Methods and compositions for manufacturing tinted ophthalmic lenses

• US 6,149,842 A
• Filed: 11/12/1998
• Issued: 11/21/2000
• Est. Priority Date: 11/12/1998
• Status: Expired due to Term

• Current Assignee: Novartis Ag
• Original Assignee: Novartis Ag
• Inventors: Cooper, Charlotte Lynn, Lally, John Martin, Stockinger, Friedrich, Seiferling, Bernhard, Muller, Achim, Mulcahy, Deborah Jean
• Primary Examiner(s): Vargot, Mathieu D.
• Application Number:
  US09/191,063
• Time in Patent Office: 740 Days
• Field of Search: 264/1.1, 264/1.36, 264/1.38, 264/2.6, 351/159, 351/162, 351/160 H
• US Class Current: 264/1.36
• CPC Class Codes: B29C 35/02 Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mouldcold vulcanisation B29C35/18 ; vulcanising tyres, presses therefor B29D30/0601
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• CPC Class Codes: B29D 11/00317 Production of lenses with markings or patterns
• CPC Class Codes: B29D 11/00913 full body; edge-to-edge

Abstract

The invention relates to a process for the manufacture of tinted ophthalmic moldings comprising the steps of

(a) providing a water soluble polymer precursor having crosslinkable or polymerizable groups;

(b) providing a pigment dispersion comprising an inorganic or organic pigment and a dispersing agent;

(c) mixing the metal phthalocyanine dye or pigment with the polymer precursor to form a tinted prepolymerization mixture,

(d) dispensing the tinted prepolymerization mixture into a mold,

(e) applying radiation to the tinted prepolymerization mixture in the mold, thereby crosslinking or polymerizing the polymer precursor and entrapping the dye or pigment within the polymeric network of the resultant ophthalmic molding, and

(f) opening the mold so that the ophthalmic molding can be removed from the mold.

According to the process, tinted ophthalmic moldings, particularly full-body tinted soft contact lenses having improved properties, are prepared with an improved efficiency.

Claims

1. A process for the manufacture of a tinted ophthalmic molding comprising the steps of:

(a) providing a water soluble polymer having crosslinkable groups and having a weight average molecular weight of at least 2000;

(b) providing an aqueous pigment dispersion comprising a phthalocyanine pigment and a physiologically acceptable, water soluble, polymeric dispersing agent;

(c) mixing the pigment dispersion with the polymer to form a tinted prepolymerization mixture,

(d) dispensing the tinted prepolymerization mixture into a mold,

(e) applying radiation to the tinted prepolymerization mixture in the mold, thereby crosslinking or polymerizing the polymer and entrapping the pigment within the polymeric network of the resultant ophthalmic molding, and

(f) opening the mold so that the ophthalmic molding can be removed from the mold.

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

3. A process according to claim 1, wherein the water soluble polymer is a polyvinyl alcohol having a weight-average molecular weight of at least about 2000 that, based on the number of hydroxy groups of the polyvinyl alcohol, include from about 0.5% to about 80% of units of formula I:

##STR5## 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 copolymerizable radical.

4. A process according to claim 1, wherein the water soluble polymer is a polyvinyl alcohol having a weight average molecular weight of at least about 2000 that, based on the a number of hydroxyl groups of the polyvinyl alcohol, includes from about 0.5% to about 80% of units of formula III:

##STR6## where R is lower alkylene, R₁ is hydrogen or lower alkyl, p is zero or one, q is zero or one, R₃ is an olefinically unsaturated copolymerizable radical having from 2 to 8 carbon atoms, and R₄ and R₅ are each, independently of the other, lower alkylene having from 2 to 8 carbon atoms, arylene having from 6 to 12 carbon atoms, a saturated divalent cycloaliphatic group having from 7 to 14 or arylenealkylenearylene having from 13 to 16 carbon atoms.

5. A process according to claim 4, wherein R is lower alkylene having up to 6 carbon atoms, p is zero and R₃ is alkenyl having from 2 to 8 carbon atoms.

6. A process according to claim 1, wherein the water soluble polymer according to step a) is provided in form of a 15 to 50 weight percent aqueous solution.

7. A process according to claim 1, wherein the pigment dispersion according to step b) is an aqueous dispersion comprising the pigment and a water soluble polymeric dispersing agent selected from the group consisting of a polymer according to a), a polyacrylic acid and a polyvinyl alcohol.

8. A process according to claim 1, wherein the pigment according to step b) is an aqueous dispersion selected from the group consisting of a polymer according to a) and a polyvinyl alcohol.

9. A process according to claim 8, wherein the aqueous dispersion comprises 1 to 70% by weight of pigment and 1 to 60% by weight of polymer, in each case relative to the weight of the entire dispersion.

10. A process according to claim 1, wherein the weight percentage of pigment, based on the total weight of polymer and optional comonomers present in the prepolymerization mixture according to c), is from about 0.0001 to 0.05%.

11. A process according to claim 1, wherein a photoinitiator is added to the prepolymerization mixture according to step c).

12. A process according to claim 1, wherein the prepolymerization mixture according to step c) is devoid of a comonomer.

13. A process according to claim 1, wherein the crosslinking and/or polymerizing of the polymer and the entrapping of the pigment according to step e) occurs in a period of ≦

5 minutes.

14. A process according to claim 1 for the manufacture of a tinted contact lens which comprises the following steps:

(a) providing an aqueous solution of polyvinyl alcohol having polymerizable or crosslinkable groups;

(b) providing an aqueous dispersion containing a copper phthalocyanine pigment;

(c) mixing the polyvinyl alcohol solution with pigment dispersion to form a tinted prepolymerization mixture;

(d) introducing the tinted prepolymerization mixture into a mold;

(e) applying radiation to the tinted prepolymerization mixture in the mold, thereby crosslinking or polymerizing the polymer precursor and entrapping the pigment within the polymeric network of the resultant contact lens, and

(f) opening the mold so that the tinted contact lens can be removed from the mold.

