Resorcinolic derivative for rubber compounds
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.