Method for producing modified conjugated diene rubber, modified conjugated diene rubber, and rubber composition
This invention relates to a method for producing a modified conjugated diene rubber wherein the method involves: (a) a step in which a conjugated diene polymer having an alkali metal or alkaline earth metal active end and obtained by polymerizing a conjugated diene compound or by polymerizing a conjugated diene compound with an aromatic vinyl compounds is reacted with a first alkoxysilane compound which has an alkoxysilyl group having two or more alkoxy groups and has a group protected by a protecting group wherein deprotection is possible to obtain a modified conjugated-diene polymer having an alkoxysilyl group; and (b) a step in which the modified conjugated-diene polymer is reacted with a second alkoxysilane compound which has an alkoxysilyl group.
1. A method for producing a modified conjugated diene rubber, the method comprising:
(a) reacting a conjugated diene polymer comprising an alkali metal or alkaline earth metal active end with a first alkoxysilane compound comprising: an alkoxysilyl group comprising two or more alkoxy groups; and a group protected by a protecting group and capable of being deprotected, to obtain a modified conjugated-diene polymer comprising a first alkoxysilyl group; and
(b) reacting the modified conjugated-diene polymer comprising the first alkoxysilyl group with a second alkoxysilane compound comprising a second alkoxysilyl group in the presence of a condensation catalyst comprising a metallic element,
to form a modified conjugated-diene rubber,
wherein the conjugated diene polymer is obtained by polymerizing a conjugated diene compound or by polymerizing a conjugated diene compound with an aromatic vinyl compound.
2. The method according to claim 1 , wherein the group protected by a protecting group is at least one selected from the group consisting of
a nitrogen-containing group in which two hydrogen atoms of a primary amine have been replaced by two protecting groups,
a nitrogen-containing group in which one hydrogen atom of a secondary amine has been replaced by one protecting group,
a sulfur-containing group in which one hydrogen atom of a thiol has been replaced by one protecting group,
a phosphorus-containing group in which two hydrogen atoms of a primary phosphine have been replaced by two protecting groups, and
a phosphorus-containing group in which one hydrogen atom of a secondary phosphine has been replaced by one protecting group.
3. The method according to claim 1 , wherein the condensation catalyst is a metal compound comprising at least one metallic element within Group 4, Group 12, Group 13, Group 14, and Group 15 of the periodic table.
4. The method according to claim 3 , wherein the condensation catalyst is an alkoxide, carboxylic acid salt, or acetylacetonato complex salt of the metallic element.
5. The method according to claim 1 , further comprising:
(c) contacting water with a mixture obtained by the reacting (b).
6. A modified conjugated diene rubber obtained by the method according to claim 1 .
7. A rubber composition, comprising the modified conjugated diene rubber of claim 6 , silica and/or carbon black, and a crosslinking agent.
8. A crosslinked rubber composition obtained by crosslinking the rubber composition according to claim 7 .
9. A tire, comprising the crosslinked rubber composition according to claim 8 .
10. The method according to claim 2 , further comprising:
(c) contacting water with a mixture obtained by the reacting (b).
11. A modified conjugated diene rubber obtained by the method according to claim 2 .
12. A rubber composition, comprising the modified conjugated diene rubber of claim 11 , silica and/or carbon black, and a crosslinking agent.
13. A crosslinked rubber composition obtained by crosslinking the rubber composition according to claim 12 .
14. The method according to claim 1 , wherein the protecting group is a group which protects against a reaction with the alkali metal or alkaline earth metal active end of the conjugated diene polymer.
15. The method according to claim 2 , wherein the condensation catalyst is a metal compound comprising at least one metallic element within Group 4, Group 12, Group 13, Group 14, and Group 15 of the periodic table.
16. The method according to claim 15 , wherein the condensation catalyst is an alkoxide, carboxylic acid salt, or acetylacetonato complex salt of the metallic element.