IP Library › Granted Patent US 7,495,131
Granted Patent B2
US 7,495,131 · App. 11/083,452 · Granted Feb 24, 2009

Blowing catalyst compositions containing hydroxyl and surface active groups for the production of polyurethane foams

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Quick Facts
Patent No.
US 7,495,131
App. No.
11/083,452
Granted
Feb 24, 2009
Kind
B2
Abstract

Tertiary amines useful as catalysts for preparing polyurethane foams are provided. Tertiary amines are employed to catalyze the trimerization reaction of isocyanates and the reaction between isocyanates and active hydrogen-containing compounds, such as a polyol and/or a blowing agent. Such tertiary amine has the general formula wherein R 1 , R 2 , Y, Z, and n are defined herein.

Claims (79)

1. A compound having the general formula

wherein

R 1 and R 2 are methyl;

Y is methyl

Z is

R 3 is hydrogen;

R 4 is a substituted or unsubstituted alkyl group having from 1 to about 36 carbon atoms, or a substituted or unsubstituted alkenyl group having from 1 to about 36 carbon atoms; and

n is an integer from 2 to 3, inclusive.

2. A compound according to claim 1 , wherein R 4 is a substituted or unsubstituted alkyl group having from 1 to about 18 carbon atoms, or a substituted or unsubstituted alkenyl group having from 1 to about 18 carbon atoms.

3. A compound according to claim 1 , wherein the compound is

N-(2-hydroxypropyl-octadecyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-heptadecyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-hexadecyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-pentadecyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-tetradecyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-tridecyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-dodecyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-undecyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-decyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-nonyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-octyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-heptyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-hexyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-pentyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-butyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-ethyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-methyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-octadecyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-heptadecyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-hexadecyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-pentadecyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-tetradecyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-tridecyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-dodecyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-undecyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-decyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-nonyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-octyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-heptyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-hexyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-pentyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-butyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-ethyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-methyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine; or any combination thereof.

4. A compound according to claim 3 , wherein the compound is

N-(2-hydroxypropyl-octadecyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-hexadecyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-tetradecyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-dodecyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-decyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-octyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-hexyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-butyl ether)-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine;

N-(2-hydroxypropyl-octadecyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-hexadecyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-tetradecyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-dodecyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-decyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-octyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-hexyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine;

N-(2-hydroxypropyl-butyl ether)-N,N′,N″,N″ tetramethyldiethylenetriamine; or any combination thereof.

5. A compound according to claim 4 , wherein the compound is a mixture of

N-[2-hydroxypropyl-(dodecyl)-ether]-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine and

N-[2-hydroxypropyl-(tetradecyl)-ether]-N,N′,N″,N′″,N′″ pentamethyltriethylenetetramine.

6. A compound according to claim 1 , wherein the compound is produced by reacting an alkyl glycidyl ether with an ethyleneamine.

7. A compound according to claim 6 , wherein the alkyl glycidyl ether is octadecyl glycidyl ether, heptadecyl glycidyl ether, hexadecyl glycidyl ether, pentadecyl glycidyl ether, tetradecyl glycidyl ether, tridecyl glycidyl ether, dodecyl glycidyl ether, undecyl glycidyl ether, decyl glycidyl ether, nonyl glycidyl ether, octyl glycidyl ether, heptyl glycidyl ether, hexyl glycidyl ether, pentyl glycidyl ether, butyl glycidyl ether, ethyl glycidyl ether, methyl glycidyl ether, or any combination thereof.

8. A compound according to claim 6 , wherein the ethyleneamine is diethylenetriamine or triethylenetetramine.

9. A method to produce a compound having the general formula

wherein

R 1 and R 2 are methyl;

Y is methyl

Z is

R 3 is hydrogen;

R 4 is a substituted or unsubstituted alkyl group having from 1 to about 36 carbon atoms, a substituted or unsubstituted alkenyl group having from 1 to about 36 carbon atoms; and

n is an integer from 2 to 3, inclusive;

the method comprising reacting an alkyl glycidyl ether with an ethyleneamine.

10. A method according to claim 9 , wherein the alkyl glycidyl ether has an alkyl group having from 1 to about 35 carbon atoms.

11. A method according to claim 10 , wherein the alkyl group is octadecyl, heptadecyl, hexadecyl, pentadecyl, tetradecyl, tridecyl, dodecyl, undecyl, decyl, nonyl, octyl, heptyl, hexyl, pentyl, butyl, ethyl, or methyl.

12. A method according to claim 9 , wherein the ethyleneamine is diethylenetriamine or triethylenetetramine.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 18, 2017
From: AIR PRODUCTS AND CHEMICALS, INC.
To: EVONIK DEGUSSA GMBH
Reel/Frame 042491/0684 →