Disperse and acid azo dyes having one or two cinnamoyl substituents on a phenyl diazonium moiety and containing an aniline, tetrahydroquinoline or benzomorpholine coupler

Abstract

This invention relates to azo dyes which may be unsubstituted or substituted with a variety of groups known to the dye art, and containing a diazonium moieties from an aniline type compound and certain coupler moieties from aniline, tetrahydroquinoline, or benzomorpholine compounds, wherein the diazonium moiety has one or two cinnamoyl substituents, and wherein one or more water-solubilizing groups such as a sulfonic acid group or its metal or amine salt may be present as a substituent in the dye molecule for acid dyeing. These dyes are particularly useful in dyeing one or more of polyamide cellulose acetate polyester, wool and other fibers.

Description

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 molecule. 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: ##STR1## wherein C.sup.1 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 R.sub.1 ; R.sub.5 is H or alkyl; and each R.sub.1 is alkyl, alkenyl of 2-6 carbons, aryl, cyclohexyl, alkoxy, halogen, hydroxy, alkylsulfonyl, cyano, carbamoyl, alkanoyl, alkanoyloxy, aroyl, alkoxycarbonyl, sulfamoyl, alkylsulfamoyl, dialkylsulfamoyl, alkanoylamino, SO.sub.3 C.sub.6 H.sub.5, amino, alkylthio, thiocyano, arylsulfonyl, formyl, alkylcarbamoyl, dialkylcarbamoyl, NO.sub.2, --SO.sub.3 M, --OSO.sub.3 M, --COOH, aryloxy, arylthio, alkylsulfonylamino, aroylamino, arylsulfonylamino, or cyclohexylthio, wherein the alkyl, alkylene, alkenyl, aryl, and cyclohexyl moieties of the above R.sub.1 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 (C.sub.4 H.sub.4 O.sub.2 N), --NO.sub.2, alkanoylamino, alkylsulfonylamino, 1-(2-pyrrolidono) (C.sub.4 H.sub.6 ON), halogen, cyano, alkoxy, aryl, cyclohexyl, hydroxy, --SO.sub.3 M, --OSO.sub.3 M, aryloxy, furyl (C.sub.4 H.sub.3 O), aroyloxy, alkoxycarbonyl, --SO.sub.2 N-(alkyl).sub.2, --NHCOO-alkyl, --NHCONH-alkyl, glutarimido (C.sub.5 H.sub.6 O.sub.2 N), phthalimido (C.sub.8 H.sub.4 O.sub.2 N), CONH.sub.2, CONH-alkyl, CON(alkyl).sub.2, alkoxyalkoxy, alkylthio, arylthio, alkylsulfonyl, and arylsulfonyl, wherein M is selected from H.sup.+, NH.sub.4.sup.+, Na.sup.+, K.sup.+, 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 especially trimethylamine.

The couplers C.sup.1 preferably have the formulae: ##STR2## wherein R.sub.1 is defined above; R.sub.2 and R.sub.7 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.sub.1 groups; and R.sub.3, R.sub.4 and R.sub.8 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 R.sub.1 groups: CH.sub.3, Cl, SO.sub.2 C.sub.2 H.sub.5, CN, CONH.sub.2, COC.sub.2 H.sub.5, COC.sub.6 H.sub.5, COOC.sub.2 H.sub.5, SO.sub.2 NH.sub.2, SO.sub.2 NHCH.sub.3, SO.sub.2 N(C.sub.2 H.sub.5).sub.2, NHCOC.sub.2 H.sub.5, SO.sub.3 C.sub.6 H.sub.5, SCH.sub.3, SCN, SO.sub.2 C.sub.6 H.sub.5, CHO, CONHC.sub.2 H.sub.5, CON(C.sub.2 H.sub.5).sub.2, OH, NO.sub.2, C.sub.6 H.sub.5, C.sub.6 H.sub.11, SO.sub.3 K, CF.sub.3, CH.sub.2 OOCC.sub.2 H.sub.5, Br, SO.