WO2000027197A1 - Composition renfermant un melange actif insectifuge - Google Patents

Composition renfermant un melange actif insectifuge Download PDF

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Publication number
WO2000027197A1
WO2000027197A1 PCT/US1998/024021 US9824021W WO0027197A1 WO 2000027197 A1 WO2000027197 A1 WO 2000027197A1 US 9824021 W US9824021 W US 9824021W WO 0027197 A1 WO0027197 A1 WO 0027197A1
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WO
WIPO (PCT)
Prior art keywords
fragrance
composition
methyl
aldehyde
insect repellent
Prior art date
Application number
PCT/US1998/024021
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English (en)
Inventor
Gong-Xiang Chen
Victorio Tan Wee
Shingo Ishii
Hidekazu Tanaka
Original Assignee
The Procter & Gamble Company
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Filing date
Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to PCT/US1998/024021 priority Critical patent/WO2000027197A1/fr
Priority to AU13971/99A priority patent/AU1397199A/en
Publication of WO2000027197A1 publication Critical patent/WO2000027197A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION 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
    • A01N27/00—Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/02—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings containing insect repellants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures

Definitions

  • the present invention relates to a topical composition.
  • it relates to an insect repellent composition.
  • N,N-diethyl-m-toluamide which is sometimes referred to as "DEET”
  • dimethyl phthalate are widely used insect as repellent actives.
  • DEET is very effective in protecting outdoors persons from insects, provided it is properly applied such that it adequately covers the skin of the user. See U.S. Patent 2,932,665, Wagner et al., issued April 12, 1960; U.S. Patent 4,756,905, Melnik, issued July 12, 1988; U.S. Patent 4,416,881 , McGovern et al., issued November 22, 1983; and U.S. Patent 4,419,360, Smolanoff, issued December 6, 1983.
  • DEET Certain formulations containing DEET have been designed for cosmetic uses, for example in sunscreen products such as lotions. See U.S. Patent 5,518,712, Stewart, issued May 21 , 1996; U.S. Patent 5,575,988, Knowles, issued November 19, 1996.
  • relatively high concentrations of insect repellent actives such as DEET may give rise to allergic or toxic reactions in some individuals when applied to the skin.
  • some users may find the smell of DEET to be unpleasant.
  • a certain insect repellent blend such as TREOTM containing terpineol, citronella, rhodinol extras, and geraniol has also been used as a non-toxic and natural repellent. See, U.S. Patent 5,227,406, issued July 13, 1993; U.S.
  • Such an insect repellent blend tends to be more pleasantly scented but provides only weak repellency.
  • there is still a need for effective insect repellent which is non-allergic and non-toxic to the skin as well as easy to formulate in compositions.
  • the present invention is directed to an insect repellent composition
  • an insect repellent composition comprising : a) an insect repellent active blend comprising a fragrance carbonyl compound, a fragrance alcohol, a fragrance ester, a nitrile compound, an epoxide, and an ether compound; and b) a cosmetically-acceptable carrier.
  • topical application means to apply or spread a material onto the surface of the skin.
  • compositions or components thereof so described are suitable for use in contact with human skin without undue toxicity, incompatibility, instability, allergic response, and the like.
  • 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.
  • mixtures is meant to include a simple combination of materials and any compounds that may result from their combination.
  • composition of the present invention comprises an insect repellent active blend ("active blend") including a fragrance carbonyl compound, a fragrance alcohol, a fragrance ester, a nitrile compound, an epoxide, and an ether compound, and a cosmetically-acceptable carrier.
  • active blend an insect repellent active blend including a fragrance carbonyl compound, a fragrance alcohol, a fragrance ester, a nitrile compound, an epoxide, and an ether compound, and a cosmetically-acceptable carrier.
  • the composition is, preferably, a dermatologically-acceptable topical composition; more preferably, a cosmetic composition used for insect repellent.
  • the cosmetic composition provides superior insect repellent efficacy in addition to other skin benefits such as moisturizing, smoothness, skin lightening, and the like, as well as those provided by conventional cosmetic compositions.
  • the composition of the present invention especially provides a prolonged repellent efficacy.
  • composition useful herein may be made into a wide variety of products depending on the type of carriers utilized. These include, but are not limited to, skin care products such as liquid type products including lotions, creams, gels, powders, sticks, sprays, ointments, and pastes and cosmetics such as foundation (e.g., solid, semi-solid, or liquid make-up).
  • skin care products such as liquid type products including lotions, creams, gels, powders, sticks, sprays, ointments, and pastes and cosmetics such as foundation (e.g., solid, semi-solid, or liquid make-up).
  • liquid type products such as lotions and creams of the present invention generally comprise a solution carrier and one or more emollients.
  • emollient refers to a material used for the prevention or relief of dryness, as well as for the protection of the skin.
  • Such liquids typically contain from about 1% to about 30%, preferably from about 5% to about 15% of the emollient; from about 70% to about 95%, preferably from about 70% to about 90% of water; in addition to the active blends described herein.
  • a cream typically contains from about 5% to about 70%, preferably from about 10% to about 35% of an emollient; from about 30% to about 90%, preferably from about 45% to about 85% of water; in addition to the active blends described herein.
  • Powder type products such as skin powder including cosmetic powder foundation, are other embodiments used over a large area of the skin, such as over the face.
  • Such powder products of the present invention include a cosmetically acceptable carrier and may further include conventional ingredients such as oils and waxes, pigments, stabilizers, colorants, and the like.
