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1. US20200148794 - Amine compound, modified conjugated diene-based polymer containing functional group derived therefrom, and method of preparing the modified conjugated diene-based polymer

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Claims

1. A modified conjugated diene-based polymer comprising a functional group derived from a tertiary amine compound represented by the following Formula 1:

(MOL) (CDX)
in Formula 1,
A is an alkylene group of 1 to 20 carbon atoms, and
X 1 to X 3 are each independently an oxygen atom or an oxygen-containing alkylene group of 1 to 4 carbon atoms.
2. The modified conjugated diene-based polymer of claim 1, wherein in Formula 1,
A is an alkylene group of 1 to 10 carbon atoms, and
X 1 to X 3 are each independently an oxygen atom or an oxygen-containing alkylene group of 1 to 2 carbon atoms.
3. The modified conjugated diene-based polymer of claim 1, wherein the tertiary amine compound represented by Formula 1 is represented by the following Formula 2:
4. The modified conjugated diene-based polymer of claim 1, wherein the polymer has a number average molecular weight of 150,000 g/mol to 1,000,000 g/mol.
5. The modified conjugated diene-based polymer of claim 1, wherein the polymer has molecular weight distribution (Mw/Mn) of 1.0 to 3.0.
6. The modified conjugated diene-based polymer of claim 1, wherein the polymer comprises an aromatic vinyl-based monomer unit in 40 wt % or less.
7. A method of preparing a modified conjugated diene-based polymer described in claim 1, the method comprising:
1) polymerizing a conjugated diene-based monomer, or an aromatic vinyl-based monomer and a conjugated diene-based monomer in the presence of an organometal compound in a hydrocarbon solvent, to prepare an active polymer which is coupled with an organometal at one terminal; and
2) reacting the active polymer with a tertiary amine compound represented by Formula 1:

(MOL) (CDX)
in Formula 1,
A is an alkylene group of 1 to 20 carbon atoms, and
X 1 to X 3 are each independently an oxygen atom or an oxygen-containing alkylene group of 1 to 4 carbon atoms.
8. The method of preparing a modified conjugated diene-based polymer of claim 7, wherein the organometal compound is used in 0.01 mmol to 10 mmol based on total 100 g of the monomers.
9. The method of preparing a modified conjugated diene-based polymer of claim 7, wherein the organometal compound is one or more selected from the group consisting of methyllithium, ethyllithium, propyllithium, n-butyllithium, s-butyllithium, t-butyllithium, hexyllithium, n-decyllithium, t-octyllithium, phenyllithium, 1-naphthyl lithium, n-eicosyl lithium, 4-butylphenyl lithium, 4-tolyl lithium, cyclohexyl lithium, 3,5-di-n-heptylcyclohexyl lithium, 4-cyclopentyl lithium, naphthyl sodium, naphthyl potassium, lithium alkoxide, sodium alkoxide, potassium alkoxide, lithium sulfonate, sodium sulfonate, potassium sulfonate, lithium amide, sodium amide, potassium amide, and lithium isopropylamide.
10. The method of preparing a modified conjugated diene-based polymer of claim 7, wherein the polymerization of step 1) is performed by additionally adding a polar additive.
11. The method of preparing a modified conjugated diene-based polymer of claim 10, wherein the polar additive is added in an amount of 0.001 parts by weight to 10 parts by weight based on total 100 parts by weight of the monomer.
12. The method of preparing a modified conjugated diene-based polymer of claim 7, wherein the tertiary amine compound represented by Formula 1 is used in 0.01 mol to 5 mol with respect to 1 mol of the organometal compound.
13. A modified conjugated diene-based polymer comprising a functional group derived from a tertiary amine compound represented by Formula 1, and having a polystyrene conversion weight average molecular weight (Mw) analyzed by gel permeation chromatography of 100,000 g/mol to 3,000,000 g/mol,
molecular weight distribution (Mw/Mn) of 1.30 to 2.50, and
a ratio (Mw/Mp) of a weight average molecular weight (Mw) and a peak top molecular weight (Mp) of 0.70 to 1.125:

(MOL) (CDX)
in Formula 1,
A is an alkylene group of 1 to 20 carbon atoms, and
X 1 to X 3 are each independently an oxygen atom or an oxygen-containing alkylene group of 1 to 4 carbon atoms.
14. A method of preparing the modified conjugated diene-based polymer described in claim 13, the method comprising:
1) polymerizing a conjugated diene-based monomer, or an aromatic vinyl-based monomer and a conjugated diene-based monomer in the presence of an organometal compound in a hydrocarbon solvent, to prepare an active polymer which is coupled with an organometal at one terminal; and
2) reacting the active polymer with the tertiary amine compound represented by Formula 1:
15. The method of claim 14, wherein the organometal compound is used in 0.01 mmol to 10 mmol based on total 100 g of the monomers.
16. The method of claim 14, wherein the organometal compound is one or more selected from the group consisting of methyllithium, ethyllithium, propyllithium, n-butyllithium, s-butyllithium, t-butyllithium, hexyllithium, n-decyllithium, t-octyllithium, phenyllithium, 1-naphthyl lithium, n-eicosyl lithium, 4-butylphenyl lithium, 4-tolyl lithium, cyclohexyl lithium, 3,5-di-n-heptylcyclohexyl lithium, 4-cyclopentyl lithium, naphthyl sodium, naphthyl potassium, lithium alkoxide, sodium alkoxide, potassium alkoxide, lithium sulfonate, sodium sulfonate, potassium sulfonate, lithium amide, sodium amide, potassium amide, and lithium isopropylamide.
17. The method of claim 14, wherein the polymerization of step 1) is performed by additionally adding a polar additive, and
wherein the polar additive is added in an amount of 0.001 parts by weight to 10 parts by weight based on total 100 parts by weight of the monomer.
18. The method of claim 14, wherein the tertiary amine compound represented by Formula 1 is used in 0.01 mol to 5 mol with respect to 1 mol of the organometal compound.
19. A tertiary amine compound represented by the following Formula 1:

(MOL) (CDX)
in Formula 1,
A is an alkylene group of 1 to 20 carbon atoms, and
X 1 to X 3 are each independently an oxygen atom or an oxygen-containing alkylene group of 1 to 4 carbon atoms.
20. The tertiary amine compound of claim 19, wherein the tertiary amine compound represented by Formula 1 is represented by the following Formula 2: