Polyether carbamate compounds, compositions containing such compounds, and methods related thereto

Abstract

The present invention provides a reaction product having polyether carbamate groups formed from (A) polyoxyalkylene amine, and (B) cyclic carbonate, in an equivalents ratio ranging from 1:0.5 to 1:1.5. Further provided is a process for preparing the aforementioned reaction product. The present invention also is directed to an improved curable coating composition including (1) a reactive functional group-containing polymer, and (2) a curing agent having functional groups reactive with the functional groups of (1), the improvement being the inclusion in the coating composition the reaction product. Multilayer composite coatings including a first coating layer formed from the curable coating composition and a second coating layer over the curable coating composition are also provided, as well as coated substrates.

1 - 35 . (canceled) 
     
     
         36 . In a multilayer composite coating comprising a first coating layer deposited over at least a portion of a substrate from a first curable coating composition, and a second coating layer deposited over at least a portion of the first coating layer, the second coating layer formed from a second curable coating composition,
 the first curable coating composition comprising:   (1) a reactive functional group-containing polymer; and   (2) a curing agent having functional groups reactive with the functional groups of (1),   the improvement comprising the inclusion in the first curable coating composition of (3) at least one reactive product of the following reactants:
 (A) at least one polyoxyalkylene amine selected from the group consisting of polyoxyalkylene monoamine, polyoxyalkylene diamine, polyoxyalkylene triamine, and mixtures thereof, 
 wherein the polyoxyalkylene diamine comprises a compound having the following structure (I).
   H 2 N[R 1 —O] n [R 3 —O] m —R 2 —NH 2   (I) 
 
 where R 1 , R 2 , and R 3  can be the same or different and each independently represent a C 2  to C 12  alkylene group, and (n+m) represents a value greater than 2, provided that when R 1  and R 3  are different (n+m) represents a value greater than or equal to 2; and 
 (B) at least one cyclic carbonate, 
   wherein the ratio of equivalents of amine (A) to equivalents of cyclic carbonate (B) ranges from 1:0.5 to 1.5.   
     
     
         37 . The multilayer composite coating of  claim 36 , wherein the ratio of equivalents of amine (A) to equivalents of cyclic carbonate (B) ranges from 1.0.8 to 1.1. 
     
     
         38 . The multilayer composite coating of  claim 36 , wherein the ratio of equivalents of amine (A) to equivalents of cyclic carbonate (B) ranges from 1:0.9 to 1.1. 
     
     
         39 . The multilayer composite coating of  claim 36 , wherein the reaction product (3) is present in the first coating composition in an amount sufficient to provide at least 50% interlayer adhesion between the first and second coating layers as determined in accordance with ASTM D3359-97. 
     
     
         40 . The multilayer composite coating of  claim 36 , wherein the reaction product (3) is present in the first coating composition in an amount sufficient to provide at least 75% interlayer adhesion between the first and second coating layers as determined in accordance with ASTM D3359-97. 
     
     
         41 . The multilayer composite coating of  claim 36 , wherein the reaction product (3) is present in the first coating composition in an amount sufficient to provide at least 80% interlayer adhesion between the first and second coating layers as determined by ASTM D3359-97. 
     
     
         42 . The multilayer composite coating of  claim 36 , wherein the reaction product (3) is present in the first coating composition in an amount ranging from 1 to 50 weight percent resin solids, based on the total weight of the resin solids present in the first coating composition. 
     
     
         43 . The multilayer composite coating of  claim 36 , wherein the reaction product (3) is present in the first coating composition in an amount ranging from 5 to 25 weight percent resin solids, based on the total weight of the resin solids present in the first coating composition. 
     
     
         44 . The multilayer composite coating of  claim 36 , wherein the cyclic carbonate comprises a cyclic carbonate selected from the group consisting of ethylene carbonate, propylene carbonate, butylene carbonate, glycerine carbonate, and mixtures thereof. 
     
     
         45 . The multilayer composite coating of  claim 36 , wherein the cyclic carbonate is selected from at least one of ethylene carbonate, propylene carbonate, and butylene carbonate. 
     
     
         46 . The multilayer composite coating of  claim 36 , wherein the first coating layer comprises one or more pigments and the second coating layer is substantially pigment free. 
     
     
         47 . The multilayer composite coating of  claim 36 , wherein the first coating layer comprises one or more pigments, and the second coating layer comprises one or more pigments. 
     
     
         48 . The multilayer composite coating of  claim 36 , wherein the first coating layer is substantially pigment free and the second coating layer comprises one or more pigments. 
     
     
         49 . (canceled) 
     
     
         50 . In a multilayer composite coating comprising a first coating layer deposited over at least a portion of a substrate from a first curable coating composition and a second coating layer deposited over at least a portion of the first coating layer, the second coating layer formed from a second curable coating composition, the first curable coating composition comprising:
 (1) one or more hydroxyl functional polymers selected from the group consisting of a hydroxy-functional polyurethane polymer, a hydroxy-functional acrylic polymer, and mixtures thereof, and   (2) an aminoplast curing agent,   the improvement comprising the inclusion in the first coating composition of (3) at least one reaction product of the following reactants:
 (A) a polyisopropylether diamine, and 
 (B) an ethylene carbonate, 
   wherein the ratio of equivalents of amine (A) to equivalents of cyclic carbonate (B) ranges from 1:0.9 to 1:1.1;   wherein the reaction product (3) is present in the first curable coating composition at a level ranging from 10 to 20 weight percent resin solids, based on weight of total resin solids present in first curable coating composition.   
     
     
         51 . (canceled) 
     
     
         52 . A coated substrate comprising a substrate and a cured coating layer over at least a portion of the substrate, the cured layer formed from a curable coating composition comprising:
 (1) a reactive functional group-containing polymer, and   (2) a curing agent having functional groups reactive with the functional groups of (A),   the improvement comprising the inclusion in the coating composition of (3) at least one reaction product of the following reactants.
 (A) at least one polyoxyalkylene amine selected from the group consisting of polyoxyalkylene monoamine, polyoxyalkylene diamine, polyoxyalkylene triamine, and mixtures thereof, wherein the polyoxyalkylene diamine comprises a compound having the following structure (I):
   H 2 N[R 1 —O] n [R 3 —O] m —R 2 —NH 2   (I) 
 
 where R 1 , R 2 , and R 3  can be the same or different and each independently represent a C 2  to C 12  alkylene group, and (n+m) represents a value greater than 2, provided that when R 1  and R 3  are different (n+m) represents a value greater than or equal to 2; and 
 (B) at least one cyclic carbonate, 
 wherein the ratio of equivalents of amine (A) to equivalents of cyclic carbonate (B) ranges from 1:0.8 to 1:1.1, 
   characterized in that the reaction product (3) is present in the coating composition in an amount sufficient to provide at least 50% adhesion between the coating and substrate as determined in accordance with ASTM-D3359-97.   
     
     
         53 . The coated substrate of  claim 52  wherein the reaction product (3) is present in the coating composition in an amount sufficient to provide at least 75% adhesion between the coating and substrate as determined in accordance with ASTM-D3359-97. 
     
     
         54 . The coated substrate of  claim 52  wherein the reaction product (3) is present in the coating composition in an amount sufficient to provide at least 80% adhesion between the coating and substrate as determined in accordance with ASTM-D3359-97.