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Mixture of polymerizable compound and method for producing same

A technology for polymerizable compounds and manufacturing methods, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of narrow temperature range of display liquid crystallinity, insufficient abnormal wavelength dispersion, and difficulty in coating films.

Active Publication Date: 2017-12-01
ZEON CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the low-molecular-weight polymerizable compounds described in these documents have insufficient anomalous wavelength dispersion, or have high melting points that are not suitable for processing in industrial processes, so it is difficult to apply them to films, and the temperature range for exhibiting liquid crystallinity is extremely narrow. There are many problems in terms of performance, such as low solubility in solvents generally used in industrial processes
In addition, these low-molecular-weight polymerizable compounds are synthesized in multiple steps using a synthesis method using very expensive reagents, so there is also a problem in terms of cost.

Method used

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  • Mixture of polymerizable compound and method for producing same
  • Mixture of polymerizable compound and method for producing same
  • Mixture of polymerizable compound and method for producing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0289] (Example 1) Preparation of Mixture 1

[0290] [chemical formula 31]

[0291]

[0292] In a 3-port reactor with a thermometer, 10.0 g (47.83 mmol) of trans-1,4-cyclohexane dicarboxylic acid chloride and cyclopentyl methyl ether ( CPME) 200ml. 12.64 g (47.83 mmol) of 4-(6-acryloyloxy-1-hexyloxy)phenol (manufactured by DKSH) represented by formula (IVa) was added thereto, and the reactor was immersed in an ice bath to allow the reaction The liquid internal temperature was 0°C. Next, 4.83 g (47.83 mmol) of triethylamine was slowly added dropwise over 5 minutes while keeping the internal temperature of the reaction liquid at 10° C. or lower. After completion of the dropwise addition, the entire contents were returned to 25° C. and stirred for further 1 hour.

[0293] 100 ml of distilled water was added to the obtained reaction liquid, and after washing|cleaning at 25 degreeC for 2 hours, the water layer was extracted. Further, the organic layer was washed twice with ...

Embodiment 2

[0297] (Example 2) Production of Mixture 2

[0298] The same operation as in Example 1 was performed except that 200 ml of CPME as a reaction solvent was replaced with 150 ml of tetrahydrofuran (THF). As a result, 17.91 g of a white solid was obtained.

[0299] The composition of the obtained white solid was confirmed by the same method as in Example 1. As a result, it was found that 12.89 g (30.81 mmol) of the target monoester, 4.98 g (7.49 mmol) of the diester, and 41 mg (0.24 mmol) of cyclohexanedicarboxylic acid. When the molar content was calculated from the respective composition ratios, the monoester content: 79.94 mol%, the diester content: 19.44 mol%, and the cyclohexanedicarboxylic acid content: 0.61 mol%.

Embodiment 3

[0300] (Example 3) Preparation of Mixture 3

[0301] The same operation as in Example 1 was performed except that 200 ml of CPME as a reaction solvent was replaced with 200 ml of methyl tert-butyl ether (MTBE). As a result, 17.70 g of a white solid was obtained.

[0302] The composition was confirmed by the same method, and it was found that 12.52 g (29.92 mmol) of the target monoester, 5.14 g (7.73 mmol) of the diester, and 43 mg (0.25 mmol) of cyclohexanedicarboxylic acid were included. . When the molar content was calculated from the respective composition ratios, the monoester content: 78.94 mol%, the diester content: 20.39 mol%, and the cyclohexanedicarboxylic acid content: 0.67 mol%.

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Abstract

The present invention provides: a mixture containing a compound (I) and a polymerizable compound (II), wherein the content of the compound (I) is 50% by mole or more of the entire mixture and the content of 1, 4-cyclohexane dicarboxylic acid is less than 5% by mole; a method for producing this mixture, which comprises a step for reacting 1, 4-cyclohexane dicarboxylic acid dichloride and a compound (IV) in the presence of a base in a water-immiscible organic solvent and a step for cleaning the thus-obtained reaction solution with a weak acidic buffer solution; and the like. The present invention provides: a mixture which is useful for producing a polymerizable compound at low cost, said polymerizable compound having a practically low melting point and excellent solubility in common solvents and enabling the achievement of an optical film that is able to be produced at low cost and is capable of uniform polarization conversion over a wide wavelength range; and a method for producing this mixture. (In the formulae, A represents a hydrogen atom, a methyl group or a chlorine atom; and n represents an integer of 1-20.)

Description

technical field [0001] The present invention relates to a mixture that can be used for inexpensive production of a polymeric compound that has a practically low melting point, is excellent in solubility in general-purpose solvents, and can be produced at low cost and has a wide wavelength range. Optical film that can perform the same polarized light conversion. Background technique [0002] There are 1 / 4 wave plates that convert linearly polarized light into circularly polarized light, 1 / 2 wave plates that convert the polarization vibration plane of linearly polarized light by 90 degrees, and the like as retardation plates. These phase difference plates can correctly convert a specific monochromatic light into a phase difference of 1 / 4λ or 1 / 2λ of the light wavelength. [0003] However, the conventional retardation film has a problem of converting the polarized light outputted through the retardation film into colored polarized light. This is due to the fact that the mater...

Claims

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Application Information

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IPC IPC(8): C07C69/75C07C67/14C07C67/58C07C69/017C07D277/82G02B5/30
CPCC07C67/14C07C69/017C07C69/75C07D277/82G02B5/30C07C67/08C07C67/52C07C2601/14C07C67/58C07C69/757G02B1/08
Inventor 坂本圭奥山久美佐贯加奈子
Owner ZEON CORP
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