IP Library Granted Patent US 11,945,952
Granted Patent B2
US 11,945,952 · App. 17/414,120 · Granted Apr 2, 2024

Rubber composition comprising esters from renewable sources as plasticizers

Inventors: Franco Cataldo (Rome, IT); Louis Plancq (Levallois-Perret, FR); Francine Genin (Houilles, FR); Zubin Arora (Paris, FR)
Assignee: TOTAL MARKETING SERVICES
C08L9/06B60C1/0016C08F136/08C08K3/04C08K3/36C08K5/05C08K5/092C08K5/11C08K5/12C08L7/00C08L2205/025
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Quick Facts
Patent No.
US 11,945,952
App. No.
17/414,120
Granted
Apr 2, 2024
Kind
B2
Abstract

The present invention relates to a rubber composition for tire applications comprising: rubber polymer(s) comprising at least optionally-functionalized styrene-butadiene rubber (SBR) and at least one rubber selected from polybutadiene rubber (BR), natural rubber (NR), polyisoprene rubber (IR) and mixtures thereof, and at least one ester derived from renewable sources resulting from the esterification of trimer and/or dimer acids having the formula A-(COOH)q, with q being 2 or 3 and A being an acyclic, cyclic or polycyclic, saturated or unsaturated, linear or branched hydrocarbon group having from 3 to 69 carbon atoms, with acyclic or cyclic, saturated or unsaturated, linear or branched alcohols.

Claims (41)

1. Rubber composition for tire applications comprising:

rubber polymers comprising at least optionally functionalized styrene-butadiene rubber (SBR) and at least one rubber selected from polybutadiene rubber (BR), natural rubber (NR), polyisoprene rubber (IR) and mixtures thereof, and

at least one ester derived from renewable sources resulting from the esterification of trimer and/or dimer acids having the formula A-(COOH) q , with q being 2 or 3 and A being identical or different, acyclic, cyclic or polycyclic, saturated or unsaturated, linear or branched hydrocarbon groups having from 3 to 69 carbon atoms, with acyclic or cyclic, saturated or unsaturated, linear or branched alcohols,

said rubber polymers comprising:

from 20 to 90% by weight of styrene-butadiene rubber(s) optionally functionalized and

from 10 to 80% by weight of at least one rubber selected from polybutadiene rubber (BR), natural rubber (NR), polyisoprene rubber (IR) and mixtures thereof,

based on the total weight of the rubber polymers,

wherein the rubber composition comprises from 5 to 80 PHR of the ester derived from renewable sources.

2. Rubber composition according to claim 1 , wherein the at least one ester derived from renewable sources comprise from 50 to 100 wt %, based on the total weight of the at least one ester, of at least one trimer ester resulting from the esterification of trimer acids having the formula A-(COOH) 3 , with A being identical or different, acyclic, cyclic or polycyclic, saturated or unsaturated, linear or branched hydrocarbon group having from 3 to 69 carbon atoms, with acyclic or cyclic, saturated or unsaturated, linear or branched alcohols.

3. Rubber composition according to claim 1 , wherein the at least one ester derived from renewable sources comprises:

at least one trimer ester, said trimer ester(s) resulting from the esterification of trimer acids having the formula A-(COOH) 3 , with A being identical or different, acyclic, cyclic or polycyclic, saturated or unsaturated, linear or branched hydrocarbon group having from 3 to 69 carbon atoms, with acyclic or cyclic, saturated or unsaturated, linear or branched alcohols; and

at least one dimer ester, said dimer ester(s) resulting from the esterification of dimer acid(s) dimer acids having the formula A-(COOH) 2 , with A being identical or different, acyclic, cyclic or polycyclic, saturated or unsaturated, linear or branched hydrocarbon groups having from 3 to 46 carbon atoms, with acyclic or cyclic, saturated or unsaturated, linear or branched alcohols.

4. Rubber composition according to claim 1 , wherein the trimer and/or dimer acids result from one or more addition reactions of unsaturated fatty acids.

5. Rubber composition according to claim 4 , wherein the unsaturated fatty acids have from 4 to 24 carbon atoms (C4 to C24).

6. Rubber composition according to claim 4 , wherein the unsaturated fatty acids have 18 carbon atoms (C18).

7. Rubber composition according to claim 4 , wherein the unsaturated fatty acids are chosen from oleic acid, linoleic acid, linolenic acid, and mixtures thereof.

8. Rubber composition according to claim 4 , wherein the unsaturated fatty acids are obtained from Tall Oil Fatty Acid.

9. Rubber composition according to claim 1 , wherein the acyclic or cyclic, saturated or unsaturated, linear or branched alcohols are chosen from ethanol, 1-nonanol, lauryl alcohol, stearyl alcohol, tetrahydrofurfuryl alcohol, and mixtures thereof.

