Preparation of poly(octatriazacane)

Patent metadata

Field	Value
Publication number	US-9296863-B2
Application number	US-201414305648-A
Country	US
Kind code	B2
Filing date	Jun 16, 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 polyoctatriazacane, comprising:
a plurality of octatriazacane groups having the structure

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.

2. The polyoctatriazacane of claim 1 , wherein at least one of the divalent bridging groups 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.

3. The polyoctatriazacane of claim 1 , wherein at least one of the divalent bridging groups has 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.

4. The polyoctatriazacane of claim 3 , wherein the at least one divalent bridging group has 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″ are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, phenyl, and combinations thereof.

5. The polyoctatriazacane of claim 3 , wherein L′ is —SO 2 —.

6. The polyoctatriazacane of claim 3 , wherein L′ is —N(R′)—, and R′ is selected from the group consisting of methyl, ethyl, propyl, isopropyl, phenyl, and combinations thereof.

7. The polyoctatriazacane of claim 3 , wherein L′ is a linear hydrocarbyl group having from 1 to 4 carbon atoms.

8. The polyoctatriazacane of claim 2 , wherein at least one of R 1 , R 2 , R 3 , and R 4 is a fluoromethyl group having 1 to 3 fluorine atoms.

9. The polyoctatriazacane of claim 1 , wherein the polyoctatriazacane further comprises a monovalent aromatic group (diluent group) selected from the group consisting of:
formula (8):

and combinations thereof, wherein W′ is a monovalent radical selected from the group consisting of —N(R 1 )(R 2 ), —OR 3 , —SR 4 , wherein R 1 , R 2 , R 3 , and R 4 are monovalent radicals independently comprising at least 1 carbon, and the starred bond in each of formulas (8), (9), (10) and (11) is linked to a nitrogen of a hexahydrotriazine group of the PHT.

10. The polyoctatriazacane of claim 9 , wherein the diluent group is:

Assignees

• IBM

Inventors

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

Classifications

• C08G73/06 Primary

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule · CPC title

• C09D179/04

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

• C08L61/32

  Modified amine-aldehyde condensates · CPC title

• 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

• C08G12/08

  aromatic · CPC title