IP Library › Granted Patent US 9,540,463
Granted Patent B2
US 9,540,463 · App. 15/043,702 · Granted Jan 10, 2017

Method for producing polydienes and polydiene copolymers with reduced cold flow

Inventor: Steven Luo (Akron, OH)
Assignee: Bridgestone Corporation
C08F136/06
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Quick Facts
Patent No.
US 9,540,463
App. No.
15/043,702
Granted
Jan 10, 2017
Kind
B2
Abstract

A method for preparing a coupled polymer, the method comprising the steps of (i) polymerizing monomer to form a reactive polymer, and (ii) reacting the reactive polymer with an imide compound containing an oxiranyl group.

Claims (32)

1. A method for preparing a coupled polymer, the method comprising the steps of:

(i) polymerizing monomer to form a reactive polymer; and

(ii) reacting the reactive polymer with an imide compound containing an oxiranyl group.

2. The method of claim 1 , where the imide compound containing an oxiranyl group includes an imido group selected from the formulae:

3. The method of claim 1 , where the imide compound containing an oxiranyl group includes an oxiranyl group selected from the group consistent of unsubstituted oxiranyl, 2-methyl-2-oxiranyl, 3-methyl-2-oxiranyl, 2,3-dimethyl-2-oxiranyl, 3,3-dimethyl-2-oxiranyl, 2,3,3-trimethyl-2-oxiranyl, 2-ethyl-2-oxiranyl, 3-ethyl-2-oxiranyl, 2,3-diethyl-2-oxiranyl, 3,3-diethyl-2-oxiranyl, 2,3,3-triethyl-2-oxiranyl, 2-phenyl-2-oxiranyl, 3-phenyl-2-oxiranyl, 2,3-diphenyl-2-oxiranyl, 3,3-diphenyl-2-oxiranyl, and 2,3,3-triphenyl-2-oxiranyl.

4. The method of claim 1 , where the imide compound containing an oxiranyl group is defined by the formula I:

where R 1 is a divalent organic group, R 2 is a bond or a divalent organic group, and R 3 , R 4 , and R 5 are each independently a hydrogen atom or a monovalent organic group, or where R 3 joins with R 4 or R 5 to form a divalent organic group, or where R 4 and R 5 join to form a divalent organic group.

5. The method of claim 1 , where the imide compound containing an oxiranyl group is selected from the group consisting of N-(oxiranylmethyl) phthalimide, N-[(2-methyl-2-oxiranyl)methyl]phthalimide, N-[(3-methyl-2-oxiranyl)methyl]phthalimide, N-[(2,3-dimethyl-2-oxiranyl)methyl]phthalimide, N-[(3,3-dimethyl-2-oxiranyl)methyl]phthalimide, N-[(2,3,3-trimethyl-2-oxiranyl)methyl]phthalimide, N-(2-oxiranylethyl) phthalimide, N-[(2-methyl-2-oxiranyl)ethyl]phthalimide, N-[(3-methyl-2-oxiranyl)ethyl]phthalimide, N-[(2,3-dimethyl-2-oxiranyl)ethyl]phthalimide, N-[(3,3-dimethyl-2-oxiranyl)ethyl]phthalimide, N-[(2,3,3-trimethyl-2-oxiranyl)ethyl]phthalimide, N-(3-oxiranyl-1-propyl)phthalimide, N-[3-(2-methyl-2-oxiranyl)-1-propyl]phthalimide, N-[3-(3-methyl-2-oxiranyl)-1-propyl]phthalimide, N-[3-(2,3-dimethyl-2-oxiranyl)-1-propyl]phthalimide, N-[3-(3,3-dimethyl-2-oxiranyl)-1-propyl]phthalimide, N-[3-(2,3,3-trimethyl-2-oxiranyl)-1-propyl]phthalimide, N-[(2-ethyl-2-oxiranyl)methyl]phthalimide, N-[(3-ethyl-2-oxiranyl)methyl]phthalimide, N-[(2,3-diethyl-2-oxiranyl)methyl]phthalimide, N-[(3,3-diethyl-2-oxiranyl)methyl]phthalimide, N-[(2,3,3-triethyl-2-oxiranyl)methyl]phthalimide, N-[(2-ethyl-2-oxiranyl)ethyl]phthalimide, N-[(3-ethyl-2-oxiranyl)ethyl]phthalimide, N-[(2,3-diethyl-2-oxiranyl)ethyl]phthalimide, N-[(3,3-diethyl-2-oxiranyl)ethyl]phthalimide, N-[(2,3,3-triethyl-2-oxiranyl)ethyl]phthalimide, N-[3-(2-ethyl-2-oxiranyl)-1-propyl]phthalimide, N-[3-(3-ethyl-2-oxiranyl)-1-propyl]phthalimide, N-[3-(2,3-diethyl-2-oxiranyl)-1-propyl]phthalimide, N-[3-(3,3-diethyl-2-oxiranyl)-1-propyl]phthalimide, N-[3-(2,3,3-triethyl-2-oxiranyl)-1-propyl]phthalimide, N-[(2-phenyl-2-oxiranyl)methyl]phthalimide, N-[(3-phenyl-2-oxiranyl)methyl]phthalimide, N-[(2,3-diphenyl-2-oxiranyl)methyl]phthalimide, N-[(3,3-diphenyl-2-oxiranyl)methyl]phthalimide, N-[(2,3,3-triphenyl-2-oxiranyl)methyl]phthalimide, N-[(2-phenyl-2-oxiranyl)ethyl]phthalimide, N-[(3-phenyl-2-oxiranyl)ethyl]phthalimide, N-[(2,3-diphenyl-2-oxiranyl)ethyl]phthalimide, N-[(3,3-diphenyl-2-oxiranyl)ethyl]phthalimide, N-[(2,3,3-triphenyl-2-oxiranyl)ethyl]phthalimide, N-[3-(2-phenyl-2-oxiranyl)-1-propyl]phthalimide, N-[3-(3-phenyl-2-oxiranyl)-1-propyl]phthalimide, N-[3-(2,3-diphenyl-2-oxiranyl)-1-propyl]phthalimide, N-[3-(3,3-diphenyl-2-oxiranyl)-1-propyl]phthalimide, and N-[3-(2,3,3-triphenyl-2-oxiranyl)-1-propyl]phthalimide.

