US 12,320,059 B2
Adducts between carbon allotropes and pyrrole derivatives, elastomer mixtures comprising them and tyres comprising such mixtures
Maurizio Stefano Galimberti, Milan (IT); Vincenzina Barbera, Milan (IT); Gea Prioglio, Milan (IT); and Luca Giannini, Milan (IT)
Assigned to PIRELLI TYRE S.p.A., Milan (IT)
Appl. No. 17/594,787
Filed by PIRELLI TYRE S.p.A., Milan (IT)
PCT Filed Nov. 5, 2019, PCT No. PCT/IB2019/059473
§ 371(c)(1), (2) Date Oct. 29, 2021,
PCT Pub. No. WO2020/225595, PCT Pub. Date Nov. 12, 2020.
Prior Publication US 2022/0213035 A1, Jul. 7, 2022
Int. Cl. C09C 1/44 (2006.01); C01B 32/15 (2017.01); C01B 32/20 (2017.01); C07D 207/325 (2006.01); C07D 513/02 (2006.01); C07D 513/12 (2006.01); C08J 5/24 (2006.01); C08K 5/3415 (2006.01); C08K 5/378 (2006.01); C08K 5/46 (2006.01); C08K 9/04 (2006.01); C09C 1/48 (2006.01); D06M 11/74 (2006.01); D06M 13/352 (2006.01); B82Y 30/00 (2011.01); B82Y 40/00 (2011.01); D06M 101/00 (2006.01)
CPC D06M 13/352 (2013.01) [C01B 32/15 (2017.08); C01B 32/20 (2017.08); C07D 207/325 (2013.01); C07D 513/02 (2013.01); C07D 513/12 (2013.01); C08J 5/244 (2021.05); C08J 5/248 (2021.05); C08K 5/3415 (2013.01); C08K 5/378 (2013.01); C08K 5/46 (2013.01); C09C 1/48 (2013.01); D06M 11/74 (2013.01); B82Y 30/00 (2013.01); B82Y 40/00 (2013.01); D06M 2101/005 (2013.01)] 15 Claims
 
1. An adduct between an sp2 hybridized carbon allotrope and a pyrrole derivative, wherein the pyrrole derivative is represented by formula (1)

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wherein
R1, R2, R3, and R4 are independently chosen from: hydrogen, linear or branched C1-C22 alkyl, linear or branched C2-C22 alkenyl or alkynyl, aryl, linear or branched C1-C22 alkyl-aryl, linear or branched C2-C22 alkenyl-aryl, linear or branched C2-C22 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 C1-C18 alkyl, linear or branched C2-C18 alkenyl or alkynyl, and formulae (II)-(V) depicted below

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wherein R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, and R21 are independently chosen from: hydrogen, linear or branched C1-C18 alkyl, linear or branched C2-C18 alkenyl or alkynyl, aryl, linear or branched C1-C22 alkyl-aryl, linear or branched C2-C22 alkenyl-aryl, linear or branched C2-C22 alkynyl-aryl, heteroaryl, carboxyl, acyl-alkyl with linear or branched C1-C18 alkyl, acyl-alkenyl or acyl-alkynyl with linear or branched C2-C18 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 C1-C3 alkyl, carboxyl, and acyl-alkyl with C1-C3 alkyl;
or R12 and R13 together form a pyrrole ring optionally substituted by one or more C1-C3 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 R1-R4 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:

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or
when only the dashed line (b′) represents a double bond, then Y is hydrogen, W is a —CH2—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 R1-R4 and Z have the meanings stated above:

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or
when both the dashed lines represent a single bond, then Y and W are both a —CH2—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 R1-R4 and Z have the meanings stated above:

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