  • the composition of the present invention contains the insect repellent active blend including a fragrance carbonyl compound, a fragrance alcohol, a fragrance ester, an nitrile compound, an epoxide, and an ether compound.
  • the active blend herein provides excellent repellency, particularly against mosquitoes, when applied to skin.
  • the composition containing the active blend herein can provide protection from at least 80% of bites over a 4 hours exposure period.
  • the fragrance carbonyl compound useful herein preferably has a molecular weight of from about 100 to about 300.
  • the fragrance carbonyl compound is selected from the group consisting of a fragrance aldehyde, a fragrance ketone, and mixtures thereof.
  • Preferred fragrance aldehydes useful herein include an aliphatic aldehyde, a terpenic aldehyde, and an aromatic aldehyde.
  • Nonlimiting examples of the aliphatic aldehyde useful herein include hexyl aldehyde (caproaldehyde), heptyl aldehyde, octyl aldehyde (caprylaldehyde), nonyl aldehyde (pelargonaldehyde), decyl aldehyde (capraldehyde), undecyl aldehyde, dodecyl aldehyde (lauric aldehyde), tridecyl aldehyde, 3,5,5- trimethylhexanal, 2-methyldecanal (methyloctylacetaldehyde), 2- methylundecanal (methylnonylacetaldehyde), frat7s-2-hexenal (leaf aldehyde), c/s-4-heptenal, rat?s-2-c/ ' s-6-nonadienal (cucumber aldehyde), c
  • Nonlimiting examples of the terpenic aldehyde herein include 3,7- dimethyl-7-methoxyoctan-1-al (methoxydihydrocitronellal), citronellyloxy acetaldehyde, 2,4-diemthyl-3-cyclohexenyl carboxyaldehyde, 2,4,6-trimethyl-3- cyclohexene-1 -carboxyaldehyde (isocyclocitral), 5-methoxy-octahydro-4,7- menthano-1 H-indene-2-carboxyaldehyde (scentenal), 4-(4-methyl-3-pentenyl)-3- cyclohexen-1 -carboxyaldehyde (myrac aldehyde), 4-(4-hydroxy-4-methyl-pentyl)- 3-cyclohexen-1 -carboxyaldehyde (lyral), 1 -methyl-4-(4-methyl-pentyl
  • Nonlimiting examples of the aromatic aldehyde useful herein include benzaldehyde, phenylacetaldehyde (hyacinth aldehyde), 3-phenylpropanal (phenylpropylaldehyde), 3-pheny-2-propenal (cinnamic aldehyde), 2-pentyl-3- phenyl-2-propenal ( ⁇ -amyl cinnamic aldehyde), 2-hexyl-3-phenyl-2-propenal ( ⁇ - hexyl cinnamic aldehyde), 2-phenylpropanal (hydratropic aldehyde), 4- methoxybenzaldehyde (anis aldehyde), p-methylphenylacetaldehyde (p-tolyl acetaldehyde), 4-isopropylbenzaldehyde (cumin aldehyde), 2-methyl-3-(4- isopropylphenyl)-prop
  • the preferred fragrance ketones useful herein include an aliphatic ketone, a terpenic and sesquiterpenic ketone, a cyclic ketone, and an aromatic ketone.
  • the ketones can be saturated, unsaturated, linear, branched, or cyclic, preferably including alkyl, alkenyl, or aryl moieties.
  • the ketones can include other functional groups such as ethers or esters.
  • Nonlimiting examples of the aliphatic ketone useful herein include 3- hydroxy-2-butanone (acetoine), 2,3-butanedione (diacetyl), 2-heptanone (methyl amyl ketone), 3-octanone (ethyl amyl ketone), 2-octanone (methyl hexyl ketone), 2-undecanone (methyl nonyl ketone), 6-methyl-5-hepten-2-one, acetyl diisoamylene (koavone).
  • Examples of the terpenic and sesquiterpenic ketone useful herein include 1 ,7,7-trimethyl bicyclo[2.2.1]heptan-2-one (camphor), 1 ,8-p-menthadien-6-one (carvone), p-menthan-3-one (menthone), -p-menth-4(8)-en-3-one (d-pulegone), p-menth-1-en-3-one (piperitone), 1 ,3,3-trimethyl-bicyclo[2.2.1]heptan-2-one (fenchone), 6,10,-dimethyl-5,9-undecadiene-2-one (geranyl acetone), acetyl cedrene (cedryl methyl ketone), 5,6-dimethyl-8-isopropenylbicyclo-[4.4.0]-1- decen-3-one (nootkatone), 4-(2,2,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
  • cyclic ketone examples include 3-hydroxy-2-methyl- 4H-pyran-4-one (maltol), 2-ethyl-3-hydroxy-4H-pyran-4-one (ethyl maltol), 2,5- diemthyl-4-hydroxy-2H-furan-3-one, 4,5-dimethyl-3-hydroxy-5H-furan-2-one (sugar lactone), p-f-butylcyclohexanone, 2-amylcyclopentanone, 2- heptylcyclopentanone, 3-methyl-2-pentyl-2-cyclopenten-1-one (dihydrojasmone), 3-methyl-2-(2-cis-penten-1-yl)-2-cyclopenten-1-one (c/s-jasmone), 6 (or 7)- ethylidene-octahydro-5,8-methano-2H-benzopyrane (florex), 7-methyl-octahydro- 1 ,4-methane
  • ketones include Ethyl ketopropinate (ethyl pyruvate), isoamyl ketopropionate (isoamyl pyruvate), ethyl acetoacetate, ethyl ⁇ -ketovalerate (ethyl levulinate), methyl jasmonate, and methyl dihydrojasmonate.
