JPH10263062A - Odor restraining product containing glycoside and deodorizing powder - Google Patents
Odor restraining product containing glycoside and deodorizing powderInfo
- Publication number
- JPH10263062A JPH10263062A JP9074256A JP7425697A JPH10263062A JP H10263062 A JPH10263062 A JP H10263062A JP 9074256 A JP9074256 A JP 9074256A JP 7425697 A JP7425697 A JP 7425697A JP H10263062 A JPH10263062 A JP H10263062A
- Authority
- JP
- Japan
- Prior art keywords
- flavor
- glycoside
- cyclodextrin
- fragrance
- suppressing
- 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.)
- Pending
Links
- 229930182470 glycoside Natural products 0.000 title claims abstract description 123
- 150000002338 glycosides Chemical class 0.000 title claims abstract description 116
- 230000000452 restraining effect Effects 0.000 title abstract 4
- 239000000843 powder Substances 0.000 title description 9
- 230000001877 deodorizing effect Effects 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 102
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 101
- 239000000203 mixture Substances 0.000 claims abstract description 83
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims abstract description 68
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 43
- 229960001047 methyl salicylate Drugs 0.000 claims abstract description 34
- 235000017803 cinnamon Nutrition 0.000 claims abstract description 16
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 claims abstract description 14
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims abstract description 13
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229940041616 menthol Drugs 0.000 claims abstract description 13
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims abstract description 13
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims abstract description 13
- 235000012141 vanillin Nutrition 0.000 claims abstract description 13
- -1 aromatic glycoside Chemical class 0.000 claims abstract description 9
- 239000005844 Thymol Substances 0.000 claims abstract description 7
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- 239000000796 flavoring agent Substances 0.000 claims description 135
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- 235000019634 flavors Nutrition 0.000 claims description 58
- 239000001116 FEMA 4028 Substances 0.000 claims description 55
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 55
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 55
- 229960004853 betadex Drugs 0.000 claims description 55
- 239000002304 perfume Substances 0.000 claims description 43
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 22
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 22
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 20
- 244000223760 Cinnamomum zeylanicum Species 0.000 claims description 14
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 12
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 11
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 11
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- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 claims description 10
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- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 10
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- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 8
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- RCSBILYQLVXLJG-UHFFFAOYSA-N 2-Propenyl hexanoate Chemical compound CCCCCC(=O)OCC=C RCSBILYQLVXLJG-UHFFFAOYSA-N 0.000 claims description 3
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- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 235000013355 food flavoring agent Nutrition 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
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- 230000032683 aging Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
- 150000008209 arabinosides Chemical class 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 229940115397 bornyl acetate Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000008195 galaktosides Chemical class 0.000 description 1
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- SFMJNHNUOVADRW-UHFFFAOYSA-N n-[5-[9-[4-(methanesulfonamido)phenyl]-2-oxobenzo[h][1,6]naphthyridin-1-yl]-2-methylphenyl]prop-2-enamide Chemical compound C1=C(NC(=O)C=C)C(C)=CC=C1N1C(=O)C=CC2=C1C1=CC(C=3C=CC(NS(C)(=O)=O)=CC=3)=CC=C1N=C2 SFMJNHNUOVADRW-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000008265 rhamnosides Chemical class 0.000 description 1
- 150000008223 ribosides Chemical class 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229920000247 superabsorbent polymer Polymers 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 description 1
- 201000004647 tinea pedis Diseases 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
- Housing For Livestock And Birds (AREA)
- Toilet Supplies (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
Abstract
Description
【０００１】[0001]
【発明が属する技術分野】本発明は、異臭抑制組成物に
関し、詳しくは人間あるいはペットの排泄物などに起因
する異臭を抑制するのに好適な異臭抑制組成物並びにこ
れを有する衛生用品及びペット用品に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an off-flavor suppressing composition, and more particularly to an off-flavor suppressing composition suitable for suppressing off-flavor caused by human or pet excrement, and sanitary articles and pet articles having the same. About.
【０００２】[0002]
【従来の技術】近年になって平均寿命が延びたことによ
って、現代社会は老齢社会へと歩み始めている。この様
な状況において、例えば、紙オムツのような衛生用品の
需要が延びている。この様な衛生用品は本来乳幼児用に
開発された商品のサイズを変えて老人などにそのまま適
用しているケースが少なくない。老人と乳幼児では、食
べ物の種類やその代謝のシステムが著しく異なるため、
異臭の発生などの問題が生じている。2. Description of the Related Art As life expectancy has increased in recent years, modern society has begun to move toward an aging society. Under such circumstances, for example, demand for sanitary articles such as disposable diapers has been increasing. In many cases, such hygiene articles are applied to elderly people by changing the size of products originally developed for infants. Old people and infants have very different types of food and their metabolic systems,
There are problems such as generation of off-flavors.
【０００３】そこで異臭発生などの問題を解決するため
にいくつかの手段が考え出されたが、いずれも一定の効
果はあるものの十分満足いくものではなかった。例え
ば、香料などによるマスキングは香料成分によってはあ
る程度の効果が得られるが、持続性に乏しく一時しのぎ
に過ぎないことが多い。これに対して、β−サイクロデ
キストリン等に香料を包接させ、異臭成分と香料とを交
換させ異臭を抑制しながら同時に異臭をマスキングする
方法等が考案されたが、すべての異臭成分が必ずしもβ
−サイクロデキストリンに包接されやすいわけではな
く、思うような効果が得られなかった。さらに、香気を
徐放することにより持続性を改善する方法も考案された
が、持続性は改善できてもマスキング作用を損なう場合
が少なくなかった為、これも思う様な効果が得られなか
った。即ち、この様な異臭をより効果的に抑制する手段
が求められていた。[0003] In order to solve the problem such as the generation of offensive odor, some means have been devised. However, all of them have a certain effect but are not satisfactory. For example, masking with a fragrance or the like can provide a certain effect depending on the fragrance component, but is often poor in persistence and only temporary. On the other hand, a method has been devised in which a perfume is included in β-cyclodextrin or the like, and an off-odor component is exchanged with the perfume to suppress the off-odor and at the same time mask the off-odor.
-It was not easy to be included by cyclodextrin, and the desired effect was not obtained. Further, a method of improving sustainability by releasing the fragrance gradually has been devised. However, even if the sustainability can be improved, the masking action is often impaired, so that the desired effect cannot be obtained. That is, there has been a demand for means for more effectively suppressing such off-flavors.
【０００４】又、異臭の発生については、近年流行とな
ってきているペットについても、その排泄物や体臭等で
同様に問題になっており、各種のペット用トイレ等が考
案されているが、吸水性高分子等の技術を応用して、尿
などを外に漏れない様にするトイレは出来ているが、異
臭まで抑制するペット用トイレはまだ得られていない。[0004] Also, regarding the generation of off-flavors, pets that have become popular in recent years are also problematic due to their excretion and body odor, and various pet toilets have been devised. Toilet that prevents urine from leaking out has been made by applying technologies such as water-absorbing polymers, but a pet toilet that suppresses unusual odors has not yet been obtained.
【０００５】又、メチルサリシレートガラクトピラノシ
ド、メントールガラクトピラノシド、桂皮アルコールガ
ラクトピラノシド、シス−３−ヘキセノールガラクトピ
ラノシド、バニリンガラクトピラノシド、オイゲノール
ガラクトピラノシド、シトロネロールガラクトピラノシ
ド、ゲラニオールガラクトピラノシド、ジヒドロミルセ
ノールガラクトピラノシド等の香料配糖体と、サイクロ
デキストリン等の包接香料とを混合して用いることにつ
いては何等の報告もなされていなかった。Also, methyl salicylate galactopyranoside, menthol galactopyranoside, cinnamon alcohol galactopyranoside, cis-3-hexenol galactopyranoside, vanillin galactopyranoside, eugenol galactopyranoside, citronellol No report has been made on the use of a mixture of a perfume glycoside such as galactopyranoside, geraniol galactopyranoside, dihydromyrcenol galactopyranoside, and an inclusion perfume such as cyclodextrin. Was.
【０００６】[0006]
【発明が解決しようとする課題】本発明はこの様な状況
を踏まえてなされたものであり、人間或いはペットの排
泄物などに起因する異臭を抑制する手段を提供すること
を課題とする。SUMMARY OF THE INVENTION The present invention has been made in view of such circumstances, and it is an object of the present invention to provide means for suppressing an unpleasant odor caused by human or pet excrement.
【０００７】[0007]
【課題を解決するための手段】本発明者等はこの様な状
況に鑑みて、異臭の抑制手段を求めて鋭意研究を重ねた
結果、サイクロデキストリン包接香料と香料配糖体とを
含有する組成物が異臭をマスキングする作用に優れるこ
と、及びこの様な組成物を紙オムツなどの衛生用品やペ
ット用品に用いると、そこから発せられる異臭を抑制で
きることを見いだし発明を完成させた。Means for Solving the Problems In view of such circumstances, the present inventors have conducted intensive studies in search of means for suppressing off-flavors. As a result, the present inventors have found that cyclodextrin inclusion flavors and fragrance glycosides are contained. The inventors have found that the composition has an excellent action of masking off-flavors, and that when such a composition is used in sanitary articles such as disposable diapers and pet articles, the off-flavors generated therefrom can be suppressed, and the invention has been completed.
【０００８】すなわち、本発明は、サイクロデキストリ
ン包接香料と香料配糖体とを含有することを特徴とする
異臭抑制組成物である。本発明に用いるサイクロデキス
トリン包接香料としてはβ−サイクロデキストリン包接
香料が好ましい。β−サイクロデキストリン包接香料に
おいて、β−サイクロデキストリンに包接される香料と
しては、メチルサリシレート、メントール、桂皮アルコ
ール、シス−３−ヘキセノール、バニリン、オイゲノー
ル、イソアミルアセテート、シンナミックアルデヒド、
パラクレシルアセテート、リナリルアセテート、ベンジ
ルアセテート、シトロネロール、ゲラニオール、ジヒド
ロミルセノール、カプロン酸アリル、酢酸ヘキシル、レ
モンオイル、スペアミントオイル、ユーカリ油等から１
種又は２種以上を好ましく用いることができる。[0008] That is, the present invention is an off-flavor suppressing composition characterized by containing a cyclodextrin inclusion flavor and a perfume glycoside. As the cyclodextrin inclusion flavor used in the present invention, β-cyclodextrin inclusion flavor is preferable. In the β-cyclodextrin inclusion flavor, the flavor included in β-cyclodextrin includes methyl salicylate, menthol, cinnamon alcohol, cis-3-hexenol, vanillin, eugenol, isoamyl acetate, cinnamic aldehyde,
Paracresyl acetate, linalyl acetate, benzyl acetate, citronellol, geraniol, dihydromyrcenol, allyl caproate, hexyl acetate, lemon oil, spearmint oil, eucalyptus oil, etc.
Species or two or more species can be preferably used.
【０００９】本発明の異臭抑制組成物が含有する香料配
糖体の香料部分を具体的に示す香料配糖体としては、メ
チルサリシレート、メントール、桂皮アルコール、チモ
ール、シス−３−ヘキセノール、バニリン、オイゲノー
ル、フェネチルアルコール、シトロネロール、ゲラニオ
ール、ジヒドロミルセノール、リナリルアルコール等の
香料の各配糖体を挙げることができ、これらから選ばれ
る１種又は２種以上を好ましく用いることができる。ま
た、香料配糖体の糖部分を具体的に示す香料配糖体とし
ては、香料のα−グルコピラノシド及び／又はβ−ガラ
クトピラノシド等を挙げることができる。[0009] Examples of the fragrance glycoside specifically showing the fragrance portion of the fragrance glycoside contained in the off-flavor suppressing composition of the present invention include methyl salicylate, menthol, cinnamon alcohol, thymol, cis-3-hexenol, vanillin, Examples include flavor glycosides such as eugenol, phenethyl alcohol, citronellol, geraniol, dihydromyrcenol, and linalyl alcohol, and one or more glycosides selected from these can be preferably used. In addition, examples of the flavor glycoside specifically showing the sugar portion of the flavor glycoside include α-glucopyranoside and / or β-galactopyranoside of the flavor.
【００１０】異臭抑制組成物中でのサイクロデキストリ
ン包接香料と香料配糖体との重量含有比は、１：９９〜
９９：１とすることが好ましい。また、本発明は、上記
異臭抑制組成物を有する衛生用品である。この衛生用品
として好ましくは、紙オムツ、衛生シート、簡易トイレ
等を挙げられる。[0010] The weight content ratio of cyclodextrin inclusion flavor and flavor glycoside in the off-flavor suppressing composition is 1:99 to
Preferably, the ratio is 99: 1. The present invention is also a sanitary article having the above-mentioned off-flavor suppressing composition. Preferred examples of the sanitary article include a disposable diaper, a sanitary sheet, a simple toilet, and the like.
【００１１】また、本発明は、上記異臭抑制組成物を有
するペット用品である。このペット用品として好ましく
は、床敷き、ペット用トイレ、ペット用シート等を挙げ
られる。Further, the present invention is a pet article having the above-mentioned composition for suppressing an off-flavor. Preferably, the pet supplies include floor coverings, pet toilets, pet sheets, and the like.
【００１２】[0012]
【発明の実施の形態】以下、本発明について詳細に説明
する。 （１）本発明で用いるサイクロデキストリン包接香料 本発明で用いるサイクロデキストリン包接香料は、サイ
クロデキストリンに香料を包接したものである。BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. (1) Cyclodextrin clathrate perfume used in the present invention The cyclodextrin clathrate perfume used in the present invention is a cyclodextrin clathrate with a perfume.
【００１３】サイクロデキストリンとしては、α−サイ
クロデキストリン、β−サイクロデキストリン、γ−サ
イクロデキストリン等種々のサイクロデキストリンを用
いることが可能であるが、本発明で用いるサイクロデキ
ストリンとして好ましくはβ−サイクロデキストリンが
挙げられる。As the cyclodextrin, various cyclodextrins such as α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin and the like can be used, and β-cyclodextrin is preferably used as the cyclodextrin used in the present invention. No.
【００１４】サイクロデキストリン包接香料に包接され
る香料としては、サイクロデキストリンに包接すること
ができ、またサイクロデキストリン包接香料から徐々に
放出されて異臭をマスキングすることができるものを用
いる。サイクロデキストリンの種類により包接すること
ができる香料は必ずしも同じではないが、例えば、β−
サイクロデキストリンに包接する場合に好ましい香料と
しては、メチルサリシレート、メントール、桂皮アルコ
ール、シス−３−ヘキセノール、バニリン、オイゲノー
ル、イソアミルアセテート、シンナミックアルデヒド、
パラクレシルアセテート、リナリルアセテート、ベンジ
ルアセテート、シトロネロール、ゲラニオール、ジヒド
ロミルセノール、カプロン酸アリル、酢酸ヘキシル、レ
モンオイル、スペアミントオイル、ユーカリ油、フェネ
チルアルコール、ボルニルアセテート等を例示でき、こ
のうちでも特に好ましくは、メチルサリシレート、桂皮
アルコール、バニリン、シンナミックアルデヒド等が挙
げられる。As the fragrance to be included in the cyclodextrin inclusion fragrance, a fragrance that can be included in the cyclodextrin and that can be gradually released from the cyclodextrin inclusion fragrance to mask an off-odor is used. Fragrances that can be included according to the type of cyclodextrin are not necessarily the same, for example, β-
Preferred flavors for inclusion in cyclodextrin include methyl salicylate, menthol, cinnamon alcohol, cis-3-hexenol, vanillin, eugenol, isoamyl acetate, cinnamic aldehyde,
Paracresyl acetate, linalyl acetate, benzyl acetate, citronellol, geraniol, dihydromyrcenol, allyl caproate, hexyl acetate, lemon oil, spearmint oil, eucalyptus oil, phenethyl alcohol, bornyl acetate, etc. Particularly preferred are methyl salicylate, cinnamon alcohol, vanillin, cinamic aldehyde and the like.
【００１５】香料は、香料を包接させる際に単独でサイ
クロデキストリンに包接させてもよいし、２種以上を混
合した香料を包接させてもよい。さらに、１種類の香料
を包接させたサイクロデキストリン包接香料を、複数種
類混合してもよい。The fragrance may be included in the cyclodextrin alone when the fragrance is included, or may be a mixture of two or more fragrances. Further, a plurality of cyclodextrin inclusion flavors in which one kind of flavor is included may be mixed.
【００１６】香料をサイクロデキストリンに包接させる
場合、その方法は、従来知られている方法に準じて行え
ば良く、例えば、香料をエタノール等の溶媒に溶かした
後サイクロデキストリンと混合し、溶媒を減圧除去した
り、サイクロデキストリンにエタノールなどの溶媒に溶
かした香料を噴霧しコーティングしたりすれば良い。こ
の時の香料とサイクロデキストリンとは、その重量比で
１：１００〜５０：１００とすることが好ましく、３：
１００〜２５：１００とすることがより好ましく、５：
１００〜２０：１００とすることが更に好ましい。When the flavor is included in the cyclodextrin, the method may be performed according to a conventionally known method. For example, the flavor is dissolved in a solvent such as ethanol, and then mixed with the cyclodextrin, and the solvent is removed. Removal may be performed under reduced pressure, or a cyclodextrin may be coated by spraying a flavor dissolved in a solvent such as ethanol. At this time, the weight ratio of the fragrance and the cyclodextrin is preferably from 1: 100 to 50: 100, and 3:
The ratio is more preferably 100 to 25: 100, and 5:
The ratio is more preferably set to 100 to 20: 100.
【００１７】サイクロデキストリン包接香料は、包接さ
れた香料を徐放することによる持続性のマスキング作用
を有し、また異臭成分の種類によっては、異臭成分と香
料とを交換し、異臭成分を吸着しながら同時に異臭をマ
スキングすることができる。The cyclodextrin clathrate has a sustained masking action by gradually releasing the included perfume, and, depending on the type of off-flavor component, exchanges the off-flavor component with the perfume to remove the off-flavor component. At the same time, the off-flavor can be masked while being adsorbed.
【００１８】（２）本発明で用いる香料配糖体 本発明で用いる香料配糖体としては、構造式中に水酸基
を有しかつ香気を有する化合物、すなわち構造式中に水
酸基を有する香料と、糖とがグリコシド結合したもので
あれば特段の限定無く用いることが出来る。(2) Fragrance Glycoside Used in the Present Invention As the fragrance glycoside used in the present invention, a compound having a hydroxyl group in the structural formula and having an odor, that is, a fragrance having a hydroxyl group in the structural formula, Any sugar can be used without particular limitation as long as it is a glycosidic bond.
【００１９】香料配糖体に用いる、構造式中に水酸基を
有する香料としては、例えば、メチルサリシレート、メ
ントール、桂皮アルコール、チモール、シス−３−ヘキ
セノール、バニリン、オイゲノール、フェネチルアルコ
ール、シトロネロール、ゲラニオール、ジヒドロミセノ
ール、リナリルアルコール、ヘキセノール等が例示で
き、これらの中でも好ましくはメチルサリシレート、メ
ントール、桂皮アルコール、チモール、シス−３−ヘキ
セノール、バニリン、オイゲノール、シトロネロール、
ゲラニオール、ジヒドロミセノール等を挙げることがで
きる。Examples of the fragrance having a hydroxyl group in the structural formula used for the fragrance glycoside include methyl salicylate, menthol, cinnamon alcohol, thymol, cis-3-hexenol, vanillin, eugenol, phenethyl alcohol, citronellol, geraniol, Examples thereof include dihydromycenol, linalyl alcohol, and hexenol, and among these, methyl salicylate, menthol, cinnamon alcohol, thymol, cis-3-hexenol, vanillin, eugenol, citronellol,
Geraniol, dihydromycenol and the like can be mentioned.
【００２０】本発明に用いる香料配糖体の糖部分は単糖
類でも多糖類でもよく、例えば、ピラノグルコシド、ア
ラビノシド、リボシド、リボノシルアラビノシド、ラム
ノシド、マルトトレオシド、ガラクトシド等が例示でき
る。これらの内好ましいものは、α−グルコピラノシ
ド、β−ガラクトピラノシド、β−マンノピラノシド、
α−マルトシドであり、更に好ましくは、α−グルコピ
ラノシド、β−ガラクトピラノシド等を挙げることがで
きる。The sugar moiety of the flavor glycoside used in the present invention may be a monosaccharide or a polysaccharide, for example, pyranoglucoside, arabinoside, riboside, ribonosylarabinoside, rhamnoside, maltotreoside, galactoside and the like. it can. Of these, α-glucopyranoside, β-galactopyranoside, β-mannopyranoside,
α-maltoside, more preferably α-glucopyranoside, β-galactopyranoside and the like.
【００２１】本発明に用いる香料配糖体は、上記のよう
に香料と糖類とがグリコシド結合により結合した化合物
であるので、加水分解酵素等の作用により容易にグリコ
シド結合が切断され糖類と香料とに分解される。このよ
うにして生じる香料は、異臭を抑制する作用を有する。
したがって、糖類と香料とが分解され得る条件下におい
て香料配糖体は異臭を効果的に抑制することができる。The fragrance glycoside used in the present invention is a compound in which a fragrance and a saccharide are linked by a glycosidic bond as described above. Therefore, the glycoside bond is easily cleaved by the action of a hydrolase or the like, and the saccharide and the fragrance are combined. Is decomposed into The fragrance thus generated has an action of suppressing an off-flavor.
Therefore, the fragrance glycoside can effectively suppress the off-flavor under the condition that the saccharide and the fragrance can be decomposed.
