition
A non-aqueous composition of the present invention is prepared by a method comprising the steps of mixing an active compound to a oily component for obtaining a liquid active solvent. The active component has the following formula (I):
Figure imgf000020_0001
wherein R^ and R2 are independently selected from saturated, straight or branched alkyl group of from 1 to about 10 carbons; preferably independently from 1 to about 3 carbons. The oily component has less than 50 °C of melting point.
EXAMPLES
The following examples further describe and demonstrate embodiments within the scope of the present invention. The examples are given solely for the purpose of illustration and are not to be construed as limitations of the present invention, as many variations thereof are possible without departing from the spirit and scope of the invention.
The compositions shown below can be prepared by any conventional method known in the art. Suitable methods and formulations are as follows: wt %
Figure imgf000021_0001
1 d-8-acetoxycarvotanacetone
2 C12-15 alkyl benzoate
3 polysaccharides
4 hydroxyethylcellulose
The embodiments disclosed and represented by the previous examples have many advantages. For example, the composition comprising a solubilized composition of 8-ACA into oily compounds provides desirable repellent efficacy; better and long-lasting efficacy than water-base composition. Further, the present composition, with a surfactant or an emulsifier, can easily apply to any application which is an aqueous base without lack of repellency and long-lasting efficacy.

Claims

What is claimed is:
1. A non-aqueous composition comprising
(1 ) a safe and effective amount of an active compound having the following formula (I):
Figure imgf000022_0001
wherein R1 and R are independently selected from saturated, straight or branched alkyl group of from 1 to about 10 carbons; and
(2) a oily component for obtaining a liquid active solution, having less than 50 °C of melting point.
2. The non-aqueous composition of Claim 1 , wherein the oily component is selected from the group consisting of mineral oil, petrolatum, straight or branched, saturated or unsaturated hydrocarbons having from about 7 to about 40 carbon atoms, vegetable oils and hydrogenated vegetable oils, animal fats and oils, polyhydric alcohols, silicone oils, and C<|_30 mono- and poly- esters of sugars and related materials, fatty alcohols, fatty acids, and fatty acid derivatives or fatty alcohol derivatives.
3. The composition of claim 2, wherein R1 and R2 are independently selected from saturated, straight or branched alkyl group of from 1 to about 3 carbons.
4. The non-aqueous composition of Claim 3 comprising from about 0.1 wt% to about 85 wt% of the active compound.
5. The non-aqueous composition of claim 4 further comprising a safe and effective amount of a component for obtaining an emulsion in an aqueous solution, selected from the group consisting of a surfactant, an emulsifier, and mixtures thereof.
6. A dust mite repellent composition comprising
(1 ) a safe and effective amount of at least one active compound having the following formula (I):
Figure imgf000023_0001
wherein R1 and R2 are independently selected from saturated, straight or branched alkyl group of from 1 to about 10 carbons; and
(2) a oily component for obtaining a liquid active solvent, the oily component selected from the group consisting of mineral oil, petrolatum, straight or branched, saturated or unsaturated hydrocarbons having from about 7 to about 40 carbon atoms, vegetable oils and hydrogenated vegetable oils, animal fats and oils, polyhydric alcohols, silicone oils, C-1.30 mono- and poly- esters of sugars and related materials, fatty alcohols, fatty acids, and fatty acid derivatives or fatty alcohol derivatives; and (3) an emulsion forming component selected from the group consisting of a surfactant, an emulsifier, and mixtures thereof.
7. The dust mite repellent composition of Claim 6 comprising from about 0.1 wt% to about 85 wt% of the active compound.
8. The dust mite repellent composition of Claim 7, wherein R1 and R2 is independently, methyl, ethyl, or propyl.
9. The dust mite repellent composition of Claim 8, wherein the oily component has a viscosity of from about 0 to about 10,000 cps.
0. A method for making non-aqueous composition comprising the steps of mixing an active compound having the following formula (I):
Figure imgf000024_0001
wherein R^ and R2 are independently selected from saturated, straight or branched alkyl group of from 1 to about 10 carbons, to a oily component for obtaining a liquid active solution, having less than 50 °C of melting point.
PCT/US1999/026581 1999-11-09 1999-11-09 A composition comprising solubilized repellent active component WO2001033963A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU18164/00A AU1816400A (en) 1999-11-09 1999-11-09 A composition comprising solubilized repellent active component
PCT/US1999/026581 WO2001033963A1 (en) 1999-11-09 1999-11-09 A composition comprising solubilized repellent active component

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1999/026581 WO2001033963A1 (en) 1999-11-09 1999-11-09 A composition comprising solubilized repellent active component

Publications (1)

Publication Number Publication Date
WO2001033963A1 true WO2001033963A1 (en) 2001-05-17

Family

ID=22274033

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/026581 WO2001033963A1 (en) 1999-11-09 1999-11-09 A composition comprising solubilized repellent active component

Country Status (2)

