GB2147602A - Disperse and acid azo dyes having one or two cinnamoyl substituents on a phenyl diazonium moiety - Google Patents

Disperse and acid azo dyes having one or two cinnamoyl substituents on a phenyl diazonium moiety Download PDF

Info

Publication number
GB2147602A
GB2147602A GB08326869A GB8326869A GB2147602A GB 2147602 A GB2147602 A GB 2147602A GB 08326869 A GB08326869 A GB 08326869A GB 8326869 A GB8326869 A GB 8326869A GB 2147602 A GB2147602 A GB 2147602A
Authority
GB
United Kingdom
Prior art keywords
alkyl
substituted
so3m
unsubstituted
so4m
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
GB08326869A
Other versions
GB8326869D0 (en
GB2147602B (en
Inventor
Robert Nicholas Gourley
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kodak Ltd
Original Assignee
Kodak Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kodak Ltd filed Critical Kodak Ltd
Priority to GB08326869A priority Critical patent/GB2147602B/en
Publication of GB8326869D0 publication Critical patent/GB8326869D0/en
Publication of GB2147602A publication Critical patent/GB2147602A/en
Application granted granted Critical
Publication of GB2147602B publication Critical patent/GB2147602B/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)

Abstract

New dyes of formula (I) give red to blue shades on wool, polyamide, polyester and cellulose ester fibres: <IMAGE> wherein C<1> is an aniline, tetrahydroquinoline, or benzomorpholine type coupler which may be substituted; the A ring is unsubstituted or substituted in any positions not occupied by cinnamoyl groups; R5 is H or alkyl; and each R1 is a substituent. The molecule may include water-solubilizing groups (e.g. SO3H or its metal or amine salts) for acid dyeing.