6. The method of claim 1 , where the imide compound containing an oxiranyl group is selected from the group consisting of N-(oxiranylmethyl) maleimide, N-[(2-methyl-2-oxiranyl)methyl]maleimide, N-[(3-methyl-2-oxiranyl)methyl]maleimide, N-[(2,3-dimethyl-2-oxiranyl)methyl]maleimide, N-[(3,3-dimethyl-2-oxiranyl)methyl]maleimide, N-[(2,3,3-trimethyl-2-oxiranyl)methyl]maleimide, N-(2-oxiranylethyl)maleimide, N-[(2-methyl-2-oxiranyl)ethyl]maleimide, N-[(3-methyl-2-oxiranyl)ethyl]maleimide, N-[(2,3-dimethyl-2-oxiranyl)ethyl]maleimide, N-[(3,3-dimethyl-2-oxiranyl)ethyl]maleimide, N-[(2,3,3-trimethyl-2-oxiranyl)ethyl]maleimide, N-(3-oxiranyl-1-propyl)maleimide, N-[3-(2-methyl-2-oxiranyl)-1-propyl]maleimide, N-[3-(3-methyl-2-oxiranyl)-1-propyl]maleimide, N-[3-(2,3-dimethyl-2-oxiranyl)-1-propyl]maleimide, N-[3-(3,3-dimethyl-2-oxiranyl)-1-propyl]maleimide, N-[3-(2,3,3-trimethyl-2-oxiranyl)-1-propyl]maleimide, N-[(2-ethyl-2-oxiranyl)methyl]maleimide, N-[(3-ethyl-2-oxiranyl)methyl]maleimide, N-[(2,3-diethyl-2-oxiranyl)methyl]maleimide, N-[(3,3-diethyl-2-oxiranyl)methyl]maleimide, N-[(2,3,3-triethyl-2-oxiranyl)methyl]maleimide, N-[(2-ethyl-2-oxiranyl)ethyl]maleimide, N-[(3-ethyl-2-oxiranyl)ethyl]maleimide, N-[(2,3-diethyl-2-oxiranyl)ethyl]maleimide, N-[(3,3-diethyl-2-oxiranyl)ethyl]maleimide, N-[(2,3,3-triethyl-2-oxiranyl)ethyl]maleimide, N-[3-(2-ethyl-2-oxiranyl)-1-propyl]maleimide, N-[3-(3-ethyl-2-oxiranyl)-1-propyl]maleimide, N-[3-(2,3-diethyl-2-oxiranyl)-1-propyl]maleimide, N-[3-(3,3-diethyl-2-oxiranyl)-1-propyl]maleimide, N-[3-(2,3,3-triethyl-2-oxiranyl)-1-propyl]maleimide, N-[(2-phenyl-2-oxiranyl)methyl]maleimide, N-[(3-phenyl-2-oxiranyl)methyl]maleimide, N-[(2,3-diphenyl-2-oxiranyl)methyl]maleimide, N-[(3,3-diphenyl-2-oxiranyl)methyl]maleimide, N-[(2,3,3-triphenyl-2-oxiranyl)methyl]maleimide, N-[(2-phenyl-2-oxiranyl)ethyl]maleimide, N-[(3-phenyl-2-oxiranyl)ethyl]maleimide, N-[(2,3-diphenyl-2-oxiranyl)ethyl]maleimide, N-[(3,3-diphenyl-2-oxiranyl)ethyl]maleimide, N-[(2,3,3-triphenyl-2-oxiranyl)ethyl]maleimide, N-[3-(2-phenyl-2-oxiranyl)-1-propyl]maleimide, N-[3-(3-phenyl-2-oxiranyl)-1-propyl]maleimide, N-[3-(2,3-diphenyl-2-oxiranyl)-1-propyl]maleimide, N-[3-(3,3-diphenyl-2-oxiranyl)-1-propyl]maleimide, and N-[3-(2,3,3-triphenyl-2-oxiranyl)-1-propyl]maleimide.

