WO2002043491A1 - Extended duration insect repellent composition and method of application to the skin - Google Patents

Extended duration insect repellent composition and method of application to the skin Download PDF

Info

Publication number
WO2002043491A1
WO2002043491A1 PCT/US2001/044299 US0144299W WO0243491A1 WO 2002043491 A1 WO2002043491 A1 WO 2002043491A1 US 0144299 W US0144299 W US 0144299W WO 0243491 A1 WO0243491 A1 WO 0243491A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
polyurethane
insect repellent
urethane polymer
skin
Prior art date
Application number
PCT/US2001/044299
Other languages
French (fr)
Other versions
WO2002043491A9 (en
Inventor
Anthony Gonzalez
Andrew H. Pechko
Robert E. Kalafsky
Original Assignee
Avon Products, Inc.
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 Avon Products, Inc. filed Critical Avon Products, Inc.
Priority to CA 2393290 priority Critical patent/CA2393290A1/en
Priority to DE2001605389 priority patent/DE60105389T2/en
Priority to EP20010998225 priority patent/EP1250043B1/en
Priority to US10/203,839 priority patent/US7150878B2/en
Priority to AU2002217888A priority patent/AU2002217888B2/en
Priority to AU1788802A priority patent/AU1788802A/en
Publication of WO2002043491A1 publication Critical patent/WO2002043491A1/en
Publication of WO2002043491A9 publication Critical patent/WO2002043491A9/en

Links

Classifications

    • 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
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A01N25/06—Aerosols
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A01N25/10—Macromolecular compounds
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/24—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients to enhance the sticking of the active ingredients
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system
    • 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
    • A01N37/00—Biocides, 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
    • A01N37/18—Biocides, 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 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • 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
    • A01N37/00—Biocides, 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
    • A01N37/44—Biocides, 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 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • 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
    • A01N61/00—Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action
    • 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
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • 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
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • A01N65/20—Fabaceae or Leguminosae [Pea or Legume family], e.g. pea, lentil, soybean, clover, acacia, honey locust, derris or millettia
    • 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
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/40—Liliopsida [monocotyledons]
    • A01N65/44—Poaceae or Gramineae [Grass family], e.g. bamboo, lemon grass or citronella grass
    • 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
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/42—Amides
    • 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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/87—Polyurethanes
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00—Drug, bio-affecting and body treating compositions
    • Y10S424/10—Insect repellent

