JP2018068730A - Deodorant for basic odor - Google Patents
Deodorant for basic odor Download PDFInfo
- Publication number
- JP2018068730A JP2018068730A JP2016213204A JP2016213204A JP2018068730A JP 2018068730 A JP2018068730 A JP 2018068730A JP 2016213204 A JP2016213204 A JP 2016213204A JP 2016213204 A JP2016213204 A JP 2016213204A JP 2018068730 A JP2018068730 A JP 2018068730A
- Authority
- JP
- Japan
- Prior art keywords
- mercapto
- odor
- deodorant
- oil
- basic
- 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.)
- Granted
Links
- 239000002781 deodorant agent Substances 0.000 title claims abstract description 63
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 150000001412 amines Chemical class 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 239000003205 fragrance Substances 0.000 claims description 54
- 230000001877 deodorizing effect Effects 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- XLMPYCGSRHSSSX-UHFFFAOYSA-N 3-Mercapto-2-butanone Chemical compound CC(S)C(C)=O XLMPYCGSRHSSSX-UHFFFAOYSA-N 0.000 claims description 7
- SZECUQRKLXRGSJ-UHFFFAOYSA-N 3-Mercapto-2-pentanone Chemical compound CCC(S)C(C)=O SZECUQRKLXRGSJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000001356 (3R)-3-sulfanylbutan-2-one Substances 0.000 claims description 6
- 239000001082 (3R)-3-sulfanylpentan-2-one Substances 0.000 claims description 6
- GVDXJPHOFKMDJV-UHFFFAOYSA-N 4-methyl-3-sulfanylpentan-2-one Chemical compound CC(C)C(S)C(C)=O GVDXJPHOFKMDJV-UHFFFAOYSA-N 0.000 claims description 6
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 241000251468 Actinopterygii Species 0.000 claims description 5
- LOAIDFOHKPUHQT-UHFFFAOYSA-N SC(C(C)=O)CCC(C)C Chemical compound SC(C(C)=O)CCC(C)C LOAIDFOHKPUHQT-UHFFFAOYSA-N 0.000 claims description 5
- 210000003608 fece Anatomy 0.000 claims description 5
- YTISVSDAQITBDE-UHFFFAOYSA-N 3-sulfanylhexan-2-one Chemical compound CCCC(S)C(C)=O YTISVSDAQITBDE-UHFFFAOYSA-N 0.000 claims description 4
- RYHVKGHMNAUHTJ-UHFFFAOYSA-N 3-sulfanyloctan-2-one Chemical compound CCCCCC(S)C(C)=O RYHVKGHMNAUHTJ-UHFFFAOYSA-N 0.000 claims description 4
- ZRSJBRLWARLYGS-UHFFFAOYSA-N 5-methyl-3-sulfanylhexan-2-one Chemical compound CC(C)CC(S)C(C)=O ZRSJBRLWARLYGS-UHFFFAOYSA-N 0.000 claims description 4
- HZLSFHFOBZDIPR-UHFFFAOYSA-N SC(C(C)=O)CCCC Chemical compound SC(C(C)=O)CCCC HZLSFHFOBZDIPR-UHFFFAOYSA-N 0.000 claims description 4
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- 239000010871 livestock manure Substances 0.000 claims description 4
- DXLFJSOTLSRGGF-UHFFFAOYSA-N SC(C(C)=O)CCCCCCC Chemical compound SC(C(C)=O)CCCCCCC DXLFJSOTLSRGGF-UHFFFAOYSA-N 0.000 claims description 3
- OYHVSDPRUJLGBA-UHFFFAOYSA-N SC(C(C)=O)CCCCCCCC Chemical compound SC(C(C)=O)CCCCCCCC OYHVSDPRUJLGBA-UHFFFAOYSA-N 0.000 claims description 3
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract description 28
- 239000000126 substance Substances 0.000 abstract description 17
- 125000003118 aryl group Chemical group 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 10
- 239000002304 perfume Substances 0.000 abstract description 4
- 230000000873 masking effect Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 33
- 235000019198 oils Nutrition 0.000 description 33
- 230000000052 comparative effect Effects 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- -1 sinensar Chemical compound 0.000 description 18
- 210000004209 hair Anatomy 0.000 description 13
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- 239000000796 flavoring agent Substances 0.000 description 10
- 235000019634 flavors Nutrition 0.000 description 10
- 238000009472 formulation Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
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- 239000011521 glass Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229940022663 acetate Drugs 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 244000061176 Nicotiana tabacum Species 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000008213 purified water Substances 0.000 description 5
- JWMDAOZVXXCQCN-UHFFFAOYSA-N CCC(C)C(C(=O)C)S Chemical compound CCC(C)C(C(=O)C)S JWMDAOZVXXCQCN-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
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- 239000000443 aerosol Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 4
- 229960002216 methylparaben Drugs 0.000 description 4
- 230000001953 sensory effect Effects 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 4
- PRNCMAKCNVRZFX-UHFFFAOYSA-N 3,7-dimethyloctan-1-ol Chemical compound CC(C)CCCC(C)CCO PRNCMAKCNVRZFX-UHFFFAOYSA-N 0.000 description 3
- QRNZMFDCKKEPSX-UHFFFAOYSA-N 4-mercapto-4-methylpentan-2-one Chemical compound CC(=O)CC(C)(C)S QRNZMFDCKKEPSX-UHFFFAOYSA-N 0.000 description 3
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZYEMGPIYFIJGTP-UHFFFAOYSA-N Eugenol methyl ether Natural products COC1=CC=C(CC=C)C=C1OC ZYEMGPIYFIJGTP-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 235000019864 coconut oil Nutrition 0.000 description 3
- 239000003240 coconut oil Substances 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000779 smoke Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- OHEFFKYYKJVVOX-UHFFFAOYSA-N sulcatol Natural products CC(O)CCC=C(C)C OHEFFKYYKJVVOX-UHFFFAOYSA-N 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- ULDHMXUKGWMISQ-SECBINFHSA-N (-)-carvone Chemical compound CC(=C)[C@@H]1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-SECBINFHSA-N 0.000 description 2
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- JSNRRGGBADWTMC-UHFFFAOYSA-N (6E)-7,11-dimethyl-3-methylene-1,6,10-dodecatriene Chemical compound CC(C)=CCCC(C)=CCCC(=C)C=C JSNRRGGBADWTMC-UHFFFAOYSA-N 0.000 description 2
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- NJXYRZMLVYMJHM-UHFFFAOYSA-N 1,1-dimethoxy-2-methylundecane Chemical compound CCCCCCCCCC(C)C(OC)OC NJXYRZMLVYMJHM-UHFFFAOYSA-N 0.000 description 2
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- FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 2
- QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 2
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- FZXRXKLUIMKDEL-UHFFFAOYSA-N 2-Methylpropyl propanoate Chemical compound CCC(=O)OCC(C)C FZXRXKLUIMKDEL-UHFFFAOYSA-N 0.000 description 2
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Abstract
Description
本発明は、アンモニア臭又はアミン臭などの塩基性悪臭に対して特異的に消臭効果を有する消臭剤、該消臭剤を用いた消臭用香料組成物およびトイレタリー製品又はハウスホールド製品並びに該消臭剤を用いた消臭方法に関する。 The present invention relates to a deodorant having a deodorizing effect specifically with respect to a basic malodor such as ammonia odor or amine odor, a deodorant fragrance composition using the deodorant, a toiletry product or a household product, and The present invention relates to a deodorizing method using the deodorant.
塩基性悪臭に対する消臭方法としては、感覚的消臭方法と化学的消臭方法があり、悪臭源に応じて様々な製品が開発されてきている。一般的に用いられている手法は、悪臭をマスキングする芳香性組成物を用い、感覚的に悪臭を感じさせなくする方法であり、数多くの芳香性消臭剤が市販されている。一方、強い悪臭に対しては化学的消臭、例えば塩基性悪臭に対して酸性物質による中和方法が用いられることが一般的である。しかしながら、いずれの方法においても、心地よい芳香と持続性のある消臭効果の両立は難しく、感覚的消臭効果と化学的消臭効果の両方の効果を併せ持つ素材の開発が求められていた。 There are a sensory deodorizing method and a chemical deodorizing method as a deodorizing method for a basic malodor, and various products have been developed according to the malodor source. A commonly used technique is a method of using a fragrance composition that masks malodors to prevent the odor from being felt sensuously, and many aromatic deodorants are commercially available. On the other hand, for strong malodor, chemical deodorization, for example, neutralization with an acidic substance is generally used for basic malodor. However, in any of the methods, it is difficult to achieve both a pleasant fragrance and a long-lasting deodorizing effect, and there has been a demand for the development of a material having both a sensory deodorizing effect and a chemical deodorizing effect.
塩基性悪臭に対する消臭剤としては、例えば、アミルシンナミックアルデヒド、桂皮酸エチル、ヌートカトン、6−メチル−5−ヘプテン−2−オン等から選ばれる香料物質と、カンラン科植物等の抽出物からなる塩基性悪臭用消臭剤(特許文献1)等が提案されているが、効果の点でさらなる技術の開発が求められていた。 As a deodorant for basic malodor, for example, a fragrance substance selected from amylcinnamic aldehyde, ethyl cinnamate, nootkatone, 6-methyl-5-hepten-2-one and the like, and an extract of an orchidaceae plant Although the basic deodorant for a bad odor (patent document 1) etc. which have become is proposed, development of the further technique was calculated | required by the point of the effect.
近年、消費者の嗜好性が多様化してきていることに伴い、各種各様の商品の開発が望まれている。特に香粧品、飲食品業界はこの傾向が強く、消費者の嗜好に合うバラエティーに富んだ香粧品、飲食品の開発が強く要求されている。これらの要求に対し、本出願人は先に、新規硫黄化合物である3−メルカプト−2−アルカノン類に着目し合成、その香気香味特性について検討した結果、シトラス様、ミート様、果物様、茶様、コーヒー様等の香気香味特性を有すること見出し、さらに当該化合物類を調合香料に含有させることにより、自然で天然感が向上した調合香料の提供を可能とした(特許文献2)。 In recent years, with the diversification of consumer preferences, development of various products has been desired. This trend is particularly strong in the cosmetics and food / beverage industries, and there is a strong demand for the development of cosmetics and food / beverage products that are rich in variety to suit consumer preferences. In response to these requirements, the present applicants first focused on a novel sulfur compound, 3-mercapto-2-alkanones, and synthesized and studied its aroma and flavor characteristics. As a result, citrus-like, meat-like, fruit-like, tea It has become possible to provide a blended fragrance that is naturally natural and has an improved natural feeling by finding that it has aroma and flavor characteristics such as coffee and coffee, and by adding the compounds to the blended fragrance (Patent Document 2).
さらに上記3−メルカプト−2−アルカノン類の特性を精査したところ、該化合物類がアミン臭等の塩基性悪臭に対して強い化学的消臭効果を示すことを見いだした。 Furthermore, when the characteristics of the 3-mercapto-2-alkanones were scrutinized, it was found that the compounds showed a strong chemical deodorizing effect against basic malodor such as amine odor.
従来よりメルカプトアルカノン化合物は強い香気を有することが知られており、例えば、4−メルカプト−4−メチルペンタン−2−オンを含有する香粧品用香料組成物(特許文献3)、3級メルカプトケトンを含有する消臭・芳香剤(特許文献4)、α−ケトチオールを添加する食料品の香味を変える方法(特許文献5)などが提案されているが、3−メルカプト−2−アルカノン類が特定の悪臭、すなわち魚臭、生ゴミ臭のキー成分として知られるトリメチルアミンのアミン臭に対し化学的消臭効果を示すことはこれまで知られていなかった。 Conventionally, it is known that a mercapto alkanone compound has a strong aroma. For example, a perfume composition for cosmetics containing 4-mercapto-4-methylpentan-2-one (Patent Document 3), a tertiary mercapto A deodorizing and aromatic agent containing a ketone (Patent Document 4), a method for changing the flavor of a food product to which α-ketothiol is added (Patent Document 5), and the like have been proposed, but 3-mercapto-2-alkanones are proposed. Until now, it has not been known to exhibit a chemical deodorizing effect on the amine odor of trimethylamine, which is known as a key component of specific malodor, that is, fish odor and garbage odor.
本発明が解決しようとする課題は、アミン臭等の塩基性悪臭に対し化学的消臭効果を示し、かつ、塩基性悪臭と調和した優れた芳香性を有するマスキング効果を示す素材の提供である。 The problem to be solved by the present invention is to provide a material that exhibits a chemical deodorizing effect on basic malodors such as amine odor and has a masking effect having excellent fragrance in harmony with the basic malodor. .
上記課題を解決するために、本発明者が鋭意検索した結果、特定構造を有する3−メルカプト−2−アルカノン化合物が、アミン臭等の塩基性悪臭に対する強い化学的消臭効果のみならず、塩基性悪臭と調和した優れた芳香性を有するマスキング効果を示すことを見いだし、本発明を完成させた。すなわち本発明は以下に示すとおりのものである。 In order to solve the above-mentioned problems, as a result of intensive search by the present inventors, a 3-mercapto-2-alkanone compound having a specific structure is not only a strong chemical deodorizing effect against basic malodor such as amine odor but also a base. The present invention has been completed by finding that it has a masking effect having an excellent fragrance in harmony with natural odor. That is, the present invention is as follows.
1.下記一般式(1)
2.一般式(1)で表される化合物が、3−メルカプト−2−ブタノン、3−メルカプト−2−ペンタノン、3−メルカプト−2−ヘキサノン、3−メルカプト−2−ヘプタノン、3−メルカプト−2−オクタノン、3−メルカプト−2−ノナノン、3−メルカプト−2−デカノン、3−メルカプト−2−ウンデカノン、3−メルカプト−2−ドデカノン、3−メルカプト−4−メチル−2−ペンタノン、3−メルカプト−4−メチル−2−ヘキサノン、3−メルカプト−5−メチル−2−ヘキサノン、3−メルカプト−6−メチル−2−ヘプタノンであることを特徴とする、前記塩基性悪臭用消臭剤。
3.前記塩基性悪臭用消臭剤を1ppt〜5000ppm含有することを特徴とする、トイレタリー製品又はハウスホールド製品。
4.前記塩基性悪臭用消臭剤を含有することを特徴とする、消臭用香料組成物。
5.前記塩基性悪臭用消臭剤を0.01ppm〜10000ppm含有することを特徴とする、消臭用香料組成物。
6.前記消臭用香料組成物を0.01質量%〜50質量%含有することを特徴とするトイレタリー製品又はハウスホールド製品。
7.前記塩基性悪臭用消臭剤を1ppt〜5000ppm濃度噴霧することを特徴とする、塩基性悪臭の消臭方法。
8.塩基性悪臭がアンモニア臭、アミン臭、魚臭、生ゴミ臭、糞尿臭又はタバコ臭であることを特徴とする、前記消臭方法。
1. The following general formula (1)
2. The compound represented by the general formula (1) is 3-mercapto-2-butanone, 3-mercapto-2-pentanone, 3-mercapto-2-hexanone, 3-mercapto-2-heptanone, 3-mercapto-2- Octanone, 3-mercapto-2-nonanone, 3-mercapto-2-decanone, 3-mercapto-2-undecanone, 3-mercapto-2-dodecanone, 3-mercapto-4-methyl-2-pentanone, 3-mercapto- The deodorizer for basic malodor, which is 4-methyl-2-hexanone, 3-mercapto-5-methyl-2-hexanone, 3-mercapto-6-methyl-2-heptanone.
3. A toiletry product or a house hold product, which contains 1 ppm to 5000 ppm of the basic deodorant for bad odor.
4). A deodorant fragrance composition comprising the basic malodor deodorant.
5. A deodorant fragrance composition comprising 0.01 ppm to 10,000 ppm of the basic malodor deodorant.
6). A toiletry product or a household product containing 0.01% to 50% by mass of the deodorant fragrance composition.
7). A method of deodorizing a basic malodor, which comprises spraying the basic deodorant with a concentration of 1 ppt to 5000 ppm.
8). The deodorizing method as described above, wherein the basic malodor is ammonia odor, amine odor, fish odor, garbage odor, manure odor or tobacco odor.
本発明の3−メルカプト−2−アルカノン化合物を使用することにより、アミン臭等の塩基性悪臭に対し化学的消臭効果を示し、かつ、塩基性悪臭と調和した優れた芳香性を有するマスキング効果を示す消臭製品を提供することができる。 By using the 3-mercapto-2-alkanone compound of the present invention, it exhibits a chemical deodorizing effect on basic malodors such as amine odor, and has an excellent fragrance in harmony with the basic malodor. The deodorant product which shows can be provided.
