Adducts between carbon allotropes and pyrrole derivatives, elastomer mixtures comprising them and tyres comprising such mixtures

Patent metadata

Field	Value
Publication number	US-12320059-B2
Application number	US-201917594787-A
Country	US
Kind code	B2
Filing date	Nov 5, 2019
Priority date	May 8, 2018
Publication date	Jun 3, 2025
Grant date	Jun 3, 2025

Abstract

The present invention relates to adducts between sp 2 hybridized carbon allotropes and pyrrole derivatives comprising at least one sulphur atom, and crosslinkable elastomer compositions comprising such adducts. The present invention further relates to tyres for vehicle wheels comprising at least one structural element comprising a crosslinked elastomer material obtained by crosslinking of such crosslinkable elastomer compositions.

First claim

The invention claimed is:

1. An adduct between an sp 2 hybridized carbon allotrope and a pyrrole derivative, wherein the pyrrole derivative is represented by formula (1)

wherein
R 1 , R 2 , R 3 , and R 4 are independently chosen from: hydrogen, linear or branched C 1 -C 22 alkyl, linear or branched C 2 -C 22 alkenyl or alkynyl, aryl, linear or branched C 1 -C 22 alkyl-aryl, linear or branched C 2 -C 22 alkenyl-aryl, linear or branched C 2 -C 22 alkynyl-aryl, and heteroaryl;
the dashed lines (a′) and (b′) independently represent a double bond or a single bond; and
W, Y and Z are independently chosen from: hydrogen, linear or branched C 1 -C 18 alkyl, linear or branched C 2 -C 18 alkenyl or alkynyl, and formulae (II)-(V) depicted below

wherein R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , and R 21 are independently chosen from: hydrogen, linear or branched C 1 -C 18 alkyl, linear or branched C 2 -C 18 alkenyl or alkynyl, aryl, linear or branched C 1 -C 22 alkyl-aryl, linear or branched C 2 -C 22 alkenyl-aryl, linear or branched C 2 -C 22 alkynyl-aryl, heteroaryl, carboxyl, acyl-alkyl with linear or branched C 1 -C 18 alkyl, acyl-alkenyl or acyl-alkynyl with linear or branched C 2 -C 18 alkenyl and alkynyl, acyl-aryl, acyl-heteroaryl, and acyl-amine, wherein the aryl and heteroaryl groups are optionally substituted by one or more groups chosen from C 1 -C 3 alkyl, carboxyl, and acyl-alkyl with C 1 -C 3 alkyl;
or R 12 and R 13 together form a pyrrole ring optionally substituted by one or more C 1 -C 3 alkyl groups;
and wherein m is an integer ranging from 1 to 4, and n, o, p, q, r, and s are, independently of one another, an integer ranging from 1 to 12;
and wherein
when both the dashed lines (a′) and (b′) represent a double bond, then formula (1) is represented by formula (1a) wherein R 1 -R 4 and W, Y, and Z have the meanings stated above, and wherein at least one among W, Y, and Z is represented by one of formulae (II)-(III) above:

or
when only the dashed line (b′) represents a double bond, then Y is hydrogen, W is a —CH 2 —S— group which together with the carbon in position “a” forms a 5-membered ring, and formula (1) is represented by formula (1b) below wherein R 1 -R 4 and Z have the meanings stated above:

or
when both the dashed lines represent a single bond, then Y and W are both a —CH 2 —S — group, and each of together with the carbons in position “a” and “b” forms a 5-membered ring, and formula (1) is represented by formula (1c) wherein R 1 -R 4 and Z have the meanings stated above:

2. The adduct according to claim 1 , wherein the sp 2 hybridized carbon allotrope is chosen from: carbon black, graphene, 2 layer graphene, from 3 to 10 layer graphene, graphite, high surface area graphite, single wall or multiwall carbon nanotubes, carbon nanotubes of longitudinal or helicoid extension, nanocones, nanohorns, nanotoroids, fullerene, and mixtures thereof.

3. The adduct according to claim 2 , wherein the sp 2 hybridized carbon allotrope is chosen from carbon black, graphene, graphite, high surface area graphite, single wall or multiwall carbon nanotubes, and mixtures thereof.

4. The adduct according to claim 2 , wherein the sp 2 hybridized carbon allotrope is carbon black, high surface area graphite, or mixtures thereof.