Description

SPECIFICATION Disperse and acid azo dyes having one or two cinnamoyl substituents on a phenyl diazonium moiety This invention relates to azo dyes containing a diazonium moiety from an aniline type compound, and certain coupler moieties from aniline, tetrahydroquinoline, and benzomorpholine type compounds, wherein the diazonium moiety has one or two cinnamoyl groups, and wherein a wide variety of groups, e.g., one or more water-solubilizing substituents such as sulfonic acid groups or their metal or amine salts may be present in the dye molecuie. These dyes are useful for dyeing materials selected from polyamide, cellulose ester, polyester, wool and other natural and synthetic fibers and generally exhibit improvements in dyeability and fastness properties.
The present dyes have the general structure:
wherein C' is an aniline, tetrahydroquinoline, or benzomorpholine type coupler which may be substituted; ring A is unsubstituted or substituted in any positions not occupied by cinnamoyl groups, with 1-3 substituents preferably each of which is a substituent as defined for R1;R5 is H or alkyl; and each R1 is alkyl, alkenyl of 2-6 carbons, aryl, cyclohexyl, alkoxy, halogen, hydroxy, alkylsulfonyl, cyano, carbamoyl, alkanoyl, alkanoyloxy, aroyl, alkoxycarbonyl, sulfamoyl, alkylsulfamoyl, dialkylsulfamoyl, alkanoylamino, SO3C6Hs, amino, alkylthio, thiocyano, arylsulfonyl, formyl, alkylcarbamoyl, dialkylcarbamoyl, NO2, -SO3M, -OSO3M, -COOH, aryloxy, arylthio, alkylsulfonylamino, aroylamino, arylsulfonylamino, or cyclohexylthio, wherein the alkyl, alkylene, alkenyl, aryl, and cyclohexyl moieties of the above R, groups, e.g., the alkyl portions of the alkanoyl groups, are unsubstituted or substituted with 1-3 substituents different from the said moieties and independently selected from alkanoyloxy, alkyl, alkenyl, succinimido (C4H402N), -NO2, alkan oylamino, alkylsulfonylamino, 1-(2-pyrrolidono) (C4H6ON), halogen, cyano, alkoxy, aryl, cyclohexyl, hydroxy, -SO3M, -OSO3M, aryloxy, furyl (C4HSO), aroyloxy, alkoxycarbonyl, -SO2N- (alkyl)2, -NHCOO-alkyl, -NHCONH-alkyl, glutarimido (C5H602N), phthalimido (C8H402N), CONH2, CONH-alkyl, CON(alkyl)2, alkoxyalkoxy, alkylthio, arylthio, alkylsulfonyl, and arylsulfonyl, wherein M is selected from H+, NH+, Na+, K+, and the colorless cations of salts of primary, secondary, and tertiary aliphatic and arylamines, such as triethylamine, tri(2-hydroxyethyl)amine, di(2-hydroxyethyl)amine, N,N-dimethylaniline, and and espe- cially trimethyiamine.
The couplers C' preferably have the formulae:
wherein R1 is defined above; R2 and R7 are each selected independently from hydrogen, alkyl, alkenyl of 2-6 carbons, aryl, and cyclohexyl, all of which groups including alkylene moieties are unsubstituted or substituted as defined above for the substituted R, groups; and R3, R4 and R8 are each selected from hydrogen and alkyl.
The various alkyl and alkylene moieties such as contained, for example, in alkoxy, alkanoyl, and alkoxyalkoxy groups within the above definitions preferably contain 1-6 carbons, and they and the alkenyl groups may be straight or branched chain, and the above aryl groups preferably contain from 6-10 ring carbons.
The following are typical specific R1 groups: CH3, Cl, SO2C2Hs, CN, CON H2, COC2Hs, COC6Hsw COOC2H5, SO2NH2, SO2NHCH3, SO2N(C2H5)2, NHCOC2H5, SO3C6H5, SCH3, SCN, SO2C6H5, CHO, CONHC2H5, CON(C2H5)2, OH, NO2, C6H5, C6Hll, SO3K, CF3, CH2OOCC2Hs, Br, SO2CH2CH2OC2H5, 1, CONHCH2CN, COCH2CH2OH, COC6H3-o CH3-p-OCH3, COOC2H4-CH = CH2, SO2NHCH2CH2CN, SO2NHCH2- succinimido, SO2NHC2H4-C6Hs, NHCOCH2CH2CI.SO3C6H4-p-NO2, SCH2CH2OH, SC2H4-C6H11, SO2C6H4-eNHCOCH3, C6H4eNHSO2CH3, CONHC2H4NHSO2CH3, CONHCH2CH2OH, CH2CH2NO2, C6H4-e(2-pyrro- lidono), C6H,o-4-CN, OSO3K, CH2SO3Na, OC6Hs, SO2C2H4OSO3K, C2H4furyl, C2H4OOCC6Hs, COCH2CH2COOCH3, COC6H4-pSO2NHC6H5, COOCH2CH2-SO2NHCH3, SO2NHCH2SO2N(C2H5)2, SO2NHCH2NHCOOCH3, SO2NHC2H4NHCONHCH3, NHCOCH2CH2- glu- tarimido, SO3C6H4-p-phthalimido, SCH2CONH2, C6H4-p-SO2CH3, SO 2C5H4-pCONHCH2SO3Na, CH2SO2C6Hs, CONHCH2CH2CON(CH3)2, CONHCH2CH2OCH2CH2OCH2CH3, CH2CH2SO3H, C6H4-p-SC2H5, C6H,0-4-SC6H4(p-OSO3H), CH2CH = CH2, COOH, OC6H,, OCH3, SC6H5, NHSO2CH3, NHCOC6H5, NH2, NHSO2C6H5, SC6H11, and -OOCCH3.
Typical for R3, R4, R5 and R8 are: H, CH3, C2H5, C4Hg-n, and CH2(CH3)2.
The following are typical specific R2 and R7 substituents: H, CH3, C2Hs, C4H9-n, CH2CH=CH2, C6H5, C6H11. CH2OOCC2H5, CH2CH2OC2H5, CH2CN, CH2CH2OH, C6H3-o-CH3-p-OCH3, C2H4-CH = CH2, CH2-succin- imido, CH2CH2-C6H5, CH2CH2CI, QH4-pNO2, CH2CH2C6H", C6H4-eNHSO2CH3, C2H4NHSO2CH3, CH2CH2NO2, C6H4-pt2-pyrroíi- dono), C6H10-4-CN, CH2SO3Na, CH2CH2OSO3K, CH2CH2-furyl, CH2CH2OOCC6H5, CH2CH2COOCH3, C6H5-p-SO2NHC6H5, CH2CH2SO2NHCH3, CH2SO2N(C2H5)2, CH2NHCOOCH3, CH2CH2NHCONHCH3, CH2CH2-glutarimido, C6H4-pphthalimido, CH2CONH2, C6H4-eSO2CH3, C6H4-eCONHCH2SO3Na, CH2SO2C6Hs, CH2CH2CON(CH3)2, CH2CH2OCH2CH2OC2H5, CH2CH2SO3H, C6H4-p-SC2H5, and C6H10-4-SC6H4(p-OSO3H).
