CN113073006A - 有机化合物中或与之相关的改进 - Google Patents
有机化合物中或与之相关的改进 Download PDFInfo
- Publication number
- CN113073006A CN113073006A CN202110456946.9A CN202110456946A CN113073006A CN 113073006 A CN113073006 A CN 113073006A CN 202110456946 A CN202110456946 A CN 202110456946A CN 113073006 A CN113073006 A CN 113073006A
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- China
- Prior art keywords
- acetate
- formula
- compound
- ethyl
- methyl
- 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.)
- Withdrawn
Links
- 150000002894 organic compounds Chemical class 0.000 title description 4
- 230000006872 improvement Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 239000002304 perfume Substances 0.000 claims abstract description 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 18
- 239000003921 oil Substances 0.000 claims description 36
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 claims description 36
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 claims description 35
- BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 claims description 35
- 239000004615 ingredient Substances 0.000 claims description 33
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 claims description 20
- -1 galbanum ester Chemical class 0.000 claims description 17
- 240000007436 Cananga odorata Species 0.000 claims description 16
- 238000004140 cleaning Methods 0.000 claims description 10
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 10
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims description 10
- 235000012141 vanillin Nutrition 0.000 claims description 10
- 239000003599 detergent Substances 0.000 claims description 9
- 229940073505 ethyl vanillin Drugs 0.000 claims description 9
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 claims description 8
- 235000007571 Cananga odorata Nutrition 0.000 claims description 8
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 8
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims description 8
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 8
- HCRBXQFHJMCTLF-ZCFIWIBFSA-N ethyl (2r)-2-methylbutanoate Chemical compound CCOC(=O)[C@H](C)CC HCRBXQFHJMCTLF-ZCFIWIBFSA-N 0.000 claims description 8
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 7
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- KGEKLUUHTZCSIP-HOSYDEDBSA-N [(1s,4s,6r)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-HOSYDEDBSA-N 0.000 claims description 6
- IGODOXYLBBXFDW-UHFFFAOYSA-N alpha-Terpinyl acetate Chemical compound CC(=O)OC(C)(C)C1CCC(C)=CC1 IGODOXYLBBXFDW-UHFFFAOYSA-N 0.000 claims description 6
- 230000001166 anti-perspirative effect Effects 0.000 claims description 6
- 239000003213 antiperspirant Substances 0.000 claims description 6
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 claims description 6
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 claims description 6
- 239000002781 deodorant agent Substances 0.000 claims description 6
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 claims description 6
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 claims description 6
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 claims description 6
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 5
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 claims description 5
- 239000004744 fabric Substances 0.000 claims description 5
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 claims description 5
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims description 4
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 4
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims description 4
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 4
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims description 4
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 claims description 4
- 239000005770 Eugenol Substances 0.000 claims description 4
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 4
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims description 4
- 229940007550 benzyl acetate Drugs 0.000 claims description 4
- 229960002903 benzyl benzoate Drugs 0.000 claims description 4
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims description 4
- 229940043350 citral Drugs 0.000 claims description 4
- 235000000484 citronellol Nutrition 0.000 claims description 4
- 239000001813 ethyl (2R)-2-methylbutanoate Substances 0.000 claims description 4
- 229940090910 ethyl 2-methylbutyrate Drugs 0.000 claims description 4
- 229960002217 eugenol Drugs 0.000 claims description 4
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 claims description 4
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 claims description 4
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 claims description 4
- 229930007744 linalool Natural products 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 claims description 4
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 claims description 4
- 229940116411 terpineol Drugs 0.000 claims description 4
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 claims description 3
- CRIGTVCBMUKRSL-FNORWQNLSA-N 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enone Chemical compound C\C=C\C(=O)C1C(C)=CCCC1(C)C CRIGTVCBMUKRSL-FNORWQNLSA-N 0.000 claims description 3
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 claims description 3
