AU730685B2 - Insect repellent emulsions - Google Patents
Insect repellent emulsions Download PDFInfo
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- AU730685B2 AU730685B2 AU74022/98A AU7402298A AU730685B2 AU 730685 B2 AU730685 B2 AU 730685B2 AU 74022/98 A AU74022/98 A AU 74022/98A AU 7402298 A AU7402298 A AU 7402298A AU 730685 B2 AU730685 B2 AU 730685B2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8164—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-maleic anhydride)
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- 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
- 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
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- 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
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Dermatology (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
WO 98/23150 PCT/US97/20358 INSECT REPELLENT EMULSIONS INTRODUCTION TO THE INVENTION The present invention relates to fluid -formulations-containing the insect repel-ent agent DEET, and more particularly to emulsion formulations thereof..
Man has long used various chemical agents to reduce attacks by bothersome insects, such as mosquitoes, flies, ticks, wasps and bees. The most widely used insect repellent agent at the present time is NN-Diethyl-m-toluamide, frequently called "DEET." DEET is an unctuous, somewhat hygroscopic,..light- -sensitive, oily material having a very high solvency for other water-insoluble materials. It has some notoriety for being difficult to emulsify, so is frequently used in concentrated..form or formulated- as an'aerosol spray or dilute solution, or in solid or semi-solid form such as in a stick. To repel insects, one applies DEET or 'formulations containing up to about- 100% DEET to clothing and exposed skin.
However, humans usually prefer the feel- of aqueous materials on their skin. In the cosmetic and medical fields, it has been found that oily materials can be S made more pleasing by their incorporation, into oil-inwater emulsions. Since the droplets of insoluble material are completely surrounded by the aqueous phase, the sensation to the--skin is essentially one of applying aqueous materials. Emulsions are also easier to apply evenly to skin, than are solutions, sprays and gelled materials in stick form. DEET, however, does not typically form emulsions having commercially required stability, and it is quite undesirable to require users to mix the separated phases before using products.
SUMMARY OF THE INVENTION The invention provides an insect repellent emulsion composition comprising: an insect repelling effective amount of N,N-Diethyl-m-toluamide; water; 0.1 to 5 percent by weight of a film-forming polymer selected from the group consisting of copolymers of octadecene and maleic anhydride, copolymers of 1-triacontane and vinyl pyrrolidone, acrylates/octylacrylamide copolymer, acrylates/PVP copolymer, acrylates/acrylamide copolymer, acrylates/VA copolymer, ethylene/maleic anhydride copolymer, polyisobutene, polyvinyl alcohol,.PVP/eicosane copolymer, starch/acrylates/acrylamide copolymer, hexanedioic acid polymers and mixtures of any two or more 20 thereof; 0.01 to 5 percent by weight of an emulsifieremulsion stabilizer selected from the group consisting of acrylates/Cl0-30 alkyl acrylate crosspolymer, carbomer, methyl vinyl ether/maleic anhydride copolymer, a salt of triethanolamine and stearic acid, and mixtures of any two 25 of more thereof; and, optionally, from 0.1 to 10 percent by weight of an emulsifying agent selected from the group consisting of sorbitan stearate, stearic acid, sorbitan oleate, cetyl alcohol, glyceryl oleates, glycerl stearates, sorbitan sesquioleate, DEA-cetyl phosphate, Oleth-20, PEG-8 distearate, PEG-8 oleate, PEG-2 stearate, Polysorbate 20, Polysorbate 60, Polysorbate 80, propylene glycol stearate, sodium laureth sulfate and mixtures of two or more thereof.
34116.DOC DETAILED DESCRIPTION OF THE INVENTION In this application, all references to "percent" shall mean percent by weight, unless the context clearly indicates otherwise. Many of the formulation components (surfactants, emulsion stabilizers, filmformers, etc.) are identified herein by their names as given in the monographs of J. A. Wenninger et al., Eds., CTFA Cosmetic Ingredient Handbook, Second Edition, The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1992.
