CA2271387A1 - Insect repellent emulsions - Google Patents
Insect repellent emulsions Download PDFInfo
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- CA2271387A1 CA2271387A1 CA002271387A CA2271387A CA2271387A1 CA 2271387 A1 CA2271387 A1 CA 2271387A1 CA 002271387 A CA002271387 A CA 002271387A CA 2271387 A CA2271387 A CA 2271387A CA 2271387 A1 CA2271387 A1 CA 2271387A1
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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)
-
- 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
-
- 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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- 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)
Abstract
The invention relates to storage stable insect repellent emulsion formulations containing N,N-Diethyl-m-toluamide, together with water, a film-forming polymer and an emulsifier-emulsion stabilizer.
Description
INSECT REPELLENT EMULSIONS
INTRODUCTION TO THE INVENTION
The present invention relates to fluid formulations containing the insect repellent 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 N,N-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 in-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 100o 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 made more pleasing by their incorporation into oil-in-a 35 water 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 WO 98/23150 . PCT/LTS97/20358 __ -2-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 includes a water-in-oil insect repellent emulsion comprising an effective amount of N,N-Diethyl-m-toluamide, water, a film-forming polymer and an emulsifier-emulsion stabilizer.
The emulsion has commercially acceptable storage-stability and a pleasing feel when applied to the skin.
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, film-formers, 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, D.C., 1992.
DEET is commercially available in the form of a technical concentrate which contains at least about 950 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 DEFT
concentration shall ignore the other components of the concentrate: "10% DEET" shall indicate that a WO 98/23150 - ~ PCT/US97/20358 formulation contains 10% of a commercial technical concentrate.
The emulsions of the present invention contain DEFT, at 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 l0 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 60, Polysorbate 80~"~xapylene glycol stearate, sodium laureth sulfate, sorbitan sesquioleate and many others known in the art. In general, and keeping in mind that there are numeroLrs exceptions to this statement, oil-in-water emulsions are prepared using emulsifiers having hydrophilic-lipophilic balance ("HLB") values about 8 to about 18. Combinations of emulsifi-ers 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
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 O.lo 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 CA 02271387 1999-OS-11 _ sports or work activities and perspire Tzeavily. Useful film formers include: copolymers of octadecene and malefic anhydride; copolymers of 1-triacontane and vinyl pyrrolidone; acrylates/octylacrylamide copolymer;
-5 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 generally be present in a formulation in amounts about 0 . 1% to about 5% . - '---w-----w Also required-in the formulation. is an emulsifier-emulsion stabilizer, such as an acrylates/C10-30 alkyl acrylate crosspolymer, carbomer, methyl vinyl ether/maleic anhydride copolymer or a triethanolamine salt of stearic acid. Suitable acrylates/C10-30 alkyl acrylate 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 50. In some formulations, it has been found that the concentration of the emulsion stabilizer - PEMULEN TR-2 should not exceed about 0.80, to avoid viscosity increases which adversely affect 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 microbial contamination. These include emollients, fragrances, preservatives, vitamins, humectants, skin conditioners, antioxidants and others. Any of such - materials may be included as desired, in addition to 35the required components.
Sunscreening ingredients are also useful optional components of the formulations, when the user desires 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 will 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-et~hylhexyl 2-cyano-3,3-diphenylacrylate; ethylhexyl p-methoxycinnamate; 2-ethylhexyl salicylate; glyceryl aminobenzoate;
homosalate; lawsone with dihydroxyacetone; menthyl anthranilate; oxybenzone,; Padimate A; Padimat-a O-; 2-phenylbenzimidazole-5-sulfonic acid; 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 sunscreen effective 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 3S2, 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.
-6=
Example 1 A storage-stable insect repellent lotion is prepared using the following ingredients:
Name * Percent Water 4l.89 C12-15 alkyl benzoate C 2l.50 DEFT D 10.00 Sorbitol, 70% aqueous solution B S.00 Sorbitan oleate C 4..00 Sorbitan stearate C 3.00 Glyceryl stearate, self emulsifying C 3.00_ Stearic acid C 2.00 Octadecene/maleic anhydride copolymer C 2.00 Hydrogenated vegetable oil C 2.00 Triethanolamine B 1.80 Benzyl alcohol E 1.00 Propylparaben - C 1.00 Fragrance E 0.70 Dimethicone C 0.40 Methylparaben C :-0.20 Imidazolidinyl urea F -0.20 PEMULEN~ TR-2 A 0.10 Vitamin E - C __~-.10 Jojoba oil C 0.05 Aloe vera lipoquinone C 0.05 Disodium EDTA B 0 a01 * Letter identifies components added during particular process steps The emulsion is prepared as follows: (1) a11 but a small portion of the water and the Pemulen TR-2 are mixed to form a clear solution and heated to about 60-65°C; (?) components identified.with a "B" above are sequentially added to the step 1 solution, with mixing - to dissolve; (3) a11 components identified as "C" are _7_ mixed, except for the vitamin E, dimethicone and octadecene/maleic anhydride copolymer, to form a solution and heated to about 82-85°C; (4) the octadecene/maleic anhydride copolymer is added to the step 3 mixture, and dissolved; (5) the step 4 mixture_ is cooled to about 65-71°C and the remaining "C"
components are added and dissolved; (6) the-warm "D"
component is added to the warm mixture from step 5 and dissolved; (7) 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°C; (8) the "E" components are added to the emulsion from step 7, with continued mixing;(g) the remaining water and the "G"-component are mixed to form a solution, then added to the emulsion of step 8; and (10) the emulsion is cooled to room temperature and water is added to compensate for evaporative losses during the preparation.
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:
Name Percent Water 42.79 DEET 10.00 Octyl methoxycinnamate 7.50 Octyl salicylate 5.00 Homomenthyl salicylate 5.00 Sorbitol, 70% aqueous solution 5.00 Oxybenzone 4.00 Sorbitan oleate 4.00 _.
Glyceryl stearate, self 'ei~iz~sifying - 3 . 00 Sorbitan stearate 3.00 WO 98I23150 . PCT/US97I20358 .
_g-Steari:e --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 Imidazol-idinyl urea 0.20 PEMULEN~ TR-2 0.10 Propylparaben 0.l0 Vitamin E 0.l0 Jojoba oil 0.05 Aloe vera lipoquinone Q.05 Disodium EDTA 0.01 For this emulsion preparation, sunscreen active ingredients are added as "C" components.
Example 3 A storage-stable insect repellent lotion, containing sufficient sunscreen components to provide a waterproof SPF of 30, is prepared using the following ingredients:
Name - * Percent Water 57.09 Homomenthyl salicylate B 13.00 DEET D l0.00 Octyl methoxycinnamate B 7.50 Oxybenzone B 6.00 Sorbitol, 70o aqueous solution A 2.00 Octadecene/maleic anhydride copolymer C 2a00 Triethanolamine A Z.00 Dimethicone C 0.40 Pemulen~ TR-2 A 0.30 Fragrance E 0.30 _g_ Imidazolidinyl urea -F' 0.20 Vitamin E acetate B 0.10 Aloe vera lipoquinone B 0.05 Jojoba oil B 0.05 -5 Disodium EDTA A 0.01 * Letter identifies components added during particular process steps The emulsion is prepared as follows: (1) the components identified in the table with an "A" are - ----.~-..-w., mixed with a11 but a small portion of the water, while heating to about 49-55°C to form a solution; (2) the "B" components are mixed and heated to about 80-82°C, to form a solution; (3) to the step 2 solution are _ sequentially added the "C" components, with sufficient mixing after each addition to form a solution; (4) the step 3 solution is cooled to about 62-68°C; (5) the DEET is added to the step 4 solution and thoroughly mixed; (6) 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 49-52°C; (7) the fragrance is _ added to the mixture from step 6 and mixing is continued as the batch cools to ambient temperature;
- _. (8) the "F" 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.
INTRODUCTION TO THE INVENTION
The present invention relates to fluid formulations containing the insect repellent 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 N,N-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 in-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 100o 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 made more pleasing by their incorporation into oil-in-a 35 water 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 WO 98/23150 . PCT/LTS97/20358 __ -2-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 includes a water-in-oil insect repellent emulsion comprising an effective amount of N,N-Diethyl-m-toluamide, water, a film-forming polymer and an emulsifier-emulsion stabilizer.
The emulsion has commercially acceptable storage-stability and a pleasing feel when applied to the skin.
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, film-formers, 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, D.C., 1992.
DEET is commercially available in the form of a technical concentrate which contains at least about 950 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 DEFT
concentration shall ignore the other components of the concentrate: "10% DEET" shall indicate that a WO 98/23150 - ~ PCT/US97/20358 formulation contains 10% of a commercial technical concentrate.
The emulsions of the present invention contain DEFT, at 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 l0 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 60, Polysorbate 80~"~xapylene glycol stearate, sodium laureth sulfate, sorbitan sesquioleate and many others known in the art. In general, and keeping in mind that there are numeroLrs exceptions to this statement, oil-in-water emulsions are prepared using emulsifiers having hydrophilic-lipophilic balance ("HLB") values about 8 to about 18. Combinations of emulsifi-ers 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
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 O.lo 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 CA 02271387 1999-OS-11 _ sports or work activities and perspire Tzeavily. Useful film formers include: copolymers of octadecene and malefic anhydride; copolymers of 1-triacontane and vinyl pyrrolidone; acrylates/octylacrylamide copolymer;
-5 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 generally be present in a formulation in amounts about 0 . 1% to about 5% . - '---w-----w Also required-in the formulation. is an emulsifier-emulsion stabilizer, such as an acrylates/C10-30 alkyl acrylate crosspolymer, carbomer, methyl vinyl ether/maleic anhydride copolymer or a triethanolamine salt of stearic acid. Suitable acrylates/C10-30 alkyl acrylate 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 50. In some formulations, it has been found that the concentration of the emulsion stabilizer - PEMULEN TR-2 should not exceed about 0.80, to avoid viscosity increases which adversely affect 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 microbial contamination. These include emollients, fragrances, preservatives, vitamins, humectants, skin conditioners, antioxidants and others. Any of such - materials may be included as desired, in addition to 35the required components.
Sunscreening ingredients are also useful optional components of the formulations, when the user desires 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 will 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-et~hylhexyl 2-cyano-3,3-diphenylacrylate; ethylhexyl p-methoxycinnamate; 2-ethylhexyl salicylate; glyceryl aminobenzoate;
homosalate; lawsone with dihydroxyacetone; menthyl anthranilate; oxybenzone,; Padimate A; Padimat-a O-; 2-phenylbenzimidazole-5-sulfonic acid; 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 sunscreen effective 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 3S2, 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.
-6=
Example 1 A storage-stable insect repellent lotion is prepared using the following ingredients:
Name * Percent Water 4l.89 C12-15 alkyl benzoate C 2l.50 DEFT D 10.00 Sorbitol, 70% aqueous solution B S.00 Sorbitan oleate C 4..00 Sorbitan stearate C 3.00 Glyceryl stearate, self emulsifying C 3.00_ Stearic acid C 2.00 Octadecene/maleic anhydride copolymer C 2.00 Hydrogenated vegetable oil C 2.00 Triethanolamine B 1.80 Benzyl alcohol E 1.00 Propylparaben - C 1.00 Fragrance E 0.70 Dimethicone C 0.40 Methylparaben C :-0.20 Imidazolidinyl urea F -0.20 PEMULEN~ TR-2 A 0.10 Vitamin E - C __~-.10 Jojoba oil C 0.05 Aloe vera lipoquinone C 0.05 Disodium EDTA B 0 a01 * Letter identifies components added during particular process steps The emulsion is prepared as follows: (1) a11 but a small portion of the water and the Pemulen TR-2 are mixed to form a clear solution and heated to about 60-65°C; (?) components identified.with a "B" above are sequentially added to the step 1 solution, with mixing - to dissolve; (3) a11 components identified as "C" are _7_ mixed, except for the vitamin E, dimethicone and octadecene/maleic anhydride copolymer, to form a solution and heated to about 82-85°C; (4) the octadecene/maleic anhydride copolymer is added to the step 3 mixture, and dissolved; (5) the step 4 mixture_ is cooled to about 65-71°C and the remaining "C"
components are added and dissolved; (6) the-warm "D"
component is added to the warm mixture from step 5 and dissolved; (7) 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°C; (8) the "E" components are added to the emulsion from step 7, with continued mixing;(g) the remaining water and the "G"-component are mixed to form a solution, then added to the emulsion of step 8; and (10) the emulsion is cooled to room temperature and water is added to compensate for evaporative losses during the preparation.
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:
Name Percent Water 42.79 DEET 10.00 Octyl methoxycinnamate 7.50 Octyl salicylate 5.00 Homomenthyl salicylate 5.00 Sorbitol, 70% aqueous solution 5.00 Oxybenzone 4.00 Sorbitan oleate 4.00 _.
Glyceryl stearate, self 'ei~iz~sifying - 3 . 00 Sorbitan stearate 3.00 WO 98I23150 . PCT/US97I20358 .
_g-Steari:e --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 Imidazol-idinyl urea 0.20 PEMULEN~ TR-2 0.10 Propylparaben 0.l0 Vitamin E 0.l0 Jojoba oil 0.05 Aloe vera lipoquinone Q.05 Disodium EDTA 0.01 For this emulsion preparation, sunscreen active ingredients are added as "C" components.
Example 3 A storage-stable insect repellent lotion, containing sufficient sunscreen components to provide a waterproof SPF of 30, is prepared using the following ingredients:
Name - * Percent Water 57.09 Homomenthyl salicylate B 13.00 DEET D l0.00 Octyl methoxycinnamate B 7.50 Oxybenzone B 6.00 Sorbitol, 70o aqueous solution A 2.00 Octadecene/maleic anhydride copolymer C 2a00 Triethanolamine A Z.00 Dimethicone C 0.40 Pemulen~ TR-2 A 0.30 Fragrance E 0.30 _g_ Imidazolidinyl urea -F' 0.20 Vitamin E acetate B 0.10 Aloe vera lipoquinone B 0.05 Jojoba oil B 0.05 -5 Disodium EDTA A 0.01 * Letter identifies components added during particular process steps The emulsion is prepared as follows: (1) the components identified in the table with an "A" are - ----.~-..-w., mixed with a11 but a small portion of the water, while heating to about 49-55°C to form a solution; (2) the "B" components are mixed and heated to about 80-82°C, to form a solution; (3) to the step 2 solution are _ sequentially added the "C" components, with sufficient mixing after each addition to form a solution; (4) the step 3 solution is cooled to about 62-68°C; (5) the DEET is added to the step 4 solution and thoroughly mixed; (6) 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 49-52°C; (7) the fragrance is _ added to the mixture from step 6 and mixing is continued as the batch cools to ambient temperature;
- _. (8) the "F" 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.
Claims (18)
1. An insect repellent emulsion composition comprising an insect repelling effective amount of N,N-Diethyl-m-toluamide, water, a film-forming polymer and an emulsifier-emulsion stabilizer.
2. The composition of claim 1, further comprising an emulsifying agent.
3. The composition of claim 2, wherein the emulsifying agent is selected from the group consisting of 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 60, Polysorbate 80, propylene glycol stearate, sodium laureth sulfate, sorbitan sesquioleate and mixtures of any two or more thereof.
4. The composition of claim 1, wherein the polymer is selected from the group consisting of: copolymers of octadecene and malefic 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.
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.
5. The composition of claim 1, wherein the stabilizer is 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 acid, and mixtures of any two or more thereof.
6. The composition of claim 1, wherein the DEET is present in amounts about 5 to about 25 percent by weight.
7. The composition of claim 1, wherein the emulsifier is present in amounts about 0.1 to about 10 percent by weight.
8. The composition of claim 1, wherein the polymer is present in amounts about 0.1 to about 5 percent by weight.
9. The composition of claim 1, wherein the stabilizer is present in amounts about 0.01 to about 5 percent by weight.
10. The composition of claim 1, further comprising a sunscreening effective amount of a sunscreening agent.
11. The composition of claim 10, 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 aminobenzoate;
homosalate; lawsone with dihydroxyacetone; menthyl anthranilate; oxybenzone; Padimate A; Padimate O;
2-phenylbenzimidazole-5-sulfonic acid; red petrolatum;
sulisobenzone; triethanolamine salicylate; avobenzone;
titanium dioxide; phenylbenzimidazole sulfonic acid; and mixtures of any two or more thereof.
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 aminobenzoate;
homosalate; lawsone with dihydroxyacetone; menthyl anthranilate; oxybenzone; Padimate A; Padimate O;
2-phenylbenzimidazole-5-sulfonic acid; red petrolatum;
sulisobenzone; triethanolamine salicylate; avobenzone;
titanium dioxide; phenylbenzimidazole sulfonic acid; and mixtures of any two or more thereof.
12. The composition of claim 10, in which the sunscreening agent comprises up to about 30 percent by weight.
13. An insect repellent emulsion composition comprising:
(a) about 5 to about 25 percent by weight N,N-Diethyl-m-toluamide;
(b) about 0.1 to about 5 percent by weight of a film-forming polymer selected from the group consisting of:
copolymers of octadecene and malefic 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;
(c) about 0.01 to about 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 triethanolamine and stearic acid, and mixtures of any two or more thereof; and (d) water.
(a) about 5 to about 25 percent by weight N,N-Diethyl-m-toluamide;
(b) about 0.1 to about 5 percent by weight of a film-forming polymer selected from the group consisting of:
copolymers of octadecene and malefic 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;
(c) about 0.01 to about 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 triethanolamine and stearic acid, and mixtures of any two or more thereof; and (d) water.
14. The composition of claim 13, further comprising about 0.1 to about 10 percent by weight of an emulsifier having an HLB value about 8 to about 18.
15. The composition of claim 13, further comprising a sunscreening effective amount of a sunscreening agent.
16. The composition of claim 15, wherein the sunscreening 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 aminobenzoate;
homosalate; lawsone with dihydroxyacetone; menthyl anthranilate; oxybenzone; Padimate A; Padimate O;
2-phenylbenzimidazole-5-sulfonic acid; red petrolatum;
sulisobenzone; triethanolamine salicylate; avobenzone;
titanium dioxide; phenylbenzimidazole sulfonic acid; and mixtures of any two or more thereof.
2-ethylhexyl salicylate; glyceryl aminobenzoate;
homosalate; lawsone with dihydroxyacetone; menthyl anthranilate; oxybenzone; Padimate A; Padimate O;
2-phenylbenzimidazole-5-sulfonic acid; red petrolatum;
sulisobenzone; triethanolamine salicylate; avobenzone;
titanium dioxide; phenylbenzimidazole sulfonic acid; and mixtures of any two or more thereof.
17. The composition of claim 15, in which the sunscreening agent comprises up to about 30 percent by weight.
18. An insect repellent emulsion composition comprising:
(a) about 5 to about 25 percent by weight N,N-Diethyl-m-toluamide;
(b) 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; polyvinyl alcohol; PVP/eicosane copolymer;
starch/acrylates/acrylamide copolymer; hexanedioic acid polymers; and mixtures of any two or more thereof;
(c) about 0.01 to about 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 triethanolamine and stearic acid, and mixtures of any two or more thereof;
(d) water;
(e) up to about 10 percent by weight of an emulsifier having an HLB value about 8 to about 18; and (f) up to about 30 percent by weight of a sunscreening agent 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 aminobenzoate;
homosalate; lawsone with dihydroxyacetone; menthyl anthranilate; oxybenzone; Padimate A; Padimate O;
2-phenylbenzimidazole-5-sulfonic acid; red petrolatum;
sulisobenzone; triethanolamine salicylate; avobenzone;
titanium dioxide; phenylbenzimidazole sulfonic acid; and mixtures of any two or more thereof.
