Hydrophilic contact lens made from polysiloxanes which are thermally bonded to polymerizable groups and which contain hydrophilic sidechains

• US 4,260,725 A
• Filed: 12/10/1979
• Issued: 04/07/1981
• Est. Priority Date: 12/10/1979
• Status: Expired due to Term

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Kunzler, Jay F., Keogh, Philip L., Niu, Gregory C. C.
• Primary Examiner(s): Marquis, Melvyn I.
• Application Number:
  US06/102,009
• Time in Patent Office: 484 Days
• Field of Search: 351/160 H, 351/160 R, 528/33, 528/35, 528/25, 528/26, 528/28, 528/37, 528/32, 526/279, 526/75, 264/1, 264/2, 525/419, 525/479
• US Class Current: 526/279
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A water absorbing, soft, hydrophilic, flexible, hydrolytically stable, biologically inert contact lens with the capability of transporting oxygen sufficiently to meet the requirements of the human cornea comprising a polysiloxane which is α,ω terminally bonded through divalent hydrocarbon groups to polymerizably activated unsaturated groups and which contain hydrophilic sidechains is disclosed.

Claims

1. A water absorbing, soft, hydrophilic, flexible, hydrolytically stable, biologically inert contact lens with the capability of transporting oxygen sufficiently to meet the requirements of the human cornea comprising a polysiloxane which is α

,ω

terminally bonded through divalent hydrocarbon groups to polymerizable activated unsaturated groups and which contain hydrophilic sidechains is disclosed.

2. The contact lens according to claim 1 wherein said hydrophilic sidechain is selected from the group consisting of ##STR109## wherein n₂₄ is an integer from 2 to 3, ##STR110## wherein R₇₄ and R₇₅ are the same or different and are seleced from the group consisting of hydrogen, methyl and --CH₂ --CH₂ --OH, ##STR111## wherein R₇₆ is selected from the group consisting of hydrogen and methyl, ##STR112## ##STR113## wherein n₂₅ is an integer from 2 to 3 ##STR114##

3. The contact lens according to claim 1 wherein X is selected from the group consisting of ##STR115## wherein n₂₆ is an integer from 1 to about 10, ##STR116## wherein n₂₇ is an integer from 1 to 10, ##STR117## wherein n₂₈ is an integer from 1 to about 10 and ##STR118## wherein n₂₉ is an integer from 0 to about 10.

4. The contact lens according to claim 3 wherein X is selected from the group consisting of ##STR119## wherein n₃₀ is an integer from 3 to 4, and ##STR120## wherein n₃₁ is an integer from 3 to 4.

5. The polysiloxane monomer according to claim 4 wherein ##STR121## wherein R₇₇ is selected from the group consisting of hydrogen and methyl.

6. The contact lens according to claim 1 wherein Y₁ is methyl and Y₂ is phenyl.

7. The contact lens according to claim 1 wherein Y₁ and Y₂ are methyls.

8. The contact lens according to claim 1 wherein at least one but not all of Z₁ through ##STR122## wherein ##STR123## and n₃₂ equals 1.

9. The contact lens according to claim 1 wherein only one of Z₁, Z₂, Z₅ and Z₆ is a hydrophilic sidechain.

10. The contact lens according to claim 9 wherein a is equal to 1 to about 1,000, b is equal to zero, c is equal to 1, d is equal to 1 to about 1,000, e is equal to one and f is equal to zero.

11. The contact lens according to claim 10 wherein a is equal to about 10 l to about 500, b is equal to zero, c is equal to 1, d is equal to about 10 to about 500, e is equal to 1 and f is equal to zero.

12. The contact lens according to claim 11 wherein a is equal to about 75 to about 150, b is equal to zero, c is equal to one, d is equal to about 25 to about 50, e is equal to one and f is equal to zero.

13. The contact lenss according to claim 12 wherein a is equal to about 75, b is equal to zero, c is equal to one, d is equal to about 25, e is equal to one and f is equal to zero.

14. The contact lens according to claim 13 wherein Z₁, Z₂ and Z₅ are methyls and Z₆ is selected from the group consisting of ##STR124## wherein n₃₃ is an integer from 2 to 3, ##STR125## wherein R₇₉ is selected from the group consisting of methyl and hydrogen, R₈₀ is selected from the group consisting of methyl, hydrogen and --CH₂ --CH₂ --OH, Y₁ and Y₂ equal methyl and ##STR126## wherein n₃₄ is an integer from 3 to 4.

15. The contact lens according to claim 1 wherein only one of Z₁ -Z₇ is a hydrophilic sidechain.

16. Th contact lens according to claim 15 wherein a is equal to one, b is equal to about 2 to about 4, c is equal to zero, d is equal to one, e is equal to about 25 to about 500 and f is equal to about 25 to 500.

17. The contact lens according to claim 16 wherein a is equal to one, b is equal to about 2 to about 3, c is equal to zero, d is equal to one, e is equal to about 25 to about 250 and f is equal to about 25 to about 250.

18. The contact lens according to claim 17 wherein a is equal to one, b is equal to about 2 to about 3, c is equal to zero, d is equal to one, e is equal to from about 50 to about 100 and f is equal to from about 50 to about 100.

19. The contact lens according to claim 18 wherein a is equal to one, b is equal to from about 2 to about 3, c is equal to zero, d is equal to one, e is equal to from about 50 to about 75 and f is equal to from about 50 to about 75.

20. The contact lens according to claim 19 wherein Z₁, Z₂, Z₅, Z₆, Y₁ and Y₂ are methyls, Z₃ and Z₄ are hydrogens and ##STR127##

21. The contact lens according to claim 1 wherein the comonomer is ##STR128## wherein R₈₁ is selected from the group consisting of hydrogen and methyl and B is --0--R₈₂ wherein R₈₂ is selected from the group consisting of a monovalent hydrocarbon having from 1 to 12 carbon atoms a monovalent hydrocarbon derivative having from 1 to 12 carbon atoms and hydrogen.

22. The contact lens according to claim 21 wherein R₈₂ is selected from the group consisting of hydrogen, methyl, ethyl, n-propyp, isopropyl, n-butyl and isobutyl.

23. The contact lens according to claim 21 wherein R₈₂ is selected from the group consisting of ##STR129##

24. The contact lens according to claim 21 wherein R₈₂ is ##STR130## wherein n₃₅ is an integer from 1 to 3.

25. The contact lens according to claim 21 wherein ##STR131## wherein R₈₃ and R₈₄ are the same or different and are selected from the group consisting of hydrogen, methyl and --CH₂ --CH₂ --OH.

26. The contact lens according to claim 1 wherein the comonomer is ##STR132##

27. The contact lens according to claim 1 wherein the comonomer is ##STR133##

28. The contact lens according to claim 1 wherein the comonomer is ##STR134## wherein R₈₅ and R₈₇ are the same or different and are selected from the group consisting of hydrogen and methyl and R₈₆ is --CH₂ --CH₂ --.

29. The contact lens according to claim 1 wherein the comonomer is ##STR135## wherein R₈₈ is selected from the group consisting of methyl, ethyl, n-propyl and n-butyl.