Two-component coating system
The present invention relates to a two-component coating system comprising a first component and a second component each of which is separate and distinct from each other, wherein the first component comprises a carboxylic acid functional polymer dissolved and/or dispersed in an aqueous medium, and the second component comprises a multi-aziridine compound having: a) from 2 to 6 of the following structural units (A): b) whereby m is an integer from 1 to 8; and R′ and R″ are both H b) one or more linking chains wherein each one of these linking chains links two of the structural units A; c) one or more connecting groups whereby each one of the connecting groups connects two of the structural units A; and d) a molecular weight in the range from 840 Daltons to 5000 Daltons, wherein the molecular weight is measured using MALDI-TOF mass spectrometry.
1. A two-component coating system comprising a first component and a second component each of which is separate and distinct from each other, wherein
the first component comprises a carboxylic acid functional polymer dissolved and/or dispersed in an aqueous medium, whereby the carboxylic acid functional polymer contains carboxylic acid groups and/or carboxylate groups, and
the second component comprises 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 both H;
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;
c) one or more connecting groups whereby each one of the connecting groups connects two of the structural units A and whereby 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 iminooxadiazinedione 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; and
d) 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 two-component coating system according to claim 1 , wherein m is 1.
3. The two-component coating system according to claim 1 , wherein the multi-aziridine compound contains 2 or 3 structural units (A).
4. The two-component coating system 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.
5. The two-component coating system according to claim 1 , wherein the number of consecutive C atoms and optionally O atoms between the N atom of the urethane group in a structural unit A 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 A is at most 9.
6. The two-component coating system according to claim 1 , wherein the multi-aziridine compound has a molecular weight of from 840 to 3800 Daltons.
7. The two-component coating system according to claim 1 , wherein X is O and R 7 and R 8 are H.
8. The two-component coating system according to claim 1 , wherein the multi-aziridine compound contains 2 structural units (A).
9. The two-component coating system according to claim 8 , wherein the connecting group consists of the array of the following consecutive functionalities: a first aliphatic hydrocarbon functionality, an isocyanurate functionality or an iminooxadiazinedione 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.
10. The two-component coating system 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.
11. The two-component coating system 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.
12. The two-component coating system according to claim 11 , 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.
13. The two-component coating system according to claim 1 , wherein the second component is a crosslinker composition comprising at least one of the multi-aziridine compound and further comprising at least one additional component.
14. The two-component coating system according to claim 13 , wherein the amount of aziridine functional molecules having a molecular weight lower than 820 Daltons is lower than 1.5 wt. % relative to the total weight of the crosslinker composition, whereby the molecular weight is determined using LC-MS, and wherein the crosslinker composition contains less than 5 wt. % of water.
15. A substrate having a coating obtained by (i) applying a coating composition obtained by mixing the first and second component of the two-component system according to claim 1 to a substrate and (ii) drying the coating composition by evaporation of volatiles.
16. 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 both H,
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 link two structural units A;
c) one or more connecting groups wherein each one of these connecting groups connects two of the structural units A and 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 iminooxadiazinedione 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, and
d) a molecular weight in the range from 840 Daltons to 5000 Daltons, wherein the molecular weight is measured using MALDI-TOF mass spectrometry.
17. The multi-aziridine compound according to claim 16 , wherein X is O and R 7 and R 8 are independently H.
18. The multi-aziridine compound according to claim 16 , wherein the multi-aziridine compound contains 2 structural units (A).
19. The multi-aziridine compound according to claim 16 , wherein the connecting group consists of the array of the following consecutive functionalities: a first aliphatic hydrocarbon functionality, an isocyanurate functionality or an iminooxadiazinedione 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.