# US 2008/0184499 A1 · Phthalimidyl-azo dyes, process for their preparation and their use

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- Number: US 2008/0184499 A1
- Document ID: US20080184499A1
- Status: Published application
- Kind: A1
- Application number: 12/059,344
- Filed: 2008-03-31
- Published: 2008-08-07
- Earliest claimed: 2002-11-11
- Assignees: Huntsman International LLC
- Inventors: Antoine CLEMENT; Alfons ARQUINT; Urs LAUK
- Web page: https://patentgrep.com/patent/US20080184499A1

## CPC

- C09B 29/0003: {from diazotized anilines}
- C09B 29/0033: {containing a five-membered heterocyclic ring with one nitrogen atom}
- C09B 29/0809: {substituted amino group}
- C09B 43/42: by substituting radicals containing hetero atoms for —CN radicals
- C09B 67/0051: {mixture of two or more monoazo 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

The present invention relates to dyes of formula wherein R1 is 2-methoxyethyl, 2-ethoxyethyl or 2-(2-ethoxyethoxy)ethyl, R2 is C1-C6alkyl which is unsubstituted or substituted by one or more hydroxy groups, halogen atoms, C1-C4alkoxy groups, C2-C8alkoxyalkoxy groups, C1-C4alkyl-COO— groups or C1-C4alkyl-OCO— groups, R3 is methyl, hydroxy, halogen, —NH—SO2—R5 or —NH—CO—R6, wherein R5 is methyl or ethyl and R6 is methyl, ethyl, methoxymethyl or 2-methoxyethyl, and R4 is ethyl or n-propyl, and also to a process for their preparation and to their use in the dyeing or printing of semi-synthetic and, especially, synthetic hydrophobic fibre materials, more especially textile materials.

## Claims

### Claim 1

A dye of formula
wherein R1 is 2-methoxyethyl, 2-ethoxyethyl or 2-(2-ethoxyethoxy)ethyl,
R2 is C1-C6alkyl which is unsubstituted or substituted by one or more hydroxy groups, halogen atoms, C1-C4alkoxy groups, C2-C8alkoxyalkoxy groups, C1-C4alkyl-COO— groups or C1-C4alkyl-OCO— groups,
R3 is methyl, hydroxy, halogen, —NH—SO2—R5 or —NH—CO—R6, wherein R5 is methyl or ethyl and R6 is methyl, ethyl, methoxymethyl or 2-methoxyethyl, and
R4 is ethyl or n-propyl.

### Claim 2 (depends on 1)

A dye according to claim 1, wherein R1 and R2 are the same.

### Claim 3 (depends on 1)

A dye according to claim 1, wherein R1 is 2-methoxyethyl.

### Claim 4 (depends on 1)

A dye according to claim 1, wherein R3 is —NH—CO—R6.

### Claim 5 (depends on 4)

A dye according to claim 4, wherein R6 is methyl.

### Claim 6 (depends on 1)

A dye according to claim 1, wherein R4 is ethyl.

### Claim 7 (depends on 1)

A dye of formula (1a), (1b) or (1c) according to claim 1

### Claim 8 (depends on 1)

A process for the preparation of a dye of formula (1) according to claim 1, in which a phthalimide of formula
wherein R4 is as defined in claim 1,
is nitrated in the acidic range, the resulting nitro compound is then alkylated and converted by means of reductive treatment into an intermediate of formula
the intermediate of formula (3) is monohalogenated in an acidic medium and then diazotised, coupled to a compound of formula (4)
wherein R1, R2 and R3 are as defined in claim 1, and then the halogen substituent is replaced by cyano.

### Claim 9 (depends on 1)

A dye mixture comprising at least two structurally different dyes of formula (1) according to claim 1.

### Claim 10 (depends on 1)

A method of dyeing or printing a semi-synthetic or synthetic hydrophobic fibre material, in which a dye of formula (1) according to claim 1 is applied to the fibre material or incorporated therein.

### Claim 11 (depends on 10)

A semi-synthetic or synthetic hydrophobic fibre material which has been dyed or printed by the process according to claim 10.

### Claim 12 (depends on 1)

A method of dyeing or printing a semi-synthetic or synthetic hydrophobic fibre material in which a dye mixture comprising at least two structurally different dyes of formula (1) according to claim 1 is applied to the fibre material or incorporated therein.

### Claim 13 (depends on 10)

A semi-synthetic or synthetic hydrophobic textile fibre material which has been dyed or printed by the process according to claim 10.