公开(公告)号：US08716531B2

公开(公告)日：2014-05-06

申请号：US13379133

申请日：2010-05-13

Applicant: Shinichi Komatsu ,  Hisashi Sone ,  Takeshi Koike ,  Sayako Kawahama

Inventor： Shinichi Komatsu ,  Hisashi Sone ,  Takeshi Koike ,  Sayako Kawahama

IPC: C07C45/61 ,  C07C49/653

CPC classification number: C07C45/68 ,  C07C45/69 ,  C07C45/80 ,  C07C2602/42 ,  C07C2603/94 ,  C07C49/643 ,  C07C49/683 ,  C07C49/798

Abstract: A method for producing a norbornene derivative includes forming a Mannich base represented by any of general formulae (5) to (7) by reacting a carbonyl compound represented by any of general formulae (1) to (3) and an amine compound represented by general formula (4) with each other in an acidic solvent, to thereby obtain a reaction liquid comprising the Mannich base in the acidic solvent, wherein the acidic solvent comprises a formaldehyde derivative and 0.01 mol/L or more of an acid represented by formula HX; reacting the Mannich base and a diene compound represented by general formula (8) with each other by adding an organic solvent, a base in an amount of 1.0 to 20.0 equivalents to the acid, and the diene compound to the reaction liquid, and then heating the reaction liquid, to thereby form the norbornene derivative represented by any of general formulae (9) to (11).

Abstract translation: 降冰片烯衍生物的制造方法包括通过使由通式（1）〜（3）中的任一个表示的羰基化合物与通式（1）〜（3）所示的胺化合物反应而形成由通式（5）〜（7）中任一项所示的曼尼希碱， 式（4）在酸性溶剂中彼此反应，从而在酸性溶剂中获得包含曼尼希碱的反应液，其中酸性溶剂包含甲醛衍生物和0.01mol / L以上由式HX表示的酸; 使曼尼希碱和通式（8）表示的二烯化合物相互反应，加入有机溶剂，碱的量为1.0至20.0当量，向反应液中加入二烯化合物，然后加热 反应液，从而形成由通式（9）至（11）中的任一个表示的降冰片烯衍生物。

公开(公告)号：US08507728B2

公开(公告)日：2013-08-13

申请号：US13130881

申请日：2009-11-24

Applicant: Kiyotomi Kaneda ,  Hisashi Sone

Inventor： Kiyotomi Kaneda ,  Hisashi Sone

IPC: C07C45/34

CPC classification number: C07C45/34 ,  C07C2601/08 ,  C07C2601/14 ,  C07C49/10 ,  C07C49/403 ,  C07C49/395 ,  C07C49/04

Abstract: A method for manufacturing a ketone includes oxidizing an internal olefin or a cyclic olefin having one carbon-carbon double bond or more at a position other than terminals of a molecule thereof in an amide-based solvent in the presence of water, a palladium catalyst, and molecular oxygen, thereby bonding an oxo group to at least one of the carbon atoms constituting the carbon-carbon double bond, in which the amide-based solvent is represented by the formula in the formula (1), R1 represents an alkyl group having 1 to 4 carbon atoms, R2 and R3 each independently represent an alkyl group having 1 to 4 carbon atoms or an aryl group, and when R1 and R2 are alkyl groups, R1 and R2 may be bonded to each other to form a ring structure.