7. The method of claim 1 , where the imide compound containing an oxiranyl group is selected from the group consisting of N-(oxiranylmethyl) citraconimide, N-[(2-methyl-2-oxiranyl)methyl]citraconimide, N-[(3-methyl-2-oxiranyl)methyl]citraconimide, N-[(2,3-dimethyl-2-oxiranyl)methyl]citraconimide, N-[(3,3-dimethyl-2-oxiranyl)methyl]citraconimide, N-[(2,3,3-trimethyl-2-oxiranyl)methyl]citraconimide, N-(2-oxiranylethyl) citraconimide, N-[(2-methyl-2-oxiranyl)ethyl]citraconimide, N-[(3-methyl-2-oxiranyl)ethyl]citraconimide, N-[(2,3-dimethyl-2-oxiranyl)ethyl]citraconimide, N-[(3,3-dimethyl-2-oxiranyl)ethyl]citraconimide, N-[(2,3,3-trimethyl-2-oxiranyl)ethyl]citraconimide, N-(3-oxiranyl-1-propyl) citraconimide, N-[3-(2-methyl-2-oxiranyl)-1-propyl]citraconimide, N-[3-(3-methyl-2-oxiranyl)-1-propyl]citraconimide, N-[3-(2,3-dimethyl-2-oxiranyl)-1-propyl]citraconimide, N-[3-(3,3-dimethyl-2-oxiranyl)-1-propyl]citraconimide, N-[3-(2,3,3-trimethyl-2-oxiranyl)-1-propyl]citraconimide, N-[(2-ethyl-2-oxiranyl)methyl]citraconimide, N-[(3-ethyl-2-oxiranyl)methyl]citraconimide, N-[(2,3-diethyl-2-oxiranyl)methyl]citraconimide, N-[(3,3-diethyl-2-oxiranyl)methyl]citraconimide, N-[(2,3,3-triethyl-2-oxiranyl)methyl]citraconimide, N-[(2-ethyl-2-oxiranyl)ethyl]citraconimide, N-[(3-ethyl-2-oxiranyl)ethyl]citraconimide, N-[(2,3-diethyl-2-oxiranyl)ethyl]citraconimide, N-[(3,3-diethyl-2-oxiranyl)ethyl]citraconimide, N-[(2,3,3-triethyl-2-oxiranyl)ethyl]citraconimide, N-[3-(2-ethyl-2-oxiranyl)-1-propyl]citraconimide, N-[3-(3-ethyl-2-oxiranyl)-1-propyl]citraconimide, N-[3-(2,3-diethyl-2-oxiranyl)-1-propyl]citraconimide, N-[3-(3,3-diethyl-2-oxiranyl)-1-propyl]citraconimide, N-[3-(2,3,3-triethyl-2-oxiranyl)-1-propyl]citraconimide, N-[(2-phenyl-2-oxiranyl)methyl]citraconimide, N-[(3-phenyl-2-oxiranyl)methyl]citraconimide, N-[(2,3-diphenyl-2-oxiranyl)methyl]citraconimide, N-[(3,3-diphenyl-2-oxiranyl)methyl]citraconimide, N-[(2,3,3-triphenyl-2-oxiranyl)methyl]citraconimide, N-[(2-phenyl-2-oxiranyl)ethyl]citraconimide, N-[(3-phenyl-2-oxiranyl)ethyl]citraconimide, N-[(2,3-diphenyl-2-oxiranyl)ethyl]citraconimide, N-[(3,3-diphenyl-2-oxiranyl)ethyl]citraconimide, N-[(2,3,3-triphenyl-2-oxiranyl)ethyl]citraconimide, N-[3-(2-phenyl-2-oxiranyl)-1-propyl]citraconimide, N-[3-(3-phenyl-2-oxiranyl)-1-propyl]citraconimide, N-[3-(2,3-diphenyl-2-oxiranyl)-1-propyl]citraconimide, N-[3-(3,3-diphenyl-2-oxiranyl)-1-propyl]citraconimide, and N-[3-(2,3,3-triphenyl-2-oxiranyl)-1-propyl]citraconimide.

