N,N,N′-trimethyl-bis-(aminoethyl) ether and its derivatives as catalysts for polyurethanes

Patent metadata

Field	Value
Publication number	US-9878317-B2
Application number	US-201213401971-A
Country	US
Kind code	B2
Filing date	Feb 22, 2012
Priority date	Jul 13, 2006
Publication date	Jan 30, 2018
Grant date	Jan 30, 2018

Abstract

The present invention provides compounds produced by the reaction of glycidyl ethers and glycidyl esters with ether compounds including N,N,N′-trimethyl-bis-(aminoethyl)ether. N,N,N′-trimethyl-bis-(aminoethyl)ether and its derivatives can be used as polyurethane catalysts.

First claim

The invention claimed is:

1. A catalyst composition for use with reacting an isocyanate and at least one polyol to produce a polyurethane foam wherein the catalyst composition comprises at least one gelling catalyst comprising at least one compound having the formula:

wherein:
n in each occurrence is selected independently from 1, 2, or 3;
R b is a hydrogen atom;
and at least one blowing catalyst; wherein the blowing catalyst is capable of reacting with an isocyanate, and the catalyst composition has a thermal stability of up to about 150 C; and,
wherein the blowing catalyst comprises at least one compound having the formula:

wherein:
n in each occurrence is selected independently from 1, 2, or 3;
R b is

R 1 is selected independently from a hydrogen atom or a substituted or unsubstituted C 1 -C 5 alkyl or alkenyl group; and
R 2 and R 3 are selected independently from a substituted or unsubstituted C 1 -C 24 alkenyl, aryl, or aralkyl group.

2. The composition of claim 1 wherein R 2 and R 3 are substituted or unsubstituted C 1 -C 24 alkyl, alkenyl, aryl or aralkyl groups.

3. The catalyst 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.

4. The catalyst composition of claim 3 , wherein the at least one additive is a chain extender selected from the group consisting of ethylene glycol and butane diol.

5. The catalyst composition of claim 1 , wherein the at least one polyol comprises at least one polyether polyol, at least one polyester polyol, at least one polymer polyol, or any combination thereof.

6. The catalyst composition of claim 1 , further comprising at least one member selected from the group consisting of triethylenediamine, N-methylimidazole, 1,2-dimethylimidazole, N-methylmorpholine, N-ethylmorpholine, trimethylamine N,N′dimethylpiperazine, 1,3,5-tris(dimethylaminopropyl)hexahydrotriazine, 2,4,6-tris(dimethylaminomethyl)phenol, N-methyldicyclohexylamine, pentamethyldipropylene triamine, N-methyl-N′-(2-dimethylamino)-ethyl-piperazine, tributylamine, dimethylaminocyclohexylamine, pentamethyldipropylene-triamine, triethanolamine, dimethylethanolamine, tris(3-dimethylamino)propylamine, and 1,8 diazabicyclo[5.4.0] undecene.

7. The catalyst 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 epoxy resin, at least one acrylic resin, at least one filler, at least one pigment, or any combination thereof.

8. The catalyst composition of claim 7 , wherein the at least one additive is a flame retardant selected from the group consisting of organophosphorous compounds and non-halogenated compounds.

9. The catalyst composition of claim 1 , wherein the catalyst composition further comprises at least one member selected from the group consisting of metal salt catalysts, and organometallic compounds.

10. The catalyst composition of claim 1 , further comprising at least one member selected from the group consisting of diethanolamine, diisopropanolamine, triethanolamine, and tripropanolamine.

11. The catalyst composition of claim 1 , further comprising at least one silicon surfactant.

12. The catalyst composition of claim 1 , wherein n=2.

13. The catalyst composition of claim 1 wherein the catalyst composition comprises N,N,N′-trimethyl-N′-(2-hydroxypropyl-butylether)-bis-(aminoethyl)ether.

14. The catalyst composition of claim 1 wherein the catalyst composition comprises N,N,N′-trimethyl-N′-(2-hydroxypropyl-2-ethylhexylether)-bis-(aminoethyl)ether.

15. The catalyst composition of claim 1 wherein the catalyst composition comprises N,N,N′-trimethyl-N′-(2-hydroxypropyl-tetradecylether)-bis-(aminoethyl)ether.

16. The catalyst composition of claim 1 wherein the catalyst composition has a thermal stability up to about 120 degrees C.

17. The catalyst composition of claim 1 wherein the catalyst composition has a thermal stability up to about 100 degrees C.

Assignees

• Burdeniuc Juan Jesus
• Wendel Stephan Hermann
• Mitchell John William
• Evonik Degussa Gmbh

Inventors

• Burdeniuc Juan Jesus
• Wendel Stephan Hermann
• Mitchell John William

Classifications

• C08G18/7657

  containing two or more aromatic rings · CPC title

• C08G2101/005

  Chemistry & Metallurgy · mapped topic

• C08G2101/0058

  Chemistry & Metallurgy · mapped topic

• C08G18/1833

  having ether, acetal, or orthoester groups · CPC title

• B01J31/0204

  Ethers · CPC title