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

• US 10,502,867 B2
• Filed: 08/03/2018
• Issued: 12/10/2019
• Est. Priority Date: 05/25/2012
• Status: Active Grant

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Inventors: Scales, Charles W., McCabe, Kevin P., Healy, Brent Matthew
• Primary Examiner(s): Salamon, Peter A
• Application Number:
  US16/053,865
• Publication Number:
  US 20180341044A1
• Time in Patent Office: 494 Days
• Field of Search: None
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: C08F 293/005 using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
• CPC Class Codes: C08J 7/00 Chemical treatment or coating of shaped articles made of macromolecular substances coating with metallic material C23C; electrolytic deposition of metals C25
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 53/00 Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 81/00 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 Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Provided are compositions comprising a block copolymer of the following formula: [A]-B-[Q], wherein [A] is a polymer that has an affinity for a substrate; B is a linking group comprising an optionally-substituted, polyvalent linking group having a molecular weight of no more than 1000 g/mole; and [Q] comprises a semi-crosslinked, ungelled polymer derived from copolymerization of an ethylenically unsaturated monomer with a poly-functional ethylenically unsaturated monomer. Such block copolymers are cross-linked via the [Q] segment, but not macroscopically gelled. The [Q] segment is hydrophilic and has a degree of polymerization in the range of about 10 to about 10,000. The [A] segment is located on at least one terminal end of said block copolymer, comprises between about 1 and about 200 repeating units. The block copolymer is associated, via the linear substrate associative segment with a surface comprising at least one hydrophobic site, such as a silicone hydrogel. The polymers may be incorporated into a formulation from which the silicone hydrogel is made or may be contacted with the silicone hydrogel post-formation.

Claims

1. An ophthalmic device comprising a silicone-containing polymer substrate and an amphiphilic nanogel material, the amphiphilic nanogel material comprising at least one stable, block copolymer that is cross-linked but not macroscopically gelled comprising in said block copolymer'"'"'s backbone, a hydrophilic segment that has a degree of polymerization in the range of about 10 to about 10,000, and a linear substrate associative segment on at least one terminal end of said block copolymer, wherein said linear substrate associative segment comprises between about 1 and about 200 siloxy units, wherein said block copolymer is associated, via the linear substrate associative segment with a surface comprising at least one hydrophobic site and provides said ophthalmic device with a reduction in lipid uptake compared to the silicone-containing polymer of at least about 20%.

2. The ophthalmic device of claim 1 wherein said lipid uptake is less than about 12 μ

g/lens.

3. The ophthalmic device of claim 2 wherein said lipid uptake is about 10 μ

g/lens or less.

4. The ophthalmic device of claim 1 wherein said hydrophilic segment has a cross-linker to primary chain molar ratio in the range of about 0.01 to about 1.5.

5. The ophthalmic device of claim 1 wherein said at least one stable block copolymer comprises 6 to 60 siloxy repeat units.

6. The ophthalmic device of claim 1 wherein said hydrophilic segment of said block copolymer has a degree of polymerization in the range of about 50 to about 5,000.

7. The ophthalmic device of claim 6 wherein said hydrophilic segment of said block copolymer has a degree of polymerization in the range of about 100 to about 1000.

8. The ophthalmic device of claim 1 wherein hydrophilic segment and the linear substrate associative segment comprising a linear silicone are present in said block copolymer in a weight ratio, based upon the degree of polymerization, in the range of about 1:

1 and about 500;

1.

9. The ophthalmic device of claim 8 wherein the weight ratio of hydrophilic segment to the linear silicone, based upon degree of polymerization is in the range of about 1:

1 and about 200;

1.

10. The ophthalmic device of claim 1 wherein said at least one stable block copolymer comprises 6 to 20 siloxy repeat units.