[4-(hydroxymethyl)cyclohexyl]methyl prop-2-enoate

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Air was introduced into a reaction vessel equipped with a stirrer, a thermometer, a cooling tube, and an air-inlet tube. Subsequently, 196.80 g (0.39 mol) of polycarbonate diol (manufactured by Daicel Chemical Industries, Ltd., product name PLACCEL CD205PL, number-average molecular weight: 500), 58.30 g (0.39 mol) of 2,2-bis(hydroxymethyl)butanate, 37.60 g (0.35 mol) of diethylene glycol, 148.10 g (0.75 mol) of 1,4-cyclohexanedimethanol monoacrylate, 0.55 g of p-methoxyphenol, 0.55 g of dibutyltin dilaurate, and 110.20 g of methyl ethyl ketone were added into the reaction vessel and heated to 65° C. under stirring uniformly in an air stream. Into a dripping vessel, 305.90 g (1.46 mol) of trimethyl hexamethylene diisocyanate was added. Then, trimethyl hexamethylene diisocyanate was dropped from the dripping vessel into the reaction vessel over 3 hours under stirring uniformly at 65° C. After the dropping, the dripping vessel was washed by use of 76.50 g of methyl ethyl ketone. After the dripping vessel was washed, a solution in the dripping vessel was charged as it is into the reaction vessel, and a resultant mixture was kept stirred uniformly for 2 hours at that temperature, Then, the resultant mixture was heated to 75° C. and stirred uniformly for 5 hours. Next, 9.30 g of methanol was added into the reaction vessel and was stirred uniformly at 60° C. for 30 minutes. Subsequently, 56.40 g of methyl ethyl ketone was added thereto to give a transparent resin solution. In this manner, a resin solution having a urethane bond and a methacryloyl group in its molecule was prepared. The resin solution thus prepared had a solid content concentration of 75% and a weight-average molecular weight of 14,800. Note that the solid content concentration and the weight-average molecular weight were measured in the same manner as in Synthesis Example 1. Then, (i) 66.7 g (solid content 50 g) of the resin solution thus prepared, (ii) 30 g of 2,2′-bis(4-methacryloxypentaethoxy phenyl)propane which served as a radical polymerizable compound, (iii) 162.5 g (solid content 65 g) of a resin solution which served as a binder resin and was obtained by copolymerizing methacrylate, methyl methacrylate, and butyl acrylate in a weight ratio of 22:71:7 (a solution which had a weight-average molecular weight of 80,000 and a solid content acid value of 143 mgKOH/g and was obtained by dissolving methacrylate, methyl methacrylate, and butyl acrylate in a solution of methyl cellsolve/toluene=6/4 (weight ratio) so as to have a solid content concentration of 40%), (iv) 3.5 g of benzophenone and 0.1 g of N,N′-tetraethyl-4,4′-diaminobenzophenone, both of which served as a photo-polymerization initiator, (v) 20 g (solid content 15 g) of a 75% methyl ethyl ketone solution of a block isocyanate compound which served as a thermosetting resin and was obtained by reacting an isocyanurate type hexamethylene diisocyanate isocyanate compound and methylethyl ketone oxime which served as a blocking agent, (vi) 40 g of CR-747 (a name of a product manufactured by DAIHACHI CHEMICAL INDUSTRY CO., LTD.) which served as a phosphorous flame retardant, (vii) 85 g of acetone which served as a diluent were blended, stirred, and then dispersed by use of a triple-roll mill to prepare a photosensitive resin composition. Physical properties of the photosensitive resin composition thus prepared was evaluated in the same manner as in Example 1. Evaluation results are shown in Table 2. Note that the photosensitive resin composition does not contain the component (B). Air was introduced into a reaction vessel equipped with a stirrer under stirring uniformly at 65° C After the dropping, the dripping vessel was washed by use of 76.50 g of methyl ethyl ketone After the dripping vessel was washed a solution in the dripping vessel was charged as it a resultant mixture was kept stirred uniformly for 2 hours at that temperature the resultant mixture was heated to 75° C. stirred uniformly for 5 hours Next, 9.30 g of methanol was added into the reaction vessel was stirred uniformly at 60° C. for 30 minutes Subsequently, 56.40 g of methyl ethyl ketone was added to give a transparent resin solution a methacryloyl group in its molecule was prepared The resin solution thus prepared Note that the solid content concentration the weight-average molecular weight were measured in the same manner as in Synthesis Example 1

