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Production method of reactive epoxy carboxylate compound, resin composition containing the compound, and cured product thereof

A technology of epoxy carboxylate and resin composition, which is applied in the photoplate-making process of pattern surface, photosensitive material and coating of optical mechanical equipment, etc., which can solve the problems of reduced reliability and achieve storage stability excellent effect

Active Publication Date: 2018-01-19
NIPPON KAYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this technique, it is necessary to strictly control the temperature and time in the synthesis process and the catalyst deactivation process in order to ensure the stability during synthesis and the developability of the unexposed area.
[0006] In addition, in Patent Document 4, quaternary salts are used as esterification catalysts, but bromide is used as a counter anion, and the final product contains a large amount of halogen, so there is a problem that reliability is lowered.

Method used

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  • Production method of reactive epoxy carboxylate compound, resin composition containing the compound, and cured product thereof
  • Production method of reactive epoxy carboxylate compound, resin composition containing the compound, and cured product thereof
  • Production method of reactive epoxy carboxylate compound, resin composition containing the compound, and cured product thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1～1-4

[0125] Embodiment 1-1~1-4: The manufacture of reactive epoxy carboxylate compound (A)

[0126] NC-3000H (manufactured by Nippon Kayaku Co., Ltd., epoxy equivalent 288 g / equivalent), XD-1000 (manufactured by Nippon Kayaku Co., Ltd., epoxy equivalent 254 g / equivalent) were added as epoxy resin (a) in the amount listed in Table 1 equivalent), the acrylic acid (abbreviated as AA, Mw=72) of the amount recorded in Table 1 as the compound (b), the dimethylol propionic acid (DMPA, Mw=134 for short) as the compound (c) of the amount recorded in Table 1 ). Add 3 g of trimethylglycine (TMG) as a catalyst, and propylene glycol monomethyl ether monoacetate as a solvent so that the solid content reaches 80% by mass of the reaction solution, and react at 100° C. for 24 hours to obtain a reactive epoxy carboxylic acid Ester compound (A) or reactive epoxy carboxylate compound (A') solution. The next reaction was carried out with the solid content acid value (AV: mgKOH / g) being 5 mgKOH / g or l...

Embodiment 2-1～2-4

[0131] Embodiment 2-1~2-4: Preparation of reactive polycarboxylic acid compound (B)

[0132] In the reactive epoxy carboxylate compound (A) solution obtained in Examples 1-1 to 1-4, add tetrahydrophthalic anhydride (abbreviated as THPA) as polybasic acid anhydride (d) in Table 2 , and propylene glycol monomethyl ether monoacetate as a solvent to make the solid content 65% by mass, and after heating to 100°C, carry out an acid addition reaction to obtain a reactive polycarboxylic acid compound (B) or a reactive polycarboxylic acid Compound (B') solution. Table 1 describes the solid content acid value (AV: mgKOH / g).

Embodiment 3 and comparative example 3

[0137] Example 3 and Comparative Example 3: Preparation of dry film resist composition

[0138] Add the reactive polycarboxylic acid compound (B) obtained in Example 2 or 54.44 g of the reactive polycarboxylic acid compound obtained in Comparative Example 2, and HX-220 (trade name: Nippon Ka Yakuza Co., Ltd. diacrylate monomer) 3.54 g, 4.72 g of Irugakyua-907 (manufactured by Ciba Seika Chemical Co., Ltd.) as a photopolymerization initiator (D), and 0.47 g of Kayakuer DETX-S (manufactured by Nippon Kayaku Co., Ltd.) , 14.83 g of GTR-1800 (manufactured by Nippon Kayaku Co., Ltd.) as a curing component, 1.05 g of melamine as a thermosetting catalyst, and 20.95 g of methyl ethyl ketone as a concentration adjustment solvent were kneaded by a bead mill to make It is uniformly dispersed to obtain a resist resin composition.

[0139] The obtained composition is uniformly coated on a polyethylene terephthalate film as a support film by a roll coating method, and after passing through...

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Abstract

PROBLEM TO BE SOLVED: To provide a resin composition which gives a cured film excellent in curability, flexibility, toughness, and electrical reliability.SOLUTION: A method for producing a reactive epoxy carboxylate compound (A) reacts an epoxy resin (a) having at least two or more epoxy groups in one molecule, a compound (b) having one or more polymerizable ethylenically unsaturated groups and one or more carboxyl groups in one molecule, and optionally (c) a compound having at least two or more hydroxyl groups and one or more carboxyl groups in one molecule in the presence of trimethylglycine. A method for producing a reactive epoxy carboxylate compound (A') reacts an epoxy resin (a) having at least two or more epoxy groups in one molecule, a compound (b) having one or more polymerizable ethylenically unsaturated groups and one or more carboxyl groups in one molecule, and (c) a compound having at least two or more hydroxyl groups and one or more carboxyl groups in one molecule in the presence of trimethylglycine.

Description

technical field [0001] The present invention relates to a method for producing a reactive epoxy carboxylate compound using trimethylglycine as an esterification catalyst, a resin composition containing the reactive epoxy carboxylate compound, and a resin composition containing the reactive epoxy carboxylate compound as a reactive epoxy carboxylate compound. A resin composition of a reactive polyvalent carboxylic acid compound that is an acid-modified product of an ester compound, and a cured product thereof. Background technique [0002] Hitherto, as described in Patent Document 1 and Patent Document 2, many resin compositions containing reactive epoxy carboxylate compounds are known. [0003] Patent Document 1 describes an acid-modified epoxy acrylate compound having an epoxy resin having a polycyclic hydrocarbon group as a basic skeleton and its cured product, and it is also known that it has relatively high toughness after curing. In addition, a solder resist using the s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G59/17C08G59/14G03F7/004G03F7/027
CPCC08F290/14C08G59/02C08G59/186C08J7/04C08K5/175C08L63/00
Inventor 小木聪山本和义小渊香津美
Owner NIPPON KAYAKU CO LTD
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