Method of converting a polymerizable composition into thermoplastic polyurethane of improved yellowness index and article obtained by this method
View Patent ↗Method of producing a thermoplastic polyurethane having a light stabilization useful for ophthalmic applications, comprising combining precursors of a polyurethane and at least one antioxidant, and incorporating therein, either before, during or after polymerization, at least one light stabilizer, said method being characterized in that the antioxidant is benzenepropanoic acid, 3(1,1-dimethylethyl)-4-hydroxy-5-methyl-1,1′-[1,2-ethanediylbis(oxy-2,1-ethanediyl)]ester and the light stabilizer is bis(1,2,2,6,6-pentamethyl-4-piperidinyl)-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate together with at least one additional component chosen from among phenol, 2-(5-chloro-2H-benzotriazole-2-yl)-6-(1,1-dimethylethyl)-4-methyl and 2,2′-methylenebis(6-(2H-benzotriazol-2-yl)-4-1,1,3,3-tetramethylbutyl)phenol).
1. A method of converting a polymerizable composition into thermoplastic polyurethane for use as an ophthalmic lens, said method comprising:
combining precursors of the polyurethane with a plurality of additives including:
(i) an antioxidant which is benzenepropanoic acid, 3(1,1-dimethylethyl)-4-hydroxy-5-methyl-1,1′-[1,2-ethanediylbis(oxy-2,1-ethanediyl)] ester is present in the amount of 0.1 to 1% by weight;
(ii) a light stabilizer component bis(1,2,2,6,6-pentamethyl-4-piperidinyl)-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate is present in the amount of 0.1 to 1% by weight; and
(iii) phenol, 2-(5-chloro-2H-benzotriazole-2-yl)-6-(1,1-dimethylethyl)-4-methyl present in the amount of 0.1 to 1% by weight;
and conducting a conversion step forming a thermoplastic polyurethane.
2. The method of claim 1 wherein the components (ii) and (iii) are combined with the polyurethane precursors and antioxidant by being fed from a side feeder in a reaction extruder.
3. A method of converting a polymerizable composition into a thermoplastic polyurethane for use as an ophthalmic lens, said method comprising:
combining precursors of the polyurethane with the antioxidant which is benzenepropanoic acid, 3(1,1-dimethylethyl)-4-hydroxy-5-methyl-1,1′-[1,2-ethanediylbis(oxy-2,1-ethanediyl)]ester and is present in the amount of 0.1 to 1% by weight;
conducting a polymerization reaction;
combining the antioxidant polymerized product with:
(i) the light stabilizer component bis(1,2,2,6,6-pentamethyl-4-piperidinyl)-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate which is present in the amount of 0.1 to 1% by weight; and
(ii) phenol, 2-(5-chloro-2H-benzotriazole-2-yl)-6-(1,1-dimethylethyl)-4-methyl is present in the amount of 0.1 to 1% by weight; and
shaping the thermoplastic polyurethane into the ophthalmic lens.
4. The method of claim 3 wherein the combining of components (i) and (ii) with the antioxidant polymerized product occurs in an extruder.
5. The method according to claim 1 or 3 , wherein benzenepropanoic acid, 3(1,1-dimethylethyl)-4-hydroxy-5-methyl-1,1′-[1,2-ethanediylbis(oxy-2,1-ethanediyl)]ester is Irganox® 245, the commercial product sold by Ciba part of BASF; bis(1,2,2,6,6-pentamethyl-4-piperidinyl)-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate is the commercial product Tinuvin® 144, sold by Ciba part of BASF; phenol, 2-(5-chloro-2H-benzotriazole-2-yl)-6-(1,1-dimethylethyl)-4-methyl is the commercial product Tinuvin® 326, sold by Ciba part of BASF; and 2,2′-methylenebis(6-(2H-benzotriazol-2-yl)-4-1,1,3,3-tetramethylbutyl)phenol) is the commercial product Tinuvin® 360,sold by Ciba part of BASF.
6. The method according to claim 1 or 3 , wherein the antioxidant is benzenepropanoic acid, 3(1,1-dimethylethyl)-4-hydroxy-5-methyl-1,1′-[1,2-ethanediylbis(oxy-2,1-ethanediyl)]ester and the light stabilizer is bis(1,2,2,6,6-pentamethyl-4-piperidinyl)-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate together with phenol, 2-(5-chloro-2H-benzotriazole-2-yl)-6-(1,1-dimethylethyl)-4-methyl.
7. The method according to claim 1 , wherein the plurality of additives also includes
a 2,2′-methylenebis(6-(2H-benzotriazol-2-yl)-4-1,1,3,3-tetramethylbutyl)phenol) present in the amount of 0.1 to 1% by weight.
8. The method according to claim 1 or 3 , wherein
the benzenepropanoic acid, 3(1,1-dimethylethyl)-4-hydroxy-5-methyl-1,1′-[1,2-ethanediylbis(oxy-2,1-ethanediyl)]ester is present in the amount of 0.1 to 0.5% by weight
the bis(1,2,2,6,6-pentamethyl-4-piperidinyl)-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate is present in the amount of from 0.1 to 0.5% by weight,
the phenol, 2-(5-chloro-2H-benzotriazole-2-yl)-6-(1,1-dimethylethyl)-4-methyl when present is in the amount of from 0.1 to 0.5% by weight, and
the 2,2′-methylenebis(6-(2H-benzotriazol-2-yl)-4-1,1,3,3-tetramethylbutyl)phenol) when present is in the amount of from 0.1 to 0.5% by weight.
9. The thermoplastic polyurethane product obtained by the method of claim 1 or 3 .
10. The thermoplastic polyurethane product obtained by the method of claim 5 .
11. The thermoplastic polyurethane product obtained by the method of claim 6 .
12. The thermoplastic polyurethane product obtained by the method of claim 7 .
13. The thermoplastic polyurethane product obtained by the method of claim 8 .
14. The ophthalmic lens according to claim 9 wherein its Yellowness Index does not increase by more than 4.0, after exposure in the Suntest for 200 hours.
15. The ophthalmic lens according to claim 10 wherein its Yellowness Index does not increase by more than 4.0, after exposure in the Suntest for 200 hours.
16. The ophthalmic lens according to claim 11 wherein its Yellowness Index does not increase by more than 4.0, after exposure in the Suntest for 200 hours.
17. The ophthalmic lens according to claim 12 wherein its Yellowness Index does not increase by more than 4.0, after exposure in the Suntest for 200 hours.
18. The ophthalmic lens according to claim 13 wherein its Yellowness Index does not increase by more than 4.0, after exposure in the Suntest for 200 hours.
19. The ophthalmic lens according to claim 14 wherein its Yellowness Index does not increase by more than 2.5, after exposure in the Suntest for 200 hours.
20. The ophthalmic lens according to claim 15 wherein its Yellowness Index does not increase by more than 2.5, after exposure in the Suntest for 200 hours.
21. The ophthalmic lens according to claim 16 wherein its Yellowness Index does not increase by more than 2.5, after exposure in the Suntest for 200 hours.
22. The ophthalmic lens according to claim 17 wherein its Yellowness Index does not increase by more than 2.5, after exposure in the Suntest for 200 hours.
23. The ophthalmic lens according to claim 18 wherein its Yellowness Index does not increase by more than 2.5, after exposure in the Suntest for 200 hours.
24. The ophthalmic lens according to claim 9 which further comprises a coating over at least part of a surface of the lens.
25. The method of claim 1 , further comprising the step of shaping the thermoplastic polyurethane into the ophthalmic lens.
26. The method of claim 3 , wherein the antioxidant polymerized product is also combined with 2,2′-methylenebis(6-(2H-benzotriazol-2-yl)-4-1,1,3,3-tetramethylbutyl)phenol) present in the amount of 0.1 to 1% by weight.