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WO2019111839A1 - Composition pour l'émission d'une substance volatile - Google Patents

Composition pour l'émission d'une substance volatile Download PDF

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Publication number
WO2019111839A1
WO2019111839A1 PCT/JP2018/044339 JP2018044339W WO2019111839A1 WO 2019111839 A1 WO2019111839 A1 WO 2019111839A1 JP 2018044339 W JP2018044339 W JP 2018044339W WO 2019111839 A1 WO2019111839 A1 WO 2019111839A1
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WO
WIPO (PCT)
Prior art keywords
volatile substance
composition
oxide
compound
diisocyanate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2018/044339
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English (en)
Japanese (ja)
Inventor
増田　剛
西口　英明
洋嗣 河田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Seika Chemicals Co Ltd
Original Assignee
Sumitomo Seika Chemicals Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Seika Chemicals Co Ltd filed Critical Sumitomo Seika Chemicals Co Ltd
Priority to KR1020207007001A priority Critical patent/KR102652555B1/ko
Priority to CN201880066685.6A priority patent/CN111212883B/zh
Priority to JP2019558193A priority patent/JP7185641B2/ja
Publication of WO2019111839A1 publication Critical patent/WO2019111839A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A01N25/18—Vapour or smoke emitting compositions with delayed or sustained release
    • 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
    • A01N27/00—Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/01—Deodorant compositions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6607—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/02—Halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/08—Polyurethanes from polyethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere

Definitions

  • the present invention relates to a composition for volatile substance emission and the like.
  • compositions containing useful volatile materials in resin gels are used in a variety of applications.
  • the volatile substance is an aromatic substance, a good odor can be dissipated into the room.
  • the volatile substance is a pest or pest-inducing substance, then the pest or pest can be attracted and this can be easily controlled.
  • An object of the present invention is to provide a volatile substance-containing composition which is excellent in sustained release of volatile substances.
  • the present inventors have found that a composition containing a specific polyalkylene oxide modified product, a filler, and a volatile substance is excellent in the sustained release of the volatile substance, and further improvement is completed to complete the present invention. It came to
  • the present invention includes, for example, the subject matters described in the following sections.
  • Item 1. A modified polyalkylene oxide obtained by reacting a polyalkylene oxide compound, a diol compound, and a diisocyanate compound, The composition for volatile substance radiation which contains (B) a filler and (C) volatile substance.
  • Item 2. A modified polyalkylene oxide obtained by reacting a polyalkylene oxide compound, a diol compound, and a diisocyanate compound, The composition for volatile substance radiation which contains (B) a filler and (C) volatile substance.
  • the polyalkylene oxide compound is polyethylene oxide, polypropylene oxide, polybutylene oxide, ethylene oxide / propylene oxide copolymer, ethylene oxide / butylene oxide copolymer, propylene oxide / butylene oxide copolymer, and ethylene oxide / propylene oxide / butylene oxide
  • the diol compound is ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, trimethylene glycol, 1,3-butanediol, 2,3-butanediol, 1,4-butanediol,
  • the composition for volatile substance emission according to Item 1 or 2 which comprises at least one selected from the group consisting of 1,5-pentanediol, 1,6-hexanediol, and 1,9-nonanediol.
  • the diisocyanate compound is 4,4'-diphenylmethane diisocyanate (MDI), 1,6-hexamethylene diisocyanate (HDI), dicyclohexylmethane-4,4'-diisocyanate (HMDI), 3-isocyanatomethyl-3, At least one selected from the group consisting of 5,5-trimethylcyclohexyl isocyanate (IPDI), 1,8-dimethylbenzene-2,4-diisocyanate, and 2,4-tolylene diisocyanate (TDI) 4.
  • MDI 4,4'-diphenylmethane diisocyanate
  • HDI 1,6-hexamethylene diisocyanate
  • HMDI dicyclohexylmethane-4,4'-diisocyanate
  • 3-isocyanatomethyl-3 At least one selected from the group consisting of 5,5-trimethylcyclohexyl isocyanate (IPDI), 1,8-dimethyl
  • the sustained release of volatile substances can be enhanced.