Definitions

  • the present invention relates to an insect repellent composition. More particularly, the present invention relates to an insect repellent exhibiting extended duration of repellency on the skin. Further, the present invention relates to such a composition exhibiting water, sweat, and wear resistance. As used herein, the term "insect” is intended to mean any insect or arachnid.
  • Insect repellent compositions are available commercially in a variety of product forms, such as aerosol and pump sprays, creams, lotions and gels. Depending upon the product form, the compositions may be administered to both the skin and to clothing. The compositions may be administered in preparation for a variety of outdoor situations, such as picnicking, hiking, fishing, swimming and exercise.
  • a common problem associated with insect repellent compositions is a lack of duration of repellency. This translates into insufficient repellency and the need to re-apply often. Insect repellent compositions may wash off from exposure to water, sweating and/or physical contact with the skin. It would be desirable to increase the duration of repellency of insect repellent compositions on the skin. It would further be desirable to have insect repellent compositions that resist removal by exposure to water, sweating and physical contact.
  • U.S. Patent No. 4,913,897 to Chvapil et al. is directed to hydrogel compositions that form films on the surface of the skin to protect it against exposure to toxic substances and infections. This patent provides that such films may also contain an insect repellent.
  • the urethane polymers of the present invention are not hydrogels nor do they form hydrogels in the present invention.
  • an insect repellent composition having an amount of an insect repellent active sufficient to repel insects when the composition is applied to the skin.
  • the composition also has an amount of urethane polymer sufficient to form a thin, substantially continuous film on the skin.
  • the composition also has a cosmetically acceptable vehicle.
  • a method of repelling insects from the skin is provided.
  • the composition described above is applied to the skin.
  • This urethane film is substantially uniform and provides superior coverage over the peaks and valleys of the skin surface, allowing for reduction of unprotected skin areas.
  • Figure 1 is a bar graph illustrating the duration of insect repellency with varying levels of urethane polymers.
  • Figure 2 is a view of a photograph of showing the topography of an artificial skin substrate without the application of the present invention.
  • Figure 3 is a view of a photograph showing the topography of a skin substrate with and without the application of an acrylic polymer not of the present invention.
  • Figure 4 is a view of a photograph showing the appearance of a skin substrate with and without the application of the present invention.
  • an insect repellent composition can be produced that exhibits extended duration of repellency on the skin, and also enhanced insect repellency.
  • the composition has superior spread characteristics on the skin.
  • the composition may also exhibit water, sweat and wear resistance.
  • the composition can be formulated to be substantially transparent or otherwise aesthetically acceptable to impart a pleasant feel or sensation to the skin.
  • the present composition leaves a uniform film on the surface of the skin.
  • the composition which exhibits superior spread characteristics, provides more uniform and consistent coverage on the skin.
  • the film has been found to maintain the duration of the insect repellent active(s) for a longer period of time than it would otherwise remain without the urethane polymer.
  • the film also affords sustained release of the active. Additionally, enhanced resistance to water, sweat, and wear may be observed.
  • the film has an enhanced degree of insect repellency for a given amount of insect repellent active employed. Thus, the amount of insect repellent active applied to the skin can be minimized.
  • the film-forming component of the present composition is a urethane polymer resin.
  • Urethane polymers are formed by reactions of diisocyanate and glycol monomers.
  • Preferred urethane polymer resins for use in the present invention are of the following formula:
  • R and R' are, independently, any linear or branched alkyl, alkylene, aliphatic or aromatic group having from 1 to about 30 carbon atoms, preferably about 6 to about 24 carbon atoms, and n is an integer from 2 to about 1000.
  • R' is cyclic, it preferably contains 6 or more carbon atoms.
  • Urethane polymer resins useful in the present invention can be either hydrophobic or hydrophilic.
  • urethane polymer resins are those referred to in the art as Polyurethane-1 , Polyurethane-2, Polyurethane-4, Polyurethane-5 or mixtures thereof. These urethane polymer resins are described in the International Cosmetic Ingredient Dictionary and Handbook, 8 th edition, Printed Edition Pages 1152-1153, which is incorporated herein by reference.
  • the urethane polymer is present in an amount about 0.1 wt.% to about 20 wt.% based on the total weight of the composition.
  • the amount of the urethane polymer is preferably about 0.5 wt.% to about 10 wt.%, and, most preferably, about 1 wt.% to about 5 wt.%, based on the total weight of the composition.
  • the insect repellent or insect repellent active employed in the present composition may be any known in the art.
  • Such actives include, but are not limited to, N,N diethyl- m-toluamide (DEET), ethyl butylacetylaminopropionate (IR3535 by Merck Co.), hydroxy-ethyl isobutyl piperidine carboxylate (1-piperidinecarboxylic acid) (Bayer KBR 3023), oil of citronella, soy bean oil, lemon grass oil, geranium/geraniol oil, p-menthane-3,8-diol, or mixtures thereof.
  • DEET N,N diethyl- m-toluamide
  • IR3535 ethyl butylacetylaminopropionate
  • hydroxy-ethyl isobutyl piperidine carboxylate (1-piperidinecarboxylic acid) Bayer KBR 3023
  • oil of citronella soy bean oil, lemon grass oil, geranium/geraniol oil, p-menthane
  • the amount of insect repellent active is about 0.1 wt.% to about 70 wt.% based on the total weight of the composition.
  • the amount of insect repellent active is preferably about 0.1 wt.% to about 25 wt.%, and, most preferably, about 5 wt.% to about 25 wt.%, based on the total weight of the composition.
  • the present composition may take any form known in the art. Such forms include, but are not limited to, a cream, lotion, gel, solution, ointment, towelette, mousse, stick, or pump spray or aerosol. If an aerosol spray, the composition may contain propellents, such as hydrocarbons, hydrofluorocarbons, chlorofluorocarbons and ethers.
  • the composition may be aqueous or anhydrous.
  • the composition may further be in an emulsion form.
  • the present composition preferably has a vehicle.
  • Such vehicles may be any known in the art including, for example, water; vegetable oils; esters such as octyl palmitate, isopropyl myristate and isopropyl palmitate; ethers such as dicapryl ether and dimethyl isosorbide; alcohols such as ethanol and isopropanol; fatty alcohols such as cetyl alcohol, stearyl alcohol and behenyl alcohol; isoparaffins such as isooctane, isododecane and isohexadecane; silicone oils such as cyclomethicone, dimethicone, dimethicone cross-polymers, polysiloxanes and their derivatives, preferably organomodified derivatives; hydrocarbon oils such as mineral oil, petrolatum, isoeicosane and polyisobutene; polyols such as propylene glycol, glycerin, butylene glycol, pentylene glycol and hexylene glycol; waxes
  • the present composition may further include a sunscreen.
  • the sunscreen may be any sunscreen know in the art. Such sunscreens include, but are not limited to, oxybenzone, sulisobenzone, dioxybenzone,
  • the sunscreen is preferably about 1 wt.% to about 45 wt.% of the total weight of the composition.
  • the sunscreen is about 2 wt.% to about 35 wt.% of the total weight of the composition.
  • the sunscreen protects against both UVA and UVB radiation, and provides a SPF factor of at least about 2 and more preferably at least about 4.
  • the preferred range of SPF protection is about 10 to about 50 and most preferably about 15 to about 30.
  • the present composition may have one or more of the following additional ingredients: anesthetics, anti-allergenics, antifungals, anti-inflammatories, antiseptics, chelating agents, colorants, depigmenting agents, emollients, emulsifiers, exfollients, fragrances, humectants, lubricants, moisturizers, pharmaceutical agents, preservatives, skin penetration enhancers, stabilizers, surfactants, thickeners, viscosity modifiers, vitamins or any combinations of these ingredients. Examples 1 and 2 and Control
  • compositions of the present invention were tested for duration of insect repellency.
  • a control composition (“the Control") was likewise tested.
  • compositions of Examples 1 and 2 had polyurethane concentrations of 1.0 wt.% and 2.0 wt.%, respectively, based upon the total weight of the compositions.
  • the Control did not have any polyurethane (zero wt.%).
  • the polyurethane resin employed was Polyurethane-1. All the compositions had 20 wt.% of IR3535 (Merck) as an insect repellent active, and q.s. with a mixture of alcohol and water.
  • the duration of insect repellency was tested on five subjects in a cage test utilizing a 1 cubic meter cage containing 200 mosquitoes.
  • FIG. 2 shows a 3-dimensional interactive display of the bare substrate as viewed under an optical profiler microscope. The peaks and valleys of the skin surface are clearly pronounced.
  • tape was placed over the left side of a substrate sample.
  • An insect repellent composition containing a conventional acrylic film forming polymer was applied to the right side of the substrate, allowed to dry and the tape was removed.
  • a digital image was taken of this substrate surface using a Wyko NT1000 Optical Profiler made by Vecco.

Abstract

Disclosed is an insect repellent composition. The composition has an amount of an insect repellent active effective to repel insects when the composition is applied to the skin, and an amount of a urethane polymer sufficient to form a film on the surface of the skin. The composition also has a cosmetically-acceptable vehicle. Also disclosed is a method of repelling insects from the skin by applying the composition to the skin.

Description

EXTENDED DURATION INSECT REPELLENT
COMPOSITION AND METHOD OF
APPLICATION TO THE SKIN
BACKGROUND OF THE INVENTION
Field of the Invention
The present invention relates to an insect repellent composition. More particularly, the present invention relates to an insect repellent exhibiting extended duration of repellency on the skin. Further, the present invention relates to such a composition exhibiting water, sweat, and wear resistance. As used herein, the term "insect" is intended to mean any insect or arachnid.
2. Description of the Prior Art
Insect repellent compositions are available commercially in a variety of product forms, such as aerosol and pump sprays, creams, lotions and gels. Depending upon the product form, the compositions may be administered to both the skin and to clothing. The compositions may be administered in preparation for a variety of outdoor situations, such as picnicking, hiking, fishing, swimming and exercise.
A common problem associated with insect repellent compositions is a lack of duration of repellency. This translates into insufficient repellency and the need to re-apply often. Insect repellent compositions may wash off from exposure to water, sweating and/or physical contact with the skin. It would be desirable to increase the duration of repellency of insect repellent compositions on the skin. It would further be desirable to have insect repellent compositions that resist removal by exposure to water, sweating and physical contact. U.S. Patent No. 4,913,897 to Chvapil et al. is directed to hydrogel compositions that form films on the surface of the skin to protect it against exposure to toxic substances and infections. This patent provides that such films may also contain an insect repellent. The urethane polymers of the present invention are not hydrogels nor do they form hydrogels in the present invention.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide an insect repellent composition exhibiting extended duration and enhanced degree of repellency on the skin.
It is another object of the present invention to provide such a composition that provides even application and is water, sweat, and wear
resistant.
It is a further object of the present invention to provide such a composition that is aesthetically acceptable.
These and other objects of the present invention are achieved by an insect repellent composition having an amount of an insect repellent active sufficient to repel insects when the composition is applied to the skin. The composition also has an amount of urethane polymer sufficient to form a thin, substantially continuous film on the skin. The composition also has a cosmetically acceptable vehicle.
Further according to the present invention, there is provided a method of repelling insects from the skin. The composition described above is applied to the skin. A thin urethane film, that is different from a hydrogel film, remains on the skin to enhance the function and effectiveness of the insect repellent. This urethane film is substantially uniform and provides superior coverage over the peaks and valleys of the skin surface, allowing for reduction of unprotected skin areas.
DESCRIPTION OF THE DRAWINGS
Figure 1 is a bar graph illustrating the duration of insect repellency with varying levels of urethane polymers. Figure 2 is a view of a photograph of showing the topography of an artificial skin substrate without the application of the present invention.
Figure 3 is a view of a photograph showing the topography of a skin substrate with and without the application of an acrylic polymer not of the present invention. Figure 4 is a view of a photograph showing the appearance of a skin substrate with and without the application of the present invention. DETAILED DESCRIPTION OF THE INVENTION
The present invention surprisingly found that an insect repellent composition can be produced that exhibits extended duration of repellency on the skin, and also enhanced insect repellency. In addition, the composition has superior spread characteristics on the skin. The composition may also exhibit water, sweat and wear resistance.
The composition can be formulated to be substantially transparent or otherwise aesthetically acceptable to impart a pleasant feel or sensation to the skin. When applied to the skin, the present composition leaves a uniform film on the surface of the skin. The composition, which exhibits superior spread characteristics, provides more uniform and consistent coverage on the skin. The film has been found to maintain the duration of the insect repellent active(s) for a longer period of time than it would otherwise remain without the urethane polymer. The film also affords sustained release of the active. Additionally, enhanced resistance to water, sweat, and wear may be observed. In view of the foregoing advantages, the film has an enhanced degree of insect repellency for a given amount of insect repellent active employed. Thus, the amount of insect repellent active applied to the skin can be minimized.
The film-forming component of the present composition is a urethane polymer resin. Urethane polymers are formed by reactions of diisocyanate and glycol monomers. Preferred urethane polymer resins for use in the present invention are of the following formula:
Figure imgf000007_0001
wherein R and R' are, independently, any linear or branched alkyl, alkylene, aliphatic or aromatic group having from 1 to about 30 carbon atoms, preferably about 6 to about 24 carbon atoms, and n is an integer from 2 to about 1000. When R' is cyclic, it preferably contains 6 or more carbon atoms. Urethane polymer resins useful in the present invention can be either hydrophobic or hydrophilic.
The most preferred urethane polymer resins are those referred to in the art as Polyurethane-1 , Polyurethane-2, Polyurethane-4, Polyurethane-5 or mixtures thereof. These urethane polymer resins are described in the International Cosmetic Ingredient Dictionary and Handbook, 8th edition, Printed Edition Pages 1152-1153, which is incorporated herein by reference.
The urethane polymer is present in an amount about 0.1 wt.% to about 20 wt.% based on the total weight of the composition. The amount of the urethane polymer is preferably about 0.5 wt.% to about 10 wt.%, and, most preferably, about 1 wt.% to about 5 wt.%, based on the total weight of the composition. The insect repellent or insect repellent active employed in the present composition may be any known in the art. Such actives that can be used in the present invention include, but are not limited to, N,N diethyl- m-toluamide (DEET), ethyl butylacetylaminopropionate (IR3535 by Merck Co.), hydroxy-ethyl isobutyl piperidine carboxylate (1-piperidinecarboxylic acid) (Bayer KBR 3023), oil of citronella, soy bean oil, lemon grass oil, geranium/geraniol oil, p-menthane-3,8-diol, or mixtures thereof. Other actives that can be used in the present invention are disclosed in U.S. Patent Nos. 5,130,136 and 5,698,209, which are incorporated herein by reference.
The amount of insect repellent active is about 0.1 wt.% to about 70 wt.% based on the total weight of the composition. The amount of insect repellent active is preferably about 0.1 wt.% to about 25 wt.%, and, most preferably, about 5 wt.% to about 25 wt.%, based on the total weight of the composition.
The present composition may take any form known in the art. Such forms include, but are not limited to, a cream, lotion, gel, solution, ointment, towelette, mousse, stick, or pump spray or aerosol. If an aerosol spray, the composition may contain propellents, such as hydrocarbons, hydrofluorocarbons, chlorofluorocarbons and ethers. The composition may be aqueous or anhydrous. The composition may further be in an emulsion form. The present composition preferably has a vehicle. Such vehicles may be any known in the art including, for example, water; vegetable oils; esters such as octyl palmitate, isopropyl myristate and isopropyl palmitate; ethers such as dicapryl ether and dimethyl isosorbide; alcohols such as ethanol and isopropanol; fatty alcohols such as cetyl alcohol, stearyl alcohol and behenyl alcohol; isoparaffins such as isooctane, isododecane and isohexadecane; silicone oils such as cyclomethicone, dimethicone, dimethicone cross-polymers, polysiloxanes and their derivatives, preferably organomodified derivatives; hydrocarbon oils such as mineral oil, petrolatum, isoeicosane and polyisobutene; polyols such as propylene glycol, glycerin, butylene glycol, pentylene glycol and hexylene glycol; waxes such as beeswax and botanical waxes; and mixtures of the foregoing. The vehicle is about 0.1 wt.% to about 99.8 wt.% of the total weight of the composition. Preferably, the vehicle is about 10 wt.% to about 93 wt.% of the total weight of the composition.
Optionally, the present composition may further include a sunscreen. The sunscreen may be any sunscreen know in the art. Such sunscreens include, but are not limited to, oxybenzone, sulisobenzone, dioxybenzone,
menthyl antranilate, para aminobenzoic acid, dea methoxycinnamate, octyl methoxycinnamate, octocrylene, drometrizole trisiloxane, octyl salicylate, homomenthyl salicylate, octyl dimethyl PABA, TEA salicylate, titanium dioxide, zinc oxide, butylmethoxy dibenzoylmethane, methyl benzilidene camphor, octyl triazone, terephthalydiene dicamphor sulfonic acid, ethyl PABA, hydroxy methylphenyl benzotriazole, methylene bis- benzotriazoyltetramethylbutylphenol (MBBT), bis-ethylhexyl oxyphenol methoxyphenol triazine (BEMT), and mixtures thereof. Other sunscreens include those disclosed in U.S. Patent No. 5,000,937, which is incorporated herein.
The sunscreen is preferably about 1 wt.% to about 45 wt.% of the total weight of the composition. Preferably, the sunscreen is about 2 wt.% to about 35 wt.% of the total weight of the composition. Most preferably, the sunscreen protects against both UVA and UVB radiation, and provides a SPF factor of at least about 2 and more preferably at least about 4. The preferred range of SPF protection is about 10 to about 50 and most preferably about 15 to about 30. Further optionally, the present composition may have one or more of the following additional ingredients: anesthetics, anti-allergenics, antifungals, anti-inflammatories, antiseptics, chelating agents, colorants, depigmenting agents, emollients, emulsifiers, exfollients, fragrances, humectants, lubricants, moisturizers, pharmaceutical agents, preservatives, skin penetration enhancers, stabilizers, surfactants, thickeners, viscosity modifiers, vitamins or any combinations of these ingredients. Examples 1 and 2 and Control
Two compositions of the present invention were tested for duration of insect repellency. A control composition ("the Control") was likewise tested.
The compositions of Examples 1 and 2 had polyurethane concentrations of 1.0 wt.% and 2.0 wt.%, respectively, based upon the total weight of the compositions. The Control did not have any polyurethane (zero wt.%). The polyurethane resin employed was Polyurethane-1. All the compositions had 20 wt.% of IR3535 (Merck) as an insect repellent active, and q.s. with a mixture of alcohol and water.
The duration of insect repellency was tested on five subjects in a cage test utilizing a 1 cubic meter cage containing 200 mosquitoes.
The results are set forth in Figure 1. The inclusion of polyurethane significantly increased the duration of repellency at both the 1.0 wt.% and 2.0 wt.% levels.
Optical Profilometry of Polymer Films To determine the attributes of the present invention, an optical profilometry study of the present invention was performed on samples of an artificial skin substrate. Figure 2 shows a 3-dimensional interactive display of the bare substrate as viewed under an optical profiler microscope. The peaks and valleys of the skin surface are clearly pronounced. As a comparison, tape was placed over the left side of a substrate sample. An insect repellent composition containing a conventional acrylic film forming polymer was applied to the right side of the substrate, allowed to dry and the tape was removed. A digital image was taken of this substrate surface using a Wyko NT1000 Optical Profiler made by Vecco. As is evident in Figure 3, there was bleeding of the insect repellent composition under the tape, as well as non-uniform coverage of the peaks and valleys over which it was applied. As a further comparison, similar insect repellent composition having the urethane polymer film former of the present invention was prepared. Tape was placed over the left side of a substrate sample, and the inventive composition was applied to the right side and allowed to dry. The tape was removed and a digital image was taken of the substrate surface. As is evident from Figure 4, this composition stayed where applied and did not run under the tape. Moreover, there was maximum, substantially uniform coverage of the peaks and valleys over which it was applied.
It should be understood that the foregoing description is only illustrative of the present invention. Various alternatives and modifications can be devised by those skilled in the art without departing from the invention. Accordingly, the present invention is intended to embrace all such alternatives, modifications and variances that fall within the scope of the appended claims.