Preferred substituents, in addition to H, for the A ring are halogen, CN, methoxycarbonyl alkoxy, CF3, NO2, alkanoyl, alkylsulfonyl, ss-hydroxyethylcarbamoyl, ss-potassiosulfatoethylcarbamoyl, methylcarbamoyl, carbamoyl, ethoxycarbonyl, or methyl; for R, on the cinnamoyl rings are H, alkyl, aralkyl, aralkyl substituted with -SO3M or -SO4M, cyclohexylalkyl, cyclohexylalkyl substituted with -SO3M or -S04M, alkoxy, or alkanoylamino: for R2 are H, alkyl, aralkyl, alkyl or aralkyl substituted with -SO3M or -SO4M, cyclohexylalkyl, cyclohexylalkyl substituted with -SO3M or -SO4M; for R7 are H, alkyl, aralkyl, aralkyl substituted with -SO3M or -SO4M, cyclohexylalkyl, cyclohexylalkyl substituted with -SO3M or -SO 4M, sodio- or potassiosulfatoalkyl, sodio- or potassiosulfonicalkyl, or alkanoyloxyalkyl; for R, on the couplers are H, aralkyl, aralkyl substituted with -SO3M or -S04M, cyclohexylalkyl, cyclohexylalkyl substituted with -SO3M or-SO4M, -SO3Na, -SO3K, halogen, -SO4Na, -SO4K, alkyl, alkoxy, -COO H, or -OH; for R3, R4 and R8 are H and alkyl; and for R5 is hydrogen.
The dyes of this invention impart red to blue shades on natural and synthetic fibers and exhibit improvements over such dyes as disclosed in U.S. Patent 2,805,218 and British Patent 1,021,399 in one or more properties such as fastness to light, ozone, chlorine, oxides of nitrogen, washing, sublimation, heat disintegration, perspiration, and crocking, leveling, transfer, exhaustion, build, pH stability, and resistance to blooming.
The intermediate compounds used in this invention are prepared according to procedures well known to the art. The present dyes are readily prepared, for example, by reacting the acetyl group of the intermediate azo compound, which itself is a dye, with benzaldehyde or a substituted benzaldehyde in acetic acid with concentrated sulphuric acid as catalyst. The acetyl dye is thus converted to a cinnamoyl substituted dye in high yield. The water-solubilizing group may be the substituent on the benzaldehyde or it may be introduced into the cinnamoyl dye at a later stage by known methods. For example, a hydroxy group in either the diazonium component or the coupling component could be reacted with sulphuric acid and then with MOH to give the -OSO3M group. Alternatively a chloroalkyl group in the dye could be reacted with K2SO3 to give the -CH2S03K group.Also, sulphonation of an aromatic ring or other reactive group in the dye with a sulphonating agent such as H2S04 or Cl-S03H would give the solubilizing group. Such groups could also be present in the coupling component prior to diazotisation and coupling.
The following Preparations, Example and tables will illustrate the making and use of intermediates for the synthesis of dyes of the present invention.
PREPARATION A-&alpha;-(N-Ethylanilino)- Toluenesulfonic Acid To a 30.0 g. of 100% sulfuric acid is added N-benzyl-N-ethylaniline (30.0 g.) dropwise below about 50 C. To this solution is added, at 50-60 C., 60% oleum (30.0 g.) with good stirring.
The mixture is stirred and heated at about 60 C. for three hours and then drowned into 200 ml.
of water. The free sulfonic acid which is mostly the meta isomer with a small amount of para, precipitates on standing and is collected by filtration, washed with water, and dried. N Benzylines containing groups such as alkyl, alkoxy, and halogen in the ortho, meta, or para positions of the benzyl group may also be sulfonated by this procedure. The exact location of the sulfonic acid group in these cases is often not known and mixtures usually are produced.
Aromatic amines which contain N-aralkyl groups and which are sulfonated by the above procedure to give Couplers 2 to 11 are listed below.
COUPLER NO.
2 N-Benzyl-N-ethyl-m-toluidine; 3 N-Benzyl-2, 7-dimethyl-1 ,2,3,4- tetrahydroquinoline; 4 N-Benzyl-2,3-dihydro-3,6-dimethyl- 1 ,4-benzoxazine; 5 N-Methyl-N-(2-phenylethyl)aniline; 6 N-Ethyl-N-(4-phenylbutyl)-3 chloroaniline; 7 N,N-Dibenzylaniline; 8 N-Benzyl-2,5-dimethylaniline; 9 N-Benzyl-2-methoxy-5-methylaniline; 10 N-Benzyl-2-methoxy-5-chloroaniline; and 11 N-Benzyl-N-cyclohexylaniline.
PREPARATION B-Diazotiazation and Coupling of 2, 6-dibromo-4-acetylaniline To 1 50 g. of 60% acetic acid containing 10 g. of concentrated H2SO4 is added 8.2 g. (0;055 m.) of 2,6-dibromo-4-acetylaniline at room temperature. The solution is cooled to - 5"C., and a solution of 3.6 g. NaNO2 in 20 ml. of concentrated H2SO4 is added below 0 C. The reaction mixture is stirred at - 5 to 0 C. for 1.5 hours. Each of the Couplers 1 to 11 (0.005 m.) is added to water, or a 0.005 mole aliquot of the coupler in dilute sulfuric acid is added to water, and cooled in an ice bath.
To each chilled coupler is added a 0.005 mole aliquot of the diazonium solution. The coupling mixture is treated with enough potassium acetate to neutralize the mineral acid. Water is added to the coupling mixture to a total volume of about 200 ml. and the dyes collected by filtration, washed with 10% KCI solution, and dried in air. The dyes usually are admixed with about an equal weight of K2SO4 and are used for dyeing without further purification to produce red shades on polyamides. These dyes are intermediates for the preparation of dyes of the present invention.
PREPARATION C-Sulfonation of Dye Containing an N-Aralkylamino Group The dye from 2,6-dibromo-4-acetyaniline N-benzyl-N-ethylaniline (1.5 g.) is added portionwise to 1 5 ml. of concentrated H2SO4 over 20 min., allowing the temperature to rise to 30"C. The reaction mixture is then heated at 70"C., when the reaction is completed as evidenced by thinlayer chromatography. After the reaction mixture is drowned on ice-water mixture, 50% NaOH is added until the pH is about 7. The dye is collected by filtration, washed with water, and dried in air. The structure is as follows:
