公开(公告)号：US06528668B2

公开(公告)日：2003-03-04

申请号：US10047895

申请日：2002-01-14

申请人： Hideaki Takaoka ,  Sigeru Wada ,  Nobuhiko Ito ,  Akio Hasebe ,  Shinzo Imamura ,  Hideo Muraoka

发明人： Hideaki Takaoka ,  Sigeru Wada ,  Nobuhiko Ito ,  Akio Hasebe ,  Shinzo Imamura ,  Hideo Muraoka

IPC分类号： C07C5100

CPC分类号： C07D307/33 ,  C07C51/43 ,  C07C67/32 ,  C07C69/716 ,  C07C59/215

摘要： Methods for making 2-(&ohgr;-alkoxycarbonylalkanoyl)-4-butanolide and derivatives thereof, esters of &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid and derivatives thereof, which are useful as a variety of synthetic raw materials and intermediates, and are prepared as intermediates in the production step of &ohgr;-hydroxyaliphatic acid being important intermediates of large cyclic lactone-based perfumes in the perfume industry.

摘要翻译： 制备2-（ω-烷氧基羰基烷酰基）-4-丁醇酸及其衍生物的方法，可用作各种合成原料和中间体的ω-羟基 - （ω-3） - 酮脂肪酸及其衍生物的酯，以及 在生产步骤中作为中间体被制备成ω-羟基脂肪酸，是香料工业中大环内酯类香料的重要中间体。

公开(公告)号：US06291688B1

公开(公告)日：2001-09-18

申请号：US09242805

申请日：1999-02-24

申请人： Hideaki Takaoka ,  Sigeru Wada ,  Nobuhiko Ito ,  Akio Hasebe ,  Shinzo Imamura ,  Hideo Muraoka

发明人： Hideaki Takaoka ,  Sigeru Wada ,  Nobuhiko Ito ,  Akio Hasebe ,  Shinzo Imamura ,  Hideo Muraoka

IPC分类号： C07D30726

CPC分类号： C07D307/33 ,  C07C51/43 ,  C07C67/32 ,  C07C69/716 ,  C07C59/215

摘要： A method, with high yield and improved selectively, for making a 2-(&ohgr;-alkoxycarbonylalkanoyl)-4-butanolide and an alkaline metal salt thereof, an ester of &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid as a novel compound and a derivative thereof, and a method for making the same are provided.

摘要翻译： 一种制备2-（ω-烷氧基羰基烷酰基）-4-丁醇和其碱金属盐的高产率和选择性改进的方法，作为新化合物的ω-羟基 - （ω-3） - 脂肪酸的酯 及其衍生物及其制备方法。

公开(公告)号：US06600070B2

公开(公告)日：2003-07-29

申请号：US09997140

申请日：2001-11-29

申请人： Hideaki Takaoka ,  Sigeru Wada ,  Nobuhiko Ito ,  Akio Hasebe ,  Shinzo Imamura ,  Hideo Muraoka

发明人： Hideaki Takaoka ,  Sigeru Wada ,  Nobuhiko Ito ,  Akio Hasebe ,  Shinzo Imamura ,  Hideo Muraoka

IPC分类号： C07C5142

CPC分类号： C07D307/33 ,  C07C51/43 ,  C07C67/32 ,  C07C69/716 ,  C07C59/215

摘要： In industrial production of &ohgr;-hydroxyaliphatic acid being an important intermediate for large cyclic lactone-based perfumes, using dicarboxylate ester which is inexpensive and readily obtainable, a method, with high yield and improved selectively, for making a 2-(&ohgr;-alkoxycarbonylalkanoyl)-4-butanolide and an alkaline metal salt thereof, an ester of &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid as a novel compound and a derivative thereof, and a method for making the same are provided. Condensation reaction of &ggr;-butyrolactone with a dicarboxylate ester represented by the general formula (1) ROOC(CH2)nCOOR wherein n is an integer of 7 to 13 and R is an alkyl group forms a condensation solution containing an alkaline metal salt of 2-(&ohgr;-alkoxycarbonylalkanoyl)-4-butanolide represented by the general formula (3): wherein n is an integer of 7 to 13, R is an alkyl group, and M is an alkaline metal; the solution is extracted with water or an aqueous alkaline solution and subjected to hydrolysis and decarboxylation to form an alkaline metal salt of &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid represented by the general formula (5): wherein n is an integer of 7 to 13 and M is an alkaline metal; and the compound is selectively and effectively separated and recovered and then acidified to form an &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid represented by the general formula (10): wherein n is an integer of 7 to 13.

