# US 4,400,319 A · Monoazo pigments containing heterocycles, and high-molecular organic materials dyed therewith

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- Number: US 4,400,319 A
- Document ID: US4400319A
- Status: Granted
- Kind: A
- Application number: 06/305,305
- Filed: 1981-09-24
- Granted: 1983-08-23
- Earliest claimed: 1980-10-03
- Assignees: Ciba-Geigy Corporation
- Inventors: Stefan Hari; Arnold Wick
- Web page: https://patentgrep.com/patent/US4400319A

## CPC

- C09B 29/338: {Heterocyclic arylides, e.g. acetoacetylaminobenzimidazolone}
- C09B 29/0025: {from diazotized amino heterocyclic compounds}
- Y10S 534/01: Mixtures of azo compounds
- 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)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

Compounds of the formula I ##STR1## wherein the symbols Z, R.sub.1, R.sub.2, m and n have the meanings defined in claim 1, are suitable, as high-grade pigments, for dyeing high-molecular organic material. They are characterized in particular by good fastness to migration and to cross-lacquering, as well as to weather and light.

## Claims

### Claim 1

A compound of the formula I ##STR8## wherein R.sub.1 is hydrogen, methyl, chlorine, methoxy, ethoxy, phenoxy or C.sub.2 -C.sub.5 -alkoxycarbonyl, R.sub.2 is methyl, chlorine, fluorine, bromine, C.sub.1 -C.sub.4 -alkoxy, phenoxy, methoxycarbonyl, ethoxycarbonyl, carbamoyl, nitro or a group --NHCO--R.sub.3, in which R.sub.3 is a C.sub.1 -C.sub.3 -alkyl group, Z together with the two carbon atoms to whih it is bound forms a 5- or 6-membered heterocyclic ring, where Z is a bivalent radical of the formula --CONHCO--, --CONHCONH--, --CONHCR.sub.5 .dbd.N--, --NHCONR.sub.4 --, --NHCOCONH--, --NR.sub.4 COO--, --NR.sub.4 COS--, --N.dbd.CR.sub.6 O--, --N.dbd.CR.sub.6 S--, --N.dbd.CR.sub.6 NH--, --NHCOCH.dbd.CR.sub.4 -- or --NHCOCH.sub.2 O--, in which R.sub.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, R.sub.5 is hydrogen or a group ##STR9## where R.sub.4 has the meaning defined above, and R.sub.6 is hydrogen, methyl or phenyl, n is 1 or 2, and m is 1, 2 or 3.

### Claim 2 (depends on 1)

A compound according to claim 1 of the formula I wherein m and n are each 1.

### Claim 3 (depends on 1)

A compound according to claim 1 of the formula I wherein R.sub.1 and R.sub.2 have the meanings given in claim 1, and Z is a group --NHCOCH.dbd.CR.sub.4 --, with R.sub.4 being hydrogen or methyl, or Z is a group --CONHCO-- or a group --NHCONR.sub.4 --, where R.sub.4 has the meaning defined in claim 1.

### Claim 4 (depends on 3)

A compound according to claim 3, wherein Z is a group --NHCONH--.

### Claim 5 (depends on 1)

A compound according to claim 1, of the formula II ##STR10## wherein R.sub.1 is methyl, chlorine or methoxy, and R.sub.2 is methyl, chlorine, straight-chain C.sub.1 -C.sub.4 -alkoxy or a group --NHCO--R.sub.3, where R.sub.3 is a C.sub.1 -C.sub.3 -alkyl group.

### Claim 6 (depends on 1)

A compound according to claim 1 of the formula ##STR11##

### Claim 7 (depends on 1)

A compound according to claim 1 of the formula ##STR12##

### Claim 8 (depends on 1)

A compound according to claim 1 of the formula ##STR13##

### Claim 9 (depends on 1)

A compound according to claim 1 of the formula ##STR14##

### Claim 10 (depends on 1)

A compound according to claim 1 of the formula ##STR15##