【００２２】上記加水分解酵素は、人間やペットの排泄
物、唾液、体内からの代謝物等の中に含まれていること
が本発明者らにより確認されており、香料配糖体に、排
泄物、唾液または代謝物等が何らかのかたちで触れる
と、香料配糖体のグリコシド結合が切断され香料が徐々
に分離されることで異臭が抑制される。つまり、香料配
糖体を人間やペットの排泄物等からの異臭を抑制するた
めに用いれば、その異臭の原因物質中に前記香料配糖体
を加水分解して香料を分離する作用を有する成分が含ま
れているので、異臭の抑制が必要なときにこれに対して
必要量の香料が分離され、それ以外のときには香料は香
料配糖体のかたちで保持される。したがって、上記香料
配糖体は、特に人間やペットの排泄物等からの異臭に対
して効率的な持続性のマスキング作用を有し、異臭を抑
制することができる。It has been confirmed by the present inventors that the above-mentioned hydrolase is contained in human and pet excretions, saliva, metabolites from the body, and the like. When an object, saliva, metabolite, or the like touches in any way, the glycoside bond of the perfume glycoside is broken, and the perfume is gradually separated, thereby suppressing the off-flavor. In other words, if the perfume glycoside is used to suppress off-flavor from human or pet excrement, etc., a component having an action of hydrolyzing the perfume glycoside to separate the perfume in a substance causing the off-flavor. , The necessary amount of the fragrance is separated from the odor when it is necessary to suppress the off-flavor, and otherwise, the fragrance is retained in the form of a fragrance glycoside. Therefore, the above-mentioned fragrance glycoside has an effective and persistent masking action particularly against an odor from human or pet excrement, and can suppress the odor.
【００２３】ここで、上記香料配糖体に作用する加水分
解酵素は、香料配糖体の構造に応じて異なるが、人間や
ペットの排泄物や唾液、体内からの代謝物中に含まれる
加水分解酵素のうちでも、α−グルコシダーゼ、β−ガ
ラクトシダーゼ等は他の加水分解酵素に比べて上記異臭
の原因物質中での含有量が比較的高いことが本発明者ら
により以下の表１に示されるとおり確認されており、こ
れにより本発明に用いる好ましい香料配糖体として、糖
部分がα−グルコピラノシド、β−ガラクトピラノシド
等である香料配糖体が挙げられるのである。Here, the hydrolase that acts on the fragrance glycoside varies depending on the structure of the fragrance glycoside. However, the hydrolase contained in the excrement, saliva, and metabolites from the body of humans and pets. Among the hydrolytic enzymes, α-glucosidase, β-galactosidase and the like are shown by the present inventors in Table 1 below to have a relatively high content in the above-mentioned off-flavor causative substances as compared with other hydrolytic enzymes. Thus, preferred flavor glycosides used in the present invention include flavor glycosides having a sugar moiety of α-glucopyranoside, β-galactopyranoside, or the like.
【００２４】表１は、人間の尿中に含まれる加水分解酵
素を調べるために、表中に示すニトロフェノールの各種
の配糖体にヒトの尿を作用させたときに、グリコシド結
合切断（加水分解）により分離されるニトロフェノール
量を４０５ｎｍでの吸光度を測定することにより測定し
た結果を示す表である。なお、表中＋＋＋は分離された
（発生した）ニトロフェノール量が多い（４０５ｎｍの
光吸収が強い）ことを、＋＋は発生したニトロフェノー
ル量が比較的多い（４０５ｎｍの光吸収が比較的強い）
ことを、＋はニトロフェノールが明らかに発生した（４
０５ｎｍの光を明らかに吸収した）ことを、−はニトロ
フェノールが発生していないか、極わずかに発生した
（４０５ｎｍの光を吸収しないか、極わずかに吸収し
た）ことをそれぞれ示す。また、犬および猫の尿中に含
まれる加水分解酵素についても上記と同様の試験がなさ
れており、下記表１に示される結果と同様の傾向が確認
されている。Table 1 shows that, when human urine was allowed to act on various nitrophenol glycosides shown in the table in order to examine hydrolases contained in human urine, glycosidic bond cleavage (hydrolysis) was carried out. 3 is a table showing the results obtained by measuring the amount of nitrophenol separated by decomposition) by measuring the absorbance at 405 nm. In the table, +++ indicates that the amount of separated (generated) nitrophenol is large (light absorption at 405 nm is strong), and ++ indicates that the amount of generated nitrophenol is relatively large (light absorption of 405 nm is relatively strong).
In addition, + means that nitrophenol was clearly generated (4
-Indicates that nitrophenol was not generated or was slightly generated (light of 405 nm was not absorbed or was slightly absorbed). In addition, the same test as described above has been performed for hydrolases contained in urine of dogs and cats, and the same tendency as the results shown in Table 1 below has been confirmed.
【００２５】[0025]
【表１】 本発明の異臭抑制組成物が含有する香料配糖体は、上記
のような香料配糖体のうちの１種であってもよく、また
２種以上であってもよい。[Table 1] The fragrance glycoside contained in the off-flavor suppression composition of the present invention may be one kind or two or more kinds of the fragrance glycosides as described above.
【００２６】かかる香料配糖体は既知の物質であり、こ
れらの製造方法は既に常法として知られている。例え
ば、糖類と香料とを硝酸銀などを触媒として縮合させる
ことにより製造することができる。あるいは糖類と香料
とを、グルコシダーゼ、ガラクトシダーゼ、グリコシル
トランスフェラーゼ等のグリコシル化反応を触媒し得る
酵素を用いて、所定の条件下で縮合させることにより容
易に得られる。また、香料配糖体は天然にも広く存在す
るので、このような香料配糖体を含有する起源物より、
通常の方法で抽出、精製することでも容易に得られる。
このような香料配糖体の各種製造方法のうちでも、立体
選択性のよい酵素を用いて糖類と香料とを縮合させる方
法が本発明においては好ましい。Such fragrance glycosides are known substances, and their production methods are already known as ordinary methods. For example, it can be produced by condensing a saccharide and a flavor with silver nitrate or the like as a catalyst. Alternatively, it can be easily obtained by condensing a saccharide and a flavor under predetermined conditions using an enzyme capable of catalyzing a glycosylation reaction such as glucosidase, galactosidase, glycosyltransferase or the like. In addition, since fragrance glycosides are widely present in nature, from sources containing such fragrance glycosides,
It can also be easily obtained by extraction and purification by a usual method.
Among the various methods for producing such perfume glycosides, a method of condensing a saccharide and a perfume using an enzyme having good stereoselectivity is preferred in the present invention.
【００２７】さらに、アセチル化等により糖部分が誘導
体化された香料配糖体の誘導体も、本発明で用いる香料
配糖体の範疇に属するものとして扱われる。Further, a derivative of a fragrance glycoside having a sugar moiety derivatized by acetylation or the like is also treated as belonging to the category of the fragrance glycoside used in the present invention.
【００２８】（３）本発明の異臭抑制組成物 本発明の異臭抑制組成物は、上記サイクロデキストリン
包接香料と香料配糖体とを含有することを特徴とする。(3) Off-odor Control Composition of the Present Invention The off-odor control composition of the present invention is characterized by containing the above cyclodextrin inclusion flavor and a perfume glycoside.
【００２９】本発明の異臭抑制組成物における、サイク
ロデキストリン包接香料と香料配糖体の好ましい重量含
有比は、１：９９〜９９：１であり、より好ましくは
５：９５〜９５：５であり、更に好ましくは１：９〜
９：１である。この範囲であれば、サイクロデキストリ
ン包接香料および香料配糖体による異臭抑制効果が相乗
的に得られるが、この範囲外であると両者を混合してい
ることによる最適な効果はあまり期待できない。The preferred weight content ratio of cyclodextrin inclusion flavor and flavor glycoside in the off-flavor suppressing composition of the present invention is 1: 99-99: 1, more preferably 5: 95-95: 5. Yes, more preferably 1: 9-
9: 1. Within this range, the effect of cyclodextrin clathrate and flavor glycosides can be synergistically obtained, but if it is outside this range, the optimal effect due to the mixture of both cannot be expected much.
【００３０】本発明の異臭抑制組成物はサイクロデキス
トリン包接香料と香料配糖体とを配合し、このまま粉体
等として用いることができる。また、本発明の異臭抑制
組成物にはサイクロデキストリン包接香料および香料配
糖体以外に任意成分としてナイロンパウダー等の粉体及
び／又はアクリル系高分子などの高吸水性ポリマーやス
ラッシュパルプなどセルロース等の吸水性物質を配合す
ることができる。また、任意成分を配合した異臭抑制組
成物は粉体の他、半固体としてもよいし、粉体を固めて
固形物にする等してもよい。本発明の異臭抑制組成物に
於ける、これら任意成分の好ましい含有量は、組成物全
体に対して１０〜５０重量％である。The composition for suppressing an offensive odor of the present invention can be used as a powder or the like by mixing a cyclodextrin inclusion flavor and a fragrance glycoside. In addition to the cyclodextrin clathrate and perfume glycoside, the off-odor control composition of the present invention may contain, as optional components, powder such as nylon powder and / or superabsorbent polymer such as acrylic polymer or cellulose such as slush pulp. And other water-absorbing substances. In addition, the off-flavor suppressing composition containing an optional component may be semi-solid, or may be solidified by solidifying the powder, in addition to powder. The preferable content of these optional components in the off-flavor suppressing composition of the present invention is 10 to 50% by weight based on the whole composition.
【００３１】本発明の異臭抑制組成物は、サイクロデキ
ストリン包接香料と香料配糖体とを混合すればよく、通
常の粉体組成物の製法など通常の方法に従って製造でき
る。例えば、粉体組成物とするのであれば、ヘンシェル
ミキサー等で均一に混合し、パルベライザー等で解砕す
ればよいし、ペースト状、軟ワックス状の半固体の組成
物とするのであれば、ロールやニーダーで混合すればよ
い。The composition for suppressing an offensive odor of the present invention may be prepared by mixing a cyclodextrin inclusion flavor and a perfume glycoside, and can be produced according to a usual method such as a method for producing a usual powder composition. For example, if it is a powder composition, it may be uniformly mixed with a Henschel mixer or the like, and may be crushed with a pulverizer or the like, or if it is a paste-like or soft wax-like semi-solid composition, it may be rolled. Or kneading with a kneader.
【００３２】かくして得られた異臭抑制組成物は、香料
配糖体の酵素分解による香料の放出、およびサイクロデ
キストリン包接体からの香料の徐放という異なる作用に
基づく放香成分を組み合わせることにより異臭を抑制す
る効果に優れる。また、この異臭抑制効果は持続性にも
優れる。さらに、異臭成分の種類によってはサイクロデ
キストリン包接香料が香料を放出しつつ異臭成分を吸着
し得るため、さらに優れた異臭抑制効果も期待できる。The thus obtained off-flavor suppressing composition is obtained by combining the off-flavor components based on different actions such as the release of the perfume by enzymatic decomposition of the perfume glycoside and the sustained release of the perfume from the cyclodextrin clathrate. It is excellent in suppressing effect. In addition, the effect of suppressing the off-flavor is excellent in persistence. Further, depending on the type of the off-flavor component, the cyclodextrin clathrate can adsorb the off-flavor component while releasing the perfume, so that a more excellent off-flavor suppressing effect can be expected.
