公开(公告)号：US09249256B2

公开(公告)日：2016-02-02

申请号：US14344698

申请日：2012-09-04

申请人： Kyuhei Kitao ,  Hideyuki Takai ,  Michihiro Sugahara

发明人： Kyuhei Kitao ,  Hideyuki Takai ,  Michihiro Sugahara

IPC分类号： C08G59/32 ,  C08G59/34 ,  C07D301/14 ,  C07D303/12 ,  C08G59/02 ,  C07D303/04 ,  C08L63/00 ,  C07C2/76 ,  C07C6/04

CPC分类号： C08G59/3218 ,  C07C2/76 ,  C07C6/04 ,  C07C2601/16 ,  C07D301/14 ,  C07D303/04 ,  C07D303/12 ,  C08G59/02 ,  C08G59/027 ,  C08L63/00 ,  C07C13/28

摘要： Provided are: a novel triepoxy compound capable of forming, through polymerization, a cured article having excellent heat resistance; a production method thereof; a curable composition including the triepoxy compound; and a cured article obtained by curing the curable composition.The triepoxy compound according to the present invention is represented by Formula (1). The triepoxy compound represented by Formula (1) may be obtained typically by oxidizing a compound represented by Formula (2) with an oxidizing agent. In Formulae (1) and (2), R1 to R2° are the same as or different from one another and each represent hydrogen atom, methyl group, or ethyl group. Formulae (1) and (2) are expressed as follows:

摘要翻译： 提供：能够通过聚合形成耐热性优异的固化物的新型三环氧化合物; 其制造方法; 包含所述三环氧化合物的可固化组合物; 和通过固化该固化性组合物而得到的固化物。 根据本发明的三环氧化合物由式（1）表示。 式（1）所示的三环氧化合物通常可以通过用氧化剂氧化式（2）表示的化合物来获得。 在式（1）和（2）中，R 1至R 2°彼此相同或不同，各自表示氢原子，甲基或乙基。 式（1）和（2）表示如下：

公开(公告)号：US20140357836A1

公开(公告)日：2014-12-04

申请号：US14344698

申请日：2012-09-04

申请人： Kyuhei Kitao ,  Hideyuki Takai ,  Michihiro Sugahara

发明人： Kyuhei Kitao ,  Hideyuki Takai ,  Michihiro Sugahara

IPC分类号： C08G59/32 ,  C07D301/14 ,  C07C2/76 ,  C07D303/04

CPC分类号： C08G59/3218 ,  C07C2/76 ,  C07C6/04 ,  C07C2601/16 ,  C07D301/14 ,  C07D303/04 ,  C07D303/12 ,  C08G59/02 ,  C08G59/027 ,  C08L63/00 ,  C07C13/28

摘要： Provided are: a novel triepoxy compound capable of forming, through polymerization, a cured article having excellent heat resistance; a production method thereof; a curable composition including the triepoxy compound; and a cured article obtained by curing the curable composition.The triepoxy compound according to the present invention is represented by Formula (1). The triepoxy compound represented by Formula (1) may be obtained typically by oxidizing a compound represented by Formula (2) with an oxidizing agent. In Formulae (1) and (2), R1 to R2° are the same as or different from one another and each represent hydrogen atom, methyl group, or ethyl group. Formulae (1) and (2) are expressed as follows:

摘要翻译： 提供：能够通过聚合形成耐热性优异的固化物的新型三环氧化合物; 其制造方法; 包含所述三环氧化合物的可固化组合物; 和通过固化该固化性组合物而得到的固化物。 根据本发明的三环氧化合物由式（1）表示。 式（1）所示的三环氧化合物通常可以通过用氧化剂氧化式（2）表示的化合物来获得。 在式（1）和（2）中，R 1至R 2°彼此相同或不同，各自表示氢原子，甲基或乙基。 式（1）和（2）表示如下：

