Aqueous coating composition

Patent metadata

Field	Value
Publication number	US-11124671-B2
Application number	US-201816483820-A
Country	US
Kind code	B2
Filing date	Feb 7, 2018
Priority date	Feb 8, 2017
Publication date	Sep 21, 2021
Grant date	Sep 21, 2021

Abstract

The present invention relates to a radiation-curable aqueous coating composition comprising a polyurethane A comprising as building blocks at least: (a) a polyisocyanate(s) containing at least one cyclic group, (b) a non-cyclic aliphatic diisocyanate(s) whereby the non-cyclic aliphatic group connecting the two isocyanate groups has 5 carbon atoms, and (c) a component(s) containing an isocyanate-reactive group(s), whereby the summed amount of (a) and (b) is 10 to 60 wt. %, relative to the total weight amount of components used to prepare the polyurethane A; and optionally radiation-curable diluent; whereby the weight ratio between (a) and (b) is in the range from 50:50 to 99:1; and whereby the ethylenically unsaturated bond concentration of the coating composition is in the range from 0.5 to 6 milliequivalents per g of polyurethane A and radiation-curable diluent.

First claim

The invention claimed is:

1. A radiation-curable aqueous coating composition comprising a polyurethane A and optionally a radiation-curable diluent, wherein the polyurethane A comprises as building blocks at least the following components:
(a) at least one polyisocyanate which comprises at least one cyclic group,
(b) at least one non-cyclic aliphatic diisocyanate which comprises a non-cyclic aliphatic group having 5 carbon atoms connecting two isocyanate groups, and
(c) at least one component comprising at least one isocyanate-reactive group, wherein
the components (a) and (b) are present in a summed amount of 10 to 60 wt. %, relative to the total weight amount of components used to prepare the polyurethane A and in a weight ratio of the component (a) to the component (b) which is in a range of 50:50 to 99:1; and wherein
the coating composition has an ethylenically unsaturated bond concentration which is in a range of 0.5 to 6 milliequivalents per gram (meg/g) of the polyurethane A and if present the radiation-curable diluent.

2. The aqueous coating composition according to claim 1 , wherein the weight ratio of the component (a) to the component (b) is from 60:40 to 95:5.

3. The aqueous coating composition according to claim 1 , wherein the component (a) comprises at least one polyisocyanate containing at least one cycloaliphatic group.

4. The aqueous coating composition according to claim 1 , wherein the component (a) comprises at least one polyisocyanate which contains either one cycloaliphatic group or two cycloaliphatic groups.

5. The aqueous coating composition according to claim 1 , wherein the component (a) comprises at least one polyisocyanate containing either one cyclohexane group or two cyclohexane groups.

6. The aqueous coating composition according to claim 1 , wherein the component (a) is H12MDI (CAS number 5124-30-1).

7. The aqueous coating composition according to claim 1 , wherein the component (a) is isophorone diisocyanate (CAS number 4098-71-9).

8. The aqueous coating composition according to claim 1 , wherein the component (b) is 1,5-pentane diisocyanate (CAS number 4538-42-5).

9. The aqueous coating composition according to claim 1 , wherein the coating composition has an ethylenically unsaturated bond concentration which is introduced into the coating composition by the presence of (meth)acryloyl groups in the polyurethane (A) and/or the presence of the radiation-curable diluent.

10. The aqueous coating composition according to claim 1 , wherein polyurethane A comprises a building block derived from at least one isocyanate-reactive component containing at least one (meth)acryloyl group per molecule as component (c).

11. The aqueous coating composition according to claim 1 , wherein
the component (a) comprises at least one polyisocyanate containing one cycloaliphatic group, and wherein
the polyurethane A is an isocyanate-terminated polyurethane pre-polymer which is neutralized with a neutralizing agent and thereafter dispersed in water and thereafter subsequently chain-extended with at least one chain-extending compound selected from the group consisting of water, hydrazine, a primary diamine, a secondary diamine, a compound containing a primary amino group, a compound containing a secondary amino group and any mixture thereof.

