GB2125424A - Acid dyes from acid substituted 2-aminothiophenes and aniline, tetrahydroquinoline, and benzomorpholine couplers - Google Patents
Acid dyes from acid substituted 2-aminothiophenes and aniline, tetrahydroquinoline, and benzomorpholine couplers Download PDFInfo
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- GB2125424A GB2125424A GB08222579A GB8222579A GB2125424A GB 2125424 A GB2125424 A GB 2125424A GB 08222579 A GB08222579 A GB 08222579A GB 8222579 A GB8222579 A GB 8222579A GB 2125424 A GB2125424 A GB 2125424A
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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
- C09B29/3686—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing nitrogen and oxygen as heteroatom
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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
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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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0801—Amino benzenes containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H, OPO3H2; SO2NHSO2R or salts thereof, R being hydrocarbonyls
- C09B29/0803—Amino benzenes containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H, OPO3H2; SO2NHSO2R or salts thereof, R being hydrocarbonyls containing SO3H, OSO3H
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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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- Plural Heterocyclic Compounds (AREA)
Abstract
Novel azo dyes are derived from 2-aminothiophenes substituted at the 4- position with a methylene group bearing an acid group of the formula -SO3M, -OSO3M, or -SSO3M wherein M is H<+>, K<+>, Na<+> or NH4<+>, and also substituted at the 3- and 5-positions with any of a variety of groups such as -CN and -CHO, and from aniline, tetrahydroquinoline or benzomorpholine couplers which may contain any of a great variety of substituents. The dyes impart red to blue shades on hydrophobic fibers, including polyesters, polyamides, and cellulose esters, and are of particular interest for dyeing polyamide fibers, exhibiting improved properties thereon such as fastness to light and migration. The dyes have the general formula: <IMAGE> wherein R<12>, R<14> are independently selected from -CN, -CHO, -OOCR<15>, -COOR<15>, -SCN and -CONR<15>R<16>; R<15> is alkyl or aryl; each R<16> is independently selected from H, alkyl, and aryl; R<13> is -SO3M, -OSO3M or -SSO3M where M is H<+>, K<+>, Na<+> or NH4<+>.
Description
SPECIFICATION
Acid dyes from acid substituted 2-aminothiophenes and aniline, tetrahydroquinoline, and benzomorpholine couplers
This invention relates to new azo dyes derived from 2-amino-thiophenes substituted at the 4position with a methylene group bearing an acid group of the type 503 M, 0503 M, 0 r-SSO3M wherein M is H+, K+, Na+ or NH4+, and also substituted at the 3- and 5-positions with any of a variety of groups such as -CN, -CHO or the like, and wherein the couplers are selected from aniline, tetrahydroquinoline and benzomorpholine compounds which may be extensively substituted.The dyes impart red to blue shades on hydrophobic fibers, including polyesters, polyamides, and cellulose esters, and are of particular interest for dyeing polyamide fibers, exhibiting improved properties thereon such as fastness to light and migration.
The dyes of this invention have the general formula:
wherein R12 and R14 are independently selected from --CN, --CHO, --00CR'5, --COOR'6, --SCN and -C0NR16R16; R15 is alkyl or aryl; each R16 is independently selected from H, alkyl, and aryl;R13 is an acid group of the type, -SO3 M,-O SO3M or -SSO3M where M is H+, K+, Na+ or NH4+; and
wherein 'COUPLER' is the residue of an aniline, tetrahydroquinoline or benzomorpholine coupling component selected from those of the formulae
wherein
R' and R2 are each selected from hydrogen, fluorine, chlorine, bromine, alkyl, cycloalkyl, alkoxy, phenoxy, alkylthio, arylthio, and radicals having the formula -NH-X-R9 in which X is -CO-, -COO-, or SO2, and R9 is selected from alkyl, aryl, alkoxyaryl, cycloalkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy, and when X is -CO-, R9 also can be hydrogen, amino, alkenyl, alkylamino, dialkylamino, arylamino or furyl;
R3 and R4 are each selected from hydrogen; cycloalkyl; cycloalkyl substituted with one or two groups selected from alkyl, -OH, alkoxy, halogen and hydroxy substituted alkyl; phenyl; phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl; straight or branched alkenyl of 2-6 carbons; straight or branched alkyl; and R3 and R4 combined forming pentamethylene, ethyleneoxyethylene or ethylenesulfonylethylene which, with the nitrogen atom to which it is attached, forms a ring;
wherein the alkyl, alkylene, and such moieties of the other groups comprising R1, R2, R3, R4, R12 and
R'4 may be substituted with 1-3 of the following: hydroxy; halogen; cyano; amino; alkoxy; alkoxycarbonyl substituted aroyloxy; alkoxyca rbonyl substituted aryl; alkoxyalkoxy; hydroxya I koxy; succinimido; glutarimido; phthalimido; phthalimidino; 2-pyrrolidono; cyclohexyl; phenoxy; phenyl; phenyl substituted with alkyl, alkoxy, alkoxycarbonyl, halogen, alkanoylamino or cyano; acrylamido; obenzoicsulfimido; alkenylcarbonylamino; groups of the formula wherein
or -CH2-0-; -S-R10 wherein R'O is selected from alkyl, alkyl substituted with one or more of halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy, phenyl, phenyl substituted with halogen, alkyl, alkoxy, alkanoylamino, cyano or alkoxycarbonyl, pyridyl, pyrimidinyl, 2-benzoxazolyl, 2-benzimidazolyl, 2-benzothiazolyl or
-S02R9; -COOR9; -OXR9; -NH-X-R9; -C0NR11R11; -502NR11R 11; wherein R9 and X are as defined above and R11 is selected from H, alkyl, aryl, alkoxyaryl, cycloalkyl, amino, alkenyl, alkylamino, dialkylamino, arylamino, furyl, and alkyl substituted with one or more of halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy; alkoxy substituted with hydroxy, cyano or alkanoyloxy; alkoxyalkoxy substituted with hydroxy, cyano, alkanoyloxy or alkoxy; phenoxy substituted with 1-3 of alkyl, alkoxy or halogen;
R5, R6, R7, and R8 are each selected from hydrogen and alkyl;
and wherein each of the above alkyl, alkylene, and such portions or moieties of the alkoxy, alkanoyl, and other groups defined above contain 1-6 carbons.
The present dyes exhibit improvements in one or more properties such as fastness to light, sublimation, chlorine, heat, ozone, gas, perspiration, crock, and wash, build, pH stability, bloom resistance, depth of shade, leveling, strike rate, energy of dyeing, migration, and the like.
The dyeing of the fibre material with the present dyestuffs may be carried out for example, from an aqueous solution in the presence of ammonium acetate, at pH 6 in the presence of a wetting agent at a temperature of 980C for 1 hour.
This invention is illustrated by the following examples.
EXAMPLES
2-Amino-3-ethoxycarbonyl-4-bromo-methyl-5-cyano thiophene (1.0 g) was diazotised in 1:5 (by volume) acetic- propionic acid, then was added to a solution of N-ethyl-2,2,4,7-tetramethyl-1 ,2,3,4- tetrahydroquinoline (0.75 g) in ethanol at OOC. After 1 hour the mixture was drowned into water, filtered and dried. The dye (1.3 g) was then dissolved in ethanol (50 ml) and to this was added potassium sulphite (0.5 g), potassium iodide (0.1 g) and water (10 ml). The mixture was then heated to reflux for 6 hours, cooled, evaporated and dried to yield 1.9 g of the acid dye. This general procedure was used to prepare the dyes of the following tables wherein Table 1 gives several of the preferred dyes.
