# US 5,352,760 A · Polymerization of oligomeric multiple aromatic ether-containing phthalonitriles

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- Number: US 5,352,760 A
- Document ID: US5352760A
- Status: Granted
- Kind: A
- Application number: 08/019,373
- Filed: 1993-02-18
- Granted: 1994-10-04
- Earliest claimed: 1993-02-18
- Assignees: The United States of America as represented by the Secretary of the Navy
- Inventors: Teddy M. Keller
- Web page: https://patentgrep.com/patent/US5352760A

## CPC

- C08G 65/48: Polymers modified by chemical after-treatment
- C08G 65/4012: {Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Oligomeric monomers are produced by reaction of a bisphenol compound with ther a dihalobenzophenone or a (2, 2) bis (4-halophenyl) hexafluoropropane and any other activated halogen containing aromatic compounds in the presence of a base and an appropriate solvent. The resulting oligomeric product, a dialkaline bisphenate terminated salt, is then reacted with 4-nitrophthalonitrile to form an oligomer-based phthalonitrile. These oligomers, in the presence or absence of an curing agent, may then be heated to form high temperature thermosetting polymers. These polymers can potentially be used as advanced materials for composites, as adhesives, and for microelectronic applications.

## Claims

### Claim 1

A phthalonitrile polymer obtained by heating an oligomeric arylether-containing phthalonitrile monomer having the formula: ##STR7## wherein Ar represents an aromatic group, R represents ##STR8## R' represents ##STR9## y is an integer having a value of 0 to 4; and n represents an average value of from 1 to about 100.

### Claim 2 (depends on 1)

The phthalonitrile polymer of claim 1, wherein Ar has from 1 to 3 aromatic rings, attached or fused, said rings being attached directly or through an aliphatic group, sulfur or oxygen.

### Claim 3 (depends on 1)

The phthalonitrile polymer of claim 1, wherein Ar represents a unit selected from the group consisting of phenylene, diphenylene, terphenylene, anthracenediyl, naphthalendiyl, and phenanthrenediyl.

### Claim 4 (depends on 3)

The phthalonitrile polymer of claim 3, wherein Ar is a phenylene unit or diphenylene unit.

### Claim 5 (depends on 1)

The phthalonitrile polymer of claim 1, wherein Ar is selected from the group consisting of: ##STR10## wherein X is selected from the group consisting of --O--, --, --CO--, ##STR11## and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are selected from the group consisting of hydrogen, fluoride, methyl and ethyl, and R.sub.9 is selected from the group consisting of bromine, chlorine and fluorine.

### Claim 6 (depends on 5)

The phthalonitrile polymer of claim 5, wherein R.sub.1 through R.sub.8 are hydrogen.

### Claim 7 (depends on 5)

The phthalonitrile polymer of claim 5, wherein X is selected from the group consisting of --O--, --, --CO--, ##STR12##

### Claim 8 (depends on 7)

The phthalonitrile polymer of claim 7, wherein X is selected from the group consisting of: ##STR13##

### Claim 9 (depends on 7)

The phthalonitrile polymer of claim 7, wherein X is selected from the group consisting of: ##STR14##