Coated substrates and methods for producing the same

Abstract

Novel coated substrates comprise a substrate and a coating thereon. The coating comprises a polymeric component and a colorant compound. The colorant compound is produced by reacting an isocyanate compound and an active hydrogen-terminated colorant.

What is claimed is: 
     
         1 . A coated substrate comprising:
 (a) a substrate having at least one surface; and   (b) a coating on the surface of the substrate, the coating comprising:
 (i) a polymeric component selected from the group consisting of prepolymers, polymers, resins, and mixtures thereof; and 
 (ii) a colorant compound, the colorant compound comprising a product produced by the reaction of an isocyanate compound and an active hydrogen-terminated colorant, wherein the active hydrogen-terminated colorant conforms to the structure of Formula (I) 
   
       
         
           
           
               
               
           
         
         wherein R 1  or R 1 -[E] a  is an organic chromophore; E is a linking moiety independently selected from the group consisting of nitrogen, oxygen, sulfur, a sulfonyl group, a sulfonate group, a sulfonamide group, and a carboxyl group; each R 2  is independently selected from the group consisting of hydrogen, alkyl groups, alkoxy groups, and aryl groups; the variable a is a positive integer; the variables b and c are independently selected from the group consisting of integers from 0 to 2; each X is an end group independently selected from the group consisting of hydrogen, a hydroxyl group, a sulfhydryl group, thiol groups, amine groups, alkyl groups, aryl groups, alkyl ester groups, aryl ester groups, organic sulfonate groups, organic sulfate groups, and amide groups; each Z is a divalent organic moiety independently selected from the group consisting of alkanediyl groups, arenediyl groups, and R 5 ; R 5  is a divalent substituent selected from the group consisting of:
 (1) divalent substituents comprising two or more divalent repeating units independently selected from repeating units conforming to the structure of Formula (XX) 
 
       
       
         
           
           
               
               
           
         
         
           wherein R 101  and R 102  are independently selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, aryl, alkoxyalkyl, and aryloxyalkyl; 
           (2) divalent substituents conforming to the structure of Formula (XXI) 
         
       
       
         
           
           
               
               
           
         
         
           wherein R 111  and R 112  are independently selected from the group consisting of hydrogen, hydroxyl, and C 1 -C 10  alkyl, c is an integer from 1 to 12, and d is an integer greater than zero (e.g., an integer from 1 to 100); 
           (3) divalent substituents conforming to the structure of Formula (XXII) 
         
       
       
         
           
           
               
               
           
         
         
           wherein R 121  and R 122  are independently selected from the group consisting of hydrogen, hydroxyl, and C 1 -C 10  alkyl, e is an integer from 1 to 12, and f is an integer greater than zero (e.g., an integer from 1 to 100); and 
           (4) divalent substituents comprising two or more substituents selected from the group consisting of substituents conforming to a structure of Formula (XX), (XXI), or (XXII); 
         
         wherein the colorant comprises three or more —Z—X substituents. 
       
     
     
         2 . The coated substrate of  claim 1 , wherein R 5  is a divalent substituent conforming to a structure of Formula (XXA), (XXB), or (XXC) 
       
         
           
           
               
               
           
         
         wherein s, t, and v are zero or positive integers, and the sum of s, t, and v is 2 or more. 
       
     
     
         3 . The coated substrate of  claim 1 , wherein the active hydrogen-terminated colorant conforms to the structure of Formula (V) 
       
         
           
           
               
               
           
         
         wherein each R 11  is independently selected from the group consisting of hydrogen, halogen atoms, alkyl groups, alkoxy groups, nitrile groups, nitro groups, amide groups, and sulfonamide groups; q is an integer from 0 to 4; R 12  is selected from the group consisting of aromatic groups and heteroatom-containing aromatic groups; Q is a divalent linking group selected from the group consisting of oxygen, sulfur, a carbonyl group, a sulfonyl group, substituted and unsubstituted 1,3-benzothiazole groups, C 1 -C 8  alkanediyl groups, C 2 -C 8  alkenediyl groups, a p-phenylenediamine group, a m-hydroxybenzene group, and a m-di(C 1 -C 4 ) alkoxybenzene group; and r is equal to 2. 
       
     
     
         4 . The coated substrate of  claim 3 , wherein Z is R 5 , and R 5  is a divalent substituent conforming to a structure of Formula (XXA), (XXB), or (XXC) 
       
         
           
           
               
               
           
         
         wherein s, t, and v are zero or positive integers, and the sum of s, t, and v is 2 or more. 
       
     
     
         5 . The coated substrate of  claim 3 , wherein the active hydrogen-terminated colorant conforms to the structure of one of Formulae (VI), (VII), (VIII), (IX), or (X) below: 
       
         
           
           
               
               
           
         
       
     
     
         6 . The coated substrate of  claim 5 , wherein Z is R 5 , and R 5  is a divalent substituent conforming to a structure of Formula (XXA), (XXB), or (XXC) 
       
         
           
           
               
               
           
         
         wherein s, t, and v are zero or positive integers, and the sum of s, t, and v is 2 or more. 
       
     
     
         7 . The coated substrate of  claim 6 , wherein s, t, and v are selected from the group consisting of zero and positive integers from 1 to 150. 
     
     
         8 . The coated substrate of  claim 1 , wherein the colorant is produced from a reaction mixture in which the ratio of isocyanate groups from the isocyanate compound to active hydrogen groups from the active hydrogen-terminated colorant is about 10 to about 1. 
     
     
         9 . The coated substrate of  claim 8 , wherein the colorant compound is produced by first reacting the isocyanate compound and the active hydrogen-terminated colorant to produce a first product, and then reacting the first product with a chain extender. 
     
     
         10 . The coated substrate of  claim 9 , wherein the ratio of isocyanate groups from the isocyanate compound to active hydrogen groups from the active hydrogen-terminated colorant and the chain extender is about 1.8 to about 0.8. 
     
     
         11 . The coated substrate of  claim 1 , wherein the colorant is produced from a reaction mixture in which the ratio of isocyanate groups from the isocyanate compound to active hydrogen groups from the active hydrogen-terminated colorant is about 1.8 to about 0.8.