Method for producing polyisocyanates of (cyclo)aliphatic diisocyanates which are flocculation-stable in solvents

Patent metadata

Field	Value
Publication number	US-11807709-B2
Application number	US-201716339124-A
Country	US
Kind code	B2
Filing date	Oct 2, 2017
Priority date	Oct 7, 2016
Publication date	Nov 7, 2023
Grant date	Nov 7, 2023

Abstract

The present invention relates to a new process for preparing polyisocyanates containing isocyanurate groups and being flocculation-stable in solvents from (cyclo)aliphatic diisocyanates.

First claim

The invention claimed is:

1. A method comprising:
adding at least one additive into a polyisocyanate mixture comprising at least one solvent, and reducing flocculation and/or precipitation in the polyisocyanate mixture,
wherein the additive comprises a salt of:
(A1) at least one phosphorus-containing acidic compound selected from the group consisting of
(A1a) a mono- and/or di-C 1 to C 18 alkyl phosphate,
(A1b) a mono- and/or di-C 1 to C 18 alkyl phosphonate,
(A1c) a mono-C 1 to C 12 alkyl phosphinate, and
(A1d) an alkyl derivative of a phosphorus-containing diacid, and

(A2) at least one open-chain trisubstituted amine;
wherein the at least one additive is used in a concentration of 200 to 300 ppm by weight based on the polyisocyanate.

2. The method according to claim 1 , wherein the polyisocyanate is (cyclo)aliphatic.

3. The method according to claim 1 , wherein the polyisocyanate is at least one polyisocyanate made from at least one monomer selected from the group consisting of hexamethylene 1,6-diisocyanate, pentamethylene 1,5-diisocyanate, isophorone diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, 4,4′-di(isocyanato-cyclo-hexyl)-methane 2,4′-di(isocyanatocyclohexyl)methane.

4. The method according to claim 1 , wherein the polyisocyanate has isocyanurate, iminooxadiazinedione, biuret or allophanate optionally with urethane structures.

5. The method according to claim 1 , wherein the at least one open-chain trisubstituted amine (A2) is a trialkylamine.

6. The method according to claim 1 , wherein the at least one open-chain trisubstituted amine (A2) has a first corresponding acid having a pKa of between 5 and 14 at 25° C. in an aqueous solution.

7. The method according to claim 1 , wherein the solvent comprises water and the additive is used substoichiometrically in relation to the amount of water present in the solvent.

8. The method according to claim 1 , wherein the polyisocyanate admixed with additive further comprises at least one phenol or bridged bisphenol which has exactly one phenolic hydroxyl group on each aromatic ring and has alkyl groups in the ortho positions to the phenolic hydroxyl group.

9. The method according to claim 1 , wherein the polyisocyanate admixed with additive further comprise at least one Lewis acid.

10. A method for stabilizing a polyisocyanate or a polyisocyanate mixture in solvent against flocculation during storage, the method comprising:
mixing the polyisocyanate or polyisocyanate mixture with at least one additive comprising a salt of:
(A1) at least one phosphorus-containing acidic compound selected from the group consisting of
(A1a) a mono- and/or di-C 1 to C 18 alkyl phosphate,
(A1b) a mono- and/or di-C 1 to C 18 alkyl phosphonate,
(A1c) a mono-C 1 to C 12 alkyl phosphinate, and
(A1d) an alkyl derivate of a phosphorus-containing diacid, and

(A2) at least one open-chain trisubstituted amine,
thereby obtaining mixture (I); and
storing mixture (I), thereby stabilizing mixture (I) against flocculation during storage;
wherein the at least one additive is used in a concentration of 200 to 300 ppm by weight based on the polyisocyanate.

11. The method according to claim 10 , wherein the mixture (I) further comprises Lewis acids as catalysts and/or antioxidants and/or other customary coatings additives.

12. A method for coating a substrate with a polyisocyanate or a polyisocyanate mixture stabilized against flocculation during storage in solvents, the method comprising:
mixing the polyisocyanate or polyisocyanate mixture with 200 to 300 ppm of at least one additive based on the polyisocyanate or polyisocyanate mixture, the at least one additive is a salt of:
(A1) at least one phosphorus-containing acidic compound selected from the group consisting of
(A1a) a mono- and/or di-C 1 to C 18 alkyl phosphate,
(A1b) a mono- and/or di-C 1 to C 18 alkyl phosphonate,
(A1c) a mono-C 1 to C 12 alkyl phosphinate, and
(A1d) an alkyl derivate of a phosphorus-containing diacid, and

(A2) at least one open-chain trisubstituted amine,
thereby obtaining mixture (I);
mixing the mixture (I) with a solvent and optionally other additives, thereby obtaining mixture (II);
storing the mixture (II) thereby reducing flocculation in the mixture (II);
subsequently mixing the mixture (II) with at least one binder-comprising component, thereby obtaining mixture (III); and
subsequently applying the mixture (III) to the substrate.

13. The method according to claim 12 , wherein the binder-comprising component is at least one selected from the group consisting of a polyacrylate polyol, a polyester polyol, a polyurethane polyol, a polycarbonate polyol and a polyether polyol.

14. The method according to claim 12 , wherein severe flocculation is not seen in the mixture (II) until at least 126 days.

15. The method according to claim 12 , wherein the at least one polyisocyanate mixture further comprises at least one antioxidant.

16. The method according to claim 15 , wherein the at least one additive is added in an amount which is substoichiometric in relation to the total amount of water in the mixture.

Assignees

• Basf Se

Inventors

• Schaefer Harald
• Flojhar Daniel
• Scheidel Jens
• Genger Thomas
• Emmerling Sebastian
• Kroner Matthias
• Arens Guillermo

Classifications

• C08G18/792 Primary

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C08G18/73

  acyclic · CPC title

• C08K5/17

  Amines; Quaternary ammonium compounds · CPC title

• C08K5/521

  Esters of phosphoric acids, e.g. of H3PO4 · CPC title

• C08K5/5313

  Phosphinic compounds, e.g. R2=P(:O)OR' · CPC title