Biomedical devices containing internal wetting agents

Patent metadata

Field	Value
Publication number	US-10935696-B2
Application number	US-202016839156-A
Country	US
Kind code	B2
Filing date	Apr 3, 2020
Priority date	Sep 10, 2001
Publication date	Mar 2, 2021
Grant date	Mar 2, 2021

Abstract

This invention includes a wettable biomedical device containing a high molecular weight hydrophilic polymer and a hydroxyl-functionalized silicone-containing monomer.

First claim

What is claimed is:

1. A silicone hydrogel formed from a reaction mixture comprising a high molecular weight hydrophilic polymer; an effective amount of an hydroxyl-functionalized silicone-containing monomer; an ultra-violet absorbing compound; and a photochromic compound.

2. The silicone hydrogel of claim 1 wherein said hydrophilic polymer is selected from the group consisting of polyamides, polylactones, polyimides, polylactams, functionalized polyamides, functionalized polylactones, functionalized polyimides, functionalized polylactams, and mixtures thereof.

3. The silicone hydrogel of claim 1 wherein said hydrophilic polymer is selected from the group consisting of poly-N-vinyl pyrrolidone, poly-N-vinyl-2-piperidone, poly-N-vinyl-2-caprolactam, poly-N-vinyl-3-methyl-2-caprolactam, poly-N-vinyl-3-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-caprolactam, poly-N-vinyl-3-ethyl-2-pyrrolidone, and poly-N-vinyl-4,5-dimethyl-2-pyrrolidone, polyvinylimidazole, poly-N—N-dimethylacrylamide, polyvinyl alcohol, polyacrylic acid, polyethylene oxide, poly 2 ethyl oxazoline, heparin polysaccharides, polysaccharides, mixtures and copolymers thereof.

4. The silicone hydrogel of claim 1 wherein said hydrophilic polymer comprises poly-N-vinylpyrrolidone.

5. The silicone hydrogel of claim 1 comprising about 1 to about 15 weight % high molecular weight hydrophilic polymer.

6. The silicone hydrogel of claim 1 wherein said hydroxyl-functionalized silicone-containing monomer is a compound of Formula I or II

wherein:
n is an integer between 3 and 35
R 1 is hydrogen, C 1-6 alkyl,
R 2 , R 3 , and R 4 , are independently, C 1-6 alkyl, triC 1-6 alkylsiloxy, phenyl, naphthyl, substituted C 1-6 alkyl, substituted phenyl, or substituted naphthyl
where the alkyl substitutents are selected from one or more members of the group consisting of C 1-6 alkoxycarbonyl, C 1-6 alkyl, C 1-6 alkoxy, amide, halogen, hydroxyl, carboxyl, C 1-6 alkylcarbonyl and formyl, and
where the aromatic substitutents are selected from one or more members of the group consisting of C 1-6 alkoxycarbonyl, C 1-6 alkyl, C 1-6 alkoxy, amide, halogen, hydroxyl, carboxyl, C 1-6 alkylcarbonyl and formyl;
R 5 is a hydroxyl, an alkyl group containing one or more hydroxyl groups, or (CH 2 (CR 9 R 10 ) y O) x )—R 11 wherein y is 1 to 5, preferably 1 to 3, x is an integer of 1 to 100, preferably 2 to 90 and more preferably 10 to 25; R 9 -R 11 are independently selected from H, alkyl having up to 10 carbon atoms and alkyls having up to 10 carbon atoms substituted with at least one polar functional group;
R 6 is a divalent group comprising up to 20 carbon atoms;
R 7 is a monovalent group that can undergo free radical or cationic polymerization, comprising up to 20 carbon atoms, and
R 8 is a divalent or trivalent group comprising up to 20 carbon atoms.

7. The silicone hydrogel of claim 6 wherein said hydroxyl-functionalized silicone-containing monomer is selected from the group consisting of 2-propenoic acid, 2-methyl-2-hydroxy-3-[3-[1,3,3,3-tetramethyl-1-[trimethylsily)oxy]disiloxanyl]propoxy]propyl ester, (3-methacryloxy-2-hydroxypropyloxy)propyltris(trimethylsiloxy)silane, (2-methacryloxy-3-hydroxypropyloxy)propylbis(trimethylsiloxy)methylsilane and mixtures thereof.

8. The silicone hydrogel of claim 1 further comprising at least one additional silicone containing monomer.

9. The silicone hydrogel of claim 8 wherein said additional silicone containing monomers are selected from the group consisting of amide analogs of 3-methacryloxypropyltris(trimethylsiloxy)silane; siloxane vinyl carbamate analogs, siloxane vinyl carbonate analogs, and siloxane containing monomers, combinations and oligomers thereof.

10. The silicone hydrogel of claim 8 wherein said additional silicone containing monomers are selected from the group consisting of 3-methacryloxypropyltris(trimethylsiloxy)silane, monomethacryloxypropyl terminated polydimethylsiloxanes, polydimethylsiloxanes, 3-methacryloxypropylbis(trimethylsiloxy)methylsilane, methacryloxypropylpentamethyl disiloxane and combinations thereof.

11. The silicone hydrogel of claim 1 further comprising at least one hydrophilic monomer.

12. The silicone hydrogel of claim 11 wherein said at least one hydrophilic monomer comprises at least one acrylic group, vinyl group or a combination thereof.

13. The silicone hydrogel of claim 12 wherein said acrylic group has the formula CH 2 ═CRCOX, where R is hydrogen or C 1-6 alkyl and X is O or N.

14. The silicone hydrogel of claim 11 wherein said at least one hydrophilic monomer is selected from the group consisting of N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxyethyl methacrylamide, polyethyleneglycol monomethacrylate, methacrylic acid, acrylic acid, N-vinyl pyrrolidone, N-vinyl-N-methyl acetamide, N-vinyl-N-ethyl acetamide, N-vinyl-N-ethyl formamide, N-vinyl formamide, hydrophilic vinyl carbonate monomers, vinyl carbamate monomers, hydrophilic oxazolone monomers, polydextran and copolymers and combinations thereof.

15. The silicone hydrogel of claim 11 wherein said at least one hydrophilic monomer comprises at least one polyoxyethylene polyol having one or more of the terminal hydroxyl groups replaced with a functional group containing a polymerizable double bond.

16. The silicone hydrogel of claim 15 wherein said at least one hydrophilic monomer is selected from the group consisting of polyethylene glycol, ethoxylated alkyl glucoside, and polyethylene polyols having one or more terminal polymerizable olefinic groups bonded to the polyethylene polyol.

17. The silicone hydrogel of claim 11 wherein said at least one hydrophilic monomer is selected from the group consisting of N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxyethyl methacrylamide, N-vinylpyrrolidone, polyethyleneglycol monomethacrylate, methacrylic acid, acrylic acid and combinations thereof.

18. The silicone hydrogel of claim 11 wherein said at least one hydrophilic monomer comprises N,N-dimethylacrylamide.

19. The silicone hydrogel of claim 1 comprising about 1% to about 15% high molecular weight hydrophilic polymer; about 5 to about 90 weight % hydroxyl-functionalized silicone containing monomer; 5 to about 60 weight % additional silicone containing monomer and 5 to about 60 weight % hydrophilic monomer.

20. The silicone hydrogel of claim 1 wherein said hydrophilic polymer has a weight average molecular weight of at least about 10,000 daltons.

21. The silicone hydrogel of claim 1 wherein said hydrophilic polymer comprises at least one cyclic moiety along a backbone portion of said hydrophilic polymer.

22. The silicone hydrogel of claim 1 wherein said hydrophilic polymer is selected from the group consisting of polymers comprising cyclic amides, cyclic imides and combinations thereof.

23. An ophthalmic device comprising the silicone hydrogel of claim 1 .

Assignees

• Johnson & Johnson Vision Care

Inventors

• Mccabe Kevin P
• Molock Jr Frank F
• Hill Gregory A
• Alli Azaam
• Steffen Robert B
• Vanderlaan Douglas G
• Ford James D

Classifications

• C08F290/068

  Polysiloxanes · CPC title

• A61L2430/16

  for reconstruction of eye parts, e.g. intraocular lens, cornea · CPC title

• C08F283/06

  on to polyethers, polyoxymethylenes or polyacetals {(C08F283/004 takes precedence)} · CPC title

• G02B1/043 Primary

  Contact lenses · CPC title

• C08F290/06

  Polymers provided for in subclass C08G · CPC title