- MBZRJSQZCBXRGK-UHFFFAOYSA-N 4-tert-Butylcyclohexyl acetate Chemical compound CC(=O)OC1CCC(C(C)(C)C)CC1 MBZRJSQZCBXRGK-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- JOZKFWLRHCDGJA-LLVKDONJSA-N Citronellyl acetate Natural products CC(=O)OCC[C@H](C)CCC=C(C)C JOZKFWLRHCDGJA-LLVKDONJSA-N 0.000 claims description 3
- 239000005792 Geraniol Substances 0.000 claims description 3
- DUKPKQFHJQGTGU-UHFFFAOYSA-N Hexyl salicylic acid Chemical compound CCCCCCOC(=O)C1=CC=CC=C1O DUKPKQFHJQGTGU-UHFFFAOYSA-N 0.000 claims description 3
- 229940022663 acetate Drugs 0.000 claims description 3
- CRIGTVCBMUKRSL-UHFFFAOYSA-N alpha-Damascone Natural products CC=CC(=O)C1C(C)=CCCC1(C)C CRIGTVCBMUKRSL-UHFFFAOYSA-N 0.000 claims description 3
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 claims description 3
- 229940062909 amyl salicylate Drugs 0.000 claims description 3
- 229940115397 bornyl acetate Drugs 0.000 claims description 3
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 claims description 3
- NYNCZOLNVTXTTP-UHFFFAOYSA-N ethyl 2-(1,3-dioxoisoindol-2-yl)acetate Chemical compound C1=CC=C2C(=O)N(CC(=O)OCC)C(=O)C2=C1 NYNCZOLNVTXTTP-UHFFFAOYSA-N 0.000 claims description 3
- 229940113087 geraniol Drugs 0.000 claims description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000002453 shampoo Substances 0.000 claims description 3
- NPFVOOAXDOBMCE-PLNGDYQASA-N (3Z)-hex-3-en-1-yl acetate Chemical compound CC\C=C/CCOC(C)=O NPFVOOAXDOBMCE-PLNGDYQASA-N 0.000 claims description 2
- KRLBLPBPZSSIGH-CSKARUKUSA-N (6e)-3,7-dimethylnona-1,6-dien-3-ol Chemical compound CC\C(C)=C\CCC(C)(O)C=C KRLBLPBPZSSIGH-CSKARUKUSA-N 0.000 claims description 2
- DNRJTBAOUJJKDY-UHFFFAOYSA-N 2-Acetyl-3,5,5,6,8,8-hexamethyl-5,6,7,8- tetrahydronaphthalene Chemical compound CC(=O)C1=C(C)C=C2C(C)(C)C(C)CC(C)(C)C2=C1 DNRJTBAOUJJKDY-UHFFFAOYSA-N 0.000 claims description 2
- MJTPMXWJHPOWGH-UHFFFAOYSA-N 2-Phenoxyethyl isobutyrate Chemical compound CC(C)C(=O)OCCOC1=CC=CC=C1 MJTPMXWJHPOWGH-UHFFFAOYSA-N 0.000 claims description 2
- BJLRAKFWOUAROE-UHFFFAOYSA-N 2500-83-6 Chemical compound C12C=CCC2C2CC(OC(=O)C)C1C2 BJLRAKFWOUAROE-UHFFFAOYSA-N 0.000 claims description 2
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims description 2
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- XRHCAGNSDHCHFJ-UHFFFAOYSA-N Ethylene brassylate Chemical compound O=C1CCCCCCCCCCCC(=O)OCCO1 XRHCAGNSDHCHFJ-UHFFFAOYSA-N 0.000 claims description 2
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- ZPUKHRHPJKNORC-UHFFFAOYSA-N Longifolene Natural products CC1(C)CCCC2(C)C3CCC1(C3)C2=C ZPUKHRHPJKNORC-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
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Abstract
Description
本申请是申请日为2013年11月12日、申请号为201380058686.3、发明名称为“有机化合物中或与之相关的改进”的中国专利申请的分案申请。
本发明涉及用于给消费品传递期望的香味香型的香料成分和香料制品,特别地,本发明涉及可以用作用于完全或部分替代具有过敏反应争议的化合物异丁子香酚的成分和香料油。
