CN107074714B - 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
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- CN107074714B CN107074714B CN201480083296.6A CN201480083296A CN107074714B CN 107074714 B CN107074714 B CN 107074714B CN 201480083296 A CN201480083296 A CN 201480083296A CN 107074714 B CN107074714 B CN 107074714B
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- 230000006872 improvement Effects 0.000 title description 2
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 239000002304 perfume Substances 0.000 claims abstract description 88
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- 239000004615 ingredient Substances 0.000 claims abstract description 65
- 239000000203 mixture Substances 0.000 claims description 90
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical class CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 38
- 239000003205 fragrance Substances 0.000 claims description 32
- 150000001299 aldehydes Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000003599 detergent Substances 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 108090000790 Enzymes Proteins 0.000 claims description 10
- 102000004190 Enzymes Human genes 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 241000700159 Rattus Species 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 claims description 6
- 239000004744 fabric Substances 0.000 claims description 5
- 230000015556 catabolic process Effects 0.000 claims description 4
- 238000006731 degradation reaction Methods 0.000 claims description 4
- UKZXPOJABTXLMK-UHFFFAOYSA-N 3-[2-methyl-4-(2-methylpropyl)phenyl]propanal Chemical compound CC(C)CC1=CC=C(CCC=O)C(C)=C1 UKZXPOJABTXLMK-UHFFFAOYSA-N 0.000 claims description 2
- 150000007854 aminals Chemical class 0.000 claims description 2
- 150000002081 enamines Chemical class 0.000 claims description 2
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- 210000003494 hepatocyte Anatomy 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 claims description 2
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims 3
- 239000000047 product Substances 0.000 description 87
- -1 2-methylobutyl Chemical group 0.000 description 42
- 125000005394 methallyl group Chemical group 0.000 description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
- 235000019645 odor Nutrition 0.000 description 26
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000012190 activator Substances 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 5
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 5
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 239000002386 air freshener Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
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- 150000001558 benzoic acid derivatives Chemical class 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 229910052681 coesite Inorganic materials 0.000 description 5
- 229910052906 cristobalite Inorganic materials 0.000 description 5
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- 239000010410 layer Substances 0.000 description 5
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- 239000000377 silicon dioxide Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
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- 229910052682 stishovite Inorganic materials 0.000 description 5
- 229910052905 tridymite Inorganic materials 0.000 description 5
- LOKPJYNMYCVCRM-UHFFFAOYSA-N 16-Hexadecanolide Chemical compound O=C1CCCCCCCCCCCCCCCO1 LOKPJYNMYCVCRM-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 4
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 4
- 150000001447 alkali salts Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N beta-linalool Natural products CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
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- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 4
- 239000000645 desinfectant Substances 0.000 description 4
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- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 4
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/235—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
- C07C47/238—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/235—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
-
- 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
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Abstract
由式(I)表示的化合物,R1是‑(CHR4)m‑(CHR5)n‑(CHR6)o‑CHO,其中R4、R5、R6独立地选自H或Me,并且其中m、n、o独立地选自0和1;R2是H或Me;和R3是C3‑C6支链、直链或环状的烯基残基。所述化合物可用作个人护理和家庭护理产品中的香料成分。
Description
本发明涉及香料成分和包含所述香料成分的香料制品。特别地,本发明涉及表现出特定气味特征并且可能对铃兰(山谷百合)气味特征有贡献的所述香料成分或香料制品。更具体地,本发明涉及不含或基本上不含LilialTM的所述香料制品。本发明还涉及制备所述香料成分和香料制品的方法以及所述香料成分和香料制品在精细香料和消费品如个人护理和家庭护理产品中的用途。本发明还涉及包含所述香料成分或香料制品的所述精细香料和消费品。
具有铃兰气味特征的化合物作为香料成分是特别寻求的。这些化合物是花香基质中的重要成分,并且可以通过许多不同类型的香料创造作为协调剂(harmonizer)起作用。这种类型的化合物广泛用于消费品如个人护理和消费者护理产品以及精细香料,以产生令人愉快的气味或掩盖令人不快的气味。
因其铃兰气味香型而具有广泛价值的极佳香料成分是LilialTM。LilialTM是芳基取代的烷醛、更特别是芳基取代的丙醛的实例。具体来说,它的化学名称是3-(4-叔丁基苯基)-2-甲基丙醛(CAS 80-54-6)。这种化合物在精细香料制造以及个人和家庭护理产品中广泛使用。然而,鉴于近期发现它对雄性大鼠和狗的生殖器官显示毒性作用,因此其使用受到监管审查。在小鼠、豚鼠和灵长类动物的研究中没有发现任何影响,然而,在全球协调***(Global Harmonized Sys tem)(GHS)分类***中,这种化合物被归类为CMR2材料。对于CMR第2类材料,有必要确立为应用提出的用量对消费者是无害的。鉴于LilialTM的监管情况,需要用其他香料成分替代它。
WO2010105873解决了替代LilialTM的问题。所提出的解决方案在于使用在香料制造人调色板上通常发现的已知成分的混合物,以便重现与LilialTM基本相似的气味特征。
同样地,WO2009027957提出了一种解决方案,其在于来自香料制造人调色板的已知香料成分组合的制品。
WO2013045301还提出了LilialTM替代品的解决方案,其在于选择成分的混合物,所述成分包括化合物LilyfloreTM和某些茚满基丙醛化合物与其它次要加香成分的组合。
申请人现在已经发现可以在香料组合物和消费品中用作香料成分的化合物。更具体地,申请人已经发现具有令人感兴趣的气味特征的化合物。更具体地说,申请人已经发现可用于重构LilialTM气味的化合物,因此可用于替代LilialTM。此外,与LilialTM相比,所述化合物可具有相似或甚至改善的香料性能。最后,申请人已经发现不会引起与LilialTM相关的监管问题的化合物。特别地,申请人已经发现芳基取代的烷醛香料成分具有令人感兴趣的气味特征,但是如体外数据所示令人惊奇地不具有与LilialTM相关的CMR相关问题,所述芳基取代的烷醛香料成分是具有与LilialTM接近结构的类似物,但是其关键地在芳基环上含有位于具有醛官能团的基团的邻位的取代基和/或在芳基环上含有位于具有醛官能团的基团的对位的烯基取代基。
因此,本发明在第一方面提供了由式I表示的化合物,
其中R1是-(CHR4)m-(CHR5)n-(CHR6)o-CHO,其中R4、R5、R6独立地选自H或Me,并且其中m、n、o独立地选自0和1;
R2是H或Me;和
R3是C3-C6支链、直链或环状的烯基残基。
优选地,由式I表示的化合物具有如上所定义的R1和R2,并且其中R3是C3-C6支链、直链或环状的2-烯基(alk-2-enyl)残基,特别优选具有外型-亚甲基基团的C3-C6 2-烯基残基。
在本发明的另一方面,提供了由式1表示的化合物,其中R1和R2如上所定义,并且其中R3是在苯基环的α位上带有CH2基团的C3-C6支链、直链或环状的2-烯基残基。
在本发明的特定方面,提供了由式1表示的化合物,其中R1和R2如上所定义,并且其中R3选自烯丙基、2-甲基烯丙基、2-亚甲基丁基、3-甲基丁-2-烯-1-基、3-甲基丁-3-烯-2-基和丁-2-烯-1-基。
在本发明的另一方面,由式1表示的化合物的总碳原子数不超过16。
在本发明的更具体的方面,提供了选自以下的化合物:3-(4-(2-甲基烯丙基)苯基)丙醛、3-(2-甲基-4-(2-甲基烯丙基)苯基)丙醛、3-(4-(2-甲基烯丙基)苯基)丁醛、2-甲基-3-(4-(2-甲基烯丙基)苯基)丙醛、3-(2-甲基-4-(2-亚甲基丁基)苯基)丙醛、2-(2-甲基-4-(2-甲基烯丙基)苯基)乙醛、3-(4-(3-甲基丁-2-烯-1-基)苯基)丙醛、3-(4-(2-亚甲基丁基)苯基)丙醛、2-(4-(2-甲基烯丙基)苯基)乙醛、3-(4-(3-甲基丁-3-烯-2-基)苯基)丙醛、2-(4-(3-甲基丁-2-烯-1-基)苯基)乙醛、2-(2-甲基-4-(3-甲基丁-2-烯-1-基)苯基)乙醛和3-(4-(丁-2-烯-1-基)苯基)丙醛。
本发明的化合物具有特定的气味特征和良好的性能特征,并且这些化合物可能对类似于LilialTM的气味特征有贡献。
此外,本发明的化合物可以产生特别直接和持久的气味特征,并且它们可能对特别直接和持久的铃兰气味特征有贡献。
本发明的化合物是适合的香料成分。
本发明的化合物可能是特别有影响力的香料成分。香料成分赋予的影响与其气味值有关。气味值是蒸气压与检测阈值浓度之比。
一些化合物可能具有极高的气味值。例如,结构相关的化合物
在芳基环上在具有醛官能团的基团的邻位上具有取代基,其气味值为559'071。通过对比,相关的香料成分不具有影响力。例如,LilialTM的气味值仅为32'978,而兔耳草醛的气味值仅为21'986。
例如,当与LilialTM相比时,3-(2-甲基-4-(2-甲基烯丙基)苯基)丙醛具有高的气味值。
本发明的一些化合物的高气味值是重要的,因为需要持续性并提供有影响力的香料成分使得香料制造人能够以较低浓度的材料产生所需的谐香。
围绕LilialTM的监管问题源于其在大鼠和狗中被酶促降解为叔丁基苯甲酸(t-BBA)的事实,叔丁基苯甲酸已知可以在体外抑制葡萄糖合成和脂肪酸合成(McCune等,ArchBiochem Biophys(1982)214(1):124-133)。
已知叔丁基苯甲酸在雄性大鼠中引起睾丸效应(Hunter等,FoodCosmet.Toxicol.1965,3:289-298;Cagen等,J.Am.Coll.Toxicol.1989,8(5):1027-1038)。
相比之下,本发明的化合物潜在地避免了毒性问题。
与Lilial(其中芳环被丙醛侧链对位的代谢惰性的叔丁基取代)不同的是,本发明化合物带有直链或支链烯基取代基(通式I的R3)。这种烯基取代基可能在脊椎动物中进行进一步的氧化代谢降解步骤,例如羟基化或环氧化,随后水解成连位二醇。因此,所得到的代谢物与对叔丁基苯甲酸相比将具有不同的物理性质,例如更高的水溶性,并因此预期不会产生对叔丁基苯甲酸对雄性大鼠和狗的生殖毒性作用。或者,例如如果所描述的作用于烯基取代基的代谢步骤发生得比丙醛侧链的氧化降解更快的话,烯基取代基可以防止或减少丙醛侧链降解为取代的苯甲酸。
因此,本发明的另一方面提供了上文定义的化合物作为香料成分的用途。
本发明的另一方面提供了上文定义的化合物在香料组合物中的用途,作为芳基取代的丙醛增香剂的替代品,所述增香剂在芳基环上在具有醛官能团的取代基的邻位位置上是未被取代的和/或在具有醛官能团的取代基的对位位置上带有烯基取代基,特别是LilialTM。
在本发明的另一方面,提供了一种给香料组合物赋予青香气味特征的方法,所述方法包括将上文定义的化合物掺入到所述香料组合物中的步骤。
在本发明的另一方面,提供了包含上文定义的化合物的香料组合物。
在本发明的另一方面,提供了一种香料组合物,其具有铃兰气味特征的青香方面(aspects)、包含上文定义的化合物。
在本发明的另一方面,提供了一种包含上文定义的化合物的香料组合物,其具有减少量的或基本上不含任何芳基取代的丙醛增香剂,所述增香剂在芳基环上在与具有醛官能团的取代基相邻的位置上是未被取代的,特别是LilialTM。
根据本发明的香料组合物可以完全由一种或多种本发明的化合物制成。然而,除了一种或多种本发明化合物之外,香料组合物还可以含有一种或多种另外的香料成分。
本发明的化合物可以以任何量存在于香料组合物中,这取决于香料制造人希望实现的特定的嗅觉效果。在本发明的一个具体实施方案中,本发明的香料组合物可含有上文定义的化合物,其含量为所述组合物的0.1-100重量%。
如果使用一种或多种另外的香料成分,它们可以选自本领域已知的香料成分。
优选地,可以用于香料组合物中的至少一种另外的香料成分具有铃兰气味特征,如3-(4-异丁基-2-甲基苯基)丙醛。
特别地,可以用于本发明的香料组合物的所述香料成分包括(E/Z)-9-羟基-5,9-二甲基癸-4-烯醛、6-甲氧基-2,6-二甲基庚-1-醛(甲氧基甜瓜醛)、5,9-二甲基-4,8-癸二烯醛(香叶醛)、β-甲基-3-(1-甲基乙基)苯丙醛(花青醛)、八氢-8,8-二甲基萘-2-甲醛(Cyclomyral)、α-甲基-1,3-苯并间二氧杂环戊烯-5-丙醛(新洋茉莉醛)、5-甲基-2-(1-甲基丁基)-5-丙基-1,3-二噁烷(Troenan)、3-(邻-乙基苯基)-2,2-二甲基丙醛(清风醛)、金合欢醇、任选地作为异构体混合物的3,7,11-三甲基十二碳-1,6,10-三烯-3-醇(橙花叔醇)、2-甲基-4-苯基丁-2-醇(二甲基苯基乙基甲醇)、顺式-4-(异丙基)环己烷甲醇(五月铃兰醇)、1-(1-羟基乙基)-4-(1-甲基乙基)环己烷(任选地作为非对映异构体的混合物)(新铃兰醇(mugetanol))、(4-甲基-3-戊烯基)环己烯甲醛(Citrusal)、水杨酸环己酯、水杨酸己酯、水杨酸苄酯、水杨酸戊酯、3-(对-(2-甲基丙基)苯基)-2-甲基丙醛(银醛)、3-对-枯烯基-2-甲基丙醛(兔耳草醛)、如下成分的混合物:顺式-四氢-2-异丁基-4-甲基吡喃-4-醇;反式-四氢-2-异丁基-4-甲基吡喃-4-醇;(白花醇)、柠檬酸三乙酯和一缩二丙二醇。
所述香料成分还可以包括水杨酸戊酯(2050-08-0);(89-43-0);水杨酸苄酯(118-58-1);水杨酸顺式-3-己烯酯(65405-77-8);香茅基氧基乙醛(7492-67-3);环铃兰醛(7775-00-0);水杨酸环己酯(25485-88-5);(68738-94-3);香茅醇(106-22-9);香叶醇(106-24-1);环戊醇Hc 937165(84560-00-9);Cymal(103-95-7);道比卡尔(30168-23-1);乙基芳樟醇(10339-55-6);超级铃兰醛(71077-31-1);(125109-85-5);(63500-71-0);吉兰吡喃(24237-00-1);水杨酸己酯(6259-76-3);新洋茉莉醛(TM)(1205-17-0);羟基香茅醛(107-75-5);芳樟醇(78-70-6); (31906-04-4);甲基铃兰醇(Majantol)(103694-68-4); (13828-37-0);美乐馥(68991-97-9);甜瓜醛(106-72-9);新铃兰醇(63767-86-2);铃兰醇(Mugues ia)(56836-93-2);铃兰醇(13351-61-6);菩提花酯(91-51-0);(10461-98-0); (55066-48-3);(215231-33-7);(6658-48-6);Suzural(6658-48-6);(18479-57-7);四氢芳樟醇(78-69-3);甲基戊基桂醛(Acalea)(84697-09-6);二氢异茉莉酮酸酯(Dihydro Iso Jasmonate)(37172-53-5);己基肉桂醛(101-86-0);(24851-98-7);乙偶姻(513-86-0);阿道克醛(141-13-9);(207228-93-1);(211299-54-6);龙涎呋喃(3738-00-9);(362467-67-2);(28219-61-6);西瓜酮(28940-11-6);(3738-00-9);肉桂醇(104-54-1);柠檬醛(5392-40-5);异丁酸三环癸烯酯(67634-20-2);乙酸三环癸烯酯(TM)(5413-60-5);丙酸三环癸烯酯TM(17511-60-3);环十六内酯(109-29-5);环十六烯酮(3100-36-5);环十五烷酮(507-72-7);丁位突厥酮(57378-68-4);(67801-20-1);超级爱林太尔(40910-49-4);乙基香草醛(121-32-4);巴西酸亚乙酯(105-95-3);环十五烯酮942008(14595-54-1);环十五内酯935985(106-02-5);清风醛(67634-14-4);浆果乙酯(72903-27-6);γ癸内酯(706-14-9);环十五烯内酯(111879-80-2);(141773-73-1);六甲基茚满并吡喃(1222-05-5);(118562-73-5);(54464-57-2);异己烯基环己烯基甲醛(37677-14-8);乙酸茉莉酯(18871-14-2);(198404-98-7);月桂醛(112-54-9);梅弗兰醛(55066-49-4);麝香烯酮(63314-79-4);(1506-02-1);(95962-14-4);赛木香醇(70788-30-6);对羟基苯基丁酮(5471-51-2);松乙醛(33885-51-7);(236391-76-7);圣檀醇(28219-61-6);(109-29-5/507-72-7);萜品醇(8000-41-7);香草醛(121-33-5);和(37609-25-9),其中括号中的数值是CAS编号。
香料组合物不必限于上述列出的香料成分。可以使用通常用于香料制造的其它香料成分,例如在“Perfume and Flavour Chemicals”,S.Arctander,Allured PublishingCorporation,1994,IL,USA中描述的那些成分的任意种,其通过引用并入本文,包括精油、植物提取物、净油、香树脂、由天然产物获得的增香剂等。
