Modified pigment products and black matrixes comprising same

Abstract

The present invention describes modified pigment products comprising a pigment having attached at least one photopolymerizable group and at least one ionic or ionizable group. Dispersions, black matrixes, and resin compositions comprising these modified pigment products are also disclosed.

1 . A modified pigment product comprising a pigment having attached at least one polymeric group, wherein the polymeric group comprises at least one photopolymerizable group and at least one ionic or ionizable group.  
   
   
       2 . The modified pigment product of  claim 1 , wherein the ionic or ionizable group is an anionic or anionizable group.  
   
   
       3 . The modified pigment product of  claim 1 , wherein the pigment is carbon black.  
   
   
       4 . The modified pigment product of  claim 3 , wherein the carbon black has a dibutylphthalate absorption (DBP) of from about 25 to 70 mL/100 g.  
   
   
       5 . The modified pigment product of  claim 4 , wherein the carbon black has a dibutylphthalate absorption (DBP) of from about 30 to 50 mL/100 g.  
   
   
       6 . The modified pigment product of  claim 5 , wherein the carbon black has a dibutylphthalate absorption (DBP) of from about 30 to 40 mL/100 g.  
   
   
       7 . The modified pigment product of  claim 1 , wherein the photopolymerizable group comprises an ethylenically unsaturated group.  
   
   
       8 . The modified pigment product of  claim 1 , wherein the photopolymerizable group comprises an acrylate group, a methacrylate group, a vinyl group, or a styrenic group.  
   
   
       9 . The modified pigment product of  claim 8 , wherein the photopolymerizable group is an acrylate ester or methacrylate ester.  
   
   
       10 . The modified pigment product of  claim 2 , wherein the anionic or amonizable group comprises a carboxylic acid or salt thereof.  
   
   
       11 . The modified pigment product of  claim 2 , wherein the anionic or anionizable group is a group having the formula —OOC-Alk-COOH or salt thereof, wherein Alk represents a saturated or unsaturated cyclic or linear alkyl group.  
   
   
       12 . The modified pigment product of  claim 11 , wherein Alk represents a cyclohexanediyl group.  
   
   
       13 . The modified pigment product of  claim 1 , wherein the polymeric group comprises a phenyl ether group and a substituted propanediyl group.  
   
   
       14 . The modified pigment product of  claim 1 , wherein the polymeric group comprises a polymer prepared from epoxy bisphenol-A, oligomers of epoxy bisphenol-A, or epoxy novolac.  
   
   
       15 . The modified pigment product of  claim 1 , wherein the modified pigment product is in a liquid vehicle to form a dispersion.  
   
   
       16 . The modified pigment product of  claim 15 , wherein the liquid vehicle is a non-aqueous vehicle comprising a solvent selected from the group consisting of: ethylcellosolve, ethylcellosolve acetate, butylcellosolve, butylcellosolve acetate, ethylcarbitol, ethylcarbitol acetate, diethyleneglycol, cyclohexanone, propyleneglycol monomethylether, propyleneglycol monomethylether acetate, lactate esters, and mixtures thereof.  
   
   
       17 . The modified pigment product of  claim 15 , further comprising a photosensitive resin.  
   
   
       18 . The modified pigment product of  claim 17 , wherein the photosensitive resin is a resin prepared from an epoxy bisphenol-A resin or an epoxy novolac resin.  
   
   
       19 . A modified pigment product comprising a pigment having attached at least one polymeric group having the formula —X-Sp-[PP], wherein X, which is directly attached to the pigment, represents an arylene, a heteroarylene, or an alkylene group, Sp represents a spacer group, and PP represents a polymer comprising at least one photopolymerizable group and at least one ionic or ionizable group.  
   
   
       20 . The modified pigment product of  claim 19 , wherein the ionic or ionizable group is an anionic or anionizable group.  
   
   
       21 . The modified pigment product of  claim 19 , wherein the pigment is carbon black.  
   
   
       22 . The modified pigment product of  claim 21 , wherein the carbon black has a dibutylphthalate absorption (DBP) of from about 25 to 70 mL/100 g.  
   
   
       23 . The modified pigment product of  claim 22 , wherein the carbon black has a dibutylphthalate absorption (DBP) of from about 30 to 50 mL/100 g.  
   
   
       24 . The modified pigment product of  claim 23 , wherein the carbon black has a dibutylphthalate absorption (DBP) of from about 30 to 40 mL/100 g.  
   
   
       25 . The modified pigment product of  claim 19 , wherein the photopolymerizable group comprises an ethylenically unsaturated group.  
   
   
       26 . The modified pigment product of  claim 19 , wherein the photopolymerizable group comprises an acrylate group, a methacrylate group, a vinyl group, or a styrenic group.  
   
   
       27 . The modified pigment product of  claim 19 , wherein the photopolymerizable group is an acrylate ester or methacrylate ester.  
   
   
       28 . The modified pigment product of  claim 20 , wherein the anionic or anionizable group comprises a carboxylic acid or salt thereof.  
   
   
       29 . The modified pigment product of  claim 20 , wherein the anionic or anionizable group is a group having the formula —OOC-Alk-COOH or salt thereof, wherein Alk represents a saturated or unsaturated cyclic or linear alkyl group.  
   
   
       30 . The modified pigment product of  claim 29 , wherein Alk represents a cyclohexanediyl group.  
   
   
       31 . The modified pigment product of  claim 19 , wherein the polymeric group comprises a phenyl ether group and a substituted propanediyl group.  
   
   
       32 . The modified pigment product of  claim 19 , wherein the polymeric group comprises a polymer prepared from epoxy bisphenol-A, oligomers of epoxy bisphenol-A, or epoxy novolac.  
   
   
       33 . The modified pigment product of  claim 19 , wherein PP represents a polymer having the formula [T-Y-(Q-Y) n -T], wherein Q comprises a bisphenyl ether group, Y comprises a substituted propanediyl group, T comprises a terminating group, and n is an integer from 1 to 20.  
   
   
       34 . The modified pigment product of  claim 33 , wherein T comprises the photopolymerizable group.  
   
   
       35 . The modified pigment product of  claim 33 , wherein T comprises an alkyl ester.  
   
   
       36 . The modified pigment product of  claim 33 , wherein: 
 Q is —O—C 6 H 4 —C(CH 3 ) 2 —C 6 H 4 —O—, —O—C 6 H 4 —CH 2 —C 6 H 4 —O—, or —O—C 6 H 4 -fluorenyl-C 6 H 4 —O—;    Y is —CH 2 —CH(Z)-CH 2 —, wherein Z is —OH, —OOC-Alk-COOH, or salt thereof, or a bond to Sp, and Alk represents a saturated or unsaturated cyclic or linear alkyl group; and    T is CH 2 ═CH—COO— or CH 2 ═C(CH 3 )—COO—.    
   
   
       37 . The modified pigment product of  claim 36 , wherein Sp is —OOC-Alk-COO—, —OOC-Alk-CONR—, —OOC-Alk-CONR(CH 2 —CH 2 ) x NR—(CH 2 —CH 2 )—SO 2 —, —OOC-Alk-COO(CH 2 —CH 2 ) x O—(CH 2 —CH 2 )—SO 2 —, —OOC-Alk-COO(AOX) x —(CH 2 —CH 2 )—SO 2 —, —OOC-Alk-CONR(AOX) x -Alk-NR—(CH 2 —CH 2 )—SO 2 —, or —O—(CH 2 —CH 2 )—SO 2 —, wherein R, which can be the same or different, is hydrogen or a substituted or unsubstituted aryl or alkyl group, AOX represents an alkylene oxide group of from about 1 to about 12 carbons, and x is an integer between 1 and 500.  
   
