CN107249322A - Suppress insects repellant to the method for Cutaneous permeation and suppress infiltration inhibitor of the insects repellant to Cutaneous permeation - Google Patents
Suppress insects repellant to the method for Cutaneous permeation and suppress infiltration inhibitor of the insects repellant to Cutaneous permeation Download PDFInfo
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- CN107249322A CN107249322A CN201680010760.8A CN201680010760A CN107249322A CN 107249322 A CN107249322 A CN 107249322A CN 201680010760 A CN201680010760 A CN 201680010760A CN 107249322 A CN107249322 A CN 107249322A
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- skin
- insects repellant
- insects
- repellant
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- 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
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system
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- A—HUMAN NECESSITIES
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- 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
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- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/02—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings containing insect repellants
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
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- Birds (AREA)
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Abstract
The problem of the present invention is to provide in a kind of method, this method, in order that the continuation for stimulating less and making the pest repelling effect on skin for a long time caused by medicament is improved, and suppresses insects repellant to the infiltration inside skin.Present invention offer is a kind of to suppress method of the pest repelling effect to Cutaneous permeation by the way that PAG is applied into skin together with insects repellant.
Description
Technical field
The present invention relates to suppress insects repellant to the method for Cutaneous permeation and suppress insects repellant to Cutaneous permeation
Infiltration inhibitor.
Background technology
In the prior art, to prevent biting for the hematophaguses such as horsefly, bed bug headed by mosquito, various insects repellants are
It is used widely.For these insects repellants, in order to improve use feeling, reduction excitant, improve continuing for repellent effect
Property, carry out various researchs.
For example, Patent Document 1 discloses a kind of pest repelling composition, in order that the repellent effect of pest repelling composition
Fruit continues, and specific silicic acid anhydride particle has been coordinated in the pest repelling composition.In addition, Patent Document 2 discloses
It is a kind of to the addition of the pest repelling composition of ultra-violet absorber, in order to suppress to decompose caused by light in order to suppress as insect
The DEET (DEET) of repellent composition stimulation and and with the human body insects repellant of natural mineral water.
Prior art literature
Patent document
Patent document 1：Japanese Unexamined Patent Publication 9-208406 publications
Patent document 2：Japanese Unexamined Patent Publication 2009-126804 publications
The content of the invention
Invent the technical problem to be solved
However, for the pest repelling composition of patent document 1, in keeping, the silicic acid anhydride particle of cooperation can be precipitated
In container bottom, it must be mixed when using every time.Therefore, using in the case of pest repelling composition, have not mixing
When produce the problems such as spout, the blocking of spreader, silicic acid anhydride particle are set in jet face, process face.
In addition, in the human body insects repellant of patent document 2, the acquisition of the natural mineral water of cooperation can not say appearance
Easily, and it is difficult to be stably supplied, it is therefore, impracticable.
In addition, in the case where above-mentioned pest repelling composition, insects repellant are applied into skin, because insect drives
Agent is kept away to skin internal penetration, therefore, it is impossible to make insects repellant fully rest on skin for a long time.Therefore, apply
Continuation to the pest repelling effect of the insects repellant of skin is insufficient.Further, the insects repellant such as DEET has
Skin irritation, therefore, once insects repellant is to skin internal penetration, then can cause to stimulate, during applied to human body to skin
Security it is insufficient.
Therefore, problem of the invention is to provide in a kind of method, this method, in order that the stimulation caused by medicament less and
For a long time improve the continuation of the pest repelling effect on skin, and suppress insects repellant to the infiltration inside skin.
Technological means for solving problem
Present inventor has performed further investigation, as a result find, by the way that PAG is answered together with insects repellant
Use on skin, so as to suppress insects repellant to skin internal penetration, insects repellant is stopped epidermis for a long time
(skin surface), so far completes the present invention.
That is, the present invention is as described below.
1. a kind of method, wherein, by the way that PAG is applied into skin together with insects repellant, so as to suppress
Insects repellant is to Cutaneous permeation.
2. the method according to above-mentioned 1, wherein, the logP values of the insects repellant are more than 1.
3. the method according to above-mentioned 1 or 2, wherein, the molecular weight of the PAG is 200~20000.
4. the method according to any one of above-mentioned 1~3, wherein, the PAG is polypropylene glycol.
5. a kind of suppression infiltration inhibitor of the insects repellant to Cutaneous permeation, wherein, the infiltration inhibitor contains poly-
Aklylene glycol.
6. the suppression that is used for of PAG is applied to use of the insects repellant on skin to Cutaneous permeation.
Invention effect
According to the present invention, when insects repellant is applied into skin, PAG is coordinated to apply together, so as to
Enough suppress insects repellant to skin internal penetration.As a result, insects repellant can be made to rest on for a long time on skin, energy
Enough improve the continuation of the pest repelling effect on skin.
Further, even if using insects repellant with low concentration, pest repelling effect can also be made long lasting for energy
Enough provide stimulates human body few preparation.In addition, in the case where using insects repellant with high concentration, due to that can suppress harmful
Worm repellant is to skin internal penetration, therefore, it is possible to suppress stimulation of the insects repellant to skin, using the teaching of the invention it is possible to provide to the peace of human body
The higher preparation of full property.
Brief description of the drawings
Fig. 1 is the schematic diagram that the horizontal diffusion cell for suppressing to be used in experiment is absorbed in skin.
Symbol description
1. skin
2. reception tank
3. stirrer
4. water jacket
5. heater/circulator
6. pinch grip
7. sample tap
8. aluminium foil
9. physiological saline
10. horizontal diffusion cell
Embodiment
Hereinafter, the present invention will be described in more detail.