8. The method of claim 1 , where the imide compound containing an oxiranyl group is selected from the group consisting of N-(oxiranylmethyl) succinimide, N-[(2-methyl-2-oxiranyl)methyl]succinimide, N-[(3-methyl-2-oxiranyl)methyl]succinimide, N-[(2,3-dimethyl-2-oxiranyl)methyl]succinimide, N-[(3,3-dimethyl-2-oxiranyl)methyl]succinimide, N-[(2,3,3-trimethyl-2-oxiranyl)methyl]succinimide, N-(2-oxiranylethyl)succinimide, N-[(2-methyl-2-oxiranyl)ethyl]succinimide, N-[(3-methyl-2-oxiranyl)ethyl]succinimide, N-[(2,3-dimethyl-2-oxiranyl)ethyl]succinimide, N-[(3,3-dimethyl-2-oxiranyl)ethyl]succinimide, N-[(2,3,3-trimethyl-2-oxiranyl)ethyl]succinimide, N-(3-oxiranyl-1-propyl)succinimide, N-[3-(2-methyl-2-oxiranyl)-1-propyl]succinimide, N-[3-(3-methyl-2-oxiranyl)-1-propyl]succinimide, N-[3-(2,3-dimethyl-2-oxiranyl)-1-propyl]succinimide, N-[3-(3,3-dimethyl-2-oxiranyl)-1-propyl]succinimide, N-[3-(2,3,3-trimethyl-2-oxiranyl)-1-propyl]succinimide, N-[(2-ethyl-2-oxiranyl)methyl]succinimide, N-[(3-ethyl-2-oxiranyl)methyl]succinimide, N-[(2,3-diethyl-2-oxiranyl)methyl]succinimide, N-[(3,3-diethyl-2-oxiranyl)methyl]succinimide, N-[(2,3,3-triethyl-2-oxiranyl)methyl]succinimide, N-[(2-ethyl-2-oxiranyl)ethyl]succinimide, N-[(3-ethyl-2-oxiranyl)ethyl]succinimide, N-[(2,3-diethyl-2-oxiranyl)ethyl]succinimide, N-[(3,3-diethyl-2-oxiranyl)ethyl]succinimide, N-[(2,3,3-triethyl-2-oxiranyl)ethyl]succinimide, N-[3-(2-ethyl-2-oxiranyl)-1-propyl]succinimide, N-[3-(3-ethyl-2-oxiranyl)-1-propyl]succinimide, N-[3-(2,3-diethyl-2-oxiranyl)-1-propyl]succinimide, N-[3-(3,3-diethyl-2-oxiranyl)-1-propyl]succinimide, N-[3-(2,3,3-triethyl-2-oxiranyl)-1-propyl]succinimide, N-[(2-phenyl-2-oxiranyl)methyl]succinimide, N-[(3-phenyl-2-oxiranyl)methyl]succinimide, N-[(2,3-diphenyl-2-oxiranyl)methyl]succinimide, N-[(3,3-diphenyl-2-oxiranyl)methyl]succinimide, N-[(2,3,3-triphenyl-2-oxiranyl)methyl]succinimide, N-[(2-phenyl-2-oxiranyl)ethyl]succinimide, N-[(3-phenyl-2-oxiranyl)ethyl]succinimide, N-[(2,3-diphenyl-2-oxiranyl)ethyl]succinimide, N-[(3,3-diphenyl-2-oxiranyl)ethyl]succinimide, N-[(2,3,3-triphenyl-2-oxiranyl)ethyl]succinimide, N-[3-(2-phenyl-2-oxiranyl)-1-propyl]succinimide, N-[3-(3-phenyl-2-oxiranyl)-1-propyl]succinimide, N-[3-(2,3-diphenyl-2-oxiranyl)-1-propyl]succinimide, N-[3-(3,3-diphenyl-2-oxiranyl)-1-propyl]succinimide, and N-[3-(2,3,3-triphenyl-2-oxiranyl)-1-propyl]succinimide.

