Multi-aziridine compound

Patent metadata

Field	Value
Publication number	US-12378189-B2
Application number	US-202117791860-A
Country	US
Kind code	B2
Filing date	Jan 21, 2021
Priority date	Jan 22, 2020
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

The present invention relates to a multi-aziridine compound having: a) from 2 to 6 of the following structural units (A): whereby R′, R″ are as defined herein m is an integer from 1 to 6; b) one or more linking chains wherein each one of these linking chains links two of the structural units A; and c) a molecular weight in the range from 840 Daltons to 5000 Daltons. The multi-aziridine compound can be used for example for crosslinking of for example carboxylic acid functional polymers dissolved and/or dispersed in an aqueous medium.

First claim

The invention claimed is:

1. A multi-aziridine compound having:
a) from 2 to 6 of the following structural units (A):

whereby
m is an integer from 1 to 6; and
R′ and R″ are according to (1) or (2):
(1) R′=H or an aliphatic hydrocarbon group containing from 1 to 14 carbon atoms,
R″=a cycloaliphatic hydrocarbon group containing from 5 to 12 carbon atoms, an aromatic hydrocarbon group containing from 6 to 12 carbon atoms, CH 2 —O—(C═O)—R′″, CH 2 —O—R″″, or CH 2 —(OCR′″″HCR′″″H) n —OR″″″, whereby R′″ is an aliphatic hydrocarbon group containing from 1 to 14 carbon atoms and R″″ is an aliphatic hydrocarbon group containing from 1 to 14 carbon atoms or an aromatic hydrocarbon group containing from 6 to 12 carbon atoms, n being from 1 to 35, R′″″ independently being H or an aliphatic hydrocarbon group containing from 1 to 14 carbon atoms and R″″″ being an aliphatic hydrocarbon group containing from 1 to 4 carbon atoms, and

(2) R′ and R″ form together a saturated cycloaliphatic hydrocarbon group containing from 5 to 8 carbon atoms;

b) one or more linking chains wherein each one of these linking chains links two of the structural units A, whereby a linking chain is the shortest chain of consecutive atoms that links two structural units A; and
c) a molecular weight in the range from 840 Daltons to 5000 Daltons, wherein the molecular weight is determined using MALDI-TOF mass spectrometry.

2. The multi-aziridine compound according to claim 1 , wherein
m is 1;
R′ and R″ are according to (1) or (2):
(1) R′=H or an alkyl group containing from 1 to 2 carbon atoms, and
R″=CH 2 —O—(C═O)—R′″, CH 2 —O—R″″, or CH 2 —(OCR′″″HCR′″″H) n —OR″″″, whereby R′″ is an alkyl group containing from 1 to 14 carbon atoms and R″″ is an alkyl group containing from 1 to 14 carbon atoms, n being from 1 to 35, R′″″ independently being H or a methyl group and R″″″ being an alkyl group containing from 1 to 4 carbon atoms, and;

(2) R′ and R″ form part of a saturated cycloaliphatic hydrocarbon group containing from 5 to 8 carbon atoms.

3. The multi-aziridine compound according to claim 1 , wherein
R′=H, and
R″=a cycloaliphatic hydrocarbon group containing from 5 to 12 carbon atoms, an aromatic hydrocarbon group containing from 6 to 12 carbon atoms, CH 2 —O—(C═O)—R′″, CH 2 —O—R″″, or CH 2 —(OCR+′″″HCR′″″H) n —OR″″″, whereby R′″ is an aliphatic hydrocarbon group containing from 1 to 14 carbon atoms and R″″ is an aliphatic hydrocarbon group containing from 1 to 14 carbon atoms or an aromatic hydrocarbon group containing from 6 to 12 carbon atoms, n being from 1 to 35, R′″″ independently being H or an aliphatic hydrocarbon group containing from 1 to 14 carbon atoms and R″″″ being an aliphatic hydrocarbon group containing from 1 to 4 carbon atoms.

4. The multi-aziridine compound according to claim 1 , wherein R′ is
H and R″=CH 2 —O—(C═O)—R′″, CH 2 —O—R″″, or CH 2 —(OCH 2 CH 2 ) n —OCH 3 , whereby R′″ is an alkyl group containing from 3 to 12 carbon atoms and R″″ is an alkyl group containing from 1 to 14 carbon atoms.

5. The multi-aziridine compound according to claim 1 , wherein the multi-aziridine compound contains 2 or 3 structural units (A).

6. The multi-aziridine compound according to claim 1 , wherein the linking chains consist of from 4 to 300 atoms and the linking chains are a collection of atoms covalently connected which collection of atoms consists of i) carbon atoms, ii) carbon and nitrogen atoms, or iii) carbon, oxygen and nitrogen atoms.

7. The multi-aziridine compound according to claim 1 , wherein the multi-aziridine compound has a molecular weight of from 840 to 3800 Daltons, whereby the molecular weight is determined using MALDI-TOF mass spectrometry.

8. The multi-aziridine compound according to claim 1 , wherein the multi-aziridine compound comprises one or more connecting groups wherein each one of these connecting groups connects two of the structural units A, whereby the connecting groups consist of at least one functionality selected from:
aliphatic hydrocarbon functionality, cycloaliphatic hydrocarbon functionality, aromatic hydrocarbon functionality, isocyanurate functionality, iminooxadiazindione functionality, ether functionality, ester functionality, amide functionality, carbonate functionality, urethane functionality, urea functionality, biuret functionality, allophanate functionality, uretdione functionality and any combination thereof.

9. The multi-aziridine compound according to claim 8 , wherein the connecting groups of the multi-aziridine compound consist of at least one functionality selected from:
aliphatic hydrocarbon functionality, cycloaliphatic hydrocarbon functionality, aromatic hydrocarbon functionality, isocyanurate functionality, iminooxadiazindione functionality, urethane functionality, urea functionality, biuret functionality and any combination thereof.

10. The multi-aziridine compound according to claim 1 , wherein the multi-aziridine compound comprises one or more connecting groups wherein each one of these connecting groups connects two of the structural units A, wherein the connecting groups consist of (i) at least two aliphatic hydrocarbon functionality or at least two cycloaliphatic hydrocarbon functionality and (ii) an isocyanurate functionality or an iminooxadiazindione functionality, and wherein a pendant group is present on a connecting group, whereby the pendant group has the following structural formula:

n′ is the number of repeating units and is an integer from 1 to 50,
X is O or NH,
R 7 and R 8 are independently H or CH 3 in each repeating unit,
R 9 is an aliphatic hydrocarbon group or a cycloaliphatic hydrocarbon group and
R 10 contains at most 20 carbon atoms and is an aliphatic, cycloaliphatic or aromatic hydrocarbon group or a combination thereof.

11. The multi-aziridine compound according to claim 10 , wherein X is O and R 7 and R 8 are H.

12. The multi-aziridine compound according to claim 10 , wherein the multi-aziridine compound contains 2 structural units (A).

13. The multi-aziridine compound according to claim 12 , wherein the connecting group consists of the array of the following consecutive functionalities: a first aliphatic hydrocarbon functionality, an isocyanurate functionality or an iminooxadiazindione functionality, and a second aliphatic hydrocarbon functionality, and R 9 is an aliphatic hydrocarbon group, whereby the first and second aliphatic hydrocarbon functionality and R 9 are identical.

14. The multi-aziridine compound according to claim 1 , wherein the multi-aziridine compound contains polyoxyethylene (—O—CH2-CH2-) x group(s) in an amount of at least 0.1 wt. % and in an amount of less than 45 wt. % relative to the multi-aziridine compound.

15. The multi-aziridine compound according to claim 1 , wherein the multi-aziridine compound is obtained by reacting at least a polyisocyanate and a compound B with the following structural formula:

whereby the molar ratio of compound B to polyisocyanate is from 2 to 6.

16. The multi-aziridine compound according to claim 15 , wherein the polyisocyanate is a polyisocyanate with aliphatic reactivity that is a compound in which all of the isocyanate group

Assignees

• Covestro Netherlands Bv

Inventors

• Stals Patrick Johannes Maria
• Van Der Zwaag Daan
• Bückmann Alfred Jean Paul
• Overbeek Gerardus Cornelis
• Van Riel Jan

Classifications

• C08G18/44

  Polycarbonates · CPC title

• C08F220/1804

  C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate · CPC title

• C09D11/101

  Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing · CPC title

• C07D403/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D251/32

  Cyanuric acid; Isocyanuric acid · CPC title