Trigonox 121

Example 29

[Figure (not displayed)]

An autoclave reactor was loaded with t-butanol (242.00 g). A monomer solution of N-vinyl-2-pyrrolidone (36.00 g), methacrylic acid (32.40 g), di-octyl maleate (36.00 g), methyl methacrylate (61.20 g), hydroxypropyl methacrylate (9.00 g) and t-butylaminoethyl methacrylate (5.40 g) was prepared and charged into a syringe pump. Then, 25.0% of the monomer solution was charged into the reactor. The mixture in the reactor was de-aerated and heated to 85° C. under nitrogen with mechanical stirring at 200 rpm. At t=0, t-amyl peroxy-2-ethylhexanoate initiator (Trigonox® 121, Akzo Nobel) (0.28 g) was charged into the reactor to initiate the polymerization. Then, the remaining monomer solution in the syringe pump was emptied into the reactor at a constant rate over the next 3 hours. Additional shots of the initiator were added at t=1, 2, 3 hour (0.28 g each). The reaction temperature then was raised to 91° C. at t=4 hour and additional initiator was charged at t=5, 8 and 10 hour (0.75 g each). After the last initiator addition, stirring continued at 91° C. for 4 hours. Then, DI water (30.00 g) was added into the reactor and stirred for 30 min. After cooling, a viscous copolymer solution was discharged into a glass bottle.

The glass transition temperature (T_g) was measured at 10° C./min and found to be 179° C.

Example 35

[Figure (not displayed)]

An autoclave reactor was loaded with t-butanol (148.50 g). A monomer solution of N-vinyl-2-pyrrolidone (32.40 g), acrylic acid (30.60 g), di-isobutyl fumarate (39.60 g), methyl methacrylate (63.00 g), hydroxypropyl methacrylate (9.00 g) and t-butylaminoethyl methacrylate (5.40 g) was prepared and charged into a syringe pump. Then, 25.0% of the monomer solution was charged into the reactor. The mixture in the reactor was de-aerated and heated to 85° C. under nitrogen with mechanical stirring at 200 rpm. At t=0, t-amyl peroxy-2-ethylhexanoate initiator (Trigonox® 121, Akzo Nobel) (0.28 g) was charged into the reactor to initiate the polymerization. Then, the remaining monomer solution in the syringe pump was emptied into the reactor at a constant rate over the next 3 hours. Additional shots of the initiator were added at t=1, 2, 3 hour (0.28 g each). The reaction temperature then was raised to 91° C. at t=4 hour and additional initiator was charged at t=5, 8 and 10 hour (0.75 g each). After the last initiator addition, stirring continued at 91° C. for 4 hours. Then, ethanol (45.00 g) and DI water (45.00 g) were added into the reactor and stirred for 30 min. After cooling, a viscous copolymer solution was discharged into a glass bottle.

The glass transition temperature (T_g) was measured at 10° C./min and found to be 118° C.

Example 26

[Figure (not displayed)]

An autoclave reactor was loaded with t-butanol (242.00 g). A monomer solution of N-vinyl-2-pyrrolidone (36.00 g), acrylic acid (30.60 g), di-octyl maleate (36.00 g), methyl methacrylate (63.00 g), hydroxypropyl methacrylate (9.00 g) and t-butylaminoethyl methacrylate (5.40 g) was prepared and charged into a syringe pump. Then, 25.0% of the monomer solution was charged into the reactor. The mixture in the reactor was de-aerated and heated to 85° C. under nitrogen with mechanical stirring at 200 rpm. At t=0, t-amyl peroxy-2-ethylhexanoate initiator (Trigonox® 121, Akzo Nobel) (0.32 g) was charged into the reactor to initiate the polymerization. Then, the remaining monomer solution in the syringe pump was emptied into the reactor at a constant rate over the next 3 hours. Additional shots of the initiator were added at t=1, 2, 3 hour (0.32 g each). The reaction temperature then was raised to 91° C. at t=4 hour and additional initiator was charged at t=5, 8 and 10 hour (0.75 g each). After the last initiator addition, stirring continued at 91° C. for 4 hours. Then, DI water (30.00 g) was added into the reactor and stirred for 30 min. After cooling, a viscous copolymer solution was discharged into a glass bottle.

The glass transition temperature (T_g) was measured at 10° C./min and found to be 134° C.

