GB2148920A - Disperse and acid azo dyes from phenylamines and 1 ,2-dihydroquinoline couplers - Google Patents
Disperse and acid azo dyes from phenylamines and 1 ,2-dihydroquinoline couplers Download PDFInfo
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- GB2148920A GB2148920A GB08328584A GB8328584A GB2148920A GB 2148920 A GB2148920 A GB 2148920A GB 08328584 A GB08328584 A GB 08328584A GB 8328584 A GB8328584 A GB 8328584A GB 2148920 A GB2148920 A GB 2148920A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3643—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from quinolines or hydrogenated quinolines
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Abstract
New disperse and acid azo dyes giving bright, green to blue shades having good fastness and non- red flaring on polyamide fibres, have the formula <IMAGE> wherein: ring A is unsubstituted or substituted and C<1> is a 1 ,2-dihydroquinoline coupler which may be substituted.
Description
SPECIFICATION
Disperse and acid azo dyes from phenylamines and I ,2-Dihydrnquinoline couplers
This invention concerns disperse and acid dyes particularly suited for the dyeing of polyamide fibres, and having the general formula D - N = N -C1 wherein D is phenyl, which may be substituted and C' is a 1,2-dihydroquinoline coupler which may be substituted preferably in any of the 1, 2, 4 and 7 positions;
Preferably the dyes correspond to the formula
wherein: ring A is unsubstituted for substituted with 1-3 substituents independently selected from alkyl, alkoxy, halogen, trifluoromethyl, thiocyano, cyano, phenylazo, formyl, alkanoyl, alkanoylamino, aroyl, arylsulfonyl, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, sulfamoyl, alkylsulfamoyl, dialkyl-sulfamoyl, alkylsulfonyl, alkylthio, arylthio, alkyl-SO3M, aryloxy, alkoxycarbonyl, alkoxy-carbonyloxy, acylamido, aryloxycarbonyl,
alkyl;;
R, is H, alkyl, aryl or cyclohexyl, wherein said alkyl, aryl and cyclohexyl groups are unsubstituted or substituted with 1-3 substituents different from the parent group and independently selected from hydroxy, alkyl, alkoxy, aryl, aryloxy, cyclohexyl, cyclohexoxy, furyl (C4H30), aroyloxy, alkoxycarbonyl, alkanoyloxy, SO2NH2, SO2NHaryl, SO2NHalkyl, SO2N-(alkyl)2, NHCOOalkyl, N HCON Halkyl, acylamido, alkylsulfonamido, succinimido (C4H4O2N), glutarimido (C5H6O2N), phthalimido (C8H4O2N), 1-(2-pyrrolidono) (C4H6ON), alkyl-SO3M, cyano, CONY2, CON Halkyl, CON(alkyl)2, alkoxyalkoxy, alkylthio, halogen, arylthio, alkylsulfonyl and arylsulfonyl; R2 - R3 are each independently selected from H and alkyl;
R4 is H, alkyl or alkyl-SO3M; and
R5 is selected from H, alkyl, alkoxy, alkenyl of 2-8 carbons, halogen, acylamido, alkylthio and formamido, wherein the alkyl moieties thereof may be substituted with 1-3 substituents independently selected from hydroxy, halogen, cyano, alkoxy, alkyl-SO3M, alkylthio, alkanoyl, alkanoyloxy, and alkoxycarbonyl;
M is selected from H, Na, K, NH4,
Ca Zn
2 2 and the colorless cations of salts of primary, secondary and tertiary aliphatic and aryl amines;;
all of the alkyl and cyclic moities in the defined A ring substitients may bear 1-3 substituents different from the parent moiety and independently selected from hydroxy, alkyl, alkoxy, aryl, aryloxy, cyclohexyl, furyl (C4H 30), aroyloxy, alkoxycarbonyl, alkoxycarbonyloxy, alkanoyloxy,
SO2NH2, SO2NHaryl, SO2NHalkyl, SO2N(alkyl)2, NHCOOalkyl, NHCONHalkyl, acylamido, alkylsulfonamido, succinimido (C4H404N), glutarimido (C5H802N), phthalimido (C8H402N), alkyl SO3M, 1-(2-pyrrolidono) (C4H6ON), cyano, CONH2, CONHalkyl, CON(alkyl)2, alkoxyalkoxy, alkylthio, halogen, arylthio, alkylsulfonyl and arylsulfonyl.
The various alkyl and alkylene moieties in, for example, alkoxy, alkanoyl and the like within the above definitions of R1 - R5, and the A ring substituents have 1-6 carbons, and they and the alkenyl groups are straight or branched chain.
Preferred of the above dyes.are where ring A is unsubstituted or substituted with 1-3 substituents independently selected from acyl, alkylsulfonyl, alkyl-SO3M, acylamido, alkyl, carboalkoxy, halogen and cyano, R, is hydrogen, alkyl, aryl, cyclohexyl, or said alkyl or cyclohexyl substituted with 1-3 substituents independently selected from halogen, cyano, hydroxy and aryl, and R5 is hydrogen, alkyl or acylamido.
The dyes of this invention impart blue to green shades on fibers, particularly polyamides, exhibiting improvements in one or more properties such as fastness to light, ozone, perspiration, oxides of nitrogen, washing, sublimation or crocking, leveling, transfer, pH stability, exhaustion, build and diminished red flaring.
The diazo components used in this invention are prepared according to procedures well known to the art. The present disperse dyes may be applied to polyamide fibers by conventional dyeing procedures, e.g., dispersed in a lignin sulfonate and dyed at 98'C. on nylon fabric for one hour from an aqueous bath. The following examples illustrate procedures which are generally applicable for preparation of the present couplers and dyes.
The acid dyes of the invention may be applied to polyamide fiber by the following method:
The test dye, as a mixture with a sulphate such as ammonium sulfate, is pasted with boiling water and then made up to a known volume with water to give a weight ratio of water to dye of 30:1. Four percent on weight of fiber (owf) of a lignin sulphonate leveling agent is added, followed by ammonium acetate (about 3.0% owf) to adjust the pH to 6. The initial dyeing temperature is 40"C. which is raised to the final dyeing temperature of 98'C. over 30 minutes.
The dye bath is held at 98"C. for 60 minutes, then cooled, and the test fabric given a warm water rinse and air drying.
EXAMPLE 1
(a)- Procedure For the Preparation of 1,2-Dihydro2,2,4,7-Tetramethylquinoline Meta-toluidine (535 g.) and iodine (6 g.) are charged to a 2 liter, 3 neck, round bottom flask.
The reaction is heated to 155"C. and about 3,500 g. of acetone is added at 155-160"C.
beneath the surface over a 1 2 hour period. A mixture of acetone and water distills off during the addition. The reaction mixture is heated one-half hour at 1 60'C. and then distilled to about 690 g. of 1,2-dihydro-2,2,4,7-tetramethylquinoline boiling at 107-111 C. at 0.55 mm., a 74% yield. The product is then ethylated with triethylphosphate in the presence of ethyl iodide in known manner.
(b) Sodium nitrite (0.72 g.) is added portionwise to 5 ml. of concentrated sulfuric acid. The solution is cooled and 10 ml. of 1:5 acid is added below 1 5'C. The mixture is cooled further and 2.5 g 2,4-bis(methylsulfonyl)aniline is added followed by 10 ml. of 1:5 acid, all below 5"C. After stirring for 2 hours at 0-5"C., the diazonium solution is added to a chilled solution of 3.16 g. of N-ethyl-1,2-dihydro-2,2,4,7-tetramethylquinoline in 50 ml. of 1:5 acid below 5'C.
The reaction is kept cold and ammonium acetate added until the coupling mixture is neutral to
Congo red test paper. After allowing to couple for 1 hour at about 5'C., the reaction mixture is drowned in water and the product collected by filtration, washed with water, and dried in air.
The azo compound obtained gives dyeings having excellent fastness properties on polyamide fibers and has the structure:
The preparation of the sulfonated 1 ,2-hydroquinoline is given in German Offen. 3,0005,874 (C.A. 94, 15593K, 1981) and H2S04, ClSO3H, and/or SO3 and converting, if desired, the acid group to its salt in known manner.
EXAMPLE 2
2,6-Dichloroaniline (0.01 mole) is added to 60% aqueous acetic acid (25.0 cc), with stirring, followed by concentrated sulphuric acid (2.0 cc.). The mixture is cooled to 0 C. Sodium nitrite (0.72 g.), 0.0104 mole) is added to concentrated sulphuric acid (9.2 cc.) and the solution heated to 70'C., for 5 minutes. On cooling to 0 C. the solution is added slowly to the above amine mixture, at 0-5"C. After stirring at 0-5"C. for a further one hour, the diazo solution is added to the potassium salt of 1-ethyl-2,2,7-trimethyl-1,2-dihydroquinolin-4-yl-methyl sulphonic acid (3.33 g., 0.01 mole), in water (11.0 cc.) at < 5eC. After stirring at 0-5'C. for one hour the dye is warmed to room temperature and precipitated by adding to saturated potassium chloride solution.The product is filtered and washed with diethyl ether to give the final dye product
The following table further shows specific dyes of the present invention which are prepared as above. TABLE 1
Substituents on
Ring A R5 R2 R3 R4 R1
None H H H H H 4-CH2SO3K H H CH3 CH3 C2H5 4-Cl CH3 CH3 CH3 CH3 C2H5 2,5-di-Cl CH2CH2OH CH3 CH3 CH3 C2H5 2,4-di-Cl CH2Cl H CH(CH3)2 CH3 C2H5 2-CH3-5-Cl OCH2Cl H CH3 CH3 C2H5 2,5-di-CH3 OCH3 H CH3 CH2SO3K CH3 2-CH3 OCH3 H CH3 H C6H5 4-CH3 CH2CH2CN H CH3 H C6H11 3,4-di-CH3 Cl H CH3 CH3 C2H5 2-Cl-4-SO2CH3 Cl H CH3 CH3 CH2CH2OH 2-Br-4-SO2CH3 CH2SO3K H CH3 CH3 CH2CH2OH 2-I-4-SO3CH3 OCH3 C2H5 C2H5 C2H5 CH2CH2OH 2-Cl-4-SO2CH3 NHCHO CH3 CH3 CH3 CH2CH2OC2H5 4-CO2C2H4-OH NHCOCH2OCCCH3 CH3 CH3 CH3 CH2CN 4-CO2C2H4-Cl NHCOCH2CH3 CH3 CH3 CH2SO3Na CH2CONH2 4-CO2C2H4-C6H11 NHCOC2H5 C3H7-n C3H7-n H CH2CONHCH3 4-CO2C2H4-OCH3 NHCOC6H5 CH3 CH3 CH2SO3K CH2CON(C2H5)2 4-CO2C2H4-OC6H5 NHCOC2H5 C4H9-n C4H9-n H CH2NHCOCH3 4-CO2C2H4-CN NHCOC6H11 CH3 CH3 H CH2NHCOOCH3 4-CO2C2H4-OC2H4OC2H5 H CH3 CH3 H CH2OOCCH3 4-CO2C2H4-OCOCH3 CH2SCH3 H CH3 H CH2(C4H6ON) 4-CONHC2H4-SC6H5 CH2CH=CH2 H H CH2SO3NH(Et)3 CH2CH2COOCH3 4-CONHC2H4-Cl Br H CH3 CH3 CH2CH2COOCH3 4-CONHC2H4-C6H5 I H CH3 CH3 H 4-CONHC2H4-C6H11 F H CH3 CH3 C2H5 4-CONHC2H4-OOCCH3 SCH3 H CH3 CH3 C2H5 4-CONHC2H4-SCH3 CH2OOCCH3 H H CH2CH2SO3K C2H5 4-CONHC2H4-NHCOCH3 OCH3 H CH3 CH3 C2H5 4-CONHC2H4-CN CH3 H CH3 CH3 C2H5 4-CONHC2H4-OC2H4OC2H5 CH3 H CH3 CH3 CH3 4-CONHC2H4-OCOCH3 CH2CH2COOCH3 C2H5 C2H5 CH3 C6H5
0 rl U 9 c" U H4 0011J CR2 CR (OR)COH C2R5 C2R5 CHS03(Ca12) C6R11 uh CF3 C2R5 C2H5 CR3 C2R5 rd e u N v o" -A?) CF3 H CR3 CH2S03(Zn12) CH2CH2Oll cn cn gs 5 5es Q U U Un S 5 FS FS 5 S S FS es U Q 5 5 o S U 8 5 es e e 5 1 es Ses 5tS S S g U Vo oe U\z? Z U\Z/CJ l 5 5 5 Z Z 5Z O O O Q t; C-7 5-CON(C2H5)-C2H4-SO3K H CH3 CH3 CH3 CH2CH2OH 4-CON(C2H5)-C2H4-OH H CH3 CH3 CH3 CH2CH2OH 4-CON(C2H5)-C2H4-SC6H5 CH2CH(Cl)CH2Cl CH3 CH3 CH3 CH2CH2OC2H5 4-CON(C2H5)-C2H4-Cl CH2CH(OCH3)CH2OCH3 CH3 CH3 CH3 CH2CN 4-CON(C2H5)-C2H4-C6H5 CH3 CH3 CH3 CH2SO3K CH2CONH2 4-CON(C2H5)-C2H4-OOCCH3 CH3 CH3 CH3 CH3 CH2CONHCH3 4-CON(C2H5)-C2H4-C6H10-p-SO3K CH3 CH3 CH3 CH3 CH2CON(C2H5)2 4-CON(C2H5)-C2H4-OCH3 CH3 CH3 CH3 CH3 CH2NHCOCH3 4-CON(C2H5)-C2H4-SCH3 CH3 CH3 CH3 CH3 CH2NHCOOCH3 4-CON(C2H5)-C2H4-OC6H5 CH3 CH3 CH3 CH3 CH2OOCCH3 4-CON(C2H5)-C2H4-NHCOCH3 H CH3 CH3 CH3 CH2(C4H6ON) 4-CON(C2H5)-C2H4-CN H CH3 CH3 H CH2CH2COOCH3 4-CON(C2H5)-C2H4-OC2H4OCH3 CH3 CH3 CH3 H CH2CH2COOCH3 4-CON(C2H5)-C2H4-OCOCH3 CH2CH2OH H H C3H7-n H
m u\ 2 2 I N N U O U e I fez CR2ci CR3 3: N CI I U c24/110;R22 OCR3 H CR(cR3)2 C2H5 C2R5 Sn ç 5 H c; c; es n es :: S S C) s U C; O o es es cs 5 S S S Q m tv es I es O O O O 5 c) > z/D 5n 4uZoL) l S S S es es es cJ U Q l 5 S S es cJes < Js Z Z Z O o O Y Y Y 4-SO2NHC2H5 OCH3 H CH3 C2H5 C2H5 4-SO2NH-C2H4-SC6H4-p-CH2SO3K CH2CH2CN H CH3 CH3 C2H5 4-SO2NH-C2H4-Cl Cl H CH3 CH2SO3NH(CH2CH2OH)2 CH3 4-SO2NHC2H4-C6H11 Cl H CH3 CH3 C6H5 4-SO2NH-C2H4-OOCCH3 H H CH3 CH3 C6H11 4-SO2NH-C2H4-OCH3 OCH3 H CH3 CH3 C2H5 4-SO2NH-C2H4-SC2H5 NHCHO H CH3 CH3 CH2CH2OH 4-SO2NH-C2H4-NHCOCH3 NHCOCH2OCCH3 C2H5 C2H5 CH3 CH2CH2OH 4-SO2NHC2H4-CN NHCOCH2CH3 CH3 CH3 CH3 CH2CH2OH 4-SO2NH-C2H4-OC2H4OCH3 NHCOC2H5 CH3 CH3 CH3 CH2CH2OC2H5 4-SO2NH-C2H4-OCOCH3 NHCOC6H5 CH3 CH3 CH3 CH2CN
CV m z o u c\r m m N 4- so2 NH-C2 H4 -A)011 NRCOC2R5 C3 H7 -n C3 Rj -n CR3 CR2CONH2 z 2 NH-C2 H4NRSO2 C2 115 11 11 H CR2 503 Na 11 U U U = 5 5 U U C; S e S CD S C; 5 C; S S 5 S o 5 Z :z: S 5 FS CS es cS FS 5 5 = 5 cD no oeS S UX D en Eg l 5 < S Zit cS uFS cS Z Z Z Oes ofs oFS en tn tn l 4-SO2N(C2H5)C2H5 CH3 CH3 CH3 CH3 C2H5 4-SO2N(C2H5)-C2H4-OH CH2CH2OH CH3 CH3 CH2CH2SO3H C2H5 4-SO2N(C2H5)-C2H4-SC6H5 CH2Cl H CH(CH3)2 CH3 C2H5 4-SO2N(C2H5)-C2H4-Cl OCH2Cl H CH3 CH3 C2H5 4-SO2N(C2H5)-C2H4-OOCCH3 OCH3 H CH3 H CH3 4-SO2N(C2H5)-C2H4-C6H11 OCH3 H CH3 H C6H5 4-SO2N(C2H5)-C2H4-C6H5 CH2CH2CN H CH3 H C6H11 4-SO2N(C2H5)-C2H4-OCH3 Cl H CH3 CH3 C2H5 4-SO2N(C2H5)-C2H4-SCH3 Cl H CH3 CH3 CH2CH2OH 4-SO2N(C2H5)-C2H4-NHCOCH3 H H CH3 CH3 CH2CH2OH 4-SO2N(C2H4)-C2H4-CN OCH3 C2H5 C2H5 C2H5 CH2CH2OH 4-SO2N(C2H5)-C2H4-OC2H4OCH3 NHCHO CH3 CH3 CH3 CH2CH2OC2H5 4-SO2N(C2H5)-C2H4-OCOCH3 NHCOCH2OCCH3 CH3 CH3 CH3 CH2CN
