Coating compositions, their preparation, and coated articles made therefrom

Abstract

A coating composition comprising components A, B and optionally C, wherein component A comprises at least one hydroxy-terminated polyarylate. Component B is an organic species which can react with the hydroxy terminal groups of component A, and component C is a catalyst or mixture of catalysts. The hydroxy-terminated polyarylates are prepared by a solution polymerization method.

1 - 36 . (canceled)  
     
     
         37 . A method of making a polyarylate comprising structural units derived from at least one dihydroxy-substituted aromatic hydrocarbon and at least one aromatic dicarboxylic acid dichloride, said polyarylate further comprising phenolic hydroxy groups, said method comprising the steps of: 
 (a) combining at least one dihydroxy-substituted aromatic hydrocarbon moiety, and at least one organic base in an inert organic solvent to form a mixture, said dihydroxy-substituted aromatic hydrocarbon moiety being substantially soluble in said mixture, said dihydroxy-substituted aromatic hydrocarbon being used in an amount corresponding to a molar amount of dihydroxy-substituted aromatic hydrocarbon moieties;    (b) adding to the mixture formed in step (a) at least one dicarboxylic acid dichloride in a molar amount such that the molar amount of dicarboxylic acid dichloride in the mixture is stoichiometrically deficient relative to the total molar amount of dihydroxy-substituted aromatic hydrocarbon moieties, to form a reaction mixture; and    (c) agitating the reaction mixture formed in step (b) until essentially all of the dicarboxylic acid dichloride has reacted.    
     
     
         38 . A method according to  claim 37  wherein said dihydroxy-substituted aromatic hydrocarbon moiety comprises structure V  
       
         
           
           
               
               
           
         
       
       wherein A 1  is independently an aromatic group; E is alkylene, alkylidene, or cycloaliphatic group; a sulfur-containing linkage; a phosphorus-containing linkage; an ether linkage; a carbonyl group; a tertiary amino linkage; or a silicon-containing linkage; R 3  is independently at each occurrence a monovalent hydrocarbon group; Y 1  is independently at each occurrence a monovalent hydrocarbon group, halogen, and nitro; “m” represents any integer from and including zero through the number of positions on A1 available for substitution; “p” represents an integer from and including zero through the number of positions on E available for substitution; “t” represents an integer equal to at least one; “s” is either zero or one; and “u” represents any integer including zero.  
     
     
         39 . A method according to  claim 37  wherein said dicarboxylic acid dichloride is selected from the group consisting of monocyclic dicarboxylic acid dichlorides and polycyclic aromatic dicarboxylic acid dichlorides.  
     
     
         40 . A method according to  claim 37  wherein said dicarboxylic acid dichloride is selected from the group consisting of isophthaloyl dichloride, terephthaloyl dichloride, mixtures of isophthaloyl and terephthaloyl dichlorides, diphenyl dicarboxylic acid dichloride, diphenylether dicarboxylic acid dichloride, and naphthalene-2,6-dicarboxylic acid dichloride.  
     
     
         41 . A method according to  claim 37  wherein the organic base is at least one tertiary amine.  
     
     
         42 . The method according to  claim 41  wherein said tertiary amine is selected from the group consisting of triethylamine, dimethylbutylamine, diisopropylethylamine, N-ethylpiperidine, N-methylpiperidine, N-methylmorpholine, N,N-dimethyldecylamine; N,N-dimethyloctadecylamine; 2,2,6,6-tetramethylpiperidine, and diazabicylco[2.2.2]octane.  
     
     
         43 . A method according to  claim 37  wherein the organic base is present in an amount corresponding to about 0.9 to about 10 equivalents with respect to the dihydroxy-substituted aromatic hydrocarbon moiety.  
     
