IP Library Granted Patent US 10,590,228
Granted Patent B2
US 10,590,228 · App. 15/556,841 · Granted Mar 17, 2020

Production of low-emission polyurethanes

Inventors: Thomas Günther (Neuss, DE); Mladen Vidakovic (Duisburg, DE); Collins Wettey (Essen, DE)
Assignee: Evonik Operations GmbH
C08G18/1825C08G18/3206C08G18/3275C08G18/4009C08G18/4072C08G18/4829C08G18/61C08G18/632C08G18/6688C08G18/7621C08G18/7664C08J9/141C08G18/18C08G2101/0008C08G2101/0025C08J2203/14C08J2205/06C08J2205/10
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Quick Facts
Patent No.
US 10,590,228
App. No.
15/556,841
Granted
Mar 17, 2020
Kind
B2
Abstract

The use of a mixture (M) comprising nitrogen compound(s) in the preparation of polyurethanes, especially polyurethane foams, wherein said mixture (M) comprises the following constituents: (a) N,N-dimethylaminopropylamine, at least in an amount of ≥5% by weight, advantageously in an amount of ≥20% by weight, preferably 20%-95% by weight, further preferably 30%-70% by weight, especially 30%-60% by weight, and (b) at least one solvent, especially water, advantageously in a total amount of ≥5% by weight, preferably ≥10% by weight, more preferably 10%-60% by weight, especially 10%-40% by weight, % by weight based in each case on the overall mixture (M), is described.

Claims (26)

1. A polyurethane prepared from an isocyanate component, a polyol component, and a mixture (M) comprising the following constituents:

(a) N,N-dimethylaminopropylamine, in an amount of from 40% to 95% by weight, and

(b) at least one solvent, in an amount of ≥5% by weight,

(c) from a tertiary amine in an amount of from 15% to 60% by weight, wherein the tertiary amine is selected from the group consisting of

2-(dimethylamino)ethanol, 1,1′-{[3-(dimethylamino)propyl]imino}bis-2-propanol, bis(3-dimethylaminopropyl)amine, 1-[bis[3-(dimethylamino)propyl]amino]-2-propanol, 2-(diethylamino)ethanol, 1-(2-hydroxyethyl)pyrrolidine, 2-(2-(dimethylamino)ethoxy)ethanol, 2-(2-(diethylamino)ethoxy)ethanol, 2-(2-(pyrrolidin-1-yl)ethoxy)ethanol, bis(2-dimethylaminoethyl) ether, 1,1′-(oxybis(ethane-2,1-diyl))dipyrrolidine, N-(2-(dimethylamino)ethyl)-N,N′,N′-trimethylethylene-1,2-diamine, N,N,N′,N′-tetramethyl-1,6-hexanediamine, 2-((2-(dimethylamino)ethyl)(methyl)amino)ethanol, 2-((2-(2-(dimethylamino)ethoxy)ethyl)(methyl)amino)ethanol, or N-(2-(2-(dimethylamino)ethoxy)ethyl)-N-methylpropane-1,3-diamine.

2. The polyurethane according to claim 1 , wherein (c) comprises bis(3-dimethylaminopropyl)amine in a total amount of from 35% to 60% by weight, based on the total weight of the mixture (M).

3. The polyurethane according to claim 1 , wherein (c) comprises 1,1′-{[3-(dimethylamino)propyl]imino}bis-2-propanol in a total amount of from 35% to 60% by weight, based on the total weight of the mixture (M).

4. The polyurethane according to claim 2 , wherein (c) comprises 1-[bis[3-(dimethylamino)propyl]amino]-2-propanol in a total amount of from 35% to 60% by weight, based on the total weight of the mixture (M).

5. The polyurethane according to claim 1 , wherein the mixture (M) has a flashpoint of >60° C., measured by the Pensky-Martens method with a closed crucible in accordance with DIN EN ISO 2719:2003-09.

6. The polyurethane according to claim 1 , wherein the mixture (M) comprises

(a) N,N-dimethylaminopropylamine, in an amount of from 50% to 70% by weight, and

(b) water as the at least one solvent, in an amount of ≥5% by weight.

7. The polyurethane according to claim 1 wherein the mixture (M) comprises

(a) N,N-dimethylaminopropylamine, in an amount of from 50% to 95% by weight, and

(b) at least one organic solvent, in a total amount of ≥10% by weight.

8. The polyurethane according to claim 1 wherein the mixture (M) comprises

(a) N,N-dimethylaminopropylamine, in an amount of from 60% to 95% by weight, and

(b) water and/or organic solvent as the at least one solvent in an amount of from 10% to 60% by weight.

9. The polyurethane according to claim 2 , wherein (b) said at least one solvent is an organic solvent, and (c) comprises at least one amine selected from the group consisting of 1,1′-{[3-(dimethylamino)propyl]imino}bis-2-propanol, bis(3-dimethylaminopropyl)amine, and 1-[bis[3-(dimethylamino)propyl]amino]-2-propanol.

10. The polyurethane according to claim 9 , wherein the molar ratio of the total amount of (c) relative to the total amount of isocyanate-reactive groups of the polyol component is from 4×10 −4 :1 to 0.2:1.

11. The polyurethane according to claim 9 , wherein (c) is used in a proportion by mass of 0.01 to 20.0 parts by weight per 100 parts by weight of polyol component.

12. A polyurethane foam comprising the polyurethane of claim 1 .

13. The polyurethane foam according to claim 12 , wherein said polyurethane foam is a rigid polyurethane foam, a flexible polyurethane foam, a viscoelastic foam, a cold-cure foam, a semi-rigid polyurethane foam, a thermoformable polyurethane foam or an integral foam, obtained using the mixture (M) in an amount of 0.005% to 10% by weight, based on the weight of the polyurethane foam.

14. The polyurethane according to claim 1 , wherein the mixture (M) comprises

(a) N,N-dimethylaminopropylamine in an amount of from 70% to 95% by weight, and

(b) water as the at least one solvent in an amount of 10% to 40% by weight.

Assignments (2)
CHANGE OF NAME Recorded Dec 27, 2019
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051428/0710 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 8, 2017
From: GÜNTHER, THOMAS; VIDAKOVIC, MLADEN; WETTEY, COLLINS
To: EVONIK DEGUSSA GMBH
Reel/Frame 043535/0500 →
Priority Claims (1)
EP 15162741 · Apr 8, 2015 · regional
Continuity (1)
Related Publication 20180044463A1 · Feb 15, 2018
Cited By (1)
US 12,595,332