Curable colored inks for making colored silicone hydrogel lenses

Patent metadata

Field	Value
Publication number	US-10364365-B2
Application number	US-201615348346-A
Country	US
Kind code	B2
Filing date	Nov 10, 2016
Priority date	Dec 28, 2015
Publication date	Jul 30, 2019
Grant date	Jul 30, 2019

Abstract

The present invention provides an actinically or thermally curable ink for making colored silicone hydrogel contact lenses. The ink of the invention comprises at least a pigment, a polymeric dispersant, a solvent and an actinically or thermally curable silicone-containing binder polymer including ethylenically unsaturated groups and segments derived from at least one silicone-containing vinylic monomer or macromere. The ink of the invention is characterized by having capability to be cured actinically or thermally to form a colored coat on a silicone hydrogel contact lens, wherein the ink is characterized by having an longer print life using a pad-printing system by at least 30% comparing to the ink which has the same composition except of no polymeric dispersant, wherein ink life is a number of printed parts that can be achieved in a print cycle.

First claim

What is claimed is:

1. An ink for making colored silicone hydrogel contact lenses, comprising at least a pigment, a polymeric dispersant, a synergist, a solvent and an actinically or thermally curable silicone-containing binder polymer including ethylenically unsaturated groups and segments derived from at least one silicone-containing vinylic monomer or macromer, wherein the synergist is selected from a group consisting of sulfonated Cu-phthalocyanine, copper phthalocyaninesulfonic acid and combinations thereof, wherein the ink is substantially free of water and has capability to be cured actinically or thermally to form a colored coat on a contact lens, wherein the ink is characterized by having a longer print life using a pad-printing system by at least 30% comparing to the ink which has the same composition except with no polymeric dispersant, wherein ink life is a number of printed parts that can be achieved in a print cycle.

2. The ink of the claim 1 , wherein the polymeric dispersant is selected from a group consisting of polyvinylpyrrolidone, alkylamino- functionalized polyethylene oxide and polypropylene oxides, polyoxyethylene alkylether polymers with a phosphate ester functionality, polyacrylic acid, polymer comprising a vinyl monomer containing dialkylamine groups, polymer comprising a vinyl monomer containing a phosphate ester group, and combinations therefore.

3. The ink of the claim 2 , wherein the polymeric dispersant is a polyvinylpyrrolidone.

4. The ink of the claim 3 , wherein polyvinylpyrrolidone has a weight average molecular weight of 4000 to 20000.

5. The ink of the claim 1 , wherein the pigment comprises at least 2.5 percent of organic pigment selected from a group consisting of phthalocyanine blue, phthalocyanine green, carbazole violet and combinations thereof.

6. The ink of the claim 1 , wherein the pigment comprises at least 3 percent of organic pigment selected from a group consisting of phthalocyanine blue, phthalocyanine green, carbazole violet and combinations thereof.

7. The ink of the claim 1 , wherein the pigment comprises at least 4 percent of organic pigment selected from a group consisting of phthalocyanine blue, phthalocyanine green, carbazole violet and combinations thereof.

8. The ink of the claim 1 , wherein the pigment comprises at least 4.5 percent of organic pigment selected from a group consisting of phthalocyanine blue, phthalocyanine green, carbazole violet and combinations thereof.

9. The ink of claim 1 , wherein the solvent is one or more organic solvents selected from the group consisting of acetone, methanol, ethanol, propanol, 2-ethoxyethanol, isopropanol, glycols, ketones, esters, cyclopentanone, cyclohexanone, tetrahydrofuran, acetone, methyl-2-pyrrolidone, dimethyl formamide, acetophenone, methylene dichloride, dimethyl sulfoxide, gamma-butyrolactone, ethylene dichloride, isophorone, o-dichlorobenzene, tetrahydrofuran, diacetone alcohol, methyl ethyl ketone, acetone, 2-nitropropane, ethylene glycol monoethyl ether, propylene carbonate, cyclohexanol, chloroform, trichloroethylene, 1,4-dioxane, ethyl acetate, ethylene glycol monobutyl ether, chlorobenzene, nitroethane, ethylene glycol monomethyl ether, butyl acetate, 1-butanol, methyl isobutyl ketone, nitromethane, toluene, ethanol, diethylene glycol, benzene, diethyl ether, ethanolamine, carbon tetrachloride, propylene glycol, hexane, ethylene glycol, and formamide.