Country Link
AU (1) AU1816400A (en)
WO (1) WO2001033963A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002000022A1 (en) * 2000-06-26 2002-01-03 Forskarpatent I Syd Composition for inhibiting feeding of weevils
CN110269071A (en) * 2019-07-31 2019-09-24 王鹏 A kind of mosquito repellent composition and preparation method thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4127672A (en) * 1972-09-21 1978-11-28 Beiersdorf Aktiengesellschaft Insect repellants
US4335104A (en) * 1978-08-16 1982-06-15 United Chemical Corporation Anhydrous multi-purpose moisturizing composition
CN1105658A (en) * 1994-01-22 1995-07-26 中国科学院昆明植物研究所 d-8-acyloxy-allodihydro-carvones compounds and synthetic method thereof
JPH10316507A (en) * 1997-05-15 1998-12-02 Kuraray Co Ltd Miticide
US5854288A (en) * 1993-11-18 1998-12-29 Hoechst Schering Agrevo Gmbh Use of benzoylureas for controlling house dust mites
US5972983A (en) * 1997-12-05 1999-10-26 Sumitomo Chemical Company Limited Pest repellent

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4127672A (en) * 1972-09-21 1978-11-28 Beiersdorf Aktiengesellschaft Insect repellants
US4335104A (en) * 1978-08-16 1982-06-15 United Chemical Corporation Anhydrous multi-purpose moisturizing composition
US5854288A (en) * 1993-11-18 1998-12-29 Hoechst Schering Agrevo Gmbh Use of benzoylureas for controlling house dust mites
CN1105658A (en) * 1994-01-22 1995-07-26 中国科学院昆明植物研究所 d-8-acyloxy-allodihydro-carvones compounds and synthetic method thereof
JPH10316507A (en) * 1997-05-15 1998-12-02 Kuraray Co Ltd Miticide
US5972983A (en) * 1997-12-05 1999-10-26 Sumitomo Chemical Company Limited Pest repellent

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 124, no. 5, 29 January 1996, Columbus, Ohio, US; abstract no. 56354, SUN, HANDONG ET AL: "Preparation of (+)-8-acyloxy-allodihydrocarvones compounds as repellents" XP002142986 *
PATENT ABSTRACTS OF JAPAN vol. 1999, no. 03 31 March 1999 (1999-03-31) *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002000022A1 (en) * 2000-06-26 2002-01-03 Forskarpatent I Syd Composition for inhibiting feeding of weevils
CN110269071A (en) * 2019-07-31 2019-09-24 王鹏 A kind of mosquito repellent composition and preparation method thereof
CN110269071B (en) * 2019-07-31 2021-04-13 王鹏 Mosquito-repellent composition and preparation method thereof

Also Published As

Publication number Publication date
AU1816400A (en) 2001-06-06

Similar Documents

Publication Publication Date Title
US6120782A (en) Methods of delivering materials into the skin, and compositions used therein
US7771753B2 (en) Topical formulations comprising ceramic hydroxyapatite particles
EP1032363B1 (en) Conjugated linoleic acid delivery system in cosmetic preparations
JP2010506036A (en) Novel natural oil gel and its application
WO2006103037A2 (en) COMPOSITION CONTAINING β-DEFENSIN 2
JP5645808B2 (en) Cosmetics, method for producing the same, cosmetic composition, cosmetic containing the cosmetic composition, and method for producing the same
CN1980631A (en) Highly concentrated self-emulsifying emulsion bases used for the production of oil-in-water emulsions
GB2450727A (en) Perfumed silicone microemulsion
DE102016225659A1 (en) Anhydrous deodorant compositions with absorber combination II
DE102007024384A1 (en) Cosmetic and dermatological compositions against dry skin
CN113727694B (en) Sprayable film-forming compositions for improved topical formulation performance
JPH0421642B2 (en)
JPH08301725A (en) Cleansing composition having low irritation
JP2003192533A (en) Ultrafine particulate emulsion comprising haloalkynyl derivative
WO2001033963A1 (en) A composition comprising solubilized repellent active component
GB2367490A (en) Skin barrier enhancing absorbent tissues
EP3166589B1 (en) Sweat-inhibiting cosmetics with proteins from legume of genus pisum, and which do not contain aluminium and/or zirconium halogenides and/or hydroxyhalognides
US20050276772A1 (en) Antiperspirant composition comprising polyol, antiperspirant active article containing same and method for using same
JP7298863B2 (en) emulsified cosmetic
JP5834404B2 (en) O / W UV protection skin cosmetics
DE102014213226A1 (en) Antiperspirant cosmetic preparations containing specific proteins from skin appendages of mammals, birds, fish, insects or crustaceans which do not contain halides and / or hydroxyhalides of aluminum and / or zirconium
CA2510933C (en) Methods of delivering materials into the skin, and compositions used therein
JP2008255028A (en) Deodorizing agent composition for pet
EP3166588B1 (en) Use of a specific protein to reduce transpiration of the body
CA2584797C (en) Methods of delivering materials into the skin, and compositions used therein

Legal Events

Date Code Title Description
ENP Entry into the national phase

Ref country code: AU

Ref document number: 2000 18164

Kind code of ref document: A

Format of ref document f/p: F

AK Designated states

Kind code of ref document: A1

Designated state(s): AE AL AM AT AT AU AZ BA BB BG BR BY CA CH CN CR CU CZ CZ DE DE DK DK DM EE EE ES FI FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SK SL TJ TM TR TT UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642