Polyisocyanates, their production and uses

• US 5,086,175 A
• Filed: 12/18/1989
• Issued: 02/04/1992
• Est. Priority Date: 12/28/1988
• Status: Expired due to Fees

• Current Assignee: Takeda Chemical Industries, Ltd. (Takeda Pharmaceutical Company Limited)
• Original Assignee: Takeda Chemical Industries, Ltd. (Takeda Pharmaceutical Company Limited)
• Inventors: Hirata, Fumiaki, Nakashima, Tatsuya, Minato, Ichiro
• Primary Examiner(s): RICHTER, JOHANN R
• Application Number:
  US07/451,746
• Time in Patent Office: 778 Days
• Field of Search: 544/221
• US Class Current: 544/221
• CPC Class Codes: C08G 18/791 containing isocyanurate groups
• CPC Class Codes: C08G 18/8064 with monohydroxy compounds

Abstract

A polyisocyanate having an isocyanurate ring which is obtained by reacting a diisocyanate compound selected from the group consisting of alkylene, cycloalkylene and aralkylene diisocyanates with a monoalcohol of 10 to 50 carbon atoms in the presence of an isocyanuration catalyst, and removing of the unreacted diisocyanate compound from the reaction mixture, can be used in combination with various polyols, in the main, for the preparation of coatings, adhesives, architectural materials, molding materials, etc.

Claims

1. A polyisocyanate having an isocyanurate ring which can be diluted with a nonpolar solvent to a concentration of 75% or less and remains a clear homogeneous liquid without showing turbidity at 5°

C. and which is obtained by reacting a diisocyanate compound selected from the group consisting of alkylene, cycloalkylene and aralkylene diisocyanates with a monoalcohol of 10- to 50 carbon atoms in the presence of an isocyanuration catalyst, and removing the unreacted diisocyanate compound from the reaction mixture.

2. The polyisocyanate as claimed in claim 1, wherein the diisocyanate compound is an alkylene diisocyanate.

3. The polyisocyanate as claimed in claim 2, wherein the alkylene diisocyanate is 1,6-hexamethylene diisocyanate.

4. The polyisocyanate as claimed in claim 1, wherein the diisocyanate compound is a cycloalkylene diisocyanate.

5. The polyisocyanate as claimed in claim 4, wherein the cycloalkylene diisocycanate is 1,3-bis(isocyanato methyl)cyclohexane.

6. The polyisocyanate as claimed in claim 1, wherein the monoalcohol is a branched monoalcohol of 12 to 30 carbon atoms.

7. The polyisocyanate as claimed in claim 1, wherein the monoalcohol of 10 to 50 carbon atoms is n-decanol.

8. The polyisocyanate as claimed in claim 1, wherein the monoalcohol of 10 to 50 carbon atoms is 5-ethyl-2-nonanol.

9. The polyisocyanate as claimed in claim 1, wherein the monoalcohol of 10 to 50 carbon atoms is 2-hexyldecanol.

10. The polyisocyanate as claimed in claim 1, wherein the monoalcohol of 10 to 50 carbon atoms is 2-octyldodecanol.

11. The polyisocyanate as claimed in claim 1, wherein the monoalcohol is used in the amount of about 0.1 to 30 percent by weight based on the amount of the diisocyanate compound.

12. The polyisocyanate as claimed in claim 1, wherein the monoalcohol is used in the amount of about 0.5 to 20 percent by weight based on the amount of the diisocyanate compound.

13. The polyisocyanate as claimed in claim 1, wherein the isocyanuration catalyst is a hydroxyalkyl quaternary ammonium compound of the zwitterion type.

14. The polyisocyanate as claimed in claim 1, wherein the isocyanuration catalyst is trimethyl-N-2-hydroxypropylammonium 2-ethylhexanoate.

15. The polyisocyanate as claimed in claim 1, wherein the isocyanuration catalyst is used in the amount of about 0.001 to 0.1 percent by weight based on the amount of the diisocyanate compound.

16. The polyisocyanate as claimed in claim 1, wherein the isocyanuration catalyst is used in the amount of about 0.002 to 0.05 percent by weight based on the amount of the diisocyanate compound.

17. A process for producing a polyisocyanate having an isocyanurate ring which can be diluted with a nonpolar solvent to a concentration of 75% or less and remains a clear homogeneous liquid without showing turbidity at 5°

C. and which is obtained by reacting a diisocyanate compound selected from the group consisting of alkylene, cycloalkylene and aralkylene diisocyanates with a monoalcohol of 10 to 50 carbon atoms in the presence of an isocyanuration catalyst, and removing the unreacted diisocyanate compound from the reaction mixture.

18. A process for producing a polyisocyanate having an isocyanurate ring which can be diluted with a nonpolar solvent to a concentration of 75% or less and remains a clear homogeneous liquid without showing turbidity at 5°

C. and which comprises reacting a diisocyanate compound selected from the group consisting of alkylene, cycloalkylene and aralkylene diisocyanates with a monoalcohol of 10 to 50 carbon atoms in the presence of an isocyanuration catalyst, followed by removing the unreacted diisocyanate compound from the reaction mixture.

20. The process for producing a polyisocyanate as claimed in claim 18, wherein the isocyanuration reaction is conducted at about 30°

to 100°

C.

22. The process for producing a polyisocyanate as claimed in claim 18, wherein the isocyanuration reaction is conducted at about 40°

to 80°

C.

24. The process for producing a polyisocyanate as claimed in claim 18, wherein the rate of conversion based on the combined charge of diisocyanate compound and monoalcohol is about 10 to 50 percent by weight.

26. The process for producing a polyisocyanate as claimed in claim 18, wherein the rate of conversion based on the combined charge of diisocyanate compound and monoalcohol is about 15 to 40 percent by weight.

19. A process for producing a polyisocyanate having an isocyanurate ring which can be diluted with a nonpolar solvent to a concentration of 75% or less and remains a clear homogeneous liquid without showing turbidity at 5°

C. and which comprises reacting a diisocyanate compound selected from the group consisting of alkylene, cycloalkylene and aralkylene diisocyanates in the presence of an isocyanuration catalyst, followed by removing the unreacted diisocyanate compound from the reaction mixture and reacting the reaction product with a monoalcohol of 10 to 50 carbon atoms.

21. The process for producing a polyisocyanate as claimed in claim 19, wherein the isocyanuration reaction is conducted at about 30°

to 100°

C.

23. The process for producing a polyisocyanate as claimed in claim 19, wherein the isocyanuration reaction is conducted at about 40°

to 80°

C.

25. The process for producing a polyisocyanate as claimed in claim 19, wherein the rate of conversion based on the combined charge of diisocyanate compound and monoalcohol is about 10 to 50 percent by weight.

27. The process for producing a polyisocyanate as claimed in claim 19, wherein the rate of conversion based on the combined charge of diisocyanate compound and monoalcohol is about 15 to 40 percent by weight.