Surface treatment of silicone materials

1. A surface treated intraocular lens, comprising:

a) the product of a reaction mixture comprising a platinum catalyst, a silicon-hydride cross-linker, and a polymer having formula (I):

wherein:

the sum of m and n is x;

x is from 0 to about 5000;

y is from 0 to about 500;

z is from 0 to about 500;

the sum of x, y, and z is at least 1;

R 1 -R 8 are each independently selected from the group consisting of hydrogen, —CH 3 , —C 6 H 5 and —CH═CH 2 ;

wherein at least one of R 1 , R 2 and R 3 is —CH═CH 2 ;

wherein at least one of R 6 , R 7 , or R 8 is —CH═CH 2 ; and

b) a surface treatment consisting essentially of a compound comprising at least one Si—H bond.

2. The lens of claim 1 , wherein in is 0 and z is 0.

3. The lens of claim 1 , wherein the polymer has a mole ratio of diphenylsiloxane monomer units of about 0.10 to about 0.20, and a mole ratio of dimethylsiloxane units of about 0.80 to about 0.90.

4. The lens of claim 1 , wherein R 1 , R 2 , R 3 , R 6 , R 7 , and R 8 are each —CH═CH 2 .

5. The lens of claim 1 , wherein the cross-linker is selected from the group consisting of phenyltris(dimethylsiloxy)silane, 1,1,3,3-tetraisopropyldisiloxane, 1,1,3,3-tetramethyldisiloxane, 1,1,4,4-tetramethyldisilethane, bis(dimethylsilyl)ethane, 1,1,3,3-tetramethyldisilazane, tetrakis(dimethylsiloxy)silane, a hydride-terminated polyphony-(dimethylhydrosiloxy)siloxane, a hydride terminated polydimethylsiloxane, a hydride terminated methylhydrosiloxane-phenylmethylsiloxane copolymer, and a hydride Q resin, (silicic acid (H 4 SiO 4 ), tetraethyl ester, reaction products with chlorodimethylsilane), and a mixture of any thereof.

6. The lens of claim 1 , wherein the surface treatment consists essentially of a compound selected from the group consisting of phenyltris(dimethylsiloxy)silane, 1,1,3,3-tetraisopropyldisiloxane, 1,1,3,3-tetramethyldisiloxane, 1,1,4,4-tetramethyldisilethane, bis(dimethylsilyl)ethane, 1,1,3,3-tetramethyldisilazane, tetrakis(dimethylsiloxy)silane, a hydride-terminated polyphony-(dimethylhydrosiloxy)siloxane, a hydride terminated polydimethylsiloxane, a hydride terminated methylhydrosiloxane-phenylmethylsiloxane copolymer, and a hydride Q resin (silicic acid (H 4 SiO 4 ), tetraethyl ester, reaction products with chlorodimethylsilane), and a mixture of any thereof.

7. The lens of claim 6 , wherein the surface treatment consists essentially of a hydride Q resin (silicic acid (H 4 SiO 4 ), tetraethyl ester, reaction products with chlorodimethylsilane).

8. A method for manufacturing a surface treated intraocular lens, comprising:

a) providing a reaction mixture comprising:

(i) a polymer having formula (I):

wherein:

the sum of m and n is x;

x is from 0 to about 500;

y is from 0 to about 500;

z is from 0 to about 500;

the sum of x, y, and z is at least 1;

R 1 -R 8 are each independently selected from the group consisting of hydrogen, —CH 3 , —C 6 H 5 and —CH═CH 2 ;

wherein at least one of R 1 , R 2 and R 3 is —CH═CH 2 ;

wherein at least one of R 6 , R 7 , or R 8 is —CH═CH 2 ;

(ii) a silicon hydride cross-linker; and

(iii) a platinum catalyst;

b) curing the reaction mixture to provide a cured silicone material;

c) surface treating the cured silicone material with a surface treatment composition consisting essentially of a compound comprising at least one Si—H bond to provide a surface treated silicone material; and

d) drying the surface treated silicone material to provide the surface treated intraocular lens.

9. The method of claim 8 , wherein in is 0 and z is 0.

10. The method of claim 8 , wherein the polymer has a mole ratio of diphenylsiloxane monomer units of about 0.10 to about 0.20, and a mole ratio of dimethylsiloxane units of about0.80 to about 0.90.

11. The method of claim 8 , wherein R 1 , R 2 , R 3 , R 6 , R 7 , and R 8 are each —CH═CH 2 .

12. The method of claim 8 , wherein the cross-linker is selected from the group consisting of phenyltris(dimethylsiloxy)silane, 1,1,3,3-tetraisopropyldisiloxane, 1,1,3,3, -tetramethyldisiloxane, 1,1,4,4-tetramethyldisilethane, bis(dimethylsilyl)ethane, 1,1,3,3-tetramethyldisilazane, tetrakis(dimethylsiloxy)silane, a hydride-terminated polyphony-(dimethylhydrosiloxy)siloxane, a hydride terminated polydimethylsiloxane, a hydride terminated methylhydrosiloxane-phenylmethylsiloxane copolymer, and a hydride Q resin (silici acid (H 4 SiO 4 ), tetraethyl ester, reaction products with chlorodimethylsilane), and a mixture of any thereof.

