Polyazo dye compounds having plural vinylsulfone type fiber reactive groups in one molecule
First Claim
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1. A polyazo compound of the following formula, ##STR854## wherein A is phenylene which is unsubstituted or substituted once or twice by methyl, ethyl, methoxy, ethoxy, chloro, bromo or sulfo, naphthylene which is unsubstituted or substituted by sulfo, or alkylene which is selected from the group consisting of:
- ##STR855## wherein the linkage **** bonds to the --N--, alk is polymethylene having 1 to 6 carbon atoms or its branched isomer, R'"'"' is hydrogen, chloro, bromo, fluoro, hydroxy, sulfato, C1 -C4 acyloxy, cyano, carboxy, C1 -C5 alkoxycarbonyl or carbamoyl, R" is hydrogen or C1 -C6 alkyl, each alk'"'"' is independently polymethylene having 2 to 6 carbon atoms or its branched isomer, or each alk'"'"' is taken together with R" to form a ring through methylene, and m and n are each independently an integer of 1to 6,X is --NR2 R3, --OR4 or --SR5 in which R2, R3, R4 and R5 independently of one another are each hydrogen, C1 -C4 alkyl which is unsubstituted or substituted once or twice by C1 -C4 alkoxy, sulfo, carboxy, hydroxy, chloro, phenyl or sulfato, phenyl which is unsubstituted or substituted once or twice by C1 -C4 alkyl, C1 -C4 alkoxy, sulfo, carboxy, chloro or bromo, naphthyl which is unsubstituted or substituted once, twice or thrice by hydroxy, carboxy, sulfo, C1 -C4 alkyl, C1 -C4 alkoxy or chloro or benzyl which is unsubstituted or substituted once or twice by C1 -C4 alkyl, C1 -C4 alkoxy, sulfo or chloro,Z is --SO2 CH═
CH2 or --SO2 CH2 CH2 Z'"'"' in which Z'"'"' is a group capable of being split by the action of an alkali,R1 is hydrogen or C1 -C4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C1 -C4 alkoxy, halogen, carboxy, carbamoyl, C1 -C4 alkoxycarbonyl, C1 -C4 alkylcarbanoyloxy, sulfo or sulfamoyl, andF is a polyazo dye moiety selected from the group consisting of those represented by the following formulas (1), (2), (3) and (4) each in free acid form, the formula (1) being ##STR856## wherein B is ##STR857## in which the asterisked linkage bonds to the azo group, and R7 is hydrogen, methyl, methoxy or sulfo,D is phenylene which is unsubstituted or substituted once or twice by methyl, ethyl, methoxy, ethoxy, chloro, bromo or sulfo or naphthalene which is unsubstituted or substituted by sulfo,R6 is hydrogen or C1 -C4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C1 -C4 alkoxy, halogen, carboxy, carbamoyl, C1 -C4 alkoxycarbonyl, C1 -C4 alkylcarbonyloxy, sulfo or sulfamoyl,any one of X1 and X2 is --NH2 and the other is --OH, andZ1 is --SO2 CH═
CH2 or --SO2 CH2 CH2 Z1 '"'"' in which Z1 '"'"' is a group capable of being split by the action of an alkali,the formula (2) being ##STR858## wherein D and Z1 are as defined above, R8 is hydrogen or C1 -C4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C1 -C4 alkoxy, halogen, carboxy, carbamoyl, C1 -C4 alkoxycarbonyl, C1 -C4 alkylcarbonyloxy, sulfur or sulfamoyl,B1 is ##STR859## in which the linkage marked as ** bonds to the group --N═
N--D, R9 is hydrogen, C1 -C4 alkyl, C1 -C4 alkoxy or sulfo, and R10 is hydrogen, halogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 alkylsulfonylamino, C1 -C4 acylamino or ureido,the formula (3) being ##STR860## wherein B1, D and Z1 are as defined above, R11 is hydrogen or C1 -C4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C1 -C4 alkoxy, halogen, carboxy, carbamoyl, C1 -C4 alkoxycarbonyl, C1 -C4 alkylcarbonyloxy, sulfo or sulfamoyl,E is ##STR861## in which the linkage marked with *** bonds to the group ##STR862## R12 is hydrogen, halogen, C1 -C4 alkyl, C1 -C4 alkoxy or sulfo, and R13 is hydrogen, halogen, C1 -C4 alkyl, C1 -C4 alkylsulfonylamino, C1 -C4 alkoxy, C1 -C4 acylamino or uriedo,and the formula (4) being ##STR863## wherein B1, D and Z1 are as defined above, and E is as defined above, provided that the linkage marked with *** bonds to the azo group of ##STR864## R14 is hydrogen, C1 -C4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C1 -C4 alkoxy, halogen, carboxy, carbamoyl, C1 -C4 alkoxycarbonyl, C1 -C4 alkylcarbonyloxy, sulfo or sulfamoyl, and l is 1 or 2,provided that R4 is alkyl, phenyl, naphthyl or benzyl as defined above, when F is a polyazo dye moiety of formula (1) or (2).
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Abstract
A polyazo compound of the following formula, ##STR1## wherein A is phenylene, naphthylene or alkylene, X is --NR2 R3, --OR4 or --SR5 in which R2, R3, R4 and R5 are each hydrogen, alkyl, phenyl, naphthylene or benzyl, Z is --SO2 CH═CH2 or --SO2 CH2 CH2 Z'"'"' in which Z'"'"' is a splittable group, R1 is hydrogen or alkyl, and F is polyazo dye moiety carrying a fiber reactive group like that represented by Z. This compound is useful for the dyeing or printing of fiber materials to obtain a product dyed or printed in a color superior in various fastness properties with superior build-up property.
11 Citations
17 Claims
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1. A polyazo compound of the following formula, ##STR854## wherein A is phenylene which is unsubstituted or substituted once or twice by methyl, ethyl, methoxy, ethoxy, chloro, bromo or sulfo, naphthylene which is unsubstituted or substituted by sulfo, or alkylene which is selected from the group consisting of:
- ##STR855## wherein the linkage **** bonds to the --N--, alk is polymethylene having 1 to 6 carbon atoms or its branched isomer, R'"'"' is hydrogen, chloro, bromo, fluoro, hydroxy, sulfato, C1 -C4 acyloxy, cyano, carboxy, C1 -C5 alkoxycarbonyl or carbamoyl, R" is hydrogen or C1 -C6 alkyl, each alk'"'"' is independently polymethylene having 2 to 6 carbon atoms or its branched isomer, or each alk'"'"' is taken together with R" to form a ring through methylene, and m and n are each independently an integer of 1to 6,
X is --NR2 R3, --OR4 or --SR5 in which R2, R3, R4 and R5 independently of one another are each hydrogen, C1 -C4 alkyl which is unsubstituted or substituted once or twice by C1 -C4 alkoxy, sulfo, carboxy, hydroxy, chloro, phenyl or sulfato, phenyl which is unsubstituted or substituted once or twice by C1 -C4 alkyl, C1 -C4 alkoxy, sulfo, carboxy, chloro or bromo, naphthyl which is unsubstituted or substituted once, twice or thrice by hydroxy, carboxy, sulfo, C1 -C4 alkyl, C1 -C4 alkoxy or chloro or benzyl which is unsubstituted or substituted once or twice by C1 -C4 alkyl, C1 -C4 alkoxy, sulfo or chloro, Z is --SO2 CH═
CH2 or --SO2 CH2 CH2 Z'"'"' in which Z'"'"' is a group capable of being split by the action of an alkali,R1 is hydrogen or C1 -C4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C1 -C4 alkoxy, halogen, carboxy, carbamoyl, C1 -C4 alkoxycarbonyl, C1 -C4 alkylcarbanoyloxy, sulfo or sulfamoyl, and F is a polyazo dye moiety selected from the group consisting of those represented by the following formulas (1), (2), (3) and (4) each in free acid form, the formula (1) being ##STR856## wherein B is ##STR857## in which the asterisked linkage bonds to the azo group, and R7 is hydrogen, methyl, methoxy or sulfo, D is phenylene which is unsubstituted or substituted once or twice by methyl, ethyl, methoxy, ethoxy, chloro, bromo or sulfo or naphthalene which is unsubstituted or substituted by sulfo, R6 is hydrogen or C1 -C4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C1 -C4 alkoxy, halogen, carboxy, carbamoyl, C1 -C4 alkoxycarbonyl, C1 -C4 alkylcarbonyloxy, sulfo or sulfamoyl, any one of X1 and X2 is --NH2 and the other is --OH, and Z1 is --SO2 CH═
