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Aromatic amine resin having n-alkyl group, curable resin composition, and cured product thereof

A kind of hardening resin, aromatic amine technology, used in condensation/addition reaction to prepare amino compounds, organic chemistry, etc., can solve the problems of insufficient hygroscopicity or electrical properties, insufficient reactivity, unsatisfactory electrical properties, etc. , to achieve the effect of excellent hardenability and excellent heat resistance

Active Publication Date: 2020-12-18
NIPPON KAYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, Patent Document 1 uses acryl-substituted phenol resins in their entirety, but their hygroscopicity and electrical properties are insufficient.
In addition, in Patent Document 2, all allyl-substituted phenolic resins are used, but the reactivity is insufficient, and Claisen rearrangement (Claisen Rearrangement) occurs simultaneously during the curing process to generate hydroxyl groups, so the electrical characteristics are not satisfactory.

Method used

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  • Aromatic amine resin having n-alkyl group, curable resin composition, and cured product thereof
  • Aromatic amine resin having n-alkyl group, curable resin composition, and cured product thereof
  • Aromatic amine resin having n-alkyl group, curable resin composition, and cured product thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0168] 150 g of toluene and 56.0 g of N-methylaniline were added to a flask equipped with a thermometer, a cooling pipe, and a stirrer, and stirred. Then, 43.5 g of 4,4'- bischloromethylene biphenyl was added over 1 hour, and it was made to react at 65 degreeC for 2 hours. Next, 36.1 g of 35% hydrochloric acid was added dropwise at 80°C or lower. After completion of the dropwise addition, the temperature was raised to 210° C. while azeotropic dehydration, and the reaction was carried out at 210° C. for 15 hours. After the reaction, 100 g of 17% caustic soda aqueous solution was added dropwise to make the reaction solution alkaline, and 100 g of toluene and 150 g of N-methylaniline were added thereto, followed by stirring for 6 hours. After standing still and waste water, wash with water until the waste water becomes neutral. Solvent, water, unreacted N-methylaniline were distilled off by concentration under reduced pressure, and biphenyl-N-methylaniline novolac (BNMAN-1) was...

Embodiment 2

[0170] 50 g of toluene and 171.5 g of N-methylaniline were added to a flask equipped with a thermometer, a cooling pipe, and a stirrer, and stirred. Then, 50.2 g of 4,4'- bischloromethylene biphenyl was added over 1 hour, and it was made to react at 65 degreeC for 2 hours. Next, 41.7 g of 35% hydrochloric acid was added dropwise at 80° C. or lower. After completion of the dropwise addition, the temperature was raised to 210° C. while azeotropic dehydration, and the reaction was carried out at 210° C. for 15 hours. After completion of the reaction, 40 g of 48% caustic soda aqueous solution was added dropwise to make the reaction liquid alkaline, and 50 g of toluene was further added, followed by stirring for 6 hours. After standing still and waste water, wash with water until the waste water becomes neutral. Solvent, water, unreacted N-methylaniline were distilled off by concentrating under reduced pressure, and biphenyl-N-methylaniline novolac (BNMAN-2) was obtained in the f...

Embodiment 3

[0172] 200 g of water and 214 g of N-methylaniline were added to a flask equipped with a thermometer, a cooling pipe, and a stirrer, and stirred. Then, 209 g of 35% hydrochloric acid was dripped at 40 degreeC or less. Next, 108 g of 37% formaldehyde aqueous solution was dripped at 40 degreeC or less. After completion of the dropwise addition, the mixture was reacted at 75°C to 80°C for 5 hours. After completion of the reaction, 168 g of 48% caustic soda aqueous solution was added dropwise to make the reaction liquid alkaline, and 300 g of toluene was further added, followed by stirring for 6 hours. After standing still and waste water, wash with water until the waste water becomes neutral. The solvent, water, and unreacted N-methylaniline were distilled off by concentration under reduced pressure to obtain 200 g of N-methylaniline novolac (NMAN-1) in the form of a black liquid resin (amine equivalent: 116 g / eq., composition The ratio is GPC area %: n=1 component: 37%, n=2 c...

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Abstract

Provided is the provision of an aromatic amine resin compound having an N-alkyl group that presents exceptional heat resistance and electrical characteristics, and a curable resin composition thereof.An aromatic amine resin having an N-alkyl group represented by formula (1). (In formula (1), the plurality of R present each independently represent a hydrogen or a C1-15 hydrocarbon group; however,this excludes the instance in which all R are hydrogen. The plurality of X present each independently represent a hydrogen atom or a C1-15 hydrocarbon group. I1, I2, and m represent integers of 1 or higher and satisfy the relationships I1 + m <=5 and I2 + m <= 4. n represents 1 <= n <=15.).

Description

technical field [0001] The present invention relates to an aromatic amine resin having an N-alkyl group, a curable resin composition, and a cured product thereof, which can be preferably used for sealing materials for semiconductor elements, sealing materials for liquid crystal display elements, organic electroluminescence (electroluminescence) , EL) component sealing materials, printed wiring boards, build-up laminates and other electrical - electronic parts or carbon fiber reinforced plastics, glass fiber reinforced plastics and other lightweight high-strength structural materials in composite materials. Background technique [0002] In recent years, due to the expansion of the field of use of laminated boards on which electric and electronic components are mounted, a wide range of characteristics and high-level requirements are required. In particular, with the miniaturization, thinning, and high density of semiconductor packages (packages) (hereinafter referred to as PKG...

Claims

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Application Information

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IPC IPC(8): C08G61/02C07C209/60C07C211/50C08L65/00
CPCC08G61/02C07C211/50C08L65/00C07C209/60C08G12/08C08L61/04C08G61/04
Inventor 远岛隆行中西政隆鎗田正人长谷川笃彦
Owner NIPPON KAYAKU CO LTD
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