Resorcinolic derivative for rubber compounds

Abstract

A vulcanizable rubber composition and method for making the same are disclosed. The rubber composition comprises a rubber component mixed with a methylene donor and methylene acceptor; the methylene acceptor is 3-hydroxydiphenylamine.

1. A vulcanizable rubber composition comprising:
 a) a rubber component selected from natural rubber, synthetic rubber, or combinations thereof;  
 b) a methylene donor; and  
 c) a methylene acceptor selected from the group consisting of  that is substituted or unsubstituted 3-hydroxydiphenylamine.  
 
     
     
       2. The composition of  claim 1 , wherein said methylene acceptor is incorporated into said rubber component in an amount from about 1 to 25 parts by weight based on 100 parts by weight of said rubber component. 
     
     
       3. The composition of  claim 2 , wherein said methylene acceptor is incorporated into said rubber component in an amount from about 1 to 5 parts by weight based on 100 parts by weight of said rubber component. 
     
     
       4. The composition of  claim 1 , wherein the weight ratio of methylene acceptor to methylene donor is between about 1:10 and 10:1. 
     
     
       5. The composition of  claim 1 , wherein said methylene donor is selected from the group consisting of hexamethylenetetraamine, di-, tri-, tetra-, penta-, or hexa-N-methylol-melamine, hexamethoxymethylmelamine, oxazolidine and N-methyl-1,3,5-dioxazene. 
     
     
       6. The compound of  claim 5 , wherein said methylene donor is hexamethylenetetraamine and the weight ratio of methylene acceptor to methylene donor is at least 2:1. 
     
     
       7. The composition of  claim 1 , further including (d) a reinforcing material. 
     
     
       8. The composition of  claim 1 , further comprising one or more additives selected from the group consisting of sulfur, carbon black, zinc oxide, silica, an antioxidant, a stearate, an accelerator, an oil and an adhesion promoter. 
     
     
       9. The compound of  claim 1 , wherein the methylene acceptor is unsubstituted 3-hydroxydiphenylamine. 
     
     
       10. A method for making a rubber composition comprising the steps of mixing:
 a) a rubber component selected from natural rubber, synthetic rubber, or combinations thereof;  
 b) a methylene donor; and  
 c) a methylene acceptor selected from the group consisting of  that is substituted or unsubstituted 3-hydroxydiphenylamine.  
 
     
     
       11. The method of  claim 10 , wherein said methylene acceptor is incorporated into said rubber component in an amount from about 1 to 25 parts by weight based on 100 parts by weight of said rubber component. 
     
     
       12. The method of  claim 11 , wherein said methylene acceptor is incorporated into said rubber component in an amount from about 1 to 5 parts by weight based on 100 parts by weight of said rubber component. 
     
     
       13. The method of  claim 10 , wherein the weight ratio of methylene acceptor to methylene donor is between about 1:10 and 10:1. 
     
     
       14. The method of  claim 10 , wherein said methylene donor is selected from the group consisting of hexamethylenetetraamine, di-, tri-, tetra-, penta-, or hexa-N-methylolmelamine, hexamethoxymethylmelamine, oxazolidine and N-methyl- 1,3 ,5-dioxazene. 
     
     
       15. The method of  claim 10 , wherein said methylene acceptor is unsubstituted 3-hydroxydiphenylamine. 
     
     
       16. The method of  claim 10 , wherein  3 - hydroxydiphenylamine is prepared by reacting dihydroxybenzene and an aromatic amine.   
     
     
       17. The method of  claim 16 , wherein the dihydroxybenzene is resorcinol and the aromatic amine is aniline. 
     
     
       18. The method of  claim 10 , wherein the substituted or unsubstituted  3 - hydroxydiphenylamine is prepared by reacting unsubstituted or substituted resorcinol with unsubstituted or substituted aniline.   
     
     
       19. The method of  claim 18 , wherein the aniline is substituted with one or more C 1 -   6  alkyl groups.   
     
     
       20. The method of  claim 18 , wherein the resorcinol is meta- substituted with a C 1   -   6  alkyl or OH group.   
     
     
       21. The method of  claim 16 , wherein the dihydroxybenzene is represented by the following formula: 
                     wherein R   1    and R   2    can be the same or different group which independently is hydrogen, halogen, alkyl, cycloalkyl, alkoxy, phenyl, phenyloxy, cyano, carboxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylcarbonyl or a sulphonic acid ester group.     
     
     
       22. The method of  claim 16 , wherein the aromatic amine is represented by the following formula: 
                     R   3    and R   4    can be the same or different group which independently is hydrogen, halogen, alkyl, cycloalkyl, alkoxy, phenyl, phenyloxy, cyano, carboxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylcarbonyl or a sulphonic acid ester group.     
     
     
       23. The method of  claim 16 , wherein the  3 - hydroxydiphenylamine is represented by the following formula:                        wherein R   1    and R   2    can be the same or different group which independently is hydrogen, halogen, alkyl, cycloalkyl, alkoxy, phenyl, phenyloxy, cyano, carboxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylcarbonyl or a sulphonic acid ester group; and R   3    and R   4    can be the same or different group which independently is hydrogen, halogen, alkyl, cycloalkyl, alkoxy, phenyl, phenyloxy, cyano, carboxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylcarbonyl or a sulphonic acid ester group.     
     
     
       24. The vulcanizable rubber composition of  claim 1 , wherein the substituted or unsubstituted  3 - hydroxydiphenylamine is prepared by reacting unsubstituted or substituted resorcinol with unsubstituted or substituted aniline.   
     
     
       25. The vulcanizable rubber composition of  claim 24 , wherein the aniline is substituted with one or more C 1-6    alkyl groups.   
     
     
       26. The vulcanizable rubber composition of  claim 24 , wherein the resorcinol is meta- substituted with a C   1-6    alkyl or OH group.   
     
     
       27. The vulcanizable rubber composition of  claim 1 , wherein the  3 - hydroxydiphenylamine is prepared by reacting dihydroxybenzene and an aromatic amine.   
     
     
       28. The vulcanizable rubber composition of  claim 27 , wherein the dihydroxybenzene is resorcinol and the aromatic amine is aniline. 
     
     
       29. The vulcanizable rubber composition of  claim 27 , wherein the dihydroxybenzene is represented by the following formula: 
                     wherein R   1    and R   2    can be the same or different group which independently is hydrogen, halogen, alkyl, cycloalkyl, alkoxy, phenyl, phenyloxy, cyano, carboxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylcarbonyl or a sulphonic acid ester group.     
     
     
       30. The vulcanizable rubber composition of  claim 27 , wherein the aromatic amine is represented by the following formula: 
                     R   3    and R   4    can be the same or different group which independently is hydrogen, halogen, alkyl, cycloalkyl, alkoxy, phenyl, phenyloxy, cyano, carboxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylcarbonyl or a sulphonic acid ester group.     
     
     
       31. The vulcanizable rubber composition of  claim 27 , wherein the  3 - hydroxydiphenylamine is represented by the following formula:                        wherein R   1    and R   2    can be the same or different group which independently is hydrogen, halogen, alkyl, cycloalkyl, alkoxy, phenyl, phenyloxy, cyano, carboxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylcarbonyl or a sulphonic acid ester group; and R   3    and R   4    can be the same or different group which independently is hydrogen, halogen, alkyl, cycloalkyl, alkoxy, phenyl, phenyloxy, cyano, carboxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylcarbonyl or a sulphonic acid ester group.