Claims

WHATIS CLAIMED IS
1. An insect repellent composition, comprising:
5 an amount, of an insect repellent active effective to repel insects when the composition is applied to skin; and
an amount: of a urethane polymer sufficient to form a film on the surface of the skin. 10
2. The composition of claim 1 , further comprising a cosmetically- acceptable vehicle.
3. The composition of claim 1 , wherein the urethane polymer 15 has the following formula:
Figure imgf000013_0001
2.0 wherein R and R' are, independently, any linear or branched alkyl, alkylene, aliphatic or aromatic group having from 1 to about 30 carbon atoms, and n is an integer from 2 to about 1000.
4. The composition of claim 3, wherein R' is cyclic and has 6 or more carbon atoms.
5. The composition of claim 1 , wherein the urethane polymer is about 0.1 wt.% to about 20 wt.% based on the total weight of the composition.
6. The composition of claim 1 , wherein the urethane polymer is about 0.5 wt.% to about 10 wt.% based on the total weight of the composition.
7. The composition of claim 1 , wherein the amount of insect repellent active is about 0.1 wt.% to about 70 wt.% based on the total weight of the composition.
8. The composition of claim 1 , wherein the urethane polymer is selected from the group consisting of Polyurethane-1 , Polyurethane-2, Polyurethane-4, Polyurethane-5, and mixtures thereof.
9. The composition of claim 1 , wherein the insect repellent active is selected from the group consisting of N,N diethyl-m-toluamide, ethyl butylacetylaminopropionate, hydroxy-ethyl isobutyl piperidine carboxylate, oil of citronella, soy bean oil, lemon grass oil, geranium/geraniol oil, p-menthane-3,8-diol, and mixtures thereof.
10. The composition of claim 1 , wherein the composition is in the form selected from the group consisting of a cream, lotion, gel, solution, towelette, mousse, stick, ointment, spray, and aerosol.
11. The composition of claim 1 , further comprising a sunscreen.
12. The composition of claim 1 , wherein the sunscreen is selected from a group consisting of oxybenzone, sulisobenzone, dioxybenzone, menthyl anthranilate, para aminobenzoic acid, octyl methoxycinnamate, octocrylene, drometrizole trisiloxane, octyl salicylate, homomenthyl salicylate, octyl dimethyl PABA, TEA salicylate, titanium dioxide, zinc oxide, butylmethoxy dibenzoylmethane, methyl benzilidene camphor, octyl triazone, terephthalydiene dicamphor, sulfonic acid, ethyl PABA, hydroxy methylphenyl benzotriazole, methylene bis- benzotriazoyltetramethylbutylphenol, bis-octyloxyphenol methoxyphenol triazine, and mixtures thereof.
13. The composition of claim 12, wherein the sunscreen is selected from a group consisting of oxybenzone, octyl methoxycinnamate, octocrylene, octyl salicylate, titanium dioxide, zinc oxide, butylmethoxy dibenzoylmethane, methylene bis-benzotriazoyltetramethylbutylphenol, bis- octyloxyphenol methoxyphenol triazine, and mixtures thereof.
14. The composition of claim 1, wherein the urethane polymer does notform a hydrogel or a hydrogel film.
15. An insect repellent composition, comprising:
an amount of an insect repellent active effective to repel insects when the composition is applied to skin;
aboutθ.1 wt.% to about 20 wt.% based on the total weight of the composition of a urethane polymer, wherein the urethane polymer forms a film on the surface of the skin; and
a cosmetically-acceptable vehicle.
16. The composition of claim 15, wherein the urethane polymer has the following formula:
Figure imgf000016_0001
wherein R and R' are, independently, any linear or branched alkyl, alkylene, aliphatic or aromatic group having from 1 to about 30 carbon atoms, and n is an integer from 2 to about 1000.
17. The composition of claim 16, wherein R' is cyclic and has 6 or more carbon atoms.
18. The composition of claim 15, wherein the urethane polymer is selected from the group consisting of Polyurethane-1 , Polyurethane-2,
Polyurethane-4, Polyurethane-5, and mixtures thereof.
19. A method of repelling insects from the skin, comprising applying to the skin the composition of claim 1.
20. The method of claim 19, wherein the urethane polymer is about 0.1 wt.% to about 20 wt.% based on the total weight of the composition.
21. The method of claim 19, wherein the urethane polymer has the following formula: wherein R and R' are, independently, any linear or branched alkyl, alkylene, aliphatic or aromatic group having from 1 to about 30 carbon atoms, and n is an integer from 2 to about 1000.
22. The composition of claim 21 , wherein R' is cyclic and has 6 or more carbon atoms.
23. The method of claim 19, wherein the polyurethane is selected from the group consisting of Polyurethane-1 , Polyurethane-2, Polyurethane-4, Polyurethane-5, and mixtures thereof.
24. The method of claim 19, wherein the insect repellent active is about 0.1 wt.% to about 70 wt.% based on the total weight of the composition.
25. An insect repellent composition comprising: an effective amount of an insect repellent; a film-forming urethane polymer; and a volatile component, wherein the composition is dispensed from a spray container.
26. The composition of claim 25, wherein the composition is substantially anhydrous.
27. The composition of claim 25, wherein the spray container is selected from the group consisting of a pump spray container and an aerosol spray container.
28. The composition of claim 25, wherein the volatile component is selected from the group consisting of one or more alcohols, hydrocarbons, ethers, silicones, water, and mixtures thereof.
PCT/US2001/044299 2000-11-28 2001-11-27 Extended duration insect repellent composition and method of application to the skin WO2002043491A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CA 2393290 CA2393290A1 (en) 2000-11-28 2001-11-27 Extended duration insect repellent composition and method of application to the skin
DE2001605389 DE60105389T2 (en) 2000-11-28 2001-11-27 INSECT-SPRAYING COMPOSITION WITH EXTENDED DURATION AND PROCEDURE FOR APPLYING TO SKIN
EP20010998225 EP1250043B1 (en) 2000-11-28 2001-11-27 Extended duration insect repellent composition and method of application to the skin
US10/203,839 US7150878B2 (en) 2000-11-28 2001-11-27 Extended duration insect repellent composition and method of application to the skin
AU2002217888A AU2002217888B2 (en) 2000-11-28 2001-11-27 Extended duration insect repellent composition and method of application to the skin
AU1788802A AU1788802A (en) 2000-11-28 2001-11-27 Extended duration insect repellent composition and method of application to the skin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/724,160 US6719959B1 (en) 2000-11-28 2000-11-28 Extended duration insect repellent composition and method of application to the skin
US09/724,160 2000-11-28

Publications (2)

Publication Number Publication Date
WO2002043491A1 true WO2002043491A1 (en) 2002-06-06
WO2002043491A9 WO2002043491A9 (en) 2003-08-14

Family

ID=24909268

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/044299 WO2002043491A1 (en) 2000-11-28 2001-11-27 Extended duration insect repellent composition and method of application to the skin

Country Status (6)

Country Link
US (2) US6719959B1 (en)
EP (1) EP1250043B1 (en)
AU (2) AU1788802A (en)
CA (1) CA2393290A1 (en)
DE (1) DE60105389T2 (en)
WO (1) WO2002043491A1 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1213010A2 (en) * 2000-12-09 2002-06-12 Beiersdorf AG Use of water-soluble and film-forming polymers for increasing the light protection factor and/or the protection performance to UV-A in cosmetic or dermatological formulations
EP1762221A1 (en) * 2005-07-20 2007-03-14 Beiersdorf AG Insect repellent with long lasting affect
EP3099381A4 (en) * 2014-01-28 2017-07-19 Avon Products, Inc. Extended release fragrance compositions
US10842729B2 (en) 2017-09-13 2020-11-24 Living Proof, Inc. Color protectant compositions
US10987300B2 (en) 2017-09-13 2021-04-27 Living Proof, Inc. Long lasting cosmetic compositions
US11622929B2 (en) 2016-03-08 2023-04-11 Living Proof, Inc. Long lasting cosmetic compositions

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6719959B1 (en) * 2000-11-28 2004-04-13 Avon Products, Inc. Extended duration insect repellent composition and method of application to the skin
US20060057084A1 (en) * 2004-09-14 2006-03-16 Gonzalez Anthony D Attero-chromic color aggregates
US20070264294A1 (en) * 2006-05-10 2007-11-15 Lance-Gomez Edward T Insect control compositions
US8114386B2 (en) * 2006-05-12 2012-02-14 3M Innovative Properties Company Topical insect repellent composition and method of application
US20070298063A1 (en) * 2006-06-23 2007-12-27 Riannon Walsh Equine gnat repellant
US7744911B2 (en) * 2006-08-25 2010-06-29 Avon Products, Inc Water based clear sunscreen and insect repellent composition
WO2009082565A1 (en) 2007-12-20 2009-07-02 Avon Products, Inc. Cosmetic compositions for imparting superhydrophobic films
CN101980686A (en) * 2008-03-04 2011-02-23 雅芳产品公司 Cosmetic compositions for imparting superhydrophobic fimls
US8747875B2 (en) * 2008-09-29 2014-06-10 The Hartz Mountain Corporation Photo-stable pest control
CN102596152A (en) * 2009-11-06 2012-07-18 雅芳产品公司 Methods and compositions for preventing or reducing frizzy appearance of hair
ES2646862T3 (en) 2009-11-06 2017-12-18 Avon Products, Inc. Methods and compositions to prevent or reduce the curly appearance of hair
EP2324819B1 (en) * 2009-11-19 2015-07-08 L'Oréal Coloured perfume composition comprising a hydrophilic UVA filter without alkyl diphenylacrylate
US9956432B2 (en) 2010-11-05 2018-05-01 Avon Products, Inc. Method for improving color retention in artificially colored hair
US9491942B2 (en) 2011-10-17 2016-11-15 The Regents Of The University Of California Methods for assessing repellant quality of organic materials and methods and compositions for repelling arthropods
US8592376B2 (en) 2011-12-06 2013-11-26 Avon Products, Inc Hair care compositions
WO2014153190A1 (en) 2013-03-14 2014-09-25 The Regents Of The University Of California Methods for identifying arthropod repellents based on modulation of ionotropic receptors, and compounds and compositions identified thereby
WO2014144685A2 (en) 2013-03-15 2014-09-18 The Regents Of The University Of California Methods for identifying arthropod repellents and attractants, and compounds and compositions identified by such methods
EP3270692A4 (en) 2015-03-18 2019-02-13 The Regents of the University of California Anthropod repellent chemicals
US10405552B2 (en) 2017-05-22 2019-09-10 S. C. Johnson & Son, Inc. Composite insecticidal composition
US10264787B1 (en) 2017-11-28 2019-04-23 BIOVECBLOK s.r.l. Natural mosquito larvicide
US10306894B1 (en) 2017-11-28 2019-06-04 BIOVECBLOK s.r.l. Natural mosquito repellant
CN107857858B (en) * 2017-11-29 2021-05-25 黄山佳杰新材料科技有限公司 Hydroterpineol modified polyurethane, preparation method thereof and coating composition containing polyurethane
CN110495457A (en) * 2018-05-18 2019-11-26 南通宏洋化工有限公司 A kind of long-acting insect repellent
CN113226029A (en) * 2018-12-28 2021-08-06 花王株式会社 Pest repellent composition

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5882633A (en) * 1996-12-17 1999-03-16 Societe L'oreal S.A. Compositions comprising a dibenzoylmethane derivative, a 1,3,5-triazine derivative and an amide compound, and methods of use therefor
US5911980A (en) * 1996-06-27 1999-06-15 Macrochem Corporation Lipophilic and amphiphilic or hydrophilic film-forming polymer compositions, and use thereof in topical agent delivery system and method of delivering agents to the skin
US5916541A (en) * 1992-06-25 1999-06-29 Stewart; Ernest G. Water resistant sunscreen and insect repellent composition