TABLE 1
Shade
R12 R13 R14 Coupler on Nylon
NEt2 CO2Et SO3K CO2Et g red Et-N-C2H4Cfl CO2Et SSO3Na CO2Et 'Me red Me NPr2 CO2Et SO3K COVET hl violet NHCOM e CO2Et SO3K CO2Et eMe violet & H4 OH HNEt CN SO3K CN bleO < blue NHCOMe NEt2 CN OSO4K CN MeO blue rOMe TABLE 1 (Continued)
Shade
R12 R13 R14 Coupler on Nylon
Me CN SO,K CO,Et me blue Me N Me Et 0 CN SO3NH4 CO2Et Me Me blue Et Me CO2Et SO3K CN < Me blue blue Me CHO SSO3Na CN 93 blue NHCOMe 0 t NC1Hq-N'3 blue CHO SO3K CN Me j blue 0 OMe E --CZHqC1 CHO SO3K CO2Et Et};;C2HM4eC n violetviolet TABLE 1 (Continued)
Shade
R12 R13 R14 Coupler on Nylon
CHO SOsK CO2Et p1e < N Me blue CZH40H Me CO2Et SO3K CHO blue Me N(c2 H40COiMe)2 CN OSO3Na CHO Me0 Me blue StZ C2s14Ct / CONHPh SO3K CO2Et h red CN SO3Na CONHEt XMe blue C2 H40H TABLE 1 (Continued)
Shade
R12 R13 R14 Coupler on Nylon
SCN 501K CN Nt2 red NEt2 NFr SCN SO3K CO2Et XNH C0P1 violet TABLE 2
R1,R2 R3 R4 R12 R14 R13
H C2H5 C2H5 -CN -CONHCH3 -SO3Na 3-CH3 " " " -CN " 3-Cl " " -CO2Ph " " 2-OCH3-5-Cl H " -SCN -CHO -OSO3K 2-OCH3-5-CH3 " " " -CONHCH3 " 2,5-di-OCH3 " " -CO2-CH3 " " 2,5-di-CH3 " " " -CO2Ph -S-SO3K 2,5-di-Cl " " " -SCN " 2-SCH3 C6H5 " -CONHCH3 -CN " 3-OC6H5 C2H5 " -CONHPh -CHO " 3-SC6H5 " " -CONHCH3 -CONHCH3 -SO3NH4 3-Br " " -CN " " 3,5-di-NHCOCH3 " " -CO2C2H5 " " 3,5-di-CH3 " " -CN " -SO3Na 3-NHSO2C6H11 " " " " " TABLE 2 (Continued)
R1,R2 R3 R4 R12 R14 R13 3-NHSO2C2H4Cl C2H5 C2H5 -CN -CONHCH3 -SO3Na 3-NHSO2C2H4OH " " " " " 3-NHSO2CH2CN " " " " " 3-NHCOCH3 C2H4OC2H5 C2H4OC2H5 " -CN " 3-NHCOCH(CH3)2 C2H5 C3H7-n -CO2Ph " " 3-NHCOC4H9-n CH3 CH3 -SCN -CHO -OSO3K 3-NHCOCH2Cl " " " -CONHCH3 " 3-NHCOCH2OCH3 CH2C6H5 C2H5 -CO2-CH3 " " 3-NHCOCH2OC6H5 CH2CH2OCOCH3 CH2CH2OCOCH3 " -CO2Ph -S-SO3K 3-NHCOCH2C6H5 CH2CH2CN C2H5 " -SCN " 3-NHCONHC2H5 CH2CH2CONH2 " -CONHCH3 -CN " 3-NHCOC2H5 CH2CH2C6H5 CH2CH2C6H5 " -CHO " 3-NHCOC6H11 CH2CH2CH2CH2OCOCH3 CH2CH2CH2CH2OCOCH3 " -CONHCH3 -SO3NH4 3-NHCOC6H4-p-OCH3 C2H5 C2H5 -CN " " 3-NHCOCH2CN " " -CO2C2H5 " " 3-NHCOCH2CH2OCOCH3 " " -CN " -SO3Na 3-NHCOCH2SCH3 " " " -CN " 3-NHCHO " " -CO2Ph -CN " 3-NHSO2C6H5 " " -SCN -CHO -OSO3K TABLE 2 (Continued)
u q m Y O R2 R1 R4 R12 R14 R11 v, oS O H =::I O OH(CH1)O2H5 55 -C02-CH1 -CONHCH1 s 3-NHCO O2H, C2Hs Z Z 0 r r r I 5' '5 5' -SON '5 ^ I I N O o" I o Zo" 5' 5' '5 5' '5 N O 0 = '5 5' 55 5' 5' 3-OH1 OH2OH1CN '5 -OONHOH1 -ON '5 OH2OH2OO0O6H 55 5' -OHO 'I 55 OH2OH2OOONHO2H5 5' '5 -CONHCH1 -S01NH4 3-NHOOOOH1 OH2OH2OOONHO6H5 55 -ON '5 5' n N 3-NHCOOO6H11 CH2OH2OH OH2O6H5 -ON ON -SO3Na I CH2CH(OH1)-OH O6H11 55 -ON '5 3-NHOOOOH2ON CH2OH2OO6H5 O2H5 -CO2Ph -ON m CH2CH2OCH2CH2OO1H IN -SON -OHO -0501K I I I I IN n I I I I I I I t )N I IN N Z I 9 N r 0vI g A o O O 8 8 8 8 8 NC I a: z z z z z z O Z Z Zl Zl Z TABLE 2 (Continued)
