Energy curable high reactivity multi vinylether or acrylate functional resins

Abstract

A polycarbonate polyfunctional-vinyl ether molecule of formula (I):

1 . An ink, coating, or adhesive composition comprising a polyfunctional acrylate molecule of formula (II): 
       
         
           
           
               
               
           
         
       
       wherein
 G is S or N; 
 each A is independently a C 1 -C 10  alkylene group; 
 each D is independently S, O, or N R10 , wherein R 10  has the structure: 
 
       
         
           
           
               
               
           
         
         each x is independently an integer from 0 to 10; 
         each n is independently an integer from 0 to 20; and 
         z is 2 when G is S or z is 3 when G is N. 
       
     
     
         2 . The ink, coating, or adhesive composition of  claim 1 , wherein A is an optionally substituted C 1 -C 10  alkylene group. 
     
     
         3 . The ink, coating, or adhesive composition of  claim 1 , wherein A is —CH 2 CH 2 —. 
     
     
         4 . The ink, coating, or adhesive composition of  claim 1 , wherein the molecule of formula (II) is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         5 . The ink, coating, or adhesive composition of  claim 1 , wherein the molecule exhibits a viscosity from about 10 centipoise to about 15000 centipoise at 25° C. 
     
     
         6 . The ink, coating, or adhesive composition of  claim 1 , wherein the molecule exhibits a viscosity of about 10 centipoise to about 1000 centipoise at 25° C. 
     
     
         7 . The ink, coating, or adhesive composition of  claim 1 , wherein the composition is configured for use in conventional printing, 3D printing, inks, inkjet inks, paints, and packaging applications. 
     
     
         8 . The ink, coating, or adhesive composition of  claim 1 , wherein the composition is a coating composition, wherein the coating is configured for use in automotive original equipment manufacturer paint applications or automotive refinishing applications. 
     
     
         9 . A process for preparing a polyfunctional acrylate molecule, the process comprising
 contacting in a solvent a heteroatom-containing polyol with an acrylate in the presence of a catalyst to form a reaction mixture; and   heating the reaction mixture under azeotropic reflux conditions to form an alcohol or water from the reaction mixture;   wherein:
 the alcohol or water is removed from the reaction mixture under the azeotropic reflux conditions; and 
 the polyfunctional acrylate molecule is a molecule of formula (II): 
   
       
         
           
           
               
               
           
         
       
       wherein
 G is S or N; 
 each A is independently a C 1 -C 10  alkylene group; 
 each D is independently S, O, or N R10 , wherein R 10  has the structure: 
 
       
         
           
           
               
               
           
         
         each x is independently an integer from 0 to 10; 
         each n is independently an integer from 0 to 20; and 
         z is 2 when G is S or z is 3 when G is N. 
       
     
     
         10 . The process of  claim 9 , wherein the heating is conducted from about 70° C. to about 140° C. 
     
     
         11 . The process of  claim 9 , wherein the catalyst comprises a strong acid, strong base, a transesterification catalyst, a Lewis acid, a Brønsted acid, or an amine. 
     
     
         12 . The process of  claim 9 , wherein an overhead temperature of the reaction has an azeotropic distillation temperature from about 40° C. to about 80° C. 
     
     
         13 . The process of  claim 9 , wherein the acrylate comprises a (meth)acrylate comprising acrylic acid, methacrylic acid, methylmethacrylic acid, methylmethacrylate, ethylmethacrylate, hydroxy vinyl ether, methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-butyl acrylate (BA), n-decyl acrylate, isobutyl acrylate, n-amyl acrylate, n-hexyl acrylate, isoamyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, N,N-dimethylaminoethyl acrylate, N,N-diethylaminoethyl acrylate, t-butylaminoethyl acrylate, 2-sulfoethyl acrylate, trifluoroethyl acrylate, glycidyl acrylate, benzyl acrylate, allyl acrylate, 2-n-butoxyethyl acrylate, 2-chloroethyl acrylate, sec-butyl-acrylate, tert-butyl acrylate, 2-ethylbutyl acrylate, cinnamyl acrylate, crotyl acrylate, cyclohexyl acrylate, cyclopentyl acrylate, 2-ethoxyethyl acrylate, furfuryl acrylate, hexafluoroisopropyl acrylate, methallyl acrylate, 3-methoxybutyl acrylate, 2-methoxybutyl acrylate, 2-nitro-2-methylpropyl acrylate, n-octylacrylate, 2-ethylhexyl acrylate, 2-phenoxyethyl acrylate, 2-phenylethyl acrylate, phenyl acrylate, propargyl acrylate, tetrahydrofurfuryl acrylate, tetrahydropyranyl acrylate, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, n-butyl methacrylate (BMA), isopropyl methacrylate, isobutyl methacrylate, n-amyl methacrylate, n-hexyl methacrylate, isoamyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, N,N-dimethylaminoethyl methacrylate, N,N-diethylaminoethyl methacrylate, t-butylaminoethyl methacrylate, 2-sulfoethyl methacrylate, trifluoroethyl methacrylate, glycidyl methacrylate (GMA), benzyl methacrylate, allyl methacrylate, 2-n-butoxyethyl methacrylate, 2-chloroethyl methacrylate, sec-butyl-methacrylate, tert-butyl methacrylate, 2-ethylbutyl methacrylate, cinnamyl methacrylate, crotyl methacrylate, cyclohexyl methacrylate, cyclopentyl methacrylate, 2-ethoxyethyl methacrylate, furfuryl methacrylate, hexafluoroisopropyl methacrylate, methallyl methacrylate, 3-methoxybutyl methacrylate, 2-methoxybutyl methacrylate, 2-nitro-2-methylpropyl methacrylate, n-octylmethacrylate, 2-ethylhexyl methacrylate, 2-phenoxyethyl methacrylate, 2-phenylethyl methacrylate, phenyl methacrylate, propargyl methacrylate, tetrahydrofurfuryl methacrylate and tetrahydropyranyl methacrylate. Examples of other suitable acrylic and methacrylic moieties include, but are not limited to hydroxyalkyl acrylates and methacrylates, acrylic acid and its salts, acrylonitrile, acrylamide, methyl α-chloroacrylate, methyl 2-cyanoacrylate, N-ethylacrylamide, N,N-diethylacrylamide, acrolein, methacrylic acid and its salts, methacrylonitrile, methacrylamide, N-methylmethacrylamide, N-ethylmethacrylamide, N,N-diethylmethacrylamide, N,N-dimethylmethacrylamide, N-phenylmethacrylamide, or methacrolein. 
     
     
         14 . The process of  claim 9 , wherein the solvent comprises C 5 -C 10  alkanes, C 5 -C 10  cycloalkane, or C 6 -C 12  aromatic solvents.