Modified conjugated diene-based polymer, modified rubber composition containing same, and method for preparing modified conjugated diene-based polymer

Patent metadata

Field	Value
Publication number	US-2016355612-A1
Application number	US-201515117653-A
Country	US
Kind code	A1
Filing date	Jun 10, 2015
Priority date	Jun 16, 2014
Publication date	Dec 8, 2016
Grant date	—

Abstract

Disclosed are a method of preparing a modified conjugated diene-based polymer, a modified conjugated diene-based polymer prepared thereby, a rubber composition including the modified conjugated diene-based polymer, and a tire including the rubber composition. The method of preparing the modified conjugated diene-based polymer includes (a) polymerizing a vinyl aromatic monomer and a conjugated diene monomer through continuous solution polymerization using a multifunctional anionic polymerization initiator in the presence of a hydrocarbon solvent, thus forming an active polymer having a reactive end; and (b) coupling or linking the reactive end of the active polymer with an aminosiloxane compound.

First claim

1 . A method of preparing a modified conjugated diene-based polymer, comprising:
(a) polymerizing a conjugated diene monomer or a vinyl aromatic monomer and a conjugated diene monomer through continuous solution polymerization using a multifunctional anionic polymerization initiator in presence of a hydrocarbon solvent, thus forming an active polymer having a reactive end; and (b) coupling or linking the reactive end of the active polymer with an aminosiloxane compound.

2 . The method of claim 1 , wherein the active polymer is a random copolymer comprising the conjugated diene monomer and the vinyl aromatic monomer.

3 . The method of claim 2 , wherein the active polymer is a random copolymer resulting from anionic polymerization of the conjugated diene monomer and the vinyl aromatic monomer.

4 . The method of claim 1 , wherein the active polymer has a ratio of the conjugated diene monomer and the vinyl aromatic monomer ranging from 100:0 to 60:40.

5 . The method of claim 2 , wherein the random copolymer has a ratio of the conjugated diene monomer and the vinyl aromatic monomer ranging from 90:10 to 60:40.

6 . The method of claim 1 , wherein the multifunctional anionic polymerization initiator is a multi-lithium compound, which comprises at least one selected from the group consisting of 1,1-diphenylethylene (DPE) dimer, 1,3-divinylbenzene (DVB), 1,3-bis(1-phenylethenyl)benzene (PEB), 1,3-diisopropenylbenzene (DIB), 2,6-lutidine, and 1-bromo-4-(4′-bromophenoxy)-2-pentadecyl benzene.

7 .- 8 . (canceled)

9 . The method of claim 1 , wherein the reactive end is a lithium metal end.

10 . The method of claim 1 , wherein the aminosiloxane compound is any one of Chemical Formulas 1 to 3 below.
(R 1 —O) n R 2 3-n Si—R 3 -A  [Chemical Formula 1]
(wherein R 1 is a C1-C20 hydrocarbon containing at least one oxygen or nitrogen, R 2 and R 3 are C1-C20 hydrocarbons, A is amine, n is an integer of 1 to 3, two or three R 1 s are identical to or different from each other when n is 2 or 3, and two R 2 s are identical to or different from each other when n is 1.)

(wherein R 1 , R 2 and R 3 are C1-C20 hydrocarbons, and A is amine.)

(wherein R 1 , R 2 and R 3 are C1-C20 hydrocarbons, and A is amine.)

11 . The method of claim 1 , wherein the modified conjugated diene-based polymer has a modification efficiency of 40 to 95%.

12 . The method of claim 1 , wherein the modified conjugated diene-based polymer has a single peak in a molecular weight range from 10,000 to 10,000,000 g/mol when analyzed using gel permeation chromatography (GPC).

13 . The method of claim 12 , wherein the modified conjugated diene-based polymer has a single peak molecular weight distribution of 1.5 or more, as measured using GPC.

14 . A modified conjugated diene-based polymer, which is configured such that an end of a random copolymer comprising a conjugated diene monomer and a vinyl aromatic monomer is modified with an aminosiloxane compound, and which has a modification efficiency of 40 to 95%.

15 . The modified conjugated diene-based polymer of claim 14 , wherein the modified conjugated diene-based polymer has a single peak in a molecular weight range from 10,000 to 10,000,000 g/mol when analyzed using GPC,
wherein the modified conjugated diene-based polymer has a single peak molecular weight distribution of 1.5 or more, as measured using GPC.

