CN117813368A - 取代的环戊烯酮和环戊酮作为芳香成分的用途 - Google Patents
取代的环戊烯酮和环戊酮作为芳香成分的用途 Download PDFInfo
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- CN117813368A CN117813368A CN202280055935.2A CN202280055935A CN117813368A CN 117813368 A CN117813368 A CN 117813368A CN 202280055935 A CN202280055935 A CN 202280055935A CN 117813368 A CN117813368 A CN 117813368A
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- 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
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/597—Unsaturated compounds containing a keto groups being part of a ring of a five-membered ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/613—Unsaturated compounds containing a keto groups being part of a ring polycyclic
- C07C49/617—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system
- C07C49/623—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
- C07C49/633—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing eight or nine carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/613—Unsaturated compounds containing a keto groups being part of a ring polycyclic
- C07C49/617—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system
- C07C49/643—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having three rings
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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
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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
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
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- C07—ORGANIC CHEMISTRY
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Abstract
本发明涉及至少一种具有式(I)的化合物作为芳香成分的用途。具有式(I)的化合物用于赋予组合物使人联想到甜香调、工业香调、烟草香调、香脂香调、草本香调、果香香调、木香香调、松针香调、桉树香调、粉香香调、或两种或更多种香调的组合的芳香效果,并且还增强和/或改变组合物的芳香。本发明进一步涉及一种组合物,其包含具有式(I)的化合物以及(i)至少一种不同于具有式(I)的化合物的芳香化学品或(ii)至少一种非芳香化学品载体,或者(iii)(i)和(ii)两者。
Description
技术领域
本发明涉及至少一种具有式(I)的化合物作为芳香成分的用途。具有式(I)的化合物用于赋予组合物使人联想到甜香调、工业香调(technical note)、烟草香调、香脂香调、草本香调、果香香调、木香香调、松针香调、桉树香调、粉香香调、或两种或更多种香调的组合的芳香效果,并且还增强和/或改变组合物的芳香。本发明进一步涉及一种组合物,其包含具有式(I)的化合物以及(i)至少一种不同于具有式(I)的化合物的芳香化学品或(ii)至少一种非芳香化学品载体,或者(iii)(i)和(ii)两者。
背景技术
芳香化学品,尤其是香料,尤其在化妆品、清洁和洗衣用组合物领域中非常令人感兴趣。
尽管已经存在大量合成的芳香化学品,但仍持续需要新的组分以便能够满足极为多样化的应用领域所希望的众多特性。这些首先包括感觉特性,即化合物应具有有利的气味(嗅觉)特性。此外,芳香化学品还应具有额外的正面的次要特性,例如像有效的制备方法,由于与其他芳香化学品的协同效应而有可能提供更好的感觉属性,在某些应用条件下更高的稳定性,和/或更高的牢固性。
此类特性对于组合物例如像护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物以及用于香气分配器的组合物而言特别令人感兴趣。
特别令人感兴趣的是芳香化学品,其可以赋予组合物一种或多种不同的感觉效果,从而有助于组合物产生丰富且有趣的感觉属性,尤其是嗅觉属性。在这方面,主要令人感兴趣的是可以赋予甜香调、工业香调、烟草香调、香脂香调、草本香调、果香香调、木香香调、松针香调、桉树香调、粉香香调、或两种或更多种香调的组合的芳香化学品。此外,为了在组合物中以及在用该组合物处理的表面上获得持久的气味效果,牢固性和持久性是特别令人感兴趣的。
然而,由于即使是化学结构的微小变化也会引起感觉特性如气味和/或风味的巨大变化,因此有针对性地寻找具有某些且不同的感觉特性如某种气味的物质是极其困难的。因此,在不知道实际上是否真的会找到具有所希望的气味和/或风味的物质的情况下,寻找新的芳香化学品在大多数情况下是困难且费力的。
当前要求保护的发明的一个目的是提供可以单独或作为组合物中的混合物用作芳香化学品的物质,特别是寻求具有宜人的气味的气味密集物质。此外,它们应该可与其他芳香化学品组合,从而允许产生新颖的有利的感觉属性并且可以用于组合物中。
当前要求保护的发明的一个目的是提供一种新的芳香化学品,其具有宜人的嗅觉效果;优选选自甜香调、工业香调、烟草香调、香脂香调、草本香调、果香香调、木香香调、松针香调、桉树香调、粉香香调效果中的两种或更多种的组合。
本发明的另一个目的是提供芳香化学品,其是无毒的,并且这些芳香化学品应当可从容易获得的起始材料获得,从而允许其快速且经济地制造。
发明内容
本发明的目的通过提供具有式(I)的化合物来实现,这些化合物可以容易地制造并且具有宜人的芳香。
当前要求保护的发明涉及至少一种具有式(I)的化合物
具有式(I)的化合物
或其立体异构体用于赋予组合物芳香效果的用途,
其中,
……虚线代表单键或双键,
R1、R2、R3和R4独立地选自H、或直链或支链的C1-C5烷基,或者
R1和R2组合形成取代或未取代的5元或6元脂环族环,并且R3和R4组合形成取代或未取代的5元或6元脂环族环。
在另一方面,当前要求保护的发明涉及具有式(Ia)的化合物
具有式(Ia)的化合物
或其立体异构体用于赋予组合物芳香效果的用途,
其中,
R1、R2、R3和R4独立地选自H、或直链或支链的C1-C5烷基,
或者
R1和R2组合形成取代或未取代的5元或6元脂环族环,并且R3和R4组合形成取代或未取代的5元或6元脂环族环。
当前要求保护的发明的另外的方面涉及具有式(Ib)的化合物
具有式(Ib)的化合物
或其立体异构体用于赋予组合物芳香效果的用途,
其中,
R1、R2、R3和R4独立地选自H、或直链或支链的C1-C5烷基。
当前要求保护的发明的另外的方面涉及一种赋予组合物芳香效果的方法,该方法至少包括向组合物中添加具有式(I)的化合物、具有式(Ia)的化合物、或具有式(Ib)的化合物的步骤。
当前要求保护的发明的另一个方面涉及具有式(I)的化合物、具有式(Ia)的化合物、或具有式(Ib)的化合物用于改变组合物的芳香特征的用途。
当前要求保护的发明的另外的方面涉及具有式(I)的化合物、具有式(Ia)的化合物、或具有式(Ib)的化合物用于赋予甜香调、工业香调、烟草香调、香脂香调、草本香调、果香香调、木香香调、松针香调、桉树香调、粉香香调、或两种或更多种香调的组合的用途。
当前要求保护的发明的另外的方面涉及一种促进组合物的芳香的方法。所述方法包括将具有式(I)的化合物、具有式(Ia)的化合物、或具有式(Ib)的化合物与其他成分例如像至少一种不同于具有式(I)的化合物的其他芳香化学品和/或至少一种非芳香化学品载体混合以获得芳香组合物的步骤。
当前要求保护的发明的又另一个方面涉及一种改变组合物的芳香的方法。所述方法包括将至少一种当前要求保护的发明的化合物掺入芳香组合物中以获得芳香改变的芳香组合物的步骤。
此外,具有式(I)的化合物可以通过从容易获得的起始材料开始的简单合成以良好的产率和纯度生产。因此,当前要求保护的发明的化合物可以以简单且成本高效的方式大规模生产。
具体实施方式
贯穿本说明书对“一个实施例”或“实施例”或者“优选实施例”的引用意指结合该实施例描述的特定特征、结构或性质被包括在当前要求保护的发明的至少一个实施例中。因此,贯穿本说明书的不同地方出现的短语“在一个实施例中”或“在优选实施例中(In apreferred embodiment或in a preferred embodiment)”并不一定都指代同一个实施例,但是可以指代同一个实施例。此外,在一个或多个实施例中,如本领域技术人员从本披露中显而易见的,特征、结构或性质可以以任何合适的方式组合。此外,尽管本文描述的一些实施例包括其他实施例中包括的一些但不是其他特征,但是不同实施例的特征的组合意指在本主题的范围内,并且形成不同实施例,如本领域技术人员将理解的。例如,在所附权利要求中,以任何组合使用所要求保护的实施例中的任何一个。
