Surface Modification of Pigments and Compositions Comprising the Same

Abstract

Disclosed herein is a method of making a modified pigment, comprising: reacting, under Mitsunobu conditions: (a) a first reactant comprising a protonated nucleophile having a pK a <15, and (b) a second reactant comprising a hydroxyl-containing organic group, wherein a pigment is attached to either the first or second reactant. The method further comprises forming the modified pigment having attached an organic species comprising the nucleophile bonded to the organic group, with the net elimination of a proton and a hydroxyl. Also disclosed herein are modified pigments, which can have applications in chemical toners, inkjet ink and electrophoretic ink compositions, black matrix materials, color filters, and coatings.

1 - 41 . (canceled) 
     
     
         42 . A modified pigment comprising a pigment attached to an organic group via an —N—C— bond, wherein the nitrogen atom of the —N—C— bond is native to the pigment and the carbon atom of the —N—C— bond, and substituents thereof, are not native to the pigment prior to modification. 
     
     
         43 . The modified pigment of  claim 42 , wherein the pigment is organic. 
     
     
         44 . (canceled) 
     
     
         45 . The modified pigment of  claim 42 , wherein the —N—C— bond forms a linkage selected from imides, amides, and amines. 
     
     
         46 . (canceled) 
     
     
         47 . The modified pigment of  claim 42 , wherein the pigment is selected from Pigment Yellow 185 and Pigment Red 269. 
     
     
         48 . A modified pigment comprising an organic pigment attached to an organic group via an —O—C— bond, wherein the —O—C— bond forms phenolate or naphtholate linkages, and wherein the phenolate or naphtholate linkages have aromatic groups that are native to the pigment, and wherein the carbon atom of the —O—C— bond, and substituents thereof, are not native to the pigment prior to modification. 
     
     
         49 - 50 . (canceled) 
     
     
         51 . The modified pigment of  claim 42 , wherein the organic group comprises a polymer. 
     
     
         52 - 53 . (canceled) 
     
     
         54 . A chemical toner composition, comprising the modified pigment of  claim 42 , the chemical toner composition further comprising a resin. 
     
     
         55 . An inkjet ink composition, comprising the modified pigment of  claim 42 . 
     
     
         56 . (canceled) 
     
     
         57 . A black matrix composition, comprising the modified pigment of  claim 42 . 
     
     
         58 - 59 . (canceled) 
     
     
         60 . A color filter comprising the modified pigment of  claim 42 , wherein the modified pigment is an organic pigment. 
     
     
         61 . A coating composition, comprising the modified pigment of  claim 42 . 
     
     
         62 . A UV-curable ink composition, comprising the modified pigment of  claim 42 , and further comprising a UV-curable resin. 
     
     
         63 . An electrophoretic ink composition, comprising the modified pigment of  claim 42 . 
     
     
         64 . The modified pigment of  claim 48 , wherein the organic group comprises a polymer. 
     
     
         65 . A chemical toner composition, comprising the modified pigment of  claim 48 , the chemical toner composition further comprising a resin. 
     
     
         66 . An inkjet ink composition, comprising the modified pigment of  claim 48 . 
     
     
         67 . A black matrix composition, comprising the modified pigment of  claim 48 . 
     
     
         68 . A color filter comprising the modified pigment of  claim 48 , wherein the modified pigment is an organic pigment. 
     
     
         69 . A coating composition, comprising the modified pigment of  claim 48 . 
     
     
         70 . A UV-curable ink composition, comprising the modified pigment of  claim 48 , and further comprising a UV-curable resin. 
     
     
         71 . An electrophoretic ink composition, comprising the modified pigment of  claim 48 .