JP5567029B2 - 香料システム - Google Patents
香料システム Download PDFInfo
- Publication number
- JP5567029B2 JP5567029B2 JP2011539613A JP2011539613A JP5567029B2 JP 5567029 B2 JP5567029 B2 JP 5567029B2 JP 2011539613 A JP2011539613 A JP 2011539613A JP 2011539613 A JP2011539613 A JP 2011539613A JP 5567029 B2 JP5567029 B2 JP 5567029B2
- Authority
- JP
- Japan
- Prior art keywords
- perfume
- delivery system
- consumer product
- enyl
- methylbut
- 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.)
- Active
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- 239000002304 perfume Substances 0.000 title claims description 158
- 239000000203 mixture Substances 0.000 claims description 139
- 239000003205 fragrance Substances 0.000 claims description 44
- 229920000642 polymer Polymers 0.000 claims description 41
- 238000004140 cleaning Methods 0.000 claims description 39
- 239000004744 fabric Substances 0.000 claims description 35
- -1 3-methylbut-2-enyl Chemical group 0.000 claims description 33
- 239000003599 detergent Substances 0.000 claims description 31
- 150000001412 amines Chemical class 0.000 claims description 30
- 239000000835 fiber Substances 0.000 claims description 21
- 239000003094 microcapsule Substances 0.000 claims description 17
- 239000002994 raw material Substances 0.000 claims description 15
- 229920002472 Starch Polymers 0.000 claims description 14
- 239000008107 starch Substances 0.000 claims description 14
- 235000019698 starch Nutrition 0.000 claims description 14
- 229920000858 Cyclodextrin Polymers 0.000 claims description 8
- 235000011888 snacks Nutrition 0.000 claims description 8
- 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 description 7
- 239000002088 nanocapsule Substances 0.000 claims description 5
- 230000036541 health Effects 0.000 claims description 4
- 230000003796 beauty Effects 0.000 claims description 3
- 235000013361 beverage Nutrition 0.000 claims description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 6
- HFRXONNVPHSVNN-UHFFFAOYSA-N 2-[1-(3-methylbut-2-enyl)cyclobutyl]butan-2-ol Chemical compound CC(C)=CCC1(C(C)(O)CC)CCC1 HFRXONNVPHSVNN-UHFFFAOYSA-N 0.000 claims 4
- QGMXAJZCHWNICA-UHFFFAOYSA-N 1-[1-(3-methylbut-2-enyl)cyclobutyl]butan-2-ol Chemical compound CC(=CCC1(CCC1)CC(CC)O)C QGMXAJZCHWNICA-UHFFFAOYSA-N 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 239000000047 product Substances 0.000 description 80
- 238000000034 method Methods 0.000 description 58
- 239000000243 solution Substances 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- 150000001875 compounds Chemical class 0.000 description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 36
- 230000015572 biosynthetic process Effects 0.000 description 35
- 238000003786 synthesis reaction Methods 0.000 description 35
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 239000003921 oil Substances 0.000 description 32
- 239000000463 material Substances 0.000 description 28
- 239000003208 petroleum Substances 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 28
- 238000003756 stirring Methods 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 229920006395 saturated elastomer Polymers 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000007788 liquid Substances 0.000 description 21
- 239000011159 matrix material Substances 0.000 description 17
- 239000012230 colorless oil Substances 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- 238000005516 engineering process Methods 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- 102000004190 Enzymes Human genes 0.000 description 12
- 108090000790 Enzymes Proteins 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 12
- 229940088598 enzyme Drugs 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- 235000019645 odor Nutrition 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 150000001299 aldehydes Chemical class 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 101150049281 PRM1 gene Proteins 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000010828 elution Methods 0.000 description 9
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 229920001296 polysiloxane Polymers 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
- 239000007844 bleaching agent Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 7
- 229920000877 Melamine resin Polymers 0.000 description 7
- 238000009825 accumulation Methods 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000010779 crude oil Substances 0.000 description 7
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 7
- 238000009792 diffusion process Methods 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 210000004209 hair Anatomy 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000002671 adjuvant Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 208000012839 conversion disease Diseases 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 5
- 230000003750 conditioning effect Effects 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 239000002453 shampoo Substances 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- KLSVXRHCBQWEME-UHFFFAOYSA-N 5-(4-methylcyclohex-3-en-1-yl)hexan-3-ol Chemical compound CCC(O)CC(C)C1CCC(C)=CC1 KLSVXRHCBQWEME-UHFFFAOYSA-N 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 229920002873 Polyethylenimine Polymers 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000002738 chelating agent Substances 0.000 description 4
- 229940043279 diisopropylamine Drugs 0.000 description 4
- 238000004851 dishwashing Methods 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
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- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000012943 hotmelt Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
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- 150000003624 transition metals Chemical class 0.000 description 4
- LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- KPVQNXLUPNWQHM-RBEMOOQDSA-N 3-acetylpyridine adenine dinucleotide Chemical compound CC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 KPVQNXLUPNWQHM-RBEMOOQDSA-N 0.000 description 3
- ZATIMOAGKJEVGN-UHFFFAOYSA-N 3-methyl-1-phenylbutan-2-one Chemical group CC(C)C(=O)CC1=CC=CC=C1 ZATIMOAGKJEVGN-UHFFFAOYSA-N 0.000 description 3
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- VJYFMQREUJXCQV-UHFFFAOYSA-N Limonene aldehyde Chemical compound O=CCC(C)C1CCC(C)=CC1 VJYFMQREUJXCQV-UHFFFAOYSA-N 0.000 description 3
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- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical class NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/293—Saturated compounds containing keto groups bound to rings to a three- or four-membered ring
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- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
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- C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
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- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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- A61Q5/02—Preparations for cleaning the hair
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
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- Chemical Kinetics & Catalysis (AREA)
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Description
本明細書で使用するとき、「消費者製品」は、販売される形態での使用又は消費を一般に意図する、ベビーケア、ビューティケア、衣類及びホームケア、ファミリーケア、フェミニンケア、ヘルスケア、スナック、並びに/又は飲料製品若しくは装置を意味する。このような製品としては、おむつ、よだれかけ、拭き取り用品;脱色、着色、染色、コンディショニング、シャンプー、スタイリングなどの毛髪(ヒト、イヌ及び/若しくはネコ)処理用製品及び/又はその処理に関する方法;脱臭剤及び制汗剤;パーソナルクレンジング;化粧品;クリーム、ローション、及び高級芳香剤を含む消費者使用のための他の局所塗布製品などのスキンケア;シェービング製品;エアフレッシュナー及び香り送達システム、自動車ケア、食器洗浄、布地コンディショニング(柔軟化及び/若しくはフレッシュニングを含む)、洗濯洗浄、洗濯及びすすぎ添加剤及び/又はケア、床及び便器クリーナーなどの硬質表面の洗浄及び/又は処理、消費者若しくは業務用の他の洗浄などの、布地及びホームケアの領域のうちの布地、硬質表面及び任意の他の表面の処理用製品及び/又はその処理に関する方法;トイレットペ−パー、顔用ティッシュ、紙ハンカチ及び/若しくはペーパータオルに関する製品及び/又は方法;タンポン、女性用ナプキン;練り歯磨き、歯用ゲル、歯用リンス、義歯接着剤、歯のホワイトニングなどの口腔ケアに関する製品及び/又は方法;咳及び風邪治療薬、鎮痛剤、処方薬、ペットヘルスと栄養などの店頭販売ヘルスケア;主として慣習的な食事間用又は食事随伴物としての消費が意図される加工食品(非限定的な実施例としては、ポテトチップス、トルティーヤチップス、ポップコーン、プレッツェル、コーンチップス、シリアルバー、野菜チップス又はクリスプ、スナックミックス、パーティミックス、マルチグレインチップス、スナッククラッカー、チーズスナック、ポークラインズ、コーンスナック、ペレットスナック、押出成形スナック及びベーグルチップが挙げられる);並びにコーヒーが挙げられるが、これらに限定されない。
特定の香料送達システム、特定の香料送達システムの製造方法及びかかる香料送達システムの使用が、米国特許出願第2007/0275866(A1)号に開示されている。かかる香料送達システムには以下のものが挙げられる。
香料を配合するために、表1に開示されたPRMが使用され得る。かかる香料は、表1のPRMの組み合わせ、又は表1のPRMのうちの1つ、及び、1つ以上の追加的なPRMを含み得る、PRMの組み合わせである。香料において使用する場合、表1のPRMは、香料総重量に基づいて、約0.01%〜約50%、約0.1%〜約15%、約0.1%〜約10%、又は更には約0.5%〜約10%の濃度で使用され得る。かかる香料は、未希釈での部位への適用、あるいは、消費者製品、洗浄及び/若しくは処理組成物、布地及び硬質表面用の、洗浄及び/若しくは処理組成物、洗剤並びに/又は超コンパクト洗剤の中での使用などの多用途で使用され得る。
本発明の目的のために、以下に例示される補助剤の非限定的な一覧は、本発明の組成物での使用に適しており、例えば、性能を補助若しくは向上させるために、洗浄される基材の処理のために、又は香料、着色剤、染料などを用いる場合のように組成物の審美性を変化させるために、望ましくは本発明の特定の実施形態に組み込むことができる。かかる補助剤は、本出願人らの香料及び/又は香料システムを介して供給される構成成分に追加されると理解される。このような追加的構成成分の明確な性質、及びそれを組み込む濃度は、組成物の物理的形態及び組成物が使用される作業の性質に依存する。好適な補助剤物質としては、界面活性剤、ビルダー、キレート化剤、移染抑制剤、分散剤、酵素、及び酵素安定剤、触媒物質、漂白活性化剤、ポリマー系分散剤、粘土及び汚れ除去/再付着防止剤、増白剤、泡抑制剤、染料、追加の香料及び香料送達系、構造弾性化剤、柔軟剤、キャリア、ヒドロトロープ、加工助剤、及び/又は色素が挙げられるが、これらに限定されない。下記開示に加えて、このような他の補助剤の好適な例、及び使用濃度は、米国特許第5,576,282号、同第6,306,812(B1)号及び同第6,326,348(B1)号に見られ、これらは参照により組み込まれる。
本明細書に開示される特定の消費者製品は、部位を、とりわけ、表面又は布地を、洗浄又は処理することができる。通常、このような部位の少なくとも一部は、希釈されない形態又は希釈された液体、例えば洗浄液の、本出願人らの組成物の実施形態と接触させ、そしてその後、任意に、その部位を洗浄及び/又はすすぎ洗いしてもよい。1つの態様では、ある部位が任意で洗浄及び/又はすすがれ、本発明による粒子に又はこの粒子を含む組成物に接触され、次に任意で洗浄及び/又はすすがれる。本発明の目的のために、洗浄には擦ること及び機械的撹拌が含まれるが、これらに限定されない。布地には、通常の消費者の使用条件で洗濯又は処理することが可能なほとんどいかなる布地が含まれ得る。開示される組成物を含み得る液体のpHは、約3〜約11.5であってよい。こうした組成物は、典型的には溶液中で約500ppm〜約15,000ppmの濃度で使用される。洗浄溶媒が水である場合、水の温度は通常約5℃〜約90℃であり、部位が布地を含む場合、水対布地の比は通常約1:1〜約30:1である。
表1の分子No.31の合成手順(7.5mmolスケールで例示):
工程1(30mmolのスケールで例示):
フラスコにおいて、1.6mmolの3−メチル−1−フェニルブタン−2−オン(1当量)と、1.9mmolのn−ブチルブロミド(1.2当量)と、0.022mmolのN−ベンジルトリエチルアンモニウムブロミド(2mol%)とを、0.5mLの50% NaOHと共に室温にて混合した。この反応混合物を室温で1時間にわたって激しく撹拌した。反応液の温度は60℃に上昇したが、その間、5時間にわたって撹拌を続けた。次に、反応混合物を、冷却した1MのHCl溶液に添加することによりクエンチした。10mLのメチルtert−ブチルエーテル(MTBE)を添加し、組み合わせた有機画分をMTBE(2×5mL)で抽出し、NaHCO3飽和水溶液(5mL)及び食塩水(5mL)で洗浄した。MgSO4上での乾燥、濾過及び濃縮の後、粗生成油を得た。98:2の石油エーテル/エチルアセテートの混合液の溶媒条件から計算されたBiotageのPS1:TLCに基づく方法を用いて行われたフラッシュクロマトグラフィーの後、純粋化合物が得られた。
オーブンにおいて二口4Lフラスコを24時間にわたって2kPa(20mBar)及び80℃にて乾燥させた。このガラス器具を窒素雰囲気下で周囲温度にまで放冷させ、その後、乾燥条件(カニューレ)下にて140グラムの3−(4−メチルシクロヘキサ−3−エニル)ブタナール(リモネンアルデヒド、1当量、0.85mol)を2.8L(5重量%)の無水2−メチルテトラヒドロフラン(2−MeTHF)中に溶解させた。この溶液を冷却して1時間にわたって−50℃にした。次に、2−MeTHF(3.2M、1.06当量)中に溶解させた280mLのエチルマグネシウムブロミドを乾燥している滴下漏斗を介して窒素雰囲気下にて添加した(およそ45分以上にわたって;反応混合物の温度は測定されており、−40℃を超えて温まらないようにした)。反応を−50℃にて1時間にわたって持続させた。次に、反応液を0℃にて一晩撹拌した。反応液を、アイスキューブ(およそ600グラムの氷)で冷却した1リットルの1MのHClに添加することにより、クエンチした。次に、水相を2−MeTHF(2×200mL)で抽出した。組み合わせた有機相を重炭酸塩飽和水溶液(2×100mL)及び食塩水(2×100mL)で洗浄した。組み合わせた画分をMgSO4上で乾燥させ、濾過し、回転蒸発器にて濃縮した。蒸留(111〜127℃、0.5〜1kPa(5〜10mbar))後、純粋化合物が得られた。
オーブンで乾燥させたフラスコにおいて、室温にて、ヘリウム雰囲気下で、15mLの2−メチルテトラヒドロフラン(2−MeTHF)と、0.15グラムの4−(ジメチルアミノ)ピリジン(DMAP、0.08当量)と、8.2グラムのN−メチルモルホリン(NMM、5.3当量、8.9mL)と、3グラムの5−(4−メチルシクロヘキサ−3−エニル)ヘキサン−3−オール(15mmol、1当量)と、を乾燥条件下で混合した。この反応混合物を氷浴中で10分にわたって撹拌し、その後、7.8グラムの無水酢酸(5当量、7.17mL)を滴下漏斗を介して10分間添加した。反応を0℃にて1時間にわたって持続させた。次に、氷浴を取り除き、反応を室温にて1時間にわたって継続させたが、反応の転換に続いて、注射器により取り出された反応混合物のアリコートの分析を介してGC−FIDを行った。次に、30mLの水を添加し、反応混合物を加熱して15分にわたって50℃にし、抽出をこの温度にて行った(2−MeTHF;2×10mL)。有機画分を飽和重炭酸塩及び食塩水で洗浄し、MgSO4上で乾燥させ、濾過し、回転蒸発器で濃縮した。更に、85:15の石油エーテル/エチルアセテートの混合液の溶媒条件から計算されたBiotageのPS1:TLCに基づく方法を用いて、フラッシュクロマトグラフィーを行ったところ、高純度で化合物が得られた。
2Lのフラスコと滴下漏斗と撹拌棒と隔膜とをオーブンにおいて80℃及び2kPa(20mbar)にて24時間にわたって乾燥させた。ガラス器具を窒素雰囲気下で室温まで冷却し、その後、152グラムの三塩化アルミニウム(AlCl3、1.2当量)を300mLの無水ベンゼン中に溶解させた。次に、140グラムのシクロペンチルアセチルクロリド(1当量)を2時間にわたって非常にゆっくりと滴下して反応混合物に添加したが、その間、温度は、この酸塩化物の添加速度により40℃より低く制御した。反応開始及び進行に伴ない、気体が発生した。その後、反応物の混合を、45℃にて16時間にわたって継続した。この反応混合物を、大量の砕氷(1.5kg)に添加することにより、クエンチした。氷で温度を制御しながら、1Lの脱塩水を添加した。白色懸濁液を形成した。ガラス器具を100mLのメチルtert−ブチルエーテル(MTBE)で洗浄し、組み合わせた有機層を濾過し、MTBE(2×100mL)で抽出した。次に、有機層をNaHCO3水溶液及び食塩水で洗浄した。有機画分を採取し、Na2SO4上で乾燥させ、濾過し、減圧下(1.5kPa(15mbar)にて70℃)にて乾燥させたところ、赤色油が得られた。この油を10重量%の活性炭素と混合し、室温にて16時間にわたって撹拌した。次に、この混合物を短いセライト経路で濾過し、ガラス器具及びフィルターを100mLのリグロインですすいだ。有機画分を組み合わせ、回転蒸発器で乾燥させたところ、黄色油が得られた。
反応フラスコにおいて、室温にて、10.61molのケトン(1.7当量)と6.24molのアルデヒド(1当量)と0.5mol%のRuCl3・nH2O(9.2グラム)とを混合した。次に、油浴の温度を115〜130℃に上げながら、反応混合物を撹拌した。注射器により反応混合物のアリコートを取り出し、GC−FIDにより分析した。GC結果に基づき、出発物質の85%が7日間にわたって転化するまで、反応を進行させておいた(この特定のケースにおいて)。次に、この反応混合物を室温に冷却し、その後、1.5Lのトルエンを添加した。有機相を重炭酸塩飽和水溶液で抽出した(4×750mL)。各回、水相をトルエンで洗浄した(2×100mL)。この洗浄の後、全有機相を組み合わせ、重炭酸塩飽和水溶液(750mL)でもう一回、及び、食塩水(3×250mL)で洗浄した。
2:より多くのRuCl3触媒を添加した。
2Lのフラスコにおいて、330グラムのベンズアルデヒド(1当量)を1リットルの2−ペンタノン(3当量)と混合した。反応混合物を5〜10℃に冷却し、徹底的に撹拌し、その後、40mLのNaOH、50重量%水溶液(0.5当量、61g)をゆっくりと一回で添加した。30分後、反応混合物の温度を20℃に上昇させておいた。反応は周囲温度にて5時間にわたって継続した。次に、反応混合物を、等量の氷で冷却した2MのHCl溶液に添加することにより、クエンチした。2−ペンタノン(2×100mL)での抽出後、組み合わせた有機画分を重炭酸塩飽和水溶液(50mL)及び食塩水(50mL)で洗浄した。有機画分を組み合わせ、回転蒸発器で濃縮したところ、黄色油が得られた。この粗生成油を、400mLのジエチルエーテル(Et2O)を含有する三角フラスコに注入した。このフラスコを100mLのEt2Oですすぎ、これを有機相に添加した。次に、500mLの飽和NaHSO3水溶液を、組み合わせた有機画分に室温にて添加した。この混合物を1時間にわたって激しく撹拌し、その後、有機相をデカントし、重炭酸塩飽和水溶液(25mL)及び食塩水(25mL)で洗浄した。得られた黄色油を回転蒸発器で濃縮し、膜ポンプで乾燥させた(0.4kPa(4mbar)にて70℃)。この化合物をまず蒸留(115〜125℃、0.1〜0.3kPa(1〜3mbar))により精製した。その後、更に2回の亜硫酸水素塩洗浄を行った。
1.:Cao,Y.−Q.、Dai,Z.、Zhang,R.及びChen,B−H、Synth.Commum.,2005,35,1045〜1049と同様。
n−ブチルリチウムの溶液(シクロヘキサン中2.2M−1当量)を、無水THF中の氷冷ジイソプロピルアミン(1当量)溶液に滴加した。この温度にて10分にわたって撹拌した後、この混合物にプロピオニトリル(5当量)を添加した。更に10分にわたって0℃にて混合した後、プレニルブロミド(1当量)を添加した。反応転換に続き、GC−MSを行い、0℃における15分の撹拌後、完了したものとみなした。
メチルリチウム溶液(1.2当量)をニトリル(1当量)の無水THF(0.5M)中の溶液に−20℃にて滴加した。−10/−20℃にて15分にわたって撹拌した後、完全転化がGC−MSにより観察された。この反応液をH2SO4溶液(2M−2当量)でクエンチし、その場で形成されたイミンの完全な加水分解が観察されるまで、周囲温度にて撹拌した。次に、この混合物をEt2Oで抽出し、NaHCO3飽和水溶液で洗浄した。組み合わせた有機相をMgSO4上で乾燥させ、減圧下で濃縮した。この得られた油を、石油エーテル−MTBE混合液(95−5)で溶出させることにより、カラムクロマトグラフィーを用いて精製した。減圧下での所望の画分の濃縮により、無色油として化合物が得られた。
4,4−ジメチル−3−オキソペンタノエート(1当量)とK2CO3(2.2当量)との無水アセトン(0.9M)中の溶液にヨードメタン(3.3当量)を60℃にて添加した。この混合物を同じ温度にて16時間にわたって撹拌し、室温に冷却後、MgSO4上で乾燥させた。有機混合物を減圧下で濃縮して、更なる精製なしに生成物を得た。
工程1で形成されたβ−ケトエステルをMTBE(0.6M)中に溶解させ、ナトリウムt−ブトキシド(1.1当量)及びプレニルブロミド(1.5当量)を室温にて添加した。この得られた混合物を同じ温度にて16時間にわたって撹拌し、H2SO4飽和水溶液(0.5M)でクエンチした。混合物をMTBEで抽出した後、採取した有機層をMgSO4上で乾燥させ、減圧下で濃縮した。この得られた油を、溶出剤として石油エーテル−MTBE混合液(95−5)を用いるカラムクロマトグラフィーにより、精製した。減圧下での溶出液の濃縮により、無色油として化合物が得られた。
ホスホニウムブロミド[50889−29−7](1.2当量)の無水THF(0.3M)中の溶液に、周囲温度にてKHMDS(ヘキサメチルジシラザンカリウム−2.4当量)を添加した。同じ温度にて30分にわたって撹拌した後、アセトン(1当量)の無水THF(0.3M)中の溶液を滴加した。この混合物を3時間にわたって撹拌し、水(0.3M)でクエンチし、Et2Oで抽出した。この得られた水層をHCl水溶液(10%)でpH 2が得られるまで酸性化した。この混合物をEt2Oで抽出し、この抽出物をMgSO4上で乾燥させ、減圧下で濃縮した。この得られた油を、石油エーテル−Et2O混合液(1−1)での溶出によりシリカゲル上で急速濾過を用いて、精製した。減圧下での濃縮により、わずかに黄色の油として化合物が生じた。
工程1で形成された酸(1当量)の無水CH2Cl2(0.5M)中の溶液に、1,1’−カルボニルジイミダゾール(1当量)を周囲温度にて添加した。この混合物を15分にわたって撹拌し、N,O−ジメチルヒドロキシルアミン塩酸塩(1当量)を添加した。撹拌を同じ温度にて1時間にわたって継続し、この混合物をHCl水溶液(1M−1.1当量)でクエンチした。この水層をEt2Oで抽出し、NaHCO3で洗浄し、MgSO4上で乾燥させた。減圧下での濃縮により、無色油として化合物が得られた。
工程2で形成されたWeinrebアミドを無水THF(0.5M)中に溶解させ、−15℃に冷却した。この混合物にEtMgBrの溶液(1M−1.5当量)を滴加した。−10/−15℃での10分の撹拌の後、完全な反応転換がGC−MSにより観察された。この反応混合物をNH4Cl飽和水溶液でクエンチし、Et2Oで抽出し、MgSO4上で乾燥させ、減圧下で濃縮した。この得られた油を、石油エーテル−Et2O混合液(9−1)での溶出によりシリカゲル上で急速濾過を用いて、精製した。減圧下での濃縮により、無色油として化合物が得られた。
4−フルオロ−2−メチルアニソール(1当量)を無水THF(0.7M)中に溶解させ、KHMDS(ヘキサメチルジシラザンカリウム−1.5当量)を室温にて添加した。この混合物を、イソ−ブチロニトリル(4当量)の添加後に、60℃に加熱した。還流を12時間にわたって継続した。この反応液をHCl水溶液(1M)でクエンチし、Et2Oで抽出した。この有機層をMgSO4で乾燥させ、減圧下(55℃にて0.1kPa(1mbar))で濃縮した。この得られた油を、石油エーテル−Et2O混合液(9−1)での溶出によりシリカゲル上で急速濾過を用いて、精製した。減圧下での濃縮により、無色油として化合物が得られた。
工程1で形成されたニトリルを無水THF(0.5M)中に溶解させ、−20℃に冷却した。メチルリチウム(1.3当量−1.6M)の溶液を滴加した。−20℃での10分の撹拌の後、反応完了を観察した。この反応液をH2SO4溶液(2M−2当量)でクエンチし、その場で形成されたイミンの完全な加水分解が観察されるまで、周囲温度にて撹拌した(一晩、周囲温度)。次に、この混合物をEt2Oで抽出し、NaHCO3飽和水溶液で洗浄した。組み合わせた有機相をMgSO4上で乾燥させ、減圧下で濃縮した。この得られた油を、石油エーテル−Et2O混合液(9−1)での溶出によりシリカゲル上で急速濾過を用いて、精製した。減圧下での溶出液の濃縮により、無色油として化合物が得られた。
1−フェニル−1−シクロプロパンカルボン酸(1当量)の無水CH2Cl2(0.5M)中の溶液に、1,1’−カルボニルジイミダゾール(1当量)を周囲温度にて添加した。この混合物を15分にわたって撹拌し、N,O−ジメチルヒドロキシルアミン塩酸塩(1当量)を添加した。撹拌を同じ温度にて1時間にわたって継続し、この混合物をHCl水溶液(1M−1.1当量)でクエンチした。この水層をEt2Oで抽出し、NaHCO3で洗浄し、MgSO4上で乾燥させた。減圧下での濃縮により、無色油として化合物が得られた。
工程2で形成されたWeinrebアミドを無水THF(0.5M)中に溶解させ、−15℃に冷却した。この混合物にEtMgBrの溶液(1M−1.5当量)を滴加した。−10/−15℃での10分の撹拌の後、完全な反応転換がGC−MSにより観察された。この反応混合物をNH4Cl飽和水溶液でクエンチし、Et2Oで抽出し、MgSO4上で乾燥させ、減圧下で濃縮した。この得られた油を、石油エーテル−Et2O混合液(9−1)での溶出によりシリカゲル上で急速濾過を用いて、精製した。減圧下での濃縮により、無色油として化合物が得られた。
以下の成分:
1つ以上の表1のPRMを含む香料材料を50%、
BASFからのLupasol WF(CAS番号09002−98−6)を50%を秤量し、ガラスバイアル瓶に加え、60℃の温水浴中に使用前に1時間載置した。Ultra−Turrax T25ベーシック装置(IKA製)を使用して、2種類の成分の混合を5分間行った。混合が完了したら、サンプルを60℃の温水浴中に±12時間載置した。均質な粘稠材料が得られる。
25グラムのブチルアクリレート−アクリル酸コポリマー乳化剤(Colloid C351、25%固形分、pKa 4.5〜4.7(Kemira Chemicals,Inc.(Kennesaw,Georgia U.S.A.))を脱イオン水200グラムに溶解及び混合する。溶液のpHを、水酸化ナトリウム溶液でpH 4.0に調整する。部分メチル化メチロールメラミン樹脂(Cymel 385、80%固形分、Cytec Industries West Paterson(New Jersey,U.S.A.))8グラムを乳化剤溶液に添加する。1つ以上の表1のPRMを含む香油200グラムを、先の混合物に機械撹拌しながら添加したところ、温度は50℃に上昇した。安定なエマルションが得られるまで高速で混合した後に、第2の溶液及び4グラムの硫酸ナトリウム塩をこのエマルションに添加する。この第2の溶液は、ブチルアクリレート−アクリル酸コポリマー乳化剤(Colloid C351、25%固形分、pKa 4.5〜4.7、Kemira)10グラム、蒸留水120グラム、pHを4.8に調整するための水酸化ナトリウム溶液、部分メチル化メチロールメラミン樹脂(Cymel 385、80%固形分、Cytec)25グラムを含有する。この混合物を70℃まで加熱し、連続的に攪拌しながら1晩にわたって維持して、カプセル封入プロセスを完了させる。アセトアセトアミド(Sigma−Aldrich(Saint Louis,Missouri,U.S.A.))23グラムをこの懸濁液に添加する。モデル780 Accusizerにより分析したときに30μmの平均カプセルサイズを得る。
混合物は、1つ以上の表1のPRMを含む香料組成物を50%、カルボキシル末端Hycar(登録商標)1300X18(CAS番号0068891−50−9)(Noveon製)(混合前に1時間にわたって60℃の温水浴中に置く)を40%、Lupasol(登録商標)WF(CAS番号09002−98−6)(BASF製)(混合前に1時間にわたって60℃の温水浴中に置く)を10%、含む。Ultra−Turrax T25基本装備(IKA製)を用いて5分間混合することにより、混合を達成する。混合後、混合物を±12時間60℃の温水浴中に置く。均質な、粘稠かつ粘着性のある物質が得られる。
本明細書に開示されたPRM、香料及びアミンを含有する製品配合の非限定的な例を、以下の表に要約する。
bメチル−ビス(タローアミドエチル)−2−ヒドロキシエチルアンモニウムメチルサルフェート。
c脂肪酸とメチルジエタノールアミンとのモル比1.5:1での反応生成物を塩化メチルで四級化して得られる、N,N−ビス(ステアロイル−オキシ−エチル)N,N−ジメチルアンモニウムクロライドとN−(ステアロイル−オキシ−エチル)N−ヒドロキシエチルN,Nジメチルアンモニウムクロライドとの1:1モル混合物。
dNational Starchから商品名CATO(登録商標)で入手可能なカチオン性高アミローストウモロコシデンプン。
e1つ以上の表1のPRMを含む香料
f米国特許第5,574,179号、第15欄、1〜5行目に記載の式を有する、エチレンオキシドとテレフタレートとのコポリマーであって、式中、各Xはメチルであり、各nは40であり、uは4であり、各R1は本質的に1,4−フェニレン部分であり、各R2は、本質的にエチレン、1,2−プロピレン部分、又はこれらの混合物である。
gWackerからのSE39
hジエチレントリアミン五酢酸。
iRohm and Haas Co.から入手可能なKATHON(登録商標)CG。「PPM」は、「百万分の一」。
jグルタルアルデヒド
kDC2310の商品名でDow Corning Corp.から入手可能なシリコーン消泡剤。
lRohm and Haas Co.から商品名Aculan 44で入手可能な、疎水変性エトキシル化ウレタン。
*本明細書に開示されているようなアミン部分を含む1種以上の材料。
†残部
Claims (9)
- 2−(R,S)−(1−(3−メチルブタ−2−エニル)シクロブチル)ブタン−2−オールを含んでなる、香料原材料。
- 香料総重量に基づいて、0.01%〜50%の2−(R,S)−(1−(3−メチルブタ−2−エニル)シクロブチル)ブタン−2−オールを含んでなる、香料。
- 消費者製品総重量に基づいて、0.0001%〜25%の2−(R,S)−(1−(3−メチルブタ−2−エニル)シクロブチル)ブタン−2−オールを含んでなり、
ベビーケア、ビューティケア、衣類及びホームケア、ファミリーケア、フェミニンケア、ヘルスケア、スナック、並びに/又は飲料製品若しくは装置からなる群から選択される、消費者製品。 - 前記消費者製品が、洗浄及び/又は処理組成物であり、前記組成物が、前記組成物総重量に基づいて、0.0001%〜25%の2−(R,S)−(1−(3−メチルブタ−2−エニル)シクロブチル)ブタン−2−オールを含んでなる、請求項3に記載の消費者製品。
- 前記消費者製品が、布地及び/又は硬質表面の、洗浄及び/又は処理組成物であり、前記組成物が、前記組成物総重量に基づいて、0.00001%〜25%の2−(R,S)−(1−(3−メチルブタ−2−エニル)シクロブチル)ブタン−2−オールを含んでなる、請求項3に記載の消費者製品。
- 前記消費者製品が、洗剤であり、前記洗剤が、前記洗剤総重量に基づいて、0.00001%〜25%の2−(R,S)−(1−(3−メチルブタ−2−エニル)シクロブチル)ブタン−2−オールを含んでなる、請求項3に記載の消費者製品。
- 前記消費者製品が、コンパクト化消費者製品であり、前記コンパクト化消費者製品が、前記コンパクト化消費者製品総重量に基づいて、0.00001%〜25%の2−(R,S)−(1−(3−メチルブタ−2−エニル)シクロブチル)ブタン−2−オールを含んでなる、請求項3に記載の消費者製品。
- 香料送達システムであって、
前記香料送達システムが、0.001%〜50%の2−(R,S)−(1−(3−メチルブタ−2−エニル)シクロブチル)ブタン−2−オールを含んでなり、前記香料送達システムが、ポリマー支援型送達システム、分子支援型送達システム、繊維支援型送達システム、アミン支援型送達システム、シクロデキストリン送達システム、デンプン封入アコード、無機担体送達システム、またはプロ香料である、香料送達システム。 - 前記香料送達システムが、ナノカプセルまたはマイクロカプセルであり、前記ナノカプセルまたはマイクロカプセルが、前記ナノカプセルまたはマイクロカプセル総重量に基づいて、0.1%〜99%の2−(R,S)−(1−(3−メチルブタ−2−エニル)シクロブチル)ブタン−2−オールを含んでなる、請求項8に記載の香料送達システム。
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2009
- 2009-11-30 CN CN200980156274.7A patent/CN102300550B/zh not_active Expired - Fee Related
- 2009-11-30 CA CA2744033A patent/CA2744033A1/en not_active Abandoned
- 2009-11-30 RU RU2011120488/15A patent/RU2588972C2/ru not_active IP Right Cessation
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CN102300550B (zh) | 2014-04-23 |
MX2011005801A (es) | 2011-06-20 |
WO2010065446A2 (en) | 2010-06-10 |
US20130012422A1 (en) | 2013-01-10 |
RU2588972C2 (ru) | 2016-07-10 |
CN102300550A (zh) | 2011-12-28 |
EP2362765B1 (en) | 2020-04-08 |
BRPI0922770A2 (pt) | 2019-09-24 |
EP2362765A2 (en) | 2011-09-07 |
RU2011120488A (ru) | 2013-01-10 |
WO2010065446A3 (en) | 2011-05-26 |
JP2012510561A (ja) | 2012-05-10 |
US20100137178A1 (en) | 2010-06-03 |
US8431520B2 (en) | 2013-04-30 |
CA2744033A1 (en) | 2010-06-10 |
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