此外,贯穿本说明书定义的范围也包括端值,即1至10的范围意味着1和10两者都包括在该范围内。为避免疑义,申请人有权根据适用法律获得任何等效方式。
在本发明的上下文中,术语“芳香”是指感觉特性并且包括气味和/或风味。
术语“芳香化学品”表示用于获得感觉或感官(在本文中可互换使用)效果的物质并且包括其获得嗅觉和/或风味效果的用途。术语“嗅觉效果”或“香调”(在此可互换使用)表示没有任何正面或负面判断的气味效果,而如本文所用的术语“香气效果”或“香味效果”或“芳香效果”(在本文中可互换使用)与通常感觉宜人的气味效果有关。因此,“香味”或“香气”表示主要引起宜人的气味效果的芳香化学品。风味表示引起味觉效果的芳香化学品。
如本文所用,术语“芳香组合物”是指引起芳香的组合物。术语芳香组合物包括“气味组合物”和/或“风味组合物”。气味组合物是主要引起气味效果的组合物,风味组合物是主要引起味觉效果的组合物。
术语“芳香属性”表示芳香化学品的总体芳香效果并由芳香化学品的各个芳香效果构成。
术语“气味组合物”包括“香味组合物”或“香气组合物”(在本文中可互换使用),其主要引起通常感觉宜人的气味效果。
通用表述“有利的感觉特性”或“有利的感官特性”描述了芳香化学品所传递的感官效果的美好性和清晰性。“美好性”和“清晰性”是本领域技术人员、如调香师熟悉的术语。美好性通常是指自发引起的、正面感知的、宜人的感觉效果。然而,“美好”不一定与“甜”同义。“美好”也可以是麝香或檀香的气味。“清晰性”通常是指自发引起的感觉效果,其对于同一测试小组而言,引起可再现地令人想起相同的具体事物。例如,物质可以具有自发使人联想到“苹果”的气味:该气味然后将清晰地是“苹果”。如果此苹果气味非常宜人,因为该气味使人联想到例如甜的、完全成熟的苹果,则该气味将被称为“美好”。然而,典型的酸涩苹果的气味也可以是清晰的。如果在闻到该物质后产生这两种反应,在该实例中因此是美好且清晰的苹果气味,则此物质具有特别有利的感觉特性。
当在本文中使用表述“……的组合”或“与……组合(in combination with或combined with)”来指代两种化合物的组合物、方法或用途时,考虑到这两种化合物无需以所述化合物的物理混合物的形式使用,而是可以单独使用(例如,添加)的事实。当化合物单独使用时,它们可以以任何顺序依次地(即一个接一个地)或同时地(即基本上同一时间)使用(例如,添加)。
术语“促进(boosting)”或“促进(boost)”在本文中用于描述增强和/或改变芳香化学品或组合物(相应地是芳香组合物)的芳香的作用。术语“增强”包括芳香的美好性和/或清晰性的改善和/或强度的改善。术语“改变”包括芳香属性的变化。术语“美好性”和“清晰性”是本领域技术人员、如调香师熟悉的并且具有相应的含义。
强度可以通过阈值确定来确定。气味的阈值是相关气体空间中的物质的浓度,在该浓度下,虽然不再需要对气味效果进行定义,但气味效果刚好仍然可被代表性测试小组感知。
当需要以前调为特征的应用、其中要特别快速且强烈地传递气味时,在香味组合物中特别希望促进剂作用,例如在除臭剂、空气清新剂中或在口香糖中的味觉部分中。
术语“本发明涉及(the invention relates to)”和“本发明涉及(the inventionis directed to)”贯穿本发明同义地使用。
术语“持久性”描述了芳香化学品随时间推移的蒸发行为。持久性可以例如通过将芳香化学品施用于测试条,并通过随后对测试条的气味效果的嗅觉评估来确定。对于具有高持久性的芳香化学品,小组仍然能够识别芳香效果的时间跨度是长的。
术语“牢固性”描述了芳香化学品与表面(例如像皮肤或纺织品)的相互作用,尤其是在表面的随后处理(例如像洗涤)之后。牢固性可以例如通过用包含芳香化学品的纺织品洗涤剂组合物洗涤纺织品并随后在洗涤后直接对纺织品(湿纺织品)进行嗅觉评价以及在长时间储存后对干纺织品进行评价来确定。
术语“稳定性”描述了芳香化学品在与氧气、光和/或其他物质接触后的行为。具有高稳定性的芳香化学品在长时间内保持其芳香属性,优选在多种组合物中和在各种储存条件下。
为了赋予组合物或用组合物处理的表面持久的芳香效果,组合物中的芳香化学品的持久性、牢固性以及稳定性应当优选地是高的。
术语“C1-C5-烷基”是指具有1至5个碳原子的直链或支链饱和烃基,例如,甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、1,1-二甲基丙基、1,2-二甲基丙基。
除非本文另有说明,否则本文所述的“化合物(I)”涉及由式(I)所定义的化合物、或其盐或立体异构体。
具有式(I)的化合物包括由具有式(Ia)的化合物和具有式(Ib)的化合物代表的化合物。
术语“立体异构体”是用于单个化合物的所有异构体的通用术语,这些异构体的区别仅在于其原子在空间上的取向,而不在于原子的连接方式因此,术语立体异构体包括镜像异构体(对映异构体)、几何(顺/反或E/Z)异构体、和非对映异构体。对于这些术语的精确定义,参见Houben-Weyl E21a,Stereoselective Synthesis[立体选择性合成]G.Helmchen,R.W.Hoffmann,J.Mulzer,E.Schaumann(Hrsg.),1995,1-74中的G.Helmchen:“Vocabulary and Nomenclature of Organic Stereochemistry[有机立体化学的词汇和命名法]”。可能的异构体可以作为混合物存在(即外消旋体、顺式/反式混合物或非对映异构体的混合物)。
用途:
当前要求保护的发明的一个实施例涉及至少一种具有式(I)的化合物
具有式(I)的化合物
或其立体异构体用于赋予组合物芳香效果的用途,
其中,
……虚线代表单键或双键,
R1、R2、R3和R4独立地选自H、或直链或支链的C1-C5烷基,或者
R1和R2组合形成取代或未取代的5元或6元脂环族环,并且R3和R4组合形成取代或未取代的5元或6元脂环族环。
在另一个实施例中,当前要求保护的发明涉及至少一种具有式(Ia)的化合物
具有式(Ia)的化合物
或其立体异构体用于赋予组合物芳香效果的用途,
其中,
R1、R2、R3和R4独立地选自H、或直链或支链的C1-C5烷基,或者
R1和R2组合形成取代或未取代的5元或6元脂环族环,并且R3和R4组合形成取代或未取代的5元或6元脂环族环。
在另一个实施例中,当前要求保护的发明涉及至少一种具有式(Ib)的化合物
具有式(Ib)的化合物
或其立体异构体用于赋予组合物芳香效果的用途,
其中,
R1、R2、R3和R4独立地选自H、或直链或支链的C1-C5烷基。
在本发明的实施例中,R1、R2、R3、R4独立地选自H、甲基、乙基、丙基、异丙基、丁基、异丁基、戊基、或异戊基。
优选地,R1、R2、R3、R4独立地选自H、甲基、乙基、异丙基或异丁基。
在优选实施例中,至少一种具有式(Ia)的化合物是:R1、R2、R3中的每一个是甲基并且R4是乙基。
在另一个优选实施例中,至少一种具有式(Ia)的化合物是:R1、R3中的每一个是甲基,R2是异丙基,R4是异丁基。
在又另一个优选实施例中,至少一种具有式(Ia)的化合物是:R1、R3、R4中的每一个是甲基,R2是H。
在另一个优选实施例中,至少一种具有式(Ia)的化合物是:R1和R2组合形成未取代的6元脂环族环,并且R3和R4组合形成未取代的6元脂环族环。
在实施例中,至少一种具有式(Ia)的化合物是
具有式I(a’)的化合物。
在另一个实施例中,具有式I(a’)的化合物包含较少量的具有式(II)的化合物
具有式II的化合物。
本领域技术人员可以分离具有式(II)的化合物,并且其可以用于制备具有式I(a’)的化合物和具有式II的化合物呈任何希望比率的混合物。该比率可由本领域技术人员根据任何合适的组合物中的组合的最终用途来确定。
在优选实施例中,至少一种具有式(Ib)的化合物是:R1、R2、R3中的每一个是甲基并且R4是乙基。
当前要求保护的发明的优选实施例涉及至少一种具有式(I)的化合物作为芳香化学品用于赋予选自以下的芳香效果的用途:甜香调、工业香调、烟草香调、香脂香调、草本香调、果香香调、木香香调、松针香调、桉树香调、粉香香调、或两种或更多种香调的组合。
在另一个实施例中,当前要求保护的发明涉及至少一种具有式(I)的化合物、至少一种具有式(Ia)的化合物、或至少一种具有式(Ib)的化合物用于促进组合物的芳香的用途。
在当前要求保护的发明的实施例中,至少一种具有式(I)的化合物、至少一种具有式(Ia)的化合物、或至少一种具有式(Ib)的化合物用作香料或香料组合物的成分。
特别地,至少一种具有式(I)的化合物、至少一种具有式(Ia)的化合物、或至少一种具有式(Ib)的化合物用于赋予组合物选自以下的香调:甜香调、工业香调、烟草香调、香脂香调、草本香调、果香香调、木香香调、松针香调、桉树香调、粉香香调、或两种或更多种香调的组合。
优选地,至少一种具有式(I)的化合物、至少一种具有式(Ia)的化合物、或至少一种具有式(Ib)的化合物用于赋予组合物选自以下的效果中的两种或更多种的组合:甜香调、工业香调、烟草香调、香脂香调、草本香调、果香香调、木香香调、松针香调、桉树香调、粉香香调。
合适的组合物是例如用于个人护理、家庭护理、工业应用中的组合物以及用于其他应用中的组合物,如药物组合物或作物保护组合物。
优选地,根据当前要求保护的发明的具有式(I)的化合物用于选自以下的组合物中:香水组合物、身体护理组合物(包括化妆品组合物以及用于口腔和牙齿卫生的产品)、卫生制品、清洁组合物(包括餐具洗涤组合物)、纺织品洗涤剂组合物、用于香气分配器的组合物、食品、食品补充剂、药物组合物或作物保护组合物。
组合物已在下文段落中描述。
化合物:
本发明的一个实施例涉及具有式(Ia)的化合物
具有式(Ia)的化合物
或其立体异构体,
其中,
R1和R3独立地选自H、和直链或支链的C1-C5烷基,
R2选自直链或支链的C2-C5烷基,并且
R4选自直链或支链的C1-C5烷基,或者
R1和R2组合形成取代或未取代的5元或6元脂环族环,并且R3和R4组合形成取代或未取代的5元或6元脂环族环。
在本发明的实施例中,R1、R3、R4独立地选自H、甲基、乙基、丙基、异丙基、丁基、异丁基、戊基、或异戊基,R2选自乙基、丙基、异丙基、丁基、异丁基、戊基、或异戊基。
在本发明的优选实施例中,R1、R3中的每一个是甲基,R2是异丙基,R4是异丁基。
组合物:
在实施例中,当前要求保护的发明涉及一种组合物,其包含:至少一种具有式(I)的化合物,以及
