Polyisocyanate resins

Patent metadata

Field	Value
Publication number	US-12054579-B2
Application number	US-202318211691-A
Country	US
Kind code	B2
Filing date	Jun 20, 2023
Priority date	Nov 19, 2020
Publication date	Aug 6, 2024
Grant date	Aug 6, 2024

Abstract

A polyisocyanate resin can include from 25 wt % to 50 wt % of a first cycloaliphatic polyisocyanate and from 50 wt % to 75 wt % of a flexibilizing component based on a total weight of the polyisocyanate resin. The flexibilizing component can include a linear aliphatic polyisocyanate having a number average isocyanate functionality of from 2 to 3 based on gel permeation chromatography and an isocyanate-terminated reaction product of a second cycloaliphatic polyisocyanate and an isocyanate-reactive material, the reaction product having a Tg of less than −30° C. based on a Differential Scanning calorimetry (2nd Heating) temperature scan from −100° ° C. to 150° C. using 20° C./min heating and cooling ramps. The isocyanate-terminated reaction product and the linear aliphatic polyisocyanate can be present at a weight ratio of from 0.5 to 2.5.

First claim

What is claimed is:

1. A polyisocyanate resin, comprising:
from 25 wt % to 50 wt %, based on a total weight of the polyisocyanate resin, of a first cycloaliphatic polyisocyanate; and
from 50 wt % to 75 wt %, based on a total weight of the polyisocyanate resin, of a flexibilizing component, comprising
an isocyanate-terminated reaction product of a second cycloaliphatic polyisocyanate and an isocyanate-reactive material, the isocyanate-terminated reaction product having a Tg of less than −30° C. based on a Differential Scanning calorimetry (2 nd Heating) temperature scan from −100° C. to 150° C. using 20° C./min heating and cooling ramps, and
a linear aliphatic polyisocyanate having a number average isocyanate functionality of from 2 to 3 based on gel permeation chromatography,
wherein the isocyanate-terminated reaction product and the linear aliphatic polyisocyanate are present at a weight ratio of from 0.5 to 3.

2. The polyisocyanate resin of claim 1 , wherein the first cycloaliphatic polyisocyanate has a number average isocyanate functionality of from 2.4 to 3.8.

3. The polyisocyanate resin of claim 1 , wherein the first cycloaliphatic polyisocyanate comprises an IPDI polyisocyanate.

4. The polyisocyanate resin of claim 3 , wherein the IPDI polyisocyanate comprises an IPDI trimer, an IPDI allophanate, or a combination thereof.

5. The polyisocyanate resin of claim 1 , wherein the isocyanate-terminated reaction product has a number average isocyanate functionality of from 1.8 to 2.8.

6. The polyisocyanate resin of claim 1 , wherein the isocyanate-terminated reaction product has an NCO % of from 2 wt % to 14 wt % based on ISO 11909:2007.

7. The polyisocyanate resin of claim 1 , wherein the second cycloaliphatic polyisocyanate comprises an IPDI polyisocyanate.

8. The polyisocyanate resin of claim 7 , wherein the IPDI polyisocyanate comprises an IPDI trimer, an IPDI allophanate, or a combination thereof.

9. The polyisocyanate resin of claim 1 , wherein the linear aliphatic polyisocyanate has an NCO % of from 15 wt % to 25 wt % based on ISO 11909:2007.

10. The polyisocyanate resin of claim 1 , wherein linear aliphatic polyisocyanate comprises an HDI polyisocyanate, a PDI polyisocyanate, or a combination thereof.

11. The polyisocyanate resin of claim 1 , wherein the linear aliphatic polyisocyanate comprises an allophanate.

12. The polyisocyanate resin of claim 1 , wherein the polyisocyanate resin is diluted in a solvent to form a polyisocyanate composition having a total solids content of from 80 wt % to 99 wt % based on a total weight of the polyisocyanate composition.

13. The polyisocyanate resin of claim 12 , wherein the solvent comprises ethyl acetate, butyl acetate, 1-methoxy propyl-acetate-2, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, toluene, xylene, solvent naphtha, or a combination thereof.

14. The polyisocyanate resin of claim 12 , wherein the polyisocyanate composition has a viscosity of from 500 mPas to 1300 mPas at 25° C. based on ISO 3219/A.3.

15. The polyisocyanate resin of claim 12 , wherein the polyisocyanate composition has an NCO % of from 8 wt % to 16 wt % based on ISO 11909:2007.

16. A coating composition, comprising:
the polyisocyanate resin of claim 1 ; and
a polyaspartate composition,
wherein the polyisocyanate resin and the polyaspartate composition are combined at an NCO:NH equivalent ratio of from 1:1 to 1.2:1.

17. A polyurea coating, comprising:
the coating composition of claim 16 applied to a surface portion of a substrate at a coating thickness of from 1 mil to 16 mil.

18. The polyurea coating of claim 17 , wherein the polyurea coating has a change in 60° gloss value of less than 7 gloss units from 4 hours to 4 weeks after applying the coating composition to the surface portion based on ASTM D523 and storage conditions of 75° F. and relative humidity of 55%.

19. The polyurea coating of claim 17 , wherein the polyurea coating has a deformation resistance of at least 30 inch-pounds 4 weeks after applying the coating composition to the surface portion based on ASTM D2794 and initial storage conditions at 120° F. for and 80% relative humidity for 30 minutes and subsequent storage conditions of 104° F. and relative humidity of 80%.

20. A method of manufacturing a polyisocyanate resin, comprising:
combining a first cycloaliphatic polyisocyanate and a flexibilizing component at a weight ratio of from 0.3 to 1, wherein the flexibilizing component, comprises:
an isocyanate-terminated reaction product of a second cycloaliphatic polyisocyanate and an isocyanate-reactive material, the reaction product having a Tg of less than −30° C. based on a Differential Scanning calorimetry (2 nd Heating) temperature scan from −100° ° C. to 150° C. using 20° C./min heating and cooling ramps, and
a linear aliphatic polyisocyanate having a number average isocyanate functionality of from 2 to 3 based on gel permeation chromatography,

wherein the isocyanate-terminated reaction product and the linear aliphatic polyisocyanate are combined at a weight ratio of from 0.5 to 3.

Assignees

• Covestro Llc

Inventors

• Best Kurt E
• Wang Daniel P
• Kleer Joseph

Classifications

• C09D175/02

  Polyureas · CPC title

• C08G18/7825

  containing ureum groups · CPC title

• C08G18/73 Primary

  acyclic · CPC title

• C08G18/5042

  containing ureum groups · CPC title

• C08G18/12

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