Aqueous coating composition

Patent metadata

Field	Value
Publication number	US-11098223-B2
Application number	US-201816483155-A
Country	US
Kind code	B2
Filing date	Feb 7, 2018
Priority date	Feb 8, 2017
Publication date	Aug 24, 2021
Grant date	Aug 24, 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 two cyclic groups, (b) a non-cyclic aliphatic diisocyanate(s) whereby the non-cyclic aliphatic group connecting the two isocyanate groups has from 4 to 36 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), (b) and (c):
(a) a polyisocyanate containing at least two cyclic groups,
(b) a non-cyclic aliphatic diisocyanate which includes a non-cyclic aliphatic group connecting two isocyanate groups having from 4 to 36 carbon atoms, and
(c) a component containing an isocyanate-reactive group, wherein
the summed amount of components (a) and (b) is 10 to 60 wt. %, relative to the total weight amount of components used to prepare the polyurethane A; and wherein
components (a) and (b) are present in a weight ratio of the component (a) to the component (b) is in a range from 75:25 to 95:5; and wherein

the polyurethane A has an acid value which is in a range from 4 to 60 mg KOH/g polyurethane A, and wherein
the aqueous coating composition has an ethylenically unsaturated bond concentration in a range from 0.5 to 6 milliequivalents per gram of the polyurethane A and the radiation-curable diluent.

2. The aqueous coating composition according to claim 1 , wherein the weight ratio of the components (a) to (b) is from 75:25 to 90:10.

3. The aqueous coating composition according to claim 1 , wherein the component (a) is a polyisocyanate containing at least two cycloaliphatic groups.

4. The aqueous coating composition according to claim 1 , wherein the component (a) is dicyclohexylmethane diisocyanate.

5. The aqueous coating composition according to claim 1 , wherein the component (b) is a non-cyclic aliphatic C4-C9 diisocyanate.

6. The aqueous coating composition according to claim 1 , wherein component (b) is 1,6-diisocyanatohexane.

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

8. The aqueous coating composition according to claim 1 , wherein the component (c) comprises at least one isocyanate-reactive component containing at least one (meth)acryloyl group per molecule.

9. The aqueous coating composition according to claim 1 , wherein the polyurethane A is prepared by forming a neutralized isocyanate-terminated polyurethane pre-polymer which is dispersed in water and thereafter subsequently chain-extended with a chain-extending compound selected from the group consisting of hydrazine, a primary diamine, a secondary diamine, a compound containing a primary amino group and a secondary amino group, and mixtures thereof.

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

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

12. The aqueous coating composition according to claim 1 , wherein the aqueous coating composition contains 1-methyl-2-pyrrolidinone in an amount less than 3 wt. % by weight of solids content of the coating composition.

13. The aqueous coating composition according to claim 1 , wherein the coating composition contains tin in amount of at most 2 ppm.

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

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

16. The aqueous coating composition according claim 1 wherein the aqueous coating composition comprises a photo-initiator.

17. The aqueous coating composition according to claim 5 , wherein the component (b) is a C4-C8 diisocyanate.

18. The aqueous coating composition according to claim 1 , wherein the component (c) comprises:
at least one isocyanate-reactive component containing at least one (meth)acryloyl group per molecule; and
at least one isocyanate-reactive component containing ionic and/or potentially ionic water-dispersing groups; and wherein
component (c) further optionally comprises an isocyanate-reactive component different from any other component (c) and is selected from the group consisting of polyester(amide) polyols, polyether polyols, polycarbonate polyols and any mixture thereof.

19. A process for preparing the aqueous coating composition according to claim 1 comprising the following steps:
I. preparing an isocyanate-terminated polyurethane pre-polymer optionally in the presence of a diluent by reacting at least the following components (a), (b), (c):
(a) a polyisocyanate containing at least two cyclic groups,
(b) a non-cyclic aliphatic diisocyanate which includes a non-cyclic aliphatic group connecting two isocyanate groups having from 4 to 36 carbon atoms, and
(c) a component containing at least one isocyanate-reactive group comprising:
(c)(i) an isocyanate-reactive component containing ionic and/or potentially ionic water-dispersing groups, and/or
(c)(ii) an isocyanate-reactive component containing at least one (meth)acryloyl group per molecule, and/or
(c)(iii) an isocyanate-reactive component other than the components by (c)(i) and (c)(ii); wherein

the summed amount of the components (a) and (b) is 10 to 60 wt. %, relative to the total weight amount of components used to prepare the polyurethane A; and wherein
the components (a) and (b) are present in a weight ratio of the component (a) to the component (b) is in the range from 75:25 to 95:5;

II. either blending the isocyanate-terminated polyurethane pre-polymer with an aqueous phase comprising neutralizing agent and optionally further comprising a chain extending compound or either neutralizing the isocyanate-terminated polyurethane pre-polymer by adding neutralizing agent to the isocyanate-terminated polyurethane pre-polymer and subsequently (i) adding the neutralized isocyanate-terminated polyurethane prepolymer to water optionally comprising a further chain extending compound or (ii) adding water optionally comprising a further chain extending compound to the neutralized isocyanate-terminated polyurethane prepolymer; and
III. feeding to a reactor, at the start of the reaction to prepare the isocyanate-terminated polyurethane pre-polymer, either
(A) components (a) and (b) and at least one of the components (c)(i), (c)(ii) and (c)(iii),
(B) component (a) and at least two of the components (b), (c)(i), (c)(ii) and (c)(iii) or
(C) component (b) and at least two of the components (a), (c)(i), (c)(ii) and (c)(iii); and wherein

the preparation of the polyurethane A is effected in the presence of <3 wt. % of 1-methyl-2-pyrrolidone by weight of the polyurethane A.

20. The process according to claim 19 , wherein the weight ratio of the components (a) to (b) is from 75:25 to 90:10.

21. The process according to claim 19 , wherein the chain-extending of the isocyanate-terminated polyurethane pre-polymer is effected with a compound selected from the group consisting of hydrazine, a primary diamine, a secondary diamine, a compound containing a primary amino group and a secondary amino group, and mixtures t

Assignees

• Dsm Ip Assets Bv
• Covestro Netherlands Bv

Inventors

• Van Casteren Ilse
• Tennebroek Ronald
• Overbeek Gerardus Cornelis
• Celestijn Jourraine

Classifications

• C09D11/102

  containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds · CPC title

• C09D11/30

  Inkjet printing inks · CPC title

• C08L75/16

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

• C09D15/00

  Woodstains · CPC title

• C08G18/73

  acyclic · CPC title