(i)至少一种不同于以下的芳香化学品(X):至少一种具有式(I)的化合物、至少一种具有式(Ia)的化合物、或至少一种具有式(Ib)的化合物,或
(ii)至少一种非芳香化学品载体,或者
(iii)(i)和(ii)两者。
优选地,在此实施例中,组合物包含基于组合物的总重量在≥0.01wt.%至≤70.0wt.%范围内的总量的具有式(I)的化合物。
优选地,该组合物是芳香组合物,更优选香料组合物。
不同于具有式(I)的化合物的芳香化学品。
出于本发明的目的,具有式(I)的化合物包括具有式(Ia)的化合物和具有式(Ib)的化合物。
在一个优选实施例中,组合物包含至少一种不同于该至少一种具有式(I)的化合物的芳香化学品。不同于具有式(I)的化合物的芳香化学品也称为芳香化学品(X)。
由于其物理特性,具有式(I)的化合物可与芳香组合物、特别是香料组合物中的不同于具有式(I)的化合物的芳香化学品和其他常规成分很好地组合。这允许例如产生具有新颖的有利感觉属性的芳香组合物(优选香料组合物)。尤其是如上所述的,这些化合物可以为其他芳香化学品(如香料)提供促进剂作用。
芳香化学品(X)优选地选自:
乙酸香叶酯、α-己基肉桂醛、异丁酸2-苯氧基乙酯、二氢月桂烯醇、二氢茉莉酮酸甲酯、4,6,6,7,8,8-六甲基-1,3,4,6,7,8-六氢环戊并[g]苯并吡喃、四氢芳樟醇、乙基芳樟醇、水杨酸苄酯、2-甲基-3-(4-叔丁基苯基)丙醛、肉桂醇、乙酸4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-5-茚基酯和/或乙酸4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-6-茚基酯、香茅醇、乙酸香茅酯、四氢香叶醇、香草醛、乙酸芳樟酯、乙酸苏合香酯、八氢-2,3,8,8-四甲基-2-萘乙酮和/或2-乙酰基-1,2,3,4,6,7,8-八氢-2,3,8,8-四甲基萘、水杨酸己酯、4-叔丁基环己基乙酸酯、2-叔丁基环己基乙酸酯、α-紫罗兰酮、α-正甲基紫罗兰酮、α-异甲基紫罗兰酮、香豆素、乙酸松油酯、2-苯基乙醇、4-(4-羟基-4-甲基戊基)-3-环己烯-甲醛、α-戊基肉桂醛、巴西酸乙二醇酯、(E)和/或(Z)-3-甲基环十五碳-5-烯酮、15-十五碳-11-烯内酯和/或15-十五碳-12-烯内酯、15-环十五烷内酯、1-(5,6,7,8-四氢-3,5,5,6,8,8-六甲基-2-萘基)乙酮、2-异丁基-4-甲基四氢-2H-吡喃-4-醇、2-乙基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇、顺式-3-己烯基乙酸酯、反式-3-己烯基乙酸酯、反式-2/顺式-6-壬二烯醇、2,4-二甲基-3-环己烯甲醛、2,4,4,7-四甲基辛-6-烯-3-酮、2,6-二甲基-5-庚烯-1-醛、冰片、3-(3-异丙基苯基)丁醛、2-甲基-3-(3,4-亚甲基二氧基苯基)丙醛、3-(4-乙基苯基)-2,2-二甲基丙醛、7-甲基-2H-1,5-苯并二氧杂-3(4H)-酮、3,3,5-三甲基环己基乙酸酯、2,5,5-三甲基-1,2,3,4,4a,5,6,7-八氢萘-2-酚、3-(4-叔丁基苯基)-丙醛、2-甲基戊酸乙酯、乙氧基甲氧基环十二烷、2,4-二甲基-4,4a,5,9b-四氢茚并[1,2-d][1,3]二噁英、(2-叔丁基环己基)乙酸酯、或3-[5,5,6-三甲基双环[2.2.1]庚-2-基]环己-1-醇。
在优选实施例中,至少一种芳香化学品(X)选自苯甲酸甲酯、乙酸苄酯、乙酸香叶酯、2-异丁基-4-甲基四氢-2H-吡喃-4-醇、芳樟醇、2-异丁基-4-甲基四氢-2H-吡喃-4-醇、或苯甲酸甲酯。
在另一个优选实施例中,至少一种芳香化学品(X)选自乙基香草醛、香草醛、2,5-二甲基-4-羟基-2H-呋喃-3-酮(呋喃酮)或3-羟基-2-甲基-4H-吡喃-4-酮(麦芽酚)。
具有式(I)的化合物可以与其组合以得到根据当前要求保护的发明的组合物的另外的芳香化学品可以例如在S.Arctander,Perfume and Flavor Chemicals[香水和香精化学品],第I和II卷,蒙特克莱尔,新泽西州,1969,自出版或H.Surburg和J.Panten,CommonFragrance and Flavor Materials[常见的香料和香精材料],第4版,威利VCH出版社,魏因海姆2016中找到。具体地,可以提及:
来自天然原材料的提取物,如精油、冷凝脂、净油、树脂、香膏、香脂、酊剂,例如像
龙涎香酊剂;阿米香树油;当归籽油;当归根油;茴芹籽油;缬草油;罗勒油;树藓净油;月桂油;艾蒿油;安息香树脂;香柠檬油;蜂蜡净油;桦焦油;苦杏仁油;香薄荷油;布枯叶油;卡鲁瓦油;杜松油;菖蒲油;樟脑油;依兰油;小豆蔻油;卡藜油;肉桂油;肉桂净油;海狸香净油;雪松叶油;雪松木油;岩蔷薇油;香茅油;柠檬油;古巴香脂;古巴香脂油;芫荽油;木香根油;枯茗油;丝柏油;印蒿油;莳萝叶油;莳萝籽油;淡香水净油;橡苔净油;榄香脂油;龙蒿油;柠檬桉油;桉树油;茴香油;松针油;白松香油;白松香树脂;天竺葵油;葡萄柚油;愈创木油;古芸香脂;古芸香脂油;蜡菊净油;蜡菊油;姜油;鸢尾根净油;鸢尾根油;茉莉净油;菖蒲油;蓝春黄菊油;罗马甘菊油;胡萝卜籽油;卡藜油;松针油;留兰香油;葛缕子油;赖百当油;赖百当净油;赖百当树脂;醒目薰衣草净油;醒目薰衣草油;薰衣草净油;薰衣草油;柠檬草油;独活草油;蒸馏酸橙油;压榨酸橙油;芳樟醇油;山苍子油;月桂叶油;肉豆蔻油;马郁兰油;橘子油;香厚壳桂皮油;含羞草净油;麝香籽油;麝香酊剂;香紫苏油;肉豆蔻仁油;没药净油;没药油;桃金娘油;丁香叶油;丁香花油;橙花油;乳香净油;乳香油;红没药油;橙花净油;橙油;牛至油;玫瑰草油;广藿香油;紫苏油;秘鲁香脂油;欧芹叶油;欧芹籽油;橙叶油;薄荷油;胡椒油;甘椒油;松树油;胡薄荷油;玫瑰净油;玫瑰木油;玫瑰油;迷迭香油;达尔马堤亚鼠尾草油;西班牙鼠尾草油;檀香油;芹菜籽油;宽叶熏衣草油;八角油;苏合香油;万寿菊油;冷杉油;茶树油;松节油;百里香油;吐鲁香脂;香豆净油;晚香玉净油;香草提取物;紫罗兰叶净油;马鞭草油;香根草油;杜松子油;酒渣油;苦艾油;冬青油;牛膝草油;麝猫香净油;肉桂叶油;肉桂皮油,及其馏分,或从中分离的成分;
来自以下的组的单独的香料:烃,例如像3蒈烯;α-蒎烯;β-蒎烯;α-萜品烯;γ-萜品烯;对伞花烃;没药烯;莰烯;石竹烯;雪松烯;法呢烯;柠檬烯;长叶烯;月桂烯;罗勒烯;香橙烯;(E,Z)-1,3,5-十一碳三烯;苯乙烯;二苯甲烷;
脂肪族醇,例如像己醇;辛醇;3-辛醇;2,6-二甲基庚醇;2-甲基-2-庚醇;2-甲基-2-辛醇;(E)-2-己烯醇;(E)-和(Z)-3-己烯醇;1-辛烯-3-醇;3,4,5,6,6-五甲基-3/4-庚烯-2-醇和3,5,6,6-四甲基-4-亚甲基庚-2-醇的混合物;(E,Z)-2,6-壬二烯醇;3,7-二甲基-7-甲氧基辛-2-醇;9-癸烯醇;10-十一烯醇;4-甲基-3-癸烯-5-醇;
脂肪族醛及其缩醛,例如像己醛;庚醛;辛醛;壬醛;癸醛;十一醛;十二醛;十三醛;2-甲基辛醛;2-甲基壬醛;(E)-2-己烯醛;(Z)-4-庚烯醛;2,6-二甲基-5-庚烯醛;10-十一烯醛;(E)-4-癸烯醛;2-十二烯醛;2,6,10-三甲基-9-十一烯醛;2,6,10-三甲基-5,9-十一碳二烯醛;庚醛二乙基缩醛;1,1-二甲氧基-2,2,5-三甲基-4-己烯;香茅氧基乙醛;(E/Z)-1-(1-甲氧基丙氧基)-己-3-烯;脂肪族酮及其肟,例如像2-庚酮;2-辛酮;3-辛酮;2-壬酮;5-甲基-3-庚酮;5-甲基-3庚酮肟;2,4,4,7-四甲基-6-辛烯-3-酮;6-甲基-5-庚烯-2-酮;
脂肪族含硫化合物,例如像3-甲硫基己醇;乙酸3-甲硫基己基酯;3-巯基己醇;乙酸3-巯基己基酯;丁酸3-巯基己基酯;乙酸3-乙酰硫基己基酯;1-薄荷烯-8-硫醇;
脂肪族腈,例如像2-壬烯腈;2-十一碳烯腈;2-十三碳烯腈;3,12-十三碳二烯腈;3,7-二甲基-2,6-辛二烯腈;3,7-二甲基-6-辛烯腈;
脂肪族羧酸的酯,例如像(E)和(Z)-3-己烯基甲酸酯;乙酰乙酸乙酯;乙酸异戊酯;乙酸己酯;乙酸3,5,5-三甲基己基酯;乙酸3-甲基-2-丁烯基酯;乙酸(E)-2-己烯基酯;乙酸(E)和(Z)-3-己烯基酯;乙酸辛酯;乙酸3-辛基酯;乙酸1-辛烯-3-基酯;丁酸乙酯;丁酸丁酯;丁酸异戊酯;丁酸己酯;异丁酸(E)和(Z)-3-己烯基酯;巴豆酸己酯;异戊酸乙酯;2-甲基戊酸乙酯;己酸乙酯;己酸烯丙酯;庚酸乙酯;庚酸烯丙酯;辛酸乙酯;(E,Z)-2,4-癸二烯酸乙酯;2-辛炔酸甲酯;2-壬炔酸甲酯;2-异戊氧基乙酸烯丙酯;甲基-3,7-二甲基-2,6-辛二烯酸酯;巴豆酸4-甲基-2-戊基酯;
无环萜烯醇,例如像香叶醇;橙花醇;芳樟醇;薰衣草醇;橙花叔醇;法呢醇;四氢芳樟醇;2,6-二甲基-7-辛烯-2-醇;2,6-二甲基辛-2-醇;2-甲基-6-亚甲基-7-辛烯-2-醇;2,6-二甲基-5,7-辛二烯-2-醇;2,6-二甲基-3,5-辛二烯-2-醇;3,7-二甲基-4,6-辛二烯-3-醇;3,7-二甲基-1,5,7-辛三烯-3-醇;2,6-二甲基-2,5,7-辛三烯-1-醇;及其甲酸酯、乙酸酯、丙酸酯、异丁酸酯、丁酸酯、异戊酸酯、戊酸酯、己酸酯、巴豆酸酯、惕各酸酯和3-甲基-2-丁烯酸酯;
无环萜烯醛和酮,例如像香叶醛;橙花醛;香茅醛;7-羟基-3,7-二甲基辛醛;7-甲氧基-3,7-二甲基辛醛;2,6,10-三甲基-9-十一烯醛;香叶基丙酮;以及香叶醛、橙花醛、7-羟基-3,7-二甲基辛醛的二甲基和二乙基缩醛;环状萜烯醇,例如像薄荷醇;异蒲勒醇;α-萜品醇;萜品-4-醇;薄荷烷-8-醇;薄荷烷-1-醇;薄荷烷-7-醇;冰片;异冰片;氧化芳樟醇;诺卜醇;雪松醇;龙涎醇;岩兰草醇;愈创木醇;及其甲酸酯、乙酸酯、丙酸酯、异丁酸酯、丁酸酯、异戊酸酯、戊酸酯、己酸酯、巴豆酸酯、惕各酸酯和3-甲基-2-丁烯酸酯;
环状萜烯醛和酮,例如像薄荷酮;异薄荷酮;8-巯基薄荷烷-3-酮;香芹酮;樟脑;茴香酮;α-紫罗兰酮;β-紫罗兰酮;α-正甲基紫罗兰酮;β-正甲基紫罗兰酮;α-异甲基紫罗兰酮;β-异甲基紫罗兰酮;α-鸢尾酮;α-突厥酮;β-突厥酮;β-突厥烯酮;δ-突厥酮;γ-突厥酮;1-(2,4,4-三甲基-2-环己烯-1-基)-2-丁烯-1-酮;1,3,4,6,7,8a-六氢-1,1,5,5-四甲基-2H-2,4a-桥亚甲基萘-8(5H)-酮;2-甲基-4-(2,6,6-三甲基-1-环己烯-1-基)-2-丁烯醛;诺卡酮;二氢诺卡酮;4,6,8-巨豆三烯-3-酮;α-甜橙醛;β-甜橙醛;乙酰化雪松木油(甲基柏木酮);
