Desmodur w

Example 2

In a 3-necked flask equipped with an overhead stirrer, thermocouple, and a vacuum adapter, 1210 g (9.15 equivalents) of 4,4′-dicyclohexylmethanediisocyanate (H12MDI, available from Bayer as Desmodur W) was charged into the reactor and stirred at ambient temperature. 3000 g (6.03 equivalents) of a polycaprolactone diol having an OH number of 112 mg KOH/g and a number average molecular weight of about 1000 g/mole (available from Dow Chemical as Tone™ 2221) was preheated in an oven to 80° C. and added to the reactor. The mixture was allowed to stir for about 15 minutes, before adding 12 g of dibutyltin dilaurate catalyst (available from Air Products as T-12). The reaction flask was evacuated (<0.1 mm HG) and held at 90° C. for 6 hours. An aliquot of the prepolymer was withdrawn and titrated for isocyanate content using standard n-butyl amine titration. The isocyanate content was found to be 3.07% (theory; 3.10%). The polyurethane prepolymer had a molecular weight of 6,000 measured by Viscotek GPC.

Example 4

In a 3-necked flask equipped with an overhead stirrer, thermocouple, and a vacuum adapter, 335 g (2.55 equivalents) of 4,4′-dicyclohexylmethanediisocyanate (available from Bayer as Desmodur W) was charged into the reactor and stirred at ambient temperature. 664.8 g (1.33 equivalents) of a polycaprolactone diol having an OH number of 112 mg KOH/g (available from Dow Chemical as Tone™ 2221) was preheated in an oven to 80° C. and added to the reactor. The mixture was allowed to stir for about 15 minutes, before adding 2.5 g of dibutyltin dilaurate catalyst (available from Air Products as T-12). The reaction flask was evacuated (<0.1 mm HG) and held at 80° C. for 3 hours and cooled down. The resulted product was titrated and resulted in NCO content of 5.10%.

Example 4

122.4 g of G1-1000 (hydrogenated polybutadiene polyol, manufactured by Nippon Soda Co., Ltd.), 13.6 g of TCD Alcohol DM (tricyclodecane dimethanol, manufactured by OXEA GmBH), 44.2 g of DESMODUR W (methylene bis(4-cyclohexylisocyanate), manufactured by Bayer AG), 92.9 g of VISCOAT #155 (cyclohexyl acrylate, manufactured by Osaka Organic Chemical Industry Ltd.), 92.9 g of IBXA (isobornyl acrylate, manufactured by Osaka Organic Chemical Industry Ltd.), 0.19 g of hydroquinone monomethyl ether (manufactured by Wako Pure Chemical Industries, Ltd.), and 0.04 g of KS-1260 (dibutyltin dilaurate, manufactured by Sakai Chemical Industry Co., Ltd.) were added to a reaction container provided with a stirrer, a thermometer, and a condenser, and the solution was heated to 80° C. to 85° C. using an oil bath while being stirred. Then, the reaction was continued while the solution was stirred for 2.5 hours. Thereafter, 5.6 g of HEA (2-hydroxyethyl acrylate, manufactured by Osaka Organic Chemical Industry Ltd.) was added thereto, the reaction was continued while the solution was stirred for 2.5 hours, thereby obtaining a cyclohexyl acrylate/isobornyl acrylate solution (50 wt %) of polyurethane acrylate (a2-1). The theoretical amount of the hydroxy group in the polyurethane acrylate (a2-1) acquired from the raw materials is 0 mmol/g (solid content).

Example 3

142.5 g of Priplast 3197 (hydrogenated dimer acid polyester polyol, manufactured by Croda Corporation), 13.6 g of TCD Alcohol DM (tricyclodecane dimethanol, manufactured by OXEA GmBH), 31.4 g of DESMODUR W (methylene bis(4-cyclohexylisocyanate), manufactured by Bayer AG), 93.8 g of VISCOAT #155 (cyclohexyl acrylate, manufactured by Osaka Organic Chemical Industry Ltd.), 93.8 g of IBXA (isobornyl acrylate, manufactured by Osaka Organic Chemical Industry Ltd.), 0.19 g of hydroquinone monomethyl ether (manufactured by Wako Pure Chemical Industries, Ltd.), and 0.04 g of KS-1260 (dibutyltin dilaurate, manufactured by Sakai Chemical Industry Co., Ltd.) were added to a reaction container provided with a stirrer, a thermometer, and a condenser, and the solution was heated to 80° C. to 85° C. using an oil bath while being stirred. Thereafter, the reaction was continued while the solution was stirred for 2.5 hours, thereby obtaining a cyclohexyl acrylate/isobornyl acrylate solution (50 wt %) of polyurethane polyol (a1-3). The theoretical amount of the hydroxy group in the polyurethane polyol (a1-3) acquired from the raw materials is 0.261 mmol/g (solid content).

Example 4

In a 3-necked flask equipped with an overhead stirrer, thermocouple, and a vacuum adapter, 335 g (2.55 equivalents) of 4,4′-dicyclohexylmethanediisocyanate (available from Bayer as Desmodur W) was charged into the reactor and stirred at ambient temperature. 664.8 g (1.33 equivalents) of a polycaprolactone diol having an OH number of 112 mg KOH/g (available from Dow Chemical as Tone™ 2221) was preheated in an oven to 80° C. and added to the reactor. The mixture was allowed to stir for about 15 minutes, before adding 2.5 g of dibutyltin dilaurate catalyst (available from Air Products as T-12). The reaction flask was evacuated (<0.1 mm HG) and held at 80° C. for 3 hours and cooled down. The resulted product was titrated and resulted in NCO content of 5.10%.

Example 4

In a 3-necked flask equipped with an overhead stirrer, thermocouple, and a vacuum adapter, 335 g (2.55 equivalents) of 4,4′-dicyclohexylmethanediisocyanate (available from Bayer as Desmodur W) was charged into the reactor and stirred at ambient temperature. 664.8 g (1.33 equivalents) of a polycaprolactone diol having an OH number of 112 mg KOH/g (available from Dow Chemical as Tone™ 2221) was preheated in an oven to 80° C. and added to the reactor. The mixture was allowed to stir for about 15 minutes, before adding 2.5 g of dibutyltin dilaurate catalyst (available from Air Products as T-12). The reaction flask was evacuated (<0.1 mm HG) and held at 80° C. for 3 hours and cooled down. The resulted product was titrated and resulted in NCO content of 5.10%.

Example 2

138.7 g of GI-1000 (hydrogenated polybutadiene polyol, manufactured by Nippon Soda Co., Ltd.), 15.4 g of TCD Alcohol DM (tricyclodecane dimethanol, manufactured by OXEA GmBH), 36.5 g of DESMODUR W (methylene bis(4-cyclohexylisocyanate), manufactured by Bayer AG), 95.3 g of VISCOAT #155 (cyclohexyl acrylate, manufactured by Osaka Organic Chemical Industry Ltd.), 95.3 g of IBXA (isobornyl acrylate, manufactured by Osaka Organic Chemical Industry Ltd.), 0.19 g of hydroquinone monomethyl ether (manufactured by Wako Pure Chemical Industries, Ltd.), and 0.04 g of KS-1260 (dibutyltin dilaurate, manufactured by Sakai Chemical Industry Co., Ltd.) were added to a reaction container provided with a stirrer, a thermometer, and a condenser, and the solution was heated to 80° C. to 85° C. using an oil bath while being stirred. Thereafter, the reaction was continued while the solution was stirred for 2.5 hours, thereby obtaining a cyclohexyl acrylate/isobornyl acrylate solution (50 wt %) of polyurethane polyol (a1-2). The theoretical amount of the hydroxy group in the polyurethane polyol (a1-2) acquired from the raw materials is 0.258 mmol/g (solid content).