Surface modification of polymer objects

• US 5,364,918 A
• Filed: 03/29/1993
• Issued: 11/15/1994
• Est. Priority Date: 11/27/1990
• Status: Expired due to Term

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: McGee, Joseph A., Lai, Yu-Chin, Valint, Paul L. Jr.
• Primary Examiner(s): Michl, Paul R.
• Assistant Examiner(s): DeWitt, LaVonda R.
• Application Number:
  US08/038,384
• Time in Patent Office: 596 Days
• Field of Search: 526/245, 526/286, 526/288, 526/279, 526/318.41, 526/318.42, 524/377, 524/558, 524/762
• US Class Current: 526/245
• CPC Class Codes: C08F 290/04 Polymers provided for in subclasses C08C or C08F
• CPC Class Codes: C08F 290/14 Polymers provided for in subclass C08G
• CPC Class Codes: C08L 51/00 Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds for ABS polymers C08L55/02; Compositions of derivatives of such polymers
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A method of modifying the surfaces of the polymeric objects by adding a polymerizable surfactant to the monomer mix used to form the object. Also disclosed are surface-modified objects prepared by this method, which is particularly suited for modifying the surfaces of contact lenses.

Claims

1. A surface-modified contact lens prepared by adding a polymerizable surfactant to a monomer mix used to form the contact lens.

3. The contact lens of claim 1, wherein the polymerizable surfactant is a surface active macromonomer described by the formula:

space="preserve" listing-type="equation">DC(A.sub.x B.sub.y)

wherein A is a monomer unit derived from at least one ethylenically unsaturated hydrophilic monomer, B is a monomer unit derived from at least one ethylenically unsaturated hydrophobic monomer, C is a functional chain transfer agent, D is an ethylenically unsaturated end group, and y is within the range of about 0.1 to about 0.9, and x+y=1.

4. The contact lens of claim 3 wherein A is selected from the group consisting of ethylenically unsaturated polyoxyalkylenes, polyacrylamides, polyvinylpyrrolidones, polyvinyl alcohols, poly (HEMA), and N-alkyl-N-vinyl acetamide.

5. The contact lens of claim 3 wherein A is an ethylenically unsaturated polyoxyalkylene selected from the group consisting of (meth)acrylated polyoxyalkylenes, (meth)acrylamido polyoxyalkylenes, styrenyl polyoxyalkylenes, alkenyl polyoxyalkylenes, vinyl carbonate polyoxyalkylenes and vinyl carbamate polyoxyalkylenes.

6. The contact lens of claim 5 wherein the polyoxyalkylene is polyethylene oxide.

7. The contact lens of claim 3 wherein A is (meth)acrylated polyethylene oxide.

8. The contact lens of claim 7 wherein A is methoxy polyethylene glycol methacrylate.

9. The contact lens of claim 4 wherein A is a methacrylate endcapped poly-N-vinylpyrrolidinone.

10. The contact lens of claim 4 wherein A is a methacrylate endcapped poly-N,N-dimethylacrylamide.

11. The contact lens of claim 3 wherein B is selected from the group consisting of alkyl (meth)acrylates, N-alkyl (meth)acrylamides, alkyl vinylcarbonates, alkyl vinylcarbamates, fluoroalkyl (meth)acrylates, N-fluoroalkyl (meth)acrylamides, N-fluoroalkyl vinylcarbonates, N-fluoroalkyl vinylcarbamates, silicone-containing (meth)acrylates, (meth)acrylamides, vinyl carbonates, vinyl carbamates, styrenic monomers and polyoxypropylene (meth)acrylates.

12. The contact lens of claim 11 wherein the styrenic monomers are selected from the group consisting of styrene, alpha-methyl styrene, para-methyl styrene, para-t-butyl monochloro styrene, and para-t-butyl dichloro styrene.

13. The contact lens of claim 11 wherein B is 1-H,1-H,5-H-octafluoropentyl methacrylate.

14. The contact lens of claim 13 wherein C is selected from the group consisting of mercapto carboxylic acids, mercapto alcohols, and aminomercaptans.

15. The contact lens of claim 14 wherein C is thioglycolic acid.

16. The contact lens of claim 14 wherein C is 2-mercaptoethanol.

17. The contact lens of claim 14 wherein C is 2-aminoethane thiol.

18. The contact lens of claim 15 wherein D is a (meth)acrylated hydroxy ester moiety derived from glycidyl (meth)acrylate.

19. The contact lens of claim 16 wherein D is a (meth)acrylated ester moiety derived from (meth)acryloyl chloride.

20. The contact lens of claim 16 wherein D is a (meth)acrylated urethane moiety derived from (meth)acrylated isocyanate.

21. The contact lens of claim 17 wherein D is a (meth)acrylated urea moiety derived from (meth)acrylated isocyanate.

22. The contact lens of claim 16 wherein D is a vinylcarbonate moiety derived from vinyl chloroformate.

23. The contact lens of claim 17 wherein D is a (meth)acrylated amide moiety derived from (meth)acryloyl chloride.

24. The contact lens of claim 17 wherein D is a vinylcarbamate moiety derived from vinyl chloroformate.

25. The contact lens of claim 3 which is a hydrogel contact lens.

26. The contact lens of claim 3 which is a rigid gas permeable lens.

27. The contact lens of claim 3 which is a silicone elastomer contact lens.

2. A surface-modified polymeric object prepared by adding a polymerizable surfactant to a monomer mix used to form the polymeric object, wherein the polymerizable surfactant is a surface active macromonomer described by the formula:

space="preserve" listing-type="equation">DC(A.sub.x B.sub.y)

wherein A is a monomer unit derived from at least one ethylenically unsaturated hydrophilic monomer, B is a monomer unit derived from at least one ethylenically unsaturated hydrophobic monomer, C is a functional chain transfer agent, D is an ethylenically unsaturated end group, y is within the range of about 0.1 to about 0.9, and x+y=1.