Itaconate copolymeric compositions for contact lenses

• US 5,346,976 A
• Filed: 03/29/1993
• Issued: 09/13/1994
• Est. Priority Date: 03/29/1993
• Status: Expired due to Term

• Current Assignee: B&L International Holdings Corp.
• Original Assignee: Polymer Technology Group, Inc. (DSM-Firmenich AG)
• Inventors: Bonafini, James A. Jr., Olson, Alfred P., Ellis, Edward J.
• Primary Examiner(s): Zitomer, Fred
• Application Number:
  US08/038,970
• Time in Patent Office: 533 Days
• Field of Search: 526/279, 526/253, 526/245, 523/107, 523/108
• US Class Current: 526/279
• CPC Class Codes: C08F 230/08 containing silicon
• 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: G02B 1/043 Contact lenses
• CPC Class Codes: Y10S 525/937 Utility as body contact e.g. implant, contact lens or I.U.D.

Abstract

Copolymers useful as contact lens materials are the polymerization product of a mixture comprising:

(a) an itaconate;

(b) a compound represented by formula (I): ##STR1## wherein: each A is independently an activated unsaturated radical;

each R is independently selected from the group consisting of a C₁ -C₁₂ monovalent hydrocarbon radical, a C₁ -C₁₂ monovalent hydrocarbon radical containing ether linkages, a halogen-substituted C₁ -C₁₂ monovalent hydrocarbon radical, and a halogen-substituted C₁ -C₁₂ monovalent hydrocarbon radical containing ether linkages;

each R'"'"' is independently a C₁ -C₂₂ divalent hydrocarbon radical; and

n averages about 15 to about 50;

(c) an ethylenically unsaturated organosiloxane monomer; and

(d) a hydrophilic monomer.

Claims

1. A copolymer useful as a contact lens material which is the polymerization product of a mixture comprising:

(a) an itaconate;

(b) a siloxane compound represented by formula (I);

##STR7## wherein;

each A is independently an activated unsaturated radical;

each R is independently selected from the group consisting of a C₁ -C₁₂ monovalent hydrocarbon radical, a C₁ -C₁₂ monovalent hydrocarbon radical containing ether linkages, a halogen-substituted C₁ -C₁₂ monovalent hydrocarbon radical, and a halogen-substituted C₁ -C₁₂ monovalent hydrocarbon radical containing ether linkages;

each R'"'"' is independently a C₁ -C₂₂ divalent hydrocarbon radical; and

n averages about 15 to about 50;

(c) an ethylenically unsaturated, monofunctional organosiloxane monomer; and

(d) a hydrophilic monomer.

2. The copolymer of claim 1, wherein compound (b) is ##STR8## wherein n averages about 25.

3. The copolymer of claim 2, wherein itaconate (a) is bis(1,1,1,3,3,3-hexafluoro-2-propyl) itaconate.

4. The copolymer of claim 1, wherein said mixture comprises:

(a) the itaconate at about 5 to about 60 weight percent;

(b) the siloxane compound of formula (I) at about 3 to about 25 weight percent;

(c) the ethylenically unsaturated, monofunctional organosiloxane monomer at about 2 to about 60 weight percent;

(d) the hydrophilic monomer at about 1 to about 25 weight percent;

(e) a hardness modifying (meth)acrylate monomer at 0 to about 50 weight percent; and

(f) a non-silicone containing crosslinking agent at 0 to about 20 weight percent.

5. The copolymer of claim 4, wherein said mixture comprises:

(a) the itaconate at about 20 to about 55 weight percent;

(b) the siloxane compound of formula (I) at about 9 to about 20 weight percent;

(c) the ethylenically unsaturated, monofunctional organosiloxane monomer at about 5 to about 50 weight percent;

(d) the hydrophilic monomer at about 5 to about 15 weight percent;

(e) the (meth)acrylate monomer at about 5 to about 35 weight percent; and

(f) the non-silicone containing crosslinking agent at about 1 to about 10 weight percent.

6. The copolymer of claim 5, wherein the organosiloxane monomer (c) includes tris(trimethylsiloxy)silylpropyl methacrylate.

7. The copolymer of claim 5, wherein the (meth)acrylate monomer (e) includes at least one alkyl (meth)acrylate.

8. The copolymer of claim 7, wherein the alkyl (meth)acrylate is selected from the group consisting of methyl methacrylate, neopentyl methacrylate, and mixtures thereof.

