Polyurethane and UV-moisture dual cure PU reactive hotmelt comprising the same

Patent metadata

Field	Value
Publication number	US-11912867-B2
Application number	US-202017426777-A
Country	US
Kind code	B2
Filing date	Jan 14, 2020
Priority date	Feb 1, 2019
Publication date	Feb 27, 2024
Grant date	Feb 27, 2024

Abstract

Described herein is a polyurethane having an isocyanate group and having C—C double bonds on a side chain, a process for preparing such a polyurethane, and an UV-moisture dual cure polyurethane reactive hotmelt including the polyurethane.

First claim

The invention claimed is:

1. A UV-moisture dual cure polyurethane reactive hotmelt comprising (i) at least one polyurethane which has an isocyanate group and has C—C double bonds on a side chain and (ii) at least one photoinitiator, wherein an isocyanate in an isocyanate component for synthesizing the at least one polyurethane is diisocyanate and the isocyanate component comprises at least one diisocyanate having C—C double bonds on a side chain.

2. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 1 , wherein the amount of the C—C double bond is 0.07 to 0.5 mol/kg, based on the total weight of the at least one polyurethane.

3. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 1 , wherein the content of isocyanate groups is in the range from 0.2 to 6% by weight, based on the total weight of the at least one polyurethane.

4. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 1 , wherein the at least one polyurethane is obtained from the reaction of the isocyanate component with a polyol component.

5. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 1 , wherein the average number of C—C double bonds in the diisocyanate having C—C double bonds on the side chain is 1 to 6 per molecule.

6. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 1 , wherein the amount of the diisocyanate having C—C double bonds on the side chain is in the range from 5 to 35% by weight, based on the total weight of the isocyanate component and the polyol component.

7. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 1 , wherein the isocyanate component comprises at least one further isocyanate and said further isocyanate is diisocyanate.

8. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 4 , wherein the polyol component comprises at least one crystalline polyester polyol and/or at least one non-crystalline polyester polyol.

9. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 8 , wherein the crystalline polyester polyol has a hydroxyl number in the range from 15 to 50 mg KOH/g.

10. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 8 , wherein the non-crystalline polyester polyol has a hydroxyl number in the range from 10 to 80 mg KOH/g.

11. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 8 , wherein the amount of crystalline polyester polyol is in the range from 4 to 80% by weight, based on the total weight of the isocyanate component and the polyol component.

12. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 8 , wherein the amount of non-crystalline polyester polyol is in the range from 1 to 30% by weight, based on the total weight of the isocyanate component and the polyol component.

13. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 4 , wherein the polyol component comprises 0 to 75% by weight of at least one crystalline polyether polyol.

14. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 4 , wherein the polyol component comprises 0 to 10% by weight of at least one non-crystalline polyether polyol.

15. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 4 , wherein said isocyanate component comprises:
5 to 35% by weight of the diisocyanate having C—C double bonds on the side chain;
0 to 20% by weight of at least one further isocyanate and said further isocyanate being diisocyanate;
and
the polyol component comprises:
8 to 80% by weight of at least one crystalline polyester polyol;
1 to 30% by weight of at least one non-crystalline polyester polyol;
0 to 60% by weight of at least one crystalline polyether polyol; and
0 to 10% by weight of at least one non-crystalline polyether polyol;
wherein the weight % is based on total weight of the isocyanate component and the polyol component.

16. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 4 , wherein said isocyanate component comprises:
5 to 35% by weight of the diisocyanate having C—C double bonds on the side chain;
0 to 20% by weight of at least one further isocyanate and said further isocyanate being diisocyanate;
and
the polyol component comprises:
4 to 80% by weight of at least one crystalline polyester polyol;
1 to 30% by weight of at least one non-crystalline polyester polyol;
0 to 75% by weight of at least one crystalline polyether polyol; and
0 to 10% by weight of at least one non-crystalline polyether polyol;
wherein the weight % is based on total weight of the isocyanate component and the polyol component.

17. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 4 , wherein the polyols used in the polyol component have a functionality of 2.

18. The UV-moisture dual cure polyurethane reactive hotmelt according to claim 1 , which further comprises at least one urea reaction catalyst.

19. A method of using the UV-moisture dual cure polyurethane reactive hotmelt according to claim 1 , the method comprising using the UV-moisture dual cure polyurethane reactive hotmelt as an adhesive or in additive manufacturing.

20. A method for manufacturing a three-dimensional object, the method comprising using the UV-moisture dual cure polyurethane reactive hotmelt as defined in claim 1 to manufacture the three-dimensional object.

21. The method according to claim 20 , which comprises a step of forming a layer of the UV-moisture dual cure polyurethane reactive hotmelt as defined in claim 1 and irradiating the layer with the UV light to set the layer, repeating the step until the three-dimensional object is formed.

22. The method according to claim 21 , wherein the method is an additive manufacturing (3D printing) method.

23. A three-dimensional object obtained by the method according to claim 20 .

Assignees

• Basf Se

Inventors

• Peng-Poehler Xuyuan
• Guo yun fei
• Chen Li

Classifications

• C08L75/14 Primary

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

• B29C64/129

  characterised by the energy source therefor, e.g. by global irradiation combined with a mask · CPC title

• C08G18/12

  using two or more compounds having active hydrogen in the first polymerisation step · CPC title

• C08G18/4018

  Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48 · CPC title

• C08G18/4202

  Two or more polyesters of different physical or chemical nature (C08G18/44 takes precedence) · CPC title