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4047505A (en) 1976-08-02 1977-09-13 Canada, Her Majesty The Queen In Right Of, As Represented By The Secretary Of National Defence Insect repellent collar
GB2161078B (en) 1983-12-29 1988-01-20 Takiron Co Pest-repellent
US4913897A (en) 1987-12-28 1990-04-03 Bio-Products, Inc. Use of hydrogel solutions to form a hydrophilic protective film on the skin against toxic substances, pollutants, infections and skin secretions
US5143900A (en) 1989-05-19 1992-09-01 Colgate-Palmolive Company Perfumes containing N-lower alkyl neoalkanamide (s)
US5102662A (en) 1989-12-08 1992-04-07 Dow Corning Corporation Insect repellent plastic
US5196200A (en) 1991-04-25 1993-03-23 International Flavors & Fragrances Inc. Bisabolene-containing composition, process for preparing same, organoleptic uses thereof and uses thereof as insect repellent
CA2077828A1 (en) 1991-10-10 1993-04-11 William J. Raleigh Silicone polyether alkyl copolymer synthesis
US5576010A (en) 1993-05-14 1996-11-19 International Flavors & Fragrances Inc. Use of dimethyl substituted oxymethyl cyclohexane derivatives for their insect repellency properties
FR2760361B1 (en) 1997-03-10 1999-12-10 Oreal PHOTOPROTECTIVE COSMETIC COMPOSITIONS CONTAINING A SYSTEM FILTERING UV RAYS, A DISPERSION OF NON-FILMOGENOUS POLYMER PARTICLES AND A FAT PHASE
US6203812B1 (en) * 1998-06-29 2001-03-20 Hydromer, Inc. Hydrophilic polymer blends used to prevent cow skin infections
US6719959B1 (en) * 2000-11-28 2004-04-13 Avon Products, Inc. Extended duration insect repellent composition and method of application to the skin
US7097828B2 (en) * 2001-06-29 2006-08-29 Schering-Plough Healthcare Products, Inc. Sunscreen formulations containing waterborne polyurethane polymers

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5916541A (en) * 1992-06-25 1999-06-29 Stewart; Ernest G. Water resistant sunscreen and insect repellent composition
US5911980A (en) * 1996-06-27 1999-06-15 Macrochem Corporation Lipophilic and amphiphilic or hydrophilic film-forming polymer compositions, and use thereof in topical agent delivery system and method of delivering agents to the skin
US5882633A (en) * 1996-12-17 1999-03-16 Societe L'oreal S.A. Compositions comprising a dibenzoylmethane derivative, a 1,3,5-triazine derivative and an amide compound, and methods of use therefor

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP1250043A4 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1213010A2 (en) * 2000-12-09 2002-06-12 Beiersdorf AG Use of water-soluble and film-forming polymers for increasing the light protection factor and/or the protection performance to UV-A in cosmetic or dermatological formulations
EP1762221A1 (en) * 2005-07-20 2007-03-14 Beiersdorf AG Insect repellent with long lasting affect
EP3099381A4 (en) * 2014-01-28 2017-07-19 Avon Products, Inc. Extended release fragrance compositions
US10052277B2 (en) 2014-01-28 2018-08-21 Avon Products, Inc. Extended release fragrance compositions
US11622929B2 (en) 2016-03-08 2023-04-11 Living Proof, Inc. Long lasting cosmetic compositions
US10842729B2 (en) 2017-09-13 2020-11-24 Living Proof, Inc. Color protectant compositions
US10987300B2 (en) 2017-09-13 2021-04-27 Living Proof, Inc. Long lasting cosmetic compositions
US11707426B2 (en) 2017-09-13 2023-07-25 Living Proof, Inc. Color protectant compositions

Also Published As

Publication number Publication date
AU1788802A (en) 2002-06-11
CA2393290A1 (en) 2002-06-06
US7150878B2 (en) 2006-12-19
US20030099679A1 (en) 2003-05-29
DE60105389T2 (en) 2005-09-22
WO2002043491A9 (en) 2003-08-14
EP1250043B1 (en) 2004-09-08
US6719959B1 (en) 2004-04-13
AU2002217888B2 (en) 2006-11-16
EP1250043A1 (en) 2002-10-23
EP1250043A4 (en) 2003-04-02
DE60105389D1 (en) 2004-10-14

Similar Documents

Publication Publication Date Title
EP1250043B1 (en) Extended duration insect repellent composition and method of application to the skin
AU2002217888A1 (en) Extended duration insect repellent composition and method of application to the skin
AU2002217882B2 (en) Anhydrous insect repellent composition
US7097828B2 (en) Sunscreen formulations containing waterborne polyurethane polymers
EP2061308B1 (en) A water based clear sunscreen and insect repellent composition
AU2005202294B2 (en) Skincare compositions
AU2002217882A1 (en) Anhydrous insect repellent composition
MXPA04002645A (en) Sunscreen compositions.
US6858200B2 (en) Sunscreen formulations
CA2549725A1 (en) A base composition for preparing multi-functional formulations for care and protection of the skin and hair
US6555095B1 (en) Topical compositions and methods of application
US7078022B2 (en) Sunscreen compositions and methods of use thereof
WO2002043656A2 (en) Water-in-oil insect repellent composition and method of application to the skin
CA2271387A1 (en) Insect repellent emulsions
CN113924074A (en) Topical compositions
CN117320687A (en) Sun protection composition containing Bei Mo triazinyl alcohol

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 2393290

Country of ref document: CA

AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES 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 MZ NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ 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 MZ SD SL SZ TZ UG ZM 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 TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

WWE Wipo information: entry into national phase

Ref document number: 2001998225

Country of ref document: EP

Ref document number: 10203839

Country of ref document: US

WWP Wipo information: published in national office

Ref document number: 2001998225

Country of ref document: EP

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: 2002217888

Country of ref document: AU

COP Corrected version of pamphlet

Free format text: PAGES 1/4-4/4, DRAWINGS, REPLACED BY NEW PAGES 1/4-4/4

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWG Wipo information: grant in national office

Ref document number: 2001998225

Country of ref document: EP

NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Ref document number: JP