Long wearable soft contact lens

• US 20020016383A1
• Filed: 07/02/2001
• Published: 02/07/2002
• Est. Priority Date: 12/16/1999
• Status: Active Grant

• Current Assignee: Coopervision International Limited (The Cooper Cos., Inc.)
• Original Assignee: AsahiKasei Aime Co. Ltd. (Asahi Kasei Corporation)
• Inventors: Hoki, Tsuneo, Ikawa, Seiichirou, Iwata, Junichi
• Granted Patent: US 6,867,245 B2
• Time in Patent Office: Days
• US Class Current: 523/106
• CPC Class Codes: B29D 11/00125 Auxiliary operations, e.g. removing oxygen from the mould, conveying moulds from a storage to the production line in an inert atmosphere
• CPC Class Codes: C08F 220/1806 C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (meth)acrylate
• CPC Class Codes: C08F 220/54 Amides , e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 226/02 by a single or double bond to nitrogen
• CPC Class Codes: C08F 226/10 N-Vinyl-pyrrolidone
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08F 283/12 on to polysiloxanes
• CPC Class Codes: C08F 290/06 Polymers provided for in subclass C08G
• CPC Class Codes: C08F 290/061 Polyesters; Polycarbonates
• CPC Class Codes: C08F 290/065 Polyamides; Polyesteramides; Polyimides
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 7/04 Contact lenses for the eyes disinfection or sterilisation of contact lenses A61L12/00

Abstract

The present invention relates to a soft contact lens, and provides a contact lens which shows small and stable contact angle to water at its surface in water as well as in air, little deposition in wearing, high oxygen permeability, no adhesion of lens to a cornea and superior extended-wearing characteristics. The present invention provides a hydrogel soft contact lens which has contact angle at a lens surface in a range of 10-50° by the captive bubble method in water and 30-90° by the sessile drop method in air, oxygen permeability of not less than 30 and water content of not less than 5%, and also a hydrogel soft contact lens consisting of a polymer comprising a hydrophilic siloxanyl monomer shown by a specified general formula.

Claims

1. A hydrogel soft contact lens with contact angle of a surface in a range of 10-50°

and 30-90°

by the captive bubble method in water and the sessile drop method in air, respectively, oxygen permeability of not less than 30 and water content of not less than 5%.

3. The hydrogel soft contact lens according to claim 1 or 2, comprising a copolymer obtained by a polymerization of at least one kind of hydrophilic siloxane monomer.

4. The hydrogel soft contact lens according to claim 3, wherein the hydrophilic siloxane monomer is a hydrophilic polysiloxane monomer shown by the following formula (1):

5. The hydrogel soft contact lens according to claim 4, wherein the structure [Y1] is a structural unit shown by the following formula:

6. The hydrogel soft contact lens according to claim 5, wherein the structural unit [Y1] according to claim 5 is a polysiloxane monomer with R9 and R10 being methyl group.

7. The hydrogel soft contact lens according to claim 4 consisting of a hydrophilic polysiloxane monomer, wherein the structural unit [Y1] according to claim 4 comprises sequentially linked structural units (Ia) and (IIa) shown below, the linking ratio of the units (Ia) and (IIa) being 1:

10-10;

1, and the total number of the linking of (Ia) and (IIa) being 7-1000;

8. The hydrogel soft contact lens according to claim 7 consisting of a hydrophilic polysiloxane monomer, wherein R11, R12 and R13 are methyl groups and R14 is a trifluoropropyl group in the structural unit [Y1] according to claim 7.

9. The hydrogel soft contact lens according to claim 4 consisting of a hydrophilic polysiloxane monomer, wherein the structural unit [Y1] according to claim 4 comprises sequentially linked structural units (Ib) and (IIb) shown below, the linking ratio of the structural units (Ib) and (IIb) being (Ib)/(IIb)=0.1-200, and the total number of the linking of (Ib) and (IIb) being 7-1000:

10. The hydrogel soft contact lens according to claim 4 consisting of a hydrophilic polysiloxane monomer, wherein the structural unit [Y1] according to claim 4 comprises sequentially linked structural units (Ic), (IIc) and (IIIc) shown by the following formulas:

11. The hydrogel soft contact lens according to claim 10, wherein the linking ratio of the structural units (Ic), (IIc) and (IIIc) in the structural unit [Y1] according to claim 10 is ((Ic)+(IIc))/(IIIC)=1-50, (IIc)/(Ic)=0.01-0.50, and the total number of the linking of (Ic), (IIc) and (IIIc) is 20-500.

