Trimer catalyst additives for improving foam processability

Patent metadata

Field	Value
Publication number	US-9878318-B2
Application number	US-201314021083-A
Country	US
Kind code	B2
Filing date	Sep 9, 2013
Priority date	May 4, 2006
Publication date	Jan 30, 2018
Grant date	Jan 30, 2018

Abstract

The present invention provides trimerization catalyst compositions and methods to produce a polyisocyanurate/polyurethane foam using such trimerization catalyst compositions. The catalyst composition is the contact product of at least one α,β-unsaturated carboxylate salt and at least one second carboxylate salt.

First claim

The invention claimed is:

1. A catalyst composition comprising the contact product of
a) at least one α,β-unsaturated carboxylate salt having a 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 1 ; or a hydrogen atom; and
wherein M 1 in each occurrence is a tetraalkylammonium ion selected from the group consisting of tetramethylammonium, tetraethylammonium, tetrapropylammonium, tetrabutylammonium and combinations thereof; and

b) at least one second carboxylate salt;

wherein the catalyst composition is thermally stable at a temperature up to about 150° C.

2. The catalyst 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 1 .

3. The catalyst 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.

4. The catalyst 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, mono-tetraethylammonium fumarate, bis-tetraethylammonium fumarate, mono-tetrapropylammonium fumarate, bis-tetrapropylammonium fumarate, mono-tetrabutylammonium fumarate, bistetrabutylammonium fumarate, mono-tetramethylammonium maleate, bis-tetramethylammonium maleate, mono-tetraethylammonium maleate, bis-tetraethylammonium maleate, mono-tetrapropylammonium maleate, bistetrapropylammonium maleate, monotetrabutylammonium maleate, bis-tetrabutylammonium maleate, or any combination thereof.

5. The catalyst composition of claim 1 , wherein the catalyst composition, when in the presence of an isocyanate, trimerizes the isocyanate to produce an isocyanurate.

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

7. The catalyst composition of claim 1 , wherein the weight ratio of the at least one α,β-unsaturated carboxylate salt to the at least one second carboxylate salt is from about 0.02:1 to about 50:1.

8. The catalyst composition of claim 7 , wherein the weight ratio of the at least one α,β-unsaturated carboxylate salt to the at least one second carboxylate salt is from about 0.05:1 to about 20:1.

9. The catalyst composition of claim 8 , wherein the weight ratio of the at least one α,β-unsaturated carboxylate salt to the at least one second carboxylate salt is from about 0.1:1 to about 10:1.

10. The catalyst composition of claim 1 , wherein the at least one second carboxylate salt is:
(a) an alkali metal carboxylate salt;
(b) an alkaline earth metal carboxylate salt;
(c) a quaternary ammonium carboxylate salt, or any combination thereof.

11. The catalyst composition of claim 1 wherein the at least one second carboxylate salt is a salt of formic acid, acetic acid, propionic acid, butanoic acid, butyric acid, isobutyric acid, pivalic acid, pentanoic acid, hexanoic acid, neohexanoic acid, heptanoic acid, neoheptanoic acid, octanoic acid, neooctanoic acid, 2-ethyl-hexanoic acid, nonanoic acid, neononanoic acid, decanoic acid, neodecanoic acid, undecanoic acid, neoundecanoic acid, dodecanoic acid, neododecanoic acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, ricinoleic acid, or any combination thereof.

12. The catalyst composition of claim 10 , wherein the at least one second carboxylate salt is potassium pivalate, potassium formate, potassium acetate, potassium propionate, potassium butanoate, potassium pentanoate, potassium hexanoate, potassium neohexanoate, potassium heptanoate, potassium octoate, potassium neooctoate, potassium decanoate, potassium butyrate, potassium isobutyrate, potassium nonante, potassium stearate, potassium neodecanoate, potassium neoheptanoate, sodium octoate, lithium stearate, sodium caprioate, lithium octoate, or any combination thereof.

13. The catalyst composition of claim 12 , wherein the at least one second carboxylate salt is potassium pivalate, potassium acetate, potassium octoate, or any combination thereof.

14. The catalyst composition of claim 1 , wherein the at least one second carboxylate salt has a formula:
A-CO 2 M 2
wherein A is a hydrogen atom, or a C 1 -C 17 alkyl, alkenyl, aryl, or aralkyl, any of which are substituted or unsubstituted; and
wherein M 2 is:
(i) an alkali metal ion,
(ii) an alkaline earth metal ion, or
(iii) a quaternary ammonium ion.

15. The catalyst composition of claim 14 , wherein A is a hydrogen atom, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, or octyl.

16. The catalyst composition of claim 14 , wherein M 2 is an ion of lithium, potassium, sodium, rubidium, magnesium, or calcium, or a quaternary ammonium ion.

17. The catalyst composition of claim 16 , wherein M 2 is a potassium ion.

18. The catalyst composition of claim 16 , wherein the quaternary ammonium ion is tetramethylammonium, tetraethylammonium, tetrapropylammonium, or tetrabutylammonium.

19. The catalyst composition of claim 1 wherein the contact product comprises tetramethylammonium acrylate and at least one second carboxylate salt having a formula:
A-CO 2 M 2 ,
wherein: A is a hydrogen atom, or a C 1 -C 17 alkyl, alkenyl, aryl, or aralkyl, any of which are substituted or unsubstituted; and M 2 is:
(i) an alkali metal ion, or,
(ii) a quaternary ammonium ion.

20. The catalyst composition of claim 1 wherein the contact product comprises tetramethylammonium acrylate; and at least one member selected from the group consisting of potassium pivalate, potassium acetate, and potassium octoate.

21. The catalyst composition of claim 1 wherein the contact product comprises at least one α,β-unsaturated carboxylate salt having 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 1 ; or a hydrogen atom; and M 1 in each occurrence is tetraalkylammonium ion selected from the group consisting of tetramethylammonium, tetraethylammonium, tetrapropylammonium, tetrabutylammonium and combinations thereof, and wherein the at least one α,β-unsaturated carboxylate salt comprises a salt of at least one of acrylic acid and methacrylic acid; and at least one second carboxylate salt having a formula
A-CO 2 M 2

wherein: A is a hydrogen atom, or a C 1 -C 17 alkyl, alkenyl, aryl, or aralkyl, any of which are substituted or unsubstituted; and M 2 is potassium or a quaternary ammonium ion, and the second carboxylate salt comprises a salt of at least one acid selected from the group consisting of formic, acetic, propionic, butanoic, butyric, isobutyric, pivalic, pentanoic, hexanoic, neohexanoic, heptanoic, neoheptanoic, octanoic, neooctanoic, 2-ethyl-hexanoic, nonanoic, neononanoic, decanoic, neodecanoic, undecan

Assignees

• Evonik Degussa Gmbh

Inventors

• Burdeniuc Juan Jesus
• Panitzsch Torsten
• Dewhurst John Elton
• Vedage Gamini Ananda

Classifications

• C08G18/42

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

• C08G18/225

  of alkali or alkaline earth metals · CPC title

• C08J2375/04

  Polyurethanes · CPC title

• C08J9/141

  Hydrocarbons · CPC title

• B01J2231/34

  Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N · CPC title