Conjugated diene polymer, conjugated diene polymer composition, and process for producing conjugated diene polymer
A conjugated diene polymer is provided that includes a conjugated diene-based constituent unit and a group represented by Formula (I) below at both termini of a polymer chain. There are also provided a conjugated diene polymer composition formed by combining the conjugated diene polymer and a filler, a process for producing the conjugated diene polymer, a process for producing the conjugated diene polymer composition, a vulcanizate, and a process for producing the vulcanizate.
1. A conjugated diene polymer comprising:
a conjugated diene-based constituent unit; and
a group represented by Formula (I) at both termini of a polymer chain;
wherein R 1 denotes a hydrogen atom, a hydrocarbyl group having 1 to 20 carbons, or a substituted hydrocarbyl group having 1 to 20 carbons, X 1 , X 2 , and X 3 independently denote a group represented by Formula (II), a hydroxy group, a hydrocarbyl group, or a substituted hydrocarbyl group, and at least one selected from among X 1 , X 2 , and X 3 is a group represented by Formula (II) or a hydroxy group,
wherein R 2 and R 3 independently denote a hydrocarbyl group having 1 to 6 carbons, a substituted hydrocarbyl group having 1 to 6 carbons, a silyl group, or a substituted silyl group, and R 2 and R 3 may be bonded so as to form, together with the N atom, a ring structure.
2. The polymer according to claim 1 , wherein R 2 and R 3 in Formula (II) independently denote a methyl group, an ethyl group, an n-propyl group, or an n-butyl group.
3. The polymer according to claim 1 , wherein two groups selected from among X 1 , X 2 , and X 3 in Formula (I) are represented by Formula (II), or each of the two groups denotes a hydroxy group.
4. The polymer according to claim 1 , wherein the conjugated diene polymer has a vinyl bond content of 20 to 70 mol % related to 100 mol % of the conjugated diene-based constituent unit.
5. The polymer according to claim 1 , wherein the conjugated diene polymer has a molecular weight distribution of 1 to 2.
6. A conjugated diene polymer composition comprising the conjugated diene polymer according to claim 1 , and a filler.
7. The composition according to claim 6 , wherein the amount of filler is 10 to 150 parts by weight relative to 100 parts by weight of the conjugated diene polymer.
8. A process for producing a conjugated diene polymer, comprising the steps of A, B, and C:
(Step A) contacting an organoalkali metal compound catalyst having 2 to 20 carbons and a silicon compound represented by Formula (III) in a hydrocarbon solvent to prepare a reaction product of the organoalkali metal compound catalyst and the silicon compound;
(Step B) polymerizing a monomer comprising a conjugated diene by contacting the monomer with the reaction product prepared in Step A and the monomer comprising a conjugated diene in a hydrocarbon solvent to prepare a polymer having at a polymer chain terminal an alkali metal originating from the organoalkali metal compound catalyst; and
(Step C) reacting a silicon compound represented by Formula (III) with a polymer chain terminal, of the polymer prepared in Step B, having the alkali metal originating from the organoalkali metal compound catalyst by contacting the silicon compound represented by Formula (III) with the polymer in a hydrocarbon solvent
wherein X 4 , X 5 , and X 6 independently denote a group represented by Formula (II), a hydrocarbyl group, or a substituted hydrocarbyl group, and at least one selected from among X 4 , X 5 , and X 6 is a group represented by Formula (II),
wherein R 2 and R 3 independently denote a hydrocarbyl group having 1 to 6 carbons, a substituted hydrocarbyl group having 1 to 6 carbons, a silyl group, or a substituted silyl group, and R 2 and R 3 may be bonded so as to form, together with the N atom, a ring structure.
9. The process according to claim 8 , wherein R 2 and R 3 in Formula (II) independently denote a methyl group, an ethyl group, an n-propyl group, or an n-butyl group.
10. The process according to claim 8 , wherein two groups selected from among X 1 , X 2 , and X 3 in Formula (III) are represented by Formula (II).
11. The process according to claim 8 , wherein the conjugated diene polymer obtained has a vinyl bond content of 20 to 70 mol % related to 100 mol % of the conjugated diene-based constituent unit.
12. The process according to claim 8 , wherein the conjugated diene polymer has a molecular weight distribution of 1 to 2.
13. A process for producing a conjugated diene polymer composition, comprising the step of mixing a filler and the polymer obtained by the process according to claim 8 .
14. The process according to claim 13 , wherein the conjugated diene polymer composition has a filler content of 10 to 150 parts by weight relative to 100 parts by weight of the polymer.
15. A vulcanizate obtained by vulcanizing the composition according to claim 6 .
16. The process according to claim 13 , further comprising the step of mixing a vulcanizing agent with the conjugated diene polymer composition.
17. A process for producing a vulcanizate, comprising the step of vulcanizing a conjugated diene polymer composition obtained by the process according to claim 16 .