公开(公告)号：US06475133B2

公开(公告)日：2002-11-05

申请号：US09894014

申请日：2001-06-28

申请人： Hideaki Takaoka ,  Sigeru Wada ,  Nobuhiko Ito ,  Akio Hasebe ,  Shinzo Imamura ,  Hideo Muraoka

发明人： Hideaki Takaoka ,  Sigeru Wada ,  Nobuhiko Ito ,  Akio Hasebe ,  Shinzo Imamura ,  Hideo Muraoka

IPC分类号： C07C5100

CPC分类号： C07D307/33 ,  C07C51/43 ,  C07C67/32 ,  C07C69/716 ,  C07C59/215

摘要： In industrial production of &ohgr;-hydroxyaliphatic acid being an important intermediate for large cyclic lactone-based perfumes, using dicarboxylate ester which is inexpensive and readily obtainable, a method, with high yield and improved selectively, for making a 2-(&ohgr;-alkoxycarbonylalkanoyl)-4-butanolide and an alkaline metal salt thereof, an ester of &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid as a novel compound and a derivative thereof, and a method for making the same are provided. Condensation reaction of &ggr;-butyrolactone with a dicarboxylate ester represented by the general formula (1) ROOC(CH2)nCOOR wherein n is an integer of 7 to 13 and R is an alkyl group forms a condensation solution containing an alkaline metal salt of 2-(&ohgr;-alkoxycarbonylalkanoyl)-4-butanolide represented by the general formula (3): wherein n is an integer of 7 to 13, R is an alkyl group, and M is an alkaline metal; the solution is extracted with water or an aqueous alkaline solution and subjected to hydrolysis and decarboxylation to form an alkaline metal salt of &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid represented by the general formula (5): wherein n is an integer of 7 to 13 and M is an alkaline metal; and the compound is selectively and effectively separated and recovered and then acidified to form an &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid represented by the general formula (10): wherein n is an integer of 7 to 13.

摘要翻译： 在工业生产中，ω-羟基脂肪酸是大环内酯基香料的重要中间体，使用廉价且易于获得的二羧酸酯，可以制备2-（ω-烷氧羰基烷酰基） -4-丁醇酸及其碱金属盐，作为新化合物的ω-羟基 - （ω-3） - 酮脂肪酸的酯及其衍生物及其制备方法。 （1）ROOC（CH 2）n COOR表示的二羧酸酯的丁内酯，其中n为7〜13的整数，R为烷基，形成含有2-（ω-烷氧基羰基烷酰基）的碱金属盐的缩合溶液， 由通式（3）表示的4-丁醇酯：其中n为7〜13的整数，R为烷基，M为碱金属; 溶液用水或碱性水溶液萃取，并进行水解和脱羧，形成由通式（5）表示的ω-羟基 - （ω-3） - 酮脂肪酸的碱金属盐：其中n为整数 为7〜13，M为碱金属; 选择性且有效地分离和回收化合物，然后酸化以形成由通式（10）表示的ω-羟基 - （ω-3） - 酮脂肪酸：其中n为7至13的整数。

公开(公告)号：US06525207B1

公开(公告)日：2003-02-25

申请号：US10110794

申请日：2002-04-17

申请人： Nobuhiko Ito ,  Motoo Higashi ,  Yuki Konno ,  Hideaki Takaoka

发明人： Nobuhiko Ito ,  Motoo Higashi ,  Yuki Konno ,  Hideaki Takaoka

IPC分类号： C07D30306

CPC分类号： C07D303/04 ,  A23L2/56 ,  A23L27/203 ,  A61K8/31 ,  A61K8/33 ,  A61K8/34 ,  A61K8/35 ,  A61K8/4973 ,  A61K8/922 ,  A61Q13/00 ,  C07D301/26

摘要： This invention provides a process for producing an epoxy compound industrially advantageously at low cost in a short process. Furthermore, this invention provides a novel fruity, camphoric, floral, amber or woody fragrance-, flavor- or scent-imparting composition containing said epoxy compound, and foods & drinks, perfumes, cosmetics and tobaccos containing said composition. The epoxy compound can be produced by letting an &agr;-halocyclododecanone and an organic magnesium compound react with each other for Grignard reaction, hydrolyzing to obtain a halohydrin and letting the halohydrin and a base react with each other in the presence of an phase transfer catalyst or adding an aprotic polar solvent for reaction.

