WO2019107366A1 - Agent de modification de mauvaise odeur pour modification des odeurs d'asphalte, boue, eaux usées, ginkgo biloba, fumier, animaux marins, légumes, ordures ou peintures et vernis, et procédé de modification de mauvaise odeur d'odeurs d'asphalte, boue, eaux usées, ginkgo biloba, fumier, animaux marins, légumes, ordures ou peintures et vernis - Google Patents

Agent de modification de mauvaise odeur pour modification des odeurs d'asphalte, boue, eaux usées, ginkgo biloba, fumier, animaux marins, légumes, ordures ou peintures et vernis, et procédé de modification de mauvaise odeur d'odeurs d'asphalte, boue, eaux usées, ginkgo biloba, fumier, animaux marins, légumes, ordures ou peintures et vernis Download PDF

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Publication number
WO2019107366A1
WO2019107366A1 PCT/JP2018/043628 JP2018043628W WO2019107366A1 WO 2019107366 A1 WO2019107366 A1 WO 2019107366A1 JP 2018043628 W JP2018043628 W JP 2018043628W WO 2019107366 A1 WO2019107366 A1 WO 2019107366A1
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Prior art keywords
odor
methyl
ethyl
vanillin
mass
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PCT/JP2018/043628
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English (en)
Japanese (ja)
Inventor
旭旭 包
裕 辻本
芳邦 山本
隆一 肥下
Original Assignee
山本香料株式会社
シキボウ株式会社
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Priority to CN201880076984.8A priority Critical patent/CN111565764A/zh
Publication of WO2019107366A1 publication Critical patent/WO2019107366A1/fr

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    • 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
    • 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
    • A61L9/14—Disinfection, sterilisation or deodorisation of air using sprayed or atomised substances including air-liquid contact processes
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F11/00—Treatment of sludge; Devices therefor
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/18—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C07D307/44—Furfuryl alcohol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C07D307/48—Furfural
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/60—Two oxygen atoms, e.g. succinic anhydride
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol

Definitions

  • the present invention relates to an odor modulator for modulating the odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage or paints, and asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage or paints Odor modulation method.
  • polyphenol is contained as an active ingredient a colored compound obtained by reacting at a pH value of 6.5 or more at the time of reaction in the presence of molecular oxygen in a solvent exhibiting alkalinity.
  • a deodorant composition is disclosed, and the use of the deodorant composition for the deodorization of malodor is disclosed (see, for example, Patent Document 1).
  • the above-mentioned odor is hard to disappear, and there is a problem that even if it uses a deodorizer which deodorizes by depleting the above-mentioned odor, it can not deodorize sufficiently.
  • the present invention is an odor modulator which can easily modulate odors of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage, or paints into different odors, and solve these odors easily, and It aims to provide an odor modulation method.
  • the present inventor modulates the odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage, or paint into different odors and makes them feel other unpleasant odors. According to the agent, it has been found that the unpleasant feeling due to these malodors can be sufficiently reduced.
  • the present inventor uses an odor modulator for modulating the odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage, or paint as a causative agent of these odors, and / or By using it in the smelly place, it has been found that the offensive odor can be modulated to another odor, the unpleasant feeling can be easily reduced, and the above object can be achieved, and the present invention has been completed.
  • the present invention includes the following asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, odor modulators for modulating the odor of garbage or paint, and asphalt, sludge, sewage, ginkgo, compost, marine, vegetables,
  • the present invention relates to an odor modulation method of odor of raw garbage or paint. 1.
  • An odor modulator for modulating the odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage, or paints An odor modulator comprising at least one oxygen-containing cyclic compound selected from furan compounds, pyran compounds and cyclopentanone derivatives. 2.