CH2 or --SO2 CH2 CH2 Z1 '"'"' in which Z1 '"'"' is a group capable of being split by the action of an alkali,the formula (2) being ##STR858## wherein D and Z1 are as defined above, R8 is hydrogen or C1 -C4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C1 -C4 alkoxy, halogen, carboxy, carbamoyl, C1 -C4 alkoxycarbonyl, C1 -C4 alkylcarbonyloxy, sulfur or sulfamoyl, B1 is ##STR859## in which the linkage marked as ** bonds to the group --N═
N--D, R9 is hydrogen, C1 -C4 alkyl, C1 -C4 alkoxy or sulfo, and R10 is hydrogen, halogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 alkylsulfonylamino, C1 -C4 acylamino or ureido,the formula (3) being ##STR860## wherein B1, D and Z1 are as defined above, R11 is hydrogen or C1 -C4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C1 -C4 alkoxy, halogen, carboxy, carbamoyl, C1 -C4 alkoxycarbonyl, C1 -C4 alkylcarbonyloxy, sulfo or sulfamoyl, E is ##STR861## in which the linkage marked with *** bonds to the group ##STR862## R12 is hydrogen, halogen, C1 -C4 alkyl, C1 -C4 alkoxy or sulfo, and R13 is hydrogen, halogen, C1 -C4 alkyl, C1 -C4 alkylsulfonylamino, C1 -C4 alkoxy, C1 -C4 acylamino or uriedo, and the formula (4) being ##STR863## wherein B1, D and Z1 are as defined above, and E is as defined above, provided that the linkage marked with *** bonds to the azo group of ##STR864## R14 is hydrogen, C1 -C4 alkyl which is unsubstituted or substituted by hydroxy, cyano, C1 -C4 alkoxy, halogen, carboxy, carbamoyl, C1 -C4 alkoxycarbonyl, C1 -C4 alkylcarbonyloxy, sulfo or sulfamoyl, and l is 1 or 2, provided that R4 is alkyl, phenyl, naphthyl or benzyl as defined above, when F is a polyazo dye moiety of formula (1) or (2). - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17)
- ##STR855## wherein the linkage **** bonds to the --N--, alk is polymethylene having 1 to 6 carbon atoms or its branched isomer, R'"'"' is hydrogen, chloro, bromo, fluoro, hydroxy, sulfato, C1 -C4 acyloxy, cyano, carboxy, C1 -C5 alkoxycarbonyl or carbamoyl, R" is hydrogen or C1 -C6 alkyl, each alk'"'"' is independently polymethylene having 2 to 6 carbon atoms or its branched isomer, or each alk'"'"' is taken together with R" to form a ring through methylene, and m and n are each independently an integer of 1to 6,
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Current AssigneeSumitomo Chemical Company Limited
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Original AssigneeSumitomo Chemical Company Limited
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InventorsHarada, Naoki, Miyamoto, Tetsuya, Omura, Takashi, Kayane, Yutaka, Akahori, Kingo, Yokogawa, Kazufumi, Washimi, Takeshi
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Primary Examiner(s)Lee, Mary C.
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Assistant Examiner(s)POWERS, FIONA
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Application NumberUS07/526,708Time in Patent Office721 DaysField of Search534/637, 534/642US Class Current534/642CPC Class CodesC09B 62/513 Disazo or polyazo dyes