9. The copolymer of claim 5, wherein the hydrophilic monomer (d) is selected from the group consisting of methacrylic acid, N-vinylpyrrolidone, and mixtures thereof.

10. The copolymer of claim 5, wherein the crosslinking agent (f) includes neopentyl glycol dimethacrylate.

11. The copolymer of claim 4, wherein said mixture comprises:

(a) the itaconate at about 20 to about 55 weight percent;

(b) the siloxane compound of formula (I) at about 9 to about 20 weight percent;

(c) the ethylenically unsaturated, monofunctional organosiloxane monomer at about 5 to about 50 weight percent;

(d) the hydrophilic monomer at about 5 to about 15 weight percent; and

(e) the (meth)acrylate monomer at about 5 to about 35 weight percent.

12. The copolymer of claim 4, wherein said mixture comprises:

(a) the itaconate at about 20 to about 55 weight percent;

(b) the siloxane compound of formula (I) at about 9 to about 20 weight percent;

(c) the ethylenically unsaturated, monofunctional organosiloxane monomer at about 5 to about 50 weight percent;

(d) the hydrophilic monomer at about 5 to about 15 weight percent; and

(f) the non-silicone containing crosslinking agent at about 1 to about 10 weight percent.

13. A copolymer of claim 1, wherein said mixture consists essentially of:

bis(1,1,1,3,3,3-hexafluoro-2-propyl) itaconate;

the compound ##STR9## wherein n averages about 25;

tris(trimethylsiloxy)silylpropyl methacrylate;

methacrylic acid;

N-vinylpyrrolidone;

at least one monomer selected from the group consisting of methyl methacrylate and neopentyl methacrylate; and

at least one free radical initiator.

14. A copolymer of claim 1, wherein said mixture consists essentially of:

bis(1,1,1,3,3,3-hexafluoro-2propyl) itaconate;

the compound ##STR10## wherein n averages about 25;

tris(trimethylsiloxy)silylpropyl methacrylate;

methacrylic acid;

N-vinylpyrrolidone;

neopentyl glycol dimethacrylate;

neopentyl methacrylate; and

at least one free radical initiator.

15. A rigid, gas permeable contact lens formed of a copolymer which is the polymerization product of a mixture comprising:

(a) an itaconate;

(b) a siloxane compound represented by formula (I);

##STR11## wherein;

each A is independently an activated unsaturated radical;

each R is independently selected from the group consisting of a C₁ -C₁₂ monovalent hydrocarbon radical, a C₁ -C₁₂ monovalent hydrocarbon radical containing ether linkages, a halogen-substituted C₁ -C₁₂ monovalent hydrocarbon radical, and a halogen-substituted C₁ -C₁₂ monovalent hydrocarbon radical containing ether linkages;

each R'"'"' is independently a C₁ -C₂₂ divalent hydrocarbon radical; and

n average about 15 to about 50; and

(c) an ethylenically unsaturated, monofunctional organosiloxane monomer; and

(d) a hydrophilic monomer.

16. The contact lens of claim 15, wherein compound (b) has the formula ##STR12## wherein n averages about 25.

17. The contact lens of claim 16, wherein the itaconate is bis(1,1,1,3,3,3-hexafluoro-2-propyl) itaconate.

18. The contact lens of claim 15, wherein the copolymer is the polymerization product of a mixture consisting essentially of:

bis(1,1,1,3,3,3-hexafluoro-2-propyl) itaconate;

the compound ##STR13## wherein n averages about 25;

tris(trimethylsiloxy)silylpropyl methacrylate;

methacrylic acid;

N-vinylpyrrolidone;

at least one monomer selected from the group consisting of methyl methacrylate and neopentyl methacrylate; and

at least one free radical initiator.

19. The contact lens of claim 15, wherein the copolymer is the polymerization product of a mixture consisting essentially of:

bis(1,1,1,3,3,3-hexafluoro-2-propyl) itaconate;

the compound ##STR14## wherein n averages about 25;

tris(trimethylsiloxy)silylpropyl methacrylate;

methacrylic acid;

N-vinylpyrrolidone;

neopentyl glycol dimethacrylate;

neopentyl methacrylate; and

at least one free radical initiator.