# US 10,308,765 B2 · Porous/nanoporous PHT

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- Number: US 10,308,765 B2
- Document ID: US10308765B2
- Status: Granted
- Kind: B2
- Application number: 15/399,365
- Filed: 2017-01-05
- Published: 2017-04-27
- Granted: 2019-06-04
- Earliest claimed: 2014-10-16
- Assignees: International Business Machines Corporation
- Applicants: International Business Machines Corporation
- Inventors: Dylan J. Boday; Jeannette M. Garcia; James L. Hedrick; Rudy J. Wojtecki
- Web page: https://patentgrep.com/patent/US10308765B2

## CPC

- C08G 73/0644: {Poly(1,3,5)triazines}
- C08G 73/0638: {with at least three nitrogen atoms in the ring}
- C08G 73/065: {Preparatory processes}
- C08J 9/0085: {Use of fibrous compounding ingredients (C08J9/0076 takes precedence)}
- C08J 9/26: by elimination of a solid phase from a macromolecular composition or article, e.g. leaching out
- C08K 7/06: Elements
- C08L 79/02: Polyamines
- C08G 73/0206: {Polyalkylene(poly)amines}
- C08J 2201/042: Elimination of an organic solid phase
- C08J 2205/042: Nanopores, i.e. the average diameter being smaller than 0,1 micrometer
- C08J 2361/20: Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08J 2361/32: Modified amine-aldehyde condensateS
- C08J 2379/04: Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- 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)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

Methods of forming nanoporous materials are described herein that include forming a polymer network with a chemically removable portion. The chemically removable portion may be polycarbonate polymer that is removable on application of heat or exposure to a base, or a polyhexahydrotriazine (PHT) or polyhemiaminal (PHA) polymer that is removable on exposure to an acid. The method generally includes forming a reaction mixture comprising a formaldehyde, a solvent, a primary aromatic diamine, and a diamine having a primary amino group and a secondary amino group, the secondary amino group having a base-reactive substituent, and heating the reaction mixture to a temperature of between about 50 deg C. and about 150 deg C. to form a polymer. Removing any portion of the polymer results in formation of nanoscopic pores as polymer chains are decomposed, leaving pores in the polymer matrix.

## Claims

### Claim 1

A thermally stable polymer material comprising a porous polyhemiaminal having average pore size less than about 100 nm and density less than about 1.5 g/cm3.

### Claim 2 (depends on 1)

The thermally stable polymer material of claim 1, further comprising carbon fibers.

### Claim 3 (depends on 1)

The thermally stable polymer material of claim 1, wherein the polyhemiaminal is a material having a plurality of hemiaminal units with the general structure
wherein at least one starred bond of each hemiaminal unit is bonded to a hydrogen atom, and at least one starred bond of each hemiaminal unit is bonded to a divalent linking group.

### Claim 4 (depends on 3)

The thermally stable polymer material of claim 3, wherein each divalent linking group has the structure
wherein L′ is a divalent linking group selected from the group consisting of —O—, —S—, —N(R′)—, —N(H)—, —R″—, and combinations thereof, wherein R′ and R″ independently comprise at least 1 carbon, and each starred bond of each divalent linking group is covalently bonded to a respective starred bond of a hemiaminal unit.

### Claim 5

An article comprising a porous polymer having a plurality of hemiaminal units and having average pore size less than about 100 nm and density less than about 1.5 g/cm3.

### Claim 6 (depends on 5)

The article of claim 5, further comprising a plurality of carbon fibers disposed in the porous polymer.

### Claim 7 (depends on 5)

The article of claim 5, wherein the porous polymer has a plurality of hemiaminal units having the general structure
wherein at least one starred bond of each hemiaminal unit is bonded to a hydrogen atom, and at least one starred bond of each hemiaminal unit is bonded to a linking group having the general structure
wherein y′ is 2 or 3, and K′ is a divalent or trivalent radical.

### Claim 8

A thermally stable polymer material comprising:
a porous polyhemiaminal having average pore size less than about 100 nm and density less than about 1.5 g/cm3; and
carbon fibers.