R1,R2 R3 R4 R12 R14 R13
Y Yn d /COCH2 c n Z,O co l o l F I 1 '5 -O02-OH1 '5 cJ o O I I y CM2CH2fl ;Co;y I 55 -SON Y Y Co CHO O CH2Cllfl\ O -CONHCH1 -ON 55 SOz so2CJi3 '5 Cfl2Ctt2 '5 '5 -OHO 5' Cfl2C!i2CAI (ONH In I ~ : ~ : : 55 Cfi2CH2N(CO5I 5' -ON '5 55 COCH2 I o Q O\ / szz 2 Z W t7 CD o Q so :E; CD IN N O O O O TABLE 2 (Continued)
R1,R2 R3 R4 R12 R14 R13
Y o /CO = =I:I Im I CH2 o z I o o" Z o z I r I : 1 Cf I Y Y y CU2 55 OH2OH2NHOOO6H5 55 -ON ON oN Z II II 55 C!12CH2OCCOCN3 '5 -OO2Ph '5 f cn3 '5 -SON -OHO -OSO1K 55 0H20H1502NH2 5' '5 -OONHCH1 5' OH2OH2SO2N(O2H, )2 '5 -002-0H1 5' oN ~ ~ 5' '5 -OO2Ph S-SOaK 0H20H2502CH1 5' 55 -SON '5 55 0H20H2 SOH1 5' -OONHOH1 -ON 5' 55 0H20H2506H5 5' '5 -OHO R 0H2OH200006H5 o I sZ / to I t I I I I < IN I Q I = Q t I I ON I ON I N .N Q C) P P CD C) C) C) C) WN 8 Z TABLE 2 (Continued)
R1,R2 R3 R4 R12 R14 R13
(d N-----NH II o A -ON -OONHOH1 -SO3NH4 l : l l - r I = = I w N 3-NHOOOH1 z o -O01O2H5 z 55 CH2Cfl2S-C 8 51 CHaCH2OON(OaHs I I I -OONHOH3 -SO3Na 55 OH2OH2OO2O2Hs I n -ON IN OH(0H1)OH1O0202H5 S C > I IN o o o o r O Z oN z -OSO1K Y OH1OH=OH2 OH2OH=OH2 Y -OONHOH1 3-OH1 OH2CH2ON OH2OH2OOOOH1 -O02-OH1 '5 5, 5' CH2OH2OO2H5 '5 -OO2Ph -S-501K 5' -OH2OH2SO2OH2OH2- 5' -SON '5 -OH1OH1OOH2OH2- -OONHOH1 -ON 5' 00 OH2OH2OOOOH3 '5 -OHO 5' I N N N | N H 55 55 ; I X 55 ON oN OH2O6H11 C2H5 -O02O2H5 o 5' t) CD l O -ON ON % X 8 8 z 11 O N I N N Q I I I I I I I cD 3 Q I I I I I IN I I IN 8 tod zI z I ~ z TABLE 2 (Continued)
R1,R2 R3 R4 R12 R14 R13
Zo" OH2OH2ON Z Z o" o" OH1OH2OO2OH1 5' -SON -OHO -OSO1K = Y '5 5' -OONHOH1 5' I I I 3-OH1 CJi2CtJ2N( 1 -0O2-OH1 55 55 COCH2 - /COCfl\2 5' 15 000 0 00 s C}(2Cfl2N cs o"Z z a I I : I : : I : = I I Y g T COCH2 ON '5 O6H11 OH2OH2ON 55 -OHO f: OH2OH2ON z z O 0 O O O O O O O 0 s" irI I OH2OH2OOOOH1 -O02O1H5 I I oN o" OH2OH2OOH2OH2OO2H5 -ON 5' -SO1Na 55 '5 OH1OH2ON '5 -ON 3-NHOOOH1 OH(OH1)O2H5 H -OO2Ph '5 5' 5' OH2OH2OOOCH1 C2H5 -SON -OHO -0503K P OH2O6Hs g '5 -OONHCH3 55 I IN ob oa C 8 8 n O IN I I : ZJ Q Q O O O : C) C) Q O O O O I I I z TABLE 3
R1,R2,R5,R6,R7,R8 R3 R12 R14 R13
