Copolymer end-functionalized with functional silane, compositions thereof and related processes

Patent metadata

Field	Value
Publication number	US-10828937-B2
Application number	US-201615740052-A
Country	US
Kind code	B2
Filing date	Jun 30, 2016
Priority date	Jul 1, 2015
Publication date	Nov 10, 2020
Grant date	Nov 10, 2020

Abstract

Disclosed herein are copolymers end-functionalized with functionalized silanes of specified structure, rubber compositions comprising the copolymer, and related processes for preparing the end-functionalized copolymer. The present disclosure also relates to tires having at least one component (e.g., a tread) containing the end-functionalized copolymer or a rubber composition thereof. The copolymer comprises 55-80% by weight of a conjugated diene monomer and 20-45% by weight of an aromatic vinyl monomer lacking any nitrogen substitution on its aromatic ring, wherein the total amount of conjugated diene monomer and aromatic vinyl monomer comprise 100% (of the total monomers in the copolymer), and the end-functionalization comprises at least one group having formula (I).

First claim

What is claimed is:

1. An end-functionalized copolymer comprising 55-80% by weight of a conjugated diene monomer and 20-45% by weight of an aromatic vinyl monomer lacking any nitrogen substitution on its aromatic ring,
wherein the total amount of conjugated diene monomer and aromatic vinyl monomer comprise 100% of the total monomers in the copolymer, and the aromatic vinyl monomer consists of styrene, and
the end-functionalization comprises at least one group having formula (I)

wherein R 1 and R 2 are the same or different and are independently selected from C1-C20 alkyl and alkoxy,
a and c are the same or different and are each an integer from 1 to 10,
b is 1,
W is O, S, or NZ where Z is selected from Si(R 4 )3 and each R 4 is independently selected from C1-C20 alkyl, C2-C20 alkenyl, or C6-C20 aryl,
X is selected from 5 membered aromatic rings, 6 membered aromatic rings, or fused combinations thereof and each ring of X contains 1 sulfur, 1 nitrogen, 1 oxygen, or a combination thereof, and optionally is substituted with at least one substituent on the aromatic ring.

2. The end-functionalized copolymer of claim 1 , wherein the vinyl bond content in the butadiene portion of the copolymer is greater than 35%.

3. The end-functionalized copolymer of claim 1 , wherein at least one of the following is met:
a. the copolymer has a Mw of 100,000 to 800,000 g/mole (SBR standard); or
b. the copolymer has a Tg of −20 to −70° C.

4. The end-functionalized copolymer of claim 1 , wherein X is substituted with at least one group selected from C1-C10 alkyl groups, C6 to C20 aryl groups, C2 to C10 alkenyl groups, C3-C10 non-terminal alkynyl groups, each optionally containing one or more heteroatoms selected from O, Si, N, S, and P wherein any heteroatom lacks active hydrogen.

5. The end-functionalized copolymer of claim 1 , wherein W comprises S.

6. The end-functionalized copolymer of claim 1 , wherein X comprises a 5 or 6 membered aromatic ring containing 1 nitrogen, optionally substituted with at least one substituent on the aromatic ring.

7. The end-functionalized copolymer of claim 1 , wherein the conjugated diene consists of 1,3-butadiene.

8. A rubber composition comprising
5-100 parts by weight of the end-functionalized copolymer of claim 1 ,
0-95 parts by weight of at least one conjugated diene-monomer containing polymer or copolymer, and
5 to 200 phr of at least one reinforcing filler selected from carbon black, silica, and combinations thereof.

9. A tire having a tread comprising the rubber composition of claim 8 .

10. The end-functionalized copolymer of claim 2 , wherein the conjugated diene consists of 1,3-butadiene.

11. The end-functionalized copolymer of claim 3 , wherein both (a) and (b) are met.

12. The rubber composition of claim 8 , wherein the vinyl bond content in the butadiene portion of the copolymer is greater than 35%.

13. The rubber composition of claim 8 , wherein at least one of the following is met:
a. the copolymer has a Mw of 100,000 to 800,000 g/mole (SBR standard); or
b. the copolymer has a Tg of −20 to −70° C.

14. The rubber composition of claim 13 , wherein both (a) and (b) are met.

15. The rubber composition of claim 8 , wherein X is substituted with at least one group selected from C1-C10 alkyl groups, C6 to C20 aryl groups, C2 to C10 alkenyl groups, C3-C10 non-terminal alkynyl groups, each optionally containing one or more heteroatoms selected from O, Si, N, S, and P wherein any heteroatom lacks active hydrogen.

16. The rubber composition of claim 8 , wherein W comprises S.

17. The rubber composition of claim 8 , wherein X comprises a 5 or 6 membered aromatic ring containing 1 nitrogen, optionally substituted with at least one substituent on the aromatic ring.

18. The rubber composition of claim 8 , wherein the conjugated diene consists of 1,3-butadiene.

19. The rubber composition of claim 13 , wherein the conjugated diene consists of 1,3-butadiene.

20. The rubber composition of claim 1 , wherein the end-functionalized copolymer has a head end bearing a hydrocarbyl residue from an anionic initiator.

Assignees

• Bridgestone Corp

Inventors

• Yan Yuan-Yong

Classifications

• C08C19/42

  reacting with metals or metal-containing groups · CPC title

• B60C1/00

  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

• C08C19/20

  Incorporating sulfur atoms into the molecule · CPC title

• C08F236/06

  Butadiene · CPC title