12. The aqueous coating composition according to claim 1 , wherein
the component (a) comprises at least one polyisocyanate containing at least two cycloaliphatic groups, and wherein
the polyurethane A is an prisocyanate-terminated polyurethane pre-polymer which is neutralized with a neutralizing agent and thereafter dispersed in water and subsequently chain-extended with at least one chain-extending compound selected from the group consisting of hydrazine, a primary diamine, a secondary diamine, a compound c mp und(s) containing a primary amino group, a compound containing a secondary amino group and any mixture thereof.

13. The aqueous coating composition according to claim 1 , wherein the polyurethane A has an acid value which is in a range from 4 to 60 mg KOH/g polyurethane A.

14. The aqueous coating composition according to claim 1 , wherein the coating composition has a minimum film formation temperature of lower than 35° C. in substantial absence of a coalescent.

15. The aqueous coating composition according to claim 1 , wherein the coating composition has a minimum film formation temperature of lower than 35° C. in substantial absence of the radiation-curable diluent.

16. The aqueous coating composition according to claim 1 , wherein the aqueous coating composition comprises less than 3 wt. %, based on weight of solids content of the coating composition, of 1-methyl-2-pyrrolidinone.

17. The aqueous coating composition according to claim 1 , wherein the coating composition comprises at most 2 ppm of tin.

18. The aqueous coating composition according to claim 1 , wherein the coating composition contains at most 1.5 wt. % of tertiary amines.

19. The aqueous coating composition according to claim 1 wherein the polyurethane A is present in the aqueous coating composition in an amount of 20 to 55 wt. %, relative to the total weight of the aqueous coating composition.

20. The aqueous coating composition according to claim 1 , wherein the aqueous coating composition further comprises a photo-initiator.

21. The aqueous coating composition according to claim 1 , wherein the weight ratio of the component (a) to the component (b) is from to 65:35 to 90:10.

22. A process for preparing the aqueous coating composition according to claim 1 , wherein the polyurethane A is prepared in the presence of <3 wt. % of 1-methyl-2-pyrrolidone by weight of the polyurethane A, and wherein the process comprises the following steps:
I. preparing an isocyanate-terminated polyurethane pre-polymer of the polyurethane A in the presence of a diluent by reacting at least the following components (a), (b), (c):
(a) at least one polyisocyanate which comprises at least one cyclic group,
(b) at least one non-cyclic aliphatic diisocyanate which comprises a non-cyclic aliphatic group having carbon atoms connecting two isocyanate groups, and
(c) at least one component containing at least one isocyanate-reactive group comprising at least one component selected from the group consisting of:
(c)(i) an isocyanate-reactive component containing an ionic and/or a potentially ionic water-dispersing groups,
(c)(ii) an isocyanate-reactive component containing at least one (meth)acryloyl group per molecule, and
(c)(iii) an isocyanate-reactive component other than the components (c)(i) and (c)(ii); wherein

the components (a) and (b) are present in a summed amount of 10 to 60 wt. %, relative to the total weight amount of components used to prepare the polyurethane A and in a weight ratio of the component (a) to the component (b) which is in a range of 50:50 to 99:1; and thereafter either

II(1) blending the isocyanate-terminated polyurethane pre-polymer of the polyurethane A with an aqueous phase comprising a neutralizing agent and optionally further comprising a chain extending compound, or
II(2) neutralizing the isocyanate-terminated polyurethane pre-polymer of the polyurethane A by adding a neutralizing agent to the isocyanate-terminated polyurethane pre-polymer and then subsequently either (i) adding the neutralized isocyanate-terminated polyurethane prepolymer to water optionally comprising a further chain extending compound or (ii) adding water optionally co

Assignees

• Covestro Netherlands Bv

Inventors

• Van Casteren Ilse
• Tennebroek Ronald
• Overbeek Gerardus Cornelis
• Celestijn Jourraine
• Griffioen Jacobus Willem

Classifications

• C08G18/758

  containing two or more cycloaliphatic rings · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title

• C08G18/722 Primary

  Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates · CPC title

• C09D175/16

  having terminal carbon-to-carbon unsaturated bonds · CPC title

• C08G18/706

  the liquid medium being water · CPC title