# US 11,078,320 B2 · Porous materials based on aromatic amines

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- Number: US 11,078,320 B2
- Document ID: US11078320B2
- Status: Granted
- Kind: B2
- Application number: 13/515,139
- Filed: 2010-12-06
- Published: 2012-12-06
- Granted: 2021-08-03
- Earliest claimed: 2009-12-11
- Assignees: BASF SE
- Applicants: Marc Fricke; Mark Elbing
- Inventors: Marc Fricke; Mark Elbing
- Web page: https://patentgrep.com/patent/US11078320B2

## CPC

- C08G 18/3243: {containing two or more aromatic rings}
- C08J 9/286: {the liquid phase being a solvent for the monomers but not for the resulting macromolecular composition, i.e. macroporous or macroreticular polymers}
- C08G 2110/0091: Aerogels; Xerogels
- C08G 2330/50: Evacuated open-celled polymer material
- C08J 2201/0502: the liquid phase being organic
- C08J 2375/02: Polyureas
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)

## Abstract

The invention relates to a porous material comprising at least one polyfunctional isocyanate (a1) and at least one polyfunctional substituted aromatic amine (a2-s) of the general formula (I): where R1 and R2 are selected from among hydrogen and linear or branched alkyl groups having from 1 to 6 carbon atoms and all substituents Q1 to Q5 and Q1′ to Q5′ are selected from among hydrogen, a primary amino group and a linear or branched alkyl group having from 1 to 12 carbon atoms, where at least one of Q1, Q3 and Q5 and at least one of Q1′, Q3′ and Q5′ is a primary amino group and the compound has at least one linear or branched alkyl group having from 1 to 12 carbon atoms in the α position relative to at least one primary amino group bound to the aromatic ring in formula (I).

## Claims

### Claim 1

A porous material comprising, in reacted form:
(a1) a polyfunctional isocyanate; and
(a2) a polyfunctional substituted aromatic amine (a2-s) of formula (I):
wherein:
R1 and R2 are each hydrogen; and
Q1 and Q1′ are each a primary amino group;
Q3, Q3′, Q5, Q5′ are each hydrogen; and
Q2, Q2′, Q4 and Q4′ are each independently a linear or branched alkyl group comprising from 1 to 12 carbon atoms, and
wherein the component (a2) optionally comprises a further polyfunctional amine which is different from the amine (a2-s) of formula (I) and is selected from the group consisting of a polyfunctional aliphatic amine (a2-a) and polyfunctional aromatic amine (a2-u),
wherein the polyfunctional aromatic amine (a2-u) is selected from the group consisting of isomers and derivatives of diaminodiphenylmethane and isomers and derivatives of toluenediamine,
wherein the polyfunctional aliphatic amine (a2-a) is a polyalkylenepolyamine,
wherein the porous material is in the form of a xerogel and has a volume-weighted average pore diameter of at least 1.4 μm and at most 4 μm,
wherein the porous material comprises, in reacted form, from 35 to 65% by weight of the isocyanate component (a1) and from 35 to 65% by weight of the amine component (a2), where a sum of the % by weight of the components (a1) and (a2) is 100% by weight,
wherein the porous material has a porosity of at least 85% by volume and a pore volume of 5.5 to 6.3 mL/g,
wherein the porous material has a density of 100 to 200 g/L, and
wherein the component (a1) is at least one polyfunctional isocyanate selected from the group consisting of diphenylmethane 4,4′-diisocyanate, diphenylmethane 2,4′-diisocyanate, diphenylmethane 2,2′-diisocyanate, and oligomeric diphenylmethane diisocyanate.

### Claim 2 (depends on 1)

The porous material of claim 1, wherein the alkyl groups of the polyfunctional aromatic amine (a2-s) of formula (I) are selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl.

### Claim 3 (depends on 1)

The porous material of claim 1, wherein the polyfunctional aromatic amine (a2-u) is selected from the group consisting of a 4,4′-diaminodiphenylmethane, a 2,4′-diaminodiphenylmethane, a 2,2′-diaminodiphenylmethane, and an oligomeric diaminodiphenylmethane.

### Claim 4 (depends on 1)

The porous material of claim 1, wherein the polyfunctional aromatic amine (a2-u) has a functionality of at least 2.1, and is an oligomeric diaminodiphenylmethane.

### Claim 5 (depends on 1)

The porous material of claim 1, wherein the polyfunctional aromatic amine (a2-s) of formula (I) is a 3,3′,5,5′-tetraethyl-4,4′-diaminodiphenylmethane.

### Claim 6 (depends on 1)

A process for producing the porous material of claim 1, the process comprising:
(a) reacting the components (a1) and (a2) in the presence of a solvent (C), to form a gel; and then
(b) drying the gel, to obtain the porous material.

### Claim 7 (depends on 6)

The process of claim 6, wherein the drying (b) is carried out by converting a liquid comprised in the gel into a gas at a temperature and a pressure below a critical temperature and a critical pressure of the liquid.

### Claim 8 (depends on 6)

The process of claim 6, wherein the drying (b) is carried out under supercritical conditions.

### Claim 9 (depends on 6)

A porous material, obtained by the process of claim 6.

### Claim 10 (depends on 1)

A process for thermally insulating a material, the process comprising incorporating the porous material of claim 1 into an insulation material.

### Claim 11 (depends on 1)

A process for thermally insulating a vacuum insulation panel, the process comprising:
incorporating the porous material of claim 1 into a vacuum insulation panel.