Polymers comprising sulfonic acid groups

Patent metadata

Field	Value
Publication number	US-9459377-B2
Application number	US-201414155678-A
Country	US
Kind code	B2
Filing date	Jan 15, 2014
Priority date	Jan 15, 2014
Publication date	Oct 4, 2016
Grant date	Oct 4, 2016

Abstract

The present invention relates to a polymers and hydrogels comprising a sulfonic acid component formed from reactive components comprising (i) at least one hydrophobic monomer and (ii) at least one sulfonic acid-containing component, wherein the sulfonic acid-containing component is comprised of a salt formed by a non-polymerizable, hydrophilic base and a polymerizable sulfonic acid. One or more embodiments provide that the at least one hydrophobic monomer comprises a silicone component.

First claim

What is claimed is:

1. A silicone-containing polymer comprising a sulfonic acid component formed from reactive components comprising (i) at least one silicone component and (ii) at least one sulfonic acid-containing component, wherein said sulfonic acid-containing component is comprised of a salt formed by a non-polymerizable, hydrophilic base comprising a component whose conjugate acid has a pKa is 9 or less and a polymerizable sulfonic acid.

2. The silicone-containing polymer of claim 1 , wherein said polymerizable sulfonic acid is selected from the group consisting of 2-acrylamido-2-methylpropane sulfonic acid, p-styrenesulfonic acid, 2-methacryloyloxyethylsulfonic acid, 3-methacryloyloxy-2-hydroxypropylsulfonic acid, allylsulfonic acid, 3-methacryloyloxypropylsulfonic acid, vinylsulfonic acid, and combinations thereof.

3. The silicone-containing polymer of claim 1 , wherein said hydrophilic base comprises an aromatic amine whose conjugate acid has a pKa of 7.8 or less.

4. The silicone-containing polymer of claim 3 , wherein said aromatic amine is selected from the group consisting of imidazole, aniline, pyridine, and derivatives thereof.

5. A silicone-containing polymer of claim 1 , wherein said at least one silicone component is selected from compounds of Formula I:

wherein:
R 1 is independently selected from monovalent reactive groups, monovalent alkyl groups, or monovalent aryl groups, any of the foregoing which may further comprise functionality selected from hydroxy, amino, oxa, carboxy, alkyl carboxy, alkoxy, amido, carbamate, carbonate, halogen or combinations thereof; and monovalent siloxane chains comprising 1-100 Si—O repeat units which may further comprise functionality selected from alkyl, hydroxy, amino, oxa, carboxy, alkyl carboxy, alkoxy, amido, carbamate, halogen or combinations thereof;
where b=0 to 500, where it is understood that when b is other than 0, b is a distribution having a mode equal to a stated value; and
wherein at least one R 1 comprises a monovalent reactive group.

6. The silicone-containing polymer of claim 1 , wherein said at least one silicone component is selected from the group consisting of methacryloxypropyl terminated, mono-n-alkyl terminated polydialkylsiloxane; bis-3-acryloxy-2-hydroxypropyloxypropyl polydialkylsiloxane; methacryloxypropyl-terminated polydialkylsiloxane; mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-alkyl terminated polydialkylsiloxane; and mixtures thereof.

7. The silicone-containing polymer of claim 1 , wherein said at least one silicone component is selected from monomethacrylate terminated polydimethylsiloxanes; bis-3-acryloxy-2-hydroxypropyloxypropyl polydialkylsiloxane; mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-butyl terminated polydialkylsiloxane; and mixtures thereof.

8. The silicone-containing polymer of claim 1 , wherein said at least one silicone component comprises 3-methacryloxy-2-hydroxypropyloxy-n-butyl terminated polydialkylsiloxane.

9. The silicone-containing polymer of claim 1 , wherein said reactive components further comprise at least one non-ionic hydrophilic acrylic-containing monomer.

10. The silicone-containing polymer of claim 9 , wherein said at least one non-ionic hydrophilic acrylic-containing monomer comprises HEMA, DMA and mixtures thereof.

11. The silicone-containing polymer of claim 1 , wherein the ratio of (i) said at least one silicone component and (ii) said sulfonic acid-containing component is less than about 100 kg/mol.

12. A silicone hydrogel comprising the silicone-containing polymer of claim 1 .

13. A silicone hydrogel formed from a reaction mixture comprising (i) at least one silicone component and (ii) at least one sulfonic acid-containing component, wherein said sulfonic acid-containing component is comprised of a salt formed by a non-polymerizable, hydrophilic base comprising a component whose conjugate acid has a pKa is 9 or less and a polymerizable sulfonic acid.

14. The silicone hydrogel of claim 13 , wherein the sulfonate group of the at least one sulfonic acid-containing component is present in a concentration to all components excluding diluent of less than 2 mol/kg.

15. The silicone hydrogel of claim 13 , wherein the reaction mixture further comprises a polyamide.

16. The silicone hydrogel of claim 13 , wherein said polymerizable sulfonic acid is selected from the group consisting of 2-acrylamido-2-methylpropane sulfonic acid, p-styrenesulfonic acid, 2-methacryloyloxyethylsulfonic acid, 3-methacryloyloxy-2-hydroxypropylsulfonic acid, allylsulfonic acid, 3-methacryloyloxypropylsulfonic acid, vinylsulfonic acid, and combinations thereof, and wherein the hydrophilic base comprises an aromatic amine whose conjugate acid has a pKa of 7.8 or less.

17. The silicone hydrogel of claim 16 , wherein said aromatic amine is selected from the group consisting of imidazole, aniline, pyridine, and derivatives.

18. A contact lens comprising a silicone-containing polymer of claim 1 .

19. A contact lens formed from a silicone hydrogel of claim 13 .

20. A biomedical device comprising a silicone-containing polymer of claim 1 .

21. A biomedical device formed from a silicone hydrogel of claim 13 .

22. A method of making a contact lens or a biomedical device, the method comprising:
reacting the reactive components of claim 1 to form the contact lens or the biomedical device.

23. The silicone hydrogel of claim 16 , wherein said aromatic amine is N-methyl imidazole.

Assignees

• Johnson & Johnson Vision Care

Inventors

• Mahadevan Shivkumar
• Maggio Thomas L
• Healy Brent Matthew
• Sonoda Leilani K
• Carman Turnage Michelle
• Vashi Hemantkumar

Classifications

• C08L81/08

  Polysulfonates · CPC title

• G02B1/043 Primary

  Contact lenses · CPC title

• C08F230/08

  containing silicon · CPC title

• C08G77/442

  containing vinyl polymer sequences · CPC title

• C08L83/04

  Polysiloxanes · CPC title