# US 5,349,057 A · Water soluble azo dyes containing a cyanoamino-triazinyl-amino group and a fiber-reactive of the sulfone series

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- Number: US 5,349,057 A
- Document ID: US5349057A
- Status: Granted
- Kind: A
- Application number: 07/772,375
- Filed: 1992-01-10
- Granted: 1994-09-20
- Earliest claimed: 1989-05-10
- Assignees: Hoechst Aktiengesellschaft
- Inventors: Holger M. Buch; Hartmut Springer
- Web page: https://patentgrep.com/patent/US5349057A

## CPC

- C09B 62/4411: {Azo dyes}
- 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)

## Abstract

Water-soluble azo dyes and their heavy metal complex derivatives, such as copper, cobalt and chromium complex azo dyes are described, which have the general formula (1) shown below, have fiber-reactive properties and dye natural and synthetic hydroxyl- and/or carboxamido-containing materials, in particular fiber materials, such as wool and in particular cellulose fiber materials, by the dyeing and printing processes customary for fiber-reactive dyes, in hues which have high color strength and good fastness properties. ##STR1##

## Claims

### Claim 1

A water-soluble azo dye of the general formula (4) ##STR38## in which Y is vinyl, .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-alkanoyloxyethyl of 2 to 5 carbon atoms in the alkanoyl radical, .beta.-benzoyloxyethyl, .beta.-(sulfobenzyoxyloxy)ethyl, .beta.-(p-toluenesulfonyloxy)ethyl or .beta.-halogenoethyl;
P is the number 1 or 2
M is hydrogen or an alkali metal,
R.sup.1 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trifluoromethyl, carboxyl or sulfo,
R.sup.2 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen or sulfo,
D.sup.1 is a benzene or naphthalene ring and
Z.sup.1 is a group of the general formula (3a) ##STR39## in which X is chlorine, bromine, sulfo, alkoxysulfonyl of 1 to 4 carbon atoms or phenylsulfonyl.

### Claim 2

A water-soluble azo dye of the general formula (9) ##STR40## in which Y is vinyl, .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-alkanoyloxyethyl of 2 to 5 carbon atoms in the alkanoyl radical, .beta.-benzoyloxyethyl, .beta.-(sulfobenzyoxyloxy)ethyl, .beta.-(p-toluenesulfonyloxy)ethyl or .beta.-halogenoethyl;
P is the number 1 or 2,
M is hydrogen or an alkali metal,
m is the number zero, 1 or 2,
R.sup.1 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trifluoromethyl, carboxyl or sulfo,
R.sup.2 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen or sulfo,
D.sup.1 is a benzene or naphthalene ring and
Z.sup.1 is a group of the general formula (3a) ##STR41## in which X is chlorine, bromine, sulfo, alkoxysulfonyl of 1 to 4 carbon atoms or phenylsulfonyl.

### Claim 3

A water-soluble azo dye of the general formula (4a) ##STR42## in which Y is vinyl, .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-alkanoyloxyethyl of 2 to 5 carbon atoms in the alkanoyl radical, .beta.-benzoyloxyethyl, .beta.-(sulfobenzyoxyloxy)ethyl, .beta.-(p-toluenesulfonyloxy)ethyl or .beta.-halogenoethyl;
P is the number 1 or 2
M is hydrogen or an alkali metal,
R.sup.1 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trifluoromethyl, carboxyl or sulfo,
R.sup.2 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen or sulfo,
D.sup.1 is a benzene or naphthalene ring and
Z.sup.1 is a group of the general formula (3a) ##STR43## in which X is chlorine, bromine, sulfo, alkoxysulfonyl of 1 to 4 carbon atoms or phenylsulfonyl.

### Claim 4 (depends on 1)

A dye as claimed in claim 1 wherein X is chlorine.

### Claim 5 (depends on 2)

A dye as claimed in claim 2, wherein X is chlorine.

### Claim 6 (depends on 3)

A dye as claimed in claim 3, wherein X is chlorine.

### Claim 7 (depends on 1)

A dye as claimed in claim 1, wherein Y is vinyl or .beta.-sulfatoethyl.

### Claim 8 (depends on 2)

A dye as claimed in claim 2, wherein Y is vinyl or .beta.-sulfatoethyl.

### Claim 9 (depends on 3)

A dye as claimed in claim 3, wherein Y is vinyl or .beta.-sulfatoethyl.

### Claim 10 (depends on 1, 2, 3)

A process for dyeing of hydroxyl- and or carboxamido-containing material in which a dye is applied to or incorporated in the material and fixed by means of heat and/or may means of an alkaline agent, wherein the dye used is a compound as claimed in one of claims 1, 2 and 3.

### Claim 11 (depends on 1)

A process for dyeing a material containing hydroxy or carboxamide groups, comprising applying a dye as claimed in claim 1, to the material and fixing it by a means of heat or by a means of alkaline agent or by both.

### Claim 12 (depends on 2)

A process for dyeing a material containing hydroxy or carboxamide groups, comprising applying a dye as claimed in claim 2, to the material and fixing it by a means of heat or by a means of alkaline agent or by both.

### Claim 13 (depends on 3)

A process for dyeing a material containing hydroxy or carboxamide groups, comprising applying a dye as claimed in claim 3, to the material and fixing it by a means of heat or by a means of alkaline agent or by both.

### Claim 14 (depends on 11)

The process as claimed in claim 11, wherein said material is a fiber material.

### Claim 15 (depends on 12)

The process as claimed in claim 12, wherein said material is a fiber material.

### Claim 16 (depends on 13)

The process as claimed in claim 13, wherein said material is a fiber material.