Method for making contact lenses

• US 9,802,339 B2
• Filed: 12/11/2014
• Issued: 10/31/2017
• Est. Priority Date: 12/13/2013
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Medina, Arturo Norberto, Huang, Jinyu, Ard, Katherine, Lu, Honghui, Haken, Uwe
• Primary Examiner(s): Vargot, Mathieu
• Application Number:
  US14/567,401
• Publication Number:
  US 20150165653A1
• Time in Patent Office: 1,055 Days
• CPC Class Codes: B29C 33/64 Silicone
• CPC Class Codes: B29C 39/003 characterised by the choice of material
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• CPC Class Codes: B29D 11/00192 Demoulding, e.g. separating lenses from mould halves
• CPC Class Codes: B29D 11/00519 Reusable moulds
• CPC Class Codes: B29K 2083/00 Use of polymers having silicon, with or without sulfur, nitrogen, oxygen, or carbon only, in the main chain, as moulding material
• CPC Class Codes: C08G 77/26 nitrogen-containing groups
• CPC Class Codes: C08G 77/44 containing only polysiloxane sequences
• CPC Class Codes: C08G 77/54 Nitrogen-containing linkages C08G77/485 takes precedence
• CPC Class Codes: C08L 83/10 Block- or graft-copolymers containing polysiloxane sequences obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C08L51/08, C08L53/00
• CPC Class Codes: C09D 183/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The instant invention pertains to a method and a fluid composition for producing contact lenses with improved lens quality and with increased product yield. The method of the invention involves applying to a molding surface of the mold a layer of mold releasing agent selected from a group consisting of fatty amines of carbon chain length C18 or less and silicones bearing pendant substituted pyrrolidone groups solution to reduce an averaged mold separation force by at least about 50% in comparison with that without the releasing agent.

Claims

1. A method for making contact lenses, comprising the steps of:

(1) providing a contact lens mold, wherein the mold has a first mold half with a first molding surface defining the anterior surface of a contact lens and a second mold half with a second molding surface defining the posterior surface of the contact lens, wherein said first and second mold halves are configured to receive each other such that a cavity is formed between said first and second molding surfaces;

(2) applying a layer solution of mold releasing agent selected from the group consisting of fatty amines of carbon chain length C18 or less and silicones bearing pendant substituted pyrrolidone groups onto the first molding surface and/or the second molding surface, wherein the weight percentage of mold releasing agent in the solution is from 0.01% to 10% based on the entire weight of the solution;

(3) at least partially drying said layer solution to form a coat of releasing agent on the first and/or second molding surface, wherein the formation of the coat of releasing agent vesicles on the first and/or second molding surfaces is characterized by having a percentage of reduction in mold separation force of at least about 50% relative to a control mold without any coat of the releasing agent vesicles thereon,

(4) introducing a fluid composition into the cavity formed by the first and second molding surfaces with the coat of the mold releasing agent formed in step (3) thereon, wherein the fluid composition comprises a lens-forming material, wherein the lens-forming material is crosslinkable and/or polymerizable by actinic radiation, wherein the lens-forming material comprises at least one member selected from the group consisting of a hydrophilic vinylic monomer, a silicone containing vinylic monomer, a silicone-containing crosslinker, a silicone-containing prepolymer, a hydrophilic prepolymer free of silicone, and combinations thereof;

(5) crosslinking/polymerizing the lens-forming material in the mold to form a contact lens having a polymer matrix; and

(6) separating the mold and removing the formed contact lens from the mold.

2. The method of claim 1, wherein the mold is a reusable mold.

3. The method of claim 2, wherein the reusable mold is made of glass or quartz.

4. The method of claim 1, wherein the mold releasing agent is a fatty amine of carbon chain length no greater than C18.

5. The method of claim 4, wherein the mold releasing agent is a stearyl amine.

6. The method of claim 1, wherein the mold releasing agent is a silicones bearing pendant substituted pyrrolidone groups.

7. The method of claim 6, wherein silicones bearing pendant substituted pyrrolidone groups is a (N-PYRROLIDONEPROPYL)METHYLSILOXANE-DIMETHYLSILOXANE COPOLYMER as shown by the formula 1:

8. The method of claim 6, wherein silicones bearing pendant substituted pyrrolidone groups

is a [(4-N,N-DIMETHYLAMIDO)-1-PYRROLYDINOPROPYL]METHYLSILOXANE)-(DIMETHYLSILOXANE) COPOLYMER as shown by the formula 2:

9. The method of claim 6, wherein the solution of mold releasing agent is a water solution.

10. The method of claim 1, wherein the step of applying a layer solution of mold releasing agent is carried by spraying the mold releasing agent solution onto the molding surfaces of the mold.

11. A method for producing a contact lens, comprising:

the steps of;

(1) introducing a fluid composition into a mold for making a contact lens, wherein the fluid composition comprises a lens-forming material and a mold releasing agent selected from the group consisting of a fatty amine of carbon chain length C18 or less and a silicones bearing pendant substituted pyrrolidone groups, wherein the lens-forming material is crosslinkable and/or polymerizable by actinic radiation or by heating, wherein the lens-forming material comprises at least one member selected from the group consisting of a hydrophilic vinylic monomer, a silicone containing vinylic monomer, a silicone-containing crosslinker, a silicone-containing prepolymer, a hydrophilic prepolymer free of silicone, and combinations thereof;

(2) crosslinking/polymerizing the lens-forming material in the mold to form a lens having a polymer matrix, wherein at least part of the mold releasing agent migrates to the interface between the mold and the polymer matrix of the formed lens; and

(3) separating the mold, wherein the mold releasing agent is present in an amount sufficient to reduce an averaged mold separation force by at least about 50% in comparison with that without the releasing agent.

12. The method of claim 11, wherein the mold is a reusable mold.

13. The method of claim 12, wherein the reusable mold is made of glass or quartz.

14. The method of claim 11, wherein the mold releasing agent is a fatty amine of carbon chain length no greater than C18.

15. The method of claim 14, wherein the mold releasing agent is a stearyl amine.

16. The method of claim 11, wherein the mold releasing agent is a silicones bearing pendant substituted pyrrolidone groups.

17. The method of claim 16, wherein silicones bearing pendant substituted pyrrolidone groups is a (N-PYRROLIDONEPROPYL) METHYLSILOXANE-DIMETHYLSILOXANE COPOLYMER as shown by the formula 1:

18. The method of claim 16, wherein silicones bearing pendant substituted pyrrolidone groups

is a [(4-N,N-DIMETHYLAMIDO)-1-PYRROLYDINOPROPYL]METHYLSILOXANE)-(DIMETHYLSILOXANE) COPOLYMER as shown by the formula 2: