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

1. A method of making a polyurethane comprising contacting at least one polyisocyanate with at least one active hydrogen-containing compound in the presence of a catalytically effective amount of a catalyst composition under conditions sufficient to produce the polyurethane, the catalyst composition comprising 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 alkyl, alkenyl, aryl, or aralkyl group.

2. The method of claim 1 , wherein the at least one compound has the formula:

wherein:

R 1 is a hydrogen atom or a methyl group; and

R 2 is a methyl, an ethyl, a propyl, a butyl, a pentyl, a hexyl, a heptyl, an octyl, a 2-ethylhexyl, a nonyl, a decyl, a dodecyl, a tetradecyl, a hexadecyl, an octadecyl, a phenyl, a tolyl, or a benzyl group.

3. The method of claim 1 , wherein the at least one compound is:

N,N,N′-trimethyl-N′-(2-hydroxypropyl-butylether)-bis-(aminoethyl) ether;

N,N,N′-trimethyl-N′-(2-hydroxypropyl-hexylether)-bis-(aminoethyl) ether;

N,N,N′-trimethyl-N′-(2-hydroxypropyl-2-ethylhexylether)-bis-(aminoethyl) ether;

N,N,N′-trimethyl-N′-(2-hydroxypropyl-dodecylether)-bis-(aminoethyl) ether;

N,N,N′-trimethyl-N′-(2-hydroxypropyl-tetradecylether)-bis-(aminoethyl) ether;

N,N,N′-trimethyl-N′-(2-hydroxypropyl-hexadecylether)-bis-(aminoethyl) ether; N,N,N′-trimethyl-N′-(2-hydroxypropyl-benzylether)-bis-(aminoethyl) ether;

or any combination thereof.

4. The method of claim 1 , wherein the at least one compound has the formula:

wherein:

R 1 is a hydrogen atom or a methyl group; and

R 3 is a methyl, an ethyl, a propyl, a butyl, a pentyl, a hexyl, a heptyl, an octyl, a 2-ethylhexyl, a nonyl, a decyl, a dodecyl, a tetradecyl, a hexadecyl, an octadecyl, a phenyl, a tolyl, or a benzyl group.

5. The method of claim 1 , wherein the at least one compound is:

N,N,N′-trimethyl-N′-(2-hydroxypropyl-butylester)-bis-(aminoethyl) ether;

N,N,N′-trimethyl-N′-(2-hydroxypropyl-2-ethylhexylester)-bis-(aminoethyl) ether;

N,N,N′-trimethyl-N′-(2-hydroxypropyl-neodecylester)-bis-(aminoethyl) ether;

N,N,N′-trimethyl-N′-(2-hydroxypropyl-dodecylester)-bis-(aminoethyl) ether;

N,N,N′-trimethyl-N′-(2-hydroxypropyl-tetradecylester)-bis-(aminoethyl) ether;

N,N,N′-trimethyl-N′-(2-hydroxypropyl-octadecylester)-bis-(aminoethyl) ether;

N,N,N′-trimethyl-N′-(2-hydroxypropyl-benzylester)-bis-(aminoethyl) ether;

or any combination thereof.

6. The method of claim 1 , wherein the at least one polyisocyanate is diphenyl methane diisocyanate, toluene diisocyanate, or a combination thereof.

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

8. The method of claim 1 , wherein the contacting of the at least one polyisocyanate and the at least one active hydrogen-containing compound occurs in the presence of at least one blowing agent under conditions sufficient to produce a polyurethane foam, wherein the at least one blowing agent is water, methylene chloride, acetone, a chlorofluorocarbon, a hydrofluorocarbon, a hydrochlorofluorocarbon, a hydrocarbon, or any combination thereof.

9. The method of claim 1 , wherein the catalyst composition further comprises at least one gelling urethane catalyst, at least one blowing urethane catalyst, or a combination thereof, wherein the at least one gelling urethane catalyst or the at least one blowing urethane catalyst is not the at least one compound having the formula of claim 1 .