Storage-stable polyisocyanate composition and preparation method

Patent metadata

Field	Value
Publication number	US-12304993-B2
Application number	US-202017790433-A
Country	US
Kind code	B2
Filing date	Jul 22, 2020
Priority date	Jan 2, 2020
Publication date	May 20, 2025
Grant date	May 20, 2025

Abstract

The present application provides a storage-stable polyisocyanate composition and a preparation method. The polyisocyanate composition is obtained by selecting one or more diisocyanate from aliphatic diisocyanates and alicyclic diisocyanates, and reacting same with an alcohol compound; the polyisocyanate composition contains an isocyanurate group, a uretdione group, a carbamate group, and an allophanate group; within the polyisocyanate composition, the molar ratio of the carbamate group/(uretdione group+isocyanurate group) is 0.01-0.2, and preferably 0.01-0.1. Compared to existing techniques, the present application has the advantage of a noticeable increase in system viscosity of uretdione polyisocyanate during storage. With the present application, by means of controlling the ratio of the carbamate group/(uretdione group+isocyanurate group) within the system, the increase in viscosity of a product during storage is inhibited, thereby improving the storage stability of the product.

First claim

What is claimed is:

1. A storage-stable polyisocyanate composition, which is obtained by reacting one or more diisocyanates selected from aliphatic diisocyanates and alicyclic diisocyanates, with an alcohol compound, and the polyisocyanate composition comprises an isocyanurate group, a uretdione group, a carbamate group and an allophanate group;
in the polyisocyanate composition, a molar ratio of the carbamate group/(the uretdione group+the isocyanurate group) is 0.08-0.2, and a molar ratio of the carbamate group/(the allophanate group+the carbamate group) is 0.17-0.4.

2. The storage-stable polyisocyanate composition according to claim 1 , wherein an isocyanate group concentration is 16-24% by weight.

3. The storage-stable polyisocyanate composition according to claim 1 , wherein an isocyanate group concentration is 20-23% by weight.

4. The storage-stable polyisocyanate composition according to claim 3 , wherein a viscosity of the polyisocyanate composition at 25° C. is 100-1500 cp.

5. The storage-stable polyisocyanate composition according to claim 1 , wherein the alcohol compound has a relative molecular weight of 32-200, wherein the alcohol compound is one or more of methanol, ethanol, n-propanol, isopropanol, n-butanol, n-hexanol, 2-ethyl-1-hexanol, 1-methoxy-2-propanol, ethylene glycol, propylene glycol, isomeric butanediol, hexylene glycols, caprylyl glycols, diethylene glycol, dipropylene glycol, 2-ethyl-1,3-hexanediol, 2,2,4-trimethylpentanediol, glycerol and trimethylolpropane.

6. The storage-stable polyisocyanate composition according to claim 1 , wherein the aliphatic diisocyanate and the alicyclic diisocyanate are an organic diisocyanate containing 4-20 carbon atoms in the carbon skeleton in addition to the NCO group.

7. The storage-stable polyisocyanate composition according to claim 6 , wherein the organic diisocyanate is one or more of hexamethylene diisocyanate, isophorone diisocyanate, cyclohexyl dimethylene diisocyanate, dicyclohexylmethane diisocyanate, norbornane dimethylene diisocyanate, cyclohexyl diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate.

8. The storage-stable polyisocyanate composition according to claim 1 , wherein after the polyisocyanate composition has been stored at less than or equal to 40° C. for 6 months, the product viscosity changes less than or equal to 10%.

9. A preparation method of the storage-stable polyisocyanate composition according to claim 1 , comprising: mixing and reacting the diisocyanate and the alcohol compound, and controlling a reaction temperature to be 50-160° C.; controlling a reaction time to be 0.5-4 hours; then adding a tertiary phosphine catalyst, and controlling a reaction temperature to be 60-120°° C. and a reaction time to be 1-12 hours;
or, mixing and reacting the diisocyanate and a tertiary phosphine catalyst, and controlling a reaction temperature to be 50-150° C.; controlling a reaction time to be 0.5-12 hours; then adding the alcohol compound, and controlling a reaction temperature to be 60-120° C. and a reaction time to be 1-3 hours.

10. The preparation method of the storage-stable polyisocyanate composition according to claim 9 , wherein the tertiary phosphine catalyst has the following structural formula:

wherein R 1 , R 2 and R 3 are independently selected from an aliphatic substituent or an aromatic substituent.

11. The preparation method of the storage-stable polyisocyanate composition according to claim 9 , wherein when the diisocyanate and the alcohol compound are mixed and reacted, the reaction temperature is controlled to be 50-150° C.

12. The preparation method of the storage-stable polyisocyanate composition according to claim 9 , wherein when the diisocyanate and the alcohol compound are mixed and reacted, the reaction time is controlled to be 1 hour.

13. The preparation method of the storage-stable polyisocyanate composition according to claim 9 , wherein when the diisocyanate and the tertiary phosphine catalyst are mixed and reacted, the reaction temperature is controlled to be 50-80° C.

14. The storage-stable polyisocyanate composition according to claim 2 , wherein a viscosity of the polyisocyanate composition at 25° C. is 130-1000 cp.

15. The preparation method of the storage-stable polyisocyanate composition according to claim 12 , wherein after adding the tertiary phosphine catalyst, the reaction temperature is controlled to be 60-100° C.

16. The preparation method of the storage-stable polyisocyanate composition according to claim 9 , wherein after adding the tertiary phosphine catalyst, the reaction time is controlled to be 1-8 hours.

17. The preparation method of the storage-stable polyisocyanate composition according to claim 13 , wherein when the diisocyanate and the tertiary phosphine catalyst are mixed and reacted, the reaction time is controlled to be 1-10 hours.

18. The preparation method of the storage-stable polyisocyanate composition according to claim 13 , wherein after adding the alcohol compound, the reaction temperature is controlled to be 80-100° C.

19. The preparation method of the storage-stable polyisocyanate composition according to claim 13 , wherein after adding the alcohol compound, the reaction time is controlled to be 1-2 hours.

Assignees

• Wanhua Chemical Group Co Ltd
• Wanhua Chemical Ningbo Co Ltd

Inventors

• Zhu Zhicheng
• Shi Bin
• Yan Chengyue
• Zheng Bing
• Li Li
• Shang Yonghua
• Liu Wei
• Li Haijun
• Wang Nuancheng
• Li Yuan

Classifications

• C08G18/282

  Alkanols, cycloalkanols or arylalkanols including terpenealcohols · CPC title

• C08G18/2815

  Monohydroxy compounds · CPC title

• C09D175/04

  Polyurethanes · CPC title

• C08G2150/00

  Compositions for coatings · CPC title

• C08G18/8016

  Masked aliphatic or cycloaliphatic polyisocyanates · CPC title