Method for grafting polyphenols

Patent metadata

Field	Value
Publication number	US-2020032002-A1
Application number	US-201816603381-A
Country	US
Kind code	A1
Filing date	Apr 13, 2018
Priority date	Apr 13, 2017
Publication date	Jan 30, 2020
Grant date	—

Abstract

The invention relates to a process for producing at least one grafted polyphenol, comprising at least the step of reacting, in the presence of at least one catalyst, at least one polyphenol with at least one compound of formula (I) below:

wherein:
R 1 is a linear or branched, saturated or unsaturated, C 3 -C 30 , preferably C 3 -C 20 , more preferentially C 8 -C 20 , even more preferentially C 8 -C 18 , hydrocarbon-based chain, optionally comprising one or more saturated or unsaturated rings, said chain being optionally interrupted by one or more heteroatoms chosen from O, S and N, preferably chosen from O and S, more preferably O; R 2 is chosen from a hydrogen atom and a linear or branched, saturated or unsaturated, C 1 -C 60 hydrocarbon-based chain, optionally comprising one or more saturated or unsaturated rings, said chain being optionally interrupted by one or more heteroatoms chosen from O, S and N, preferably chosen from O and S, more preferably O, the number of moles of said compound of formula (I) being greater than or equal to the number of —OH functions present per mole of said polyphenol.

First claim

1 . A process for producing at least one grafted polyphenol, comprising at least the following step:
(a) reacting, in the presence of at least one catalyst, at least one polyphenol with at least one compound of formula (I) below:

wherein:
R 1 is a linear or branched, saturated or unsaturated, C 3 -C 30 hydrocarbon-based chain, optionally comprising one or more saturated or unsaturated rings, said chain being optionally interrupted by one or more heteroatoms chosen from the oxygen atom (O), the sulfur atom (S) and the nitrogen atom (N);
R 2 is chosen from a hydrogen atom and a linear or branched, saturated or unsaturated, C 1 -C 60 hydrocarbon-based chain, optionally comprising one or more saturated or unsaturated rings, said chain being optionally interrupted by one or more heteroatoms chosen from the oxygen atom (O), the sulfur atom (S) and the nitrogen atom (N),
the number of moles of said compound of formula (I) being greater than or equal to the number of —OH functions present per mole of said polyphenol.

2 . The process as claimed in claim 1 , wherein said polyphenol is chosen from tannins, lignins and natural polyphenols other than tannins and lignins.

3 . The process as claimed in claim 2 , wherein said polyphenol is a lignin.

4 . The process as claimed in claim 1 , wherein the catalyst is chosen from alkali metal hydroxides, sodium or potassium alkoxides, and tertiary amines chosen from trialkylamines and tetramethylguanidine.

5 . The process as claimed in claim 1 , wherein R 1 is chosen from:
a group of formula (II) below: —(CH 2 ) n —CH 3 (II), wherein n is an integer ranging from 2 to 29; a group of formula (III) below:

wherein:
R 3 is chosen from a hydrogen atom, a C 1 -C 3 alkyl radical and a phenyl group;
m is an integer ranging from 1 to 15; and
R 4 denotes a hydrogen atom or a C 1 -C 20 hydrocarbon-based chain;
a group of formula (IV) below:

wherein R 5 denotes a linear or branched, saturated or unsaturated, C 5 -C 20 hydrocarbon-based radical.

6 . The process as claimed in claim 1 , wherein R 2 is chosen from a hydrogen atom and a linear or branched, saturated or unsaturated, C 1 -C 40 hydrocarbon-based chain.

7 . The process as claimed in claim 1 , wherein the number of moles of said compound of formula (I) is at least 1.1 times greater than or equal to the number of —OH functions present per mole of said polyphenol.

8 . A process for producing at least one alkoxylated polyphenol comprising step (a), as defined in claim 1 , followed by the following step:
(b) reacting the grafted polyphenol obtained at the end of step (a) with at least one alkoxylating agent of formula (V) below:

wherein R 6 denotes a hydrogen atom or a C 1 -C 2 alkyl radical.

9 . The process as claimed in claim 8 , wherein step (b) is carried out in the presence of a catalyst which is identical to or different than the catalyst as defined in claim 1 .

10 . The process as claimed in claim 8 , wherein the grafted polyphenol/alkoxylating agent weight ratio ranges from 0.05 to 2.

11 . A grafted polyphenol that can be obtained by the process as defined in claim 1 .

12 . An alkoxylated polyphenol that can be obtained by the process as defined in claim 8 .

13 . The use of the grafted polyphenol as defined in claim 11 , as a reagent in alkoxylation processes.

14 . The use of the grafted polyphenol as defined in claim 11 , as a solvent for polyphenols.

15 . The use of the grafted polyphenol as defined in claim 11 , as a solvent in polyphenol alkoxylation processes.

16 . The use of the grafted polyphenol as defined in claim 11 , for producing polyurethanes, polyesters, nonionic or cationic surfactants, biobased precursors of carbon fiber.

Assignees

• Arkema France

Inventors

• Gillet Jean-Philippe
• Allard-Breton Béatrice
• Teissier Rémy
• Blanc Jérôme

Classifications

• C08G18/6492

  Lignin containing materials; Wood resins; Wood tars; Derivatives thereof · CPC title

• C08G18/4879

  containing aromatic groups · CPC title

• C08H6/00 Primary

  Macromolecular compounds derived from lignin, e.g. tannins, humic acids · CPC title

• C08L97/005

  Lignin · CPC title