Silane functionalized poly (farnesene) and rubber compound comprising the same

• US 10,457,752 B2
• Filed: 06/07/2017
• Issued: 10/29/2019
• Est. Priority Date: 06/07/2017
• Status: Active Grant

• Current Assignee: Fina Technology, Inc. (Totalenergies Se)
• Original Assignee: Fina Technology, Inc. (Totalenergies Se)
• Inventors: Henning, Steven K., Monsallier, Jean-Marc, Tian, Nan
• Primary Examiner(s): Scott, Angela C
• Application Number:
  US15/616,169
• Publication Number:
  US 20180355073A1
• Time in Patent Office: 874 Days
• Field of Search: 524492
• CPC Class Codes: C08C 19/25 Incorporating silicon atoms into the molecule
• CPC Class Codes: C08C 19/28 Reaction with compounds containing carbon-to-carbon unsaturated bonds graft polymers C08F279/00
• CPC Class Codes: C08C 19/44 of polymers containing metal atoms exclusively at one or both ends of the skeleton
• CPC Class Codes: C08F 236/10 with vinyl-aromatic monomers
• CPC Class Codes: C08K 3/36 Silica
• CPC Class Codes: C08K 5/548 containing sulfur C08K5/5477 takes precedence
• CPC Class Codes: C08K 9/06 with silicon-containing compounds
• CPC Class Codes: C08L 47/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers C08L45/00 takes precedence; of conjugated diene rubbers C08L9/00 - C08L21/00
• CPC Class Codes: C08L 9/00 Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
• CPC Class Codes: C08L 9/06 Copolymers with styrene
• CPC Class Codes: Y02T 10/86 Optimisation of rolling resistance, e.g. weight reduction

Abstract

According to an aspect of the invention, a curable rubber composition is provided which includes a high molecular weight diene elastomer; optionally, a carbon black composition; a silica composition; and a farnesene polymer comprising farnesene monomers. The farnesene polymer is modified with at least one silane group, has a number average molecular weight of 1,000 g/mol to 100,000 g/mol, and has a glass transition temperature of equal to or less than −50° C. According to another aspect of the invention, a method for producing a rubber composition for use in a tire is provided. The method includes forming a composition by mixing a farnesene polymer modified with at least one silane group, a silica composition, a high molecular weight diene elastomer, and optionally a carbon black composition, the farnesene polymer comprising farnesene monomers; and curing the composition.

Claims

1. A curable rubber composition comprising:

a high molecular weight diene elastomer having a number average molecular weight M_n above 80,000 Da;

a silica;

a carbon black; and

a farnesene polymer produced via living anionic polymerization of at least one farnesene monomer, the farnesene polymer having at least one terminal end modified with at least one silane group, wherein the farnesene polymer has a number average molecular weight of 1,000 g/mol to 100,000 g/mol, a silane functionality of two or less and a glass transition temperature of equal to or less than −

40°

C., wherein the farnesene polymer is produced by process i) or process ii);

i) a process comprising polymerizing farnesene monomers to obtain a living farnesene polymer having one or more living ends and capping the living ends of the living farnesene polymer with a silane ester;

ii) a process comprising polymerizing farnesene monomers to obtain a living farnesene polymer, modifying at least one terminal end of the living farnesene polymer by reacting the living farnesene polymer with an alkylene oxide followed by a proton source to produce a hydroxyl-terminated farnesene polymer having at least one terminal hydroxyl group, and modifying at least one terminal hydroxyl group of the hydroxyl-terminated farnesene polymer by converting the at least one terminal hydroxyl group to a silane group.

2. The curable rubber composition of claim 1, wherein the farnesene polymer is produced via living anionic polymerization of at least one farnesene monomer and at least one of a vinyl aromatic monomer or a diene monomer.

3. The curable rubber composition of claim 1, wherein the number average molecular weight of the farnesene polymer is 2,000 g/mol to 50,000 g/mol.

4. The curable rubber composition of claim 3, wherein the number average molecular weight of the farnesene polymer is 2,500 g/mol to 10,000 g/mol.

5. The curable rubber composition of claim 1, wherein the silica is obtained from precipitation of soluble silicate.

6. The curable rubber composition of claim 1, further comprising at least one silane coupling agent.

7. The curable rubber composition of claim 1, wherein the silane group is represented by the following formula:

—

Si(OR)₃, where each R is independently a C1-C6 alkyl group or an aryl group.

8. The curable rubber composition of claim 1, wherein the farnesene polymer is produced by process ii) and converting the at least one terminal hydroxyl group to a silane group comprises either i) reacting the at least one terminal hydroxyl group with an isocyanatosilane or ii) reacting the at least one terminal hydroxyl group with a diisocyanate and then an aminosilane.

9. A tire comprising a rubber composition obtained by curing the curable rubber composition of claim 1.

10. The tire of claim 9, wherein the farnesene polymer is produced via living anionic polymerization of at least one farnesene Monomer and at least one of a diene monomer and a vinyl aromatic monomer.

11. The tire of claim 9, wherein the number average molecular weight of the farnesene polymer is 2,000 g/mol to 50,000 g/mol.

12. The tire of claim 11, wherein the number average molecular weight of the farnesene polymer is 2,500 g/mol to 10,000 g/mol.

13. The tire of claim 9, wherein the curable rubber composition further comprises at least one silane coupling agent.

14. The tire of claim 9, wherein the silica is obtained from precipitation of soluble silicate.

15. The tire of claim 9, wherein the curable rubber composition has been cured using at least one sulfur vulcanizing agent.

16. A method for producing a rubber composition adapted for use in a tire, the method comprising:

forming the curable rubber composition of claim 1 by mixing the farnesene polymer, the silica, the high molecular weight diene elastomer having a number average molecular weight M_n above 80,000 Da, and the carbon black; and

curing the curable rubber composition.

17. The method of claim 16, wherein the farnesene polymer has been prepared by process ii).

18. A curable rubber composition comprising:

a high molecular weight diene elastomer having a number average molecular weight M_n above 80,000 Da;

a silica;

a carbon black; and

a farnesene polymer produced via living anionic polymerization of at least one farnesene monomer, wherein the farnesene polymer consists of farnesene monomers and has at least one terminal end modified with at least one silane group, a number average molecular weight of 1,000 g/mol to 100,000 g/mol, a silane functionality of two or less and a glass transition temperature of equal to or less than −

40°

C.