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, I, CONHCH.sub.2 CN, COCH.sub.2 CH.sub.2 OH, COC.sub.6 H.sub.3 -o-CH.sub.3 -p-OCH.sub.3, COOC.sub.2 H.sub.4 -CH.dbd.CH.sub.2, SO.sub.2 NHCH.sub.2 CH.sub.2 CN, SO.sub.2 NHCH.sub.2 -succinimido, SO.sub.2 NHC.sub.2 H.sub.4 -C.sub.6 H.sub.5, NHCOCH.sub.2 CH.sub.2 Cl, SO.sub.3 C.sub.6 H.sub.4 -p-NO.sub.2, SCH.sub.2 CH.sub. 2 OH, SC.sub.2 H.sub.4 -C.sub.6 H.sub.11, SO.sub.2 C.sub.6 H.sub.4 -p-NHCOCH.sub.3, C.sub.6 H.sub.4 -p-NHSO.sub.2 CH.sub.3, CONHC.sub.2 H.sub.4 NHSO.sub.2 CH.sub.3, CONHCH.sub.2 CH.sub.2 OH, CH.sub.2 CH.sub.2 NO.sub.2, C.sub.6 H.sub.4 -p-(2-pyrrolidono), C.sub.6 H.sub.10 -4-CN, OSO.sub.3 K, CH.sub.2 SO.sub.3 Na, OC.sub.6 H.sub.5, SO.sub.2 C.sub.2 H.sub.4 OSO.sub.3 K, C.sub.2 H.sub.4 -furyl, C.sub.2 H.sub.4 OOCC.sub.6 H.sub.5, COCH.sub.2 CH.sub.2 COOCH.sub.3, COC.sub.6 H.sub.4 -p-SO.sub.2 NHC.sub.6 H.sub.5, COOCH.sub.2 CH.sub.2 -SO.sub.2 NHCH.sub.3, SO.sub.2 NHCH.sub.2 SO.sub.2 N(C.sub.2 H.sub.5).sub.2, SO.sub.2 NHCH.sub.2 NHCOOCH.sub.3, SO.sub.2 NHC.sub.2 H.sub.4 NHCONHCH.sub.3, NHCOCH.sub.2 CH.sub.2 -glutarimido, SO.sub.3 C.sub.6 H.sub.4 -p-phthalimido, SCH.sub.2 CONH.sub.2, C.sub.6 H.sub.4 -p-SO.sub.2 CH.sub.3, SO.sub.2 C.sub.6 H.sub.4 -p-CONHCH.sub.2 SO.sub.3 Na, CH.sub.2 SO.sub.2 C.sub.6 H.sub. 5, CONHCH.sub.2 CH.sub.2 CON(CH.sub.3).sub.2, CONHCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3, CH.sub.2 CH.sub.2 SO.sub.3 H, C.sub.6 H.sub.4 -p-SC.sub.2 H.sub.5, C.sub.6 H.sub.10 -4-SC.sub.6 H.sub.4 (p-OSO.sub.3 H), CH.sub.2 CH.dbd.CH.sub.2, COOH, OC.sub.6 H.sub.5, OCH.sub.3, SC.sub.6 H.sub.5, NHSO.sub.2 CH.sub.3, NHCOC.sub.6 H.sub.5, NH.sub.2, NHSO.sub.2 C.sub.6 H.sub.5, SC.sub.6 H.sub.11, and --OOCCH.sub.3.

Typical for R.sub.3, R.sub.4, R.sub.5 and R.sub.8 are: H, CH.sub.3, C.sub.2 H.sub.5, C.sub.4 H.sub.9 -n, and CH.sub.2 (CH.sub.3).sub.2.

The following are typical specific R.sub.2 and R.sub.7 substituents: H, CH.sub.3, C.sub.2 H.sub.5, C.sub.4 H.sub.9 -n, CH.sub.2 CH.dbd.CH.sub.2, C.sub.6 H.sub.5, C.sub.6 H.sub.11, CH.sub.2 OOCC.sub.2 H.sub.5, CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, CH.sub.2 CN, CH.sub.2 CH.sub.2 OH, C.sub.6 H.sub.3 -o-CH.sub.3 -p-OCH.sub.3, C.sub.2 H.sub.4 -CH.dbd.CH.sub.2, CH.sub.2 -succinimido, CH.sub.2 CH.sub.2 -C.sub.6 H.sub.5, CH.sub.2 CH.sub.2 Cl, C.sub.6 H.sub.4 -p-NO.sub.2, CH.sub.2 CH.sub.2 C.sub.6 H.sub.11, C.sub.6 H.sub.4 -p-NHSO.sub.2 CH.sub.3, C.sub.2 H.sub.4 NHSO.sub.2 CH.sub.3, CH.sub.2 CH.sub.2 NO.sub.2, C.sub.6 H.sub.4 -p-(2-pyrrolidono), C.sub.6 H.sub.10 -4-CN, CH.sub.2 SO.sub.3 Na, CH.sub.2 CH.sub.2 OSO.sub.3 K, CH.sub.2 CH.sub.2 -furyl, CH.sub.2 CH.sub.2 OOCC.sub.6 H.sub.5, CH.sub.2 CH.sub.2 COOCH.sub.3, C.sub.6 H.sub.5 -p-SO.sub.2 NHC.sub.6 H.sub.5, CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.3, CH.sub.2 SO.sub.2 N(C.sub.2 H.sub.5).sub.2, CH.sub.2 NHCOOCH.sub.3, CH.sub.2 CH.sub.2 NHCONHCH.sub.3, CH.sub.2 CH.sub.2 -glutarimido, C.sub.6 H.sub.4 -p-phthalimido, CH.sub.2 CONH.sub.2, C.sub.6 H.sub.4 -p-SO.sub.2 CH.sub.3, C.sub.6 H.sub.4 -p-CONHCH.sub.2 SO.sub.3 Na, CH.sub.2 SO.sub.2 C.sub.6 H.sub.5, CH.sub.2 CH.sub.2 CON(CH.sub.3).sub.2, CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, CH.sub.2 CH.sub.2 SO.sub.3 H, C.sub.6 H.sub.4 -p-SC.sub.2 H.sub.5, and C.sub.6 H.sub. 10 -4-SC.sub.6 H.sub.4 (p-OSO.sub.3 H).