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Air was introduced into a reaction vessel equipped with a stirrer, a thermometer, a cooling tube, and an air-inlet tube. Subsequently, 196.80 g (0.39 mol) of polycarbonate diol (manufactured by Daicel Chemical Industries, Ltd., product name PLACCEL CD205PL, number-average molecular weight: 500), 58.30 g (0.39 mol) of 2,2-bis(hydroxymethyl)butanate, 37.60 g (0.35 mol) of diethylene glycol, 148.10 g (0.75 mol) of 1,4-cyclohexanedimethanol monoacrylate, 0.55 g of p-methoxyphenol, 0.55 g of dibutyltin dilaurate, and 110.20 g of methyl ethyl ketone were added into the reaction vessel and heated to 65° C. under stirring uniformly in an air stream. Into a dripping vessel, 305.90 g (1.46 mol) of trimethyl hexamethylene diisocyanate was added. Then, trimethyl hexamethylene diisocyanate was dropped from the dripping vessel into the reaction vessel over 3 hours under stirring uniformly at 65° C. After the dropping, the dripping vessel was washed by use of 76.50 g of methyl ethyl ketone. After the dripping vessel was washed, a solution in the dripping vessel was charged as it is into the reaction vessel, and a resultant mixture was kept stirred uniformly for 2 hours at that temperature, Then, the resultant mixture was heated to 75° C. and stirred uniformly for 5 hours. Next, 9.30 g of methanol was added into the reaction vessel and was stirred uniformly at 60° C. for 30 minutes. Subsequently, 56.40 g of methyl ethyl ketone was added thereto to give a transparent resin solution. In this manner, a resin solution having a urethane bond and a methacryloyl group in its molecule was prepared. The resin solution thus prepared had a solid content concentration of 75% and a weight-average molecular weight of 14,800. Note that the solid content concentration and the weight-average molecular weight were measured in the same manner as in Synthesis Example 1. Then, (i) 66.7 g (solid content 50 g) of the resin solution thus prepared, (ii) 30 g of 2,2′-bis(4-methacryloxypentaethoxy phenyl)propane which served as a radical polymerizable compound, (iii) 162.5 g (solid content 65 g) of a resin solution which served as a binder resin and was obtained by copolymerizing methacrylate, methyl methacrylate, and butyl acrylate in a weight ratio of 22:71:7 (a solution which had a weight-average molecular weight of 80,000 and a solid content acid value of 143 mgKOH/g and was obtained by dissolving methacrylate, methyl methacrylate, and butyl acrylate in a solution of methyl cellsolve/toluene=6/4 (weight ratio) so as to have a solid content concentration of 40%), (iv) 3.5 g of benzophenone and 0.1 g of N,N′-tetraethyl-4,4′-diaminobenzophenone, both of which served as a photo-polymerization initiator, (v) 20 g (solid content 15 g) of a 75% methyl ethyl ketone solution of a block isocyanate compound which served as a thermosetting resin and was obtained by reacting an isocyanurate type hexamethylene diisocyanate isocyanate compound and methylethyl ketone oxime which served as a blocking agent, (vi) 40 g of CR-747 (a name of a product manufactured by DAIHACHI CHEMICAL INDUSTRY CO., LTD.) which served as a phosphorous flame retardant, (vii) 85 g of acetone which served as a diluent were blended, stirred, and then dispersed by use of a triple-roll mill to prepare a photosensitive resin composition. Physical properties of the photosensitive resin composition thus prepared was evaluated in the same manner as in Example 1. Evaluation results are shown in Table 2. Note that the photosensitive resin composition does not contain the component (B). Air was introduced into a reaction vessel equipped with a stirrer under stirring uniformly at 65° C After the dropping, the dripping vessel was washed by use of 76.50 g of methyl ethyl ketone After the dripping vessel was washed a solution in the dripping vessel was charged as it a resultant mixture was kept stirred uniformly for 2 hours at that temperature the resultant mixture was heated to 75° C. stirred uniformly for 5 hours Next, 9.30 g of methanol was added into the reaction vessel was stirred uniformly at 60° C. for 30 minutes Subsequently, 56.40 g of methyl ethyl ketone was added to give a transparent resin solution a methacryloyl group in its molecule was prepared The resin solution thus prepared Note that the solid content concentration the weight-average molecular weight were measured in the same manner as in Synthesis Example 1