摘要翻译： 本发明提供一种在短时间内以低成本有利地工业生产环氧化合物的方法。 此外，本发明提供了含有所述环氧化合物和含有所述组合物的食品和饮料，香料，化妆品和烟草的新颖的水果，樟脑，花香，琥珀或木质香料，香味或香味赋予组合物。环氧化合物可以 通过使α-卤代环十二烷酮和有机镁化合物彼此反应进行格氏反应，水解得到卤代醇并使卤代醇和碱在相转移催化剂存在下相互反应或加入非质子极性溶剂 用于反应。

公开(公告)号：US07569535B2

公开(公告)日：2009-08-04

申请号：US11579173

申请日：2005-04-27

申请人： Hideaki Takaoka

发明人： Hideaki Takaoka

IPC分类号： A61K8/00

CPC分类号： C07C59/01 ,  C07D307/33 ,  C07D313/02 ,  C07D313/18 ,  C11B9/0084

摘要： Among the compounds represented by the general formula (1), (in the formula, n is an integer of 7 to 13) in particular, 11-methyl-13-tridecanolide of which n=8, 12-methyl-14-tetradecanolide of which n=9, and 13-methyl-15-pentadecanolide of which n=10 are novel compounds which have not been reported in prior art and the evaluation of the compounds for fragrance characteristics revealed that the compounds are macrocyclic lactone musks having not only strong fragrance of musk excellent in persistency but also fragrance characteristics like nitro musks. Furthermore, in the present invention, by containing at least one of those novel compounds, perfume compositions or perfume products having distinctive fragrance characteristics are obtained. The invention also provides a novel process for the production of compounds represented by the general formula (1).

摘要翻译： 在通式（1）表示的化合物中，（式中，n为7〜13的整数），特别优选n = 8,12-甲基-14-十四内酯的11-甲基-13-十三内酯 其中n = 9和13-甲基-15-十五内酯，其中n = 10是在现有技术中没有报道的新化合物，并且用于香料特性的化合物的评价显示，化合物是不仅具有强的大环内酯麝香 麝香香气持久，而且香味特色如硝麝香。 此外，在本发明中，通过含有这些新化合物中的至少一种，得到具有鲜明特征的香料组合物或香料。 本发明还提供了用于制备由通式（1）表示的化合物的新方法。

公开(公告)号：US4725648A

公开(公告)日：1988-02-16

申请号：US916339

申请日：1986-10-07

申请人： Tetsuo Fujimoto ,  Hideaki Takaoka ,  Takafumi Imai

发明人： Tetsuo Fujimoto ,  Hideaki Takaoka ,  Takafumi Imai

IPC分类号： C08L83/04 ,  C08F8/00

CPC分类号： C08L83/04 ,  C08G77/12 ,  C08G77/20

摘要： The present invention relates to a polyorganosiloxane composition and, more particularly, to a polyorganosiloxane composition having good curing properties at room temperature and producing cured materials having good water absorption properties. The polyorganosiloxane composition comprises:(A) a curable silicone rubber composition containing polysiloxane which is liquid at room temperature as a base polymer; and(B) a polymer containing acrylic acid or an alkali metal salt of acrylic acid as a monomer unit.

摘要翻译： 本发明涉及聚有机硅氧烷组合物，更具体地说，涉及在室温下具有良好固化性能的聚有机硅氧烷组合物，并且生产具有良好吸水性能的固化材料。 聚有机硅氧烷组合物包含：（A）含有聚硅氧烷的可固化硅橡胶组合物，其在室温下为基体聚合物; 和（B）含有丙烯酸或丙烯酸的碱金属盐作为单体单元的聚合物。

公开(公告)号：US20080020963A1

公开(公告)日：2008-01-24

申请号：US11579173

申请日：2005-04-27

申请人： Hideaki Takaoka

发明人： Hideaki Takaoka

IPC分类号： C07D313/00 ,  C07C51/09 ,  C11B9/00 ,  C07D307/33

CPC分类号： C07C59/01 ,  C07D307/33 ,  C07D313/02 ,  C07D313/18 ,  C11B9/0084

摘要： Among the compounds represented by the general formula (1),  (in the formula, n is an integer of 7 to 13) in particular, 11-methyl-13-tridecanolide of which n=8, 12-methyl-14-tetradecanolide of which n=9, and 13-methyl-15-pentadecanolide of which n=10 are novel compounds which have not been reported in prior art and the evaluation of the compounds for fragrance characteristics revealed that the compounds are macrocyclic lactone musks having not only strong fragrance of musk excellent in persistency but also fragrance characteristics like nitro musks. Furthermore, in the present invention, by containing at least one of those novel compounds, perfume compositions or perfume products having distinctive fragrance characteristics are obtained. The invention also provides a novel process for the production of compounds represented by the general formula (1).

摘要翻译： 在通式（1）表示的化合物中，（式中，n为7〜13的整数），特别优选n = 8,12-甲基-14-十四内酯的11-甲基-13-十三内酯 其中n = 9和13-甲基-15-十五内酯，其中n = 10是在现有技术中没有报道的新化合物，并且用于香料特性的化合物的评价显示，化合物是不仅具有强的大环内酯麝香 麝香香气持久，而且香味特色如硝麝香。 此外，在本发明中，通过含有这些新化合物中的至少一种，得到具有鲜明特征的香料组合物或香料。 本发明还提供了用于制备由通式（1）表示的化合物的新方法。