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Curable polyvinyl benzyl compound and process for producing the same

a polyvinyl benzyl compound and polyvinyl benzyl technology, applied in the direction of synthetic resin layered products, woven fabrics, metal layered products, etc., can solve the problems of low crosslinking density, linear expansion coefficient, low chemical resistance,

Inactive Publication Date: 2008-05-15
SHOWA HIGHPOLYMER CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The resulting resin exhibits superior dielectric properties, including a low dielectric dissipation factor and high heat resistance, making it suitable for high-frequency applications while maintaining stability and performance across a wide temperature range.

Problems solved by technology

However, the above materials proposed in the prior art have various problems such as a low crosslinking density and a large linear expansion coefficient; low chemical resistance; poor tenacity; a large number of complicated steps required for the production of a resin from raw materials; and the need for a special solvent for shaping.
Therefore, they have not been put to practical use yet.
However, the requirements for dielectric properties of electronic materials are becoming more and more demanding.
Next-generation communication devices have begun to appear, which require, in particular, a low dielectric dissipation factor, which cannot be satisfied even by the above vinylbenzyl ether compound.

Method used

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  • Curable polyvinyl benzyl compound and process for producing the same
  • Curable polyvinyl benzyl compound and process for producing the same
  • Curable polyvinyl benzyl compound and process for producing the same

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0195] 49.8 g (0.3 mol) of fluorene, 200 g of methylisobutyl ketone, 2.91 g (9×10−3 mol) of tetra-n-butylammonium bromide, 0.73 g of hydroquinone and 96 g of a 50 wt % aqueous solution of NaOH (NaOH purity of 95%, 1.14 mol) were charged into a 1-liter four-necked flask equipped with a thermoregulator, stirrer, cooling condenser and dropping funnel and heated at 62° C. under agitation to prepare a uniform solution. 117 g of vinylbenzyl chloride CMS-AM (m- / p-isomers: 50 / 50 wt % mixture) available from Seimi Chemical Co., Ltd. (purity of 91%, 0.7 mol) was added dropwise to this dark blue green solution over 20 minutes and then a reaction was carried out at 60 to 61° C. for 7 hours. After 200 ml of toluene was added to the obtained green reaction product, the obtained solution was neutralized with 2N hydrochloric acid and washed with distilled water three times, toluene was removed under reduced pressure, and the obtained light yellow viscous solid was recrystallized from fresh toluene ...

example 2

[0198] 49.8 g (0.3 mol) of fluorene, 220 g of toluene, 2.91 g (9×10−3 mol) of tetra-n-butylammonium bromide and 96 g of a 50 wt % aqueous solution of NaOH (purity of 95%, 1.14 mol) were added to the reactor used in Example 1 and heated at 65° C., and 21 g (0.12 mol) of p-xylylene dichloride was added, and reacted for 2.5 hours. After it was confirmed from the results of the 1H-NMR measurement of a small amount of the reaction product that p-xylylene dichloride was consumed, 54 g of CMS-AM (purity of 91%, 0.36 mol) was added dropwise to the reaction system and the reaction was continued at 65° C. for 6.5 hours. After the reaction solution was cooled to room temperature, 2N hydrochloric acid was added to neutralize the reaction mixture, and distilled water was added to the organic layer, which was then washed three times. After the solvent was distilled off under reduced pressure, the obtained solid was pulverized and filtered in methanol to collect solid matter through filtration, wh...

example 3

[0200] A solution containing 60 wt % of Compound 2 synthesized in Example 2 and 40 wt % of divinyl benzene (purity of 82%) was prepared, poured into the gap between glass plates and cured at 100° C. for 6 hours, at 160° C. for 4 hours and after-cured at 180° C. for 2 hours. Test specimens required for each measurement were prepared from the obtained resin plate. The results are shown in Table 1.

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PUM

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Abstract

A curable polyvinyl benzyl compound represented by the following general formula (1) wherein R1 represents a C2-20 organic group, R2 represents a hydrogen atom, etc., x is an integer of 0 to 4, and n is an integer of 0 to 2. The compound is obtained by reacting a fluorene compound with a vinylbenzyl halide in the presence of an alkali.

Description

CROSS REFERENCE TO RELATED APPLICATIONS [0001] This application is a Divisional of U.S. application Ser. No. 10 / 954,214 filed Oct. 1, 2004, which is a Continuation-In-Part of U.S. application Ser. No. 10 / 474,453 filed Oct. 8, 2003, which is the National Stage of PCT / JP02 / 02851 filed on Mar. 25, 2002.TECHNICAL FIELD [0002] The present invention relates to a compound which provides a cured product having high heat resistance, low water absorption and excellent dielectric properties which are required for organic insulating materials for use in electronic equipment such as communication equipment and to a process for producing the same. More specifically, the present invention relates to a curable polyvinyl benzyl compound obtained by reacting a fluorene compound with a vinylbenzyl halide, a process for producing the same, and a curable resin composition and a cured resin obtained by using the same. Further, the present invention relates to a substrate, a prepreg and a metal foil havin...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): B32B15/08C07C13/567C08F12/34C08F290/06C08G61/02H05K1/03H05K3/46
CPCB32B15/08C07C13/567C07C2103/18C08F12/34Y10T428/24917C08G61/02H05K1/0326H05K3/4626C08F290/06C07C2603/18Y10T428/31656Y10T428/31678Y10T428/31522Y10T428/249933Y10T428/31855Y10T442/2934
Inventor NISHIGUCHI, SHOUJIIKEYA, TATSUHIROYOSHIDA, HARUOSHIBATA, JYOUJIKOFUNE, HIROTAKA
Owner SHOWA HIGHPOLYMER CO LTD
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