Preferred substituents, in addition to H, for the A ring are halogen, CN, methoxycarbonyl, alkoxy, CF.sub.3, NO.sub.2, alkanoyl, alkylsulfonyl, .beta.-hydroxyethylcarbamoyl, .beta.-potassiosulfatoethylcarbamoyl, methylcarbamoyl, carbamoyl, ethoxycarbonyl, or methyl; for R.sub.1 on the cinnamoyl rings are H, alkyl, aralkyl, aralkyl substituted with --SO.sub.3 M or --SO.sub.4 M, cyclohexylalkyl, cyclohexylalkyl substituted with --SO.sub.3 M or --SO.sub.4 M, alkoxy, or alkanoylamino; for R.sub.2 are H, alkyl, aralkyl, alkyl or aralkyl substituted with --SO.sub.3 M or --SO.sub.4 M, cyclohexylalkyl, cyclohexylalkyl substituted with --SO.sub.3 M or --SO.sub.4 M; for R.sub.7 are H, alkyl, aralkyl, aralkyl substituted with --SO.sub.3 M or --SO.sub.4 M, cyclohexylalkyl, cyclohexylalkyl substituted with --SO.sub.3 M or --SO.sub.4 M, sodio- or potassiosulfatoalkyl, sodio- or potassiosulfonicalkyl, or alkanoyloxyalkyl; for R.sub.1 on the couplers are H, aralkyl, aralkyl substituted with --SO.sub.3 M or --SO.sub.4 M, cyclohexylalkyl, cyclohexylalkyl substituted with --SO.sub.3 M or --SO.sub.4 M, --SO.sub.3 Na, --SO.sub.3 K, halogen, --SO.sub.4 Na, --SO.sub.4 K, alkyl, alkoxy, --COOH, or --OH; for R.sub.3, R.sub.4 and R.sub.8 are H and alkyl; and for R.sub.5 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. Pat. No. 2,805,218 and British Pat. No. 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 --OSO.sub.3 M group. Alternatively a chloroalkyl group in the dye could be reacted with K.sub.2 SO.sub.3 to give the --CH.sub.2 SO.sub.3 K group. Also, sulphonation of an aromatic ring or other reactive group in the dye with a sulphonating agent such as H.sub.2 SO.sub.4 or Cl--SO.sub.3 H 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.degree. C. To this solution is added, at 50.degree.-60.degree. C., 60% oleum (30.0 g.) with good stirring. The mixture is stirred and heated at about 60.degree. 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; and11 N--Benzyl-N--cyclohexylaniline.______________________________________

PREPARATION B--Diazotization and Coupling of 2,6-dibromo-4-acetylaniline

To 150 g. of 60% acetic acid containing 10 g. of concentrated H.sub.2 SO.sub.4 is added 8.2 g. (0.055 m.) of 2,6-dibromo-4-acetylaniline at room temperature. The solution is cooled to -5.degree. C., and a solution of 3.6 g. NaNO.sub.2 in 20 ml. of concentrated H.sub.2 SO.sub.4 is added below 0.degree. C. The reaction mixture is stirred at -5.degree. to 0.degree. 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% KCl solution, and dried in air. The dyes usually are admixed with about an equal weight of K.sub.2 SO.sub.4 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-acetylaniline N-benzyl-N-ethylaniline (1.5 g.) is added portionwise to 15 ml. of concentrated H.sub.2 SO.sub.4 over 20 min., allowing the temperature to rise to 30.degree. C. The reaction mixture is then heated at 70.degree. C., when the reaction is completed as evidenced by thin-layer 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: ##STR3##

EXAMPLE ##STR4##

A mixture of compound (I) (2 g.), benzaldehyde (1.5 g.), acetic acid (25 ml.) and concentrated sulphuric acid (5 ml.) was stirred at 100.degree. 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-4-acetylaniline 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 ##STR5## Cinnamoyl Group Substituents Position R.sub.1 on D R.sub.5 on A R.sub.1 on C R.sub.2 R.sub.7 4 H H H H H H 4 4-NO.sub.2 H 6-COCH.sub.3 2-CH.sub.3 C.sub.2 H.sub.5 Ph 4 4-CN H 6-NO.sub.2 5-COCH.sub.3 C.sub.2 H.sub.5 C.sub.6 H.sub.11 4 5-COCH.sub.3 H 5,6-di-Cl 5-OCH.sub.3 CH.sub.2C.sub.6 H.sub.4-p-SO.sub. 4 K CH.sub.2CHCH.sub.2 4 4-COPh CH.sub.3 6-CN 5-SO.sub.3 Na H CH.sub.2 OOCC.sub.2 H.sub.5 5 2,4-di-COOH CH.sub.3 4-NHSO.sub.2 CH.sub.3 5-OCH.sub.2 CH.sub.2 SO.sub.4 K CH.sub.2C.sub.6 H.sub.104-SO.sub.3 K C.sub.6 H.sub.4-p-OOCCH.sub.3 6 4-OOCCH.sub.3 CH.sub.3 5-CH.sub.3 5-OCH.sub.2 CH.sub.2 SO.sub.4 NH(Et).sub.3 H C.sub.6 H.sub.104-CH.sub.3 4 4-NHCOCH.sub.3 CH.sub.3 6-OCH.sub.3 2-CH.sub.3 CH.sub.2C.sub.6 H.sub.4-p-SO.sub.4 NH(Et).sub.3 CH.sub.2 CH.sub.2 (C.sub.4 H.sub.4 O.sub.2 N) 6 4-NHCOPh CH.sub.3 4-Ph 2-Ph CH.sub.3 CH.sub.2 CH.sub.2 NO.sub.2 4 4-C.sub.2 H.sub.5 CH.sub.3 H 2-NO.sub.2 CH.sub.3 C.sub.6 H.sub.4-p-NO.sub.2 6 4-Ph H H 2-OCH.sub.3 CH.sub.3 CH.sub.2 NHOCCH.sub.3 4 Cl H 5,6-di-SO.sub.3 Na 5-NHCOCH.sub.3 C.sub.2 H.sub.5 CH.sub.2 NHSO.sub.2 CH.sub.3 4 SO.sub.3 K H H 3NHCOCH.sub.3 H C.sub.2 H.sub.5 4 2-Cl4-SO.sub.2 CH.sub.3 H 6-SO.sub.3 Na 3-NHSO.sub.2 CH.sub.3 C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-NHOCCH.sub.3 4 4-NHSO.sub.2 CH.sub.3 H 6-OCH.sub.2 CH.sub.2 SO.sub.4 K 3-COOCH.sub.3 C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-NHSO.sub.2 CH.sub.3 4 4-COOCH.sub.3 H 6-OCH.sub.2 CH.sub.2 SO.sub.4 K 3-COOH C.sub.2 H.sub.5 C.sub.6 H.sub.104-NHOOCH.sub.3 4 2-OCH.sub.3 C.sub.2 H.sub.5 6-NHCOPh 2-Cl CH.sub.2 CH.sub.2 Cl CH.sub.2 CH.sub.2 Cl 5 4-OC.sub.2 H.sub.5 C.sub.2 H.sub.5 4-NHCOPh 2,6-di-Br C.sub.6 H.sub.4-p-Br C.sub.6 H.sub.4-p-Br 6 4-SO.sub.3 Na C.sub.2 H.sub.5 4-NHCOCH.sub.3 2,6-di-Br C.sub.6 H.sub.4-p-CN C.sub.6 H.sub.4-p-CN 6 2-SO.sub.3 Na C.sub.2 H.sub.5 4-OOCC.sub.2 H.sub.5 2-OCH.sub.35-NHCOCH.sub.3 CH.sub.2 CH.sub.2 CN CH.sub.2 CH.sub.2 CN 4 2-OCH.sub.34-SO.sub.3 K H 5-COOH 2-CH.sub.2 OOCCH.sub.3 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OC.sub. 2 H.sub.5 4 4-OCH.sub.2 CH.sub.2 OSO.sub.3 K H H 2-CH.sub.2 Cl CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 4 2-SO.sub.3 Na5-Cl H H 2-CN CH.sub.2 Ph CH.sub.2C.sub.6 H.sub.4-p-SO.sub.4 N.sup.