Adducts between carbon allotropes and serinol derivatives

Patent metadata

Field	Value
Publication number	US-10160652-B2
Application number	US-201515514350-A
Country	US
Kind code	B2
Filing date	Sep 30, 2015
Priority date	Oct 1, 2014
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

An adduct consists of derivatives of serinol pyrrole and of carbon allotropes in which the carbon is sp 2 hybridized, such as carbon nanotubes, graphene or nano-graphites or carbon black, in order to improve the chemical-physical properties of the allotropes increasing above all their dispersibility and stability in liquid media and in polymer matrices, and a process for preparation of the adduct.

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 selected from the group consisting of: hydrogen, C 1 -C 3 alkyl, C 2 -C 22 linear or branched alkenyl or alkynyl, aryl, C 1 -C 22 linear or branched alkyl-aryl, C 2 -C 22 linear or branched alkenyl-aryl, and C 2 -C 22 linear or branched alkynyl-aryl, heteroaryl; and
a carbon allotrope or a carbon allotrope derivative, wherein the carbon is sp 2 hybridized and wherein said carbon allotrope derivative is an sp 2 hybridized carbon allotrope with at least one functional group selected from the group consisting of: oxygenated functional groups, functional groups containing carbonyls, functional groups containing nitrogen atoms, and functional groups containing sulfur atoms,
wherein the oxygenated functional groups are hydroxyls or epoxies; wherein the functional groups containing carbonyls are aldehydes, ketones or carboxylic acids; wherein the functional groups containing nitrogen atoms are amines, amides, nitriles, diazonium salts, or imines; and wherein the functional groups containing sulfur atoms are sulfides, disulfides, mercaptans, sulfones, or sulfonic groups.

2. The adduct according to claim 1 , wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of: H, CH 3 , CH 2 CH 3 , and phenyl.

3. The adduct according to claim 1 , wherein said carbon allotrope or it's derivative are selected from the group consisting of: carbon black, fullerene, single-wall or multiwall carbon nanotubes, graphene, and graphite with a number of graphene layers from 2 to 10000.

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

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

6. A process for the preparation of an adduct comprising a compound of formula (I)

wherein R 1 , R 2 , R 3 , R 4 are independently selected from the group consisting of: hydrogen, C 1 -C 3 alkyl, C 2 -C 22 linear or branched alkenyl or alkynyl, aryl, C 1 -C 22 linear or branched alkyl-aryl, C 2 -C 22 linear or branched alkenyl-aryl, and C 2 -C 22 linear or branched alkynyl-aryl, heteroaryl; and
a carbon allotrope or a carbon allotrope derivative, wherein the carbon is sp 2 hybridized and wherein said carbon allotrope derivative is an sp 2 hybridized carbon allotrope with at least one functional group selected from the group consisting of: oxygenated functional groups, functional groups containing carbonyls, functional groups containing nitrogen atoms, and functional groups containing sulfur atoms;
wherein the oxygenated functional groups are hydroxyls or epoxies;
wherein the functional groups containing carbonyls are aldehydes, ketones or carboxylic acids; wherein the functional groups containing nitrogen atoms are amines, amides, nitriles, diazonium salts, or imines; and wherein the functional groups containing sulfur atoms are sulfides, disulfides, mercaptans, sulfones, or sulfonic groups; and

wherein the process comprises:
i. providing a solution of a 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 in i.;
iii. mixing said solution and said suspension;
iv. removing said solvent from said mixture obtained in iii.; and
v. providing thermal and/or mechanical energy and/or photon irradiation energy to the mixture obtained in iv.

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

8. The process according to claim 6 , wherein said mechanical energy is provided from 15 to 360 minutes.

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

Assignees

• Milano Politecnico
• Pirelli

Inventors

• Galimberti Maurizio Stefano
• Barbera Vincenzina
• Sebastiano Roberto
• Valerio Antonio Marco
• Leonardi Gabriella
• Citterio Attilio

Classifications

• C01B32/174 Primary

  Derivatisation; Solubilisation; Dispersion in solvents · CPC title

• C01B32/21

  After-treatment · CPC title

• C09C1/56

  Treatment of carbon black {; Purification} · CPC title

• C01P2002/82

  by IR- or Raman-data · CPC title

• B82Y30/00

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