CN109843055B - Method for inhibiting penetration of pest repellent into skin and penetration inhibitor for inhibiting penetration of pest repellent into skin - Google Patents
Method for inhibiting penetration of pest repellent into skin and penetration inhibitor for inhibiting penetration of pest repellent into skin Download PDFInfo
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- CN109843055B CN109843055B CN201780049350.9A CN201780049350A CN109843055B CN 109843055 B CN109843055 B CN 109843055B CN 201780049350 A CN201780049350 A CN 201780049350A CN 109843055 B CN109843055 B CN 109843055B
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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
- 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
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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
- 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
- A01N25/30—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 characterised by the surfactants
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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
- 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
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
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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
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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
- A01N37/44—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
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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
- 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
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Abstract
The invention provides a method for inhibiting penetration of an insect repellent into the skin, which is used for reducing irritation caused by a medicament and improving persistence of insect repellent effect on the skin for a long time. The method of inhibiting penetration of a pest repellent into skin of the present invention is to apply at least one ether compound selected from the group consisting of polyoxyethylene polyoxypropylene alkyl ether, polyoxypropylene diglycerol ether, and polyoxypropylene alkyl ether to skin together with the pest repellent.
Description
Technical Field
The present invention relates to a method for inhibiting the penetration of a pest repellent into the skin and a penetration inhibitor for inhibiting the penetration of a pest repellent into the skin.
Background
In the prior art, various pest repellents have been widely used in order to prevent the biting of blood-sucking insects such as gadflies, bed bugs, and the like including mosquitoes. Various studies have been made on these pest repellents in order to improve the feeling of use, reduce irritation, and improve the persistence of the repellent effect.
For example, patent document 1 discloses an insect repellent composition in which a pore volume of 1ml/g or less and an average pore diameter of 1ml/g or less are blended in order to improve the persistence, dispersibility, storage stability and feeling of use of an insect repellent effect by an insect repellent component
Below and a specific surface area of less than 500m2Anhydrous silicic acid particles per gram and is described for use as an aerosol.
Documents of the prior art
Patent document
Patent document 1: japanese laid-open patent publication No. 9-208406
Patent document 2: japanese patent laid-open publication No. 2009-126804
Disclosure of Invention
Technical problem to be solved by the invention
However, in the pest repellent composition of patent document 1, since the anhydrous silicic acid particles are hydrophobic, the anhydrous silicic acid particles are precipitated on the bottom of the container during storage, and the container must be shaken to disperse the anhydrous silicic acid particles each time they are used. In the case of aerosol, if the aerosol is used without shaking the mixing container, when a large amount of anhydrous silicic acid particles are sprayed, problems such as clogging of the spray port, rod hole, and the like, adhesion to the spray surface in the form of a lump, and the like may occur, and therefore, if the aerosol is used improperly, the desired effect cannot be obtained.
In addition, the natural mineral water to be blended in the human pest repellent of patent document 2 is not easy to obtain and is difficult to stably supply, and thus, it is not practical.
Further, since the active ingredient, that is, the pest repellent easily permeates into the skin, it is not possible to leave an effective repellent amount of the pest repellent on the skin for a long time with respect to the conventional pest repellent composition and pest repellent. Therefore, the persistence of the pest repellent effect of the pest repellent applied to the skin is insufficient. Further, since insect repellents such as DEET have skin irritability, once the insect repellents permeate into the skin, they cause irritation to the skin, and thus the safety is insufficient when applied to the human body.
Accordingly, an object of the present invention is to provide a method for suppressing the penetration of an insect repellent into the skin, which is intended to reduce irritation caused by a chemical and to improve the persistence of an insect repellent effect on the skin for a long period of time.
Means for solving the problems
As a result of intensive studies, the present inventors have found that, by applying a specific ether-based compound to the skin together with a pest repellent, it is possible to inhibit the pest repellent from penetrating into the skin and to allow the pest repellent to stay on the epidermis (skin surface) for a long period of time, thereby leading to completion of the present invention.
Namely, the present invention is as follows.
(1) A method for inhibiting penetration of a pest repellent into skin, wherein at least one ether compound selected from the group consisting of polyoxyethylene polyoxypropylene alkyl ether, polyoxypropylene diglycerol ether, and polyoxypropylene alkyl ether is applied to the skin together with the pest repellent.
(2) The method for inhibiting penetration of a pest repellent into skin according to the above (1), wherein the pest repellent is at least one selected from the group consisting of N, N-diethyl-m-toluamide, ethyl 3- (N-butyl-N-acetyl) aminopropionate, and 2- (2-hydroxyethyl) -1-methylpropyl 1-piperidinecarboxylate.
(3) The method for inhibiting penetration of an insect repellent into skin according to the above (1) or (2), wherein the ether compound has an average molar number of addition of oxypropylene groups of 3 to 100.
(4) The method for inhibiting penetration of a pest repellent into the skin according to any one of the above (1) to (3), wherein the ether-based compound is used in an amount of 1 to 300 parts by mass per 100 parts by mass of the pest repellent.
(5) The method for inhibiting penetration of a pest repellent into skin according to any one of the above (1) to (4), wherein the pest repellent is N, N-diethyl-m-toluamide and the amount of N, N-diethyl-m-toluamide attached is 1.5mg/100cm 2The above ether compound has an attachment amount of 0.3mg/100cm2The above manner is used.
(6) A penetration inhibitor for inhibiting penetration of a pest repellent into skin, comprising at least one ether compound selected from the group consisting of polyoxyethylene polyoxypropylene alkyl ether, polyoxypropylene diglycerol ether, and polyoxypropylene alkyl ether.
(7) The penetration inhibitor for inhibiting penetration of a pest repellent into skin according to the above (6), wherein the pest repellent is at least one selected from the group consisting of N, N-diethyl-m-toluamide, ethyl 3- (N-butyl-N-acetyl) aminopropionate, and 2- (2-hydroxyethyl) -1-methylpropyl 1-piperidinecarboxylate.
(8) The penetration inhibitor for inhibiting penetration of a pest repellent into the skin according to the above (6) or (7), wherein the average molar number of addition of oxypropylene groups is 3 to 100.
(9) A method for inhibiting irritation of a pest repellent to skin, wherein at least one ether compound selected from the group consisting of polyoxyethylene polyoxypropylene alkyl ether, polyoxypropylene diglycerol ether, and polyoxypropylene alkyl ether is applied to the skin together with the pest repellent.
Effects of the invention
According to the present invention, when the pest repellent is applied to the skin, at least one ether compound selected from the group consisting of polyoxyethylene polyoxypropylene alkyl ether, polyoxypropylene diglycerol ether, and polyoxypropylene alkyl ether is applied in combination, whereby the penetration of the pest repellent into the skin can be suppressed. As a result, the pest repellent can be left on the skin for a long time, and the persistence of the pest repellent effect on the skin can be improved.
Further, even when the pest repellent is used at a low concentration, the pest repellent effect can be maintained for a long period of time, and a preparation with little irritation to the human body can be provided. In addition, according to the method of the present invention, it is possible to suppress the penetration of the pest repellent into the skin, and therefore, even when the pest repellent is used at a high concentration, it is possible to suppress the irritation of the pest repellent to the skin, and it is possible to provide a preparation having higher safety to the human body.
Drawings
Fig. 1 is a schematic diagram of a horizontal diffusion cell used in a skin absorption inhibition test.
Fig. 2 is a graph showing the results of test example 2.
Fig. 3 is a graph showing the results of test example 3.
Description of the symbols
1 skin of human body
2 receiving pool
3 stirrer
4 water jacket
5 Heater/circulator
6 fastening handle
7 sampling port
8 aluminum foil
9 physiological saline
10 horizontal diffusion cell
11 supply tank
Detailed Description
The present invention will be described in more detail below.
In the present specification, all percentages and parts by mass are the same as percentages and parts by weight.
The present invention provides a method for inhibiting penetration of a pest repellent into the skin by applying at least one ether compound selected from the group consisting of polyoxyethylene polyoxypropylene alkyl ether, polyoxypropylene diglycerol ether, and polyoxypropylene alkyl ether to the skin together with the pest repellent. In addition, the present invention provides a method of using at least one ether compound selected from the group consisting of polyoxyethylene polyoxypropylene alkyl ether, polyoxypropylene diglycerol ether, and polyoxypropylene alkyl ether to inhibit penetration of a pest repellent applied to skin into the skin.
As the pest repellent of the present invention, various synthetic or natural compounds having a repellent effect or a blood-sucking inhibiting effect on biting pests can be used. For example, there may be mentioned: n, N-diethyl-m-toluamide (hereinafter, referred to as "DEET"), ethyl 3- (N-butyl-N-acetyl) aminopropionate (hereinafter, referred to as "IR 3535"), 2- (2-hydroxyethyl) -1-methylpropyl 1-piperidinecarboxylate (hereinafter, referred to as "ecadotin"), p-menthane-3, 8-diol, 2-ethyl-1, 3-hexanediol, butyl 3, 4-dihydro-2, 2-dimethyl-4-oxo-2H-pyran-6-carboxylate, N-hexyltriethylene glycol monoether, methyl 6-N-pentyl-cyclohexene-1-carboxylate, dimethyl phthalate, eucalyptol, menthol acetate, methyl-N-pentyl-cyclohexene-1-carboxylate, dimethyl phthalate, eucalyptol, menthol, and mixtures thereof, Alpha-pinene, geraniol, citronellal, citronellol, citral, terpineol, camphor, linalool, terpene alcohols, carboxylic acids, dioctyl phthalate, dibutyl phthalate, naphthalene, and the like.
Further, for example, an essential oil or an extract extracted from citronella, peppermint, cedar, lavender, tea tree essential oil, cinnamon, camphor, lemon grass, clover, thyme, geranium, bergamot, bay tree, pine, mastic, pulegate, eucalyptus, Indian downy basin, or the like may be used, and further, pyrethroid-based compounds such as pyrethrin, allethrin, tetramethrin, resmethrin, bifenthrin, permethrin, cyphenothrin, propargyl, ethofenprox, transfluthrin, metofluthrin, profluthrin (profluthrin) and the like may be used.
These pest repellents can be used in combination of 1 or 2 or more, and among them, DEET, IR3535, and ecadotin are preferably used from the viewpoint of high versatility.
It is known that the top layer of the epidermis of the skin, that is, the stratum corneum, has high lipid solubility and is a hydrophobic surface, and therefore, it has good affinity with a drug having a logP value of 1 to 4 measured at 20 to 25 ℃, and the drug easily permeates into the skin. Therefore, the pest repellent having a logP value in the range of 1 to 4 has good affinity with the hydrophobic stratum corneum and is likely to permeate into the stratum corneum.
Therefore, the more the pest repellent having a logP value of 1 to 4 and a larger amount of penetration into the skin, the more remarkably the effect of the present invention of suppressing the penetration of the pest repellent into the skin by at least one ether compound selected from the group consisting of polyoxyethylene polyoxypropylene alkyl ether, polyoxypropylene diglycerol ether, and polyoxypropylene alkyl ether described later can be obtained.
In the present invention, the logP value is a coefficient defined by Chemical Reviews vol71(6),525(1971) and the like, which indicates polarity in terms of the ease with which a substance is dispersed into water and octanol. The logP value of a drug can be calculated by calculation software (PALAAS: Comprodug Chemistry Ltd.), for example, LogP of DEET is 2, LogP of IR3535 is 1.7, and LogP of Elcamantin is 2.1.
In the present invention, at least one ether-based compound (hereinafter, also referred to as "specific ether-based compound") selected from the group consisting of polyoxyethylene polyoxypropylene alkyl ether, polyoxypropylene diglycerol ether, and polyoxypropylene alkyl ether is applied to the skin together with the pest repellent. By applying the specific ether compound to the skin together with the pest repellent, it is possible to inhibit the penetration of the pest repellent into the interior of the skin.
Although the mechanism of action by which a specific ether compound can inhibit penetration of a pest repellent into the skin by applying it to the skin together with the pest repellent is not clear, it is presumed from the results of various studies by the present inventors that a polyoxyethylene polyoxypropylene alkyl ether, a polyoxypropylene diglycerol ether, and an ethylene oxide group or a propylene oxide group of a polyoxypropylene alkyl ether have an effect of retaining the pest repellent and defend against penetration into the skin, and thus exhibit an excellent effect of inhibiting penetration of the pest repellent into the skin.
By applying the specific ether compound to the skin, it is possible to inhibit the penetration of the pest repellent into the skin, and therefore, it is possible to make the pest repellent stay on the skin for a longer time, and as a result, it is possible to improve the persistence of the pest repellent effect of the pest repellent on the skin. Accordingly, the present invention also provides a method, namely: by applying a specific ether compound to the skin together with the pest repellent, the penetration of the pest repellent to the skin is suppressed, and the persistence of the pest repellent effect of the pest repellent on the skin is improved.
In addition, by applying a specific ether compound to the skin, the penetration of the pest repellent into the skin is suppressed, and therefore, the irritation of the pest repellent to the skin can be suppressed. Accordingly, the present invention also provides a method, namely: by applying a specific ether compound to the skin together with the pest repellent, the penetration of the pest repellent into the skin is suppressed, and the irritation of the pest repellent to the skin is suppressed.
The specific ether compound used in the present invention preferably has a weight average molecular weight of 500 to 10,000. When the weight average molecular weight of the specific ether compound is 500 or more, the desired effect of the present invention can be sufficiently obtained, and when it is 10,000 or less, the preparation can be easily prepared. The weight average molecular weight of the specific ether compound is preferably 600 or more, more preferably 650 or more, further preferably 5,000 or less, and further preferably 4,000 or less.
The weight average molecular weight can be determined by gel permeation chromatography.
The polymerization degree of the specific ether compound is preferably 3 to 200. The desired effect of the present invention can be sufficiently obtained if the polymerization degree of the specific ether compound is 3 or more, and the specific ether compound having a polymerization degree of 200 or less is preferable because it has high versatility. The polymerization degree of the specific ether compound is more preferably 5 or more, further preferably 9 or more, further preferably 100 or less, further preferably 80 or less. In the case of the copolymer, the sum may be within the above range.
The carbon number of the specific ether compound is preferably 10 to 600. If the number of carbon atoms of the specific ether compound is 10 or more, the desired effect of the present invention is sufficiently obtained, and if it is 600 or less, compatibility with various components becomes high when the compound is used as a pest repellent composition. The carbon number of the specific ether compound is more preferably 20 or more, still more preferably 30 or more, still more preferably 400 or less, and still more preferably 200 or less.
The average molar number of addition of oxypropylene groups in the specific ether compound is preferably 3 to 100. The preferred range of the average number of addition mols of oxypropylene groups in each of polyoxyethylene polyoxypropylene alkyl ether, polyoxypropylene diglycerol ether and polyoxypropylene alkyl ether is 5 to 100, 3 to 20 and 3 to 100.
Examples of the polyoxyethylene polyoxypropylene alkyl ether include: polyoxyethylene (9) polyoxypropylene (10) butyl ether, polyoxyethylene (17) polyoxypropylene (17) butyl ether, polyoxyethylene (30) polyoxypropylene (30) butyl ether, polyoxyethylene (37) polyoxypropylene (38) butyl ether, polyoxyethylene (10) polyoxypropylene (8) cetyl ether, polyoxyethylene (20) polyoxypropylene (8) cetyl ether, and the like.
The number of carbon atoms of the alkyl group is preferably 1 to 30, more preferably 1 to 5. When the number of carbon atoms of the alkyl group is within the above range, the desired effect of the present invention can be sufficiently obtained, and when the composition is used as an insect repellent composition, the composition has high compatibility with various components, and further has an effect of providing a good feeling in use. The average molar number of addition of the oxyethylene group is preferably 5 to 100, more preferably 5 to 50. The average molar number of addition of the oxypropylene group is preferably 5 to 100, more preferably 5 to 50. When the average molar number of addition of the oxypropylene group is within the above range, the desired effects of the present invention can be sufficiently obtained.
Commercially available polyoxyethylene polyoxypropylene alkyl ethers may be used, and examples thereof include: "UNILUBE 50 MB-11", "UNILUBE 50 MB-26", "UNILUBE 50 MB-72", "UNILUBE 50 MB-168", "UNISAFE 10P", "UNISAFE 20P-8" (trade names), and "Newpol 50 HB-55", "Newpol 50 HB-100", "Newpol 50 HB-260", "Newpol 50 HB-400", "Newpol 50 HB-660", "Newpol 50 HB-2000", "Newpol 50 HB-5100" (trade names), all available from Nissan oil Co., Ltd.
Examples of the polyoxypropylene diglycerol ether include: polyoxypropylene (9) diglycerol ether, polyoxypropylene (14) diglycerol ether, and the like.
The average molar number of addition of the oxypropylene group is preferably 3 to 20, more preferably 5 to 15. When the average molar number of addition of the oxypropylene group is within the above range, the desired effects of the present invention can be sufficiently obtained.
As the polyoxypropylene diglycerol ether, commercially available products can be used, and examples thereof include: "UNILUBE DGP-700" available from Nichiyu oil Co., Ltd "," UNILUBE DGP-950 "(trade name)," SY-DP14 "available from Kagaku chemical industries, Ltd", "SY-DP 9" (trade name), and the like.
