GB2148918A - Disperse and acid azo dyes having 1,2-dihydroquinoline couplers and heterocyclic diazos - Google Patents

Disperse and acid azo dyes having 1,2-dihydroquinoline couplers and heterocyclic diazos Download PDF

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GB2148918A
GB2148918A GB08328547A GB8328547A GB2148918A GB 2148918 A GB2148918 A GB 2148918A GB 08328547 A GB08328547 A GB 08328547A GB 8328547 A GB8328547 A GB 8328547A GB 2148918 A GB2148918 A GB 2148918A
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formula
alkyl
dye according
so3m
alkoxy
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GB8328547D0 (en
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Paul William Law
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Kodak Ltd
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Kodak Ltd
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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
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
    • C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
    • C09B29/0085—Thiazoles or condensed thiazoles
    • 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
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
    • C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
    • C09B29/0081—Isothiazoles or condensed isothiazoles
    • 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
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
    • C09B29/0092—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with two nitrogen and one sulfur as heteroatoms
    • 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

Abstract

New dyes of formula (I) give blue to green shades on polyamide fibres: D-N=N-C'???????????? (I> wherein C' is an optionally substituted 1,2-dihydroquinoline coupler, and D is selected from: <IMAGE> wherein rings I-IV are optionally substituted.a

Description

SPECIFICATION Disperse and acid azo dyes having 1,2-dihydroquinoline couplers and heterocyclic diazos 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 thiazol-2-yl, isothiazol-3-yl, 1 ,2,4-thiadiazol-5-yl or 1 ,3,4-thiadiazol-2-yl, each of which is unsubstituted or substituted with substituents such as acyl, acylamido, alkyl, SO3M, carboalkoxy, halogen, cyano and alkyl-SO3M, as defined below, and C' is a 1,2-dihydroquinoline coupler which is unsubstituted or substituted with such substituents as alkyl, aryl, alkyl-SO3M, and substituted alklyl.
More particularly, with regard to the above formula, D is selected from
wherein the rings l-IV are either unsubstituted or substituted with substituents selected from alkyl, alkoxy, halogen, alkylsulfonyl, S02NH2, SO2NHalkyl, SO3M, alkyl-SO3M, SO2N(alkyl)2, arylsulfonyl, acylamido, aryl, arylthio, alkenylthio, cyclohexylthio, SO3C6H5, cyano, thiocyano, cyclohexylsulfonyl, alkylthio, nitro, formyl, alkanoyl, alkoxycarbonyl, aroyl, dialkylcarbamoyl, aroylamino alkylsulfonamido, CF3, carbamoyl, alkylcarbamoyl, and cyclohexyl, wherein the alkyl, alkyl and cyclic moieties in said ring substituents may bear up to three substituents different from the moiety and independently selected from hydroxy, alkyl, alkoxy, aryl, cyclohexyl, furyl (C4H 30), aroyloxy, alkoxycarbonyl, alkanoyloxy, SO2NH2, SO2NHaryl, SO2NHalkyl, SO2N-(alkyl)2, NHC00alkyl, NHCONHalkyl, acylamido, alkylsulfonamido, succinimido (C4H402N), alkyl-SO3M, glutarimido (C5H602N), phthalimido (C8H402 N), 1-(2-pyrrolidono) (C4H6ON), cyano, CONY2, CONHalkyl, CON(alkyl)2, alkoxy-alkoxy, alkylthio, halogen, arylthio, alkylsulfonyl, arylsulfonyl, and aryloxy, and the coupler C' has the formula
wherein R1 is H or a group selected from alkyl, aryl and cyclohexyl, which groups may themselves be substituted with 1-3 substituents different from the said group and independently selected from hydroxy, alkoxy, aryl, aryloxy, cyclohexyl, cyclohexoxy, furyl (C4H30), aroyloxy, alkoxycarbonyl, alkanoyloxy, SO2NH2, SO2NHaryl. SO2NHalkyl, SO2N-(alkyl)2, NHCOOalkyl, N HCON Halkyl, acylamido, alkylsulfonamido, succinimido (C4H402N), glutarimido (C5H602N), phthalimido (CBH4O2N), 1-(2-pyrrolidono) (C4H6ON), cyano, CONY2, CONHalkyl, -SO3M, alkyl-SO3M, CON(alkyl)2, alkoxyalkoxy, alkylthio, halogen, arylthio, alkylsulfonyl and arylsulfonyl, R2 and 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 2-6 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, alkanoyloxy, and alkoxycarbonyl, wherein M is selected from H, Na, K, NH4, Ca Zn 2 2 and the colorless cations of primary, secondary and tertiary aliphatic and aryl amines.
