Silicone hydrogel polymers

• US 6,020,445 A
• Filed: 10/09/1997
• Issued: 02/01/2000
• Est. Priority Date: 10/09/1997
• Status: Expired due to Term

• Current Assignee: Johnson & Johnson Vision Products, Inc.
• Original Assignee: Johnson & Johnson Vision Products, Inc.
• Inventors: Nunez, Ivan M., Hargiss, Marcie, Vanderlaan, Douglas G.
• Primary Examiner(s): Lipman, Bernard
• Assistant Examiner(s): Sarofim, N.
• Application Number:
  US08/948,128
• Time in Patent Office: 845 Days
• Field of Search: 526/279, 526/212
• US Class Current: 526/279
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08F 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08F 290/148 Polysiloxanes
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

This invention relates to polymers that are formed by polymerizing a reaction mixture that comprises at least one silicone-containing monomer and at least one hydrophilic monomer. More particularly, this invention relates to polymers formed by polymerizing a reaction mixture that comprises at least one silicone-containing monomer and at least one hydrophilic monomer in the presence of a diluent.

Claims

1. A reaction mixture comprising one or more olefinic silicone-containing monomers, one or more hydrophilic monomers, and a diluent comprising the following structure:

##STR11## where R, R'"'"' and R" are independently selected from H, or unsubstituted, linear, branched or cyclic monovalent alkyl groups having 1 to 7 carbons with the proviso that no more than one of R, R'"'"' or R" is H; and

wherein said hydrophilic monomer is selected from the group consisting of N,N-dimiethyl acrylamide (DMA), 2-hydroxyethyl methacrylate (HEMA), glycerol methylacrylate, 2-hydroxyethyl methacrylamide, polyethyleneglycol, monomethacrylate, methacrylic acid, acrylic acid, N-vinyl prrolidone (NVP), N-vinyl-N-methyl acetamide, N-viny-N-ethyl acetamide, N-vinyl-N-methyl acctamide, N-vinyl-N-ethyl fomiamide and N-vinyl formamide;

said reaction mixture to be used to form a contact lens.

2. The reaction mixture of claim 1 wherein R, R'"'"', and R" are independently selected from unsubstituted linear, branched or cyclic alkyl groups having 1 to 7 carbons.

3. The reaction mixture of claim 1 wherein said structure of said diluent has 4 or more total carbons.

4. The reaction mixture of claim 1 wherein said structure of said diluent has 5 or more total carbons.

5. The reaction mixture of claim 1 wherein said diluent comprises a secondary alcohol.

6. The reaction mixture of claim 1 wherein said diluent comprises a tertiary alcohol.

7. The reaction mixture of claim 1 wherein said diluent is selected from the group consisting of 2-butanol, 2-propanol, menthol, cyclohexanol, cyclopentanol and exo-norbooreol, 2-pentanol, 3-pentanol, 2-hexanol, 3-hexanol, 3-methyl-2-butanol, 2-heptanol, 2-octanol, 2-nonanol, 2-decanol, 3-octanol, norborneol, and menthol.

8. The reaction mixture of claim 1 wherein said diluent is selected from the group consisting of tert-butanol, tert-amyl alcohol, 2-methyl-2-pentanol, 2,3-dimethyl-2-butanol, 3-methyl-3-pentanol, 1-methylcyclohexanol, 2-methyl-2-hexanol, 3,7-dimethyl-3-octanol, 1-chloro-2-methyl-2-propanol, 2-methyl-2-heptanol, 2-methyl-2-octanol, 2-2methyl-2-nonanol, 2-methyl-2-decanol, 3-methyl-3-hexanol, 3-methyl-3-heptanol, 4-methyl-4-heptanol, 3-methyl-3-octanol, 4-methyl-4-octanol, 3-methyl-3-nonanol, 4-methyl-4-nonanol, 3-methyl-3-octanol, 3-ethyl-3-hexanol, 3-ethyl-3-heptanol, 4-ethyl-4-heptanol, 4-propyl-4-heptanol, 4-isopropyl-4-heptanol, 2,4-dimethyl-2-pentanol, 1-methylcyclopentanol, 1-ethylcyclopentanol, 1-ethylcyclopentanol, 3-hydroxy-3-methyl-1-butene, 4-hydroxy-4-methyl-1-cyclopentanol, 2-phenyl-2-propanol, 2-methoxy-2-methyl-2-propanol 2,3,4-trimethyl-3-pentanol, 3,7-dimethyl-3-octanol, 2-phenyl-2-butanol, 2-methyl-1-phenyl-2-propanol and 3-ethyl-3-pentanol.

9. The reaction mixture of claim 1 wherein said diluent is selected from the group consisting of tert-butanol, tert-amyl alcohol, 2-butanol, 2-methyl-2-pentanol, 2,3-dimethyl-2-butanol, 3-methyl-3-pentanol, 3-ethyl-3-pentanol, and 3,7-dimethyl-3-octanol.

10. The reaction mixture of claim 1 wherein said diluent is selected from the group consisting of tert-butanol, 3-methyl-3-pentanol and 3,7-dimethyl-3-octanol.

11. The reaction mixture of claim 1 wherein said silicone-containing monomer has Si and attached O present in an amount greater than 20 weight percent of the total molecular weight of said silicone-containing monomer.

12. The reaction mixture of claim 1 wherein said silicone-containing monomer has Si and attached O present in an amount greater than 30 weight percent of the total molecular weight of said silicone-containing monomer.

13. The reaction mixture of claim 1 wherein said silicone-containing monomers comprise polymerizable functional groups selected from the group consisting of acrylate, methacrylate, acrylamide, methacrylamide, N-vinyl lactam, and styryl functional groups.

14. The reaction mixture of claim 1 wherein said silicone-containing monomers are selected from the group consisting of methacryloxypropyl tris(trismethylsiloxy) silane and α

,ω

-bismethacryloxypropyl polydimethylsiloxane.

15. The reaction mixture of claim 1 wherein said hydrophilic monomers are selected from the group consisting of N,N-dimethyl acrylamide (DMA) and N-vinyl pyrrolidone (NVP).

16. The reaction mixture of claim 1 further comprising a crosslinking agent.

17. The reaction mixture of claim 16 wherein said crosslinking agent is selected from the group consisting of ethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, and glycerol trimethacrylate, polyethylene glycol dimentacrylate, polyacrylate ester, and polymethacrylate ester, end-capped polyoxyethylene polyoxylethylene polyols containing two or more terminal methacrylate moieties and alkoxylated glucose or sucrose which is reacted with an isocyanate, methacrylic acid or a methacrylating agent.

18. The reaction mixture of claim 1 further comprising a catalyst.

19. The reaction mixture of claim 18 wherein said catalyst is selected from the group consisting of lauroyl peroxide, benzoyl peroxide, isopropyl percarbonate, azobisisobutyronitrile, 2-hydroxy-2-metnyl-1-phyenyl-propan-1-one, and a combination of camphorquinone and ethyl 4-(N,N-dimethylamino)benzoate.

20. The reaction mixture of claim 1 wherein said silicone-containing monomer is selected from the group consisting of tris(trimethylsiloxy)silylpropyl methacrylate and α

,ω

-bismethacryloxypropyl polydimethylsiloxane, and wherein said hydrophilic monomer comprises N,N-dimethylacrylamide, and said diluent is a tertiary alcohol.

21. The reaction mixture of claim 1 wherein said silicone-containing monomer comprises 10 to 90 weight percent of the polymerizable components, and wherein said hydrophilic monomer comprises 5 to 60 weight percent of the polymerizable components, and said diluent comprises 1 to 40 weight percent of the combined weight of polymerizable components and diluent.

22. The reaction mixture of claim 1 wherein said silicone-containing monomer comprises 30 to 80 weight percent of the polymerizable components, and wherein said hydrophilic monomer comprises 10 to 40 weight percent of the polymerizable components, and said diluent comprises 3 to 30 weight percent of the combined weight of polymerizable components and diluent weight.

23. The reaction mixture of claim 1 wherein said silicone-containing monomer has Si and attached O present in an amount greater than 20 weight percent of the total molecular weight of said silicone-containing monomer.

24. The reaction mixture of claim 1 wherein said silicone-containing monomer has Si and attached O present in an amount greater than 20 weight percent of the total molecular weight of said silicone-containing monomer.

25. The reaction mixture of claim 1 wherein said silicone-containing monomer has Si and attached O present in an amount greater than 30 weight percent of the total molecular weight of said silicone-containing monomer.