异丁子香酚是香料中广泛使用的成分。它因其花香和花香-辛香谐香例如康乃馨和百合而具有价值。一般而言,它可以以宽范围的剂量使用,例如0.1-10%重量。然而,由于在其引起皮肤过敏症的可能性方面的关注,对于大部分实际目的而言,其应用限于在消费品中200ppm,相当于在香料油中使用约0.2-2%。
因此,需要提供可以在香料制品中用作异丁子香酚替代品的成分或其在香料制品中的应用可以显著减少异丁子香酚在这样的制品中的用量的成分。
显示为异丁子香酚的花香-辛香香型的香料成分包括香草醛和甲基丹提力士。然而,这些成分各自的应用并非没有其问题。例如,香草醛在用于横跨一定范围的消费品基质的香料制品中时显示倾向于脱色的趋势。另一方面,甲基丹提力士因其高水溶性而难以用于香料油,且结果是不易于以足够高的用量配制用于大部分消费品。除此之外,甲基丹提力士在香料油中高于1或2%的应用水平存在一些不期望的享乐特性,特别地,它开始赋予不期望的愈创木酚或酚香型。
对在香料油中可以用作异丁子香酚的部分或完全替代品的香料成分仍然存在需求,这些成分无过敏性且在加速条件下贮存时在消费品基质中显示良好的颜色稳定性。
本发明在第一个方面提供包含式(I)的化合物的香料油
其中R1表示甲基或乙基且R2表示甲基或乙基。
式(I)的具体化合物是这样的化合物,其中R1是甲基且R2是甲基;或其中R1是甲基且R2是乙基。最优选这样的化合物,其中R1是乙基且R2表示甲基。
本领域技术人员可以理解,式(I)的化合物在有关碳—氮双键方面可以是E和Z异构体形式。当本文涉及式(I)的化合物时,预以包括纯形式的E或Z异构体及其混合物。
式(I)的化合物是本领域已知的。实际上,一些化合物及其气味描述公开在EP0672746B1中。特别地,3-乙氧基-4-羟基苯甲醛o-甲基肟被描述为具有香草、辛香气味。然而,申请人未能找到有关包含这些具体化合物的香料组合物的文献中的任何参考信息,且由此申请人未能发现任何涉及这些化合物在香料组合物或包含它们的消费品中的性能的参考信息。
实际上,肟醚类倾向于具有远高于其相应醛类的气味感觉阈值。例如,(2E,6Z)-壬-2,6-二烯醛具有0.06ng/l空气的感觉阈值,而其相应的肟醚-(1E,2E,6Z)-壬-2,6-二烯醛O-甲基肟具有2.94ng/l的感觉阈值,3-(3-异丙基苯基)丁醛具有0.07ng/l的感觉阈值,而其相应的肟醚-E)-3-(3-异丙基苯基)丁醛O-甲基肟-具有22.4ng/l的感觉阈值。
由于肟醚类一般远弱于其相应的芳香醛,所以可能不令人惊讶地是它们未使香料制造者产生兴趣,且文献中未提及包含它们的香料组合物。本发明的肟醚类不寻常的方面在于它们是非特征性强烈的(实际上,就3-乙氧基-4-羟基苯甲醛O-甲基肟而言,它在强度方面与强力的增香剂乙基香草醛相差无几)。
此外,申请人令人惊讶地发现,异丁子香酚或一些异丁子香酚“替代品”例如香草醛在消费品基质中显示颜色的不稳定性,而式(I)的肟醚类是颜色稳定的。所谓术语“颜色稳定”是指在以0.02%施用于无色消费品基质中并且保存在45℃下4周时,包含式(I)的化合物的基质在视觉检查时仍然是无色的。另一方面,包含相同浓度的异丁子香酚和异丁子香酚“替代品”例如香草醛的基质变色,显示具有淡黄色、橙色、桃色或棕色的不同色彩。
在本发明的一个具体的实施方案中,提供包含式(I)的化合物且不包含异丁子香酚的香料油,更具体地,式(I)的化合物是这样的化合物,其中R1表示乙基且R2表示甲基。
在本发明的另一个具体的实施方案中,提供香料油,其包含式(I)的化合物和异丁子香酚,更具体地式(I)的化合物是这样的化合物,其中R1表示乙基且R2表示甲基,其中异丁子香酚的水平低于1%重量。
在本发明的另一个方面中,提供消费品,其包含香料油,所述香料油包含式(I)的化合物且不包含异丁子香酚,更具体地,式(I)的化合物是这样的化合物,其中R1表示乙基且R2表示甲基。
在本发明的另一个方面中,提供消费品,其包含式(I)的化合物和异丁子香酚,更具体地式(I)的化合物是这样的化合物,其中R1表示乙基且R2表示甲基,其中异丁子香酚的水平低于100ppm。
式(I)的化合物因其期望的气味特性和/或其良好的颜色稳定性和/或其低过敏可能性而为香料制造者提供以宽范围用量使用它们的宽容度,并且对其使用水平的限制低于目前对异丁子香酚或实际上异丁子香酚“替代者”例如香草醛或甲基丹提力士施加的限制。
在本发明的一个具体的实施方案中,可以以在香料油中0.1%-20%重量的水平使用式(I)的化合物,相当于在消费品中10-2000ppm的使用水平。
因此,式(I)的化合物具有远宽于异丁子香酚的使用水平,并且可以以远高于异丁子香酚的水平用于香料油中,并且可以横跨宽范围的消费品种类。
在本发明的一个具体的实施方案中,式(I)的化合物可以以50-1000ppm的用量用于除臭剂或止汗剂制品。
在本发明的一个具体的实施方案中,式(I)的化合物可以以100-1000ppm的用量用于清洗制品如香波和护发素。
在本发明的一个具体的实施方案中,式(I)的化合物可以以50-1000ppm的用量用于织物整理剂制品。
在本发明的一个具体的实施方案中,式(I)的化合物可以以10-1000ppm的用量用于液体洗涤剂制品。
在本发明的一个具体的实施方案中,式(I)的化合物可以以10-1000ppm的用量用于WC边缘清洁剂(WC rim cleaner)制品。
在本发明的一个具体的实施方案中,式(I)的化合物可以以10-1000ppm的用量用于通用清洁剂制品。
还令人惊讶地发现,式(I)的化合物显示极为天然的依兰依兰-型香气。依兰依兰(依兰(cananga odorata))提取物的应用限于在IFRA 2类产品中0.06%重量(止汗剂/除臭剂组合物)。
在这样的产品中,其中期望依兰依兰型香型,结果是式(I)的化合物可以作为依兰依兰提取物的部分或完全替代者使用。
因此,本发明在其另一个方面提供香料油,其包含式(I)的化合物和依兰依兰提取物,更具体地式(I)的化合物是这样的化合物,其中R1表示乙基且R2表示甲基,其中依兰依兰提取物的水平低于1%重量。
本发明在另一个方面提供香料油,其包含式(I)的化合物且不含依兰依兰提取物,更具体地式(I)的化合物是这样的化合物,其中R1表示乙基且R2表示甲基。
本发明在另一个方面提供止汗剂或除臭剂组合物,其包含香料油,所述香料油包含式(I)的化合物和600ppm或以下水平的依兰依兰提取物,更具体地式(I)的化合物是这样的化合物,其中R1表示乙基且R2表示甲基。