The various alkyl moieties in, for example, alkoxy, alkanoyl and the like within the above definitions of R1, R5, and the D radical substituents preferably have 1-6 carbons, and they and the alkenyl groups are straight or branched chain. Any aryl moiety preferably has 6-10 ring carbon atoms.
Preferred of the present dyes are where the substituents on the D rings are selected from alkylthio, arylthio, cyclohexylthio, alkyl-SO3M, cyanoalkyl, alkyl and halogen, R1 is H, alkyl, hydroxyalkyl, alkanoyloxyalkyl or alkoxycarbonylalkyl, and R5 is H or alkyl.
The dyes of this invention impart blue to green shades on fibers, particularly polyamides, exhibiting improvements in fastness to one or more of light, ozone, perspiration, oxides of nitrogen, washing, sublimation and 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 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.
The following examples illustrate procedures which are generally applicable for preparation of the present couplers and dyes.
EXAMPLE 1 (a9Preparation of 1, 2-Dihydro-2, 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 leave about 690 g. of 1,2-dihydro-2,2,4,7-tetramethylquinoline boiling at 107-111 C. at 0.55 mm., a 74% yield. This product is then ethylated with triethylphosphate in the presence of ethyl iodide.
(b)-Diazotization and Coupling Sodium nitrite (3.6 g.) is added portionwise to 25 ml. of concentrated H2SO4. The solution is cooled and 100 ml. of 1:5 acid (1 vol. propionic:5 vol. acetic) is added below 15"C. The mixture is cooled and 8.05 g. (0.05 m) of 2-amino-5-ethylthio-1,3,4-thiadiazole is added below 10"C. After stirring at 0-5"C. for one hour, the diazo solution is added to 1-ethyl-2,2,4,7 tetramethyl-1,2-dihydroquinoline (10.75 g., 0.05 mole) in 50% aqueous ethanol (54.0 cc.) containing sodium acetate (2.05 g), at < 5 C. After stirring at 0-5"C. for one hour the dye is warmed to room temperture and precipitated by adding to cold water.The product is filtered and washed well with water to yield the dye.
The preparation of the sulfonated 1,2-dihydro-quinoline is given in German Offen. 3,005,874 (C.A. 94, 15593K, 1981) and comprises sulfonating the 4-alkyl-1,2-dihydroquinoline with H2S04, ClSO3H, and/or SO3 and converting, if desired, the acid group to its salt in known manner.
EXAMPLE 2 The diazonium from Example 1 (b) is added to the potassium salt of 1-ethyl-2,2,7-trimethyl1,2-dihydroquinoline-4-yl methyl sulfonic acid (0.01 mole) in water (11 cc.) at < 5'C. After stirring at 0-5"C. for one hour the dye was warmed to room temperature and precipitated by adding to a saturated potassium chloride solution. The product was filtered and washed with diethyl ether, to yield the final dye product.
