公开(公告)号：US20190016662A1

公开(公告)日：2019-01-17

申请号：US16069994

申请日：2017-01-20

Applicant: ZEON CORPORATION

Inventor： Kanako SANUKI ,  Kei SAKAMOTO ,  Kumi OKUYAMA ,  Hiroki IWAKI

IPC: C07C51/64 ,  C07C51/60 ,  C07C67/14

Abstract: Provided is a method of producing an acid halide solution that is useful in production of a polymerizable liquid-crystal compound. The method of producing an acid halide solution includes: a first step of reacting a specific dicarboxylic acid compound with a halogenating agent in a water-immiscible organic solvent in the presence of at least 1.1 equivalents and not more than 3.0 equivalents of an activator relative to the dicarboxylic acid compound to obtain a reaction liquid including a solution that contains an acid halide compound and an oily liquid that is immiscible with the solution containing the acid halide compound; and a second step of removing the oily liquid from the reaction liquid obtained in the first step to obtain a purified liquid containing the acid halide compound.

公开(公告)号：US20160002374A1

公开(公告)日：2016-01-07

申请号：US14768016

申请日：2014-02-12

Applicant: ZEON CORPORATION

Inventor： Kei SAKAMOTO ,  Satoshi KIRIKI ,  Kumi OKUYAMA ,  Kanako SANUKI

IPC: C08F128/06 ,  C07D277/82

CPC classification number: C08F128/06 ,  C07C251/88 ,  C07D277/82 ,  C08F22/10 ,  C08F2222/102 ,  C09K19/3068 ,  C09K19/32 ,  C09K19/3497 ,  C09K19/3809 ,  C09K2019/0444 ,  C09K2019/0448 ,  C09K2019/3075 ,  G02B5/3025

Abstract: According to the invention, a polymerizable compound, a polymerizable composition, and a polymer that have a low melting point at a practical level, exhibit excellent solubility in a general-purpose solvent, can be produced at low cost, and can produce an optical film that exhibits excellent transparency, and achieves uniform conversion of polarized light over a wide wavelength band, and an optically anisotropic article can be provided. In formula (I), Y1 to Y8 are, —O—, —O—C(═O)—, —C(═O)—O—, etc., G1 and G2 are a divalent linear aliphatic group of 1-20 carbon atoms, Z1 and Z2 are an alkenyl group of 2-10 carbon atoms that is substituted with a halogen atom, or unsubstituted, Ax is an organic group of 2-30 carbon atoms that includes at least one aromatic ring, Ay is a hydrogen atom, an alkyl group of 1-20 carbon atoms, etc., A1 is a trivalent aromatic group, A2 and A3 are a substituted or unsubstituted divalent alicyclic hydrocarbon group of 3-30 carbon atoms, A4 and A5 are a divalent aromatic group of 6-30 carbon atoms, and Q1 is a hydrogen atom, or an alkyl group of 1-6 carbon atoms.

Abstract translation: 根据本发明，可以以低成本制造在实用水平上具有低熔点的可聚合化合物，可聚合组合物和聚合物在通用溶剂中表现出优异的溶解性，并且可以制备光学膜 表现出优异的透明性，并且在宽波长带上实现偏振光的均匀转化，并且可以提供光学各向异性物品。 在式（I）中，Y 1至Y 8是-O-，-O-C（= O） - ， - C（= O）-O-等，G 1和G 2是1- 20个碳原子，Z1和Z2是被卤素原子取代的2-10个碳原子的链烯基，或未取代的，Ax是含有至少一个芳香环的2-30个碳原子的有机基团，Ay是 氢原子，1-20个碳原子的烷基等，A1是三价芳族基团，A2和A3是3-30个碳原子的取代或未取代的二价脂环族烃基，A4和A5是二价芳族基团 为6-30个碳原子，而Q1为氢原子或1-6个碳原子的烷基。

公开(公告)号：US20180346401A1

公开(公告)日：2018-12-06

申请号：US15761541

申请日：2016-09-29

Applicant: ZEON CORPORATION

Inventor： Kumi OKUYAMA ,  Kei SAKAMOTO ,  Kanako SANUKI ,  Hiroki IWAKI

IPC: C07C67/14

CPC classification number: C07C67/14 ,  C07B61/00 ,  C07C51/60 ,  C07C2601/14 ,  C07C69/75 ,  C07C61/09

Abstract: The present disclosure provides a method for producing an acid halide solution that is useful as a production intermediate or the like that allows industrially advantageous production of a polymerizable liquid crystal compound. The method for producing an acid halide solution of the present disclosure includes a step α of reacting a halogenating agent and a dicarboxylic acid compound in a water-immiscible organic solvent in the presence of a tetraalkylammonium salt to obtain a water-immiscible organic solvent solution including an acid halide, and a step β of concentrating the obtained water-immiscible organic solvent solution.

