GB2148917A - Disperse and acid azo dyes from 2-aminothiophene and 1 ,2-dihydroquinoline couplers - Google Patents
Disperse and acid azo dyes from 2-aminothiophene and 1 ,2-dihydroquinoline couplers Download PDFInfo
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- GB2148917A GB2148917A GB08328546A GB8328546A GB2148917A GB 2148917 A GB2148917 A GB 2148917A GB 08328546 A GB08328546 A GB 08328546A GB 8328546 A GB8328546 A GB 8328546A GB 2148917 A GB2148917 A GB 2148917A
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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
- C09B29/0059—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only sulfur as heteroatom
-
- 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: <IMAGE> wherein C<1> is an optionally substituted 1,2-dihydroquinoline coupler and each R is a substituent.
Description
SPECIFICATION
Disperse and acid azo dyes from 2-aminothiophene and 1,2-dihydroquinoline couplers
This invention concerns disperse and acid dyes particularly suited for the dyeing of polyamide fibres.
The dyes of the present invention are made by coupling a diazotized 2-aminothiophene with a 1 2-dihydroquinoline coupler and so have the general formula:
wherein C1 is an unsubstituted or substituted 1,2-dihydroquinoline moiety and each R is a halogen atom or an alkyl, alkoxy, alkanoyl, nitro, alkylsulfonyl, SO2 NH2, SO2NHalkyl, SO2N(alkyl)2, SO3M, alkyl-SO3M, CONY2, CONHalkyl, CON(alkyl)2, alkoxycarbonyl, alkanoyloxy, SO3al- kyi, arylsulfonyl, acylamido, aryl, aroyl, aryloxy, arylthio, alkenyl of 2-8 carbon atoms, alkenylthio of 2-8 carbon atoms, cyclohexyl, cyclohexylthio, cyclohexylsulfonyl, cyano, thiocyano, SO3C6H5, or alkylthio group, M being hydrogen, sodium, potassium, ammonium, Ca/2,
Zn/2 or a colourless cation of a primary, secondary or tertiary aliphatic or aromatic amine. Any alkyl, alkenyl or cyclic moiety in a group R may be substituted as specified below.
Preferred dyes of the invention are of the general formula:
wherein R1 is H or an alkyl, aryl, or cyclohexyl group; R2 and R3 are each independently selected from H and alkyl; R4 is H, alkyl or alkyl-SO3M; and R5 is H, alkyl, alkoxy, alkenyl of 2-8 carbons, halogen, acylamido, alkylthio or formamido, wherein any alkyl moiety may be substituted with 1-3 of - OH, halogen, - CN, alkoxy, SO3M, alkylthio, alkanyoyl, alkanoyloxy, or alkoxycarbonyl; and wherein any alkyl, alkenyl and cyclic moieties in the defined ring substituents of the thiophene or in R, may bear up to three substituents different from the moiety and independently selected from hydroxy, alkyl, alkoxy, aryl, aryloxy, cyclohexyl, furyl, (C4H30), aroyloxy, alkoxycarbonyl, alkanoyloxy, SO2NH2, SO3M, alkyl-SO3M, SO2NHaryl, SO2N- Halkyl, SO2N(alkyl)2, NHC0Oalkyl, NHCONHalkyl, acylamido, alkylsulfonamido, succinimido (C4H402N), glutarimido (C5H602N), aroyl, phthalimido (C8H402N), 1-(2-pyrrolidono) (C4H8OH), cyclohexoxy, cyano, CONY2, CON Halkyl, CON(alkyl)2, alkoxy-alkoxy, alkylthio, halogen, arylthio, alkylsulfonyl, arylsulfonyl, alkoxycarbonylamino, - NO2 and aryloxy.
The various alkyl and alkylene moieties in, for example, alkoxy, alkanoyl and the like within the above definitions of R1 - R5, and the thiophene ring substituents preferably have 1-6 carbons, and they and the alkenyl groups are straight or branched chain.
Preferred dyes of the present invention are where the thiophene ring substituents are selected from alkyl, nitro, CONH2, CONHalkyl, CON(alkyl)2, alkyl-SO3M, SO2-alkyl, SO2-aryl, alkoxycarbonyl, CONHalkyl-OH, SO2NH2, SO2NHalkyl, and SO2N-(alkyl)2.
