Silicone hydrogels having consistent concentrations of multi-functional polysiloxanes

• US 8,097,565 B2
• Filed: 06/04/2004
• Issued: 01/17/2012
• Est. Priority Date: 06/30/2003
• Status: Active Grant

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Inventors: Hill, Gregory A., Heaton, John C., Clark, Michael R., Mahadevan, Shivkumar, Molock, Frank F., Caison, Carrie L
• Primary Examiner(s): Marschel, Ardin
• Assistant Examiner(s): BOESEN, CHRISTIAN C
• Application Number:
  US10/861,798
• Publication Number:
  US 20050255231A1
• Time in Patent Office: 2,783 Days
• Field of Search: 504/14
• US Class Current: 506/14
• CPC Class Codes: C08G 77/04 Polysiloxanes
• CPC Class Codes: C08L 33/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The present invention relates to a process comprising forming a monomer mixture comprising at least one monofunctional silicone containing component which comprises at least one difunctional byproduct and adding to said monomer mixture a normalizing amount of said at least one difunctional byproduct and curing said monomer mixture to form a biomedical device.

Claims

1. A process comprising forming a monomer mixture comprising at least one monofunctional silicone containing component which comprises at least one difunctional byproduct;

determining the concentration of said difunctional byproduct in said monofunctional silicone containing component; and

adding to said monomer mixture a normalizing amount of said at least one difunctional byproduct and curing said monomer mixture to form a biomedical device.

2. The process of claim 1 wherein said normalizing amount is between about 0.1 and about 5%, based upon the weight of said monofunctional silicone-containing component.

3. The process of claim 1 wherein said normalizing amount is between about 1 and about 3%, based upon the weight of said monofunctional silicone-containing component.

4. The process of claim 1 wherein said monofunctional silicone containing component is selected from the group consisting of polysiloxanylalkyl(meth)acrylic monomers, hydroxyl functionalized silicone-containing monomers, poly(organosiloxane) prepolymer, vinyl carbonate monomers, vinyl carbamate monomers, polysiloxanes with a polar fluorinated graft or side group having a hydrogen atom attached to a terminal difluoro-substituted carbon atom and combinations thereof.

5. The process of claim 1 wherein said monofunctional silicone containing component comprises a polysiloxanylalkyl(meth)acrylic monomers of Formula I

6. The process of claim 1 wherein said wherein said monofunctional silicone-containing component is selected from the group consisting of methacryloxypropyl tris(trimethylsiloxy) silane, pentamethyldisiloxanyl methylmethacrylate, and methyldi(trimethylsiloxy)methacryloxymethyl silane.

7. The process of claim 1 wherein said wherein said monofunctional silicone-containing component comprises methacryloxypropyl tris(trimethylsiloxy)silane.

8. The process of any of claims 1, 6, or 7 wherein said difunctional silicone-containing byproduct comprises bis(trimethylsiloxy)methylsilylpropyl-1,2-dimethacrylate.

9. The process of claim 1 wherein said monofunctional silicone containing component is a hydroxyl-functionalized silicone containing monomer of Formula I

10. The process of claim 9 wherein R¹ is hydrogen,

R², R³, and R⁴ are independently selected from the group consisting of C_1-6alkyl and triC_1-6alkylsiloxy;

R⁵ selected from the group consisting of hydroxyl, —

CH₂OH or CH₂CHOHCH₂OH;

R⁶ is selected from the group consisting of divalent C_1-6alkyl, C_1-6alkyloxy, C_1-6alkyloxyC_1-6alkyl, phenylene, naphthalene, C_1-12cycloalkyl, C_1-6alkoxycarbonyl, amide, carboxy, C_1-6alkylcarbonyl, carbonyl, C_1-6alkoxy, substituted C_1-6alkyl, substituted C_1-6alkyloxy, substituted C_1-6alkyloxyC_1-6alkyl, substituted phenylene, substituted naphthalene, substituted C_1-12cycloalkyl, where the substituents are selected from one or more members of the group consisting of C_1-6alkoxycarbonyl, C_1-6alkyl, C_1-6alkoxy, amide, halogen, hydroxyl, carboxyl, C_1-6alkylcarbonyl and formyl;

