Imine group-containing novel compound, modified conjugated diene-based polymer including same, method for preparing the polymer, and rubber composition including the polymer
Disclosed is an imine group-containing novel compound which is useful as a polymer modifier, a modified conjugated diene-based polymer including a functional group derived from the novel compound and having excellent affinity with a filler, a method for preparing the polymer, and a rubber composition including the polymer, and provides an imine group-containing compound represented by Formula 1, a modified conjugated diene-based polymer including a functional group derived therefrom, and a method for preparing the polymer.
1 . An imine group-containing compound represented by the following Formula 1:
wherein in Formula 1,
R 1 is a mono-substituted, di-substituted or tri-substituted alkylsilyl group, wherein the alkyl group has 1 to 20 carbon atoms,
R 2 is an alkyl group having 1 to 20 carbon atoms; or a substituent represented by the following Formula 1a,
R 3 is an alkylene group having 1 to 20 carbon atoms, wherein the alkylene group is unsubstituted or substituted with a substituent,
R 4 is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, wherein the alkyl group is unsubstituted or substituted with a substituent,
R 5 is an alkyl group having 1 to 20 carbon atoms, wherein the alkyl group is unsubstituted or substituted with a substituent, and
the substituent is an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms,
wherein in Formula 1a,
R 6 is an alkylene group having 1 to 20 carbon atoms, wherein the alkylene group is unsubstituted or substituted with a substituent,
R 7 is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, wherein the alkyl group is unsubstituted or substituted with a substituent,
R 8 is an alkyl group having 1 to 20 carbon atoms, wherein the alkyl group is unsubstituted or substituted with a substituent, and
the substituent is an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms.
2 . The imine group-containing compound of claim 1 , wherein, in Formula 1,
R 1 is a mono-substituted, di-substituted or tri-substituted alkylsilyl, wherein the alkyl group has 1 to 10 carbon atoms,
R 2 is an alkyl group having 1 to 10 carbon atoms; or a substituent represented by Formula 1a,
R 3 is an unsubstituted alkylene group having 1 to 10 carbon atoms,
R 4 is an unsubstituted alkyl group having 1 to 10 carbon atoms,
R 5 is an unsubstituted alkyl group having 1 to 10 carbon atoms, and in Formula 1a,
R 6 is an unsubstituted alkylene group having 1 to 10 carbon atoms,
R 7 is an unsubstituted alkyl group having 1 to 10 carbon atoms, and
R 8 is an unsubstituted alkyl group having 1 to 10 carbon atoms.
3 . The imine group-containing compound of claim 1 , wherein the compound represented by Formula 1 is one or more selected from compounds represented by the following Formulae 1-1 and 1-2:
wherein in Formula 1-1 and Formula 1-2, Me is a methyl group.
4 . A modified conjugated diene-based polymer comprising:
a repeating unit derived from a conjugated diene-based monomer; and
a functional group derived from the imine group-containing compound represented by Formula 1 in claim 1 .
5 . The modified conjugated diene-based polymer of claim 4 , wherein the conjugated diene-based polymer has a cis-1,4 bond content and a vinyl bond content, wherein the cis-1,4 bond content is 85% or more and the vinyl bond content is 5% or less.
6 . The modified conjugated diene-based polymer of claim 4 , wherein the imine group-containing compound represented by Formula 1 is one or more selected from compounds represented by the following Formulae 1-1 and 1-2:
wherein in Formula 1-1 and Formula 1-2, Me is a methyl group.
7 . A method for preparing a modified conjugated diene-based polymer, the method comprising:
1) Polymerizing a conjugated diene-based monomer in the presence of a catalyst composition comprising a neodymium compound in a hydrocarbon solvent to prepare an active polymer; and
2) reacting the active polymer with an imine group-containing compound represented by the following Formula 1:
wherein in Formula 1,
R 1 is a mono-substituted, di-substituted or tri-substituted alkylsilyl group, wherein the alkyl group has 1 to 20 carbon atoms,
R 2 is an alkyl group having 1 to 20 carbon atoms; or a substituent represented by the following Formula 1a,
R 3 is an alkylene group having 1 to 20 carbon atoms, wherein the alkylene group is unsubstituted or substituted with a substituent,
R 4 is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, wherein the alkyl group is unsubstituted or substituted with a substituent,
R 5 is an alkyl group having 1 to 20 carbon atoms, wherein the alkyl group is unsubstituted or substituted with a substituent, and
the substituent is an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms,
wherein in Formula 1a,
R 6 is an alkylene group having 1 to 20 carbon atoms, wherein the alkylene group is unsubstituted or substituted with a substituent,
R 7 is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, wherein the alkyl group is unsubstituted or substituted with a substituent,
R 8 is an alkyl group having 1 to 20 carbon atoms, wherein the alkyl group is unsubstituted or substituted with a substituent, and
the substituent is an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms.
8 . The method for preparing a modified conjugated diene-based polymer of claim 7 , wherein the catalyst composition comprises the neodymium compound in an amount of 0.1 mmol to 0.5 mmol based on 100 g of the conjugated diene-based monomer.
9 . The method for preparing a modified conjugated diene-based polymer of claim 7 , wherein the neodymium compound is a compound represented by the following Formula 2:
wherein in Formula 2,
R a to R c are each independently a hydrogen atom, or an alkyl group having 1 to 12 carbon atoms,
where R a to R c are not hydrogen atoms, simultaneously.
10 . The method for preparing a modified conjugated diene-based polymer of claim 7 , wherein the amount of imine group-containing compound represented by Formula 1 is in a ratio of 0.5 mol to 20 mol based on 1 mol of the neodymium compound.
11 . A rubber composition comprising the modified conjugated diene-based polymer of claim 4 , and a filler.
12 . The rubber composition of claim 11 , wherein the filler is carbon black.