As the polyoxypropylene alkyl ether, for example, there can be mentioned: polyoxypropylene (12) butyl ether, polyoxypropylene (52) butyl ether, polyoxypropylene (15) stearyl ether and the like.
The number of carbon atoms of the alkyl group is preferably 1 to 30, more preferably 1 to 5. If the number of carbon atoms in the alkyl group is within the above range, the desired effect of the present invention can be sufficiently obtained, and when the composition is used as a pest repellent composition, the composition has high compatibility with various components, and further, the effect of providing a good feeling in use can be obtained. The average molar number of addition of the oxypropylene group is preferably 3 to 100, more preferably 3 to 60. When the average molar number of addition of the oxypropylene group is within the above range, the desired effects of the present invention can be sufficiently obtained.
As the polyoxypropylene alkyl ether, commercially available ones can be used, and examples thereof include: "UNILUBE MB-7", "UNILUBE MB-700", "UNILUBE MS-70K" (trade name), manufactured by Nichiya Japan K.K. "ARLAMOL PS 15E" (trade name), manufactured by Croda Japan K.K., and the like.
The specific ether compounds may be used alone or in combination of two or more.
In the present invention, from the viewpoint of compatibility with various components when used as a pest repellent composition, polyoxyethylene (9) polyoxypropylene (10) butyl ether, polyoxyethylene (17) polyoxypropylene (17) butyl ether, polyoxyethylene (30) polyoxypropylene (30) butyl ether, polyoxyethylene (37) polyoxypropylene (38) butyl ether is preferably used as the polyoxyethylene polyoxypropylene alkyl ether, polyoxypropylene (9) diglycerol ether is preferably used as the polyoxypropylene alkyl ether, polyoxypropylene (12) butyl ether and polyoxypropylene (52) butyl ether are preferably used as the polyoxypropylene alkyl ether. In addition, from the viewpoint of having a good effect of inhibiting penetration of the pest repellent into the skin, polyoxyethylene polyoxypropylene alkyl ether is preferably used.
When the specific ether compound of the present invention is applied to the skin together with an insect repellent, the specific ether compound is preferably used in an amount of 1 to 300 parts by mass, more preferably 3 to 200 parts by mass, and still more preferably 5 to 100 parts by mass, based on 100 parts by mass of the insect repellent. By using 1 part by mass or more of the specific ether compound per 100 parts by mass of the pest repellent, an effect of inhibiting penetration of the pest repellent into the skin can be suitably obtained, and by using 300 parts by mass or less, a pest repellent effect can be suitably obtained, and the desired effect of the present invention can be sufficiently obtained. If the amount is too large, the active ingredient may not be volatilized and may not be repelled effectively.
When the specific ether compound of the present invention is applied to the skin together with the pest repellent, both the pest repellent and the specific ether compound may be applied simultaneously or separately. From the viewpoint of ease of application to the entire skin, from the viewpoint of mitigating the irritation of an insect repellent such as DEET, and from the viewpoint of simplicity, it is preferable to apply both to the skin as a preparation.
When the pest repellent and the specific ether compound are applied to the skin, they can be applied to the skin as various preparations such as a pump, a lotion, a wet wipe, a roll-on, a coating, a gel, a cream, an aerosol, and the like.
When these preparations are produced, the preparations can be produced using known solvents, emulsifying/dispersing agents, propellants and the like, and can be combined with a nonwoven fabric, an applicator, a pump device, an aerosol device or the like as needed to produce a desired preparation form, as long as the effects of the present invention can be achieved.
Examples of the solvent that can be used include: tap water, purified water, ionized water, and the like; lower alcohols such as ethanol, isopropanol, lauryl alcohol, cetyl alcohol, 2-hexyldecyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, lanolin alcohol, etc.; polyhydric alcohols such as ethylene glycol, diethylene glycol monoethyl ether, triethylene glycol, propylene glycol, dipropylene glycol, 1, 3-butanediol, 1, 3-pentanediol, and glycerin; hydrocarbon solvents, and the like.
Examples of the emulsifying/dispersing agent include: sorbitan trioleate, polyoxyethylene monooleate, polyoxyethylene alkyl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene hydrogenated castor oil, polyoxyethylene alkyl ether, decaglyceryl monooleate (デカグリセリンモノオレート), propylene glycol dioleate, polyoxyethylene stearamide, polyoxyethylene lauryl ether phosphoric acid, glycerin fatty acid ester, stearyl alcohol, polyvinylpyrrolidone, lanolin fatty acid, surfactant such as polyoxyethylene glyceryl triisostearate, lower alcohol, polyhydric alcohol and the like.
In the case where the pest repellent and the specific ether-based compound are applied to the skin, for example, in the case where the pest repellent is DEET, it is preferable that the amount of attachment of DEET to the skin is 1.5mg/100cm2Above, more preferably 5.0mg/100cm2Above, and preferably, the amount of the specific ether compound adhered to the skin is 0.3mg/100cm2The above is applied. By setting the amount of DEET and the specific ether compound adhering to the skin to the above range, it is possible to sufficiently obtain the pest-repelling effect and the effect of inhibiting penetration into the skin. Further, from the viewpoint of obtaining a good feeling in use, DEET is more preferably 1.5 to 150mg/100cm2The specific ether compound is 0.3-450 mg/100cm2The amount of the deposit of (3) is used.
In order to obtain such preferable conditions, for example, when the insect repellent and the specific ether compound are applied to the skin, the amount of the insect repellent and the specific ether compound attached to the skin may be adjusted by adjusting the nozzle, valve, spray pressure, and the like in the case of using an aerosol or a pump, or by adjusting the shape of the application surface, the material properties of the application part, and the like in the case of using a coating agent, a bead-moving agent, or a wet wipe agent.
When the preparation is applied to the skin in the form of an aerosol, the preparation may be pressurized and filled into an aerosol container so that the amount of the propellant is 40 to 95 v/v% with respect to the entire preparation. As the propellant, for example, liquefied petroleum gas, dimethyl ether, freon substitute (substitute フロン), compressed gas (carbon dioxide, nitrogen gas), a mixture thereof, or the like can be used.
In addition, when the preparation is applied to the skin in the form of a wet tissue, the weight per unit area of the support is preferably 20 to 80g/m2. The weight per unit area of the support is 20-80 g/m2Thereby enabling the desired pest repellent and the incorporation, holding, coating, impregnation of the specific ether compound.
Further, it is preferable that the support is held at a thickness of about 0.1 to 5mm in a range of 70 to 300ml/m2The pest repellent of (1). By using the pest repellent at the concentration of 70-300 ml/m2The insect repellent and the ether compound of the present invention can be taken in, held, coated, or impregnated by being held on a support.
As the support, there can be used: woven fabrics such as velvet, cotton, silk, polyester, nylon, and products made of these materials; non-woven fabrics such as polyester, polyolefin, nylon, cotton, rayon, vinylon, cellulose, and products made from these materials; and sheet-like resin foams obtained by foaming polyethylene, polypropylene, ethylene-vinyl acetate copolymer, polyvinyl chloride, or the like.
In order to further improve the feeling of use, enhance the pest repellent effect, and impart the bactericidal effect, various preparations may contain, for example, powders, perfume components, bactericidal/antiseptic components, moisturizing components, thickeners, lubricants, solubilizers, pH adjusters, stabilizers, and the like in any amounts.
For example, there may be mentioned: inorganic powders such as hydrophobic silica, calcium silicate, diatomaceous earth, high-purity silica, anhydrous silicic acid, talc, calcium carbonate, magnesium stearate, acid clay, white carbon, pearlite, etc.; metal salts of starch alkenyl succinates such as aluminum corn starch octenyl succinate; silk powder and other natural powders; powders of resins such as nylon and polypropylene; perfume ingredients such as menthol, peppermint oil (peppermint oil), and mentha oil (mentha oil); bactericidal and antiseptic components such as phenol, paraben, salicylic acid and its salt, benzalkonium chloride, cetylpyridinium chloride, chlorhexidine gluconate, and phenoxyethanol; moisturizing components (moisturizer) such as sodium hyaluronate, ceramide, collagen, placenta extract, milk protein, sorbitol, glycerol, ascorbic acid (vitamin C derivative), N-stearoyl sphingosine (N- ステアロイルフィトスフィンゴジン), dipotassium glycyrrhizinate, meadowfoam seed oil, and natural vitamin E; thickeners such as carboxyvinyl polymer, 3-octadecyloxy-2-hydroxypropyl methylcellulose, and acrylic acid-alkyl methacrylate copolymer; ultraviolet absorbing/blocking components such as p-aminobenzoate, cinoxate, and oxybenzene; antiperspirant/deodorant components such as aluminum chlorohydrate, aluminum/zirconium chlorohydrate (アルミニウム, ジルコニウムクロロヒドレート), etc.; coloring components such as Carthami flos; lubricants such as octamethyltrisiloxane, decamethyltetrasiloxane, methylpolysiloxane, and polyoxyethylene-methylpolysiloxane copolymers; citric acid, sodium citrate, arginine, triisopropanolamine and other pH regulators; and stabilizers such as monoglyceride 2-ethylhexyl ether and pentasodium pentaethylenetriaminepentaacetate solution (ジエチレントリアミン pentaacetic acid penta ナトリウム solution).
Further, by blending higher fatty acid esters such as isopropyl myristate and hexyl laurate; aloe, peach, angelica, cordyceps sinensis, tomato, carrot, tomato, red grape, angelica keiskei, althea, arnica, kelp, cucumber, black tea, burdock, mushroom, prepared rhizome of rehmannia, rhubarb, sweet tea, prune, towel gourd, peony, lily, apple, lychee and other plant extracts; silicone, etc., thereby enabling the persistence of the pest repellent effect and further improvement of the feeling of use.
Examples of pests that can be repelled by the present invention include: various stinging and biting pests such as mosquitoes, black flies, ticks, fleas, stable flies, bugs, leeches, ticks, bees, ants, gadflies, chiggers and the like.
The present invention relates to an invention relating to the use of at least one ether compound selected from the group consisting of polyoxyethylene polyoxypropylene alkyl ether, polyoxypropylene diglycerol ether, and polyoxypropylene alkyl ether together with a pest repellent for application to the skin in order to inhibit penetration of the pest repellent into the skin, and the application of the invention can provide a pest repellent composition in which the persistence of the pest repellent effect is improved and irritation to the skin is suppressed.
Examples of the pest repellent include various compounds described above. The content of the pest repellent is usually 0.1 to 99.5 w/v%, more preferably 0.1 to 50 w/v%, still more preferably 0.5 to 50 w/v%, and particularly preferably 1 to 30 w/v% with respect to the pest repellent composition. If the content of the pest repellent is 1 w/v% or more, the persistent effect is remarkable, and therefore, it is preferable that the content is 30 w/v% or less, since the stickiness is small.
In order to obtain an effect of continuously improving the pest repellent effect in the skin, it is necessary to apply an effective amount of a specific ether compound to the skin. The effective amount of the specific ether compound is preferably 0.1 to 99.5 w/v%, more preferably 0.1 to 50 w/v%, even more preferably 0.5 to 30 w/v%, and particularly preferably 0.5 to 10 w/v% with respect to the pest repellent composition. The content of the specific ether compound is preferably 0.5 w/v% or more because the persistent effect is remarkable, and preferably 10 w/v% or less because the viscosity is small.
In the pest repellent composition, the content of the specific ether compound is preferably 1 to 300 parts by mass, and more preferably 5 to 100 parts by mass, based on 100 parts by mass of the pest repellent. If the amount is within the above range, the effect of the specific ether compound on inhibiting the penetration of the pest repellent into the skin is more excellent.
