Process for producing porous materials based on isocyanate

Patent metadata

Field	Value
Publication number	US-9321876-B2
Application number	US-201314033708-A
Country	US
Kind code	B2
Filing date	Sep 23, 2013
Priority date	Sep 27, 2012
Publication date	Apr 26, 2016
Grant date	Apr 26, 2016

Abstract

The present invention relates to a process for producing porous materials, which comprises reaction of at least one polyfunctional isocyanate with at least one polyfunctional aromatic amine in the presence of at least one catalyst and a solvent. The invention further relates to the porous materials which can be obtained in this way and the use of the porous materials as insulation material, in particular for applications in the building sector and in vacuum insulation panels.

First claim

The invention claimed is:

1. A process for producing a porous material, the process comprising reacting:
(a1) from 25 to 94.9% by weight of at least one polyfunctional isocyanate;
(a2) from 0.1 to 30% by weight of at least one polyfunctional aromatic amine having the general formula (I);

wherein:
R 1 and R 2 can be identical or different and are each selected independently from among hydrogen and linear or branched alkyl groups having from 1 to 6 carbon atoms; and
all substituents Q 1 to Q 5 and Q 1 ′ to Q 5 ′ are identical or different and are each selected independently from among hydrogen, a primary amino group and a linear or branched alkyl group having from 1 to 12 carbon atoms, where the alkyl group can bear further functional groups,
with the proviso that the amine of formula (I) comprises at least two primary amino groups, where at least one of Q 1 , Q 3 , and Q 5 is a primary amino group and at least one of Q 1 ′, Q 3 ′, and Q 5 ′ is a primary amino group;

(a3) from 5 to 30% by weight of at least one catalyst,

in each case based on the total weight of the components (a1) to (a3),
wherein the % by weight of the components (a1) to (a3) add up to 100% by weigh,
wherein no water is present, and
wherein the reaction is occurs in the presence of a solvent (C) which is removed after the reaction.

2. The process according to claim 1 which comprises reacting
from 35 to 93.8% by weight of component (a1),
from 0.2 to 25% by weight of component (a2), and
from 6 to 30% by weight of component (a3),

in each case based on the total weight of the components (a1) to (a3), where the % by weight of the components (a1) to (a3) add up to 100% by weight.

3. The process according to claim 1 , wherein at least 5% by weight and at most 20% by weight of component (a2) are used, based on the total weight of the components (a1) to (a3).

4. The process according to claim 1 , which comprises reacting
from 52 to 92.5% by weight of component (a1),
from 0.5 to 18% by weight of component (a2), and
from 7 to 24% by weight of component (a3),

in each case based on the total weight of the components (a1) to (a3), where the % by weight of the components (a1) to (a3) add up to 100% by weight.

5. The process according to claim 1 , wherein Q 2 , Q 4 , Q 2 ′ and Q 4 ′ are selected so that the aromatic amine (a2) having the general formula (I) comprises at least two primary amino groups which each have a linear or branched alkyl group which can bear further functional groups, having from 1 to 12 carbon atoms, in the α position relative to at least one primary amino group bound to the aromatic ring.

6. The process according to claim 1 , wherein the amine component (a2) comprises at least one compound selected from the group consisting of 3,3′,5,5′-tetraalkyl-4,4′-diaminodiphenylmethane, 3,3′,5,5′-tetraalkyl-2,2″-diaminodiphenylmethane and 3,3′,5,5′-tetraalkyl-2,4′-diaminodiphenylmethane, where the alkyl groups in the 3, 3′, 5 and 5′ positions can be identical or different and are selected independently from among linear or branched alkyl groups which have from 1 to 12 carbon atoms and can bear further functional groups.

7. The process according to claim 1 , wherein the alkyl groups of the polyfunctional aromatic amines (a2) having the general formula (I) are selected from among methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and tert-butyl.

8. The process according to claim 1 , wherein polyfunctional aromatic amines (a2) having the general formula (I) e 3,3′,5,5′-tetraalkyl-4,4′-diaminodiphenylmethanes, preferably 3,3′,5,5′-tetraethyl-4,4′-diaminodiphenylmethane and/or 3,3′,5,5′-tetramethyl-4,4′-diaminodiphenylmethane.

9. The process according to claim 1 , wherein component (a3) is selected from the group consisting of primary, secondary and tertiary amines, triazine derivatives, metal-organic compounds, metal chelates, oxides of phospholenes, quaternary ammonium salts, ammonium hydroxides and alkali metal and alkaline earth metal hydroxides, alkoxides and carboxylates.

10. The process according to claim 1 , wherein component (a3) is selected from the group consisting of dimethylcyclohexylamine, bis(2-dimethylaminoethyl) ether, N,N,N,N,N-pentamethyldiethylenetriamine, methylimidazole, dimethylimidazole, aminopropylimidazole, dimethylbenzylamine, 1,6-diazabicyclo[5.4.0]undec-7-ene, trisdimethylaminopropylhexahydrotriazine, triethylamine, tris(dimethylaminomethyl)phen 1, triethylenediamine(diazabicyclo[2.2.2]octane), dimethylaminoethanolamine, dimethylaminopropylamine, N,N-dimethylaminoethoxyethanol, N,N,N-trimethylaminoethylethanolamine, triethanolamine, diethanolamine, triisopropanolamine, diisopropanolamine, methyldiethanolamine, butyldiethanolamine, metal acetylacetonates, ammonium ethylhexanoates and metal ethylhexanoates.

11. The process according to claim 1 , wherein component (a3) is selected from the group consisting of alkali metal carboxylates, alkaline earth metal carboxylates and ammonium carboxylates.

12. The process according to claim w component (a3) comprises potassium 2-ethylhexanoate.

13. The process according to claim 1 , comprising:
a) reacting the components (a1), (a2), and (a3) in the solvent (C), to form a gel; and
b) drying of the gel.

14. The process according to claim 13 , wherein the components (a1) and (a2) to (a3) are provided separately, in each case in a partial amount of the solvent (C).

15. The process according to claim 13 , wherein the drying of the gel occurs by converting a liquid comprised in the gel into the gaseous state at a temperature and a pressure below the critical temperature and the critical pressure of the liquid comprised in the gel.

16. The process according to claim 13 , wherein the drying of the gel occurs under supercritical conditions.

17. A porous material obtained by the process of claim 1 .

18. An insulation material or a vacuum insulation panel, comprising the porous material of claim 17 .

Assignees

• Basf Se

Inventors

• Fricke Marc
• Elbing Mark

Classifications

• C08J9/28

  by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum · CPC title

• C08J2201/0502

  the liquid phase being organic · CPC title

• C08G2101/0091

  Chemistry & Metallurgy · mapped topic

• C08J2375/04

  Polyurethanes · CPC title

• C08G18/2063

  having two nitrogen atoms in the condensed ring system · CPC title