EXAMPLE 3 By application of the above procedure, in Example 2, the following dye is prepared
The exemplary dyes of the following tables are prepared as in the above examples by procedural modifications if such are needed, as known to those skilled in the art. TABLE 1
Substituent on Ring I or II R5 R2 R3 R4 R1 None H H H H H None H H CH3 CH3 C2H5 CN CH3 CH3 CH3 CH3 C3H7-n CH3 CH2CH2OH CH3 CH3 CH2SO3K C4H9-n CH2CH2SCH3 CH2Cl H CH(CH3)2 CH3 CH2CH2-SO2NHC6H5 CH2CH2OCH2CH2OC2H5 OCH2Cl H CH3 CH2SO3Na CH2CH2OC6H5 CH2CH(CH3)2 OCH3 H H H CH3 C6H4-p-SO3K OCH3 H H CH2SO3(Ca/2) C6H4-p-SO3K C6H11 CH2CH2CN H H CH2SO3(Zn/2) C6H11 C6H4-o-Cl Cl H CH3 CH3 CH2CH2OC6H11 C6H4-m-CH3 Cl H CH3 CH2SO3NH4 CH2CH2SO2NH2 C6H4-p-OCH3 H H CH3 CH3 CH2CH2OH OC2H5 OCH3 CH3 CH3 CH3 CH2CH2SO2N(C2H5)2 CH2SO2NHCH3 NHCHO CH3 CH3 CH3 CH2CH2OC2H5 CH2SO2NH2 NHCOCH2OCCH3 C4H9-n C4H9-n CH3 CH2CN CH2OOCCH3 NHCOCH2CH3 C4H9-n C4H9-n H CH2CONR2 CH2COOCH3 NHCOC2H5 C4H9-n C4H9-n H CH2COMHCH3 CH2OOCC6H5 NHCOC6H5 C3H7-n C3H7-n H CH2CON(C2H5)2 SO2NHCH3 NHCOC2H5 C3H7-n C3H7-n H CH2NHCOCH3 CH2CON(C2H5)2 NHCOC6H11 C3H7-n C3H7-n CH2SO3N H(Et)3 CH2NHCOOCH3 Cl H CH3 CH3 H CH2OOCCH2-SO3K CH2CH2(C4H3O) CH2SCH3 H CH3 CH2SO3N HCH3(Ph)2 CH(C4H6ON) SO2C6H11 CH2CH=CH2 H H H CH2CH2COOCH3 I Br H CH3 CH3 CH2CH2COOCH3 Br I H CH3 CH3 H SO2CH3 F H CH3 CH2SO3K CH2CH2C2H5 SO2NH2 SCH3 H CH3 CH3 C3H7-n SO2NHCH2SO3K CH2OOCCH3 H CH3 CH3 C2H5 SO2N(C2H5)2 OCH3 H CH3 CH3 CH2CH2C6H5 SO2NHCH2CH2CH2OCH3 CH3 H CH3 CH3 CH2C6H11 SO2CH2CH2OC2H5 CH3 H CH3 CH3 CH2Cl SC6H5 CH2CH2COOCH3 H CH3 CH3 C6H5 SC6H11 CH2CH(OH)CH2OH H CH3 CH3 C6H4-p-OCH3 SO2C6H5 CF3 H CH3 CH3 C6H10-p-OH SO3C6H5 CF3 H CH3 CH3 CH2CH2SC6H5 SCH2CH2OH H CH3 CH3 CH3 CH2CH2SO2CH3 SCH2CH=CH2 H CH3 CH3 CH3 CH2CH2SO2C6H5 SCH2COOC2H4-SO3K CH2CH(Cl)CH2Cl CH3 CH3 CH3 CH2CH2OCH2CH2OC2H5 SCH2C6H5 CH2CH(OCH3)CH2OCH3 CH3 CH3 CH3 CH2CH SCH2C6H11 CH3 CH3 CH3 CH2SO3K CH2(C8H4O2N) SCH2CH2OC2H5 CH3 CH3 CH3 CH3 CH2CONHCH3 SCN H CH3 CH3 CH3 CH2CON(C2H5)2 SCH2CH2NHCOCH3 H CH3 CH3 CH2SO2Na CH2NHCOCH3 SCH2CH2(C4H4O2N) CH3 CH3 CH3 CH3 CH2NHCOOCH3 CH2SC6H5 CH2CH2OH CH3 CH3 CH3 CH2OOCCH3 CH2CH2SO2CH3 CH2Cl CH3 CH3 CH3 CH2(C4H6O2N) CH2SO2C6H5 OCH2Cl CH3 CH3 H CH2CH2COOCH3 SCH2CH2OC6H5 OCH3 CH3 CH3 H CH2CH2COOCH3 SCH2CH3 OCH3 CH3 CH3 C3H7-n CH2OOCC6H5 CH2(C8H4O2N) CH2CH2CN CH3 CH3 C3H7-n C2H5 CH2NHCONHCH3 Cl CH3 CH3 C2H5 C2H5 CH2NHCOOCH3 H CH3 CH3 C2H5 C2H5 CH2SO2NHC6H5 OCH3 CH3 CH3 CH3 C2H5 CH2SO2N(C2H5)2 NHCHO H H H CH3 SCH3 NHCOCH2OCCH3 H H H C6H5 CH2(C4H4O2N) NHCOCH2CH2OCH3 CH3 CH3 CH3 C6H11 CH2SO2NHCH3 NHCOC2H5 CH3 CH3 CH2SO3K C2H5 CH2CH2NHCOCH3 NHCOC6H5 CH3 CH3 CH3 CH2CH2OH NHCOCH3 NHCOC2H5 CH3 CH3 CH3 CH2CH2OH CH2CH2(C4H6ON) NHCOC6H11 CH3 CH3 CH2 SO3NH4 CH2CH2OH C6H4-p-CN H CH3 CH3 CH3 CH2CH2OC2H5 CH2CONH2 CH2SCH3 CH3 CH3 CH3 CH2CN CH2CONHCH3 CH2CH=CH2 CH3 CH3 CH3 CH2CONH2 NO2 H H H H H CHO H H CH3 CH3 C2H5 COCH3 CH3 CH3 CH3 CH3 C2H5 COOCH3 CH2CH2OH CH3 CH3 CH3 C2H5 COC6H5 CH2Cl H CH(CH3)2 CH3 C2H5 NHCOC6H5 OCH2Cl H CH3 CH2SO3NH4 C2H5 NHSO2CH3 OCH3 H H H CH3 CH3 OCH3 H H CH2CH2SO3K C6H5 CONH2 CH2CH2CN H H H C6H11 CONHCH3 Cl H CH3 CH2SO3K C2H5 CON(C2H5)2 Cl H CH3 CH3 CH2CH2OH SCH2CH3 H H H H C2H5 C6H5 CH3 CH3 CH3 CH3 C2H5 Cl CH3 CH3 CH3 H CH2CH2C6H5 CH3 CH3 CH3 CH3 H C2H5 C6H5 CH3 CH3 H H CH2CH2OH SCH2CH3 CH3 CH3 CH3 CH3 CH2C6H5 SCH2CH3 H H H CH2SO3NH4 C2H5 C6H5 CH3 CH3 CH3 CH2SO3Na C2H5 Cl CH3 CH3 CH3 CH2SO3Na CH2CH2C6H5 CH3 CH3 CH3 CH3 CH2SO3Na C2H5 C6H5 CH3 CH3 H CH2SO3NHEt3 CH2CH2OH SCH2CH3 CH3 CH3 H CH2SO3K CH2C6H5 TABLE 2
R6 R7 R5 R2 R3 R4 R1 H H H H H H H H H H H CH3 CH3 C2H5 Cl CN CH3 CH3 CH3 CH3 C2H5 Br CH3 CH2CH2OH CH3 CH3 CH3 CH2CH2SO2N(CH3)2 CH3 CH2CH2SCH3 CH2Cl H CH(CH3)2 CH2SO3K C2H5 CH CH2CH2OCH2CH2OC2H5 OCH2Cl H CH3 CH2SO3NH4 C2H5 C2H5 CH2CH(CH3)2 OCH3 H N H CH2C6H4-p-SCH3 COOCH3 C6H5 OCH3 H H CH2SO3(Ca/2) C6H5 CONH2 C6H11 CH2CH2CN H H H C6H11 CON(C2H5)2 C6H4-o-Cl Cl H CH3 CH2SO3(Zn/2) C2H5 CH2OOC2H5 C6H4-m-CH3 Cl H CH3 CH3 CH2CH2OH C6H5 C6H4-p-OCH3 H H CH3 CH3 CH2CH2OH CH2CH2SCH3 OC2H5 OCH3 CH3 CH3 CH3 CH2CH2OH CH2CH2OCH2CH2OC2H5 CH2SO2NHCH3 NHCHO CH3 CH3 CH3 CH2CH2OC2H5 CH2CH(CH3)2 CH2SO2NH2 NHCOCH2OCCH3 C4H9-n C4H9-n CH3 CH2CN C6H5 CH2OOCCH3 NHCOCH2CH3 C4H9-n C4H9-n H CH2CONH2 C6H11 CH2COOCH3 NHCOC2H5 C4H9-n C4H9-n H CH2CONHCH3 C6H4-n-Cl CH2OOCC6H5 NHCOC6H5 C3H7-n C3H7-n CH2CH2SO3K CH2CON(C2H5)2 C6H4-m-CH3 SO2NHCH3 NHCOC2H5 C3H7-n C3H7-n H CH2NHCOCH3 C6H4-p-OCH3 CH2CON(C2H5)2 NHCOC6H11 C3H7-n C3H7-n CH2SO3Na CH2NHCOOCH3 OC2H5 Cl H CH3 CH3 H CH2OOCCH3 CH2SO2NHCH3 CH2CH2(C4H3O) CH2SCH3 H CH3 CH2SO3N H(Et)3 CH(C4H6ON) CH2SO2NH2 SO2C6H11 CH2CH=CH2 H H H CH2CH2COOCH3 CH2OOCCH3 I Br H CH3 CH3 CH2CH2COOCH3 CH2COOCH2SO3K Br I H CH3 CH3 H CH2OOCC6H5 SO2CH3 F H CH3 CH2SO3K C2H5 SO2NHCH3 SO2NH2 SCH3 H CH3 CH3 C2H5 CH2CON(C2H5)2 SO2NHCH2SO3K CH2OOCCH3 H CH3 CH3 C2H5 Cl SO2N(C2H5)2 OCH3 H CH3 CH2SO3NH4 C2H5 CH2CH2(C4H3O) CO2NHCH2CH2CH2OCH3 CH3 H CH3 CH3 C2H5 CH2(C8H4O2N) SO2CH2CH2OC2H5 CH3 H CH3 CH3 CH3 CH2NHCONHCH3 SC6H5 CH2CH2COOCH3 H CH3 CH3 C6H5 CH2NHCOOCH3 SC6H11 CH2CH(OH)CH2OH H CH3 CH3 C6H11 CH2SO2NHC6H5 SO2C6H5 CF3 H CH3 CH2SO3Na C2H5 CH2SO2N(C2H5)2 SO3C6H5 CF3 H CH3 CH3 CH2CH2OH SCH3 SCH2CH2OH H CH3 CH3 CH3 CH2CH2OH CH2(C4H4O2N) SCH2CH=CH2 H CH3 CH3 CH3 CH2CH2OH CH2SO2NHCH3 SCH2COOC2H5 CH2CH(Cl)CH2Cl CH3 CH3 CH3 CH2CHOC2H5 CH2CH2NHCOCH3 SCH2C6H5 CH2CH(OCH3)CH2OCH3 CH3 CH3 CH3 CH2CN NHCOCH3 SCH2C6H11 CH3 CH3 CH3 CH3 CH2CONH2 CH2CH2(C4H6ON) SCH2CH2OC2H5 CH3 CH3 CH3 CH2SO3K CH2CONHCH3 C6H4-p-CN SCN H CH3 CH3 CH3 CH2CON(C2H5)2 CH2CONH2 SCH2CH2NHCOCH3 H CH3 CH3 CH3 CH2NHCOCH3 CH2CONHCH3 SCH2CH2(C4H4O2N) CH3 CH3 CH3 CH3 CH2NHCCOCH3 H CH2SC6H5 CH2CH2OH CH3 CH3 CH3 CH2OOCCH3 H CH2CH2SO2CH3 CH2Cl CH3 CH3 CH3 CH2(C4H6O2N) Cl CH2SO2C6H5 OCH2Cl CH3 CH3 H CH2CH2COOCH3 Br SCH2CH2OC6H5 OCH3 CH3 CH3 H CH2CH2COOCH3 CH3 SCH2CH3 OCH3 CH3 CH3 C3H7-n H CN CH2(C8H4O2N) CH2CH2CN CH3 CH3 C3H7-n C2H5 C2H5 CH2NHCONHCH3 Cl CH3 CH3 C2H5 C2H5 COOCH3 CH2NHCOOCH3 H CH3 CH3 C2H5 C2H5 CONH2 CH2SO2NHC6H5 OCH3 CH3 CH3 CH3 C6H4-o,p-di-Cl CON(C2H5)2 CH2SO2N(C2H5)2 NHCHO H H H CH3 CH2COC2H5 SCH3 NHCOCH2OCCH3 H H H C6H5 C6H5 CH2(C4H4O2N) NHCOCH2CH2OCH3 CH3 CH3 CH2SO3K C6H10-p-Cl CH2CH2SCH3 CH2SO2NHCH3 NHCOC2H5 CH3 CH3 CH3 C2H5 CH2CH2OCH2CH2OC2H5 CH2CH2NHCOCH3 NHCOC6H5 CH3 CH3 CH3 CH2CH2OH CH2CH(CH3)2 NHCOCH3 NHCOC2H5 CH3 CH3 CH2SO3K CH2CH2OH C6H5 CH2CH2(C4H6ON) NHCOC6H11 CH3 CH3 CH3 CH2CH2OH C6H11 C6H4-p-CN H CH3 CH3 CH3 CH2CH2OC2H5 C6H4-o-Cl CH2CONH2 CH2SCH3 CH3 CH3 CH3 CH2CN C6H4-m-CH3 CH2CONHCH3 CH2CH=CH2 CH3 CH3 CH3 CH2CONH2 C6H4-p-OCH3 NO2 H H H H H OC2H5 CHO H H CH3 CH3 C2H5 CH2SO2NHCH3 COCH3 CH3 CH3 CH3 CH3 C3H7-n CH2SO2NH2 COOCH3 CH2CH2OH CH3 CH3 CH3 C4H9-n CH2OOCCH3 COC6H5 CH2Cl H CH(CH3)2 CH3 C2H5 CH2COOCH3 NHCOC6H5 OCH2Cl H CH3 CH2SO3K C2H5 CH2OOCC6H5 NHSO2CH3 OCH3 H N H CH3 SO2NHCH3 CF3 OCH3 H H H C6H5 CH2CON(C2H5)2 CONH2 CH2CH2CN H H H C6H11 Cl CONHCH3 Cl H CH3 CH2SO3NH4 C2H5 CH2CH2(C4H3O) CON(C2H5)2 Cl H CH3 CH3 CH2CH2OH CH3 Cl CH3 CH3 CH3 CH3 C2H5 CH3 Br H CH3 H CH3 CH2CH2CH CH3 CN CH3 CH3 CH3 CH3 C2H5 CH3 COOCH3 CH3 CH3 H CH3 CH2CH2OOCCH3 CH3 COOCH3 CH3 CH3 CH3 CH3 CH2CH2OH H SO2CH3 H CH3 H CH3 C2H5 H CN CH3 H H CH2 CH2CH2OOCCH3 CH3 Cl CH3 CH3 CH3 CH2SO3Na C2H5 CH3 Br H CH3 H CH2SO3Na CH2CH2OH CH3 CN CH3 CH3 CH3 CH2SO3Na C2H5 CH3 COOCH3 CH3 CH3 H CH2SO3K CH2CH2OOCCH3 CH3 COOCH3 CH3 CH3 CH3 CH2SO3K CH2CH2OH H SO2CH3 H CH3 H CH2SO3K C2H5 H CN CH3 H H CH2SO3K CH2CH2OOCCH3

Claims (29)

  1. CLAIMS 1. A dye of the formula D - N = N - C' wherein D is selected from
    wherein the rings l-IV are either unsubstituted or substituted with substitutents selected from alkyl, alkoxy, halogen, alkylsulfonyl, SO2NH2, SO2NHaikyl, SO2N(alkyl)2, arylsulfonyl, acylamido, aryl, arylthio, alkenylthio, cyclohexylthio, SO3M, alkyl-SO3M, SO3C6H5, cyano, thiocyano, cyclohexyl-sulfonyl, alkylthio, nitro, formyl, alkanoyl, alkoxycarbonyl, aroyl, dialkylcarbamoyl, aroylamino, alkylsulfonamido, CF3, carbamoyl, alkylcarbamoyl. and cyclohexyl, wherein the alkyl, alkenyl and cyclic moities in said ring substituents may bear up to three substituents different from the moiety and independently selected from hydroxy, alkyl, alkoxy, aryl, SO3M, alkyl-SO3M, cyclohexyl, furyl, (C4H3O), aroyloxy, alkoxy carbonyl, alkanoyloxy, SO2NH2, SO2 N- Haryl, SO2NH-alkyl, SO2N(alkyl)2, NHCOOalkyl, NHCONHalkyl, acylamido, alkysulfonamido, succinimido (C4H4O2N), glutarimido (C5H6O2N), phthalimido (C8H4O2N), 1 -(2-pyrrolidono) (C4H6ON), cyano, CONY2, CONHalkyl, CON-(alkyl)2, alkoxyalkoxy, alkylthio, halogen, arylthio, alkylsulfonyl, arylsulfonyl, and aryloxy 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 C' is a substituted or unsubstituted 1 ,2-dihydroquinoline radical.
  2. 2. A dye according to Claim 1 wherein the coupler C has the formula
    wherein R, is H or a group selected from alkyl, aryl and cyclohexyl, which groups may themselves be substituted with 1-3 substituents different from the said group and independently selected from hydroxy, alkoxy, aryl, aryloxy, cyclohexyl, cyclohexoxy, furyl (C4H30), aroyloxy, alkoxy-carbonyl, alkanoyloxy, SO2NH2, SO 2NHaryl, SO2NHalkyl, SO2N(alkyl)2, NHCOOalkyl, SO3M, alkyl-SO3M, N HCON Halkyl, acylamido, alkylsulfonamido, succinimido (C4H4O2N), glutarimido (C5H8O2N), phthalimido (C8H4O2N), 1-(2-pyrrolidono) (C4H6ON), cyano, CONY2, CO NHalkyl, CON(alkyl)2, alkoxyalkoxy, alkylthio, halogen, arylthio, alkylsulfonyl and arylsulfonyl, R2 and 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 2-6 carbons, halogen, acylamido, alkylthio and formamido, wherein the alkyl moieties thereof may be substituted with 1-3 substituents independently selected from hyroxy, halogen, cyano, alkoxy, alkylthio, alkanoyl, alkanoyloxy, and alkoxycarbonyl.
