Curable solid particulate compositions

Abstract

The present invention relates to curable solid particulate compositions that include: (a) a first reactant having at least two cyclic carbonate groups; and (b) a second reactant having at least two active hydrogen groups that are reactive with the cyclic carbonate groups of the first reactant. With some embodiments, the first reactant is a polyol residue having at least two cyclic carbonate groups, such as bisphenol A that has been reacted with epichlorohydrin, and in which the oxirane groups thereof have been converted to cyclic carbonate groups. The active hydrogen groups of the second reactant, with some embodiments, are each independently selected from hydroxyl groups, thiol groups, and amine groups. The curable solid particulate compositions, with some embodiments, are in the form of curable powder coating compositions.

What is claimed is: 
     
         1 . A curable solid particulate composition comprising:
 (a) a first reactant having at least two cyclic carbonate groups; and   (b) a second reactant having at least two active hydrogen groups that are reactive with the cyclic carbonate groups of said first reactant.   
     
     
         2 . The curable solid particulate composition of  claim 1 , wherein said first reactant is selected from,
 polyol residues having at least two cyclic carbonate groups,   isocyanurates having at least two cyclic carbonate groups,   polyesters having at least two cyclic carbonate groups,   polyethers having at least two cyclic carbonate groups,   polyurethanes having at least two cyclic carbonate groups,   polymers prepared by free radical polymerization having at least two cyclic carbonate groups,   polymers prepared by controlled radical polymerization having at least two cyclic carbonate groups, and   combinations of two or more thereof.   
     
     
         3 . The curable solid particulate composition of  claim 2 , wherein polyol residues having at least two cyclic carbonate groups are each independently formed from a polyol residue having at least two oxirane groups that have been converted to cyclic carbonate groups. 
     
     
         4 . The curable solid particulate composition of  claim 3 , wherein said polyol residue is a residue of a polyol selected from glycerin, trimethylolpropane, trimethylolethane, trishydroxyethylisocyanurate, pentaerythritol, ethylene glycol, propylene glycol, trimethylene glycol, butanediol, heptanediol, hexanediol, octanediol, 4,4′-(propane-2,2-diyl)dicyclohexanol, 4,4′-methylenedicyclohexanol, neopentyl glycol, 2,2,3-trimethylpentane-1,3-diol, 1,4-dimethylolcyclohexane, 2,2,4-trimethylpentane diol, 4,4′-(propane-2,2-diyl)diphenol, 4,4′-methylenediphenol, and combinations thereof. 
     
     
         5 . The curable solid particulate composition of  claim 4 , wherein said polyol is selected from 4,4′-(propane-2,2-diyl)diphenol, 4,4′-(propane-2,2-diyl)dicyclohexanol, 4,4′-methylenediphenol, 4,4′-methylenedicyclohexanol, and combinations thereof. 
     
     
         6 . The curable solid particulate composition of  claim 2 , wherein isocyanurates having at least two cyclic carbonate groups are each independently formed from an isocyanurate having at least two oxirane groups that have been converted to cyclic carbonate groups. 
     
     
         7 . The curable solid particulate composition of  claim 6 , wherein said isocyanurate having at least two oxirane groups is tris(2,3-epoxypropyl)isocyanurate. 
     
     
         8 . The curable solid particulate composition of  claim 2 , wherein,
 polyesters having at least two cyclic carbonate groups are each individually formed from a polyester having at least two oxirane groups that have been converted to cyclic carbonate groups,   polyethers having at least two cyclic carbonate groups are each individually formed from a polyether having at least two oxirane groups that have been converted to cyclic carbonate groups, and   polyurethanes having at least two cyclic carbonate groups, are each individually formed from a polyurethane having at least two oxirane groups that have been converted to cyclic carbonate groups.   
     
     
         9 . The curable solid particulate composition of  claim 2 , wherein,
 polymers prepared by free radical polymerization having at least two cyclic carbonate groups each independently comprise at least two residues of oxirane functional ethylenically unsaturated monomers in which the oxirane groups have been converted to cyclic carbonate groups, and   polymers prepared by controlled radical polymerization having at least two cyclic carbonate groups each independently comprise at least two residues of oxirane functional ethylenically unsaturated monomers in which the oxirane groups have been converted to cyclic carbonate groups.   
     
     
         10 . The curable solid particulate composition of  claim 1 , wherein each active hydrogen group of said second reactant is independently chosen from hydroxyl groups, thiol groups, and amine groups. 
     
     
         11 . The curable solid particulate composition of  claim 10 , wherein each active hydrogen group of said second reactant is independently selected from amine groups, and each amine group of said second reactant is independently selected from primary amines and secondary amines. 
     
     
         12 . The curable solid particulate composition of  claim 11 , wherein said second reactant comprises at least one of linear or branched aliphatic amines, cycloaliphatic amines, heterocycloaliphatic amines, aromatic amines, and heteroaromatic amines. 
     
     
         13 . The curable solid particulate composition of  claim 12 , wherein said second reactant comprises at least one of diaminocyclohexane, 4,4′-methylenedi(cyclohexylamine), 4,4′-(propane-2,2-diyl)dicyclohexanamine, 3,3′-dimethyl-methylenedi(cyclohexylamine), 4,4′-(propane-2,2-diyl)dianiline, 4,4′-methylenedianiline, piperazine, N-amino ethyl piperazine, 5-amino-1-aminomethyl-1,3,3-trimethyl-cyclohexane, diamino ethane, diamino propane, diaminobutane, diaminopentane, diaminohexane, diaminoheptane, diaminooctane, diaminodecane, diaminoundecane, diaminododecane, dicyanamide, 4,4′-diaminodiphenyl sulfone, and melamine. 
     
     
         14 . The curable solid particulate composition of  claim 1 , wherein the ratio of cyclic carbonate equivalents of said first reactant to amine equivalents of said second reactant is from 0.7:1 to 2:1. 
     
     
         15 . The curable solid particulate composition of  claim 1 , wherein said first reactant is present in said curable solid particulate composition in an amount of from 50 to 98 percent by weight, based on total resin solids weight, and said second reactant is present in said curable solid particulate composition in an amount of from 2 to 50 percent by weight, based on total resin solids weight. 
     
     
         16 . The curable solid particulate composition of  claim 1 , wherein said first reactant is resinous and has a glass transition temperature. 
     
     
         17 . The curable solid particulate composition of  claim 1 , wherein said first reactant is crystalline and has a crystalline melting point. 
     
     
         18 . The curable solid particulate composition of  claim 1 , wherein said curable solid particulate composition is free flowing. 
     
     
         19 . The curable solid particulate composition of  claim 18 , wherein said curable solid particulate composition is a powder coating composition. 
     
     
         20 . The curable solid particulate composition of  claim 1 , wherein said curable solid particulate composition is thermosetting.