Amines suitable for use in the manufacture of polyurethanes

Patent metadata

Field	Value
Publication number	US-9505895-B2
Application number	US-201414766015-A
Country	US
Kind code	B2
Filing date	Jan 7, 2014
Priority date	Feb 5, 2013
Publication date	Nov 29, 2016
Grant date	Nov 29, 2016

Abstract

The present invention relates to the use of nitrogenous compounds of formula (I) or of corresponding quaternized, or protonated compounds, for producing polyurethanes, to compositions containing these compounds and also to polyurethane systems obtained using the compounds.

First claim

The invention claimed is:

1. A method of producing polyurethane, said method comprising:
reacting at least one polyol component and at least one isocyanate component in the presence of a nitrogenous compound, said nitrogenous compound is a compound of formula (I)

wherein
R is hydrogen or an organic moiety of 1 to 60 carbon atoms with or without heteroatoms,
R 1 in each occurrence is the same or different and is hydrogen or an organic moiety of 1 to 30 carbon atoms with or without oxygen, nitrogen and/or halogen atoms, or is a corresponding quaternized or protonated compound.

2. The method according to claim 1 , wherein said nitrogenous compound of formula (I) is a compound of formula (II)

wherein R is as defined in claim 1 , or is a corresponding quaternized or protonated compound.

3. The method according to claim 1 , wherein R is one of

wherein
m=1 to 20
n=1 to 36
y in each occurrence is the same or different and is 1 to 10, X represents O or NH,
R 2 in each occurrence is the same or different and is —H, —CH 3 , —CH 2 CH 3 or phenyl,
R 3 in each occurrence is the same or different and is —H, alkyl, ester moieties, urethane moieties or amide moieties,
R 4 is C 1 -C 22 alkyl, aryl or alkylaryl,
R 5 is H, C 1 -C 22 alkyl, aryl or alkylaryl with or without OH functions,
R 6 is H or a radical of formula (X):

wherein
R 5 and X are each as defined above.

4. The method according to claim 1 , wherein said nitrogenous compound of formula (I) is a compound of formula (III)

or is a corresponding quaternized or protonated compound.

5. The method according to claim 1 , wherein R is an organic moiety which is reactive with regard to an isocyanate group.

6. The method according to claim 1 wherein said nitrogenous compound catalyzes the reaction of said at least polyol component and said at least one isocyanate component.

7. The method according to claim 1 , wherein reacting provides a polyurethane foam.

8. The method according to claim 1 , wherein a composition of said nitrogenous compound of formula (I), said at least one polyol component, and said at least one isocyanate component is prepared prior to said reacting.

9. A polyurethane system obtained by the method of claim 1 .

10. The polyurethane system according to claim 9 , wherein said polyurethane system is a rigid polyurethane foam, a flexible polyurethane foam, a viscoelastic foam, a high-resilience foam, a semi-rigid polyurethane foam, a thermoformable polyurethane foam or an integral foam.

11. The polyurethane system according to claim 9 , wherein from 0.005 to 10 wt % mass fraction of said nitrogenous compound of formula (I), or of moieties obtained by conversion thereof, is present in a polyurethane foam.

12. A composition comprising:
at least one polyol component, and at least one nitrogenous compound, said at least one nitrogenous compound is a compound of formula (I)

wherein
R in each occurrence is the same or different and is hydrogen or an organic moiety of 1 to 60 carbon atoms with or without heteroatoms,
R 1 in each occurrence is the same or different and is hydrogen or an organic moiety of 1 to 30 carbon atoms with or without oxygen, nitrogen and/or halogen atoms,
or is a corresponding quaternized or protonated compound.

13. The composition according to claim 12 , further comprising at least one isocyanate component.

14. The composition according to claim 12 , wherein a molar ratio of said at least one nitrogenous compound to isocyanate-reactive groups of said polyol component is in a range from 4×10 −4 :1 to 0.2:1.

15. The composition according to claim 12 , further comprising one or more blowing agents.

16. A polyurethane foam comprising from 0.005 to 10 wt % mass fraction base on the entire polyurethane foam of a nitrogenous compound, said nitrogenous compound is a compound of formula (I)

wherein
R in each occurrence is the same or different and is hydrogen or an organic moiety of 1 to 60 carbon atoms with or without heteroatoms,
R 1 in each occurrence is the same or different and is hydrogen or an organic moiety of 1 to 30 carbon atoms with or without oxygen, nitrogen and/or halogen atoms,
or is a corresponding quaternized or protonated compound.

Assignees

• Evonik Degussa Gmbh

Inventors

• Schmitz Sarah
• Glos Martin
• Hubel Roland
• Terheiden Annegret

Classifications

• C08G18/7664 Primary

  containing alkylene polyphenyl groups · CPC title

• C08G18/48

  Polyethers · CPC title

• C08J2205/10

  Rigid foams · CPC title

• C08G18/7614 Primary

  containing only one aromatic ring · CPC title

• C08G18/2081

  containing at least two non-condensed heterocyclic rings · CPC title