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Bis ether compounds having fluorene skeleton and resin composition

A compound and composition technology, applied in the field of aromatic bishalogenated methyl compounds, can solve the problems of high refractive index and insufficient dimensional stability of optical lenses, and achieve small dielectric loss tangent, high heat resistance, The effect of excellent optical characteristics

Active Publication Date: 2014-06-18
NIPPON STEEL CHEMICALL &MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the optical lens obtained therefrom does not satisfy the high refractive index demanded by recent thinning of the lens unit, and is also insufficient in terms of dimensional stability.

Method used

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  • Bis ether compounds having fluorene skeleton and resin composition
  • Bis ether compounds having fluorene skeleton and resin composition
  • Bis ether compounds having fluorene skeleton and resin composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0137] Add 140.16g (0.40 mol) of 9,9-bis(4-hydroxyphenyl)fluorene, 141.40g (0.88 mol) of 4,4'-bis(chloromethyl)biphenyl and 1200ml of acetone into the reaction vessel, stirring While raising the temperature to 78°C. Next, KOH-MeOH (KOH: 0.88 mol) was dropped into the reaction vessel kept at 78° C. over 30 minutes. After completion of the dropping, stirring was further continued at 78° C. for 4 hours. After 4 hours, it was cooled to room temperature, 900 ml of toluene was added, and 10% HCl was further added for neutralization. Then, the aqueous phase was separated by liquid separation, and further washed three times with 300 ml of water.

[0138] The obtained organic phase was concentrated by distillation, methanol was added, and the product was reprecipitated. The precipitate was filtered and dried to obtain the aromatic bischloromethyl compound A which is a reaction product of 9,9-bis(4-hydroxyphenyl)fluorene and 4,4'-bis(chloromethyl)biphenyl (2CM-DMBP-BPFZ) 169.33g. T...

Embodiment 2

[0151] Add 140.16g (0.40 mole) of 9,9-bis(4-hydroxyphenyl)fluorene, 157.20g (0.88 mole) of α,α'-dichloro-p-xylene and 1200ml MEK into the reaction vessel, and heat up while stirring to 78°C. Next, KOH-MeOH (KOH: 0.88 mol) was dripped into the reaction container maintained at 78 degreeC over 30 minutes. After completion of the dropping, stirring was further continued at 78° C. for 4 hours. After 4 hours, it was cooled to room temperature, 900 ml of toluene was added, and 10% HCl was further added for neutralization. Then, the aqueous phase was separated by liquid separation, and further liquid separation washing was performed three times with 300 ml of water.

[0152] The obtained organic phase was concentrated by distillation, methanol was added, and the product was reprecipitated.

[0153] The precipitate was filtered and dried to obtain the aromatic bischloromethyl compound B ( 2CM-Xy-BPFZ) 123.57g.

[0154] Gel permeation chromatography (GPC), infrared spectroscopy (IR...

Embodiment 3

[0165] 15.28 g (0.11 mol) of potassium carbonate and 500 ml of N,N-dimethylformamide (DMF) were placed in a reaction vessel, and heated and stirred. After the internal temperature of the reaction container reached 80° C., a solution obtained by dissolving 19.13 g (0.22 mol) of methacrylic acid in 50 ml of DMF was dropped over 30 minutes. Maintaining this temperature, the reaction was carried out for 1 hour. Next, a solution obtained by dissolving 58.27 g of 2CM-DMBP-BPFZ obtained in Example 1 in 500 ml of DMF was added dropwise over 30 minutes. After completion of the dropping, stirring was further continued at 80° C. for 3 hours. After 3 hours, it was cooled to room temperature, and the precipitated solid was separated by filtration. Then, 2000 ml of toluene was added to the reaction solution. Then, the reaction solution was washed with water four times, and the oily phase was dried over magnesium sulfate and filtered. The obtained organic phase was reprecipitated with a ...

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Abstract

The invention provides a curable resin composition with high dielectric property (low dielectric constant. low dielectric loss tangent) and having condensates with high glass-transition temperature and flame resistance, bis (methyl) acryloyl tail end benzyl ether compound and aromatic bis-halogenated methyl compound as an intermediate. Aromatic bis-halogenated methyl compounds are reacted with bisphenol fluorene compounds, and the obtained aromatic bis-halogenated methyl compounds with halogenated methyl groups at two tail ends are employed as intermediates. Next, the intermediates are reacted with compounds of (methyl) acrylic acid series such as (methyl) acrylic acid, (methyl) potassium acrylate and the like, thus the halogenated methyl groups at two tail ends are changed into (methyl) acryloyl groups and bis (methyl) acryloyl tail end benzyl ether compounds are obtained. In addition, the invention relates to a curable resin composition comprising bis (methyl) acryloyl tail end benzyl ether compounds and polymerization initiators (B).

Description

technical field [0001] The present invention relates to a diether compound having a fluorene skeleton, a bis(meth)acrylate compound, a method for producing the same, an aromatic bishalogenated methyl compound as an intermediate thereof, and a resin composition containing the same. Background technique [0002] In recent years, with the development of miniaturization of electronic equipment, in order to carry out high integration of electronic components and multi-layer development of printed wiring, the so-called combination (buldup) of alternately forming and stacking insulating layers and conductive layers has been widely used. Construction method. In addition, the resin insulating material used therein is required to have a low dielectric constant in order to increase the speed of information processing and reduce the heat loss caused by the increase in frequency of signals. [0003] JP-A No. 6-1938 and the like are known as photo- or thermosetting resin compositions, bu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/225C07C69/54C07C67/10C08F222/26C09D4/02G02B1/04
CPCC07C43/225C07C67/11C07C69/54C07C2603/18C09D4/00G02B1/041C07C69/602C08G65/005C08J5/18
Inventor 川边正直
Owner NIPPON STEEL CHEMICALL &MATERIAL CO LTD
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