Process for the production of isocyanurate polyisocyanates, the compounds obtained by this process and their use

• US 5,144,031 A
• Filed: 05/06/1991
• Issued: 09/01/1992
• Est. Priority Date: 05/11/1990
• Status: Expired due to Term

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Pedain, Josef
• Primary Examiner(s): Kight, III, John
• Assistant Examiner(s): SERGENT, RABON A
• Application Number:
  US07/696,433
• Time in Patent Office: 484 Days
• Field of Search: 252/182.2, 252/182.21, 252/182.22, 528/45, 528/59, 528/76, 528/80, 528/85, 528/49, 544/193, 544/222, 560/330
• US Class Current: 544/193
• CPC Class Codes: C07D 251/34 Cyanuric or isocyanuric esters
• CPC Class Codes: C08G 18/3256 Reaction products of polyamines with aldehydes or ketones
• CPC Class Codes: C08G 18/792 formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
• CPC Class Codes: C08G 18/8061 masked with compounds having only one group containing active hydrogen
• CPC Class Codes: C08G 18/8064 with monohydroxy compounds

Abstract

The present invention relates to a process for the production of isocyanurate group-containing polyisocyanates by partially trimerizing the isocyanate groups of (cyclo)aliphatic diisocyanates in the presence of catalysts which accelerate the trimerization of isocyanate groups and optionally in the presence of an inert solvent, terminating the trimerization reaction at the desired degree of trimerization and removing unreacted starting diisocyanate and any other volatile constituents, characterized in that at least one monohydric alcohol containing ester groups corresponding to the formula ##STR1## is added to the reaction mixture prior to removing the excess starting diisocyanate in a quantity of 1 to 30% by weight, based on the weight of the diisocyanate starting material, and reacted with a portion of the isocyanate groups to form urethane groups, provided that after the trimerization and urethanization reactions, the reaction mixture contains at least 10% by weigth of unreacted starting diisocyanate, based on the weight of the reaction mixture excluding the weight of inert solvent.

The present invention also relates to the isocyanurate polyisocyanates obtained by this process and to their use, optionally after blocking with blocking agents for isocyanate groups, for the production of polyurethane plastics and, more particularly, two-component polyurethane coating compositions.

Claims

1. A process for the production of an isocyanurate group-containing polyisocyanate which comprises

a) partially trimerizing the isocyanate groups of a (cyclo)aliphatic diisocyanate in the presence of a catalyst which accelerates the trimerization of isocyanate groups and optionally in the presence of an inert solvent,

b) terminating the trimerization reaction at the desired degree of trimerization required and

c) removing unreacted starting diisocyanate and any other volatile constituents,

said process additionally comprising

d) adding to the reaction mixture prior to step c) 1 to 30% by weight, based on the weight of said diisocyanate, of at least one monohydric alcohol containing ester groups and corresponding to the formula ##STR6## wherein R is an optionally olefinically unsaturated (cyclo)aliphatic C_1-18 hydrocarbon radical which may contain ether groups,

m is a whole or a fractional number having a value from 1 to 2 and

n is an integer of 3 to 5,

and reacting said alcohol with a portion of the isocyanate groups present to form urethane groups,

provided that on completion of the reactions of steps a) and d), the reaction mixture contains at least 10% by weight of unreacted diisocyanate, based on the weight of the reaction mixture excluding inert solvent.

2. The process of claim 1 wherein

R is a saturated aliphatic C_1-12 hydrocarbon radical and

n is 5.

3. The process of claim 1 wherein said diisocyanate comprises hexane-1,6-diisocyanate.

4. The process of claim 2 wherein said diisocyanate comprises hexane-1,6-diisocyanate.

5. An isocyanurate group-containing polyisocyanate which is prepared by a process which comprises

a) partially trimerizing the isocyanate groups of a (cyclo)aliphatic diisocyanate in the presence of a catalyst which accelerates the trimerization of isocyanate groups and optionally in the presence of an inert solvent,

b) terminating the trimerization reaction at the desired degree of trimerization required and

c) removing unreacted starting diisocyanate and any other volatile constituents,

said process additionally comprising

d) adding to the reaction mixture prior to step c) 1 to 30% by weight, based on the weight of said diisocyanate, of at least one monohydric alcohol containing ester groups and corresponding to the formula ##STR7## wherein R is an optionally olefinically unsaturated (cyclo)aliphatic C_1-18 hydrocarbon radical which may contain ether groups,

m is a whole or a fractional number having a value from 1 to 2 and

n is an integer of 3 to 5,

and reacting said alcohol with a portion of the isocyanate groups present to form urethane groups,

provided that on completion of the reactions of steps a) and d), the reaction mixture contains at least 10% by weight of unreacted diisocyanate, based on the weight of the reaction mixture excluding inert solvent.

6. The polyisocyanate of claim 5 wherein

R is a saturated aliphatic C_1-12 hydrocarbon radical and

n is 5.

7. The polyisocyanate of claim 5 wherein said diisocyanate comprises hexane-1,6-diisocyanate.

8. The polyisocyanate of claim 6 wherein said diisocyanate comprises hexane-1,6-diisocyanate.

9. A composition comprising the isocyanurate group-containing polyisocyanate of claim 5, wherein the isocyanate are optionally blocked with blocking agents, and a compound which contains at least two isocyanate-reactive groups.