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

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

Example Embodiment

[0167](Example 1)

[0168]150 g of toluene and 56.0 g of N-methylaniline were added to a flask equipped with a thermometer, a cooling tube, 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 dropping, the temperature was raised to 210°C while azeotropic dehydration, and the reaction was carried out at 210°C for 15 hours. After the completion of the reaction, 100 g of a 17% caustic soda aqueous solution was added dropwise to make the reaction liquid alkaline, and 100 g of toluene and 150 g of N-methylaniline were further added and stirred for 6 hours. After standing 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 biphenyl-N-methylaniline novolac (BNM...

Example Embodiment

[0169](Example 2)

[0170]To a flask equipped with a thermometer, a cooling tube, and a stirrer, 50 g of toluene and 171.5 g of N-methylaniline were added and stirred. Then, 4,4'-bischloromethylene biphenyl 50.2g 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 the completion of the reaction, 40 g of a 48% aqueous caustic soda solution was added dropwise to make the reaction liquid alkaline, and 50 g of toluene was further added and stirred for 6 hours. After standing 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 biphenyl-N-methylaniline novolac (BNMAN-2) as a black solid resi...

Example Embodiment

[0171](Example 3)

[0172]Into a flask equipped with a thermometer, a cooling tube, and a stirrer, 200 g of water and 214 g of N-methylaniline were added and stirred. Then, 209 g of 35% hydrochloric acid was added dropwise below 40°C. Next, 108 g of 37% formaldehyde aqueous solution was added dropwise at 40°C or lower. After the dropping, the reaction was carried out at 75°C to 80°C for 5 hours. After the completion of the reaction, 168 g of a 48% aqueous caustic soda solution was added dropwise to make the reaction liquid alkaline, and 300 g of toluene was further added and stirred for 6 hours. After standing 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, and 200 g of N-methylaniline novolac (NMAN-1) (amine equivalent: 116g / eq., composition) was obtained as a black liquid resin. The ratio is in terms of GPC area %: n=1 component: 37%, n=2 component: 19...

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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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