  • the fragrance alcohol useful herein preferably has a molecular weight of from about 100 to about 250.
  • the fragrance alcohols can be any alcohols which are commercially available and known in the art.
  • the fragrance alcohols can be saturated, unsaturated, linear or branched compound, preferably those having alkyl, alkenyl, aryl, aralkyl, alkylalkoxylate derivatives with one or more OH groups.
  • the fragrance alcohol can be alkoxylated with 1 to 30 units of ethylene oxide, propylene oxide or mixtures thereof.
  • Aromatic or aliphatic alcohols are useful.
  • the alcohols can contain additional functionality such as amines, amides, ethers, or esters as a part of their structure.
  • Nonlimiting examples include, but are not limited to, phenylethyl alcohol, frans-2-hexenol, c/s-3-hexenol, 1-octen-3-ol (amyl vinyl carbinol), 9-decenol, 4-methyl-3-decen-5- ol, 10-undecenol, and frat7s-2-c s-6-nonadien-1-ol (violet leaf alcohol).
  • alcohols herein include 3,7-dimethyl-1 ,6-octadiene-3-ol (linalool), 3,7-dimetyl-frans-2,6-octadien-1-ol (geraniol), 3,7-dimethyl-cs-2,6- octadien-1-ol (nerol), 3,7-dimethyl-6-octen-1-ol (citronellol), 2-methyl-6- methylene-7-octen-2-ol (myrcenol), 2,6-dimethyl-5-hydroxymethyl-2,6-heptadien (lavandulol), 3,7-dimethyloctanol (tetrahydrogeraniol), 3,7-dimethyloctan-3-ol (tetrahydrolinalool), 3,7-dimethyloctan-1 ,7-diol (hydroxy citronellol), 2,6-dimethyl- 7-octen-2-o
  • the fragrance ester useful herein preferably has a molecular weight of from about 150 to about 300.
  • the fragrance ester herein include ethyl formate, linalyl formate, citronellyl formate, geranyl formate, benzyl formate, phenylethyl formate, butyl acetate, isoamyl acetate, cis-3-hexenyl acetate (leaf acetate), citronellyl acetate, linalyl acetate, geranyl acetate, benzyl acetate, phenylethyl acetate, terpinyl acetate, flor, acetate, 3,5,5-trimethylhexyl acetate, 3,7-dimethyl-6-octen-1-yl acetate, 2-isopropenyl-5-methyl-4-hexenyl acetate, 3,7- dimethyl-2,6-octadien-1-yl acetate
  • the nitrile compound useful herein preferably has a molecular weight of from about 100 to about 200.
  • the nitrile compounds are 3,7- dimethyl-2,6-octadiene-1 -nitrile (geranyl nitrile), 3, 7-dimethyl-6-octen-1 -nitrile (citronellyl nitrile), 5-phenyl-3-methyl-2-penten nitrile and 3,7-dimethyl-2,6- nonadien nitrile.
  • the epoxide useful herein has a molecular weight of from about 100 to about 200.
  • 2,2-dimethyl-3-(3-methyl-2,4-pentadienyl) oxirane is exemplary.
  • the ether compound useful herein has a molecular weight of from about 100 to about 300. Examples of the ether compounds include 1 ,8- cineol (eucalyptol), 4-methyl-1-propenyl) tetrahydropyrane, and 4-acetoxy-3- amyltetrahydropyrane.
  • the active blend includes from about 2% to about 35% of a fragrance carbonyl compound selected from the group consisting of a fragrance aldehyde, a fragrance ketone, and mixtures thereof, from about 1% to about 25% of a fragrance alcohol and from about 3% to about 20% of a fragrance ester.
  • a nitrile compound, an epoxide, and an ether compound are contained from about 0.1 to about 5% of each by weight of the composition.
  • composition of the present invention contains a cosmetically- acceptable carrier.
  • cosmetically acceptable carrier means one or more compatible solid or liquid fillers, diluents, extenders and the like, which are cosmetically acceptable as defined herein.
  • compatible herein means that the components of the compositions of this invention are capable of being commingled with each other, in a manner such that there is no interaction which would substantially reduce the efficacy of the composition under ordinary use situations.
  • the type of the carrier utilized in the present invention depends on the type of the product desired and may comprise several types of carriers including, but not limited to, solutions, aerosols, emulsions (including oil-in-water or water- in-oil), gels, solids, and liposomes.
  • the cosmetically-acceptable carrier of the present invention is preferably selected from the group consisting of a water soluble thickening polymer, a hydrophobic component, an amphiphilic surfactant, a hydrophilic liquid carrier, a water, and mixtures thereof.
  • the water-soluble polymer is selected from the group consisting of a carbonic acid polymer, a polysacchahde, a gum, and mixtures thereof. While not wishing to be bound by theory, it is believed that water-soluble polymer of the composition prevents and/or retards the evaporation of volatile repellent actives when present into the atmosphere and minimize the penetration of the repellent actives into the skin. Such performances tend to show the repellent active compound staying on the skin surface longer, resulting in a longer lasting repellent efficacy.
  • the repellent actives can stay on the skin surface longer, resulting in providing long lasting repellent efficacy.