13. The method of claim 8 , wherein the surface treatment composition consists essentially of a compound selected from the group consisting of phenyltris(dimethylsiloxy)silane, 1,1,3,3-tetraisopropyldisiloxane,1,1,3,3-tetramethyldisiloxane, 1,1,4,4-tetramethyldisilethane, bis(dimethylsilyl)ethane, 1,1,3,3-tetramethyldisilazane, tetrakis(dimethylsiloxy)silane, a hydride-terminated polyphony-(dimethylhydrosiloxy)siloxane, a hydride terminated polydimethylsiloxane, a hydride terminated methylhydrosiloxane-phenylmethylsiloxane copolymer, and a hydride Q resin (silici acid (H 4 SiO 4 ), tetraethyl ester, reaction products with chlorodimethylsilane), and a mixture of any thereof.

14. The method of claim 13 , wherein the surface treatment composition consists essentially of a hydride Q resin (silici acid (H 4 SiO 4 ), tetraethyl ester, reaction products with chlorodimethylsilane).

15. The method of claim 8 , wherein the surface treating step comprises contacting the cured silicone material with the surface treatment composition for about 10 seconds to about 10 minutes.

16. The method of claim 8 , wherein the drying step comprises drying the surface treated silicone material for about 1 minute to about 60 minutes.

17. The method of claim 8 , wherein the surface treated silicone material is dried at a temperature of about 100° C. to about 180° C.

18. The method of claim 8 , further comprising a step of extracting the cured silicone product with an organic solvent, between steps c) and d).

19. The method of claim 18 , wherein the extracting step comprises Soxhlet extraction.

20. The method of claim 17 , wherein the organic solvent is selected from the group consisting of ethanol and isopropanol.

21. An intraocular lens prepared by a process comprising the steps of:

a) providing a reaction mixture comprising:

(i) a polymer having formula (I):

wherein:

the sum of m and n is x;

x is from 0 to about 5000;

y is from 0 to about 500;

z is from 0 to about 500;

the sum of x, y, and z is at least 1;

R 1 -R 8 are each independently selected from the group consisting of hydrogen, —CH 3 , —C 6 H 5 and —CH═CH 2 ;

wherein at least one of R 1 , R 2 and R 3 is —CH═CH 2 ;

wherein at least one of R 6 , R 7 , or R 8 is —CH═CH 2 ;

(ii) a silicon hydride cross-linker; and

(iii) a platinum catalyst;

b) curing the reaction mixture to provide a cured silicone material;

c) surface treating the cured silicone material with a surface treatment composition consisting essentially of a compound comprising at least one Si—H bond to provide a surface treated silicone material; and

d) drying the surface treated silicone material.

22. The lens of claim 21 , wherein m is 0 and z is 0.

23. The lens of claim 21 , wherein the polymer has a mole ratio of diphenylsiloxane monomer units of about 0.10 to about 0.20, and a mole ratio of dimethylsiloxane units of about 0.80 to about 0.90.

24. The lens of claim 21 , wherein R 1 , R 2 , R 3 , R 6 , R 7 , and R 8 are each —CH═CH 2 .

25. The lens of claim 21 , wherein the cross-linker is selected from the group consisting of phenyltris(dimethylsiloxy)silane, 1,1,3,3-tetraisopropyldisiloxane, 1,1,3,3-tetramethyldisiloxane, 1,1,4,4-tetramethyldisilethane, bis(dimethylsilyl)ethane, 1,1,3,3-tetramethyldisilazane, tetrakis(dimethylsiloxy)silane, a hydride-terminated polyphony-(dimethylhydrosiloxy)siloxane, a hydride terminated polydimethylsiloxane, a hydride terminated methylhydrosiloxane-phenylmethylsiloxane copolymer, and a hydride Q resin (silici acid (H 4 SiO 4 ), tetraethyl ester, reaction products with chlorodimethylsilane), and a mixture of any thereof.

26. The lens of claim 21 , wherein the surface treatment composition consists essentially of a compound selected from the group consisting of phenyltris(dimethylsiloxy)silane, 1,1,3,3-tetraisopropyldisiloxane, 1,1,3,3-tetramethyldisiloxane, 1,1,4,4-tetramethyldisilethane, bis(dimethylsilyl)ethane, 1,1,3,3-tetramethyldisilazane, tetrakis(dimethylsiloxy)silane, a hydride-terminated polyphony-(dimethylhydrosiloxy)siloxane, a hydride terminated polydimethylsiloxane, a hydride-terminated methylhydrosiloxane-phenylmethylsiloxane copolymer, and a hydride Q resin (silici acid (H 4 SiO 4 ), tetraethyl ester, reaction products with chlorodimethylsilane), and a mixture of any thereof.

27. The lens of claim 26 , wherein the surface treatment composition consists essentially of a hydride Q resin (silici acid (H 4 SiO 4 ), tetraethyl ester, reaction products with chlorodimethylsilane).

28. The lens of claim 21 , wherein the surface treating step comprises contacting the cured silicone material with the surface treatment composition for about 10 seconds to about 10 minutes.

29. The lens of claim 21 , wherein the drying step comprises drying the surface treated silicone material for about 1 minute to about 60 minutes.

30. The lens of claim 21 , wherein the surface treated silicone material is dried at a temperature of about 100° C. to about 180° C.

31. The lens of claim 21 , further comprising a step of extracting the surface treated silicone material with an organic solvent, between steps c) and d).

32. The lens of claim 31 , wherein the extracting step comprises Soxhlet extraction.

33. The lens of claim 31 , wherein the organic solvent is selected from the group consisting of ethanol and isopropanol.