PI o U U 5 2 m S T o S z es es 5 S 2 O cv U\ oC) l un 5 s z Oes tIn 4-SO2N(C2H5)-C2H4-OC6H5 NHCOC2H5 C3H7-n C3H7-n H CH2CONHCH3 4-SO2N(C2H5)-C2H4-NHSO2C2H5 NHCOC6H5 CH3 CH3 H CH2CON(C2H5)2
cc U 0 U s Z N 2 U 2 4-sO2N(c2 115 ) -C2 H4 11 NRCOC2R5 C4 H9 -n C4 119 -n CR2SO3R cH2NHCOcR3 S z es tes 0 5 l S xjS 5 S z oes xIn 4-SO2C2H4 NHCOC6H11 CH3 CH3 H CH2NHCOOCH3 4-SO2-C2H4-OH H CH3 CH3 H CH2OOCCH3 4-SO2C2H4-SC6H5 CH2SCH3 H CH3 H CH2(C4H6ON) 4-SO2-C2H4-Cl CH2CH=CH2 H H H CH2CH2COOCH3 4-SO2-C2H4-C6H11 Br H CH3 CH3 CH2CH2COOCH3 4-SO2-C2H4-SCH3 I H CH3 CH3 H 4-SO2-C2H4-OC6H5 F H CH3 CH3 C2H5 4-SO2-C2H4-NHCOCH3 SCH3 H CH3 CH3 C2H5 4-SO2-C2H4-CN CH2OOCCH3 H H H C2H5 4-SO2-C2H4-OC2H4OC2H5 OCH3 H CH3 CH3 C2H5 4-SO2-C2H4-OCOCH3 CH3 H CH3 CH3 C2H5
rl s s m m m \o \o d" 2" CR3 rn U CH2CR2C0OCR3 C2R5 C2R5 CR3 C6R5 4-so2-c2 R4N%OoR2 s CH(OR)CH2 OR C2H5 C2115 CR3 C6R11 5 cS FS 7 S S FS FS S t.) U 5 o e tS 5 5 O O 5fS t" t; Q rtn 5S 5S ÇS sS 5cs e 5S CM FS O O O O O v Z U\Z/ l 5 taFS ys evS oS Oes oFS tn cn cn l 2-CN-4-SO2CH3 CF3 C2H5 C2H5 CH3 C2H5 2-CN-4-Cl CF3 H CH3 CH3 CH2CH2OH 2-CN-4-COCH3 H CH3 CH3 CH3 CH2CH2OH 2-CN-4-COOC2H5 H CH3 CH3 CH3 CH2CH2OH 2,4-di-CN CH2CH(Cl)CH2Cl CH3 CH3 CH3 CH2CH2OC2H5 4-SO2C6H5 CH2CH(OCH3)CH2OCH3 CH3 CH3 CH3 CH2CN 4-SO2NH2 CH3 CH3 CH3 CH3 CH2CONH2 4-SO2N(C2H5)2 CH3 CH3 CH3 CH3 CH2CONHCH3 2-Cl-5-SO2NHC2H4OH CH3 CH3 CH3 CH3 CH2CON(C2H5)2 2-Cl-5-SO2CH3 CH3 CH3 CH3 CH3 CH2NHCOCH3
cr) m u o o u 2,5-di-Cl-4-502 N,,,,\ > CR3 CR3 CR3 CR3 cR2NRcoocR3 5 S CD sz/ Oes n l un es 2,6-di-Cl-4-SO2CH3 CH3 CH3 CH3 CH3 CH2OOCCH3 2,6-di-CN-4-SO2CH3 H CH3 CH3 CH3 CH2(C4H6ON) 2,6-di-CN-4-CHO H CH3 CH3 H CH2CH2COOCH3 2,6-di-CN-4-Cl CH3 CH3 CH3 H CH2CH2COOCH3 2,6-di-CN-4-COCH3 CH2CH2OH H H C3H7-n H 2,6-di-CN-4-CONHC2H5 CH2Cl CH3 CH3 C2H7-n C2H5 2,6-di-CN-4-COOC2H5 OCH2Cl CH3 CH3 C2H5 C2H5 2-CF3-4-Br OCH3 H CH(CH3)2 C2H5 C2H5
r es hl U r m \. OCR3 H C; o 1 oS tIn U l ur s 2-COOCH3-4-SCN CH2CH2CN H CH3 CH3 C2H5 2-SO2CH3-4-SCN Cl H CH3 CH3 CH3 2-COCH3-4-SCN Cl H CH3 CH3 C6H5 2-Br-4-CONH2 H H CH3 CH3 C6H11 2-CN-4-CONH2 OCH3 H CH3 CH3 C2H5 2-CN-4-CONH2 NHCHO H CH3 CH3 CH2CH2OH
m o cu 5 u N m 4-\ /ON=N NRCOCR2OCCH3 C2R5 C2R5 CR3 CR2CR2oH e u un e es u eul es en 5 o ees 5o z H Z 4-COC6H5 NHCOCH2CH3 CH3 CH3 CH3 CH2CH2OH 2-SO2C6H5 NHCOC2H5 CH3 CH3 CH3 CH2CH2OC2H5 4-SO3C6H5 NHCOC6H5 CH3 CH3 CH3 CH2CN 2-OCH3-4,6-di-Cl NHCOC2H5 C3H7-n C3H7-n CH3 CH2CONH2 2-OCH3-5-CH3 H H H H H 4-NHCOCH3 H H CH3 CH3 C2H5 4-NHCOH CH3 CH3 CH3 CH3 C2H5 2-CN-4-SCN CH2CH2OH CH3 CH3 CH3 C2H5 2,4-di-Br-6-COOCH3 CH2Cl H CH(CH3)2 CH3 C2H5 2-Br-4-SCN-6-COOCH3 OCH2Cl H CH3 CH3 C2H5 4-NHSO2C2H5 H 3 CH H 3 CH 3 2-CN-4-SCN-6-COOCH3 OCH3 H CH3 H C6H5 2-CN-4,6-di-Cl CH2CH2CN H CH3 H C6H11 2,5-di-CN Cl H CH3 CH3 C2H5 2-CN-4-SO2C2H5 Cl H CH3 CH3 CH2CH2OH 3,5-di-COOCH3 H H CH3 CH3 CH2CH2OH 3,4-di-CN OCH3 C2H5 C2H5 C2H5 CH2CH2OH 3,4-di-Cl-2,6-di-CN NHCHO CH3 CH3 CH3 CH2CH2OC2H5 2,6-di-Br-4-SO2CH3 NHCOCH2OCCH3 CH3 CH3 CH3 CH2CN 2,6-di-Br-4-SO2N(CH3)2 NHCOCH2CH3 CH3 CH3 H CH2CONH2 2,6-di-Br-4-CHO NHCOC2H5 C3H7-n C3H7-n H CH2CONHCH3 2,6-di-Br-4-COCH3 NHCOC6H5 CH3 CH3 H CH2CON(C2H5)2 2-CN-4-CHO NHCOC2H5 C4H9-n C4H9-n H CH2NHCOCH3 2-CN-4-COOCH(CH3)2 NHCOC6H11 CH3 CH3 H CH2NHCOOCH3 2-SO2CH3-4-Cl H CH3 CH3 H CH2OOCCH3 2-SO2CH3-4-CN CH2SCH3 H CH3 H CH2(C4H6ON) 2-COOCH3-4-SO2CH3 CH2CH=CH2 H H H CH2CH2COOCH3 2-CONHC2H4OH-4-Cl Br H CH3 CH3 CH2CH2COOCH3 2-Cl-4-SO2CH3 I H CH3 CH3 H 2-Cl-4-SO2C4H9-n F H CH3 CH3 C2H5 2-Br-4-COOC4H9-n SCH3 H CH3 CH3 C2H5 2,6-di-Br-4-CHO CH2OOCCH3 H H H C2H5 2,6-di-Cl-4-SO2CH3 OCH3 H CH3 CH3 C2H5 2-I-4-SO2CH3 CH3 H CH3 CH3 C2H5 4-CN-2-SC2H4OH CH3 H CH3 CH3 CH3 4-CN-2,6-di-SCH2CH3 CH2CH2COOCH3 C2H5 C2H5 CH3 C6H5 4-CN-2-OC6H5 CH2CH(OH)CH2OH C2H5 C2H5 CH3 C6H11 4-CO2C6H5 CF3 C2H5 C2H5 CH2SO3K C2H5 4-CONHC2H4OH CF3 H CH3 CH3 CH2CH2OH 4-CONHC3H6OCH3 H CH3 CH3 CH3 CH2CH2OH 4-COOCH2CH2C6H5 H CH3 CH3 CH2SO3NH4 CH2CH2OH 4-SO2NHC2H4Cl CH2CH(Cl)CH2Cl CH3 CH3 CH3 CH2CH2OC2H5 4-SO2NHCH2C6H11 CH2CH(OCH3)CH2OCH3 CH3 CH3 CH2SO3K CH2CN 4-CONHC2H4OC2H4CN CH3 CH3 CH3 CH3 CH2CONH2 4-CONHC2H4OC6H5 CH3 CH3 CH3 CH3 CH2CONHCH3 4-SC6H5 CH3 CH3 CH3 CH3 CH2CON(C2H5)2
m m U 0 U 5rS U 5 5 V FN 5 5 CD es es O O UxzF 5cS ~eS 8 y 4-COOC2H4NHCOCH3 CH3 CH3 CH3 CH3 CH2NHCOOCH3 4-COOC2H4NHSO2CH3 CH3 CH3 CH3 CH3 CH2OOCCH3
0 9 0 U ees ICI 5 5 es CS 5 5 UE SeS z e s g y 4-COOC2H4S-CH3 H CH3 CH3 CH2SO3Na CH2CH2COOCH3 4-COOC2H4S-C6H5 CH3 CH3 CH3 CH2SO3K CH2CH2COOCH3 4-SO2NHCH2CH(OH)CH2OH CH2CH2OH H H C3H7-n H 4-SO2N(CH3)C2H4OH CH2Cl CH3 CH3 C3H7-n C2H5 4-SO2N(C2H5)2 OCH2Cl CH3 CH3 C2H5 C2H5 4-SO2N(CH3)CH2CH2OH OCH3 H CH(CH3)2 C2H5 C2H5 4-SO2CH2CH2OCOCH3 OCH3 H CH3 C2H5 C2H5 4-SO2CH2CH2OC2H5 CH2CH2CN H CH3 CH3 C2H5 4-SO2CH2CH2OH Cl H CH3 CH3 CH3 2,4-di-SO2CH3 Cl H CH3 CH3 C6H5 2-Br-4,6-di-SO2CH3 H H CH3 CH3 C6H11 2-CN-4,6-di-SO2CH3 OCH3 H CH3 CH3 C2H5 4-OCOOCH3 NHCHO H CH3 CH3 CH2CH2OH 4-OCOOCH2CH2OCOOCH3 NHCOCH2OCCH3 C2H5 C2H5 CH3 CH2CH2OH 4-C2H4-(C4H3O) NHCOCH2CH3 CH3 CH3 CH3 CH2CH2OH 4-C6H4-p-CH3 NHCOC2H5 CH3 CH3 CH3 CH2CH2OC2H5 4-CH2CH2-OOCC6H5 NHCOC6H5 CH3 CH3 CH3 CH2CN 4-CH2CH2-SO2NH2 NHCOC2H5 C3H7-n C3H7-n CH3 CH2CONH2 4-CH2CH2-SO2NHPh H H H H H 4-CH2CH2-SO2NHCH3 H H CH3 CH3 C2H5 4-CH2CH2-SO2N(C2H5)2 CH3 CH3 CH3 CH3 C2H5 4-CH2CH2-NHCOOCH3 CH2CH2OH CH3 CH3 CH3 C2H5 4-CH2CH2-NHCONHCH3 CH2Cl H CH(CH3)2 CH3 C2H5 4-CH2CH2-(C5H6O2N) OCH2Cl H CH3 CH3 C2H5 4-CH2CH2-(C8H4O2N) OCH3 H CH3 CH2SO3K CH3 4-CH2CH2-CONH2 OCH3 H CH3 H C6H5 4-CH2CH2-CONHCH3 CH2CH2CN H CH3 CH2SO3K C6H11 4-CH2CH2-CON(CH3)2 Cl H CH3 CH3 C2H5 4-CH2CH2-SO2CH3 Cl H CH3 CH3 CH2CH2OH 4-CH2CH2-SO2Ph H H CH3 CH3 CH2CH2OH 4-COCH3 CH3 CH3 CH3 H C2H5 3-Cl CH3CONH CH3 CH3 H C2H5 4-Cl,2,6-di-CN CH3 CH3 CH3 H C2H5 2-CH3,4-CH3SO2 H H H H C2H5
H H H H H C2H5 4-COCH3 CH3 CH3 CH3 CH2SO3K C2H5 3-Cl CH3CONH CH3 CH3 CH2SO3Na C2H5 4-Cl,2,6-di-CN CH3 CH3 CH3 CH2SO3K C2H5 2,4-di-CH3SO2 CH3 CH3 CH3 CH2SO3K C2H5 2,CH3,4-CH3SO2 H H H CH2SO3(Ca/2) C2H5
H H H H CH2SO3NH4 C2H5
Claims (17)
1. A dye of the general formula: DN=NC' wherein D is a phenyl or substituted phenyl group and C1 is a 1 ,2-dihydroquinoline coupler which may be substituted.
2. A dye according to Claim 1 of the formula
wherein ring A is unsubstituted or substituted with 1-3 substituents independently selected from alkyl, alkoxy, halogen, trifluoromethyl, thiocyano, cyano, phenylazo, formyl, alkanoyl, alkanoylamino, aroyl, arylsulfonyl, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, sulfamoyl, alkyl
SO3M, alkylsulfamoyl, dialkylsulfamoyl, alkylsulfonyl, alkylthio, arylthio, aryloxy, alkoxycarbonyl, alkoxycarbonyloxy, acyla mido, aryloxycarbonyl,
SO2O-aryl, and NHSO2-alkyl, wherein M is selected from H, Na, K, NH4,
Ca Zn
2 2 and the colorless cations of salts of primary, secondary and tertiary aliphatic and aryl amines and wherein all of the alkyl and cyclic moieties in the defined A ring substituents may bear 1-3 substituents different from the parent moiety and independently selected from hydroxy, alkyl, alkoxy, aryl, aryloxy, cyclohexyl, furyl (C4H30), aroyloxy, alkoxycarbonyl, alkoxycarbonyloxy, alkanoyloxy, SO2NH2, SO2NHaryl, SO2NHalkyl, SO2N(alkyl)2, alkyl-SO3M, NHC0Oalkyl, NHCON
Halkyl, acylamido, alkyl-sulfonamido, succinimido (C4H4O2N), glutarimido (C5HsO2N), phthalimido (C8H4O2N), 1-(2-pyrrolidono) (C4H6ON), cyano, CONH2, CONHalkyl, CON(alkyl)2, alkoxyalkoxy, alkylthio, and C' is a 1 ,2-dihydroquinoline coupler which is unsubstituted or substituted in any of the 1, 2, 4 and 7 positions.
3. A dye according to Claim 1 or 2 wherein C' has the formula
wherein R1 is H, alkyl, aryl or cyclohexyl, wherein said alkyl, aryl and cyclohexyl groups are unsubstituted or substituted with 1-3 substituents different from the parent group and independently selected from hydroxy, alkyl, alkoxy, aryl, aryloxy, cyclohexyl, cyclohexoxy, furyl (C4H30), aroyloxy, alkoxycarbonyl, alkanoyloxy, SO2NH2, SO2NHaryl, SO2NHalkyl, alkyl-SO3M,
SO2N(alkyl)2, NHCOOalkyl, NHCONH-alkyl, acylamido, alkylsulfonamido, succinimido (C4H402N), glutarimido (C5H6O2N), phthalimido (C8H402N), 1-(2-pyrrolidono) (C4H60N), cyano, CONH2,
CONHalkyl, CON(alkyl)2, alkoxyalkoxy, alkylthio, halogen, arylthio, alkylsulfonyl and arylsulfonyl; R2 - R3 are each inependently selected from H and alkyl;;
R4 is H, alkyl or alkyl - SO3M; and R5 is selected from H, alkyl, alkoxy, alkenyl of 2-8 carbons, halogen, acylamido, alkylthio and formamido, wherein the alkyl moieties thereof may be substituted with 1-3 substituents independently selected from hydroxy, halogen, cyano, alkoxy, alkylthio, alkanoyl, alkyl-SO3M, alkanoyloxy, and alkoxycarbonyl.
4. A dye according to Claim 2 wherein ring A is unsubstituted or substituted with 1-3 substituents independently selected from acyl, alkylsulfonyl, alkyl-SO3M, acylamido, alkyl, carboalkoxy, halogen and cyano, R1 is hydrogen, alkyl, aryl, cyclohexyl, or said alkyl or cyclohexyl substituted with 1-3 substituents independently selected from halogen, cyano, hydroxy and aryl, and R5 is hydrogen, alkyl or acylamido.
5. The dye according to Claim 1 of the formula
6. The dye according to Claim 1 of the formula
7. The dye according to Claim 1 of the formula
8. The dye according to Claim 1 of the formula
9. The dye according to Claim 1 of the formula
10. The dye according to Claim 1 of the formula
11. The dye according to Claim 1 of the formula
12. The dye according to Claim 1 of the formula
1 3. The dye according to Claim 1 of the formula
14. The dye according to Claim 1 of the formula
1 5. The dye according to Claim 1 of the formula
16. The dye according to Claim 1 of the formula
17. The dye according to claim 1 of the formula
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08328584A GB2148920B (en) | 1983-10-26 | 1983-10-26 | Disperse and acid azo dyes from phenylamines and 1,2-dihydroquinoline couplers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08328584A GB2148920B (en) | 1983-10-26 | 1983-10-26 | Disperse and acid azo dyes from phenylamines and 1,2-dihydroquinoline couplers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8328584D0 GB8328584D0 (en) | 1983-11-30 |
| GB2148920A true GB2148920A (en) | 1985-06-05 |
| GB2148920B GB2148920B (en) | 1987-11-04 |
Family
ID=10550755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08328584A Expired GB2148920B (en) | 1983-10-26 | 1983-10-26 | Disperse and acid azo dyes from phenylamines and 1,2-dihydroquinoline couplers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2148920B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005003086A3 (en) * | 2003-07-02 | 2006-02-23 | Atto Tec Gmbh | Sulfonic acid derivatives of polycyclic dyes used for analytical applications |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB327394A (en) * | 1928-10-01 | 1930-04-01 | Ig Farbenindustrie Ag | Improvements relating to the dyeing and printing of cellulose acetate |
| GB1425205A (en) * | 1972-07-13 | 1976-02-18 | Bayer Ag | Basic azo dyestuffs |
-
1983
- 1983-10-26 GB GB08328584A patent/GB2148920B/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB327394A (en) * | 1928-10-01 | 1930-04-01 | Ig Farbenindustrie Ag | Improvements relating to the dyeing and printing of cellulose acetate |
| GB1425205A (en) * | 1972-07-13 | 1976-02-18 | Bayer Ag | Basic azo dyestuffs |
Non-Patent Citations (1)
| Title |
|---|
| }COLOUR INDEX} THIRD EDITION, 1971, SOCIETY OF DYERS AND COLOURISTS, VOLUME 4, PAGES 4041, 4042 AND 4135 (C.I. NO'S 12790, 12795, 19360) * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005003086A3 (en) * | 2003-07-02 | 2006-02-23 | Atto Tec Gmbh | Sulfonic acid derivatives of polycyclic dyes used for analytical applications |
| US8614317B2 (en) | 2003-07-02 | 2013-12-24 | Atto-Tec Gmbh | Sulfonamide derivatives of polycyclic dyes used for analytical applications |
| US8846924B2 (en) | 2003-07-02 | 2014-09-30 | Atto-Tec Gmbh | Sulfonamide derivatives of polycyclic dyes used for analytical applications |
| US9035042B2 (en) | 2003-07-02 | 2015-05-19 | Atto-Tec Gmbh | Sulfonamide derivatives of polycyclic dyes used for analytical applications |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8328584D0 (en) | 1983-11-30 |
| GB2148920B (en) | 1987-11-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19921026 |