Abstract translation: 酮的制造方法包括在水，钯催化剂，钯催化剂的存在下，在酰胺类溶剂中，在其分子的末端以外的位置进行氧化内部烯烃或具有一个碳 - 碳双键的环状烯烃， 和分子氧，由此将氧基团键合到构成碳 - 碳双键的至少一个碳原子上，其中酰胺类溶剂由式（1）表示，式中R1表示具有式 1至4个碳原子，R 2和R 3各自独立地表示具有1至4个碳原子的烷基或芳基，并且当R 1和R 2是烷基时，R 1和R 2可以彼此键合以形成环结构。

公开(公告)号：US20120302713A1

公开(公告)日：2012-11-29

申请号：US13519770

申请日：2010-12-24

Applicant: Takeshi Koike ,  Shinichi Komatsu ,  Tetsuya Uesaka ,  Hisashi Sone ,  Yuji Takahashi

Inventor： Takeshi Koike ,  Shinichi Komatsu ,  Tetsuya Uesaka ,  Hisashi Sone ,  Yuji Takahashi

IPC: C08F236/20

CPC classification number: C08J5/18 ,  C08G61/08 ,  C08G2261/3324 ,  C08G2261/418 ,  C08J2365/00 ,  G02B5/3083 ,  G02F2001/133638 ,  G02F2413/14 ,  H01L51/5281

Abstract: A retardation film, formed by stretching a film comprising a norbornene-based ring-opening copolymer containing a structural unit (A) represented by the following general formula (1): [in the formula (1), n represents an integer of any one of 0 and 1, R1 represents a hydrogen atom or the like, X1 represents a group represented by a formula: —CH═CH— or the like, a and b each independently represent an integer of 0 to 6, Ys each independently represent a methylene group or the like, and Zs each independently represent a methylene group or the like], and a structural unit (B) represented by the following general formula (2): [in the formula (2), m represents an integer of any one of 0 and 1, X2 represents a group represented by a formula: —CH═CH— or the like, and R2, R3, R4, and R5 each independently represent a hydrogen atom or the like], wherein a content of the structural unit (A) is not less than 5 mol % but not more than 95 mol % relative to a total amount of the structural units (A) and (B).

Abstract translation: 通过拉伸包含由以下通式（1）表示的结构单元（A）的降冰片烯系开环共聚物的膜形成的延迟膜：[式（1）中，n表示任意一个的整数 为0和1，R1表示氢原子等，X1表示由式-CH = CH-等表示的基团，a和b各自独立地表示0〜6的整数，Y分别独立地表示 亚甲基等，Z各自独立地表示亚甲基等]和由以下通式（2）表示的结构单元（B）：[式（2）中，m表示任意的 0和1中的一个，X2表示由式-CH = CH-等代表的基团，R2，R3，R4和R5各自独立地表示氢原子等]，其中结构 单位（A）相对于结构物总量不小于5mol％但不大于95mol％ （A）和（B）。

公开(公告)号：US20120197036A1

公开(公告)日：2012-08-02

申请号：US13500677

申请日：2010-10-08

Applicant: Kiyotomi Kaneda ,  Hisashi Sone

Inventor： Kiyotomi Kaneda ,  Hisashi Sone

IPC: C07C253/30 ,  C07C67/29 ,  C07C45/34

CPC classification number: C07C253/30 ,  C07C45/34 ,  C07C45/36 ,  C07C45/38 ,  C07C67/29 ,  C07C2601/14 ,  C07C49/303 ,  C07C49/175 ,  C07C49/17 ,  C07C69/14 ,  C07C69/716 ,  C07C255/17

Abstract: A method for manufacturing a ketone, includes oxidizing an internal olefin or a cyclic olefin having a functional group containing a hetero atom and one carbon-carbon double bond or more at a position other than terminals of a molecule thereof in an amide-based solvent in the presence of water, a palladium catalyst, and molecular oxygen, without oxidizing the functional group, thereby bonding an oxo group to at least one of the carbon atoms constituting the carbon-carbon double bond. The amide-based solvent is represented by formula (1): wherein R1 represents an alkyl group having 1 to 4 carbon atoms; R2 and R3 each independently represent an alkyl group having 1 to 4 carbon atoms or an aryl group; and when R1 and R2 are alkyl groups, R1 and R2 may be bonded to each other to form a ring structure.

