Polymers and nanogel materials and methods for making and using the same

Patent metadata

Field	Value
Publication number	US-9726906-B2
Application number	US-201514948474-A
Country	US
Kind code	B2
Filing date	Nov 23, 2015
Priority date	May 25, 2012
Publication date	Aug 8, 2017
Grant date	Aug 8, 2017

Abstract

Provided are articles such as medical devices which comprise at least one water soluble, crosslinked copolymer. The primary polymer chains of the copolymer are hydrophilic and independently have a degree of polymerization in the range of about 10 to about 10,000. The water soluble, crosslinked copolymers of the present invention are free from terminal substrate associating segments. The copolymers may be incorporated into a formulation from which the article is made or may be contacted with the article post-formation.

First claim

What is claimed is:

1. A process comprising contacting a contact lens with a solution comprising a lipid uptake reducing amount of at least one water soluble, crosslinked copolymer under contacting conditions suitable to associate said copolymer with said contact lens; wherein said cross-linked copolymer comprises a plurality of crosslinked primary polymer chains each having a degree of polymerization in the range of about 10 to about 10,000, wherein said cross-linked copolymer does not comprise repeating units derived from a substituted or unsubstituted acrylic acid bonded directly to the polymer backbone.

2. The process of claim 1 wherein said contact lens comprises a silicone hydrogel contact lens.

3. The process of claim 1 wherein said water soluble, cross-linked copolymer has a cross-linker to primary polymer chain molar ratio in the range of about 0.01 to about 3.

4. The process of claim 1 wherein said lipid uptake reducing amount is at least about 10 ppm.

5. The process of claim 1 wherein said lipid uptake reducing amount is in the range of about 10 ppm to about 10,000 ppm.

6. The process of claim 1 wherein the lipid uptake by the lens is no more than about 10 μg/lens.

7. The process of claim 1 , wherein said primary polymer chains are selected from the group consisting of hydrophilic polymers and copolymers, proton donating polymers and copolymers, proton accepting polymers and copolymers, ionic polymers and copolymers, complexing polymers and copolymers, stimuli responsive polymers and copolymers and mixtures thereof.

8. The process of claim 7 , wherein the proton donating polymers and copolymers comprise one or more alcohols.

9. The process of claim 7 , wherein the proton accepting polymers and copolymers comprise one or more amides.

10. The process of claim 7 , wherein the ionic polymers and copolymers comprise one or more of the following: a carboxylate, a sulfonate, an ammonium salt, and a phosphonium salt.

11. The process of claim 7 , wherein the complexing polymers and copolymers comprise one or more boronic acid functionalities and/or hydroxyl functionalities.

12. The process of claim 7 , wherein the stimuli responsive polymers and copolymers comprise a polymer selected from the group consisting of temperature-responsive polymers, pH responsive polymers, electrolyte responsive polymers, light responsive polymers and mixtures thereof.

13. The process of claim 12 , wherein the temperature-responsive polymer is poly(N-isopropylacrylamide).

14. The process of claim 7 wherein the copolymers are both hydrophilic and proton donating.

15. The process of claim 14 wherein the copolymers comprise repeating units derived from the polymerization of at least one monomer selected from the group consisting of N-vinyl pyrrolidone, N,N-dimethyl acrylamide, and N-hydroxypropyl methacrylamide.

16. The process of claim 1 wherein the copolymers are formed from monomers selected from the group consisting of vinyl amides, vinyl lactones, vinylimides, vinyl lactams, hydrophilic (meth)acrylates, (meth)acrylamides, and mixtures thereof.

17. The process of claim 1 wherein said primary polymer chains are cross-linked by at least one cross-linking agent selected from the group consisting of an N,N′-alkylenebis(meth)acrylamide, polyalkyleneglycoldi(meth)acrylate, polyalkyleneglycoldi(meth)acrylamide, and combinations thereof.

18. The process of claim 1 wherein said primary polymer chains independently have a degree of polymerization in the range of about 50 to about 5,000.

19. The process of claim 1 wherein said primary polymer chains independently have a degree of polymerization in the range of about 100 to about 1000.

20. The process of claim 1 wherein said primary polymer chains independently have a degree of polymerization in the range of about 100 to about 500.

21. The process of claim 1 wherein said primary polymer chains independently have a degree of polymerization in the range of about 100 to about 300.

22. The process of claim 1 wherein said cross-linked copolymer has a cross-linker to primary polymer chain molar ratio in the range of about 0.01 to about 3.

23. The process of claim 1 wherein said primary polymer chains are cross-linked to other primary polymer chains of said hydrophilic nanogel having polydispersity indices (PDIs) of less than about 1.5.

24. The process of claim 22 wherein said primary polymer chains are cross-linked by covalent bonding, ionic bonding, hydrogen bonding, or a combination thereof.

25. The process of claim 1 wherein said primary polymer chains, ζ, are represented by the formula

wherein R 1 is a divalent group selected from the group consisting of optionally substituted alkylene; optionally substituted saturated, unsaturated or aromatic carbocyclic or heterocyclic rings; optionally substituted alkylthio; optionally substituted alkoxy; or optionally substituted dialkylamino;
U is independently selected from the group consisting of hydrogen, halogen, C 1 -C 4 alkyl which may be optionally substituted with hydroxyl, alkoxy, aryloxy (OR″), carboxy, acyloxy, aroyloxy (O 2 CR″), alkoxy-carbonyl, aryloxy-carbonyl (CO 2 R″) and combinations thereof;
V is independently selected from the group consisting of R″, —CO 2 R″, —COR″, —CN, —CONH 2 , —CONHR″, —CONR″ 2 , —O 2 CR″, —OR″, cyclic and acyclic N-vinyl amides and combinations thereof;
R″ is independently selected from the group consisting of optionally substituted C 1 -C 18 alkyl, C 2 -C 18 alkenyl, aryl, heterocyclyl, alkaryl wherein the substituents are independently selected from the group that consists of epoxy, hydroxyl, alkoxy, acyl, acyloxy, carboxy, carboxylate, sulfonic acid, and sulfonate, alkoxy- or aryloxy-carbonyl, isocyanato, cyano, silyl, halo, dialkylamino; phosphoric acids, phosphates, phosphonic acids, phosphonates and combinations thereof;
R 15 ′ and R 15 are residues of hydrophilic, free radical reactive cross-linking agents;
R 18 is a controlled radical polymerization agent;
ζ i is another primary chain, are mole fractions, and α is equal to about 0.85 to about 0.999, β is not 0, and the mole fractions of β and γ combined are about 0.15 to about 0.001.

26. The process of claim 25 wherein said primary polymer chains, ζ, are represented by the formula

Wherein R 1 , U, V, R 15 , R 15′ , α, β, γ and m are as defined in claim 25 .

27. The process of claim 25 or 26 wherein R 1 is selected from the group consisting of 4-cyanopentanoate, isobutanoic, or a benzylic group.

28. The process of claim 25 or 26 wherein R 1 is selected from the group consisting of a cyano-methy or cumyl group.

29. The process of claim 25 or 26 wherein R 1 is polyvalent.

30. The process of claim 25 or 26 wherein U is selected from H or methyl.

31. The process of claim 25 or 26 wherein R″ is selected from the group consisting of methyl, —CH 2 OH, —CH 2 CH 2 OH, —CH 2 CH 2 CH 2 OH, —CH 2 —CO 2 − , —CH 2 CH 2 —CO 2 − , —CH 2 CH 2 CH 2 —CO 2 − , —CH 2 CH 2 CH 2 CH 2 —CO 2 − , —CH 2 CH 2 CH 2 CH 2 CH 2 —CO 2 − , —CH 2 —SO 3 − , —C

Assignees

• Johnson & Johnson Vision Care

Inventors

• Scales Charles W
• Mccabe Kevin P
• Healy Brent Matthew

Classifications

• G02B1/043 Primary

  Contact lenses · CPC title

• G02C2202/16

  Laminated or compound lenses · CPC title

• G02C7/049 Primary

  Contact lenses having special fitting or structural features achieved by special materials or material structures · CPC title

• C08L81/00

  Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers · CPC title

• C08L101/14

  the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels · CPC title