  • the furan compound is, for example, furaneol, furfural, 5-methylfurfural, furfuryl mercaptan, furfuryl alcohol, 2-propionyl furan, 2-ethyl furan, menthofuran, 2-methyl-3-furan thiol, 2-methyl-3 -Tetrahydrofuranthiol, 2-methyl-4,5-dihydro-3-furanthiol, 2-methylfuran, 2-methyltetrahydrofuran, 2-hexanoylfuran, 2-pentylfuran, 2-propylfuran, 2- (3- (3-) Phenylpropyl) tetrahydrofuran, 2,3-dihydrobenzofuran, 2,4-dimethyl-4-phenyltetrahydrofuran, 2-furfuryl-5-methyl
  • the odor modulator according to any one of Items 1 to 3, wherein the content of the furan compound is 0.8 to 5% by mass, based on 100% by mass of the odor modulator.
  • the pyran compound is maltol, ethyl maltol, 4-acetoxy-3-pentyltetrahydropyran, 3,5-dihydroxy-6-methyl-2,3-dihydro-4 (4H) -pyranone, 6-ethenyl-2,2 , 6-trimethyltetrahydropyran, 5-methyl-3-butyltetrahydropyran-4-yl acetate, octahydro-2H-1-benzopyran-2-one, 4-methyl-2- (2-methyl-1-propenyl) tetrahydro Pyrane, theaspirane, vity spilane, (2S, 4aR, 8aS) -2, 5, 5, 8a-tetramethyl-3, 4, 4a, 5, 6, 8a-hexahydro-2H-1-benz
  • the odor modulator according to any one of Items 1 to 5, wherein the content of the pyran compound is 5 to 20% by mass based on 100% by mass of the odor modulator.
  • the cyclopentanone derivatives include cyclopentanone, cyclotene, cyclotene acetate, cyclotene propionate, cyclotenobutyrate, cyclotene isobutyrate, 2-geranyl cyclopentanone, 2-hexyl cyclopentanone, 2-he Xylidenecyclopentanone, 2-cyclopentylcyclopentanone, 2-amyl-2-cyclopentenone, 3-methyl-2-pentyl-2-cyclopentenone, 3-ethyl-2-hydroxy-2-cyclopentenone , 2-hydroxy-3,4-dimethyl-2-cyclopentenone, 2-methyl-3- (2-pentenyl) -2-cyclopentenone, 3-methyl-2- (cis-2-pentenyl) -2 -Cyclopen
  • Item 9 The odor modulator according to any one of Items 1 to 8, further comprising a vanillin-based compound. 10.
  • the vanillin compounds include vanillin, ethyl vanillin, acetaldehyde ethyl vanillin acetal, vanillin acetate, ethyl vanillin isobutyrate, acetovanillon, ethyl vanillate, ethyl vanillin propylene glycol acetal, methyl vanylate, vanillic acid, vanillin isobutyrate, butyl vanai 10.
  • the odor modulator according to item 9 or 10 wherein the content of the vanillin compound is 10 to 20% by mass, based on 100% by mass of the odor modulator.
  • Item 12 The odor modulator according to any one of Items 1 to 11, further containing pyridines. 13.
  • the pyridines are 2-acetylpyridine, 3-acetylpyridine, 4-acetylpyridine, 2-acetyl-1,4,5,6-tetrahydropyridine, 2-acetyl-4-isopropenylpyridine, 4-acetyl-2 -Isopropenylpyridine, 2-acetyl-4-isopropylpyridine, 3,5-dimethyl-4,5,6,7-tetrahydrothieno [3,2-c] pyridine, and 2-acetyl-3,4,5, Item 13.
  • the odor modulator according to item 12 which is at least one selected from the group consisting of 6-tetrahydropyridine. 14.
  • the odor modulator according to any one of Items 1 to 13, further containing pyrazines.
  • the pyrazines are 2-methylthio-3-methylpyrazine, 2-methoxy-3-methylpyrazine, 2-ethyl-3 (5/6) dimethylpyrazine, 2-ethyl-3-methylpyrazine, 2-methoxy-5 -Methylpyrazine, 2-acetyl-3, (5/6) -dimethylpyrazine, 2-acetyl-3-ethylpyrazine, 2-acetyl-3-methylpyrazine, acetylpyrazine, 2- (furfurylthio)-(3/5) / 6) -Methylpyrazine, 2-methyl- (5/6)-(methylthio) pyrazine, 2-ethyl-3- (methylthio) pyrazine 2-isopropyl-3- (methylthio) pyrazine, 2-sec-butyl-3 -Methoxy
  • the odor modulator according to item 14 which is at least one selected from the group consisting of pyrazines. 16.