  • Nonlimiting examples of suitable water-soluble polymers in the compositions of the present invention include carboxylic acid polymers, polysaccharides, and gums.
  • the carboxylic acid polymers useful herein are crosslinked compounds containing one or more monomers derived from acrylic acids, substituted acrylic acids, and salts and esters of these acrylic acids and the substituted acrylic acids, wherein the crosslinking agent contains two or more carbon-carbon double bonds and is derived from a polyhydric alcohol.
  • the preferred carboxylic acid polymers are of two general types.
  • the first type of polymer is a crosslinked homopolymer of an acrylic acid monomer or derivative thereof (e.g., wherein the acrylic acid has substituents on the two and three carbon positions independently selected from the group consisting of C1.4 alkyl, -CN, -COOH, and mixtures thereof).
  • the second is a crosslinked copolymer having a first monomer selected from the group consisting of an acrylic acid monomer or derivative thereof (as just described in the previous sentence), a short chain alcohol (i.e., C .A) acrylate ester monomer or derivative thereof (e.g., wherein the acrylic acid portion of the ester has substituents on the two and three carbon positions independently selected from the group consisting of C1.4 alkyl, -CN, -COOH, and mixtures thereof), and mixtures thereof; and a second monomer which is a long chain alcohol (i.e., C8-40) acrylate ester monomer or derivative thereof (e.g., wherein the acrylic acid portion of the ester has substituents on the two and three carbon positions independently selected from the group consisting of C-]_4 alkyl, -CN, -COOH, and mixtures thereof). Combinations of these two types of polymers are also useful herein.
  • Examples of commercially available homopolymers of the first type useful herein include the carbomers, which are homopolymers of acrylic acid crosslinked with allyl ethers of sucrose or pentaerythhtol.
  • the carbomers are available as the Carbopol® 900 series from B.F. Goodrich (e.g., Carbopol® 954).
  • Examples of commercially available copolymers of the second type useful herein include copolymers of C ⁇
  • copolymers are known as acrylates/C 10-30 alkyl acrylate crosspolymers and are commercially available as Carbopol® 1342, Carbopol® 1382, Pemulen TR-1 , and Pemulen TR-2, from B.F. Goodrich.
  • carboxylic acid polymer thickeners useful herein are those selected from the group consisting of carbomers, acrylates/C 10-30 alkyl acrylate crosspolymers, and mixtures thereof.
  • polysaccharides refers to the water-soluble polymers containing a backbone of repeating sugar (i.e., carbohydrate) units.
  • Nonlimiting examples of polysaccharides include those selected from the group consisting of cellulose, carboxymethyl hydroxyethylcellulose, cellulose acetate propionate carboxylate, hydroxyethylcellulose, hydroxyethyl ethylcellulose, hydroxypropylcellulose, hydroxypropyl methylcellulose, methyl hydroxyethylcellulose, microcrystalline cellulose, sodium cellulose sulfate, and mixtures thereof.
  • Alkyl substituted celluloses are also useful.
  • the hydroxy groups of the cellulose polymer are preferably hydroxyalkylated (preferably, hydroxyethylated or hydroxypropylated), forming a hydroxyalkylated cellulose that is further modified with a Cio-30 straight or branched alkyl group of from about 10 to about 30 carbon atoms through an ether linkage.
  • Preferred polymers are ethers of straight or branched alcohols of from about 10 to about 30 carbons with hydroxyalkylcellulose.
  • alkyl groups useful herein include those selected from the group consisting of stearyl, isostearyl, lauryl, myristyl, cetyl, isocetyl, cocoyl (i.e.
  • alkyl groups derived from the alcohols of coconut oil palmityl, oleyl, linoleyl, linolenyl, ricinoleyl, behenyl, and mixtures thereof.
  • Preferred among the alkyl hydroxyalkyl cellulose ethers is the material given in the CTFA designation as cetyl hydroxyethylcellulose, which is the ether of cetyl alcohol and hydroxyethylcellulose. This material is sold under the tradename Natrosol® CS Plus from Aqualon Corporation.
  • polysaccharides include scleroglucans comprising a linear chain of 1 to less than 3 linked glucose units with a 1 to less than 6 linked glucose every three units, a commercially available example of which is ClearogelTM CS11 from Michel Mercier Products Inc. (Mountainside, NJ, USA).
  • Gums Other water-soluble polymers useful herein include materials which are primarily derived from natural sources.
  • Nonlimiting examples of these gums include materials selected from the group consisting of acacia, agar, algin, alginic acid, ammonium alginate, amylopectin, calcium alginate, calcium carrageenan, carnitine, carrageenan, dextrin, gelatin, gellan gum, guar gum, guar hydroxypropyltrimonium chloride, hyaluroinic acid, hydroxypropyl chitosan, hydroxypropyl guar, karaya gum, kelp, locust bean gum, natto gum, potassium alginate, potassium carrageenan, propylene glycol alginate, sclerotium gum, sodium carboyxmethyl dextran, sodium carrageenan, tragacanth gum, xanthan gum, and mixtures thereof.
  • water-soluble polymers include those disclosed in U.S. Patent 4,387,107, Klein et al., issued June 7, 1983 and "Encyclopedia of Polymer and Thickeners for Cosmetics," R.Y. Lochhead and W. R. Fron, eds., Cosmetics & Toiletries, vol. 108, pp. 95-135 (May 1993), the disclosures of which are herein incorporated by reference.
  • Hydrophobic components useful in the present invention include a lipid, oil, oily or other hydrophobic component.