R⁷ is selected from the group consisting of acrylate, styryl, vinyl, vinyl ether, itaconate group, C_1-6alkylacrylate, acrylamide, C_1-6alkylacrylamide, N-vinyllactam, N-vinylamide, C_2-12alkenyl, C_2-12alkenylphenyl, C_2-12alkenylnaphthyl, C_2-6alkenylphenylC_1-6alkyl, vinyl ether and epoxide groups;

R⁸ is selected from the group consisting of divalent C_1-6alkyl, C_1-6alkyloxy, C_1-6alkyloxyC_1-6alkyl, phenylene, naphthalene, C_1-12cycloalkyl, C_1-6alkoxycarbonyl, amide, carboxy, C_1-6alkylcarbonyl, carbonyl, C_1-6alkoxy, substituted C_1-6alkyl, substituted C_1-6alkyloxy, substituted C_1-6alkyloxyC_1-6alkyl, substituted phenylene, substituted naphthalene, substituted C_1-2cycloalkyl, where the substituents are selected from one or more members of the group consisting of C_1-6alkoxycarbonyl, C_1-6alkyl, C_1-6alkoxy, amide, halogen, hydroxyl, carboxyl, C_1-6alkylcarbonyl and formyl.

11. The process of claim 1 wherein said monofunctional silicone-containing component is selected from the group consisting of (3-methacryloxy-2-hydroxypropyloxy)propylbis(trimethylsiloxy)methylsilane, (2-methacryloxy-3-hydroxypropyloxy)propylbis(trimethylsiloxy)methylsilane, (3-methacryloxy-2-hydroxypropyloxy)propyltris(trimethylsiloxy)silane, 3-methacryloxy-2-(2-hydroxyethoxy)propyloxy)propylbis(trimethylsiloxy)methylsilane, monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane, and mixtures thereof.

12. The process of claim 1 wherein said monofunctional silicone-containing component is selected from the group consisting of (3-methacryloxy-2-hydroxypropyloxy)propylbis(trimethylsiloxy)methylsilane), (2-methacryloxy-3-hydroxypropyloxy)propylbis(trimethylsiloxy)methylsilane, monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane, and mixtures thereof.

13. The process of claims 9, 10, 11 or 12 wherein said difunctional silicone-containing byproduct comprises bis(trimethylsiloxy)methylsilylpropyl-1,2-dimethacrylate.

14. The process of claim 1 wherein said monofunctional silicone-containing component is present in an amount between about 25 and about 60 weight %, based upon weight of all reactive components in the monomer mixture.

15. The process of claim 1 wherein said monomer mixture further comprises at least one hydrophilic component.

16. The process of claim 15 wherein said hydrophilic component is present in an amount between about 10 and about 60%, based upon weight of all reactive components in the monomer mixture.

17. The process of claim 15 wherein said hydrophilic component is selected from the group consisting of N,N-dimethyl acrylamide, 2-hydroxyethyl acrylate, glycerol methacrylate, 2-hydroxyethyl methacrylamide, N-vinylpyrrolidone, polyethyleneglycol monomethacrylate, and mixtures thereof.

18. The process of claim 15 wherein said hydrophilic component is selected from the group consisting of N,N-dimethyl acrylamide, 2-hydroxyethyl macrylate and mixtures thereof.

19. The process of claim 1 wherein said monofunctional silicone containing component comprises (3-methacryloxy-2-hydroxypropyloxy)propylbis(trimethylsiloxy)methylsilane, monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane and mixtures thereof, said at least one difunctional byproduct comprises bis(trimethylsiloxy)methylsilylpropyl-1,2-dimethacrylate and said monomer mixture further comprises at least one high molecular weight hydrophilic polymer, and at least one hydrophilic component is selected from the group consisting of N,N-dimethyl acrylamide, 2-hydroxyethyl macrylate and mixtures thereof.

20. The process of claim 1 wherein said biomedical device is an ophthalmic device.

21. The process of claim 1 wherein said biomedical device is a contact lens.

22. The process of claim 1 wherein only one difunctional byproduct is added to said monomer mixture.