Porous materials based on aromatic amines

Patent metadata

Field	Value
Publication number	US-11078320-B2
Application number	US-201013515139-A
Country	US
Kind code	B2
Filing date	Dec 6, 2010
Priority date	Dec 11, 2009
Publication date	Aug 3, 2021
Grant date	Aug 3, 2021

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 R 1 and R 2 are selected 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 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 Q 1 , Q 3 and Q 5 and at least one of Q 1′ , Q 3′ and Q 5′ 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).

First claim

The invention claimed is:

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:
R 1 and R 2 are each hydrogen; and
Q 1 and Q 1′ are each a primary amino group;
Q 3 , Q 3′ , Q 5 , Q 5′ are each hydrogen; and
Q 2 , Q 2′ , Q 4 and Q 4′ 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.

2. 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.

3. 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.

4. 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.

5. 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.

6. 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.

7. 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.

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

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

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

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

Assignees

• Fricke Marc
• Elbing Mark
• Basf Se

Inventors

• Fricke Marc
• Elbing Mark

Classifications

• C08J2375/02

  Polyureas · CPC title

• C08J9/00

  Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof (mechanical aspects of shaping of plastics or substances in a plastic state for the production of porous or cellular articles B29C) · CPC title

• C08G2110/0091

  Aerogels; Xerogels · CPC title

• C08G2330/50

  Evacuated open-celled polymer material · CPC title

• C08J9/28

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