# US 4,396,545 A · Bis(arylazo)diimides pigments

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- Number: US 4,396,545 A
- Document ID: US4396545A
- Status: Granted
- Kind: A
- Application number: 06/261,398
- Filed: 1981-05-07
- Granted: 1983-08-02
- Earliest claimed: 1981-05-07
- Assignees: Gulf Oil Corporation
- Inventors: Clarence D. Bertino; Robert W. Hill; James E. Owen
- Web page: https://patentgrep.com/patent/US4396545A

## CPC

- C09B 29/06: from coupling components containing amino as the only directing group
- C09B 43/00: Preparation of azo dyes from other azo compounds
- Y10T 428/31855: Of addition polymer from unsaturated monomers
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

The products of the invention are high melting, highly insoluble N,N'-bis(arylazo)diimides prepared by reacting 2 mols of an arylazoaromatic amine with pyromellitic acid dianhydride or 3,3',4,4'-benzophenone tetracarboxylic acid dianhydride. The products are colored and useful as pigments in surface coating compositions and plastics.

## Claims

### Claim 1

An N,N'bis(arylazo)diimide having the structure: ##STR13## where R has the structure: ##STR14## where R.sub.1 is phenylene bearing up to 2 substituents, or naphthylene bearing up to 2 substituents, or has the structure: ##STR15## and where R.sub.2 is phenyl bearing up to 2 substituents, or naphthyl bearing up to 2 substituents, or has the structure: ##STR16## with the further limitation that any substituents on R.sub.1 or R.sub.2 are independently selected from the group consisting of alkyl containing up to 3 carbon atoms, alkoxy containing up to 3 carbon atoms, chlorine, bromine, nitro, trifluoromethyl, cyano, acetyl or benzoyl.

### Claim 2 (depends on 1)

An N,N' bis(arylazo)diimide of claim 1 in which R has the structure: ##STR17##

### Claim 3 (depends on 1)

An N,N' bis(arylazo)diimide of claim 1 in which R has the structure: ##STR18##

### Claim 4 (depends on 1)

An N,N' bis(arylazo)diimide of claim 1 in which R.sub.1 is phenylene and R.sub.2 is phenyl.

### Claim 5 (depends on 2)

An N,N' bis(arylazo)diimide of claim 2 in which R.sub.1 is phenylene group and R.sub.2 is phenyl group.

### Claim 6 (depends on 3)

An N,N' bis(arylazo)diimide of claim 3 in which R.sub.1 is phenylene and R.sub.2 is phenyl.

### Claim 7 (depends on 4)

A bis(arylazo)diimide of claim 4 in which neither the phenyl nor the phenylene bears a substituent.

### Claim 8 (depends on 6)

A bis(arylazo)diimide of claim 6 in which the phenyl bears an acetyl substituent.

### Claim 9 (depends on 8)

A bis(arylazo)diimide of claim 8 in which the phenylene bears a methoxy substituent.

### Claim 10 (depends on 4)

A bis(arylazo)diimide of claim 4 in which the phenyl bears a nitro substituent.

### Claim 11 (depends on 10)

A bis(arylazo)diimide of claim 10 in which the phenylene bears a methoxy substituent.

### Claim 12 (depends on 10)

A bis(arylazo)diimide of claim 10 in which the phenylene bears two methyl substituents.

### Claim 13 (depends on 10)

A bis(arylazo)diimide of claim 10 in which the phenylene bears two methoxy substituents.

### Claim 14 (depends on 6)

A bis(arylazo)diimide of claim 6 in which the phenyl bears one methyl substituent.

### Claim 15 (depends on 14)

A bis(arylazo)diimide of claim 14 in which the phenylene bears one methyl substituent.

### Claim 16 (depends on 7)

A bis(arylazo)diimide of claim 7 in which the phenyl bears one cyano substituent.

### Claim 17 (depends on 16)

A bis(arylazo)diimide of claim 16 in which the phenylene bears one methoxy substituent.