Abstract translation: 一种制造酮的方法包括在酰胺类溶剂中，在其分子末端以外的位置，在酰胺类溶剂中氧化含有杂原子和1个碳 - 碳双键的官能团的内烯烃或环状烯烃 存在水，钯催化剂和分子氧，而不氧化官能团，从而将氧代基键合到构成碳 - 碳双键的至少一个碳原子上。 酰胺类溶剂由式（1）表示：其中R 1表示具有1至4个碳原子的烷基; R2和R3各自独立地表示具有1至4个碳原子的烷基或芳基; 并且当R 1和R 2是烷基时，R 1和R 2可以彼此键合以形成环结构。

公开(公告)号：US08211514B2

公开(公告)日：2012-07-03

申请号：US13145826

申请日：2009-12-24

Applicant: Tadahiro Kaminade ,  Shinichi Komatsu ,  Hisashi Sone ,  Takeshi Koike ,  Sayako Kawahama

Inventor： Tadahiro Kaminade ,  Shinichi Komatsu ,  Hisashi Sone ,  Takeshi Koike ,  Sayako Kawahama

IPC: C09K19/00 ,  C08G61/06 ,  C08F8/04

CPC classification number: G02B5/3083 ,  C08G61/08 ,  C08G2261/3324 ,  C08G2261/418 ,  Y10T428/10

Abstract: A reverse dispersion retardation film is formed by stretching a film containing a norbornene-based ring-opening copolymer containing a structural unit (A) represented by a general formula (1) and a structural unit (B) represented by a general formula (2), wherein a total amount of the structural unit (A) and an exo-form structural unit, among the structural units (B), is not less than 20 mol % but not more than 65 mol % of all the structural units.

Abstract translation: 通过拉伸含有由通式（1）表示的结构单元（A）和由通式（2）表示的结构单元（B））的降冰片烯系开环共聚物的膜来形成反分散延迟膜， 其中，结构单元（B）中的结构单元（A）和外形结构单元的总量不小于所有结构单元的20摩尔％但不大于65摩尔％。

公开(公告)号：US20110313121A1

公开(公告)日：2011-12-22

申请号：US13145826

申请日：2009-12-24

Applicant: Tadahiro Kaminade ,  Shinichi Komatsu ,  Hisashi Sone ,  Takeshi Koike ,  Sayako Kawahama

Inventor： Tadahiro Kaminade ,  Shinichi Komatsu ,  Hisashi Sone ,  Takeshi Koike ,  Sayako Kawahama

IPC: C08F232/08

CPC classification number: G02B5/3083 ,  C08G61/08 ,  C08G2261/3324 ,  C08G2261/418 ,  Y10T428/10

Abstract: A reverse dispersion retardation film, formed by stretching a film comprising a norbornene-based ring-opening copolymer containing a structural unit (A) represented by the following general formula (1): [in the formula (1), m represents an integer of any one of 0 and 1, R1 represents a hydrogen atom or the like, X1 represents a group represented by a formula: —CH2CH2— or the like, a and b each independently represent an integer of 0 to 6, Y represents a methylene group or the like, and represents a methylene group or the like] and a structural unit (B) represented by the following general formula (2): [in the formula (2), n represents an integer of any one of 0 and 1, X2 represents a group represented by a formula: —CH2CH2— or the like, R2, R3, R4, and R5 each represent a hydrogen atom or the like, wavy lines d and e each represent a configuration of any one of an endo and an exo, and a wavy line f represents a configuration of any one of an endo and an exo], wherein a total amount of the structural unit (A) and an exo-form structural unit, in which the wavy line f represents the exo configuration, among the structural units (B) is not less than 20 mol % but not more than 65 mol % of all the structural units.

Abstract translation: 通过拉伸含有由以下通式（1）表示的结构单元（A）的降冰片烯系开环共聚物的膜形成的反色散相位差膜：[式（1）中，m表示 0和1中的任一个，R 1表示氢原子等，X 1表示由式-CH 2 CH 2 - 等表示的基团，a和b各自独立地表示0〜6的整数，Y表示亚甲基 并且表示亚甲基等]和由以下通式（2）表示的结构单元（B）：[式（2）中，n表示0和1中任一项的整数， X 2表示由式-CH 2 CH 2 - 等表示的基团，R 2，R 3，R 4和R 5各自表示氢原子等，波浪线d和e分别表示内酯和 exo，波浪线f表示endo和exo]中任何一个的构型，其中总数为am 结构单元（A）的结构单元（B）中的波浪线f表示外部构型的外部结构单元，其结构单元（B）中的结构单元（B）不小于20mol％但不大于65mol％ 结构单位。

公开(公告)号：US08946468B2

公开(公告)日：2015-02-03

申请号：US13579396

申请日：2011-02-18

Applicant: Kiyotomi Kaneda ,  Hisashi Sone

Inventor： Kiyotomi Kaneda ,  Hisashi Sone

IPC: C07C67/055

CPC classification number: C07C67/055 ,  C07C2601/16 ,  C07C69/145 ,  C07C69/16 ,  C07C69/708

Abstract: A process for producing an unsaturated bond-containing ester compound includes reacting an internal olefin or a cyclic olefin having one carbon-carbon double bond or more at a position other than terminals of a molecule thereof (the internal olefin and the cyclic olefin may each contain a hetero atom) with a carboxylic acid in an amide-based solvent represented by a formula (1) in the presence of a palladium catalyst, a base, and molecular oxygen, to obtain an ester compound having an unsaturated bond.

Abstract translation: 一种含有不饱和键的酯化合物的制造方法包括使内部烯烃或在其分子末端以外的位置具有一个碳 - 碳双键的环状烯烃（内部烯烃和环状烯烃可以各自含有 杂原子）与羧酸在式（1）表示的酰胺类溶剂中，在钯催化剂，碱和分子氧的存在下反应，得到具有不饱和键的酯化合物。

公开(公告)号：US08629226B2

公开(公告)日：2014-01-14

申请号：US13519770

申请日：2010-12-24

Applicant: Takeshi Koike ,  Shinichi Komatsu ,  Tetsuya Uesaka ,  Hisashi Sone ,  Yuji Takahashi

Inventor： Takeshi Koike ,  Shinichi Komatsu ,  Tetsuya Uesaka ,  Hisashi Sone ,  Yuji Takahashi

IPC: C08G61/06 ,  C09K19/00 ,  C08F8/04

CPC classification number: C08J5/18 ,  C08G61/08 ,  C08G2261/3324 ,  C08G2261/418 ,  C08J2365/00 ,  G02B5/3083 ,  G02F2001/133638 ,  G02F2413/14 ,  H01L51/5281

Abstract: A retardation film, formed by stretching a film having a norbornene-based ring-opening copolymer containing a structural unit (A) represented by the general formula (1) and a structural unit (B) represented by the general formula (2), wherein the content of structural unity (A) is not less than 5 mol % but not more than 95 mol % relative to the total amount of structural units (A) and (B).

Abstract translation: 通过拉伸含有由通式（1）表示的结构单元（A）和由通式（2）表示的结构单元（B））的降冰片烯系开环共聚物的膜形成的延迟膜，其中 结构单位（A）的含量相对于结构单元（A）和（B）的总量不小于5mol％但不大于95mol％。

公开(公告)号：US20120316360A1

公开(公告)日：2012-12-13

申请号：US13579396

申请日：2011-02-18

Applicant: Kiyotomi Kaneda ,  Hisashi Sone

Inventor： Kiyotomi Kaneda ,  Hisashi Sone

IPC: C07C67/04

CPC classification number: C07C67/055 ,  C07C2601/16 ,  C07C69/145 ,  C07C69/16 ,  C07C69/708

Abstract: A process for producing an α,β-unsaturated bond-containing ester compound, comprising: reacting an internal olefin or a cyclic olefin having one carbon-carbon double bond or more at a position other than terminals of a molecule thereof (the internal olefin and the cyclic olefin may each contain a hetero atom) with a carboxylic acid in an amide-based solvent in the presence of a palladium catalyst, a base, and molecular oxygen, thereby bonding a carboxyl group of the carboxylic acid to at least one of carbon atoms constituting the carbon-carbon double bond and carbon atoms at allylic positions of the internal olefin or the cyclic olefin, to obtain an ester compound having an α,β-unsaturated bond, the amide-based solvent being represented by the following formula (1): (in the formula (1), R1 represents an alkyl group having 1 to 4 carbon atoms; R2 and R3 each independently represent an alkyl group having 1 to 4 carbon atoms or an aryl group; and when R1 and R2 are alkyl groups, R1 and R2 may be bonded to each other to form a ring structure).

Abstract translation: 一种制备含α，β-不饱和键的酯化合物的方法，包括：使内部烯烃或在其分子末端以外的位置（内部烯烃）与一个碳 - 碳双键或更多个的环状烯烃反应 环状烯烃可以各自含有杂原子）与羧酸在酰胺类溶剂中，在钯催化剂，碱和分子氧的存在下，将羧酸的羧基键合至至少一种 构成碳 - 碳双键的碳原子和内烯烃或环烯烃的烯丙基位置的碳原子，得到具有α，β-不饱和键的酯化合物，酰胺系溶剂由下式 （1）表示：（式（1）中，R 1表示碳原子数1〜4的烷基，R 2，R 3各自独立地表示碳原子数1〜4的烷基或芳基， 烷基， R1和R2可以彼此键合形成环结构）。

公开(公告)号：US20120108851A1

公开(公告)日：2012-05-03

申请号：US13379133

申请日：2010-05-13

Applicant: Shinichi Komatsu ,  Hisashi Sone ,  Takeshi Koike ,  Sayako Kawahama

Inventor： Shinichi Komatsu ,  Hisashi Sone ,  Takeshi Koike ,  Sayako Kawahama

IPC: C07C45/61

CPC classification number: C07C45/68 ,  C07C45/69 ,  C07C45/80 ,  C07C2602/42 ,  C07C2603/94 ,  C07C49/643 ,  C07C49/683 ,  C07C49/798

Abstract: A method for producing a norbornene derivative includes forming a Mannich base represented by any of general formulae (5) to (7) by reacting a carbonyl compound represented by any of general formulae (1) to (3) and an amine compound represented by general formula (4) with each other in an acidic solvent, to thereby obtain a reaction liquid comprising the Mannich base in the acidic solvent, wherein the acidic solvent comprises a formaldehyde derivative and 0.01 mol/L or more of an acid represented by formula HX; reacting the Mannich base and a diene compound represented by general formula (8) with each other by adding an organic solvent, a base in an amount of 1.0 to 20.0 equivalents to the acid, and the diene compound to the reaction liquid, and then heating the reaction liquid, to thereby form the norbornene derivative represented by any of general formulae (9) to (11).

Abstract translation: 降冰片烯衍生物的制造方法包括通过使由通式（1）〜（3）中的任一个表示的羰基化合物与通式（1）〜（3）所示的胺化合物反应而形成由通式（5）〜（7）中任一项所示的曼尼希碱， 式（4）在酸性溶剂中彼此反应，从而在酸性溶剂中获得包含曼尼希碱的反应液，其中酸性溶剂包含甲醛衍生物和0.01mol / L以上由式HX表示的酸; 使曼尼希碱和通式（8）表示的二烯化合物相互反应，加入有机溶剂，碱的量为1.0至20.0当量，向反应液中加入二烯化合物，然后加热 反应液，从而形成由通式（9）至（11）中的任一个表示的降冰片烯衍生物。