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WO2002041927A1 - Deodorant, agent de masquage de l'odeur de l'ammoniac, deodorant de masquage des odeurs excretoires, et substance desodorisante apte a l'absorption d'eau - Google Patents

Deodorant, agent de masquage de l'odeur de l'ammoniac, deodorant de masquage des odeurs excretoires, et substance desodorisante apte a l'absorption d'eau Download PDF

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Publication number
WO2002041927A1
WO2002041927A1 PCT/JP2001/010274 JP0110274W WO0241927A1 WO 2002041927 A1 WO2002041927 A1 WO 2002041927A1 JP 0110274 W JP0110274 W JP 0110274W WO 0241927 A1 WO0241927 A1 WO 0241927A1
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WO
WIPO (PCT)
Prior art keywords
deodorant
jasmonic acid
general formula
acid compound
compound represented
Prior art date
Application number
PCT/JP2001/010274
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English (en)
Japanese (ja)
Inventor
Hiroshi Fujisawa
Koushirou Kanazawa
Hiroshi Hashimoto
Yoshiharu Ishimaru
Original Assignee
Zeon Corporation
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
Priority claimed from JP2000360093A external-priority patent/JP2002159565A/ja
Priority claimed from JP2001053275A external-priority patent/JP2002253651A/ja
Priority claimed from JP2001053247A external-priority patent/JP2002253653A/ja
Priority claimed from JP2001082724A external-priority patent/JP2002285001A/ja
Application filed by Zeon Corporation filed Critical Zeon Corporation
Publication of WO2002041927A1 publication Critical patent/WO2002041927A1/fr

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Classifications

    • 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

Definitions

  • the present invention relates to a novel deodorant and a deodorizing method.
  • the present invention relates to a masking agent for ammonia and a method for masking ammonia odor, and a deodorant for manure odor and a method for deodorizing the same.
  • the present invention relates to a highly water-absorbing deodorant suitable for absorbent articles such as disposable diapers and sanitary napkins, and a method for producing the same.
  • Examples of the physical deodorant include those in which an odor decomposition catalyst such as platinum or palladium is supported on a carrier such as activated carbon, zeolite, silica gel, and alumina, and those using an organic compound such as an ascorbic acid-based compound.
  • an odor decomposition catalyst such as platinum or palladium
  • a carrier such as activated carbon, zeolite, silica gel, and alumina
  • an organic compound such as an ascorbic acid-based compound.
  • Japanese Unexamined Patent Publication No. Hei 8-17638 Use of an adsorbent as described in Japanese Unexamined Patent Publication No. Hei 8-1763838; Use of wood vinegar solution (Japanese Unexamined Patent Publication No. 5-200666); Plant extract ⁇ lease inhibitor (Japanese Unexamined Patent Publication No. Hei 8-19595); methods using plant components such as methods using flavonoids (Japanese Unexamined Patent Application Publication No. Hei 5-23367); A method using an enzyme, such as a method for adsorbing lipase (Japanese Patent Application Laid-Open No. 6-136694), has been proposed. However, diapers that efficiently deodorize urine have not yet been obtained. Disclosure of the invention
  • An object of the present invention is to provide a novel organic compound-based deodorant and a deodorizing method.
  • Another object of the present invention is to provide a method capable of masking ammonia odor effectively.
  • An object of the present invention is to provide an effective deodorant for feces and urine and a method for deodorizing the same.
  • an object of the present invention is to provide a deodorant material having high water absorbability, which is suitable for an absorbent article such as a disposable diaper, and a method for producing the same.
  • methyldihydroxysmonate effectively masks the ammonia odor, and added a Noeon surfactant to this, dispersed it in water, and sprayed it directly around the barn. It was found that the odor disappeared.
  • a mixture of methino-residence dolodiasmonic acid and delta-decalactone was dispersed in water using a non-ionic surfactant, and this was sprayed directly onto the place where feces and urine odors were generated. I found that.
  • a deodorant containing a jasmonic acid compound represented by the following general formula (1) as an active ingredient is a deodorant containing a jasmonic acid compound represented by the following general formula (1) as an active ingredient.
  • R 1 represents a hydrocarbon group
  • R 2 represents a hydrocarbon group
  • the deodorant according to claim 1 comprising a jasmonic acid compound represented by the general formula (1) and a nonionic surfactant.
  • the deodorant according to (1) or (2) comprising an aqueous solution containing the jasmonic acid compound represented by the general formula (1) and a nonionic surfactant.
  • a deodorizing method using an aqueous solution containing a jasmonic acid compound represented by the general formula (1) and a nonionic surfactant as a deodorant is a deodorizing method using an aqueous solution containing a jasmonic acid compound represented by the general formula (1) and a nonionic surfactant as a deodorant.
  • ammonia as described in (6) or (7) above, comprising an aqueous solution containing a jasmonic acid compound represented by the general formula (1) and a nonionic surfactant.
  • Masking agent for ammonia as described in (6) or (7) above, comprising an aqueous solution containing a jasmonic acid compound represented by the general formula (1) and a nonionic surfactant.
  • a feces urine deodorant which is an aqueous solution containing the deodorant for feces and urine described in (11) or (12) and a nonionic surfactant.
  • a method for deodorizing manure odor which comprises spraying the manure odor deodorant described in any one of (11) to (14) on or around the manure odor generation surface.
  • a water-absorbing deodorant comprising a jasmonic acid compound represented by the general formula (1) and a highly water-absorbing resin.
  • the superabsorbent resin is impregnated with an aqueous emulsion or an organic solvent solution of the jasmonic acid compound represented by the general formula (1), and then dried.
  • the method for producing odorants is -
  • fragrance is a mixture of one or more fragrance compounds of a heliotrope type, a rose type, an orange flower type, an amber type or a musk type.