16 . (canceled)

17 . The modified conjugated diene-based polymer of claim 14 , wherein the random copolymer has a ratio of the conjugated diene monomer and the vinyl aromatic monomer ranging from 90:10 to 60:40.

18 . The modified conjugated diene-based polymer of claim 14 , wherein the multifunctional anionic polymerization initiator is a multi-lithium compound. which comprises at least one selected from the group consisting of 1,1-diphenylethylene (DPE) dimer, 1,3-divinylbenzene (DVB), 1,3-bis(1-phenylethenyl)benzene (PEB), 1,3-diisopropenylbenzene (DIB), 2,6-lutidine, and 1-bromo-4-(4′-bromophenoxy)-2-pentadecyl benzene.

19 .- 20 . (canceled)

21 . The modified conjugated diene-based polymer of claim 14 , wherein the aminosiloxane compound is any one of Chemical Formulas 1 to 3 below.
(R 1 —O) n R 2 3-n Si—R 3 -A  [Chemical Formula 1]
(wherein R 1 is a C1-C20 hydrocarbon containing at least one oxygen or nitrogen, R 2 and R 3 are C1-C20 hydrocarbons, A is amine, n is an integer of 1 to 3, two or three R 1 s are identical to or different from each other when n is 2 or 3, and two R 2 s are identical to or different from each other when n is 1.)

(wherein R 1 , R 2 and R 3 are C1-C20 hydrocarbons, and A is amine.)

(wherein R 1 , R 2 and R 3 are C1-C20 hydrocarbons, and A is amine.)

22 . A modified conjugated diene-based polymer, which is configured such that an end of an active polymer comprising a conjugated diene monomer is modified with an aminosiloxane compound, and which has a modification efficiency of 40 to 95%.

23 . The modified conjugated diene-based polymer of claim 22 , wherein the modified conjugated diene-based polymer has a single peak in a molecular weight range from 10,000 to 10,000,000 g/mol when analyzed using GPC
wherein the modified conjugated diene-based polymer has a single peak molecular weight distribution of 1.5 or more, as measured using GPC.

24 . (canceled)

25 . The modified conjugated diene-based polymer of claim 22 , wherein the multifunctional anionic polymerization initiator is a multi-lithium compound which comprises at least one selected from the group consisting of 1,1-diphenylethylene (DPE) dimer, 1,3-divinylbenzene (DVB), 1,3-bis(1-phenylethenyl)benzene (PEB), 1,3-diisopropenylbenzene (DIB), 2,6-lutidine, and 1-bromo-4-(4′-bromophenoxy)-2-pentadecyl benzene.

26 - 27 . (canceled)

28 . The modified conjugated diene-based polymer of claim 22 , wherein the aminosiloxane compound is any one of Chemical Formulas 1 to 3 below.
(R 1 —O) n R 2 3-n Si—R 3 -A  [Chemical Formula 1]
(wherein R 1 is a C1-C20 hydrocarbon containing at least one oxygen or nitrogen, R 2 and R 3 are C1-C20 hydrocarbons, A is amine, n is an integer of 1 to 3, two or three R 1 s are identical to or different from each other when n is 2 or 3, and two R 2 s are identical to or different from each other when n is 1.)

(wherein R 1 , R 2 and R 3 are C1-C20 hydrocarbons, and A is amine.)

(wherein R 1 , R 2 and R 3 are C1-C20 hydrocarbons, and A is amine.)

29 - 33 . (canceled)

Assignees

• Lg Chemical Ltd

Inventors

• Chun Moon-Seok
• Lee Soo-Yong
• Lee Seong-Du

Classifications

• C08F8/42

  Introducing metal atoms or metal-containing groups · CPC title

• C08L9/10

  Latex (C08L9/04, C08L9/08 take precedence) · CPC title

• C08F236/10 Primary

  with vinyl-aromatic monomers · CPC title

• C08F212/04

  containing one ring · CPC title

• C08G77/42

  Block-or graft-polymers containing polysiloxane sequences (polymerising aliphatic unsaturated monomers on to a polysiloxane C08F283/12) · CPC title