EXAMPLE
A mixture of compound (I) (2 g.), benzaldehyde (1.5 g.), acetic acid (25 ml.) and concentrated sulphuric acid (5 ml.) was stirre at 1 00 C. for 1.5 hours.The reaction mixture was poured into cold water and the product dye (II) filtered off, washed with water and dried.
Compound (I) had previously been prepared by diazotising the known 2,6-dibromo-4acetylaniline and coupling with N-ethyl-2,2,4,7-tetra-methyl-1,2,3,4-tetrahydroquinoline by known procedures. The dye (II) when applied to nylon, polyester and other synthetic fibres by known techniques gave bright, bluish red shades with good dyeing and fastness properties.
By using the methods described hereinabove, the following dyes are obtained.
TABLE 1
Cinnamoyl Group Substituents Position R1 on D R5 on A R1 on C R2 R7 4 H H H H H H 4 4-NO2 H 6-COCH3 2-CH3 C2H5 Ph 4 4-CN H 6-NO2 5-COCH3 C2H5 C6H11 4 5-COCH3 H 5,6-di-Cl 5-OCH3 CH2-C6H4-p-SO4K CH2-CH=CH2 4 4-COPh CH3 6-CN 5-SO3Na H CH2OOCC2H5 5 2,4-di-COOH CH3 4-NHSO2CH3 5-OCH2CH2SO4K CH2-C6H10-4-SO3K C6H4-p-OOCCH3 6 4-OOCCH3 CH3 5-CH3 5-OCH2CH2SO4N H(Et)3 H C6H10-4-CH3 4 4-NHCOCH3 CH3 6-OCH3 2-CH3 CH2-C6H4-p-SO4N H(Et)3 CH2CH2(C4H4O2N) 6 4-NHCOPh CH3 4-Ph 2-Ph CH3 CH2CH2NO2 4 4-C2H5 CH3 H 2-NO2 CH3 C6H4-p-NO2 6 4-Ph H H 2-OCH3 CH3 CH2NHOCCH3 4 Cl H 5,6-di-SO3Na 5-NHCOCH3 C2H5 CH2NHSO2CH3 4 SO3K H H 3NHCOCH3 H C2H5 4 2-Cl-4-SO2CH3 H 6-SO3Na 3-NHSO2CH3 C2H5 C6H4-p-NHOCCH3 4 4-NHSO2CH3 H 6-OCH2CH2SO4K 3-COOCH3 C2H5 C6H4-p-NHSO2CH3 4 4-COOCH3 H 6-OCH2CH2SO4K 3-COOH C2H5 C6H10-4-NHOOCH3 4 2-OCH3 C2H5 6-NHCOPh 2-Cl CH2CH2Cl CH2CH2Cl 5 4-OC2H5 C2H5 4-NHCOPh 2,6-di-Br C6H4-p-Br C6H4-p-Br 6 4-SO3Na C2H5 4-NHCOCH3 2,6-di-Br C6H4-p-CN C6H4-p-CN 6 2-SO3Na C2H5 4-OOCC2H5 2-OCH3-5-NHCOCH3 CH2CH2CN CH2CH2CN 4 2-OCH3-4-SO3K H 5-COOH 2-CH2OOCCH3 CH2CH2OC2H5 CH2CH2OC2H5 4 4-OCH2CH2OSO3K H H 2-CH2Cl CH2CH2OCH2CH2OC2H5 CH2CH2OCH2CH2OC2H5 4 2-SO3Na-5-Cl H H 2-CN CH2Ph CH2-C6H4-p-SO4N+H(CH3)3 4 4-Cl H 6-SO2CH3 2-OOCCH3 CH2C6H11 CH2C6H10-4-SO3Na 4 4-OH H 6-CF3 5-COOH H C6H4-o-OH 4 4-CH2OOCCH3 C3H7-n 6-COOCH3 5-OH C2H5 CH2CH2OH 4 4-SO3K C3H7-n 6-CHO 5-CH2CH=CH2 CH2CH2-SO3K CH2CH2-SO3K 6 4-OPh H 4-CONH2 2-CH3 H CH2-C6H4-p-OSO3K 6 4-NO2 H 4-CONHCH3 5-COCH3 H CH2OPh 6 5-CN H 4-CH2Ph 5-OCH3 H CH2SO2NHPh 4 4-SO3K H H 3-CH3 C2H5 CH2CH2SO3K 4 4-COCH3 H 6-CH2SO3K 5-SO3Na CH2SO2NHCH3 CH2SO2NHCH3 4 5-CH3 H 6-CH2OSO3K 5-OCH2CH2SO4K H CH2-C6H4-p-SO2NHCH3 4 5-C6H4-p-SO3K H 6-C6H4-p-SO3K 5-OCH2CH2SO3K CH2COOCH3 CH2COOCH3 4 5-OCH3 H 6-CH2CH2OH 2-CH3 H CH2SO2N(CH3)2 4 4,5-di-Br H 6-CH2Cl 2-C6H4-p-SO3K C2H5 C6H4-p-NHCOOCH3 4 5-COOH C4H9-n 6-C6H4-p-Br 2-NO2 C2H5 CH2CH2CONH2 4 H H H 2-OCH3 C2H5 C6H4-p-CONHCH3 4 4-NO2 H 5-COCH3 5-NHCOCH3 C2H5 C6H4-p-SCH3 4 4-CN H 5-NO2 3-NHSO2CH3 CH2CH2SCH3 CH2CH2SCH3 4 5-COCH3 H 5-Cl 3-COOCH3 H CH2-C6H4-p-SCH3 4 4-COPh CH3 5,6-di-CN 3-COOH CH2SO2C2H5 CH2SO2C2H5 4 2,4-di-COOH CH3 5-NHSO2CH3 2-Cl H CH2SO2Ph 4 4-OOCCH3 CH3 6-CH3 2,6-di-Br H CH2CH2OSO3K 4 4-NHCOCH3 CH3 6-OCH3 2,6-di-Br H C6H4-p-OSO3K 4 4-NHCOPh CH3 6-Ph 2-OCH3-5-NHCOCH3 H CH2(C8H4O2N) 4 4-CH2CH=CH2 H H 3-NHCOCH3 C2H5 C2H5 4,6 H CH3 H 3-OCPh C2H5 C2H5 4 4-SO3K H H 2-OCH3-5-NHCOCH3 C2H5 CH2CH2SO3K 4 4-CONH2 H H 5-CH2CONHCH3 H H 4 3-SO2NH2 H 6-COCH3 5-CH2CON(CH3)2 C2H5 Ph 4 4-SO2NHCH3 H 6-NO2 5-CH2CH2OCH2CH2OC2H5 C2H5 C6H11 4 4-SO2N(C2H5)2 H 6-Cl 5-CH2SC2H5 H CH2-CH=CH2 4 4-SO3C6H5 CH3 6-CN 2-CH2SC6H5 H CH2OOCC2H5 4 4-SCH3 CH3 6-NHSO2CH3 5-CH2SO2C2H5 H C6H4-p-OOCCH3 4 2,4-di-SCN CH3 5-CH3 5-CH2SO2C6H5 H C6H10-4-CH3 4 4-SO2C6H5 CH3 5-OCH3 5-C6H3-o,p-di-CN H CH2CH2(C4H4O2N) 4 2-CHO-4-CN CH3 6-Ph 5-C6H2-o,m,p-tri-Cl CH3 CH2CH2NO2 4 4-CONHC2H5 CH3 H 2,6-di-OSO3N H(CH3)3 CH3 C6H4-p-NO2 4 4-CON(C2H5)2 H H 2,6-di-SO3N H(CH3)3 CH3 CH2NHOCCH3 4 3-C6H11 H 6-SO3Na 2,6-di-OSO3K C2H5 CH2NHSO2CH3 4 3-SC6H5 H 6-SO3Na 2-SO3N H(CH3)3 C2H5 C6H4-p-NHOCCH3 4 4-NHSO2C6H5 H 5-OCH2CH2SO4K 2-OSO3N H(CH3)3 C2H5 C6H4-p-NHSO2CH3 4 4-SC6H11 H 5-OCH2CH2SO4K 5-SC6H10-p-SO3K C2H5 C6H10-4-NHOCCH3 4 4-C6H4-p-CH3 C2H5 6-NHCOPh 5-C6H4-p-CH3 CH2CH2Cl CH2CH2Cl 4 4-C6H4-p-CH2CH=CH2 C2H5 6-NHCOPh 5-C6H4-p-CH2CH=CH2 C6H4-p-Br C6H4-p-Br 4 4-OCH2CH2NO2 C2H5 5-NHCOCH3 5-OCH2CH2NO2 C6H4-p-CN C6H4-p-CN 4 2-CH2NHCOCH3 C2H5 5-OOCC2H5 2-CH2NHCOCH3 CH2CH2CN CH2CH2CN 4 4-CH2NHSO2C2H5 H 6-COOH 5-CH2NHSO2C2H5 CH2CH2OC2H5 CH2CH2OC2H5 4,6 4-CH2CH2Cl H H 5-CH2CH2Cl CH2CH2OCH2CH2OC2H5 CH2CH2OCH2CH2OC2H5 6 2,6-di-CH2CN H H 2,6-di-CH2CN CH2Ph CH2Ph 6 4-CH2CH2OC2H5 H 4-SO2CH3 5-CH2CH2OC2H5 CH2C6H11 CH2C6H11 6 4-CH2C6H5 H 4-CH2C6H5 5-COOH H C6H4-o-OH 6 4-CH2C6H11 C3H7-n 4-COOCH3 5-CH2C6H11 C2H5 CH2CH2OH 6 4-CH2CH(OH)CH2OH C3H7-n 4-CHO 5-CH2CH(OH)CH2OH CH2CH2-SO3K CH2CH2-SO3K 4 4-CH2CH2-SO3K H 5-CONH2 5-CH2CH2-SO3K H C6H4-p-OSO3K 4 4-CH2OC6H5 H 5-CONHCH3 5-CH2OC6H5 H CH2OPh 4 4-CH2OOCC6H5 H 5-CH2Ph 5-CH2OOCC6H5 H CH2SO2NHPh 4 5-CH2COOCH3 H 6-CH2SO3K 5-CH2COOCH3 CH2SO2NHCH3 CH2SO2NHCH3 4 4-C6H4-p-SO2N(C2H5)2 H 6-CH2OSO3K 5-C6H4-p-SO2N(C2H5)2 H C6H4-p-SO2NHCH3 4 4-CH2CH2NHCOOCH3 H 6-C6H4-p-SO3K 5-CH2CH2NHCOOCH3 CH2COOCH3 CH2COOCH3 4 4-CH2NHCONHCH3 H 6-CH2CH2OH 5-CH2NHCONHCH3 H CH2SO2N(CH3)2 4 4-CH2CONH2 H 6-CH2Cl 5-CH2CONH2 C2H5 C6H4-p-NHCOOCH3 4 5-CH2CONHCH3 C4H9-n 6-C6H4-p-Br 5-CONH2 C2H5 CH2CH2CONH2 4 4-CH2CON(CH3)2 H H 3-SO2NH2 C2H5 C6H4-p-CONHCH3 4 4-CH2CH2OCH2CH2OC2H5 H 5-COCH3 5-SO2NHCH3 C2H5 C6H4-p-SCH3 4,6 4-CH2SC2H5 H 5-NO2 5-SO2N(C2H5)2 CH2CH2SCH3 CH2CH2SCH3 6 5-CH2SC6H5 H 4-Cl 5-SO3C6H5 H CH2-C6H4-p-SCH3 4 4-CH2SO2C2H5 CH3 6-CN 5-SCH3 CH2SO2C2H5 CH2SO2C2H5 4 2,4-di-CH2SO2C6H5 CH3 6-NHSO2CH3 2,5-di-SCN H CH2SO2Ph 4 4-C6H3-o,p-di-CN CH3 5-CH3 5-SO2C6H5 H CH2CH2OSO3K 4 4-C6H2-o,m,p-tri-Cl CH3 5-OCH3 2-CHO-6-CN H C6H4-p-OSO3K 4 2,6-di-OSO3Na CH3 6-Ph 5-CONHC2H5 H CH2-(C8H4O2N) 4 H H 6-CH2(C4H4O2N) 5-CON(C2H5)2 C2H5 C2H5 4 H H 6-CH2(C4H3O) 3-C6H11 C2H5 C2H5 4 5-CH2(C8H4O2N) H H 3-SC6H5 C2H5 C2H5 4 5-CH2(C4H3O) H H 6-NHSO2C6H5 C2H5 C2H5 4 2-Cl,SO3M H 2,6-di-Br 2-OCH3-5-CH3 H C2H5 4 H H 2,6-di-Br 2-OCH3-5-CH3 H C2H5 TABLE 2
Cinnamoyl Group Substituents Position R1 on D R5 on A R1 on C R3 R4 R8 R7 4 H H H H H H H H 4 4-NO2 H 5-COCH3 7-CH3 CH3 CH3 CH3 Ph 4 4-CN H 5-NO2 5-COCH3 CH3 CH3 H C6H11 4 5-COCH3 H 5-Cl 5-OCH3 CH3 CH3 H CH2-CH=CH2 4,5 4-COPh CH3 6-CN 7-SO3Na CH3 CH3 H CH2OOCC2H5 5 2,4-di-COOH CH3 4-NHSO2CH3 7-OCH2CH2SO4K CH3 CH3 H C6H4-p-OOCCH3 6 4-OOCCH3 CH3 5-CH3 7-OCH2CH2SO4N @(Et)3 CH3 CH3 H C6H10-4-CH3 6 4-NHCOCH3 CH3 4,5-di-OCH3 7-CH3 CH3 H H CH2CH2(C4H4O2N) 6 4-NHCOPh CH3 4-Ph 7-Ph CH3 H H CH2CH2NO2 4 4-C2H5 CH3 H 7-NO2 CH3 H H C6H4-p-NO2 6 4-Ph H H 7-OCH3 CH3 H H CH2NHOCCH3 4 2,5-di-Cl H 6-SO2Na 7-NHCOCH3 CH3 H H CH2NHSO2CH3 4 2-Cl-4-SO2CH3 H 6-SO3Na 7-NHSO2CH3 CH3 H H C6H4-p-NHOCCH3 4 4-NHSO2CH3 H 5-OCH2CH2SO4K 7-COOCH3 CH3 C2H5 C2H5 C6H4-p-NHSO2CH3 4 4-COOCH3 H 5-OCH2CH2SO4K 7-COOH H H H C6H10-4-NHOCCH3 4 2-OCH3 C2H5 6-NHCOPh 7-Cl CH3 CH3 CH3 CH2CH2Cl 4 4-OC2H5 C2H5 6-NHCOPh 5,7-di-Br CH3 CH3 H C6H4-p-Br 4 4-SO3Na C2H5 6-NHCOCH3 5,7-di-Br CH3 CH3 H C6H4-p-CN 4 2-SO3Na C2H5 5-OOCC2H5 5-OCH3-7-NHCOCH3 CH3 CH3 H CH2CH2CN 4 2-OCH3-4-SO3K H 6-COOH 7-CH2OOCCH3 CH3 CH3 H CH2CH2OC2H5 4 4-OCH2CH2OSO3K H H 7-CH2Cl CH3 CH3 H CH2CH2OCH2CH2OC2H5 4 2-SO3Na-5-Cl H H 7-CN CH3 H H CH2Ph 4 4-Cl H 5-SO2CH3 7-OOCCH3 CH3 H H CH2C6H11 4 4-OH H 5-CF3 5-COOH CH3 H H C6H4-o-OH 4 4-CH2OOCCH3 C3H7-n 5-COOCH3 5-OH CH3 H H CH2CH2OH 4 4-SO3K C3H7-n 5-CHO 5-CH2CH=CH2 CH3 H H CH2CH2-SO3K 4,6 4-OPh H 5-CONH2 7-CH3 CH3 H H C6H4-p-OSO3K 6 4-NO2 H 4-CONHCH3 7-COCH3 CH3 C2H5 C2H5 CH2OPh 4 5-CN H 5-CH2Ph 7-OCH3 H H H CH2SO2NHPh 4 4-COCH3 H 5-CH2SO3K 7-SO3Na CH3 CH3 CH3 CH2SO2NHCH3 4 5-CH3 H 5-CH2OSO3K 7-OCH2CH2SO4K CH3 CH3 H C6H4-p-SO2NHCH3 4 5-Ph H 5-C6H4-p-SO3K 7-OCH2CH2SO3K CH3 CH3 H CH2COOCH3 4 5-OCH3 H 5-CH2CH2OH 7-CH3 CH3 CH3 H CH2SO2N(CH3)2 4 4,5-di-Br H 5-CH2Cl 7-Ph CH3 CH3 H C6H4-p-NHCOOCH3 4 5-COOH C4H9-n 6-C6H4-p-Br 7-NO2 H H H CH2CH2CONH2 4 H H H 7-OCH3 CH3 CH3 CH3 C6H4-p-CONHCH3 4 4-NO2 H 6-COCH3 7-NHCOCH3 CH3 CH3 H C6H4-p-SCH3 4 4-CN H 6-NO2 7-NHSO2CH3 CH3 CH3 H CH2CH2SCH3 4 5-COCH3 H 6-Cl 7-COOCH3 CH3 CH3 H CH2-C6H4-p-SCH3 4 4-COPh CH3 6-CN 7-COOH CH3 CH3 H CH2SO2C2H5 4 2,4-di-COOH CH3 5-NHSO2CH3 7-Cl CH3 CH3 H CH2SO2Ph 4 4-OOCCH3 CH3 6-CH3 5,7-di-Br CH3 H H CH2CH2OSO3K 4 4-NHCOCH3 CH3 6-OCH3 5,7-di-Br CH3 H H C6H4-p-OSO3K 4 4-NHCOPh CH3 6-Ph 5-OCH3-7-NHCOCH3 CH3 H H CH2(C8H4O2N) 5 4-CH2CH=CH2 H H 7-NHCOCH3 C2H5 H H C2H5 4 H CH3 H 7-OCPh C2H5 H H C2H5 4,6 4-CONH2 H H 7-CH2CONHCH3 H H H H 6 3-SO2NH2 H 4-COCH3 7-CH3CON(CH3)2 CH3 CH3 CH3 Ph 6 4-SO2NHCH3 H 4-NO2 7-CH2CH2OCH2CH2OC2H5 CH3 CH3 H C6H11 6 4-SO2N(C2H5)2 H 4-Cl 7-CH2SC2H5 CH3 CH3 H CH2-CH=CH2 4 4-SO3C6H5 CH3 6-CN 7-CH2SC6H5 CH3 CH3 H CH2OOCC2H5 5 4-SCH3 CH3 4-NHSO2CH3 7-CH2SO2C2H5 CH3 CH3 H C6H4-p-OOCCH3 4 2,4-di-SCN CH3 6-CH3 7-CH2SO2C6H5 CH3 CH3 H C6H10-4-CH3 4 4-SO2C6H5 CH3 6-OCH3 7-C6H3-o,p-di-CN CH3 H H CH2CH2-(C4H4O2N) 4 2-CHO-4-CN CH3 6-Ph 6-C6H2-o,m,p-tri-Cl CH3 H H CH2CH2NO2 4 4-CONHC2H5 CH3 H 5,7-di-OSO3N H(CH3)3 CH3 H H C6H4-p-NO2 4 4-CON(C2H5)2 H H 5,7-di-OSO3Na CH3 H H CH2NHOCCH3 4 3-C6H11 H 6-SO3Na 5,7-di-SO3N H(CH3)3 CH3 H H CH2NHSO2CH3 4 3-SC6H5 H 6-SO3Na 7-OSO3N H(CH3)3 CH3 H H C6H4-p-NHOCCH3 4 4-NHSO2C6H5 H 6-OCH2CH2SO4K 5,7-di-OSO3Na CH3 C2H5 C2H5 C6H4-p-NHSO2CH3 4 4-SC6H11 H 6-OCH2CH2SO4K 7-SC6H11 H H H C6H10-4-NHOCCH3 4 4-C6H4-p-CH3 C2H5 6-NHCOPh 7-C6H4-p-CH3 CH3 CH3 CH3 CH2CH2Cl 5 4-C6H4-p-CH2CH=CH2 C2H5 4-NHCOPh 7-C6H4-p-CH2CH=CH2 CH3 CH3 H C6H4-p-Br 6 4-OCH2CH2NO2 C2H5 4-NHCOCH3 7-OCH2CH2NO2 CH3 CH3 H C6H4-p-CN 6 2-CH2NHCOCH3 C2H5 4-OOCC2H5 7-CH2NHCOCH3 CH3 CH3 H CH2CH2CN 4 4-CH2NHSO2C2H5 H 5-COOH 7-CH2NHSO2C2H5 CH3 CH3 H CH2CH2OC2H5 4,6 4-CH2CH2Cl H H 7-CH2CH2Cl CH3 CH3 H CH2CH2OCH2CH2OC2H5 6 2,6-di-CH2CN H H 5,7-di-CH2CN CH3 H H CH2Ph 6 4-CH2CH2OC2H5 H 4-SO2CH3 7-CH2CH2OC2H5 CH3 H H CH2C6H11 4 4-CH2C6H5 H 6-CH2C6H5 7-COOH CH3 H H C6H4-p-OH 4 4-CH2C6H11 C3H7-n 6-COOCH3 7-CH2C6H11 CH3 H H CH2CH2OH 4 4-CH2CH(OH)CH2OH C3H7-n 6-CHO 7-CH2CH(OH)CH2OH CH3 H H CH2CH2-SO3K 4 4-CH2CH2-SO3K H 6-CONH2 7-CH2CH2-SO3K CH3 H H C6H4-p-OSO3K 4 4-CH2OC6H5 H 6-CONHCH3 7-CH2OC6H5 CH3 C2H5 C2H5 CH2OPh 4 4-CH2OOCC6H5 H 5-CH2Ph 7-CH2OOCC6H5 H H H CH2SO2NHPh 4 5-CH2COOCH3 H 5-CH2SO3K 7-CH2COOCH3 CH3 CH3 CH3 CH2SO2NHCH3 4 4-C6H4-p-SO2N(C2H5)2 H 6-CH2OSO3K 7-C6H4-p-SO2N(C2H5)2 CH3 CH3 H C6H4-p-SO2NHCH3 4 4-CH2CH2NHCOOCH3 H 6-C6H4-p-SO3K 7-CH2CH2NHCOOCH3 CH3 CH3 H CH2COOCH3 4 4-CH2NHCONHCH3 H 6-CH2CH2OH 7-CH2NHCONHCH3 CH3 CH3 H CH2SO2N(CH3)2 6 4-CH2CONH2 H 4-CH2Cl 7-CH2CONH2 CH3 CH3 H C6H4-p-NHCOOCH3 4 5-CH2CONHCH3 C4H9-n 5-C6H4-p-Br 7-CONH2 H H H CH2CH2CONH2 4 4-CH2CON(CH3)2 H H 7-SO2NH2 CH3 CH3 CH3 C6H4-p-CONHCH3 4 4-CH2CH2OCH2CH2OC2H5 H 6-COCH3 7-SO2NHCH3 CH3 CH3 H C6H4-p-SCH3 4 4-CH2SC2H5 H 6-NO2 7-SO2N(C2H5)2 CH3 CH3 H CH2CH2SCH3 4,5 5-CH2SC6H5 H 6-Cl 7-SO3C6H5 CH3 CH3 H CH2-C6H4-p-SCH3 6 4-CH2SO2C2H5 CH3 4-CN 7-SCH3 CH3 CH3 H CH2SO2C2H5 6 2,4-di-CH2SO2C6H5 CH3 4-NHSO2CH3 5,7-di-SCN CH3 CH3 H CH2SO2Ph 4 4-C6H3-o,p-di-CN CH3 6-CH3 7-SO2C6H5 CH3 H H CH2CH2OSO3K 4 4-C6H2-o,m,p-tri-Cl CH3 6-OCH3 5-CHO-7-CN CH3 H H C6H4-p-OSO3K 4 2,6-di-OSO3Na CH3 6-Ph 7-CONHC2H5 CH3 H H CH2(C8H4O2N) 4 H H 6-CH2(C4H4O2N) 7-CON(C2H5)2 CH3 H H C2H5 4 H H 5-CH2(C4H3O) 7-C6H11 CH3 H H C2H5 4 5-CH2(C8H4O2N) H H 7-SC6H5 CH3 H H C2H5 4 5-CH2(C4H3O) H H 7-NHSO2C6H5 CH3 C2H5 C2H5 C2H5 2 4-OSO3K H H 7-CH3 CH3 CH3 CH3 H TABLE 3
Cinnamoyl Group Substituents Position R1 on D R5 on A R1 on C R3 R7 4 H H H H H H 4 4-NO2 H 5-COCH3 6-CH3 CH3 Ph 4 4-CN H 5-NO2 6-COCH3 C2H5 C6H11 4 5-COCH3 H 6-Cl 6-OCH3 H CH2-CH=CH2 4 4-COPh CH3 6-CN 6-SO3Na H CH2OOCC2H5 5 2,4-di-COOH CH3 4-NHSO2CH3 6-OCH2CH2SO4K H C6H4-p-OOCCH3 6 4-OOCCH3 CH3 4-CH3 6-OCH2CH2SO4K H C6H10-4-CH3 6 4-NHCOCH3 CH3 4-OCH3 6-CH3 H CH2CH2(C4H4O2N) 4,6 4-NHCOPh CH3 5-Ph 6-Ph CH3 CH2CH2NO2 4 4-C2H5 CH3 H 6-NO2 CH3 C6H4-p-NO2 6 4-Ph H H 6-OCH3 CH3 CH2NHOCCH3 4 4-OSO3K H H H H CH2CH2SO3K 4 2,5-di-Cl H 5-SO3Na 6-NHCOCH3 C2H5 CH2NHSO2CH3 4 2-Cl-4-SO2CH3 H 5-SO3Na 6-NHSO2CH3 CH3 C6H4-p-NHOCCH3 4 4-NHSO2CH3 H 6-OCH2CH2SO4K 6-COOCH3 CH3 C6H4-p-NHSO2CH3 4 4-COOCH3 H 6-OCH2CH2SO4K 6-COOH H C6H10-4-NHOCCH3 4 2-OCH3 C2H5 5-NHCOPh 6-Cl CH3 CH2CH2Cl 5 4-OC2H5 C2H5 4-NHCOPh 5,6-di-Br C2H5 C6H4-p-Br 6 4-SO3Na C2H5 4-NHCOCH3 5,6-di-Br H C6H4-p-CN 6 2-SO3Na C2H5 4-OOCC2H5 5-OCH3-6-NHCOCH3 H CH2CH2CN 4 2-OCH3-4-SO3K H 5-COOH 6-CH2OOCCH3 H CH2CH2OC2H5 6 4-OCH2CH2OSO3K H H 6-CH2Cl H CH2CH2OCH2CH2OC2H5 4,6 2-SO3Na-5-Cl H H 6-CN H CH2Ph 6 4-Cl H 4-SO2CH3 6-OOCCH3 CH3 CH2C6H11 4 4-OH H 6-CF3 5-COOH CH3 C6H4-o-OH 4 4-CH2OOCCH3 C3H7-n 6-COOCH3 5-OH CH3 CH2CH2OH 4 4-SO3K C3H7-n 6-CHO 5-CH2CH=CH2 C2H5 CH2CH2-SO3K 4 4-OPh H 6-CONH2 6-CH3 CH3 C6H4-p-OSO3K 4 4-NO2 H 6-CONHCH3 6-COCH3 CH3 CH2OPh 4 5-CN H 6-CH2Ph 6-OCH3 H CH2SO2NHPh 4 4-COCH3 H 6-CH2SO3K 6-SO3Na CH3 CH2SO2NHCH3 4 5-CH3 H 6-CH2OSO3K 6-OCH2CH2SO4K H C6H4-p-SO2NHCH3 4 5-Ph H 5-C6H4-p-SO3K 6-OCH2CH2SO3K H CH2COOCH3 4 5-OCH3 H 5-CH2CH2OH 6-CH3 H CH2SO2N(CH3)2 4 4,5-di-Br H 5-CH2Cl 6-Ph H C6H4-p-NHCOOCH3 4 5-COOH C4H9-n 6-C6H4-p-Br 6-NO2 C2H5 CH2CH2CONH2 4 H H H 6-OCH3 C2H5 C6H4-p-CONHCH3 4 4-NO2 H 6-COCH3 6-NHCOCH3 CH3 C6H4-p-SCH3 4 4-CN H 6-NO2 6-NHSO2CH3 C3H7-n CH2CH2SCH3 4 5-COCH3 H 6-Cl 6-COOCH3 H CH2-C6H4-p-SCH3 4 4-COPh CH3 5-CN 6-COOH CH3 CH2SO2C2H5 4 2,4-di-COOH CH3 5-NHSO2CH3 8-Cl H CH2SO2Ph 4 4-OOCCH3 CH3 5-CH3 5,6-di-Br H CH2CH2OSO3K 4 4-NHCOCH3 CH3 5-OCH3 5,6-di-Br H C6H4-p-OSO3K 4 4-NHCOPh CH3 6-Ph 5-OCH3-6-NHCOCH3 H CH2(C8H4O2N) 5 4-CH2CH=CH2 H H 6-NHCOCH3 C2H5 C2H5 4,6 H CH3 H 6-OCPh C2H5 C2H5 6 4-CONH2 H H 6-CH2CONHCH3 H H 6 3-SO2NH2 H 4-COCH3 6-CH2CON(CH3)2 CH3 Ph 4 4-SO2NHCH3 H 5-NO2 6-CH2CH2OCH2CH2OC2H5 C2H5 C6H11 4 4-SO2N(C2H5)2 H 6-Cl 6-CH2SC2H5 H CH2-CH=CH2 4 4-SO3C6H5 CH3 6-CN 6-CH2SC6H5 H CH2OOCC2H5 5 4-SCH3 CH3 4-NHSO2CH3 6-CH2SO2C2H5 H C6H4-p-OOCCH3 6 2,4-di-SCN CH3 4-CH3 6-CH2SO2C6H5 H C6H10-4-CH3 4 4-SO2C6H5 CH3 6-OCH3 6-C6H3-o,p-di-CN H CH2CH2-(C4H4O2N) 4 2-CHO-4-CN CH3 6-Ph 6-C6H2-o,m,p-tri-Cl CH3 CH2CH2NO2 4 4-CONHC2H5 CH3 H 6,8-di-OSO3N H(CH3)3 CH3 C6H4-p-NO2 4 4-CON(C2H5)2 H H 5,6-di-OSO3Na CH3 CH2NHOCCH3 4 3-C6H11 H 5,6-di-SO3Na 5,6-di-OSO3Na C2H5 CH2NHSO2CH3 4 3-SC6H5 H 6-SO3Na 5,6-di-SO3N H(CH3)3 CH3 C6H4-p-NHOCCH3 4 4-NHSO2C6H5 H 6-OCH2CH2SO4K 5,6-di-OSO3Na CH3 C6H4-p-NHSO2CH3 4 4-SC6H11 H 5-OCH2CH2SO4K 6-SC6H11 H C6H10-4-NHOCCH3 4 4-C6H4-p-CH3 C2H5 6-NHCOPh 6-C6H4-p-CH3 CH3 CH2CH2Cl 5 4-C6H4-p-CH2CH=CH2 C2H5 4-NHCOPh 6-C6H4-p-CH2CH=CH2 C2H5 C6H4-p-Br 6 4-OCH2CH2NO2 C2H5 4-NHCOCH3 6-OCH2CH2NO2 H C6H4-p-CN 4 2-CH2NHCOCH3 C2H5 6-OOCC2H5 6-CH2NHCOCH3 H CH2CH2CN 4 4-CH2NHSO2C2H5 H 6-COOH 6-CH2NHSO2C2H5 H CH2CH2OC2H5 4 4-CH2CH2Cl H H 6-CH2CH2Cl H CH2CH2OCH2CH2OC2H5 4,6 2,6-di-CH2CN H H 5,6-di-CH2CN H CH2Ph 6 4-CH2CH2OC2H5 H 4-SO2CH3 6-CH2CH2OC2H5 CH3 CH2C6H11 6 4-CH2C6H5 H 4-CH2C6H5 6-COOH CH3 C6H4-o-OH 4 4-CH2C6H11 C3H7-n 6-COOCH3 6-CH2C6H11 CH3 CH2CH2OH 4 4-CH2CH(OH)CH2OH C3H7-n 6-CHO 6-CH2CH(OH)CH2OH C2H5 CH2CH2-SO3K 4 4-CH2CH2-SO3K H 5-COHN2 6-CH2CH2-SO3K CH3 C6H4-p-OSO3K 4 4-CH2OC6H5 H 5-CONHCH3 6-CH2OC6H5 CH3 CH2OPh 4 4-CH2OOCC6H5 H 5-CH2Ph 6-CH2OOCC6H5 H CH2SO2NHPh 4 5-CH2COOCH3 H 6-CH2SO3K 5-CH2COOCH3 CH3 CH2SO2NHCH3 4 4-C6H4-p-SO2N(C2H5)2 H 6-CH2OSO3K 6-C6H4-p-SO2N(C2H5)2 H C6H4-p-SO2NHCH3 4 4-CH2CH2NHCOOCH3 H 6-C6H4-p-SO3K 6-CH2CH2NHCOOCH3 H CH2COOCH3 4 4-CH2NHCONHCH3 H 6-CH2CH2OH 6-CH2NHCONHCH3 H CH2SO2N(CH3)2 4 4-CH2CONH2 H 6-CH2Cl 6-CH2CONH2 H C6H4-p-NHCOOCH3 4 5-CH2CONHCH3 C4H9-n 6-C6H4-p-Br 6-CONH2 C2H5 CH2CH2CONH2 4 4-CH2CON(CH3)2 H H 6-SO2NH2 C2H5 C6H4-p-CONHCH3 4 4-CH2CH2OCH2CH2OC2H5 H 5-COCH3 6-SO2NHCH3 CH3 C6H4-p-SCH3 4 4-CH2SC2H5 H 5-NO2 6-SO2N(C2H5)2 C3H7-n CH2CH2SCH3 4 5-CH2SC6H5 H 5-Cl 6-SO3C6H5 H CH2-C6H4-p-SCH3 4 4-CH2SO2C2H5 CH3 5-CN 6-SCH3 CH3 CH2SO2C2H5 4,5 2,4-di-CH2SO2C6H5 CH3 6-NHSO2CH3 5,6-di-SCN H CH2SO2Ph 6 4-C6H3-o,p-di-CN CH3 4-CH3 6-SO2C6H5 H CH2CH2OSO3K 4 4-C6H2-o,m,p-tri-Cl CH3 5-OCH3 5-CHO-6-CN H C6H4-p-OSO3K 4 2,6-di-OSO3Na CH3 5-Ph 6-CONHC2H5 H CH2-(C8H4O2N) 4 H H 6-CH2(C4H4O2N) 6-CON(C2H5)2 H C2H5 4 H H 6-CH2(C4H3O) 6-C6H11 H C2H5 4 5-CH2(C8H4O2N) H H 6-SC6H5 H C2H5 4 5-CH2(C4H3O) H H 6-NHSO2C6H5 H C2H5