(a) about 5 to about 25 percent by weight N,N-Diethyl-m-toluamide;
(b) 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; polyvinyl alcohol; PVP/eicosane copolymer;
starch/acrylates/acrylamide copolymer; hexanedioic acid polymers; and mixtures of any two or more thereof;
(c) about 0.01 to about 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 triethanolamine and stearic acid, and mixtures of any two or more thereof;
(d) water;
(e) up to about 10 percent by weight of an emulsifier having an HLB value about 8 to about 18; and (f) up to about 30 percent by weight of a sunscreening agent 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 aminobenzoate;
homosalate; lawsone with dihydroxyacetone; menthyl anthranilate; oxybenzone; Padimate A; Padimate O;
2-phenylbenzimidazole-5-sulfonic acid; red petrolatum;
sulisobenzone; triethanolamine salicylate; avobenzone;
titanium dioxide; phenylbenzimidazole sulfonic acid; and mixtures of any two or more thereof.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75673696A | 1996-11-26 | 1996-11-26 | |
| US08/756,736 | 1996-11-26 | ||
| PCT/US1997/020358 WO1998023150A1 (en) | 1996-11-26 | 1997-11-21 | Insect repellent emulsions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2271387A1 true CA2271387A1 (en) | 1998-06-04 |
Family
ID=25044836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002271387A Abandoned CA2271387A1 (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) |
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| 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 |
| HRP20231679T1 (en) | 2011-10-17 | 2024-04-12 | The Regents Of The University Of California | Methods for assessing repellant 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 |
| BR112015023640A2 (en) | 2013-03-15 | 2017-07-18 | Univ California | methods for identifying attractive repellents of arthropods and compounds and compositions identified by such methods |
| WO2016149567A1 (en) | 2015-03-18 | 2016-09-22 | The Regents Of The University Of California | Anthropod repellent chemicals |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5087445A (en) * | 1989-09-08 | 1992-02-11 | Richardson-Vicks, Inc. | Photoprotection compositions having reduced dermal irritation |
| JPH0592915A (en) * | 1991-03-29 | 1993-04-16 | Shiseido Co Ltd | Medicine for external use |
| US5518712A (en) * | 1992-06-25 | 1996-05-21 | Stewart; Ernest | Water resistant sunscreen protection and insect repellent compound |
| AU4650893A (en) * | 1992-06-25 | 1994-01-24 | Ernest G. Stewart | 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 |
| US5716602A (en) * | 1996-06-26 | 1998-02-10 | S. C. Johnson & Sons, Inc. | Insect repellent sunscreen |
-
1997
- 1997-11-21 AR ARP970105476A patent/AR010303A1/en unknown
- 1997-11-21 CO CO97068364A patent/CO4900083A1/en unknown
- 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 CA CA002271387A patent/CA2271387A1/en not_active Abandoned
- 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 NZ NZ335296A patent/NZ335296A/en unknown
- 1997-11-21 JP JP10524668A patent/JP2000505811A/en active Pending
- 1997-11-24 ZA ZA9710555A patent/ZA9710555B/en unknown
- 1997-12-09 TW TW086117553A patent/TW450806B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| WO1998023150A1 (en) | 1998-06-04 |
| AU730685B2 (en) | 2001-03-08 |
| BR9713547A (en) | 2000-01-25 |
| CO4900083A1 (en) | 2000-03-27 |
| ZA9710555B (en) | 1998-05-25 |
| NZ335296A (en) | 2000-10-27 |
| TW450806B (en) | 2001-08-21 |
| AR010303A1 (en) | 2000-06-07 |
| EP0946092A1 (en) | 1999-10-06 |
| AU7402298A (en) | 1998-06-22 |
| JP2000505811A (en) | 2000-05-16 |
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| EEER | Examination request | ||
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20021121 |