本发明在另一个方面提供止汗剂或除臭剂组合物,其包含香料油,其包含式(I)的化合物且不含依兰依兰提取物,更具体地式(I)的化合物是这样的化合物,其中R1表示乙基且R2表示甲基。
然而,申请人并不知晓具有精确地相当于异丁子香酚或依兰依兰的气味特性的任意单一香料成分。式(I)的化合物由此具有与异丁子香酚或依兰依兰类似、但并非一定相同的气味特性。照此,香料制造者可能期望混合式(I)的化合物与一些其它香料成分,得到香料油,其具有与异丁子香酚或依兰依兰气味特性更接近一致的性能,乃至达到与异丁子香酚或依兰依兰的气味特性基本上等同。所谓“基本上等同”是指一小组非专业人员例如消费者不能察觉到包含异丁子香酚或依兰依兰的消费品与包含含有本发明式(I)的化合物的香料油的同样产品之间的差别。
在本发明的一个具体的实施方案中,式(I)的化合物可以与选自如下的香料成分的一种或多种组合形成香料油:乙酸邻叔丁基环己酯(Agrumex)、格蓬酯、黄葵内酯、龙涎呋喃(Ambrofix)、水杨酸戊酯、大茴香醛、乙酸苄酯、苯甲酸苄酯、水杨酸苄酯、乙酸龙脑酯、4-叔丁基环己基乙酸酯、超级龙涎醚(Cetalox)、柠檬醛、香茅醇、乙酸香茅酯、香豆素、兔耳草醛、α突厥酮、δ突厥酮、γ癸内酯、癸醛、二氢月桂烯醇、二苯基氧、月桂醛、黑檀醇、乙基芳樟醇、乙基麦芽酚、2-甲基丁酸乙酯、乙基香草醛、十三烷二酸亚乙基酯、丁子香酚、合成橡苔、吐纳麝香、丙酸三环癸烯酯、加乐麝香、乙酸苏合香酯(Gardenol)、香叶醇、乙酸香叶酯、环十五烯内酯、二氢茉莉酮酸甲酯、洋茉莉醛、Z-3-己烯醇、Z-3-己烯基乙酸酯、Z-3-己烯基水杨酸酯、乙酸己酯、α己基肉桂醛、水杨酸己酯、吲哚、α紫罗兰酮、β紫罗兰酮、龙涎酮(Iso ESuper)、异甲基紫罗兰酮、异丁子香酚、乙酸三环癸烯酯(Jasmacyclene)、爪哇檀香、铃兰醛、芳樟醇、乙酸芳樟酯、长叶烯、麦芽酚、母菊酯(Manzanate)、2-(1-巯基-1-甲基乙基)-5-甲基环己酮、苯甲酸甲酯、甲基丹提力士、甲基萘基酮、2-甲基十一醛、麝香烯酮、仙酒酮、桃醛(Peach Pure)、牡丹腈、黑塔利亚(Petalia)、苯氧基乙基异丁酸酯、乙酸2-苯基乙基酯、苯基乙醛、2-苯基乙醇、白檀醇、结晶玫瑰(Rosacetol)、螺环格蓬酮(Spirogalbanone)、松油醇、异松油醇、乙酸松油酯、四氢芳樟醇、4,7,7-三甲基-6-噻二环[3.2.1.]辛烷、三环萜醛(Tricyclal)、新洋茉莉醛(Tropional)、9-十一碳烯醛、甲基癸烯醇和香草醛。
在本发明的一个具体的实施方案中,如果期望可以用于再生依兰依兰这样的特性的香料,则式(I)的化合物可以与一种或多种成分组合,所述一种或多种成分选自水杨酸戊酯、乙酸苄酯、苯甲酸苄酯、水杨酸苄酯、柠檬醛、香茅醇、乙酸香茅酯、对甲酚基甲基醚、α突厥酮、δ突厥酮、癸醛、月桂醛、乙基芳樟醇、2-甲基丁酸乙酯、乙基香草醛、丁子香酚、香叶醇、乙酸香叶酯、环十五烯内酯、二氢茉莉酮酸甲酯、Z-3-己烯醇、Z-3-己烯基乙酸酯、Z-3-己烯基水杨酸酯、乙酸己酯、α己基肉桂醛、水杨酸己酯、吲哚、α紫罗兰酮、β紫罗兰酮、异丁子香酚、芳樟醇、乙酸芳樟酯、母菊酯、苯甲酸甲酯、甲基丹提力士、乙酸2-苯基乙基酯、苯基乙醛、2-苯基乙醇、松油醇、异松油醇、乙酸松油酯、四氢芳樟醇、三环萜醛和香草醛。
香料油无需限于上述举出的那些成分的混合物,且可以使用常用于香料的其它成分,例如描述在“Perfume and Flavour Chemicals”,S.Arctander,Allured PublishingCorporation,1994,IL,USA中的那些成分的任意一种,将该文献引入本文参考。
本发明的香料油和包含它们的消费品还可以包含常用的佐剂。术语“佐剂”是指可以影响组合物性能而非其愉悦性能的成分。例如,佐剂可以是作为加工香料油或包含所述香料油的消费品的助剂起作用的成分,或它可以改善香料油或消费品的处理或贮存。它还可以是提供另外的有益性例如传递颜色或质地的成分。它还可以是给香料油或消费品中包含的一种或多种成分传递耐光性或化学稳定性的成分。常用于香料油或消费品中的佐剂性质和类型的详细描述可能不是穷尽的,但必须提及的是所述成分是本领域技术人员众所周知的,佐剂的实例包括溶剂和助溶剂;表面活性剂和乳化剂;粘度和流变改性剂;增稠剂和胶凝剂;防腐材料;颜料、染料和着色物质;增量剂、填充剂和增强剂;防热和光的有害作用的稳定剂、填料、酸化剂、缓冲剂和抗氧化剂。
如果香料油使用再生异丁子香酚或依兰依兰特性的成分混合物,则这些成分均具有不同的物理或化学特性,例如挥发性和直接性。因此,对于在其使用周期至始至终保持异丁子香酚或依兰依兰相关特性的香料油,可以期望根据具体最终应用的不同加速或延缓一种或多种成分的释放。例如,当香料油用于洗衣洗涤剂组合物时,可以期望用递送媒介物配制一种或多种非直接性的成分,所述递送媒介物给所述成分提供必需的直接性,使得异丁子香酚或依兰依兰的特性通过从瓶中的整个使用周期到干燥的洗涤周期都是明显的。
或者,在最终用品中,如果预期香料在稀释时散发香味时,例如在硬表面清洁剂的情况中,则期望按照这样的方式配制成分,使得每种成分在清洁期间都展示出基本上相同的比例。
因此,可以用递送媒介物配制一种或多种在所述香料油或消费品中所使用的成分以得到期望的效果。递送媒介物可以包括胶囊技术。或者,递送媒介物可以是固体支持物的形式,例如,其上可以以化学或物理方式结合有一种或多种香料成分的聚合物支持材料。此外,可以将一种或多种香料成分溶于或分散于基质材料,其用于控制所述成分发散的速率。在一个可选的实施方案中,可以使一种或多种成分支持在多孔基质上,例如环糊精或沸石或其它无机材料。在另一个实施方案中,一种或多种成分可以以前香料(pro-perfume)的形式提供,它们在适合的环境中反应以便以受控方式释放香料成分。
式(I)的化合物和包含它们的香料油可以用于所有形式的IFRA分类中举出的个人和家庭护理消费品中。用品的非限制性清单包括织物处理产品;熨烫助剂;擦布;洗衣用洗涤剂;清洁产品,特别是硬和/或软表面用清洁产品;家庭清洁剂;护理产品;洗涤护理产品;洗衣护理产品;室内芳香剂和空气清新剂;调理剂;着色剂;织物整理剂;整理基质;药物;作物保护产品;抛光剂;食品;化妆品;肥料;建筑材料;粘合剂;漂白剂;脱钙剂;汽车维护产品;地板维护产品;厨具维护产品;皮革护理产品或家具护理产品;洗刷物品;消毒剂;芳香剂;除霉菌剂;精细香料;润肤露;皮肤保护剂;蜡烛;空气清新剂;插件和香皂。