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, and show improvements in one or more of leveling, transfer, pH stability, exhaustion, build and are non-red flaring.
The diazo components used in this invention are prepared according to procedures well known to the art.
The preparation of the sulfonated 1 ,2-dihydroquinoline is given in German Offen. 3,005,874 (C.A. 94, 15593K, 1981) and comprises sulfonating the 4alkyl-1,2-dihydroquinoline with
H2SO4, ClSO3H, and/or SO3 and converting, if desired, the acid group to its salt in known manner. 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 temperture is 40"C. which is raised to the final dyeing temperture of 98'C. for 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. The examples are included merely for purposes of illustration and are not intended to limit the scope of the invention.
EXAMPLE 1
(a) - Preparation of 1, 2-Dlnydro-Z 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 3500 g. of acetone is added at 155-160"C.
beneath the surface over a 12 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 9. of 1,2-dihydro-2,2,4,7-tetramethylquinoline boiling at 107-111 C. at 0.55 mm., a 74% yield. Where it is desired, for example, to obtain the > N-ethyl derivative, the above product can be ethylated with triethylphosphate in the presence of ethyl iodide.
(b) - Diazotization and Coupling
2-Amino-3-carbomethoxy-5-isobutyryl thiophene (11.35 g., 0.05 mole) was added to 60% aqueous acetic acid (125.0 cm3), with stirring, followed by concentrated sulphuric acid (10.0 cm3). The mixture was cooled to 0 C. Sodium nitrite (3.59 g., 0.05 mole) was added to concentrated sulphuric acid (46.0 cc.) and the solution heated to 70'C., for 5 minutes.On cooling to 0 C. the solution was 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 was added to 1-ethyl-2,2,4,7tetramethyl-1,2-dihydro-quinoline (10.75 g., 0.05 mole) in 50% aqueous ethanol (54.0 cc.) containing sodium acetate (2.05 g), at < S'C. After stirring at 0-5"C. for one hour the dye was warmed to room temperature and precipitated by adding to cold water. The product was filtered and washed well with water to yield 11.32 g. (50%) of the final dye product, I, of the formula
EXAMPLE 2
Dye 1(4.53 g., 0.01 mole) was dissolved in 23 cc. of dimethylformamide and 10 cc. of 40% aqueous methylamine was added and stirred at room temperature for 12 hours.The mixture was poured into 150 cc. of water and the precipitated product filtered and washed well with water to yield 4.06 g. (90%) of the final dye product, II, of the formula
EXAMPLE 3
Using the above procedure in Example 2, Dye Ill of the formula below was prepared from ethanolamine.
EXAMPLE 4 2-Amino-3-carbomethoxy-5-isobutyrylthiophene (2.27 g., 0.01 mole) was added to 60% aqueous acetic acid (25.0 cc.), with stirring, followed by concentrated sulphuric acid (2.0 cc.).
The mixture was cooled to 0 C. Sodium nitrite (0.72 g., 0.0104 mole) was added to concentrated sulphuric acid (9.2 cc.) and the solution heted to 70"C., for 5 minutes. On cooling to O"C. the solution was added slowly to the above amine mixture, at 0-5"C. After stirring at 0-5"C. for a further 1 hour, the diazo solution was added to the potassium salt of 1-ethyl-2,2,7trimethyl-1,2-dihydroquinolin-4-yl-methyl sulphonic acid (3.33 g., 0.01 mole), in water (11.0 cc.) at < 5 C.
After stirring at 0-5"C. for 1 hour the dye was warmed to room temperture and precipitated by adding to saturated potassium chloride solution. The product was filtered and washed with diethyl ether, to yield 3.70 g. (64.8%) of the final dye product, IV.
EXAMPLE 5
Dye IV (5.71 g., 0.01 mole) was dissolved in a 30% ethanolic solution of methylamine (28.5 cc.) and stirred at room temperature for 2 hours. The excess ethanol and methylamine were evaporated, yielding 5.70 g. (100%) of the final dye product, V.
EXAMPLE 6
Using the above procedure, in Example 5, Dye VI was prepared from ethanolamine, resulting in a yield of 6.0 g. (100%).
