Photocrosslinked polymers

• US 5,508,317 A
• Filed: 08/04/1994
• Issued: 04/16/1996
• Est. Priority Date: 08/06/1993
• Status: Expired due to Term

• Current Assignee: Novartis Ag
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Muller, Beat
• Primary Examiner(s): Szekely, Peter A.
• Application Number:
  US08/286,035
• Time in Patent Office: 621 Days
• Field of Search: 264/1.1, 522/84, 522/85, 522/86, 523/106, 523/107, 523/108, 525/57, 525/59, 525/61, 525/937
• US Class Current: 522/85
• CPC Class Codes: B29C 2035/0827 using UV radiation
• CPC Class Codes: B29C 31/041 using filling or dispensing heads placed in closed moulds or in contact with mould walls B29C45/27 takes precedence
• CPC Class Codes: B29C 33/303 centering mould parts or halves, e.g. during mounting
• CPC Class Codes: B29C 35/0894 provided with masks or diaphragms
• CPC Class Codes: B29C 37/0003 Discharging moulded articles from the mould constructions for removing the articles B29C33/44
• CPC Class Codes: B29C 37/0007 using means operable from outside the mould for moving between mould parts, e.g. robots
• CPC Class Codes: B29C 37/005 Compensating volume or shape change during moulding, in general
• CPC Class Codes: B29C 39/24 Feeding the material into the mould
• CPC Class Codes: B29C 39/36 Removing moulded articles
• CPC Class Codes: B29C 39/42 Casting under special conditions, e.g. vacuum
• CPC Class Codes: B29D 11/00057 characterised by the shape or surface condition of the edge, e.g. flashless, burrless, smooth
• CPC Class Codes: B29D 11/00134 Curing of the contact lens material
• CPC Class Codes: B29D 11/00442 Curing the lens material
• CPC Class Codes: B29L 2011/0041 Contact lenses
• CPC Class Codes: C08L 29/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: Y10S 525/937 Utility as body contact e.g. implant, contact lens or I.U.D.

Abstract

The invention relates to a novel process for the manufacture of mouldings, especially contact lenses, in which a soluble prepolymer comprising crosslinkable groups is crosslinked in solution, and also to mouldings, especially contact lenses, obtainable in accordance with that process. The present invention relates also to novel prepolymers that can be used in the process according to the invention, especially derivatives of a polyvinyl alcohol having a molecular weight of at least about 2000 that, based on the number of hydroxy groups of the polyvinyl alcohol, comprise from approximately 0.5 to approximately 80% of units of formula I ##STR1## wherein R is lower alkylene having up to 8 carbon atoms,

R¹ is hydrogen or lower alkyl and

R² is an olefinically unsaturated, electron-attracting, copolymerisable radical preferably having up to 25 carbon atoms, to crosslinked polymers, either homo- or co-polymers of those novel prepolymers, to processes for the preparation of the novel prepolymers and the homo- and co-polymers obtainable therefrom, to mouldings made from the said homo- or co-polymers, especially contact lenses made from those homo- or co-polymers, and to processes for the manufacture of contact lenses using the said homo- or co-polymers.

Claims

1. A process for the manufacture of a moulding, which comprises the following steps:

a) preparing a substantially aqueous solution of a prepolymer, said prepolymer being a water-soluble polymer that comprises crosslinkable groups, but which is substantially uncrosslinked, wherein the concentration of the prepolymer in said solution is up to 40% by weight;

b) introducing the solution obtained into a mould;

c) triggering crosslinking for a period of less than about 30 seconds;

d) opening the mould such that the moulding can be removed.

2. A process according to claim 1, wherein the moulding is a contact lens.

3. A process according to claim 1, wherein the substantially aqueous solution of the water-soluble prepolymer comprising crosslinkable groups is free or substantially free from undesired constituents, selected from the group consisting of monomeric, oligomeric and polymeric starting compounds used for the preparation of the prepolymer, and secondary products that have formed during the preparation of the prepolymer.

4. A process according to claim 1, wherein the substantially aqueous solution of the water-soluble prepolymer comprising crosslinkable groups is used without the addition of a vinylic comonomer or other comonomer.

5. A process according to claim 1, wherein an initiator for the crosslinking is added to the solution of the prepolymer.

6. A process according to claim 1, wherein an extraction for removal of undesired constituents following the crosslinking is dispensed with.

7. A process according to claim 1, which comprises the following steps:

a) preparing a substantially aqueous solution of a water-soluble prepolymer that comprises crosslinkable groups, which is free or substantially free from undesired constituents, selected from the group consisting of monomeric, oligomeric and polymeric starting compounds used for the preparation of the prepolymer, and secondary products that have formed during the preparation of the prepolymer, and which is used without the addition of a comonomer,

b) introducing the solution obtained into a mould,

c) triggering crosslinking, and

d) opening the mould such that the moulding can be removed from the mould.

8. A process according to claim 7, wherein the moulding is a contact lens.

9. A process for the manufacture of a contact lens according to claim 8, wherein the substantially aqueous solution is a pure aqueous solution or a solution in an artificial lacrimal fluid, which is unbuffered or buffered.

10. A process for the manufacture of a contact lens according to claim 8, wherein a crosslinking initiator is added to the solution and wherein the crosslinking is photocrosslinking.

11. A moulding obtainable in accordance with the process of claim 1.

12. A contact lens according to claim 11, which is suitable for its intended use without extraction.

13. A contact lens obtainable according to any one of claims 8 to 10, which is suitable for its intended use without extraction.

14. A moulding according to claim 11 which is a contact lens.

15. A contact lens of claim 14, which contact lens is suitable for its intended use without extraction.

16. A contact lens of claim 8, which contact lens is suitable for its intended use without extraction.

17. A contact lens of claim 10, which contact lens is suitable for its intended use without extraction.

18. A process for the manufacture of a molding, which comprises the following steps:

(a) preparing a substantially aqueous solution of a prepolymer, said prepolymer being a water-soluble polymer that comprises crosslinkable groups, but which is substantially uncrosslinked;

(b) introducing the solution obtained into a mold;

(c) triggering crosslinking by applying energy for a period of less than about 30 seconds; and

(d) opening the mold such that the molding can be removed.

19. A process of claim 18, wherein said molding is a contact lens.