# US 5,350,838 A · High temperature process for preparing fiber reactive dyes

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- Number: US 5,350,838 A
- Document ID: US5350838A
- Status: Granted
- Kind: A
- Application number: 08/014,905
- Filed: 1993-02-08
- Granted: 1994-09-27
- Earliest claimed: 1993-02-08
- Assignees: Hoechst Celanese Corporation
- Inventors: Mark A. Helle; Walter Helmling
- Web page: https://patentgrep.com/patent/US5350838A

## CPC

- C09B 62/4413: {Non-metallized monoazo dyes}
- C07D 251/50: with a halogen atom attached to the third ring carbon atom
- C07D 251/54: Three nitrogen atoms
- C09B 41/006: {characterised by process features}
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A process for preparing monoazo dyes by coupling a aromatic diazonium salt with an amino-4-hydroxy-naphthalene sulfonic acid derivative at a temperature of 40.degree.-85.degree. C. The process of the invention provides a isomerically purer dye.

## Claims

### Claim 1

A process for preparing a monoazo dye of the formula: ##STR7## wherein the amino linking group may be in the 6, or 7 ring position on the naphthalene ring; the moiety D represent a phenylene or naphthylene group; R.sub.1 and R.sub.2 are independently selected from hydrogen, sulfo, phosphato, carboxy, hydroxy, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, aryl and halogen; R.sub.3 and R.sub.4 are independently selected from hydrogen and C.sub.1 to C.sub.4 alkyl and n and n' are independently an integer from 1 to 3; X is selected from chloro, fluoro or --NHCN; Y is --CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --Z wherein Z represent a leaving group capable of being split off in an alkaline medium which comprises contacting a diazonium salt of an aromatic amine and a coupling component of an amino-4-hydroxy-2-naphthalene sulfonic acid derivative at a temperature from 60.degree. to 85.degree. C. wherein said diazonium salt has the formula:
(R.sub.1 .sub.n --D--N.sup.+ .tbd.N
wherein D, R.sub.1 and n are defined above; and wherein said a coupling component has the formula: ##STR8## wherein R.sub.2, R.sub.3, R.sub.4, X, Y and n' are defined above.

### Claim 2 (depends on 1)

A process according to claim 1 where said temperature is from about 60.degree. to 70.degree. C.

### Claim 3 (depends on 1)

A process according to claim 1 wherein R.sub.1 is sulfo; n is 1 or 2; R.sub.2, R.sub.3, R.sub.4 are hydrogen and n' is 1.

### Claim 4 (depends on 1)

A process according to claim 1 wherein said diazonlum salt is selected from the group consisting of diazotized:
aniline-2,5 disulfonic acid,
aniline-2-sulfonic acid,
2-naphthylamine-1,5-disulfonic acid,
anlline-2,4 disulfonic acid,
p-anisidine-2,5 disulfonic acid, and
p-anisidine-2-sulfonic acid.

### Claim 5 (depends on 1)

A process according to claim 1 wherein said amino linking group is in the sixth ring position.

### Claim 6 (depends on 1)

A process according to claim 1 wherein the moiety SO.sub.2 Y is a beta-sulfatoethyl sulfonyl group.

### Claim 7 (depends on 1)

A process according to claim 1 wherein said monoazo dye has the formula: ##STR9##

### Claim 8 (depends on 1)

A process according to claim 1 wherein said monoazo dye has the formula: ##STR10##

### Claim 9 (depends on 1)

A process according to claim 1 wherein said monoazo dye has the formula: ##STR11##