【００３３】このような本発明の異臭抑制組成物は異臭
の抑制のために広く用いることができる。本発明の異臭
抑制組成物に含まれる香料配糖体は、糖部分と香料とに
分解され得る条件下で効果的に異臭抑制の作用をするも
のであることから、本発明の異臭抑制組成物はそのよう
な条件下で好適に用いることができる。特に、本発明の
異臭抑制組成物は、人間のペットの排泄物、唾液、体内
からの代謝物等に起因する異臭の抑制に好適に用いるこ
とができる。また、人間やペットの排泄物、唾液、体内
からの代謝物等に起因する異臭は、時間の経過とともに
臭いの程度がきつくなることがあるが、本発明の異臭抑
制組成物の異臭抑制作用は持続性があり、この点におい
ても本発明の異臭抑制組成物はこのような異臭を抑制す
るのに好適である。さらに、本発明の異臭抑制組成物中
にはサイクロデキストリン包接香料も含まれており、上
記のように香料配糖体が特に優れた異臭抑制作用を発揮
し得る条件下でなくてもサイクロデキストリン包接香料
からは香料が徐放される。したがって、本発明の異臭抑
制組成物は、人間やペットの排泄物、唾液、体内からの
代謝物等に起因する異臭の抑制に特に好適に用いること
ができる一方で、その他にも広くさまざまな条件下にお
いて好適に用いることができる。The composition for suppressing an offensive odor according to the present invention can be widely used for suppressing offensive odor. Since the fragrance glycoside contained in the off-flavor suppressing composition of the present invention effectively acts on the off-flavor under conditions that can be decomposed into a sugar portion and a fragrance, the off-flavor suppressing composition of the present invention Can be suitably used under such conditions. In particular, the composition for suppressing offensive odor of the present invention can be suitably used for suppressing offensive odor caused by excretion, saliva, metabolites and the like of human pets. Further, the odor caused by excretion of humans and pets, saliva, metabolites from the body, and the like, the degree of odor may become severe over time, but the odor control effect of the odor control composition of the present invention is It is persistent, and in this respect, the off-flavor suppressing composition of the present invention is suitable for suppressing such off-flavors. Further, the off-flavor suppressing composition of the present invention also contains a cyclodextrin clathrate perfume, and the cyclodextrin does not need to be under the condition where the perfume glycoside can exert a particularly excellent off-flavor suppressing action as described above. The fragrance is gradually released from the clathrate. Accordingly, the off-flavor suppressing composition of the present invention can be particularly suitably used for suppressing off-flavors caused by excretion of humans and pets, saliva, metabolites from the body, etc. It can be suitably used below.
【００３４】（４）本発明の応用範囲 本発明の異臭抑制組成物は、異臭に係わる製品に特段の
限定無く用いることが出来る。この様な製品としては、
例えば、紙オムツ、衛生シート、簡易トイレ等の人体用
の衛生用品、床敷き、ペット用トイレ、ペット用シート
等のペット用品等が例示できる。この他、生ゴミや動物
の糞尿にふりかけて異臭を抑制する防臭粉体やトイレ等
の異臭を抑制するトイレタリー製品等が挙げられる。
又、成分が化粧料などで広く用いられているものである
ことから、デオドラント等の化粧料や水虫薬のような皮
膚外用剤にも配合することが出来る。(4) Range of Application of the Present Invention The off-flavor suppressing composition of the present invention can be used for products relating to off-flavors without any particular limitation. Such products include:
For example, sanitary articles for the human body such as disposable diapers, sanitary sheets and simple toilets, and pet articles such as floor coverings, pet toilets and pet sheets can be exemplified. In addition, there are deodorizing powders that suppress unpleasant odor by sprinkling on garbage and animal excrement, and toiletry products that suppress unpleasant odor such as toilets.
In addition, since the components are widely used in cosmetics and the like, they can be blended in cosmetics such as deodorants and skin external preparations such as athlete's foot.
【００３５】異臭抑制作用を有する上記のような衛生用
品又はペット用品等は、例えば上記本発明の異臭抑制組
成物をこれらの衛生用品、ペット用品等の表面等に保持
させることにより得ることができる。異臭抑制組成物を
保持させる箇所、方法、量などは衛生用品、ペット用品
等の種類に応じて適宜調整してよい。The above-mentioned sanitary articles or pet articles having an off-flavor suppressing action can be obtained, for example, by holding the above-mentioned off-odor suppressing composition of the present invention on the surfaces of these sanitary articles, pet articles, etc. . The location, method, amount, and the like for holding the off-flavor suppressing composition may be appropriately adjusted according to the types of sanitary articles, pet articles, and the like.
【００３６】[0036]
【実施例】以下に実施例を挙げて本発明について詳細に
説明するが、本発明がこれら実施例にのみ限定を受けな
いことは言うまでもない。EXAMPLES The present invention will be described in detail below with reference to Examples, but it goes without saying that the present invention is not limited to these Examples.
【００３７】＜β−サイクロデキストリン包接香料の製
造例＞まず、製造例１−１から製造例１−１９にβ−サ
イクロデキストリン包接香料の製造例を示す。なお、β
−サイクロデキストリンは、市販されているＢＣＤ（メ
ルシャン株式会社製）を用いた。<Production example of β-cyclodextrin inclusion flavor> First, Production Examples 1-1 to 1-19 show production examples of β-cyclodextrin inclusion flavor. Note that β
-The cyclodextrin used was a commercially available BCD (manufactured by Mercian Corporation).
【００３８】[0038]
【製造例１−１】β−サイクロデキストリン１００ｇを
５０％エタノール水溶液２０００ｍｌに加熱溶解し、こ
れに２０ｍｌのエタノールに溶解した１０ｇのメチルサ
リシレートを徐々に加え、冷却して結晶を析出させて濾
取し風乾してβ−サイクロデキストリン包接香料１を９
１ｇ得た。Production Example 1-1 100 g of β-cyclodextrin was dissolved by heating in 2000 ml of a 50% aqueous ethanol solution, and 10 g of methyl salicylate dissolved in 20 ml of ethanol was gradually added thereto. And air-dried to give 9 of β-cyclodextrin clathrate 1
1 g was obtained.
【００３９】[0039]
【製造例１−２】β−サイクロデキストリン１００ｇを
５０％エタノール水溶液２０００ｍｌに加熱溶解し、こ
れに２０ｍｌのエタノールに溶解した１０ｇのメントー
ルを徐々に加え、冷却して結晶を析出させて濾取し風乾
してβ−サイクロデキストリン包接香料２を９５ｇ得
た。Production Example 1-2 100 g of β-cyclodextrin was dissolved by heating in 2000 ml of a 50% aqueous ethanol solution, and 10 g of menthol dissolved in 20 ml of ethanol was gradually added thereto. The mixture was air-dried to obtain 95 g of β-cyclodextrin inclusion flavor 2.
【００４０】[0040]
【製造例１−３】β−サイクロデキストリン１００ｇを
５０％エタノール水溶液２０００ｍｌに加熱溶解し、こ
れに２０ｍｌのエタノールに溶解した１０ｇの桂皮アル
コールを徐々に加え、冷却して結晶を析出させて濾取し
風乾してβ−サイクロデキストリン包接香料３を８９ｇ
得た。Production Example 1-3 100 g of β-cyclodextrin was dissolved by heating in 2000 ml of a 50% aqueous ethanol solution, and 10 g of cinnamon alcohol dissolved in 20 ml of ethanol was gradually added thereto. And air-dried, 89 g of β-cyclodextrin inclusion flavor 3
Obtained.
【００４１】[0041]
【製造例１−４】β−サイクロデキストリン１００ｇを
５０％エタノール水溶液２０００ｍｌに加熱溶解し、こ
れに２０ｍｌのエタノールに溶解した１０ｇのシス−３
−ヘキセノールを徐々に加え、冷却して結晶を析出させ
て濾取し風乾してβ−サイクロデキストリン包接香料４
を９２ｇ得た。Production Example 1-4 100 g of β-cyclodextrin was dissolved by heating in 2000 ml of a 50% aqueous ethanol solution, and 10 g of cis-3 dissolved in 20 ml of ethanol was dissolved therein.
-Hexenol is gradually added, and the crystals are precipitated by cooling, collected by filtration, air-dried and β-cyclodextrin inclusion flavor 4
Was obtained in an amount of 92 g.
【００４２】[0042]
【製造例１−５】β−サイクロデキストリン１００ｇを
５０％エタノール水溶液２０００ｍｌに加熱溶解し、こ
れに２０ｍｌのエタノールに溶解した１０ｇのバニリン
を徐々に加え、冷却して結晶を析出させて濾取し風乾し
てβ−サイクロデキストリン包接香料５を９０ｇ得た。Preparation Example 1-5 100 g of β-cyclodextrin was dissolved by heating in 2000 ml of a 50% aqueous ethanol solution, and 10 g of vanillin dissolved in 20 ml of ethanol was gradually added thereto. The mixture was air-dried to obtain 90 g of β-cyclodextrin clathrate incense flavor 5.
【００４３】[0043]
【製造例１−６】β−サイクロデキストリン１００ｇを
５０％エタノール水溶液２０００ｍｌに加熱溶解し、こ
れに２０ｍｌのエタノールに溶解した１０ｇのオイゲノ
ールを徐々に加え、冷却して結晶を析出させて濾取し風
乾してβ−サイクロデキストリン包接香料６を９３ｇ得
た。Production Example 1-6 100 g of β-cyclodextrin was dissolved by heating in 2000 ml of a 50% aqueous ethanol solution, and 10 g of eugenol dissolved in 20 ml of ethanol was gradually added thereto. After air-drying, 93 g of β-cyclodextrin inclusion flavor 6 was obtained.
【００４４】[0044]
【製造例１−７】β−サイクロデキストリン１００ｇを
５０％エタノール水溶液２０００ｍｌに加熱溶解し、こ
れに２０ｍｌのエタノールに溶解した１０ｇのイソアミ
ルアセテートを徐々に加え、冷却して結晶を析出させて
濾取し風乾してβ−サイクロデキストリン包接香料７を
９４ｇ得た。Production Example 1-7 100 g of β-cyclodextrin was dissolved by heating in 2000 ml of a 50% aqueous ethanol solution, and 10 g of isoamyl acetate dissolved in 20 ml of ethanol was gradually added thereto. The mixture was air-dried to obtain 94 g of β-cyclodextrin inclusion flavor 7.
【００４５】[0045]
【製造例１−８】β−サイクロデキストリン１００ｇを
５０％エタノール水溶液２０００ｍｌに加熱溶解し、こ
れに２０ｍｌのエタノールに溶解した１０ｇのシンナミ
ックアルデヒドを徐々に加え、冷却して結晶を析出させ
て濾取し風乾してβ−サイクロデキストリン包接香料８
を９１ｇ得た。Preparation Example 1-8 100 g of β-cyclodextrin was dissolved in 2000 ml of a 50% aqueous ethanol solution under heating, and 10 g of cinnamic aldehyde dissolved in 20 ml of ethanol was gradually added thereto. Take air-dried and add β-cyclodextrin inclusion flavor 8
Was obtained in an amount of 91 g.
【００４６】[0046]
【製造例１−９】β−サイクロデキストリン１００ｇを
５０％エタノール水溶液２０００ｍｌに加熱溶解し、こ
れに２０ｍｌのエタノールに溶解した１０ｇのパラクレ
シルアセテートを徐々に加え、冷却して結晶を析出させ
て濾取し風乾してβ−サイクロデキストリン包接香料９
を９３ｇ得た。Production Example 1-9 100 g of β-cyclodextrin was dissolved by heating in 2000 ml of a 50% aqueous ethanol solution, and 10 g of paracresyl acetate dissolved in 20 ml of ethanol was gradually added thereto, followed by cooling to precipitate crystals. Filter and air-dry to give β-cyclodextrin inclusion flavor 9
Was obtained in 93 g.
【００４７】[0047]
【製造例１−１０】β−サイクロデキストリン１００ｇ
を５０％エタノール水溶液２０００ｍｌに加熱溶解し、
これに２０ｍｌのエタノールに溶解した１０ｇのリナリ
ルアセテートを徐々に加え、冷却して結晶を析出させて
濾取し風乾してβ−サイクロデキストリン包接香料１０
を８５ｇ得た。[Production Example 1-10] 100 g of β-cyclodextrin
Is dissolved in 2000 ml of a 50% aqueous ethanol solution by heating.
10 g of linalyl acetate dissolved in 20 ml of ethanol was gradually added thereto, and the crystals were precipitated by cooling, collected by filtration, air-dried, and dried with β-cyclodextrin clathrate.
Was obtained in an amount of 85 g.
【００４８】[0048]
【製造例１−１１】β−サイクロデキストリン１００ｇ
を５０％エタノール水溶液２０００ｍｌに加熱溶解し、
これに２０ｍｌのエタノールに溶解した１０ｇのベンジ
ルアセテートを徐々に加え、冷却して結晶を析出させて
濾取し風乾してβ−サイクロデキストリン包接香料１１
を８７ｇ得た。[Production Example 1-11] 100 g of β-cyclodextrin
Is dissolved in 2000 ml of a 50% aqueous ethanol solution by heating.
To this was slowly added 10 g of benzyl acetate dissolved in 20 ml of ethanol, cooled to precipitate crystals, collected by filtration and air-dried to give β-cyclodextrin clathrate fragrance 11
87 g were obtained.
【００４９】[0049]
【製造例１−１２】β−サイクロデキストリン１００ｇ
を５０％エタノール水溶液２０００ｍｌに加熱溶解し、
これに２０ｍｌのエタノールに溶解した１０ｇのシトロ
ネロールを徐々に加え、冷却して結晶を析出させて濾取
し風乾してβ−サイクロデキストリン包接香料１２を９
２ｇ得た。Production Example 1-12 100 g of β-cyclodextrin
Is dissolved in 2000 ml of a 50% aqueous ethanol solution by heating.
10 g of citronellol dissolved in 20 ml of ethanol was gradually added thereto, and the mixture was cooled to precipitate crystals, collected by filtration and air-dried to give β-cyclodextrin clathrate perfume 12 in 9 parts.
2 g were obtained.
【００５０】[0050]
【製造例１−１３】β−サイクロデキストリン１００ｇ
を５０％エタノール水溶液２０００ｍｌに加熱溶解し、
これに２０ｍｌのエタノールに溶解した１０ｇのゲラニ
オールを徐々に加え、冷却して結晶を析出させて濾取し
風乾してβ−サイクロデキストリン包接香料１３を９４
ｇ得た。Production Example 1-13 100 g of β-cyclodextrin
Is dissolved in 2000 ml of a 50% aqueous ethanol solution by heating.
10 g of geraniol dissolved in 20 ml of ethanol was gradually added thereto, and the mixture was cooled to precipitate crystals, collected by filtration and air-dried to give β-cyclodextrin clathrate 13 in 94 parts.
g was obtained.
【００５１】[0051]
【製造例１−１４】β−サイクロデキストリン１００ｇ
を５０％エタノール水溶液２０００ｍｌに加熱溶解し、
これに２０ｍｌのエタノールに溶解した１０ｇのジヒド
ロミルセノールを徐々に加え、冷却して結晶を析出させ
て濾取し風乾してβ−サイクロデキストリン包接香料１
４を１０５ｇ得た。[Production Example 1-14] 100 g of β-cyclodextrin
Is dissolved in 2000 ml of a 50% aqueous ethanol solution by heating.
To this was slowly added 10 g of dihydromyrcenol dissolved in 20 ml of ethanol, cooled to precipitate crystals, collected by filtration and air-dried to obtain β-cyclodextrin clathrate 1
105g was obtained.
【００５２】[0052]
【製造例１−１５】β−サイクロデキストリン１００ｇ
を５０％エタノール水溶液２０００ｍｌに加熱溶解し、
これに２０ｍｌのエタノールに溶解した１０ｇのアリル
カプロネートを徐々に加え、冷却して結晶を析出させて
濾取し風乾してβ−サイクロデキストリン包接香料１５
を９１ｇ得た。[Production Example 1-15] 100 g of β-cyclodextrin
Is dissolved in 2000 ml of a 50% aqueous ethanol solution by heating.
To this, 10 g of allyl capronate dissolved in 20 ml of ethanol was gradually added, and the mixture was cooled to precipitate crystals, collected by filtration, air-dried, and β-cyclodextrin inclusion flavor 15
Was obtained in an amount of 91 g.
【００５３】[0053]
【製造例１−１６】β−サイクロデキストリン１００ｇ
を５０％エタノール水溶液２０００ｍｌに加熱溶解し、
これに２０ｍｌのエタノールに溶解した１０ｇのヘキシ
ルアセテートを徐々に加え、冷却して結晶を析出させて
濾取し風乾してβ−サイクロデキストリン包接香料１６
を８９ｇ得た。[Production Example 1-16] 100 g of β-cyclodextrin
Is dissolved in 2000 ml of a 50% aqueous ethanol solution by heating.
To this was slowly added 10 g of hexyl acetate dissolved in 20 ml of ethanol, cooled to precipitate crystals, collected by filtration and air-dried to give β-cyclodextrin inclusion flavoring agent 16.
89g was obtained.
【００５４】[0054]
【製造例１−１７】β−サイクロデキストリン１００ｇ
を５０％エタノール水溶液２０００ｍｌに加熱溶解し、
これに２０ｍｌのエタノールに溶解した１０ｇのレモン
オイルを徐々に加え、冷却して結晶を析出させて濾取し
風乾してβ−サイクロデキストリン包接香料１７を９２
ｇ得た。[Production Example 1-17] 100 g of β-cyclodextrin
Is dissolved in 2000 ml of a 50% aqueous ethanol solution by heating.
To this was slowly added 10 g of lemon oil dissolved in 20 ml of ethanol, cooled to precipitate crystals, collected by filtration and air-dried to give β-cyclodextrin clathrate perfume 17
g was obtained.
【００５５】[0055]
【製造例１−１８】β−サイクロデキストリン１００ｇ
を５０％エタノール水溶液２０００ｍｌに加熱溶解し、
これに２０ｍｌのエタノールに溶解した１０ｇのスペア
ミントオイルを徐々に加え、冷却して結晶を析出させて
濾取し風乾してβ−サイクロデキストリン包接香料１８
を９０ｇ得た。[Production Example 1-18] 100 g of β-cyclodextrin
Is dissolved in 2000 ml of a 50% aqueous ethanol solution by heating.
10 g of spearmint oil dissolved in 20 ml of ethanol was gradually added thereto, and the crystals were precipitated by cooling, collected by filtration, and air-dried to obtain β-cyclodextrin clathrate 18
90 g was obtained.
【００５６】[0056]
【製造例１−１９】β−サイクロデキストリン１００ｇ
を５０％エタノール水溶液２０００ｍｌに加熱溶解し、
これに２０ｍｌのエタノールに溶解した１０ｇのユーカ
リオイルを徐々に加え、冷却して結晶を析出させて濾取
し風乾してβ−サイクロデキストリン包接香料１９を９
４ｇ得た。Production Example 1-19 β-cyclodextrin 100 g
Is dissolved in 2000 ml of a 50% aqueous ethanol solution by heating.
10 g of eucalyptus oil dissolved in 20 ml of ethanol was slowly added thereto, and the crystals were precipitated by cooling, collected by filtration, and air-dried to obtain 9 parts of β-cyclodextrin clathrate perfume.
4 g were obtained.
【００５７】＜香料配糖体の製造例＞次に、香料配糖体
の製造例を製造例２−１から２−２０に示す。<Production Examples of Perfume Glycosides> Next, Production Examples of perfume glycosides are shown in Production Examples 2-1 to 2-20.
【００５８】[0058]
【香料配糖体の製造例２−１】１０ｇのβ−ガラクトシ
ルガラクトースと１０ｍｇのβ−ガラクトシダーゼを水
５００ｍｌに溶かして得られた水溶液に、アセトン２０
ｍｌにメチルサリシレート１ｇを溶解させた溶液を加え
て３７℃で４８時間撹拌した。その後水相を分離し、シ
リカゲルカラムクロマトグラフィー、（溶出溶媒；メタ
ノール：クロロホルム＝１：１）、ＯＤＳカラムクロマ
トグラフィー（溶出溶媒；１０％アセトニトリル水溶
液）、ダイアイオンＨＰ−２０カラムクロマトグラフィ
ー（溶出溶媒；２０％エタノール水溶液→５０％エタノ
ール水溶液）で順次精製し、１２４ｍｇのメチルサリシ
レート−β−ガラクトピラノシド（香料配糖体１）を得
た。[Production Example 2-1 of Perfume Glycoside] Acetone 20 was added to an aqueous solution obtained by dissolving 10 g of β-galactosylgalactose and 10 mg of β-galactosidase in 500 ml of water.
A solution prepared by dissolving 1 g of methyl salicylate in 100 ml was added and the mixture was stirred at 37 ° C. for 48 hours. Thereafter, the aqueous phase was separated, silica gel column chromatography, (elution solvent; methanol: chloroform = 1: 1), ODS column chromatography (elution solvent; 10% acetonitrile aqueous solution), Diaion HP-20 column chromatography (elution solvent) ; 20% ethanol aqueous solution → 50% ethanol aqueous solution) to obtain 124 mg of methyl salicylate-β-galactopyranoside (flavor glycoside 1).
【００５９】[0059]
【香料配糖体の製造例２−２】香料配糖体の製造例２−
１において、メチルサリシレート１ｇの替わりにメント
ール１ｇを用いた以外は上記製造例２−１と同様にし
て、８６ｍｇのメントール−β−ガラクトピラノシド
（香料配糖体２）を得た。[Production Example 2-2 of Fragrance Glycoside] Production Example 2- of Fragrance Glycoside
In Example 1, 86 mg of menthol-β-galactopyranoside (flavor glycoside 2) was obtained in the same manner as in Production Example 2-1 except that 1 g of menthol was used instead of 1 g of methyl salicylate.
【００６０】[0060]
【香料配糖体の製造例２−３】香料配糖体の製造例２−
１において、メチルサリシレート１ｇの替わりに桂皮ア
ルコール１ｇを用いた以外は上記製造例２−１と同様に
して、１３１ｍｇの桂皮アルコール−β−ガラクトピラ
ノシド（香料配糖体３）を得た。[Production Example 2-3 of Perfume Glycoside] Production Example 2- of Perfume Glycoside
In Example 1, 131 mg of cinnamon alcohol-β-galactopyranoside (fragrance glycoside 3) was obtained in the same manner as in Production Example 2-1 except that 1 g of cinnamon alcohol was used instead of 1 g of methyl salicylate.