所述香料组合物中包含的香料成分如上所述,但是,当然,香料组合物可以不限于所述成分。特别地,香料混合物可以包含常用于香料制品的佐剂。术语“佐剂”是指因不在于或不具体涉及组合物的嗅觉性能的原因而可以用于香料组合物的成分。例如,佐剂可以是作为加工香料成分或包含所述成分的组合物的助剂起作用的成分,或它可以改善香料成分或包含它的组合物的操作或储存。它还可以是提供另外的有益性例如赋予颜色或质地的成分。它还可以是给香料成分或包含它的组合物中包含的一种或多种成分赋予耐光性或化学稳定性的成分。常用于包含香料成分的香料混合物或组合物的佐剂的性质和类型的详细描述可能无法穷尽,但是必须提及,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;粘度和流变调节剂;增稠剂和胶凝剂;防腐材料;色素、染料和着色物质;增充剂、填充剂和补益剂;抵抗热和光的有害作用的稳定剂、填充剂、酸化剂、缓冲剂和抗氧化剂。
此外,如果期望,则可以用递送媒介物配制用于本发明的香料成分或佐剂的任意一种或多种,以便得到期望的效果。递送媒介物可以包括包囊材料。或者,递送媒介物可以是固体支持物形式,例如其上可以以化学或物理方式结合一种或多种香料成分的聚合物支持物材料。此外,可以将一种或多种香料成分或佐剂溶于或分散于基质材料,该基质材料用于控制所述成分从其中释放出的速率。在一个可选的实施方案中,可以使一种或多种成分或佐剂支持在多孔底物上,例如,环糊精或沸石或其它无机材料。在另一个实施方案中,可以以前-香料的形式提供一种或多种香料成分,其在适合的环境中反应以便以受控方式释放香料成分。
优选地,在具有羰基官能团的另外的香料成分的情况下,相应的前-香料是伯和/或仲胺化合物与香料成分的反应产物。
特别优选这种前-香料,也称为香料前体,是合适的氨基化合物与式I表示的化合物的反应产物
其中
R1是-(CHR4)m-(CHR5)n-(CHR6)o-CHO;其中R4、R5、R6独立地选自H或Me,并且其中m、n、o独立地选自0和1;
R2是H或Me;和
R3是C3-C6支链、直链或环状的烯基残基。
通过这样的反应,可以获得不同的产物,例如相应的亚胺、烯胺、半-缩醛胺或缩醛胺。
用于形成上述前-香料的合适的氨基化合物可以选自芳族胺,特别是2-氨基苯甲酸甲酯(邻氨基苯甲酸甲酯),2-氨基-苯乙酮,式I I的邻、间或对氨基苯甲酸酯类(其中R1=C1-C12直链或支链烷基、烯基、环烷基、环烯基或烷基芳基,且R2=H、Me、Et);伯或仲脂族胺,优选C8-C30直链或支链烷基胺或烷基二胺类;醚胺;乙烯-和丙烯-胺;氨基酸和衍生物;聚胺,特别是伯和仲聚醚胺、聚乙烯亚胺、聚丙烯亚胺、聚酰胺基胺、聚氨基酸、聚乙烯胺、聚(乙二醇)双(胺)、氨基取代的聚乙烯醇;N-(3-氨基丙基)咪唑,哌啶甲酰胺,粪臭素和吲哚。
或者,可以提供适于释放式I化合物的前-香料,作为Knoevenagel缩合、醛醇形成的产物,作为氧化裂解的前-香料或缩醛或半-缩醛。
考虑到前述内容,应当理解,香料组合物可以至少部分为固体形式、凝胶形式、泡沫形式和/或液体形式。如果它以固体形式存在,则其可以采取颗粒、粉末或片剂的形式。
本发明在另一方面提供了精细香料或消费品如个人护理或家庭护理组合物,其由式I表示的化合物加香,
其中
R1是-(CHR4)m-(CHR5)n-(CHR6)o-CHO;其中R4、R5、R6独立地选自H或Me,并且其中m、n、o独立地选自0和1;
R2是H或Me;和
R3是C3-C6支链、直链或环状的烯基残基。
在一个具体实施方案中,本发明提供了精细香料或消费品如个人护理或家庭护理组合物,其由式I表示的化合物加香,其中R1和R2如上所定义,并且其中R3是C3-C6支链、直链或环状的2-烯基残基,特别优选具有外型-亚甲基基团的C3-C6 2-烯基残基。
在另一个具体实施方案中,本发明提供了精细香料或消费品如个人护理或家庭护理组合物,其由式1表示的化合物加香,其中R1和R2如上所定义,其中并且R3是C3-C6支链、直链或环状的2-烯基残基,其在苯基环的α位上带有CH2基团。
在另一个具体实施方案中,本发明提供了精细香料或消费品如个人护理或家庭护理组合物,其由式I表示的化合物加香,其中R1和R2如上所定义,并且其中R3选自烯丙基、2-甲基烯丙基、2-亚甲基丁基、3-甲基丁-2-烯-1-基、3-甲基丁-3-烯-2-基和丁-2-烯-1-基。
在本发明的更具体的实施方案中,提供了精细香料或消费品如个人护理或家庭护理组合物,其由至少一种或多种选自以下的化合物加香:3-(4-(2-甲基烯丙基)苯基)丙醛、3-(2-甲基-4-(2-甲基烯丙基)苯基)丙醛、3-(4-(2-甲基烯丙基)苯基)丁醛、2-甲基-3-(4-(2-甲基烯丙基)苯基)丙醛、3-(2-甲基-4-(2-亚甲基丁基)苯基)丙醛、2-(2-甲基-4-(2-甲基烯丙基)苯基)乙醛、3-(4-(3-甲基丁-2-烯-1-基)苯基)丙醛、3-(4-(2-亚甲基丁基)苯基)丙醛、2-(4-(2-甲基烯丙基)苯基)乙醛、3-(4-(3-甲基丁-3-烯-2-基)苯基)丙醛、2-(4-(3-甲基丁-2-烯-1-基)苯基)乙醛、2-(2-甲基-4-(3-甲基丁-2-烯-1-基)苯基)乙醛和3-(4-(丁-2-烯-1-基)苯基)丙醛或相应的前-香料。
当添加到精细香料或消费品如个人护理或家庭护理组合物中时,上文定义的化合物可以赋予所述组合物特征气味,优选青香气味。根据本发明的另一方面,提供了一种赋予精细香料或消费品如个人护理或家庭护理组合物特定气味特征,优选青香气味特征的方法,其包括向所述组合物中添加上文定义的化合物或含有所述化合物的香料组合物的步骤。
在本发明的另一方面,提供了一种赋予精细香料或消费品如个人护理或家庭护理组合物特定气味特性,特别是青香气味特征的方法,其包括选择性地向所述精细香料或消费品添加上文定义的芳基取代的烷醛化合物并选择性地从所述精细香料或消费品中排除任何芳基取代的烷醛化合物的步骤,所述被排除的化合物在芳基环上在具有醛官能团的取代基邻位位置上是未被取代的或者在环上在含有醛官能团的取代基对位位置上未被烯基残基取代。
在本发明的另一方面,提供了一种赋予精细香料或消费品如个人护理或家庭护理组合物青香气味特征的方法,其包括选择性地向所述精细香料或消费品添加上文定义的芳基取代的烷醛化合物并选择性地从所述精细香料或消费品中排除任何芳基取代的烷醛化合物的步骤,所述被排除的化合物在芳基环上在具有醛官能团的取代基邻位位置上是未被取代的或者在环上在含有醛的取代基对位位置上未被烯基残基取代,所述选择性添加或排除是基于当与从大鼠分离的肝细胞一起孵育时所述化合物对酶介导降解为其苯甲酸衍生物的敏感性,所述化合物适于添加,是因为在测试条件下它们不降解为其苯甲酸衍生物或者它们降解为非毒性的苯甲酸衍生物,而所述化合物被排除,是因为在测试条件下它们降解为其苯甲酸衍生物。
在本发明的另一方面,提供了一种香料组合物,其包含在合适的容器中的芳基取代的烷醛化合物以及不含任何CMR2分类的标记,所述芳基取代的烷醛化合物在芳基环上在具有醛官能团的取代基对位位置上具有烯基取代基和/或在环上在具有醛官能团的基团的邻位位置上具有甲基取代基。
消费品例如个人和家庭护理组合物包括、但不限于织物处理产品、熨衣助剂、擦布、洗衣房清洁剂、清洁产品特别是用于硬和/或软表面的清洁产品、家庭清洁剂、护理产品、洗涤护理产品、洗衣房护理产品、室内香料和空气清新剂、调理剂、着色剂、织物调理剂、调理底物、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、汽车护理产品、地板护理产品、餐具护理产品、皮革护理产品或家具护理产品、洗刷物品、消毒剂、香料、霉菌去除剂和/或上述举出产品的前体。
本领域技术人员完全知晓香料成分和组合物对精细香料应用以及所有形式的消费品应用如个人和家庭护理组合物的适用性,且这类组合物的极为详细的描述在本文中不再详举。然而,可以举出的具体组合物包括清洁组合物;汽车护理组合物;化妆品组合物;织物处理组合物;和空气清新剂和空气护理组合物。
清洁用品包括:-
