# US 8,785,512 B2 · Porous gels based on aromatic and cycloaliphatic amines

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- Number: US 8,785,512 B2
- Document ID: US8785512B2
- Status: Granted
- Kind: B2
- Application number: 13/389,969
- Filed: 2010-08-02
- Published: 2012-06-07
- Granted: 2014-07-22
- Earliest claimed: 2009-08-13
- Assignees: BASF SE
- Applicants: Marc Fricke; Mark Elbing
- Inventors: Marc Fricke; Mark Elbing
- Web page: https://patentgrep.com/patent/US8785512B2

## CPC

- C08G 18/3237: {aromatic (C08G18/3234 takes precedence)}
- C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G 18/12: using two or more compounds having active hydrogen in the first polymerisation step
- C08G 18/3225: {Polyamines}
- C08G 18/3234: {cycloaliphatic}
- 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 2205/02: the finished foam itself being a gel or a gel being temporarily formed when processing the foamable composition
- C08J 2375/12: from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
- 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 gel comprising the following components, in reacted form: (a1) at least one polyfunctional isocyanate, (a2) at least one polyfunctional aromatic amine and (a3) at least one polyfunctional cycloaliphatic amine. The invention further relates to a process for preparing porous gels, to the porous gels thus obtainable and to the use of the porous gels as an insulating material and in vacuum insulation panels.

## Claims

### Claim 1

A porous gel, comprising:
a polyfunctional isocyanate,
a polyfunctional aromatic amine, and
a polyfunctional cycloaliphatic amine,
wherein the porous gel has a porosity of at least 70% by volume, and
the polyfunctional isocyanate, the polyfunctional aromatic amine, and the polyfunctional cycloaliphatic amine are present as polymeric or polymer-bound components.

### Claim 2 (depends on 1)

The porous gel of claim 1, wherein the porous gel is a xerogel.

### Claim 3 (depends on 1)

The porous gel of claim 1, comprising:
from 20 to 90% by weight of the polyfunctional isocyanate,
from 9.99 to 45% by weight of the polyfunctional aromatic amine, and
from 0.01 to 35% by weight of the polyfunctional cycloaliphatic amine,
wherein a sum of total percentages by weight of the polyfunctional isocyanate, the polyfunctional aromatic amine, and the polyfunctional cycloaliphatic amine is 100%.

### Claim 4 (depends on 1)

The porous gel of claim 1,
wherein the polyfunctional cycloaliphatic amine comprises a compound comprising at least two amino groups of a structure comprising a ring,
the structure comprising a ring is of formula:
where R1 to R4 are each independently hydrogen or a linear or branched alkyl group having from 1 to 12 carbon atoms,
the ring is an optionally substituted cycloaliphatic ring, optionally joined to a further cycloaliphatic ring.

### Claim 5 (depends on 1)

The porous gel of claim 1,
wherein the polyfunctional cycloaliphatic amine comprises a compound comprising at least two amino groups, each joined to an optionally substituted cyclohexyl ring, optionally joined directly or indirectly to a further, optionally substituted cyclohexyl ring.

### Claim 6 (depends on 1)

The porous gel of claim 1,
wherein the polyfunctional cycloaliphatic amine comprises a compound of a structure:
and
R1 to R10 are each independently hydrogen or a linear or branched alkyl group having from 1 to 12 carbon atoms.

### Claim 7 (depends on 1)

The porous gel of claim 1,
wherein the polyfunctional cycloaliphatic amine is 3,3′,5,5′-tetraalkyl-4,4′-diaminodicyclohexylmethane,
alkyl groups in the 3,3′,5 and 5′ positions each independently a linear or branched alkyl group having from 1 to 12 carbon atoms.

### Claim 8 (depends on 1)

The porous gel of claim 1, wherein the polyfunctional cycloaliphatic amine is 3,3′,5,5′-tetramethyl-4,4′-diaminodicyclohexylmethane.

### Claim 9 (depends on 1)

The porous gel of claim 1, wherein the polyfunctional aromatic amine consists of at least one polyfunctional aromatic amine selected from the group consisting of 4,4′-diaminodiphenylmethane, 2,4′-diaminodiphenylmethane, 2,2′-diaminodiphenylmethan, and oligomeric diaminodiphenylmethane.

### Claim 10 (depends on 1)

The porous gel of claim 1, wherein the polyfunctional aromatic amine comprises oligomeric diaminodiphenylmethane and has a functionality of at least 2.3.

### Claim 11 (depends on 1)

The porous gel of claim 1, wherein the polyfunctional isocyanate consists of 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 12 (depends on 1)

The porous gel of claim 1, wherein the polyfunctional isocyanate comprises oligomeric diphenylmethane diisocyanate and has a functionality of at least 2.5.

### Claim 13 (depends on 1)

The porous gel of claim 1,
wherein the polyfunctional isocyanate comprises oligomeric diphenylmethane diisocyanate,
the polyfunctional aromatic amine comprises oligomeric diaminodiphenylmethane, and
a sum of a functionality of the polyfunctional isocyanate and of a functionality of the polyfunctional aromatic amine is at least 5.5.

### Claim 14 (depends on 1)

The porous gel of claim 1, wherein a volume-weighted mean pore diameter of the porous gel is at most 3 micrometers.

### Claim 15 (depends on 1)

A process for preparing the porous gel of claim 1, comprising:
providing the polyfunctional isocyanate and, separately therefrom, the polyfunctional aromatic amine and the polyfunctional cycloaliphatic amine, each in a solvent;
converting the polyfunctional isocyanate, the polyfunctional aromatic amine, and the polyfunctional cycloaliphatic amine in the presence of the solvent, to obtain a gel; and
drying the gel.

### Claim 16 (depends on 15)

The process of claim 15, wherein drying the porous gel comprises converting the solvent to a gas at a temperature and a pressure below a critical temperature and a critical pressure of the solvent.

### Claim 17 (depends on 15)

A porous gel obtained by the process of claim 15.

### Claim 18 (depends on 1)

An insulating material, comprising the porous gel of claim 1.

### Claim 19 (depends on 1)

A vacuum insulation panel, comprising the porous gel of claim 1.

### Claim 20 (depends on 1)

The porous gel of claim 1, wherein the porosity is at least 80% by volume.