  • the hydrophobic component is used as an emollient.
  • suitable hydrophobic components include mineral oil, petrolatum, C7-40 straight and branched hydrocarbons, C-1-C30 alcohol esters, glycerides, alkylene glycol esters, propoxylated and ethoxylated derivatives, sugar ester, vegetable oils and hydrogenated vegetable oils, animal fats and oils, and C4-20 alkyl ethers of polypropylene glycols, C1-20 carboxylic acid esters of polypropylene glycols, and di-Cs-30 alkyl ethers.
  • the composition contains from about 1% to about 98% of the hydrophobic component, more preferably from about 1% to about 50%, and still more preferably from about 1% to about 30%.
  • the hydrophobic component may be derived from animals, plants, or petroleum and may be natural or synthetic (e.g., man-made). 3) Amphiphilic Surfactant
  • amphiphilic surfactant useful herein can include any of a wide variety of nonionic, cationic, anionic, zwittehonic, amphoteric, as well as mixtures of these surfactants.
  • Such surfactants are well known to those skilled in the detergency art.
  • Nonlimiting examples of possible surfactants include isoceteth-20, sodium methyl cocoyl taurate, sodium methyl oleoyl taurate, and sodium lauryl sulfate. See U.S. Patent No. 4,800,197, to Kowcz et al., issued January 24, 1989, which is incorporated herein by reference in its entirety, for exemplary surfactants useful herein.
  • the cleansing compositions can optionally contain, at their art-established levels, other materials which are conventionally used in cleansing compositions. 4) Hydrophilic Liquid Carrier
  • the composition of the present invention may contain a hydrophilic liquid carrier (HLC).
  • HLC can contain a dermatologically acceptable, non- aqueous hydrophilic diluent.
  • hydrophilic diluents are polyhydric alcohols such as low molecular weight monovalent alcohols (i.e., C ⁇
  • hydrophilic diluents are polyhydric alcohols such as low molecular weight monovalent alcohols (i.e., C ⁇
  • the composition contains from about 1% to about 99% of HLC, more preferably from about 20% to about 95%.
  • the HLC includes water and one or more water soluble or dispersible ingredients.
  • the compositions of the present invention may comprise from about 25% to about 99%, more preferably from about 50% to about 95%, and most preferably from about 60% to about 90% water. The exact amount of water in the formulation will vary with the ranges of the required and optional components chosen.
  • compositions of the present invention contain other actives capable of functioning in different ways to enhance the benefits of the active blend and/or to provide other benefits.
  • actives capable of functioning in different ways to enhance the benefits of the active blend and/or to provide other benefits.
  • examples of such substances include, but are not limited to, anti-oxidants/radical scavengers, anti-inflammatory agents, antimicrobial agents, sunscreens and sunblocks, and chelators.
  • Anti-Oxidants/Radical Scavengers Anti-oxidant/radical scavengers are especially useful for providing protection against UV radiation which can cause increased scaling or texture changes in the stratum corneum and against other environmental agents which can cause skin damage.
  • Anti-oxidants/radical scavengers such as ascorbic acid (vitamin C) and its salts, ascorbyl esters of fatty acids, ascorbic acid derivatives (i.e., magnesium ascorbyl phosphate), 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, argin
  • Preferred anti- oxidants/radical scavengers are selected from tocopherol sorbate and other esters of tocopherol, more preferably tocopherol sorbate.
  • tocopherol sorbate in topical compositions and applicable to the present invention is described in U.S. Patent 4,847,071 , Bissett et al, issued on July 11 , 1989.
  • Anti-Inflammatory Agents enhance the skin appearance benefits, by for example, contribution of uniformity and acceptable skin tone and/or color.
  • the anti-inflammatory agent includes a steroidal anti- inflammatory agent and an non-steroidal anti-inflammatory agent.
  • Preferred steroidal anti-inflammatory for use is hydrocortisone.
  • Such agents may suitably be obtained as an extract by suitable physical and/or chemical isolation from natural sources (i.e., plants, fungi, by-products of microorganisms).
  • natural sources i.e., plants, fungi, by-products of microorganisms.
  • natural sources i.e., plants, fungi, by-products of microorganisms.
  • alpha bisabolol, aloe vera, Manjistha extracted from plants in the genus Rubia, particularly Rubia Cordifolia
  • Guggal extracted from plants in the genus Commiphora, particularly Commiphora Mukul.
  • kola extract, chamomile, and sea whip extract may be used.
  • Additional anti-inflammatory agents useful herein include compounds of the Licorice (the plant genus/species Glvcyrrhiza glabra) family, including glycyrrhetic acid, glycyrrhizic acid, and derivatives thereof (e.g., salts and esters).
  • Suitable salts of the foregoing compounds include metal and ammonium salts.
  • Suitable esters include C2-24 saturated or unsaturated esters of the acids, preferably C-J O-24- more preferably C-i ⁇ -24-
  • antimicrobial agents means a compound capable of destroying microbes, preventing the development of microbes or preventing the pathogenic action of microbes.
  • Antimicrobal agents are useful, for example, in controlling acne.
  • Preferred antimicrobial agents useful in the present invention are benzoyl peroxide, erythromycin, tetracycline, clindamycin, azelaic acid, sulfur resorcinol phenoxyethanol, and IrgasanTM DP 300 (Ciba Geigy Corp., U.S.A.).
