Gas-permeable materials and medical devices
View Patent ↗Gas-permeable polymeric materials comprise poly(disubstituted acetylene) and a siloxanyl-based polymer. Medical devices, such as ophthalmic devices, are manufactured from such gas-permeable materials.
1. A polymeric material comprising a poly(disubstituted acetylene) and a siloxanyl-based polymer, wherein the poly(disubstituted acetylene) has a formula of
wherein the group R 1 of different repeating units is independently selected from the group consisting of lower alkyl, substituted lower alkyl, C 6-36 aryl, and C 6-36 substituted aryl, and some or all of the R 1 groups are trifluoromethyl; R 2 comprises a substituted silyl group having a formula of
wherein R 3 , R 4 , and R 5 are independently selected from the group consisting of lower alkyl, substituted lower alkyl, C 6-36 aryl, and C 6-36 substituted aryl; and n is a positive integer in the range from about 20 to about 500.
2. The polymeric material of claim 1 , wherein the R 1 groups are independently selected from the group consisting of trifluoromethyl, lower alkyl and substituted lower alkyl groups.
3. The polymeric material of claim 1 , wherein said aryl groups are selected from the group consisting of phenyl, biphenyl, naphthyl, benzyl, anthryl, and combinations thereof.
4. The polymeric material of claim 1 , wherein at least some of the R 1 groups are methyl or phenyl.
5. The polymeric material of claim 4 , wherein said R 3 , R 4 , and R 5 are independently selected from the group consisting of methyl and phenyl groups.
6. The polymeric material of claim 1 , wherein the siloxanyl-based polymer comprises a polymerization product of at least one of vinyl-, (meth)acrylate-, hydride-, epoxy-, hydroxyl-, and amino-terminated siloxanes having from 1 to about 20 siloxy units.
7. The polymeric material of claim 6 , wherein substituents on said siloxy units are selected from the group consisting of substituted and unsubstituted lower alkyl, and substituted and unsubstituted C 6-36 aryl groups.
8. The polymeric material of claim 1 , wherein the siloxanyl-based polymer comprises a polymerization product of tris(trimethylsiloxy)silylpropyl methacrylate (“TRIS”).
9. The polymeric material of claim 1 , wherein the siloxanyl-based polymer comprises a polymerization product of a vinyl carbonate or vinyl carbamate siloxane-containing macromonomer.
10. The polymeric material of claim 1 , wherein the siloxanyl-based polymer comprises a copolymer of polyurethane and polysiloxane.
11. A medical device comprising a poly(disubstituted acetylene) and a siloxanyl-based polymer, wherein the poly(disubstituted acetylene) has a formula of
wherein the group R 1 of different repeating units is independently selected from the group consisting of lower alkyl, substituted lower alkyl, C 6-36 aryl, and C 6-36 substituted aryl, and some or all of the R 1 groups are trifluoromethyl; R 2 comprises a substituted silyl group having a formula of
wherein R 3 , R 4 , and R 5 are independently selected from the group consisting of lower alkyl, substituted lower alkyl, C 6-36 aryl, and C 6-36 substituted aryl; and n is a positive integer in the range from about 20 to about 500, and the medical device is an ophthalmic device.
12. The medical device of claim 11 , wherein the R 1 groups are independently selected from the group consisting of lower alkyl and substituted lower alkyl groups.
13. The medical device of claim 11 , wherein said aryl groups are selected from the group consisting of phenyl, biphenyl, naphthyl, benzyl, anthryl, and combinations thereof.
14. The medical device of claim 11 , wherein at least some of the R 1 groups are methyl or phenyl.
15. The medical device of claim 14 , wherein said R 3 , R 4 , and R 5 are independently selected from the group consisting of methyl and phenyl groups.
16. The medical device of claim 11 , wherein the siloxanyl-based polymer comprises a polymerization product of at least one of vinyl-, (meth)acrylate-, hydride-, epoxy-, hydroxyl-, and amino-terminated siloxanes having from 1 to about 20 siloxy units.
17. The medical device of claim 16 , wherein substituents on said siloxy units are selected from the group consisting of substituted and unsubstituted lower alkyl, and substituted and unsubstituted C 6-36 aryl groups.
18. The medical device of claim 16 , wherein substituents on said siloxy units are selected from the group consisting of substituted and unsubstituted C 1-3 alkyl, phenyl, and substituted phenyl groups.
19. The medical device of claim 11 , wherein the siloxanyl-based polymer comprises a polymerization product of tris(trimethylsiloxy)silylpropyl methacrylate (“TRIS”).
20. The medical device of claim 19 , wherein the medical device further comprises units of a hydrophilic monomer, a hydrophobic monomer, or both.
21. The medical device of claim 11 , wherein the siloxanyl-based polymer comprises a polymerization product of a vinyl carbonate or vinyl carbamate siloxane-containing macromonomer.
22. The medical device of claim 11 , wherein the siloxanyl-based polymer comprises a copolymer of polyurethane and polysiloxane.
23. The medical device of claim 11 , further comprising units of a radiation absorber.
24. The medical device of claim 23 , wherein the radiation absorber is capable of absorbing at least a portion of UV radiation or visible light having wavelengths in a range of violet or blue light.
25. The medical device of claim 11 , wherein the medical device has an oxygen permeability (Dk) in a range from about 140 to about 1000 barrers.
26. The medical device of claim 11 , wherein the medical device has an oxygen permeability (Dk) in a range from about 160 to about 300 barrers.
27. A method for making a gas-permeable contact lens, the method comprising:
forming a solid block of a polymeric material comprising poly(disubstituted acetylene) and at least a siloxanyl-based polymer, wherein the poly(disubstituted acetylene) has a formula of
wherein the group R 1 of different repeating units is independently selected from the group consisting of lower alkyl, substituted lower alkyl, C 6-36 aryl, and C 6-36 substituted aryl, and some or all of the R 1 groups are trifluoromethyl; R 2 comprises a substituted silyl group having a formula of
wherein R 3 , R 4 , and R 5 are independently selected from the group consisting of lower alkyl, substituted lower alkyl, C 6-36 aryl, and C 6-36 substituted aryl; and n is a positive integer in the range from about 20 to about 500; and
shaping the block to form the contact lens.
28. The method of claim 27 , wherein the step of shaping comprises: (1) cuffing the block into wafers; and (2) machining or lathing the wafer into the form of the contact lens.
29. The method of claim 27 , further comprising forming a hydrophilic coating on said contact lens.
30. The method of claim 29 , wherein the step of forming said hydrophilic coating comprises creating a plurality of surface reactive functional groups on a surface of the contact lens and attaching a hydrophilic polymer thereto.
31. The method of claim 30 , wherein the step of creating a plurality of surface reactive functional groups on a surface of the contact lens is effected by exposing the medical device surface to a plasma containing an oxidizing gas.