DEET is commercially available in the form of a technical concentrate which contains at least about DEET. The remaining 5% or less comprises moisture and isomers other than the meta-toluic isomer, which other isomers are considered to also have some insect repellent activity,..plus small amounts of impurities which are artifacts of the manufacturing process employed.-..For.simplicity, a recitation herein of-DEET concentration shall ignore the other components of the concentrate: "10% DEET" shall indicate that a 3 34116.DOC 3 formulation contains 10% of a commercial technical concentrate.
The emulsions of the present invention contain an insect repelling effective amount of DEET, generally about 5 to about 25 percent, together with water, a film-forming polymer and an emulsifier-emulsion stabilizer. In some instances, a supplemental emulsifying agent may be useful as a formulation component.
Suitable supplemental emulsifiers include, without limitation, the surfactants sorbitan stearate, stearic acid, sorbitan oleate, cetyl alcohol, glyceryl oleates, glyceryl stearates, sorbitan sesquioleate, DEA-cetyl phosphate, Oleth-20, PEG-8 distearate, PEG-8 oleate, PEG-2 stearate, Polysorbate 20, Polysorbate S* 15 Polysorbate 80, .,.prppylene glycol stearate, sodium laureth sulfate, sorbitan sesquioleate and many others known in the art. In general, and keeping in mind that there are numerous exceptions to this statement, oil- S. in-water emulsions are prepared using emulsifiers 20 having hydrophilic-lipophilic balance values about 8 to about 18. Combinations of emulsifiers may *be used, and frequently will be found to impart a greater emulsion stability than single emulsifiers.
When combinations a-e used, all of the individual HLB 25 values may not always be within the above range, but the overall HLB value usually will be. In general, when present, the emulsifier component will amount to about 0.1% to about 10% of the formulation.
A film-forming polymer is present to provide a continuous film upon skin application and water resistance to the formulation. Water resistance may assist in obtaining an enhanced duration of action for the insect repellent agent. This would be particularly desirable for users participating in water-related activities, such as fishing, water skiing, swimming or activities which may incidentally involve water contact, or for users who are engaged in strenuous WO 98/23150 PCT/US97/20358.
-4sports or work activities and perspire heavily. Useful film formers include: copolymers of octadecene and maleic anhydride; copolymers of 1-triacontane and vinyl pyrrolidone; acrylates/octylacrylamide copolymer; acrylates/PVP copolymer; acrylates/acrylamide copolymer; acrylates/VA copolymer; ethylene/maleic anhydride copolymer; polyisobutene; polyvinyl alcohol; PVP/eicosane copolymer; starch/acrylates/acrylamide copolymer; and. hexanedioic acid polymers. Such ingredients will generaily be present in a formulation in amounts about 0.1% to about Also required in the formulation is an emulsifieremulsion stabilizer, such as'-an acrylates/C1-0-30 alkyl acrylate crosspolymer, carbomer, methyl vinyl ether/maleic anhydride copolymer or a triethanolamine salt of stearic-acid. Suitable acrylates/C10-30 alkylacrylate crosspolymer materials are commercially -available from B.F. Goodrich Chemicals, Akron, Ohio under the trade names PEMULEN® TR-1 and TR-2, or CARBOPOL®. The concentration of emulsifier-emulsion.
stabilizer in the formulation will typically be about 0.01% to about In some formulations, it has been found that the concentration of the emulsion stabilizer PEMULEN TR-2 should not exceed about to avoid viscosity increases which adversely affecE emulsion preparation and handling.
Other components, while not required, are commonly included in skin care products to enhance the feel of the material upon.application, to treat dry skin conditions and/or---to protect the formulation against midrbbial contamination. These include emollients, fragrances, preservatives, vitamins, humectants, skin conditioners, antioxidants and others. Any of such materials may be_included as desired, in addition-tothe required components.
SU ncsreening ingredients are also useful optional components of the formulations,--when the user desires WO 98/23150 PCT/US97/20358 concomitant protection against excessive ultraviolet radiation exposure. Since the choice of sunscreen active agents is usually limited to those having governmental approvals, those skilled in the art wil-l be aware of acceptable compounds. In the United States, these currently include: aminobenzoic acid; cinoxate; diethanolamine p-methoxycinnamate; digalloyl trioleate; dioxybenzone;-ethyl 4-[bis(hydroxypropyl)] .aminobenzoate; 2-ethylhexyl 2-cyano-3,3diphenylacrylate; ethylhexyl p-methoxycinnamate; 2ethylhexyl. salicylate; glyceryl aminobenzoate; .homosalate; lawsone with dihydroxyacetone; menthyl anthranilate; oxybenzone; Padimate A; Padimate 0; 2acid; red petrolatum; sulisobenzone; and triethanolamine salicylate. Other active sunscreen ingredients,. such as avobenzone, titanium dioxide and phenylbenzimidazole sulfonic acid, are approved for use in many countries and may also be incorporated into the insect repellent formulations of the present invention.
Sunscreening ingredients will be used in sunscreeneffective-amounts-.as needed to.provide a desired sun protection factor (SPF), which may be measured using at least the-essence of the procedure proposed to be established by the United States Food and Drug Administration as Title 21,-Code of Federal Regulations,.Part 352, Subpart D (Sections 352.70- 352.77), which proposal was published in the Federal Register on May 12, 1993 at pages 28298-28301. In general, up to about 30 percent sunscreens can be used.
The invention will be further illustrated by the following examples, which are not intended to limit the scope of the invention as defined in-the appended claims.
WO 98/23150 PCT1US97/20358 -6- Example 1 A storage-stable insect repellent loti prepared using the following ingredients: Name Water.- C12-15 alkyl benzoate
DEET
Sorbitol, 70% aqueous solution Sorbitan oleate Sorbitan stearate Glyceryl stearate, self emulsifying Stearic acid Octadecene/maleic anhydride copolymer Hydrogenated'vegetable oil Triethanolamine Benzyl alcohol Propylparaben- Fragrance Dimethicone Methylparaben .Imidazolidinyl urea- PEMULEN® TR-2 Vitamin E Jojoba.oil Aloe vera lipoquinone Disodium EDTA Letter identifies components particular process steps on is Percent 41.89 21.50 10.00 5.00 00 3.00 3.00_- 2.00 2.00 2.00 .1.80 1.00 1.00 0.70 0.40 ,0.20 0 0.20 0.10 7 0.05 0.05 0 01 added during The emulsion is prepared as follows: all but a small portion.of the water and the Pemulen TR-2 are mixed to form a clear solution and heated to about 65 0 C; components identified with a above-are sequentially added to the step 1 solution,-.with mixing to dissolve; all components identified as are WO 98/23150 PCT/US97/20358 -7mixed, except for the vitamin E, dimethicohe and octadecene/maleic anhydride copolymer, to form a solution and heated to about 82-85 0 C; the octadecene/maleic anhydride copolymer is added to the step 3 mixture, and dissolved; the step 4 mixture is cooled to about 65-71 0 C and the remaining "C" components are added and dissolved; the warm "D" component is added to the warm mixture from step 5 and dissolved; the-solution from step 6 is added to the solution from step 2, with sufficient agitation to form an emulsion, and mixing is continued until the emulsion cools to about 49-54 0 the -eomponents are added to the emulsion.from step 7, with cont-iuedmixing; the remaining water and the component are mixed-to-f-orm a solution, then added to the emulsion of step 8; and (10)-the emulsion is cooled toroom temperature and water is added to compensate for evaporative losses during the preparation.
20 Example 2 A storage-stable insect repellent lotion, containing sufficient sunscreen components to provide a waterproof sun protection factor (SPF) of 15, is prepared using the following ingredients and the general procedure of the preceding example: SName Percent--- Water DEET Octyl methoxycinnamate Octyl salicylate Homomenthyl...salicylate Sorbitol, 70% aqueous-- solut-i-on Oxybenzone -35 Sorbitan oleate Glyceryl stearate, self emulsifying Sorbitan stearate 42.79 10.00 7.50 5.00 5.00 S 5.00 4.00 4.00 3.00 3 .00 WO 98/23150 PCT/US97/20358 Stearic acid 2.00 Hydrogenated-vegetable oil 2.00 Octadecene/maleic anhydride copolymer 2.00 Triethanolamine 1.80 Benzyl alcohol .1.00 Fragrance '0.70 Dimethicone 0..40 Methylparaben 0.20 Imidazolidinyl urea 0.20 PEMULEN® TR-2 0.10 Propylparaben 0.10 Vitamin E 0.10 Jojoba oil 0.05 Aloe vera lipoquinone 0.05 Disodium EDTA 0.01 For this..emulsion preparation, sunscreen active ingredients are added as components.
Example 3 A storage-stable insect repellent lotion, containing sufficient sunscreen components toprovide a waterproof SPF of 30, is prepared using the following ingredients: Name Water Homomenthyl salicylate
DEET
Octyl methoxycinnamate Oxybenzone Sorb'itol, 70% aqueous solution.
Octadecene/maleic anhydride copolymer Triethanolamine Dimethicone Pemulen® TR-2 Fragrance Percent 57.09 B 13.00 D 10.00 B 7.50 B 6.00 A 2.00 -C 2.00 A 1.00 C 0.40 A -0.-30 E 0.30 Imidazolidinyl urea F 0.20 Vitamin E acetate B 0.10 Aloe vera lipoquinone B 0.05...
Jojoba oil B 0.05 Disodium EDTA A 0.01 Letter identifies components added during particular process steps The emulsion is prepared as follows: the components identified in the table with an are mixed with all but a small portion of the water, while heating to about 49-55 0 C to form a solution.:_12). the components are mixed and heated to about 80-82 0
C,
to form a so-lution; to the step 2 solution are sequentially added the components, with sufficient.
mixing after each addition to form a solution; the step 3 solution is cooled to about 62-68 0 C; the DEET is added to the step 4 solution and thoroughly.
20 mixed; the solution of step 1 is agitated to form a vortex and the solution of step 5 is slowly added, to form an emulsion, then mixing is continued as the mixture cools to about 49-52C; the fragrance is added to-the mixture from step 6 and mixing is 25 continued as the batch cools to ambient temperature; the component is dissolved in the remaining water and added to the mixture of step 7; and (9) sufficient water is added, with mixing, to compensate for evaporative losses during the preparation.
30 In the claims which follow and in the preceding description of the invention, except where the context requires otherwise due to express language or necessary implication, the words "comprising" and "comprises" are used in the sense of "including" and "includes", ie. the features specified may be associated with further features in various embodiments of the invention.
Claims (13)
1. An insect repellent emulsion composition comprising: an insect repelling effective amount of N,N- Diethyl-m-toluamide; water; 0.1 to 5 percent by weight of a film-forming polymer selected from the group consisting of copolymers of octadecene and maleic anhydride, copolymers of 1-triacontane and vinyl pyrrolidone, acrylates/octylacrylamide copolymer, acrylates/PVP copolymer, acrylates/acrylamide copolymer, acrylates/VA copolymer, ethylene/maleic anhydride copolymer, polyisobutene, polyvinyl alcohol, PVP/eicosane copolymer, starch/acrylates/acrylamide copolymer, hexanedioic acid polymers and mixtures of any two or more thereof; 0.01 to 5 percent by weight of an emulsifier-emulsion stabilizer selected from the group consisting of acrylates/C10-30 alkyl acrylate crosspolymer, carbomer, methyl vinyl ether/maleic anhydride copolymer, a salt of es S. triethanolamine and stearic acid, and mixtures of any two 20 of more thereof; and, optionally, from 0.1 to 10 percent by weight of an emulsifying agent selected from the group consisting of sorbitan stearate, stearic acid, sorbitan oleate, cetyl alcohol, glyceryl oleates, glycerl stearates, sorbitan sesquioleate, DEA-cetyl phosphate, 25 Oleth-20, PEG-8 distearate, PEG-8 oleate, PEG-2 stearate, Polysorbate 20, Polysorbate 60, Polysorbate 80, propylene see**: glycol stearate, sodium laureth sulfate and mixtures of two or more thereof. 00* 30
2. The composition of claim 1, further comprising an emulsifying agent. J*iASpec3O 39940 3.4934116.doc -11-
3. The composition of claim 1, wherein the DEET is present in amounts about 5 to about 25 percent by weight.
4. The composition of claim 1, further comprising a sunscreening effective amount of a sunscreening agent.
The composition of claim 4, wherein the sunscreen agent is selected from the group consisting of: aminobenzoic acid; cinoxate; diethanolamine p- methoxycinnamate; digalloyl trioleate; dioxybenzone; ethyl 4-[bis(hydroxypropyl)] aminobenzoate; 2-ethylhexyl 2- cyano-3,3-diphenylacrylate; ethylhexyl p-methoxycinnamate; 2-ethylhexyl salicylate; glyceryl ami-nbenzoate; homosalate; lawsone with dihydroxyacetone; menthyl anthranilate; oxybenzone; Padimate A; Padimate 0; 2- acid; red petrolatum; sulisobenzone; triethanolamine salicylate; avobenzone; titanium dioxide; phenylbenzimidazole sulfonic"acid; and mixtures of any two or more thereof.
6. The composition of claim 4, in which the sunscreening agent comprises up to about 30 percent-by. weight. o *o J:\Spci3OO 3990M 349k341 16doc -12-
7. An insect repellent emulsion composition comprising: about 5 to about 25 percent by weight N,N- Diethyl-m-toluamide; about 0.1 to about 5 percent by weight of a film- forming polymer selected from the group consisting of: copolymers of octadecene and maleic anhydride; copolymers of 1-triacontane and vinyl pyrrolidone; acrylates/octylacrylamide copolymer; acrylates/PVP copolymer; acrylates/acrylamide copolymer; acrylates/VA copolymer; ethylene/maleic anhydride copolymer; polyisobutene; polyvinyLXalcohol; PVP/eicosane copolymer; starch/acrylates/acryiamide copolymer; hexanediec acid polymers; and mixtures of any two or more thereof; about -0-.01 to about 5 percent by weight of an emulsiier -emulsion stabilizer selected from the group consisting of acrylates/C10-30 alkyl-acrylate crosspolymer, carbomer, methyl vinyl ether/maleic anhydride copolymer, a salt of triethanolamine and stearic V acid, and mixtures of any two or more thereof; and water.
8. The composition of -claim 7, further comprising about 0.1 to about 10 percent by weight of an emulsifier having an HLB value about 8 to about 18. S: The composition of claim 7, further comprising a sunscreening effective amount of a sunscreening agent.
S.
10. The composition of claim 9, wherein the sunscreening agent is selected from the group onsisting 'of: aminobenzoic acid; cinoxate; diethanolamine p- methoxycinnamate; digalloyl- tri-oleate; dioxybenzone; ethyl 4-[bis(hydroxypropyl)1 aminobenzoate; 2-ethylhexyl 2- cyano-3,3-diphenylacrylate; ethylhexyl p-methoxycinnamate; 2-ethylhexyl salicylate; glyceryl aminobenzoate; homosalate; lawsone with dihydroxyacetone; menthyl -13- anthranilate; oxybenzone; Padimate A; Padimate 0; 2- acid; red petrolatum; sulisobenzone; triethanolamine salicylate; avobenzone; titanium dioxide; phenylbenzimidazole sulfonic acid; and mixtures of any two or_more thereof.
11. The composition of claim 9, in which the sunscreening agent comprises up to about 30 percent by weight.
12. An insect repellent emulsion composition comprising: about 5 to about 25 percent by weight N,N- Diethyl-m-toluamide; about 0.1 to about 5 percent by weight of a film- forming polymer.selected from the group consisting of: copolymers of octadecene and maleic anhydride; copolymers of 1-triacontane and vinyl pyrrolidone; .i acrylates/octylacrylamide copolymer; acrylates/PVP copolymer; acrylates/acrylamide copolymer; acrylates/VA copolymer; ethylene/maleic anhydride copolymer; polyisobutene; polyvinyl alcohol; PVP/eicosane copolymer; starch/acrylates/acrylamide copolymer; hexanedioic acid polymers; and mixtures of any two -or more thereof; about 0.0. to about 5 percent by weight of an *o*o emulsifier-emulsion stabilizer selected from the group consisting of acrylates/C10-30 alkyl acrylate Scrosspolymer, carbomer, methyl vinyl ether/maleic anhydride copolymer,. a salt. of triethanolamine and stearic acid, and mixtures -of any two or more thereof; water; up to about 10 percent by weight of an emulsifier having an HLB value about 8 to about 18; and up to abut .30 percent by weight of a sunscreening agent selected from the group consisting of: aminobenzoic acid; cinoxate; diethanolamine p- methoxycinnamate; digalloyl trioleate; dioxybenzone; ethyl -14- 4- Ibis (hydroxypropyl) 3 aminobenzoate; 2-ethyihexyl 2- cyano-3, 3-diphenylacrylate; ethyihexyl p-methoxycinnamate; 2-etyihxylsalicylate; glyceryl aminobenzoate; homosalate; lawsone with dihydroxyacetone; menthyl anthranilate; oxybenzone; Padimate'A; Padimate 0; 2- acid; red petrolatum; sulisobenzone; triethanolamine salicylate; avQ):enzone; titanium dioxide; phenylbenzimidazole sulfonic acid; and mixtures of any two or more thereof.
13. An insect repellent emulsion composition substantially as herein described with reference to Example 1, Example 2 or Example 3. Dated this 22nd day of December 1999 SCHERING-PLOUGH HEALTHCARE PRODUCTS, INC. By their Patent Attorneys GRIFFITH HACK
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75673696A | 1996-11-26 | 1996-11-26 | |
| US08/756736 | 1996-11-26 | ||
| PCT/US1997/020358 WO1998023150A1 (en) | 1996-11-26 | 1997-11-21 | Insect repellent emulsions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7402298A AU7402298A (en) | 1998-06-22 |
| AU730685B2 true AU730685B2 (en) | 2001-03-08 |
Family
ID=25044836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU74022/98A Ceased AU730685B2 (en) | 1996-11-26 | 1997-11-21 | Insect repellent emulsions |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0946092A1 (en) |
| JP (1) | JP2000505811A (en) |
| AR (1) | AR010303A1 (en) |
| AU (1) | AU730685B2 (en) |
| BR (1) | BR9713547A (en) |
| CA (1) | CA2271387A1 (en) |
| CO (1) | CO4900083A1 (en) |
| NZ (1) | NZ335296A (en) |
| TW (1) | TW450806B (en) |
| WO (1) | WO1998023150A1 (en) |
| ZA (1) | ZA9710555B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19904703A1 (en) * | 1999-02-05 | 2000-08-24 | Georg Noga | Aqueous plant strengthening composition containing tocopherol and methoxycinnamic acid, providing protection against damage by e.g. heat, frost, drought or especially ultraviolet light |
| US6391290B1 (en) * | 2001-03-21 | 2002-05-21 | Schering-Plough Healthcare Products, Inc. | Skin care compositions |
| GB0704709D0 (en) | 2007-03-12 | 2007-04-18 | Croda Singapore P L | Dispersion, gel and emulsification system |
| ES2969412T3 (en) | 2011-10-17 | 2024-05-17 | Univ California | Methods for evaluating the repellent quality of organic materials and methods and compositions for repelling arthropods |
