Adducts of pyrrole derivatives to carbon allotropes

Patent metadata

Field	Value
Publication number	US-11098012-B2
Application number	US-201716347069-A
Country	US
Kind code	B2
Filing date	Nov 9, 2017
Priority date	Nov 9, 2016
Publication date	Aug 24, 2021
Grant date	Aug 24, 2021

Abstract

Adducts are described formed between pyrrole derivatives of formula (I) an carbon allotropes in which the carbon is sp2 hybridized, such as for example carbon nanotubes, graphene or nanographites, carbon black. The pyrrole derivatives bear substituents on the nitrogen atom suitable for improving the physicochemical characteristics of said allotropes. A process for preparing said adducts is also described. The adducts are formed with a pyrrole of formula (I) wherein X is selected from the group consisting of: The other substituents are as defined in the claims.

First claim

The invention claimed is:

1. An adduct of a compound of formula (I)

wherein R 1 , R 2 , R 3 , R 4 are independently chosen from: hydrogen, C 1 -C 3 alkyl, C 2 -C 18 linear or branched alkenyl, C 2 -C 18 linear or branched alkynyl, aryl, C 1 -C 18 linear or branched alkyl-aryl, C 2 -C 18 linear or branched alkenyl-aryl, C 2 -C 18 linear or branched alkynyl-aryl, and heteroaryl; and X is chosen from:

wherein R 5 and R 6 are independently chosen from: hydrogen, C 1 -C 18 alkyl, C 2 -C 18 linear or branched alkenyl, C 2 -C 18 linear or branched alkynyl, aryl, C 1 -C 22 linear or branched alkyl-aryl, C 2 -C 22 linear or branched alkenyl-aryl, C 2 -C 22 linear or branched alkynyl-aryl, and heteroaryl; or
R 5 or R 6 are each or both

wherein m is 0, 1, or 2 and n is an integer from 1 to 30, wherein if only one of R 5 or R 6 is

wherein m is 0, 1, or 2 and n is an integer from 1 to 30, then the other is chosen from: hydrogen, C 1 -C 18 alkyl, C 2 -C 18 linear or branched alkenyl, and C 2 -C 18 linear or branched alkynyl; or
R 5 and/or R 6 are:

wherein n is 0, 1, 2, or 3 and R 7 , R 7 ′, R 7 ″ are independently chosen from: C 1 -C 4 alkyl, and oxygen-alkyl C 1 -C 4 ; or
R 5 and/or R 6 are:

wherein n is 0, 1, 2, or 3 and R 8 is C 1 -C 4 alkyl; or
R 5 and/or R 6 are:

wherein n is an integer from 1 to 10;
R 9 is chosen from: hydrogen, alkyl, aryl, benzyl, amine, alkylamine, arylamine, benzylamine, and aminoaryl;
R 10 , R 11 , R 12 , R 13 , and R 14 are independently chosen from: hydrogen, C 1 -C 18 alkyl, C 2 -C 18 linear or branched alkenyl, C 2 -C 18 linear or branched alkynyl, and 1-(4-aminocyclohexyl)methylene;
and a carbon allotrope containing carbon atoms hybridized sp 2 or a derivative thereof, and
wherein the carbon allotrope derivative comprises functional groups chosen from:
oxygenated functional groups;
functional groups containing carbonyls;
functional groups containing nitrogen atoms; and
functional groups containing sulfur atoms.

2. The adduct according to claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are independently chosen from: H, CH3, CH2CH3, and phenyl.

3. The adduct according to claim 1 , wherein the carbon allotrope or the derivative thereof is chosen from: carbon black, fullerene, single-wall or multiwall carbon nanotubes, graphene, and graphite with a number of graphene layers ranging from 2 to 10000.

4. The adduct according to claim 1 , wherein the carbon allotrope derivative is graphite oxide.

5. The adduct according to claim 1 , wherein the carbon allotrope derivative is graphene oxide.

6. A process for preparing an adduct of a compound of formula (I) according to claim 1 , the process comprising:
i. providing a solution of the compound of formula (I) in a protic or aprotic polar solvent;
ii. providing a suspension of the carbon allotrope in the protic or aprotic polar solvent used for the preparation of the solution referred to in step i.;
iii. mixing the solution and the suspension to form a mixture;
iv. removing the solvent from the mixture; and
v. providing energy in a form chosen from thermal, mechanical, photon irradiation, and combinations thereof, to the mixture.

7. The process according to claim 6 , wherein the energy is thermal and is provided at a temperature ranging from 50 to 180° C. and for a time ranging from 15 to 360 minutes.

8. The process according to claim 6 , wherein the energy is mechanical and is provided for a time ranging from 15 to 360 minutes.

9. The process according to claim 6 , wherein the energy is photon irradiation and is provided at a wavelength ranging from 200 to 380 nm and for a time ranging from 30 to 180 minutes.

Assignees

• Pirelli
• Milano Politecnico

Inventors

• Galimberti Maurizio Stefano
• Barbera Vincenzina

Classifications

• C01B32/198

  Graphene oxide · CPC title

• C07D403/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• B82Y30/00

  Nanotechnology for materials or surface science, e.g. nanocomposites · CPC title

• C07D207/325

  with substituted hydrocarbon radicals directly attached to the ring nitrogen atom · CPC title

• B82Y40/00

  Manufacture or treatment of nanostructures · CPC title