US2011313109A1PendingUtilityA1

Modified hydrocarbylphenol-aldehyde resins for use as tackifiers and rubber compositions containing them

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Individually held — no corporate assignee on recordPriority: Sep 5, 2006Filed: Sep 1, 2011Published: Dec 22, 2011
Est. expirySep 5, 2026(~0.1 yrs left)· nominal 20-yr term from priority
Inventors:Timothy Edward BanachL. Scott HowardTodd Scott MakenzieRonald K. Smith
C08G 59/08C08L 61/14C08L 21/00C08L 61/00C08L 63/00C08G 8/10C08L 59/00C08G 8/00C08J 3/24C08L 71/126C08L 61/06
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Claims

Abstract

The invention relates to a modified hydrocarbylphenol-aldehyde resin prepared by reacting a hydrocarbylphenol-aldehyde resin with a primary or secondary amine and further with an epoxide. The invention also provides a process for preparing a modified, hydrocarbylphenol-aldehyde resin and a rubber composition containing such resin.

Claims

exact text as granted — not AI-modified
1 . A modified, hydrocarbylphenol-aldehyde resin prepared by reacting an epoxide with a resin of Formula (I) in the presence of a basic catalyst and at a basic pH, 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is a straight or branched C 1 -C 30  alkyl; 
         R 2  is —CH 2 R 5 ,
 wherein R 5  is an amine of formula (i) 
 
       
       
         
           
           
               
               
           
         
         
           wherein R′ and R″ are independently H, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, aryl, or wherein R′ and R″, together with the N carrying them, form a 5-7 membered heterocyclic ring; 
         
         R 3  is R 2  or —CH(R 5 )OH; 
         R 4  is H or C 1 -C 4  alkyl; and 
         m plus n is at least 1. 
       
     
     
         2 . The modified, hydrocarbylphenol-aldehyde resin of  claim 1 , wherein said resin is prepared by reacting about 1 to about 25 weight percent the epoxide with the resin of Formula (I). 
     
     
         3 . The modified, hydrocarbylphenol-aldehyde resin of  claim 1 , wherein R 5  is morpholinyl. 
     
     
         4 . The modified, hydrocarbylphenol-aldehyde resin of  claim 1 , wherein R 1  is a straight or branched C 1 -C 15  alkyl. 
     
     
         5 . The modified, hydrocarbylphenol-aldehyde resin of  claim 4 , wherein R 1  is tertiary butyl or tertiary octyl. 
     
     
         6 . A process for preparing a modified, hydrocarbylphenol-aldehyde resin comprising the step of:
 (a) reacting an epoxide with a resin of Formula (I) in the presence of a basic catalyst and at a basic pH,   
       
         
           
           
               
               
           
         
         
           wherein 
           R 1  is a straight or branched C 1 -C 30  alkyl; 
           R 2  is —CH 2 R 5 ,
 wherein R 5  is an amine of formula (i) 
 
         
       
       
         
           
           
               
               
           
         
         
           
             wherein R′ and R″ are independently H, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, aryl, or wherein R′ and R″, together with the N carrying them, form a 5-7 membered heterocyclic ring; 
           
           R 3  is R 2  or —CHR 5 OH; 
           R 4  is H or C 1 -C 4  alkyl; and 
           m plus n is at least 1. 
         
       
     
     
         7 . The process for preparing a modified, hydrocarbylphenol-aldehyde resin according to  claim 6 , wherein step (a) comprises reacting about 1 to about 25 weight percent of the epoxide. 
     
     
         8 . The process for preparing a modified, hydrocarbylphenol-aldehyde resin of  claim 6 , wherein R 5  is morpholinyl. 
     
     
         9 . The process for preparing a modified, hydrocarbylphenol-aldehyde resin of  claim 6 , wherein R 1  is a straight or branched C 1 -C 15  alkyl. 
     
     
         10 . The process for preparing a modified, hydrocarbylphenol-aldehyde resin of  claim 9 , wherein R 1  is tertiary butyl or tertiary octyl. 
     
     
         11 . A rubber composition having improved tack, comprising a rubber or mixtures of rubbers, and 0.5 to 7 phr of a modified, hydrocarbylphenol-aldehyde resin of  claim 1 . 
     
     
         12 . The rubber composition of  claim 11 , wherein R 5  is morpholinyl. 
     
     
         13 . The rubber composition of  claim 11 , wherein R 1  is a straight or branched C 1 -C 15  alkyl. 
     
     
         14 . The rubber composition of  claim 13 , wherein R 1  is tertiary butyl or tertiary octyl. 
     
     
         15 . The rubber composition of  claim 11 , wherein said rubber composition is a 30/70 natural rubber/butadiene rubber composition, a 70/30 styrene butadiene rubber/butadiene rubber composition, or a natural rubber composition. 
     
     
         16 . A modified, hydrocarbylphenol-aldehyde resin prepared by reacting a C 16  alkyl epoxide with a resin of Formula (I) in the presence of a basic catalyst and at a basic pH, 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is a straight or branched C 1 -C 30  alkyl; 
         R 2  is —CH 2 R 5 , wherein R 5  is a morpholinyl group; 
         R 3  is R 2  or —CH(R 5 )OH; 
         R 4  is H or C 1 -C 4  alkyl; and 
         m plus n is at least 1. 
       
     
     
         17 . The modified, hydrocarbylphenol-aldehyde resin of  claim 16 , wherein R 1  is tertiary butyl or tertiary octyl. 
     
     
         18 . A rubber composition having improved tack, comprising
 a rubber or mixtures of rubbers, and   0.5 to 7 phr of a modified, hydrocarbylphenol-aldehyde resin of  claim 16 .   
     
     
         19 . A process for preparing a modified, hydrocarbylphenol-aldehyde resin comprising the step of:
 (a) reacting a C 16  alkyl epoxide with a resin of Formula (I) in the presence of a basic catalyst and at a basic pH,   
       
         
           
           
               
               
           
         
         
           wherein 
           R 1  is a straight or branched C 1 -C 30  alkyl; 
           R 2  is —CH 2 R 5 , wherein R 5  is a morpholinyl group; 
           R 3  is R 2  or —CHR 5 OH; 
           R 4  is H or C 1 -C 4  alkyl; and 
           m plus n is at least 1. 
         
       
     
     
         20 . The process preparing a modified, hydrocarbylphenol-aldehyde resin of  claim 19 , wherein R 1  is tertiary butyl or tertiary octyl.

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