12. The hydrogel soft contact lens according to any one of claims 9-11 consisting of a hydrophilic polysiloxane monomer, wherein the hydrophilic substituent is shown by the following formula (4) or (5):

—

R20(OH)a 

 

(4)

wherein, R20 is a hydrocarbon group with 3-12 carbon atoms;

the group may have a group of —

O—

, —

CO—

or —

COO—

inserted between carbon atoms;

only one OH group can be substituted on one carbon atom; and

a is a number larger than 1.

—

R21—

(OR22)_b—

OZ2 

 

(5)

wherein, R21 is a hydrocarbon group with 3-12 carbon atoms;

the group may have a group of —

O—

, —

CO—

or —

COO—

inserted between carbon atoms;

R22 is a hydrocarbon group with 2-4 carbon atoms, and the number of the carbon atoms may be different from each other when b is not less than 2;

b is 1-200;

Z2 is a group selected from hydrogen atom, hydrocarbon group with 1-12 carbon atoms and —

OCOR23 (R23 is a hydrocarbon group with 1-12 carbon atoms).

13. The hydrogel soft contact lens according to any one of claims 9-11, wherein the hydrophilic substituent is selected from the group consisting of the following formulas (6), (7) and (8):

—

C₃H₆OH 

 

(6) —

C₃H₆OCH₂CH(OH)CH₂OH 

 

(7) —

C₃H₆OC₂H₄OH 

 

(8)

14. The hydrogel soft contact lens according to claims 9-11, wherein the hydrophilic substituent is selected from the group of the following formulas (9) and (10) in claim 9:

—

C₃H₆(OC₂H₄)_cOH 

 

(9) —

C₃H₆(OC₂H₄)_dOCH₃ 

 

(10)

wherein, c and d are 1-40.

15. The hydrogel soft contact lens according to claim 4, wherein the structural unit [Y1] in the hydrophilic polysiloxane monomer shown by the formula (1) according to claim 4 is expressed by the following formula (11):

16. The hydrogel soft contact lens according to claim 15 consisting of a polymer from a hydrophilic polysiloxane monomer, wherein R30 in the Z3 liking group shown by the formula (11) according to claim 15 is selected from hexamethylene, tetramethylene, dicyclohexylmethane, hydrogenated xylylene and isophorone groups and R31 is selected from polyethylene glycol, polypropylene glycol and polybutylene glycol.

17. The hydrogel soft contact lens according to any one of claims 4-14, wherein the polymerizable Z1 liking group shown by the formula (2) according to claim 4 is shown by the following formula (13):

—

B—

COHN—

R32—

NHCOO—

R33—

CONH—

R32—

NHCO—

B—

 

 

(13)

wherein, R32 is a hydrocarbon group with 4-20 carbon atoms and may be interrupted by oxygen atom;

R33 is polyoxyalkylene or polyoxyfluoloalkylene group;

B means —

O—

or —

NH—

linkage.

18. The hydrogel soft contact lens according to claim 17 consisting of a polymer from a hydrophilic polysiloxane monomer, wherein R32 in the formula (13) is selected from hexamethylene, tetramethylene, dicyclohexylmethane, hydrogenated xylylene and isophorone groups and R33 is selected from polyethylene glycol, polypropylene glycol and polybutylene glycol.

20. The hydrogel soft contact lens according to claim 19, wherein the hydrophilic monomer is an amide monomer.

21. The hydrogel soft contact lens according to claim 19, wherein the hydrophilic monomer is an amide monomer containing N-vinyl group.

22. The hydrogel soft contact lens according to claim 21, wherein the amide monomer containing N-vinyl group is selected from N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methylacetamide, N-vinylpyrrolidone and N-vinyl caprolactam.

23. The hydrogel soft contact lens according to claim 21, wherein the amide monomer containing N-vinyl group is N-vinyl N-methylacetamide or N-vinylpyrrolidone.

24. The hydrogel soft contact lens according to any one of claims 21-23, consisting of a copolymer composed of 10-99% by weight of a hydrophilic polysiloxane monomer and 1-80% by weight of an amide monomer containing N-vinyl group.

25. The hydrogel soft contact lens according to any one of claims 21-23, consisting of a copolymer composed of 30-95% by weight of a hydrophilic polysiloxane monomer and 5-60% by weight of a monomer containing an amide group with N-vinyl group.

26. The hydrogel soft contact lens according to any one of claims 3-25, obtained by a polymerization of a crosslinkable monomer linked with urethane groups.

27. The hydrogel soft contact lens according to claim 26, wherein the crosslinkable monomer is shown by the following formula (14):

28. The hydrogel soft contact lens according to claim 26, wherein the crosslinkable monomer is shown by the following formula (15):

30. The hydrogel soft contact lens according to claim 29, wherein surface contact angle is in a range of 10-40°

and 30-80°

by air bubble method in water and by droplet method in air, respectively, oxygen permeation coefficient is not less than 80 and water content is not less than 9%.

31. The hydrogel soft contact lens according to any one of claims 1-30, manufactured by a polymerization in a mold.

32. The hydrogel soft contact lens according to claim 3, wherein the hydrophilic siloxanyl monomer is shown by the following formula (16):

33. The hydrogel soft contact lens according to claim 3, consisting of a polymer comprising at least the hydrophilic siloxanyl monomer shown by the above formula (16), a hydrophilic monomer and a crosslinkable monomer.

34. The hydrogel soft contact lens according to any of claim 32 or 33, wherein the hydrophilic siloxanyl monomer according to claim 32 is shown by the following formula (17):

35. The hydrogel soft contact lens according to any one of claims 32-34, consisting of a polymer comprising at least a hydrophilic siloxanyl monomer shown by the above formula (16), a siloxanyl monomer shown by the following formula (18), a hydrophilic monomer and a crosslinkable monomer:

36. The hydrogel soft contact lens according to claim 35, wherein the siloxanyl monomer shown by the formula (18) is tris(trimethylsiloxy)silylpropyl methacrylate.

37. The hydrogel soft contact lens according to any of claims 33 or 35, wherein the hydrophilic monomer is an amide monomer containing N-vinyl group in claim 33 or 35.

38. The hydrogel soft contact lens according to claim 37, wherein the amide monomer containing N-vinyl group is N-vinyl-N-methylacetamide or N-vinyl pyrrolidone.

39. The hydrogel soft contact lens according to any one of claims 32-38, prepared by processing a polymer comprising a hydrophilic siloxanyl monomer by lathe-cutting and polishing method followed by swelling with water.

47. The hydrogel soft contact lens according to any one of claims 1-38, manufactured by a polymerization in a mold according to any one of claims 40-44.

48. A method for manufacturing a contact lens according to any one of claims 1-38, wherein the method is a polymerization in a mold.

2. A hydrogel soft contact lens with a surface contact angle in a range of 10-40°

and 30-80°

by the captive bubble method in water and the sessile drop method in air, respectively, oxygen permeability of not less than 80 and water content of not less than 9%.

19. A hydrogel soft contact lens obtained by a copolymerization of at least 1 kind of hydrophilic polysiloxane monomer in the formula (1) with at least 1 kind of hydrophilic monomer.

29. The hydrogel soft contact lens according to any one of items 19-28, wherein surface contact angel is in a range of 10-50°

and 30-90°

by the captive bubble method in water and by the sessile drop method in air, respectively, oxygen permeability is not less than 30 and water content is not less than 5%.

40. A hydrogel soft contact lens manufactured by a polymerization in a mold, wherein a mold material is insoluble to a composition of polymerizable monomers and at least one side of the mold for forming a lens surface has a polar group.

41. The hydrogel soft contact lens according to claim 40, wherein the mold material consists of a resin with a contact angle to water of not higher than 90°

by the sessile drop method.

42. The hydrogel soft contact lens according to claim 40, wherein the mold material consists of a resin with a contact angel to water is 65-80°

by the sessile drop method.

43. The hydrogel soft contact lens according to any one of claims 40-42, wherein the mold consists of a resin selected from polyamide, polyethylene terephthalate and ethylene-vinylalcohol copolymer.

44. The hydrogel soft contact lens according to any one of claims 40-42, wherein the mold material consists of ethylene-vinylalcohol copolymer.

45. The hydrogel soft contact lens according to any one of claims 40-44, wherein contact angle of a surface is in a range of 10-50°

and 30-90°

by the captive bubble method in water and by the sessile drop method in air, respectively, and water content is not less than 5%.

46. The hydrogel soft contact lens according to any one of claims 40-44, wherein surface contact angle is in a range of 10-40°

and 30-80°

by the captive bubble method in water and by the sessile drop method in air, respectively, and water content is not less than 9%.

49. A method for manufacturing a contact lens, wherein the mold according to claim 48 consists of the material according to any one of claims 40-44.