+ H(CH.sub.3).sub.3 4 4-Cl H 6-SO.sub.2 CH.sub.3 2-OOCCH.sub.3 CH.sub.2 C.sub.6 H.sub.11 CH.sub.2 C.sub.6 H.sub.10 4-SO.sub.3 Na 4 4-OH H 6-CF.sub.3 5-COOH H C.sub.6 H.sub.4-o-OH 4 4-CH.sub.2 OOCCH.sub.3 C.sub.3 H.sub.7n 6-COOCH.sub.3 5-OH C.sub.2 H.sub.5CH.sub.2 CH.sub.2 OH 4 4-SO.sub.3 K C.sub.3 H.sub.7n 6-CHO 5-CH.sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2SO.sub.3 K CH.sub.2 S CH.sub.2O.sub.3 K 6 4-OPh H 4-CONH.sub.2 2-CH.sub.3 H CH.sub.2C.sub.6 H.sub.4-p-OSO.sub.3 K 6 4-NO.sub.2 H 4-CONHCH.sub.3 5-COCH.sub.3 H CH.sub.2 OPh 6 5-CN H 4-CH.sub.2 Ph 5-OCH.sub.3 H CH.sub.2 SO.sub.2 NHPh 4 4-SO.sub.3 K H H 3-CH.sub.3 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 SO.sub.3 K 4 4-COCH.sub.3 H 6-CH.sub.2 SO.sub.3 K 5-SO.sub.3 Na CH.sub.2 SO.sub.2 NHCH.sub.3 CH.sub.2 SO.sub.2 NHCH.sub.3 4 5-CH.sub.3 H 6-CH.sub.2 OSO.sub.3 K 5-OCH.sub.2 CH.sub.2 SO.sub.4 K H CH.sub.2C.sub.6 H.sub.4-p-SO.sub.2 NHCH.sub.3 4 5-C.sub.6 H.sub.4-p-SO.sub.3 K H 6-C.sub.6 H.sub.4-p-SO.sub.3 K 5-OCH.sub.2 CH.sub.2 SO.sub.3 K CH.sub.2 COOCH.sub.3 CH.sub.2 COOCH.sub.3 4 5-OCH.sub.3 H 6-CH.sub.2 CH.sub.2 OH 2-CH.sub.3 H CH.sub.2 SO.sub.2 N(CH.sub.3).sub.2 4 4,5-di-Br H 6-CH.sub.2 Cl 2-C.sub.6 H.sub.4-p-SO.sub.3 K C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-NHCOOCH.sub.3 4 5-COOH C.sub.4 H.sub.9n 6-C.sub.6 H.sub.4-p-Br 2-NO.sub.2 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 CONH.sub. 2 4 H H H 2-OCH.sub.3 C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-CONHCH.sub.3 4 4-NO.sub.2 H 5-COCH.sub.3 5-NHCOCH.sub.3 C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-SCH.sub.3 4 4-CN H 5-NO.sub.2 3-NHSO.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 SCH.sub.3 CH.sub.2 CH.sub.2 SCH.sub.3 4 5-COCH.sub.3 H 5-Cl 3-COOCH.sub.3 H CH.sub.2C.sub.6 H.sub.4-p-SCH.sub.3 4 4-COPh CH.sub.3 5,6-di-CN 3-COOH CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 4 2,4-di-COOH CH.sub.3 5-NHSO.sub.2 CH.sub.3 2-Cl H CH.sub.2 SO.sub.2 Ph 4 4-OOCCH.sub.3 CH.sub.3 6-CH.sub.3 2,6-di-Br H CH.sub.2 CH.sub.2 OSO.sub.3 K 4 4-NHCOCH.sub.3 CH.sub.3 6-OCH.sub.3 2,6-di-Br H C.sub.6 H.sub.4-p-OSO.sub.3 K 4 4-NHCOPh CH.sub.3 6-Ph 2-OCH.sub.35-NHCOCH.sub.3 H CH.sub.2 (C.sub.8 H.sub.4 O.sub.2 N) 4 4-CH.sub.2 CHCH.sub.2 H H 3-NHCOCH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 4,6 H CH.sub.3 H 3-OCPh C.sub.2 H.sub.5 C.sub.2 H.sub.5 4 4-SO.sub.3 K H H 2-OCH.sub.35-NHCOCH.sub.3 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 SO.sub.3 K 4 4-CONH.sub.2 H H 5-CH.sub.2 CONHCH.sub.3 H H 4 3-SO.sub.2 NH.sub.2 H 6-COCH.sub.3 5-CH.sub.2 CON(CH.sub.3).sub.2 C.sub.2 H.sub.5 Ph 4 4-SO.sub.2 NHCH.sub.3 H 6-NO.sub.2 5-CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 C.sub.2 H.sub.5 