环状醇,例如像4-叔丁基环己醇;3,3,5-三甲基环己醇;3-异莰基环己醇;2,6,9-三甲基-Z2,Z5,E9-环十二碳三烯-1-醇;2-异丁基-4-甲基四氢-2H-吡喃-4-醇;
脂环族醇,例如像α-3,3-三甲基环己基甲醇;1-(4-异丙基环己基)乙醇;2-甲基-4-(2,2,3-三甲基-3-环戊-1-基)丁醇;2-甲基-4-(2,2,3-三甲基-3-环戊-1-基)-2-丁烯-1-醇;2-乙基-4-(2,2,3-三甲基-3-环戊-1-基)-2-丁烯-1-醇;3-甲基-5-(2,2,3-三甲基-3-环戊-1-基)戊-2-醇;3-甲基-5-(2,2,3-三甲基-3-环戊-1-基)-4-戊烯-2-醇;3,3-二甲基-5-(2,2,3-三甲基-3-环戊-1-基)-4-戊烯-2-醇;1-(2,2,6-三甲基环己基)戊-3-醇;1-(2,2,6-三甲基环己基)己-3-醇;
环状和脂环族醚,例如像桉树脑;甲基柏木醚;环十二烷基甲基醚;1,1-二甲氧基环十二烷;(乙氧基甲氧基)环十二烷;α-雪松烯环氧化物;3a,6,6,9a-四甲基十二氢萘并[2,1-b]呋喃;3a-乙基-6,6,9a-三甲基十二氢萘并[2,1-b]呋喃;1,5,9-三甲基-13-氧杂双环-[10.1.0]十三碳-4,8-二烯;玫瑰醚;2-(2,4-二甲基-3-环己烯-1-基)-5-甲基-5-(1-甲基丙基)-1,3-二噁烷;
环酮和大环酮,例如像4-叔丁基环己酮;2,2,5-三甲基-5-戊基环戊酮;2-庚基环戊酮;2-戊基环-戊酮;2-羟基-3-甲基-2-环戊烯-1-酮;3-甲基-顺式-2-戊烯-1-基-2-环戊烯-1-酮;3-甲基-2-戊基-2-环戊烯-1-酮;3-甲基-4-环十五烷酮;3-甲基-5-环十五烷酮;3-甲基环十五烷酮;4-(1-乙氧基乙烯基)-3,3,5,5-四甲基环己酮;4-叔戊基环己酮;5-环十六碳烯-1-酮;6,7-二氢-1,1,2,3,3-五甲基-4(5H)-茚酮;8-环十六碳烯-1-酮;7-环十六碳烯-1-酮;(7/8)-环十六碳烯-1-酮;9-环十七碳烯-1-酮;环十五烷酮;环十六烷酮;
脂环族醛,例如像2,4-二甲基-3-环己烯甲醛;2-甲基-4-(2,2,6-三甲基环己烯-1-基)-2-丁烯醛;4-(4-羟基-4-甲基戊基)-3-环己烯甲醛;4-(4-甲基-3-戊烯-1-基)-3-环己烯甲醛;
脂环族酮,例如像1-(3,3-二甲基环己基)-4-戊烯-1-酮;2,2-二甲基-1-(2,4-二甲基-3-环己烯-1-基)-1-丙酮;1-(5,5-二甲基-1-环己烯-1-基)-4-戊烯-1-酮;2,3,8,8-四甲基-1,2,3,4,5,6,7,8-八氢-2-萘基甲基酮;甲基2,6,10-三甲基-2,5,9-环十二碳三烯基酮;叔丁基(2,4-二甲基-3-环己烯-1-基)酮;
环状醇的酯,例如像乙酸2-叔丁基环己基酯;乙酸4-叔丁基环己基酯;乙酸2-叔戊基环己基酯;乙酸4-叔戊基环己基酯;乙酸3,3,5-三甲基环己基酯;乙酸十氢-2-萘基酯;巴豆酸2-环戊基环戊基酯;乙酸3-戊基四氢-2H-吡喃-4-基酯;乙酸十氢-2,5,5,8a-四甲基-2-萘基酯;乙酸4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-5或6-茚基酯;丙酸4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-5或6-茚基酯;异丁酸4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-5或6-茚基酯;乙酸4,7-桥亚甲基八氢-5或6-茚基酯;
脂环族醇的酯,例如像巴豆酸1-环己基乙基酯;
脂环族羧酸的酯,例如像3-环己基丙酸烯丙酯;环己氧基乙酸烯丙酯;顺式和反式二氢茉莉酮酸甲酯;顺式和反式茉莉酮酸甲酯;2-己基-3-氧代环戊烷甲酸甲酯;2-乙基-6,6-二甲基-2-环己烯甲酸乙酯;2,3,6,6-四甲基-2-环己烯甲酸乙酯;2-甲基-1,3-二氧戊环-2-乙酸乙酯;
芳脂族醇,例如像苄醇;1-苯基乙醇、2-苯基乙醇、3-苯基丙醇;2-苯基丙醇;2-苯氧基乙醇;2,2-二甲基-3-苯基丙醇;2,2-二甲基-3-(3-甲基苯基)丙醇;1,1-二甲基-2-苯基乙醇;1,1-二甲基-3-苯基丙醇;1-乙基-1-甲基-3-苯基丙醇;2-甲基-5-苯基戊醇;3-甲基-5-苯基戊醇;3-苯基-2-丙烯-1-醇;4-甲氧基-苯甲醇;1-(4-异丙基苯基)乙醇;
芳脂族醇和脂肪族羧酸的酯,例如像乙酸苄酯;丙酸苄酯;异丁酸苄酯;异戊酸苄酯;乙酸2-苯基乙基酯;丙酸2-苯基乙基酯;异丁酸2-苯基乙基酯;异戊酸2-苯基乙基酯;乙酸1-苯基乙基酯;乙酸α-三氯甲基苄基酯;乙酸α,α-二甲基苯基乙基酯;丁酸α,α-二甲基苯基乙基酯;乙酸肉桂酯;异丁酸2-苯氧基乙基酯;乙酸4-甲氧基苄基酯;
芳脂族醚,例如像2-苯基乙基甲基醚;2-苯基乙基异戊基醚;2-苯基乙基1-乙氧基乙基醚;苯乙醛二甲基缩醛;苯乙醛二乙基缩醛;氢化阿托醛二甲基缩醛;苯乙醛甘油缩醛;2,4,6-三甲基-4-苯基-1,3-二噁烷;4,4a,5,9b-四氢茚并[1,2-d]-间二噁英;4,4a,5,9b-四氢-2,4-二甲基茚并[1,2-d]-间-二噁英;
芳香族和芳脂族醛,例如像苯甲醛;苯乙醛;3-苯基丙醛;氢化阿托醛;4-甲基苯甲醛;4-甲基苯乙醛;3-(4-乙基苯基)-2,2-二甲基丙醛;2-甲基-3-(4-异丙基苯基)丙醛;2-甲基-3-(4-叔丁基苯基)丙醛;2-甲基-3-(4-异丁基苯基)丙醛;3-(4-叔丁基苯基)丙醛;肉桂醛;α-丁基肉桂醛;α-戊基肉桂醛;α-己基肉桂醛;3-甲基-5-苯基戊醛;4-甲氧基苯甲醛;4-羟基-3-甲氧基苯甲醛;4-羟基-3-乙氧基苯甲醛;3,4-亚甲基二氧基苯甲醛;3,4-二甲氧基苯甲醛;2-甲基-3-(4-甲氧基苯基)丙醛;2-甲基-3-(4-亚甲基二氧基苯基)丙醛;
芳香族和芳脂族酮,例如像苯乙酮;4-甲基苯乙酮;4-甲氧基苯乙酮;4-叔丁基-2,6-二甲基苯乙酮;4-苯基-2-丁酮;4-(4-羟基苯基)-2-丁酮;1-(2-萘基)-乙酮;2-苯并呋喃基乙酮;(3-甲基-2-苯并呋喃基)乙酮;二苯甲酮;1,1,2,3,3,6-六甲基-5-茚满基甲基酮;6-叔丁基-1,1-二甲基-4-茚满基甲基酮;1-[2,3-二氢-1,1,2,6-四甲基-3-(1-甲基乙基)-1H-5-茚基]乙酮;5',6',7',8'-四氢-3',5',5',6',8',8'-六甲基-2'-萘乙酮;
芳香族和脂肪族羧酸及其酯,例如像苯甲酸;苯基乙酸;苯甲酸甲酯;苯甲酸乙酯;苯甲酸己酯;苯甲酸苄酯;苯基乙酸甲酯;苯基乙酸乙酯;苯基乙酸香叶酯;苯基乙酸苯基乙基酯;肉桂酸甲酯;肉桂酸乙酯;肉桂酸苄酯;肉桂酸苯基乙基酯;肉桂酸肉桂酯;苯氧基乙酸烯丙酯;水杨酸甲酯;水杨酸异戊酯;水杨酸己酯;水杨酸环己酯;水杨酸顺式-3-己烯基酯;水杨酸苄酯;水杨酸苯基乙基酯;2,4-二羟基-3,6-二甲基苯甲酸甲酯;3-苯基缩水甘油酸乙酯;3-甲基-3-苯基缩水甘油酸乙酯;
含氮芳香族化合物,例如像2,4,6-三硝基-1,3-二甲基-5-叔丁基苯;3,5-二硝基-2,6-二甲基-4-叔丁基苯乙酮;肉桂腈;3-甲基-5-苯基-2-戊烯腈;3-甲基-5-苯基戊腈;邻氨基苯甲酸甲酯;甲基-N-甲基邻氨基苯甲酸酯;邻氨基苯甲酸甲酯与7-羟基-3,7-二甲基辛醛、2-甲基-3-(4-叔丁基苯基)丙醛或2,4-二甲基-3-环己烯甲醛的席夫碱;6-异丙基喹啉;6-异丁基喹啉;6-仲丁基喹啉;2-(3-苯基丙基)吡啶;吲哚;粪臭素;2-甲氧基-3-异丙基吡嗪;2-异丁基-3-甲氧基吡嗪;
酚、苯基醚和苯基酯,例如像草蒿脑;茴香脑;丁子香酚;丁子香酚甲基醚;异丁子香酚;异丁子香酚甲基醚;百里酚;香芹酚;二苯醚;β-萘基甲基醚;β-萘基乙基醚;β-萘基异丁基醚;1,4-二甲氧基苯;乙酸丁子香酚酯;2-甲氧基-4-甲基苯酚;2-乙氧基-5-(1-丙烯基)苯酚;苯乙酸对甲酚酯;
杂环化合物,例如像2,5-二甲基-4-羟基-2H-呋喃-3-酮;2-乙基-4-羟基-5-甲基-2H-呋喃-3-酮;3-羟基-2-甲基-4H-吡喃-4-酮;2-乙基-3-羟基-4H-吡喃-4-酮;
内酯,例如像1,4-辛内酯;3-甲基-1,4-辛内酯;1,4-壬内酯;1,4-癸内酯;8-癸烯-1,4-内酯;1,4-十一内酯;1,4-十二内酯;1,5-癸内酯;1,5-十二内酯;4-甲基-1,4-癸内酯;1,15-十五内酯;顺式-和反式-11-十五碳烯-1,15-内酯;顺式-和反式-12-十五碳烯-1,15-内酯;1,16-十六内酯;9-十六碳烯-1,16-内酯;10-氧杂-1,16-十六内酯;11-氧杂-1,16-十六内酯;12-氧杂-1,16-十六内酯;1,12-十二烷二酸亚乙酯;1,13-十三烷二酸亚乙酯;香豆素;2,3-二氢香豆素;八氢香豆素。
组合物中使用的芳香化学品(X)从已知的商业来源获得并且购自德国。
在优选实施例中,组合物包含至少一种具有式(I)的化合物和至少一种芳香化学品(X)。
非芳香化学品载体:
本发明组合物中的非芳香化学品载体优选地选自表面活性剂、油组分抗氧化剂、除臭剂活性剂和溶剂。
优选至少一种非芳香化学品载体是化合物、化合物的混合物或其他添加剂,其不具有感觉特性或不具有显著的感觉特性。非芳香化学品载体可以用于稀释和/或固定如上所定义的具有式(I)的化合物和可选地至少一种芳香化学品(X)(如果包含在组合物中)。
本发明组合物中的非芳香化学品载体优选地选自表面活性剂、油组分、溶剂、或前述中的两种或更多种的任何混合物。
溶剂
在当前要求保护的发明的上下文中,“溶剂”用于稀释根据本发明使用的具有式(I)的化合物,而不具有其自身的芳香。
溶剂的量根据组合物进行调节并且代表本领域技术人员的常规任务。
优选地,溶剂以基于组合物的总重量0.01wt.%至99.0wt.%的总量、更优选0.05wt.%至95.0wt.%的总量、还更优选0.1wt.%至80.0wt.%的总量、最优选0.1wt.%至70.0wt.%、特别是0.1wt.%至60.0wt.%的总量存在于组合物中。
在优选实施例中,该组合物包含基于组合物的总重量0.05wt.%至10wt.%、更优选0.1wt.%至5wt.%、还更优选0.2wt.%至3wt.%的总溶剂。在本发明的又另一个优选实施例中,该组合物包含基于组合物的总重量20wt.%至70wt.%、更优选25wt.%至50wt.%的总溶剂。
优选的溶剂选自乙醇、异丙醇、二甘醇单乙醚、甘油、丙二醇、1,2丁二醇、二丙二醇、柠檬酸三乙酯、肉豆蔻酸异丙酯、或前述中的两种或更多种的任何混合物。
在优选实施例中,组合物包含具有式(I)的化合物和至少一种溶剂以及可选地至少一种芳香化学品(X)。
油组分
优选地,总油组分以基于组合物的总重量0.1至80wt.%、更优选0.5至70wt.%、还更优选1至60wt.%、甚至更优选1至50wt.%、特别是1至40wt.%、更特别是5至25wt.%并且具体是5至15wt.%的量存在。
优选地,油组分选自基于含有6至18、优选8至10个碳原子的脂肪醇的格尔伯特醇和其他额外的酯,如肉豆蔻酸肉豆蔻酯、棕榈酸肉豆蔻酯、硬脂酸肉豆蔻酯、异硬脂酸肉豆蔻酯、油酸肉豆蔻酯、山萮酸肉豆蔻酯、芥酸肉豆蔻酯、肉豆蔻酸鲸蜡酯、棕榈酸鲸蜡酯、硬脂酸鲸蜡酯、异硬脂酸鲸蜡酯、油酸鲸蜡酯、山萮酸鲸蜡酯、芥酸鲸蜡酯、肉豆蔻酸硬脂酯、棕榈酸硬脂酯、硬脂酸硬脂酯、异硬脂酸硬脂酯、油酸硬脂酯、山萮酸硬脂酯、芥酸硬脂酯、肉豆蔻酸异硬脂酯、棕榈酸异硬脂酯、硬脂酸异硬脂酯、异硬脂酸异硬脂酯、油酸异硬脂酯、山萮酸异硬脂酯、油酸异硬脂酯、肉豆蔻酸油酯、棕榈酸油酯、硬脂酸油酯、异硬脂酸油酯、油酸油酯、山萮酸油酯、芥酸油酯、肉豆蔻酸山萮酯、棕榈酸山萮酯、硬脂酸山萮酯、异硬脂酸山萮酯、油酸山萮酯、山萮酸山萮酯、芥酸山萮酯、肉豆蔻酸芥酯、棕榈酸芥酯、硬脂酸芥酯、异硬脂酸芥酯、油酸芥酯、山萮酸芥酯和芥酸芥酯。也合适的是C18-C38烷基-羟基羧酸与直链或支链C6-C22脂肪醇的酯,更尤其是苹果酸二辛酯,直链和/或支链脂肪酸与多元醇(例如丙二醇、二聚体二醇或三聚体三醇)的酯,基于C6-C10脂肪酸的甘油三酯,液体的基于C6-C18脂肪酸的甘油单酯、甘油二酯和甘油三酯混合物,C6-C22脂肪醇和/或格尔伯特醇与芳香族羧酸、更特别是苯甲酸的酯,二羧酸与含有2至10个碳原子和2至6个羟基的多元醇的酯,植物油,支链伯醇,取代的环己烷,直链和支链C6-C22脂肪醇碳酸酯,例如像碳酸二辛酰酯(CC),基于含有6至18、优选8至10个碳原子的脂肪醇的格尔伯特碳酸酯,苯甲酸与直链和/或支链C6至C22醇的酯(例如/>TN),每个烷基含有6至22个碳原子的直链或支链、对称或不对称的二烷基醚,例如像二辛酰醚(/>OE),环氧化脂肪酸酯与多元醇的开环产物和烃或其混合物。
在优选实施例中,组合物包含至少一种具有式(I)的化合物和至少一种油组分以及可选地至少一种芳香化学品(X)。
抗氧化剂
应当理解,抗氧化剂能够抑制或防止由氧效应和其他氧化过程引起的待保护的组合物中的不希望的变化。在大多数情况下,抗氧化剂的作用在于其充当自动氧化期间产生的自由基的自由基清除剂。
在优选实施例中,抗氧化剂选自
·氨基酸(例如甘氨酸、丙氨酸、精氨酸、丝氨酸、苏氨酸、组氨酸、酪氨酸、色氨酸)及其衍生物,
·咪唑(例如尿刊酸)及其衍生物,
·肽,如D,L-肌肽、D-肌肽、L-肌肽(=β-丙氨酰-L-组氨酸)及其衍生物,
·类胡萝卜素、胡萝卜素(例如α-胡萝卜素、β-胡萝卜素、番茄红素、叶黄素)或其衍生物,
·绿原酸及其衍生物,
·硫辛酸及其衍生物(例如二氢硫辛酸),
·金硫葡糖、丙硫氧嘧啶和其他硫醇(例如硫氧还原蛋白、谷胱甘肽、半胱氨酸、胱氨酸、胱胺及其糖基、N-乙酰基、甲基、乙基、丙基、戊基、丁基和月桂基、棕榈酰基、油烯基、γ-亚麻基、胆甾醇基和甘油基酯)及其盐,
·硫代二丙酸二月桂基酯、硫代二丙酸二硬脂基酯、硫代二丙酸及其衍生物(酯、醚、肽、脂类、核苷酸、核苷和盐),
·亚砜亚胺化合物(例如丁硫氨酸亚砜亚胺,高半胱氨酸亚砜亚胺,丁硫氨酸砜,戊-、己-、庚硫堇亚砜亚胺),
·(金属)螯合剂(例如α-羟基脂肪酸、棕榈酸、植酸、乳铁蛋白),
·α-羟基酸(例如柠檬酸、乳酸、苹果酸),
·腐殖酸、胆汁酸、胆汁提取物、胆红素、胆绿素、波尔定碱(=来自植物波尔多树的生物碱,波尔多提取物,
·EDTA、EGTA及其衍生物,
·不饱和脂肪酸及其衍生物(例如γ-亚麻酸、亚油酸、油酸),
·叶酸及其衍生物,
·泛醌和泛醇及其衍生物,
·维生素C和衍生物(例如抗坏血酸棕榈酸酯、抗坏血酸磷酸镁、抗坏血酸乙酸酯),
·生育酚和衍生物(例如维生素E乙酸酯),
·维生素A和衍生物(例如维生素A棕榈酸酯),
·安息香胶、芸香酸及其衍生物的松柏醇苯甲酸酯,α-糖基芸香苷,阿魏酸,亚糠基葡萄糖醇,
·丁羟基甲苯(BHT)、丁羟基茴香醚(BHA),
·去甲二氢愈创木脂酸、去甲二氢愈创木酸、三羟基苯丁酮、尿酸及其衍生物、甘露糖及其衍生物,
·超氧化物歧化酶,
·锌及其衍生物(例如ZnO、ZnSO4),
·硒及其衍生物(例如硒代蛋氨酸),
·茋及其衍生物(例如,氧化茋、反式-氧化茋),
或前述中的两种或更多种的混合物。
在优选实施例中,抗氧化剂选自季戊四醇、四-二-叔丁基羟基氢化肉桂酸酯、去甲二氢愈创木酸、阿魏酸、白藜芦醇、没食子酸丙酯、丁基羟基甲苯(BHT)、丁基羟基茴香醚(BHA)、抗坏血酸棕榈酸酯、生育酚、或前述中的两种或更多种的混合物。
优选地,根据当前要求保护的发明的组合物包含基于组合物的总重量0.001至25wt.-%、优选0.005至10wt.-%、更优选0.01至8wt.-%、还更优选0.025至7wt.-%、甚至更优选0.05至5wt.-%的总量的抗氧化剂。
在优选实施例中,组合物包含至少一种具有式(I)的化合物和至少一种抗氧化剂以及可选地至少一种芳香化学品(X)。
除臭剂活性剂
除臭组合物(除臭剂和止汗剂)抵消、掩盖或消除体味。体味是通过皮肤细菌对顶泌汗液的作用形成的,这导致难闻气味的降解产物的形成。
优选地,除臭剂活性剂选自止汗剂、酯酶抑制剂、抗菌剂、或前述中的两种或更多种的混合物。
合适的止汗剂选自铝、锆或锌的盐。实例是氯化铝、氯化羟铝、二氯化羟铝、倍半氯化羟铝及其络合化合物(例如与1,2-丙二醇)、羟基尿囊素铝、酒石酸氯化铝、三氯羟铝锆、四氯羟铝锆、五氯羟铝锆及其络合化合物(例如与氨基酸如甘氨酸)。优选使用氯化羟铝、四氯羟铝锆、五氯羟铝锆或其络合化合物。
优选地,止汗剂选自氯化铝、氯化羟铝、二氯化羟铝、倍半氯化羟铝、羟基尿囊素铝、酒石酸氯化铝、三氯羟铝锆、四氯羟铝锆、五氯羟铝锆、或前述中的两种或更多种的混合物。
当汗液存在于腋下区域时,细胞外酶-酯酶、主要是蛋白酶和/或脂肪酶由细菌形成并分解汗液中存在的酯,在该过程中释放气味。合适的酯酶抑制剂是例如柠檬酸三烷基酯,如柠檬酸三甲酯、柠檬酸三丙酯、柠檬酸三异丙酯、柠檬酸三丁酯,并且特别是柠檬酸三乙酯。酯酶抑制剂抑制酶活性并且从而减少气味形成。游离酸可能通过柠檬酸酯的裂解而释放并将皮肤的pH值降低到酶通过酰化失活的程度。其他酯酶抑制剂是甾醇硫酸盐或磷酸盐,例如像羊毛甾醇、胆固醇、菜油甾醇、豆甾醇和谷甾醇硫酸盐或磷酸盐,二羧酸及其酯,例如戊二酸、戊二酸单乙酯、戊二酸二乙酯、己二酸、己二酸单乙酯、己二酸二乙酯、丙二酸和丙二酸二乙酯,羟基羧酸及其酯,例如柠檬酸、苹果酸、酒石酸或酒石酸二乙酯、甘氨酸锌、和前述中的两种或更多种的混合物。
优选地,酯酶抑制剂选自柠檬酸三甲酯、柠檬酸三丙酯、柠檬酸三异丙酯、柠檬酸三丁酯柠檬酸三乙酯、羊毛甾醇、胆固醇、菜油甾醇、豆甾醇、谷甾醇硫酸盐、谷甾醇磷酸盐、戊二酸、戊二酸单乙酯、戊二酸二乙酯、己二酸、己二酸单乙酯、己二酸二乙酯、丙二酸、丙二酸二乙酯、柠檬酸、苹果酸、酒石酸、酒石酸二乙酯、甘氨酸锌、或前述中的两种或更多种的混合物。
优选地,根据当前要求保护的发明的组合物包含基于组合物的总重量在0.01至20wt.-%、优选0.1至10wt.-%、并且更特别是0.5至5wt.-%范围内的总量的酯酶抑制剂。
如本文所用的术语“抗菌剂”涵盖具有杀菌和/或抑菌特性的物质。典型地,这些物质作用于革兰氏阳性菌,例如像4-羟基苯甲酸及其盐和酯、N-(4-氯苯基)-N'-(3,4-二氯苯基)-脲、2,4,4'-三氯-2'-羟基二苯基醚(三氯生)、4-氯-3,5-二甲基苯酚、2,2'-亚甲基-双-(6-溴-4-氯苯酚)、3-甲基-4-(1-甲基乙基)-苯酚、2-苄基-4-氯苯酚、3-(4-氯苯氧基)-丙烷-1,2-二醇、氨基甲酸3-碘-2-丙炔基丁基酯、洗必太、3,4,4'-三氯碳酰苯胺(TTC)、苯氧基乙醇、甘油单癸酸酯、甘油单辛酸酯、甘油单月桂酸酯(GML)、双甘油单癸酸酯(DMC)、水杨酸-N-烷基酰胺例如像水杨酸-正辛基酰胺或水杨酸-正癸基酰胺。
优选地,抗菌剂选自壳聚糖、苯氧基乙醇、5-氯-2-(2,4-二氯苯氧基)-苯酚、4-羟基苯甲酸及其盐和酯、N-(4-氯苯基)-N'-(3,4-二氯苯基)-脲、2,4,4'-三氯-2'-羟基二苯基醚(三氯生)、4-氯-3,5-二甲基苯酚、2,2'-亚甲基-双-(6-溴-4-氯苯酚)、3-甲基-4-(1-甲基乙基)-苯酚、2-苄基-4-氯苯酚、3-(4-氯苯氧基)-丙烷-1,2-二醇、氨基甲酸3-碘-2-丙炔基丁基酯、洗必太、3,4,4'-三氯碳酰苯胺(TTC)、苯氧基乙醇、甘油单癸酸酯、甘油单辛酸酯、甘油单月桂酸酯(GML)、双甘油单癸酸酯(DMC)、水杨酸-N-烷基酰胺、或前述中的两种或更多种的混合物。
优选地,根据当前要求保护的发明的组合物包含基于组合物的总重量在0.01至5wt.%并且优选0.1至2wt.%的范围内的总量的一种或多种抗菌剂。
在优选实施例中,组合物包含至少一种具有式(I)的化合物和至少一种除臭剂活性剂以及可选地至少一种芳香化学品(X)。
表面活性剂
优选地,表面活性剂选自阴离子、非离子、阳离子、两性、两性离子表面活性剂、或前述中的两种或更多种的混合物。更优选地,表面活性剂是阴离子表面活性剂。
优选地,根据本发明的组合物含有基于组合物的总重量0至40wt.%、更优选0至20wt.%、更优选0.1至15wt.%、并且特别是0.1至10wt.%的总量的一种或多种表面活性剂。
优选的非离子表面活性剂是脂肪醇聚乙二醇醚、烷基酚聚乙二醇醚、脂肪酸聚乙二醇酯、脂肪酸酰胺聚乙二醇醚、脂肪胺聚乙二醇醚、烷氧基化甘油三酯、混合醚和混合缩甲醛、可选部分氧化的烷基(烯基)低聚糖苷或葡糖醛酸衍生物、脂肪酸-N-烷基葡糖酰胺、蛋白质水解物(特别是基于小麦的植物产品)、多元醇脂肪酸酯、糖酯、脱水山梨糖醇酯、聚山梨醇酯和氧化胺。如果非离子表面活性剂含有聚乙二醇醚链,则它们可以具有常规的同系物分布,但是它们优选具有窄范围的同系物分布。
两性离子表面活性剂是表面活性化合物,其在分子中含有至少一个季铵基团和至少一个COO(-)或SO3(-)基团。
特别合适的两性离子表面活性剂是所谓的甜菜碱,如N-烷基-N,N-二甲基甘氨酸铵,例如,椰油烷基二甲基甘氨酸铵,N-酰基氨基丙基-N,N-二甲基甘氨酸铵,例如,椰油酰基氨基丙基二甲基甘氨酸铵,和2-烷基-3-羧甲基-3-羟基乙基咪唑啉,在烷基或酰基中含有8至18个碳原子,以及椰油酰基氨基乙基羟基乙基羧甲基甘氨酸盐。特别优选以椰油酰胺丙基甜菜碱的CTFA名称已知的脂肪酸酰胺衍生物。
两性表面活性剂也是合适的,特别是作为助表面活性剂。两性表面活性剂是表面活性化合物,其在分子中除了C8至C18烷基或酰基之外还含有至少一个游离氨基和至少一个-COOH或-SO3H基团并能够形成内盐。合适的两性表面活性剂的实例是N-烷基甘氨酸、N-烷基丙酸、N-烷基氨基丁酸、N-烷基亚氨基二丙酸、N-羟基乙基-N-烷基酰胺丙基甘氨酸、N-烷基牛磺酸、N-烷基肌氨酸、2-烷基氨基丙酸和烷基氨基乙酸,其在烷基中含有约8至18个碳原子。特别优选的两性表面活性剂是N-椰油烷基氨基丙酸盐、椰油酰基氨基乙基氨基丙酸盐和酰基肌氨酸。
阴离子表面活性剂的特征在于水溶性阴离子基团(例如像羧酸根、硫酸根、磺酸根或磷酸根基团)和亲脂性基团。在皮肤病学上安全的阴离子表面活性剂是许多从业者从相关教科书中已知的并且是可商购的。它们特别是呈其碱金属、铵或烷醇铵盐形式的烷基硫酸盐,烷基醚硫酸盐,烷基醚羧酸盐,酰基羟乙基磺酸盐,酰基肌氨酸盐,含有直链C12-C18烷基或酰基的酰基牛磺酸和磺基琥珀酸盐以及呈其碱金属或铵盐形式的酰基谷氨酸盐。
特别合适的阳离子表面活性剂是季铵化合物,优选卤化铵,更尤其是氯化物和溴化物,如烷基三甲基氯化铵,二烷基二甲基氯化铵和三烷基甲基氯化铵,例如,鲸蜡基三甲基氯化铵,硬脂基三甲基氯化铵,二硬脂基二甲基氯化铵,月桂基二甲基氯化铵,月桂基二甲基苄基氯化铵和三鲸蜡基甲基氯化铵。此外,易于生物降解的季酯化合物,例如像以Stepantexe的名称销售的甲基硫酸二烷基铵和甲基硫酸甲基羟烷基二烷氧基烷基铵以及相应的系列的产品,可以用作阳离子表面活性剂。“酯季铵盐”通常被理解为季铵化的脂肪酸三乙醇胺酯盐。它们可以向组合物提供特定的软度。它们是通过有机化学的相关方法制备的已知物质。适于根据本发明使用的其他阳离子表面活性剂是季铵化的蛋白质水解物。
由于具有式(I)的化合物的特征感觉特性及其牢固性、持久性以及稳定性,它尤其可以用于向含表面活性剂的组合物、例如像清洁剂(特别是衣物护理产品和多功能清洁剂)提供气味、优选芳香效果。其优选地可以用于赋予含表面活性剂的组合物持久的选自以下的香调:甜香调、工业香调、烟草香调、香脂香调、草本香调、果香香调、木香香调、松针香调、桉树香调、粉香香调、或两种或更多种香调的组合。
在优选实施例中,组合物包含至少一种具有式(I)的化合物和至少一种表面活性剂以及可选地至少一种芳香化学品(X)。
合适的组合物是例如香水组合物、身体护理组合物(包括化妆品组合物以及用于口腔和牙齿卫生的产品)、卫生制品、清洁组合物(包括餐具洗涤组合物)、纺织品洗涤剂组合物、用于香气分配器的组合物、食品、食品补充剂、药物组合物和作物保护组合物。
香水组合物可以选自精制香料,呈液体形式、凝胶状形式或施加到固体载体上的形式的空气清新剂,气溶胶喷雾剂,有香气的清洁剂、香水蜡烛,或油、如灯油或用于按摩的油。
精制香料的实例是香水提取物、淡香精、淡香水、古龙水、固体香水和浓香精。
身体护理组合物包括化妆品组合物以及用于口腔和牙齿卫生的产品,并且可以选自须后水,须前产品,古龙水喷剂(splash cologne),固体和液体皂,淋浴露,洗发剂,剃须皂,剃须泡沫,浴油,水包油型、油包水型和水包油包水型的化妆乳,例如像护肤霜和乳剂,面霜和乳剂,防晒霜和乳剂,晒后霜和乳剂,护手霜和乳剂,护足霜和乳剂,脱毛霜和乳剂,须后霜和乳剂,美黑霜和乳剂,头发护理产品,例如像喷发剂、发胶、头发定型乳剂、头发调理剂,洗发剂,永久和半永久头发着色剂,头发定型组合物,如冷烫和头发顺滑组合物,生发油,发膏和发乳,除臭剂和止汗剂,例如像腋下喷剂,走珠,除臭棒和除臭膏;装饰性化妆品产品,例如像眼线笔、眼影、指甲油、粉底、唇膏和睫毛膏;以及用于口腔和牙齿卫生的产品,如牙膏、牙线、漱口水、呼吸清新剂、牙科泡沫、牙科凝胶和牙条。
卫生制品可以选自香条、杀昆虫剂、驱虫剂、推进剂、除锈剂、芳香清新湿巾、腋下垫、婴儿尿布、卫生巾、卫生纸、化妆巾、手帕纸、洗碗剂和除臭剂。
清洁组合物,例如像用于固体表面的清洁剂,可以选自芳香的酸性、碱性和中性清洁剂,例如像地板清洁剂,窗户清洁剂,用于手洗和机洗用途两者的洗碗组合物,洗浴和卫生清洁剂,擦洗乳,固体和液体厕所清洁剂,粉末和泡沫地毯清洁剂,蜡和抛光剂,如家具抛光剂,地板蜡,鞋油,消毒剂,表面消毒剂和卫生清洁剂,制动器清洁剂,管道清洁剂,水垢去除剂,烤架和烤箱清洁剂,藻类和苔藓去除剂,霉菌去除剂,立面清洁剂。
纺织品洗涤剂组合物可以选自液体洗涤剂、粉末洗涤剂、洗衣预处理剂(如漂白剂、浸泡剂和去污剂)、织物软化剂、洗涤皂、洗涤片剂。
食品意指用于或旨在用于全部或部分用于人体消耗的生的、煮熟的或经加工的可食用物质、冰、饮料或成分,或者口香糖、软糖、果冻和糖果。
食品补充剂是旨在用于摄入的产品,其含有旨在为饮食增加另外的营养价值的饮食成分。饮食成分可以是以下物质中的一种或任何组合:维生素、矿物质、草药或其他植物制剂、氨基酸、供人们通过增加总饮食摄入来补充饮食的饮食物质、浓缩物、代谢物、组分或提取物。食品补充剂可以以多种形式如片剂、胶囊、软凝胶、软胶囊、液体或粉末存在。
药物组合物包括旨在用于疾病的诊断、治愈、减轻、治疗或预防的组合物,以及旨在影响人或其他动物的身体的结构或任何功能的制品(除食品外)。
作物保护组合物包括旨在用于管理破坏农业作物和林业的植物疾病、杂草和其他有害生物(脊椎动物和无脊椎动物两者)的组合物。
优选地,根据本发明的组合物进一步包含至少一种选自以下的辅助剂:防腐剂、研磨剂、抗痘剂、抗皮肤老化剂、抗橘皮组织剂、去头屑剂、抗炎剂、防刺激剂、刺激减轻剂、收敛剂、抑汗剂、杀菌剂、抗静电剂、粘合剂、缓冲剂、载体材料、螯合剂、细胞兴奋剂、护理剂、脱毛剂、乳化剂、酶、精油、纤维、成膜剂、固定剂、泡沫形成剂、泡沫稳定剂、防止发泡的物质、泡沫促进剂、杀真菌剂、胶凝剂、凝胶形成剂、护发剂、头发定型剂、头发顺滑剂、增水剂、保湿物质、润湿物质、漂白剂、增强剂、去污剂、光学增亮剂、浸渍剂、防污剂、减摩剂、润滑剂、保湿霜、软膏、遮光剂、增塑剂、遮盖剂、抛光剂、发光剂、聚合物、粉末、蛋白质、加脂剂、剥离剂、硅酮、皮肤舒缓剂、洁肤剂、护肤剂、皮肤愈合剂、皮肤增亮剂、皮肤保护剂、皮肤软化剂、冷却剂、皮肤冷却剂、保暖剂、皮肤保暖剂、稳定剂、UV吸收剂、UV过滤剂、织物软化剂、悬浮剂、皮肤美黑剂、增稠剂、维生素、蜡、脂肪、磷脂、饱和脂肪酸、单-或多不饱和脂肪酸、α-羟基酸、多羟基脂肪酸、液化剂、染料、护色剂、颜料、缓蚀剂、多元醇、电解质和硅酮衍生物。
组合物的制备以及赋予组合物芳香效果的方法。
本发明的一个实施例涉及一种用于制备至少一种具有式(I)的化合物的组合物的方法,该组合物包含:
(i)至少一种除根据本发明的化合物之外的芳香化学品(X)或
(ii)至少一种非芳香化学品载体,或者
(i)和(ii)两者。
本发明还涉及一种用于促进组合物的芳香效果的方法,其中该方法包括将至少一种具有式(I)的化合物掺入组合物中。
特别地,本发明涉及一种制备香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、用于香气分配器的组合物、食品、食品补充剂、药物组合物或作物保护组合物的方法,该方法包括使香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、用于香气分配器的组合物、食品、食品补充剂、药物组合物或作物保护组合物中包含至少一种具有式(I)的化合物。
在一个实施例中,本发明涉及一种用于赋予香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、用于香气分配器的组合物、食品、食品补充剂、药物组合物或作物保护组合物使人联想到甜香调、工业香调、烟草香调、香脂香调、草本香调、果香香调、木香香调、松针香调、桉树香调、粉香香调、或两种或更多种香调的组合的香调的方法,该方法包括使香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、用于香气分配器的组合物、食品、食品补充剂、药物组合物或作物保护组合物中包含至少一种具有式(I)的化合物。
量
通常,根据本发明的组合物、方法和用途中的具有式(I)的化合物的总量典型地适于特定预期用途或预期应用并且因此可以在宽范围内变化。通常,使用用于芳香化学品、优选用于香气的常规标准商业量。
优选地,根据本发明的组合物包含基于组合物的总重量0.001至99.9wt.%的总量的具有式(I)的化合物。
特别地,组合物包含基于组合物的总重量0.001至99.5wt.%、优选50至99wt.%、更优选80至95wt.%、并且特别是90至95wt.%的总量的具有式(I)的化合物。
特别地,组合物包含基于组合物的总重量0.005至80wt.%、优选0.1至30wt.%、更优选1至20wt.%、并且特别是5至15wt.%的总量的具有式(I)的化合物。
特别地,组合物包含基于组合物的总重量0.001至20wt.%、优选0.005至6wt.%、更优选0.05至4wt.%、并且特别是0.1至3wt.%的总量的具有式(I)的化合物。
术语化合物(I)和具有式(I)的化合物在整个说明书中可互换使用。另外,术语多种化合物(I)和多种具有式(I)的化合物在整个说明书中可互换使用。
方法:
当前要求保护的发明的实施例涉及用于制备具有式(I)的化合物的方法,该方法包括至少以下步骤;
a)对称炔二醇的一锅法酸催化重排。
在当前要求保护的发明的实施例中,该反应是形成不饱和酮的Rupe重排反与随后不饱和酮的纳扎罗夫(Nazarov)环化的组合。
出于本发明的目的,该方法如Chimia[化学],39:(1985)第4期第100-101页标题为Synthese von spiro-substituierten Cyclopentenonen und analogen Verbindungen[螺取代环戊烯酮及类似化合物的合成]中描述的进行,并做了一些修改。
在实施例中,对称二醇是进一步被C1-C4直链或支链碳链或脂环族环取代的炔二醇。
在优选实施例中,炔二醇选自,
其中R是C1-C4直链或支链碳链。
在当前要求保护的发明的实施例中,反应在酸的存在下进行。
优选地,酸选自布朗斯台德酸或路易斯酸。
在优选实施例中,布朗斯台德酸选自无机酸、磺酸、有机酸、酸性离子交换树脂、或上述两种或更多种的组合。
无机酸优选地选自硫酸、盐酸、磷酸、高氯酸、硝酸、亚硝酸、亚硫酸、氯酸、亚氯酸或次氯酸。