The present invention provides one kind by the way that PAG is applied into skin together with insects repellant, so as to suppress harmful
Method from worm repellant to Cutaneous permeation.In addition, the suppression that is used for that the present invention provides PAG is applied on skin
Application method from insects repellant to Cutaneous permeation.
As the insects repellant of the present invention, can use to thorn stinging property insect has repellent action or obstruction work of sucking blood
Synthesis or natural various compounds.For example, can enumerate：N, N- dimethyl-toluoyl amine (hereinafter also referred to as
DEET), to terpane -3,8- glycol, 3- (N- acetyl group-n- butyl) alanine ethyl ester, 2- (2- ethoxys) -1- piperidines
Formic acid 1- methyl-props base ester, 2- ethyl -1,3- hexylene glycols, butyl 3,4- dihydro -2,2- dimethyl -4- oxygen -2H- pyrans -6- carboxylics
Acid esters, n- hexyl triethylene glycols monoether, methyl 6- n-pentyls-cyclohexene -1- carboxylates, dimethyl phthalate, eucalyptus
Brain, menthol, peppermint alcohol acetic ester, australene, geraniol, citronellal, citronellol, citral, terpinol, camphor, linalool,
Terpenol, carboxylic acid, dioctyl phthalate, di-n-butyl phthalate, naphthalene etc..
In addition, for example, it is also possible to using from lemongrass, lemongrass, deodar, lavender, tea tree ethereal oil, cassia bark, camphor, lemon
Carried in grass, clover, thyme, fish pelargonium, bergamot, bay tree, pine, Ternstroemia gymnanthera, general row peppermint, eucalyptus, the vertical basin of India etc.
The essential oil or extract taken, it is further possible to use pyrethrins, allethrin, tetramethrin, resmethrin, alkynes
Furan chrysanthemum ester, phenothrin, Permethrin, cyphenothrin, ene-alkyne chrysanthemum ester, ethofenprox, empenthrin, transfluthrin, methoxy
Pyrethroid based compounds such as benzyl Flumethrin, the third Flumethrin (profluthrin) etc..
These insects repellants can use a kind or two or more be applied in combination, in them, from the high viewpoint of versatility
Consider, preferably DEET.
It is preferred that the logP values of the insects repellant of the present invention are more than 1.
In the present invention, logP values refer to, in Chemical Reviews vol71 (6), defined in 525 (1971) etc.
The coefficient of polarity is represented according to the material easy degree scattered into water and octanol.The logP values of medicament can be soft by calculating
Part (PALAAS：CompDrug Chemistry Ltd. systems) calculate.
It is generally believed that logP values are bigger, the compatibility with the keratoderma as hydrophobic surface is better, easier to skin
Skin permeates.The insects repellant that logP values are more than 1 is good due to the compatibility with hydrophobicity cuticula, therefore, in cuticula
Wetting on surface is good.Therefore, the infiltrating area to skin becomes big.To the infiltration of Cutaneous permeation and insects repellant and skin
Area is proportional, therefore, and infiltrating area is big, then infiltration capacity also becomes many.
Therefore, logP values be more than 1, to skin infiltration capacity more than insects repellant, more can significantly obtain
The present invention's suppresses effect of the insects repellant to Cutaneous permeation based on PAG described later, therefore preferably.
In the present invention, PAG is applied to skin together with the insects repellant.By by poly- alkylene
Base glycol is applied to skin together with insects repellant, so as to suppress insects repellant to skin internal penetration.
In addition, by the way that PAG is applied into skin, oozed so as to suppress insects repellant to inside skin
Thoroughly, therefore, it is possible to make insects repellant for longer periods rest on skin, as a result, the insect that can be improved on skin drives
Keep away the continuation of the pest repelling effect of agent.Therefore, the present invention is also provided by by PAG and insects repellant one
Skin is applied to suppress insects repellant to Cutaneous permeation and improve the pest repelling of insects repellant on skin and imitate
The method of the continuation of fruit.
In addition, by the way that PAG is applied into skin, oozed so as to suppress insects repellant to inside skin
Thoroughly, therefore, it is possible to suppressing stimulation of the insects repellant to skin.Therefore, the present invention also provide by by PAG with
Insects repellant is applied to skin to suppress insects repellant to Cutaneous permeation and suppress insects repellant to skin together
The method of stimulation.
By the way that PAG is applied into skin together with insects repellant so as to suppress insects repellant to
The mechanism of action of skin internal penetration is still not clear, but it is because in the alkylidene chain part of PAG that can speculate
Insects repellant is kept, and suppresses insects repellant to skin internal penetration.
It is used as the molecular weight of the PAG, preferably 200~20000, more preferably 200~5000.If poly-
The molecular weight of aklylene glycol is more than 200, then effect significantly, therefore preferably, if less than 20000, then easily make by preparation
It is standby, therefore preferably.
In addition, the degree of polymerization of PAG is preferably more than 3, more preferably 4~400.If PAG
The degree of polymerization be more than 3, then fully obtain the effect of the present invention, therefore preferably, if more than 4, then its effect is more notable,
Therefore preferably.In addition, the degree of polymerization is high for the versatility of less than 400 PAG, therefore preferably.
In addition, the carbon number of PAG is preferably 2~4, more preferably 2~3.If PAG
Carbon number is more than 2, then effect of the invention is notable, therefore preferably, if less than 4, is then combined as pest repelling
During thing and various composition intersolubility it is high, therefore preferably.
In addition, PAG can be straight chain or side chain.Specifically, it can enumerate：Polypropylene glycol and
Polyethylene glycol etc..From the viewpoint of small from versatility, stability and to skin irritation, preferably polypropylene glycol and polyethylene glycol,
Particularly preferred polypropylene glycol.In addition, various PAGs can be used alone, can also two or more combination make
With.