   
       38 . The modified pigment product of  claim 19 , wherein PP represents a polymer having the formula [A-(CR 2 B) n —CR 2 A], wherein A and B comprise a phenyl ether group and a substituted propanediyl group, R, which can be the same or different, is hydrogen or a substituted or unsubstituted aryl or alkyl group and n is an integer from 1 to 20.  
   
   
       39 . The modified pigment product of  claim 38 , wherein A and B further comprise the photopolymerizable group.  
   
   
       40 . The modified pigment product of  claim 38 , wherein: 
 A is                          B is                          Y is —CH 2 —CH(Z)-CH 2 —, wherein Z is —OH, —OOC-Alk-COOH or salt thereof, or a bond to Sp, and Alk represents a saturated or unsaturated cyclic or linear alkyl group; and T is CH 2 ═CH—COO— or CH 2 ═C(CH 3 )—COO—.    
   
   
       41 . The modified pigment product of  claim 40 , wherein T comprises an alkyl ester.  
   
   
       42 . The modified pigment product of  claim 40 , wherein Sp is —OOC-Alk-COO—, —OOC-Alk-CONR—, —OOC-Alk-CONR(CH 2 —CH 2 ) x NR—(CH 2 —CH 2 )—SO 2 —, —OOC-Alk-COO(CH 2 —CH 2 ) x O—(CH 2 —CH 2 )—SO 2 —, —OOC-Alk-COO(AOX) x —(CH 2 —CH 2 )—SO 2 —, —OOC-Alk-CONR(AOX) x -Alk-NR—(CH 2 —CH 2 )—SO 2 —, or —O—(CH 2 —CH 2 )—SO 2 —, wherein R, which can be the same or different, is hydrogen or a substituted or unsubstituted aryl or alkyl group, AOX represents an alkylene oxide group of from about 1 to about 12 carbons, and x is an integer between 1 and 500.  
   
   
       43 . The modified pigment product of  claim 19 , wherein the modified pigment product is in a liquid vehicle to form a dispersion.  
   
   
       44 . The modified pigment product of  claim 43 , wherein the liquid vehicle is a non-aqueous vehicle comprising a solvent selected from the group consisting of: ethylcellosolve, ethylcellosolve acetate, butylcellosolve, butylcellosolve acetate, ethylcarbitol, ethylcarbitol acetate, diethyleneglycol, cyclohexanone, propyleneglycol monomethylether, propyleneglycol monomethylether acetate, lactate esters, and mixtures thereof.  
   
   
       45 . The modified pigment product of  claim 43 , further comprising a photosensitive resin.  
   
   
       46 . The modified pigment product of  claim 45 , wherein the photosensitive resin is a resin prepared from an epoxy bisphenol-A resin or an epoxy novolac resin.  
   
   
       47 . A modified pigment product comprising a pigment having attached at least one polymeric group, wherein the pigment is carbon black having a dibutylphthalate absorption (DBP) of from about 25 to 70 mL/100 g.  
   
   
       48 . The modified pigment product of  claim 47 , wherein the modified pigment product is in a liquid vehicle to form a dispersion.  
   
   
       49 . The modified pigment product of  claim 48 , wherein the liquid vehicle is a non-aqueous vehicle comprising a solvent selected from the group consisting of: ethylcellosolve, ethylcellosolve acetate, butylcellosolve, butylcellosolve acetate, ethylcarbitol, ethylcarbitol acetate, diethyleneglycol, cyclohexanone, propyleneglycol monomethylether, propyleneglycol monomethylether acetate, lactate esters, and mixtures thereof.  
   
   
       50 . The modified pigment product of  claim 48 , further comprising a photosensitive resin.  
   
   
       51 . The modified pigment product of  claim 50 , wherein the photosensitive resin is a resin prepared from an epoxy bisphenol-A resin or an epoxy novolac resin.  
   
   
       52 - 84 . (canceled)