The following table gives additional exemplary dyes of the present invention. TABLE 1
Substituents on
Ring A R5 R2 R3 R4 R1
None H H H H H
None H H CH3 CH3 C2H5 3,5-di-CH2CH2CH CH3 CH3 CH2SO3K C3H7-n 5-CH2OC6H5 CH2CH2CH CH3 CH3 C4H9-n 4-CH2CH2OC6H11 CH2Cl H CH(CH3)2 CH3 CH2CH2-SO2NHC6H5 5-NO2 OCH2CL H CH3 CH3 CH2CH2OC6H5 3-CH2COOCH3 OCH3 H CH3 H CH2SO3K 3-CH2(C4H3O) OCH3 H CH2 CH2CH2SO3K C6H5 3-CH2-CH2-OOCC6H5 CH2CH2CH H CH3 H C6H11 3-CH2COCCH3 Cl H CH3 CH2SO3Na C2H4OC6H11 3-SCH2SO2NH2 Cl H CH3 CH3 CH2CH2SO2NH2 3-CH3 H H CH3 CH3 CH2CH2CH 3-CONHCH3 OCH3 C2H5 C2H5 C2H5 CH2CH2SO2N(C2H5)2 5-CON(C2H5)2 NHCHO CH3 CH3 CH3 CH2CH2OC2H5 5-CH2SO2NHCH3 NHCOCH2OCCH3 CH3 CH3 CH3 CH2CN 5-C6H5 NHOOCH2CH3 C3H7-n C3N7-n H CH2CONH2 5-CH3 NHCOCH2Cl CH3 CH3 CH2SO3NH4 CH2CONHCH3 5-CH2NHCOOCH3 NHCOC6H5 CH3 CH3 H CH2CON(C2H5)2 4-SCN NHCOC2H5 C4H9-n C4H9-n H CH2NHCOOCH3 4-CH2NHCONHCH3 NHCOC6H11 CH3 CH3 H CH2NHCOOCH3 4-OCH3 H CH3 CH3 CH2SO3N HCH3(h)2 CH2OOCCH3 3-Br CH2SCH3 H CH3 H CH(C4H6ON) 3-CF3 CH2CH=CH2 H H H H CH2CH2COOCH3 3-OCH2CH3 Br H CH3 CH2SO3K CH2CH2COOCH3 3-SCH3 I H CH3 CH3 H 3-SCN F H CH3 CH3 C2H4SC2H5 3-SO2NH2 SCH3 H CH3 CH3 C3H7-n 3-SO2NHC4H9-n CH2OOCCH3 H CH3 CH3 C4H9-n 3-SO2N(CH3)2 OCH3 H CH3 CH3 C2H4C6H5 3-SO3C6H5 CH3 H CH3 CH2 C2H4C6H10-p-SO3K 4-CN H H H H CH2Cl 4-CONH2 CH2CH2COOCH3 H CH3 CH3 C6H4-p-OCH3 4-COOCH2SO3K CH2CH(OH)CH2CH H CH3 CH3 C6H10-p-OH 4-COCH3 CF3 H CH3 CH3 C2H5 4-OO C6H5 CF3 H CH3 CH3 CH2CH2SC6H5 4-Cl H C2H5 C2H5 CH3 CH2CH2SO2CH3 4,5-di-Cl H C2H5 C2H5 CH3 CH2CH2SO2C6H5 4-Br CH2CH(Cl)CH2Cl C2H5 C2H5 CH3 CH2CH2OC2H4OC2H5 4-CF3 CH2CH(OCH3)CH2OCH3 CH3 CH3 CH3 CH2(C8H4O2N 5-NHCOCH3 CH3 CH3 CH3 CH3 CH2CONH2 5-SO2CH3 CH3 CH3 CH3 CH2SO4K CH2(C4H4O2N) 5-CH2SO2NHC2H5 CH3 CH3 CH3 CH3 CH2CON(C2H5)2 5-CH2SO2N(C2H502 CH3 CH3 CH3 CH3 CH2NHCONHCH3 5-SO2NHC2H5 H CH3 CH3 CH3 CH2NHSO2CH2NO2 5-CH2CH2NHCOCH2Cl H CH3 CH3 CH3 CH2OOCCH3 5-CH2NHSO2CH3 CH3 CH3 CH3 CH2SO3NH4 CH2(C4H3O) 5-CH2CH2CH2(C4H6ON) CH2CH2CH CH3 CH3 H CH2CH2COOCH3
None CH2Cl CH3 CH3 H CH2CH2OOCC6H5 3-CH2CH2CN OCH2Cl CH3 CH3 C3H7-n H 3-NHCOCH2ON OCH3 CH3 CH3 C3H7-n C2H5 3-CH2(C4H4O2N) OCH3 CH3 CH3 C2H5 C3H7-n 3-CH29C5H6O2N) CH2CH2CN CH3 CH3 C2H5 C4H9-n 3-CH2CH2(C8H4O2N) Cl CH3 CH3 C2H5 C2H5 3-CH2CONH2 Cl CH3 CH3 CH3 C2H5 3-CH2CONHCH3 H CH3 CH3 CH3 CH3 3-CH2CH2OCHCH2OC2H5 CH3 CH3 CH3 C6H4-p-CH3 3-COOCH2CH2OCH3 NHCHO CH3 CH3 CH3 CH2SO3NH4 C6H11 3-CH2CH2SCH3 NHCOCH2OCCH3 CH3 CH3 CH3 CH2OC6H5 3-CH2CH2CH2Cl NHCOCH2CH3 H H H CH2CH2OH 3-CH2SC6H5 NHCOCH2Cl H CH3 CH3 CH2CH2OH 5-CH2SO2CH3 NHCOC6H5 CH3 CH3 CH3 CH2CH2OH 4-CH2SO2C6H5 NHCOC2H5 CH3 CH3 CH2SO3Na CH2CH2OCH2CH2NHCOCH3 4-CH2CH(OH)CH2OH NHCOC6H11 H CH(CH3)2 CH3 CH2CN 4-CH2CH(OH)CH-CH2 H H CH3 CH3 CH2CONH2 4-C6H4-p-CH CH2SCH3 H CH3 H CH2CONHCN3 5-C6H4-p-C2H5 CH2CH=CH2 H CH3 H CH2CON(C2H5)2 5-C6H4-p-OC6H5 Br H CH3 CH2SO3K CH2NHCOCH3 5-C6H4-p-C6H11 I H CH3 CH3 CH2NHCOOCH3 5-C6H4-p-(C4H3O) F H CH3 CH3 CH2OOCCH3 5-C6H4-p-OCC6H5 SCH3 H CH3 CH3 CH2(C4H6ON) 5-C6H4-o-COOCH3 CH2OOCCH3 CH5 C2H5 C2H5 CH2CH2COCH3 5-C6H4-m-SO2NH2 OCH3 CH3 CH3 CH3 CH2Cl2COOCH3 5-C6H4-p-CONH2 CH3 CH3 CH3 CH2SO3K H 5-C6H4-p-NHCONHCH3 H C3H7-n C3H7-n H C2H5 5-C6H4-p-(C8H4O2N) CH2CH2COOCH3 CH3 CH3 H C3H7-n 5-C6H3-o,p-di-CN CH2CH(0H)CH2OH CH3 CH3 H C4H9-n 3-C6H2-o,m,p-tri -Cl CF3 C4H9-n C4H9-n H C2H5 3-C6H4-p-OCH2CH2OCH3 CF3 CH3 CH3 H C2H5 3-C6H4-p-SC6H5 H CH3 CH3 H CH3 5-C6H4-p-SO2CH2SO3K H H CH3 H C6H5 5-C6H4-p-SO2C6H5 CH2CH(Cl)CH2Cl H H H C6H11 5-C6H10-p-Cl CH2CH(OCH3)CH2OCH3 H CH3 CH2SO3K C2H5 3-C6H9-o,p-di-OH CH3 H CH3 CH3 CH2CH2CH 3-C6H10-p-CH3 CH3 H CH3 CH3 CH2CH2CH 3-C6H10-p-OC2H5 CH3 H CH3 CH3 CH2CH2CH 3-CH2CH2SO2NHC6H5 CH3 H CH3 CH3 CH2CH2OC2H5 3-C6H4-p-SO2NHC6H5 H H CH3 CH3 CH2CN 3-CH2CH2COH2C6H5 H H CH3 CH2SO3N H(CH3)3 CH2CONH2 5-C6H11 H H CH3 CH3 C6H4-p-(C4H4O2N) 5-SC6H5 H H CH3 CH3 C6H10-p-OCH3 4-OOCCH3 CH3 CH3 CH3 CH2SO3K C6H4-p-Cl 4-SO3-CH3 CH3 CH3 CH3 CH3 CH2(C5H6O2N) 5-SO2C6H4-p-SO3K CH3 CH3 CH3 CH3 C2H5 5-SC6H11 CH3 CH3 CH3 CH3 CH2CH2CH 5-SO2-C6-H11 CH3 CH3 CH3 CH3 CH2CH2CH 4-SO3K CH3 CH3 CH3 CH3 CH2CH2Br 3-CON(CH3)2,5-COCH(CH3)2 CH3 CH3 CH3 CH3 C2H5 3-CON(C2H5)2,5-COCH(CH3)2 CH3 CH3 CH3 CH3 C2H5 3-SO2C6H5,5-COCH(CH3)2 CH3 CH3 CH3 CH3 C2H5 3-SO2CH3,5-COCH(CH3)2 CH3 CH3 CH3 CH3 C2H5 3-CONHCH3, 5-SO2NH2 H CH3 CH3 CH3 C2H5 3-CN, 5-SO2N(C2H5)2 H CH3 CH3 CH3 C2H5 3-CON(CH3)2,5-COCH(CH3)2 CH3 CH3 CH3 CH2SO3K C2H5 3-CON(C2H5)2,5-COCH(CH3)2 CH3 CH3 CH3 CH2SO3K C2H5 3-SO2C6H5, 5-COCH(CH3)2 CH3 CH3 CH3 CH2SO3K C2H5 3-SO2CH3, 5-COCH(CH3)2 CH3 CH3 CH3 CH2SO3K C2H5 3-CONHCH3, 5-SO2NH2 H CH3 CH3 CH2SO3K C2H5 3-CN, 5-SO2N(C2H5)2 H CH3 CH3 CH2SO3K C2H5
Claims (21)
1. A dye of the formula
wherein C' is a 1 ,2-dihydroquinoline moiety which is unsubstituted or substituted, and wherein each R is alkyl, alkoxy, alkanoyl, - NO2 halogen, alkylsufonyl, SO2NH2, SO2NHalkyl, SO2N(alkyl)2, SO3M, alkyl-SO3M, CONH2, CONHalkyl, CON(alkyl)2, alkoxycarbonyl, alkanoyloxy, SO3alkyl, arylsulfonyl, acylamido, aryl, aroyl, aryloxy, arylthio, alkenyl of 2-8 carbons, alkenylthio, cyclohexylthio, SO3C6H5, cyano, thiocyano, cyclohexyl-sulfonyl, alkylthio, or cyclohexyl, any alkyl, alkenyl or cyclic moiety in a substituent R possibly bearing up to three substituents different from the moiety and independently selected from hydroxy, aklkyl, alkoxy, aryl, aryloxy, cyclohexyl, furyl (C4H30), aroyloxy, alkoxycarbonyl, alkanoyloxy, SO2NH2, SO3M, alkyl-SO3M, SO2NH-aryl, SO2NHalkyl, SO2N(alkyl)2, N HCOO-alkyl, N HCON Halkyl, acylamido, alkylsulfonamido, succinimido (C2H4O2N), glutarimido (C5H6O2N), aroyl, phthalimido (C8H4O2N), 1-(2-pyrrolidono) (C4H6OH), cyano, COHN2, CONHalkyl, CON(alkyl)2, alkoxyalkoxy, alkylthio, halogen, cyclchesoxy, arylthio, alkylsulfonyl, arylsulfonyl, alkoxycarbonylamino, ~ NO2 and aryloxy, and
M being selected from H, Na, K, NH4, Ca/2, Zn/2 and colorless cations of primary, secondary and tertiary aliphatic and aryl amines.