清洁产品的具体实例包括卫生间清洁剂或盥洗室清洁剂,这些产品以粉末、块、片或液体形式提供;或凝胶、管道清洁产品或排水管清洁剂;万能或通用或一般用途的清洁剂,例如常用于所有家居和商业硬表面的可以擦拭掉湿或潮湿的那些;卫生清洁剂、烘箱清洁剂或烤架清洁剂,它们可以以凝胶或泡沫喷雾剂的形式提供;金属抛光剂,包括作为抛光布、浸浴、糊剂和液体提供的那些;玻璃清洁剂和窗户清洁剂;全专用目的清洁产品,例如用于玻璃陶瓷架的那些;地毯清洁剂和污渍去除剂。
汽车维护产品的具体实例包括油漆保护剂、油漆抛光剂、油漆清洁剂、清洗保护剂、汽车清洗用洗涤剂、汽车清洗和蜡产品、用于装饰金属的抛光剂、用于装饰金属的保护膜、塑料清洁剂、焦油去除剂、屏幕清洁剂、发动机清洁剂等。
化妆品的具体实例包括美容护肤品,例如浴室用产品、皮肤洗涤和清洁产品、护肤品、眼粉底、护唇用品、指甲护理产品、私密护理产品、脚护理产品;具有特殊效果的化妆品,例如防晒霜、晒成褐色产品、脱色素产品、除臭剂、止汗剂、脱毛发剂、剃毛产品;牙科美容医疗产品,例如牙齿和口腔护理产品、牙齿护理产品、牙修复体清洁剂、牙修复体粘合剂;美发护理产品,例如洗发香波、护发产品、头发定型产品、头发成型产品和染发产品。
织物处理产品的具体实例包括洗涤剂或织物整理剂。
空气清新剂和室内芳香剂的具体实例包括用于空间例如汽车、橱、洗盘机、冰箱或鞋和真空吸尘器中的芳香剂。
目前下文是用于示例本发明的一系列实施例。
实施例1
实施例:用于皮肤致敏的KeratinoSensTM试验中测试的化合物
KeratinoSensTM细胞系包含在基因AKR1C2的ARE-元件控制下的荧光素酶基因的稳定插入物。这种细胞系的优化和测试化学品的标准方法详细描述在Emter等人2010(EmterR.,Ellis G.,Natsch A.,2010“Performance of a novel keratinocyte-based reportercell line to screen skin sensitizers in vitro.Toxicol Appl Pharmacol 245,281-290)中。使细胞在96-孔培养板中生长24h。然后用包含测试化合物和溶剂二甲亚砜(DMSO)的培养基以1%的最终水平替代该培养基。对每种化合物测试0.98-2000μM范围内的12个二等分稀释液。在每次重复中,平行地运行3个重复培养板,设定相同,且使用MTT测定法制备第4个培养板用于细胞毒性测定。将细胞与测试活性剂一起温育48h,然后测定荧光素酶活性和细胞毒性。对于每种化学物质将该完整的程序重复至少3次。对于每次重复和每种浓度中的每种化学物质,确定与DMSO对照相比的基因诱导和超过1.5阈值的具有统计学显著性诱导的孔(即50%增强的基因活性)。此外,计算最大诱导倍数(Imax)和EC1.5值(高于阈值的以μM计的诱导浓度)。在本试验中将化学物质定为阳性(即可能是皮肤致敏物),条件是满足如下3个标准:(i)EC1.5值在全部3次重复或在至少2次重复中低于1000μM;(ii)在高于1.5倍的使用基因诱导的最低浓度(即EC 1.5测定值)下,细胞存活率高于70%;和(iii)对于荧光素酶诱导存在显而易见的总体剂量响应,与所述重复之间的响应类似。
图1显示异丁子香酚和乙氧基-4-羟基苯甲醛O-甲基肟(式(I)的化合物,其中R1是乙基且R2是甲基)的基因诱导和细胞存活率曲线。后者不诱导高于1.5-倍阈值的荧光素酶活性且由此被试验定为非致敏性的。在至多1000微摩尔也没有显著的细胞毒性。另一方面,异丁子香酚显然在较低微摩尔范围中已经诱导基因,表明它是致敏性的化合物。此外,在高于500微摩尔的浓度下,它是细胞毒性的。这些结果显示3-乙氧基-4-羟基苯甲醛O-甲基肟而不是异丁子香酚可以用于香料制品,以减少对消费者的致敏风险。
实施例2:消费品中的颜色稳定性
实施例2a:精细香料中的颜色稳定性
制备测试化合物(下表中指定的式(I)的化合物)在香料级乙醇(96%EtOH,4%水)中的1和0.5%wt/wt溶液。将该溶液放入用塑料盖封闭的2.5ml透明玻璃小瓶。将小瓶放置在暴露于室内日光的窗户后面。
在1个月期限内目视检查该溶液的颜色。
测试化合物 | 1个月后乙醇溶液的颜色 | 气味 |
香草醛 | 黄色 | 香草 |
乙基香草醛 | 黄色 | 香草 |
化合物I(R<sub>1</sub>=Et,R<sub>2</sub>=Me) | 无色 | 辛香香草花香 |
使用本发明化合物I加香的乙醇溶液在1个月后在两种浓度下均通过了无色精细香料的要求,而包含香草醛或乙基香草醛的乙醇溶液已经展示出不可接受的黄色颜色。
实施例2b:肥皂块中的颜色稳定性
通过将2%wt/wt的10%wt/wt的乙基香草醛或化合物I(R1=Et,R1=Me)的一缩二丙二醇(DPG)溶液添加到肥皂基质中制备标准牛油香皂样品。将挤出的24x8mm肥皂条切成8cm片,将其在45℃放入恒温箱中1个月。将不含香料的对照样品加入到稳定性试验系列中。1个月后,包含乙基香草醛的肥皂的颜色变成巧克力棕色,气味为香草样。包含式I的化合物的肥皂颜色仍然保持为对照品样,其气味是香草辛香花香样。
Claims (14)
2.包含式(I)的化合物的香料油,其中R1是乙基且R2表示甲基。
3.权利要求1或权利要求2的香料油,其包含低于1%重量的异丁子香酚。
4.上述权利要求任一项的香料油,其中式(I)的化合物以0.1%-20%范围的水平使用。
5.上述权利要求任一项的香料油,还包含一种或多种香料成分,其选自:乙酸邻叔丁基环己酯、格蓬酯、龙涎呋喃、水杨酸戊酯、大茴香醛、乙酸苄酯、苯甲酸苄酯、水杨酸苄酯、乙酸龙脑酯、4-叔丁基环己基乙酸酯、超级龙涎醚、柠檬醛、香茅醇、乙酸香茅酯、香豆素、兔耳草醛、α突厥酮、g-癸内酯、癸醛、二氢月桂烯醇、二苯基氧、月桂醛、乙基芳樟醇、2-甲基丁酸乙酯、乙基香草醛、十三烷二酸亚乙基酯、丁子香酚、合成橡苔、吐纳麝香、丙酸三环癸烯酯、加乐麝香、乙酸苏合香酯、香叶醇、乙酸香叶酯、环十五烯内酯、二氢茉莉酮酸甲酯、洋茉莉醛、Z-3-己烯醇、Z-3-己烯基乙酸酯、乙酸己酯、a-己基肉桂醛、水杨酸己酯、吲哚、b-紫罗兰酮、龙涎酮、异甲基紫罗兰酮70、异丁子香酚、乙酸三环癸烯酯、铃兰醛、芳樟醇、乙酸芳樟酯、长叶烯、甲基丹提力士、2-甲基十一醛、麝香烯酮、桃醛、牡丹腈、苯氧基乙基异丁酸酯、乙酸2-苯基乙基酯、2-苯基乙醇、结晶玫瑰、松油醇、异松油醇、乙酸松油酯、四氢芳樟醇、三环萜醛、新洋茉莉醛、甲基癸烯醇和香草醛。
