Method for the production of a thermoplastic polyoxazolidinone

Patent metadata

Field	Value
Publication number	US-12378348-B2
Application number	US-202118017116-A
Country	US
Kind code	B2
Filing date	Aug 17, 2021
Priority date	Aug 24, 2020
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

A process for producing a thermoplastic polyoxazolidinone comprising copolymerizing a diisocyanate compound (A) with a bisepoxide compound (B) in the presence of a specific a quaternary ammonium, quaternary phoshonium and/or quaternary stibonium-based catalyst (C), a compound (D), a compound (F) wherein compound (D) and compound (F) independently comprises at least one of a monofunctional isocyanate, a monofunctional epoxide, a cyclic carbonate, a monofunctional alcohol, a monofunctional amine optionally in a solvent (E), and wherein the catalyst (C) is added in at least two portions (C-1) and (C-2). The invention is also related to the resulting thermoplastic polyoxazolidinone.

First claim

The invention claimed is:

1. A process for producing a thermoplastic polyoxazolidinone comprising copolymerization of a diisocyanate compound (A) with a bisepoxide compound (B) in the presence of a catalyst (C), a compound (D), a compound (F) optionally in a solvent (E);
wherein the catalyst (C) is represented by the formula (I)
[A] + n [Y] n−   (I)

wherein n is an integer having a value of 1, 2, or 3;
wherein [A] + is a quaternary ammonium, quaternary phosphonium and/or quaternary stibonium;
wherein [Y] n− is a monovalent, divalent or trivalent anion;

wherein the compound (D) comprises at least one of a monofunctional isocyanate, a monofunctional epoxide, a cyclic carbonate, a monofunctional alcohol, a monofunctional amine, or a combination thereof; and
wherein the compound (F) comprises at least one of a monofunctional isocyanate, a monofunctional epoxide, a cyclic carbonate, a monofunctional alcohol, a monofunctional amine, or a combination thereof;
wherein the catalyst (C) is added in at least two portions comprising a first portion (C-1) and a second portion (C-2), and
wherein the process comprises:
(α) reacting of the diisocyanate compound (A) with the bisepoxide compound (B) in the presence of the catalyst (C) and the compound (D) that is optionally in the solvent (E) to form an intermediate compound; and
(β) reacting the compound (F) with the intermediate compound formed in step (α).

2. The process according to claim 1 , wherein the process is conducted in the absence of a solvent (G), wherein the solvent (G) has a boiling point higher than 200° C. at 1 bar (absolute).

3. The process according to claim 1 , wherein catalyst (C) comprises at least one of a tetraalkylphosphonium halogenide, a tetracycloalkylphosphonium halogenide, a tetraarylphosphonium halogenide, a tetraalkylammonium halogenide, a tetracycloalkylammonium halogenide, and/or a tetraarylammonium halogenide.

4. The process according to claim 1 , wherein catalyst (C) is at least one compound selected from the group consisting of tetraphenylphosphonium chloride, tetraphenylphosphonium bromide, tetraphenylphosphonium iodide, bis(triphenylphosphine) iminium chloride, tetraphenylphosphonium nitrate, and tetraphenylphosphonium carbonate.

5. The process according to claim 1 , wherein step (α) comprises:
(α-1) placing the solvent (E) and the catalyst (C) in a reactor to provide a mixture (α-1),
(α-2) placing the compound (A), the bisepoxide compound (B) and the compound (D) in a second vessel to provide a mixture (α-2), and
(α-3) adding the mixture (α-2) to the mixture (α-1) and forming a copolymerization reaction product.

6. The process according to claim 5 , wherein the first portion (C-1) of the catalyst (C) is added in step (α-1).

7. The process according to claim 5 , wherein step (α) further comprises:
(α-4) adding the second portion (C-2) of the catalyst (C) to the mixture resulting from step (α-3).

8. The process according to claim 5 , wherein an epoxy-terminated oxazolidone-based prepolymer is formed in step (α-3).

9. The process according to claim 8 , wherein the epoxy-terminated oxazolidone-based prepolymer formed in step (α-3) is the copolymerization reaction product of a first portion (A-1) of the diisocyanate compound (A) with the bisepoxide compound (B) in the presence of the first portion (C-1) of the catalyst (C) optionally in the solvent (E), wherein the molar ratio of the epoxy groups of the bisepoxide compound (B) to the isocyanate groups of the first portion (A-1) of the diisocyanate compound (A) is from 1.1:1 to less than 25:1.

10. The process according to claim 8 , wherein the epoxy-terminated oxazolidone-based prepolymer is formed in the absence of the solvent (E).

11. The process according to claim 7 , wherein step (α-4) comprises adding a second portion (A-2) of the diisocyanate compound (A), the compound (D) in the solvent (E).

12. The process according to claim 1 , wherein the process is conducted in the presence of the solvent (E) wherein the solvent (E) is one or more compounds selected from the group consisting of chlorobenzene, an isomer of dichlorobenzene, dimethylformamide, N,N-dimethylacetamide, tetrahydrofurane, acetone, methyl ethyl ketone, 1,2-dimethoxyethane, 1-methoxy-2-(2-methoxyethoxy)ethane, and an isomer of dioxane.

13. The process according to claim 1 wherein compound (D) and compound (F) are monofunctional epoxides.

14. A thermoplastic polyoxazolidinone produced by the process according to claim 1 , wherein the thermoplastic polyoxazolidinone has a number average molecular weight Mn from ≥500 to ≤500,000 g/mol as determined with gel permeation chromatography (GPC).

15. The process according to claim 1 , wherein [A] + is a quaternary phosphonium.

16. The process according to claim 1 , wherein [Y] n− is a monovalent anion.

17. The process according to claim 1 , wherein the compound (D) comprises a monofunctional epoxide.

18. The process according to claim 1 , wherein the compound (F) comprises a monofunctional epoxide.

19. The process according to claim 3 , wherein catalyst (C) comprises a tetraalkylphosphonium halogenide, a tetracycloalkylphosphonium halogenide, a tetraarylphosphonium halogenide, or any combination thereof.

20. The process according to claim 4 , wherein catalyst (C) is at least one compound selected from the group consisting of tetraphenylphosphonium chloride, tetraphenylphosphonium bromide and tetraphenylphosphonium iodide.

Assignees

• Covestro Deutschland Ag

Inventors

• Movahhed Sohajl
• Westhues Stefan
• Thiel Daniel
• Laemmerhold Kai
• Wolf Aurel
• Guertler Christoph

Classifications

• C08G59/4028

  Isocyanates; Thioisocyanates · CPC title

• C08G18/7671

  containing only one alkylene bisphenyl group · CPC title

• C08G18/168

  Organic compounds · CPC title

• C08G18/003 Primary

  with epoxy compounds having no active hydrogen (with epoxy resins containing active hydrogen C08G18/58) · CPC title