The pest repellent composition can be applied to various preparations such as pump agent, lotion, wet wipe, bead agent, coating agent, gel, cream, aerosol, etc. as described above.
When these preparations are produced, the preparations can be produced using known solvents, emulsifying/dispersing agents, propellants and the like as described above, and can be combined with a nonwoven fabric, an actuator, an applicator, a pump device, an aerosol device or the like as needed to obtain a desired preparation form, as long as the effects of the present invention can be achieved.
Further, the present invention provides a penetration inhibitor for inhibiting penetration of a pest repellent into skin, comprising at least one ether compound selected from the group consisting of polyoxyethylene polyoxypropylene alkyl ether, polyoxypropylene diglycerol ether, and polyoxypropylene alkyl ether. The penetration inhibitor contains the specific ether compound of the present invention, and thus can inhibit penetration of the pest repellent into the skin, and allow the pest repellent to stay on the epidermis for a longer period of time.
[ examples ]
The present invention will be further described below with reference to examples and comparative examples, but the present invention is not limited to the following examples.
< test example 1: skin absorption inhibition test
Examples 1 to 7, comparative examples 1 to 3, and reference example 1
The components were mixed with stirring according to the formulation shown in table 1 to prepare an insect repellent composition.
Using the resulting pest-repelling composition, the residual amount of DEET (logP: 2) on the skin was measured according to the following test method.
[ Table 1]
TABLE 1 (compounding amount: w/v%)
[ test method ]
As the test apparatus, a horizontal diffusion cell (a horizontal PERMCELL for a flat membrane, manufactured by ビードレックス) shown in fig. 1 was used. The horizontal diffusion cell 10 is a device in which the receiving cell 2 and the supply cell 11 covered with the water jacket 4 are disposed to face each other in a horizontal state with a sample film (skin 1) therebetween, and the receiving cell 2 and the supply cell 11 can be joined to and separated from each other. In this test, the supply cell 11 side was used for fixing the sample film.
1. The skin 1 of a mouse (test skin, obtained from breeding of a wild laboratory animal, ltd.) was attached to the horizontal diffusion cell 10 such that the dermis side of the skin 1 was located on the receiving cell 2 side.
2. To the stratum corneum side (4.9 cm) of skin 12) Approximately 45 μ L of the pest repellent composition prepared above was treated, covered with aluminum foil 8, and skin 1 was fixed using fastening handle 6.
3. The receiving tank 2 is filled with 50mL of physiological saline 9, and the tank is filled with the physiological saline 9.
4. During the experiment, the receiving tank 2 was stirred with the physiological saline in the tank by the stirrer 3, and warm water of 37 ℃ was circulated in the water jacket 4 covering the receiving tank 2 by the heater/circulator 5, so that the temperature in the receiving tank 2 was kept constant at 37 ℃.
5. 3mL of physiological saline 9 was sampled from the sampling port 7 of the receiving tank 2 every 1 hour from the time when the temperature in the receiving tank 2 reached 37 ℃. Then, the same amount of physiological saline was added to the receiving tank 2 to keep the liquid amount constant.
6. The amount of DEET in the sample solution was measured by High Performance Liquid Chromatography (HPLC).
HPLC measurement conditions
The column used: STR ODS-II (250L X4.6 mm I.D. manufactured by SHIMADZU GLC, LTD.)
A detector: ultraviolet absorption light detector
Wavelength: 254mm
Mobile phase: 60/40% acetonitrile/water
Flow rate: 1mL/min
Column temperature: 40 deg.C
7. The residual amount on the skin was calculated according to the following formula. The residual amount on the skin (mg/cm)2) Is a value obtained by rounding off the third digit after the decimal point.
Residual amount on skin of DEET (mg/cm)2) Treatment of DEET volume-samplingDEET amount in afterliquid X50/3)/treated area
The results obtained in the above test are shown in table 2. The residual amount on the skin was 0.05mg/cm 2In this way, it can be judged that the repellent effect is exhibited.
[ Table 2]
TABLE 2
According to the results shown in Table 2, in comparative examples 1 to 3, the amount of DEET remaining on the skin after 3 hours from the start of measurement was 0.04mg/cm2Hereinafter, an effective amount that does not provide a repellent effect remains on the skin for 3 hours or more. In contrast, in examples 1 to 7, the amount of DEET remaining was 0.05mg/cm even after 3 hours from the start of the measurement2Above, an effective amount capable of imparting a repellent effect remains on the skin for 3 hours or more. In particular, in examples 1 to 4, 6 and 7, the amount of DEET remaining after 3 hours from the start of the measurement was 0.10mg/cm2Of the above, examples 1 to 3 and 6 had a DEET content of 0.05mg/cm even after 4 hours from the start of the measurement2The above.
From these results, it is understood that examples 1 to 7 can suppress the penetration of the pest repellent into the skin and can make the pest repellent stay on the skin for a long time.
< test example 2: test for blood sucking hindrance
(examples 8 to 9, comparative examples 4 to 5)
The components were mixed with stirring according to the formulation shown in table 3 to prepare an insect-repellent composition.
Using the obtained pest repellent composition, the repellent rate was measured according to the following test method.
[ Table 3]
TABLE 3 (compounding amount: w/v%)
| Example 8 | Example 9 | Comparative example 4 | Comparative example 5 | |
| N, N-diethyl-m-toluamide (DEET) (logP ═ 2) | 6.0 | 6.0 | 6.0 | 10.0 |
| Polyoxyethylene (9) polyoxypropylene (10) butyl ether | 0.5 | 20 | - | - |
| Acrylic resin alkanolamine solution | - | - | 2.0 | - |
| Anhydrous ethanol | Proper amount of | Proper amount of | Proper amount of | Proper amount of |
| Total up to | 100mL | 100mL | 100mL | 100mL |
[ test method ]
The test was carried out according to the following procedure.
