Coating composition

Patent metadata

Field	Value
Publication number	US-12565473-B2
Application number	US-202117791959-A
Country	US
Kind code	B2
Filing date	Jan 21, 2021
Priority date	Jan 22, 2020
Publication date	Mar 3, 2026
Grant date	Mar 3, 2026

Abstract

The present invention relates to an aqueous coating composition comprising a multi-aziridine compound and a carboxylic acid functional polymer, characterized in that (i) the composition is an aqueous dispersion having a pH ranging from 8 to 14, (ii) the aqueous dispersion comprises particles X which particles X comprise multi aziridine compound and particles Y which particles Y comprise carboxylic acid functional polymer, and (iii) said multi-aziridine compound has: a) from 2 to 6 of the following structural units A: 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 500 to 10000 Daltons.

First claim

The invention claimed is:

1 . An aqueous coating composition comprising a multi-aziridine compound and a carboxylic acid functional polymer, wherein
(i) the aqueous coating composition is an aqueous dispersion having a pH ranging from 8 to 14, (ii) the aqueous dispersion comprises particles X which particles X comprise multi-aziridine compound and particles Y which particles Y comprise carboxylic acid functional polymer, whereby the carboxylic acid functional polymer contains carboxylic acid groups and/or carboxylate groups, and (iii) said multi-aziridine compound has:
a) from 2 to 6 of the following structural units A:

whereby
R 1 is H,
R 2 and R 4 are independently chosen from H or an aliphatic hydrocarbon group containing from 1 to 4 carbon atoms,
R 3 is an aliphatic hydrocarbon group containing from 1 to 4 carbon atoms,
m is an integer from 1 to 6,
R′ and R″ are according to (1) or (2):
(1) R′=H or an aliphatic hydrocarbon group containing from 1 to 14 carbon atoms, and
R″=an aliphatic hydrocarbon group containing from 1 to 14 carbon atoms, 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,
(2) R′ and R″ form together a saturated cycloaliphatic hydrocarbon group containing from 5 to 8 carbon atoms,
t is an integer from 0 to 3,
R 5 is H or CH 3 ,

X and Y are according to (I), (II) or (III):
(I) X and Y are both N—R 6 ;
(II) X is O and Y is N—R 6 ;
(III) X is N—R 6 and Y is O,

whereby R 6 is H or a linear or branched hydrocarbon group containing from 1 to 4 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 calculated molecular weight in the range from 500 to 10000 Daltons, wherein the calculated molecular weight is the sum of the atomic masses of all atoms present in the structural formula of the multi-aziridine compound.

2 . The aqueous coating composition according to claim 1 , wherein R 2 is H, R 3 is CH 3 and R 4 is H.

3 . The aqueous coating composition according claim 1 , wherein R 2 is H, R 3 is CH 3 and R 4 is CH 3 .

4 . The aqueous coating composition according to claim 1 , wherein X is O, Y is NH, m is 1 and t is 0.

5 . The aqueous coating composition 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.

6 . The aqueous coating composition according to claim 1 , wherein the multi-aziridine compound contains 2 or 3 structural units A.

7 . The aqueous coating composition according to claim 1 , wherein
R′ is H and R″=an alkyl group containing from 1 to 4 carbon atoms, CH2-O—(C═O)—R′″, CH2-O—R″″, or CH2-(OCH2CH2)n-OCH3, 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.

8 . The aqueous coating composition 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, functionality, isocyanurate iminooxadiazindione functionality, urethane functionality, urea functionality, biuret functionality and any combination thereof.

9 . The aqueous coating composition according to claim 8 , wherein the connecting groups consist of at least one aliphatic hydrocarbon functionality and/or at least one cycloaliphatic hydrocarbon functionality and optionally at least one aromatic hydrocarbon functionality and optionally an isocyanurate functionality or an iminooxadiazindione functionality.

10 . The aqueous coating composition according to claim 8 , wherein the connecting groups consist of at least one aliphatic hydrocarbon functionality and/or at least one cycloaliphatic hydrocarbon functionality and an isocyanurate functionality or an iminooxadiazindione functionality.

11 . The aqueous coating composition 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 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:

wherein
n′ is the number of repeat units and is an integer from 1 to 50,
X is O or NH, preferably X is O,
R 7 and R 8 are independently H or CH 3 in each repeating unit,
R 9 is an aliphatic hydrocarbon group, preferably containing from 1 to 8 carbon atoms, and
R 10 is an aliphatic hydrocarbon group containing from 1 to 20 carbon atoms, a cycloaliphatic hydrocarbon group containing from 5 to 20 carbon atoms or an aromatic hydrocarbon group containing from 6 to 20 carbon atoms.

12 . The aqueous coating composition according to claim 1 , wherein structural units A are according to the following structural formula D:

13 . The aqueous coating composition 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.

14 . The aqueous coating composition according to claim 13 , wherein the polyisocyanate is a polyisocyanate with aliphatic reactivity in which all of the isocyanate groups are directly bonded to aliphatic or cycloaliphatic hydrocarbon groups, irrespective of whether aromatic hydrocarbon groups are also present.

15 . The aqueous coating composition according to claim 12 , wherein the number of consecutive C atoms and optionally O atoms between the N atom of the urethane group in a structural unit D and the next N atom which is either present in the linking chain or which is the N atom of the urethane group of another structural unit D is at most 9.

16 . The aqueous coating composition according to claim 1 , wherein the multi-aziridine compound has a

Assignees

• Covestro Netherlands Bv

Inventors

• Overbeek Gerardus Cornelis
• Stals Patrick Johannes Maria
• Van Der Zwaag Daan
• Bückmann Alfred Jean Paul
• Langermans Hermanus Adrianus
• Van Dijk Stella Josette
• Looijmans Rob

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