  • nonionic surfactant according to (8), wherein the nonionic surfactant is a polyoxyalkylene ether-based compound, a polyoxyalkylene glycol fatty acid ester-based compound or a polyoxyalkylene polyhydric alcohol-based fatty acid ester compound.
  • Masking agent is a polyoxyalkylene ether-based compound, a polyoxyalkylene glycol fatty acid ester-based compound or a polyoxyalkylene polyhydric alcohol-based fatty acid ester compound.
  • R 1 in the general formula (1) is an alkyl group having 1 to 10 carbon atoms or an alkyl group having 2 to 10 carbon atoms. Manure deodorant as described.
  • R 2 is an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 20 carbon atoms or an alkynyl group having 1 to 4 carbon atoms.
  • the deodorant for feces odor according to any one of (11) to (14), which is a droxyalkyl group.
  • nonionic surfactant is a polyoxyalkylene ether-based compound, a polyoxyalkylene glycol fatty acid ester-based compound or a polyoxyalkylene polyhydric alcohol-based fatty acid ester compound.
  • a deodorant for feces and odors comprising 0.15 parts by weight of delta ratatones with respect to 100 parts by weight of the jasmonic acid compound represented by the general formula (1).
  • the jasmonic acid compound used in the deodorant of the present invention is represented by the following general formula (1).
  • R 1 represents a hydrocarbon group
  • R 2 represents a hydrocarbon group
  • R 1 is a hydrocarbon group, for example, an alkyl group having 110, preferably 27 carbon atoms or 210, preferably 37, more preferably 46 And an alkyl group of
  • R 2 is a hydrocarbon group, for example, an alkyl group having 110, preferably 16, and more preferably 13 carbon atoms, 210, preferably 26, more preferably 2 Examples include an alkyl group having 3 carbon atoms, an alkyl group having 220 carbon atoms, preferably 28, more preferably 36, and a hydroxyalkyl group having 14 carbon atoms.
  • R 1 include, for example, a methyl group, an ethyl group, an n-propyl group, an isopropynole group, an n-butynole group, a sec-butynole group, a t-butyl / le group, an n-pentynole group, an isopentyl group, 2 _methylbutyl group, 1'methylbutyl group, n-xyl group, Isohexyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, n-heptyl, isoheptyl, n-octyl, isooctyl,
  • Examples include 3-methyl-12-pentenyl group, 5-hexenyl group, 3-hexenyl group, 2-hexenyl group, heptenyl group, otathenyl group, nonenyl group, and decyl group.
  • 3-hexenyl group, 2-hexenyl group and the like are preferable, n-pentyl group, isopentyl group, 2-methylbutyl group, 1-methylbutyl group, 4-pentenyl group, 3-pentenyl group, trans-2 —Pentenole, cis-2-pentenole, 1-pentul and the like are particularly preferred.
  • R 2 examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a pentinole group, an isoptinole group, a sec-butynole group, a t-pentynole group, a pentynole group, a hexyl group, a 2-methylbutyl group, and a aryl group.
  • the jasmonic acid compound include, for example, methyl (2-butyl-3-oxo-penticole) acetate, ethyl / le (2-petitinole-3-oxenoxy-clopentinole) acetate, and vinylinole (2-butynoley 3-oxo) Cyclo pliers A) Acetate, propyl (2-butyl-3-oxocyclopentyl) acetate, isopropyl (2-butyl-3-oxocyclopentyl) acetate, aryl (2-butyl-3-oxocyclopentyl) acetate, butyl ( 2-butyl-1-3-oxocyclopentyl acetate, methyl (2-pentyl-3-oxocyclopentynole) acetate, ethinole (2-pentynole-13-oxo-1 cyclopentizole) acetate, vinylinole (2-pentyne
  • methyl (3-oxo-1 (cis-12-pentyl) -cyclopentyl, wherein R 1 is a methyl group and R 2 is a cis-1-pentenyl group ) Acetate (hereinafter referred to as “dimethyljasmonic acid”); and, in the general formula (1), R 1 is a methyl group and R 2 is an n-pentyl group (2-pentynole-3-oxo-) One-cycle pentyl) acetate (hereinafter referred to as "dimethyldihydrodiasmonic acid”) is particularly preferred.
  • These jasmonic acid compounds can be used alone or in combination of two or more.
  • the jasmonic acid compound can be produced according to a conventional method.
  • the ester of dihydrojasmonate is an alkyl ester of 2-pentinoresic pentene-1-pentene and malonic acid. Can be easily produced by decarboxylation after adding Michael to
  • R 2 is an alkyl group having 2 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyl group having 2 to 6 carbon atoms, or a hydroxyalkyl group having 1 to 3 carbon atoms.
  • the jasmonic acid compound can be produced by the following method.
  • R 1 is the same as in the case of the general formula (1).
  • R 2 is an alkyl group having 2 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, It is a group selected from the group consisting of an alkynyl group having 2 to 6 carbon atoms and a hydroxyalkyl group having 1 to 3 carbon atoms.
  • the molar ratio of the methyl ester of jasmonic acid to the alcohol is usually 1 to 6 mol, preferably 3 to 4 mol, of alcohol per 1 mol of methyl ester of jasmonic acid.
  • Examples of the alcohol used in the transesterification reaction include methyl alcohol, ethyl alcohol, ethanol, alcohol, alcohol, alcohol, hexyl alcohol, hexyl alcohol, and 2-methylinobutyl alcohol.
  • T linoleanole cornore cis 1-pentene 1-one, trans-1 2-hexene 1-one, 4-butene 1-one, 4-meth / one- 3-pentene 1-one Cis-1-3 to xen-1-ol, prono-guinole alcohol, 2-pentin-1-one, 3-butin-1-one, 3-hexin-1-one, ethylene glycolone, propylene blender call And the like.
  • one compound represented by the general formula (2) and the compound represented by the general formula (3) may be used, or two or more compounds may be used in combination. .
