Functional initiator for anionic polymerization

Patent metadata

Field	Value
Publication number	US-10618994-B2
Application number	US-201615775685-A
Country	US
Kind code	B2
Filing date	Oct 8, 2016
Priority date	Nov 13, 2015
Publication date	Apr 14, 2020
Grant date	Apr 14, 2020

Abstract

An ethylenically unsaturated polymer includes at a terminus the radical of a compound that is the reaction product of a secondary amine and a vinyl aromatic compound. The secondary amine portion of the compound can be a cyclic compound with N as one of its ring atoms, while the vinyl aromatic compound can include one or more substituents. The polymer can be used as a component of a variety of elastomeric compounds used in the production of vulcanizates.

First claim

That which is claimed is:

1. A process for providing a polymer that comprises ethylenic unsaturation, comprising:
a) providing an initiating compound having the general formula

where
R 1 is a substituted or unsubstituted phenyl group,
R 2 is R 1 , a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and
R N is the radical of a secondary amine group,

with the proviso that each of R 1 and R 2 is free of active hydrogen atom-containing groups;

b) introducing said initiating compound to a reaction vessel that comprises one or more organic liquids and one or more ethylenically unsaturated compounds which comprise at least one polyene;
c) allowing said one or more ethylenically unsaturated compounds to polymerize, thereby providing said polymer; and
d) optionally, while said polymer is in carbanionic form, allowing it to react with a terminating compound, coupling agent or linking agent so as to provide terminal functionality to said polymer.

2. The process of claim 1 wherein said at least one polyene comprises one or more conjugated dienes.

3. The process of claim 2 wherein said one or more ethylenically unsaturated compounds further comprises at least one vinyl aromatic compound.

4. The process of claim 1 wherein each of said at least one polyene is a conjugated diene.

5. The process of claim 4 wherein said one or more ethylenically unsaturated compounds further comprises at least one vinyl aromatic compound.

6. The process of claim 1 wherein said one or more organic liquids comprise at least one C 5 -C 12 acyclic alkane.

7. The process of claim 6 wherein said one or more organic liquids is at least one C 5 -C 12 acyclic alkane.

8. The process of claim 1 wherein said initiating compound is the reaction product of a lithiated secondary amine and a vinyl aromatic compound having the general formula

where R 1 is a substituted or unsubstituted phenyl group and R 2 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group or R 1 , with the proviso that each of R 1 and R 2 is free of active hydrogen atom-containing groups.

9. The process of claim 8 wherein the N atom of said secondary amine is bonded to two hydrocarbyl groups.

10. The process of claim 9 wherein each of said hydrocarbyl groups is an alkyl group.

11. The process of claim 8 wherein the N atom of said secondary amine is part of a cyclic group having 5 to 8 ring atoms.

12. The process of claim 11 wherein at least one ring atom of said cyclic group having 5 to 8 ring atoms comprises at least one substituent.

13. The process of claim 12 wherein said at least one substituent comprises a tertiary amine group.

14. The process of claim 13 wherein said tertiary amine group is part of a cyclic group having 5 to 8 ring atoms.

15. The process of claim 14 wherein said secondary amine is 4-piperidinopiperidine.

16. The process of claim 8 wherein R 1 is a substituted phenyl group.

17. The process of claim 16 wherein at least one substituent of said substituted phenyl group comprises at least one P, O or Si atom.

18. The process of claim 1 further comprising recovering and isolating said polymer.

19. The process of claim 18 further comprising blending said polymer with ingredients that comprise at least one particulate filler so as to provide a rubber compound.

20. The process of claim 19 further comprising vulcanizing said rubber compound so as to provide a vulcanizate, said vulcanizate optionally being a tire component.

Assignees

• Bridgestone Corp

Inventors

• Yan Yuan-Yong
• Roggeman David M

Classifications

• C08C19/44

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

• C08C19/22

  Incorporating nitrogen atoms into the molecule · CPC title

• C08F236/08

  Isoprene · CPC title

• B60C11/0008

  characterised by the tread rubber · CPC title

• B01J31/0275

  also containing elements or functional groups covered by B01J31/0201 - B01J31/0269 · CPC title