     
         44 . A method according to  claim 37  wherein said at least one dicarboxylic acid dichloride comprises “soft block” structural units having formula VIII:  
       
         
           
           
               
               
           
         
       
       wherein R 4  a C 2 -C 100  aliphatic radial, or a C 4 -C 20  cycloaliphatic radical and R 5  and R 6  each independently represent a bond,  
       
         
           
           
               
               
           
         
       
     
     
         45 . A method of making an oligomeric polyarylate comprising structural units having formula I  
       
         
           
           
               
               
           
         
       
       wherein R 1  is independently at each occurrence a C 1 -C 12  alkyl radical and n is 0-3, said polyarylate further comprising phenolic hydroxy groups, said method comprising the steps of: 
 (a) combining at least one resorcinol moiety, and at least one organic base in an inert organic solvent to form a mixture, said resorcinol moiety being substantially soluble in said mixture, said resorcinol being used in an amount corresponding to a molar amount of resorcinol moieties;  
 (b) adding to the mixture formed in step (a) at least one dicarboxylic acid dichloride in a molar amount such that the molar amount of dicarboxylic acid dichloride in the mixture is stoichiometrically deficient relative to the total molar amount of resorcinol moieties, to form a reaction mixture; and  
 (c) agitating the reaction mixture formed in step (b) until essentially all of the dicarboxylic acid dichloride has reacted.  
 
     
     
         46 . The method of making an oligomeric polyarylate according to  claim 45  wherein said at least one resorcinol moiety is selected from the group consisting of unsubstituted resorcinol, 2-methyl resorcinol and mixtures thereof.  
     
     
         47 . The method of making an oligomeric polyarylate according to  claim 46  wherein said at least one resorcinol moiety is an unsubstituted resorcinol.  
     
     
         48 . The method of making an oligomeric polyarylate according to  claim 45  wherein the organic base is present in an amount corresponding to about 0.9 to about 10 equivalents with respect to the resorcinol moiety.  
     
     
         49 . The method of making an oligomeric polyarylate according to  claim 48  wherein the organic base comprises at least one tertiary amine.  
     
     
         50 . The method of making an oligomeric polyarylate according to  claim 49  wherein said tertiary amine is selected from the group consisting of triethylamine, dimethylbutylamine, diisopropylethylamine, N-ethylpiperndine, N-methylpiperidine, N-methylmorpholine, N,N-dimethyldecylamine; N,N-dimethyloctadecylamine; 2,2,6,6-tetramethylpiperidine, and diazabicylco[2.2.2]octane.  
     
     
         51 . The method of making an oligomeric polyarylate according to  claim 45  wherein at least one dicarboxylic acid dichloride is naphthalene-2,6-dicarboxylic acid dichloride.  
     
     
         52 . The method of making an oligomeric polyarylate according to  claim 45  wherein the dicarboxylic acid dichloride is a mixture of isophthaloyl dichloride and terephthaloyl dichloride.  
     
     
         53 . The method of making an oligomeric polyarylate according to  claim 52  wherein said mixture has a molar ratio of isophthaloyl dichloride to terephthaloyl dichloride in a range between about 0.2:1 and about 5:1.  
     
     
         54 . The method of making an oligomeric polyarylate according to  claim 53  wherein the molar ratio of isophthaloyl dichloride to terephthaloyl dichloride is in a range between about 0.8:1 and about 2.5:1.  
     
     
         55 . The method of making an oligomeric polyarylate according to  claim 45  wherein the organic solvent is selected from the group consisting of chloroform, chlorobenzene, toluene, methylene chloride, 1,2-dichloroethane, dichlorobenzene, xylene, trimethylbenzene, and mixtures thereof.  
     
     
         56 . The method of making an oligomeric polyarylate according to  claim 45  wherein said at least one dicarboxylic acid dichloride comprises “soft block” structural units having formula VIII:  
       
         
           
           
               
               
           
         
       
       wherein R 4  a C 2 -C 100  aliphatic radial, or a C 4 -C 20  cycloaliphatic radical and R 5  and R 6  each independently represent a bond,  
       
         
           
           
               
               
           
         
       
     
     
         57 . The method of making an oligomeric polyarylate according to  claim 56  wherein said dicarboxylic acid dichloride comprising “soft block” structural units having formula VIII is used in an amount sufficient to provide a concentration of the “soft block” having formula VIII in the product oligomeric polyarylate in a range between about 0.01 and about 20% by weight.  
     
     
         58 - 60 . (canceled)