  • the catalyst used in the transesterification reaction is not particularly limited as long as it is generally used as a transesterification catalyst.
  • the catalyst include hydroxides of alkaline metal alkaline earth metals and Basic catalysts such as alkoxides; protonic acids such as sulfuric acid and p-toluenesulfonic acid; acidic ion exchange resins; metal catalysts such as titanium alkoxides, aluminum alkoxides, tin compounds and lead compounds can be used. These catalysts may be used alone or in combination of two or more. The amount of the catalyst to be used is usually about 0.05 to 20% by weight of alcohol.
  • Solvents can be used.
  • the solvent to be used is not particularly limited as long as it does not inhibit the ester exchange reaction, but is preferably a hydrocarbon-based solvent.
  • hydrocarbon-based solvent examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene; and aliphatic hydrocarbons such as hexane and cyclohexene. These solvents can be used alone or in combination of two or more. These solvents are used in an amount of usually 100% by weight or less, preferably 500% by weight or less, more preferably 300% by weight, based on the total weight of jasmonic acid methyl ester and alcohol. Used at a rate of / 0 or less.
  • the reaction temperature for the transesterification reaction may be usually from room temperature to 300 ° C., and the reaction pressure may be normal pressure or reduced pressure.
  • the transesterification reaction is preferably performed in an inert atmosphere, but is not limited thereto. '
  • Methanol produced as a by-product during the transesterification reaction is preferably removed by distillation in order to promote the ester exchange reaction.
  • the solvent used in the transesterification reaction and the by-produced methanol azeotrope it is advantageous to promote the reaction by distilling off the solvent as an azeotrope outside the system. It is.
  • the transesterification reaction can be completed under the conditions described above, usually in about 30 minutes to 20 hours.
  • the reaction solution is cooled, and an alkaline aqueous solution such as a sodium hydroxide solution, a sodium hydrogencarbonate solution, a sodium carbonate solution is added to the system, and neutralization, filtration, washing, hydrolysis with an acid, and the like are performed.
  • an alkaline aqueous solution such as a sodium hydroxide solution, a sodium hydrogencarbonate solution, a sodium carbonate solution is added to the system, and neutralization, filtration, washing, hydrolysis with an acid, and the like are performed.
  • the aqueous layer is separated, and the organic layer is dried with magnesium sulfate, sodium sulfate, molecular sieve, or the like.
  • the desired jasmonic acid compound can be obtained by distilling off the remaining solvent and the remaining raw material compounds.
  • the obtained jasmonic acid compound can be further purified by distillation, chromatography or the like under reduced pressure or normal pressure.
  • the deodorant of the present invention is generally used in combination with at least one selected from a solid carrier, a liquid carrier and a dispersant, for an aqueous solution, emulsion, organic solvent solution, wettable powder, tablet, powder, flowable, and aerosol. Etc. can be used. Among them, aqueous solution is the best use form.
  • the solid carrier include clay group represented by kaolinite group, montmorinite group, attapulgite group, seekite, talc, mica, Inorganic substances such as pyrophyllite, pumice, vermiculite, gypsum, bentonite, calcium carbonate, dolomite, diatomaceous earth, magnesium, lime, phosphorus lime, zeolite, silicic anhydride, synthetic calcium silicate; soy flour , Tobacco flour, flour flour, barley flour, wood flour, starch, crystalline cellulose, ester gum, copal gum, dammal gum, and other vegetable organic substances; coumarone resin, petroleum resin, alkyd resin, polychlorinated butyl, ketone resin, etc.
  • the deodorant of the present invention can be included in a microcapsule and applied, for example, as a deodorant printing ink.
  • These solid carriers can be used alone or in combination of two or more.
  • liquid carrier examples include paraffinic, naphthenic, and aromatic hydrocarbons such as kerosene, mineral oil, spindle oil, white oil / oil, benzene, toluene, xylene, ethynolebenzene, tamen, and methyl naphthalene.
  • Chlorinated hydrocarbons such as tetrachlorosilane, chlorophonolem, trichloronorethylene, monochlorobenzene, and o-chlorotoluene; athenoles such as dimethyl ether, getyl ether, dioxane, tetrahydrofuran; acetone, methyl Ketones such as noretinoloketone, getyl ketone, diisobutyl ketone, cyclopentanone, cyclohexanone, acetophenonone, isophorone;
  • Estes / esters such as ethyl acetate, amino acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate, and getyl succinate; methanol / ethanol, ethanol / n-propanol, n-propanol, isopropanol / n-ptananol / Alcohols such as isoptanolone, n-hexanolone, ethylene glycolone, diethylene glycol, and glycerin; ether alcohols such as ethylene glycol phenyl ether and diethylene glycol butyl ether; organic liquids such as dimethyl honole amide and dimethyl sulfoxide And water.
  • hydrocarbons, ketones, alcohols, water and the like are particularly preferable, and alcohols and water are particularly preferable.
  • These liquid carriers can be used alone or in combination of two or more.
  • a surfactant is generally used.
  • the surfactant may be nonionic, cationic, anionic or zwitterionic, but a nonionic surfactant is preferably used.
  • Surfactants are most suitable when the deodorant is used in the form of an aqueous solution. In this case, the surfactant is used in an amount of 100 to 100 parts by weight, preferably 50 to 500 parts by weight, based on 100 parts by weight of the jasmonic acid compound represented by the general formula (1).
  • nonionic surfactant examples include: a block condensation polymer of two or more alkylene oxides such as oxyethylene oxypropylene block polymer; laurino oleanolecone; High-quality anore cornore such as nore, stearinoreal olecole, ore oleanore cornore; alkyl phenols such as octinole phenol, isootatinole phenol, and phenol, and alkyl naphthol such as butyl naphthol and octinolenophate.
  • alkylene oxides such as oxyethylene oxypropylene block polymer
  • laurino oleanolecone High-quality anore cornore such as nore, stearinoreal olecole, ore oleanore cornore
  • alkyl phenols such as octinole phenol, isootatinole phenol, and phenol
  • Glyceryl monostearate which is an ester compound of a polyhydric alcohol having three or more hydroxyl groups in the molecule, such as glycerin, pentaerythritol tonole, sorbitol, sonolebitan, mannitan, hexitane, and polycondensates thereof, and a higher fatty acid Monooleate, sorbitol monolaurate, sorbitol monopalmitate, sorbitol monostearate, sorbitol distearate, Sorbitol tristearate, sorbitol monooleate, sorbitol trioleate, sorbitol trioleate, sorbitolte traoleate, sonolebitan monolaterate, sorbitan monopalmitate, sonolebitan monostearate, sonolebitan distearate, sorbitan Stearate, sonolebitan monooleate, sonorebit
  • a polyoxyethylene sorbitan monolau obtained by polymerizing an alkylene oxide to the polyhydric alcohol-based fatty acid ester compound or by polymerizing the alkylene oxide to the polyhydric alcohol and then esterifying with the higher fatty acid.
  • Polyoxyalkylene alkylamine compounds such as polyoxyethylene alkylamine; alkyl alcohol amide compounds; and the like.
  • block condensation polymers having two or more alkylene oxides, polyoxyalkylene ether-based compounds, polyoxyalkylene dalycol fatty acid ester-based compounds, polyoxyalkylene polyhydric alcohol-based fatty acid ester compounds, and polyoxyalkylene alkyls
  • Polyoxyalkylene-based compounds which are alkylene oxide polymerized adducts such as amine compounds are preferred, and polyoxyalkylene ether-based compounds, polyoxyalkylene glycol fatty acid ester-based compounds, polyoxyalkylene polyhydric alcohol-based fatty acid ester compounds, and the like are preferable.
  • the method for preparing the deodorant of the present invention is not particularly limited, and a conventionally known method is used.
  • the jasmonic acid compound, the liquid carrier and the dispersant can be used by diluting and mixing with water.
  • diluting and mixing with an appropriate liquid such as water depending on the mode in which the deodorant is used, for example, a method of preparing an aqueous solution having an appropriate concentration in advance, a method of preparing an aqueous solution immediately before use, etc.
  • the method of deviation and deviation can also be adopted.
  • the amount of the deodorant of the present invention is appropriately selected according to the form of use, the method of use, and the like.
  • the amount of the jasmonic acid compound in the deodorant is usually based on the weight of the component generating odor. It is used in the range of 1 to 20% by weight, preferably 2 to 10% by weight.
  • the jasmonic acid compound used in the present invention has a particularly large effect of eliminating ammonia odor by masking ammonia, it can be used as a masking agent for ammonia containing the jasmonic acid compound as an active ingredient. . This has a greater elimination effect than conventional deodorants using a method such as decomposing ammonia.
  • the jasmonic acid compounds methyl jasmonic acid and dimethyldihydrodiasmonic acid are particularly preferred.
  • the masking agent for ammonia of the present invention may contain other fragrances other than the jasmonic acid compound represented by the general formula (1).
  • the above-mentioned other fragrances are not particularly limited, and generally include “Perfume Chemicals List II and IIIj (Hirokawa Shoten Co., Ltd.)”, “Synthetic fragrances (chemical and product knowledge)” (Chemical Daily) or Perfume described in “S. Arctander“ Perfume and Flavor Chemicals I and II ”j (Montc 1 air), etc., can be cited, depending on the place of use and purpose. Perfumed ones are used. Among them, for example, as the fragrance, a mixture of one or more fragrance compounds such as a heliotrope fragrance, a rose fragrance, an orange flower fragrance, an amber fragrance, and a musk fragrance is preferably used. Is done.
  • fragrance examples include helitropic fragrances, Tropine, musta ketone, coumarin, ethyne / leva dilin, acetinolesedren, horroline (meth ⁇ abietate), eugenol, methylonone, etc .;
  • Examples of the rose flavor include Damascon _ ⁇ , Damascon _ (3 ⁇ 4, Isobonoreninolemethoxycyclohexanore, Phenoinolethichinolea / Reconore, Geraniol, Iso-Ivornylmethoxycyclohexanore, etc .;
  • orange flower-based flavors include methyl anthranilate, ⁇ -endecalactone, and ⁇ -nonalactone
  • amber-based flavors include tetrahydroparamethylquinoline
  • examples of musk-based flavors include galact solid and musta ketone.
  • TABU Tebu
  • rose-, amber- and musk-based fragrance components are added to an oriental base mainly consisting of petty lily oil, together with a solvent, octyl phthalate (DO ⁇ ) Fragrances
  • oriental base examples include powder oil, herculin (methyl abiate), vanillin, ethyl valine, tamarin and the like.
  • the blending amount of the fragrance in the masking agent for ammonia of the present invention is not particularly limited, but the fragrance is usually 0.01 to 5 parts by weight based on 100 parts by weight of the jasmonic acid compound represented by the general formula (1). 100 parts by weight, preferably 1 to 100 parts by weight, is blended.
  • the form of use of the masking agent for ammonia of the present invention is usually the same as the form of use of the above-mentioned deodorant, and is usually an aqueous solution, emulsion, organic solvent solution in combination with at least one selected from solid carriers, liquid carriers and dispersants. , Wettable powders, tablets, powders, flowables, aerosols and the like. Among them, aqueous solution is the best use form.
  • specific examples of the solid carrier, the liquid carrier, and the dispersant may be the same as those described in detail in the section of the usage of the deodorant.
  • a nonionic surfactant as the above-mentioned deodorant.
  • the nonionic surfactant those similar to those described in detail in the section of the usage of the deodorant can be used.
  • 100 to 100 parts by weight of the nonionic surfactant is added to 100 parts by weight of the jasmonic acid compound represented by the general formula (1), preferably 100 to 100 parts by weight. Use 50 to 500 parts by weight.
  • the method for preparing the masking agent for ammonia of the present invention is not particularly limited, and a conventionally known method is used in the same manner as the above-described method for adjusting the deodorant.
  • a jasmonic acid compound, a liquid carrier and a dispersant can be used by diluting and mixing with water.
  • diluting and mixing with an appropriate liquid such as water
  • either a method of preparing an aqueous solution having an appropriate concentration in advance or a method of preparing an aqueous solution immediately before use is used depending on the mode of use. can do.
  • the amount of the masking agent for ammonia used in the present invention is appropriately selected according to the form of use, the method of use, and the like.
  • the jasmonic acid compound is used in an amount of 1 to 20% by weight, based on the weight of ammonia. It is preferably used in the range of 2 to 10% by weight.
  • the masking agent for ammonia of the present invention may be used in combination with a conventionally known deodorant, fragrance and the like. Further, the ammonia masking agent of the present invention can be used for various purposes. For example, a method of adding directly to a liquid that emits an ammonia odor, a method of spraying and spraying in the form of an aqueous solution on or around an ammonia odor generation source such as a livestock toilet, and a method of supporting an appropriate solid carrier such as clay and zeolite Deodorant in powder form, deodorant fiber products carried on non-woven fabric or other textile products (for example, toilet mats, toilet slippers, toilet seat covers, towels, and other toiletry products, Etc.), as a deodorizing filter by being supported on a filter base material, encapsulating to control the evaporation rate of methyl jasmonic acid, printing containing encapsulated methyl jasmonic acid How to prepare and use inks for use, use as disposable ommo sanitary products in
  • the jasmonic acid compound By combining the jasmonic acid compound and delta ratatones used in the present invention, it can be used as a deodorant for manure odor which has a quick deodorizing effect on manure odor.
  • jasmonic acid compounds particularly, methyl jasmonic acid and And dimethyldihydrodiasmonic acid are preferred.
  • the delta ratataton used in the deodorant for manure of the present invention is generally obtained as a dehydration product of ⁇ -hydroxy acid, and is a cyclic ester compound having an ester group in the ring.
  • Specific compounds include, for example, unsaturated delta lactones such as jasmine lactone, jasmolactone, massialactone, and tuberolactone; and saturated delta lactones such as otataractone, nonalataton, decalactone, pendecalactone, and dodecalataton.
  • delta ratatones having 8 or more carbon atoms are preferable.
  • the amount of the delta ratatones used in the deodorant for feces and urine of the present invention is not particularly limited, but is usually 0 based on 100 parts by weight of the jasmonic acid compound represented by the general formula (1). It is blended in a range of 0.5 to 10 parts by weight, preferably 0.5 to 10 parts by weight. An excessively small amount of the delta ratatones is not preferred because it becomes difficult to deodorize the indole compound odor among the excrement odors. If the delta lactone is used in an excessively large amount, the balance as a deodorant decreases, which is not preferable.
  • the deodorant for manure smell of the present invention may further use rifalcols in addition to the delta ratatatons.
  • the leaf alcohols include cis-3-hexenyl alcohol (hereinafter referred to as “leaf alcohol”) and derivatives thereof. Derivatives include cis-3-hexenyl esters, cis-3-hexenyl acetals and cis-3-hexenyl aldehydes.
  • leaf alcohol derivatives include cis-13-hexeninoleestenoles, cis-13-hexe-noreformate, cis-13-hexeninoleacetate, and cis-13 —Hexane-norepropionate, cis-1 3 —Hexeninoleisopropionate, cis-1—hexeninolerate, cis-1—3 hexeninole angelate, cis-1—3 Noleanthrate, cis-1-hexeninolebutyrate, cis-1-hexeneoleate / relate, cis-1-hexeninolay sonolelate, cis-3-hexenyl-methyl-2-butyrate, cis-1 3 to xeninole hexanoate, cis 1 to 3 — hexeninolysis 1 to 3 — hexenoate, cis 1 to 3 xenenoate, c
  • Cis-3-hexenylacetals include acetoaldehyde-ethyl-13-hexenylacetal and the like; cis-13-hexenylaldehydes include cis-13-hexenal and cis-13- Xenena-l-Jetice acetanore and the like.
  • the amount of the leaf alcohol to be used is not particularly limited, but is usually 0.01 to 20 parts by weight, preferably 0.1 to 100 parts by weight, based on 100 parts by weight of the jasmonic acid compound represented by the general formula (1). It is blended in the range of 5 to 10 parts by weight.
  • An excessively small amount of the leaf alcohols is not preferable because it is difficult to deodorize the merkabutane compound odor among the excrement of manure. If the amount of the leaf alcohol used is excessively large, the balance as a deodorant for excrement of manure is reduced, which is not preferable.
  • a fragrance other than the jasmonic acid compound represented by the general formula (1) can be blended similarly to the masking agent for ammonia described above.
  • Specific examples of the other fragrances include the same ones as described above.
  • the deodorant for manure of the present invention has an aqueous solution, an emulsion, an organic solvent solution, usually in combination with at least one selected from a solid carrier, a liquid carrier and a dispersant, in the same manner as the use form of the deodorant described above. It can be used in the form of wettable powders, tablets, powders, flowables, aerosols and the like. Among them, an aqueous solution is the best used form.
  • the specific examples of the solid carrier, the liquid carrier, and the dispersant those similar to those described in detail in the section of the usage of the deodorant can be used.
  • the method for preparing the deodorant for manure and urine of the present invention is not particularly limited, and a conventionally known method is used in the same manner as the above-described method for preparing the deodorant.
  • a diasmonic acid compound, a liquid carrier and a dispersant can be used by diluting and mixing with water.
  • diluting and mixing with an appropriate liquid such as water
  • either a method of preparing an aqueous solution having an appropriate concentration in advance or a method of preparing an aqueous solution immediately before use is employed depending on the mode of use. can do.
  • the amount of the deodorant for manure of the present invention to be used is appropriately selected depending on the use form, the use method, and the like.
  • the jasmonic acid compound in the deodorant for manure is usually 1 to 20% by weight based on the weight of the manure odor component. / 0 , preferably used in the range of 2 to 10% by weight c
  • the deodorant for feces and urine of the present invention may be used in combination with a conventionally known deodorant, fragrance and the like. Further, the deodorant for manure smell of the present invention can be used for various uses.
  • a method of adding directly to a liquid that emits manure a method of spraying / spraying a manure odor source such as a livestock toilet, or its surroundings in the form of an aqueous solution, or a method of supporting the solid on a suitable solid carrier such as clay-zeolite
  • a method of using as a powdered deodorant, a deodorant fiber product carried on a nonwoven fabric or other fiber product for example, toilet mats, toilet slippers, toilet seat covers, toiletry products such as towels, ommuk covers, etc.
  • Polio Fins how to use in the form of a laminated body as a container. Bags such as deodorant of the film, method, and the like to be used as flooring ⁇ door-wall material of toilet peripheral in combination with a building interior material. Water absorbent deodorant
  • the jasmon oxide compound represented by the general formula (1) used in the present invention can be used as a water-absorbing deodorant.
  • the jasmonic acid compounds methyl jasmonic acid and dimethyldihydrodiasmonic acid are particularly preferred.
  • the jasmonic acid-based compound represented by the general formula (1) is preferably used as an aqueous emulsion or an organic solvent solution.
  • the aqueous emulsion is prepared by emulsifying a jasmonic acid compound in an aqueous medium using a surfactant.
  • a surfactant a nonionic surfactant, an anionic surfactant, or the like can be used.
  • nonionic surfactant examples include polyoxyethylene lauryl phenyl ether, polyoxyethylene stearyl phenyl ether, and polyoxyethylene Polyoxyalkylene ether compounds such as ethylene olenophenyl ether and polyoxyethylene noelle ether; polyoxyethylene glycol monomonolaurate, polyethylene glycol monomonostearate, polyethylene glycol distearate, polyethylene glycol monostearate Polyoxyalkylene dalichol fatty acid ester compounds such as oleate;
  • a polyoxyalkylene ether-based compound a polyoxyalkylene glycol fatty acid ester-based compound, a polyoxyalkylene polyhydric alcohol-based fatty acid ester compound, and the like are particularly preferable.
  • the anionic surfactant include alkylaryl sulfonates such as sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, and sodium propylnaphthalenesulfonate; sodium lauryl sulfate, potassium myristyl sulfate, and tetradecyl.
  • Alkyl sulfates such as sodium sulfate; sodium dioctyl sulfosuccinate, sodium dihexyl sulfosuccinate Sulfosuccinates such as lime; fatty acid salts such as sodium laurate, sodium stearate and potassium semi-hardened tallow fatty acid; polyoxyethylene lauryl ether phenolic sodium salt; polyoxyethylene lauryl ether phenolic ether salt; Ethoxysulfate salts such as aetnadium; alkane sulfonates; alkyl ether phosphates and the like. Of these, alkylaryl sulfonates, alkyl sulfates, sulfosuccinates, and fatty acid salts are preferred.
  • nonionic surfactants are preferred.
  • the ratio of each component of the aqueous emulsion is 100 parts by weight of jasmonic acid compound, and water is usually 100 to 1,000 parts by weight, preferably 200 to 800 parts by weight. is there.
  • the surfactant is usually used in an amount of 100 to 1000 parts by weight, preferably 50 to 800 parts by weight, per 100 parts by weight of the jasmonic acid compound.
  • these three components are mixed by high-speed stirring with a homomixer or the like, or a high-speed pump is applied. :! ⁇ 1 ⁇ , preferably 0.2 to 2 / zm.
  • the jasmonic acid compound is preferably prepared from methanol, ethanol, isopropanolose; dimethinoleatenole, getyl ether; An organic solvent having a low boiling point of 80 ° C. is mixed with an organic solvent at a ratio of usually 0.6 to 2 volumes, preferably 0.8 to 2 volumes per 1 volume of the jasmonic acid compound.
  • the superabsorbent resin used in the water-absorbing deodorant of the present invention is not particularly limited, and the resin lg absorbs 35 g or more of physiological saline (0.9% by weight of sodium chloride) at normal pressure. Preferably, water absorption of 40 to 80 g can be used.
  • superabsorbent resins include polyacrylic acid amides, polyacrylates, crosslinked polyacrylic acid, polyacrylic acid-based water-absorbent resins such as polyacrylates; starch grafts and polyacetate burs, starches. Graft and starch-grafted polymer-based water-absorbing resin such as polyacrylic acid and starch-grafted poly-tararilonitrile;
  • Polyester esters such as saponified acrylic acid monoacetate copolymer, saponified acrylic acid ester monoacetate copolymer, and crosslinked polyacetate bielkene Aqueous resin; cellulosic water-absorbing resin such as cross-linked carboxymethyl cellulose, graft cellulose, cross-linked graft cellulose; cross-linked isobutylene-maleic anhydride copolymer;
  • Crosslinked polyethylene oxide ; sulfonic acid group-containing polymer; carbobetaine-type polymer; polyether compounds such as polyetherester, polyetheresteramide, and polyetheresteramide. These can be used alone or in combination of two or more.
  • the average particle diameter of the superabsorbent resin is usually 0.05 ⁇ ! It is preferred to use particles of up to 5 mm, preferably 50 to 150. In addition, if necessary, it can be used in the form of filaments of these super absorbent polymers, or woven or non-woven fabrics using the filaments.
  • the amount of the jasmonic acid compound used in the water absorbent deodorant of the present invention is usually 0.05 to 20 parts by weight, preferably 0.1 to 10 parts by weight, based on 100 parts by weight of the superabsorbent resin. Parts by weight.
  • the method for producing the water-absorbing deodorant material of the present invention includes a method of immersing the superabsorbent resin in the aqueous emulsion or organic solvent solution of the above-mentioned jasmonic acid compound, followed by drying.
  • a method of spraying the emulsion or the above-mentioned jasmonic acid organic solvent solution for impregnation, followed by drying, etc. may be mentioned.
  • the drying method is not limited, and a vacuum dryer, a rotary kiln, a hot air circulating dryer, a band dryer, or the like is used.
  • the vacuum dryer is used to heat to 25 to 40 ° C as necessary. Drying while drying is preferable because the evaporation of jasmonic acid compounds can be prevented.
  • the water-absorbing deodorant material of the present invention has a function of absorbing liquid at the same time as coming into contact with urine and deodorizing as if there was no urine odor from the beginning.
  • the method of applying the water-absorbing deodorant of the present invention to absorbent articles includes, for example, a plastic film such as porous polyethylene or polypropylene. And a cotton nonwoven fabric or water-absorbent paper (b) and the water-absorbent deodorant of the present invention (c).
  • a plastic film such as porous polyethylene or polypropylene.
  • the amount of the water-absorbing deodorant of the present invention is not particularly limited, it is usually 5 to 25 gZ for diapers and incontinence pads, and 0.2 to 2 gZ for sanitary napkins and panty liners.
  • Example 1 a known deodorant or fragrance may be used in combination.
  • Example 2 a known deodorant or fragrance may be used in combination.
  • Methinoresidic diasmonic acid [Methinole (2-pentynole-3-oxo-cyclopentyl) -acetate] (hereinafter referred to as “MDJ”) is mixed with the same amount of dispersant (polyoxyethylene sorbitan monooleate).
  • MDJ Metal-pentynole-3-oxo-cyclopentyl
  • the deodorant was added to the urine lOO g (ammonia content 0.8%) and the above deodorant 0.055 g (MDJ 3% for ammonia in urine). Further, this was diluted with 5000 g of water, and the odor was evaluated by six panelists.Evaluation was performed immediately after the addition, after one day and after two days, and the results are shown in Table 1.
  • a perfume compound was prepared by mixing the perfume mixture shown in Table 2 with MDJ (90 parts, boiling point: 305 ° C), and the odor was evaluated in the same manner as in Example 1 using this compound. However, the MDJ for ammonia in urine is 1.2%.
  • a deodorant was prepared using MDJ in the same manner as in Example 1. This deodorant was added to a mixture of 200 kg of bovine urine (100 kg) (ammonia content 0.8%) and water (100 kg) in an amount of 500 g (500 g of bovine urine). Add ammonia (3.1% in MDJ equivalent) to ammonia 200 g (1.3% in ammonia in cow urine equivalent to MDJ) 0 g (0% in cow urine in MDJ equivalent) 3 A sample for seeding was used.
  • the spray sample was sprayed on the field, and the sensory evaluation of the odor felt by the worker at that time was performed.
  • the odor disappeared about 10 seconds after the start of the work.
  • the odor was sensuously evaluated by 5 evaluators under the leeward Table 3
  • a novel deodorant particularly a deodorant having an excellent effect on malodor of urine system, and a deodorant method can be provided.
  • Methyl dihydrodiasmonic acid hereinafter referred to as “MD J”
  • other perfume mixture other perfume mixture and the dispersant (polyoxyethylene sorbitan monooleate) shown in Table 2 were added and mixed.
  • the following masking agents for ammonia (masking agents 1 to 3) were prepared.
  • the concentration of MDJ in each masking agent was masking agent 1 (50%), masking agent 2 (25%), and masking agent 3 (17%).
  • MJ methyl jasmonic acid
  • other perfume mixture and dispersant polyoxyethylene sorbitan monooleate
  • Masking agents were prepared (masking agents 4-6). The concentrations of MJ in each masking agent were masking agent 1 (50%), masking agent 2 (25%), and masking agent 3 (17%).
  • the masking agent 1-6 after adding 20m g, 4 Om g s l O Omg respectively, 50 times with water After dilution, sensory evaluation was performed on the odor of ammourea by six panelists.
  • the ratio of MDJ or MJ to ammonia in ammonia water is as follows, respectively.
  • Table 6 shows the results of evaluation immediately after the addition, one day after the addition, and two days after the addition.
  • the evaluation criteria in Table 6 are as follows.
  • An aqueous solution of a masking agent for ammonia (10 concentration: 1%) was prepared by mixing 500 g of the masking agent 1 prepared in Example 4 with 25 kg of water. Next, this aqueous solution of the ammonia masking agent was sprayed around a 500-square-meter-square barn, and the sensory evaluation of the odor felt by workers at that time was performed. I no longer feel.
  • the deodorant 2 prepared in the above Example was mixed with 500 kg of water and 25 kg of water to prepare an aqueous solution of a deodorant for feces and urine (MDJ concentration 1%). Next, this aqueous solution was sprayed around a pighouse of about 300 square meters in size, As a result of the performance evaluation, the odor of feces and urine disappeared about 10 seconds after the start of the work.
  • the present invention provides a deodorant for manure and urine having an excellent effect on manure and urine odor.
  • Methyl (2-pentinole-3-pentoxopentinole) acetate also referred to as methinolesig dolodiasmonate; hereinafter abbreviated as “MD J”
  • MD J methinolesig dolodiasmonate
  • a 100 ml beaker containing 1 g of a water-absorbent sample absorbs 2 Oml of urine just collected from an adult male, takes it out with a pair of tweezers, transfers it to a petri dish, and five persons (passed panel test) smell the following criteria. And was expressed as an average value. The smaller the value, the better the deodorant.
  • Example 11 a perfume compound was prepared by mixing MD J (90 parts) with the perfume mixture shown in Table 2 in place of MD J (however, the concentration of MD J was 19% ). Next, an aqueous emulsion B was prepared using 100 parts of the perfume compound, and the same operation as in Example 11 was performed to prepare a sample b. Table 9 shows the results of examining the deodorant properties and water absorption of sample b.
  • Example 11 was repeated in the same manner as in Example 1 except that in place of MD 100 parts, each 100 parts of a citrus flavor for flavor and 100 parts of a mint flavor for flavor were used individually. Sample c and sample d were prepared. Table 9 shows the results of examining the deodorizing properties and water absorption of Samples c and d.
  • the present invention can provide a water-absorbing deodorant having an effect of deodorizing urine odor, which is suitable for absorbent articles such as disposable diapers.
  • the novel deodorant, the masking agent for ammonia, the deodorant for manure and the water-absorbing deodorant of the present invention can be used for various applications.

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  • Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Disinfection, Sterilisation Or Deodorisation Of Air (AREA)

Abstract

La présente invention concerne un déodorant contenant, en tant que substances actives, un composé d'acide jasmonique tel qu'un méthyle jasmonate ou méthyle dihydrojasmonate, et un tensioactif non ionique tel qu'un composé polyoxyalkylène éther. Le composé d'acide jasmonique a une efficacité élevée, notamment en ce qui concerne le masquage de l'odeur de l'ammoniac. Il peut être utilisé en tant qu'agent de masquage de l'odeur de l'ammoniac. Une combinaison du composé d'acide jasmonique et d'un composé de δ-lactone peut être utilisée en tant que déodorant de masquage des odeurs excrétoires. Une substance désodorisante apte à l'absorption d'eau, comprenant une combinaison du composé d'acide jasmonique et d'une résine à capacité élevée d'absorption d'eau, peut trouver différentes applications.
PCT/JP2001/010274 2000-11-27 2001-11-26 Deodorant, agent de masquage de l'odeur de l'ammoniac, deodorant de masquage des odeurs excretoires, et substance desodorisante apte a l'absorption d'eau WO2002041927A1 (fr)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
JP2000360093A JP2002159565A (ja) 2000-11-27 2000-11-27 消臭剤と消臭方法
JP2000-360093 2000-11-27
JP2001053275A JP2002253651A (ja) 2001-02-28 2001-02-28 糞尿臭用消臭剤と消臭方法
JP2001-53275 2001-02-28
JP2001053247A JP2002253653A (ja) 2001-02-28 2001-02-28 アンモニア用マスキング剤
JP2001-53247 2001-02-28
JP2001082724A JP2002285001A (ja) 2001-03-22 2001-03-22 吸水性消臭材およびその製造方法
JP2001-82724 2001-03-22

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KR20190132961A (ko) * 2016-04-22 2019-11-29 주식회사 엘지생활건강 이취 억제용 향료 조성물

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US4840792A (en) * 1986-05-29 1989-06-20 Robertet S.A. Agent neutralizing bad smells from excretions and excrements of animals
JPH03294219A (ja) * 1990-04-11 1991-12-25 T Hasegawa Co Ltd 持続性芳香剤
JPH04114739A (ja) * 1990-09-05 1992-04-15 Nippon Shokubai Co Ltd 吸水性複合体の製造法
WO1996004940A1 (fr) * 1994-08-12 1996-02-22 The Procter & Gamble Company Composition reduisant l'impression de mauvaise odeur sur les surfaces inanimees
JPH09194340A (ja) * 1996-01-12 1997-07-29 Pola Chem Ind Inc エステル分解抑制剤及びそれを含有する化粧料
JPH10263062A (ja) * 1997-03-26 1998-10-06 Pola Chem Ind Inc 配糖体及び包摂香料を含有する異臭抑制生成物
JPH11221272A (ja) * 1998-02-06 1999-08-17 Lion Corp 消臭剤及び消臭剤組成物
JP2000143455A (ja) * 1998-11-10 2000-05-23 Kao Corp 毛髪化粧料

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JPS61179155A (ja) * 1985-02-04 1986-08-11 太平化学産業株式会社 おしめの悪臭発生防止剤
US4840792A (en) * 1986-05-29 1989-06-20 Robertet S.A. Agent neutralizing bad smells from excretions and excrements of animals
JPH03294219A (ja) * 1990-04-11 1991-12-25 T Hasegawa Co Ltd 持続性芳香剤
JPH04114739A (ja) * 1990-09-05 1992-04-15 Nippon Shokubai Co Ltd 吸水性複合体の製造法
WO1996004940A1 (fr) * 1994-08-12 1996-02-22 The Procter & Gamble Company Composition reduisant l'impression de mauvaise odeur sur les surfaces inanimees
JPH09194340A (ja) * 1996-01-12 1997-07-29 Pola Chem Ind Inc エステル分解抑制剤及びそれを含有する化粧料
JPH10263062A (ja) * 1997-03-26 1998-10-06 Pola Chem Ind Inc 配糖体及び包摂香料を含有する異臭抑制生成物
JPH11221272A (ja) * 1998-02-06 1999-08-17 Lion Corp 消臭剤及び消臭剤組成物
JP2000143455A (ja) * 1998-11-10 2000-05-23 Kao Corp 毛髪化粧料

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190132961A (ko) * 2016-04-22 2019-11-29 주식회사 엘지생활건강 이취 억제용 향료 조성물
KR20210098893A (ko) * 2016-04-22 2021-08-11 주식회사 엘지생활건강 이취 억제용 향료 조성물
KR102289696B1 (ko) 2016-04-22 2021-08-17 주식회사 엘지생활건강 이취 억제용 향료 조성물
KR102397919B1 (ko) 2016-04-22 2022-05-16 주식회사 엘지생활건강 이취 억제용 향료 조성물

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