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US4948879A Expired / Lapsed US ⏱️ 0.0 years remaining

Monoazo compounds containing a fiber-reactive group and an oxazolopyridone or oxazinopyridone coupling component

Assignee: Hoechst AG
•
Filing: 1988-11-17
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Granted: 1990-08-14
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Expires: 2008-11-17
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Abstract

Abstract Monoazo compounds conforming to the general formula (1) shown and defined hereinafter have very good fiber-reactive dye properties and dye hydroxy- and/or carboxamido-containing material, in particular fiber material, such as wool and in particular cellulose fibers, in strong fast shades. ##STR1## where the symbols have the following meanings: D is a benzene or naphthalene ring or a heterocyclic radical, R 1 and R 2 are each independently of the other hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, carboxy or sulfo, Z is a fiber-reactive grouping bonded to D either directly or via a bridge member, m stands for the number 1 or 2, preferably 1, R is alkyl of 1 to 4 carbon atoms which may be substituted for example by halogen, such as bromine and in particular chlorine, hydroxy, cyano, sulfo, carboxy, sulfato or phosphato, or is phenyl which may be substituted, for example by 1 or 2 substituents from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine, sulfo and carboxy, or is carboxy, carbamoyl or carbalkoxy of 2 to 5 carbon atoms, n stands for the number 2 or 3.

Inventors

  • 👤 Horst Tappe
  • 👤 Dieter Oehme
  • 👤 Werner H. Russ

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 05:33
CPC Classifications
C; C09; C09B; C09B62/00; C09B62/02; C09B62/20; C09B62/24; C09B62/245; C09B62/002; C09B62/006; C09B62/008; C09B62/0088

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 506 words
A monoazo compound conforming to the formula ##STR19## wherein: D is a benzene or naphthalene ring or benzothiazol-2-yl, R 1 and R 2 are each, independently of the other, hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, carboxy or sulfo, Z is a group of the formula (2) X--SO.sub.2 --A-- (2) in which X is vinyl, or is ethyl substituted in the β-position by a substituent eliminable under alkaline conditions to form a vinyl group, and A is a direct bond, methylene, ethylene or a group of the formula (2a) ##STR20## where R* is hydrogen or alkyl or 1 to 4 carbon atoms, or Z is β-bromoacryloylamino, α,β-dibromopropionylamino, β-(phenylsulfonyl)propionylamino, β-(methylsulfonyl)-propionylamino, β-chloropropionylamino, 2,2,3,3-tetrafluorocyclobutane-1-carbonylamino, N-(β-sulfatoethylsulfonyl)-N-methyl-or -N-ethyl-amino, or N-(vinylsulfonyl)-N-methyl-or -N-ethyl-amino or a group of the formula (3) ##STR21## where R* has the abovementioned meanings, Y is fluorine or chlorine and W is fluorine or chlorine or a N-nicotinamide or N-nicotinic acid group or an amino group of the formula (4) ##STR22## where R 3 is hydrogen, alkyl of 1 to 4 carbon atoms unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of sulfo, carboxy, phosphato, sulfato, hydroxy, cyano, vinylsulfonyl, β-sulfatoethylsulfonyl, β-chloroethylsulfonyl and phenyl or naphthyl each unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of sulfo, carboxy, methyl, ethyl, methoxy, ethoxy, chlorine, bromine and a group of the formula --SO 2 --X where X has one of the abovementioned meanings, or R 3 is a cycloaliphatic group, and R 4 is hydrogen or alkyl of 1 to 4 carbon atoms unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of sulfo, carboxy, phosphato, sulfato, hydroxy, cyano, vinylsulfonyl, β-sulfatoethylsulfonyl, β-chloroethylsulfonyl and phenyl or naphthyl each unsubstituted or substituted by 1, 2, or 3 substituents selected from the group consisting of sulfo, carboxy, methyl, ethyl, methoxy, ethoxy, chlorine, bromine, and a group of the formula --SO 2 --X where X has one of the abovementioned meanings, or R 4 is phenyl or naphthyl each unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of sulfo, carboxy, chlorine, bromine, methyl, ethyl, methoxy, ethoxy and a group of the formula --SO 2 --X where X has one of the abovementioned meanings, or R 3 and R 4 together with the nitrogen atom form the piperidino, piperazino or morpholino group, or Z is a group of the formula (5) ##STR23## where R 5 is chlorine, fluorine or methylsulfonyl, R 6 is chlorine, fluorine or methyl and R 7 is chlorine or cyano m is the number 1 or 2, R is hydrogen or alkyl of 1 to 4 carbon atoms unsubstituted or substituted by halogen, hydroxy, cyano, sulfo, carboxy, sulfato or phosphato, or is phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine, sulfo and carboxy, or is carboxy, carbamoyl or carbalkoxy of 2 to 5 carbon atoms, n is the number 2 or 3.
Claim 2
Dependent Claim 506 words
A monoazo compound conforming to the formula ##STR19## wherein: D is a benzene or naphthalene ring or benzothiazol-2-yl, R 1 and R 2 are each, independently of the other, hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, carboxy or sulfo, Z is a group of the formula (2) X--SO.sub.2 --A-- (2) in which X is vinyl, or is ethyl substituted in the β-position by a substituent eliminable under alkaline conditions to form a vinyl group, and A is a direct bond, methylene, ethylene or a group of the formula (2a) ##STR20## where R* is hydrogen or alkyl or 1 to 4 carbon atoms, or Z is β-bromoacryloylamino, α,β-dibromopropionylamino, β-(phenylsulfonyl)propionylamino, β-(methylsulfonyl)-propionylamino, β-chloropropionylamino, 2,2,3,3-tetrafluorocyclobutane-1-carbonylamino, N-(β-sulfatoethylsulfonyl)-N-methyl-or -N-ethyl-amino, or N-(vinylsulfonyl)-N-methyl-or -N-ethyl-amino or a group of the formula (3) ##STR21## where R* has the abovementioned meanings, Y is fluorine or chlorine and W is fluorine or chlorine or a N-nicotinamide or N-nicotinic acid group or an amino group of the formula (4) ##STR22## where R 3 is hydrogen, alkyl of 1 to 4 carbon atoms unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of sulfo, carboxy, phosphato, sulfato, hydroxy, cyano, vinylsulfonyl, β-sulfatoethylsulfonyl, β-chloroethylsulfonyl and phenyl or naphthyl each unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of sulfo, carboxy, methyl, ethyl, methoxy, ethoxy, chlorine, bromine and a group of the formula --SO 2 --X where X has one of the abovementioned meanings, or R 3 is a cycloaliphatic group, and R 4 is hydrogen or alkyl of 1 to 4 carbon atoms unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of sulfo, carboxy, phosphato, sulfato, hydroxy, cyano, vinylsulfonyl, β-sulfatoethylsulfonyl, β-chloroethylsulfonyl and phenyl or naphthyl each unsubstituted or substituted by 1, 2, or 3 substituents selected from the group consisting of sulfo, carboxy, methyl, ethyl, methoxy, ethoxy, chlorine, bromine, and a group of the formula --SO 2 --X where X has one of the abovementioned meanings, or R 4 is phenyl or naphthyl each unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of sulfo, carboxy, chlorine, bromine, methyl, ethyl, methoxy, ethoxy and a group of the formula --SO 2 --X where X has one of the abovementioned meanings, or R 3 and R 4 together with the nitrogen atom form the piperidino, piperazino or morpholino group, or Z is a group of the formula (5) ##STR23## where R 5 is chlorine, fluorine or methylsulfonyl, R 6 is chlorine, fluorine or methyl and R 7 is chlorine or cyano m is the number 1 or 2, R is hydrogen or alkyl of 1 to 4 carbon atoms unsubstituted or substituted by halogen, hydroxy, cyano, sulfo, carboxy, sulfato or phosphato, or is phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine, sulfo and carboxy, or is carboxy, carbamoyl or carbalkoxy of 2 to 5 carbon atoms, n is the number 2 or 3.
Claim 3
Dependent Claim 17 words
A compound as claimed in claim 1, wherein R is alkyl of 1 to 4 carbon atoms.
Claim 4
Dependent Claim 11 words
A compound as claimed in claim 1, wherein R is methyl.
Claim 5
Dependent Claim 11 words
A compound as claimed in claim 1, wherein m is 1.
Claim 6
Dependent Claim 11 words
A compound as claimed in claim 1, wherein n is 3.
Claim 7
Dependent Claim 49 words
A compound as claimed in claim 1, wherein R is methyl, n is 3, m is 1, and Z is a group of the formula X--SO 2 -- wherein X is vinyl or is an ethyl which is substituted in the β-position by a substituent eliminable by an alkali.
Claim 8
Dependent Claim 43 words
A compound as claimed in claim 1, wherein m is 1 and Z is a group of the formula X--SO 2 -- wherein X is vinyl or is an ethyl which is substituted in the β-position by a substituent eliminable by an alkali.
Claim 9
Dependent Claim 76 words
A compound as claimed in claim 1, wherein D is a naphthalene ring to which the azo group is bonded in the 2-position, R 1 and R 2 have the meanings mentioned in claim 1, m is 1, Z is a group of the formula X--SO 2 -- wherein X is vinyl or is an ethyl which is substituted in the β-position by a substituent eliminable by an alkali, R is methyl and n is 3.
Claim 10
Dependent Claim 19 words
A compound as claimed in claim 8, wherein R 1 is hydrogen and R 2 is hydrogen or sulfo.
Claim 11
Dependent Claim 66 words
A compound as claimed in claim 1, wherein D is a benzene ring, R 1 and R 2 have the meanings mentioned in claim 1, m is 1, Z is a group of the formula X--SO 2 -- wherein X is vinyl or is an ethyl which is substituted in the β-position by a substituent eliminable by an alkali, R is methyl and n is 3.
Claim 12
Dependent Claim 16 words
A compound as claimed in claim 6, wherein X is vinyl, β-thiosulfatoethyl, β-phosphatoethyl, β-chloroethyl or β-sulfatoethyl.
Claim 13
Dependent Claim 16 words
A compound as claimed in claim 7, wherein X is vinyl, β-thiosulfatoethyl, β-phosphatoethyl, β-chloroethyl or β-sulfatoethyl.
Claim 14
Dependent Claim 16 words
A compound as claimed in claim 8, wherein X is vinyl, β-thiosulfatoethyl, β-phosphatoethyl, β-chloroethyl or β-sulfatoethyl.
Claim 15
Dependent Claim 16 words
A compound as claimed in claim 10, wherein X is vinyl, β-thiosulfatoethyl, β-phosphatoethyl, β-chloroethyl or β-sulfatoethyl.
Claim 16
Dependent Claim 43 words
A compound as claimed in claim 1, wherein Z is a group of the formula X--SO 2 -- wherein X is vinyl or an ethyl group which is substituted in the β-position by a substituent which is eliminable by the action of alkali.
Claim 17
Dependent Claim 16 words
A compound as claimed in claim 15, wherein X is vinyl, β-thiosulfatoethyl, β-phosphatoethyl, β-chloroethyl or β-sulfatoethyl.
Claim 18
Dependent Claim 11 words
A compound as claimed in claim 15, wherein X is β-sulfatoethyl.

References Cited (Backward Citations)

GB1271226A Cited
GB2010882A Cited
EP0078024A1 Cited
US4644058A Cited
US4504273A Cited
US4585460A Cited
US4659807A Cited
EP0181585A2 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-08-13 1994-02-12 1994-08-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-08-13 1998-02-12 1998-08-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-08-13 2002-02-12 2002-08-14 $7700.00 Window Closed / Lapsed

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