JP2013534957A - 香料系 - Google Patents
香料系 Download PDFInfo
- Publication number
- JP2013534957A JP2013534957A JP2013516719A JP2013516719A JP2013534957A JP 2013534957 A JP2013534957 A JP 2013534957A JP 2013516719 A JP2013516719 A JP 2013516719A JP 2013516719 A JP2013516719 A JP 2013516719A JP 2013534957 A JP2013534957 A JP 2013534957A
- Authority
- JP
- Japan
- Prior art keywords
- branched
- linear
- moiety
- perfume
- delivery system
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002304 perfume Substances 0.000 title claims abstract description 219
- 239000000203 mixture Substances 0.000 claims abstract description 116
- 239000003205 fragrance Substances 0.000 claims abstract description 75
- 239000002994 raw material Substances 0.000 claims abstract description 53
- 239000000047 product Substances 0.000 claims description 106
- 229920000642 polymer Polymers 0.000 claims description 42
- -1 2 - cyclopropyl Chemical group 0.000 claims description 35
- 150000001412 amines Chemical class 0.000 claims description 29
- 239000004744 fabric Substances 0.000 claims description 28
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 26
- 239000003599 detergent Substances 0.000 claims description 26
- 239000000835 fiber Substances 0.000 claims description 23
- 150000002576 ketones Chemical group 0.000 claims description 23
- 238000004140 cleaning Methods 0.000 claims description 21
- 239000003094 microcapsule Substances 0.000 claims description 21
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 14
- 239000011159 matrix material Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229920000858 Cyclodextrin Polymers 0.000 claims description 10
- 229920002472 Starch Polymers 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 239000008107 starch Substances 0.000 claims description 10
- 235000019698 starch Nutrition 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000002825 nitriles Chemical group 0.000 claims description 9
- 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 9
- 239000004615 ingredient Substances 0.000 claims description 8
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 7
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
- 150000001345 alkine derivatives Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 2
- GVSTVIASYRSHQM-RYUDHWBXSA-N 3-[(1s,5r)-6,6-dimethyl-4-bicyclo[3.1.1]hept-3-enyl]-2,2-dimethylpropanal Chemical compound C1[C@@]2([H])C(CC(C)(C)C=O)=CC[C@]1([H])C2(C)C GVSTVIASYRSHQM-RYUDHWBXSA-N 0.000 claims 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 238000003756 stirring Methods 0.000 description 22
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 21
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
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- 229940088598 enzyme Drugs 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
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- 239000003208 petroleum Substances 0.000 description 11
- 239000002775 capsule Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007844 bleaching agent Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
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- 229910052751 metal Inorganic materials 0.000 description 9
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- 239000004094 surface-active agent Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 238000009792 diffusion process Methods 0.000 description 7
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- 210000004209 hair Anatomy 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 239000002453 shampoo Substances 0.000 description 7
- 235000011888 snacks Nutrition 0.000 description 7
- 238000012546 transfer Methods 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
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- 238000004851 dishwashing Methods 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 239000000123 paper Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000009825 accumulation Methods 0.000 description 5
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- 150000001299 aldehydes Chemical class 0.000 description 5
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- 230000003750 conditioning effect Effects 0.000 description 5
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- 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
- 238000011065 in-situ storage Methods 0.000 description 5
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- 238000003860 storage Methods 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- 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
- 239000002253 acid Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
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- 235000010675 chips/crisps Nutrition 0.000 description 4
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- 150000003624 transition metals Chemical class 0.000 description 4
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- LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-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
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
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- 238000013459 approach Methods 0.000 description 3
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
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- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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
- C11B9/00—Essential oils; Perfumes
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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- C11D3/2031—Monohydric alcohols unsaturated fatty or with at least 8 carbon atoms in the alkenyl chain
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
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- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
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- C07C43/162—Unsaturated ethers containing rings other than six-membered aromatic rings
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- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
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- C07C47/00—Compounds having —CHO groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/45—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings having unsaturation outside the rings
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C49/11—Saturated compounds containing keto groups bound to acyclic carbon atoms containing rings monocyclic
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
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- C07C49/553—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings polycyclic
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
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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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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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Abstract
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、布地及びホームケア、ファミリーケア、女性用ケア、ヘルスケア、スナック、及び/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、拭き取り布;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/又はネコ)を処理する製品及び/又は処理に関する方法;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系、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/又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/又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。
一態様では、任意の溶媒と、
a)以下の構造を有する香料原材料:
(i)CHO
(ii)CR3R4OR5(式中、R3、R4及びR5は、それぞれ独立して、水素、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分、ケトン部分を含む直鎖状又は分枝状C2〜C5アルキル部分、及び、ケトン部分を含む直鎖状又は分枝状C2〜C5アルケニル部分からなる群から選択される)からなる群から選択され;
式中、R2は:
(i)水素;
(ii)直鎖状又は分枝状C1〜C6アルキル部分;
(iii)直鎖状又は分枝状C2〜C6アルケニル部分;及び
(iv)直鎖状又は分枝状C2〜C6アルキン部分、からなる群から選択される);
b)以下の構造を有する香料原材料:
(i)CHO
(ii)CR4R5OR6(式中、R4、R5及びR6は、それぞれ独立して、水素、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分、ケトン部分を含む直鎖状又は分枝状C2〜C5アルキル部分、及びケトン部分を含む直鎖状又は分枝状C2〜C5アルケニル部分、からなる群から選択される)からなる群から選択され;
式中、R2及びR3は、それぞれ独立して以下:
(i)直鎖状又は分枝状C1〜C6アルキル部分;
(ii)直鎖状又は分枝状C2〜C6アルケニル部分;
(iii)直鎖状又は分枝状C2〜C6アルキン部分、からなる群から選択され、又は
一態様では、R2とR3が一緒になる場合、R2及びR3は環状構造を形成し、一態様では、C3〜C6環状構造を形成し、一態様では、上記環状構造は、シクロプロパン、シクロブタン、シクロペンタン、シクロヘキサンから選択される);
c)以下の構造を有する香料原材料:
(i)ニトリル部分;
(ii)C=OR(式中、Rは、水素、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分である);からなる群から選択され、
R2とR3は、シクロプロパン、シクロブタン、シクロペンタン、又はシクロヘキサンから選択される環状構造を形成し、
別の態様では、R1はメチルケトンであって、R2及びR3は、それぞれがメチルである);
d)以下の構造を有する香料原材料:
(i)直鎖状又は分枝状C1〜C6アルキル部分;
(ii)直鎖状又は分枝状C2〜C6アルケニル部分;
(iii)直鎖状又は分枝状C2〜C6アルキン部分;
(iv)COR5(式中、R5は、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分からなる群から選択される);
(v)COOR5(式中、R5は、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分からなる群から選択される);からなる群から選択され、
式中、R2は:
(i)水素;
(ii)直鎖状又は分枝状C1〜C6アルキル部分;
(iii)直鎖状又は分枝状C2〜C4アルケニル部分;及び
(iv)直鎖状又は分枝状C2〜C6アルキン部分、からなる群から選択され;
R3及びR4は、それぞれ独立して:
(i)直鎖状又は分枝状C1〜C6アルキル部分;
(ii)直鎖状又は分枝状C2〜C4アルケニル部分;
(iii)直鎖状又は分枝状C2〜C6アルキン部分;からなる群から選択され、又は
一態様では、R3とR4が一緒になる場合、R3とR4は環状構造を形成し、一態様では、C3〜C6環状構造を形成し、一態様では、上記環状構造は、シクロプロパン、シクロブタン、シクロペンタン、シクロヘキサンから選択される);
e)以下の構造を有する香料原材料:
(i)CHO;
(ii)CN;
(ii)COR4
(式中、R4は、直鎖状又は分枝状C1〜C6アルキル部分;直鎖状又は分枝状C2〜C6アルケニル部分;直鎖状又は分枝状C2〜C6アルキン部分;非置換フェニル部分;置換フェニル部分からなる群から選択され、一態様では、上記置換フェニル部分は、メチル及び/又はエチルから選択される置換基を含んでよい);
(iv)CR5R6OR7(式中、R5、R6及びR7は、それぞれ独立して、水素、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分、ケトン部分を含む直鎖状又は分枝状C2〜C5アルキル部分、ケトン部分を含む直鎖状又は分枝状C2〜C5アルケニル部分からなる群から選択される);
(v)COOR8(式中、R8は、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分からなる群から選択される)、からなる群から選択され;
式中、R2は:
(i)直鎖状又は分枝状C1〜C6アルキル部分;
(ii)直鎖状又は分枝状C2〜C6アルケニル部分;
(iii)直鎖状又は分枝状C2〜C6アルキン部分;及び
(iv)CH2−シクロプロピル;からなる群から選択され、
式中、R3は:
(i)直鎖状又は分枝状C1〜C6アルキル部分;
(ii)直鎖状又は分枝状C2〜C6アルケニル部分;
(iii)直鎖状又は分枝状C2〜C6アルキン部分;及び
一態様では、R2とR3が一緒になる場合、R2とR3は環状構造を形成し、一態様では、C3〜C6環状構造を形成し、一態様では、上記環状構造は、シクロプロパン、シクロブタン、シクロペンタン、又はシクロヘキサンから選択される);
f)以下の構造を有する香料原材料:
(i)直鎖状又は分枝状C1〜C6アルキル部分;
(ii)直鎖状又は分枝状C2〜C4アルケニル部分;
(iii)直鎖状又は分枝状C2〜C6アルキン部分;及び
一態様では、R1とR2が一緒になる場合、R1とR2は環状構造を形成し、一態様では、C3〜C6環状構造を形成し、一態様では、上記環状構造は、シクロプロパン、シクロブタン、シクロペンタン、又はシクロヘキサンから選択され);
g)以下の構造を有する香料原材料:
(i)CHO;
(ii)ニトリル部分;
(iii)COR4
(式中、R4は、直鎖状又は分枝状C1〜C6アルキル部分;直鎖状又は分枝状C2〜C6アルケニル部分;直鎖状又は分枝状C2〜C6アルキン部分;非置換フェニル部分;置換フェニル部分からなる群から選択され、一態様では、上記置換フェニル部分は、メチル及び/又はエチルから選択される置換基を含んでよい);
(iv)CR5R6OR7(式中、R5、R6及びR7は、それぞれ独立して、水素、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分、ケトン部分を含む直鎖状又は分枝状C2〜C5アルキル部分、ケトン部分を含む直鎖状又は分枝状C2〜C5アルケニル部分からなる群から選択される);
(v)COOR8(式中、R8は、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分からなる群から選択される)、からなる群から選択され;
式中、R2は:
(i)直鎖状又は分枝状C1〜C6アルキル部分;
(ii)直鎖状又は分枝状C2〜C6アルケニル部分;
(iii)直鎖状又は分枝状C2〜C6アルキン部分;及び
(iv)CH2−シクロプロピル;からなる群から選択され、
式中、R3は:
(i)直鎖状又は分枝状C1〜C6アルキル部分;
(ii)直鎖状又は分枝状C2〜C6アルケニル部分;
(iii)直鎖状又は分枝状C2〜C6アルキン部分;及び
一態様では、R2とR3が一緒になる場合、R2とR3は環状構造を形成し、一態様では、C3〜C6環状構造を形成し、一態様では、上記環状構造は、シクロプロパン、シクロブタン、シクロペンタン、又はシクロヘキサンから選択される);からなる群から選択される香料原材料と、を含む香料が開示されている。
一態様では、送達系の全重量に対して、約0.001重量%〜約99重量%、0.1重量%〜約90重量%、又は約1重量%〜約75重量%の上記香料を含み得る香料送達系が開示されている。
特定の香料送達系、特定の香料送達系を製造する方法、及びこのような香料送達系の使用は、米国特許出願第2007/0275866(A1)号に開示されている。このような香料送達系には以下のものが挙げられる。
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好適であり、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。このような補助剤は、本出願人らの香料及び/又は香料系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。このような追加の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使用されるべき作業の性質に依存する。好適な補助物質としては、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、布地柔軟剤、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ている特定の消費者製品は、部位を、とりわけ、表面又は布地を、洗浄又は処理するために使用することができる。通常、この部位の少なくとも一部は、未希釈形態の又は液体に希釈された、本出願人らの組成物の実施形態、例えば洗浄液と接触され、そしてその後、任意により、その部位が洗浄及び/又はすすがれてもよい。一態様では、ある部位が任意により洗浄及び/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、次に任意により洗浄及び/又はすすがれる。本発明の目的上、洗浄には、擦ること及び機械的撹拌が挙げられるが、これらに限定されない。布地は、標準的な消費者の使用条件で洗濯又は処理することが可能な大部分の任意の布地を含んでよい。開示される組成物を含み得る液体は、約3〜約11.5のpHを含んでよい。このような組成物は、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。
本出願の「試験方法」の項で開示される試験方法は、本出願人らの発明が本明細書に記載され及び特許請求されているように、本出願人らの発明のパラメータの各値を決定するために使用されるべきであると理解される。
「logPの計算値」(ClogP)は、ハンシュ及びレオのフラグメント手法(The fragment approach of Hansch and Leo(cf.,A.Leo,in Comprehensive Medicinal Chemistry,Vol.4,C.Hansch,P.G.Sammens,J.B.Taylor,and C.A.Ramsden,Eds.P.295,Pergamon Press,1990,参照により本明細書中に組み込まれる))により決定される。ClogP値は、Daylight Chemical Information Systems Inc.(Irvine,California U.S.A.)から入手可能な「CLOGP」プログラムを用いることにより計算することができる。
沸点は、ASTM法D2887−04a「ガスクロマトグラフィーによる、石油留分の沸点範囲分布のための標準試験方法(Standard Test Method for Boiling Range Distribution of Petroleum Fractions by Gas Chromatography)」(ASTMインターナショナル)により測定される。
(a)芳香剤非含有消費者製品配合物(シャンプー又はリーブオンコンディショナー)を入手する。
1.20mLのヘッドスペースバイアル
2.タイマー。
3.ガスクロマトグラフ(GC):CIS−4インジェクター、MPS−2オートサンプラー及びTDUを備えるAgilent model 6890(Gerstel,Mulheim,Germany)SPME分析において、スプリット/スプリットレスインジェクター(CIS−4インジェクターとは異なる)を使用した。
4.GCカラム:J&W DB−5 MS、30M×0.25mm ID、膜厚1.0μm(J&W Scientific of Folsom,California,USAから入手した)。
5.キャリアガス、ヘリウム、流速1.5mL/分。
6.インジェクターライナーは、Supelcoの特定のSPMEライナー(0.75mm ID)である。
7.検出器は、Agilent Technologies,Inc.(Wilmington,DE.,USA)から入手し、約230℃のソース温度と約150℃のMS四重極温度を有するモデル5973質量選択検出器である。
1.試料を適切な試料トレイに移し、SPME−GC−MS分析を続ける。
2.一連の試料充填及び分析を開始する。このステップにおいては、試料をオートサンプラートレイ上で少なくとも2時間均衡化させ、次に、トレイから直接サンプリングする。SPME繊維集合体は、DVB/CAR/PDMS(50/30μm、24ga、長さ1cm)である。サンプリング時間は、5分間である。
3.インジェクター温度は、260℃である。
4.次に、GC−MS分析の実行を開始する。脱着時間は、5分間である。
5.以下の温度プログラムを使用する。
i)約50℃の初期温度を3分間保持する。
ii)この初期温度を約6℃/分の速度で約250℃の温度に達するまで高め、次に25℃/分の速度で275℃まで高め、約4.67分間保持する。
6.Hewlett Packardから購入し、使用許諾を受けた、John Wiley & Sonsと米国国立標準技術研究所(NIST)のMSスペクトルライブラリを使用して、香料化合物を特定する。
7.Agilent Technologies,Inc.(Wilmington,DE,USA)から入手したChemstationソフトウェアを使用して、特定イオンのクロマトグラフィーピークを積分する。
8.試料A中の香料原材料のピーク面積を試料B中のピーク面積で割ることで、各PRMの比率を計算する。
9.次に、香料における香料原材料の重量組成によって、各比率を重み付けする。
10.ステップ9で得られた個別の香料原材料比率の合計によって、ヘッドスペース率を計算する。
−トナリドの原液:70mgのトナリドを秤量し、20mLの試薬用ヘキサンを加える。
−内標準溶液:20mLの試薬用ヘキサンで200μLの原液を希釈する。
−均質化するように混合する。
−液体洗剤製品を2g秤量し、抽出容器に入れる。
−2mLの内標準溶液を加えて、容器を閉じる。
−抽出容器を20回手でゆっくりとひっくり返し、香料を抽出する。
−硫酸ナトリウムを1匙加える。
−層の分離後、すぐにヘキサン層をガスクロマトグラフオートサンプラーバイアルに入れて、バイアルの蓋をする。
−ガスクロマトグラフ注入ポートにスプリットレス(1.5μL)を注入する。
−ガスクロマトグラフィー質量分析を行う。
−液体洗剤製品を2g秤量し、抽出容器に入れる。
−2mLの内標準溶液を加えて、容器を閉じる。
−抽出容器を20回手でゆっくりとひっくり返し、香料を抽出する。
−硫酸ナトリウムを1匙加える。
−層の分離後、すぐにヘキサン層をガスクロマトグラフオートサンプラーバイアルに入れて、バイアルの蓋をする。
−ガスクロマトグラフ注入ポートにスプリットレス(1.5μL)を注入する。
−ガスクロマトグラフィー質量分析を行う。
−個別の香料原材料におけるカプセルからの香料の漏れ
香料の漏れ(%)={(カプセルの香料原材料の面積×参照の内標準溶液の面積×参照の重量)/(カプセルの内標準溶液の面積×参照の香料原材料の面積×カプセルの重量)}×100
カラム:J&W Scientific DB−1
長さ:30メートル、内径0.25メートル、膜厚1マイクロメートル
方法:
−スプリット注入:17/1スプリット比
−オートサンプラー:1.13マイクロリットル/注入
−カラム流量:1.10マイクロリットル/分
−空気流:345ミリリットル/分
−入口温度:245℃
−検出器温度:285℃
−初期温度=50℃、5℃/分の昇温速度、最終温度=280℃、最終時間=6分間
−推定導入:1回嗅ぐごとに12秒、GCガスを試料希釈物に加える。
式1を有するPRMにおける合成例
表1の材料1の合成のための、代表的な手順を与える。
表1の材料9の合成のための、代表的な手順を与える。
表1の材料11の合成のための、代表的な手順を与える。
表1の材料16の合成のための、代表的な手順を与える。
表1の材料21の合成のための、代表的な手順を与える。
表1の材料26の合成のための、代表的な手順を与える。
表1の材料27の合成のための、代表的な手順を与える。
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時間載置する。Ultra−Turrax T25ベーシック装置(IKA製)を使用して、2つの成分の混合を5分間行う。混合が完了したら、試料を60℃の温水浴中に±12時間載置する。均質な粘稠材料を得る。
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℃に上昇する。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℃に加熱し、一晩撹拌し続けて、カプセル化プロセスを完了する。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を得る。
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。
d National 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。
e 1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段、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。
g WackerからのSE39
h ジエチレントリアミン五酢酸。
i Rohm and Haas Co.から入手可能なKATHON(登録商標)CG。「PPM」は、「百万分率」である。
j グルタルアルデヒド
k DC2310の商標名でDow Corning Corp.から入手可能なシリコーン消泡剤。
l Rohm 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つ以上の材料。
† 残部
Claims (15)
- 任意の溶媒と、
a)以下の構造を有する香料原材料:
(i)CHO
(ii)CR3R4OR5(式中、R3、R4及びR5は、それぞれ独立して、水素、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分、ケトン部分を含む直鎖状又は分枝状C2〜C5アルキル部分、及び、ケトン部分を含む直鎖状又は分枝状C2〜C5アルケニル部分からなる群から選択される)
からなる群から選択され;
(式中、R2は:
(i)水素;
(ii)直鎖状又は分枝状C1〜C6アルキル部分;
(iii)直鎖状又は分枝状C2〜C6アルケニル部分;及び
(iv)直鎖状又は分枝状C2〜C6アルキン部分;
からなる群から選択される)、
b)以下の構造を有する香料原材料:
(i)CHO
(ii)CR4R5OR6(式中、R4、R5及びR6は、それぞれ独立して、水素、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分、ケトン部分を含む直鎖状又は分枝状C2〜C5アルキル部分、及びケトン部分を含む直鎖状又は分枝状C2〜C5アルケニル部分、からなる群から選択される)
からなる群から選択され;
(式中、R2及びR3は、それぞれ独立して以下:
(iv)直鎖状又は分枝状C1〜C6アルキル部分;
(v)直鎖状又は分枝状C2〜C6アルケニル部分;
(vi)直鎖状又は分枝状C2〜C6アルキン部分;
からなる群から選択され、又は
R2とR3が一緒になる場合、R2とR3は環状構造を形成する);
c)以下の構造を有する香料原材料:
(iv)ニトリル部分;
(v)C=OR(式中、Rは、水素、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分である);
からなる群から選択され、
R2とR3は、シクロプロパン、シクロブタン、シクロペンタン、又はシクロヘキサンから選択される環状構造を形成し、又は
R1はメチルケトンであり、R2とR3はそれぞれメチルである);
d)以下の構造を有する香料原材料:
(i)直鎖状又は分枝状C1〜C6アルキル部分;
(ii)直鎖状又は分枝状C2〜C6アルケニル部分;
(iii)直鎖状又は分枝状C2〜C6アルキン部分;
(iv)COR5(式中、R5は、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分からなる群から選択される);
(v)COOR5(式中、R5は、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分からなる群から選択される);
からなる群から選択され、
式中、R2は:
(i)水素;
(ii)直鎖状又は分枝状C1〜C6アルキル部分;
(iii)直鎖状又は分枝状C2〜C4アルケニル部分;及び
(iv)直鎖状又は分枝状C2〜C6アルキン部分、からなる群から選択され;
R3及びR4は、それぞれ独立して:
(i)直鎖状又は分枝状C1〜C6アルキル部分;
(ii)直鎖状又は分枝状C2〜C4アルケニル部分;
(iii)直鎖状又は分枝状C2〜C6アルキン部分;
からなる群から選択され、又は
R3とR4が一緒になる場合、R3とR4は環状構造を形成する);
e)以下の構造を有する香料原材料:
(iv)CHO;
(v)CN;
(vi)COR4
(式中、R4は、直鎖状又は分枝状C1〜C6アルキル部分;直鎖状又は分枝状C2〜C6アルケニル部分;直鎖状又は分枝状C2〜C6アルキン部分;非置換フェニル部分;置換フェニル部分からなる群から選択され、一態様では、前記置換フェニル部分は、メチル及び/又はエチルから選択される置換基を含んでよい);
(iv)CR5R6OR7(式中、R5、R6及びR7は、それぞれ独立して、水素、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分、ケトン部分を含む直鎖状又は分枝状C2〜C5アルキル部分、ケトン部分を含む直鎖状又は分枝状C2〜C5アルケニル部分からなる群から選択される);
(v)COOR8(式中、R8は、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分からなる群から選択される)、からなる群から選択され;
式中、R2は:
(i)直鎖状又は分枝状C1〜C6アルキル部分;
(ii)直鎖状又は分枝状C2〜C6アルケニル部分;
(iii)直鎖状又は分枝状C2〜C6アルキン部分;及び
(iv)CH2−シクロプロピル;
からなる群から選択され、
式中、R3は:
(i)直鎖状又は分枝状C1〜C6アルキル部分;
(ii)直鎖状又は分枝状C2〜C6アルケニル部分;
(iii)直鎖状又は分枝状C2〜C6アルキン部分;
からなる群から選択され、
R2とR3が一緒になる場合、R2とR3は環状構造を形成する);
f)以下の構造を有する香料原材料:
(i)直鎖状又は分枝状C1〜C6アルキル部分;
(ii)直鎖状又は分枝状C2〜C4アルケニル部分;
(iii)直鎖状又は分枝状C2〜C6アルキン部分;
からなる群から選択され、
R1とR2が一緒になる場合、R1とR2は環状構造を形成する);及び
g)以下の構造を有する香料原材料:
(i)CHO
(ii)ニトリル部分;
(iii)COR4
(式中、R4は、直鎖状又は分枝状C1〜C6アルキル部分;直鎖状又は分枝状C2〜C6アルケニル部分;直鎖状又は分枝状C2〜C6アルキン部分;非置換フェニル部分;置換フェニル部分からなる群から選択され、一態様では、前記置換フェニル部分は、メチル及び/又はエチルから選択される置換基を含んでよい);
(iv)CR5R6OR7(式中、R5、R6及びR7は、それぞれ独立して、水素、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分、ケトン部分を含む直鎖状又は分枝状C2〜C5アルキル部分、及び、ケトン部分を含む直鎖状又は分枝状C2〜C5アルケニル部分からなる群から選択される);
(v)COOR8(式中、R8は、直鎖状又は分枝状C1〜C5アルキル部分、直鎖状又は分枝状C2〜C5アルケニル部分からなる群から選択される);
からなる群から選択され、
式中、R2は:
(i)直鎖状又は分枝状C1〜C6アルキル部分;
(ii)直鎖状又は分枝状C2〜C6アルケニル部分;
(iii)直鎖状又は分枝状C2〜C6アルキン部分;及び
(iv)CH2−シクロプロピル、からなる群から選択され;
式中、R3は:
(i)直鎖状又は分枝状C1〜C6アルキル部分;
(ii)直鎖状又は分枝状C2〜C6アルケニル部分;
(iii)直鎖状又は分枝状C2〜C6アルキン部分;からなる群から選択され、
R2とR3が一緒になる場合、R2とR3は環状構造を形成する);
からなる群から選択される香料原材料と、を含み、
但し、前記香料原材料は、3−((1R,5S)−6,6−ジメチルビシクロ[3.1.1]ヘプタ−2−エン−2−イル)−2,2−ジメチルプロパナールではない、香料。 - 香料の全重量に対して、0.0001重量%〜50重量%、又は好ましくは0.01重量%〜25重量%の前記香料原材料を含む、請求項1に記載の香料。
- 請求項1に記載の香料と、補助成分と、を含む、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って、補助成分を含む、請求項2に記載の消費者製品。
- 前記消費者製品が、布地及び/又は硬質表面用の洗浄及び/又は処理組成物であって、前記組成物が、組成物の全重量に対して、0.00001重量%〜35重量%、又は好ましくは0.01重量%〜25重量%の前記香料を含む、請求項4に記載の消費者製品。
- 前記消費者製品が洗剤であって、前記洗剤が、洗剤の全重量に対して、0.00001重量%〜35重量%、又は好ましくは0.01重量%〜25重量%の前記香料を含む、請求項4に記載の消費者製品。
- 前記消費者製品が、超コンパクト化消費者製品であって、前記超コンパクト化消費者製品が、超コンパクト化消費者製品の全重量に対して、0.00001重量%〜35重量%、又は好ましくは0.01重量%〜25重量%の前記香料を含む、請求項4に記載の消費者製品。
- 送達系の全重量に対して、0.001重量%〜99重量%、好ましくは0.1重量%〜90重量%、又はより好ましくは1重量%〜75重量%の請求項1に記載の香料を含む香料送達系であって、前記香料送達系が、ポリマー支援型送達系;分子支援型送達系;繊維支援型送達系;アミン支援型送達系;シクロデキストリン送達系;デンプン封入アコード;無機担体送達系;又はプロ香料である、香料送達系。
- 前記香料送達系が、ナノカプセル又はマイクロカプセルの全重量に対して、0.001重量%〜99重量%、好ましくは0.1重量%〜95重量%、又は更に好ましくは0.1重量%〜87重量%の請求項1に記載の香料を含むナノカプセル又はマイクロカプセルである、請求項8に記載の香料送達系。
- 前記香料送達系がデンプン封入アコードである、請求項9に記載の香料送達系。
- 前記香料送達系が、香料送達系の全重量に対して、2重量%〜20重量%、好ましくは3重量%〜10重量%、又は更に好ましくは5重量%〜8重量%の前記香料を含むシクロデキストリン送達系である、請求項9に記載の香料送達系。
- 前記香料送達系がポリマー支援型送達マトリックス系である、請求項9に記載の香料送達系。
- 前記香料送達系がアミン支援型送達系である、請求項9に記載の香料送達系。
- 前記香料送達系がプロ香料アミン反応生成物である、請求項9に記載の香料送達系。
- 請求項9〜14のいずれか一項に記載の香料送達系から選択される香料送達系を、消費者製品の全重量に対して、0.001重量%〜20重量%含む、消費者製品。
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CN106232569A (zh) * | 2014-04-21 | 2016-12-14 | 高砂香料工业株式会社 | 新化合物及含有该化合物的香料组合物 |
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- 2011-06-22 BR BR112012032621A patent/BR112012032621A2/pt not_active IP Right Cessation
- 2011-06-22 EP EP11728510.6A patent/EP2585568A1/en not_active Ceased
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US20150141310A1 (en) | 2015-05-21 |
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EP3121256A1 (en) | 2017-01-25 |
BR112012032621A2 (pt) | 2019-09-24 |
CA2799484A1 (en) | 2011-12-29 |
CA2799484C (en) | 2016-02-02 |
EP3287511A1 (en) | 2018-02-28 |
CA2900812A1 (en) | 2011-12-29 |
EP3121255B1 (en) | 2018-03-28 |
CA2900812C (en) | 2017-07-04 |
EP2585568A1 (en) | 2013-05-01 |
JP5868966B2 (ja) | 2016-02-24 |
CN102947433A (zh) | 2013-02-27 |
US9994793B2 (en) | 2018-06-12 |
US20180258371A1 (en) | 2018-09-13 |
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