US 12,460,033 B2
Modified conjugated diene-based polymer and rubber composition including the same
Yu Jin Kim, Daejeon (KR); Suk Joon Yoo, Daejeon (KR); Geun Seung Baek, Daejeon (KR); and Hyun Jun Kim, Daejeon (KR)
Assigned to LG Chem, Ltd., Seoul (KR)
Appl. No. 17/606,848
Filed by LG Chem, Ltd., Seoul (KR)
PCT Filed Sep. 11, 2020, PCT No. PCT/KR2020/012323
§ 371(c)(1), (2) Date Oct. 27, 2021,
PCT Pub. No. WO2021/049913, PCT Pub. Date Mar. 18, 2021.
Claims priority of application No. 10-2019-0113004 (KR), filed on Sep. 11, 2019; and application No. 10-2020-0116402 (KR), filed on Sep. 10, 2020.
Prior Publication US 2022/0259333 A1, Aug. 18, 2022
Int. Cl. C08F 236/06 (2006.01); B60C 1/00 (2006.01); C08C 19/22 (2006.01); C08C 19/25 (2006.01); C08F 2/06 (2006.01); C08F 8/32 (2006.01); C08F 8/42 (2006.01); C08F 226/06 (2006.01); C08F 236/10 (2006.01); C08F 236/14 (2006.01); C08K 3/36 (2006.01); C08K 5/544 (2006.01); C08L 9/06 (2006.01)
CPC C08F 236/06 (2013.01) [C08C 19/22 (2013.01); C08C 19/25 (2013.01); C08F 2/06 (2013.01); C08F 8/32 (2013.01); C08F 8/42 (2013.01); C08F 226/06 (2013.01); C08F 236/10 (2013.01); C08F 236/14 (2013.01); C08K 3/36 (2013.01); C08K 5/544 (2013.01); C08L 9/06 (2013.01); B60C 1/0016 (2013.01)] 8 Claims
 
1. A modified conjugated diene-based polymer, comprising:
a derived unit from a modifier, wherein the modifier comprising three or more alkoxy groups bonded to silicon;
a non-functional chain forming a silicon-carbon bond at one side of the derived unit from a modifier, wherein the non-functional chain comprising a repeating unit derived from a conjugated diene-based monomer;
a functional chain forming a silicon-carbon bond at the other side of the derived unit from a modifier, wherein the functional chain comprising two or more derived units from an N-functional group-containing monomer; and
wherein the non-functional chain further comprises a repeating unit derived from an aromatic vinyl-based monomer,
wherein the modified conjugated diene-based polymer has a nitrogen (N) content, based on weight, of 150 ppm or more,
wherein the N-functional group containing monomer is selected from:

OG Complex Work Unit Chemistry
wherein, X is N or CH, R8a to R8c are each independently a hydrogen atom; an alkyl group of 1 to 20 carbon atoms; an alkenyl group of 2 to 20 carbon atoms; an alkynyl group of 2 to 20 carbon atoms; a heteroalkyl group of 1 to 20 carbon atoms, a heteroalkenyl group of 2 to 20 carbon atoms; a heteroalkynyl group of 2 to 15 20 carbon atoms; a cycloalkyl group of 5 to 20 carbon atoms; an aryl group of 6 to 20 carbon atoms; or a heterocyclic group of 3 to 20 carbon atoms, R8d is a single bond, a substituted with a substituent or unsubstituted alkylene group of 1 to 20 carbon 20 atoms; a substituted with a substituent or unsubstituted cycloalkylene group of 5 to 20 carbon atoms; or a substituted with a substituent or unsubstituted arylene group of 6 to 20 carbon atoms, wherein the substituent is an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of 5 to 10 carbon atoms, or an aryl group of 6 to 20 carbon atoms, R8e is an alkyl group of 1 to 20 carbon atoms; an alkenyl group of 2 to 20 carbon atoms; an alkynyl group of 2 to 20 carbon atoms; a heteroalkyl group of 1 to 20 carbon atoms; a heteroalkenyl group of 2 to 20 carbon atoms; a heteroalkynyl group of 2 to 20 carbon atoms; a cycloalkyl 10 group of 5 to 20 carbon atoms; an aryl group of 6 to 20 carbon atoms; a heterocyclic group of 3 to 20 carbon atoms; or a functional group represented by Formula 1a, and O is an integer of 0 to 5, at least one R8e is a functional group represented by Formula 1a, and if o is 15 an integer of 2 to 5, multiple R8e groups may be the same or different, in Formula 1a, R8f is a single bond, a substituted with a substituent or unsubstituted alkylene group of 1 to 20 carbon atoms; a substituted with a substituent or unsubstituted cycloalkylene group of 5 to 20 carbon atoms; or a substituted with a substituent or unsubstituted