6.权利要求1或权利要求2的香料油,包含依兰依兰提取物,其中依兰依兰提取物的水平低于1%重量。
7.消费品,包含香料油,所述香料油包含如上述权利要求任一项中所定义的式(I)的化合物。
8.权利要求7的消费品,为除臭剂或止汗剂制品的形式,其中式(I)的化合物的存在量为50-1000ppm。
9.权利要求7的消费品,为清洗制品的形式如香波和护发素,其中式(I)的化合物的存在量为100-1000ppm。
10.权利要求7的消费品,为织物护理制品的形式如织物整理剂或滚筒式烘干器网兜,其中式(I)的化合物的存在量为100-1000ppm。
11.权利要求7的消费品,为液体洗涤剂制品的形式,其中式(I)的化合物的存在量为10-1000ppm。
12.权利要求7的消费品,为WC边缘清洁剂制品的形式,其中式(I)的化合物的存在量为10-1000ppm。
13.权利要求7的消费品,为通用清洁剂制品的形式,其中式(I)的化合物的存在量为10-1000ppm。
14.权利要求1-6任一项的香料油作为异丁子香酚替代品的用途。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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GB1220341.0 | 2012-11-12 | ||
GBGB1220341.0A GB201220341D0 (en) | 2012-11-12 | 2012-11-12 | Improvements in or relating to organic compounds |
CN201380058686.3A CN104769089A (zh) | 2012-11-12 | 2013-11-12 | 有机化合物中或与之相关的改进 |
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CN201380058686.3A Division CN104769089A (zh) | 2012-11-12 | 2013-11-12 | 有机化合物中或与之相关的改进 |
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CN113073006A true CN113073006A (zh) | 2021-07-06 |
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CN202110456946.9A Withdrawn CN113073006A (zh) | 2012-11-12 | 2013-11-12 | 有机化合物中或与之相关的改进 |
CN201380058686.3A Pending CN104769089A (zh) | 2012-11-12 | 2013-11-12 | 有机化合物中或与之相关的改进 |
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CN201380058686.3A Pending CN104769089A (zh) | 2012-11-12 | 2013-11-12 | 有机化合物中或与之相关的改进 |
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Country | Link |
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US (1) | US20150299614A1 (zh) |
EP (1) | EP2917317B1 (zh) |
JP (2) | JP6429786B2 (zh) |
CN (2) | CN113073006A (zh) |
BR (1) | BR112015009988A2 (zh) |
ES (1) | ES2646921T3 (zh) |
GB (1) | GB201220341D0 (zh) |
MX (1) | MX2015004976A (zh) |
SG (1) | SG11201502798QA (zh) |
WO (1) | WO2014072519A1 (zh) |
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GB201609467D0 (en) * | 2016-05-30 | 2016-07-13 | Givaudan Sa | Improvements in or relating to organic compounds |
US11384312B2 (en) | 2016-06-29 | 2022-07-12 | Takasago International Corporation | Fragrance compositions and methods of use thereof |
GB201906953D0 (en) * | 2019-05-17 | 2019-07-03 | Givaudan Sa | Organic compounds |
CN110983151B (zh) * | 2019-12-10 | 2021-09-21 | 华南理工大学 | 一种含纳米wc的高铁铜基含油轴承材料及其制备方法 |
Family Cites Families (13)
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GB2013493C (en) * | 1978-01-13 | 1996-02-20 | Unilever Ltd | Skin treatment product |
FR2414332A1 (fr) * | 1978-01-13 | 1979-08-10 | Unilever Nv | Articles desodorisants a jeter apres usage |
JP3558299B2 (ja) * | 1994-02-17 | 2004-08-25 | カネボウ株式会社 | 香料組成物 |
