Conjugated diene polymer, conjugated diene polymer composition, and method for producing conjugated diene polymer
A conjugated diene polymer is provided that comprises a conjugated diene-based constituent unit and a constituent unit of formula (I) below, at least one terminus of the polymer being modified by a compound of formula (II): wherein X 1 , X 2 , and X 3 independently denote a group of formula (Ia) below, a hydroxy group, a hydrocarbyl group, or a substituted hydrocarbyl group, and at least one of X 1 , X 2 , and X 3 is a group of formula (Ia) below or a hydroxy group, wherein R 1 and R 2 independently denote a hydrocarbyl group having 1 to 6 carbon atoms, a substituted hydrocarbyl group having 1 to 6 carbon atoms, a silyl group, or a substituted silyl group, and R 1 and R 2 may be bonded so as to form, together with the nitrogen atom, a ring structure, wherein n denotes an integer of 1 to 10, R 3 , R 4 , and R 5 independently denote a hydrocarbyl group having 1 to 4 carbon atoms or a hydrocarbyloxy group having 1 to 4 carbon atoms, at least one of R 3 , R 4 , and R 5 is a hydrocarbyloxy group, and A denotes a nitrogen atom-containing functional group.
1. A method for producing a conjugated diene polymer, comprising steps A and B:
step A: polymerizing monomers comprising a conjugated diene and a vinyl compound of formula (III) below in a hydrocarbon solvent in the presence of an alkali metal catalyst to produce a polymer having an alkali metal originating from the catalyst at least one terminus of a polymer chain comprising a conjugated diene-based monomer unit and a monomer unit based on the vinyl compound of formula (III):
wherein X 4 , X 5 , and X 6 independently denote a group of formula (IIIa) below, a hydrocarbyl group, or a substituted hydrocarbyl group, and at least one of X 4 , X 5 , and X 6 is a group of formula (IIIa) below,
wherein R 8 and R 9 independently denote a hydrocarbyl group having 1 to 6 carbon atoms, a substituted hydrocarbyl group having 1 to 6 carbon atoms, a silyl group, or a substituted silyl group, and R 8 and R 9 may be bonded so as to form, together with the nitrogen atom, a ring structure; and
step B: reacting the resulting polymer in step A with a compound of formula (II):
wherein n denotes an integer of 1 to 10, R 3 , R 4 , and R 5 independently denote a hydrocarbyl group having 1 to 4 carbon atoms or a hydrocarbyloxy group having 1 to 4 carbon atoms, at least one of R 3 , R 4 , and R 5 is a hydrocarbyloxy group, and A denotes a group of formula (11a) below,
wherein R 6 and R 7 independently denote a hydrocarbyl group having 1 to 6 carbon atoms.
2. The method according to claim 1 , wherein R 8 and R 9 in formula (IIIa) are hydrocarbyl groups having 1 to 6 carbon atoms.
3. The method according to claim 1 , wherein two of X 4 , X 5 , and X 6 of formula (III) are groups of formula (IIIa).