  • An odor modulation method characterized in that it is used as a causative agent and / or in a place where the odor is present.
  • the odor modulator of the present invention for modulating the odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage, or paints, modulates these odors into different odors to make them feel other unpleasant odors And can reduce the discomfort caused by these offensive odors.
  • the above-mentioned odor modulator is used as a causative substance of the odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage or paint, and / or their odor
  • These odors can be modulated to other odors, and discomfort due to these malodors can be easily reduced.
  • Asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, odors of garbage, paint or odor modulation of the present invention asphalt, sludge, sewage, ginkgo, compost, marine, vegetables, garbage, paint odor
  • the modulating odor modulator (which may also be simply referred to herein as "odor modulator") contains at least one oxygenated cyclic compound selected from furan compounds, pyran compounds and cyclopentanone derivatives .
  • the odor modulator of the present invention is used to modulate the odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage or paints.
  • Asphalts include petroleum asphalts produced by distilling crude oil, and naturally occurring natural asphalts. As the odor of asphalt, there are odors derived from asphalt components, which occur when the ground is paved with such asphalt, or which drifts in the air for a while after the paving.
  • Examples of sewage include water stored at the bottom of sewage treatment plants and septic tanks, and water from sewers.
  • Ginkgo is a seed of Ginkgo biloba, and it falls on the street from Ginkgo biloba which is vegetated as a street tree or the like to generate an odor.
  • the compost includes fecal compost and plant-based compost.
  • the marine animals generally include marine animals kept in aquariums and zoos and the like, and examples thereof include penguins, whales, killer whales, dolphins, sea otters, seals and fur seals.
  • the smells of marine animals include those in aquariums, pools, breeding rooms and exhibition areas where these marine animals are bred.
  • the odor modulators of the present invention are particularly suitable for modulating penguin odor among these.
  • Examples of vegetables include plants with a strong odor, and examples of such plants include onion, green onion, garlic which are allium plants.
  • the odor modifiers of the invention are particularly suitable for modulating the onion odor among these.
  • the raw garbage includes raw garbage which is taken out as garbage from homes and commercial facilities and transported to a waste disposal facility.
  • the odor modulator of the present invention is particularly suitable for modulating the odor of a waste pit (trash bin) which is temporarily stored until garbage is incinerated in a waste disposal facility.
  • Examples of the paint include generally used water-based paint, solvent-based paint and the like.
  • Examples of water-based paints include water-soluble acrylic / melamine resin paints, water-soluble alkyd / melamine resin paints, acrylic emulsion paints, urethane emulsion paints and the like.
  • a solvent type paint an acrylic melamine resin paint, an alkyd melamine resin paint, a urethane resin paint, an epoxy resin paint etc. are mentioned, for example.
  • the furan compound is an oxygen-containing cyclic compound and is not particularly limited as long as it has a 5-membered ring furan skeleton formed of 4 carbon atoms and 1 oxygen atom.
  • the furan compound for example, furaneol, furfural, 5-methylfurfural, furfuryl mercaptan, furfuryl alcohol, 2-propionyl furan, 2-ethyl furan, menthofuran, 2-methyl-3-furan thiol, 2-methyl furan -3-tetrahydrofuran thiol, 2-methyl-4,5-dihydro-3-furanthiol, 2-methyl furan, 2-methyl tetrahydrofuran, 2-hexanoyl furan, 2-pentyl furan, 2-propyl furan, 2- ( 3-phenylpropyl) tetrahydrofuran, 2,3-dihydrobenzofuran, 2,4-dimethyl-4-phenyltetrahydrofuran
  • the content of the furan compound is preferably 0.5 to 10% by mass, more preferably 0.8 to 5% by mass, still more preferably 0.8 to 3% by mass, based on 100% by mass of the odor modifier. -1.5% by weight is particularly preferred, and 0.9-1.2% by weight is most preferred.
  • the odor modulator tends to easily modulate the odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage and paint into different odors, which are caused by these odors. The discomfort can be reduced sufficiently.
  • the above furan compounds may be used alone or in combination of two or more.
  • the pyrane compound is an oxygen-containing cyclic compound, and is not particularly limited as long as it has a pyran skeleton having a six-membered ether compound formed by five carbon atoms and one oxygen atom as a skeleton.
  • pyrane compounds include maltol, ethyl maltol, 4-acetoxy-3-pentyltetrahydropyran, 3,5-dihydroxy-6-methyl-2,3-dihydro-4 (4H) -pyranone, 6-ethenyl-2 , 2,6-Trimethyltetrahydropyran, 5-methyl-3-butyltetrahydropyran-4-yl acetate, octahydro-2H-1-benzopyran-2-one, 4-methyl-2- (2-methyl-1-propenyl) ) Tetrahydropyran, theaspirane, vity spilane, (2S, 4aR, 8aS) -2, 5, 5, 8a-tetramethyl-3, 4, 4a, 5, 6, 8a-hexahydro-2H-1-benzopyran, 6-ethenyl -2,2,6-Trimethyltetrahydro-3 (4H) -pyranone, 6-hydroxydihydrotea Pyran, 6-ace
  • the content of the pyran compound is preferably 5 to 20% by mass, more preferably 5 to 15% by mass, still more preferably 8 to 15% by mass, and particularly preferably 8 to 12% by mass, based on 100% by mass of the odor modifier.
  • the odor modulator can easily modulate the odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage, and paints into different odors, which are caused by these odors. The discomfort can be reduced sufficiently.
  • the pyran compounds may be used singly or in combination of two or more.
  • the cyclopentanone derivative is an oxygen-containing cyclic compound, and is not particularly limited as long as it has a 5-membered cyclopentane skeleton formed of 5 carbon atoms and an oxygen atom.
  • cyclopentanone derivatives include cyclopentanone, cyclotene, cyclotene acetate, cyclotene propionate, cyclotenobutyrate, cyclotene isobutyrate, 2-geranyl cyclopentanone, 2-hexyl cyclopentanone, 2 -Hexylidenecyclopentanone, 2-cyclopentylcyclopentanone, 2-amyl-2-cyclopentenone, 3-methyl-2-pentyl-2-cyclopentenone, 3-ethyl-2-hydroxy-2-cyclo Pentenone, 2-hydroxy-3,4-dimethyl-2-cyclopentenone, 2-methyl-3- (2-pentenyl) -2-cyclopentenone, 3-methyl-2- (cis-2-pentenyl) -2-cyclopentenone, 3-methyl-2- (trans-2-pentenyl) -2-cyclo Intenone, 3-methyl-2-cyclopentenone, 3-ethyl-2-hydroxy-4-methyl-2-cycl
  • the content of the cyclopentanone derivative is preferably 0.1 to 5% by mass, more preferably 0.5 to 3% by mass, based on 100% by mass of the odor modifier.
  • the odor modulator can easily modulate the odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage, and paints into different odors, which are caused by these odors. The discomfort can be reduced sufficiently.
  • cyclopentanone derivatives may be used singly or in combination of two or more.
  • the odor-modulating agent of the present invention contains at least one oxygen-containing cyclic compound selected from furan compounds, pyran compounds and cyclopentanone derivatives, and contains at least one kind of oxo compound selected from furan compounds and pyran compounds It is preferable to contain an oxygen cyclic compound.
  • the content of the above oxygen-containing cyclic compound in the odor modifier that is, the sum of the contents of the furan compound, the pyran compound and the cyclopentanone derivative is 0.1 to 25 mass% based on 100 mass% of the odor modifier Preferably, 0.1 to 20% by mass is more preferable, 1 to 15% by mass is further more preferable, and 10 to 15% by mass is particularly preferable.
  • the odor modulator modulates the offensive odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage, and paint into different odors This makes it easy to reduce discomfort due to these odors.
  • the odor modifier of the present invention preferably further contains a vanillin-based compound.
  • the odor-modulating agent can exhibit a better odor-modulating effect, and more unpleasant feeling due to the offensive odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage, and paints It can be effectively reduced.
