Method for producing modified conjugated diene polymer, modified conjugated diene polymer, polymer composition, crosslinked body and tire
A modified conjugated diene-based polymer is produced by a method reacting a conjugated diene-based polymer having an active terminal, which is a polymer obtained by polymerizing a monomer including a conjugated diene compound in the presence of an alkali metal compound, with a compound [A] represented by formula (1). In formula (1), each of R 1 and R 2 represents a C1 to C8 hydrocarbyl group and the like; each of R 5 and R 6 represents a C1 to C8 hydrocarbyl group and the like; each of R 3 and R 4 represents a C1 to C6 hydrocarbylene group; R 7 represents a C1 to C10 hydrocarbylene group; X 1 represents a C1 to C4 hydrocarbyloxy group; each of X 2 and X 3 represent a C1 to C4 hydrocarbyl group or hydrocarbyloxy group; m is an integer of 1 to 3.
1. A method for producing a modified conjugated diene-based polymer, the method comprising:
reacting a conjugated diene-based polymer comprising an active terminal, obtained by polymerizing a monomer comprising a conjugated diene compound in the presence of an alkali metal compound, with a compound of formula (1):
wherein
R 1 and R 2 are independently a hydrogen atom or a C1 to C8 hydrocarbyl group, or R 1 and R 2 taken together are a C5 to C8 ring together with the carbon atom to which R 1 and R 2 bond, R 1 and R 2 not simultaneously being a hydrogen atom,
R 5 and R 6 are independently a hydrogen atom or a C1 to C8 hydrocarbyl group, or R 5 and R 6 taken together are a C5 to C8 ring together with the carbon atom to which R 5 and R 6 bond, R 5 and R 6 not simultaneously being a hydrogen atom,
R 3 and R 4 are independently a C1 to C6 hydrocarbylene group,
R 7 is a C1 to C10 hydrocarbylene group,
X 1 is a C1 to C4 hydrocarbyloxy group,
X 2 and X 3 are independently a C1 to C4 hydrocarbyl group or hydrocarbyloxy group,
m is an integer in a range of from 1 to 3, and
when m is 2 or 3, a plurality of groups R 3 , R 7 , X 1 , X 2 , or X 3 are identical to or different from one another.
2. The method of claim 1 , wherein the alkali metal compound comprises a compound of formula (2):
wherein R 8 is a nitrogen-comprising group,
Y 1 is a hydrocarbylene group prepared by polymerization of a conjugated diene compound or an aromatic vinyl compound,
M 1 is an alkali metal, and
n is an integer in a range of from 1 to 10.
3. The method of claim 2 , wherein the compound of formula (2) in the alkali metal compound is present in an amount of 50 mol % or more.
4. The method of claim 2 , wherein the alkali metal compound comprises, as the compound of formula (2), ((2E,6E)-11-(dimethylamino)-3,7-dimethylundeca-2,6-dien-1-yl)lithium.
5. The method of claim 1 , wherein the monomer further comprises an aromatic vinyl compound.
6. A modified conjugated diene-based polymer, which is a reaction product between a conjugated diene-based polymer comprising an active terminal and a compound of formula (1):
wherein
R 1 and R 2 are independently a hydrogen atom or a C1 to C8 hydrocarbyl group, or R 1 and R 2 taken together are a C5 to C8 ring together with the carbon atom to which R 1 and R 2 bond, R 1 and R 2 not simultaneously being a hydrogen atom,
R 5 and R 6 are independently a hydrogen atom or a C1 to C8 hydrocarbyl group, or R 5 and R 6 taken together are a C5 to C8 ring together with the carbon atom to which R 5 and R 6 bond, R 5 and R 6 not simultaneously being a hydrogen atom,
R 3 and R 4 are independently a C1 to C6 hydrocarbylene group,
R 7 is a C1 to C10 hydrocarbylene group,
X 1 is a C1 to C4 hydrocarbyloxy group,
X 2 and X 3 are independently a C1 to C4 hydrocarbyl group or hydrocarbyloxy group,
m is an integer in a range of from 1 to 3, and when m is 2 or 3, a plurality of groups R 3 , R 7 , X 1 , X 2 , or X 3 are identical to or different from one another.
7. A modified conjugated diene-based polymer of formula (3):
wherein
R 1 and R 2 are independently a hydrogen atom or a C1 to C8 hydrocarbyl group, or R 1 and R 2 taken together are a C5 to C8 ring together with the carbon atom to which R 1 and R 2 bond, R 1 and R 2 not simultaneously being a hydrogen atom,
R 5 and R 6 are independently a hydrogen atom or a C1 to C8 hydrocarbyl group, or R 5 and R 6 taken together are a C5 to C8 ring together with the carbon atom to which R 5 and R 6 bond, R 5 and R 6 not simultaneously being a hydrogen atom,
R 3 and R 4 are independently a C1 to C6 hydrocarbylene group,
R 7 is a C1 to C10 hydrocarbylene group,
Poly is an optionally modified conjugated diene-based polymer chain,
Z 1 is a C1 to C4 hydrocarbyloxy group or an optionally modified conjugated diene-based polymer chain,
Z 2 and Z 3 are independently a C1 to C4 hydrocarbyl group, a C1 to C4 hydrocarbyloxy group, or an optionally modified conjugated diene-based polymer chain,
m is an integer in a range of from 1 to 3, and when m is 2 or 3, a plurality of groups R 7 , a plurality of R 3 , R 7 , Z 1 , Z 2 , or Z 3 are identical to or different from one another.
8. A polymer composition, comprising:
the modified conjugated diene-based polymer of claim 6 ;
silica; and
a crosslinking agent.
9. A crosslinked product, produced by crosslinking the polymer composition of claim 8 .
10. A tire, comprising:
a tread; and
a sidewall,
wherein the tread and/or the sidewall comprises the polymer composition of claim 8 .