9. The method of claim 1 , where the imide compound containing an oxiranyl group is selected from the group consisting of N-(oxiranylmethyl)-1,8-naphthalimide, N-[(2-methyl-2-oxiranyl)methyl]-1,8-naphthalimide, N-[(3-methyl-2-oxiranyl)methyl]-1,8-naphthalimide, N-[(2,3-dimethyl-2-oxiranyl)methyl]-1,8-naphthalimide, N-[(3,3-dimethyl-2-oxiranyl)methyl]-1,8-naphthalimide, N-[(2,3,3-trimethyl-2-oxiranyl)methyl]-1,8-naphthalimide, N-(2-oxiranylethyl)-1,8-naphthalimide, N-[(2-methyl-2-oxiranyl)ethyl]-1,8-naphthalimide, N-[(3-methyl-2-oxiranypethyl]-1,8-naphthalimide, N-[(2,3-dimethyl-2-oxiranyl)ethyl]-1,8-naphthalimide, N-[(3,3-dimethyl-2-oxiranyl)ethyl]-1,8-naphthalimide, N-[(2,3,3-trimethyl-2-oxiranyl)ethyl]-1,8-naphthalimide, N-(3-oxiranyl-1-propyl)-1,8-naphthalimide, N-[3-(2-methyl-2-oxiranyl)-1-propyl]-1,8-naphthalimide, N-[3-(3-methyl-2-oxiranyl)-1-propyl]-1,8-naphthalimide, N-[3-(2,3-dimethyl-2-oxiranyl)-1-propyl]-1,8-naphthalimide, N-[3-(3,3-dimethyl-2-oxiranyl)-1-propyl]-1,8-naphthalimide, N-[3-(2,3,3-trimethyl-2-oxiranyl)-1-propyl]-1,8-naphthalimide, N-[(2-ethyl-2-oxiranyl)methyl]-1,8-naphthalimide, N-[(3-ethyl-2-oxiranyl)methyl]-1,8-naphthalimide, N-[(2,3-diethyl-2-oxiranyl)methyl]-1,8-naphthalimide, N-[(3,3-diethyl-2-oxiranyl)methyl]-1,8-naphthalimide, N-[(2,3,3-triethyl-2-oxiranyl)methyl]-1,8-naphthalimide, N-[(2-ethyl-2-oxiranypethyl]-1,8-naphthalimide, N-[(3-ethyl-2-oxiranyl)ethyl]-1,8-naphthalimide, N-[(2,3-diethyl-2-oxiranyl)ethyl]-1,8-naphthalimide, N-[(3,3-diethyl-2-oxiranypethyl]-1,8-naphthalimide, N-[(2,3,3-triethyl-2-oxiranypethyl]-1,8-naphthalimide, N-[3-(2-ethyl-2-oxiranyl)-1-propyl]-1,8-naphthalimide, N-[3-(3-ethyl-2-oxiranyl)-1-propyl]-1,8-naphthalimide, N-[3-(2,3-diethyl-2-oxiranyl)-1-propyl]-1,8-naphthalimide, N-[3-(3,3-diethyl-2-oxiranyl)-1-propyl]-1,8-naphthalimide, N-[3-(2,3,3-triethyl-2-oxiranyl)-1-propyl]-1,8-naphthalimide, N-[(2-phenyl-2-oxiranyl)methyl]-1,8-naphthalimide, N-[(3-phenyl-2-oxiranyl)methyl]-1,8-naphthalimide, N-[(2,3-diphenyl-2-oxiranyl)methyl]-1,8-naphthalimide, N-[(3,3-diphenyl-2-oxiranyl)methyl]-1,8-naphthalimide, N-[(2,3,3-triphenyl-2-oxiranyl)methyl]-1,8-naphthalimide, N-[(2-phenyl-2-oxiranyl)ethyl]-1,8-naphthalimide, N-[(3-phenyl-2-oxiranyl)ethyl]-1,8-naphthalimide, N-[(2,3-diphenyl-2-oxiranypethyl]-1,8-naphthalimide, N-[(3,3-diphenyl-2-oxiranyl)ethyl]-1,8-naphthalimide, N-[(2,3,3-triphenyl-2-oxiranyl)ethyl]-1,8-naphthalimide, N-[3-(2-phenyl-2-oxiranyl)-1-propyl]-1,8-naphthalimide, N-[3-(3-phenyl-2-oxiranyl)-1-propyl]-1,8-naphthalimide, N-[3-(2,3-diphenyl-2-oxiranyl)-1-propyl]-1,8-naphthalimide, N-[3-(3,3-diphenyl-2-oxiranyl)-1-propyl]-1,8-naphthalimide, and N-[3-(2,3,3-triphenyl-2-oxiranyl)-1-propyl]-1,8-naphthalimide.

10. The method of claim 1 , where the imide compound containing an oxiranyl group is selected from the group consisting of N-(oxiranylmethyl)-2,3-naphthalimide, N-[(2-methyl-2-oxiranyl)methyl]-2,3-naphthalimide, N-[(3-methyl-2-oxiranyl)methyl]-2,3-naphthalimide, N-[(2,3-dimethyl-2-oxiranyl)methyl]-2,3-naphthalimide, N-[(3,3-dimethyl-2-oxiranyl)methyl]-2,3-naphthalimide, N-[(2,3,3-trimethyl-2-oxiranyl)methyl]-2,3-naphthalimide, N-(2-oxiranylethyl)-2,3-naphthalimide, N-[(2-methyl-2-oxiranypethyl]-2,3-naphthalimide, N-[(3-methyl-2-oxiranypethyl]-2,3-naphthalimide, N-[(2,3-dimethyl-2-oxiranypethyl]-2,3-naphthalimide, N-[(3,3-dimethyl-2-oxiranyl)ethyl]-2,3-naphthalimide, N-[(2,3,3-trimethyl-2-oxiranypethyl]-2,3-naphthalimide, N-(3-oxiranyl-1-propyl)-2,3-naphthalimide, N-[3-(2-methyl-2-oxiranyl)-1-propyl]-2,3-naphthalimide, N-[3-(3-methyl-2-oxiranyl)-1-propyl]-2,3-naphthalimide, N-[3-(2,3-dimethyl-2-oxiranyl)-1-propyl]-2,3-naphthalimide, N-[3-(3,3-dimethyl-2-oxiranyl)-1-propyl]-2,3-naphthalimide, N-[3-(2,3,3-trimethyl-2-oxiranyl)-1-propyl]-2,3-naphthalimide, N-[(2-ethyl-2-oxiranyl)methyl]-2,3-naphthalimide, N-[(3-ethyl-2-oxiranyl)methyl]-2,3-naphthalimide, N-[(2,3-diethyl-2-oxiranyl)methyl]-2,3-naphthalimide, N-[(3,3-diethyl-2-oxiranyl)methyl]-2,3-naphthalimide, N-[(2,3,3-triethyl-2-oxiranyl)methyl]-2,3-naphthalimide, N-[(2-ethyl-2-oxiranypethyl]-2,3-naphthalimide, N-[(3-ethyl-2-oxiranypethyl]-2,3-naphthalimide, N-[(2,3-diethyl-2-oxiranypethyl]-2,3-naphthalimide, N-[(3,3-diethyl-2-oxiranypethyl]-2,3-naphthalimide, N-[(2,3,3-triethyl-2-oxiranypethyl]-2,3-naphthalimide, N-[3-(2-ethyl-2-oxiranyl)-1-propyl]-2,3-naphthalimide, N-[3-(3-ethyl-2-oxiranyl)-1-propyl]-2,3-naphthalimide, N-[3-(2,3-diethyl-2-oxiranyl)-1-propyl]-2,3-naphthalimide, N-[3-(3,3-diethyl-2-oxiranyl)-1-propyl]-2,3-naphthalimide, N-[3-(2,3,3-triethyl-2-oxiranyl)-1-propyl]-2,3-naphthalimide, N-[(2-phenyl-2-oxiranyl)methyl]-2,3-naphthalimide, N-[(3-phenyl-2-oxiranyl)methyl]-2,3-naphthalimide, N-[(2,3-diphenyl-2-oxiranyl)methyl]-2,3-naphthalimide, N-[(3,3-diphenyl-2-oxiranyl)methyl]-2,3-naphthalimide, N-[(2,3,3-triphenyl-2-oxiranyl)methyl]-2,3-naphthalimide, N-[(2-phenyl-2-oxiranyl)ethyl]-2,3-naphthalimide, N-[(3-phenyl-2-oxiranypethyl]-2,3-naphthalimide, N-[(2,3-diphenyl-2-oxiranypethyl]-2,3-naphthalimide, N-[(3,3-diphenyl-2-oxiranypethyl]-2,3-naphthalimide, N-[(2,3,3-triphenyl-2-oxiranyl)ethyl]-2,3-naphthalimide, N-[3-(2-phenyl-2-oxiranyl)-1-propyl]-2,3-naphthalimide, N-[3-(3-phenyl-2-oxiranyl)-1-propyl]-2,3-naphthalimide, N-[3-(2,3-diphenyl-2-oxiranyl)-1-propyl]-2,3-naphthalimide, N-[3-(3,3-diphenyl-2-oxiranyl)-1-propyl]-2,3-naphthalimide, and N-[3-(2,3,3-diphenyl-2-oxiranyl)-1-propyl]-2,3-naphthalimide.