Example 34

[Figure (not displayed)]

An autoclave reactor was loaded with t-butanol (148.50 g). A monomer solution of N-vinyl-2-pyrrolidone (30.60 g), acrylic acid (30.60 g), di-isobutyl fumarate (32.40 g), methyl methacrylate (72.00 g), hydroxypropyl methacrylate (9.00 g) and t-butylaminoethyl methacrylate (5.40 g) was prepared and charged into a syringe pump. Then, 25.0% of the monomer solution was charged into the reactor. The mixture in the reactor was de-aerated and heated to 85° C. under nitrogen with mechanical stirring at 200 rpm. At t=0, t-amyl peroxy-2-ethylhexanoate initiator (Trigonox® 121, Akzo Nobel) (0.28 g) was charged into the reactor to initiate the polymerization. Then, the remaining monomer solution in the syringe pump was emptied into the reactor at a constant rate over the next 3 hours. Additional shots of the initiator were added at t=1, 2, 3 hour (0.28 g each). The reaction temperature then was raised to 91° C. at t=4 hour and additional initiator was charged at t=5, 8 and 10 hour (0.75 g each). After the last initiator addition, stirring continued at 91° C. for 4 hours. Then, ethanol (45.00 g) and DI water (45.00 g) were added into the reactor and stirred for 30 min. After cooling, a viscous copolymer solution was discharged into a glass bottle.

The polymer was found to be at least 50% (w/w) soluble in ethanol.

Example 36

[Figure (not displayed)]

An autoclave reactor was loaded with t-butanol (148.50 g). A monomer solution of N-vinyl-2-pyrrolidone (32.40 g), methacrylic acid (32.40 g), di-isobutyl fumarate (37.80 g), isobutyl methacrylate (63.00 g), hydroxypropyl methacrylate (9.00 g) and t-butylaminoethyl methacrylate (5.40 g) was prepared and charged into a syringe pump. Then, 25.0% of the monomer solution was charged into the reactor. The mixture in the reactor was de-aerated and heated to 85° C. under nitrogen with mechanical stirring at 200 rpm. At t=0, t-amyl peroxy-2-ethylhexanoate initiator (Trigonox® 121, Akzo Nobel) (0.28 g) was charged into the reactor to initiate the polymerization. Then, the remaining monomer solution in the syringe pump was emptied into the reactor at a constant rate over the next 3 hours. Additional shots of the initiator were added at t=1, 2, 3 hour (0.28 g each). The reaction temperature then was raised to 91° C. at t=4 hour and additional initiator was charged at t=5, 8 and 10 hour (0.75 g each). After the last initiator addition, stirring continued at 91° C. for 4 hours. Then, ethanol (45.00 g) and DI water (45.00 g) were added into the reactor and stirred for 30 min. After cooling, a viscous copolymer solution was discharged into a glass bottle.

The glass transition temperature (T_g) was measured at 10° C./min and found to be 141° C.

Example 32

[Figure (not displayed)]

An autoclave reactor was loaded with t-butanol (148.50 g). A monomer solution of N-vinyl-2-pyrrolidone (30.60 g), acrylic acid (30.60 g), di-ethyl maleate (32.40 g), methyl methacrylate (72.00 g), hydroxypropyl methacrylate (9.00 g) and t-butylaminoethyl methacrylate (5.40 g) was prepared and charged into a syringe pump. Then, 25.0% of the monomer solution was charged into the reactor. The mixture in the reactor was de-aerated and heated to 85° C. under nitrogen with mechanical stirring at 200 rpm. At t=0, t-amyl peroxy-2-ethylhexanoate initiator (Trigonox® 121, Akzo Nobel) (0.28 g) was charged into the reactor to initiate the polymerization. Then, the remaining monomer solution in the syringe pump was emptied into the reactor at a constant rate over the next 3 hours. Additional shots of the initiator were added at t=1, 2, 3 hour (0.28 g each). The reaction temperature then was raised to 91° C. at t=4 hour and additional initiator was charged at t=5, 8 and 10 hour (0.75 g each). After the last initiator addition, stirring continued at 91° C. for 4 hours. Then, DI water (100.00 g) was added into the reactor and stirred for 30 min. After cooling, a viscous copolymer solution was discharged into a glass bottle.

Example 31

[Figure (not displayed)]

An autoclave reactor was loaded with t-butanol (165.00 g). A monomer solution of N-vinyl-2-pyrrolidone (20.00 g), acrylic acid (34.00 g), di-ethyl maleate (30.00 g), methyl methacrylate (100.00 g), hydroxypropyl methacrylate (10.00 g) and t-butylaminoethyl methacrylate (6.00 g) was prepared and charged into a syringe pump. Then, 25.0% of the monomer solution was charged into the reactor. The mixture in the reactor was de-aerated and heated to 85° C. under nitrogen with mechanical stirring at 200 rpm. At t=0, t-amyl peroxy-2-ethylhexanoate initiator (Trigonox® 121, Akzo Nobel) (0.28 g) was charged into the reactor to initiate the polymerization. Then, the remaining monomer solution in the syringe pump was emptied into the reactor at a constant rate over the next 3 hours. Additional shots of the initiator were added at t=1, 2, 3 hour (0.28 g each). The reaction temperature then was raised to 91° C. at t=4 hour and additional initiator was charged at t=5, 8 and 10 hour (0.75 g each). After the last initiator addition, stirring continued at 91° C. for 4 hours. After cooling, a viscous copolymer solution was discharged into a glass bottle.

The glass transition temperature (T_g) was measured at 10° C./min and found to be 92° C.