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Polyvalent carboxylic acid, composition thereof, curable resin composition, cured product, and method for manufacturing polyvalent carboxylic acid

A polycarboxylic acid and composition technology, which is applied in the preparation of organic compounds, the preparation of carboxylic acid esters, chemical instruments and methods, etc., can solve the problems of quality deterioration, inability to obtain stable performance, poor curing and other problems

Active Publication Date: 2012-05-16
NIPPON KAYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, when the above-mentioned alicyclic acid anhydride is used as a curing agent alone, because these curing agents have a high vapor pressure and partly evaporates during curing, there is a ring caused by the absence of a predetermined amount of carboxylic anhydride (curing agent) in the cured product. The problem of poor curing of the epoxy resin composition and the problem that its characteristics vary greatly depending on the curing conditions, making it difficult to obtain a cured product with stable target performance
In addition, when a large amount of cured products are produced in an open system, these curing agents volatilize into the atmosphere, which also causes problems: environmental pollution caused by the release of harmful substances into the atmosphere, adverse effects on the human body, and pollution of the production line.
[0008] In addition, when the cured product obtained by using the conventional curing agent seals LEDs, especially SMD (Surface Mount Device: surface mount components), since the amount of resin used is small, the following problems arise: the above-mentioned poor curing and failure Problems such as significant influence on stable performance, exposure of wiring or incomplete sealing due to generation of craters, cracks and / or peeling during reflow soldering, quality deterioration due to long-term lighting, etc.

Method used

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  • Polyvalent carboxylic acid, composition thereof, curable resin composition, cured product, and method for manufacturing polyvalent carboxylic acid
  • Polyvalent carboxylic acid, composition thereof, curable resin composition, cured product, and method for manufacturing polyvalent carboxylic acid
  • Polyvalent carboxylic acid, composition thereof, curable resin composition, cured product, and method for manufacturing polyvalent carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0217] Embodiment 1 (polycarboxylic acid composition A1)

[0218] In a flask equipped with a stirrer, a reflux condenser, and a stirring device, 10 parts of toluene and 2,4-diethyl-1,5-pentanediol (manufactured by Kyowa Hakka Chemical Co., Ltd.; キヨウワジオオール PD9) 80 parts, a mixture of methyl hexahydrophthalic anhydride and hexahydrophthalic anhydride (manufactured by Shin Nippon Chemical Co., Ltd.; Rikacid MH700 ratio 7:3, hereinafter referred to as acid anhydride H1) 168 parts were heated and stirred at 100° C. for 4 hours. At this point, the reaction was terminated after confirming the disappearance of the raw material (1 area % or less) by GPC. After completion|finish of reaction, the residual solvent was distilled off using the rotary evaporator, and 246 parts of polyhydric carboxylic acid compositions (A1) of this invention were obtained. The resultant was a colorless solid resin with a polycarboxylic acid content of 97 area % as measured by GPC. In addition, the function...

Embodiment 2

[0219] Embodiment 2 (curing agent composition B1)

[0220] 75 parts of acid anhydride (H1) was added to 25 parts of polyvalent carboxylic acid composition (A1) obtained in Example 1, and it was made to dissolve uniformly, and the hardening|curing agent composition (B1) of this invention was obtained. The viscosity at 50°C was 450 mPa·s (E-type viscometer).

Embodiment 3

[0221] Embodiment 3 (curing agent composition B2)

[0222] Into a flask equipped with a stirrer, a reflux condenser, and a stirring device, 2,4-diethyl-1,5-pentanediol (manufactured by Kyowa Hakka Chemical Co., Ltd.; Kiyowajiol PD9) was added while purging nitrogen gas. ) and 100 parts of acid anhydride (H1) were heated and stirred at 60° C. for 4 hours. It was confirmed by GPC that 2,4-diethyl-1,5-pentanediol was 1 area % or less. 120 parts of hardening|curing agent compositions (B2) containing the polyhydric carboxylic acid composition of this invention were obtained. The obtained reaction product was a colorless liquid resin. The composition ratio measured by GPC was 52 area % of polyhydric carboxylic acid (A1), and 48 area % of the total amount of methyl hexahydrophthalic anhydride and hexahydrophthalic anhydride. In addition, the functional group equivalent was 197 g / eq. The viscosity at 50°C is 1340 mPa·s (19700 mPa·s at 25°C; E-type viscometer).

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Abstract

Provided are: a polyvalent carboxylic acid composition containing a polyvalent carboxylic acid represented by formula (1); an epoxy resin curing agent composition containing the polyvalent carboxylic acid composition; a curable resin composition containing said curing agent composition and an epoxy resin; a cured product thereof; and a novel polyvalent carboxylic acid. When said polyvalent carboxylic acid and a composition containing same are used as curing agents for an epoxy resin, the volatility of the curing agent when curing is low, and the obtained cured product has excellent optical properties and thermal endurance. In formula (1), each R independently represents a hydrogen atom, a C1-6 alkyl group or a carboxyl group, and P represents one of the bivalent cross-linking groups defined as follows: (a) a C6-20 alkyl chain having a branched structure, said alkyl chain having a C3-12 linear main chain and two to four side chains, at least one of said side chains having between two and ten carbon atoms; or (b) at least one cross-linked polycyclic diol which may have a methyl group on a cyclo ring thereof and from which two hydroxyl groups are removed, said cross-linked polycyclic diol selected from between tricyclodecane dimethanol and pentacyclopentadecane dimethanol. If P is (b), then R represents a group other than a hydrogen atom.

Description

technical field [0001] The present invention relates to a polyvalent carboxylic acid, a polyvalent carboxylic acid composition, and a curable epoxy resin composition containing the polyvalent carboxylic acid composition as a curing agent for epoxy resins, which are particularly suitable for electrical and electronic materials. In addition, this polyvalent carboxylic acid composition is also used as a resin for coating materials, adhesives, molded products, semiconductors, optical semiconductor sealing materials, optical semiconductor die-bonding materials, and polyimide resins in other fields where polyvalent carboxylic acids are used. Such as raw materials or modifiers, plasticizers, lubricating oil raw materials, intermediate products of pharmaceuticals and pesticides, raw materials for resins for coatings, or resins for toners. Background technique [0002] Polyvalent carboxylic acids have high thermal stability, good electrical properties, excellent chemical resistance, ...

Claims

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Application Information

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IPC IPC(8): C07C69/75C07C67/08C08G59/42
CPCC08G59/4246C07C67/08C08G59/24C07C2101/14C07C69/75C07C2103/68C08L63/00C08G59/688C07C2601/14C07C2603/68
Inventor 中西政隆洼木健一宫川直房川田义浩佐佐木智江青木静铃木瑞观枪田正人小柳敬夫
Owner NIPPON KAYAKU CO LTD
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