厕所清洁剂或盥洗室清洁剂,换句话说,是用于清洁盥洗室清洗盆和尿池的产品,这些产品优选以粉末、块、片剂或液体形式提供,优选凝胶。除其它典型的成分外,例如表面活性剂,它们一般还包括有机酸,例如柠檬酸和/或乳酸)或硫酸氢钠、酰氨基硫酸或磷酸,它们用于除去石灰垢或尿垢;
管道清洁产品或排水道清洁剂。这些典型地是强碱性产品,它们通常用于除去管道阻塞物,其包含有机材料─例如毛发、脂肪、食品残留物、肥皂沉积物等。添加Al粉或Zn粉可以用于形成具有泡腾效果的H2气体。可能的成分通常是碱洗涤剂、碱式盐、氧化剂和中性盐。粉末形式的提供形式优选还包括硝酸钠和氯化钠。液体形式的管道清洁产品可以优选还包括次氯酸盐。还存在基于酶的排水道清洁剂。酸性产品同样是可能的;
通用或万能或一般用途的清洁剂。它们是可以通用于家庭和商业中的所有硬表面的清洁剂,可以以湿或潮湿的形式擦掉。一般而言,它们是中性的或弱碱性的或弱酸性的产品,尤其是液体产品。万能或一般用途的清洁剂通常包含表面活性剂、增量剂、溶剂和助水溶物、染料、防腐剂等;
具有专用消毒剂特性的万能清洁剂。它们还包括活性抗微生物成分(例如醛类、醇类、季铵化合物、两性表面活性剂、三氯生);
卫生清洁剂。这些是用于清洁浴室和厕所的产品。碱性卫生清洁剂优选用于除去脂肪污物,而酸性卫生清洁剂特别用于除去石灰垢。卫生清洁剂还有利地具有相当的消毒剂作用,特别是包含氯的强碱性卫生清洁剂;
可以以凝胶或泡沫喷雾剂形式提供的烤箱清洁剂或烤架清洁剂。它们一般用于除去烧烤或碳化的食物残留物。优选使用例如氢氧化钠、偏硅酸钠、2-氨基乙醇这样的强碱性制品得到烤箱清洁剂。此外,它们一般包含阴离子和/或非离子表面活性剂、水溶性溶剂,且在一些情况中,包含增稠剂,例如聚羧酸盐和羧甲基纤维素;
金属抛光剂。它们是用于具体类型的金属例如不锈钢或银的清洁剂。不锈钢清洁剂除包含酸(优选至多3%重量,例如柠檬酸、乳酸)、表面活性剂(特别是至多5%重量,优选非离子和/或阴离子表面活性剂)和水外,还优选包含溶剂(优选至多15%重量)以除去脂肪污物,且还包含例如增稠剂和防腐剂这样的化合物。此外,在优选用于光亮的不锈钢表面的产品中,包括极为精细的抛光结构。由此银抛光剂可以以酸性制品形式提供。特别地,为了除去硫化银的黑色沉积物,它们优选包含配位剂(例如硫脲、硫代硫酸钠)。典型的提供形式是抛光布、浸浴液、糊剂和液体。使用铜清洁剂和非铁金属清洁剂(例如用于铜锌合金和红古铜色)除去深度变色(氧化层)。它们一般具有弱碱性配方(优选含有氨)且通常包含抛光剂,且还优选包含铵肥皂和/或配位剂;
玻璃清洁剂和窗户清洁剂。这些产品优选用于从玻璃表面上除去污物,尤其是油腻污物。优选它们包含这样的化合物,例如阴离子和/或非离子表面活性剂(特别是至多5%重量)、氨和/或乙醇胺(特别是至多1%重量)、乙醇和/或2-丙醇、乙烯甘油醚类(特别是至多10-30%重量)、水、防腐剂、染料、防雾剂等;和
专用目的的清洁产品,实例是用于玻璃-陶瓷壁炉挂架的那些,并且还有地毯清洁剂和污渍去除剂。
汽车护理产品包括:-
漆保护剂、漆抛光剂、漆清洁剂、洗涤保护剂、用于自动清洗的清洗剂、自动清洗和蜡产品、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。
化妆品包括:-
(a)护肤化妆品,尤其是浴室产品、皮肤洗涤和清洁产品、护肤产品、眼用粉底、护唇用产品、指甲护理产品、私密护理产品、足护理产品;
(b)具有特殊效果的化妆品,尤其是防晒霜、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、香料;
(c)牙科医疗化妆品,尤其是牙齿和口腔护理产品、牙齿护理产品、牙修复体用清洁剂、牙修复体用粘着剂;和
(d)美容护发产品,尤其是洗发香波、护发产品、头发定型产品、头发整形产品和发色产品。
织物处理产品包括:-
洗涤剂或织物调理剂,例如液体或固体形式。
空气清新剂和室内用香料包括:-
优选包含挥发性且通常是嗅到令人愉快气味的化合物的产品,这些化合物甚至可以以极小量有利地掩蔽令人不愉快的气味。用于生活区域的空气清新剂特别地包含天然和合成精油,例如松针油、柠檬油、桉叶油、薰衣草油等,其用量为,例如至多50%重量。作为气雾剂,它们倾向于包含少量这类精油,作为实例,用量低于5%或低于2%重量,但还包括这样的化合物,例如乙醛(特别是<0.5%重量)、异丙醇(特别是<5%重量)、矿物油(特别是<5%重量)和推进剂。其它呈现形式包括棒和块。典型地使用包含精油的凝胶浓缩物制备它们。还能够添加甲醛(用于防腐)和叶绿素(优选<5%重量)且还能够添加另外的成分。然而,空气清新剂不限于生活空间,而且还预用于汽车、橱柜、洗盘机、冰箱或鞋子和甚至其在真空吸尘器中的应用是可能的。例如在家庭(例如橱柜)中,除气味改进剂外,还可以使用消毒剂,其优选包含这样的化合物,例如磷酸钙、滑石粉、硬脂精和精油,这些产品采用例如小香囊这样的形式。
上文提到的消费品组合物,特别是用于洗涤或清洁应用的消费品组合物可含有一种或多种下列物质:
增量剂物质、表面活性剂、酶、漂白剂例如优选有机和/或无机过氧化合物、过氧活化剂、与水易溶混的溶剂、多价螯合剂、电解质、pH调节剂、增稠剂,和另外的佐剂,例如污物释放活性物质、任选的增白剂、变灰色抑制剂、颜色转移抑制剂、泡沫调节剂和染料。
表面活性剂包括阴离子表面活性剂、非离子表面活性剂及其混合物,而且阳离子表面活性剂是适合的。适合的非离子表面磺酰基具体地是在烷基部分上各自具有12-18个碳原子和3-20个、优选4-10个烷基醚基团的烷基糖苷类和/或直链或支链醇类的乙氧基化和/或丙氧基化产物。另外可用的是N-烷基胺类、邻位二醇类、脂肪酸酯类和脂肪酰胺类(在烷基部分上相当于上述举出的长链醇衍生物)和在烷基残基上具有5-12个碳原子的烷基苯酚类的乙氧基化和/或丙氧基化产物。
适合的阴离子表面活性剂包括皂类和优选包含具有强碱离子作为阳离子的硫酸盐或磺酸盐基团的那些。皂类包括具有12-18个碳原子的饱和或不饱和脂肪酸的碱式盐。这类脂肪酸还可以以不完全中和的形式使用。在硫酸盐类的可用的表面活性剂中包括具有12-18个碳原子的脂肪醇的硫酸半酯类的盐和具有低乙氧基化度的上述举出的非离子表面活性剂的硫酸化产物。在磺酸盐类的可用的表面活性剂中包括在烷基部分上具有9-14个碳原子的直链烷基苯磺酸盐、具有12-18个碳原子的烷基磺酸盐和在相应的单烯属烃类与三氧化硫反应时产生的具有12-18个碳原子的烯烃磺酸盐以及在脂肪酸甲酯或乙酯磺化时产生的α-磺基脂肪酸酯类。
阳离子表面活性剂包括酯基季铵盐和/或季铵化合物(QAC)。QAC可以通过使叔胺类与烷化剂反应产生,所述烷化剂例如甲基氯、苄基氯、硫酸二甲酯、十二烷基溴,而且还有环氧乙烷。具有长烷基残基和2个甲基的叔胺类的烷基化特别易于发生,且还可以使用甲基氯在适度条件下使具有2个长残基和1个甲基的叔胺类季铵化。具有3个长烷基残基或羟基取代的烷基残基的胺类具有低反应性且例如使用硫酸二甲酯使其季铵化。适合的QAC是,例如,苯扎氯铵(N-烷基-N,N-二甲基苄基铵氯化物)、benzalkonB(间,对-二氯苄基二甲基-C12-烷基铵氯化物)、苯佐氯铵(苄基十二烷基-双(2-羟基乙基)铵氯化物)、西曲溴铵(N-十六烷基-N,N-三甲基铵溴化物)、苄索氯铵(benzetonium chloride)(N,N-二甲基-N-[2-[2-[p-(1,1,3,3-四甲基丁基)苯氧基]乙氧基]乙基]苄基铵氯化物)、二烷基二甲基铵氯化物例如二-正-癸基二甲基铵氯化物、十二烷基二甲基铵溴化物、二辛基二甲基铵氯化物、1-西吡铵和噻唑啉碘化物及其混合物。优选的QAC是具有C8-C22个烷基残基的苯扎氯铵,特别是C12-C14烷基苄基二甲基铵氯化物。
酯基季铵盐包括商购的由Stepan公司在StepantexTM商标下销售的甲磺酸甲基羟基烷基二烷酰氧基烷基铵(methylhydroxyalkyl dialkoyloxyalkylammoniummethosulfates)或已知商品名为DehyquatTM的Cognis Deutschland GmbH的产品或Goldschmidt-Witco的RewoquatTM产品。
表面活性剂在本发明消费品中的使用量为5wt%-50wt%。
