2-(2-ethoxyethoxy)ethyl acetate

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reflux condenser, a thermometer, a bleed tube, and a stirrer were set to a four-necked flask. In order to prepare a reaction solution, 203 parts by mass of cresol novolac epoxy resin “YDCN-700-5” (available from NIPPON STEEL CHEMICAL CO., LTD., epoxy equivalent weight: 203), 103 parts by mass of diethylene glycol monoethyl ether acetate, 0.2 parts by mass of hydroquinone, 72.7 parts by mass of acrylic acid, and 0.6 parts by mass of dimethyl benzyl amine were added to the four-necked flask. The reaction solution was heated at 110° C. for 10 hours to cause the addition reaction. Subsequently, into thus-obtained solution in the four-necked flask, 60.8 parts by mass of tetrahydrophthalic acid anhydride and 78.9 parts by mass of diethylene glycol monoethyl ether acetate were added, and then thus-obtained solution was heated at 81° C. for 3 hours to react them. Consequently, a 65 mass % solution (carboxyl group containing resin solution C-3) of resin containing a carboxyl group was obtained. A reflux condenser, a thermometer, a bleed tube, and a stirrer were set to a four-necked flask the addition reaction

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reflux condenser, a thermometer, a bleed tube, and a stirrer were set to a four-necked flask. In order to prepare a reaction solution, 212 parts by mass of cresol novolac epoxy resin (N-695 (item number) available from DIC Corporation, epoxy equivalent weight: 212), 221 parts by mass of diethylene glycol monoethyl ether acetate, 0.2 parts by mass of hydroquinone, 300 parts by mass of ω-carboxy-polycaprolactone monoacrylate (Aronix M-5300 (trade name) available from TOAGOSEI CO., LTD., the number average molecular weight: 290), and 3 parts by mass of triphenyl phosphine were added to the four-necked flask. The reaction solution was heated at 115° C. for 12 hours with air bubbled therein to cause the addition reaction. Subsequently, into thus-obtained solution in the four-necked flask, 76 parts by mass of tetrahydrophthalic acid anhydride and 97.3 parts by mass of diethylene glycol monoethyl ether acetate were added, and then thus-obtained solution was heated at 110° C. for 5 hours to react them. Consequently, a 65 mass % solution (carboxyl group containing resin solution C-2) of resin containing a carboxyl group was obtained. A reflux condenser, a thermometer, a bleed tube, and a stirrer were set to a four-necked flask bubbled the addition reaction

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reflux condenser, a thermometer, a bleed tube, and a stirrer were set to a four-necked flask. In order to prepare a reaction solution, 919 parts by mass of bisphenol A epoxy resin (jER1004 (item number) available from Mitsubishi Chemical Corporation, epoxy equivalent weight: 919), 470 parts by mass of diethylene glycol monoethyl ether acetate, 0.2 parts by mass of hydroquinone, 72 parts by weight of acrylic acid, and 3 parts by mass of triphenyl phosphine were added to the four-necked flask. The reaction solution was heated at 115° C. for 12 hours with air bubbled therein to cause the addition reaction. Subsequently, into thus-obtained solution in the four-necked flask, 249 parts by mass of succinic acid anhydride and 195 parts by mass of diethylene glycol monoethyl ether acetate were added, and then thus-obtained solution was heated at 110° C. for 5 hours to react them. Consequently, a 65 mass % solution (carboxyl group containing resin solution C-1) of resin containing a carboxyl group was obtained. A reflux condenser, a thermometer, a bleed tube, and a stirrer were set to a four-necked flask were added to the four-necked flask bubbled the addition reaction

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reflux condenser, a thermometer, a bleed tube, and a stirrer were set to a four-necked flask. In order to prepare a reaction solution, 919 parts by mass of bisphenol A epoxy resin (jER1004 (item number) available from Mitsubishi Chemical Corporation, epoxy equivalent weight: 919), 470 parts by mass of diethylene glycol monoethyl ether acetate, 0.2 parts by mass of hydroquinone, 300 parts by mass of ω-carboxy-polycaprolactone (n≈2) monoacrylate (Aronix M-5300 (trade name) available from TOAGOSEI CO., LTD., the number average molecular weight: 290), and 3 parts by mass of triphenyl phosphine were added to the four-necked flask. The reaction solution was heated at 115° C. for 12 hours with air bubbled therein to cause the addition reaction. Subsequently, into thus-obtained solution in the four-necked flask, 249 parts by mass of succinic acid anhydride and 322 parts by mass of diethylene glycol monoethyl ether acetate were added, and then thus-obtained solution was heated at 110° C. for 5 hours to react them. Consequently, a 65 mass % solution (carboxyl group containing resin solution A-1) of resin containing a carboxyl group was obtained, the resin having the number average molecular weight of about 3700. A reflux condenser, a thermometer, a bleed tube, and a stirrer were set to a four-necked flask bubbled the addition reaction

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reflux condenser, a thermometer, a bleed tube, and a stirrer were set to a four-necked flask. In order to prepare a reaction solution, 919 parts by mass of bisphenol A epoxy resin (jER1004 (item number) available from Mitsubishi Chemical Corporation, epoxy equivalent weight: 919), 470 parts by mass of diethylene glycol monoethyl ether acetate, 0.2 parts by mass of hydroquinone, 300 parts by mass of ω-carboxy-polycaprolactone (n≈2) monoacrylate (Aronix M-5300 (trade name) available from TOAGOSEI CO., LTD., the number average molecular weight: 290), and 3 parts by mass of triphenyl phosphine were added to the four-necked flask. The reaction solution was heated at 115° C. for 12 hours with air bubbled therein to cause the addition reaction. Subsequently, into thus-obtained solution in the four-necked flask, 249 parts by mass of succinic acid anhydride and 322 parts by mass of diethylene glycol monoethyl ether acetate were added, and then thus-obtained solution was heated at 110° C. for 5 hours to react them. Consequently, a 65 mass % solution (carboxyl group containing resin solution A-1) of resin containing a carboxyl group was obtained, the resin having the number average molecular weight of about 3700. A reflux condenser, a thermometer, a bleed tube, and a stirrer were set to a four-necked flask bubbled the addition reaction

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reflux condenser, a thermometer, a bleed tube, and a stirrer were set to a four-necked flask. In order to prepare a reaction solution, 919 parts by mass of bisphenol A epoxy resin (jER1004 (item number) available from Mitsubishi Chemical Corporation, epoxy equivalent weight: 919), 470 parts by mass of diethylene glycol monoethyl ether acetate, 0.2 parts by mass of hydroquinone, 300 parts by mass of ω-carboxy-polycaprolactone (n≈2) monoacrylate (Aronix M-5300 (trade name) available from TOAGOSEI CO., LTD., the number average molecular weight: 290), and 3 parts by mass of triphenyl phosphine were added to the four-necked flask. The reaction solution was heated at 115° C. for 12 hours with air bubbled therein to cause the addition reaction. Subsequently, into thus-obtained solution in the four-necked flask, 249 parts by mass of succinic acid anhydride and 322 parts by mass of diethylene glycol monoethyl ether acetate were added, and then thus-obtained solution was heated at 110° C. for 5 hours to react them. Consequently, a 65 mass % solution (carboxyl group containing resin solution A-1) of resin containing a carboxyl group was obtained, the resin having the number average molecular weight of about 3700. A reflux condenser, a thermometer, a bleed tube, and a stirrer were set to a four-necked flask bubbled the addition reaction