1. In an arm insertion window (about 113 cm) having an openable/closable opening2) About 50 aedes albopictus females are placed in a metal cage (25 cm in length, 25cm in width, 25cm in height).
2. The insect repellent composition prepared as described above was applied to the back of the hand of the subject, and after the application, rubber gloves were put on, in which the back of the hand was cut into a substantially square shape of 5cm × 5 cm. The coating weight was 1.34. mu.L/cm2。
3. After wearing the rubber gloves, the hands were put in from the arm insertion windows of the metal cage in which aedes albopictus was placed every 1 hour, and the Number of drops (Number of landings) of the aedes albopictus exposed to the back of the hand (5cm × 5cm) was counted while maintaining this state for 300 seconds. Each example was repeated 3 or 4 times, and the average value was calculated.
4. As a non-treated area, the same test was performed on the other hand of the subject without applying the pest-repelling composition. The rubber gloves were put on with the back of the hand being cut out in a substantially square shape of を 5cm × 5cm, and the number of aedes albopictus drops per 1 hour after putting on the gloves were counted. Each example was repeated 3 or 4 times, and the average value was calculated.
5. The repelling rate was calculated from the number of aedes albopictus drops in the treated area and the number of aedes albopictus drops in the untreated area when the insect repellent composition was applied.
The repellency rate (%) < percent (number of landings in non-treated area-number of landings in treated area)/number of landings in non-treated area x 100
The results obtained in the above tests are shown in table 4 and fig. 2.
[ Table 4]
TABLE 4
As is clear from the results in table 4 and fig. 2, in comparative example 5 containing DEET alone, the duration of time at which the repellency rate was 80% or more was exhibited was 3 hours. In contrast, in comparative example 4, the duration of the repellent ratio of 80% or more was 4 hours, but in examples 8 and 9, the duration of the repellent ratio of 80% or more was 5 hours or more.
< test example 3: test for blood sucking hindrance
(example 10, comparative examples 6 to 7)
The components were mixed with stirring according to the formulation shown in table 5 to prepare an insect-repellent composition. Comparative example 6 was prepared in the same manner as comparative example 5 of test example 2.
Using the obtained pest repellent composition, the repellent rate was measured according to the following test method.
[ Table 5]
TABLE 5 (compounding amount: w/v%)
| Example 10 | Comparative example 6 | Comparative example 7 | |
| N, N-diethyl-m-toluamide (DEET) (logP ═ 2) | 10.0 | 10.0 | 30.0 |
| Polyoxyethylene (9) polyoxypropylene (10) butyl ether | 2.0 | - | - |
| Polypropylene glycol | - | - | - |
| Anhydrous ethanol | Proper amount of | Proper amount of | Proper amount of |
| Total up to | 100mL | 100mL | 100mL |
[ test method ]
The test was carried out according to the following procedure.
1. In an arm insertion window (about 113 cm) having an openable/closable opening2) About 50 aedes albopictus females were placed in a metal cage (25 cm longitudinal. times.25 cm transverse. times.25 cm high).
2. The insect repellent composition prepared as described above was applied to the back of the hand of the subject, and after the application, rubber gloves were put on, in which the back of the hand was cut into a substantially square shape of 5cm × 5 cm. The coating weight was 0.80. mu.L/cm2。
3. After wearing rubber gloves, hands were put in from the arm insertion windows of the transparent cages containing aedes albopictus at intervals of 1 hour, and the Number of drops (Number of landings) of aedes albopictus at the exposed portion (5cm × 5cm) of the back of the hand was counted while keeping this state for 300 seconds. Each example was repeated 3 or 4 times, and the average value was calculated.
4. As a non-treated area, the same test was performed on the other hand of the subject without applying the pest-repelling composition. The rubber gloves were put on with the back of the hand being cut out in a substantially square shape of を 5cm × 5cm, and the number of aedes albopictus drops per 1 hour after putting on the gloves were counted. Each example was repeated 3 or 4 times, and the average value was calculated.
5. The repelling rate was calculated from the number of aedes albopictus drops in the treated area and the number of aedes albopictus drops in the untreated area when the insect repellent composition was applied.
The repellency rate (%) < percent (number of landings in non-treated area-number of landings in treated area)/number of landings in non-treated area x 100
The results obtained by the above tests are shown in table 6 and fig. 3.
[ Table 6]
TABLE 6
From the results shown in table 6 and fig. 3, in example 10, the duration time in which the repellency rate was 80% or more was 9 hours, and the state in which the repellency rate was 80% or more lasted 7 hours more than comparative example 6 in which the content of DEET was the same. In example 10, the duration of time in which the repellency rate was 80% or more was equal to or more than that in comparative example 7 in which the DEET content was 3 times.
From the above results, it is understood that the present invention can maintain the pest repellent effect for a long period of time even when the pest repellent is used at a low concentration.
Next, a formulation example of a formulation containing a specific ether compound as a permeation inhibitor for inhibiting the permeation of the pest repellent into the skin according to the present invention will be described below.
[ Table 7]
< formulation example 1: aerosol agent >
The amount of each component is adjusted to 100% of the total amount of the components.
[ Table 8]
< formulation example 2: pump agent >
The amount of each component is adjusted to 100% of the total amount of the components.
[ Table 9]
< formulation example 3: wet towel preparation >
The amount of each component is adjusted to 100% of the total amount of the components.
[ Table 10]
< formulation example 4: gelling agent >
The amount of each component is adjusted to 100% of the total amount of the components.
While the present invention has been described in detail with reference to the specific embodiments, it is obvious to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the present invention. In addition, the present application is based on Japanese patent application laid-open at 2016 (8/10) (Japanese patent application No. 2016-158007), the entire contents of which are incorporated herein by reference.
Claims (11)
1. A method of inhibiting the penetration of a pest repellent into the skin, wherein,
at least one ether compound selected from the group consisting of polyoxyethylene polyoxypropylene alkyl ether and polyoxypropylene diglycerol ether is applied to the skin together with the pest repellent,
the polyoxyethylene polyoxypropylene alkyl ether has an alkyl group having 4 carbon atoms.
2. The method of inhibiting the penetration of a pest repellent into skin according to claim 1,
The pest repellent is at least one selected from the group consisting of N, N-diethyl-m-toluamide, ethyl 3- (N-butyl-N-acetyl) aminopropionate, and 2- (2-hydroxyethyl) -1-methylpropyl 1-piperidinecarboxylate.
3. The method of inhibiting the penetration of a pest repellent into skin according to claim 1,
the average addition mole number of oxypropylene groups of the ether compound is 3 to 100.
4. The method of inhibiting the penetration of a pest repellent into skin according to claim 2,
the average addition mole number of oxypropylene groups of the ether compound is 3 to 100.
5. The method of inhibiting the penetration of a pest repellent into skin according to any one of claims 1 to 4,
the ether compound is used in an amount of 1 to 300 parts by mass per 100 parts by mass of the pest repellent.
6. The method of inhibiting the penetration of a pest repellent into skin according to any one of claims 1 to 4,
the pest repellent is N, N-diethyl-m-toluamide, and the attachment amount of the N, N-diethyl-m-toluamide is 1.5mg/100cm2The above ether compound has an attachment amount of 0.3mg/100cm 2The above manner is used.
7. The method of inhibiting penetration of a pest repellent to skin according to claim 5,
the pest repellent is N, N-diethyl-m-toluamide, and the attachment amount of the N, N-diethyl-m-toluamide is 1.5mg/100cm2The above ether compound has an attachment amount of 0.3mg/100cm2The above manner is used.
8. A penetration inhibitor for inhibiting penetration of a pest repellent into skin, wherein,
comprising at least one ether compound selected from the group consisting of polyoxyethylene polyoxypropylene alkyl ether and polyoxypropylene diglycerol ether,
the polyoxyethylene polyoxypropylene alkyl ether has an alkyl group having 4 carbon atoms.
9. The penetration inhibitor for inhibiting penetration of a pest repellent into skin according to claim 8,
for inhibiting penetration of a pest repellent to the skin, the pest repellent being at least one selected from the group consisting of N, N-diethyl-m-toluamide, ethyl 3- (N-N-butyl-N-acetyl) aminopropionate, and 2- (2-hydroxyethyl) -1-methylpropyl 1-piperidinecarboxylate.
10. The penetration inhibitor for inhibiting penetration of a pest repellent into skin according to claim 8 or 9,
The average addition mole number of oxypropylene groups of the ether compound is 3 to 100.
11. A method of inhibiting irritation of a pest repellent to skin, wherein,
at least one ether compound selected from the group consisting of polyoxyethylene polyoxypropylene alkyl ether and polyoxypropylene diglycerol ether is applied to the skin together with the pest repellent,
the polyoxyethylene polyoxypropylene alkyl ether has an alkyl group having 4 carbon atoms.
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| JP2016-158007 | 2016-08-10 | ||
| JP2016158007 | 2016-08-10 | ||
| PCT/JP2017/029186 WO2018030532A1 (en) | 2016-08-10 | 2017-08-10 | Method for inhibiting penetration of pest repellent into skin and agent for inhibiting penetration of pest repellent into skin |
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| CN109843055B true CN109843055B (en) | 2022-06-10 |
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| CN115530178A (en) * | 2022-10-31 | 2022-12-30 | 原上科技(河南)有限公司 | Composition for repelling ticks and killing ticks as well as preparation method and application of composition |
| CN115887303B (en) * | 2022-12-02 | 2024-10-18 | 湖南雪天精细化工股份有限公司 | Mosquito-repellent composition and preparation method thereof |
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| JP2000319643A (en) * | 1999-05-06 | 2000-11-21 | Toyo Aerosol Ind Co Ltd | Aerosol composition and aerosol product |
| JP2009126804A (en) * | 2007-11-21 | 2009-06-11 | Dainippon Jochugiku Co Ltd | Noxious insect repellent for human body |
| CN101730518A (en) * | 2007-05-21 | 2010-06-09 | 阿奎耶科技公司 | Highly charged microcapsule |
| JP2013203663A (en) * | 2012-03-27 | 2013-10-07 | Toyo Aerosol Ind Co Ltd | Insect pest-repelling crackling aerosol composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH11106327A (en) * | 1997-10-01 | 1999-04-20 | Lion Corp | Skin irritation depressant composition |
| JP4189047B2 (en) * | 1997-12-08 | 2008-12-03 | フマキラー株式会社 | Pest repellent aerosol |
| JPH11255606A (en) * | 1998-03-09 | 1999-09-21 | Sekisui Chem Co Ltd | Insect-repellent |
| JP2003171204A (en) * | 2001-12-04 | 2003-06-17 | Kowa Co | Gel-type insect repellent preparation |
| JP2004002224A (en) * | 2002-05-31 | 2004-01-08 | Showa Denko Kk | Insect pest-repellent composition and method for reducing skin irritation of insect pest-repellent ingredient |
| JP6814382B2 (en) * | 2016-02-22 | 2021-01-20 | 日油株式会社 | Pest repellent composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000319643A (en) * | 1999-05-06 | 2000-11-21 | Toyo Aerosol Ind Co Ltd | Aerosol composition and aerosol product |
| CN101730518A (en) * | 2007-05-21 | 2010-06-09 | 阿奎耶科技公司 | Highly charged microcapsule |
| JP2009126804A (en) * | 2007-11-21 | 2009-06-11 | Dainippon Jochugiku Co Ltd | Noxious insect repellent for human body |
| JP2013203663A (en) * | 2012-03-27 | 2013-10-07 | Toyo Aerosol Ind Co Ltd | Insect pest-repelling crackling aerosol composition |
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