增量成分包括水溶性和/或水不溶性有机和/或无机增量成分。具体地,它们包括水溶性有机增量成分物质,其为聚羧酸,更具体地是柠檬酸和糖酸类、单体和聚合氨基聚羧酸,特别是甲基甘氨酸二乙酸、次氮基三乙酸和乙二胺四乙酸以及聚天冬氨酸、聚膦酸特别是氨基三(亚甲基膦酸)、乙二胺四(亚甲基膦酸)和1-羟基乙烷-1,1-二膦酸、聚合羟基化合物例如糊精以及聚合(聚)羧酸、聚合丙烯酸、甲基丙烯酸、马来酸及其混合的聚合物,它们还可以包含小比例的不带有羧酸官能团的可聚合物质。不饱和羧酸的均聚物的相对分子量一般为5000-200,000,其共聚物的相对分子量为2000-200,000,在每种情况中均以游离酸为基准。这种类型的适合的化合物是丙烯酸或甲基丙烯酸与乙烯基醚类的共聚物,所述乙烯基醚类例如乙烯基甲基醚类、乙烯基酯类、丙烯和苯乙烯,其中酸的比例等于至少50wt%。另外可能的情况是,使用包含为单体的两种不饱和酸和/或其盐的三聚体作为水溶性有机增量成分物质和使用乙烯基醇和/或乙烯基醇衍生物或碳水化合物作为第三种单体。第一种酸性单体或其盐可以衍生自烯化单不饱和C3-C8羧酸。第二种酸性单体或其盐可以为C4-C8二羧酸例如马来酸的衍生物。第三种单体单元由乙烯基醇和/或酯化的乙烯基醇构成。聚合物可以包含60wt%-95wt%、特别是70wt%-90wt%的(甲基)丙烯酸或(甲基)丙烯酸酯以及5wt%-40wt%的乙烯基醇和/或醋酸乙烯酯。具体的聚合物是这样的聚合物,其中(甲基)丙烯酸分别与马来酸或马来酸酯的重量比为1:1和4:1。两种用量和重量比基于酸。第二种酸性单体或其盐还可以是烯丙基磺酸的衍生物,其在2-位上被烷基例如C1-C4烷基取代或被可以衍生自苯或苯衍生物的芳族基团取代。三聚体可以包含40wt%-60wt%、特别是45-55wt%的(甲基)丙烯酸或(甲基)丙烯酸酯、10wt%-30wt%、优选15wt%-25wt%的甲烯丙基磺酸或甲烯丙基磺酸酯和作为第三者单体的15wt%-40wt%、优选20wt%-40wt%的碳水化合物。这种碳水化合物可以是,例如单糖、二糖、寡糖或多糖,例如蔗糖。三聚体一般具有1000-200,000的相对分子量。另外的共聚物包括这样的共聚物,其包含丙烯醛和丙烯酸/丙烯酸盐或醋酸乙烯酯作为单体。尤其是为了制备液体洗涤剂,可以使用水溶液形式的有机增量成分物质,例如30-50-重量百分比的水溶液。所有上述的酸均可以以其水溶性盐、特别是其碱式盐的形式使用。
有机增量成分物质可以以至多40wt%的量使用。
水溶性无机增量成分材料包括碱性硅酸盐和聚磷酸盐,例如三磷酸五钠。结晶或无定形碱性铝硅酸盐例如结晶铝硅酸钠也可以作为水不溶性、水分散性增量成分材料使用,例如,其用量至多为50wt%。铝硅酸盐典型地包含具有小于30μm的粒度的颗粒。
还可以单独地使用结晶碱性硅酸盐或将其与无定形硅酸盐一起使用。用于本发明消费品中作为去垢增量成分的碱性硅酸盐可以具有的碱性氧化物与SiO2的摩尔比低于0.95,特别是1:1.1-1:12,且可以与无定形或结晶形式存在。碱性硅酸盐可以为硅酸钠,特别是无定形硅酸盐,其具有的Na2O:SiO2摩尔比为1:2-1:2.8。
本发明消费品组合物中可以包含至多60wt%水平的增量成分物质。
过氧化合物包括有机过酸或有机酸的过酸盐,例如邻苯二甲酰亚氨基过己酸(phthal imidopercapronic acid)、过苯甲酸或二过十二烷二酸的盐、过氧化氢和在适用条件下释放过氧化氢的无机盐,例如过硼酸盐、过碳酸盐和/或过硅酸盐。如果使用固体过氧化合物,则可以与粉末或颗粒形式使用它们,通常可以将它们以已知方式包装。
可以以至多50wt%的用量使用过氧化合物。分别添加少量已知的漂白剂稳定剂例如聚膦酸盐、硼酸盐、偏硼酸盐和偏硅酸盐以及镁盐例如硫酸镁可能是有用的。
在过度水解条件下产生优选具有1-10个碳原子、特别是2-4个碳原子的脂族过氧化羧酸和/或(任选取代的)过苯甲酸的化合物可以用作漂白活化剂。携带具有上述碳原子数的O-和/或N-酰基和/或任选取代的苯甲酰基的物质是适合的。可以使用度酰化烯烃二胺类,特别是四乙酰基乙二胺(TAED);酰化三嗪衍生物,特别是1,5-二乙酰基-2,4-二氧代六氢-1,3,5-三嗪(DADHT);酰化甘脲,特别是四乙酰基甘脲(TAGU);N-酰基亚胺类,特别是N-壬酰基琥珀酰亚胺(NOSI);酰化酚磺酸盐,特别是正壬酰基或异壬酰基氧基苯磺酸盐(正-或异-NOBS);羧酸酐,特别是苯二甲酸酐;酰化多价醇类,特别是三醋精、乙二醇双醋酸酯、2,5-二乙酰氧基-2,5-二氢呋喃和烯醇酯类以及分别与乙酰化山梨醇和甘露糖醇的混合物(SORMAN);酰化糖衍生物,特别是五乙酰基葡萄糖(PAG)、五乙酰基果糖、四乙酰基木糖和八乙酰基乳糖;以及酰化的任选N-烷基化谷氨酰胺和葡糖酸内酯和/或N-酰化内酰胺类,例如N-苯甲酰基己内酰胺。同样可以使用亲水性取代的醋酸酰酯和酰基内酰胺类。还可以使用常规漂白活化剂的组合。可以以常用量的范围包含这类漂白活化剂,优选用量为1wt%-10wt%,特别是2wt%-8wt%,以全部试剂为基准。
除上述举出的常用漂白活化剂外或除了它们,还可以包含磺基亚胺类和/或增强漂白的过渡金属盐或过渡金属配合物作为催化剂。在适合的过渡金属化合物中特别地包括锰、铁、钴、钌或钼的salen配合物及其氮-类似物化合物、锰、铁、钴、钌或钼的羰基配合物、锰、铁、钴、钌、钼、钛、钒和铜的具有含氮的三重配体的配合物、钴、铁、铜和钌的胺配合物。同样可以使用漂白活化剂和过渡金属配合物的组合。可以以常用量使用增强漂白的过渡金属配合物,特别是具有中心原子Mn、Fe、Co、Cu、Mo、V、Ti和/或Ru的增强漂白的过渡金属配合物,例如至多1wt%,以消费品组合物的重量为基准。
可以用于组合物的适合的酶是来自蛋白酶、角质酶、淀粉酶、支链淀粉酶、半纤维素酶、纤维素酶、脂肪酶、氧化酶和过氧化物酶及其混合物的类型的那些酶。从真菌或细菌中回收的酶活性物质也是适合的,所述真菌或细菌例如枯草芽孢杆菌(Bacillussubtilis)、藓样芽胞杆菌(Bacillus licheniformis)、灰色链霉菌(Streptomycesgriseus)、疏绵状毛腐质霉(Humicola lanuginosa)、特异腐质霉(Humicola insolens)、类产碱假单胞菌(Pseudomonas pseudoalcaligenes)或洋葱假单胞菌(Pseudomonascepacia)。适用的酶可以被吸附在载体物质上和/或被包埋入包装物质,以防止它们过早失活。它们可以以典型地低于5wt%的用量包含在本发明的洗涤产品中。
荧光增白剂包括二氨基均二苯代乙烯二磺酸衍生物或其碱金属盐。例如,适合的是4,4'-双(2-苯胺基-4-吗啉代-1,3,5-三嗪基-6-氨基)均二苯代乙烯-2,2'-二磺酸的盐或携带二乙醇胺基团、二甲氨基基团、苯胺基基团或2-甲氧基乙氨基基团的类似结构的化合物。也可以存在取代的二苯基苯乙烯基型增白剂,例如4,4'-双(2-磺基苯乙烯基)二苯基、4,4'-双(4-氯-3-磺基苯乙烯基)二苯基或4-(4-氯苯乙烯基)-4'-(2-磺基苯乙烯基)二苯基的碱式盐。还可以使用上述任选的增白剂的混合物。
泡沫抑制剂包括有机聚硅氧烷及其与微细的任选硅烷化(silanated)的硅酸的混合物以及石蜡及其与硅酸或双脂肪酸烯烃二酰胺类的混合物。还可以使用不同泡沫抑制剂的混合物,例如由硅氧烷、石蜡或蜡构成的那些。泡沫抑制剂、特别是包含硅氧烷和/或石蜡的泡沫抑制剂优选结合溶于或分散于水中的颗粒载体物质。特别地可以使用石蜡和双硬脂酰基乙二胺的混合物。
污物释放活性物质是正面地影响纺织品中洗涤掉油和脂肪的能力的那些化合物。这种作用在玷污的纺织品是已经用本发明包含油-和脂肪-释放成分的洗涤剂预先洗涤几次的纺织品时变得特别明显。优选的油-和脂肪-释放成分包括,例如非离子纤维素醚类,例如甲基纤维素和具有15-30wt%比例的甲氧基和1-15wt%比例的羟基丙氧基的甲基羟丙基纤维素,在每种情况中均基于非离子纤维素醚类和已知分别来自现有技术的苯二甲酸和/或对苯二甲酸或其与单体和/或聚合二元醇的衍生物的聚合物,特别是对苯二甲酸乙烯酯类和/或聚乙二醇对苯二酸酯类的聚合物或阴离子和/或其非离子修饰的衍生物。