DE59510213D1 (de) * | 1994-03-18 | 2002-07-04 | Givaudan Sa | Oximether und diese enthaltende Riech- und Geschmackstoffkompositionen |
US6576247B1 (en) * | 1994-11-10 | 2003-06-10 | Kanebo Ltd. And T. Hasegawa Co. Ltd. | Sustained-release aromatic and method of detecting micro-organism by using the same |
US5733535A (en) * | 1995-10-25 | 1998-03-31 | The Procter & Gamble Co. | Topical compositions containing N-acetylcysteine and odor masking materials |
US5965518A (en) * | 1998-02-23 | 1999-10-12 | Nakatsu; Tetsuo | Fragrance compositions having antimicrobial activity |
AU4267500A (en) * | 1999-07-08 | 2001-01-11 | Haarmann & Reimer Gmbh | Topical cosmetic compositions comprising benzaldoximes |
JP2002256282A (ja) * | 2001-12-04 | 2002-09-11 | Kanebo Ltd | 香料組成物 |
US7763238B2 (en) * | 2002-01-16 | 2010-07-27 | Monell Chemical Senses Center | Olfactory adaptation and cross-adapting agents to reduce the perception of body odors |
US7015189B2 (en) * | 2002-08-29 | 2006-03-21 | International Flavors & Fragrances Inc. | Oxime methyl ethers |
GB0802526D0 (en) * | 2008-02-12 | 2008-03-19 | Givaudan Sa | Organic compounds |
GB0914574D0 (en) * | 2009-08-20 | 2009-09-30 | Givaudan Sa | Organic compounds |
-
2012
- 2012-11-12 GB GBGB1220341.0A patent/GB201220341D0/en not_active Ceased
-
2013
- 2013-11-12 US US14/441,063 patent/US20150299614A1/en not_active Abandoned
- 2013-11-12 CN CN202110456946.9A patent/CN113073006A/zh not_active Withdrawn
- 2013-11-12 CN CN201380058686.3A patent/CN104769089A/zh active Pending
- 2013-11-12 MX MX2015004976A patent/MX2015004976A/es unknown
- 2013-11-12 BR BR112015009988A patent/BR112015009988A2/pt not_active IP Right Cessation
- 2013-11-12 JP JP2015541179A patent/JP6429786B2/ja not_active Expired - Fee Related
- 2013-11-12 WO PCT/EP2013/073560 patent/WO2014072519A1/en active Application Filing
- 2013-11-12 SG SG11201502798QA patent/SG11201502798QA/en unknown
- 2013-11-12 ES ES13799496.8T patent/ES2646921T3/es active Active
- 2013-11-12 EP EP13799496.8A patent/EP2917317B1/en active Active
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2018
- 2018-09-14 JP JP2018172024A patent/JP2019023298A/ja active Pending
Also Published As
Publication number | Publication date |
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US20150299614A1 (en) | 2015-10-22 |
EP2917317B1 (en) | 2017-08-09 |
SG11201502798QA (en) | 2015-05-28 |
EP2917317A1 (en) | 2015-09-16 |
WO2014072519A1 (en) | 2014-05-15 |
BR112015009988A2 (pt) | 2017-07-11 |
GB201220341D0 (en) | 2012-12-26 |
JP2015535536A (ja) | 2015-12-14 |
JP2019023298A (ja) | 2019-02-14 |
CN104769089A (zh) | 2015-07-08 |
JP6429786B2 (ja) | 2018-11-28 |
MX2015004976A (es) | 2015-07-17 |
ES2646921T3 (es) | 2017-12-18 |
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