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Naphthol resin, epoxy resin, epoxy resin composition, and solidified products thereof

A technology of naphthol resin and epoxy resin, which is applied in the field of epoxy resin composition and its cured product, can solve the problem of not meeting the influence of epoxy resin or curing agent, curability and physical properties, and the limitation of high filling rate and other problems, to achieve the effects of excellent curability, excellent symmetry, and excellent heat resistance

Active Publication Date: 2010-07-07
NIPPON STEEL CHEMICALL &MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, among currently known epoxy resins or curing agents, there is no epoxy resin or curing agent that meets these requirements.
For example, the well-known bisphenol-type epoxy resin is liquid at room temperature, has excellent processability, and is easy to mix with curing agents, additives, etc., so it is widely used, but it has problems in heat resistance and moisture resistance.
In addition, naphthol-type resins are known as resins that improve heat resistance, moisture resistance, and flame retardancy, but there is a limit to increasing the filling rate of fillers due to their high viscosity.
Therefore, when lowering the molecular weight with the aim of lowering the viscosity, there is a problem that curability is deteriorated and formability is lowered.
Patent Documents 5 and 6 describe reducing the molecular weight by adjusting the ratio of naphthol and crosslinking agent, but there is no description of the naphthol resin and the substitution position of crosslinking agent with respect to naphthol. The effect of the compositional ratio of different isomers on the curability and physical properties of the resin is completely unknown.
In addition, in Patent Document 7, a naphthol resin based on the reaction of 1-naphthol and 1,4-dichlorotoluene is disclosed, but there is also no teaching about the substitution position of the crosslinking agent with respect to naphthol.

Method used

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  • Naphthol resin, epoxy resin, epoxy resin composition, and solidified products thereof
  • Naphthol resin, epoxy resin, epoxy resin composition, and solidified products thereof
  • Naphthol resin, epoxy resin, epoxy resin composition, and solidified products thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065]400 g of 1-naphthol and 200 g of chlorobenzene were added to a 1 L four-neck detachable flask equipped with a stirrer, a cooling tube, and a nitrogen gas introduction tube, and heated to 60° C. while introducing nitrogen gas to dissolve them. Thereafter, a mixed solution of 152 g of 1,4-dichloromethylbenzene and 152 g of chlorobenzene was added dropwise, stirring, and reacted at 60° C. for 6 hours. During this period, hydrogen chloride produced by the reaction was discharged outside the system. Thereafter, after removing ionic components by washing with water, chlorobenzene and unreacted 1-naphthol were removed by distillation under reduced pressure to obtain 275 g of a naphthol resin (naphthol resin A). The softening point of the obtained resin was 93° C., the melt viscosity at 150° C. was 0.21 Pa·s, and the hydroxyl equivalent was 215. According to the GPC measurement results, the proportions of n=1 body, n=2 body, n=3 body, n=4 body, and n≥5 bodies are 52wt%, 24wt%, ...

Embodiment 2

[0068] 400 g of 1-naphthol and 200 g of toluene were put into a 1 L four-necked separable flask equipped with a stirrer, a cooling pipe, and a nitrogen gas introduction pipe, and heated to 40° C. while nitrogen gas was introduced to dissolve them. Thereafter, a mixed solution of 68 g of 1,4-dichloromethylbenzene and 68 g of toluene was added dropwise, stirring, and reacted at 40° C. for 12 hours. During this period, hydrogen chloride produced by the reaction was discharged outside the system. Then, after removing ionic components by water washing, toluene and unreacted 1-naphthol were removed by vacuum distillation, and 134 g of naphthol resins were obtained (naphthol resin B). The softening point of the obtained resin was 85° C., the melt viscosity at 150° C. was 0.09 Pa·s, and the hydroxyl equivalent was 218. According to the GPC measurement results, the proportions of n=1 body, n=2 body, n=3 body, n=4 body are 72wt%, 19wt%, 5wt%, 1wt%, respectively, weight average molecula...

Embodiment 3

[0070] Dissolve 100 g of naphthol resin A obtained in Example 1 in 260 g of epichlorohydrin and 36 g of diglyme, and add 48% aqueous sodium hydroxide solution 37.5 g under reduced pressure (about 100 mmHg) at 60° C. for 4 hours. g. During this period, the generated water is discharged out of the system through azeotropy with epichlorohydrin, and the distilled epichlorohydrin is returned to the system. After the dropwise addition, the reaction was continued for 1 hour. Thereafter, epichlorohydrin and diglyme were distilled off under reduced pressure, dissolved in 420 g of methyl isobutyl ketone, and the generated salt was removed by filtration. Then, 10 g of 48% sodium hydroxide aqueous solution was added, and it was made to react at 80 degreeC for 2 hours. After the reaction, filtration and water washing were performed, and methyl isobutyl ketone as a solvent was distilled off under reduced pressure to obtain 113 g of a brown epoxy resin (epoxy resin A). The obtained resin ...

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Abstract

The present invention provides a novel naphthol resin and a naphthol type epoxy resin. These resins are capable of keeping an excellent forming property and a high filling property because of low viscosity and good solidifying reactivity. Solidified products of the resins are obtained by solidifying an epoxy resin composition, has characteristics of excellent fire resistance, high adhesive bonding property, good moisture-proof property and excellent heat resisting property, and has functions of lamination, forming, cast molding, adhesive bonding and the like. The naphthol resin is representedby the following general formula (1) and the epoxy resin is obtained by performing a process of epoxidation of the naphthol resin, and the present invention is characterized in that in the general formula (1), the n=1 part is 50 wt% of the whole part, displacement position of the crosslinked radical of a 1-naphthol framework in the n=1 part is 4 which is of the position of 4', the content of the isomer of 4' is between 20wt% and 60wt%, and the total content of the isomer of 4', 2 and 2' is between 40wt% and 80wt%.[the chemical formula 1].

Description

technical field [0001] The present invention relates to a naphthol resin useful as a base resin for semiconductor seals, laminates, coating materials, composite materials, etc., an epoxy resin, a method for producing them, an epoxy resin composition using the same, and a cured product thereof . Background technique [0002] In recent years, the development of base resins with higher performance has been demanded especially with the progress in the field of advanced materials. For example, in the field of semiconductor sealing, the problem of cracking of packages has become more serious due to the thinning and larger area of ​​packages corresponding to recent high-density mounting, and the popularization of surface mounting methods. As their base resins, strong Improvements in low viscosity, moisture resistance, heat resistance, low thermal expansion, and adhesion to metal substrates are required, aiming at increasing the filling rate of fillers. Furthermore, recently, from...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G8/00C08G59/06C08L63/00
CPCC08G59/063C08G59/18C08G61/02C08L63/00
Inventor 中原和彦梶正史
Owner NIPPON STEEL CHEMICALL &MATERIAL CO LTD
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