公开(公告)号：US20170158604A1

公开(公告)日：2017-06-08

申请号：US15320512

申请日：2015-06-30

Applicant: ZEON CORPORATION

Inventor： Kumi OKUYAMA ,  Kei SAKAMOTO ,  Kanako SANUKI

IPC: C07C67/62 ,  C07C69/75 ,  C07C69/017 ,  C07C67/307

Abstract: Provided are a production method for compound (II) including reacting compound (I) with a halogenating agent in the presence of at least 0.5 equivalents, relative to compound (I), of a nitrogen atom-containing polar aprotic solvent; a composition containing compound (II), a halogenating agent or the like, and at least 0.5 equivalents, relative to compound (II), of a nitrogen atom-containing polar aprotic solvent; a stabilization method for compound (II); and compound (II).

公开(公告)号：US20190152934A1

公开(公告)日：2019-05-23

申请号：US16098198

申请日：2017-05-11

Applicant: ZEON CORPORATION

Inventor： Kei SAKAMOTO ,  Kumi OKUYAMA ,  Kanako SANUKI

IPC: C07D277/82

Abstract: Provided is a method of producing a high-purity polymerizable compound in an industrially advantageous manner. The production method is a method of producing a polymerizable compound indicated by the following formula (I). The method includes subjecting a composition containing a halogenated compound indicated by the following formula (II) to a dehydrohalogenation reaction in an organic solvent in the presence of an aqueous layer containing a basic compound.

公开(公告)号：US20180099921A1

公开(公告)日：2018-04-12

申请号：US15560646

申请日：2016-03-30

Applicant: ZEON CORPORATION

Inventor： Kei SAKAMOTO ,  Kumi OKUYAMA ,  Kanako SANUKI

IPC: C07C67/58 ,  C07C67/14 ,  C07C69/75 ,  C07D277/82

Abstract: Disclosed is a mixture containing compound (I) and polymerizable compound (II) wherein compound (I) accounts for 50 mol % or more of the entire mixture and 1,4-cyclohexanedicarboxylic acid accounts for less than 5 mol % of the entire mixture; a method of producing the mixture which includes reacting in a water-immiscible organic solvent 1,4-cyclohexanedicarboxylic acid dichloride with compound (IV) in the presence of a base, and washing the obtained reaction solution with a weakly acidic buffer solution; etc. The disclosure provides mixtures useful for low-cost production of polymerizable compounds which have low melting points suitable for practical use, show superior solubility to general-purpose solvents, can be produced at low costs, and allow for provision of optical films capable of uniform polarized light conversion over a wide wavelength range, and methods of producing the mixtures. where A represents hydrogen, methyl group or chlorine, and n represents an integer of 1 to 20.

公开(公告)号：US20170190679A9

公开(公告)日：2017-07-06

申请号：US15124092

申请日：2015-03-19

Applicant: ZEON CORPORATION

Inventor： Kumi OKUYAMA ,  Kanako SANUKI ,  Kei SAKAMOTO

IPC: C07D277/82 ,  C07C69/757 ,  C08F22/26 ,  C07C69/75

CPC classification number: C07D277/82 ,  C07C67/14 ,  C07C69/75 ,  C07C69/757 ,  C07C2601/14 ,  C08F22/22 ,  C08F22/26

Abstract: Provided is a method for producing a polymerizable compound represented by a formula (I) comprising:a step (1) that reacts a compound represented by a formula (II) with 2,5-dihydroxybenzaldehyde in an organic solvent in the presence of a base to obtain a reaction mixture including a compound represented by a formula (III); and a step (2) that adds a compound represented by a formula (IV) and an acidic aqueous solution to the reaction mixture obtained by the step (1) to effect a reaction, wherein A represents a hydrogen atom, a methyl group or the like, L represents a leaving group, n represents an integer from 1 to 20, X represents an oxygen atom, a sulfur atom, —C(R1)(R2)— or the like, R represents a hydrogen atom, an organic group or the like, and each of RX represents a hydrogen atom, a halogen atom or the like. According to the present invention, provided is a method for producing a polymerizable compound represented by a formula (I) at high purity and at high yield.

