Amine functionalized polymer

Abstract

A macromolecule includes a functional group including imine functionality bonded to a polymer chain. Where desired, the functional group also can contain additional (e.g., amine and/or silane) functionality. The material can be provided by reacting a polymer including carbonyl functionality with a compound including a primary amino group. The functional group can interact with particulate filler such as, e.g., carbon black and silica.

1 . A macromolecule comprising a polymer chain and, bonded thereto, a functional group comprising imine functionality.  
   
   
       2 . The macromolecule of  claim 1  wherein said imine functionality is defined by the general formula >C═N—(CH 2 ) n — where n is an integer of from 1 to 10 inclusive.  
   
   
       3 . The macromolecule of  claim 1  wherein said functional group is bonded to a terminus of said polymer chain through said imine functionality.  
   
   
       4 . The macromolecule of  claim 1  wherein said functional group further comprises one of amine and silane functionality.  
   
   
       5 . The macromolecule of  claim 4  wherein said silane functionality is provided in the form of an alkoxysilane or alkylalkoxysilane.  
   
   
       6 . A functional polymer comprising the reaction product of a polymer comprising carbonyl functionality and a compound comprising a primary amino group.  
   
   
       7 . The functional polymer of  claim 6  wherein said carbonyl functionality is provided by reaction of a living polymer with a compound comprising an aldehyde group.  
   
   
       8 . The functional polymer of  claim 6  wherein said carbonyl functionality is provided by reaction of a living polymer with a heterocyclic compound comprising within its ring structure a nitrogen atom and a carbonyl group.  
   
   
       9 . The functional polymer of  claim 8  wherein said heterocyclic compound is an imidazolidinone or a pyrrolidinone.  
   
   
       10 . The functional polymer of  claim 6  wherein said compound comprising a primary amino group further comprises additional amine functionality.  
   
   
       11 . The functional polymer of  claim 10  wherein said additional amine functionality is primary.  
   
   
       12 . The functional polymer of  claim 6  wherein said compound comprising a primary amino group further comprises a silane group.  
   
   
       13 . The functional polymer of  claim 12  wherein said silane group is provided in the form of an alkoxysilane or alkylalkoxysilane.  
   
   
       14 . A method of making a functional polymer comprising reacting a polymer that comprises carbonyl functionality with a compound that comprises a primary amino group.  
   
   
       15 . The method of  claim 14  wherein said carbonyl functionality is provided by reacting a living polymer with one of 
 (1) a compound comprising an aldehyde group, and    (2) a heterocyclic compound comprising within its ring structure a nitrogen atom and a carbonyl group.    
   
   
       16 . The method of  claim 15  wherein said heterocyclic compound is one of an imidazolidinone and a pyrrolidinone.  
   
   
       17 . The method of  claim 14  wherein said compound comprising a primary amino group further comprises additional amine functionality.  
   
   
       18 . The method of  claim 17  wherein said additional amine functionality is primary.  
   
   
       19 . The method of  claim 14  wherein said compound comprising a primary amino group further comprises a silane group.  
   
   
       20 . The method of  claim 19  wherein said silane group is provided in the form of an alkoxysilane or alkylalkoxysilane.