Method using zirconium catalyst for producing carbamate-functional materials

Abstract

A carbamate-functional material is prepared by reacting a carbamate compound with a hydroxy-functional material using zirconium acetylacetonates catalyst.

1 : A method of preparing a carbamate-functional material, the method comprising:
 reacting a carbamate compound with a hydroxy-functional material in the presence of a zirconium acetylacetonate catalyst to form a carbamate-functional material.   
     
     
         2 : The method according to  claim 1 , wherein the carbamate compound is an alkyl carbamate. 
     
     
         3 : The method according to  claim 2 , wherein the carbamate compound is at least one selected from the group consisting of methyl carbamate, ethyl carbamate, n-propyl carbamate, isopropyl carbamate, n-butyl carbamate, isobutyl carbamate, tert-butyl carbamate, n-hexyl carbamate, 2-ethylhexyl carbamate, cyclohexyl carbamate, and phenyl carbamate, and combinations thereof. 
     
     
         4 : The method according to  claim 1 , wherein the hydroxy-functional material is a monomeric compound comprising having from 1 to 160 carbon atoms. 
     
     
         5 : The method according to  claim 1 , wherein the hydroxy-functional material comprises from 12 to 72 carbon atoms and at least two hydroxyl groups. 
     
     
         6 : The method according to  claim 1 , wherein the hydroxy-functional material is obtained by a reduction of an addition product of unsaturated fatty acids. 
     
     
         7 : The method according to  claim 1 , wherein the hydroxy-functional material is a hyperbranched polyol. 
     
     
         8 : The method according to  claim 7 , wherein the reacting is performed during a final step of obtaining the hyperbranched polyol. 
     
     
         9 : The method according to  claim 1 , wherein the hydroxy-functional material is at least one selected from the group consisting of polyester polyols, polyether polyols, polyhydroxy polycarbonates, polyurethane polyols, polyvinyl polymer polyols, polyhydroxy polyesteramides, polysiloxane polyols, and polyhydroxy polythioethers. 
     
     
         10 : The method according to  claim 9 , wherein the hydroxy-functional material is an acrylic polymer polyol. 
     
     
         11 : The method according to  claim 10 , wherein the reacting is performed during a polymerization of the hydroxy-functional material. 
     
     
         12 : The method according to  claim 1 , wherein the zirconium acetylacetonate is present in an amount of from 0.25 wt. % to 1.4 wt. % based on the total weight of the hydroxy-functional material and the carbamate compound. 
     
     
         13 : The method according to  claim 1 , wherein the reacting is carried out at a temperature in the range of from 126° C. to 136° C. 
     
     
         14 : The method according to  claim 1 , wherein the carbamate-functional material comprises at least 60% of theoretical total replacement of the hydroxyl groups of the hydroxy-functional material with carbamate groups. 
     
     
         15 : A carbamate-functional material obtained by the method according to  claim 1 . 
     
     
         16 : A coating composition comprising the carbamate-functional material according to  claim 15 . 
     
     
         17 : The coating composition according to  claim 16  which is a clearcoat composition. 
     
     
         18 : A method of coating an article, the method comprising:
 applying the coating composition according to  claim 16  to an article.