Preparation of poly(octatriazacane)

Patent metadata

Field	Value
Publication number	US-9296862-B2
Application number	US-201414566921-A
Country	US
Kind code	B2
Filing date	Dec 11, 2014
Priority date	Jun 16, 2014
Publication date	Mar 29, 2016
Grant date	Mar 29, 2016

Abstract

A polyoctatriazacane molecule is disclosed that has a plurality of octatriazacane groups having the structure

and a plurality of divalent bridging groups, each divalent bridging group comprising an aromatic group.

First claim

What is claimed is:

1. A method, comprising:
forming a reaction mixture comprising a i) solvent, ii) an aldehyde, and iii) a monomer comprising two primary aromatic amine groups; and
forming a polyoctatriazacane by adding formic acid to the reaction mixture.

2. The method of claim 1 , wherein the solvent is selected from the group consisting of N-methylpyrollidone (NMP), propylene carbonate (PC), dimethylacetamide (DMA), dimethylsulfoxide (DMSO), propylene glycol methyl ether acetate (PGMEA), dimethylformamide (DMF), and combinations thereof.

3. The method of claim 1 , wherein the monomer is selected from the group consisting of p-phenylenedianiline, 4,4′-methylenedianiline (MDA), p-phenylenediamine (PD), 4,4′-(9-fluorenylidenyl)dianiline (FDA), and combinations thereof.

4. The method of claim 1 , wherein the polyoctatriazacane comprises:
a plurality of octatriazacane groups having the structure

 and
a plurality of divalent bridging groups, each divalent bridging group comprising an aromatic group, wherein each divalent bridging group is covalently bonded to an octatriazacane group at one of the starred bonds.

5. The method of claim 4 , wherein each divalent bridging group has the general structure

wherein R 1 , R 2 , R 3 , and R 4 are each, individually, H, Cl, CN, F, NO 2 , SO 3 , imides, benzoxazoles, benzimidazoles, phenylquinoxalines, C x H 2x+1-y R 5 y , or C 6 H 5-a R 5 a , wherein R 5 is Cl, F, SO 3 , C 6 H 5-a R 6 a , or NH 3-b R 6 b , wherein R 6 is C x H 2x+1 , C x H 2x , or C 6 H 5 , where in each instance x is an integer from 1 to 4, y is an integer from 0 to 2x+1, a is an integer from 0 to 5, and b is an integer from 0 to 3; or the general structure

wherein L′ is a divalent linking group selected from the group consisting of *—SO 2 —*, *—N(R′)—*, *—N(H)—*, *—CF 2 —*, *—C(CF 3 ) 2 )—*, —R″—, and combinations thereof, wherein R′ and R″ independently comprise at least 1 carbon.

6. The method of claim 5 , wherein the divalent linking group comprises fluorine.

7. The method of claim 5 , wherein L′ is a hydrocarbyl group having from 1 to 4 carbon atoms.

8. The method of claim 5 , wherein the aldehyde is formaldehyde or paraformaldehyde.

9. The method of claim 1 , wherein the reaction mixture is coated onto a substrate before adding the formic acid.

10. The method of claim 4 , wherein the polyoctatriazacane further comprises a plurality of diluent groups having a structure selected from the group consisting of

wherein W′ is a monovalent radical selected from the group consisting of —N(R1)(R2), —OR3, and —SR4, wherein R1, R2, R3, and R4 are independent monovalent radicals comprising at least 1 carbon, and wherein the starred bond is linked to a nitrogen of an octatriazacane group.

11. The method of claim 10 , wherein the diluent group is:

Assignees

• IBM

Inventors

• Boday Dylan J
• Garcia Jeannette M
• Hedrick James L
• Wojtecki Rudy J

Classifications

• C08L61/00

  Compositions of condensation polymers of aldehydes or ketones (with polyalcohols C08L59/00; with polynitriles C08L77/00); Compositions of derivatives of such polymers · CPC title

• C08L61/32

  Modified amine-aldehyde condensates · CPC title

• C08G73/0273 Primary

  Polyamines containing heterocyclic moieties in the main chain · CPC title

• C09D179/02

  Polyamines · CPC title

• C09D179/04

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors · CPC title