  • the composition for volatile substance emission of the present invention has a long-lasting effect (that is, excellent in sustained release) as the volatile substance contained is gradually dissipated.
  • the composition for volatile substance emission of the present invention can contain an even greater amount of volatile substance than the amount of volatile substance that the conventional resin can contain. For this reason, a fixed time (for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, The amount of volatile matter that can be released before 21, 22, 23, or 24 hours, or 1, 2, 3, 4, 5, 6, or 7 days), or the total amount of volatile matter that can be released is also a normal resin There is more than.
  • composition for volatile substance radiation included in the present invention contains (A) a specific polyalkylene oxide modified product, (B) a filler, and (C) a volatile substance. These components may be referred to as (A) component, (B) component, and (C) component, respectively. Moreover, the said composition for volatile substance radiation may be called composition for volatile substance radiation of this invention.
  • the specific polyalkylene oxide modified product (component (A)) is a compound obtained by reacting (polymerizing) a polyalkylene oxide compound, a diol compound, and a diisocyanate compound.
  • polyalkylene oxide compound examples include polyethylene oxide, polypropylene oxide, polybutylene oxide, ethylene oxide / propylene oxide copolymer, ethylene oxide / butylene oxide copolymer, propylene oxide / butylene oxide copolymer, and ethylene oxide / propylene oxide / butylene.
  • An oxide copolymer etc. can be illustrated.
  • the polyalkylene oxide compounds can be used singly or in combination of two or more.
  • "/" is a symbol used to indicate that it is a copolymer of each oxide.
  • ethylene oxide / propylene oxide copolymer refers to a copolymer of ethylene oxide and propylene oxide.
  • polyalkylene oxide compound having a number average molecular weight of 5,000 to 50,000 is preferable, and a polyalkylene oxide compound having a number average molecular weight of 10,000 to 30,000 is more preferable.
  • the value of the number average molecular weight here is a value calculated
  • Method of measuring number average molecular weight A dimethylformamide solution having a concentration of a polyalkylene oxide modified product of 1% by mass is prepared and measured using a high performance liquid chromatograph. Then, a molecular weight marker (polyethylene oxide) having a known molecular weight is measured under the same conditions, a calibration curve is created, and a number average molecular weight (Mn) is calculated.
  • the measurement conditions are as follows.
  • Measuring machine HLC-8220 (made by Tosoh Corporation) Column: Tosoh Corp. TSK GEL Multipore HXL-M Column temperature: 40 ° C Eluent: Dimethylformamide Flow rate: 0.6 ml / min Moreover, the polyalkylene oxide compound which has 90 mass% or more of ethylene oxide groups is preferable, and the polyalkylene oxide compound which has 95 mass% or more of ethylene oxide groups is more preferable.
  • diol compound examples include ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, trimethylene glycol, 1,3-butanediol, 2,3-butanediol and 1,4-butanediol And 1,5-pentanediol, 1,6-hexanediol, and 1,9-nonanediol.
  • diol compounds can be used singly or in combination of two or more.
  • the said polyalkylene oxide compound is not contained in the said diol compound. That is, the diol compound is a diol compound other than the polyalkylene oxide compound.
  • the proportion of the diol compound used is preferably 0.8 to 2.5 mol, more preferably 1.0 to 2.0 mol, per 1 mol of the polyalkylene oxide compound.
  • the number of moles of the polyalkylene oxide compound can be determined by dividing its mass by the number average molecular weight.
  • the diisocyanate compound is not particularly limited as long as it is a compound having two isocyanate groups (-NCO) in the same molecule, and, for example, 4,4'-diphenylmethane diisocyanate (MDI), 1,6-hexamethylene diisocyanate (HDI), dicyclohexylmethane-4,4'-diisocyanate (HMDI), 3-isocyanatomethyl-3,5,5-trimethylcyclohexylisocyanate (IPDI), 1,8-dimethylbenzene-2,4 And diisocyanates and 2,4-tolylene diisocyanate (TDI).
  • MDI 4,4'-diphenylmethane diisocyanate
  • HDI 1,6-hexamethylene diisocyanate
  • HMDI dicyclohexylmethane-4,4'-diisocyanate
  • IPDI 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl
  • dicyclohexylmethane-4,4'-diisocyanate HMDI
  • HDI 1,6-hexamethylene diisocyanate
  • a known method can be used as a method of reacting the polyalkylene oxide compound, the diol compound, and the diisocyanate compound.
  • the temperature of the reaction is preferably 70 to 210.degree.
  • a catalyst when producing a polyalkylene oxide modified product, a catalyst may be added to the reaction system from the viewpoint of promoting the reaction.
  • a catalyst an appropriate amount of triethylamine, triethanolamine, dibutyltin dilaurate, dioctyltin dilaurate, tin 2-ethylhexanoate, triethylenediamine and the like can be added.
  • a polyalkylene oxide modified product can be obtained.
  • the polyalkylene oxide modified product is usually obtained in the form of, for example, a pellet, a sheet, or a film. These may be used as they are in the volatile substance-releasing composition of the present invention, or may be used, for example, in the volatile substance-dissipating composition of the present invention after being crushed by a grinder or the like.
  • the grinding method is not particularly limited, but it is preferable to freeze and grind in order to prevent fusion due to shear heat generation at the time of grinding. For example, it can be frozen and crushed using liquid nitrogen.
  • the present invention can be achieved by adding the (C) component to the composition.
  • the composition of the present invention can be prepared.
  • the polyalkylene oxide modified product-containing composition obtained by adding the (B) filler into the reaction system may be used as it is for the composition for volatile substance emission of the present invention, for example, using a pulverizer or the like. After being crushed, it may be used in the volatile material-releasing composition of the present invention.
  • the grinding method is not particularly limited, but it is preferable to freeze and grind in order to prevent fusion due to shear heat generation at the time of grinding. For example, it can be frozen and crushed using liquid nitrogen.
  • the said polyalkylene oxide modified substance is water absorbency (that is, it has water absorption ability).
  • the volatile substance-containing liquid is absorbed by the polyalkylene oxide-modified product while dissolving or dispersing, or the volatile substance and water are separated into layers (two layers are separated).
  • the water absorption capacity of the modified polyalkylene oxide is preferably 10 to 40 g / g, more preferably 15 to 35 g / g.
  • the water elution content of the polyalkylene oxide modified product is preferably 10 to 40% by mass, more preferably 15 to 35%.
  • the water elution content in the present invention is obtained by measuring the mass after drying the gel after measurement of the water absorption ability with a hot air drier at 50 ° C. for 8 hours (C [g]), and using the following equation Value.
  • fillers known to be used for resins can be appropriately selected and used as long as the effects of the present invention are not impaired.
  • the filler may be an inorganic filler or an organic filler.
  • inorganic filler examples include silica, magnesium carbonate, clay, talc, calcium carbonate, titanium oxide, diatomaceous earth and the like.
  • the silica preferably has a specific surface area of 40 m 2 / g or more, 50 m 2 / g or more, 60 m 2 / g or more, 70 m 2 / g or more, 80 m 2 / g or more, 90 m 2 / g or more, 100 m 2 / g More preferred is one having a size of at least 110 m 2 / g.
  • the upper limit of the specific surface area is not particularly limited, and is, for example, 400 m 2 / g or less, 380 m 2 / g or less, 350 m 2 / g or less, or 300 m 2 / g or less.
  • the silica preferably has an oil absorption of 100 mL / 100 g or more, more preferably 150 mL / 100 g or more, and still more preferably 190 mL / 100 g or more.
  • oil absorption amount is not restrict
  • the oil absorption is a value measured by the method described in JIS K5101-13-2: 2004.
  • the clay include bentonite, smectite and the like.
  • bentonite includes organized bentonite (trimethyl stearyl ammonium bentonite, benzyl dimethyl stearyl ammonium bentonite, dimethyl distearyl ammonium bentonite, etc.).
  • smectites include organicated smectites (e.g., dimethyl distearyl ammonium hectorite, lithium sodium silicate sodium trioctylmethyl ammonium silicate, lithium sodium sodium magnesium dicarbonate dicobalt ycoalkyl (C8). To C18) methyl ammonium and the like) are included.
  • organic filler examples include cyclodextrin (eg, ⁇ -, ⁇ - or ⁇ -cyclodextrin etc.), modified cyclodextrin (eg methyl-modified cyclodextrin, hydroxypropyl-modified cyclodextrin etc.), etc. .