10. Rubber composition according to claim 1 , further comprising:

from 5 to 50 PHR of carbon black, and

from 10 to 90 PHR of silica.

11. Tire tread comprising the rubber composition according to claim 1 .

12. Tire comprising a tire tread according to claim 11 .

13. Rubber composition according to claim 2 , wherein the at least one ester derived from renewable sources comprise from 60 to 100% wt, based on the total weight of the at least one ester, of at least one trimer ester resulting from the esterification of trimer acids having the formula A-(COOH) 3 , with A being identical or different, acyclic, cyclic or polycyclic, saturated or unsaturated, linear or branched hydrocarbon group having from 3 to 69 carbon atoms, with acyclic or cyclic, saturated or unsaturated, linear or branched alcohols.

14. Rubber composition according to claim 3 wherein:

the at least one trimer ester is present in an amount, based on the total weight of the ester(s) derived from renewable sources, of from 50 to 99% wt; and

the at least one dimer ester is present in an amount, based on the total weight of the ester(s) derived from renewable sources, of from 1 to 50 wt %.

15. Rubber composition according to claim 10 , wherein the carbon black is selected from grade N375, grade N220, grade N234 or grade N134 carbon black or mixtures thereof.

16. Rubber composition for tire applications comprising:

rubber polymers comprising at least optionally functionalized styrene-butadiene rubber (SBR) and at least one rubber selected from polybutadiene rubber (BR), natural rubber (NR), polyisoprene rubber (IR) and mixtures thereof, and

at least one ester derived from renewable sources resulting from the esterification of trimer and/or dimer acids having the formula A-(COOH) q , with q being 2 or 3 and A being identical or different, acyclic, cyclic or polycyclic, saturated or unsaturated, linear or branched hydrocarbon groups having from 3 to 69 carbon atoms, with acyclic or cyclic, saturated or unsaturated, linear or branched alcohols,

said rubber polymers comprising:

from 20 to 90% by weight of styrene-butadiene rubber(s) optionally functionalized and

from 10 to 80% by weight of at least one rubber selected from polybutadiene rubber (BR), natural rubber (NR), polyisoprene rubber (IR) and mixtures thereof,

based on the total weight of the rubber polymers,

wherein the at least one ester derived from renewable sources comprise from 50 to 100 wt %, based on the total weight of the at least one ester, of at least one trimer ester resulting from the esterification of trimer acids having the formula A-(COOH) 3 , with A being identical or different, acyclic, cyclic or polycyclic, saturated or unsaturated, linear or branched hydrocarbon group having from 3 to 69 carbon atoms, with acyclic or cyclic, saturated or unsaturated, linear or branched alcohols.

17. Process to plasticize a rubber composition comprising from 20 to 90% wt of optionally functionalized styrene-butadiene rubber(s) (SBR) and from 10 to 80% of at least one rubber selected from polybutadiene rubber (BR), natural rubber (NR), polyisoprene rubber (IR) and mixtures thereof, based on the total weight of the rubber composition, the process comprising adding into the rubber composition:

an ester derived from renewable sources comprising from 50 to 100 wt % of at least one trimer ester resulting from the esterification of trimer acids having the formula A-(COOH) 3 , with A being an acyclic, cyclic or polycyclic, saturated or unsaturated, linear or branched hydrocarbon group having from 3 to 69 carbon atoms, with acyclic or cyclic, saturated or unsaturated, linear or branched alcohols,

wherein the rubber composition comprises from 5 to 80 PHR of the ester derived from renewable sources.

18. Process according to claim 17 , comprising a step of improving the viscoelastic properties of the rubber composition.

19. Process according to claim 17 , wherein the ester is added into the rubber composition.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE THE NAME OF THE ASSIGNEE PREVIOUSLY RECORDED AT REEL: 67096 FRAME: 320. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 26, 2024
From: TOTALENERGIES MARKETING SERVICES (PREVIOUSLY TOTAL MARKETING SERVICES)
To: TOTALENERGIES ONETECH
Reel/Frame 067845/0906 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 12, 2024
From: TOTALENERGIES MARKETING SERVICES (PREVIOUSLY TOTAL MARKETING SERVICES)
To: TOTALENERGIES ONETECH (PREVIOUSLY TOTALENERGIES ONE TECH)
Reel/Frame 067096/0320 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 15, 2021
From: CATALDO, FRANCO; PLANCQ, LOUIS; GENIN, FRANCINE; ARORA, ZUBIN
To: TOTAL MARKETING SERVICES
Reel/Frame 057487/0843 →
Priority Claims (1)
EP 18306771 · Dec 20, 2018 · regional
Continuity (1)
Related Publication 20220033624A1 · Feb 3, 2022