Method for producing compounds having oxazolidinone groups

Patent metadata

Field	Value
Publication number	US-11142608-B2
Application number	US-201816494546-A
Country	US
Kind code	B2
Filing date	Mar 15, 2018
Priority date	Mar 17, 2017
Publication date	Oct 12, 2021
Grant date	Oct 12, 2021

Abstract

Described herein are processes for producing moldings comprising oxazolidinone groups, where polyisocyanate (a) is mixed with at least one organic compound (b) having two or more epoxide groups, at least one catalyst (c) for the isocyanate/epoxide reaction, and optionally auxiliary and additive materials (d) to form a reaction mixture, which is introduced into or applied to a mold and reacted to give moldings including oxazolidinone groups, where the catalyst (c) for the isocyanate/epoxide reaction includes a compound of the general formula [M(R1)(R2)(R3)(R4)]+ [X In]−, where M is a nitrogen atom or a phosphorus atom, R1, R2, R3 and R4 are an organic radical, X is fluorine, chlorine, bromine or iodine, I is iodine, and n stands for rational numbers from 0.1 to 10.

First claim

What is claimed is:

1. A process for producing moldings comprising oxazolidinone groups,
wherein:
a) polyisocyanate is mixed with
b) at least one organic compound having two or more epoxide groups,
c) at least one catalyst for the isocyanate/epoxide reaction, and
d) optionally auxiliary and additive materials
to form a reaction mixture, which is introduced into or applied to a mold and reacted to give moldings comprising oxazolidinone groups, wherein the at least one catalyst c) for the isocyanate/epoxide reaction comprises a compound of the general formula [M(R 1 )(R 2 )(R 3 )(R 4 )] + [X I n ] − , and wherein:
M is a nitrogen atom or a phosphorus atom,
R 1 , R 2 , R 3 and R 4 are each an organic radical, in each case selected independently of one another from the group consisting of linear or branched-chain alkyl radicals having 1 to 22 carbon atoms and being optionally substituted by heteroatoms or substituents comprising heteroatoms, and of alkyl-bridged cycloaliphatic or aromatic groups having 3 to 22 carbon atoms and being optionally substituted by heteroatoms or by groups comprising heteroatoms, and of aryl radicals having 6 to 18 carbon atoms and being optionally substituted by alkyl groups having 1 to 10 carbon atoms and/or heteroatoms,
X is fluoride, chloride, bromide or iodide,
I is iodine, and
n stands for a rational number from 0.1 to 10.

2. The process according to claim 1 , wherein n stands for a rational number from 0.5 to 3.

3. The process according to claim 1 , wherein X is chlorine or bromine.

4. The process according to claim 1 , wherein the molar ratio of polyisocyanate groups in the polyisocyanate (a) to epoxide groups in the at least one organic compound (b) having two or more epoxide groups is 1:10 to 10:1.

5. The process according to claim 1 , wherein the at least one organic compound b) having two or more epoxide groups is selected from the group consisting of polyglycidyl ether of bisphenol A, bisphenol F and novolacs and mixtures thereof.

6. The process according to claim 1 , wherein R 1 , R 2 , R 3 and R 4 are each an organic radical in each case selected independently of one another from the group consisting of phenyl, cyclohexyl and linear or branched-chain alkyl groups having 1 to 6 carbon atoms.

7. The process according to claim 1 , wherein R 1 , R 2 , R 3 and R 4 are identical.

8. The process according to claim 1 , wherein the mold in the reaction of the reaction mixture to give the moldings comprising oxazolidinone groups has a temperature of 140° C. to 280° C.

9. The process according to claim 1 , wherein a polyol component comprising the at least one organic compound b) and the at least one catalyst c) is mixed with an isocyanate to form the reaction mixture.

10. The process according to claim 1 , wherein an isocyanate component comprising the polyisocyanate a) and the at least one organic compound b) is mixed with the at least one catalyst c) to form the reaction mixture.

11. The process according to claim 1 , wherein the polyisocyanate a) used is at least one isocyanate selected from the group consisting of dodecane 1,12-diioscyanate, 2-ethyltetramethylene 1,4-diisocyanate, 2-methylpentamethylene 1,5-diisocyanate, tetramethylene 1,4-diisocyanate, and hexamethylene 1,6-diisocyanate; cycloaliphatic diisocyanates such as cyclohexane 1,3- and 1,4-diisocyanate and also any mixtures of these isomers, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI), hexahydrotolylene 2,4- and 2,6-diisocyanate and also the corresponding isomer mixtures, dicyclohexylmethane 4,4′-, 2,2′- and 2,4′-diisocyanate and also the corresponding isomer mixtures, tolylene 2,4- and 2,6-diisocyanate and the corresponding isomer mixtures, diphenylmethane 4,4′-, 2,4′- and 2,2′-diisocyanate and the corresponding isomer mixtures, mixtures of diphenylmethane 4,4′- and 2,2′-diisocyanates, polyphenylpolymethylene polyisocyanates, mixtures of diphenylmethane 4,4′-, 2,4′- and 2,2′-diisocyanates and polyphenylpolymethylene polyisocyanates (crude MDI), and mixtures of crude MDI and tolylene diisocyanates.

12. A method for producing moldings comprising oxazolidinone groups, the method comprising using a catalyst of the general formula
[M(R 1 )(R 2 )(R 3 )(R 4 )] + [X I n ] − ,
wherein M is a nitrogen atom or a phosphorus atom,
R 1 , R 2 , R 3 and R 4 are each an organic radical, in each case selected independently of one another from the group consisting of linear or branched-chain alkyl radicals having 1 to 22 carbon atoms and being optionally substituted by heteroatoms or substituents comprising heteroatoms, and of alkyl-bridged cycloaliphatic or aromatic groups having 3 to 22 carbon atoms and being optionally substituted by heteroatoms or by groups comprising heteroatoms, and of aryl radicals having 6 to 18 carbon atoms and being optionally substituted by alkyl groups having 1 to 10 carbon atoms and/or heteroatoms,
X is fluoride, chloride, bromide or iodide,
I is iodine, and
n stands for a rational number from 0.1 to 10,
for producing moldings comprising oxazolidinone groups.

Assignees

• Basf Se

Inventors

• Eling Berend
• Thomas Hans-Josef
• Deglmann Peter
• Hengelsberg Janina
• Pelzer Tristan
• Luinstra Gerrit A

Classifications

• C08G59/688

  containing phosphorus · CPC title

• C08G18/581

  Reaction products of epoxy resins with less than equivalent amounts of compounds containing active hydrogen added before or during the reaction with the isocyanate component (with amines C08G18/584) · CPC title

• C08G18/751

  containing only one cycloaliphatic ring · CPC title

• C08G18/003 Primary

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

• C08G18/168

  Organic compounds · CPC title