  3. 3. A dye according to Claim 2 wherein the substituents on the D rings are selected from alkylthio, arylthio, cyclohexylthio, alkyl-SO3M, cyanoalkyl, alkyl and halogen, R, is H, alkyl, hydroxyalkyl, alkanoyloxyalkyl or alkoxycarbonylalkyl, and R5 is H or alkyl.
  4. 4. The dye according to Claim 1 of the formula
  5. 5. The dye according to Claim 1 of the formula
  6. 6. The dye according to Claim 1 of the formula
  7. 7. The dye according to Claim 1 of the formula
  8. 8. The dye according to Claim 1 of the formula
  9. 9. The dye according to Claim 1 of the formula
  10. 10. The dye according to Claim 1 of the formula
  11. 11. The dye according to Claim 1 of the formula
  12. 1 2. The dye according to Claim 1 of the formula
  13. 13. The dye according to Claim 1 of the formula
  14. 14. The dye according to Claim 1 of the formula
  15. 15. The dye according to Claim 1 of the formula
  16. 16.The dye according to Claim 1 of the formula
  17. 1 7. The dye according to Claim 1 of the formula
  18. 18. The dye according to Claim 1 of the formula
  19. 1 9. The dye according to Claim 1 of the formula
  20. 20. The dye according to Claim 1 of the formula
  21. 21. The dye according to Claim 1 of the formula
  22. 22. The dye according to Claim 1 of the formula
  23. 23. The dye according to Claim 1 of the formula
  24. 24. The dye according to Claim 1 of the formula
  25. 25. The dye according to Claim 1 of the formula
  26. 26. The dye according to Claim 1 of the formula
  27. 27. The dye according to Claim 1 of the formula
  28. 28. The dye according to Claim 1 of the formula
  29. 29. The dye according to Claim 1 of the formula
GB08328547A 1983-10-26 1983-10-26 Disperse and acid azo dyes having 1,2-dihydroquinoline couplers and heterocyclic diazos Expired GB2148918B (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4754022A (en) * 1984-11-13 1988-06-28 Ciba-Geigy Corporation Cationic dyes from diazotized 5-aminoisothiazoles and tetrahydroquinolines or indolines
EP0572973A2 (en) * 1992-06-02 1993-12-08 Mitsubishi Chemical Corporation Metal chelate compound and optical recording medium using the compound
EP0578870A1 (en) * 1992-07-14 1994-01-19 Agfa-Gevaert N.V. Thiazolylazoaniline dyes for use in thermal dye sublimation transfer
WO2005003086A3 (en) * 2003-07-02 2006-02-23 Atto Tec Gmbh Sulfonic acid derivatives of polycyclic dyes used for analytical applications

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4754022A (en) * 1984-11-13 1988-06-28 Ciba-Geigy Corporation Cationic dyes from diazotized 5-aminoisothiazoles and tetrahydroquinolines or indolines
EP0572973A2 (en) * 1992-06-02 1993-12-08 Mitsubishi Chemical Corporation Metal chelate compound and optical recording medium using the compound
EP0572973A3 (en) * 1992-06-02 1994-05-25 Mitsubishi Chem Ind Metal chelate compound and optical recording medium using the compound
US5447823A (en) * 1992-06-02 1995-09-05 Mitsubishi Chemical Corporation Metal chelate compound and optical recording medium using the compound
EP0578870A1 (en) * 1992-07-14 1994-01-19 Agfa-Gevaert N.V. Thiazolylazoaniline dyes for use in thermal dye sublimation transfer
US5616697A (en) * 1992-07-14 1997-04-01 Agfa-Gevaert, N.V. Thiazolylazoaniline dyes for use in thermal dye sublimination transfer
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
GB2148918B (en) 1987-11-18
GB8328547D0 (en) 1983-11-30

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