  • the vanillin-based compound is not particularly limited as long as it is a compound having a vanillin skeleton.
  • the vanillin compounds include vanillin, ethyl vanillin, acetaldehyde ethyl vanillin acetal, vanillin acetate, ethyl vanillin isobutyrate, acetovanillon, ethyl vanillate, ethyl vanillin propylene glycol acetal, methyl vanylate, vanillic acid, vanillin isobutyrate, Butyl vanylate, vanillin 2,3-butanediol acetal, vanillin lactate and the like can be mentioned. Among these, vanillin and ethylvanillin are preferred.
  • the content of the vanillin compound is preferably 5 to 25% by mass, more preferably 5 to 20% by mass, still more preferably 10 to 20% by mass, particularly preferably 10 to 15% by mass, based on 100% by mass of the odor modifier. .
  • the odor modulator is likely to modulate the offensive odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage, and paints with different odors, and these odors It is possible to reduce the discomfort caused by
  • the vanillin compounds may be used alone or in combination of two or more.
  • the odor modulator of the present invention preferably further contains pyridines.
  • the odor-modulating agent can exhibit more excellent odor-modulating effect, and more effective to offensive odor due to the offensive odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage and paints. Can be reduced.
  • Pyridines are nitrogen-containing heterocyclic aromatic compounds, and in particular, they have a pyridine skeleton having a pyridine skeleton having a six-membered ring structure formed by five carbon atoms and one nitrogen atom. It is not limited.
  • Examples of pyridines include 2-acetylpyridine, 3-acetylpyridine, 4-acetylpyridine, 2-acetyl-1,4,5,6-tetrahydropyridine, 2-acetyl-4-isopropenylpyridine, 4-acetyl -2-isopropenylpyridine, 2-acetyl-4-isopropylpyridine, 3,5-dimethyl-4,5,6,7-tetrahydrothieno [3,2-c] pyridine, 2-acetyl-3,4,5 , 6-tetrahydropyridine and the like.
  • 2-acetylpyridine is preferable.
  • the content of the pyridines is preferably 0.05 to 0.3% by mass, more preferably 0.1 to 0.2% by mass, based on 100% by mass of the odor modifier.
  • the odor modulator is likely to modulate the odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage, and paints with different odors, and these odors The discomfort can be reduced sufficiently.
  • the above pyridines may be used singly or in combination of two or more.
  • the odor modifier of the present invention preferably further contains pyrazines.
  • the odor modulator can exhibit a better odor modulation effect, and more effective to offensive odor due to the offensive odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage and paint Can be reduced.
  • Pyrazines are nitrogen-containing heterocyclic aromatic compounds, and have a pyrazine skeleton having a pyrazine skeleton which is a compound having a six-membered ring structure formed by four carbon atoms and two nitrogen atoms. There is no particular limitation if it is.
  • pyrazines for example, 2-methylthio-3-methylpyrazine, 2-methoxy-3-methylpyrazine, 2-ethyl-3 (5/6) dimethylpyrazine, 2-ethyl-3-methylpyrazine, 2-methoxy -5-methylpyrazine, 2-acetyl-3, (5/6) -dimethylpyrazine, 2-acetyl-3-ethylpyrazine, 2-acetyl-3-methylpyrazine, acetylpyrazine, 2- (furfurylthio)-(3 / 5/6) -Methylpyrazine, 2-methyl- (5/6)-(methylthio) pyrazine, 2-ethyl-3- (methylthio) pyrazine 2-isopropyl-3- (methylthio) pyrazine, 2-sec-butyl -3-methoxypyrazine, 2-ethoxy- (3/5/6) -methylpyrazine, 2-ethoxy-
  • the content of pyrazines is preferably 0.1 to 0.5% by mass, more preferably 0.1 to 0.4% by mass, based on 100% by mass of the odor modifier.
  • the odor modulator is likely to modulate the offensive odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage, and paints with different odors, and these odors The discomfort can be reduced sufficiently.
  • the pyrazines may be used singly or in combination of two or more.
  • the odor modifier of the present invention may contain other additives as long as the effects of the present invention are not impaired.