  • cyclodextrin eg, ⁇ -, ⁇ - or ⁇ -cyclodextrin etc.
  • modified cyclodextrin eg methyl-modified cyclodextrin, hydroxypropyl-modified cyclodextrin etc.
  • silica, magnesium carbonate, clay, cyclodextrin, modified cyclodextrin and the like are preferable.
  • the filler is preferably particles (powder).
  • the fillers can be used singly or in combination of two or more.
  • the volatile substance (component (C)) is not particularly limited as long as it does not volatilize at all at normal temperature and pressure (25 ° C., 1 atm) when used together with the component (A).
  • substances which are excellent in fragrance by volatilization (flavors), or substances capable of inducing and / or controlling pests or pests (for example, pheromone or control agents) are preferable. That is, one or more selected from the group consisting of a fragrance, and an insect pheromone, an animal pheromone, an insect repellent, and an animal repellent are preferable.
  • the pests are not particularly limited, and include, for example, hygienic pests and food pests, and more specifically, cockroaches, flies, flies, abs, mosquitos, centipedes, fleas, fleas, mites, bees, caterpillars, centipedes, castors, moths, Ants, termites etc. may be mentioned.
  • hygienic pests and food pests and more specifically, cockroaches, flies, flies, abs, mosquitos, centipedes, fleas, fleas, mites, bees, caterpillars, centipedes, castors, moths, Ants, termites etc.
  • cockroaches flies, flies, abs, mosquitos, centipedes, fleas, fleas, mites, bees, caterpillars, centipedes, castors, moths, Ants, termites etc.
  • small mammals
  • perfume for example, alloocimene, allyl caproate, allyl heptonate, amyl propionate, anesol, anisaldehyde, anisole, benzaldehyde, benzyl acetate, benzyl acetate, benzyl acetone, benzyl alcohol, benzyl butyrate, benzyl formate, Benzyl isovalerate, benzyl propionate, ⁇ ⁇ -hexenol, camphene, camphor, carvacrol, levo-carveol, d-carvone, d-carvone, carvocal-carvone, cinnamyl formate, citral (neral), citronellol, citronellyl acetate, isobutyric acid Citronellyl, citronellyl nitrile, citronellyl propionate, cumin alcohol, cumin aldehyde,
  • pheromone sex pheromone, aggregation pheromone, alarm pheromone and the like
  • Specific substances include attractants (especially insect inducers), and more specifically, for example, (Z) -9-trichocene, (Z) -11-beticone nodecene-1-aldehyde, (Z ) 5-Hexadecene, 1-chloro-3-methyl-bodo-2-ene, 3-chloro-3-methyl-bdo-1-ene, terpineol, farnesol, geraniol, acetic acid, iso Valerenic acid, trimethylamine, indole, piperidine, phenylethanol, ammonium carbonate, squartol, formaldehyde, hexamethylenetetramine, ammonium carbamate, papain, butyric acid, isovaleraldehyde, ethylamine, chlorinated alkenopoly
  • insecticide examples include salicylic acid, benzoic acid, sorbic acid, p-chloro-m-xylenol, 2- (4'-thiazoyl) benzimidazole and the like.
  • aliphatic linear aldehydes having 12 to 20 carbon atoms aliphatic linear acetates having 12 to 20 carbons having one or more saturated or double bonds, or 7 carbon atoms
  • Aliphatic linear alcohol of ⁇ 20, spiro acetal having 7 to 15 carbon atoms, aliphatic linear ketone having 10 to 25 carbon atoms, aliphatic hydrocarbon having 10 to 30 carbon atoms, carbonic acid having 10 to 20 carbon atoms And the like and in particular, aliphatic linear aldehydes having 12 to 20 carbon atoms, aliphatic linear acetates having 12 to 20 carbons having one or more saturated or double bonds, and 7 carbon atoms.
  • Aliphatic linear alcohols of ⁇ 20 and spiroacetals of 7 to 15 carbon atoms are preferred.
  • Z7Z11-hexadecadienyl acetate and P7E11-hexadecadienyl acetate which are sex pheromone substances of the pink ball worm (Pterus occidentalis)
  • Z-8-d which is the sex pheromone substance of the oriental fruit moss (Nashihimeshini) Decenyl acetate
  • E-5-decenyl acetate which is a sex pheromone substance of peach zig-bolger (mookibaga)
  • Z-9-dodecenyl acetate which is a sex pheromone substance of grapeberry moth (Hoshohimehamaki)
  • European grape E7Z9-dodecadienyl acetate which is the sex pheromone substance of vimus (grape hos
  • the volatile substances can be used singly or in combination of two or more. It is also possible to use a combination of a substance which is a perfume and a substance which is a pest or a pest pheromone or a control agent, but in particular, it is used singly or in combination of two or more It is preferable to use in combination one or more selected from the group consisting of pheromone, pest pheromone, pest control agent, and pest control agent.
  • the other component may be contained in the composition for volatile matter radiation of this invention in the range which does not prevent the effect of this invention.
  • non-volatile components may be included.
  • insecticidal components are preferably mentioned.
  • Preferred examples of the insecticidal component include neonicotinoid dinotefuran and acetamiprid, pyrrole chlorphenapyr, phenylpyrazole fipronil, macrolide lactone emamectin benzoate, and organophosphorus triclophone.
  • water-soluble insecticides are preferred, and dinotefuran is particularly preferred.
  • the mass ratio of the component (A) to the component (B) is preferably about 1: 0.0001 to about 0.2, preferably 1: 0.000 to 0. More preferably, it is about .15, and more preferably about 1: 0.01 to 0.1.
  • the lower limit of the mass ratio of the component (B) may be 0.0001, 0.0005, 0.001, 0.005, or 0.01.
  • the upper limit of the mass ratio of the component (B) is 0.2, 0.19, 0.18, 0.17, 0.16, 0.15, 0.14, 0.13, 0. It may be 12, 0.11, or 0.1.
  • the method for producing the volatile substance dissipating composition of the present invention is not particularly limited. For example, it can be produced by first preparing a composition ((A) and (B) -containing composition) containing the (A) component and the (B) component, and including the (C) component in this. When other components are included, for example, when the component (C) is included, the other components can be included together.
  • the component (B) may be mixed with this, or as described above, when preparing the component (A)
  • the component (B) may be added to the reaction system in advance (during the polymerization reaction).
  • a known method used when adding a filler to a resin can be used. More specifically, (A) and (B) can be obtained by mixing the (A) component and the (B) component while heating as necessary using, for example, a roller, a kneader, or an extruder. Contained compositions can be prepared.
  • a liquid composition containing the component (C) is absorbed by the compositions (A) and (B)
  • the method is mentioned.
  • the solvent of the (C) component-blended liquid composition include water, organic solvents (for example, ethanol and the like), and mixtures thereof, with water being particularly preferable.
  • the component (C) -blended liquid composition is preferably a composition containing a solvent and component (C), more preferably a composition consisting of only a solvent and component (C).
  • the solvent is preferably contained in an amount of 80 to 99% by mass, and more preferably 90 to 98% by mass.
  • the lower limit of the range may be about 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, or 94% by mass.
  • the upper limit of the said range may be about 99, 98, 97, or 96 mass%.
  • the (C) component-containing liquid composition the (C) component is preferably contained in an amount of 1 to 20% by mass, more preferably 2 to 10% by mass, and further preferably 3 to 6% by mass preferable.
  • the lower limit of the range may be 1, 2, 3, or 4% by mass.
  • the upper limit of the range may be 20, 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, or 6% by mass.
  • the liquid composition may contain components other than the solvent and the component (C).
  • Such components include, for example, surfactants, with nonionic surfactants being preferred. More specifically, for example, nonylphenol surfactants can be mentioned.
  • content of surfactant in (C) component combination liquid composition 0.05-0.5 mass% can be mentioned, for example, 0.06-0.4 mass, 0.07-0.3 It may be about mass%, 0.08 to 0.2 mass%, or about 0.09 to 0.15 mass%.
  • the mass ratio of the (C) component-blended liquid composition from which the composition absorbs liquid is preferably about 1: 1 to about 30, more preferably about 1: 1 to about 25, and 1: 1 to 20. It is further preferred that the degree is.