  • a safe and effective amount of an antimicrobial agent may be added to compositions of the present invention, preferably from about 0.001% to about 10%, more preferably from about 0.01% to about 5%, still more preferably from about 0.05% to about 2%.
  • Sunscreens and Sunblocks generally prevent excessive scaling and texture changes of the stratum corneum by exposure of ultraviolet light and may be added to the present invention.
  • Suitable sunscreens and sunblocks may be organic or inorganic.
  • sunscreens and sunblocks which are useful in the compositions are those selected from 2-ethylhexyl-p-methoxycinnamate (commercially available as PARSOL MCX), butylmethoxydibenzoyl-methane, 2-hydroxy-4-methoxybenzo- phenone, 2-phenylbenzimidazole-5-sulfonic acid, octyldimethyl-p-aminobenzoic acid, octocrylene, 2-ethylhexyl N,N-dimethyl-p-aminobenzoate, p-aminobenzoic acid, 2-phenylbenzimidazole-5-sulfonic acid, octocrylene, oxybenzone, homomenthyl salicylate, octyl salicylate, 4,4 , -methoxy-f-butyldibenzoylmethane, 4-isopropyl dibenzoylmethane, 3-
  • sunscreens and sunblocks such as those disclosed in U.S. Patent 4,937,370, Sabatelli, issued on June 26, 1990, and U.S. Patent 4,999,186, Sabatelli, issued on March 12, 1991.
  • the sunscreens and sunblocks disclosed therein have, in a single molecular, two distinct chromophore moieties which exhibit different ultraviolet radiation absorption spectra.
  • One of the chromophore moieties absorbs predominantly in the UVB radiation range and the other absorbs strongly in the UVA radiation range.
  • These sunscreens and sunblocks provide higher efficacy, broader UV absorption, lower skin penetration and longer lasting efficacy relative to conventional sunscreens and sunblocks.
  • SPF Sun Protection Factor
  • a sunscreen or sunblock herein may also be added to improve the skin, particularly to enhance their resistance to being washed off by water, or rubbed off.
  • Preferred sunscreens and sunblocks which will provide this benefit are a copolymer of ethylene and acrylic acid. Compositions comprising this copolymer are disclosed in U.S. Patent 4,663,157, Brock, issued May 5, 1987.
  • Chelators reacts for removing a metal ion from a system by forming a complex so that the metal ion cannot readily participate in or catalyze chemical reactions.
  • the inclusion of a cheiator is especially useful for providing protection against UV radiation which can contribute to excessive scaling or skin texture changes and against other environmental agents which can cause skin damage.
  • chelators that are useful herein are 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.
  • Preferred chelators are furildioxime and derivatives thereof.
  • composition of the present invention may include 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.
  • 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
  • vitamin B3 e.g., nicotinic acid esters and derivatives of niacinamide, commercially available from a number of sources, for example, the Sigma Chemical Company (St. Louis, MO); ICN Biomedicals, Inc. (Irvin, CA) and Aldrich Chemical Company (Milwaukee, Wl) and as described by W. Wenner, "The Reaction of L-Ascorbic and D-lsoascorbic Acid with Nicotinic Acid and Its Amide", J. Organic Chemistry, Vol.
  • vitamin C vitamin E and vitamin K
  • 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.
  • 4% ethyl alcohol solutions are prepared as a blend of actives. 0.75 ml of the active blend is applied to 50 cm 2 of the depilated back of a guinea pig. The treated guinea pigs are exposed to 150 - 200 female mosquitoes (Aedes aegypti) in a cage for a determined time (for example, 4 hours).
  • the number of mosquito biting sites is counted by a LDF (Laser Dopplar Flowmetry) using a template of acetate sheet having 20 holes (2 cm apart, covering approx. 50 cm 2 ) as a site marker for measurement. Measurements are before and after exposure at the specific sites and at the mosquito bite sites. The result is expressed as numbers of bites and the protection percentage calculated by ethyl alcohol control.
  • LDF Laser Dopplar Flowmetry
  • compositions shown below can be prepared by any conventional method known in the art. Suitable methods and formulations are as follows:
  • Example I - HI The active blend as shown below is suitably prepared as follows.
  • step 3 Add the rest of liquid ingredients to the mixture of step 2 until the resulting solution is uniform. If all solid ingredients are not dissolved completely, ultra sonication may be used to dissolve them.
  • the following data shows results of the experimental studies according to the testing procedure described herein.
  • the active blends described above provide excellent repellency against mosquitoes when applied to skin.
  • the protection percentages are calculated based on a control (ethyl alcohol solution). As shown below, protection from at least 80% of the number of bites is provided.
  • Example IV Spray The following example is a spray composition.
  • the spray composition is suitably prepared by the following steps:
  • the following example is a Clear Gel composition.
  • the Clear Gel is suitably prepared by the following steps:
  • Carbopol 954 Carbomer
  • the following example is a UV protect lotion composition.
  • the UV protect lotion is suitably prepared by the following steps:
  • Phase B ingredients (b) Separately, mix Phase B ingredients at a temperature of about 70-75°C until uniform and add to the mixture of Phase A to form a complete emulsion of Phase A-B;
  • the following example is a body moisturizer.
  • the body moisturizer is suitably prepared by the following steps:
  • Phase B ingredients (b) Separately, mix Phase B ingredients at a temperature of about 70-75°C until uniform and add to the mixture of Phase A to form a complete emulsion of Phase A-B;
  • the following example is a moisturizing cream.
  • the moisturizing cream is suitably prepared by the following steps:
  • Phase A ingredients (a) Mix Phase A ingredients at a temperature of about 70-80°C; (b) Separately, mix Phase B ingredients at a temperature of about 70-80°C until uniform and add to the mixture of Phase A to form a complete emulsion of Phase A-B;
  • phase D additive phase D to the batch mixture of phases A-C at about 60°C while continuing to mix until the resulting batch mixture is uniform.
  • the following example is a body powder.
  • the body powder is suitably prepared by the following steps:
  • compositions containing the active blends herein can be safe to the skin and provide long lasting repellent efficacy.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
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Abstract

L'invention concerne une composition insectifuge renfermant: (a) un mélange actif insectifuge comprenant un composé carbonyle de parfum, un alcool de parfum, un ester de parfum, un composé nitrile, un époxyde, et un composé éther; et (b) un excipient cosmétiquement acceptable.
PCT/US1998/024021 1998-11-10 1998-11-10 Composition renfermant un melange actif insectifuge WO2000027197A1 (fr)

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AU13971/99A AU1397199A (en) 1998-11-10 1998-11-10 A composition containing an insect repellent active blend

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Cited By (24)

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DE10135258A1 (de) * 2001-07-19 2003-02-06 Beiersdorf Ag Insektenabwehrende Sonnenschutzmittel
WO2003013243A1 (fr) * 2001-08-11 2003-02-20 Quest International B.V. Insectifuges
WO2006105842A1 (fr) * 2005-04-05 2006-10-12 Merck Patent Gmbh Synergistes servant a renforcer l'effet de repulsifs
US7129271B2 (en) 2000-12-08 2006-10-31 The United States Of America As Represented By The Department Of Health And Human Services Compounds for pest control and methods for their use
US7230033B2 (en) 2000-12-08 2007-06-12 United States of America as represented by the Secretary of the Department of Health and Human Services, Center for Disease Control and Prevention Pest control compositions and methods for their use
EP1964544A1 (fr) * 2007-03-02 2008-09-03 Takasago International Corporation Parfums pour peaux sensibles
US20090162409A1 (en) * 2005-12-12 2009-06-25 Sumitomo Chemical Company, Limited Microencapsulated Pesticide
US8057829B2 (en) 2008-12-30 2011-11-15 Sterling International Inc. Methods for repelling insects using sesquiterpene hydrocarbons and their derivatives
WO2012167901A2 (fr) 2011-06-07 2012-12-13 Beiersdorf Ag Composition cosmétique ou dermatologique de photoprotection, ayant une résistance à l'eau améliorée
WO2012167906A2 (fr) 2011-06-07 2012-12-13 Beiersdorf Ag Compositions cosmétiques ou dermatologiques aux propriétés rhéologiques améliorées
WO2012167905A2 (fr) 2011-06-07 2012-12-13 Beiersdorf Ag Compositions cosmétiques ou dermatologiques exemptes de polyéthylène glycol
DE102011077017A1 (de) * 2011-06-07 2012-12-13 Beiersdorf Ag Kosmetische oder dermatologische Emulsionszubereitungen mit verbesserter Parfumfreisetzung
WO2012168216A2 (fr) 2011-06-07 2012-12-13 Beiersdorf Ag Émulsions cosmétiques ou dermatologiques exemptes d'alcools gras
WO2012167900A2 (fr) 2011-06-07 2012-12-13 Beiersdorf Ag Compositions cosmétiques ou dermatologiques sous forme d'émulsions et ayant une libération de parfum améliorée
WO2012167902A2 (fr) 2011-06-07 2012-12-13 Beiersdorf Ag Compositions cosmétiques ou dermatologiques ayant une stabilité microbiologique améliorée
JP2013177342A (ja) * 2012-02-28 2013-09-09 Kao Corp 昆虫防除剤
WO2013165477A1 (fr) 2012-05-02 2013-11-07 Bedoukian Research, Inc. Lutte contre les moustiques et répulsion des moustiques
WO2015063238A1 (fr) * 2013-11-04 2015-05-07 Wageningen Universiteit Compositions insectifuges et procédés d'utilisation
WO2016136735A1 (fr) * 2015-02-26 2016-09-01 花王株式会社 Insectifuge
US20170079274A1 (en) * 2011-10-17 2017-03-23 The Regents Of The University Of California Methods for assessing repellant quality of organic materials and methods and compositions for repelling arthropods
US10768168B2 (en) 2013-03-15 2020-09-08 The Regents Of The University Of California Methods for identifying arthropod repellents and attractants, and compounds and compositions identified by such methods
US10785978B2 (en) 2012-05-02 2020-09-29 Bedoukian Research, Inc. Control and repellency of biting flies, house flies, ticks, ants, fleas, biting midges, cockroaches, spiders and stink bugs
US11186560B2 (en) 2015-03-18 2021-11-30 The Regents Of The University Of California Arthropod repellent chemicals
EP4038129A4 (fr) * 2019-10-04 2023-10-04 Global Biolife Inc. Composition insectifuge

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Cited By (40)

