Silane sulfide modified elastomeric polymers

Patent metadata

Field	Value
Publication number	US-9586980-B2
Application number	US-201214427025-A
Country	US
Kind code	B2
Filing date	Sep 14, 2012
Priority date	Sep 14, 2012
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

The present invention relates to silane sulfide modifier compounds and methods of making them. The invention also relates to a silane sulfide modified macromolecular compound obtainable by reacting a living anionic elastomeric polymer and a silane sulfide modifier. The silane sulfide modified macromolecular compound may be provided in the form of a polymer composition, and the polymer composition may be vulcanized (cross-linked) by making use of and reaction with at least one vulcanization agent, resulting in a vulcanized polymer composition.

First claim

The invention claimed is:

1. A silane sulfide modified elastomeric macromolecular compound obtainable by reacting
i) a living anionic elastomeric polymer and
ii) a silane sulfide modifier represented by the following Formula (5) or Formula (6):

wherein
M is a silicon atom or a tin atom;
R 3 is at least divalent and is (C 8 -C 16 ) alkylarylalkyl, (C 7 -C 16 ) arylalkyl, (C 7 -C 16 ) alkylaryl, or (C 1 -C 16 ) alkyl, and each group may be substituted with one or more of the following groups: tertiary amine group, silyl group, (C 7 -C 18 ) aralkyl group and (C 6 -C 18 ) aryl group;
R 1 , R 12 and R 16 are each independently selected from a hydrogen atom and (C 1 -C 4 ) alkyl;
R 2 , R 13 and R 15 are each independently selected from (C 1 -C 16 ) alkyl, (C 7 -C 16 ) alkylaryl and (C 7 -C 16 ) arylalkyl;
R 4 and R 14 are each independently selected from (C 1 -C 16 ) alkyl and (C 7 -C 16 ) alkylaryl;
b, d and f are each independently selected from an integer of 0, 1 and 2; a, c and e are each independently selected from an integer of 1, 2 and 3; a+b=3; c+d=3; and e+f=3.

2. The silane sulfide modified elastomeric macromolecular compound according to claim 1 , which is represented by the following Formula (P1)
((P) r (R 1 O) x-r (R 2 ) y Si—R 3 —S) s M(R 4 ) t (X) u   (Formula P1),

wherein
P is a polymer chain comprising monomer units derived from at least one of the following monomer groups: butadiene, isoprene, styrene and alpha-methylstyrene, the number of monomer units per macromolecule ranging from 10 to 50.000;
M is a silicon atom or a tin atom;
x is an integer selected from 1, 2 and 3; y is an integer selected from 0, 1, and 2; r is an integer selected from 1, 2 and 3; wherein x+y+r=3;
s is an integer selected from 2, 3 and 4; t is an integer selected from 0, 1 and 2; u is an integer selected from 0, 1 and 2; wherein s+t+u=4;
R 1 is independently selected from a hydrogen atom and (C 1 -C 6 ) alkyl;
R 2 is independently selected from (C 1 -C 16 ) alkyl, (C 7 -C 16 ) alkylaryl and (C 7 -C 16 ) arylalkyl;
R 3 is at least divalent and is independently selected from (C 1 -C 16 )alkyl, (C 8 -C 16 ) alkylarylalkyl, (C 7 -C 16 ) arylalkyl and (C 7 -C 16 ) alkylaryl, and each group may be substituted with one or more of the following groups: tertiary amine group, silyl group, (C 7 -C 18 ) aralkyl group and (C 6 -C 18 ) aryl group;
R 4 is independently selected from (C 1 -C 16 ) alkyl and (C 7 -C 16 ) alkylaryl; and X is independently selected from chloride, bromide and —OR 5 ; wherein R 5 is selected from (C 1 -C 16 ) alkyl and (C 7 -C 16 ) arylalkyl.

3. The silane sulfide modified elastomeric macromolecular compound according to claim 2 , wherein R 3 is divalent (C 1 -C 16 ) alkyl.

4. The silane sulfide modified elastomeric macromolecular compound according to claim 2 , wherein X is selected from chloride, bromide and —OR 5 ; wherein R 5 is selected from (C 1 -C 16 ) alkyl.

5. The silane sulfide modified elastomeric macromolecular compound according to claim 2 , wherein R 2 and R 4 are independently selected from (C 1 -C 16 ) alkyl.

6. The silane sulfide modified elastomeric macromolecular compound according to claim 2 , wherein R 1 , R 2 , R 4 and R 5 are independently selected from (C 1 -C 4 ) alkyl.

7. The silane sulfide modified elastomeric macromolecular compound according to claim 2 , wherein s and t are each 2 and u is 0; or s is 3, t is 1 and u is 0.

8. The silane sulfide modified elastomeric macromolecular compound according to claim 2 , wherein r is 1, x is 1 and y is 1; or r is 1, x is 0 and y is 2.

9. A polymer composition comprising at least one silane sulfide modified macromolecular compound as defined in claim 1 and one or more further components selected from components which are added to or formed as a result of the polymerization process used for making the modified macromolecular compound and components which remain after solvent removal from the polymerization process.

10. The polymer composition according to claim 9 , which comprises at least one filler.

11. The polymer composition according to claim 10 , wherein the filler is one or more selected from carbon black, silica, carbon-silica dual-phase-filler, clay, calcium carbonate, magnesium carbonate, lignin, and glass particles.

12. The polymer composition according to claim 11 , wherein the filler comprises silica.

13. The polymer composition according to claim 11 , wherein the filler comprises carbon black.

14. The polymer composition according to claim 9 , which comprises a vulcanization agent.

15. The polymer composition according to claim 9 , which comprises at least one polymer selected from the group consisting of polybutadiene, butadiene-styrene copolymers, butadiene-isoprene copolymers, polyisoprene and butadiene-styrene-isoprene terpolymers.

16. A vulcanized polymer composition comprising the reaction product of at least the following: at least one vulcanization agent; and the polymer composition as defined in claim 9 .

17. A method for making a vulcanized polymer composition comprising reacting at least the following components: at least one vulcanization agent; and the polymer composition as defined in claim 9 .

18. An article comprising at least one component formed from the vulcanized polymer composition as defined in claim 16 .

19. The article according to claim 18 , which is selected from the group consisting of a tire, a tire tread, a tire side wall, a tire carcass, a belt, a hose, a vibration damper, and a footwear component.

20. The silane sulfide modified elastomeric macromolecular compound according to claim 1 , wherein R 3 is a (C 1 -C 16 ) divalent alkyl group or (C 8 -C 16 ) divalent alkylarylalkyl group.

21. The silane sulfide modified elastomeric macromolecular compound according to claim 1 , wherein R 3 is selected from —CH 2 —, —(CH 2 ) 2 —, —(CH 2 ) 3 —, —(CH 2 ) 4 —, —CH 2 —C 6 H 4 —CH 2 — and —C 6 H 4 —C(CH 3 ) 2 —C 6 H 4 —.

22. The silane sulfide modified elastomeric macromolecular compound according to claim 1 , wherein R 2 , R 4 , R 13 and R 15 are each independently selected from (C 1 -C 16 ) alkyl.

23. The silane sulfide modified elastomeric macromolecular compound according to claim 1 , wherein M is a silicon atom; a, c and e are each an integer selected from 2 and 3; and b, d and f are each an integer selected from 0 and 1.

Assignees

• Thiele Sven
• Trinseo Europe Gmbh

Inventors

• Thiele Sven

Classifications

• C07F7/2264

  Chemistry & Metallurgy · mapped topic

• C08K3/36

  Silica · CPC title

• C07F7/2268 Primary

  Chemistry & Metallurgy · mapped topic

• C08F236/10

  with vinyl-aromatic monomers · CPC title

• C08J3/24

  Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K) · CPC title