颜色转移抑制剂包括乙烯基吡咯烷酮、乙烯基咪唑、乙烯基吡啶-N-氧化物或其共聚物。另外有用的是聚具有15,000-50,000分子量的乙烯吡咯烷酮和具有高于1,000,000、特别是1,500,000-4,000,000分子量的聚乙烯吡咯烷酮;N-乙烯基咪唑/N-乙烯基吡咯烷酮共聚物、聚乙烯噁唑烷酮类、基于乙烯基单体和羧酰胺类的共聚物、包含吡咯烷酮基团的聚酯类和聚酰胺类、接枝聚酰氨基胺类和聚乙烯亚胺类、具有由种胺构成的酰胺的聚合物、聚胺-N-氧化物聚合物、聚乙烯醇类和基于丙烯酰氨基烯基磺酸的共聚物。然而,另外能够使用酶***,其包括过氧化物酶和过氧化氢或在水中产生过氧化氢的物质。
变灰色抑制剂是保持污物从悬浮于洗涤介质中的纺织品纤维中脱离的那些材料。水溶性胶体、实际上通常是有机物适合于此,例如淀粉、胶料、明胶、淀粉或纤维素的醚羧酸或醚磺酸的盐或纤维素或淀粉的酸性硫酸酯类的盐。包含酸性基团的水溶性聚酰胺类也适合于该目的。还可以使用非上述的淀粉衍生物,例如醛淀粉。可以使用纤维素醚类,例如羧甲基纤维素(钠盐)、甲基纤维素、羟基烷基纤维素;和混合的醚类,例如甲基羟乙基纤维素、甲基羟丙基纤维素、甲基羧甲基纤维素及其混合物,例如,其用量占消费品重量的0.1-5wt%。
有机溶剂包括具有1-4个碳原子的醇类,特别是甲醇、乙醇、异丙醇和叔丁醇;具有2-4个碳原子的二元醇类,特别是乙二醇和丙二醇及其混合物;和衍生自上述化合物类型的醚类。这类与水易溶混的溶剂在本发明洗涤产品中的存在量典型地不超过30wt%。
pH调节剂包括柠檬酸、乙酸、酒石酸、苹果酸、乳酸、乙醇酸、琥珀酸、戊二酸和/或己二酸,以及无机酸,特别是硫酸或碱,特别是氢氧化铵或碱金属氢氧化物。这类pH调节剂包含在本发明的试剂中,其用量优选不高于20wt%,特别是1.2wt%-17wt%。
所述化合物以特别用于包含酶的家用产品,例如上文定义的那些,特别是用于含有酶的织物处理产品,例如洗涤剂。
现在以下是一系列实施例,用于进一步说明本发明。
一般地,本发明的化合物可以由市售的1,4-二卤代苯例如1,4-二溴苯来制备,通过交叉偶联反应例如与R1ZnCl类型的有机锌化合物进行的Negishi偶联反应以引入R1,然后进行第二交叉偶联反应例如与(取代的)烯丙醇进行的Heck偶联反应以引入具有醛的链。或者,Heck偶联反应可以与丙烯酸酯进行,得到肉桂酸酯,其随后被氢化物试剂如氢化锂铝还原,形成二氢肉桂醇,其然后通过标准方法被氧化成醛。或者,具有醛的链可通过有机合成领域技术人员已知的链延长反应连接到对位-R1取代的苯甲醛上,并随后以不还原R1的烯属部分的方式将肉桂醛选择性氢化成二氢肉桂醛。
其中R2=Me的本发明化合物可以通过以下方式来制备:邻甲酚与所需的烯丙基卤化物即R1Cl进行对烷基化反应,然后是所得苯酚转化成三氟甲磺酸酯,然后其进行如上所述的Heck偶联反应。
实施例1:3-(4-(2-甲基烯丙基)苯基)丙醛
将2-(二叔丁基膦基)-1-苯基-1H-吲哚(0.21g,0.61mmol)和双(二亚苄基丙酮)钯(0)(0.131g,0.227mmol)溶于二甲基甲酰胺(9ml)中,并将溶液在氩气氛下搅拌20min。然后添加N-环己基-N-甲基环己胺(3.55g,18.2mmol)、1-溴-4-(2-甲基烯丙基)苯(公开在S.Yasuda,Materials 2009,2(3),978-991中;3.20g,15.2mmol)和烯丙醇(2.64g,45.5mmol),并将所得混合物加热至100℃3小时,然后冷却至室温。将混合物用甲基叔丁基醚稀释,并用水、1N HCl水溶液和盐水洗涤。将有机层用MgSO4干燥并减压浓缩。将残余物通过SiO2快速柱色谱纯化,用己烷/乙酸乙酯(19:1)作为洗脱剂,分离出3-(4-(2-甲基烯丙基)苯基)丙醛,为无色油状物(Rf=0.19,2.1g,73%)。
1H NMR(400MHz,CDCl3):δ=9.83(t,J=1.5Hz,1H),7.14(s,4H),4.82(d,J=0.7Hz,1H),4.78-4.65(m,1H),3.31(s,2H),2.96(t,J=7.8Hz,2H),2.82-2.75(m,2H),1.72-1.66(br.s,3H)ppm。13C NMR(100MHz,CDCl3):δ=201.7(d),145.1(s),137.9(s),137.7(s),129.1(d),128.2(d),111.8(t),45.3(t),44.2(t),27.7(t),22.0(q)ppm。GC-MS(EI,70eV):188(M+),170(5),155(5),145(60),144(60),129(100),117(66),105(66),91(72),77(21),55(24),39(22)。
气味:花香,青香,兔耳草醛香,水味。
实施例2:3-(4-(2-甲基烯丙基)苯基)丁醛
使用相同量的催化剂、胺、溶剂和1-溴-4-(2-甲基烯丙基)苯重复实施例1的上述方法,但用(E)-丁-2-烯-1-醇(3.28g,45.6mmol,3当量)替代烯丙醇,在SiO2快速柱色谱(用己烷/乙酸乙酯19:1洗脱)纯化后分离出3-(4-(2-甲基烯丙基)苯基)丁醛,为无色油状物(Rf=0.22,0.7g,23%)。
1H NMR(400MHz,CDCl3):δ=9.70(t,J=1.9Hz,1H),7.13(s,4H),4.80-4.78(m,1H),4.72-4.71(m,1H),3.33(六重峰,J=7.2Hz,1H),3.31(s,2H),2.68(qd,J=6.9,2.3Hz,2H),1.70(br.s,3H),1.30(d,,J=7.0Hz,3H)ppm。13C NMR(100MHz,CDCl3):δ=202.0(d),145.1(s),143.2(s),138.0(s),129.2(d),126.7(d),111.9(t),51.8(t),44.2(t),34.0(d),22.2(q),22.1(q)ppm。GC-MS(EI,70eV):202(M+,4),187(3),169(2),159(48),147(100),143(17),129(28),117(48),105(23),91(45),77(9),55(41)。
气味:花香,青香,醛香,水味,黄油味。
实施例3:2-甲基-3-(4-(2-甲基烯丙基)苯基)丙醛
使用47%用量的催化剂、胺、溶剂和1-溴-4-(2-甲基烯丙基)苯重复实施例1的上述步骤,并用2-甲基丙-2-烯-1-醇(1.0g,13.4mmol,3当量)代替烯丙醇,在SiO2快速柱色谱(用己烷/乙酸乙酯19:1洗脱)纯化后分离出2-甲基-3-(4-(2-甲基烯丙基)苯基)丙醛,为无色油状物(Rf=0.38,0.75g,80%)。
1H NMR(400MHz,CDCl3):δ=9.70(d,J=1.5Hz,1H),7.13-7.03(m,4H),4.80-4.79(m,1H),4.72-4.71(m,1H),3.28(s,2H),3.06(dd,J=13.4,5.6Hz,2H),2.67-2.55(m,2H),1.67(br.s,3H),1.08(d,J=6.9Hz,3H)ppm。13C NMR(100MHz,CDCl3):δ=204.5(d),145.1(s),137.9(s),136.5(s),129.1(d),128.9(d),111.9(t),48.1(d),44.2(t),36.3(t),22.1(q),13.2(q)ppm。GC-MS(EI,70eV):202(M+,13),184(1.5),169(1.5),159(2),145(100),129(36),117(37),105(15),91(44),77(10),55(11),39(10)。
气味:醛香,金属味,水味,脂肪味。
实施例4:3-(2-甲基-4-(2-甲基烯丙基)苯基)丙醛
在如下所述的3个步骤中得到3-(2-甲基-4-(2-甲基烯丙基)苯基)丙醛:
A)2-甲基-4-(2-甲基烯丙基)苯酚
将邻-甲酚(54.1g,0.5mol)悬浮于水中,并在剧烈搅拌下添加KOH(36.5g,0.65mol,1.3当量)。将温度升至45℃,形成灰黄色溶液,将其再搅拌20min,然后冷却至10℃。在该温度下,在15分钟内逐滴添加3-氯-2-甲基丙-1-烯(58.9g,0.65mol,1.3当量)。将所得混合物剧烈搅拌6天,然后用甲苯(300ml)稀释。将有机层用2N NaOH水溶液(每次500ml)萃取3次。向合并的碱性水层中添加甲苯(300ml),并在冰浴冷却下添加浓HCl水溶液(350ml)。分离各层,并将水层进一步用甲苯萃取。将合并的有机层用盐水洗涤至中性,然后用MgSO4干燥并浓缩。将残余物在0.06mbar/76-83℃的Vigreux柱上蒸馏,分离出2-甲基-4-(2-甲基烯丙基)苯酚(36.2g,45%,纯度92%,剩余物为邻烷基化产物),为无色油状物。
1H NMR(400MHz,CDCl3):δ=6.92(br.s,1H),6.87(dd,J=8.0,1.8Hz,1H),6.87(d,J=8.0,Hz,1H),4.90(s,1H),4.78-4.77(m,1H),4.71-4.70(m,1H),3.20(s,2H),2.20(s,3H),1.66(s,3H)ppm。13C NMR(100MHz,CDCl3):δ=152.1(s),145.7(s),132.0(s),131.6(d),127.5(d),123.7(s),114.8(d),111.6(t),43.9(t),22.0(q),15.8(q)ppm。
B)3-(2-甲基-4-(2-甲基烯丙基)苯基)丙烯酸乙酯
将2-甲基-4-(2-甲基烯丙基)苯酚(5.0g,30.8mmol)溶于二氯甲烷(60ml)中,添加吡啶(4.63g,58.6mmol,1.9当量)并将溶液冷却至0℃。然后通过滴液漏斗添加三氟甲磺酸酐(1M,在二氯甲烷中,32.4ml,32.4mmol,1.05当量)并将所得溶液搅拌3小时。然后逐滴添加2N HCl水溶液(10ml)。分离水层,并将有机层用稀NaHCO3水溶液和盐水洗涤,然后用MgSO4干燥并在减压下浓缩,得到三氟甲磺酸2-甲基-4-(2-甲基烯丙基)苯基酯(8.9g,98%),为浅黄色油状物。对于随后的Heck偶联反应,将该产物(30.2mmol)溶于二甲基甲酰胺(50ml)中,并添加丙烯酸乙酯(5.75g,57.5mmol,1.9当量),然后添加三乙胺(15.0g,148mmol,4.9当量)。将所得溶液用氩气吹扫10分钟,然后添加二(三苯基膦)二氯化钯(I I)(1.06g,1.51mmol,5mol%),并将混合物在80℃下在氩气氛下搅拌6天。将混合物用MTBE稀释,并用水和盐水洗涤,然后用MgSO4干燥并在减压下浓缩。将残余物通过SiO2快速色谱(用己烷/乙酸乙酯19:1洗脱)纯化,得到(E)-3-(2-甲基-4-(2-甲基烯丙基)苯基)丙烯酸乙酯,为无色油状物(Rf=0.21,3.9g,53%)。
1H NMR(400MHz,CDCl3):δ=7.95(d,J=15.9Hz,1H),7.48(d,J=8.5Hz,1H),7.02(d,s,2H),6.34(d,J=15.9Hz,1H),4.83-4.82(m,1H),4.75-4.74(m,1H),4.26(q,J=7.1Hz,2H),3.28(s,2H),2.42(s,3H),1.67(s,3H),1.34(t,J=7.1Hz,3H)ppm。13C NMR(100MHz,CDCl3):δ=167.2(s),144.6(s),142.2(d),142.0(s),137.7(s),131.4(d),127.0(d),126.4(d),118.5(d),112.3(t),60.4(t),44.4(t),22.1(q),19.8(q),14.4(q)ppm。
C)3-(2-甲基-4-(2-甲基烯丙基)苯基)丙醛
在10℃下将3-(2-甲基-4-(2-甲基烯丙基)苯基)丙烯酸乙酯(2.0g,8.2mmol)逐滴添加到LiAlH4(0.47g,12.2mmol,1.5当量)在Et2O(40ml)中的混悬液中。将所得混合物在室温下在氩气氛下搅拌18小时。然后在10℃下小心地添加水(0.47g),随后添加15%NaOH水溶液(0.47ml),最后再添加水(0.9ml)。搅拌所形成的混悬液1小时后,滤出沉淀物,并浓缩滤液,得到无色油状物(1.7g)。将该油状物(8.3mmol)溶于二氯甲烷(5ml)中,并将溶液添加到戴斯-马丁高碘烷(4.24g,10mmol,1.2当量)在二氯甲烷(25ml)中的溶液中。将混合物搅拌2h,然后用MTBE稀释并用稀NaHCO3水溶液、水和盐水洗涤。将用MgSO4干燥并浓缩后得到的残留物通过S iO2快速色谱(用己烷/乙酸乙酯19:1洗脱)纯化,得到标题化合物,为无色油状物(Rf=0.14,0.60g,36%)。
1H NMR(400MHz,CDCl3):δ=9.84(d,J=1.4Hz,1H),7.04(d,J=7.5,1H),6.97(s,1H),6.96(d,J=8.2,1H),4.79(m,1H),4.73-4.72(m,1H),3.25(s,2H),2.93-2.89(m,2H),2.74-2.70(m,2H),2.28(s,3H),1.67(s,3H)ppm。13C NMR(100MHz,CDCl3):δ=201.8(d),145.2(s),137.9(s),136.1(s),135.8(s),131.0(d),128.4(d),126.7(d),111.8(t),44.2(t),44.1(t),25.1(t),22.1(q),19.3(q)ppm。GC-MS(EI,70eV):202(M+,36),187(8),184(18),169(21),159(86),143(100),131(88),117(33),115(48),105(39),91(33),77(15)。
气味:花香,醛香,青香,蜡香,肉桂味,紫丁香味。
Claims (15)
3.根据权利要求2的前-香料,该前-香料是由式I表示的化合物的缩醛胺和/或烯胺。
4.根据权利要求1的由式I表示的化合物和/或根据权利要求2或3的前-香料作为香料成分的用途。
5.根据权利要求4的用途,其中所述香料成分具有铃兰气味特征。
6.香料组合物,其包含根据权利要求1的由式I表示的化合物和/或根据权利要求2或3的前-香料。
7.根据权利要求6的香料组合物,其不含任何芳基取代的丙醛增香剂,所述增香剂在芳基环上在与具有醛官能团的取代基相邻的位置上是未被取代的。
8.根据权利要求7的香料组合物,其不含3-(4-叔丁基苯基)-2-甲基丙醛。
9.根据权利要求6-8中任一项的香料组合物,其包含一种或多种另外的香料成分。
10.根据权利要求6-8中任一项的香料组合物,其包含3-(4-异丁基-2-甲基苯基)丙醛。
11.个人护理或家庭护理组合物,其至少包含根据权利要求1的化合物,根据权利要求2或3的前-香料,或根据权利要求6-10中任一项的香料组合物。
12.根据权利要求11的个人护理或家庭护理组合物,还包含酶。
13.根据权利要求11或12的个人或家庭护理组合物,其特征在于它是织物处理产品。
14.根据权利要求11或12的个人或家庭护理组合物,其特征在于它是洗涤剂组合物。
15.向精细香料或消费品赋予铃兰气味特征的方法,其包括向其中添加根据权利要求1的化合物和/或根据权利要求2或3的前-香料并选择性地从所述精细香料或消费品中排除任何芳基取代的烷醛化合物的步骤,所述芳基取代的烷醛化合物在环上在与含有醛官能团的取代基相邻的位置上是未被取代的,选择性添加或排除是基于当与从大鼠分离的肝细胞一起孵育时所述化合物对酶介导降解为其苯甲酸衍生物的敏感性,所述化合物适于添加,是因为它们不降解为其苯甲酸衍生物,而所述化合物被排除,是因为它们降解为其苯甲酸衍生物。
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US20170297993A1 (en) | 2017-10-19 |
SG11201703026WA (en) | 2017-05-30 |
JP6491748B2 (ja) | 2019-03-27 |
BR112017008533A2 (pt) | 2017-12-19 |
BR112017008533B1 (pt) | 2021-11-23 |
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