Polymerizable compositions, polymerized compositions, and methods of making and using the same

Abstract

A polymerizable composition includes an organoborane-base complex that is a complex of an organoborane and a base, a decomplexing agent that at least partially liberates the organoborane from the organoborane-base complex, a polymerizable thiol-containing component comprising at least one polymerizable thiol-containing compound having a plurality of thiol groups in which the sulfur atom of the thiol group is covalently bonded to carbon, a hydroperoxide, and a polymerizable ethylenically-unsaturated component comprising at least one polymerizable ethylenically-unsaturated compound having a plurality of ethylenically-unsaturated groups. The combined amounts of the thiol-containing and ethylenically-unsaturated compounds total at least 50 percent by weight of all polymerizable material in the polymerizable composition. The composition may be provide as a two-part composition. Polymerized reaction product of the composition and methods of making the composition are also disclosed.

What is claimed is: 
     
         1 . A polymerizable composition comprising:
 a part A composition comprising an organoborane-base complex that is a complex of an organoborane and a base, wherein the organoborane is represented by the formula B(R 1 )(R 2 )(R 3 ) wherein:   R 1  represents an alkyl group having from 1 to 10 carbon atoms; and   R 2  and R 3  independently represent:
 alkyl groups having 1 to 10 carbon atoms; 
 cycloalkyl groups having 3 to 10 carbon atoms; 
 aryl groups having 6 to 12 carbon atoms; or 
 aryl groups substituted with alkyl groups having 1 to 10 carbon atoms or cycloalkyl groups having 3 to 10 carbon atoms; 
   or any two of R 1 , R 2 , and R 3  taken together form a divalent alkylene group having from 3 to 7 carbon atoms, and   wherein the base is a complexing agent selected from a compound having one or more amine groups, amidine groups, hydroxide groups, alkoxide groups, or a combination thereof; and   a part B composition comprising a decomplexing agent that at least partially liberates the organoborane from the organoborane-base complex;   wherein the polymerizable composition further comprises:
 a polymerizable thiol-containing component comprising at least one polymerizable thiol-containing compound having a plurality of thiol groups in which the sulfur atom of the thiol group is covalently bonded to carbon; 
 a hydroperoxide; and 
 a polymerizable ethylenically-unsaturated component comprising at least one polymerizable ethylenically-unsaturated compound having a plurality of ethylenically-unsaturated groups, 
   wherein the combined amounts of the thiol-containing and ethylenically-unsaturated compounds total at least 50 percent by weight of all polymerizable material in the polymerizable composition.   
     
     
         2 . The polymerizable composition of  claim 1 , wherein the hydroperoxide is an organic hydroperoxide. 
     
     
         3 . The polymerizable composition of  claim 1 , wherein the hydroperoxide is present in the part B composition. 
     
     
         4 . The polymerizable composition of  claim 1 , wherein upon reaction a —C—S—C—C— linkage is formed. 
     
     
         5 . The polymerizable composition of  claim 1 , wherein the base is an amine comprising at least one primary or secondary amine group. 
     
     
         6 . A composition prepared by combining components comprising:
 a part A composition comprising an organoborane-base complex that is a complex of an organoborane and a base, wherein the organoborane is represented by the formula B(R 1 )(R 2 )(R 3 ) wherein:
 R 1  represents an alkyl group having from 1 to 10 carbon atoms; and 
 R 2  and R 3  independently represent:
 alkyl groups having 1 to 10 carbon atoms; 
 cycloalkyl groups having 3 to 10 carbon atoms; 
 aryl groups having 6 to 12 carbon atoms; or 
 aryl groups substituted with alkyl groups having 1 to 10 carbon atoms or cycloalkyl groups having 3 to 10 carbon atoms; 
 
 or any two of R 1 , R 2 , and R 3  taken together form a divalent alkylene group having from 3 to 7 carbon atoms, and 
 wherein the base is a complexing agent selected from a compound having one or more amine groups, one or more amidine groups, one or more hydroxide groups, one or more alkoxide groups, or a combination thereof; and 
 a part B composition comprising a decomplexing agent that at least partially liberates the organoborane from the organoborane-base complex, 
 wherein at least one of the part A composition and the part B composition further comprises:
 a polymerizable thiol-containing component comprising at least one polymerizable thiol-containing compound having a plurality of thiol groups in which the sulfur atom of the thiol group is covalently bonded to carbon; 
 a hydroperoxide; and 
 a polymerizable ethylenically-unsaturated component comprising at least one polymerizable ethylenically-unsaturated compound having a plurality of ethylenically-unsaturated groups, 
 
 wherein the combined amounts of the thiol-containing and ethylenically-unsaturated compounds total at least 50 percent by weight of all polymerizable material in the polymerizable composition. 
   
     
     
         7 . The composition of  claim 6 , wherein the hydroperoxide is an organic hydroperoxide. 
     
     
         8 . The composition of  claim 6 , wherein the base is an amine comprising at least one primary or secondary amine group.