Rubber composition, modified diene polymer and method for producing modified diene polymer
The present invention includes a rubber composition containing a modified diene polymer having a group represented by Formula (I) below and a group represented by Formula (II) below, and silica; and a modified diene polymer and a production method thereof. In Formula (I), X 1 represents at least one selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, X 3 represents a hydrocarbon group, n3 represents from 0 to 4, and X 2 represents at least one selected from the group consisting of sulfone-based protecting groups, carbamate-based protecting groups, and —(R—O) n4 —H. In Formula (II), R 1-1 represents a divalent hydrocarbon group, R 1-2 and R 1-3 each independently represent a monovalent hydrocarbon group, m1 is from 1 to 3, m2 is from 0 to 2, m1+m2 is 3, and R 1-4 represents a hydrogen atom or a hydrocarbon group.
1. A rubber composition comprising:
a modified diene polymer having a group represented by Formula (I) and a group represented by Formula (II); and
silica:
where, in Formula (I), X 1 represents at least one selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, X 3 represents a hydrocarbon group, n3 represents from 0 to 4, and * represents a bonding position,
in the case where X 1 is a nitrogen atom, n2 is 1, X 2 represents at least one selected from the group consisting of sulfone-based protecting groups, carbamate-based protecting groups, and Formula (X 2 -1): —(R—O) n4 —H,
in Formula (X 2 -1), R each independently represents a divalent hydrocarbon group, and n4 represents from 1 to 10,
in the case where X 1 is an oxygen atom or a sulfur atom, n2 represents 0, and
in Formula (II), R 1-1 represents a divalent hydrocarbon group, R 1-2 and R 1-3 each independently represent a monovalent hydrocarbon group, m1 is from 1 to 3, m2 is from 0 to 2, m1+m2 is 3, R 1-4 represents a hydrogen atom or a monovalent hydrocarbon group, and * represents a bonding position.
2. The rubber composition according to claim 1 , wherein, in Formula (I), X 1 represents a nitrogen atom, n2 is 1, and X 2 represents Formula (X 2 -1).
3. The rubber composition according to claim 1 , wherein, in Formula (I), X 1 represents an oxygen atom or a sulfur atom, and n2 is 0.
4. The rubber composition according to claim 1 , wherein the group represented by Formula (I) is bonded to a side chain or a terminal of the modified diene polymer through an organic group.
5. The rubber composition according to claim 1 , wherein the group represented by Formula (II) is bonded to a side chain or a terminal of the modified diene polymer through an organic group.
6. The rubber composition according to claim 1 , further comprising a diene rubber (but other than the modified diene polymer).
7. A modified diene polymer comprising:
a group represented by Formula (I); and
a group represented by Formula (II):
where, in Formula (I), X 1 represents at least one selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, X 3 represents a hydrocarbon group, n3 represents from 0 to 4, and * represents a bonding position,
in the case where X 1 is a nitrogen atom, n2 is 1, X 2 represents at least one selected from the group consisting of sulfone-based protecting groups, carbamate-based protecting groups, and Formula (X 2 -1): —(R—O) n4 —H,
in Formula (X 2 -1), R each independently represents a divalent hydrocarbon group, and n4 represents from 1 to 10,
in the case where X 1 is an oxygen atom or a sulfur atom, n2 represents 0, and
in Formula (II), R 1-1 represents a divalent hydrocarbon group, R 1-2 and R 1-3 each independently represent a monovalent hydrocarbon group, m1 is from 1 to 3, m2 is from 0 to 2, m1+m2 is 3, R 1-4 represents a hydrogen atom or a monovalent hydrocarbon group, and * represents a bonding position.
8. A method for producing a modified diene polymer, wherein
the modified diene polymer described in claim 7 is produced by reacting
a diene polymer having an acid anhydride group,
a heterocyclic compound represented by Formula (III), and
an amino silane coupling agent represented by Formula (IV):
where, in Formula (III), X 1 represents at least one selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, X 3 represents a hydrocarbon group, and n3 represents from 0 to 4,
in the case where X 1 is a nitrogen atom, n2 is 1, X 2 represents at least one selected from the group consisting of sulfone-based protecting groups, carbamate-based protecting groups, and Formula (X 2 -1): —(R—O) n4 —H,
in Formula (X 2 -1), R each independently represents a divalent hydrocarbon group, and n4 represents from 1 to 10,
in the case where X 1 is an oxygen atom or a sulfur atom, n2 represents 0, and
in Formula (IV), R 1-1 represents a divalent hydrocarbon group, R 1-2 and R 1-3 each independently represent a monovalent hydrocarbon group, m1 is from 1 to 3, m2 is from 0 to 2, m1+m2 is 3, and R 1-4 represents a hydrogen atom or a monovalent hydrocarbon group.
9. The method for producing a modified diene polymer according to claim 8 , wherein a number of equivalent of active hydrogen bonding to a nitrogen atom in a heterocycle contained in the heterocyclic compound relative to the acid anhydride group (active hydrogen derived from NH< in Formula (III)/acid anhydride group) is from 0.1 to 2.0 molar equivalents.
10. The method for producing a modified diene polymer according to claim 8 , wherein a number of equivalent of active hydrogen of an amino group and/or an imino group contained in the amino silane coupling agent relative to the acid anhydride group (active hydrogen derived from NH(R 1-4 )— in Formula (IV)/acid anhydride group) is from 0.1 to 4.0 molar equivalents.
11. The method for producing a modified diene polymer according to claim 8 , wherein the diene polymer containing the acid anhydride group is liquid in an environment at 23° C.