As the PAG being adapted in the present invention, for example, it can enumerate：Polyethylene glycol 200, polyethylene glycol 400,
Macrogol 600, polyethylene glycol-800, cetomacrogol 1000, polypropylene glycol 1000, polypropylene glycol 2000 and polypropylene glycol 4000
Deng.
When PAG is applied into skin together with insects repellant, regarded by the usage amount of insects repellant
For 1 when, the usage amount of PAG by quality ratio, preferably more than 0.025, more preferably more than 0.05.This be because
For in above range, can further improve PAG suppresses effect of the insects repellant to Cutaneous permeation.
, can be by insects repellant and poly- alkylene when PAG is applied into skin together with insects repellant
Both base glycol are applied simultaneously, are applied with can also being individually separated.Calm viewpoint easy to apply in whole skin, alleviate DEET
From the viewpoint of viewpoint and simplicity Deng the stimulation of insects repellant, simultaneously should preferably in the way of the preparation containing both
With.
, for example can be by pump agent, lotion, wet when the insects repellant and PAG are applied into skin
The mode of the various preparations such as towel agent, ballpoint agent, smears, spray is applied to skin.
Make these preparations when, as long as can realize the present invention effect, can use known carrier, propellant,
Prepared by solvent, emulsification/dispersion agent etc., further, as needed with non-woven fabrics, actuator, spreader, pump installation, spray
Mist device etc. is combined, as desired preparation way.
When the insects repellant and PAG are applied on skin together, for example, in insects repellant
In the case of for DEET, the adhesion amount preferably using DEET to skin is 1.5mg/100cm2More than and PAG to
The adhesion amount of skin is 0.3mg/100cm2Mode application above.By making the attachment of DEET and PAG to skin
Amount is in the scope, so as to fully obtain pest repelling effect and suppress infiltration inhibition to Cutaneous permeation.
Further, from the viewpoint of good use feeling is obtained, more preferably using DEET as 1.5~150mg/
100cm2, PAG be 0.3~50mg/100cm2Adhesion amount use.In order to obtain the optimum condition, for example, answering
When using skin, in the case where using spray, pump agent, adjustment spout, valve, injection pressure etc. are using smears, ballpoint
In the case of agent, wet tissue agent, adjustment coated face shape, Wood characteristics of coating part etc., to adjust insects repellant and poly- alkylene
Adhesion amount of the base glycol to skin.
When the preparation is applied into skin in the way of spray, with propellant relative to preparation generally 5~
95v/v% mode, which is pressurizeed, is filled into automiser spray.As propellant, for example, it can use liquefied petroleum gas, dimethyl
Ether, freon sub (instead of Off ロ Application), compressed gas (oxygen, nitrogen) and their mixture etc..
In addition, when the preparation is applied into skin in the way of wet tissue agent, the weight per unit area of supporter is preferred
For 20~80g/m2.By making the weight per unit area of supporter be 20~80g/m2, thus allow for desired pest repelling
Agent and PAG are taken into, kept, being coated with, impregnating.
Additionally, it is preferred that keeping 70~300ml/m in thickness about 0.1~5mm supporter2Insects repellant.Pass through
Make insects repellant with 70~300ml/m2Ground is maintained at supporter, thus allows for desired insects repellant and poly- alkylene
Base glycol is taken into, kept, being coated with, impregnates.
As supporter, it can use：Suede, cotton, silk, polyester, nylon, weave cotton cloth them as raw material person etc.；It is poly-
Ester, polyolefin, nylon, cotton, artificial silk, vinylon, cellulose, it regard them as the non-woven fabrics such as raw material person；Make polyethylene, gather
Foamed resin of sheet after the foaming such as propylene, ethene-vinyl acetate copolymer, polyvinyl chloride etc..
As carrier, for example, it can enumerate：The water such as running water, pure water, ionized water；Ethanol, isopropanol, laruyl alcohol, whale
Ceryl alcohol, 2- hexyl decyl alcohols, stearyl alcohol, with lower alcohols such as stearyl alcohol, oleyl alcohol, lanolin alcohols；Ethylene glycol, diethylene glycol mono-ethyl
The polyalcohols such as ether, triethylene glycol, propane diols, 1,3 butylene glycol, glycerine；Varsol etc..
As emulsification/dispersion agent, for example, it can enumerate：It is sorbitan trioleate, Aceonon 300 MO, poly-
Oxygen vinyl alkyl ether, ethylene nonyl phenyl ether, Crodaret, polyoxyethylene alkyl ether, ten polyglycereol lists
Oleate (デ カ グ リ セ リ Application モ ノ オ レ ー ト), two oleic acid propylene glycol esters, polyoxyethylene 8 stearate acid amides, polyoxyethylene month
It is the surfactants such as osmanthus base ether phosphoric acid, fatty acid glyceride, stearyl alcohol, polyvinylpyrrolidone, lanolin fatty acid, rudimentary
Alcohol, polyalcohol etc..
In order to further improve use feeling, pest repelling effect, imparting bactericidal effect be improved, for example, can be with any amount
Powder, fragrance component, sterilization and anticorrosion composition, moisturizing ingredient, thickener etc. be applied to skin in combination.
For example, can enumerate：The silicic acid chemical combination such as hydrophobic silica, calcium silicates, diatomite, high-purity silica, silicic acid anhydride
Thing；The inorganic powders such as talcum, calcium carbonate, magnesium stearate, Emathlite, White Carbon black, pearlite；Ocentyl succinic cornstarch
The metal salt of the starch alkenyl succinates such as ester aluminium；The natural powders such as silk powder；The powder of the resins such as nylon, polypropylene etc.；Menthol,
The fragrance components such as peppermint oil (peppermint oil), peppermint oil (mentha oil)；Phenol, p-hydroxybenzoate, bigcatkin willow
The sterilization and anticorrosion composition such as acid and its salt, benzalkonium chloride, Cetylpyridinium Chloride, chlorhexidine gluconate, Phenoxyethanol；Hyaluronic acid
The moisturizing ingredients such as sodium, ceramide, collagen, intacellin, lactoprotein, vitamin C derivatives, D-sorbite, glycerine
(wetting agent)；The thickeners such as C974P, the epoxide -2- hydroxypropyl 2- hydroxypropyl methyl celluloses of 3- 18；To amino
The ultraviolet radiation absorption such as benzoic ether, Cinoxate, oxybenzene/stop composition；Aluminium chlorohydrate, aluminum chlorohydrate/zirconium (ア Le ミ ニ ウ
System ジ Le U ニ ウ system Network ロ ロ ヒ ド レ ー ト) etc. hidroschesis/deodorization composition；Pigment compositions such as safflower etc..
Further, by coordinating the high-grade aliphatic esters such as isopropyl myristate, lauric acid hexyl ester；Aloe, peach, when
Return, cordyceps sinensis, tomato, carrot, tomato, red grape, Angelica Keiskei, the another name for Sichuan Province last of the ten Heavenly stems, Arnica, sea-tangle, cucumber, black tea, ox
The plant extracts such as burdock, mushroom, cultivated land, rheum officinale, Sweet tea, prune, sponge gourd, tree peony, lily, apple, lichee；Silicone etc., so that
The further raising of the lasting and use feeling of pest repelling effect can be realized.
As the insect for the repellent object that can turn into the present invention, for example, it can enumerate：Mosquito, black fly, tick, flea, stable fly,
Various thorn the stinging property insects such as bedbug, mountain leech, tick, honeybee, ant, horsefly, trombiculid.
The present invention relates in order to suppress insects repellant to skin internal penetration by PAG and pest repelling
Agent is applied to as skin together, the purposes of PAG, and pest repelling is improved there is provided one kind by the application present invention
The continuation of effect and the pest repelling composition for suppressing the stimulation to skin.
As insects repellant, foregoing various compounds can be enumerated.Insects repellant is combined relative to pest repelling
Thing, usually 0.1~99.5w/v%, more preferably more preferably 0.1~50w/v%, 0.5~50w/v%, especially excellent
Select 1~30w/v%.If more than 1w/v%, then lasting effect is notable, therefore preferably, if below 30w/v%, then glues
Property is small, therefore preferably.
For the effect of the continuation of pest repelling effect that is improved in skin, it is necessary to by the polyalkylene of effective dose
Glycol is applied on skin.As the effective dose of PAG, preferably relative to pest repelling composition be 0.1~
99.5w/v%, more preferably 0.1~50w/v%, further preferred 0.5~30w/v%, particularly preferred 0.5~10w/v%.If
For more than 0.5%w/v, then lasting effect is notable, therefore preferably, it is if below 10w/v%, then sticky small, therefore preferably.
In above-mentioned pest repelling composition, when using the content of insects repellant as 1, the content of PAG
By quality ratio, preferably more than 0.025, more preferably more than 0.05.Because, within the above range, polyalkylene two
The suppression insects repellant of alcohol is higher to the effect of Cutaneous permeation.
Above-mentioned pest repelling composition can be used as foregoing pump agent, lotion, wet tissue agent, ballpoint agent, smears, spray
The various preparations such as mist agent and use.
When making these preparations, as long as realizing the effect of the present invention, foregoing known carrier, injection are used
It is prepared by agent, solvent, emulsification/dispersion agent etc., according further to need with non-woven fabrics, actuator, spreader, pump installation,
The combination such as sprayer unit makes desired preparation way.
The present invention is also provided suppresses infiltration inhibitor of the insects repellant to Cutaneous permeation containing PAG.Should
Infiltration inhibitor contains PAG, therefore, it is possible to suppress insects repellant to skin internal penetration, can drive insect
Keep away agent and for longer periods rest on epidermis.
Embodiment
Hereinafter, by embodiment and comparative example, the present invention is further described, but the present invention is not by following examples
Any limitation.
＜ ＜ test examples 1：Skin, which absorbs, suppresses experiment) ＞ ＞
＜ test examples 1-1 (embodiment 1~3, comparative example 1) ＞
(preparation of pest repelling composition)
Prescription according to table 1 below, while stirring mixes each composition, prepare pest repelling composition (embodiment 1~
3rd, comparative example 1).It should be noted that DEET logP values are 2.0.Moreover, PEG-200 (MACROGOL 200), PEG-1000
(MACROGOL 1000) and PP-1000 (NEWPOL PP-1000) use what is obtained from Sanyo Chemical Industries, Ltd..
[table 1]
| Embodiment 1 | Embodiment 2 | Embodiment 3 | Comparative example 1 | |
| N, N- dimethyl-toluoyl amine (DEET) | 2g | 2g | 2g | 2g |
| PEG200 (polyethylene glycol：Mean molecule quantity 200) | 5g | - | - | - |
| PEG1000 (polyethylene glycol：Mean molecule quantity 1000) | - | 5g | - | - |
| PP1000 (polypropylene glycols：Mean molecule quantity 1000) | - | - | 5g | - |
| Ethanol | In right amount | In right amount | In right amount | In right amount |
| It is total | 100mL | 100mL | 100mL | 100mL |
(test method)
Tested according to following step.It should be noted that as experimental rig, having used the level shown in Fig. 1
Formula diffusion cell (ビ ー De レ ッ Network ス societies system, Flat Membrane horizontal type PERMCELL).
1. by the skin 1 of mouse (ラ ボ ス キ Application, from the wild experimental animal feeding of Co., Ltd.'s star obtained) with skin 1
The mode that corium side is located at the side of reception tank 2 is installed to horizontal diffusion cell 10.
2. in the cuticula side (4.9cm of skin 12) processing the about 45 above-mentioned preparations of μ L pest repelling composition, with aluminium foil 8
Covering, skin 1 is fixed with pinch grip 6.
3. fill the physiological saline 9 that 50mL is free of DEET in reception tank 2.
4. during experiment, physiological saline of the reception tank 2 in the stirring pool of stirrer 3, in the water jacket 4 of covering reception tank 2,
Make 37 DEG C of Warm water circulation by heater/circulator 5, so that the temperature in reception tank 2 is held constant at 37 DEG C.
5. at the time of the temperature in reception tank 2 reaches 37 DEG C, after 0.5 hour, 1 hour, from reception tank 2
The sampling 3mL of sample tap 7 physiological saline 9, then adds the physiological saline without DEET of equivalent, liquid measure is kept certain.
6. measure the DEET amounts in sampling liquid using HPLC.According to the measurement result of DEET amounts, skin is calculated by following formula
Residual rate in upper residual quantity, skin.
Residual quantity (mg/cm on skin after 0.5 hour2)=(handles the liquid after the sampling in -0.5 hour of DEET amounts
DEET amounts × 50/3)/processing area
Residual quantity (mg/cm on skin after 1 hour2The DEET amounts of liquid after the amount sampling in -1 hour of)=(processing DEET
The DEET amounts of liquid after sampling in × 50/3-0.5 hours)/processing area
Residual quantity/processing DEET amount × 100 on the skin of residual rate (%)=each time on skin
Residual quantity (mg/cm on skin2) it is that residual rate (%) is on numerical value after the 3rd decimal is rounded up, skin
Numerical value after first decimal is rounded up.
Test example 1-1 result is shown in the (residual quantity (mg/cm on skin of table 22)) and (residual rate on skin of table 3
(%)).
[table 2]
[table 3]
As Table 2,3, be used alone DEET comparative example 1 compared with, as a result, together with DEET and land used use
In the embodiment 1~3 of polyethylene glycol or polypropylene glycol, the residual quantity and residual rate of the DEET after certain time on skin
It is significantly many or high.
It can be seen from the result, compared with the insects repellants such as DEET individually are applied into skin, by with polyethylene glycol,
Insects repellant is applied to skin by the PAGs such as polypropylene glycol together, and insects repellant can be remained in for longer periods
On skin.
<Test example 1-2 (embodiment 4~8, comparative example 1)>
Prescription according to table 4 below, prepares insects repellant composition (embodiment 4~8, comparative example 1), with experiment
Example 1-1 similarly carries out skin and absorbs suppression experiment.In table 4, PP2000 (NEWPOL PP-2000) is melted into work using from Sanyo
What industry Co., Ltd. obtained.
Test example 1-2 result is shown in the (residual quantity (mg/cm on skin of table 52)) and (residual rate on skin of table 6
(%)).
[table 4]
| Embodiment 4 | Embodiment 5 | Embodiment 6 | Embodiment 7 | Embodiment 8 | Comparative example 1 | |
| N, N- dimethyl-toluoyl amine (DEET) | 2g | 2g | 2g | 2g | 2g | 2g |
| PP2000 (polypropylene glycols：Mean molecule quantity 2000) | 0.1g | 0.5g | 1g | 30g | 50g | - |
| Ethanol | In right amount | In right amount | In right amount | In right amount | In right amount | In right amount |
| It is total | 100mL | 100mL | 100mL | 100mL | 100mL | 100mL |
[table 5]
[table 6]
Comparing embodiment 4~8 and test example 1-1 comparative example 1 understands, by DEET and using polypropylene glycol, as a result
It is that the residual quantity and residual rate of the DEET on skin after certain time become many or uprised.In addition, if polypropylene glycol
Content increase, as a result, DEET residual quantity and residual rate become many with the increase of concentration or uprised.
In addition, even in for DEET contents polypropylene glycol content it is minimum (when DEET content is being set into 1
The content of polypropylene glycol is by quality ratio in 0.05) the pest repelling composition of embodiment 4, with the experiment without polypropylene glycol
The pest repelling composition of example 1-1 comparative example 1 is compared, as a result, the insects repellant on the skin after certain time
Residual quantity and residual rate it is many or high.
<Test example 1-3 (embodiment 9, comparative example 2)>
Prescription according to table 7 below, prepares insects repellant composition (embodiment 9, comparative example 2), with test example 1-1
Similarly carry out skin and absorb suppression experiment.In table 7, PP2000 (NEWPOL PP-2000) is used from Sanyo's chemical conversion industry strain
What formula commercial firm obtained.
Test example 1-3 result is shown in the (residual quantity (mg/cm on skin of table 82)) and (residual rate on skin of table 9
(%)).
[table 7]
| Embodiment 9 | Comparative example 2 | |
| N, N- dimethyl-toluoyl amine (DEET) | 10g | 10g |
| PP2000 (poly- interior glycol：Mean molecule quantity 2000) | 1g | - |
| Ethanol | In right amount | In right amount |
| It is total | 100mL | 100mL |
[table 8]
[table 9]
Comparing embodiment 9 and comparative example 2 understand, by DEET and using polypropylene glycol, as a result, by certain time
The residual quantity of the DEET on skin and residual rate become many or uprised afterwards.
＜ test examples 1-4 (embodiment 10~11, comparative example 3~4) ＞
Prescription according to table 10 below, prepares insects repellant composition (embodiment 10~11, comparative example 3~4), with
Test example 1-1 similarly carries out skin and absorbs suppression experiment.
It should be noted that the logP values of menthol are 3.4, to terpane 3, the logP values of 8- glycol are 1.4.
Test example 1-3 result is shown in the (residual quantity (mg/cm on skin of table 112)) and (residual rate on skin of table 12
(%)).
[table 10]
| Embodiment 10 | Comparative example 3 | Embodiment 11 | Comparative example 4 | |
| Menthol | 2g | 2g | - | - |
| To terpane 3,8- glycol | - | - | 2g | 2g |
| PP2000 (polypropylene glycols：Mean molecule quantity 2000) | 5g | - | 5g | - |
| Ethanol | In right amount | In right amount | In right amount | In right amount |
| It is total | 100mL | 100mL | 100mL | 100mL |
[table 11]
[table 12]
As shown in table 11,12, insects repellant menthol has been used even in the DEET for replacing using in test example 1-1
In the case of, be used alone insects repellant comparative example 3 compared with, as a result, and land used used insects repellant with
In the embodiment 10 of polypropylene glycol, more than the residual quantity and residual rate of the insects repellant on skin after certain time or
It is high.Using to terpane 3,8- glycol is same as the situation of insects repellant.
It can be seen from the result, even in using insects repellant menthol or to terpane 3,8- glycol replaces DEET's
In the case of, compared with these insects repellants individually are applied into skin, by with the PAG one such as polypropylene glycol
Rise and insects repellant is applied to skin, insects repellant is for longer periods remained on skin.
<Test example 1-5 (reference example 1~4)>
Prescription according to table 13 below, prepares insects repellant composition (reference example 1~4), same with test example 1-1
Ground carries out skin and absorbs suppression experiment.
It should be noted that the logP values of imidacloprid are 0.8, the logP values of Acetamiprid are 0.6.
Test example 1-5 result is shown in the (residual quantity (mg/cm on skin of table 142)) and (residual rate on skin of table 15
(%)).
[table 13]
| Reference example 1 | Reference example 2 | Reference example 3 | Reference example 4 | |
| Imidacloprid | 2g | 2g | - | - |
| Acetamiprid | - | - | 2g | 2g |
| PP2000 (polypropylene glycols：Mean molecule quantity 2000) | - | 5g | - | 5g |
| Ethanol | In right amount | In right amount | In right amount | In right amount |
| It is total | 100mL | 100mL | 100mL | 100mL |
[table 14]
[table 15]
The logP values of insects repellant (imidacloprid and Acetamiprid) are less than in the insects repellant composition of reference example 1~4
1, with the property for being difficult to penetrate to the skin, therefore, even and if use PAG, also do not find skin after certain time
The residual quantity and residual rate of insects repellant on skin are changed.
《Test example 2 (obstruction of sucking blood experiment)》
<Test example 2-1 (embodiment 12~14, comparative example 5)>
(preparation of pest repelling composition)
Prescription according to table 16 below, stirs while mix each composition, prepares pest repelling composition (embodiment
12~14, comparative example 5).It should be noted that embodiment 12 is the prescription same with test example 1-2 embodiment 6, comparative example 5
It is the prescription same with test example 1-1 comparative example 1.
[table 16]
| Embodiment 12 | Embodiment 13 | Embodiment 14 | Comparative example 5 | |
| N, N- dimethyl-toluoyl amine (DEET) | 2g | 2g | 2g | 2g |
| PEG200 (polyethylene glycol：Mean molecule quantity 200) | - | 10g | - | - |
| PP2000 (polypropylene glycols：Mean molecule quantity 2000) | 1g | - | - | - |
| PP4000 (polypropylene glycols：Mean molecule quantity 4000) | - | - | 10g | - |
| Ethanol | In right amount | In right amount | In right amount | In right amount |
| It is total | 100mL | 100mL | 100mL | 100mL |
(test method)
Tested according to following step.
1. to 1 hairless mouse (male, 20~40g) whole body, control zone coating ethanol, shown in treatment region coating table 16
Each pest repelling composition (0.5mL processing), and be fixed in metal cylinder mould, it is not moved.
2. the cage for being fixed with mouse is hung in chamber into (30cm × 30cm × 30cm), then, about 40 are put in cage
Female aedes albopictus.
3. after aedes albopictus being put in cage 5 minutes, mouse is taken out out of cage, then, cage is put into 40~100 DEG C of constant temperature
Device about 1 minute, it is motionless state to make the aedes albopictus in cage, and the aedes albopictus let fly away is all broken into pieces, calculates number of elements of sucking blood, and
The rate of sucking blood is calculated according to following formula and obstruction rate of sucking blood.
Rate of sucking blood (%)=(number of sucking blood/for test worm number) × 100
Obstruction of sucking blood rate (%)={ rate of sucking blood of (rate of sucking blood of the rate of sucking blood-treatment region of control zone)/control zone } × 100
Rate of sucking blood (%) is the numerical value after first decimal is rounded up.
4. being repeated above-mentioned 2~3, obstruction rate of sucking blood is calculated within every 1 hour.
Test example 2-1 result is shown in table 17.
[table 17]
As shown in Table 17, compared with DEET comparative example 5 is used alone, poly- second two is being used with DEET and land used
In the embodiment 12~14 of alcohol or polypropylene glycol, although DEET amount is identical, certain time obstruction rate of sucking blood is significantly high.According to this
As a result understand, compared with the insects repellants such as DEET individually are applied into skin, by poly- with polyethylene glycol, polypropylene glycol etc.
Insects repellant is applied to skin by aklylene glycol together, and the continuation of the pest repelling effect of insects repellant is improved.
＜ test examples 2-2 (embodiment 15~16, comparative example 6) ＞
Prescription according to table 18 below, prepares insects repellant composition (embodiment 15~16, comparative example 6), according to
The step same with test example 2-1 is tested.
Test example 2-2 result is shown in table 19.
[table 18]
| Embodiment 15 | Embodiment 16 | Comparative example 6 | |
| N, N- dimethyl-toluoyl amine (DEET) | 3g | 3g | 5g |
| PEG400 (polyethylene glycol：Mean molecule quantity 400) | - | 10g | - |
| PP4000 (polypropylene glycols：Mean molecule quantity 4000) | 10g | - | - |
| Ethanol | In right amount | In right amount | In right amount |
| It is total | 100mL | 100mL | 100mL |
[table 19]
As can be known from the above table, in embodiment 15,16, relative to comparative example 6, although DEET amount is reduced to 3/5, pass through
Simultaneously land used uses polyethylene glycol or polypropylene glycol together with DEET, and the obstruction rate of sucking blood of certain time is uprised.
It can be seen from the result, compared with the insects repellants such as DEET individually are applied into skin, by with polyethylene glycol,
Insects repellant is applied to skin by the PAGs such as polypropylene glycol together, so that the insect of insects repellant drives in skin
The continuation of avoiding effect is improved.
《Test example 3 (skin irritatin suppresses experiment)》
In this experiment, to 10 subjects (people of male 5, the people of women 5；The evil of the dermal application present invention of No.1~10)
Worm repellant compositions, for whether suppressing stimulation of the insects repellant to skin and testing.
(preparation of pest repelling composition)
[embodiment 17~19, comparative example 7]
Prescription according to table 20 below~23, is stirred while mix each composition, is prepared embodiment 17~19, is compared
The pest repelling composition of example 7.
[table 20]
Embodiment 17
| N, N- dimethyl-toluoyl amine (DEET) | 20g |
| 1,3-BDO | 2g |
| Silicic acid anhydride | 5g |
| Fatty acid glyceride | 1g |
| PP2000 (polypropylene glycols：Mean molecule quantity 2000) | 2g |
| Ethanol | In right amount |
| It is total | 100mL |
[table 21]
Embodiment 18
| N, N- dimethyl-toluoyl amine (DEET) | 30g |
| 1,3-BDO | 2g |
| Silicic acid anhydride | 5g |
| Fatty acid glyceride | 1g |
| PP2000 (polypropylene glycols：Mean molecule quantity 2000) | 2g |
| Ethanol | In right amount |
| It is total | 100mL |
[table 22]
Embodiment 19
| N, N- dimethyl-toluoyl amine (DEET) | 10g |
| 1,3-BDO | 2g |
| Silicic acid anhydride | 5g |
| Fatty acid glyceride | 1g |
| PP2000 (polypropylene glycols：Average mark amount is 2000) | 2g |
| Ethanol | In right amount |
| It is total | 100mL |
[table 23]
Comparative example 7
| N, N- dimethyl-toluoyl amine (DEET) | 10g |
| 1,3-BDO | 2g |
| Silicic acid anhydride | 5g |
| Fatty acid glyceride | 1g |
| Ethanol | In right amount |
| It is total | 100mL |
It should be noted that in table 20~23, fatty acid glyceride uses the single glyceride of oleic acid ten (DECAGLYN 1-
OV；From daylight, chemical society obtains).
(observation/inspection project and judgement)
It is tested that timetable shown in table 24 below this experimental evidence carries out that (1) is examined in advance, (2) paste by reagent, (3) removal
Medicine, the inquiry of (4) subjective symptoms, the observation/judgement of (5) dermoreaction.
[table 24]
(1) examine in advance
Subjective symptoms (medicament allergy, pain, itch) is inquired to subject before experiment will start, judges whether to fit
Close and participate in experiment.
(2) by reagent is pasted
By each by reagent (the pest repelling composition of embodiment 17~19 and comparative example 7) and comparison medicine after above-mentioned adjustment
(pure water), drips about 0.03mL with the pad of adhesive bandage (patch tape) (libatape pharmacy society manufactures) to skin test, glues
It is attached to the two Medial upper arm portions of each subject.It should be noted that the concentration of each by reagent is set as identical multiple.
(3) by reagent is removed
Paste after by reagent, by reagent is removed after 24 hours.
(4) inquiry of subjective symptoms
After just pasting by reagent, paste by reagent 24 hours after, remove by reagent 1 hour after inquiry subject be
It is no to have pain, itch, confirm subjective symptoms.
(5) observation of dermoreaction judges
After the removal by reagent 1 hour for dermoreaction easily occur, comparison medicine (pure water) is pasted to the skin at position
Reaction is pasted the dermoreaction at by reagent position, judged as control, observation.Judge that (world connects according to following ICDRG
Chu Xing dermatitis research association) standard progress.
[ICDRG standards]
-：It is completely reactionless
±：Only small light erythema
1+：Weak (no vesicle) positive reaction, slight erythema, papule
2+：(having vesicle) positive reaction by force, obvious erythema, papule
3+：Very strong positive reaction, intensity erythema, swelling, big bubble
In addition, various result of determination are scored (-：0 point, ±：0.5 point, 1+：1 point, 2+：2 points, 3+：3 points), calculate
Average ratings point.Show the result in table 25.
[table 25]
By pest repelling composition of the embodiment 17~19 containing polypropylene glycol paste 24 hours as a result, removing 1
After hour, light erythema (evaluation ±) is confirmed in 1 subject (No.6), but other subjects do not occur skin completely
Reaction.Divide on average ratings, be low to 0.05 point of fraction.In addition, in the inquiry of subjective symptoms in each judgement, not having
There is the subject for the subjective symptoms told pain or itched.
On the other hand, by comparative example 7 do not contain polypropylene glycol pest repelling composition paste 24 hours as a result,
After removing 1 hour, light erythema (evaluation ±) is confirmed in 9 subjects.Average ratings point also reach 0.45 point, with implementation
Example is compared, and evaluation point is uprised.
It can be seen from result above, compared with the situation for not containing polypropylene glycol, the pest repelling group containing polypropylene glycol
Compound can suppress the stimulation to skin.Therefore, by the way that PAG is applied into skin together with insects repellant, from
And stimulation of the insects repellant to skin can be suppressed.
The present invention is described in detail using specific mode, but is not departing from the feelings of the intent and scope of the present invention
Under condition, various changes and deformation can be carried out, to those skilled in the art, this is obvious.In addition, the application
Combined and this based on the Japanese patent application (special Willing 2015-028648) of proposition on 2 17th, 2015, and by entire contents,
It is used as reference.
Claims (6)
1. a kind of method, wherein,
By the way that PAG is applied into skin together with insects repellant, oozed so as to suppress insects repellant to skin
Thoroughly.
2. according to the method described in claim 1, wherein,
The logP values of the insects repellant are more than 1.
3. method according to claim 1 or 2, wherein,
The molecular weight of the PAG is 200~20000.
4. according to method according to any one of claims 1 to 3, wherein,
The PAG is polypropylene glycol.
5. a kind of infiltration inhibitor, suppresses insects repellant to Cutaneous permeation, wherein,
The infiltration inhibitor contains PAG.
6. the suppression that is used for of PAG is applied to use of the insects repellant on skin to Cutaneous permeation.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015-028648 | 2015-02-17 | ||
| JP2015028648 | 2015-02-17 | ||
| PCT/JP2016/054582 WO2016133124A1 (en) | 2015-02-17 | 2016-02-17 | Method for inhibiting penetration of insect pest repellant into skin and agent for inhibiting penetration of insect pest repellant into skin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107249322A true CN107249322A (en) | 2017-10-13 |
| CN107249322B CN107249322B (en) | 2021-10-26 |
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|---|---|---|---|
| CN201680010760.8A Active CN107249322B (en) | 2015-02-17 | 2016-02-17 | Method for inhibiting penetration of pest repellent into skin and penetration inhibitor for inhibiting penetration of pest repellent into skin |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP6708623B2 (en) |
| CN (1) | CN107249322B (en) |
| WO (1) | WO2016133124A1 (en) |
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| JP7344451B2 (en) * | 2020-03-17 | 2023-09-14 | 日油株式会社 | Transdermal absorption inhibitor and insect repellent composition |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59222402A (en) * | 1983-06-02 | 1984-12-14 | Otsuka Kagu Kogyo Kk | Insecticide composition |
| JP2003171205A (en) * | 2001-12-04 | 2003-06-17 | Kowa Co | Gel-like insect repellent formulation |
| JP2003171204A (en) * | 2001-12-04 | 2003-06-17 | Kowa Co | Gel-like insect repellent formulation |
| US7172995B1 (en) * | 2000-06-05 | 2007-02-06 | Colormetric Laboratories, Inc. | Method for minimizing absorption of and effecting removal of contaminant chemicals |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3158479B2 (en) * | 1990-06-18 | 2001-04-23 | 大正製薬株式会社 | Pest repellent composition |
| JP2009126804A (en) * | 2007-11-21 | 2009-06-11 | Dainippon Jochugiku Co Ltd | Noxious insect repellent for human body |
-
2016
- 2016-02-17 JP JP2017500714A patent/JP6708623B2/en active Active
- 2016-02-17 CN CN201680010760.8A patent/CN107249322B/en active Active
- 2016-02-17 WO PCT/JP2016/054582 patent/WO2016133124A1/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59222402A (en) * | 1983-06-02 | 1984-12-14 | Otsuka Kagu Kogyo Kk | Insecticide composition |
| US7172995B1 (en) * | 2000-06-05 | 2007-02-06 | Colormetric Laboratories, Inc. | Method for minimizing absorption of and effecting removal of contaminant chemicals |
| JP2003171205A (en) * | 2001-12-04 | 2003-06-17 | Kowa Co | Gel-like insect repellent formulation |
| JP2003171204A (en) * | 2001-12-04 | 2003-06-17 | Kowa Co | Gel-like insect repellent formulation |
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| Title |
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| HONGCHUN QIU 等: ""Formulation of topical insect repellent N,N-diethyl-m-toluamide (DEET) vehicle effects on DEET in vitro skin permeation"", 《INTERNATIONAL JOURNAL OF PHARMACEUTICS》 * |
| JULIE S. ROSS 等: ""Reduction in skin permeation of N,N-diethyl-m-toluamide (DEET) by altering the skin/vehicle partition coefficient"", 《JOURNAL OF CONTROLLED RELEASE》 * |
| 罗明生 等: "《药剂辅料大全 第2版》", 31 January 2006, 四川科学技术出版社 * |
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| WO2016133124A1 (en) | 2016-08-25 |
| JP6708623B2 (en) | 2020-06-10 |
| CN107249322B (en) | 2021-10-26 |
| JPWO2016133124A1 (en) | 2017-11-24 |
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