公开(公告)号：US20200148622A1

公开(公告)日：2020-05-14

申请号：US16744489

申请日：2020-01-16

Applicant: ZEON CORPORATION

Inventor： Kei SAKAMOTO ,  Kumi OKUYAMA ,  Kanako SANUKI

IPC: C07C67/58 ,  C07D277/82 ,  C07C69/75 ,  C07C67/14 ,  C07C67/52 ,  C07C67/08 ,  C07C69/017 ,  G02B5/30

Abstract: Disclosed is a mixture containing compound (I) and polymerizable compound (II) wherein compound (I) accounts for 50 mol % or more of the entire mixture and 1,4-cyclohexanedicarboxylic acid accounts for less than 5 mol % of the entire mixture; a method of producing the mixture which includes reacting in a water-immiscible organic solvent 1,4-cyclohexanedicarboxylic acid dichloride with compound (IV) in the presence of a base, and washing the obtained reaction solution with a weakly acidic buffer solution; etc. The disclosure provides mixtures useful for low-cost production of polymerizable compounds which have low melting points suitable for practical use, show superior solubility to general-purpose solvents, can be produced at low costs, and allow for provision of optical films capable of uniform polarized light conversion over a wide wavelength range, and methods of producing the mixtures. where A represents hydrogen, methyl group or chlorine, and n represents an integer of 1 to 20.

公开(公告)号：US20170015639A1

公开(公告)日：2017-01-19

申请号：US15124092

申请日：2015-03-19

Applicant: ZEON CORPORATION

Inventor： Kumi OKUYAMA ,  Kanako SANUKI ,  Kei SAKAMOTO

IPC: C07D277/82 ,  C07C69/757 ,  C08F22/26 ,  C07C69/75

CPC classification number: C07D277/82 ,  C07C67/14 ,  C07C69/75 ,  C07C69/757 ,  C07C2601/14 ,  C08F22/22 ,  C08F22/26

Abstract: Provided is a method for producing a polymerizable compound represented by a formula (I) comprising:a step (1) that reacts a compound represented by a formula (II) with 2,5-dihydroxybenzaldehyde in an organic solvent in the presence of a base to obtain a reaction mixture including a compound represented by a formula (III); and a step (2) that adds a compound represented by a formula (IV) and an acidic aqueous solution to the reaction mixture obtained by the step (1) to effect a reaction, wherein A represents a hydrogen atom, a methyl group or the like, L represents a leaving group, n represents an integer from 1 to 20, X represents an oxygen atom, a sulfur atom, —C(R1)(R2)— or the like, R represents a hydrogen atom, an organic group or the like, and each of RX represents a hydrogen atom, a halogen atom or the like. According to the present invention, provided is a method for producing a polymerizable compound represented by a formula (I) at high purity and at high yield.

Abstract translation: 本发明提供一种由式（I）表示的可聚合化合物的制备方法，其包括：在碱的存在下，将有机溶剂中的式（II）表示的化合物与2,5-二羟基苯甲醛反应的工序（1） 得到包含由式（III）表示的化合物的反应混合物; 和将由式（IV）表示的化合物和酸性水溶液加入到通过步骤（1）获得的反应混合物中以进行反应的步骤（2），其中A表示氢原子，甲基或 L表示离去基团，n表示1〜20的整数，X表示氧原子，硫原子，-C（R 1）（R 2） - 等，R表示氢原子，有机 基团等，RX表示氢原子，卤素原子等。 根据本发明，提供了以高纯度和高产率制备由式（I）表示的可聚合化合物的方法。

公开(公告)号：US20170008862A1

公开(公告)日：2017-01-12

申请号：US15119191

申请日：2015-02-24

Applicant: ZEON CORPORATION

Inventor： Kanako SANUKI ,  Kumi OKUYAMA

IPC: C07D277/82

CPC classification number: C07D277/82

Abstract: This method for a manufacturing a 1,1-disubstituted hydrazine compound represented by a formula (II) involves reacting a hydrazino compound represented by a formula (I) with a compound represented by a formula: R-Hal in an aprotic polar solvent in the presence of a base selected from an alkali metal hydroxide and alkaline-earth metal hydroxide in an amount of 1.0 to 3.0 equivalents based on the hydrazino compound. In the formulae, X represents an oxygen atom, a sulfur atom, —CH2— or the like, and each of RX represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a cyano group, a nitro group, a fluoroalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or the like. An arbitrary C—RX that forms the ring is optionally substituted with a nitrogen atom. Hal represents a chlorine atom, a bromine atom, or an iodine atom, and R represents a substituted or unsubstituted organic group having 1 to 12 carbon atoms.

Abstract translation: 用于制备由式（II）表示的1,1-二取代肼化合物的方法包括使式（I）表示的肼基化合物与由式R-Hal表示的化合物在非质子极性溶剂中反应 基于肼基化合物，碱金属氢氧化物和碱土金属氢氧化物的碱的存在量为1.0-3.0当量。 式中，X表示氧原子，硫原子，-CH 2 - 等，RX表示氢原子，卤素原子，碳原子数1〜6的烷基，氰基， 硝基，碳原子数1〜6的氟代烷基，碳原子数1〜6的烷氧基等。 任意形成环的C-R X任选被氮原子取代。 Hal表示氯原子，溴原子或碘原子，R表示取代或未取代的碳原子数1〜12的有机基团。