Modified conjugated diene polymer and method for producing same, polymer composition, crosslinked polymer, and tire

Patent metadata

Field	Value
Publication number	US-2016009903-A1
Application number	US-201414770988-A
Country	US
Kind code	A1
Filing date	Feb 27, 2014
Priority date	Feb 28, 2013
Publication date	Jan 14, 2016
Grant date	—

Abstract

The invention provides a rubber composition which can improve low fuel consumption performance, workability, and abrasion resistance at the same time in uses of automobile tires and the like. A modified conjugated diene polymer is produced by a method comprising: a polymerization step of polymerizing a conjugated diene compound or polymerizing a conjugated diene compound and an aromatic vinyl compound to obtain a conjugated diene polymer having an active end in the presence of a metal amide compound obtained by mixing an alkali metal compound or an alkaline earth metal compound with a secondary amine compound and a first modification step of reacting the active end with a compound (C1) having a functional group (a) that interacts with silica, having one or more linear structures where three or more groups or atoms in total derived from at least either of a methylene group and a divalent atom are linearly connected, and capable of binding to a plurality of the active ends.

First claim

1 . A method for producing a modified conjugated diene polymer, comprising:
a polymerization step of polymerizing a conjugated diene compound or polymerizing a conjugated diene compound and an aromatic vinyl compound to obtain a conjugated diene polymer having an active end, in the presence of a metal amide compound obtained by mixing an alkali metal compound or an alkaline earth metal compound with a secondary amine compound and a first modification step of reacting the active end with the following compound (C1): (C1) a compound having a functional group (a) that interacts with silica, having one or more linear structures where three or more groups or atoms in total derived from at least either of a methylene group and a divalent atom are linearly connected, and capable of binding to a plurality of the active ends.

2 . The method for producing a modified conjugated diene polymer according to claim 1 , wherein (C1) is the following compound (C1′):
(C1′) a compound having a functional group (a) that interacts with silica, having a plurality of functional groups (b) capable of reacting with the active end, and capable of binding the active end to the functional group (a) through a linear structure composed of three or more atoms connected with a single bond, by a reaction of the functional group (b) with the active end.

3 . The method for producing a modified conjugated diene polymer according to claim 1 , wherein the secondary amine compound has a trisubstituted nitrogen atom to which three atoms other than a hydrogen atom are bound.

4 . The method for producing a modified conjugated diene polymer according to claim 2 , wherein the secondary amine compound has a trisubstituted nitrogen atom to which three atoms other than a hydrogen atom are bound.

5 . The method for producing a modified conjugated diene polymer according to claim 3 , wherein the secondary amine compound has, as a group containing the trisubstituted nitrogen atom, at least one selected from the group consisting of a nitrogen-containing group in which two hydrogen atoms of a primary amino group are each substituted with a monovalent protective group and a nitrogen-containing group in which one hydrogen atom of a secondary amino group is substituted with a monovalent protective group.

6 . The method for producing a modified conjugated diene polymer according to claim 4 , wherein the secondary amine compound has, as a group containing the trisubstituted nitrogen atom, at least one selected from the group consisting of a nitrogen-containing group in which two hydrogen atoms of a primary amino group are each substituted with a monovalent protective group and a nitrogen-containing group in which one hydrogen atom of a secondary amino group is substituted with a monovalent protective group.

7 . The method for producing a modified conjugated diene polymer according to claim 1 , which further comprises a second modification step of reacting the active end with a compound (M) having a functional group that interacts with silica and capable of binding to one above active end.

8 . A method for producing a modified conjugated diene polymer, comprising:
a polymerization step of polymerizing a conjugated diene compound or polymerizing a conjugated diene compound and an aromatic vinyl compound to obtain a conjugated diene polymer having an active end, using a polyfunctional lithium compound as a polymerization initiator, a first modification step of reacting the active end with the following compound (C1): (C1) a compound having a functional group (a) that interacts with silica, having one or more linear structures where three or more groups or atoms in total derived from at least either of a methylene group and a divalent atom are linearly connected, and capable of binding to a plurality of the active ends, and a second modification step of reacting the active end with a compound (M) having a functional group that interacts with silica and capable of binding to one above active end.

9 . The method for producing a modified conjugated diene polymer according to claim 8 , wherein (C1) is the following compound (C1′):
(C1′) a compound having a functional group (a) that interacts with silica, having a plurality of functional groups (b) capable of reacting with the active end, and capable of binding the active end to the functional group (a) through a linear structure composed of three or more atoms connected with a single bond, by a reaction of the functional group (b) with the active end.

10 . The method for producing a modified conjugated diene polymer according to claim 8 , wherein the compound (M) is a compound represented by the following formula (1):

wherein A 1 is a monovalent functional group which has at least one atom selected from the group consisting of a nitrogen atom, a phosphorus atom, and a sulfur atom, does not have an active hydrogen, and binds to R 3 with a nitrogen atom, a phosphorus atom, or a sulfur atom; R 1 and R 2 are a hydrocarbyl group, R 3 is a hydrocarbylene group, and n is an integer of 0 to 2, provided that R 1 and R 2 may be the same or different from each other, in the case where n is 1, a plurality of R 2 's may be the same or different from each other, and in the case where n is 2, a plurality of R 1 's may be the same or different from each other.

11 . A modified conjugated diene polymer, which has a plurality of polymer chains containing a repeating unit based on a conjugated diene compound, wherein one end of the polymer chain is bound to a binding portion having a functional group (a) that interacts with silica and a linear structure where three or more groups or atoms in total selected from at least either of a methylene group and a divalent atom are linearly connected, and which has a functional group (c) that interacts with silica in at least a part of the end portion on the side that is not bound to the binding portion in a plurality of the polymer chains.

12 . A modified conjugated diene polymer, which has a plurality of polymer chains containing a repeating unit based on a conjugated diene compound, wherein the polymer chain is bound to a functional group (a) that interacts with silica through a linear structure composed of three or more atoms connected with a single bond, and which has a functional group (c) that interacts with silica in at least a part of the end portion on the side that is not bound to the linear structure in a plurality of the polymer chains.

13 . A polymer composition comprising the modified conjugated diene polymer obtained by the production method according to claim 1 , and a crosslinking agent.

14 . A polymer composition comprising the modified conjugated diene polymer obtained by the production method according to claim 8 , and a crosslinking agent.

15 . A polymer composition comprising the modified conjugated diene polymer obtained by the production method according to claim 11 , and a crosslinking agent

16 . A polymer composition comprising the modified conjugated diene polymer obtained by the production method according to claim 12 , and a crosslinking agent

17 . A crosslinked polymer obtained by cross-linking the polymer composition according to claim 13 .

18 . A tire comprising the crosslinked polymer according to claim 14 at least as a material of a tread or a side wall.

Assignees

• Jsr Corp

Inventors

• Morita Hiroyuki
• Tani Koichiro
• Okada Koji
• Inoue Masaaki

Classifications

• B60C1/00 Primary

  Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition · CPC title

• C08C19/22

  Incorporating nitrogen atoms into the molecule · CPC title

• C08C19/25

  Incorporating silicon atoms into the molecule · CPC title

• C08K3/36

  Silica · CPC title

• C08C19/44

  of polymers containing metal atoms exclusively at one or both ends of the skeleton · CPC title