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Publication number Priority date Publication date Assignee Title
US7629387B2 (en) 2000-12-08 2009-12-08 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Compounds for pest control and methods for their use
US7129271B2 (en) 2000-12-08 2006-10-31 The United States Of America As Represented By The Department Of Health And Human Services Compounds for pest control and methods for their use
US7230033B2 (en) 2000-12-08 2007-06-12 United States of America as represented by the Secretary of the Department of Health and Human Services, Center for Disease Control and Prevention Pest control compositions and methods for their use
DE10135258A1 (de) * 2001-07-19 2003-02-06 Beiersdorf Ag Insektenabwehrende Sonnenschutzmittel
CN1310583C (zh) * 2001-08-11 2007-04-18 探索国际股份有限公司 驱虫剂
WO2003013243A1 (fr) * 2001-08-11 2003-02-20 Quest International B.V. Insectifuges
US7455852B2 (en) 2001-08-11 2008-11-25 Quest International B.V. Insect repellents
WO2006105842A1 (fr) * 2005-04-05 2006-10-12 Merck Patent Gmbh Synergistes servant a renforcer l'effet de repulsifs
US20090162409A1 (en) * 2005-12-12 2009-06-25 Sumitomo Chemical Company, Limited Microencapsulated Pesticide
US8790676B2 (en) * 2005-12-12 2014-07-29 Sumitomo Chemical Company, Limited Microencapsulated pesticide
EP1964544A1 (fr) * 2007-03-02 2008-09-03 Takasago International Corporation Parfums pour peaux sensibles
EP1964542A1 (fr) * 2007-03-02 2008-09-03 Takasago International Corporation Parfums pour peaux sensibles
US8057829B2 (en) 2008-12-30 2011-11-15 Sterling International Inc. Methods for repelling insects using sesquiterpene hydrocarbons and their derivatives
WO2012167900A2 (fr) 2011-06-07 2012-12-13 Beiersdorf Ag Compositions cosmétiques ou dermatologiques sous forme d'émulsions et ayant une libération de parfum améliorée
WO2012167905A2 (fr) 2011-06-07 2012-12-13 Beiersdorf Ag Compositions cosmétiques ou dermatologiques exemptes de polyéthylène glycol
DE102011077017A1 (de) * 2011-06-07 2012-12-13 Beiersdorf Ag Kosmetische oder dermatologische Emulsionszubereitungen mit verbesserter Parfumfreisetzung
WO2012168216A2 (fr) 2011-06-07 2012-12-13 Beiersdorf Ag Émulsions cosmétiques ou dermatologiques exemptes d'alcools gras
WO2012167906A2 (fr) 2011-06-07 2012-12-13 Beiersdorf Ag Compositions cosmétiques ou dermatologiques aux propriétés rhéologiques améliorées
WO2012167902A2 (fr) 2011-06-07 2012-12-13 Beiersdorf Ag Compositions cosmétiques ou dermatologiques ayant une stabilité microbiologique améliorée
WO2012167901A2 (fr) 2011-06-07 2012-12-13 Beiersdorf Ag Composition cosmétique ou dermatologique de photoprotection, ayant une résistance à l'eau améliorée
US10292396B2 (en) * 2011-10-17 2019-05-21 The Regents Of The University Of California Methods for assessing repellant quality of organic materials and methods and compositions for repelling arthropods
US20170079274A1 (en) * 2011-10-17 2017-03-23 The Regents Of The University Of California Methods for assessing repellant quality of organic materials and methods and compositions for repelling arthropods
JP2013177342A (ja) * 2012-02-28 2013-09-09 Kao Corp 昆虫防除剤
CN110074108A (zh) * 2012-05-02 2019-08-02 贝杜基昂研究股份有限公司 对蚊子的控制和驱避
CN104334022A (zh) * 2012-05-02 2015-02-04 贝杜基昂研究股份有限公司 对蚊子的控制和驱避
EP2849564A4 (fr) * 2012-05-02 2016-04-13 Bedoukian Res Inc Lutte contre les moustiques et répulsion des moustiques
WO2013165477A1 (fr) 2012-05-02 2013-11-07 Bedoukian Research, Inc. Lutte contre les moustiques et répulsion des moustiques
US10785978B2 (en) 2012-05-02 2020-09-29 Bedoukian Research, Inc. Control and repellency of biting flies, house flies, ticks, ants, fleas, biting midges, cockroaches, spiders and stink bugs
CN104334022B (zh) * 2012-05-02 2019-09-10 贝杜基昂研究股份有限公司 对蚊子的控制和驱避
US10768168B2 (en) 2013-03-15 2020-09-08 The Regents Of The University Of California Methods for identifying arthropod repellents and attractants, and compounds and compositions identified by such methods
WO2015063238A1 (fr) * 2013-11-04 2015-05-07 Wageningen Universiteit Compositions insectifuges et procédés d'utilisation
WO2016136735A1 (fr) * 2015-02-26 2016-09-01 花王株式会社 Insectifuge
US20180042225A1 (en) * 2015-02-26 2018-02-15 Kao Corporation Insect Repellent
CN107205382A (zh) * 2015-02-26 2017-09-26 花王株式会社 昆虫驱避剂
US10779531B2 (en) 2015-02-26 2020-09-22 Kao Corporation Insect repellent
JP2016172715A (ja) * 2015-02-26 2016-09-29 花王株式会社 昆虫忌避剤
CN107205382B (zh) * 2015-02-26 2020-10-09 花王株式会社 昆虫驱避剂
TWI740695B (zh) 2015-02-26 2021-09-21 日商花王股份有限公司 昆蟲忌避劑
US11186560B2 (en) 2015-03-18 2021-11-30 The Regents Of The University Of California Arthropod repellent chemicals
EP4038129A4 (fr) * 2019-10-04 2023-10-04 Global Biolife Inc. Composition insectifuge

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