Phosphorus-containing phenolic resin and the producing method, phenolic resin composition and cured product thereof
A phenolic resin and a technology for a manufacturing method, which are applied in the field of curable resin compositions and cured products thereof, can solve the problem of low adhesiveness, poor adhesion and heat resistance reliability of epoxy resin cured products, and difficulty in removing completely Solvents, etc.
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Embodiment 1
[0070] Bisphenol F type epoxy resin (Nippon Steel Chemical Co., Ltd. product name YDF-170, epoxy The equivalent is 168.9g / eq.) 84.5 parts, put in 10-(2,5-dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide (trade name HCA manufactured by Sanko Co., Ltd. -HQ, melting point of 256°C, phosphorus content of 9.6%, hydroxyl equivalent of 162g / eq.) 121.7 parts and propylene glycol monomethyl ether acetate (PMA) 59 parts. At this time, the functional group ratio of HCA-HQ to YDF-170 was 1.5. Triphenylphosphine was added thereto as a catalyst, and the reaction was performed at 160° C. for 2 hours. The epoxy equivalent after the first-stage reaction was completed was 4849 g / eq., and the reaction rate of epoxy groups was 92%. 28.5 parts of bisphenol A (manufactured by Nippon Steel Chemical Co., Ltd., hydroxyl equivalent: 114 g / eq.) was added thereto, and the reaction was further performed at 160° C. for 3 hours. After the reaction, it was diluted with propylene glycol monomethy...
Embodiment 2
[0072] The reaction of the first stage was performed by the method similar to Example 1 except having made 105.5 parts of HCA-HQ of Example 1, and PMA 83 parts. At this time, the functional group ratio of HCA-HQ to YDF-170 was 1.3, the epoxy equivalent after the first stage reaction was 2943g / eq., and the reaction rate of epoxy groups was 87%. Add 141.5 parts of trihydroxyphenylmethane type novolac resin (trade name RESITOP TPM-100 manufactured by Qunyei Chemical Industry Co., Ltd., hydroxyl equivalent weight is 97.5g / eq.) to it, and react in the same manner as in Example 1. After the reaction ends, Dilute with PGM. The obtained phosphorus-containing phenolic resin was red and transparent, with a non-volatile content of 70%, a phosphorus content of 3.1% in solids, a hydroxyl equivalent of 207g / eq., and a residual HCA-HQ content of 10.6%. Table 1 shows the input ratio, the reaction conditions in the first stage, and the properties of the resin, and Table 5 shows the solubility...
Embodiment 3
[0074] In the same experimental device as in Example 1, add 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (trade name HCA manufactured by Sanko Co., Ltd., phosphorus content is 14.2%) 54.9 and 39.4 parts of 1,4-naphthoquinone (manufactured by Kawasaki Chemical Industry Co., Ltd. with a moisture content of 3.4%) and 120 parts of toluene. After stirring at 75°C for 30 minutes, the reaction was carried out at 110°C for 90 Minutes, synthesized HCA-NQ. At this time, the molar ratio of HCA to 1,4-naphthoquinone was 0.98 mol of 1,4-naphthoquinone with respect to 1.00 mol of HCA. Then reflux to remove toluene, add 84.5 parts of YDF-170, 72 parts of PMA. At this time, the functional group ratio of HCA-NQ to YDF-170 was 1.0. Triphenylphosphine was added thereto as a catalyst, and the first-stage reaction was carried out in the same manner as in Example 1. The epoxy equivalent after the first-stage reaction was completed was 604 g / eq., and the reaction rate of epoxy groups was 39...
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