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Biphenylene-bridged phenol novolak resins and use thereof

A novolac resin and biphenyl technology, which is applied in the field of biphenylene cross-linked novolac resins, can solve the problems of slow curing speed, long curing time, adverse effects on productivity or production cost, etc., and achieves low water absorption. sex, improve productivity

Active Publication Date: 2011-02-09
UBE IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the biphenylene cross-linked novolac resin of the prior art has a problem of slow curing speed compared with the novolak resin.
If the curing speed is slow, the curing time will become longer, which will have an adverse effect on productivity and production cost when used in various applications

Method used

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  • Biphenylene-bridged phenol novolak resins and use thereof
  • Biphenylene-bridged phenol novolak resins and use thereof
  • Biphenylene-bridged phenol novolak resins and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] 169.2 parts (1.8 moles) of phenol, 22 parts (0.2 moles) of catechol, 112.6 parts (0.465 moles) of 4,4'-bismethoxymethylbiphenyl and 0.10 parts of 50% by weight sulfuric acid. Under nitrogen flow, the reaction was carried out at an internal temperature of 110°C to 140°C for 3 hours, then at 165°C for 3 hours, and cooled to 95°C. After cooling, 250 parts of pure water of 90° C. or higher were added and washed with water. Then, the internal temperature was raised to 160° C., and unreacted components were removed by decompression-steam treatment. A resin having a softening point of 65.3°C was obtained. As analyzed by gel permeation chromatography (hereinafter referred to as GPC), the polystyrene-equivalent number average molecular weight (Mn) was 773, and the weight average molecular weight (Mw) was 920.

Embodiment 2

[0055] 169.2 parts (1.8 moles) of phenol, 22 parts (0.2 moles) of resorcinol, 112.6 parts (0.465 moles) of 4,4'-bismethoxymethylbiphenyl and 0.10 parts of 50% by weight sulfuric acid. Under nitrogen flow, the reaction was carried out at an internal temperature of 110°C to 140°C for 3 hours, then at 165°C for 3 hours, and cooled to 95°C. After cooling, 250 parts of pure water of 90° C. or higher were thrown in and washed with water. Then, the internal temperature was raised to 160° C., and unreacted components were removed by decompression-steam treatment. A resin having a softening point of 78.8°C was obtained. By GPC analysis, the number average molecular weight (Mn) in terms of polystyrene was 858, and the weight average molecular weight (Mw) was 1116.

Embodiment 3

[0057] 169.2 parts (1.8 moles) of phenol, 22 parts (0.2 moles) of hydroquinone, 112.6 parts (0.465 moles) of 4,4'-bismethoxymethylbiphenyl and 0.10 parts of 50% by weight sulfuric acid. Under nitrogen flow, the reaction was carried out at an internal temperature of 110°C to 140°C for 3 hours, then at 165°C for 3 hours, and cooled to 95°C. After cooling, 250 parts of pure water of 90° C. or higher were thrown in and washed with water. Then, the internal temperature was raised to 160° C., and unreacted components were removed by decompression-steam treatment. A resin having a softening point of 70.6°C was obtained. By GPC analysis, the number average molecular weight (Mn) was 778 and the weight average molecular weight (Mw) was 930 in terms of polystyrene.

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Abstract

Biphenylene-bridged phenol novolak resins represented by the general formula (2), which consist of products of reaction of a biphenyl compound represented by the general formula (1) with a phenol mixture containing at least one dihydric phenol: (1) (wherein X is alkoxy having 1 to 4 carbon atoms or halogeno) (2) (wherein R<1>, R<2> and R<3> are each independently substituted or unsubstituted, linear or branched alkyl having 1 to 10 carbon atoms or substituted or unsubstituted aryl, with the proviso that R<1>'s, R<2>'s, and R<3>'s may be each the same or different from each other; p1 and p3 are each an integer of 1 to 4; p2 is an integer of 1 to 3; n is an integer of 0 to 15; m1, m2 and m3 are each an integer of 1 or 2 and m2's may be the same or different from each other, with the provisothat a case wherein all of m1, m2 and m3 are 1 and a case wherein all of m1, m2 and m3 are 2 are excepted).

Description

technical field [0001] The present invention relates to a biphenylene crosslinked linear type obtained by reacting bis(alkoxymethyl)biphenyl or bis(halogenated methyl)biphenyl with a phenolic mixture containing at least one dihydric phenol Phenolic Resin. The novolac resin of the present invention can be used not only as a curing agent for epoxy resins, but also as a raw material for epoxidized novolac resins, isocyanated polyurethane resins, triazine resins, and polyester resins. Background technique [0002] Conventionally, novolac resins obtained by reacting bis(alkoxymethyl)biphenyl or bis(halogenated methyl)biphenyl with phenols have been disclosed using bis(methoxymethyl)biphenyl compounds. A biphenylene crosslinked novolac resin of each isomer or a mixture thereof (Patent Document 1). [0003] When novolak resins having these biphenylene crosslinked structures are used as curing agents for epoxy resins, excellent low water absorption (low hygroscopicity), flame reta...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/10C08G59/62
CPCC08L61/06C08G59/621C08L63/00C08L2666/22C08G59/62C08G61/10
Inventor 三谷纪幸河野真希
Owner UBE IND LTD
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