US4400504A
Expired / Lapsed
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Dioxazine reactive dyestuffs
Assignee: Bayer AG
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Filing: 1981-11-10
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Granted: 1983-08-23
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Expires: 2001-11-10
Abstract
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 1 and X 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.
Inventors
- 👤 Wolfgang Harms
- 👤 Klaus Wunderlich
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 22:55
CPC Classifications
C; C09; C09B; C09B62/00; C09B62/44; C09B62/4401; C09B62/002; C09B62/0025
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
452 words
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 2 ; ##STR255## unsubstituted or substituted by SO 3 H, OSO 3 H, OH, O-alkyl(C 1 -C 4 ); NH-cyclohexyl; NH-aryl unsubstituted or substituted by halogen, alkyl(C 1 -C 4 ), O-alkyl(C 1 -C 4 ), NH-acetyl, SO 3 H; O-alkyl(C 1 -C 4 ); O-aryl unsubstituted or substituted by alkyl(C 1 -C 4 ) or halogen and wherein X 1 and X 2 independently of one another denote hydrogen, optionally substituted C 1 -C 4 -alkyl, cycloalkyl, optionally substituted aryl, CN, halogen, COOR 1 (wherein R 1 denotes H, alkyl or cycloalkyl) or CONR 2 R 3 (wherein R 2 and R 3 independently of one another are H, optionally substituted C 1 -C 4 -alkyl, cycloalkyl or optionally substituted aryl), said optional substituents being OH, SO 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 1 -C 2 ), O or CH 2 and wherein X 1 and X 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 1 and X 2 have the meanings given above and wherein Y denotes a bridge member of the formulae ##STR258## wherein R 5 denotes H or C 1 -C 4 -alkyl which may be substituted by OH, SO 3 H or OSO 3 H, R 6 denotes H or C 1 -C 4 -alkyl which may be substituted by OH, SO 3 H or OSO 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 3 H or OSO 3 H, and arylene denotes 1,2-, 1,3- or 1,4-phenylene radicals which may be substitutd by C 1 -C 4 -alkyl, halogen, SO 3 H, COOH or C 1 -C 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 1 -C 4 )alkylamino-s-triazinyl, 2-chloro-4-(C 1 -C 4 )alkylamino-s-triazinyl, 2-2-bromo-4-(C 1 -C 4 )alkylamino-s-triazinyl, 2-fluoro-4-di-(C 1 -C 4 )alkylamino-s-triazinyl, 2-chloro-4-di-(C 1 -C 4 )alkylamino-s-triazinyl, 2-bromo-4-di-(C 1 -C 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 3 H, COOH, SO 2 --CH 2 --CH 2 --OSO 3 H, 2-fluoro-, 2-chloro-, 2-bromo-4-(C 1 -C 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
Dependent Claim
452 words
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 2 ; ##STR255## unsubstituted or substituted by SO 3 H, OSO 3 H, OH, O-alkyl(C 1 -C 4 ); NH-cyclohexyl; NH-aryl unsubstituted or substituted by halogen, alkyl(C 1 -C 4 ), O-alkyl(C 1 -C 4 ), NH-acetyl, SO 3 H; O-alkyl(C 1 -C 4 ); O-aryl unsubstituted or substituted by alkyl(C 1 -C 4 ) or halogen and wherein X 1 and X 2 independently of one another denote hydrogen, optionally substituted C 1 -C 4 -alkyl, cycloalkyl, optionally substituted aryl, CN, halogen, COOR 1 (wherein R 1 denotes H, alkyl or cycloalkyl) or CONR 2 R 3 (wherein R 2 and R 3 independently of one another are H, optionally substituted C 1 -C 4 -alkyl, cycloalkyl or optionally substituted aryl), said optional substituents being OH, SO 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 1 -C 2 ), O or CH 2 and wherein X 1 and X 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 1 and X 2 have the meanings given above and wherein Y denotes a bridge member of the formulae ##STR258## wherein R 5 denotes H or C 1 -C 4 -alkyl which may be substituted by OH, SO 3 H or OSO 3 H, R 6 denotes H or C 1 -C 4 -alkyl which may be substituted by OH, SO 3 H or OSO 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 3 H or OSO 3 H, and arylene denotes 1,2-, 1,3- or 1,4-phenylene radicals which may be substitutd by C 1 -C 4 -alkyl, halogen, SO 3 H, COOH or C 1 -C 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 1 -C 4 )alkylamino-s-triazinyl, 2-chloro-4-(C 1 -C 4 )alkylamino-s-triazinyl, 2-2-bromo-4-(C 1 -C 4 )alkylamino-s-triazinyl, 2-fluoro-4-di-(C 1 -C 4 )alkylamino-s-triazinyl, 2-chloro-4-di-(C 1 -C 4 )alkylamino-s-triazinyl, 2-bromo-4-di-(C 1 -C 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 3 H, COOH, SO 2 --CH 2 --CH 2 --OSO 3 H, 2-fluoro-, 2-chloro-, 2-bromo-4-(C 1 -C 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 3
Dependent Claim
19 words
A compound of the formula ##STR259## wherein Y, Z, m and n have the meaning indicated in claim 1.
Claim 4
Dependent Claim
19 words
A compound of the formula ##STR260## wherein Y, Z, m and n have the meaning indicated in claim 1.
Claim 5
Dependent Claim
45 words
A compound of the formula ##STR261## wherein R 8 denotes C 1 -C 6 -alkyl which may be substituted by OSO 3 H or SO 3 H, R 9 denotes H, CH 3 , SO 3 H or COOH and Z has the meaning indicated.
Claim 6
Dependent Claim
45 words
A compound of the formula ##STR261## wherein R 8 denotes C 1 -C 6 -alkyl which may be substituted by OSO 3 H or SO 3 H, R 9 denotes H, CH 3 , SO 3 H or COOH and Z has the meaning indicated.
Claim 7
Dependent Claim
27 words
A compound according to the formula of claim 2, wherein Y denotes --CH 2 --NH--, ##STR262## m denotes 1 or 2 and n denotes 0 to 2.
Claim 8
Dependent Claim
27 words
A compound according to the formula of claim 3, wherein Y denotes --CH 2 --NH--, ##STR263## m denotes 1 or 2 and n denotes 0 to 2.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-08-22 | 1987-02-21 | 1987-08-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-08-22 | 1991-02-21 | 1991-08-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-08-22 | 1995-02-21 | 1995-08-23 | $7700.00 | Window Closed / Lapsed |