IP Library Granted Patent US 9,321,876
Granted Patent B2
US 9,321,876 · App. 14/033,708 · Granted Apr 26, 2016

Process for producing porous materials based on isocyanate

Inventors: Marc Fricke (Osnabrueck, DE); Mark Elbing (Bremen, DE)
Assignee: BASF SE
C08G18/0847C08G18/1825C08G18/2063C08G18/3243C08G18/3819C08G18/7664C08J9/28E04B1/76C08G2101/0066C08G2101/0083C08G2101/0091C08J2201/0502C08J2203/10C08J2205/024C08J2375/04
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Quick Facts
Patent No.
US 9,321,876
App. No.
14/033,708
Granted
Apr 26, 2016
Kind
B2
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.

Claims (39)

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 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 4, 2023
From: BASF SE
To: AEROGEL-IT GMBH
Reel/Frame 064496/0266 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 23, 2013
From: FRICKE, MARC; ELBING, MARK
To: BASF SE
Reel/Frame 031259/0442 →
Continuity (2)
Provisional Application 61706150 · Sep 27, 2012
Related Publication 20140088215A1 · Mar 27, 2014