【００６１】[0061]
【香料配糖体の製造例２−４】香料配糖体の製造例２−
１において、メチルサリシレート１ｇの替わりにチモー
ル１ｇを用いた以外は上記製造例２−１と同様にして、
４３ｍｇのチモール−β−ガラクトピラノシド（香料配
糖体４）を得た。[Production Example 2-4 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
1 in the same manner as in Production Example 2-1 except that 1 g of thymol was used instead of 1 g of methyl salicylate,
43 mg of thymol-β-galactopyranoside (flavor glycoside 4) was obtained.
【００６２】[0062]
【香料配糖体の製造例２−５】香料配糖体の製造例２−
１において、メチルサリシレート１ｇの替わりにシス−
３−ヘキセノール１ｇを用いた以外は上記製造例２−１
と同様にして、２０１ｍｇのシス−３−ヘキセノール−
β−ガラクトピラノシド（香料配糖体５）を得た。[Production Example 2-5 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
In Example 1, cis-glycolate was used instead of 1 g of methyl salicylate.
Preparation Example 2-1 except that 1 g of 3-hexenol was used.
In the same manner as in the above, 201 mg of cis-3-hexenol-
β-galactopyranoside (flavor glycoside 5) was obtained.
【００６３】[0063]
【香料配糖体の製造例２−６】香料配糖体の製造例２−
１において、メチルサリシレート１ｇの替わりにバニリ
ン１ｇを用いた以外は上記製造例１と同様にして、１０
８ｍｇのバニリン−β−ガラクトピラノシド（香料配糖
体６）を得た。[Production Example 2-6 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
In the same manner as in Preparation Example 1 except that 1 g of vanillin was used in place of 1 g of methyl salicylate in Example 1,
8 mg of vanillin-β-galactopyranoside (flavor glycoside 6) was obtained.
【００６４】[0064]
【香料配糖体の製造例２−７】香料配糖体の製造例２−
１において、メチルサリシレート１ｇの替わりにオイゲ
ノール１ｇを用いた以外は上記製造例２−１と同様にし
て、２１１ｍｇのオイゲノール−β−ガラクトピラノシ
ド（香料配糖体７）を得た。[Production Example 2-7 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
In Example 1, 211 mg of eugenol-β-galactopyranoside (fragrance glycoside 7) was obtained in the same manner as in Production Example 2-1 except that 1 g of eugenol was used instead of 1 g of methyl salicylate.
【００６５】[0065]
【香料配糖体の製造例２−８】香料配糖体の製造例２−
１において、メチルサリシレート１ｇの替わりにフェネ
チルアルコール１ｇを用いた以外は上記製造例２−１と
同様にして、１９４ｍｇのフェネチルアルコール−β−
ガラクトピラノシド（香料配糖体８）を得た。[Production Example 2-8 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
1 in the same manner as in Production Example 2-1 except that 1 g of phenethyl alcohol was used instead of 1 g of methyl salicylate, and 194 mg of phenethyl alcohol-β-
Galactopyranoside (flavor glycoside 8) was obtained.
【００６６】[0066]
【香料配糖体の製造例２−９】香料配糖体の製造例２−
１において、メチルサリシレート１ｇの替わりにシトロ
ネロール１ｇを用いた以外は上記製造例２−１と同様に
して、８６ｍｇのシトロネロール−β−ガラクトピラノ
シド（香料配糖体９）を得た。[Production Example 2-9 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
In Example 1, 86 mg of citronellol-β-galactopyranoside (fragrance glycoside 9) was obtained in the same manner as in Production Example 2-1 except that 1 g of citronellol was used instead of 1 g of methyl salicylate.
【００６７】[0067]
【香料配糖体の製造例２−１０】１０ｇのα−グルコシ
ルグルコースと１０ｍｇのα−グルコシダーゼを水５０
０ｍｌに溶かして得られた水溶液に、アセトン２０ｍｌ
にメチルサリシレート１ｇを溶解させた溶液を加えて３
７℃で４８時間撹拌した。その後、水相を分離し、シリ
カゲルカラムクロマトグラフィー、（溶出溶媒；メタノ
ール：クロロホルム＝１：１）、ＯＤＳカラムクロマト
グラフィー（溶出溶媒；１０％アセトニトリル水溶
液）、ダイアイオンＨＰ−２０カラムクロマトグラフィ
ー（溶出溶媒；２０％エタノール水溶液→５０％エタノ
ール水溶液）で順次精製し、１０２ｍｇのメチルサリシ
レート−α−グルコピラノシド（香料配糖体１０）を得
た。[Production Example 2-10 of Perfume Glycoside] 10 g of α-glucosyl glucose and 10 mg of α-glucosidase were added to 50 parts of water.
20 ml of acetone was added to the aqueous solution obtained by dissolving in 0 ml.
To the solution containing 1 g of methyl salicylate
Stirred at 7 ° C. for 48 hours. Thereafter, the aqueous phase was separated, silica gel column chromatography, (elution solvent; methanol: chloroform = 1: 1), ODS column chromatography (elution solvent; 10% acetonitrile aqueous solution), Diaion HP-20 column chromatography (elution) (Solvent: 20% aqueous ethanol → 50% aqueous ethanol) to give 102 mg of methyl salicylate-α-glucopyranoside (flavor glycoside 10).
【００６８】[0068]
【香料配糖体の製造例２−１１】香料配糖体の製造例２
−１０において、メチルサリシレート１ｇの替わりにメ
ントール１ｇを用いた以外は上記製造例２−１０と同様
にして、１０８ｍｇのメントール−α−グルコピラノシ
ド（香料配糖体１１）を得た。[Production Example 2-11 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
In -10, 108 mg of menthol-α-glucopyranoside (flavor glycoside 11) was obtained in the same manner as in Production Example 2-10, except that 1 g of menthol was used instead of 1 g of methyl salicylate.
【００６９】[0069]
【香料配糖体の製造例２−１２】香料配糖体の製造例２
−１０において、メチルサリシレート１ｇの替わりに桂
皮アルコール１ｇを用いた以外は上記製造例２−１０と
同様にして、１２２ｍｇの桂皮アルコール−α−グルコ
ピラノシド（香料配糖体１２）を得た。[Production Example 2-12 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
In -10, 122 mg of cinnamon alcohol-α-glucopyranoside (fragrance glycoside 12) was obtained in the same manner as in Production Example 2-10 except that 1 g of cinnamon alcohol was used instead of 1 g of methyl salicylate.
【００７０】[0070]
【香料配糖体の製造例２−１３】香料配糖体の製造例２
−１０において、メチルサリシレート１ｇの替わりにチ
モール１ｇを用いた以外は上記製造例２−１０と同様に
して、３７ｍｇのチモール−α−グルコピラノシド（香
料配糖体１３）を得た。[Production Example 2-13 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
In -10, 37 mg of thymol-α-glucopyranoside (fragrance glycoside 13) was obtained in the same manner as in Production Example 2-10, except that 1 g of thymol was used instead of 1 g of methyl salicylate.
【００７１】[0071]
【香料配糖体の製造例２−１４】香料配糖体の製造例２
−１０において、メチルサリシレート１ｇの替わりにシ
ス−３−ヘキセノール１ｇを用いた以外は上記製造例２
−１０と同様にして、１７１ｍｇのシス−３−ヘキセノ
ール−α−グルコピラノシド（香料配糖体１４）を得
た。[Production Example 2-14 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
-10, except that 1 g of cis-3-hexenol was used in place of 1 g of methyl salicylate.
In the same manner as in -10, 171 mg of cis-3-hexenol-α-glucopyranoside (fragrance glycoside 14) was obtained.
【００７２】[0072]
【香料配糖体の製造例２−１５】香料配糖体の製造例２
−１０において、メチルサリシレート１ｇの替わりにバ
ニリン１ｇを用いた以外は上記製造例２−１０と同様に
して、８９ｍｇのバニリン−α−グルコピラノシド（香
料配糖体１５）を得た。[Production Example 2-15 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
In -10, 89 mg of vanillin-α-glucopyranoside (fragrance glycoside 15) was obtained in the same manner as in Production Example 2-10, except that 1 g of vanillin was used instead of 1 g of methyl salicylate.
【００７３】[0073]
【香料配糖体の製造例２−１６】香料配糖体の製造例２
−１０において、メチルサリシレート１ｇの替わりにオ
イゲノール１ｇを用いた以外は上記製造例２−１０と同
様にして、１２１ｍｇのオイゲノール−α−グルコピラ
ノシド（香料配糖体１６）を得た。[Production Example 2-16 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
In -10, 121 mg of eugenol-α-glucopyranoside (fragrance glycoside 16) was obtained in the same manner as in Production Example 2-10, except that 1 g of eugenol was used instead of 1 g of methyl salicylate.
【００７４】[0074]
【香料配糖体の製造例２−１７】香料配糖体の製造例２
−１０において、メチルサリシレート１ｇの替わりにフ
ェネチルアルコール１ｇを用いた以外は上記製造例２−
１０と同様にして、７９ｍｇのフェネチルアルコール−
α−グルコピラノシド（香料配糖体１７）を得た。[Production Example 2-17 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
-10, except that 1 g of phenethyl alcohol was used in place of 1 g of methyl salicylate.
79 mg of phenethyl alcohol-
α-glucopyranoside (fragrance glycoside 17) was obtained.
【００７５】[0075]
【香料配糖体の製造例２−１８】香料配糖体の製造例２
−１０において、メチルサリシレート１ｇの替わりにシ
トロネロール１ｇを用いた以外は上記製造例２−１０と
同様にして、１１６ｍｇのシトロネロール−α−グルコ
ピラノシド（香料配糖体１８）を得た。[Production Example 2-18 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
In -10, 116 mg of citronellol-α-glucopyranoside (fragrance glycoside 18) was obtained in the same manner as in Production Example 2-10, except that 1 g of citronellol was used instead of 1 g of methyl salicylate.
【００７６】[0076]
【香料配糖体の製造例２−１９】香料配糖体の製造例２
−１０において、メチルサリシレート１ｇの替わりにゲ
ラニオール１ｇを用いた以外は上記製造例２−１０と同
様にして、１２０ｍｇのゲラニオール−α−グルコピラ
ノシド（香料配糖体１９）を得た。[Production Example 2-19 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
In -10, 120 mg of geraniol-α-glucopyranoside (flavor glycoside 19) was obtained in the same manner as in Production Example 2-10, except that 1 g of geraniol was used instead of 1 g of methyl salicylate.
【００７７】[0077]
【香料配糖体の製造例２−２０】香料配糖体の製造例２
−１０において、メチルサリシレート１ｇの替わりにジ
ヒドロミルセノール１ｇを用いた以外は上記製造例２−
１０と同様にして、１１１ｍｇのジヒドロミルセノール
−α−グルコピラノシド（香料配糖体２０）を得た。[Production Example 2-20 of Fragrance Glycoside] Production Example 2 of Fragrance Glycoside
-10, except that 1 g of dihydromyrcenol was used in place of 1 g of methyl salicylate.
In a similar manner to 10, 111 mg of dihydromyrcenol-α-glucopyranoside (fragrance glycoside 20) was obtained.
【００７８】[0078]
【実施例１〜４】 ＜異臭抑制組成物の製造＞表１に示す処方で香料配糖体
の種類を変え、本発明の異臭抑制組成物（実施例１〜
４）を作製した。香料配糖体の量は０．０５ｇで、β−
サイクロデキストリン包接香料はβ−サイクロデキスト
リン包接香料１を０．０５ｇ用いた。これらは乳鉢で良
く混合して製造した。Examples 1 to 4 <Production of Off-Flavor Suppressing Composition> The off-flavor suppressing composition of the present invention (Examples 1 to 4) was prepared by changing the type of fragrance glycoside according to the formulation shown in Table 1.
4) was produced. The amount of flavor glycoside is 0.05 g, β-
As the cyclodextrin inclusion flavor, 0.05 g of β-cyclodextrin inclusion flavor 1 was used. These were manufactured by mixing well in a mortar.
【００７９】＜異臭抑制効果試験＞実施例１〜４の異臭
抑制組成物に人尿３５ｍｌを加え、異臭の立ち具合を、
異種が気にならないを５点、異臭がやや認識できるを４
点、異臭が認識できるを３点、異臭が気になるを２点、
異臭が非常に気になるを１点として専門パネラー５名に
より、人尿添加直後と添加１時間後に判定し平均値を求
めた。対照１は香料配糖体もβ−サイクロデキストリン
包接香料も添加しないもの、対照２は香料配糖体を含有
しないもの、対照３は実施例１のβ−サイクロデキスト
リン包接香料１をβ−サイクロデキストリンに置換した
もの、比較１は実施例１のβ−サイクロデキストリン包
接香料をメチルサリシレート０．００５ｇに置換したも
の、比較２は実施例１の香料配糖体１をメチルサリシレ
ート０．０２ｇに置換したものを用いた。<Offensive Odor Suppression Effect Test> 35 ml of human urine was added to the off-odor suppression compositions of Examples 1 to 4, and
5 points when you do not care about different kinds, 4 points when you can recognize a strange odor a little
3 points for recognizing off-flavors, 2 for off-flavors,
One panel was determined to be very worried about off-flavors, and the results were determined by five specialized panelists immediately after the addition of human urine and one hour after the addition, and the average value was determined. Control 1 does not contain any perfume glycoside or β-cyclodextrin inclusion perfume, Control 2 does not contain perfume glycoside, and Control 3 shows β-cyclodextrin inclusion perfume 1 of Example 1 as β-cyclodextrin. Comparative Example 1 was obtained by substituting the β-cyclodextrin inclusion flavor of Example 1 with 0.005 g of methyl salicylate, and Comparative Example 2 was obtained by replacing the flavor glycoside 1 of Example 1 with methyl salicylate 0.02 g. Was used.
【００８０】表２より、本発明の異臭抑制組成物による
異臭抑制効果が優れており、しかも持続性があることが
明かとなった。また、本発明の異臭抑制組成物による効
果は、香料配糖体とβ−サイクロデキストリン包接香料
の相乗効果であることが判る。Table 2 shows that the offensive odor suppressing effect of the composition of the present invention is excellent and persistent. In addition, it is understood that the effect of the off-flavor suppressing composition of the present invention is a synergistic effect of the perfume glycoside and the β-cyclodextrin inclusion perfume.
【００８１】[0081]
【表２】 （表２中「包接香料１」とは、製造例１で得られたβ−
サイクロデキストリンデキストリン包接香料１のことを
さす。）[Table 2] (In Table 2, “inclusion perfume 1” refers to β-obtained in Production Example 1.
Cyclodextrin Refers to dextrin clathrate 1. )
【００８２】[0082]
【実施例５〜２２】０．５ｇの香料配糖体１に、表３に
示すβ−サイクロデキストリン包接香料０．０５ｇをそ
れぞれ加え乳鉢で良く混合して異臭抑制組成物を作製
し、上記の異臭抑制効果試験と同様に異臭抑制作用を調
べた。結果を表３に示す。Examples 5 to 22 To 0.5 g of fragrance glycoside 1 were added 0.05 g of the β-cyclodextrin inclusion flavor shown in Table 3 and mixed well in a mortar to prepare an off-flavor suppressing composition. The off-flavor suppressing effect was examined in the same manner as in the off-flavor suppressing effect test. Table 3 shows the results.
【００８３】[0083]
【表３】 [Table 3]
【００８４】[0084]
【実施例２３】下記処方に従って、香料配糖体とβ−サ
イクロデキストリン包接香料とを含有する異臭抑制組成
物を作製した。即ち、処方成分を乳鉢で良く混合し、本
発明の異臭抑制組成物を得た。このものについて上記異
臭抑制効果試験と同様に異種抑制作用を評価したとこ
ろ、人尿の添加直後４．２、添加一時間後３．６の異臭
抑制効果が認められた。表２、表３の結果と比較する
と、表４の処方による異臭抑制組成物は香料を単独で用
いるより異臭抑制効果に優れることが判る。Example 23 An off-flavor suppressing composition containing a flavor glycoside and a β-cyclodextrin inclusion flavor was prepared according to the following formulation. That is, the ingredients were mixed well in a mortar to obtain the off-flavor suppressing composition of the present invention. This was evaluated for its heterogeneity-suppressing effect in the same manner as in the above-mentioned off-flavor-suppressing effect test. As a result, an off-flavor suppressing effect of 4.2 immediately after the addition of human urine and 3.6 hours after the addition was observed. Comparing with the results of Tables 2 and 3, it can be understood that the off-flavor suppressing composition according to the formulation of Table 4 is more excellent in the off-flavor suppressing effect than using the fragrance alone.
【００８５】[0085]
【表４】 [Table 4]
【００８６】[0086]
【実施例２４】 紙オムツ 図１及び図２に示される紙オムツの吸水性ポリマー層
に、下記処方の本発明の異臭抑制組成物を２０ｇ混ぜ込
み、加圧成型して紙オムツを得た。このオムツに人尿１
００ｍｌを２時間おき３回しみこませ、２４時間放置し
たが異臭は殆ど感じられなかった。市販品の紙オムツで
同様の実験を行ったところ、強い異臭を感じた。本発明
の異臭抑制組成物が紙オムツにも好適に適用できること
が判る。尚、この紙オムツに用いた異臭抑制組成物は、
表５に示される各成分をヘンシェルミキサーで混合した
後、１ｍｍ丸穴スクリーンを装着したパルベライザーで
解砕して製造した。Example 24 Disposable diaper 20 g of the water-absorbing polymer layer of the disposable diaper shown in FIGS. 1 and 2 was mixed with 20 g of the off-flavor-suppressing composition of the present invention having the following formulation, followed by pressure molding to obtain a disposable diaper. Human urine 1 in this diaper
00 ml was soaked 3 times every 2 hours and left for 24 hours, but almost no off-flavor was felt. When a similar experiment was performed with a commercially available paper diaper, a strong off-flavor was felt. It can be seen that the off-flavor suppressing composition of the present invention can be suitably applied to disposable diapers. In addition, the off-flavor suppressing composition used in this paper diaper was
Each component shown in Table 5 was mixed with a Henschel mixer, and then crushed with a pulverizer equipped with a 1 mm round-hole screen to produce.
【００８７】[0087]
【表５】 [Table 5]
【００８８】[0088]
【実施例２５】 衛生シート 防水シート１×１ｍに下記処方の本発明の異臭抑制組成
物１００ｇを接着剤で張り付け、衛生シートを得た。こ
のものは、病院などでベットに引いて汚物の処理をする
のに便利であった。又、このものはペットのトイレの下
に引くとトイレの処置が楽なばかりかそれに包んでごみ
箱に捨てても異臭が気にならなかった。尚、この衛生シ
ートに用いた異臭抑制組成物は、表６に示される各成分
をヘンシェルミキサーで混合した後、１ｍｍ丸穴スクリ
ーンを装着したパルベライザーで解砕して製造した。Example 25 Sanitary sheet 100 g of an off-odor control composition of the present invention having the following formulation was adhered to a 1 x 1 m waterproof sheet with an adhesive to obtain a sanitary sheet. This was convenient for treating waste by pulling it on a bed at a hospital or the like. In addition, when this product was pulled under the pet toilet, not only the toilet treatment was easy, but even if it was wrapped in it and thrown in the trash box, no unpleasant odor was noticed. The off-flavor suppressing composition used for this sanitary sheet was produced by mixing the components shown in Table 6 with a Henschel mixer and then pulverizing the mixture with a pulverizer equipped with a 1 mm round hole screen.
【００８９】[0089]
【表６】 [Table 6]
【００９０】[0090]
【実施例２６】 ペット用床敷き 市販のマウス用床敷き１００ｇに下記処方の本発明の異
臭抑制組成物２０ｇを混ぜ込み、ペット用床敷きを得
た。このペット用床敷きを用いてマウスを１週間床敷き
を変えずに飼育したが、異臭は気にならなかった。ペッ
ト用床敷きに用いた異臭抑制組成物は、表７に示される
各成分をヘンシェルミキサーで混合した後、１ｍｍ丸穴
スクリーンを装着したパルベライザーで解砕して製造し
た。Example 26 Pet Bedding 100 g of commercially available mouse bedding was mixed with 20 g of the off-flavor suppressing composition of the present invention having the following formulation to obtain a pet bedding. Using this pet flooring, mice were bred for one week without changing the flooring, but no unpleasant odor was noticed. The off-flavor suppressing composition used for pet flooring was produced by mixing the components shown in Table 7 with a Henschel mixer and then crushing the mixture with a pulverizer equipped with a 1 mm round hole screen.
【００９１】[0091]
【表７】 [Table 7]
【００９２】[0092]
【実施例２７】 簡易トイレ 防水性の１Ｌの紙袋に下記の処方の本発明の異臭抑制組
成物５０ｇを詰め簡易トイレを得た。これに人尿３５０
ｃｃを詰め、２４時間放置したが異臭は気にならなかっ
た。尚、簡易トイレに用いた異臭抑制組成物は、表８に
示される各成分をヘンシェルミキサーで混合した後、１
ｍｍ丸穴スクリーンを装着したパルベライザーで解砕し
て製造した。Example 27 Simple Toilet A waterproof 1L paper bag was filled with 50 g of the off-flavor suppressing composition of the present invention having the following formulation to obtain a simple toilet. 350 human urine
The cc was packed and left for 24 hours, but no unpleasant odor was noticed. In addition, the unpleasant odor control composition used for the simple toilet was prepared by mixing the components shown in Table 8 with a Henschel mixer.
It was manufactured by pulverizing with a pulverizer equipped with a mm round hole screen.
【００９３】[0093]
【表８】 [Table 8]
【００９４】[0094]
【実施例２８】 ペット用トイレ（猫砂） 下記の処方に従って、ペット用トイレ（猫砂）を作製し
た。即ち、表９に示される処方成分を転動相造粒装置に
秤込み、メタノール１０重量部を噴霧しながら、４０℃
の熱風を送風し、実施例３の異臭抑制組成物と吸水性ポ
リマーとをコーティングしてペット用のトイレを得た。Example 28 Pet litter (cat litter) A pet litter (cat litter) was prepared according to the following formulation. That is, the prescription components shown in Table 9 were weighed into a rolling phase granulator and sprayed with 10 parts by weight of methanol at 40 ° C
Was blown to coat the off-odor control composition of Example 3 and the water-absorbing polymer to obtain a pet toilet.
【００９５】[0095]
【表９】 [Table 9]
【００９６】[0096]
【発明の効果】本発明の異臭抑制組成物およびこれを有
する衛生用品、ペット用品によれば、異臭、特に人間や
ペットの排泄物、唾液、体内からの代謝物等に起因する
異臭を効果的に抑制できる。また、その異臭抑制効果は
持続性にも優れる。EFFECTS OF THE INVENTION According to the composition for suppressing offensive odor of the present invention and the sanitary articles and pet articles having the same, the offensive odor, especially the odor caused by excretion of humans and pets, saliva, metabolites from the body, etc. can be effectively eliminated. Can be suppressed. In addition, the off-flavor suppressing effect is excellent in persistence.
【図１】 紙オムツの正面図FIG. 1 is a front view of a disposable diaper.
【図２】 紙オムツの断面図FIG. 2 is a cross-sectional view of a disposable diaper.
１０・・紙オムツ １・・不織布 ２・・吸水紙 ３・・スラッシュパルプ ４・・吸水ポリマー ５・・防水シート 10. Paper diaper 1. Non-woven fabric 2. Water-absorbing paper 3. Slash pulp 4. Water-absorbing polymer 5. Waterproof sheet
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ // Ａ６１Ｌ 9/12 Ａ６１Ｌ 9/12 Ｃ０７Ｈ 15/00 Ｃ０７Ｈ 15/00 (72)発明者 坂田 完三 静岡県静岡市大谷836 静岡大学農学部内 (72)発明者 碓氷 泰市 静岡県静岡市大谷836 静岡大学農学部内 (72)発明者 渡辺 修治 静岡県静岡市大谷836 静岡大学農学部内 (72)発明者 山岸 政昭 静岡県沼津市大岡3981番地１静岡県沼津工 業技術センター内 (72)発明者 大石 一男 静岡県沼津市大岡3981番地１静岡県沼津工 業技術センター内────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. 6 Identification symbol FI // A61L 9/12 A61L 9/12 C07H 15/00 C07H 15/00 (72) Inventor Kanzo Sakata 836 Otani, Shizuoka-shi, Shizuoka Inside Shizuoka University Faculty of Agriculture (72) Inventor Yasushi Usui 836 Otani Shizuoka City Shizuoka Prefecture Inside Shizuoka University Agricultural Science (72) Inventor Shuji Watanabe 836 Otani Shizuoka City Shizuoka Prefecture Shizuoka University Faculty of Agriculture (72) Inventor Masaaki Nishizu Yamagishi Shizuoka 3981 Ooka 1 Numazu Industrial Technology Center, Shizuoka Prefecture (72) Inventor Kazuo Oishi 3981 Ooka 1 Numazu City, Numazu City, Shizuoka Prefecture In Numazu Industrial Technology Center, Shizuoka Prefecture
Claims (10)
糖体とを含有することを特徴とする異臭抑制組成物。1. An off-flavor suppressing composition comprising a cyclodextrin clathrate and a fragrance glycoside.
サイクロデキストリンである請求項１に記載の異臭抑制
組成物。2. The cyclodextrin inclusion flavoring agent is β-
The composition for suppressing an offensive odor according to claim 1, which is a cyclodextrin.
メチルサリシレート、メントール、桂皮アルコール、シ
ス−３−ヘキセノール、バニリン、オイゲノール、イソ
アミルアセテート、シンナミックアルデヒド、パラクレ
シルアセテート、リナリルアセテート、ベンジルアセテ
ート、シトロネロール、ゲラニオール、ジヒドロミルセ
ノール、カプロン酸アリル、酢酸ヘキシル、レモンオイ
ル、スペアミントオイル、ユーカリ油から選ばれる１種
又は２種以上の香料を包接する請求項２に記載の異臭抑
制組成物。3. The β-cyclodextrin inclusion flavor,
Methyl salicylate, menthol, cinnamon alcohol, cis-3-hexenol, vanillin, eugenol, isoamyl acetate, cinamic aldehyde, paracresyl acetate, linalyl acetate, benzyl acetate, citronellol, geraniol, dihydromyrcenol, allyl caproate, acetic acid The off-flavor suppressing composition according to claim 2, wherein one or more kinds of fragrances selected from hexyl, lemon oil, spearmint oil, and eucalyptus oil are included.
ントール、桂皮アルコール、チモール、シス−３−ヘキ
セノール、バニリン、オイゲノール、フェネチルアルコ
ール、シトロネロール、ゲラニオール、ジヒドロミルセ
ノール、リナリルアルコールの配糖体から選ばれる１種
又は２種以上である請求項１〜３のいずれか１項に記載
の異臭抑制組成物。4. The fragrance glycoside comprises a methyl salicylate, menthol, cinnamon alcohol, thymol, cis-3-hexenol, vanillin, eugenol, phenethyl alcohol, citronellol, geraniol, dihydromyrcenol, linalyl alcohol glycoside. The unpleasant odor suppressing composition according to any one of claims 1 to 3, which is one or two or more kinds selected.
シド及び／又はβ−ガラクトピラノシドである請求項１
〜４の何れか１項に記載の異臭抑制組成物。5. The fragrance glycoside is α-glucopyranoside and / or β-galactopyranoside of the fragrance.
5. The composition for suppressing an offensive odor according to any one of items 4 to 4.
糖体との重量含有比が、１：９９〜９９：１である請求
項１〜５の何れか１項に記載の異臭抑制組成物。6. The composition according to claim 1, wherein the weight ratio of cyclodextrin clathrate to perfume glycoside is 1:99 to 99: 1.
組成物を有する衛生用品。7. A sanitary article comprising the off-flavor suppressing composition according to claim 1.
れかであることを特徴とする請求項７に記載の衛生用
品。8. The sanitary article according to claim 7, wherein the sanitary article is one of a paper diaper, a sanitary sheet, and a simple toilet.
組成物を有するペット用品。9. A pet article having the off-flavor suppressing composition according to any one of claims 1 to 6.
ートの何れかであることを特徴とする請求項９に記載の
ペット用品。10. The pet article according to claim 9, wherein the pet article is any one of a floor covering, a pet toilet, and a pet seat.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9074256A JPH10263062A (en) | 1997-03-26 | 1997-03-26 | Odor restraining product containing glycoside and deodorizing powder |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9074256A JPH10263062A (en) | 1997-03-26 | 1997-03-26 | Odor restraining product containing glycoside and deodorizing powder |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH10263062A true JPH10263062A (en) | 1998-10-06 |
Family
ID=13541897
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9074256A Pending JPH10263062A (en) | 1997-03-26 | 1997-03-26 | Odor restraining product containing glycoside and deodorizing powder |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH10263062A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000067720A1 (en) * | 1999-05-07 | 2000-11-16 | The Procter & Gamble Company | Cosmetic compositions |
| WO2002041927A1 (en) * | 2000-11-27 | 2002-05-30 | Zeon Corporation | Deodorant, masking agent for ammonia, deodorant for excretion odor, and water-absorbing deodorizing material |
| US6893647B1 (en) | 2000-05-05 | 2005-05-17 | The Procter & Gamble Company | Cosmetic compositions |
| JP2007044004A (en) * | 2005-08-12 | 2007-02-22 | Fukui:Kk | Environment improving tool for pet |
| JP2010520193A (en) * | 2007-03-01 | 2010-06-10 | ザ プロクター アンド ギャンブル カンパニー | Personal care products containing cyclodextrins as fragrance complexing substances |
| JP2010520861A (en) * | 2007-03-01 | 2010-06-17 | ザ プロクター アンド ギャンブル カンパニー | Personal care products containing cyclodextrins as fragrance complexing substances |
| WO2012065054A1 (en) * | 2010-11-12 | 2012-05-18 | Los Alamos National Security, Llc | Infection detection methods and systems and related compounds and compositions |
| US8686215B2 (en) | 2009-06-18 | 2014-04-01 | The Procter amd Gamble Company | Absorbent articles comprising an odour control system |
| US11000468B2 (en) | 2016-09-06 | 2021-05-11 | The Procter & Gamble Company | Aerosol compositions |
| US11090250B2 (en) | 2007-03-01 | 2021-08-17 | The Procter & Gamble Company | Compositions and/or articles comprising cyclodextrin complexing material |
| US11491099B2 (en) | 2016-09-06 | 2022-11-08 | The Procter & Gamble Company | Antiperspirant and deodorant compositions |
-
1997
- 1997-03-26 JP JP9074256A patent/JPH10263062A/en active Pending
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000067720A1 (en) * | 1999-05-07 | 2000-11-16 | The Procter & Gamble Company | Cosmetic compositions |
| WO2000067715A1 (en) * | 1999-05-07 | 2000-11-16 | The Procter & Gamble Company | Cosmetic compositions |
| US6893647B1 (en) | 2000-05-05 | 2005-05-17 | The Procter & Gamble Company | Cosmetic compositions |
| WO2002041927A1 (en) * | 2000-11-27 | 2002-05-30 | Zeon Corporation | Deodorant, masking agent for ammonia, deodorant for excretion odor, and water-absorbing deodorizing material |
| JP2007044004A (en) * | 2005-08-12 | 2007-02-22 | Fukui:Kk | Environment improving tool for pet |
| JP2010520861A (en) * | 2007-03-01 | 2010-06-17 | ザ プロクター アンド ギャンブル カンパニー | Personal care products containing cyclodextrins as fragrance complexing substances |
| JP2010520193A (en) * | 2007-03-01 | 2010-06-10 | ザ プロクター アンド ギャンブル カンパニー | Personal care products containing cyclodextrins as fragrance complexing substances |
| JP2013177424A (en) * | 2007-03-01 | 2013-09-09 | Procter & Gamble Co | Personal care product including cyclodextrin as fragrance-complexing material |
| US9649386B2 (en) | 2007-03-01 | 2017-05-16 | The Procter & Gamble Company | Compositions and/or articles comprising cyclodextrin complexing material |
| US9649387B2 (en) | 2007-03-01 | 2017-05-16 | The Procter & Gamble Company | Compositions and/or articles comprising cyclodextrin complexing material |
| US11090250B2 (en) | 2007-03-01 | 2021-08-17 | The Procter & Gamble Company | Compositions and/or articles comprising cyclodextrin complexing material |
| US8686215B2 (en) | 2009-06-18 | 2014-04-01 | The Procter amd Gamble Company | Absorbent articles comprising an odour control system |
| WO2012065054A1 (en) * | 2010-11-12 | 2012-05-18 | Los Alamos National Security, Llc | Infection detection methods and systems and related compounds and compositions |
| US11000468B2 (en) | 2016-09-06 | 2021-05-11 | The Procter & Gamble Company | Aerosol compositions |
| US11491099B2 (en) | 2016-09-06 | 2022-11-08 | The Procter & Gamble Company | Antiperspirant and deodorant compositions |
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