arylene group of 6 to 20 carbon atoms, wherein the substituent is an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of 5 to 10 carbon atoms, or an aryl group of 6 to 20 carbon atoms, and R8g and R8h are each independently an alkyl group of 1 to 20 carbon atoms; an alkenyl group of 2 to 20 carbon atoms; an alkynyl group of 2 to 20 carbon atoms; a heteroalkyl group of 1 to 20 carbon atoms; a heteroalkenyl group of 2 to 20 carbon atoms; a heteroalkynyl group of 2 to 20 carbon atoms; a cycloalkyl group of 5 to 20 carbon atoms; an aryl group of 6 to 20 carbon atoms; a heterocyclic group of 3 to 20 carbon atoms or a mono-substituted, di-substituted or trisubstituted alkylsilyl group with alkyl groups of 1 to 10 carbon atoms, or R8g and R8h are connected with each other to form a heterocyclic group of 2 to 10 carbon atoms together with N; in Formula 2, X1-X2 is CH2-CH2 or CH═CH, and X3-X4 is CH2-CH2, CH═N or N═N; in Formula 3, R11a and R11b are each independently an alkyl group of 1 to 20 carbon atoms; an alkenyl group of 2 to 20 carbon atoms; an alkynyl group of 2 to 20 carbon atoms; a heteroalkyl group of 1 to 20 carbon atoms; a heteroalkenyl group of 2 to 20 carbon atoms; a heteroalkynyl group of 2 to 10 20 carbon atoms; a cycloalkyl group of 5 to 20 carbon atoms; an aryl group of 6 to 20 carbon atoms; a heterocyclic group of 3 to 20 carbon atoms; or a functional group represented by Formula 3a below, R11c is an alkyl group of 1 to 20 carbon atoms; an alkenyl group of 2 to 20 carbon atoms; an alkynyl group of 2 to 20 carbon atoms; a heteroalkyl group of 1 to 20 carbon atoms, a heteroalkenyl group of 2 to 20 carbon atoms; a heteroalkynyl group of 2 to 20 carbon atoms; a cycloalkyl group of 5 to 20 carbon atoms; an aryl group of 6 to 20 carbon atoms; a heterocyclic group of 3 to 20 carbon atoms; or a functional group represented by Formula 3a and at least one of R11a, R11b and R11c is a functional group represented by Formula 3a below; in Formula 3a, R11d is a single bond, a substituted with a substituent or unsubstituted alkylene group of 1 to 20 carbon atoms; a substituted with a substituent or unsubstituted cycloalkylene group of 5 to 20 carbon atoms; or a substituted with a substituent or unsubstituted arylene group of 6 to 20 carbon atoms, wherein the substituent is an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of 5 to 10 carbon atoms, or an aryl group of 6 to 20 carbon atoms, and R11e and R11f are each independently an alkyl group of 1 to 20 carbon atoms; an alkenyl group of 2 to 20 carbon 15 atoms; an alkynyl group of 2 to 20 carbon atoms; a heteroalkyl group of 1 to 20 carbon atoms; a heteroalkenyl group of 2 to 20 carbon atoms; a heteroalkynyl group of 2 to 20 carbon atoms; a cycloalkyl group of 5 to 20 carbon atoms; an aryl group of 6 to 20 carbon atoms; a heterocyclic group 20 of 3 to 20 carbon atoms; or a mono-substituted, disubstituted or tri-substituted alkylsilyl group with alkyl groups of 1 to 10 carbon atoms; in Formula 4, R12a is a single bond or a substituted with a substituent or unsubstituted alkylene group of 1 to 20 carbon atoms; a substituted with a substituent or unsubstituted cycloalkylene group of 5 to 20 carbon atoms; or a substituted with a substituent or unsubstituted arylene group of 6 to 20 carbon atoms, wherein the substituent is an alkyl group of 1 to 10 carbon atoms, a cycloalkyl group of to 10 carbon atoms, or an aryl group of 6 to 20 carbon atoms, and R12b and R12c are each independently an alkyl group of 1 to 20 carbon atoms; an alkenyl group of 2 to 20 carbon 15 atoms; an alkynyl group of 2 to 20 carbon atoms; a heteroalkyl group of 1 to 20 carbon atoms; a heteroalkenyl group of 2 to 20 carbon atoms; a heteroalkynyl group of 2 to 20 carbon atoms; a cycloalkyl group of 5 to 20 carbon atoms; an aryl group of 6 to 20 carbon atoms; a heterocyclic group of 3 to 20 carbon atoms; or a mono-substituted, disubstituted or tri-substituted alkylsilyl group with alkyl groups of 1 to 10 carbon atoms.