Improving the rolling resistance of diene rubber tires by means of silane-modified polybutadienes

Patent metadata

Field	Value
Publication number	US-10487195-B2
Application number	US-201615569264-A
Country	US
Kind code	B2
Filing date	Apr 29, 2016
Priority date	May 13, 2015
Publication date	Nov 26, 2019
Grant date	Nov 26, 2019

Abstract

The invention relates to the use of silane-modified polybutadienes in rubber mixtures, in particular for improving the rolling resistance of diene rubber tires. In particular, the invention is directed to silane-modified polybutadienes in rubber mixtures, wherein the polybutadiene comprises the 1,3-butadiene-derived monomer units and wherein the proportion of A in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 10 to 60 mol %, and wherein the sum of the proportions of B and C in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 40 to 90 mol %.

First claim

The invention claimed is:

1. A rubber comprising silane-modified polybutadiene, wherein the polybutadiene comprises the 1,3-butadiene-derived monomer units

and wherein the proportion of A in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 10 to 60 mol %, and wherein the sum of the proportions of B and C in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 40 to 90 mol % wherein the silane-modified polybutadienes are obtainable by reacting hydroxyl-terminated polybutadienes produced by free-radical polymerization with one or more organosilane compounds, wherein the silane-modified polybutadiene has an average functionality of from 0.1 to 4.

2. The rubber according to claim 1 , wherein the proportion of A) in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 15 to 30 mol %, the proportion of B) in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 50 to 70 mol % and the proportion of C) in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 15 to 30 mol, wherein the silane-modified polybutadiene has an average functionality of from 0.7 to 2.6.

3. The rubber according to claim 1 , wherein the organosilane compound is selected from the group comprising compounds of formula I
OCN—R—Si(OR 1 ) x (R 2 ) 3-x   I

where R represents linear or branched alkylene chains having 1-4 carbon atoms and R 1 and R 2 simultaneously or independently of one another represent linear or branched alkyl chains having from 1 to 5 carbon atoms x=1, 2 or 3, wherein the silane-modified polybutadiene has an average functionality of from 1.2 to 2.5.

4. A rubber mixture comprising silane-modified polybutadienes, wherein the polybutadiene comprises the 1,3-butadiene-derived monomer units

and wherein the proportion of A in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 10 to 60 mol %, and wherein the sum of the proportions of B and C in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 40 to 90 mol % wherein the silane-modified polybutadienes are obtainable by reacting hydroxyl-terminated polybutadienes produced by free-radical polymerization with one or more organosilane compounds, wherein the silane-modified polybutadiene has an average functionality of from 0.1 to 4.

5. The rubber mixture according to claim 4 , wherein the silane-modified polybutadiene is employed in an amount of from 0.5 to 25 parts by wt based on 100 parts by wt of rubber, wherein the silane-modified polybutadiene has an average functionality of from 0.7 to 2.6.

6. The rubber mixture according to claim 4 , wherein said mixture comprise 10 to 150 parts by wt of precipitated silica, 0 to 100 parts by wt of carbon black and 0.5 to 15 parts by wt of silane-modified polybutadiene according to claim 1 , in each case based on 100 parts by weight of rubber %, wherein the silane-modified polybutadiene has an average functionality of from 1.2 to 2.5.

7. The rubber mixture according to claim 4 , wherein said mixture comprise an organosilane and wherein the silane-modified polybutadiene has a viscosity of from 8.2 to 27.8 Pa*sec at 20° C.

8. The rubber mixture according to claim 7 , wherein said mixture comprise 0.5 to 20 parts by wt of organosilane based on 100 parts by wt of rubber.

9. The rubber mixture according to claim 7 , wherein said mixture comprise natural rubber or mixtures of natural rubber and diene rubber, 10 to 150 parts by wt of precipitated silica, 0 to 100 parts by wt of carbon black, 0.5 to 20 parts by wt of organosilane and 0.5 to 25 parts by wt of the silane-modified polybutadiene, in each case based on 100 parts by weight of rubber.

10. A product comprising the rubber mixture according to claim 4 wherein the product is selected from the group consisting of tires, profiles, cable sheaths, hoses, drive belts, conveyor belts, tire treads, shoe soles, sealing rings and damping elements.

11. A process of making a silane-modified polybutadiene, the process comprising the steps of
a) providing a polybutadiene produced by free-radical polymerization and having hydroxyl groups, and
b) reacting the polybutadiene having hydroxyl groups from step a) with an organosilane compound, wherein the polybutadiene comprises the 1,3-butadiene-derived monomer units

 and wherein the proportion of A in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 10 to 60 mol %, and wherein the sum of the proportions of B and C in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 40 to 90 mol % wherein the silane-modified polybutadienes are obtainable by reacting hydroxyl-terminated polybutadienes produced by free-radical polymerization with one or more organosilane compounds, wherein the silane-modified polybutadiene has an average functionality of from 0.1 to 4.

12. The process of claim 11 wherein the silane-modified polybutadienes are obtainable by reacting hydroxyl-terminated polybutadienes produced by free-radical polymerization with one or more organosilane compounds and wherein the silane-modified polybutadiene has a viscosity of from 8.2 to 27.8 Pa*sec at 20° C.

13. The process of claim 11 wherein the proportion of A) in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 15 to 30 mol %, the proportion of B) in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 50 to 70 mol % and the proportion of C) in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 15 to 30 mol %.

14. The process of claim 11 wherein the organosilane compound is selected from the group comprising compounds of formula I
OCN—R—Si(OR 1 ) x (R 2 ) 3-x   I

where R represents linear or branched alkylene chains having 1-4 carbon atoms and R 1 and R 2 simultaneously or independently of one another represent linear or branched alkyl chains having from 1 to 5 carbon atoms x=1, 2 or 3.

15. The rubber according to claim 3 , wherein the proportion of A) in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 15 to 30 mol %, the proportion of B) in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 50 to 70 mol % and the proportion of C) in the entirety of the 1,3-butadiene-derived monomer units present in the polybutadiene is from 15 to 30 mol %.

16. The rubber according to claim 2 , wherein the organosilane compound is selected from the group comprising compounds of formula I
OCN—R—Si(OR 1 ) x (R 2 ) 3-x   I

where R represents linear or branched alkylene chains having 1-4 carbon atoms and R 1 and R 2 simultaneously or independently of one another represent linear or branched alkyl chains having from 1 to 5 carbon atoms x=1, 2 or 3.

17. The rubber mixture according to claim 5 , wherein said mixtures comprise an organosilane and wherein the silane-modified polybutadiene has a viscosity of from 8.2 to 27.8 Pa*sec at 20° C.

18. The rubber mixture accordin

Assignees

• Evonik Degussa Gmbh

Inventors

• Haberkorn Niko
• Röben Caren
• Krannig Kai-Steffen
• Wehmeier André
• Berlineanu Andreas
• Beierlein Christine
• Glöckner Patrick
• Maschke Dominik
• Moser Ralph

Classifications

• C08L15/00

  Compositions of rubber derivatives (C08L11/00, C08L13/00 take precedence) · CPC title

• C08L9/00 Primary

  Compositions of homopolymers or copolymers of conjugated diene hydrocarbons · CPC title

• C08L7/00

  Compositions of natural rubber · CPC title

• C08K3/34

  Silicon-containing compounds · CPC title

• C08C19/44

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