Vinyl functionalized urethane resins for powder coating compositions

Patent metadata

Field	Value
Publication number	US-10072179-B2
Application number	US-201414786277-A
Country	US
Kind code	B2
Filing date	Apr 22, 2014
Priority date	Apr 26, 2013
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

The invention relates to a vinyl functionalized urethane resin (VFUR) useful as a curing agent in thermosetting powder coating compositions, a process for making said vinyl functionalized urethane resin, a vinyl functionalized urethane resin composition (VFURC) useful as a curing agent in thermosetting powder coating compositions, a process for making vinyl functionalized urethane resin composition, a thermosetting powder coating composition (TPCC), a process for the preparation thereof, a cured thermosetting powder coating composition, processes for coating an article with said thermosetting powder coating composition and an article coated with said thermosetting powder coating composition as well as uses of the vinyl functionalized urethane resin or of the vinyl functionalized urethane resin composition or of the thermosetting powder coating composition or of the articles having coated and cured thereon said thermosetting powder coating composition. The invention relates also to thermosetting powder coating composition useful for powder-in-mold coating articles such as reinforced polymeric e.g. polyester resin articles and to powder-in-mold coating methods employing the thermosetting powder coating composition and use of the in-mold coated article.

First claim

The invention claimed is:

1. A vinyl functionalized urethane resin (VFUR) wherein
the VFUR is crystalline having a melting enthalpy measured via Differential Scanning calorimetry, of at least 35 J/g; and
the VFUR has a ratio (R VFUR ) of urethane bonds in the VFUR to vinyl groups in the VFUR as measured by 1 H-NMR spectroscopy of at least 1.04 and at most 1.80.

2. The VFUR according to claim 1 , wherein the VFUR is prepared from:
(A) at least a compound A comprising isocyanate groups;
(B) at least a compound B comprising hydroxyl groups, wherein the compound B is selected from compounds in the group consisting of compounds comprising vinyl ether groups (VET), compounds comprising vinyl ester groups (VES), and compounds comprising vinyl ether and vinyl ester groups (VET-VES); and
(C) at least one organic compound C comprising hydroxyl groups.

3. The VFUR according to claim 2 , wherein the compound B is selected from the group consisting of compounds comprising vinyl ether groups (VET) and compounds comprising vinyl ester groups (VES).

4. The VFUR according to claim 2 , wherein the compound B is a compound comprising vinyl ether groups (VET).

5. The VFUR according to claim 4 , wherein the compound B is a vinyl ether alcohol.

6. The VFUR according to claim 1 , wherein the VFUR has a R VFUR of at least 1.06 and of at most 1.80.

7. The VFUR according to claim 1 , wherein the VFUR has a R VFUR of at least 1.10 and of at most 1.80.

8. The VFUR according to claim 1 , wherein the VFUR has a R VFUR of at least 1.10 and of at most 1.71.

9. The VFUR according to claim 1 , wherein the VFUR has a R VFUR of at least 1.18 and of at most 1.45.

10. The VFUR according to claim 5 , wherein the VFUR has a R VFUR of at least 1.06 and of at most 1.80.

11. The VFUR according to claim 5 , wherein the VFUR has a R VFUR of at least 1.10 and of at most 1.80.

12. The VFUR according to claim 5 , wherein the VFUR has a R VFUR of at least 1.10 and of at most 1.71.

13. The VFUR according to claim 5 , wherein the VFUR has a R VFUR of at least 1.18 and of at most 1.45.

14. The VFUR according to claim 1 , wherein the VFUR is solid at 23° C. and at atmospheric pressure.

15. The VFUR according to claim 2 , wherein the VFUR is solid at 23° C. and at atmospheric pressure.

16. The VFUR according to claim 3 , wherein the VFUR is solid at 23° C. and at atmospheric pressure.

17. The VFUR according to claim 4 , wherein the VFUR is solid at 23° C. and at atmospheric pressure.

18. The VFUR according to claim 5 , wherein the VFUR is solid at 23° C. and at atmospheric pressure.

19. The VFUR according to claim 6 , wherein the VFUR is solid at 23° C. and at atmospheric pressure.

20. The VFUR according to claim 7 , wherein the VFUR is solid at 23° C. and at atmospheric pressure.

21. The VFUR according to claim 8 , wherein the VFUR is solid at 23° C. and at atmospheric pressure.

22. The VFUR according to claim 9 , wherein the VFUR is solid at 23° C. and at atmospheric pressure.

23. The VFUR according to claim 10 , wherein the VFUR is solid at 23° C. and at atmospheric pressure.

24. The VFUR according to claim 11 , wherein the VFUR is solid at 23° C. and at atmospheric pressure.

25. The VFUR according to claim 12 , wherein the VFUR is solid at 23° C. and at atmospheric pressure.

26. The VFUR according to claim 13 , wherein the VFUR is solid at 23° C. and at atmospheric pressure.

27. A process for making the VFUR as defined in claim 1 , wherein the process comprises the step of reacting a compound A which comprises isocyanate groups with a compound B comprising hydroxyl groups and an organic compound C, wherein the compound B is selected from the group of compounds consisting of compounds comprising vinyl ether groups (VET), compounds comprising vinyl ester groups (VES), and compounds comprising vinyl ether and vinyl ester groups (VET-VES), and wherein the organic compound C comprises hydroxyl groups to form the VFUR, or alternatively
the process comprises the steps of:
(i) reacting the compound A with the organic compound C to form an isocyanate terminated adduct of the compound A with the organic compound C, and
(ii) reacting the isocyanate terminated adduct of the compound A with the organic compound C obtained in step (i) with the compound B to form the VFUR.

28. The process according to claim 27 , wherein the compound B is a vinyl ether alcohol.

29. The process according to claim 27 , wherein the VFUR is solid at 23° C. and at atmospheric pressure.

30. The process according to claim 27 , wherein the VFUR is solid at 23° C. and at atmospheric pressure, and the compound B is a vinyl ether alcohol.

31. A vinyl functionalized urethane resin composition (VFURC) comprising at least a first vinyl functionalized urethane resin (FVFUR) and a second vinyl functionalized urethane resin (SVFUR), wherein either the FVFUR or the SVFUR is a VFUR according to claim 1 , and wherein
the VFURC is crystalline having a melting enthalpy measured via Differential Scanning calorimetry, of at least 35 J/g; and
the VFURC has a ratio (R VFURC ) of urethane bonds in the VFURC to vinyl groups in the VFURC as measured by 1 H-NMR spectroscopy of at least 1.04 and at most 1.80.

32. A vinyl functionalized urethane resin composition (VFURC) comprising at least a first vinyl functionalized urethane resin (FVFUR) and a second vinyl functionalized urethane resin (SVFUR), wherein each of the FVUR and the SVFUR is a VFUR according to claim 1 , and wherein
the VFURC is crystalline having a melting enthalpy measured via Differential Scanning calorimetry, of at least 35 J/g; and
the VFURC has a ratio (R VFURC ) of urethane bonds in the VFURC to vinyl groups in the VFURC as measured by 1 H-NMR spectroscopy of at least 1.04 and at most 1.80.

33. A vinyl functionalized urethane resin composition (VFURC) comprising at least a first vinyl functionalized urethane resin (FVFUR) and a second vinyl functionalized urethane resin (SVFUR), wherein either the FVFUR or the SVFUR is a VFUR according to claim 6 wherein the compound B is a vinyl ether alcohol and the VFUR is solid at 23° C. and at atmospheric pressure, and wherein
the VFURC is crystalline having a melting enthalpy measured via Differential Scanning calorimetry, of at least 35 J/g; and
the VFURC has a ratio (R VFURC ) of urethane bonds in the VFURC to vinyl groups in the VFURC as measured by 1 H-NMR spectroscopy of at least 1.04 and at most 1.80, and.

34. A vinyl functionalized urethane resin composition (VFURC) comprising at least a first vinyl functionalized urethane resin (FVFUR) and a second vinyl functionalized urethane resin (SVFUR), wherein either the FVFUR or the SVFUR is a VFUR according to claim 7 wherein the compound B is a vinyl ether alcohol and the VFUR is solid at 23° C. and at atmospheric pressure, and wherein
the VFURC is crystalline having a melting enthalpy measured via Differential Scanning calorimetry, of at least 35 J/g; and
the VFURC has a has a ratio (R VFURC ) of urethane bonds in the VFURC to vinyl groups in the VFURC as measured by 1 H-NMR spectroscopy of at least 1.04 and at most 1.80, and.

35. A vinyl functionalized urethane resin composition (VFURC) comprising at least a first vinyl functionali

Assignees

• Dsm Ip Assets Bv

Inventors

• Drijfhout Jan Pieter

Classifications

• B29C41/22

  Making multilayered or multicoloured articles · CPC title

• C08G18/73

  acyclic · CPC title

• B05D3/0413

  Heating with air · CPC title

• B05D1/06

  Applying particulate materials · CPC title

• C08F283/00

  Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G · CPC title