Carbamylation compositions of monovalent metal containing catalysts, polyols and urea compounds and carbamylation processes using the same

Patent metadata

Field	Value
Publication number	US-10457777-B2
Application number	US-201514855426-A
Country	US
Kind code	B2
Filing date	Sep 16, 2015
Priority date	Sep 22, 2014
Publication date	Oct 29, 2019
Grant date	Oct 29, 2019

Abstract

The present invention provides carbamylation compositions of one or more urea compounds, one or more polyols and a monovalent transition metal or alkali metal catalyst (i), such as lithium ethylhexanoate, which compositions are substantially isocyanate free, enjoy reduced toxicity in comparison to tin catalysts, and which are useful in making polycarbamates which themselves provide compositions for making crosslinked polyurethanes.

First claim

We claim:

1. A carbamylation composition comprising from 0.1 to 1 wt. %, based on total solids, of one or more catalyst (i) which is a monovalent or alkali metal compound containing an anionic group, one or more urea compounds and one or more polymeric polyols, wherein the ratio of moles of the urea compound to molar equivalents of hydroxyl groups in the one or more polyol (urea:OH) ranges from 0.3:1 to 2.5:1 wherein the catalyst (i) is chosen from alkali metal acetylacetonates, 2,2,6,6-tetramethyl-3,5-heptanedionato cesium, alkali metal esters from alkanoic acids, alkali metal esters from sulfonic acids, alkali metal esters from halogenated sulfonic acids, copper (I) sulfonic metal esters, copper (I) halogenated sulfonic acid metal esters, silver (I) sulfonic acid metal esters, silver (I) halogenated sulfonic acid metal esters, cesium trifluoroacetate, and mixtures thereof.

2. The carbamylation composition as claimed in claim 1 , comprising from 0.25 to 0.75 wt. %, based on total solids, of the one or more catalyst (i).

3. The carbamylation composition as claimed in claim 1 , wherein the ratio of moles of the urea compound to molar equivalents of hydroxyl groups in the one or more polyols ranges less than 1:1.

4. The carbamylation composition as claimed in claim 1 which are substantially free of isocyanate groups.

5. The carbamylation composition as claimed in claim 4 , wherein the amount of isocyanate groups is less than 1 mol %, based on the total molar equivalents of hydroxyl groups plus total moles of isocyanate groups in the carbamylation compositions.

6. The carbamylation composition as claimed in claim 1 , wherein the one or more catalyst (i) comprises lithium 2-ethylhexanoate, lithium acetylacetonate, 2,2,6,6-tetramethyl-3,5-heptanedionato cesium, or copper (I) trifluoromethanesulfonate complex (2:1).

7. The carbamylation composition as claimed in claim 1 , wherein the one or more urea compounds is urea, biuret, triuret, N-substituted C 1 to C 6 alkyl ureas, such as N-methyl urea or N-ethyl urea, and mixtures thereof.

8. The carbamylation composition as claimed in claim 1 , wherein the one or more polyols is chosen from an acrylic polyol and an alkyd polyol.

9. A method of using the carbamylation composition as claimed in claim 1 to make polycarbamates, comprising slowly adding the one or more urea compounds in water to a reaction vessel containing the one or more catalysts (i) and the one or more polymeric polyols to form a reaction mixture and heating to a temperature of from 100 to 180° C. to form the polycarbamate.

10. The carbamylation composition as claimed in claim 1 , wherein the one or more catalyst (i) comprises lithium acetylacetonate, 2,2,6,6-tetramethyl-3,5-heptanedionato cesium, or copper (I) trifluoromethanesulfonate complex (2:1).

11. The carbamylation composition as claimed in claim 1 , wherein the polymeric polyol has a hydroxyl number of 50 to 250 mg KOH/g polyol, as determined by ASTM D4274-11, Test Method A.

Assignees

• Dow Global Technologies Llc

Inventors

• Beigzadeh Daryoosh
• Clark Thomas P
• Foley Paul
• Lu Congcong
• Margl Peter
• Romer Duane R

Classifications

• C08G71/04 Primary

  Polyurethanes · CPC title

• C08L33/066

  containing -OH groups · CPC title

• C08G18/225 Primary

  of alkali or alkaline earth metals · CPC title

• C08G73/00 Primary

  Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00 {(polycarbodiimides prepared from isocyanates C08G18/025, C08G18/797)} · CPC title

• C08G18/168

  Organic compounds · CPC title