### Claim 18 (depends on 16)

A bis(arylazo)diimide of claim 16 in which the phenylene bears two methoxy substituents.

### Claim 19 (depends on 6)

A bis(arylazo)diimide of claim 6 in which the phenyl bears one chloro substituent.

### Claim 20 (depends on 6)

A bis(arylazo)diimide of claim 6 in which the phenyl bears two methyl substituents.

### Claim 21 (depends on 6)

A bis(arylazo)diimide of claim 6 in which the phenyl bears one nitro substituent and one chloro substituent.

### Claim 22 (depends on 21)

A bis(arylazo)diimide of claim 21 in which the phenylene bears one methoxy substituent.

### Claim 23 (depends on 21)

A bis(arylazo)diimide of claim 21 in which the phenylene bears two methyl substituents.

### Claim 24 (depends on 4)

A bis(arylazo)diimide of claim 4 in which the phenyl bears one chloro substituent and one trifluoromethyl substituent.

### Claim 25 (depends on 24)

A bis(arylazo)diimide of claim 24 in which the phenylene bears one methoxy substituent.

### Claim 26 (depends on 24)

A bis(arylazo)diimide of claim 24 in which the phenylene bears two methyl substituents.

### Claim 27 (depends on 6)

A bis(arylazo)diimide of claim 6 in which the phenyl bears one benzoyl substituent and one chloro substituent.

### Claim 28 (depends on 27)

A bis(arylazo)diimide of claim 27 in which the phenylene bears one methoxy substituent.

### Claim 29 (depends on 27)

A bis(arylazo)diimide of claim 27 in which the phenylene bears two methyl substituents.

### Claim 30 (depends on 6)

A bis(arylazo)diimide of claim 6 in which the phenyl bears one nitro substituent and one methoxy substituent.

### Claim 31 (depends on 30)

A bis(arylazo)diimide of claim 30 in which the phenylene bears two methyl substituents.

### Claim 32 (depends on 4)

A bis(arylazo)diimide of claim 4 in which the phenyl bears one bromo substituent and one nitro substituent.

### Claim 33 (depends on 32)

A bis(arylazo)diimide of claim 32 in which the phenylene bears two methyl substituents.

### Claim 34 (depends on 32)

A bis(arylazo)diimide of claim 32 in which the phenylene bears two methoxy substituents.

### Claim 35 (depends on 6)

A bis(arylazo)diimide of claim 6 in which the phenyl bears one methoxy substituent.

### Claim 36 (depends on 5)

A bis(arylazo)diimide of claim 5 in which neither the phenyl nor the phenylene bears a substituent.

### Claim 37 (depends on 4)

A bis(arylazo)diimide of claim 4 in which the phenylene bears one methoxy substituent.

### Claim 38 (depends on 4)

A bis(arylazo)diimide of claim 4 in which the phenylene contains two methyl substituents.

### Claim 39 (depends on 6)

A bis(arylazo)diimide of claim 6 in which R.sub.2 is naphthyl and R.sub.1 is phenylene.

### Claim 40 (depends on 39)

A bis(arylazo)diimide of claim 39 in which the naphthyl bears one chloro substituent.

### Claim 41 (depends on 4)

A bis(arylazo)diimide of claim 4 in which the phenylene bears one methoxy substituent.

### Claim 42 (depends on 6)

A bis(arylazo)diimide of claim 6 in which R.sub.2 has the structure: ##STR19## and R.sub.1 is phenylene.

### Claim 43 (depends on 42)

A bis(arylazo)diimide of claim 42 in which the phenylene bears one methoxy substituent.

### Claim 44 (depends on 4)

A bis(arylazo)diimide of claim 4 in which the phenylene bears two methoxy substituents.

### Claim 45 (depends on 4)

A bis(arylazo)diimide of claim 4 in which the phenylene bears one methyl substituent.

### Claim 46 (depends on 3)

A bis(arylazo)diimide of claim 3 in which R.sub.1 is naphthylene.