11. The method of claim 1 , where the imide compound containing an oxiranyl group is selected from the group consisting of N-(oxiranylmethyl)-1,2-cyclopentanedicarboximide, N-[(2-methyl-2-oxiranyl)methyl]-1,2-cyclopentanedicarboximide, N-[(3-methyl-2-oxiranyl)methyl]-1,2-cyclopentanedicarboximide, N-[(2,3-dimethyl-2-oxiranyl)methyl]-1,2-cyclopentanedicarboximide, N-[(3,3-dimethyl-2-oxiranyl)methyl]-1,2-cyclopentanedicarboximide, N-[(2,3,3-trimethyl-2-oxiranyl)methyl]-1,2-cyclopentanedicarboximide, N-(2-oxiranylethyl)-1,2-cyclopentanedicarboximide, N-[(2-methyl-2-oxiranyl)ethyl]-1,2-cyclopentanedicarboximide, N-[(3-methyl-2-oxiranyl)ethyl]-1,2-cyclopentanedicarboximide, N-[(2,3-dimethyl-2-oxiranyl)ethyl]-1,2-cyclopentanedicarboximide, N-[(3,3-dimethyl-2-oxiranyl)ethyl]-1,2-cyclopentanedicarboximide, N-[(2,3,3-trimethyl-2-oxiranyl)ethyl]-1,2-cyclopentanedicarboximide, N-(3-oxiranyl-1-propyl)-1, 2-cyclopentanedicarboximide, N-[3-(2-methyl-2-oxiranyl)-1-propyl]-1,2-cyclopentanedicarboximide, N-[3-(3-methyl-2-oxiranyl)-1-propyl]-1,2-cyclopentanedicarboximide, N-[3-(2,3-dimethyl-2-oxiranyl)-1-propyl]-1,2-cyclopentanedicarboximide, N-[3-(3,3-dimethyl-2-oxiranyl)-1-propyl]-1,2-cyclopentanedicarboximide, N-[3-(2,3,3-trimethyl-2-oxiranyl)-1-propyl]-1,2-cyclopentanedicarboximide, N-[(2-ethyl-2-oxiranyl)methyl]-1,2-cyclopentanedicarboximide, N-[(3-ethyl-2-oxiranyl)methyl]-1,2-cyclopentanedicarboximide, N-[(2,3-diethyl-2-oxiranyl)methyl]-1,2-cyclopentanedicarboximide, N-[(3,3-diethyl-2-oxiranyl)methyl]-1,2-cyclopentanedicarboximide, N-[(2,3,3-triethyl-2-oxiranyl)methyl]-1,2-cyclopentanedicarboximide, N-[(2-ethyl-2-oxiranyl)ethyl]-1,2-cyclopentanedicarboximide, N-[(3-ethyl-2-oxiranyl)ethyl]-1,2-cyclopentanedicarboximide, N-[(2,3-diethyl-2-oxiranyl)ethyl]-1,2-cyclopentanedicarboximide, N-[(3,3-diethyl-2-oxiranyl)ethyl]-1,2-cyclopentanedicarboximide, N-[(2,3,3-triethyl-2-oxiranyl)ethyl]-1,2-cyclopentanedicarboximide, N-[3-(2-ethyl-2-oxiranyl)-1-propyl]-1,2-cyclopentanedicarboximide, N-[3-(3-ethyl-2-oxiranyl)-1-propyl]-1,2-cyclopentanedicarboximide, N-[3-(2,3-diethyl-2-oxiranyl)-1-propyl]-1,2-cyclopentanedicarboximide, N-[3-(3,3-diethyl-2-oxiranyl)-1-propyl]-1,2-cyclopentanedicarboximide, N-[3-(2,3,3-triethyl-2-oxiranyl)-1-propyl]-1,2-cyclopentanedicarboximide, N-[(2-phenyl-2-oxiranyl)methyl]-1,2-cyclopentanedicarboximide, N-[(3-phenyl-2-oxiranyl)methyl]-1,2-cyclopentanedicarboximide, N-[(2,3-diphenyl-2-oxiranyl)methyl]-1,2-cyclopentanedicarboximide, N-[(3,3-diphenyl-2-oxiranyl)methyl]-1,2-cyclopentanedicarboximide, N-[(2,3,3-triphenyl-2-oxiranyl)methyl]-1,2-cyclopentanedicarboximide, N-[(2-phenyl-2-oxiranyl)ethyl]-1,2-cyclopentanedicarboximide, N-[(3-phenyl-2-oxiranyl)ethyl]-1,2-cyclopentanedicarboximide, N-[(2,3-diphenyl-2-oxiranyl)ethyl]-1,2-cyclopentanedicarboximide, N-[(3,3-diphenyl-2-oxiranyl)ethyl]-1,2-cyclopentanedicarboximide, N-[(2,3,3-triphenyl-2-oxiranyl)ethyl]-1,2-cyclopentanedicarboximide, N-[3-(2-phenyl-2-oxiranyl)-1-propyl]-1,2-cyclopentanedicarboximide, N-[3-(3-phenyl-2-oxiranyl)-1-propyl]-1,2-cyclopentanedicarboximide, N-[3-(2,3-diphenyl-2-oxiranyl)-1-propyl]-1,2-cyclopentanedicarboximide, N-[3-(3,3-diphenyl-2-oxiranyl)-1-propyl]-1,2-cyclopentanedicarboximide, and N-[3-(2,3,3-triphenyl-2-oxiranyl)-1-propyl]-1,2-cyclopentanedicarboximide.

12. The method of claim 1 , where the imide compound containing an oxiranyl group is selected from the group consisting of N-(oxiranylmethyl)-1,2-cyclohexanedicarboximide, N-[(2-methyl-2-oxiranyl)methyl]-1,2-cyclohexanedicarboximide, N-[(3-methyl-2-oxiranyl)methyl]-1,2-cyclohexanedicarboximide, N-[(2,3-dimethyl-2-oxiranyl)methyl]-1,2-cyclohexanedicarboximide, N-[(3,3-dimethyl-2-oxiranyl)methyl]-1,2-cyclohexanedicarboximide, N-[(2,3,3-trimethyl-2-oxiranyl)methyl]-1,2-cyclohexanedicarboximide, N-(2-oxiranylethyl)-1,2-cyclohexanedicarboximide, N-[(2-methyl-2-oxiranypethyl]-1,2-cyclohexanedicarboximide, N-[(3-methyl-2-oxiranypethyl]-1,2-cyclohexanedicarboximide, N-[(2,3-dimethyl-2-oxiranypethyl]-1,2-cyclohexanedicarboximide, N-[(3,3-dimethyl-2-oxiranyl)ethyl]-1,2-cyclohexanedicarboximide, N-[(2,3,3-trimethyl-2-oxiranypethyl]-1,2-cyclohexanedicarboximide, N-(3-oxiranyl-1-propyl)-1,2-cyclohexanedicarboximide, N-[3-(2-methyl-2-oxiranyl)-1-propyl]-1,2-cyclohexanedicarboximide, N-[3-(3-methyl-2-oxiranyl)-1-propyl]-1,2-cyclohexanedicarboximide, N-[3-(2,3-dimethyl-2-oxiranyl)-1-propyl]-1,2-cyclohexanedicarboximide, N-[3-(3,3-dimethyl-2-oxiranyl)-1-propyl]-1,2-cyclohexanedicarboximide, N-[3-(2,3,3-trimethyl-2-oxiranyl)-1-propyl]-1,2-cyclohexanedicarboximide, N-[(2-ethyl-2-oxiranyl)methyl]-1,2-cyclohexanedicarboximide, N-[(3-ethyl-2-oxiranyl)methyl]-1,2-cyclohexanedicarboximide, N-[(2,3-diethyl-2-oxiranyl)methyl]-1,2-cyclohexanedicarboximide, N-[(3,3-diethyl-2-oxiranyl)methyl]-1,2-cyclohexanedicarboximide, N-[(2,3,3-triethyl-2-oxiranyl)methyl]-1,2-cyclohexanedicarboximide, N-[(2-ethyl-2-oxiranypethyl]-1,2-cyclohexanedicarboximide, N-[(3-ethyl-2-oxiranypethyl]-1,2-cyclohexanedicarboximide, N-[(2,3-diethyl-2-oxiranypethyl]-1,2-cyclohexanedicarboximide, N-[(3,3-diethyl-2-oxiranypethyl]-1,2-cyclohexanedicarboximide, N-[(2,3,3-triethyl-2-oxiranypethyl]-1,2-cyclohexanedicarboximide, N-[3-(2-ethyl-2-oxiranyl)-1-propyl]-1,2-cyclohexanedicarboximide, N-[3-(3-ethyl-2-oxiranyl)-1-propyl]-1,2-cyclohexanedicarboximide, N-[3-(2,3-diethyl-2-oxiranyl)-1-propyl]-1,2-cyclohexanedicarboximide, N-[3-(3,3-diethyl-2-oxiranyl)-1-propyl]-1,2-cyclohexanedicarboximide, N-[3-(2,3,3-triethyl-2-oxiranyl)-1-propyl]-1,2-cyclohexanedicarboximide, N-[(2-phenyl-2-oxiranyl)methyl]-1,2-cyclohexanedicarboximide, N-[(3-phenyl-2-oxiranyl)methyl]-1,2-cyclohexanedicarboximide, N-[(2,3-diphenyl-2-oxiranyl)methyl]-1,2-cyclohexanedicarboximide, N-[(3,3-diphenyl-2-oxiranyl)methyl]-1,2-cyclohexanedicarboximide, N-[(2,3,3-triphenyl-2-oxiranyl)methyl]-1,2-cyclohexanedicarboximide, N-[(2-phenyl-2-oxiranyl)ethyl]-1,2-cyclohexanedicarboximide, N-[(3-phenyl-2-oxiranyl)ethyl]-1,2-cyclohexanedicarboximide, N-[(2,3-diphenyl-2-oxiranyl)ethyl]-1,2-cyclohexanedicarboximide, N-[(3,3-diphenyl-2-oxiranyl)ethyl]-1,2-cyclohexanedicarboximide, N-[(2,3,3-triphenyl-2-oxiranyl)ethyl]-1,2-cyclohexanedicarboximide, N-[3-(2-phenyl-2-oxiranyl)-1-propyl]-1,2-cyclohexanedicarboximide, N-[3-(3-phenyl-2-oxiranyl)-1-propyl]-1,2-cyclohexanedicarboximide, N-[3-(2,3-diphenyl-2-oxiranyl)-1-propyl]-1,2-cyclohexanedicarboximide, N-[3-(3,3-diphenyl-2-oxiranyl)-1-propyl]-1,2-cyclohexanedicarboximide, and N-[3-(2,3,3-triphenyl-2-oxiranyl)-1-propyl]-1,2-cyclohexanedicarboximide.

13. The method of claim 1 , where the monomer includes conjugated diene monomer.

14. The method of claim 13 , where said step of polymerizing employs a coordination catalyst.

15. The method of claim 14 , where the coordination catalyst is a lanthanide-based catalyst.

16. The method of claim 15 , where the lanthanide-based catalyst includes (a) a lanthanide-containing compound, (b) an alkylating agent, and (c) a halogen source.

17. The method of claim 16 , where the alkylating agent includes an aluminoxane and an organoaluminum compound represented by the formula AlR n X 3-n , where each R, which may be the same or different, is a monovalent organic group that is attached to the aluminum atom via a carbon atom, where each X, which may be the same or different, is a hydrogen atom, a halogen atom, a carboxylate group, an alkoxide group, or an aryloxide group, and where n is an integer of 1 to 3.

18. The method of claim 15 , where said step of polymerizing monomer takes place within a polymerization mixture including less than 20% by weight of organic solvent.

19. The method of claim 13 , where said step of polymerizing employs an anionic initiator.

20. The method of claim 19 , where the anionic initiator is an organolithium compound.

21. A method for preparing a coupled polymer, the method comprising the steps of:

(i) polymerizing conjugated diene monomer, and optionally monomer copolymerizable therewith, to form polymer having a reactive chain end; and

(ii) reacting the reactive chain end of the polymer with an imide compound containing an oxiranyl group.

22. The method of claim 21 , where the imide compound containing an oxiranyl group is defined by the formula I:

where R 1 is a divalent organic group, R 2 is a bond or a divalent organic group, and R 3 , R 4 , and R 5 are each independently a hydrogen atom or a monovalent organic group, or where R 3 joins with R 4 or R 5 to form a divalent organic group, or where R 4 and R 5 join to form a divalent organic group.

23. A coupled polymer prepared by the steps of:

(i) polymerizing monomer to form a reactive polymer; and

(ii) reacting the reactive polymer with an imide compound containing an oxiranyl group.

24. A tire component prepared from the coupled polymer of claim 23 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 3, 2016
From: LUO, STEVEN
To: BRIDGESTONE CORPORATION
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Continuity (2)
Provisional Application 62115899 · Feb 13, 2015
Related Publication 20160237186A1 · Aug 18, 2016