# US 4,400,504 A · Dioxazine reactive dyestuffs

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- Number: US 4,400,504 A
- Document ID: US4400504A
- Status: Granted
- Kind: A
- Application number: 06/320,044
- Filed: 1981-11-10
- Granted: 1983-08-23
- Earliest claimed: 1980-12-02
- Assignees: Bayer Aktiengesellschaft
- Inventors: Wolfgang Harms; Klaus Wunderlich
- Web page: https://patentgrep.com/patent/US4400504A

## CPC

- C09B 62/4401: {with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system}
- C09B 62/0025: {Specific dyes not provided for in groups C09B62/004 - C09B62/018}
- 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 invention relates to new dioxazine reactive dyestuffs of the formula ##STR1## a process for their preparation and their use in dyeing and printing fibre materials which contain hydroxyl groups or amide groups. In formula (I): D denotes a radical of the dioxazine system of the formula ##STR2## the radicals Y, Z, A, X.sub.1 and X.sub.2 as well as m and n having the meaning indicated in the text of the application. The invention further relates to a process for the preparation of these new dioxazine reactive dyestuffs as well as their use in dyeing and printing fibre materials which contain hydroxyl groups or amide groups.

## Claims

### Claim 1

A compound of the formula ##STR253## wherein D denotes a (m+n)-valent radical derived from a dioxazine system of the formula ##STR254## wherein A stands for NH.sub.2 ; ##STR255## unsubstituted or substituted by SO.sub.3 H, OSO.sub.3 H, OH, O-alkyl(C.sub.1 -C.sub.4); NH-cyclohexyl; NH-aryl unsubstituted or substituted by halogen, alkyl(C.sub.1 -C.sub.4), O-alkyl(C.sub.1 -C.sub.4), NH-acetyl, SO.sub.3 H; O-alkyl(C.sub.1 -C.sub.4); O-aryl unsubstituted or substituted by alkyl(C.sub.1 -C.sub.4) or halogen
and wherein
X.sub.1 and X.sub.2 independently of one another denote hydrogen, optionally substituted C.sub.1 -C.sub.4 -alkyl, cycloalkyl, optionally substituted aryl, CN, halogen, COOR.sub.1 (wherein R.sub.1 denotes H, alkyl or cycloalkyl) or CONR.sub.2 R.sub.3 (wherein R.sub.2 and R.sub.3 independently of one another are H, optionally substituted C.sub.1 -C.sub.4 -alkyl, cycloalkyl or optionally substituted aryl), said optional substituents being OH, SO.sub.3 H, COOH or halogen, or wherein
D denotes a (m+n)-valent radical derived from a dioxazine system of the formula ##STR256## wherein B stands for NH, NH-alkyl (C.sub.1 -C.sub.2), O or CH.sub.2 and wherein
X.sub.1 and X.sub.2 have the meanings given above or
wherein
D denotes a (m+n)-valent radical derived from a dioxazine system of the formulae ##STR257## wherein X.sub.1 and X.sub.2 have the meanings given above and wherein Y denotes a bridge member of the formulae ##STR258## wherein R.sub.5 denotes H or C.sub.1 -C.sub.4 -alkyl which may be substituted by OH, SO.sub.3 H or OSO.sub.3 H,
R.sub.6 denotes H or C.sub.1 -C.sub.4 -alkyl which may be substituted by OH, SO.sub.3 H or OSO.sub.3 H,
alkylene denotes alkylene radicals or cycloalkylene radicals having 1 to 6 carbon atoms, which may be interrupted by O or S and which may be substituted by OH, SO.sub.3 H or OSO.sub.3 H, and arylene denotes 1,2-, 1,3- or 1,4-phenylene radicals which may be substitutd by C.sub.1 -C.sub.4 -alkyl, halogen, SO.sub.3 H, COOH or C.sub.1 -C.sub.4 -alkoxy
wherein
m denotes 1 or 2 and
n denotes 0 to 4
and wherein
Z denotes a radical selected from 2,4-dichloro-s-triazinyl, 2,4-dibromo-s-triazinyl, 2-fluoro-4-amino-s-triazinyl, 2-chloro-4-amino-s-triazinyl, 2-bromo-4-amino-s-triazinyl, 2-carboxy-pyridinuim-4-amino-s-triazinyl, 2-fluoro-4-(C.sub.1 -C.sub.4)alkylamino-s-triazinyl, 2-chloro-4-(C.sub.1 -C.sub.4)alkylamino-s-triazinyl, 2-2-bromo-4-(C.sub.1 -C.sub.4)alkylamino-s-triazinyl, 2-fluoro-4-di-(C.sub.1 -C.sub.4)alkylamino-s-triazinyl, 2-chloro-4-di-(C.sub.1 -C.sub.4)alkylamino-s-triazinyl, 2-bromo-4-di-(C.sub.1 -C.sub.4)alkylamino-s-triazinyl, unsubstituted 2-fluoro-, 2-chloro-, 2-bromo-4-arylamino-5-triazinyl, 2-fluoro-, 2-chloro-, 2-bromo-4-arylamino-s-triazinyl substituted by SO.sub.3 H, COOH, SO.sub.2 --CH.sub.2 --CH.sub.2 --OSO.sub.3 H, 2-fluoro-, 2-chloro-, 2-bromo-4-(C.sub.1 -C.sub.4)alkoxy-s-triazinyl, 2-fluoro, 2-chloro-2-bromo-4-aryloxy-s-triazinyl, 2,4,5-trifluoropyrimidyl, 2,4,5-trichloro-pyrimidyl, 2,4-difluoro-5-chloropyrimidyl, 2-fluoro-4-methyl-5-chloropyrimidyl, 2-methyl-sulphonyl-4-methyl-5-chloropyrimidyl, 2-fluoro-4,5-dichloropyrimidyl, 2,3-dichloroquinoxalin-6-carbonyl, 2,3-dichloroquinoxalin-6-sulphonyl, 2,3-dibromopropionyl, 2-bromo-acryloyl, 1,4-dichlorophthalazin-6-carbonyl, 1,4-dibromophthalazin-6-carbonyl, and 4,5-dichloro-6-pyridazon-1-phenylcarbonyl.

### Claim 2 (depends on 1)

A compound of the formula ##STR259## wherein Y, Z, m and n have the meaning indicated in claim 1.

### Claim 3 (depends on 1)

A compound of the formula ##STR260## wherein Y, Z, m and n have the meaning indicated in claim 1.

### Claim 4

A compound of the formula ##STR261## wherein R.sub.8 denotes C.sub.1 -C.sub.6 -alkyl which may be substituted by OSO.sub.3 H or SO.sub.3 H,
R.sub.9 denotes H, CH.sub.3, SO.sub.3 H or COOH and Z has the meaning indicated.

### Claim 5 (depends on 2)

A compound according to the formula of claim 2,
wherein
Y denotes --CH.sub.2 --NH--, ##STR262## m denotes 1 or 2 and n denotes 0 to 2.

### Claim 6 (depends on 3)

A compound according to the formula of claim 3,
wherein
Y denotes --CH.sub.2 --NH--, ##STR263## m denotes 1 or 2 and n denotes 0 to 2.