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Method for producing aromatic diol mono(meth)acrylate

An aromatic diol, acrylate technology, applied in the preparation of carboxylate, the preparation of organic compounds, organic chemical methods, etc., can solve the problem of insufficient, unsatisfactory purity, and a large amount of secondary by-products of aromatic diol, etc. question

Inactive Publication Date: 2014-04-02
SHOWA DENKO KK
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, even with this method, the amount of by-products of aromatic diol di(meth)acrylate is large, and it is not yet sufficient as an economically advantageous method.
In addition, compared with the substance obtained by the method described in Patent Document 2, the aromatic diol mono(meth)acrylate obtained by this method tends to be colored and to generate solvent-insoluble matter, and the purity cannot be satisfied. Require

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  • Method for producing aromatic diol mono(meth)acrylate

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[0045] The aromatic diol mono(meth)acrylate obtained by the preparation method of the present invention is solid at normal temperature, and has the following characteristics: it is relatively stable to heat or light; and its polymerizability is the same as that of general (methyl) Acrylics are equal.

[0046] If the aromatic diol mono(meth)acrylate obtained by the production method of the present invention is used to synthesize a polymer, it is possible to obtain a high Tg polystyrene with excellent solvent solubility, alkali solubility, transparency, heat discoloration resistance, etc. , High thermal decomposition temperature, high refractive index polymer. Therefore, it can be applied to alkali-developing photoresists used in semiconductor manufacturing, display elements, printing plate-making materials, etc., protective films that require transparency and thermal discoloration resistance, and the like. In addition, it is also useful as a curing agent for epoxy resins and t...

Embodiment 1

[0064] Synthesis of 4-Hydroxyphenyl Methacrylate

[0065] Put 100 parts by mass of hydroquinone, 235 parts by mass of methacrylic acid, and 4 parts by mass of p-toluenesulfonic acid into a 1L detachable flask equipped with a condenser, a thermometer, and a stirring paddle, and start at 120°C while blowing in air. reaction. When the reaction reached equilibrium and the composition of the product was constant, the reaction was continued while performing vacuum distillation at -80 kPa so that the water content in the system was maintained at 0.2% by mass or less. When the ratio of 4-hydroxyphenyl methacrylate reached 49.9% of the moles of hydroquinone charged, the system was returned to normal pressure and cooled to complete the esterification reaction. The composition ratio, color tone, and turbidity are all shown in Table 1.

Embodiment 2

[0067] Synthesis of 4-Hydroxyphenyl Methacrylate

[0068] 100 parts by mass of hydroquinone, 235 parts by mass of methacrylic acid, and 10 parts by mass of strongly acidic ion-exchange resin Amberlyst15.DRY manufactured by Organo Co., Ltd. were put into a condenser and a thermometer. , a 1L detachable flask with a stirring paddle, and start the reaction at 120°C. When the reaction reached equilibrium and the composition of the product was constant, the reaction was continued while performing vacuum distillation at -80 kPa so that the water content in the system was maintained at 0.2% by mass or less. When the ratio of 4-hydroxyphenyl methacrylate reached 56.8% of the moles of hydroquinone charged, the system was returned to normal pressure and cooled to complete the esterification reaction. The composition ratio, color tone, and turbidity are all shown in Table 1.

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Abstract

The purpose of the present invention is to provide an economically advantageous production method for obtaining a high-purity aromatic diol mono(meth)acrylate that is suppressed in coloration and solvent-insoluble fraction. In order to achieve the purpose, the present invention provides a method for producing an aromatic diol mono(meth)acrylate by esterifying an aromatic diol and a (meth)acrylic acid in the presence of a strong acid. This method for producing an aromatic diol mono(meth)acrylate comprises a step wherein an esterification reaction is performed in the absence of a solvent or in the presence of an aprotic organic solvent at a temperature from 100 DEG C to 140 DEG C, while removing the water content in the reaction system by heating and pressure reduction.

Description

technical field [0001] The present invention relates to a method capable of obtaining high-purity aromatic diol mono(meth)acrylate that is colored and has little solvent-insoluble matter, and is an economically advantageous production method. Background technique [0002] As a method of producing aromatic diol mono(meth)acrylate, a method of reacting aromatic diol with (meth)acrylic anhydride or (meth)acryloyl chloride is known (for example, refer to Patent Document 1). [0003] In addition, as a method for obtaining high-purity aromatic diol mono(meth)acrylate, the following method for obtaining high-purity aromatic diol mono(meth)acrylate has been reported, and the method includes the following steps: A method of preparing a reaction liquid containing aromatic diol mono(meth)acrylate and aromatic diol di(meth)acrylate as a by-product by reacting aromatic diol with (meth)acrylic anhydride process; a process of preparing crude crystals by removing unreacted aromatic diol in...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C69/54C07B61/00
CPCC07C67/08C07C69/54
Inventor 辻村优实市川贵生海野笃远藤充雄
Owner SHOWA DENKO KK
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