Claims (9)

1. A dye having the structure:
wherein C, is an aniline, tetrahydroquinoline, or benzomorpholine type coupler which may be substituted; the A ring is unsubstituted or substituted in any positions not occupied by cinnamoyl groups; R5 is H or alkyl; and each R1 is a substituent.
2. A dye according to Claim 1 wherein each R, and each A ring substituent is selected from alkyl, alkenyl or 2-6 carbon atoms, aryl, cycohexyl, alkoxy, halogen, hydroxy, alkylsulfonyl, cyano, carbamoyl, alkanoyl, alkanoyloxy, aroyl, alkoxycarbonyl, sulfamoyl, alkylsulfamoyl, dialkylsulfamoyl, alkanoylamino, SO3C6H5, amino, alkylthio, thiocyano, arylsulfonyl, formyl, alkylcarbamoyl, dialkyicarbamoyl, NO2, -SO3M, -OSO3M, -COOH, aryloxy, arylthio, alkylsulfonylamino, aroylamino, arylsulfonylamino, and cyclohexylthio, wherein each of the alkyl, alkenyl, aryl, and cyclohexyl moieties of the above groups, is unsubstituted or substituted with 1-3 substituents different from the said moiety and independently selected from alkanoyloxy, alkyl, alkenyl, succinimido, -NO2, alkanoylamino, alkylsulfonylamino, 1-(2-pyrrolidono), halogen, cyano, alkoxy, aryl, cyclohexyl, hydroxy, -SO3M, -OSO3M, aryloxy, furyl, aroyloxy, alkoxycarbonyl, -SO2N - (alkyl)2, -N HCOO-alkyl, -NHCONH-alkyl, glutarimido, phthalimido, CON H2, CONHalkyl, CON(alkyl)2, alkoxyalkoxy, alkylthio, arylthio, alkylsulfonyl, and arylsulfonyl, wherein M is selected from H+, NH4+, Na+, K+, and the colorless cations of salts of primary, secondary, and tertiary aliphatic and arylamines; and the coupler C' is selected from
wherein each R1 is as defined above; R2 and R7 are each selected independently from hydrogen, alkyl, alkenyl of 2-6 carbon atoms, aryl, and cyclohexyl, all of which groups are unsubstituted or substituted as defined above for the substituted R, groups; and R3, R4 and R8 are each selected from hydrogen and alkyl.
3. A dye according to Claim 2 wherein: the A ring is unsubstituted or substituted with 1-3 substituents independently selected from methoxycarbonyl, ss-hydroxyethylcarbamoyl, CF3, NO2, alkanoyl, alkylsulfonyl, alkoxy, ss-potassiosulfatoethylcarbamoyl, halogen, CN, methylcarbamoyl, carbamoyl, ethoxycarbonyl, and methyl; the cinnamoyl ring is unsubstituted or substituted with 1-3 substituents independently selected from alkyl, aralkyl, aralkyl substituted with -SO3M or -SO4M, cyclohexylalkyl, cyclohexylalkyl substituted with -SO3M or -SO4M, alkoxy, and alkanoylamino; R2 is H, alkyl, aralkyl, alkyl or aralkyl substituted with -SO3M or -SO4M, cyclohexylalkyl, cyclohexylalkyl substituted with -SO3M or -SO4M;R7 is H, alkyl, aralkyl, aralkyl substituted with -SO3M or -SO4M, cyclohexylalkyl. cyclohexylalkyl substituted with -SO3M or -SO4M, sodio- or potassiosulfatoalkyl, sodio- or potassiosulfonicalkyl, or alkanoyloxyalkyl; the couplers are unsubstituted or substituted with 1-3 substituents independently selected from aralkyl, aralkyl substituted with -SO3M or -SO4M, cyclohexylalkyl, cyclohexylalkyl substituted with -SO3M or-SO4M, -SO3Na, -SO3K, -So3+H(Ch3)3, halogen, -SO4Na, -SO4K, -SO4N+H(CH3)3, alkyl, alkoxy, -COOH, and -OH; R3, R4 and R8 are H or alkyl; and R5 is hydrogen.
4. A dye according to Claim 1 wherein: the cinnamoyl ring is unsubstituted or substituted with halogen, COOT, OH, or SO3M; ring A is unsubstituted or substituted with alkyl, halogen, CN, alkoxy, COOalkyí, CON H2, alkanoylamino, CONHalkylene-SO4M, hydroxyethylcarbamoyl, or CONHalkyl; and wherein, in an aniline coupler each substituent R1 is a methyl, methoxy or acetamido group or a chlorine atom, each R2 is hydrogen, a methyl or ethyl group, or a sulfonated cyclohexyl or benzyl group and each R7 an ethyl or sulfonated ethyl group or an alkyl group of up to 4 carbon atoms substituted with a sulfonated phenyl group, each sulfonate group being of formula -SO3M, and wherein in a tetrahydroquinoline coupler R' and R3 are methyl groups, each of R4 and R8 is hydrogen or a methyl group, and R7 is an ethyl group or a group of formula CH2CH2OCOCH3 or CH2CH2OSO3M.
5. A dye according to Claim 1 wherein the coupler C' is selected from those of the formula
wherein R2 is alkyl, R7 is H, alkyl or alkyl substituted with OSO3M or SO3M, and the phenyl ring is substituted with 1 or 2 groups independently selected from alkyl, alkoxy and acylamido.
6. A dye according to Claim 1, 2 or 5 wherein ring A is unsubstituted or substituted with 1 or 2 substituents independently selected from cyano, halogen, alkyl, alkoxy and acylamido.
7. A dye according to Claim 1 having the formula
8. A dye according to Claim 1 having the formula
9. A dye according to Claim 1 having the formula
GB08326869A 1983-10-07 1983-10-07 Disperse and acid azo dyes having one or two cinnamoyl substituents on a phenyl diazonium moiety Expired GB2147602B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB08326869A GB2147602B (en) 1983-10-07 1983-10-07 Disperse and acid azo dyes having one or two cinnamoyl substituents on a phenyl diazonium moiety

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB08326869A GB2147602B (en) 1983-10-07 1983-10-07 Disperse and acid azo dyes having one or two cinnamoyl substituents on a phenyl diazonium moiety

Publications (3)

Publication Number Publication Date
GB8326869D0 GB8326869D0 (en) 1983-11-09
GB2147602A true GB2147602A (en) 1985-05-15
GB2147602B GB2147602B (en) 1987-04-23

Family

ID=10549824

Family Applications (1)

Application Number Title Priority Date Filing Date
GB08326869A Expired GB2147602B (en) 1983-10-07 1983-10-07 Disperse and acid azo dyes having one or two cinnamoyl substituents on a phenyl diazonium moiety

Country Status (1)

Country Link
GB (1) GB2147602B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0434611A2 (en) * 1989-12-11 1991-06-26 Ciba-Geigy Ag Azo dyestuffs, their preparation and their use

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0434611A2 (en) * 1989-12-11 1991-06-26 Ciba-Geigy Ag Azo dyestuffs, their preparation and their use
EP0434611A3 (en) * 1989-12-11 1991-11-13 Ciba-Geigy Ag Azo dyestuffs, their preparation and their use

Also Published As

Publication number Publication date
GB8326869D0 (en) 1983-11-09
GB2147602B (en) 1987-04-23

Similar Documents

Publication Publication Date Title
EP0017558B1 (en) Heterocyclic azo compounds having sulfate groups
EP0020161A2 (en) Azodyestuffs derived from 5-membered heterocyclic amines and aromatic couplers containing sulpho-groups, or salts thereof and their use in dyeing polyamide fibres
KR100847236B1 (en) Azo dyes, dye mixtures, a process for their preparation and a process for dyeing or printing of hydrophobic fiber materials using them
RU2288242C2 (en) Phthalimidylazo dyes, method for their preparing and their using
JPH07108954B2 (en) Diaminopyridine azo dye having an acyloxy group
US4459229A (en) Heterocyclic azo dyes with couplers having sulfoaralkyl groups
US4552951A (en) Disperse and acid azo dyes having one or two cinnamoyl substituents on a phenyl diazonium moiety and containing an aniline, tetrahydroquinoline or benzomorpholine coupler
RU2283328C2 (en) Phthalimidylazodyes and their using
US4247458A (en) Process for preparing azo dyes
GB2147602A (en) Disperse and acid azo dyes having one or two cinnamoyl substituents on a phenyl diazonium moiety
ITRM960342A1 (en) DYES FOR MONOAZO DISPERSION (CASE 150-5866).
US4070352A (en) Benzoisothiazoleazobenzmorpholine of tetrahydroquinone compounds
GB2143541A (en) Disperse methine dyes from 2-amino-5-carbothio-1,3,4-thiadiazole and aniline, tetrahydroquinoline, and benzomorpholine couplers
US4265812A (en) Azo dyes derived from 3-amino-2,1-benzisothiazoles and aromatic amine couplers containing sulfo groups, or salts thereof
US4593087A (en) Disperse and acid azo dyes having one or two cinnamoyl substituents on a thiazole, isothiazole or thiadiazole diazonium moiety and having an aniline, tetrahydroquinoline or benzomorpholine coupler
US4552952A (en) Disperse and acid azo dyes having one or two cinnamoyl substituents on a benzothiazole or benzoisothiazole diazonium moiety and having an aniline, tetrahydroquinoline or benzomorpholine type coupler
US4318851A (en) Disperse monoazo dyes, their preparation and their application to synthetic textile materials
DE2006261C3 (en) Disazo dyes containing sulfonic acid groups and their use for dyeing and printing natural and artificial polyamide fiber materials
ES2269490T3 (en) DISCOUNT COLORS AND COPPER COMPLEX, FOR PAPER STAINING.
Rajagopal et al. Azo disperse dyes derived from 3-amino-7-nitro-2H-1, 2-benzothiazine 1, 1-dioxide
CA1145331A (en) Anionic dyestuffs
US4063881A (en) Synthetic polyamide fibres colored with acid azobenzene dyestuffs, containing a N-alkyl (or substituted alkyl)-n-sulphophenoxyalkylamino radical in the para position to the azo linkage
US4305874A (en) Aniline azo dyes from 1,2,3,4-tetrahydroquinoline and 2,3-dihydro-1,4-benzoxazine couplers containing sulfate alkyl groups
US4530997A (en) Azo dyes from sulfonated 3-sulfonated 3-amino-2,1-benzisothiazoles with 1,2,3,4-tetrahydroquinoline or 2,3-dihydro-1,4-benzoxazine couplers
DE2117462A1 (en) Disazo dyes

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: 19921007