Ink composition for cosmetic contact lenses

Patent metadata

Field	Value
Publication number	US-2021079238-A1
Application number	US-202016987673-A
Country	US
Kind code	A1
Filing date	Aug 7, 2020
Priority date	Sep 12, 2019
Publication date	Mar 18, 2021
Grant date	—

Abstract

Provided are ink compositions for making cosmetic contact lenses, as well as cosmetic contact lenses and methods for their preparation and use. The ink composition comprises: (a) a colorant; and (b) a nonreactive hydrophilic polymer.

First claim

1 . An ink composition for making cosmetic contact lenses, the ink composition comprising: (a) a colorant; and (b) a nonreactive hydrophilic polymer; and optionally (c) a binder polymer.

2 . The ink composition of claim 1 wherein the nonreactive hydrophilic polymer comprises a polyamide.

3 . The ink composition of claim 1 wherein the nonreactive hydrophilic polymer comprises: dextran, poly(ethylene oxide), polyvinyl alcohol (PVA), poly (N-isopropylacrylamide), poly(oligoethylene oxide), polyethylene glycol (PEG), poly (N,N-dimethylaminoethyl acrylate), poly(imine), poly(acrylic acid), or mixtures of two or more thereof.

4 . The ink composition of claim 1 wherein the optional binder polymer comprises a copolymer formed from a hydrophilic monomer comprising functionality selected from the group consisting of hydroxyalkyl, aminoalkyl, and mixtures thereof; a silicone-containing macromer; and optionally a silicone-containing monomer.

5 . The ink composition of claim 1 , further comprising (d) a solvent.

6 . The ink composition of claim 5 wherein the solvent comprises: ethanol, 1-propanol, 2-propanol, 1-ethoxy-2-propanol (1E2P), t-butyl alcohol, t-amyl alcohol, and 3,7-dimethyl-1,7-octanediol (D30), tripropylene glycol methyl ether (TPME), isopropyl lactate (IPL), 1-(2-hydroxy ethyl)-2-pyrrolidone (HEP), glycerol or mixtures of two or more thereof.

7 . The ink composition of claim 1 wherein the nonreactive hydrophilic polymer comprises a cyclic polyamide.

8 . The ink composition of claim 1 wherein the colorant comprises: pthalocyanine blue, pthalocyanine green, carbazole violet, vat orange #1, iron oxide black, iron oxide brown, iron oxide yellow, iron oxide red, titanium dioxide, dichlorotriazine, vinyl sulfone-based dyes, and mixtures of two or more thereof.

9 . The ink composition of claim 1 comprising: from 0.1 to about 25 weight percent of the colorant; from about 1 to about 50 weight percent of the nonreactive hydrophilic polymer; from about 1 to 60 weight percent of the binder polymer; and from about 50 to about 95 weight percent of a solvent, each based on the total weight of the ink composition.

10 . The ink composition of any of claim 1 wherein the binder polymer has a weight average molecular weight in the range of about 10 to about 100 kDa.

11 . The ink composition claim 1 wherein the nonreactive hydrophilic polymer is poly(vinylpyrrolidone).

12 . The ink composition of claim 4 , wherein the hydrophilic monomer comprises 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, N-(2-hydroxyethyl) (meth)acrylamide, N,N-bis(2-hydroxyethyl) (meth)acrylamide, N-(2-hydroxypropyl) (meth)acrylamide, N,N-bis(2-hydroxypropyl) (meth)acrylamide, N-(3-hydroxypropyl) (meth)acrylamide, N-(2-hydroxybutyl) (meth)acrylamide, N-(3-hydroxybutyl) (meth)acrylamide, N-(4-hydroxybutyl) (meth)acrylamide, or mixtures thereof.

13 . The ink composition of claim 12 , wherein the hydrophilic monomer is 2-hydroxyethyl (meth)acrylate.

14 . The ink composition of claim 4 wherein the silicone-containing macromer comprises a polymerizable functional group selected from the group consisting of (meth)acrylate, (meth)acrylamide, styryl, vinyl, N-vinyl lactam, N-vinylamides, O-vinylethers, O-vinylcarbonates, and O-vinylcarbonates.

15 . The ink composition of claim 4 , wherein the silicone-containing macromer comprises a chemical structure shown in Formula I:

wherein Z is selected from O, N, S or NCH 2 CH 2 O; when Z═O or S, R 2 is not required; wherein R 1 is a hydrogen atom or methyl; wherein n is a whole number between 1 and 200; wherein R 3 is an alkylene segment (CH 2 ) y in which y is a whole number from 1 to 6, and each methylene group may be optionally further and independently substituted with a group selected from the group consisting of ethers, amines, esters, ketones, carbonyls, carboxylates, and carbamates, or when y is 2 or more a non-terminal methylene group is optionally replaced with a carbamate group; or wherein R 3 is an oxyalkylene segment O(CH 2 ) z in which z is a whole number from 1 to 3, or wherein R 3 is a mixture of alkylene and oxyalkylene segments and the sum of y and z is between 1 and 9; wherein R 2 and R 4 are independently a hydrogen atom, a linear, branched, or cyclic alkyl group containing between one and six carbon atoms, a linear, branched, or cyclic alkoxy group containing between one and six carbon atoms, a linear or branched polyethyelenoxyalkyl group, an alkyl-siloxanyl-alkyl group, a phenyl group, a benzyl group, a substituted or un-substituted aryl group, a fluoroalkyl group, a partially fluorinated alkyl group, a perfluoroalkyl group, a fluorine atom, a mono-, di, or tri-hydroxyalkyl group containing between one and six carbon atoms, or combinations thereof; and wherein R 5 is a substituted or un-substituted linear, branched, or cyclic alkyl group having 1 to 8 carbon atoms or an aryl group, any of which may be further substituted with one or more fluorine atoms or trimethylsiloxy groups.

16 . The ink composition of claim 4 , wherein the silicone-containing macromer is selected from the group consisting of monoalkyl terminated, mono(meth)acrylate terminated poly(dialkylsiloxanes), monoalkyl terminated, monoalkyl terminated, mono(meth)acrylate terminated poly(diarylsiloxanes), monoalkyl terminated, mono(meth)acrylate terminated poly(alkylarylsiloxanes), and mixtures thereof.

17 . The ink composition of claim 16 , wherein the silicone-containing macromer is mono-n-butyl terminated monomethacryloxypropyl terminated polydimethylsiloxane.

18 . The ink composition of claim 4 , wherein the silicone-containing macromer comprises a chemical structure shown in Formula VIII:

wherein Z is selected from O, N, S or NCH 2 CH 2 O; wherein R 1 is independently hydrogen atom or methyl group; wherein R 2 , R 3 , and R 4 are independently a hydrogen atom or a linear, branched, or cyclic alkyl group containing one to eight carbon atoms, any of which may be further substituted with at least one hydroxy group, and which may be optionally substituted with amido, ether, amino, carboxyl, carbonyl groups and combinations thereof; for Z═O and S, R 2 is not required; wherein n is the number of siloxane repeating units and is from 4 to 200; and wherein R 5 is selected from straight or branched C 1 to C 8 alkyl groups.

19 . The ink composition of claim 4 , wherein the silicone-containing macromer is mono-n-butyl terminated mono-(2-hydroxy-3-methacryloxypropyl)-propyl ether terminated polydimethylsiloxane.

20 . The ink composition of claim 4 , wherein the silicone-containing macromer is selected from the group consisting of mono-n-butyl terminated monomethacryloxypropyl terminated polydimethylsiloxane, mono-n-butyl terminated mono-(2-hydroxy-3-methacryloxypropyl)-propyl ether terminated polydimethylsiloxane, and mixtures thereof.

21 . The ink composition of claim 4 , wherein the silicone-containing macromer has a number average molecular weight greater than 500 Daltons.

22 . The ink composition of claim 4 , wherein the silicone-containing macromer has a number average molecular weigh

Assignees

• Johnson & Johnson Vision Care

Inventors

• Patton Jaqunda
• Zhang Yong
• Guzman Alexander
• Maharvi Ghulam

Classifications

• G02B1/043

  Contact lenses · CPC title

• C09D11/10 Primary

  based on artificial resins · CPC title

• C09D11/033 Primary

  characterised by the solvent · CPC title

• B29L2011/0041

  Contact lenses · CPC title

• B29D11/00134

  Curing of the contact lens material · CPC title