磺酸是具有至少一个SO3H基团的化合物。磺酸优选地选自甲磺酸、乙磺酸、1-丙磺酸、1-丁磺酸、三氟-甲磺酸、苯磺酸、对甲苯磺酸、对二甲苯-2-磺酸、萘-1-磺酸、或萘-2-磺酸。
有机酸优选地选自羧酸,尤其是乳酸、乙酸、甲酸、柠檬酸、草酸、尿酸或苹果酸。
路易斯酸是选自以下项的含金属的化合物:AsX3、GaX3、BX3、BX3·(C2H5)2O、BX3·S(CH3)2、AlX3、(C2H5)2AlX、SbX3、SbX5、SnX2、MgX2、MgX2·O(C2H5)2、ZnX2、BiX3、FeX2、TiX2、TiX4、NbX5、NiX2、CoX2、HgX2,其中X在每种情况下表示F、Cl、Br、SO3、CF3-SO3、CH3-SO3或I;BH3、B(CH3)3、GaH3、AlH3、Al(CH3COO)(OH)2、Al[OCH(CH3)2]3、Al(OCH2)3、Al(OC2H5)3、Al2O3、(CH3)3Al、Ti[OCH(CH3)2]3Cl、Ti[OCH(CH3)2]4、二-(2,6-二-叔丁基-4-甲基苯氧基)甲基铝、二-(4-溴-2,6-二-叔丁基苯氧基)甲基铝、LiClO4;Mg(CH3COO)2、Zn(CH3COO)2、Ni(CH3COO)2、Ni(NO3)2、Co(CH3COO)2、Co(NO3)2、Cu(CH3COO)2、Cu(NO3)2、Li(CH3COO)、乙酰丙酮化锆、Si(CH3COO)4、K(CH3COO)、Na(CH3COO)、Cs(CH3COO)、Rb(CH3COO)、Mn(CH3COO)2、Fe(CH3COO)2、Bi(CH3COO)3、Sb(CH3COO)3、Sr(CH3COO)2、Sn(CH3COO)3、Zr(CH3COO)2、Ba(CH3COO)2、Hg(CH3COO)2、Ag(CH3COO)、Ti(CH3COO)3、Sc(CF3SO3)3、Ln(CF3SO3)3、Ni(CF3SO3)2、Ni(CH3C6H4SO3)2、Co(CF3SO3)2、Co(CH3C6H4SO3)3、Cu(CF3SO3)3、或Cu(CH3C6H4SO3)3。
在本发明的另一个优选实施例中,反应在选自酯、醚、醇、氯化溶剂的溶剂的存在下进行。
在本发明的优选实施例中,溶剂选自酯如乙酸甲酯、乙酸乙酯,醚如四氢呋喃、甲基叔丁基醚,醇如乙醇、丁醇,氯化溶剂如二氯甲烷、氯仿。
优选地,溶剂选自乙酸甲酯、乙酸乙酯。
实施例
在下文中,提供了实施例的列表以进一步说明本披露,而不旨在将本披露限制于下面列出的具体实施例,
1.至少一种具有式(I)的化合物
具有式(I)的化合物
或其立体异构体用于赋予组合物芳香效果的用途,
其中,
……虚线代表单键或双键,
R1、R2、R3和R4独立地选自H、或直链或支链的C1-C5烷基,或者
R1和R2组合形成取代或未取代的5元或6元脂环族环,并且R3和R4组合形成取代或未取代的5元或6元脂环族环。
2.根据实施例1所述的用途,其中该至少一种具有式(I)的化合物是用于赋予组合物芳香效果的具有式(Ia)的化合物
具有式(Ia)的化合物
或其立体异构体,
其中,
R1、R2、R3和R4独立地选自H、或直链或支链的C1-C5烷基,或者
R1和R2组合形成取代或未取代的5元或6元脂环族环,并且R3和R4组合形成取代或未取代的5元或6元脂环族环。
3.根据实施例1所述的用途,其中该至少一种具有式(I)的化合物是用于赋予组合物芳香效果的具有式(Ib)的化合物
具有式(Ib)的化合物
或其立体异构体,
其中,
R1、R2、R3和R4独立地选自H、或直链或支链的C1-C5烷基。
4.根据实施例1至3中任一项所述的用途,R1、R2、R3、R4独立地选自H、甲基、乙基、丙基、异丙基、丁基、异丁基、戊基、或异戊基。
5.根据实施例2所述的用途,其中R1、R2、R3中的每一个是甲基,并且R4是乙基。
6.根据实施例2所述的用途,其中R1、R3中的每一个是甲基,R2是异丙基,R4是异丁基。
7.根据实施例2所述的用途,其中R1、R3、R4中的每一个是甲基,R2是H。
8.根据实施例2所述的用途,其中R1和R2组合形成未取代的6元脂环族环,并且R3和R4组合形成未取代的6元脂环族环。
9.根据实施例3所述的用途,其中R1、R2、R3中的每一个是甲基,并且R4是乙基。
10.一种赋予组合物芳香效果的方法,该方法至少包括向组合物中添加至少一种根据实施例1至9中任一项所述的具有式(I)的化合物的步骤。
11.根据实施例1至10中任一项所述的用途或方法,其中该组合物选自香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、用于香气分配器的组合物、食品、食品补充剂、药物组合物或作物保护组合物。
12.根据实施例1至10中任一项所述的用途或方法,其中该芳香效果选自甜香调、工业香调、烟草香调、香脂香调、草本香调、果香香调、木香香调、松针香调、桉树香调、粉香香调、或两种或更多种香调的组合。
13.根据实施例1至10中任一项所述的用途或方法,其中该具有式(I)的化合物以基于该组合物的总重量在≥0.01wt.-%至≤70.0wt.-%范围内的总量存在。
14.一种组合物,其包含至少一种根据实施例1至9中任一项所述的具有式(I)的化合物,和
a.至少一种不同于该具有式(I)的化合物的芳香化学品(X),或
b.至少一种非芳香化学品载体,或者
c.(i)和(ii)两者。
15.根据实施例14所述的组合物,其中具有式(I)的化合物以基于该组合物的总重量在≥0.01wt.-%至≤70.0wt.-%范围内的总量存在。
16.根据实施例14所述的组合物,其中该至少一种非芳香化学品载体(ii)选自表面活性剂、油组分、抗氧化剂、除臭剂活性剂、或溶剂。
17.根据实施例14至16中任一项所述的组合物,其中该组合物选自香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、用于香气分配器的组合物、食品、食品补充剂、药物组合物或作物保护组合物。
18.一种具有式(Ia)的化合物
具有式(Ia)的化合物
或其立体异构体,
其中,
R1和R3独立地选自H、和直链或支链的C1-C5烷基,
R2选自直链或支链的C2-C5烷基,并且
R4选自直链或支链的C1-C5烷基,
或者
R1和R2组合形成取代或未取代的5元或6元脂环族环,并且R3和R4组合形成取代或未取代的5元或6元脂环族环。
19.根据实施例18所述的化合物,其中R1、R3、R4独立地选自H、甲基、乙基、丙基、异丙基、丁基、异丁基、戊基、或异戊基,R2选自乙基、丙基、异丙基、丁基、异丁基、戊基、或异戊基。
20.根据实施例19所述的具有式(I)的化合物,其中R1、R3中的每一个是甲基,R2是异丙基,R4是异丁基。
实例
通过下文的非限制性工作实例详细说明了本发明。更特别地,下文中指定的试验方法是本申请的一般披露内容的一部分并且不限于具体的工作实例。
1.分析方法:
通用GC法:30m ZB-5柱,0.25mm,1.00um;温度程序:40-5-10/280-41
入口/进样/检测:0.2ul;250℃;300℃,100;1.11c.p.;N2
NMR:通过1H-NMR和13C-NMR进行表征。NMR波谱在Bruker DPX-500光谱仪上测量。
2.合成
实例1:4-乙基2,3,4-三甲基环戊-2-烯-1-酮的制备
将150g 3,6-二甲基-4-辛炔-3,6-二醇与50g Amberlyst 15(H+形式)在600ml乙酸乙酯中混合,并将混合物在回流下加热96小时。完全转化时形成希望的环戊烯酮,选择性为82.1%。
将混合物过滤,并且在真空下蒸发溶剂。蒸馏(3毫巴,80℃)获得希望的产物。
GC:停留时间:21.7min
NMR:
13C NMR(125MHz,CDCl3):δ=8,09(C6),8,92(C10),11,95(C7),25,59(C8),30,98(C9),44,87(C4),46,64(C5),135,98(C2),175,96(C3),208,45(C1)ppm
1H-NMR(125MHz,CDCl3):δ=0,71(t,3H,H10),1,19(s,3H,H8),1,50(m,2H,H9),1,7(s,3H,H7),1,85(s,3H,H6),2,15-2,30(m,2H,H5)
实例2:螺[4,5,6,7-四氢-2H-茚-3,1'-环己烷]-1-酮/4’5’6’7’-四氢螺[环己烷-1,1’-茚]-3’(2’H)-酮的制备
将20g炔二醇与20g Amberlyst 15(H+形式)在200ml乙酸乙酯中混合并加热至回流持续7小时。GC分析显示,完全转化时对于两种异构体的选择性为70.2%和13.0%。
将混合物过滤,并且在真空下蒸发溶剂。蒸馏(3毫巴,190℃)获得希望的产物。
GC:停留时间:次要产物:31.22min,主要产物:31.32min
NMR:
主要产物:
13C NMR(125MHz,CDCl3):δ=19,84(C13),21,81(C14),22,33(C11),23,34(C12),23,51(2C,C1+C5),25,37(C6),34,78(2C,C2+C4),45,75(C3),46,93(C7),136,64(C9),181,27(C10),208,22(C8)ppm
次要产物:
13C NMR(125MHz,CDCl3):δ=21,89(C6),21,99(C12),22,07(C14),23,83(C5),25,70(C1),26,18(C13),29,57(C15),37,36(C11),40,80(C10),48,87(C8),49,42(C4),132,67(C2),140,08(C3),205(C7)ppm
实例3:4-异丁基-3-异丙基-2,4-二甲基环戊-2-烯-1-酮的制备。
将10g炔二醇与10g Amberlyst 15(H+形式)在100ml乙酸乙酯中混合并加热至回流持续168小时。将混合物过滤,并且在真空下蒸发溶剂。蒸馏(1毫巴,140℃)获得希望的产物。
GC分析显示,完全转化时对于希望的产物的选择性为67.9%。
GC:停留时间:26.53min
NMR:13C NMR(125MHz,CDCl3):δ=9,20(C7),20,45(C9),20,86(C10),24,49(2C,C14+C15),24,64(C11),25,55(C13),27,27(C8),45,77(C4),46,67(C12),48,11(C5),134,15(C2),185,31(C3),209,33(C1)ppm。
实例4:2,4,4,-三甲基环戊-2-烯-1-酮的制备。
将10g 2,5-二甲基己-3-炔-2,5,-二醇与10g Amberlyst 15(H+形式)在100ml乙酸乙酯中混合,并加热至回流持续48小时。将混合物过滤,并且在真空下蒸发溶剂。蒸馏(1毫巴,80℃)获得希望的产物。
GC分析显示,完全转化时对于希望的产物的选择性为78,5%。
GC:停留时间:16.48min
NMR:
13C NMR(125MHz,CDCl3):δ=9,91(C6),28,32(2C,C7+C8),38,80(C3),50,18(C2),138,72(C5),168,05(C4),210,26(C1)ppm。
实例5:4-乙基-2,3,4-三甲基环戊-1-酮的制备。
将3.7g根据实例1制备的4-乙基2,3,4-三甲基环戊-2-烯-1-酮溶解在60mL的MeOH中并在高压釜中使用1g催化剂(5% Pd/C)在10巴的氢气压力和70℃温度下氢化1小时。将混合物过滤,并且在真空下蒸发溶剂。蒸馏获得呈异构体混合物形式的希望的产物。
GC:停留时间:20.43min,21.18min,和21.29min。
NMR:
13C NMR(125MHz,CDCl3):δ=9,23(C7),12,31(C10),13,09(C6),19,29(C8),32,95(C9),40,00(C4),47,54(C2),48,82(C3),50,82(C5),220,97(C1)ppm
3.嗅觉评估
为了测试本发明的化合物和混合物的品质和强度,进行了香气条测试。
为此目的,将吸收纸条浸入含有1至10wt.%的待测试化合物在柠檬酸三乙酯中的溶液中。在溶剂蒸发后(约30s),由受过培训的调香师对香气效果进行嗅觉评价。
本发明化合物的芳香效果在下表1中指示。本发明化合物标记为化合物A并根据表2和表3配制在香水组合物中。
表1:本发明的化合物
4.有利的组合物
根据表2和表3,将表1中指示的化合物配制成组合物。来自表1的化合物在表2和表3中标记为“化合物A”。
表2:组合物1A和1B
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表3:组合物2A和2B
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根据表2和表3的组合物,即1A、1B、2A、2B可以包括在选自由以下组成的组的各种组合物中:除臭泵喷雾剂、清洁护发素、洗面凝胶、泡沫浴浓缩物、发胶、自发泡沐浴露、可喷雾防晒护理乳液、可喷雾防晒保护乳液、润肤洁面凝胶、2相油泡沫浴、洗发剂、淋浴露、水-酒精AP/除臭泵喷雾剂、气溶胶、水/酒精AP/除臭走珠、“离床”型定型凝胶、剃须泡沫、敏感皮肤婴儿洗发剂、敏感皮肤用沐浴露、敏感头皮用光泽增强洗发剂、除臭棒、婴儿湿巾、须后香脂、面部凝胶、面部日间护理霜、洗面奶、身体乳、防晒SPF50+、可喷雾乳剂、手洗餐具清洁剂-常规、手洗餐具清洁剂-浓缩物、卫生清洁剂-浓缩物、多功能清洁剂、抗菌织物软化剂、洗涤剂组合物、粉末洗涤剂组合物和液体洗涤剂组合物。
本领域技术人员可能精通上述产品的各种通用配制品。
组合物1A、1B、2A和2B可以例如配制在如IP.com编号:IPCOM000258614D标题为NewAroma Chemicals[新芳香化学品],第6至46页,表1至表D13中所披露的特定配制品中,其中“香料组合物1A”被替换为相同量的组合物1A、1B、2A或2B。
Claims (20)
1.至少一种具有式(I)的化合物
具有式(I)的化合物
或其立体异构体用于赋予组合物芳香效果的用途,
其中,
……虚线代表单键或双键,
R1、R2、R3和R4独立地选自H、或直链或支链的C1-C5烷基,或者
R1和R2组合形成取代或未取代的5元或6元脂环族环,并且R3和R4组合形成取代或未取代的5元或6元脂环族环。
2.根据权利要求1所述的用途,其中,该至少一种具有式(I)的化合物是用于赋予组合物芳香效果的具有式(Ia)的化合物
具有式(Ia)的化合物
或其立体异构体,
其中,
R1、R2、R3和R4独立地选自H、或直链或支链的C1-C5烷基,或者
R1和R2组合形成取代或未取代的5元或6元脂环族环,并且R3和R4组合形成取代或未取代的5元或6元脂环族环。
3.根据权利要求1所述的用途,其中,该至少一种具有式(I)的化合物是用于赋予组合物芳香效果的具有式(Ib)的化合物
具有式(Ib)的化合物
或其立体异构体,
其中,
R1、R2、R3和R4独立地选自H、或直链或支链的C1-C5烷基。
4.根据权利要求1至3中任一项所述的用途,R1、R2、R3、R4独立地选自H、甲基、乙基、丙基、异丙基、丁基、异丁基、戊基、或异戊基。
5.根据权利要求2所述的用途,其中,R1、R2、R3中的每一个是甲基,并且R4是乙基。
6.根据权利要求2所述的用途,其中,R1、R3中的每一个是甲基,R2是异丙基,R4是异丁基。
7.根据权利要求2所述的用途,其中,R1、R3、R4中的每一个是甲基,R2是H。
8.根据权利要求2所述的用途,其中,R1和R2组合形成未取代的6元脂环族环,并且R3和R4组合形成未取代的6元脂环族环。
9.根据权利要求3所述的用途,其中,R1、R2、R3中的每一个是甲基,并且R4是乙基。
10.一种赋予组合物芳香效果的方法,该方法至少包括向组合物中添加至少一种根据权利要求1至9中任一项所述的具有式(I)的化合物的步骤。
11.根据权利要求1至10中任一项所述的用途或方法,其中,该组合物选自香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、用于香气分配器的组合物、食品、食品补充剂、药物组合物或作物保护组合物。
12.根据权利要求1至10中任一项所述的用途或方法,其中,该芳香效果选自甜香调、工业香调、烟草香调、香脂香调、草本香调、果香香调、木香香调、松针香调、桉树香调、粉香香调、或两种或更多种香调的组合。
13.根据权利要求1至10中任一项所述的用途或方法,其中,这些具有式(I)的化合物以基于该组合物的总重量在≥0.01wt.-%至≤70.0wt.-%范围内的总量存在。
14.一种组合物,其包含至少一种根据权利要求1至9中任一项所述的具有式(I)的化合物,和
a.至少一种不同于该具有式(I)的化合物的芳香化学品(X),或
b.至少一种非芳香化学品载体,或者
c.(i)和(ii)两者。
15.根据权利要求14所述的组合物,其中,具有式(I)的化合物以基于该组合物的总重量在≥0.01wt.-%至≤70.0wt.-%范围内的总量存在。
16.根据权利要求14所述的组合物,其中,该至少一种非芳香化学品载体(ii)选自表面活性剂、油组分、抗氧化剂、除臭剂活性剂或溶剂。
17.根据权利要求14至16中任一项所述的组合物,其中,该组合物选自香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、用于香气分配器的组合物、食品、食品补充剂、药物组合物或作物保护组合物。
18.一种具有式(Ia)的化合物
具有式(Ia)的化合物
或其立体异构体,
其中,
R1和R3独立地选自H、和直链或支链的C1-C5烷基,
R2选自直链或支链的C2-C5烷基,并且
R4选自直链或支链的C1-C5烷基,
或者
R1和R2组合形成取代或未取代的5元或6元脂环族环,并且R3和R4组合形成取代或未取代的5元或6元脂环族环。
19.根据权利要求18所述的化合物,其中,R1、R3、R4独立地选自H、甲基、乙基、丙基、异丙基、丁基、异丁基、戊基、或异戊基,R2选自乙基、丙基、异丙基、丁基、异丁基、戊基、或异戊基。
20.根据权利要求19所述的具有式(I)的化合物,其中,R1、R3中的每一个是甲基,R2是异丙基,R4是异丁基。
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PCT/EP2022/072458 WO2023017086A1 (en) | 2021-08-13 | 2022-08-10 | Use of substituted cyclopentenones and cyclopentanones as aroma ingredients |
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CH464182A (de) * | 1965-03-31 | 1968-10-31 | Givaudan & Cie Sa | Verfahren zur Herstellung von Cyclopentenonen |
NL160708C (nl) * | 1967-09-11 | 1980-04-15 | Polak Frutal Works | Werkwijze voor het verlenen van een geroosterd en gebrand aroma aan voedingsmiddelen en dranken of voor het vesterken van een dergelijk reeds in voedings- middelen en dranken aanwezig aroma. |
GB1380196A (en) * | 1971-06-23 | 1975-01-08 | Firmenich & Cie | Amide flavouring agents for tobacco |
CH629467A5 (en) * | 1978-02-27 | 1982-04-30 | Firmenich & Cie | Process for the preparation of an oxygenated alicyclic compound |
CH648282A5 (de) * | 1980-06-10 | 1985-03-15 | Sumitomo Chemical Co | Verfahren zur herstellung von oxocyclopentenen. |
DE3216085A1 (de) * | 1982-04-30 | 1983-11-03 | Chemische Werke Hüls AG, 4370 Marl | Substituierte 3-isopropyl-cyclopentanonderivate, deren herstellung und verwendung als riechstoffe sowie diese enthaltende riechstoffkompositionen |
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