本発明で用いられる3−メルカプト−2−アルカノン化合物は、3位にアルキル置換基を有する3−メルカプト−2−プロパノン誘導体であって、アルキル置換基が炭素数1〜9の直鎖状又は分岐鎖状のアルキル基であれば特に限定されることはないが、好ましくは3−メルカプト−2−ブタノン、3−メルカプト−2−ペンタノン、3−メルカプト−2−ヘキサノン、3−メルカプト−2−ヘプタノン、3−メルカプト−2−オクタノン、3−メルカプト−2−ノナノン、3−メルカプト−2−デカノン、3−メルカプト−2−ウンデカノン、3−メルカプト−2−ドデカノン、3−メルカプト−4−メチル−2−ペンタノン、3−メルカプト−4−メチル−2−ヘキサノン、3−メルカプト−5−メチル−2−ヘキサノン、3−メルカプト−6−メチル−2−ヘプタノンが用いられ、より好ましくは3−メルカプト−2−ブタノン、3−メルカプト−2−ペンタノン、3−メルカプト−2−ヘキサノン、3−メルカプト−2−ヘプタノン、3−メルカプト−2−オクタノン、3−メルカプト−2−ノナノン、3−メルカプト−4−メチル−2−ペンタノン、3−メルカプト−4−メチル−2−ヘキサノン、3−メルカプト−5−メチル−2−ヘキサノン、3−メルカプト−6−メチル−2−ヘプタノンが用いられ、最も好ましくは3−メルカプト−2−ブタノン、3−メルカプト−2−ペンタノン、3−メルカプト−4−メチル−2−ペンタノン、3−メルカプト−4−メチル−2−ヘキサノン、3−メルカプト−6−メチル−2−ヘプタノンが用いられる。 The 3-mercapto-2-alkanone compound used in the present invention is a 3-mercapto-2-propanone derivative having an alkyl substituent at the 3-position, wherein the alkyl substituent is a linear or branched group having 1 to 9 carbon atoms. Although it is not particularly limited as long as it is a chain alkyl group, it is preferably 3-mercapto-2-butanone, 3-mercapto-2-pentanone, 3-mercapto-2-hexanone, 3-mercapto-2-heptanone. 3-mercapto-2-octanone, 3-mercapto-2-nonanone, 3-mercapto-2-decanone, 3-mercapto-2-undecanone, 3-mercapto-2-dodecanone, 3-mercapto-4-methyl-2 -Pentanone, 3-mercapto-4-methyl-2-hexanone, 3-mercapto-5-methyl-2-hexanone, 3-mercap -6-methyl-2-heptanone is used, more preferably 3-mercapto-2-butanone, 3-mercapto-2-pentanone, 3-mercapto-2-hexanone, 3-mercapto-2-heptanone, 3-mercapto -2-octanone, 3-mercapto-2-nonanone, 3-mercapto-4-methyl-2-pentanone, 3-mercapto-4-methyl-2-hexanone, 3-mercapto-5-methyl-2-hexanone, 3 -Mercapto-6-methyl-2-heptanone is used, most preferably 3-mercapto-2-butanone, 3-mercapto-2-pentanone, 3-mercapto-4-methyl-2-pentanone, 3-mercapto-4 -Methyl-2-hexanone, 3-mercapto-6-methyl-2-heptanone are used.
本発明の3−メルカプト−2−アルカノン化合物は、試薬として入手可能なものもあるが、必要に応じて合成することにより入手できる。合成して入手する場合の概略方法を以下に示した。 The 3-mercapto-2-alkanone compound of the present invention is available as a reagent, but can be obtained by synthesis as necessary. The outline method in the case of obtaining by synthesis is shown below.
3−メルカプト−2−アルカノン化合物は、下記の反応式に示すように、2−アルカノン化合物からクロロ化、次いで水硫化ナトリウム(硫化水素ナトリウム;NaSH)の処理により得る。なお、クロロ化反応で副生する1−クロロ−2−アルカノン化合物を分離して水硫化ナトリウムによる処理を行ってもよいが、分離せずに水硫化ナトリウムによる処理を行い、得られた反応混合物から目的物の3−メルカプト−2−アルカノン化合物を精製してもよい。さらに不斉合成や光学分割の手法を用いることによって光学活性体を入手することも可能である。
本発明でいう塩基性悪臭とは、アンモニアによるアンモニア臭、メチルアミン、エチルアミン、トリメチルアミン、トリエチルアミン等のアルキルアミン類によるアミン臭、ピリジン、エチルピリジン、ビニルピリジン等のピリジン類によるピリジン臭、ピラジン等によるピラジン臭、スカトール、インドール等による糞便臭をいい、動物、植物の腐敗物、排泄物にしばしば含まれ複合悪臭のキーとなる悪臭である。具体的には、タバコ臭、魚臭、生ゴミ臭、雑巾のニオイ、布巾のニオイ、排水口のニオイ、糞尿臭等が挙げられる。中でもトリメチルアミンは特に閾値が低く、最も重要な消臭対象である。また、ピリジン類、ピラジン類も燃焼に伴う複合悪臭のキー成分であり、これらに基づく悪臭としては、具体的にはタバコ臭、焼肉のニオイ、調理時のニオイなどが挙げられる。 The basic malodor referred to in the present invention includes ammonia odor due to ammonia, amine odor due to alkylamines such as methylamine, ethylamine, trimethylamine, and triethylamine, pyridine odor due to pyridines such as pyridine, ethylpyridine, and vinylpyridine, pyrazine, etc. It refers to fecal odor due to pyrazine odor, skatole, indole, etc., and is a odor that is often contained in animal and plant septics and excreta and is a key to complex odor. Specifically, tobacco odor, fish odor, garbage odor, rag odor, cloth odor, drainage odor, manure odor and the like can be mentioned. Among them, trimethylamine has a particularly low threshold value and is the most important deodorizing object. Pyridines and pyrazines are also key components of complex malodor accompanying combustion. Specific examples of malodor based on these include tobacco odor, odor of grilled meat, and odor during cooking.
本発明の塩基性悪臭用消臭剤は、トイレタリー製品又はハウスホールド製品に添加することでより好適に用いることができる。その場合、当該製品中の塩基性悪臭用消臭剤の含有量は、通常は1ppt〜5000ppmの範囲で用いられ、好ましくは10ppt〜1000ppmの範囲で用いられ、より好ましくは50ppt〜500ppmの範囲で用いられる。添加量が1ppt未満であるときは、本発明の塩基性悪臭消臭効果が十分でない場合があり、添加量が5000ppmを超えた場合は、コスト的に実際的でなくなることがある。 The basic malodor deodorant of the present invention can be more suitably used by adding it to toiletry products or household products. In that case, the content of the basic malodor deodorant in the product is usually used in the range of 1 ppt to 5000 ppm, preferably in the range of 10 ppt to 1000 ppm, more preferably in the range of 50 ppt to 500 ppm. Used. When the addition amount is less than 1 ppt, the basic malodor deodorizing effect of the present invention may not be sufficient, and when the addition amount exceeds 5000 ppm, the cost may not be practical.
本発明においては、上記3−メルカプト−2−アルカノン化合物からなる塩基性悪臭用消臭剤に対して、通常の香料を加えて消臭用香料組成物として用いることがさらに好ましい。そのために用いられる香料としては、例えば、トップノートに用いられる香料、ミドルノートに用いられる香料、ベースノートに用いられる香料などが挙げられる。本発明でいうトップノートとは、揮発性の高い調合素材で構成され、香りの嗅ぎ口の部分で全体の香りの特徴を与える。香りの質は、シトラスやグリーン、フルーティーが主な構成要素となる。本発明でいうミドルノートとは、揮発性の中程度の調合素材で構成され、香りの中心部となる。香りの質はフローラルやアルデヒド、スパイスが主な構成要素となる。本発明でいうベースノートとは、揮発性の低い香料素材で構成され、後半の香りで、香りの質はウッディやムスク、アニマル、バルサムが主な構成要素となる。具体的には、例えば下記の香料を挙げることができる In the present invention, it is more preferable to add a normal fragrance to the basic malodor deodorant comprising the 3-mercapto-2-alkanone compound and use it as a deodorant fragrance composition. As a fragrance | flavor used for that purpose, the fragrance | flavor used for a top note, the fragrance | flavor used for a middle note, the fragrance | flavor used for a base note, etc. are mentioned, for example. The top note referred to in the present invention is composed of a highly volatile compound material, and gives the characteristics of the entire scent at the scent of the scent. The main components of the scent are citrus, green and fruity. The middle note referred to in the present invention is composed of a volatile medium blending material and serves as the center of the scent. The main components of the scent are floral, aldehyde, and spices. The base note referred to in the present invention is composed of a fragrance material with low volatility, and is the latter half of the scent. The main components of the scent quality are woody, musk, animal, and balsam. Specifically, for example, the following fragrances can be mentioned.
トップノート成分の香料としては、リモネン、p−サイメン、α−ピネン、β−ピネン、テルピノーレン、オシメン、シス−3−ヘキセン−1−オール、トランス−2−ヘキセノール、トランス−3−ヘキセノール、2−エチルヘキサノール、1−ペンテン−3−オール、1−オクテン−3−オール、2,6−ジメチルヘプタン−2−オール、ミルセノール、ジヒドロミルセノール、l−メントール、p−クレジルメチルエーテル、ヘキサナール、トランス−2−ヘキセナール、オクタナール、ノナナール、シネンサール、オクタナールジメチルアセタール、メチルヘプテノン、エチルイソアミルケトン、1,4−シネオール、1,8−シネオール、リモネンオキサイド、ギ酸エチル、酢酸エチル、酢酸ブチル、酢酸イソアミル、酢酸シス−3−ヘキセニル、酢酸トランス−2−ヘキセニル、酢酸ヘキシル、酢酸ミルセニル、酢酸プレニル、酢酸アミル、酢酸1−オクテン−3−イル、プロピオン酸エチル、プロピオン酸シス−3−ヘキセニル、酪酸メチル、酪酸エチル、酪酸プロピル、酪酸イソアミル、酪酸アミル、酪酸アリル、イソ酪酸エチル、イソ酪酸プロピル、2−メチル酪酸エチル、アセト酢酸エチル、吉草酸エチル、イソ吉草酸メチル、イソ吉草酸プロピル、イソ吉草酸イソプロピル、イソ吉草酸シス−3−ヘキセニル、カプロン酸エチル、カプロン酸プロピル、カプロン酸アリル、ヘプタン酸エチル、オクタン酸エチル、安息香酸メチルおよび8−メルカプトメントンからなる群から選ばれる1種又は2種以上の香料が例示される。 As a fragrance of the top note component, limonene, p-cymene, α-pinene, β-pinene, terpinolene, osimene, cis-3-hexen-1-ol, trans-2-hexenol, trans-3-hexenol, 2- Ethylhexanol, 1-penten-3-ol, 1-octen-3-ol, 2,6-dimethylheptan-2-ol, myrcenol, dihydromyrcenol, l-menthol, p-cresyl methyl ether, hexanal, Trans-2-hexenal, octanal, nonanal, sinensar, octanal dimethyl acetal, methyl heptenone, ethyl isoamyl ketone, 1,4-cineole, 1,8-cineol, limonene oxide, ethyl formate, ethyl acetate, butyl acetate, isoamyl acetate, Cis-3-acetate Xenyl, trans-2-hexenyl acetate, hexyl acetate, mircenyl acetate, prenyl acetate, amyl acetate, 1-octen-3-yl acetate, ethyl propionate, cis-3-hexenyl propionate, methyl butyrate, ethyl butyrate, propyl butyrate , Isoamyl butyrate, amyl butyrate, allyl butyrate, ethyl isobutyrate, propyl isobutyrate, ethyl 2-methylbutyrate, ethyl acetoacetate, ethyl valerate, methyl isovalerate, propyl isovalerate, isopropyl isovalerate, isovaleric acid Illustrative are one or more fragrances selected from the group consisting of cis-3-hexenyl, ethyl caproate, propyl caproate, allyl caproate, ethyl heptanoate, ethyl octoate, methyl benzoate and 8-mercaptomentone. Is done.
ミドルノート成分の香料としては、3−フェニルプロピルアルコール、α−フェンコン、9−デセン−1−オール、ジメチルオクタノール、シトロネロール、ゲラニオール、テトラヒドロムゴール、リナロール、テトラヒドロリナロール、ネロール、エチルリナロール、ターピネオール、テトラヒドロゲラニオール、テトラヒドロミルセノール、α−フェンキルアルコール、メチルオイゲノール、オイゲノール、ジメチルベンジルカルビノール、ジメチルフェニルエチルカルビノール、ジフェニルオキサイド、デュピカール、ギ酸シトロネリル、ギ酸ゲラニル、ジャスマール、酢酸ベンジル、酢酸ジメチルベンジルカルビニル、酢酸リナリル、酢酸ネリル、酢酸o−tert−ブチルシクロヘキシル、酢酸p−tert−ブチルシクロヘキシル、シクロヘキシルオキシ酢酸アリル、酢酸フェンキル、酢酸シトロネリル、酢酸ゲラニル、酢酸テトラヒドロゲラニル、酢酸テルピニル、酢酸ジヒドロテルピニル、酢酸イソボルニル、酢酸l−メンチル、酢酸ノニル、酢酸トリシクロデセニル、酢酸p−クレジル、酢酸2−フェニルエチル、酢酸3−フェニルプロピル、酢酸スチラリル、酢酸ジメチルフェニルエチルカルビニル、酢酸1−エチニルシクロヘキシル、ヘプタン酸アリル、プロピオン酸イソブチル、プロピオン酸2−フェニルエチル、プロピオン酸シトロネリル、プロピオン酸ベンジル、プロピオン酸トリシクロデセニル、プロピオン酸イソボルニル、酪酸シス−3−ヘキセニル、酪酸シクロヘキシル、イソ酪酸3−フェニルプロピル、酪酸ジメチルベンジルカルビニル、プロピオン酸ゲラニル、プロピオン酸アリル、吉草酸シス−3−ヘキセニル、カプロン酸プロピル、シクロヘキシル酪酸アリル、アンスラニル酸シス−3−ヘキセニル、フェニル酢酸イソブチル、サリチル酸イソブチル、サリチル酸2−フェニルエチル、ヘプチンカルボン酸メチル、オクチンカルボン酸メチル、オクタン酸p−クレジル、ドデカン酸エチル、安息香酸プロピル、安息香酸イソブチル、安息香酸シス−3−ヘキセニル、アンゲリカ酸2−フェニルエチル、アリルアミルグリコレート、シクロガルバネート、γ−ブチロラクトン、α−フェニルエチルアルコール、β−フェニルエチルアルコール、アフェルマート、ベンジルアルコール、アニスアルコール、ゲラニアール、シトラール、ネラール、4−イソプロピルシクロヘキサノール、ホモフラネオール、デカナール、ウンデカナール、10−ウンデセナール、ドデカナール、シクロシトラール、イソシクロシトラール、テトラヒドロムゴール、チモール、10−ウンデセン−1−オール、アニスアルデヒド、フェニルアセトアルデヒド、ヒドラトロパアルデヒド、ヒドロキシシトロネラール、マイラックアルデヒド、ホモマイラックアルデヒド、ミュゲットアルデヒド、サフラナール、2−メチル−3−(p−メトキシフェニル)−プロパナール、オクタナールジエチルアセタール、フェニルアセトアルデヒドエチレングリコールアセタール、リリアール、コアボン、トリプラール、リメトール、フロラロゾン、2−ペンチルシクロペンタノン、l−カルボン、メントン、ゲラニルアセトン、p−メチルアセトフェノン、シトロネラール、シトロネリルオキシアセトアルデヒド、メチルフェニルグリシド酸エチル、ヒドロキシシトロネラールジメチルアセタール、フェニルアセトアルデヒドジメチルアセタール、メチルノニルアセトアルデヒドジメチルアセタール、アセトアルデヒド2−フェニル−2,4−ペンタンジオールアセタール、アセト酢酸エチルプロピレングリコールアセタール、ヒドラトロパアルデヒドジメチルアセタール、ヒドラトロパアルデヒドエチレングリコールアセタール、エストラゴール、グアヤコール、アネトール、p−クレゾール、ゲラニルニトリル、シトロネリルニトリル、インドール、ルボフィックス、チオゲラニオールおよびアセチルセドレンからなる群から選ばれる1種又は2種以上の香料が例示される。 As a fragrance for the middle note component, 3-phenylpropyl alcohol, α-fencon, 9-decen-1-ol, dimethyloctanol, citronellol, geraniol, tetrahydromegol, linalool, tetrahydrolinalol, nerol, ethyllinalol, terpineol, tetrahydro Geraniol, tetrahydromyrsenol, α-fenkyl alcohol, methyl eugenol, eugenol, dimethylbenzyl carbinol, dimethylphenylethyl carbinol, diphenyl oxide, dupical, citronellyl formate, geranyl formate, jasmar, benzyl acetate, dimethylbenzyl carvinyl acetate , Linalyl acetate, neryl acetate, o-tert-butylcyclohexyl acetate, p-tert-butylcyclohexyl acetate , Allyl cyclohexyloxyacetate, fenalkyl acetate, citronellyl acetate, geranyl acetate, tetrahydrogeranyl acetate, terpinyl acetate, dihydroterpinyl acetate, isobornyl acetate, l-menthyl acetate, nonyl acetate, tricyclodecenyl acetate, p-cresyl acetate 2-phenylethyl acetate, 3-phenylpropyl acetate, styrylyl acetate, dimethylphenylethylcarbyl acetate, 1-ethynylcyclohexyl acetate, allyl heptanoate, isobutyl propionate, 2-phenylethyl propionate, citronellyl propionate, propionic acid Benzyl, tricyclodecenyl propionate, isobornyl propionate, cis-3-hexenyl butyrate, cyclohexyl butyrate, 3-phenylpropyl isobutyrate, dimethylbenzyl carvinyl butyrate, pro Geranyl onate, allyl propionate, cis-3-hexenyl valerate, propyl caproate, allyl cyclohexylbutyrate, cis-3-hexenyl anthranilate, isobutyl phenylacetate, isobutyl salicylate, 2-phenylethyl salicylate, methyl heptine carboxylate , Methyl octynecarboxylate, p-cresyl octanoate, ethyl dodecanoate, propyl benzoate, isobutyl benzoate, cis-3-hexenyl benzoate, 2-phenylethyl angelate, allyl amyl glycolate, cyclogalvanate, γ- Butyrolactone, α-phenylethyl alcohol, β-phenylethyl alcohol, afermat, benzyl alcohol, anise alcohol, geranial, citral, neral, 4-isopropylcyclohexanol Homofuraneol, decanal, undecanal, 10-undecenal, dodecanal, cyclocitral, isocyclocitral, tetrahydromegol, thymol, 10-undecen-1-ol, anisaldehyde, phenylacetaldehyde, hydratropaldehyde, hydroxycitrone Lahr, mylacaldehyde, homomylacaldehyde, mugetaldehyde, safranal, 2-methyl-3- (p-methoxyphenyl) -propanal, octanal diethyl acetal, phenylacetaldehyde ethylene glycol acetal, lyial, coavone, tripral, Limethol, florarozone, 2-pentylcyclopentanone, l-carvone, menthone, geranylacetone, p-methylacetophenone, Roneral, citronellyloxyacetaldehyde, ethyl methylphenylglycidate, hydroxycitronellal dimethyl acetal, phenylacetaldehyde dimethyl acetal, methyl nonyl acetaldehyde dimethyl acetal, acetaldehyde 2-phenyl-2,4-pentanediol acetal, ethyl propylene glycol acetoacetate From the group consisting of acetal, hydratropaldehyde dimethyl acetal, hydratropaldehyde ethylene glycol acetal, estragole, guaiacol, anethole, p-cresol, geranyl nitrile, citronellil nitrile, indole, rubofix, thiogeraniol and acetyl cedrene The 1 type or 2 or more types of fragrance | flavor chosen is illustrated.
ベースノート成分の香料としては、ファルネセン、パチュリアルコール、p−tert−ブチルシクロヘキサノール、シンナミックアルコール、スクラレオール、ベチベロール、β−カリオフィレン、酢酸グアヤック、酢酸シンナミル、プロピオン酸シンナミル、酪酸2−フェニルエチル、酪酸ゲラニル、酪酸シトロネリル、フェニル酢酸、サリチル酸アミル、サリチル酸イソアミル、サリチル酸ベンジル、サリチル酸シス−3−ヘキセニル、サリチル酸ヘキシル、アントラニル酸メチル、N−メチルアントラニル酸メチル、安息香酸ベンジル、フタール酸ジエチル、イソ酪酸フェノキシエチル、イソ酪酸ゲラニル、イソ吉草酸ゲラニル、ケイ皮酸シンナミル、ケイ皮酸エチル、フェニル酢酸シトロネリル、フェニル酢酸p−クレジル、フェニル酢酸フェニルエチル、フェニル酢酸オイゲニル、フェニル酢酸イソオイゲニル、ミリスチン酸メチル、カプロン酸2−フェニルエチル、オクタン酸2−フェニルエチル、バレリアン酸2−フェニルエチル、イソロンギホラノン、メチルアトラレート、プロピリデンフタリド、テトラデカナール、α−アミルシンナミックアルデヒド、ヒドロシンナミックアルデヒド、サイクラメンアルデヒド、リラール、ラズベリーケトン、イソジャスモン、シスジャスモン、ダマスコン類、ダマセノン類、バニリン、エチルバニリン、ヘリオナール、ヘリオトロピン、α−n−ヘキシルシンナミックアルデヒド、オーランチオール、α−ダイナスコン、イオノン類、メチルイオノン類、イロン類、イソオイゲノール、メチルオイゲノール、メチルイソオイゲノール、ベンジルイソオイゲノール、β−メチルナフチルケトン、β−ナフチルメチルエーテル、β−ナフチルエチルエーテル、2−メチルウンデカナールジメチルアセタール、2−メチル−3−(p−メトキシフェニル)プロパノール、イソカンフィルシクロヘキサノール、ネロリドール、マルトール、エチルマルトール、合成サンダル、合成ムスク、γ−オクタラクトン、γ−ウンデカラクトン、γ−デカラクトン、γ−ノナラクトン、δ−ドデカラクトン、メチルジヒドロジャスモネート、イソ−E−スーパー、セドリルメチルエーテル、イソブチルキノリン、アンブロキサン、カリオフィレンオキシド、チンベロール、ローズオキシド、ローズフェノンおよびロンギホレンからなる群から選ばれる1種又は2種以上の香料が例示される。 As perfumes for base note components, farnesene, patchouli alcohol, p-tert-butylcyclohexanol, cinnamic alcohol, sclareol, vetiverol, β-caryophyllene, guaiac acetate, cinnamyl acetate, cinnamyl propionate, 2-phenylethyl butyrate, butyric acid Geranyl, citronellyl butyrate, phenylacetic acid, amyl salicylate, isoamyl salicylate, benzyl salicylate, cis-3-hexenyl salicylate, hexyl salicylate, methyl anthranilate, methyl N-methylanthranylate, benzyl benzoate, diethyl phthalate, phenoxyethyl isobutyrate Geranyl isobutyrate, geranyl isovalerate, cinnamyl cinnamate, ethyl cinnamate, citronellyl phenyl acetate, p-cresyl phenyl acetate, fe Phenylethyl acetate, eugenyl phenylacetate, isoeugenyl phenylacetate, methyl myristate, 2-phenylethyl caproate, 2-phenylethyl octoate, 2-phenylethyl valerate, isolongifolanone, methyl atrate, propylidene phthalate Lido, tetradecanal, α-amylcinnamic aldehyde, hydrocinnamic aldehyde, cyclamenaldehyde, lyral, raspberry ketone, isojasmon, cisjasmon, damascons, damasenones, vanillin, ethyl vanillin, helional, heliotropin, α- n-hexylcinnamic aldehyde, auranthiol, α-dynascone, ionones, methylionones, irons, isoeugenol, methyleugenol, methylisoeugen Nord, benzylisoeugenol, β-methylnaphthyl ketone, β-naphthylmethyl ether, β-naphthylethyl ether, 2-methylundecanal dimethyl acetal, 2-methyl-3- (p-methoxyphenyl) propanol, isocamphylcyclo Hexanol, nerolidol, maltol, ethyl maltol, synthetic sandals, synthetic musk, γ-octalactone, γ-undecalactone, γ-decalactone, γ-nonalactone, δ-dodecalactone, methyl dihydrojasmonate, iso-E- Examples thereof include one or more fragrances selected from the group consisting of super, sedrylmethyl ether, isobutyl quinoline, ambroxan, caryophyllene oxide, timberol, rose oxide, rosephenone and longifolene.
さらに加えて、天然香料として、レモン油、オレンジ油、ライム油、ベルガモット油、ユーカリ油、マンダリン油、ウインターグリーン油、ショウノウ油、ホウショウ油、オークモス油、オポポナックス油、コパイバ油、サンダル油、シダーウッド油、トルーバルサム油、ペルーバルサム油、ベンゾイン油、バニラ油、アビエス・ファ油、アーモンド油、カラムス油、カモミル油、カルダモン油、ガルバナム油、キャラウェー油、クミン油、コリアンダー油、ジュニパーベリー油、スペアミント油、セージ油、セロリー油、タイム油、タラゴン油、ナッツメグ油、バジル油、ヒソップ油、プチグレン油、ブチュ油、ペニーロイヤル油、ペパーミント油、メース油、ラベンダー油、ローズマリー油、ロベージ油、ローレル油、アミリス油、エレミ油、カッシャ油、グァヤック油、クローブ油、スチラックス油、ゼラニウム油、タンジェリン油、パチュリ油、ベチバー油、ラブダナム油、レモングラス油、アンゲリカ油、ヒノキ油、ヒバ油、シトロネラ油、アニスシード油、イランイラン油、クラリセージ油、シンナモン油、スターアニス油、カナンガ油およびブラックカーラント油からなる群から選ばれる1種又は2種以上の香料も使用可能である。 In addition, as natural flavors, lemon oil, orange oil, lime oil, bergamot oil, eucalyptus oil, mandarin oil, winter green oil, camphor oil, pepper oil, oak moss oil, opoponax oil, copaiba oil, sandal oil, cedarwood oil , Trout balsam oil, peru balsam oil, benzoin oil, vanilla oil, abies fa oil, almond oil, columnus oil, camomil oil, cardamom oil, galvanum oil, caraway oil, cumin oil, coriander oil, juniper berry oil, spearmint Oil, sage oil, celery oil, thyme oil, tarragon oil, nutmeg oil, basil oil, hyssop oil, petitgren oil, butch oil, penny royal oil, peppermint oil, mace oil, lavender oil, rosemary oil, lobe oil, laurel Oil, Amiris oil, EL Oil, Cascia oil, Guayac oil, Clove oil, Stylax oil, Geranium oil, Tangerine oil, Patchouli oil, Vetiver oil, Labdanum oil, Lemongrass oil, Angelica oil, Cypress oil, Hiba oil, Citronella oil, Anise seed oil, Iran One or more fragrances selected from the group consisting of Iran oil, clary sage oil, cinnamon oil, star anise oil, cananga oil and black currant oil can also be used.
本発明の塩基性悪臭用消臭剤は、消臭用香料組成物に対して、通常は0.01ppm〜10000ppm、好ましくは0.1ppm〜1000ppm、最も好ましくは1ppm〜100ppm添加して用いられる。添加量が0.01ppm未満であるときは、本発明の塩基性悪臭消臭効果が十分でない場合があり、添加量が10000ppmを超えた場合は、コスト的に実際的でなくなることがある。 The basic malodor deodorant of the present invention is used usually by adding 0.01 ppm to 10000 ppm, preferably 0.1 ppm to 1000 ppm, and most preferably 1 ppm to 100 ppm to the deodorant fragrance composition. When the addition amount is less than 0.01 ppm, the basic malodor deodorizing effect of the present invention may not be sufficient, and when the addition amount exceeds 10,000 ppm, it may become impractical in terms of cost.
本発明の消臭用香料組成物は、トイレタリー製品又はハウスホールド製品に対して、通常は0.01質量%〜50質量%、好ましくは0.03質量%〜30質量%、最も好ましくは0.05質量%〜10質量%添加して用いられる。添加量が0.01質量%未満であるときは、本発明の塩基性悪臭消臭効果が十分でない場合があり、添加量が50質量%を超えた場合は、コスト的に実際的でなくなることがある。 The deodorant fragrance composition of the present invention is usually 0.01% by mass to 50% by mass, preferably 0.03% by mass to 30% by mass, and most preferably 0.00% by mass with respect to toiletry products or household products. 05 mass% to 10 mass% is added and used. When the addition amount is less than 0.01% by mass, the basic malodor deodorizing effect of the present invention may not be sufficient, and when the addition amount exceeds 50% by mass, it is not practical in cost. There is.
本発明の消臭用香料組成物は、水、アルコ−ル類、グリコ−ル類、炭化水素類等の液体担体、LPG等のガス担体、並びにケイ酸カルシウムおよびシリカゲル等の固体担体から成る公知の適当な担体と組み合わせて、液状、スプレー状、ビーズ状、ペースト状、ゲル状、固形状等の任意の形態でトイレタリー製品又はハウスホールド製品として利用することができる。 The deodorant fragrance composition of the present invention comprises a liquid carrier such as water, alcohols, glycols and hydrocarbons, a gas carrier such as LPG, and a solid carrier such as calcium silicate and silica gel. In combination with a suitable carrier, it can be used as a toiletry product or a household product in any form such as liquid, spray, bead, paste, gel, and solid.
本発明でいうトイレタリー製品とは、香水などのフレグランス、ウォッシングクリーム、バニシングクリーム、洗顔クリーム、クレンジングクリーム、コールドクリーム、乳液、化粧水、パック剤、メイク落とし、アフターシェービングローション、ファンデーション、口紅、リップクリーム、頬紅、アイライナー、マスカラ、アイシャドー、眉墨、アイブロー、マニキュア、マニキュアリムーバー、粉おしろい、固形おしろい、タルカムパウダー、ヘアトニック、ヘアクリーム、ヘアトリートメントなどの養毛剤、ヘアオイル、ポマード、チック、ヘアリキッド、セットローション、ヘアジェル、ヘアスプレー、ヘアフォーム、ヘアワックスなどの整髪剤、ヘアカラー、ヘアマニキュア、ブリーチ、白髪染めなどの染毛剤、パーマ、カーリング剤などの毛髪変形剤、日焼け止め、制汗デオドラント剤、固形石鹸、身体用ボディーソープ、シャンプー、リンス、コンディショナー、トリートメント、ヘアパック、浴用剤などが挙げられる。 Toiletries in the present invention include perfume and other fragrances, washing creams, vanishing creams, facial creams, cleansing creams, cold creams, emulsions, lotions, pack removers, makeup removers, after shaving lotions, foundations, lipsticks, lip balms, Blusher, eyeliner, mascara, eye shadow, eyebrow, eyebrow, nail polish, nail polish remover, powdered, solid, talcum powder, hair tonic, hair cream, hair treatments, hair oil, pomade, tic, hair liquid, set Hair conditioner such as lotion, hair gel, hair spray, hair foam, hair wax, hair color, hair manicure, bleach, hair dye such as hair dye, perm, curly Hair deformation agent such as grayed agent, sunscreen, antiperspirant deodorant, bar soap, body for body soap, shampoo, rinse, conditioner, treatment, hair pack, and the like bath agent.
本発明でいうハウスホールド製品とは、衣料用液体洗剤、衣料用粉末洗剤、衣料用固形石鹸、衣料用柔軟仕上剤、衣料用漂白剤、台所用洗剤、食器乾燥機用洗剤、トイレクリーナー、バスクリーナー、ガラスクリーナー、カビ取り剤、排水管用洗浄剤、水性液体芳香剤、油性液体芳香剤、水性ゲル状芳香剤、油性ゲル状芳香剤、芳香スプレー、消臭スプレー、芳香エアゾール、消臭エアゾール、含浸芳香剤、線香、燻煙剤、蚊取り線香、殺虫剤、防虫剤などが挙げられる。 Household products as used in the present invention are liquid detergents for clothes, powder detergents for clothes, soaps for clothes, softeners for clothes, bleaching agents for clothes, detergents for kitchens, detergents for dish dryers, toilet cleaners, bathrooms Cleaner, glass cleaner, mold remover, drain pipe cleaner, aqueous liquid fragrance, oil liquid fragrance, aqueous gel fragrance, oil gel fragrance, fragrance spray, deodorant spray, fragrance aerosol, deodorant aerosol, Examples include impregnating fragrances, incense sticks, smoke smoke agents, mosquito-repellent incense sticks, insecticides, and insect repellents.
本発明の塩基性悪臭消臭剤は、ポンプ式スプレーやエアゾールなどの形態で悪臭源に直接噴霧して用いることもできる。その場合、悪臭源に対して1ppt〜5000ppm濃度の状態で噴霧することが効果的である。噴霧濃度が1ppt未満の場合は、悪臭消臭効果が十分でないことがあり、噴霧濃度が5000ppmを超えた場合は、コスト的に実際的でないことがある。 The basic malodor deodorant of the present invention can be directly sprayed on a malodor source in the form of a pump spray or aerosol. In that case, it is effective to spray in the state of 1ppt-5000ppm density | concentration with respect to a malodor source. When the spray concentration is less than 1 ppt, the malodor deodorizing effect may not be sufficient, and when the spray concentration exceeds 5000 ppm, it may not be practical in cost.
本発明の塩基性悪臭消臭剤は前記のごとくトリメチルアミンによる悪臭に有効なものであるが、実用化に際してはアンモニア臭、アミン臭、魚臭、生ゴミ臭、糞尿臭又はタバコ臭等の消臭に特に適している。 As described above, the basic malodor deodorant of the present invention is effective for malodor due to trimethylamine, but in practical use, it deodorizes ammonia odor, amine odor, fish odor, garbage odor, manure odor, tobacco odor, etc. Especially suitable for.
以下に実施例を示し、本発明をさらに具体的に説明するが、本発明はこれらの実施例に限定されるものではない。 Examples Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples.
[実施例1〜8、比較例1〜3]
1Lデシケーターの底部に直径5cmのシャーレを設置した。臭気源として300ng/μLトリメチルアミン水溶液を3mL入れた。その上から各種3−メルカプト−2−アルカノン化合物並びに、比較例として6−メチル−5−ヘプテン−2−オンおよび4−メルカプト−4−メチル−2−ペンタノンを、それぞれ3mL加え、デシケーターを密封した。密封後、5分後、30分後、60分後のデシケーター内部のトリメチルアミンの濃度を、ガステック社製検知管(アミン類 180、180L)を使い測定した。なお試験検体を入れずに測定した値をコントロールとし、試験検体によるトリメチルアミン除去率を下記式にて算出した。
除去率(%)=(コントロール値−試験検体値)/コントロール値×100
結果を表1に示した。
[Examples 1-8, Comparative Examples 1-3]
A petri dish having a diameter of 5 cm was placed at the bottom of the 1 L desiccator. As an odor source, 3 mL of 300 ng / μL trimethylamine aqueous solution was added. 3 mL each of various 3-mercapto-2-alkanone compounds and 6-methyl-5-hepten-2-one and 4-mercapto-4-methyl-2-pentanone as comparative examples were added thereto, and the desiccator was sealed. . After sealing, the concentration of trimethylamine inside the desiccator after 5 minutes, 30 minutes and 60 minutes was measured using a detector tube (amines 180, 180 L) manufactured by Gastec. In addition, the value measured without putting the test sample was used as a control, and the trimethylamine removal rate by the test sample was calculated by the following formula.
Removal rate (%) = (control value−test sample value) / control value × 100
The results are shown in Table 1.
表1が示す通り、3−メルカプト−2−ブタノン(実施例1)、3−メルカプト−2−ペンタノン(実施例2)は、投入直後のみならず30分後、60分後においても非常に高いトリメチルアミンの除去効果が確認された。これらを1%又は0.1%に希釈して用いても、投入直後から60分後において非常に高いトリメチルアミンの除去効果を維持していた(実施例3、4、8)。同様にその効果は、3−メルカプト−4−メチル−2−ヘキサノン、3−メルカプト−4−メチル−2−ペンタノン、3−メルカプト−6−メチル−2−ヘプタノンでも確認することができた(実施例5、6、7)。
一方、特許文献2記載の6−メチル−5−ヘプテン−2−オンは、投入直後は高いトリメチルアミンの除去効果は示すものの、その効果は持続しないことが確認された(比較例1)。また、0.1%に希釈した場合、実施例8のような持続的な除去効果は確認されなかった(比較例2)。さらに、構造の異なる4−メルカプト−4−メチル−2−ペンタノンでは高い除去効果が認められなかった(比較例3)。
非常に高いトリメチルアミンの除去効果が長く持続するのは、3−メルカプト−2−アルカノン化合物にのみ特異的に認められる現象であることが判明した。
As Table 1 shows, 3-mercapto-2-butanone (Example 1) and 3-mercapto-2-pentanone (Example 2) are very high not only immediately after addition but also after 30 minutes and 60 minutes. The removal effect of trimethylamine was confirmed. Even when these were diluted to 1% or 0.1%, a very high trimethylamine removal effect was maintained 60 minutes after the addition (Examples 3, 4, and 8). Similarly, the effect could be confirmed with 3-mercapto-4-methyl-2-hexanone, 3-mercapto-4-methyl-2-pentanone, and 3-mercapto-6-methyl-2-heptanone. Examples 5, 6, 7).
On the other hand, although 6-methyl-5-hepten-2-one described in Patent Document 2 shows a high trimethylamine removal effect immediately after its introduction, it was confirmed that the effect was not sustained (Comparative Example 1). Further, when diluted to 0.1%, the continuous removal effect as in Example 8 was not confirmed (Comparative Example 2). Furthermore, a high removal effect was not recognized with 4-mercapto-4-methyl-2-pentanone having a different structure (Comparative Example 3).
It has been found that a very high removal effect of trimethylamine lasts for a long time, a phenomenon that is specifically observed only in 3-mercapto-2-alkanone compounds.
[実施例9〜16、比較例4、5]
表2の処方に従い、実施例9〜16、比較例4、5のオレンジ様消臭香料組成物を調製した。
According to the prescription of Table 2, the orange-like deodorant fragrance | flavor composition of Examples 9-16 and Comparative Examples 4 and 5 was prepared.
[実施例17−24、比較例6、7]
オレンジ様消臭香料組成物(実施例9〜16、比較例4、5)10質量%、イソパラフィン溶剤(出光興産株式会社製)90質量%を常法にて混合し、実施例17〜24、比較例6、7の油性芳香消臭剤を調製した。
[Examples 17-24, Comparative Examples 6 and 7]
10% by mass of orange-like deodorant fragrance composition (Examples 9 to 16, Comparative Examples 4 and 5) and 90% by mass of an isoparaffin solvent (manufactured by Idemitsu Kosan Co., Ltd.) were mixed in a conventional manner, and Examples 17 to 24, The oily aromatic deodorants of Comparative Examples 6 and 7 were prepared.
[試験例1]
8Lのガラス容器に直径3cmのミニシャーレを設置した。ミニシャーレに悪臭源として300ng/μLトリメチルアミン水溶液を1mL入れ、さらに実施例17〜24、比較例6、7の油性芳香消臭剤を、それぞれ1mL入れ、ガラス容器に蓋をして密閉した。
60分静置後、ガラス容器の蓋をあけ、下記評価基準に基づき官能評価を行った。評価は専門パネラー5名で行った。5名のスコア平均値を表3に示す。
+2:快
+1:やや快
0:快でも不快でもない
−1:やや不快
−2:不快
[Test Example 1]
A mini petri dish having a diameter of 3 cm was placed in an 8 L glass container. 1 mL of 300 ng / μL trimethylamine aqueous solution was added to the mini petri dish as a bad odor source, and 1 mL of each of the oily aromatic deodorants of Examples 17 to 24 and Comparative Examples 6 and 7 was added, and the glass container was covered and sealed.
After leaving still for 60 minutes, the lid of the glass container was opened and sensory evaluation was performed based on the following evaluation criteria. The evaluation was conducted by 5 expert panelists. Table 3 shows the average scores of the five people.
+2: pleasant +1: somewhat pleasant 0: neither pleasant nor uncomfortable -1: somewhat uncomfortable -2: unpleasant
3−メルカプト−2−アルカノン化合物を添加した実施例17〜24の油性芳香消臭剤は、比較例6,7の油性芳香消臭剤に比べ、トリメチルアミンの不快な臭気が緩和された。 Compared with the oily aromatic deodorant of Comparative Examples 6 and 7, the unpleasant odor of trimethylamine was alleviated in the oily aromatic deodorant of Examples 17 to 24 to which the 3-mercapto-2-alkanone compound was added.
[実施例25〜28、比較例8、9]
表4の処方に従い、実施例25〜28、比較例8、9のグレープフルーツ様消臭香料組成物を調製した。
[Examples 25 to 28, Comparative Examples 8 and 9]
According to the formulation of Table 4, the grapefruit-like deodorant fragrance compositions of Examples 25 to 28 and Comparative Examples 8 and 9 were prepared.
[実施例29〜32、比較例9、10]
グレープフルーツ様消臭香料組成物(実施例25〜28、比較例8、9)10質量%、イソパラフィン溶剤(出光興産株式会社製)90質量%を常法にて混合し、実施例29〜32、比較例9、10の油性芳香消臭剤を調製した。
[Examples 29 to 32, Comparative Examples 9 and 10]
Grapefruit-like deodorant fragrance composition (Examples 25 to 28, Comparative Examples 8 and 9) 10% by mass, isoparaffin solvent (manufactured by Idemitsu Kosan Co., Ltd.) 90% by mass were mixed in a conventional manner, Examples 29 to 32, The oily aromatic deodorants of Comparative Examples 9 and 10 were prepared.
[試験例2]
8Lのガラス容器に直径3cmのミニシャーレを設置した。ミニシャーレに悪臭源としてタバコ副流煙の水溶液を1mL入れ、さらに実施例29〜32、比較例9、10の油性芳香消臭剤を、それぞれ1mL入れ、ガラス容器に蓋をして密閉した。
60分静置後、ガラス容器の蓋をあけ、下記評価基準に基づき官能評価を行った。評価は専門パネラー5名で行った。5名のスコア平均値を表5に示す。
+2:快
+1:やや快
0:快でも不快でもない
−1:やや不快
−2:不快
[Test Example 2]
A mini petri dish having a diameter of 3 cm was placed in an 8 L glass container. Into the mini petri dish, 1 mL of an aqueous solution of sidestream smoke as a bad odor source was added, and 1 mL of each of the oily aromatic deodorants of Examples 29 to 32 and Comparative Examples 9 and 10 was added, and the glass container was covered and sealed.
After leaving still for 60 minutes, the lid of the glass container was opened and sensory evaluation was performed based on the following evaluation criteria. The evaluation was conducted by 5 expert panelists. Table 5 shows the average scores of the five people.
+2: pleasant +1: somewhat pleasant 0: neither pleasant nor uncomfortable -1: somewhat uncomfortable -2: unpleasant
3−メルカプト−2−アルカノン化合物を添加した実施例29〜32の油性芳香消臭剤は、比較例9、10の油性芳香消臭剤に比べ、タバコの不快な臭気が緩和された。 The oily aromatic deodorant of Examples 29 to 32 to which the 3-mercapto-2-alkanone compound was added alleviated the unpleasant odor of tobacco as compared with the oily aromatic deodorant of Comparative Examples 9 and 10.
[実施例33]
以下の処方でシャンプーを調製した。数量は全て質量%である(以下、同じ)。
POE(2)ラウリルエーテル硫酸Na(日光ケミカルズ社製) 9.0
ラウリル硫酸ナトリウム(日光ケミカルズ社製) 4.0
ヤシ油脂肪酸アミドプロピルベタイン(花王社製) 3.0
高重合メチルポリシロキサン(東レ社製) 2.0
ヤシ油脂肪酸モノエタノールアミド(花王社製) 1.0
プロピレングリコール(ADEKA社製) 2.0
ジステアリン酸エチレングリコール(花王社製) 2.0
メチルパラベン(上野製薬社製) 0.1
実施例9のオレンジ様消臭香料組成物 1.0
精製水 残部
合計 100.0
[Example 33]
A shampoo was prepared according to the following formulation. All quantities are mass% (hereinafter the same).
POE (2) lauryl ether sulfate Na (manufactured by Nikko Chemicals) 9.0
Sodium lauryl sulfate (manufactured by Nikko Chemicals) 4.0
Coconut oil fatty acid amidopropyl betaine (manufactured by Kao Corporation) 3.0
Highly polymerized methylpolysiloxane (Toray Industries, Inc.) 2.0
Coconut oil fatty acid monoethanolamide (Kao Corporation) 1.0
Propylene glycol (made by ADEKA) 2.0
Ethylene glycol distearate (Kao Corporation) 2.0
Methylparaben (manufactured by Ueno Pharmaceutical Co., Ltd.) 0.1
Orange-like deodorant fragrance composition of Example 9 1.0
Purified water balance
Total 100.0
[実施例34]
以下の処方でヘアリンスを調製した。
塩化ステアリルトリメチルアンモニウム(花王社製) 2.0
ステアリルアルコール(花王社製) 1.0
セチルアルコール(花王社製) 2.0
高重合メチルポリシロキサン(東レ社製) 2.0
メチルポリシロキサン(東レ社製) 1.0
流動パラフィン(カネダ社製) 1.0
グリセリン(阪本薬品工業社製) 6.0
メチルパラベン(上野製薬社製) 0.1
実施例13のオレンジ様消臭香料組成物 2.0
精製水 残部
合計 100.0
[Example 34]
A hair rinse was prepared according to the following formulation.
Stearyltrimethylammonium chloride (manufactured by Kao Corporation) 2.0
Stearyl alcohol (manufactured by Kao) 1.0
Cetyl alcohol (Kao Corporation) 2.0
Highly polymerized methylpolysiloxane (Toray Industries, Inc.) 2.0
Methyl polysiloxane (Toray Industries, Inc.) 1.0
Liquid paraffin (Kaneda) 1.0
Glycerin (Sakamoto Pharmaceutical Co., Ltd.) 6.0
Methylparaben (manufactured by Ueno Pharmaceutical Co., Ltd.) 0.1
Orange-like deodorant fragrance composition of Example 13 2.0
Purified water balance
Total 100.0
[実施例35]
以下の処方でボディソープを調製した。
POE(2)ラウリルエーテル硫酸Na(日光ケミカルズ社製) 15.0
ラウリル硫酸トリエタノールアミン(日光ケミカルズ社製) 5.0
ヤシ油脂肪酸アミドプロピルベタイン(花王社製) 5.0
ジステアリン酸エチレングリコール(花王社製) 2.0
モノパルミチン酸グリセリン(花王社製) 1.0
吸着精製ラノリン(花王社製) 2.0
グリセリン(阪本薬品工業社製) 2.0
プロピレングリコール(ADEKA社製) 3.0
メチルパラベン(上野製薬社製) 0.1
実施例14のオレンジ様消臭香料組成物 2.0
精製水 残部
合計 100.0
[Example 35]
A body soap was prepared according to the following formulation.
POE (2) lauryl ether sulfate Na (manufactured by Nikko Chemicals) 15.0
Lauryl sulfate triethanolamine (manufactured by Nikko Chemicals) 5.0
Coconut oil fatty acid amidopropyl betaine (manufactured by Kao Corporation) 5.0
Ethylene glycol distearate (Kao Corporation) 2.0
Glycerol monopalmitate (Kao Corporation) 1.0
Adsorption refined lanolin (manufactured by Kao) 2.0
Glycerin (Sakamoto Pharmaceutical Co., Ltd.) 2.0
Propylene glycol (made by ADEKA) 3.0
Methylparaben (manufactured by Ueno Pharmaceutical Co., Ltd.) 0.1
Orange-like deodorant fragrance composition of Example 14 2.0
Purified water balance <10.0 Total 100.0
[実施例36]
以下の処方で油性液体芳香消臭剤を調製した。
実施例25のグレープフルーツ様消臭香料組成物 10.0
3−メトキシ−3−メチル−1−ブタノール(クラレ社製) 90.0
合計 100.0
[Example 36]
An oily liquid fragrance deodorant was prepared according to the following formulation.
Grapefruit-like deodorant fragrance composition of Example 25 10.0
3-methoxy-3-methyl-1-butanol (manufactured by Kuraray Co., Ltd.) 90.0
Total 100.0
[実施例37]
以下の処方で芳香消臭スプレーを調製した。
メチルパラベン(上野製薬社製) 0.1
実施例26のグレープフルーツ様消臭香料組成物 1.0
POE硬化ひまし油(第一工業製薬社製) 4.5
エタノール(日本アルコール販売社製) 10.0
精製水 残部
合計 100.0
[Example 37]
An aroma deodorant spray was prepared according to the following formulation.
Methylparaben (manufactured by Ueno Pharmaceutical Co., Ltd.) 0.1
Grapefruit-like deodorant fragrance composition of Example 26 1.0
POE hydrogenated castor oil (Daiichi Kogyo Seiyaku Co., Ltd.) 4.5
Ethanol (manufactured by Nippon Alcohol Sales Company) 10.0
Purified water balance <10.0 Total 100.0
[実施例38]
以下の処方で芳香消臭エアゾールを調製した。
実施例10のオレンジ様消臭香料組成物 0.5
エタノール(日本アルコール販売社製) 29.5
LPG 70.0
合計 100.0
[Example 38]
An aroma deodorant aerosol was prepared according to the following formulation.
Orange-like deodorant fragrance composition of Example 10 0.5
Ethanol (manufactured by Japan Alcohol Sales Company)
LPG 70.0
Total 100.0
[実施例39]
以下の処方でオンタンク用液体洗浄剤を調製した。
実施例12のオレンジ様消臭香料組成物 10.0
プルロニック系界面活性剤(ADEKA社製) 40.0
ラウリルジメチルアミンオキシド(花王社製) 3.0
ラウリル硫酸ナトリウム(日光ケミカルズ社製) 5.0
エタノール(日本アルコール販売社製) 10.0
精製水 残部
合計 100.0
[Example 39]
An on-tank liquid detergent was prepared according to the following formulation.
Orange-like deodorant fragrance composition of Example 12 10.0
Pluronic surfactant (manufactured by ADEKA) 40.0
Lauryldimethylamine oxide (manufactured by Kao Corporation) 3.0
Sodium lauryl sulfate (manufactured by Nikko Chemicals) 5.0
Ethanol (manufactured by Nippon Alcohol Sales Company) 10.0
Purified water balance <10.0 Total 100.0
本発明の3−メルカプト−2−アルカノン化合物を使用することにより、アミン臭等の塩基性悪臭に対し化学的消臭効果を示し、かつ、塩基性悪臭と調和した優れた芳香性を有するマスキング効果を示す消臭製品を提供することができる。 By using the 3-mercapto-2-alkanone compound of the present invention, it exhibits a chemical deodorizing effect on basic malodors such as amine odor, and has an excellent fragrance in harmony with the basic malodor. The deodorant product which shows can be provided.
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JP2005107920A (en) * | 2003-09-30 | 2005-04-21 | Dainippon Printing Co Ltd | Manufacturing method and manufacturing device for sheet with ic tag |
JP2006020526A (en) * | 2004-07-06 | 2006-01-26 | Kiyomitsu Kawasaki | Coffee flavor composition, and food and drink containing the same |
JP5261185B2 (en) * | 2006-10-19 | 2013-08-14 | 小川香料株式会社 | 3-mercapto-2-alkanone and perfume composition containing said compound |
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JP2005107920A (en) * | 2003-09-30 | 2005-04-21 | Dainippon Printing Co Ltd | Manufacturing method and manufacturing device for sheet with ic tag |
JP2006020526A (en) * | 2004-07-06 | 2006-01-26 | Kiyomitsu Kawasaki | Coffee flavor composition, and food and drink containing the same |
JP5261185B2 (en) * | 2006-10-19 | 2013-08-14 | 小川香料株式会社 | 3-mercapto-2-alkanone and perfume composition containing said compound |
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JP2020196678A (en) * | 2019-05-31 | 2020-12-10 | 高砂香料工業株式会社 | Masking fragrance composition |
JP7299760B2 (en) | 2019-05-31 | 2023-06-28 | 高砂香料工業株式会社 | masking perfume composition |
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