Trimer catalysts with improved processability and surface cure

Patent metadata

Field	Value
Publication number	US-9815932-B2
Application number	US-201314060026-A
Country	US
Kind code	B2
Filing date	Oct 22, 2013
Priority date	May 4, 2006
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

Abstract

The present invention provides trimerization catalyst compositions having an α,β-unsaturated carboxylate salt and methods to produce a polyisocyanurate/polyurethane foam using such trimerization catalyst compositions.

First claim

The invention claimed is:

1. A composition comprising the contact product of:
a) at least one active hydrogen-containing compound; and
b) a catalyst composition comprising at least one α,β-unsaturated carboxylate salt wherein the at least one α,β-unsaturated carboxylate salt has the formula:

wherein X, Y, and Z are selected independently from a C 1 -C 36 alkyl, alkenyl, aryl, or aralkyl, any of which are substituted or unsubstituted; —CO 2 H; —CO 2 M; or a hydrogen atom;
wherein M in each occurrence is
a tetraalkylammonium ion, selected from the group of tetramethylammonium, tetraethylammonium, tetrapropylammonium, tetrabutylammonium, and combinations thereof.

2. The composition of claim 1 , wherein X, Y, and Z are selected independently from a hydrogen atom, methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, tolyl, benzyl, —CO 2 H, or —CO 2 M.

3. The composition of claim 1 , wherein the tetraalkylammonium ion is tetramethylammonium.

4. The composition of claim 1 , wherein the at least one α,β-unsaturated carboxylate salt is a salt of acrylic acid, methacrylic acid, fumaric acid, maleic acid, or any combination thereof.

5. The composition of claim 1 , wherein the at least one α,β-unsaturated carboxylate salt is, tetramethylammonium acrylate, tetraethylammonium acrylate, tetrapropylammonium acrylate, tetrabutylammonium acrylate, tetramethylammonium methacrylate, tetraethylammonium methacrylate, tetrapropylammonium methacrylate, tetrabutylammonium methacrylate, mono-tetramethylammonium fumarate, bis-tetramethylammonium fumarate, monotetraethylammonium fumarate, bis-tetraethylammonium fumarate, mono-tetrapropylammonium fumarate, bis-tetrapropylammonium fumarate, mono-tetrabutylammonium fumarate, bis-tetrabutylammonium fumarate, monotetramethylammonium maleate, bis-tetramethylammonium maleate, mono-tetraethylammonium maleate, bis-tetraethylammonium maleate, mono-tetrapropylammonium maleate, bis-tetrapropylammonium maleate, monotetrabutylammonium maleate, bis-tetrabutylammonium maleate, or any combination thereof.

6. The composition of claim 5 , wherein the at least one α,β-unsaturated carboxylate salt is, tetramethylammonium acrylate, tetramethylammonium maleate, or any combination thereof.

7. The composition of claim 1 , further comprising at least one urethane catalyst.

8. The composition of claim 1 , further comprising at least one additive selected from at least one cell stabilizer, at least one flame retardant, at least one chain extender, at least one epoxy resin, at least one acrylic resin, at least one filler, at least one pigment, or any combination thereof.

9. The composition of claim 1 , wherein the catalyst composition comprising at least one α,β-unsaturated carboxylate salt is thermally stable at a temperature up to about 150° C.

10. The composition of claim 1 , wherein the at least one active hydrogen-containing compound is at least one polyether polyol, at least one polyester polyol, or any combination thereof.

11. A composition comprising the contact product of:
(a) at least one polyisocyanate; and
(b) a catalyst composition comprising at least one α,β-unsaturated carboxylate salt wherein the at least one α,β-unsaturated carboxylate salt has the formula:

wherein X, Y, and Z are selected independently from a C 1 -C 36 alkyl, alkenyl, aryl, or aralkyl, any of which are substituted or unsubstituted; —CO 2 H; —CO 2 M; or a hydrogen atom;
wherein M in each occurrence is
a tetraalkylammonium ion, selected from the group of tetramethylammonium, tetraethylammonium, tetrapropylammonium, tetrabutylammonium and combinations thereof.

12. The composition of claim 11 , wherein the at least one polyisocyanate comprises diphenyl methane diisocyanate.

Assignees

• Evonik Degussa Gmbh

Inventors

• Burdeniuc Juan Jesus
• Panitzsch Torsten
• Dewhurst John Elton

Classifications

• C08G18/168 Primary

  Organic compounds · CPC title

• C08G18/1875

  containing ammonium salts or mixtures of secondary of tertiary amines and acids · CPC title

• C08G18/225

  of alkali or alkaline earth metals · CPC title

• C08G18/42

  Polycondensates having carboxylic or carbonic ester groups in the main chain · CPC title

• C08G18/14

  Manufacture of cellular products · CPC title