公开(公告)号：US07989523B2

公开(公告)日：2011-08-02

申请号：US12305906

申请日：2007-06-29

申请人： Atsushi Sato ,  Hideyuki Takai ,  Hisashi Maeshima ,  Kyuhei Kitao

发明人： Atsushi Sato ,  Hideyuki Takai ,  Hisashi Maeshima ,  Kyuhei Kitao

IPC分类号： C08G59/24 ,  C08G59/22 ,  C08G59/20 ,  C08L63/00 ,  C08L63/08 ,  B32B27/38

CPC分类号： C07D303/04 ,  B33Y70/00 ,  C08G59/24 ,  C08L63/00

摘要： Disclosed is an alicyclic diepoxy compound which gives a cured article suffering from no deterioration in properties even when used in hot and humid surroundings or used under such conditions as to give a strong acid, which is highly reactive upon curing, and which gives a cured article superior typically in thermal stability. Specifically, the alicyclic diepoxy compound includes a 3,4,3′,4′-diepoxybicyclohexyl compound represented by following Formula (1): wherein R1 to R18 each represent a hydrogen atom, a halogen atom, a hydrocarbon group which may have an oxygen atom or a halogen atom, or a substituted or unsubstituted alkoxy group, in which the alicyclic diepoxy compound contains isomers of the 3,4,3′,4′-diepoxybicyclohexyl compound in a content of less than 20% based on the total of the 3,4,3′,4′-diepoxybicyclohexyl compound and the isomers thereof in terms of peak area ratio as determined by gas chromatography.

摘要翻译： 公开了一种脂环式二环氧化合物，即使在热湿环境下使用也不会劣化的固化物，或者在固化时具有高反应性的强酸的条件下使用，得到固化物 优良的热稳定性。 具体地，脂环族二环氧化合物包括由下式（1）表示的3,4,3'，4'-二环氧双环己基化合物：其中R 1至R 18各自表示氢原子，卤素原子，可具有氧的烃基 原子或卤素原子或取代或未取代的烷氧基，其中脂环式二环氧化合物含有3,4,3'，4'-二环氧基双环己基化合物的异构体，其含量小于20％ 3,4,3'，4'-二环氧双环己基化合物及其异构体，以气相色谱法测定的峰面积比。

公开(公告)号：US20090062580A1

公开(公告)日：2009-03-05

申请号：US12226356

申请日：2007-04-11

申请人： Hideyuki Takai ,  Kenji Oka ,  Kyuhei Kitao

发明人： Hideyuki Takai ,  Kenji Oka ,  Kyuhei Kitao

IPC分类号： C07C1/24 ,  C07C13/28

CPC分类号： C07C13/28 ,  C07C1/24 ,  C07C2527/03 ,  C07C2527/054 ,  C07C2527/173 ,  C07C2601/16

摘要： Disclosed is a method for producing a cyclic olefin compound having two or more cyclohexene rings per molecule via intramolecular dehydration of an alicyclic alcohol having two or more hydroxylated cyclohexane rings per molecule. The method includes the step (i) of heating the alicyclic alcohol at a temperature of 130° C. to 230° C. and a pressure greater than 20 Torr in an organic solvent in the presence of a dehydration catalyst, to carry out dehydration of the alicyclic alcohol while distilling off by-product water, which dehydration catalyst is liquid or soluble in a liquid reaction mixture under the reaction conditions; and the subsequent step (ii) of heating the resulting reaction mixture at a temperature of 50° C. to 220° C. and a pressure of 200 Torr or less to recover the cyclic olefin compound as a distillate. According to the method, side reactions such as isomerization are suppressed, and high-purity cyclic olefin compounds with less impurities can be simply and efficiently obtained in high yields.

摘要翻译： 公开了通过每分子具有两个或更多个羟基化环己烷环的脂环醇的分子内脱水来制备每分子具有两个或更多个环己烯环的环状烯烃化合物的方法。 该方法包括在脱水催化剂存在下，在有机溶剂中，在130℃至230℃的温度和大于20托的压力下加热脂环醇的步骤（i），以进行脱水 在反应条件下蒸馏出副产物水的脂环醇，该脱水催化剂为液体或可溶于液体反应混合物; 和随后的步骤（ii）在50℃至220℃的温度和200托或更低的压力下加热所得反应混合物以回收作为馏出物的环状烯烃化合物。 根据该方法，可以抑制异构化等副反应，能够以高收率简单高效地得到杂质较少的高纯度环状烯烃化合物。

公开(公告)号：US08115043B2

公开(公告)日：2012-02-14

申请号：US12226356

申请日：2007-04-11

申请人： Hideyuki Takai ,  Kenji Oka ,  Kyuhei Kitao

发明人： Hideyuki Takai ,  Kenji Oka ,  Kyuhei Kitao

IPC分类号： C07C1/20

CPC分类号： C07C13/28 ,  C07C1/24 ,  C07C2527/03 ,  C07C2527/054 ,  C07C2527/173 ,  C07C2601/16

摘要： Disclosed is a method for producing a cyclic olefin compound having two or more cyclohexene rings per molecule via intramolecular dehydration of an alicyclic alcohol having two or more hydroxylated cyclohexane rings per molecule. The method includes the step (i) of heating the alicyclic alcohol at a temperature of 130° C. to 230° C. and a pressure greater than 20 Torr in an organic solvent in the presence of a dehydration catalyst, to carry out dehydration of the alicyclic alcohol while distilling off by-product water, which dehydration catalyst is liquid or soluble in a liquid reaction mixture under the reaction conditions; and the subsequent step (ii) of heating the resulting reaction mixture at a temperature of 50° C. to 220° C. and a pressure of 200 Torr or less to recover the cyclic olefin compound as a distillate. According to the method, side reactions such as isomerization are suppressed, and high-purity cyclic olefin compounds with less impurities can be simply and efficiently obtained in high yields.

摘要翻译： 公开了通过每分子具有两个或更多个羟基化环己烷环的脂环醇的分子内脱水来制备每分子具有两个或更多个环己烯环的环状烯烃化合物的方法。 该方法包括在脱水催化剂存在下，在有机溶剂中，在130℃至230℃的温度和大于20托的压力下加热脂环醇的步骤（i），以进行脱水 在反应条件下蒸馏出副产物水的脂环醇，该脱水催化剂为液体或可溶于液体反应混合物; 和随后的步骤（ii）在50℃至220℃的温度和200托或更低的压力下加热所得反应混合物以回收作为馏出物的环状烯烃化合物。 根据该方法，可以抑制异构化等副反应，能够以高收率简单高效地得到杂质较少的高纯度环状烯烃化合物。

公开(公告)号：US20100249341A1

公开(公告)日：2010-09-30

申请号：US12305906

申请日：2007-06-29

申请人： Atsushi Sato ,  Hideyuki Takai ,  Hisashi Maeshima ,  Kyuhei Kitao

发明人： Atsushi Sato ,  Hideyuki Takai ,  Hisashi Maeshima ,  Kyuhei Kitao

IPC分类号： C08G59/02 ,  C07D303/04

CPC分类号： C07D303/04 ,  B33Y70/00 ,  C08G59/24 ,  C08L63/00

摘要： Disclosed is an alicyclic diepoxy compound which gives a cured article suffering from no deterioration in properties even when used in hot and humid surroundings or used under such conditions as to give a strong acid, which is highly reactive upon curing, and which gives a cured article superior typically in thermal stability. Specifically, the alicyclic diepoxy compound includes a 3,4,3′,4′-diepoxybicyclohexyl compound represented by following Formula (1): wherein R1 to R18 each represent a hydrogen atom, a halogen atom, a hydrocarbon group which may have an oxygen atom or a halogen atom, or a substituted or unsubstituted alkoxy group, in which the alicyclic diepoxy compound contains isomers of the 3,4,3′,4′-diepoxybicyclohexyl compound in a content of less than 20% based on the total of the 3,4,3′,4′-diepoxybicyclohexyl compound and the isomers thereof in terms of peak area ratio as determined by gas chromatography.

摘要翻译： 公开了一种脂环式二环氧化合物，即使在热湿环境下使用也不会劣化的固化物，或者在固化时具有高反应性的强酸的条件下使用，得到固化物 优良的热稳定性。 具体地，脂环族二环氧化合物包括由下式（1）表示的3,4,3'，4'-二环氧双环己基化合物：其中R 1至R 18各自表示氢原子，卤素原子，可具有氧的烃基 原子或卤素原子或取代或未取代的烷氧基，其中脂环式二环氧化合物含有3,4,3'，4'-二环氧基双环己基化合物的异构体，其含量小于20％ 3,4,3'，4'-二环氧双环己基化合物及其异构体，以气相色谱法测定的峰面积比。

公开(公告)号：US20070179256A1

公开(公告)日：2007-08-02

申请号：US10590847

申请日：2005-03-16

申请人： Kyuhei Kitao ,  Hideyuki Takai

发明人： Kyuhei Kitao ,  Hideyuki Takai

IPC分类号： C08L63/00 ,  C08G65/00 ,  B32B27/38

CPC分类号： C07D303/04 ,  C07D303/34

摘要： The present invention provides a high-purity alicyclic epoxy compound in which an alicyclic olefin compound is epoxidized with an aliphaticpercarboxylic acid having substantially no water followed by the removal of a solvent to produce an alicyclic epoxy compound represented by the general formula (I) that is in turn subjected to purification by distillation to thereby the high-purity alicyclic epoxy compound wherein the concentration of high-molecular-weight components having an elution time shorter than that of the alicyclic epoxy compound in detection by a GPC analysis is 5.5% or less in terms of the area ratio, the concentration of impurities having a retention time shorter than that of the alicyclic epoxy compound in detection by a GC analysis is 19.5% or less in terms of the area ratio, the concentration of reactive intermediates is 4.5% or less in terms of the area ratio, and a color hue (APHA) is 60 or less; a process of efficiently producing the same by the use of a low-toxicity solvent; a curable resin composition using the same; a cured product; and applications.

摘要翻译： 本发明提供了一种高纯度脂环族环氧化合物，其中脂肪族烯烃化合物被基本上不含水的脂肪族过羧酸环氧化，然后除去溶剂，得到通式（I）表示的脂环族环氧化合物，即 然后通过蒸馏进行纯化，由此得到其中通过GPC分析检测的洗脱时间比脂环族环氧化合物的洗脱时间短的高分子量组分的浓度为5.5％以下的高纯度脂环式环氧化合物的浓度为5.5％以下 通过GC分析检测的面积比的术语，保留时间比脂环族环氧化合物的保留时间短的杂质浓度在面积比方面为19.5％以下，反应性中间体的浓度为4.5％以下 在面积比方面，色调（APHA）为60以下; 通过使用低毒溶剂有效地制备该方法的方法; 使用其的可固化树脂组合物; 固化产品; 和应用程序。

公开(公告)号：US08637623B2

公开(公告)日：2014-01-28

申请号：US12863924

申请日：2009-02-03

申请人： Hiroshi Koyama ,  Kyuhei Kitao ,  Akira Eguchi

发明人： Hiroshi Koyama ,  Kyuhei Kitao ,  Akira Eguchi

IPC分类号： C08F20/10 ,  C08F20/22 ,  C08F20/26 ,  C08F20/34 ,  C07D317/06 ,  C07C69/01 ,  C07C69/013 ,  G03F7/004 ,  G03F7/26

CPC分类号： C07D307/93 ,  C07D307/00 ,  C08F220/18 ,  C08F220/28 ,  G03F7/0397

摘要： Disclosed is a monomer having an electron-withdrawing substituent and a lactone skeleton, represented by Formula (1), wherein Ra represents, e.g., hydrogen or an alkyl group having 1 to 6 carbons; R1 represents, e.g., a halogen or an alkyl or haloalkyl group having 1 to 6 carbons; “A” represents an alkylene group having 1 to 6 carbons, oxygen, sulfur, or is nonbonding; “m” denotes an integer of 0 to 8; Xs each represent an electron-withdrawing substituent; “n” denotes an integer of 1 to 9; and Y represents a bivalent organic group having 1 to 6 carbons. The monomer is useful as a monomer component typically for a highly functional polymer, because, when the monomer is applied to a resist resin, the resin is stable and resistant to chemicals, is highly soluble in organic solvents, and has improved hydrolyzability and/or solubility in water after hydrolysis.

摘要翻译： 公开了由式（1）表示的具有吸电子取代基和内酯骨架的单体，其中，Ra表示例如氢或碳原子数为1〜6的烷基， R1表示例如卤素或具有1至6个碳原子的烷基或卤代烷基; “A”表示碳原子数为1〜6的亚烷基，氧，硫，或未键合; “m”表示0〜8的整数， Xs各自表示吸电子取代基; “n”表示1〜9的整数， Y表示碳原子数1〜6的2价有机基团。 该单体通常用作高官能聚合物的单体组分，因为当将单体施用于抗蚀剂树脂时，该树脂是稳定的并且耐化学品，高度可溶于有机溶剂，并具有改善的水解性和/或 水解后溶于水。

公开(公告)号：US20100297555A1

公开(公告)日：2010-11-25

申请号：US12863924

申请日：2009-02-03

申请人： Hiroshi Koyama ,  Kyuhei Kitao ,  Akira Eguchi

发明人： Hiroshi Koyama ,  Kyuhei Kitao ,  Akira Eguchi

IPC分类号： G03F7/20 ,  C07D307/77 ,  C08F24/00 ,  G03F7/004

CPC分类号： C07D307/93 ,  C07D307/00 ,  C08F220/18 ,  C08F220/28 ,  G03F7/0397

摘要： Disclosed is a monomer having an electron-withdrawing substituent and a lactone skeleton, represented by following Formula (1), wherein Ra represents, e.g., a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R1 represents, e.g., a halogen atom or an alkyl or haloalkyl group having 1 to 6 carbon atoms; “A” represents an alkylene group having 1 to 6 carbon atoms, oxygen atom, sulfur atom, or nonbonding; “m” denotes an integer of 0 to 8; Xs each represent an electron-withdrawing substituent; “n” denotes an integer of 1 to 9; and Y represents a bivalent organic group having 1 to 6 carbon atoms.The monomer is useful typically as a monomer component typically for a highly functional polymer, because, when the monomer is applied typically to a resist resin, the resin is satisfactory stable and resistant typically to chemicals, is highly soluble in organic solvents, and has improved hydrolyzability and/or solubility in water after hydrolysis.

摘要翻译： 公开了具有吸电子取代基和内酯骨架的单体，其由下式（1）表示，其中Ra表示例如氢原子或具有1至6个碳原子的烷基; R1表示例如卤素原子或碳原子数为1〜6的烷基或卤代烷基; “A”表示碳原子数1〜6的亚烷基，氧原子，硫原子，或非键合物。 “m”表示0〜8的整数， Xs各自表示吸电子取代基; “n”表示1〜9的整数， Y表示碳原子数为1〜6的2价有机基团。 单体通常用作高官能聚合物的单体组分，因为当单体通常用于抗蚀剂树脂时，树脂是令人满意的稳定和耐化学物质，高度可溶于有机溶剂，并改善了 水解后水解性和/或水溶性。