Process for the production of oligomeric polyisocyanates and their use in the production of polyurethane plastics

• US 4,614,785 A
• Filed: 08/14/1985
• Issued: 09/30/1986
• Est. Priority Date: 08/31/1984
• Status: Expired due to Fees

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Richter, Roland, Engbert, Theodor, Kubitza, Werner, Muller, Hanns P., Mennicken, Gerhard
• Primary Examiner(s): Welsh, Maurice J.
• Application Number:
  US06/765,472
• Time in Patent Office: 412 Days
• Field of Search: 528/45, 528/67, 528/73, 260/239 AR, 544/193
• US Class Current: 528/45
• CPC Class Codes: C07D 251/34 Cyanuric or isocyanuric esters
• CPC Class Codes: C08G 18/79 characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates

Abstract

The present invention relates to a process for the production of oligomeric polyisocyanates by the dimerization or trimerization of a portion of the isocyanate groups in organic polyisocyanates in the presence of tertiary phosphines or in the presence of a peralkylated phosphorus acid triamides as catalyst, followed by termination of the dimerization and/or trimerization reaction at the required degree of oligomerization by the addition of a catalyst poison, characterized in that a sulfonyl isocyanate is used as the catalyst poison.

The present invention also relates to the use of the oligomeric polyisocyanates obtained by this process, optionally in admixture with unreacted starting polyisocyanate or optionally blocked by blocking agents for isocyanate groups, as the polyisocyanate component in the production of polyurethane plastics.

Claims

1. A process for the production of an oligomeric polyisocyanate which comprises dimerizing and/or trimerizing a portion of the isocyanate groups of an organic polyisocyanate in the presence of a tertiary phosphine or a peralkylated phosphorus acid triamide as catalyst and terminating the dimerization and/or trimerization reaction at the desired degree of oligomerization by adding a sulfonyl isocyanate as the catalyst poison.

2. The process of claim 1 wherein said organic polyisocyanate is an organic diisocyanate having a molecular weight of 168 to about 300 and containing aliphatically, cycloaliphatically and/or aromatically bound isocyanate groups.

3. The process of claim 1 which comprises conducting said reaction at about 0°

to 100°

C. until about 5 to 70% of the isocyanate groups present in said organic polyisocyanate have been dimerized and/or trimerized and then terminating the reaction by the addition of said catalyst poison when that degree of conversion is reached.

4. The process of claim 1 wherein said sulfonyl isocyanate is used in at least an equivalent quantity, based on the catalyst.

5. The process of claim 2 wherein said sulfonyl isocyanate is used in at least an equivalent quantity, based on the catalyst.

6. The process of claim 1 wherein said sulfonyl isocyanate is used in at least twice the equivalent quantity, based on the catalyst.

7. The process of claim 2 wherein said sulfonyl isocyanate is used in at least twice the equivalent quantity, based on the catalyst.

8. The process of claim 1 wherein said sulfonyl isocyanate is used in at least an equivalent quantity, based on the catalyst, together with a quantity of an organic acid chloride such that in all at least 2 moles of sulfonyl isocyanate and acid chloride groups are available for each mole of phosphorus of the catalyst, which comprises adding the acid chloride at the same time as or after said sulfonyl isocyanate.

9. The process of claim 2 wherein said sulfonyl isocyanate is used in at least an equivalent quantity, based on the catalyst, together with a quantity of an organic acid chloride such that in all at least 2 moles of sulfonyl isocyanate and acid chloride groups are available for each mole of phosphorus of the catalyst, which comprises adding the acid chloride at the same time as or after said sulfonyl isocyanate.

10. The process of claim 1 wherein said sulfonyl isocyanate is an aromatic sulfonyl isocyanate.

11. The process of claim 2 wherein said sulfonyl isocyanate is an aromatic sulfonyl isocyanate.

12. The process of claim 4 wherein said sulfonyl isocyanate is an aromatic sulfonyl isocyanate.

13. The process of claim 1 wherein said sulfonyl isocyanate comprises tosyl isocyanate.

14. The process of claim 2 wherein said sulfonyl isocyanate comprises tosyl isocyanate.

15. The process of claim 4 wherein said sulfonyl isocyanate comprises tosyl isocyanate.

16. The process of claim 5 wherein said sulfonyl isocyanate comprises tosyl isocyanate.

17. The process of claim 6 wherein said sulfonyl isocyanate comprises tosyl isocyanate.

18. The process of claim 7 wherein said sulfonyl isocyanate comprises tosyl isocyanate.

19. The process of claim 3 which comprises removing the unreacted organic polyisocyanate from the reaction mixture by distillation after the reaction has been terminated.

20. A process for the production of a polyurethane which comprises

(a) preparing an oligomeric polyisocyanate in accordance with claim 1, and

(b) reacting said oligomeric polyisocyanate, optionally in blocked form, with a compound containing isocyanate-reactive groups wherein at least a portion of the isocyanate-reactive groups are hydroxyl groups.