  • the other additives include the above-mentioned furan compounds, pyran compounds, vanillin compounds, organic acids other than pyridines and pyrazines, ester compounds, aldehyde compounds, ketone compounds and the like.
  • the total content of the other additives in the odor modifier is preferably 30% by mass or less, more preferably 20% by mass or less, still more preferably 10% by mass or less, based on 100% by mass of the odor modifier. % Or less is particularly preferred.
  • the odor modulator is likely to modulate the offensive odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage, and paints with different odors, The discomfort due to these odors can be sufficiently reduced.
  • each of the above components is preferably dispersed in a solvent. Being dispersed in a solvent, it can be used easily by applying, adding, etc. to the odorants of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage and paints, etc. It can be easily sprayed, sprayed, etc. in the air at the place where
  • the solvent is not particularly limited, and examples thereof include alcohols, ethers, ketones, esters and the like. Among them, alcohol is preferable in that it exhibits appropriate volatility when the odor modulator is sprayed into the air, and is less harmful to humans and marine animals.
  • Alcohol or polyols such as diol and triol
  • an alcohol having 2 to 4 carbon atoms can be suitably used as the above-mentioned alcohol.
  • the carbon number of the alcohol is more preferably 2 to 3.
  • alcohol examples include ethanol, propylene glycol, glycerin and the like, which exhibit appropriate volatility when the odor-modulating agent is sprayed into the air, and are low in harmfulness to humans and marine animals, Ethanol and propylene glycol are preferred.
  • the above solvents may be used singly or in combination of two or more.
  • the content of the solvent is preferably 20 to 90% by mass, more preferably 30 to 90% by mass, still more preferably 40 to 80% by mass, and particularly preferably 50 to 80% by mass, based on 100% by mass of the odor modifier.
  • the present invention also relates to an odor modulator containing at least one kind of oxygen-containing cyclic compound selected from furan compounds, pyran compounds and cyclopentanone derivatives, asphalt, sludge, sewage, ginkgo, compost, marine animals, It is also an odor-modulating method characterized by being used as a causative substance of the smell of vegetables, raw garbage or paint and / or used in the place where those smells.
  • the above-mentioned odor modulator for modulating the odor of asphalt, sludge, sewage, ginkgo, compost, marine animals, vegetables, garbage, or paint can be used.
  • Examples of the method used for the odor causing substance include a method in which the odor causing substance is sprayed or mixed. There is no particular limitation on the method of applying to the odor causing substance, and the odor modulator may be applied to the odor causing substance. Moreover, as a method of mixing with the odor causing substance, for example, when the odor causing substance is asphalt, there is a method of adding an odor modifier to the heated molten asphalt.
  • the odor modifier may be used as the odor causing substance, may be used at the smelly place, or may be used for both.
  • the method of atomizing an odor modulator and spraying it in air As a method of using in the place where the said smell is given, the method of atomizing an odor modulator and spraying it in air, the method of dripping an odor modulator and scattering, etc. are mentioned.
  • a spraying method As a method of atomizing the odor modulator and spraying it into the air, a spraying method, a method of spraying the compost simultaneously with mania spreader, a method of scattering the mist odor modulator by wind, etc. Can be mentioned.
  • a dispersing the droplet-like odor modulator As a method of dispersing the droplet-like odor modulator, a dispersion method such as a method of spraying a liquid odor modulator from a nozzle and spraying may be mentioned.
  • the temperature of the odor modifier at the time of using the odor modifier is not particularly limited, and 10 to 25 ° C. is preferable, and 15 to 20 ° C. is more preferable.
  • the odor modulator in the above temperature range, the odor modulation effect can be further improved.
  • the pressure at which the odor modulator is sprayed or sprayed from the spray or nozzle is preferably 0.2 to 0.6 MPa, more preferably 0.3 to 0.5 MPa.
  • the odor modulator is sprayed or sprayed, and the road and construction site where the smell of asphalt smells, the sewage treatment plant where the smell of sludge smells, the vicinity of the septic tank, the sewage treatment plant where the smell of sewage flows, the septic tank, the sewer Nearby, on streets that smell of ginkgo, farms that smell of compost, aquariums and zoos that smell of sea animals, food processing sites that smell of vegetables, garbage pits of garbage processing facilities that smell of garbage,
  • the paint can be sprayed into the air at the painting site where the paint smells. By spraying the odor modulating agent into the air at these locations, the malodor can be modulated to other odors and discomfort can be easily reduced.
  • sludge was placed in a plastic internal system 2 cm cap (lid). No. 1 on the bottom of the sterile petri dish for bacteria test.
  • the filter paper of No. 2 was placed, the above-mentioned cap was placed at the center of the filter paper, and 0.2 g of the diluted solution was dropped in a loop on the filter paper around the cap to prepare a sample.
  • the blank which does not drip a dilution liquid was also prepared.
  • the samples and blanks were then covered with petri dishes and allowed to stand at room temperature (20 ° C.) for 10 minutes. After standing, the lid was opened, and the subject smelled smell from the center 10 cm above the center of the petri dish, and compared with the smell of the blank, the sensory evaluation was performed according to the following evaluation criteria.
  • the above test was conducted by eight test subjects, and evaluations were made according to the score obtained by multiplying the number of persons who performed each evaluation by the point allocation of the following evaluation criteria.
  • the asphalt odor was evaluated as follows. That is, a sample of asphalt was placed in a heat-resistant container and heated. After the asphalt was in a molten state, the above-described diluted solution was added to the molten asphalt so that the content was 0.1% by mass, and a sample was prepared by stirring. In addition, a blank to which no dilution solution was added was also prepared. The subject then smelled from the top 10 cm of the heat-resistant container while maintaining the temperature of the sample, and compared with the odor of the blank, the above-mentioned sensory evaluation was performed.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Public Health (AREA)
  • Water Supply & Treatment (AREA)
  • Engineering & Computer Science (AREA)
  • Hydrology & Water Resources (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental & Geological Engineering (AREA)
  • Veterinary Medicine (AREA)
  • Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
  • Treatment Of Sludge (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Pyrane Compounds (AREA)

Abstract

L'invention a pour objet de fournir un agent et un procédé de modification de mauvaise odeur qui modifient les odeurs d'asphalte, boue, eaux usées, ginkgo biloba, fumier, animaux marins, légumes, ordures ou peintures et vernis en odeurs différentes, et qui permettent de résoudre facilement les dommages dus à ces odeurs. Plus précisément, l'invention fournit un agent de modification de mauvaise odeur pour modification des odeurs d'asphalte, boue, eaux usées, ginkgo biloba, fumier, animaux marins, légumes, ordures ou peintures et vernis, lequel agent de modification de mauvaise odeur est caractéristique en ce qu'il comprend au moins une sorte de composé cyclique contenant de l'oxygène choisie parmi un composé furanne, un composé pyranne et un dérivé de cyclopentanone.
PCT/JP2018/043628 2017-11-29 2018-11-27 Agent de modification de mauvaise odeur pour modification des odeurs d'asphalte, boue, eaux usées, ginkgo biloba, fumier, animaux marins, légumes, ordures ou peintures et vernis, et procédé de modification de mauvaise odeur d'odeurs d'asphalte, boue, eaux usées, ginkgo biloba, fumier, animaux marins, légumes, ordures ou peintures et vernis WO2019107366A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201880076984.8A CN111565764A (zh) 2017-11-29 2018-11-27 沥青、污泥、污水、银杏、堆肥、海洋动物、蔬菜、垃圾或涂料的气味的转变用臭气转变剂和沥青、污泥、污水、银杏、堆肥、海洋动物、蔬菜、垃圾或涂料的气味的臭气转变方法

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JP2017-229636 2017-11-29
JP2017229636A JP7460981B2 (ja) 2017-11-29 2017-11-29 アスファルト、汚泥、汚水、銀杏、堆肥、海獣、野菜、生ゴミ又は塗料の臭いの変調用臭気変調剤、及びアスファルト、汚泥、汚水、銀杏、堆肥、海獣、野菜、生ゴミ又は塗料の臭いの臭気変調方法

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