2. A dye according to Claim 1 wherein the coupler C has the formula
wherein R1 is H or a group selected from alkyl, aryl, and cyclohexyl; 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 2-8 carbons, halogen, acylamido, alkylthio and formamido, wherein any alkyl moiety may be substituted with 1-3 of - OH, halogen, - ON, - SO3M, alkoxy, alkylthio, alkanoyl, alkanoyloxy, or alkoxycarbonyl; and wherein any alkyl, alkenyl and cyclic moieties in the defined ring substituents of the thiophene and of R1 may bear up to three substituents different from the moiety and independently selected from hydroxy, alkyl, alkoxy, aryl, aryloxy, cyclohexyl, furyl, (C4H30), aroyloxy, alkoxycarbonyl, alkanoyloxy, SO2NH2, SO2N
Haryl, SO2NHalkyl, SO3M, SO2N(alkyl)2, NHCOOalkyl, N HCON Halkyl, acylamido, alkylsulfonamido, succinimido (C4H4O2N), glutarimido (C5H6O2N), aroyl, phthalimido (C8H4O2N), 1-(2-pyrrolidino) (C4H5OH), cyano CONH2, CONHalkyl, DON(alkyl)2, allkoxyalkoxy, alklthio, halogen, cyclochexoxy, arylthio, alkylsulfonyl, arylsulfonyl, alkoxycarbonylamino, ~ NO2 and aryloxy.
3. A dye according to claim 2 wherein the thiophene ring substituents are selected from alkyl, nitro, CONH2, CONHalkyl, CON(alkyl)2, CN, SO2alkyl, alkyl-SO3M, SO2aryl, alkoxycarbonyl, CONHalkyl-OH, SO2NH2, SO2NHalkyl, and SO2N(alkyl)2N(alkyl)2.
4. The dye according to Claim 1 of the formula
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
1 0. The dye according to Claim 1 of the formula
11. The dye according to Claim 1 of the formula
1 2. The dye according to Claim 1 of the formula
13. The dye according to Claim 1 of the formula
14. The dye according to Claim 1 of the formula
15. The dye according to Claim 1 of the formula
16. The dye according to Claim 1 of the formula
1 7. The dye according to Claim 1 of the formula
18. The dye according to Claim 1 of the formula
19. The dye according to Claim 1 of the formula
20. The dye according to Claim 1 of the formula
21. The dye according to Claim 1 of the formula
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08328546A GB2148917B (en) | 1983-10-26 | 1983-10-26 | Disperse and acid azo dyes from 2-aminothiophene and 1,2-dihydroquinoline couplers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08328546A GB2148917B (en) | 1983-10-26 | 1983-10-26 | Disperse and acid azo dyes from 2-aminothiophene and 1,2-dihydroquinoline couplers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8328546D0 GB8328546D0 (en) | 1983-11-30 |
| GB2148917A true GB2148917A (en) | 1985-06-05 |
| GB2148917B GB2148917B (en) | 1987-05-13 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08328546A Expired GB2148917B (en) | 1983-10-26 | 1983-10-26 | Disperse and acid azo dyes from 2-aminothiophene and 1,2-dihydroquinoline couplers |
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| GB (1) | GB2148917B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2627775A1 (en) * | 1988-02-26 | 1989-09-01 | Ciba Geigy Ag | AZO COLORANTS, PROCESS FOR THEIR PREPARATION, AND USE THEREOF |
| US5071968A (en) * | 1989-03-06 | 1991-12-10 | Ciba-Geigy Corporation | Azo dyes containing a 7-sulfoalkanoylamino-1,2,3,4-tetrahydroquinoline coupling component |
| WO2005003086A3 (en) * | 2003-07-02 | 2006-02-23 | Atto Tec Gmbh | Sulfonic acid derivatives of polycyclic dyes used for analytical applications |
-
1983
- 1983-10-26 GB GB08328546A patent/GB2148917B/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2627775A1 (en) * | 1988-02-26 | 1989-09-01 | Ciba Geigy Ag | AZO COLORANTS, PROCESS FOR THEIR PREPARATION, AND USE THEREOF |
| US5013826A (en) * | 1988-02-26 | 1991-05-07 | Ciba-Giegy Corporation | Azo dyes containing 5-cyclohexylcarbonyl-thiophene diazo components and 1,2,3,4-tetrahydroquinoline coupling components |
| US5071968A (en) * | 1989-03-06 | 1991-12-10 | Ciba-Geigy Corporation | Azo dyes containing a 7-sulfoalkanoylamino-1,2,3,4-tetrahydroquinoline coupling component |
| 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 |
|---|---|
| GB2148917B (en) | 1987-05-13 |
| GB8328546D0 (en) | 1983-11-30 |
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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 |