15. A process according to claim 1 for the manufacture of a tinted contact lens which comprises the following steps:

(a) providing a 15 to 40 weight percent aqueous solution of a polyvinyl alcohol prepolymer having a weight-average molecular weight of at least about 2000 that, based on the number of hydroxy groups of the polyvinyl alcohol, includes from about 0.5% to about 80% of units of formula I;

##STR7## 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 copolymerizable radical;

(b) providing an aqueous dispersion comprising 1 to 70% by weight, based on the weight of the entire dispersion, of a copper phthalocyanine pigment and 1 to 60% by weight, based on the weight of the entire dispersion, of a dispersing agent selected from the group consisting of a polyvinyl alcohol prepolymer according to a), a polyacrylic acid and a polyvinyl alcohol;

(c) mixing the prepolymer solution according to (a) with the pigment dispersion according to (b) to form a tinted prepolymerization mixture;

(d) introducing the tinted prepolymerization mixture into a mold;

(e) applying radiation to the prepolymerization mixture in the mold in a time period of ≦

5 minutes, thereby crosslinking or polymerizing the polymer precursor and entrapping the pigment within the polymeric network of the resultant contact lens, and

(f) opening the mold so that the tinted contact lens can be removed from the mold.

16. A process according to claim 1 for the manufacture of a tinted contact lens which is suitable to be inserted into the human eye without extraction, comprising the following steps:

(a) providing a 20 to 40 weight percent aqueous solution of a polyvinyl alcohol prepolymer having a weight-average molecular weight of at least about 2000 that, based on the number of hydroxy groups of the polyvinyl alcohol, includes from about 0.5% to about 80% of units of formula III;

##STR8## where R is lower alkylene having up to 6 carbon atoms, R₁ is hydrogen or alkyl having up to 4 carbon atoms, p is zero, and R₃ is alkenyl having from 2 to 8 carbon atoms;

(b) providing an aqueous dispersion comprising 5 to 60% by weight, based on the weight of the entire dispersion, of a copper phthalocyanine pigment and 1 0 to 40% by weight, based on the weight of the entire-dispersion, of a dispersing agent selected from the group consisting of a polyvinyl alcohol prepolymer according to a) and a polyvinyl alcohol;

(c) mixing the prepolymer solution according to a) with the pigment dispersion according to b) and an additional photoinitiator to form a tinted prepolymerization mixture containing 0.0001 to 0.05 weight percent phthalocyanine pigment, based on the total weight of polymer precursor;

(d) introducing the tinted prepolymerization mixture into a mold;

(e) applying radiation to the tinted prepolymerization mixture in the mold in a time period of ≦

1 minute, thereby crosslinking or polymerizing the polymer precursor and entrapping the pigment within the polymeric network of the resultant contact lens, and

(f) opening the mold so that the tinted contact lens can be removed from the mold.

17. An ophthalmic molding which is formed by a process according to claim 1.

18. A tinted contact lens which is formed by a process according to claim 14.

19. A tinted contact lens which is formed by a process according to claim 15.

20. A tinted contact lens which is formed by a process according to claim 16.

21. A process for the manufacture of a tinted ophthalmic molding comprising the steps of:

(a) providing a water soluble polymer having crosslinkable groups and having a weight average molecular weight of at least 2000;

(b) providing an aqueous pigment dispersion comprising a phthalocyanine pigment and a dispersing agent;

(c) mixing the pigment dispersion with the polymer to form a tinted prepolymerization mixture,

(d) dispensing the tinted prepolymerization mixture into a mold,

(e) applying radiation to the tinted prepolymerization mixture in the mold, thereby crosslinking or polymerizing the polymer and entrapping the pigment within the polymeric network of the resultant ophthalmic molding, and

(f) opening the mold so that the ophthalmic molding can be removed from the mold;

wherein the dispersing agent is selected from the group consisting of the polymer according to a), polyacrylic acid, and polyvinyl alcohol.

22. A process for the manufacture of a tinted ophthalmic molding comprising the steps of:

(a) providing a water soluble polymer having crosslinkable groups and having a weight average molecular weight of at least 2000;

(b) providing an aqueous pigment dispersion comprising a phthalocyanine pigment and a dispersing agent;

(c) mixing the pigment dispersion with the polymer to form a tinted prepolymerization mixture,

(d) dispensing the tinted prepolymerization mixture into a mold,

(e) applying radiation to the tinted prepolymerization mixture in the mold, thereby crosslinking or polymerizing the polymer and entrapping the pigment within the polymeric network of the resultant ophthalmic molding, and

(f) opening the mold so that the ophthalmic molding can be removed from the mold;

wherein the crosslinking is not followed by extraction in order to remove undesired constituents.

23. A process for the manufacture of a tinted ophthalmic molding comprising the steps of:

(a) providing a water soluble polymer having crosslinkable groups and having a weight average molecular weight of at least 2000;

(b) providing an aqueous pigment dispersion comprising a phthalocyanine pigment and a dispersing agent;

(c) mixing the pigment dispersion with the polymer to form a tinted prepolymerization mixture,

(d) dispensing the tinted prepolymerization mixture into a mold,

(e) applying radiation to the tinted prepolymerization mixture in the mold, thereby crosslinking or polymerizing the polymer and entrapping the pigment within the polymeric network of the resultant ophthalmic molding, and

(f) opening the mold so that the ophthalmic molding can be removed from the mold;

wherein said ophthalmic molding is suitable for insertion into a human eye without extraction.