Acrylic Acid → Bisphenol A

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반응 단계

1,5-dihydroxynaphthalene (phenolic hydroxyl group equivalent weight: 80 g/eq.) (224 parts) and bisphenol A-type epoxy resin (EPICOAT 828, manufactured by Japan Epoxy Resin Co., Ltd., epoxy-equivalent weight: 189 g/eq.) (1075 parts) were pre-reacted in a reaction container having a gas-injection tube, stirrer, cooling tube, thermometer, and funnel for continuously dropping an alkaline metal hydroxide solution. The mixture was stirred at 110 degrees Celsius under nitrogen atmosphere to dissolve it. Subsequently, triphenylphosphine (0.65 parts) was added, and the temperature in the reaction container was increased to 150 degrees Celsius. With the temperature maintained at 150 degrees Celsius, the mixture was subjected to reaction for approximately 90 minutes. Thus, an epoxy resin (a) having an epoxy-equivalent weight of 452 g/eq. was obtained. Next, the temperature in the flask was lowered to 40 degrees Celsius, after which epichlorohydrin (1920 parts), toluene (1690 parts) and tetramethylammonium bromide (70 parts) were added, and the mixture was heated to and maintained at 45 degrees Celsius while being stirred. Subsequently, a 48 wt % aqueous solution of sodium hydroxide (364 parts) was continuously dropped into the mixture for 60 minutes, and the mixture was further subjected to a 6-hour reaction. After the reaction was completed, most of the excessive epichlorohydrin and toluene was collected by vacuum distillation, after which the reaction product containing a by-product salt and toluene was dissolved in methyl isobutyl ketone and then washed with water. After an organic solvent layer was separated from water layer, methyl isobutyl ketone was removed from the organic solvent layer by vacuum distillation. Thus, a polynuclear epoxy resin (b) having an epoxy-equivalent weight of 277 g/eq. was obtained. A calculation based on the epoxy-equivalent weight shows that approximately 1.59 alcoholic hydroxide groups out of 1.98 alcoholic hydroxide groups on the epoxy resin (a) was epoxidized in the obtained polynuclear epoxy resin (b). Accordingly, the rate of epoxidation of the alcoholic hydroxide groups was approximately 80%. Next, the polynuclear epoxy resin (b) (277 parts) was put in a flask having a stirrer, cooling tube and thermometer, after which propylene glycol monomethyl ether acetate (290 parts) was added, and the mixture was dissolved by heat. Then, methyl hydroquinone (0.46 parts) and triphenylphosphine (1.38 parts) were added. The mixture was heated to 95-105 degrees Celsius and subjected to a 4-hour reaction, with acrylic acid (72 parts) gradually dropped into it and air continuously blown into it. The reaction product was cooled to 80-90 degrees Celsius, after which tetrahydrophthalic acid anhydride (129 parts) was added, and the mixture was subjected to a 5-hour reaction. As a result, a solution with a nonvolatile content of 62% was obtained. The obtained carboxyl resin had an acid value of 100 mgKOH/g. This solution is hereinafter referred to as “B-4.”

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