10. The ink of claim 1 , wherein the binder polymer is an ethylenically functionalized derivative of a silicon-containing polymer having pendant functional groups selected from the group consisting of hydroxyl groups, primary amino groups, secondary amino groups, carboxylic groups, epoxy groups, aldehyde groups, amide groups, acid halide groups, isothiocyanate groups, isocyanate groups, halide groups, acid anhydride groups, and combinations thereof.

11. The ink of claim 10 , wherein the silicon-containing polymer is a copolymerization product of a polymerizable composition comprising: (a) at least one hydrophilic vinylic monomer; (b) at least one functionalizing vinylic monomer containing at least one functional group selected from the group consisting of hydroxyl group, primary amino group, secondary amino group, carboxylic group, epoxy group, aldehyde group, amide group, acid halide group, isothiocyanate group, isocyanate group, halide group, acid anhydride group, and combinations thereof; (c) at least one silicone-containing vinylic monomer or macromer; and (d) optionally one or more components selected from the group consisting of a polymerization initiator, a chain transfer agent, and a solvent.

12. The ink of claim 11 , wherein the hydrophilic vinylic monomer is hydroxyl-substituted C1-C8alkyl acrylates, hydroxyl-substituted C1-C8 alkyl methacrylates, acrylamide, methacrylamide, C1-C8alkyl acrylamides, C1-C8 alkyl methacrylamides, ethoxylated acrylates, ethoxylated methacrylates, hydroxyl-substituted C1-C8 alkyl acrylamides, hydroxyl-substituted C1-C8 alkyl methacrylamides, hydroxyl-substituted C1-C8 alkyl vinyl ethers, sodium vinylsulfonate, sodium styrenesulfonate, 2-acrylamido -2-methylpropanesulfonic acid, N-vinyipyrrole, N-vinyl-2-pyrrolidone, 2-vinyloxazoline, 2-vinyl-4,4′-dialkyloxazolin-5-one, 2- and 4-vinylpyridine, vinylically unsaturated carboxylic acids having a total of 3 to 5 carbon atoms, amino C1-C8-alkyl acrylates wherein the term amino also includes quaternary ammonium, mono C1-C8 alkylamino C1-C8 alkyl acrylates, di(C1-C8 alkyl amino) C1-C8 alkyl acrylates, amino C1-C8 alkyl methacrylates wherein the term amino also includes quaternary ammonium, mono C1-C8 alkyl amino C1-C8 alkyl methacrylates, di(C1-C8 alkyl amino) C1-C8 alkyl methacrylates, or allyl alcohol.

13. The ink of claim 11 , wherein the functionaiizing vinytic monomer is methacrylic acid, acrylic acid, glycidylmethacrylate, glycidytacrylate, 2-hydroxyethvl methacrylate 2-hydroxyethyl acrylate, methacrylic anhydride, N-hydroxymethylacrylamide, 2-bromoethylmethacrylate, or vinylbenzylchoride.

14. The ink of claim 1 , wherein a ratio wt % polymeric dispersant to wt % synergist is between 2:1 and 20:1.

Assignees

• Novartis Ag

Inventors

• Breitkopf Richard Charles
• Day Ellen A
• Qiu Yongxing
• Shrestha Ritu

Classifications

• C09D11/101

  Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing · CPC title

• C09D11/10

  based on artificial resins · CPC title

• C09D11/03

  characterised by features other than the chemical nature of the binder · CPC title

• B29D11/00923

  on lens surfaces for colouring or tinting (printing or marking in general B41M) · CPC title

• B29D11/00038 Primary

  Production of contact lenses · CPC title