  • the said mass upper limit is 1: 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23. , 24, 25, 26, 27, 28, 29, or 30 or so.
  • the present invention also includes embodiments in which (A) and (B) -containing compositions are used, particularly for applications in which the volatile substance-blended liquid composition is absorbed. That is, a composition containing the (A) component and the (B) component for absorbing a volatile substance-containing liquid composition is also included in the present invention.
  • the present invention includes the step of absorbing the volatile substance-blended liquid composition into (A) and (B) -containing compositions, and releasing the volatile substance in the volatile substance-blended liquid composition into the atmosphere. It also includes ways to increase sustainability. The various conditions for these embodiments are the same as described above.
  • the term “comprising” also includes “consisting essentially of” and “consisting of” (The term “comprising” includes “consisting essentially of” and “consisting of.”).
  • various characteristics (properties, structures, functions, etc.) described for each embodiment of the present invention described above may be combined in any way in specifying the subject matter included in the present invention. That is, the present invention includes all the subject matter consisting of all combinations of the combinable features described in the present specification.
  • Production Example I Production of Polyalkylene Oxide Modified Substance
  • a storage tank A equipped with a stirrer kept at 80 ° C.
  • the mixture was charged at a rate of 0.1 part by mass with 0.1 part by mass of dioctyltin dilaurate, and stirred under a nitrogen gas atmosphere to obtain a uniform mixture.
  • dicyclohexylmethane-4,4'-diisocyanate was charged into storage tank B kept at 30 ° C., and stored under nitrogen gas atmosphere.
  • the water absorption capacity of the obtained polyalkylene oxide-modified product was 25 g / g, and the water elution was 19% by mass.
  • dicyclohexylmethane-4,4'-diisocyanate adjusted to 30 ° C. is also supplied at a rate of 12.4 g / min to the screw barrel portion located downstream of the hopper port of the twin screw extruder (R The reaction was carried out continuously under a nitrogen atmosphere (setting temperature: 180 ° C.). After cooling, the strand obtained from the outlet of the twin screw extruder was pelletized by a pelletizer to obtain a modified polyalkylene oxide product.
  • the water absorption capacity of the obtained polyalkylene oxide-modified product was 20 g / g, and the water elution was 15% by mass.
  • various fillers purchased and used the commercial item. Detailed information of various fillers is as follows.
  • the specific surface area of silica is a nitrogen gas adsorption method, and the oil absorption is a value measured by the method described in JIS K 5101-13-2: 2004.
  • compositions obtained in Production Examples 1 to 16 are formed into pellets of 4 mm long by using a super straight cutter (manufactured by Dumbbell Co., Ltd. (type: SSK-1000S-D punching size (L): 100 mm)). It shape
  • Example 17a Each composition of volatile substance mixing
  • Examples 1 to 16 Examples 1a to 16a using volatile substance-containing liquid A, Examples 1b to 16b using volatile substance-containing liquid B, and volatile substance-containing liquid C The examples used are referred to as Examples 1c to 16c.
  • Example 17a an example using the volatile substance-containing liquid A is referred to as Example 17a.
  • liquid absorbing compositions obtained in Examples 1 to 16 three pellets of the composition prepared by absorbing the volatile substance-containing liquid A are collected in 25 mL vials, and then the head space at 40 ° C. The amount of volatile components released from the liquid absorption composition is analyzed by quantitative analysis of the gas in the gas phase part in a 25 mL vial by GC analysis (head space method) while maintaining in an oven for 17 minutes. did.
  • the liquid absorbent composition obtained in Example 17 0.1 g of a composition prepared by absorbing liquid of the volatile substance-containing liquid A was collected in a vial, and the liquid absorbent composition was similarly prepared. The amount of volatile components released from the product was analyzed.
  • GC conditions Device body: GC-2014 (made by Shimadzu Corporation), Autosampler device: HT-2800T (made by Alpha Moss Japan Ltd.), Column: G-250, Carrier: He (flow rate: 50 mL / min), Detector: FID, INJ temperature: 230 ° C., Detector temperature: 250 ° C.)
  • the area value (area value of peak) of limonene detected from the liquid absorption composition which absorbed the volatile substance mixing liquid A by the GC analysis is as Table 7.
  • the area value is corrected by finally confirming the substantial weight by completely drying three pellets, the corrected area value (“area value / substantial weight for three pellets” or “area value / powder used” Body weight (0.1 g) ", ie area value of limonene released per gram of pellet or powder).
  • the area value of limonene released per gram of the pellet or powder may be called a limonene correction area value.
  • the pellet or powder of the composition prepared by absorbing liquid of volatile substance-containing liquid A is placed in a blower drier set at 40 ° C. 6 The mixture was allowed to stand for 12 hours or so to evaporate the absorbed volatile components. Thereafter, three pellets of the liquid absorbent composition are collected in 25 mL vials and maintained in a head space oven at 40 ° C. for 17 minutes, and the gas of the gas phase in the 25 mL vials is analyzed by GC (head analysis The amount of evaporated volatile components was analyzed by quantitative analysis using the space method. The limonene correction area values detected by the GC analysis are shown in Table 7.
  • Comparative Examples 1 to 3 1 g (approximately 20 pellets) of pellets (length, width, thickness: 4 mm, 4 mm, 2 mm) prepared without adding filler to the polyalkylene oxide modified product, volatile substance-containing liquid A, B, or C 10 g The solution was absorbed for 24 hours, and after absorbing the liquid for 24 hours, a pellet-like liquid absorbing polyalkylene oxide modified product was obtained by separating only the excess volatile substance-containing liquid which was not absorbed by the pellet. After collecting three pellets of the liquid absorbent polyalkylene oxide modified product in a 25 mL vial, the pellet is maintained in a head space oven at 40 ° C. for 17 minutes, and the gas phase in the 25 mL vial is the same as above. The amount of volatile components evaporated from the liquid absorbable polyalkylene oxide modified product was analyzed by quantitative analysis by GC analysis (head space method) under the following conditions.
  • the pellet of the liquid absorbing polyalkylene oxide modified product was placed in a blower dryer set at 40 ° C., and the absorbed hydrophobic component was allowed to stand for 6 hours or 12 hours to evaporate the absorbed volatile component. Thereafter, three pellets of the absorbent polyalkylene oxide modified product are collected in 25 mL vials and maintained in a head space oven at 40 ° C. for 17 minutes, and the gas phase portion in the 25 mL vial is The amount of the volatile component evaporated was analyzed by analyzing quantitatively (head space method).
  • Table 10 shows the limonene corrected area values detected by GC analysis from the polyalkylene oxide-modified products obtained by absorbing the volatile substance-containing liquids A and B.

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Abstract

L'invention concerne une composition contenant une substance volatile à partir de laquelle la substance volatile est libérée de manière durable pendant une longue période. Plus particulièrement, l'invention concerne une composition destinée à émettre d'une substance volatile, la composition comprenant (A) un produit de modification de poly(oxyde d'alkylène) obtenu par réaction d'un composé de poly(oxyde d'alkylène), d'un composé diol et d'un composé diisocyanate, (B) une charge, et (C) la substance volatile.
PCT/JP2018/044339 2017-12-04 2018-12-03 Composition pour l'émission d'une substance volatile Ceased WO2019111839A1 (fr)

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US20210329915A1 (en) * 2018-09-19 2021-10-28 Dainihon Jochugiku Co., Ltd. Absorption promoter, flying-insect pest repellent fragrance-containing composition, and flying-insect pest repellent product

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CN108719282B (zh) * 2018-06-04 2021-10-15 山西农业大学植物保护学院(山西省农业科学院植物保护研究所) 一种防治梨小食心虫的专性引诱剂及防治方法
WO2021178948A1 (fr) * 2020-03-06 2021-09-10 North Carolina State University Nouveaux constituants de phéromone sexuelle destinés au légionnaire d'automne, spodoptera frugiperda
CN114271274B (zh) * 2022-01-06 2022-09-13 中国农业科学院植物保护研究所 一种草地贪夜蛾的诱剂组合物及其应用
CN116035002B (zh) * 2023-01-10 2024-04-26 河北省农林科学院植物保护研究所 一种提高白星花金龟引诱剂诱杀效果的增效剂及其应用

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