Surface modification of polymer objects

• US 5,219,965 A
• Filed: 11/27/1990
• Issued: 06/15/1993
• 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:
  US07/619,282
• Time in Patent Office: 931 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 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 method of modifying the surface of a polymeric object which comprises adding a polymerizable surfactant to the monomer mix used to form the polymeric object.

2. The method of claim 1 wherein the polymerizable surfactant is a surface active macromer 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.

3. The method of claim 2 wherein A is selected from the group consisting of ethylenically unsaturated polyoxyalkylenes, polyacrylamides, polyvinylpyrrolidones, polyvinyl alcohols, poly (HEMA), and N-alkyl-N-vinyl acetamide.

4. The method of claim 2 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.

5. The method of claim 4 wherein the polyoxyalkylene is polyethylene oxide.

6. The method of claim 2 wherein A is (meth)acrylated polyethylene oxide.

7. The method of claim 6 wherein A is methoxy polyethylene glycol methacrylate.

8. The method of claim 3 wherein A is a methacrylate endcapped poly-N-vinylpyrrolidinone.

9. The method of claim 3 wherein A is a methacrylate endcapped poly-N,N-dimethylacrylamide.

10. The method of claim 2 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.

11. The method of claim 10 wherein the styrenic monomers are selected from the group consisting of styrene, alpha-methyl styrene, paramethyl styrene, para-t-butyl monochloro styrene, and para-t-butyl dichloro styrene.

12. The method of claim 10 wherein B is 1H,1H,5H-octafluoropentyl methacrylate.

13. The method of claim 2 wherein C is selected from the group consisting of mercapto carboxylic acids, mercapto alcohols, and aminomercaptans.

14. The method of claim 13 wherein C is thioglycolic acid.

15. The method of claim 13 wherein C is 2-mercaptoethanol.

16. The method of claim 13 wherein C is 2-aminoethane thiol.

17. The method of claim 14 wherein D is a (meth)acrylated hydroxy ester moiety derived from glycidyl (meth)acrylate.

18. The method of claim 15 wherein D is a (meth)acrylated ester moiety derived from (meth)acryloyl chloride.

19. The method of claim 15 wherein D is a (meth)acrylated urethane moiety derived from (meth)acrylated isocyanate.

20. The method of claim 16 wherein D,is a (meth)acrylated urea moiety derived from (meth)acrylated isocyanate.

21. The method of claim 15 wherein D is a vinylcarbonate moiety derived from vinyl chloroformate.

22. The method of claim 16 wherein D is a (meth)acrylated amide moiety derived from (meth)acryloyl chloride.

23. The method of claim 16 wherein D is a vinylcarbamate moiety derived from vinyl chloroformate.

24. The method of claim 1 wherein the polymeric object is a contact lens.

25. The method of claim 24 wherein the contact lens is a hydrogel contact lens.

26. The method of claim 24 wherein the contact lens is a rigid gas permeable lens.

27. The method of claim 24 wherein the contact lens is a silicone elastomer contact lens.