H C2H5 -CN -CONHCH3 -SO3Na " CH2C6H5 " -CN " 7-CH3 CH2CH2CH3 -CO2Ph " " 2-CH3 CH2C6H4-p-COOCH3 -SCN -CHO -OSO3K 2-CH3-7-Cl C2H5 " -CONHCH3 " 5-CH3-8-OCH3 " -CO2-CH3 " " 7-NHCOCH3 " " -CO2Ph -S-SO3K 2-CH3-7-NHCOCH3 " " -SCN " 2-CH3-7-OC2H5 " -CONHCH3 -CN " 2-CH3-7-NHCOC2H5 CH2CH2OCOCH3 " CHO " 2-CH3-7-NHCOCH(CH3)2 CH2CH2CN " -CONHCH3 -SO3NH4 2,2,4-tri-CH3-7-NHCOCH2CH3 " -CN -CONHCH3 -SO3NH4 " C2H5 -CO2C2H5 " " TABLE 3 (Continued)
R1,R2,R5,R6,R7,R8 R3 R12 R14 R13
2 2 -ON -OONHOH3 -SO1Na 2,2,4-tri-OH1-7-NHOOOH2OH3 OH OH OOH1OH2OO2H, 257-di-0H1 0H2O6H5 5, -ON 5' (d y ^ I 55 X OH2OH2OOONHO6H5 I O I I I - ^ I : I : I1 OH2OH2OO6H1 -O02-OH1 5' '5 Im r" o o o o OZ Z OI OZ O OZ z -SON OZ y OH2OH2NHOOO6H1 y y y. y I I -ON 55 5' OH2OH2OH2NHOOOQH '5 -OHO 5' f Im '5 -OONHOH1 -SO1NH4 55 OH1OH2 OONH2 -ON 55 '5 z oo o" o zo"z o" I I I I I : I r : 5' /COCfl2 55 -ON 5' Cfl2Cfl2N\ I COCH2 I I C) O ( ) O N I t")) )=( or Cn2CH2N -002Ph (D z ON o o o I L I 0 9r 2 z N I N N IN IN IN IN IN I I I I I x O C) O O O O O ON C)N N N CS) C ) ) P N IN IN IN IN IN IN I I I I IN IN IN ~ tJ IN O0 zI A .1 t7 l A TABLE 3 (Continued)
R1,R2,R5,R6,R7,R8 R3 R12 R14 R13
Co 2,7-di-OH3 Cfl2CII2 -SON -OHO -oSO3K so Y " 1 " F I 1 = 8 Y CO-NH CO-CH2 I O ~ C112 cnzn(I -C02-OH1 z 55 Cl'2 Cfl2 OH1 y O CH2OH1 I -SON 5' OH206H5 -O0NHOH1 -ON '5 2,2,4 ,7tetr.arOHa OH2OH1 5' -OHO 0 O zo"Z 5' -OONHOH1 -S01NH4 v, o o -ON 5' 55 OH2OH1OOOOH2OOH1 -002 02H1 -OONHOH1 = I u--- -ON 5' -SO3Na t OH1O6H4-p-OjOOOH3 N Lrrs -ON '5 C Ipe OH2O6H11 I I O I I I I I IN I I IN I ~ 1 A N Cfil ^ TABLE 3 (Continued)
R1,R2,R5,R6,R7,R8 R3 R12 R14 R13 2,7-di-CH3 CH2CH2SO2NH2 -SCN -CHO -OSO3K " CH2CH2SO2NHC2H4OH " -CONHCH3 " " CH2CH2CH2SO2CH3 -CO2-CH3 " " 2,2,4-tri-CH3-7-NHSO2CH3 CH2CH3 " -CO2Ph -S-SO3K 2,2,4-tri-CH3-7-NHCHO " " -SCN " 2,2,4-tri-CH3-7-NHCONHC2H5 " -CONHCH3 -CN " 2,2,4-tri-CH3-7-NHCOC6H5 " " -CHO " 2,2,4-tri-CH3-7-NHCOC6H11 " " -CONHCH3 -SO3NH4 2,2,4-tri-CH3-7-NHCOCH2CN " -CN " " TABLE 4
R1,R2,R5 R3 R12 R14 R13
H C2H5 -CN -CONHCH3 -SO3Na 3-CH3 " " -CN " 6-CH3 " -CO2Ph " " 3,6-di-CH3 CH3 -SCN -CHO -OSO3K 3-CH3-6-NHCOCH3 CH2CH3 " -CONHCH3 " 3-CH3-6-NHCOCH(CH3)2 CH2CH(CH3)2 -CO2-CH3 " " 6-NHCHO C2H5 " -CO2Ph -S-SO3K 3-CH3-6-NHCONHC2H5 " " -SCN " 3-CH3-6-NHCOC6H5 " -CONHCH3 -CN " 3-CH3-6-NHSO2C2H5 " " -CHO " 3-CH3-6-NHCOCH3 CH2CH2CN " -CONHCH3 -SO3NH4 " CH2CH2OCOCH3 -CN " " 3-CH3-6-OCH3 CH2CH3 -CO2C2H5 " " TABLE 4 (Continued)
R1,R2,R5 R3 R12 R14 R13
3,6-di-OH1 OH2OH2OO2H5 -ON -OONHOH1 -SO1Na u 55 -ON CH2OHaOOOO6Hs -OO1Ph z OH2OH(OH)CH2Cl on o coo o j w rl o o c g cticf2'N(f 0g 0 g g g cocfla /CO.
,c o z o"o o" z Co ova 4 5' -SON 55 co-Cf'2 .55 c'i2CH2Cn2N( I -OONHOH1 -CN C112 CH2 TABLE 4 (Continued)
R1,R2,R5 R3 R12 R14 R13 3,6-di-CH3 CH2CH2CH2NHCOCH3 -CONHCH3 -CHO -S-SO3K " CH2CH2OC6H5 " -CONHCH3 -SO3NH4 " CH2CH2CH2SO2CH3 -CN " " " CH2C6H5 -CO2C2H5 " " " CH2C6H4 -p-Cl -CN " -SO3Na " CH2C6H4-p-COOCH3 " -CN " " CH2CH2SCH3 -CO2Ph " " " CH2CH2OCONHC6H5 -SCN -CHO -OSO3K " CH2CH2CONH2 " -CONHCH3 " " CH2CH2SO2NH2 -CO2-CH3 " " " CH2CH2CO2C2H5 " -CO2Ph -S-SO3K " CH2C6H11 " -SCN " " CH2CH2CH2CH3 -CONHCH3 -CN " " CH2CH2OC2H4OC2H5 " -CHO " " CH2CH2C6H5 " -CONHCH3 -SO3NH4 " CH2CH2NHCOCH2OH -CN " " " CH2CH2NHCONHC2H4 -CO2C2H5 " " " CH2CH2NHSO2CH3 -CN " -SO3Na TABLE 4 (Continued)
R1,R2,R5 R3 R12 R14 R13
- Nfl z II I -ON -ON -SO1Na d Cfl N II :== -OO2Ph '5 CO Y Cfl2 o" -SON -OHO -OSO1K CH2 '5 OH2OH2SO2N(02H5)2 5' -OONHOH3 "I -O02-OH1 '5 5, z OH2OH1OONHO2H5 N -OO2Ph 55 ! Q z=w ss X z t
Claims (6)
1. A compound having the formula
wherein R12 and R14 are independently selected from --CN, --CHO. --00CR'5, --COOR'5, --SCN and -C0NR10R16; R15 is alkyl or aryl; each R16 is independently selected from H, alkyl, and aryl;R'3 is an acid group of the type, -SO3M, -OSO3M or --SSO,M where M is H+, K+, Na+ or NH4+; and wherein 'COUPLER' is the residue of an aniline, tetrahydroquinoline or benzomorpholine coupling component selected from those of the formulae
wherein
R1 and R2 are each selected from hydrogen, fluorine, chlorine, bromine, alkyl, cycloalkyl, alkoxy, phenoxy, alkylthio, arylthio, and radicals having the formula -NH-X-R9 in which X is -CO-, -OOQ, orSO2, and R9 is selected from alkyl, aryl, alkoxyaryl, cycloalkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy, and when X is -CO-, R9 is also selected from hydrogen, amino, alkenyl, alkylamino, dialkylamino, arylamino and furyl;
R3 and R4 are each selected from hydrogen; cycloalkyl; cycloalkyl substituted with one or two groups selected from alkyl, -OH, alkoxy, halogen and hydroxy substituted alkyl; phenyl; phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl; straight or branched alkenyl of 2-6 carbons; straight or branched alkyl; and R3 and R4 combined forming pentamethylene, ethyleneoxyethylene or ethylenesulfonylethylene which, with the nitrogen atom to which it is attached, forms a ring;
wherein the alkyl, alkylene, and such moieties of the other groups comprising R1, R2, R3, R4, R12 and
R14 may be substituted with 1-3 of the following: hydroxy; halogen; cyano; amino; alkoxy; alkoxycarbonyl substituted aroyloxy; alkoxycarbonyl substituted aryl; alkoxyalkoxy; hydroxyalkoxy; succinimido; glutarimido; phthalimido; phthalimidino; 2-pyrrolidono; cyclohexyl; phenoxy; phenyl; phenyl substituted with alkyl, alkoxy, alkoxycarbonyl, halogen, alkanoylamino or cyano; acrylamido; obenzoicsulfimido; alkenylcarbonylamino; groups of the formula
O wherein Y is -NH-, -N-alkyl, -O-, -S-, #CHOH, or -0H2-O-; -S-B10 wherein R10 is selected from alkyl, alkyl substituted with one or more of
halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy,
phenyl, phenyl substituted with halogen, alkyl, alkoxy, alkanoylamino, cyano or alkoxycarbonyl, pyridyl,
pyrimidinyl, 2-benzoxazolyl, 2-benzimidazolyl, 2-benzothiazolyl or
-SO2R9; - COOR9; -OXR9; -NH-X-R9; -CONR11R11; -SO2NR11R11; wherein R9 and X are as defined above and R11 is selected from H, alkyl, aryl, alkoxyaryl, cycloalkyl, amino, alkenyl, alkylamino, dialkylamino, arylamino, furyl, and alkyl substituted with one or more of halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy; alkoxy substituted with hydroxy, cyano or alkanoyloxy; alkoxyalkoxy substituted with hydroxy, cyano, alkanoyloxy or alkoxy; phenoxy substituted with 1-3 of alkyl, alkoxy or halogen; and
R5, R6, B75 and B9 are each selected from hydrogen and alkyl.
2. A compound according to Claim 1 wherein R12 and R'4 are each selected from alkoxycarbonyl, -CN, -CHO, -SCN, and alkylcarbamoyl; R3 and R4 are each selected from H, alkyl, hydroxyalkyl, cyanoalkyl, alkanoyloxyalkyl, succinimidoalkyl, chloroalkyl, and alkoxycarbonylalkyl; and R1 and R2 are each selected from alkyl, alkoxy, and alkanoylamino.
3. The compound according to Claim 1 of the formula
4. The compound according to Claim 1 of the formula
5. The compound according to Claim 1 of the formula
6. The compound according to Claim 1 of the formula
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08222579A GB2125424A (en) | 1982-08-05 | 1982-08-05 | Acid dyes from acid substituted 2-aminothiophenes and aniline, tetrahydroquinoline, and benzomorpholine couplers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08222579A GB2125424A (en) | 1982-08-05 | 1982-08-05 | Acid dyes from acid substituted 2-aminothiophenes and aniline, tetrahydroquinoline, and benzomorpholine couplers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2125424A true GB2125424A (en) | 1984-03-07 |
Family
ID=10532125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08222579A Withdrawn GB2125424A (en) | 1982-08-05 | 1982-08-05 | Acid dyes from acid substituted 2-aminothiophenes and aniline, tetrahydroquinoline, and benzomorpholine couplers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2125424A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4751288A (en) * | 1985-04-10 | 1988-06-14 | Basf Aktiengesellschaft | Azo dyes containing 2-amino-3-cyano-5-formylthiophene derivatives as diazo components and substituted aniline compounds as coupling components |
| US5283326A (en) * | 1985-05-14 | 1994-02-01 | Sandoz Ag | Dyes containing thiophene radicals |
| US5352774A (en) * | 1985-05-14 | 1994-10-04 | Sandoz Ag | Dyes containing thiophene radicals |
-
1982
- 1982-08-05 GB GB08222579A patent/GB2125424A/en not_active Withdrawn
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4751288A (en) * | 1985-04-10 | 1988-06-14 | Basf Aktiengesellschaft | Azo dyes containing 2-amino-3-cyano-5-formylthiophene derivatives as diazo components and substituted aniline compounds as coupling components |
| US5283326A (en) * | 1985-05-14 | 1994-02-01 | Sandoz Ag | Dyes containing thiophene radicals |
| US5352774A (en) * | 1985-05-14 | 1994-10-04 | Sandoz Ag | Dyes containing thiophene radicals |
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| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |