Method of making silicone containing contact lens with reduced amount of diluents

Patent metadata

Field	Value
Publication number	US-9423528-B2
Application number	US-201313915126-A
Country	US
Kind code	B2
Filing date	Jun 11, 2013
Priority date	Jun 25, 2012
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

The present invention relates to a method of manufacturing a contact lens including the steps of: (i) adding reactive components to a mold, wherein the reactive components comprise (a) at least one hydroxy-containing silicone component having a weight average molecular weight from about 200 to about 15,000 g/mole and (b) at least one mono-ether terminated, mono-methacrylate terminated polyethylene glycol having a weight average molecular weight from about 200 to about 10,000 g/mole; (ii) curing the reactive components within the mold to form the contact lens; and (iii) removing the contact lens from said mold.

First claim

What is claimed is:

1. A method of manufacturing a contact lens, said method comprising the steps of:
(i) adding reactive components to form a reactive mixture, wherein said reactive components comprise (a) at least one hydroxy-containing silicone component having a weight average molecular weight from about 200 to about 15,000 g/mole and (b) at least one monofunctional polyethylene glycol having a weight average molecular weight from about 200 to about 10,000 g/mole; and less than about 15 wt % diluents;
(ii) curing said reactive components within said mold to form said contact lens comprising a polymer having a Tg (heating) of less than about 125° C.; and
(iii) dry removing said contact lens from said mold.

2. The method of claim 1 , wherein said at least one monofunctional polyethylene glycol is a mono-ether terminated, mono-methacrylate terminated polyethylene glycol.

3. The method of claim 2 , wherein said at least one at least one monofunctional polyethylene glycol is mPEG 475.

4. The method of claim 3 , wherein said reactive components comprises less than five percent, by weight, of one or more diluents.

5. The method of claim 4 , wherein said reactive mixture comprises about 10 to about 20 weight % (meth)acrylamide containing monomers.

6. The method of claim 4 , wherein said at least one hydroxy-containing silicone component comprises mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-butyl terminated polydialkylsiloxane.

7. A contact lens manufactured by the method of claim 6 .

8. The method of claim 3 , wherein said at least one hydroxy-containing silicone component comprises mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-butyl terminated polydialkylsiloxane.

9. The method of claim 1 , wherein said reactive components comprises less than five percent, by weight, of one or more diluents.

10. The method of claim 1 , wherein said polymer comprises a Tg (heating) of between about 115 and about 125° C.

11. The method of claim 1 , wherein said reactive mixture comprises from about 10 to about 20 weight % of at least one hydroxyalkyl containing monomer.

12. The method of claim 11 , wherein said at least one hydroxy-containing silicone component comprises mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-butyl terminated polydialkylsiloxane.

13. The method of claim 1 , wherein at least one at least one hydroxy-containing silicone component is selected from compounds of Formula I:

wherein:
R 1 is independently selected from 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 hydroxy group.

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

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

16. The method of claim 1 , wherein said at least one hydroxy-containing silicone component comprises mono-(3-methacryloxy-2-hydroxypropyloxy)propyl terminated, mono-butyl terminated polydialkylsiloxane.

17. The method of claim 1 , wherein said reactive components comprises DMA and the weight ratio of (i) said DMA and (ii) said at least one-monofunctional polyethylene glycol is from about 25:75 to about 75:25.

18. The method of claim 1 , wherein said reactive components comprises from about 20 to about 70 percent, by weight, of said at least one monofunctional polyethylene glycol.

19. A contact lens manufactured by the method of claim 1 .

20. The method of claim 1 wherein said reactive mixture further comprises at least one internal wetting agent.

21. The method of claim 20 wherein said internal wetting agent is included in said reaction mixture in an amount between about 6 and about 40 wt % based upon all components in the reaction mixture, excluding any diluents.

Assignees

• Johnson & Johnson Vision Care

Inventors

• Alli Azaam
• Mahadevan Shivkumar

Classifications

• G02B1/043 Primary

  Contact lenses · CPC title

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• B29D11/00038 Primary

  Production of contact lenses · CPC title

• B29K2023/06

  PE, i.e. polyethylene · CPC title

• B29D11/00 Primary

  Producing optical elements, e.g. lenses or prisms (grinding or polishing of optical elements B24B; constructional form of optical elements G02B; {optical parts of spectacles G02C7/00}) · CPC title