| 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 |
| EP3409115A3 (en) | 2013-03-15 | 2019-02-27 | The Regents of The University of California | Methods for identifying arthropod repellents, and compounds and compositions identified by such methods |
| US20160272612A1 (en) | 2015-03-18 | 2016-09-22 | The Regents Of The University Of California | Anthropod repellent chemicals |
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| EP0416837A1 (en) * | 1989-09-08 | 1991-03-13 | Richardson-Vicks, Inc. | Photoprotection compositions having reduced dermal irritation |
| JPH0592915A (en) * | 1991-03-29 | 1993-04-16 | Shiseido Co Ltd | Medicine for external use |
| WO1997049380A1 (en) * | 1996-06-26 | 1997-12-31 | S.C. Johnson & Son, Inc. | Insect repellent sunscreen |
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| EP0085334A3 (en) * | 1982-01-25 | 1985-08-07 | PLOUGH, INC. (a Delaware corporation) | Substantive topical compositions |
| US4816256A (en) * | 1986-10-10 | 1989-03-28 | Minnesota Mining And Manufacturing Company | Mosquito repellent compositions |
| US4774082A (en) * | 1987-01-13 | 1988-09-27 | S. C. Johnson & Son, Inc. | Volatile insect repellents |
| US4774081A (en) * | 1987-01-13 | 1988-09-27 | S. C. Johnson & Son, Inc. | Contact insect repellents |
| CH676412A5 (en) * | 1988-01-27 | 1991-01-31 | Serge Andre Leuthold | |
| GB8821587D0 (en) * | 1988-09-15 | 1988-10-12 | Euro Celtique Sa | Method for controlling lice/their ova |
| US5518712A (en) * | 1992-06-25 | 1996-05-21 | Stewart; Ernest | Water resistant sunscreen protection and insect repellent compound |
| WO1994000104A1 (en) * | 1992-06-25 | 1994-01-06 | Stewart Ernest G | Water resistant sunscreen protection and insect repellent compound |
| US5916541A (en) * | 1992-06-25 | 1999-06-29 | Stewart; Ernest G. | Water resistant sunscreen and insect repellent composition |
-
1997
- 1997-11-21 NZ NZ335296A patent/NZ335296A/en unknown
- 1997-11-21 AR ARP970105476A patent/AR010303A1/en unknown
- 1997-11-21 JP JP10524668A patent/JP2000505811A/en active Pending
- 1997-11-21 BR BR9713547-0A patent/BR9713547A/en not_active IP Right Cessation
- 1997-11-21 EP EP97949380A patent/EP0946092A1/en not_active Withdrawn
- 1997-11-21 AU AU74022/98A patent/AU730685B2/en not_active Ceased
- 1997-11-21 WO PCT/US1997/020358 patent/WO1998023150A1/en not_active Application Discontinuation
- 1997-11-21 CO CO97068364A patent/CO4900083A1/en unknown
- 1997-11-21 CA CA002271387A patent/CA2271387A1/en not_active Abandoned
- 1997-11-24 ZA ZA9710555A patent/ZA9710555B/en unknown
- 1997-12-09 TW TW086117553A patent/TW450806B/en active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0416837A1 (en) * | 1989-09-08 | 1991-03-13 | Richardson-Vicks, Inc. | Photoprotection compositions having reduced dermal irritation |
| JPH0592915A (en) * | 1991-03-29 | 1993-04-16 | Shiseido Co Ltd | Medicine for external use |
| WO1997049380A1 (en) * | 1996-06-26 | 1997-12-31 | S.C. Johnson & Son, Inc. | Insect repellent sunscreen |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ335296A (en) | 2000-10-27 |
| EP0946092A1 (en) | 1999-10-06 |
| CO4900083A1 (en) | 2000-03-27 |
| TW450806B (en) | 2001-08-21 |
| BR9713547A (en) | 2000-01-25 |
| WO1998023150A1 (en) | 1998-06-04 |
| JP2000505811A (en) | 2000-05-16 |
| ZA9710555B (en) | 1998-05-25 |
| AU7402298A (en) | 1998-06-22 |
| AR010303A1 (en) | 2000-06-07 |
| CA2271387A1 (en) | 1998-06-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |