2-oxo-1,3-dioxolane-4-carboxamide building blocks, their preparation and use

Patent metadata

Field	Value
Publication number	US-9617238-B2
Application number	US-201414760834-A
Country	US
Kind code	B2
Filing date	Jan 30, 2014
Priority date	Jan 31, 2013
Publication date	Apr 11, 2017
Grant date	Apr 11, 2017

Abstract

The present invention suggests a 2-oxo-1,3-dioxolane-4-carboxamide of formula (I),

wherein R is an n-valent radical, n is an integer from 2 to 4, preferably from 2 to 3, and x is an integer from 1 to n−1. The invention furthermore suggests a process for the preparation of the 2-oxo-1,3-dioxolane-4-carboxamide of formula (I) from 2-oxo-1,3-dioxolane-4-carboxylic acid of formula (II)

with a polyisocyanate of the formula R(NCO) n , where R and n have the meanings given, the use of the 2-oxo-1,3-dioxolane-4-carboxamide of formula (I) for the preparation of a 2-oxo-1,3-dioxolane-4-carboxamide-substituted prepolymer, and the 2-oxo-1,3-dioxolane-4-carboxamide-substituted prepolymer thus obtainable.

First claim

The invention claimed is:

1. 2-Oxo-1,3-dioxolane-4-carboxamide of formula (I),

wherein R is a radical having a valency n of 2 to 4 and x is an integer from 1 to an amount equal to the valency n minus 1.

2. 2-Oxo-1,3-dioxolane-4-carboxamide according to claim 1 , wherein the radical has a valency n from 2 to 3.

3. 2-Oxo-1,3-dioxolane-4-carboxamide according to claim 1 , wherein R is selected from straight-chain, branched or cyclic C 2-22 -alkylene groups, C 6-20 -arylene groups, C 6-20 -alkarylene groups, polyether groups, polycarbonate groups, polyester groups, and poly(meth)acrylate groups.

4. A process for the preparation of a 2-oxo-1,3-dioxolane-4-carboxamide as defined in claim 1 , characterized in that 2-oxo-1,3-dioxolane-4-carboxylic acid of formula (II)

is reacted with a polyisocyanate of the formula R(NCO) n , where R is a radical having a valency n of 2 to 4.

5. The process according to claim 4 , characterized in that the reaction is carried out in the presence of a catalyst selected from tertiary amines, organometallic compounds, and mixtures thereof.

6. The process according to claim 5 , characterized in that the catalyst is selected from dimethylcyclohexylamine, 4-dimethylaminopyridine (DMAP), diazabicyclo-octane (DABCO), diazabicycloundecene (DBU), dibutyltin dilaurate (DBTL), a bismuth carboxylate, bismuth octanoate, bismuth neodecanoate, a titanium alkoxylate, a titanium carboxylate, a zirconium alkoxylate, a zirconium carboxylate, and mixtures thereof.

7. A method comprising reacting the 2-oxo-1,3-dioxolane-4-carboxamide as defined in claim 1 with a polyol for the preparation of a 2-oxo-1,3-dioxolane -4-carboxamide-substituted prepolymer.

8. The 2-oxo-1,3-dioxolane-4-carboxamide-substituted prepolymer obtained according to claim 7 .

Assignees

• Construction Research & Technology Gmbh

Inventors

• Wölfle Heimo
• Walther Burkhard
• Putzien Sophie

Classifications

• C07D317/38 Primary

  Ethylene carbonate · CPC title

• C08G18/10

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title