5. The adduct according to claim 1 , wherein the pyrrole derivative is represented by formula (1a)

wherein
R 1 , R 2 , R 3 , and R 4 are independently chosen from: hydrogen, linear or branched C 2 -C 22 alkyl, linear or branched C 2 -C 22 alkenyl or alkynyl, aryl, linear or branched C 1 -C 22 alkyl-aryl, linear or branched C 2 -C 22 alkenyl-aryl, linear or branched C 2 -C 22 alkynyl-aryl, and heteroaryl;
W, Y and Z are independently chosen from: hydrogen, linear or branched C 1 -C 18 alkyl and linear or branched C 2 -C 18 alkenyl or alkynyl, and formulae (II)-(V) depicted below:

wherein R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , and R 21 are independently chosen from: hydrogen, linear or branched C 1 -C 18 alkyl, linear or branched C 2 -C 18 alkenyl or alkynyl, aryl, linear or branched C 1 -C 22 alkyl-aryl, linear or branched C 2 -C 22 alkenyl-aryl, linear or branched C 1 -C 22 alkynyl-aryl, heteroaryl, carboxyl, acyl-alkyl with linear or branched C 1 -C 18 alkyl, acyl-alkenyl or acyl-alkynyl with linear or branched C 1 -C 18 alkenyl and alkynyl, acyl-aryl, acyl-heteroaryl, and acyl-amine, wherein the aryl and heteroaryl groups are optionally substituted by one or more groups chosen from C 1 -C 3 alkyl, carboxyl, and acyl-alkyl with C 1 -C 3 alkyl;
or R 12 and R 13 together form a pyrrole ring optionally substituted by one or more C 1 -C 3 alkyl groups;
and wherein m is an integer ranging from 1 to 4, and n, o, p, q, and r, and s are, independently of one another, an integer ranging from 1 to 12;
and wherein at least one among W, Y, and Z is represented by one of formulae (II)-(III) above.

6. The adduct according to claim 5 , wherein the pyrrole derivative is represented by formula (1a)

wherein
R 1 , R 2 , R 3 , and R 4 are independently chosen from: hydrogen, linear or branched C 1 -C 22 alkyl, linear or branched C 2 -C 22 alkenyl or alkynyl, aryl, linear or branched C 1 -C 22 alkyl-aryl, linear or branched C 2 -C 22 alkenyl-aryl, linear or branched C 2 -C 22 alkynyl-aryl, and heteroaryl;
W and Y are independently chosen from: hydrogen, linear or branched C 1 -C 18 alkyl, linear or branched C 2 -C 18 alkenyl or alkynyl; and
Z is represented by one of formulae (II)-(III) stated below:

wherein R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 are independently chosen from:
hydrogen, linear or branched C 1 -C 18 alkyl, linear or branched C 2 -C 18 alkenyl or alkynyl, aryl, linear or branched C 1 -C 22 alkyl-aryl, linear or branched C 2 -C 22 alkenyl-aryl, linear or branched C 2 -C 22 alkynyl-aryl, heteroaryl, carboxyl, acyl-alkyl with linear or branched C 1 -C 18 alkyl, acyl-alkenyl or acyl-alkynyl with linear or branched C 2 -C 18 alkenyl and alkynyl, acyl-aryl, acyl-heteroaryl, and acyl-amine, wherein the aryl and heteroaryl groups are optionally substituted by one or more groups chosen from C 1 -C 3 alkyl, carboxyl, and acyl-alkyl with C 1 -C 3 alkyl;
or R 12 and R 13 together form a pyrrole ring optionally substituted by one or more C 1 -C 3 alkyl groups;
and wherein m is an integer ranging from 1 to 4, and n, o, and p are, independently of one another, an integer ranging from 1 to 12.

7. The adduct a

Assignees

• Pirelli

Inventors

• Galimberti Maurizio Stefano
• Barbera Vincenzina
• Prioglio Gea
• Giannini Luca

Classifications

• C07D513/02

  in which the condensed system contains two hetero rings · CPC title

• C07D513/12

  in which the condensed system contains three hetero rings · CPC title

• C09C1/48

  Carbon black · CPC title

• C08K5/3415

  Five-membered rings · CPC title

• C08K5/378

  containing heterocyclic rings · CPC title