Method to prepare a precursor for a polymer or to prepare a polymer comprising at least one unit having a tertiary amine and a pendant carboxyl group and a precursor or polymer comprising such unit

Patent metadata

Field	Value
Publication number	US-12466915-B2
Application number	US-202017754653-A
Country	US
Kind code	B2
Filing date	Oct 15, 2020
Priority date	Oct 16, 2019
Publication date	Nov 11, 2025
Grant date	Nov 11, 2025

Abstract

The invention relates to a method to prepare a precursor for a polymer or to prepare a polymer, the polymer comprising at least one unit of formula (I) or at least one unit of formula (II) having a tertiary amine and a pendant carboxyl group

Furthermore the invention relates to a precursor or polymer comprising at least one unit of formula (I) and/or at least one unit of formula (II) and to the use of such precursor or such polymer in extrusion, injection moulding, compression moulding, transfer moulding, foam moulding, thermoforming, rotation moulding or 3D printing.

First claim

The invention claimed is:

1 . A method to prepare a polymer or to prepare a precursor for a polymer, said method comprising the steps of
a) providing at least one compound Y comprising a first functional group and a second functional group,
said first functional group comprising an anhydride group, a pair of carboxyl groups or a pair of derivatives of a carboxyl group, said anhydride group, said pair of carboxyl groups or said pair of derivatives of a carboxylic group of said first functional group comprising a first carbonyl group, a second carbonyl group, a first carbon atom positioned next to said first carbonyl group, a second carbon atom positioned next to said second carbonyl group and optionally a third carbon atom positioned between said first carbon atom and said second carbon atom, said first carbon atom, said second carbon atom and said optional third carbon atom being independently from each other substituted or non-substituted and,
said second functional group comprising a polymerisable group P1, whereby in case an unsaturated bond is present between said first carbon atom and said second carbon atom, said unsaturated bond between said first carbon atom and said second carbon atom is not considered as polymerisable group P1 of said second functional group and whereby in case the bond between said first carbon atom and said second carbon atom is part of a cyclic or aromatic structure comprising an unsaturated bond in said cyclic or aromatic structure, said unsaturated bond present in said cyclic or aromatic structure is not considered as polymerisable group P1 of said second functional group;
b) providing an alcohol Z or a mixture of alcohols comprising alcohol Z or reacted with alcohol Z, said alcohol Z comprising at least one hydroxyl functional group and at least one polymerisable group P2, said alcohol Z further comprising a nitrogen atom, said nitrogen atom having three substituents comprising at least one carbon atom, said alcohol Z comprising a first carbon atom, a second carbon atom and optionally a third carbon atom between said nitrogen and said at least one hydroxyl functional groups of said alcohol Z, said first carbon atom, said second carbon atom and said optional third carbon atom being independently from each other substituted or non-substituted; c) contacting said compound Y provided in step a) and said alcohol Z or said mixture of alcohols provided in step b).

2 . The method according to claim 1 , wherein said polymerisable group P1 of said second functional group of compound Y comprises an unsaturated carbon-carbon, a carboxyl group, an anhydride group, a pair of carboxyl groups or a pair of derivatives of a carboxyl group.

3 . The method according to claim 1 , wherein said compound Y comprises a polyanhydride comprising at least two cyclic anhydride groups.

4 . The method according to claim 1 , wherein said polymerisable group P2 of said alcohol Z comprises an unsaturated carbon-carbon bond, a carboxyl group, a derivative of a carboxyl group or a hydroxyl functional group.

5 . The method according to claim 1 , wherein said compound Z comprises a beta-amino-alcohol having one, two or three hydroxyl functional groups.

6 . The method according to claim 1 , wherein said compound Y and said alcohol Z are contacted in step c) in a molar ratio of alcohol Z to compound Y lower than 2, whereby the molar ratio is defined in terms of the total number of hydroxyl functional groups of alcohol Z or the total number of hydroxyl functional groups of all alcohols of the mixture of alcohols comprising alcohol Z in case mixture of alcohols is used divided by the total number of anhydride functional groups and pairs of carboxyl groups or derivatives of a carboxyl group of compound Y.

7 . The method according to claim 1 , wherein said alcohol Z is provided by contacting an amine V and a compound X, said amine V comprising at least one reactive N—H bond and said compound X comprising at least one epoxide group, in a molar ratio V to X ranging between 0.5 and 1.5, said molar ratio being defined in terms of the number of said reactive N—H bonds and the number of said epoxide functional groups.

Assignees

• Univ Gent

Inventors

• Delahaye Maarten
• Winne Johan
• Du Prez Filip

Classifications

• C08F122/22

  Esters containing nitrogen · CPC title

• C08G63/6854

  derived from polycarboxylic acids and polyhydroxy compounds · CPC title

• C08G63/6858

  Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation · CPC title

• C08G63/6856 Primary

  Dicarboxylic acids and dihydroxy compounds · CPC title