C.sub.6 H.sub.11 4 4-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 H 6-Cl 5-CH.sub.2 SC.sub.2 H.sub.5 H CH.sub.2CHCH.sub.2 4 4-SO.sub.3 C.sub.6 H.sub.5 CH.sub.3 6-CN 2-CH.sub.2 SC.sub.6 H.sub.5 H CH.sub.2 OOCC.sub.2 H.sub.5 4 4-SCH.sub.3 CH.sub.3 6-NHSO.sub.2 CH.sub.3 5-CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 H C.sub.6 H.sub.4-p-OOCCH.sub.3 4 2,4-di-SCN CH.sub.3 5-CH.sub.3 5-CH.sub.2 SO.sub.2 C.sub.6 H.sub.5 H C.sub.6 H.sub.104-CH.sub.3 4 4-SO.sub.2 C.sub.6 H.sub.5 CH.sub.3 5-OCH.sub.3 5-C.sub.6 H.sub.3 -o,-p-di-CN H CH.sub.2 CH.sub.2 (C.sub.4 H.sub.4 O.sub.2 N) 4 2-CHO4-CN CH.sub.3 6-Ph 5-C.sub.6 H.sub.2-o,.sub.--m,-p-tri-Cl CH.sub.3 CH.sub.2 CH.sub.2 NO.sub.2 4 4-CONHC.sub.2 H.sub.5 CH.sub.3 H 2,6-di-OSO.sub.3 N H(CH.sub.3).sub.3 CH.sub.3 C.sub.6 H.sub.4-p-NO.sub.2 4 4-CON(C.sub.2 H.sub.5).sub.2 H H 2,6-di-SO.sub.3 N H(CH.sub.3).sub.3 CH.sub.3 CH.sub.2 NHOCCH.sub.3 4 3-C.sub.6 H.sub.11 H 6-SO.sub.3 Na 2,6-di-OSO.sub.3 K C.sub.2 H.sub.5 CH.sub.2 NHSO.sub.2 CH.sub.3 4 3-SC.sub.6 H.sub.5 H 6-SO.sub.3 Na 2-SO.sub.3 N H(CH.sub.3).sub.3 C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-NHOCCH.sub.3 4 4-NHSO.sub.2 C.sub.6 H.sub.5 H 5-OCH.sub.2 CH.sub.2 SO.sub.4 K 2-OSO.sub.3 N H(CH.sub.3).sub.3 C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-NHSO.sub.2 CH.sub.3 4 4-SC.sub.6 H.sub.11 H 5-OCH.sub.2 CH.sub.2 SO.sub.4 K 5-SC.sub.6 H.sub.10-p-SO.sub.3 K C.sub.2 H.sub.5 C.sub.6 H.sub.104-NHOCCH.sub.34 4-C.sub.6 H.sub.4-p-CH.sub.3 C.sub.2 H.sub.5 6-NHCOPh 5-C.sub.6 H.sub.4-p-CH.sub.3 CH.sub.2 CH.sub.2 Cl CH.sub.2 CH.sub.2 Cl 4 4-C.sub.6 H.sub.4-p-CH.sub.2 CHCH.sub.2 C.sub.2 H.sub.5 6-NHCOPh 5-C.sub.6 H.sub.4-p-CH.sub.2 CHCH.sub.2 C.sub.6 H.sub.4-p-Br C.sub.6 H.sub.4-p-Br 4 4-OCH.sub.2 CH.sub.2 NO.sub.2 C.sub.2 H.sub.5 5-NHCOCH.sub.3 5-OCH.sub.2 CH.sub.2 NO.sub.2 C.sub.6 H.sub.4-p-CN C.sub.6 H.sub.4-p-CN 4 2-CH.sub.2 NHCOCH.sub.3 C.sub.2 H.sub.5 5-OOCC.sub.2 H.sub.5 2-CH.sub.2 NHCOCH.sub.3 CH.sub.2 CH.sub.2 CN CH.sub.2 CH.sub.2 CN 4 4-CH.sub.2 NHSO.sub.2 C.sub.2 H.sub.5 H 6-COOH 5-CH.sub.2 NHSO.sub.2 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OC.sub.2 H.sub. 5 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 4,6 4-CH.sub.2 CH.sub.2 Cl H H 5-CH.sub.2 CH.sub.2 Cl CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 6 2,6-di-CH.sub.2 CN H H 2,6-di-CH.sub.2 CN CH.sub.2 Ph CH.sub.2 Ph 6 4-CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 H 4-SO.sub.2 CH.sub.3 5-CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 CH.sub.2 C.sub.6 H.sub.11 CH.sub.2 C.sub.6 H.sub.11 6 4-CH.sub.2 C.sub.6 H.sub.5 H 4-CH.sub.2 C.sub.6 H.sub.5 5-COOH H C.sub.6 H.sub.4-o-OH 6 4-CH.sub.2 C.sub.6 H.sub.11 C.sub.3 H.sub.7n 4-COOCH.sub.3 5-CH.sub.2 C.sub.6 H.sub.11 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OH 6 4-CH.sub.2 CH(OH)CH.sub.2 OH C.sub.3 H.sub.7n 4-CHO 5-CH.sub.2 CH(OH)CH.sub.2 OH CH.sub.2 CH.sub.2SO.sub.3 K CH.sub.2 CH.sub.2SO.sub.3 K 4 4-CH.sub.2 CH.sub.2SO.sub.3 K H 5-CONH.sub.2 5-CH.sub.2 CH.sub.2SO.sub.3 K H C.sub. 6 H.sub.4-p-OSO.sub.3 K 4 4-CH.sub.2 OC.sub.6 H.sub.5 H 5-CONHCH.sub.3 5-CH.sub.2 OC.sub.6 H.sub.5 H CH.sub.2 OPh 4 4-CH.sub.2 OOCC.sub.6 H.sub.5 H 5-CH.sub.2 Ph 5-CH.sub.2 OOCC.sub.6 H.sub.5 H CH.sub.2 SO.sub.2 NHPh 4 5-CH.sub.2 COOCH.sub.3 H 6-CH.sub.2 SO.sub.3 K 5-CH.sub.2 COOCH.sub.3 CH.sub.2 SO.sub.2 NHCH.sub.3 CH.sub.2 SO.sub.2 NHCH.sub.3 4 4-C.sub.6 H.sub.4-p-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 H 6-CH.sub.2 OSO.sub.3 K 5-C.sub.6 H.sub.4-p-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 H C.sub.6 H.sub.4-p-SO.sub.2 NHCH.sub.3 4 CH.sub.2 CH.sub.2 NHCOOCH.sub.3 H 6-C.sub.6 H.sub.4-p-SO.sub.3 K 5-CH.sub.2 CH.sub.2 NHCOOCH.sub.3 CH.sub.2 COOCH.sub.3 CH.sub.2 COOCH.sub.3 4 4-CH.sub.2 NHCONHCH.sub.3 H 6-CH.sub.2 CH.sub.2 OH 5-CH.sub.2 NHCONHCH.sub.3 H CH.sub.2 SO.sub.2 N(CH.sub.3).sub.2 4 4-CH.sub.2 CONH.sub.2 H 6-CH.sub.2 Cl 5-CH.sub.2 CONH.sub.2 C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-NHCOOCH.sub.3 4 5-CH.sub.2 CONHCH.sub.3 C.sub.4 H.sub.9n 6-C.sub.6 H.sub.4-p-Br 5-CONH.sub.2 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 CONH.sub.2 4 4-CH.sub.2 CON(CH.sub.3).sub.2 H H 3-SO.sub.2 NH.sub.2 C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-CONHCH.sub.3 4 4-CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 H 5-COCH.sub.3 5-SO.sub.2 NHCH.sub.3 C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-SCH.sub.3 4,6 4-CH.sub.2 SC.sub.2 H.sub.5 H 5-NO.sub.2 5-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.2 CH.sub.2 SCH.sub.3 CH.sub.2 CH.sub.2 SCH.sub.3 6 5-CH.sub.2 SC.sub.6 H.sub.5 H 4-Cl 5-SO.sub.3 C.sub.6 H.sub.5 H CH.sub.2C.sub.6 H.sub.4-p-SCH.sub.3 4 4-CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 CH.sub.3 6-CN 5-SCH.sub.3 CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 4 2,4-di-CH.sub.2 SO.sub. 2 C.sub.6 H.sub.5 CH.sub.3 6-NHSO.sub.2 CH.sub.3 2,5-di-SCN H CH.sub.2 SO.sub.2 Ph 4 4-C.sub.6 H.sub.3-o,-p-di-CN CH.sub.3 5-CH.sub.3 5-SO.sub.2 C.sub.6 H.sub.5 H CH.sub.2 CH.sub.2 OSO.sub.3 K 4 4-C.sub.6 H.sub.2-o,-m,-p-tri-Cl CH.sub.3 5-OCH.sub.3 2-CHO6-CN H C.sub.6 p H.sub.4--OSO.sub.3 K 4 2,6-di-OSO.sub.3 Na CH.sub.3 6-Ph 5-CONHC.sub.2 H.sub.5 H CH.sub.2(C.sub.8 H.sub.4 O.sub.2 N) 4 H H 6-CH.sub.2 (C.sub.4 H.sub.4 O.sub.2 N) 5-CON(C.sub.2 H.sub.5).sub.2 C.sub.2 H.sub.5 C.sub.2 H.sub.5 4 H H 6-CH.sub.2 (C.sub.4 H.sub.3 O) 3-C.sub.6 H.sub.11 C.sub.2 H.sub.5 C.sub.2 H.sub.5 4 5-CH.sub.2 (C.sub.8 H.sub.4 O.sub.2 N) H H 3-SC.sub.6 H.sub.5 C.sub.2 H.sub.5 C.sub.2 H.sub.5 4 5-CH.sub.2 (C.sub.4 H.sub.3 O) H H 6-NHSO.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.5 C.sub. 2 H.sub.5 4 2-Cl,SO.sub.3 M H 2,6-di-Br 2-OCH.sub.35-CH.sub.3 H C.sub.2 H.sub.5 4 H H 2,6-di-Br 2-OCH.sub.35-CH.sub.3 H C.sub.2 H.sub.5 TABLE 2 ##STR6## Cinnamoyl Group Substituents Position R.sub.1 on D R.sub.5 on A R.sub.1 on C R.sub.3 R.sub.4 R.sub.8 R.sub.7 4 H H H H H H H H 4 4-NO.sub.2 H 5-COCH.sub.3 7-CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 Ph 4 4-CN H 5-NO.sub.2 5-COCH.sub.3 CH.sub.3 CH.sub.3 H C.sub.6 H.sub.11 4 5-COCH.sub.3 H 5-Cl 5-OCH.sub.3 CH.sub.3 CH.sub.3 H CH.sub.2CHCH.sub.2 4,5 4-COPh CH.sub.3 6-CN 7-SO.sub.3 Na CH.sub.3 CH.sub.3 H CH.sub.2 OOCC.sub.2 H.sub.5 5 2,4-di-COOH CH.sub.3 4-NHSO.sub.2 CH.sub.3 7-OCH.sub.2 CH.sub.2 SO.sub.4 K CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-OOCCH.sub.3 6 4-OOCCH.sub.3 CH.sub.3 5-CH.sub.3 7-OCH.sub.2 CH.sub.2 SO.sub.4 N H(Et).sub.3 CH.sub.3 CH.sub.3 H C.sub.6 H.sub.104-CH.sub.3 6 4-NHCOCH.sub.3 CH.sub.3 4,5-di-OCH.sub.3 7-CH.sub.3 CH.sub.3 H H CH.sub.2 CH.sub.2 (C.sub.4 H.sub.4 O.sub.2 N) 6 4-NHCOPh CH.sub.3 4-Ph 7-Ph CH.sub.3 H H CH.sub.2 CH.sub.2 NO.sub.2 4 4-C.sub.2 H.sub.5 CH.sub.3 H 7-NO.sub.2 CH.sub.3 H H C.sub.6 H.sub.4-p-NO.sub.2 6 4-Ph H H 7-OCH.sub.3 CH.sub.3 H H CH.sub.2 NHOCCH.sub.3 4 2,5-di-Cl H 6-SO.sub.3 Na 7-NHCOCH.sub.3 CH.sub.3 H H CH.sub.2 NHSO.sub.2 CH.sub.3 4 2-Cl4-SO.sub.2 CH.sub.3 H 6-SO.sub.3 Na 7-NHSO.sub.2 CH.sub.3 CH.sub.3 H H C.sub.6 H.sub.4-p-NHOCCH.sub.3 4 4-NHSO.sub.2 CH.sub.3 H 5-OCH.sub.2 CH.sub.2 SO.sub.4 K 7-COOCH.sub.3 CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-NHSO.sub.2 CH.sub.3 4 4-COOCH.sub.3 H 5-OCH.sub.2 CH.sub.2 SO.sub.4 K 7-COOH H H H C.sub.6 H.sub.104-NHOCCH.sub.3 4 2-OCH.sub.3 C.sub.2 H.sub.5 6-NHCOPh 7-Cl CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 Cl 4 4-OC.sub.2 H.sub.5 C.sub.2 H.sub.5 6-NHCOPh 5,7-di-Br CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-Br 4 4-SO.sub.3 Na C.sub.2 H.sub.5 6-NHCOCH.sub.3 5,7-di-Br CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-CN 4 2-SO.sub.3 Na C.sub.2 H.sub.5 5-OOCC.sub.2 H.sub.5 5-OCH.sub.37-NHCOCH.sub.3 CH.sub.3 CH.sub.3 H CH.sub.2 CH.sub.2 CN 4 2-OCH.sub.34-SO.sub.3 K H 6-COOH 7-CH.sub.2 OOCCH.sub.3 CH.sub.3 CH.sub.3 H CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 4 4-OCH.sub.2 CH.sub.2 OSO.sub.3 K H H 7-CH.sub.2 Cl CH.sub.3 CH.sub.3 H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 4 2-SO.sub.3 Na5-Cl H H 7-CN CH.sub.3 H H CH.sub.2 Ph 4 4-Cl H 5-SO.sub.2 CH.sub.3 7-OOCCH.sub.3 CH.sub.3 H H CH.sub.2 C.sub.6 H.sub.11 4 4-OH H 5-CF.sub.3 5-COOH CH.sub.3 H H C.sub.6 H.sub.4-o-OH 4 4-CH.sub.2 OOCCH.sub.3 C.sub.3 H.sub.7n 5-COOCH.sub.3 5-OH CH.sub.3 H H CH.sub.2 CH.sub.2 OH 4 4-SO.sub.3 K C.sub.3 H.sub.7n 5-CHO 5-CH.sub.2 CHCH.sub.2 CH.sub.3 H H CH.sub.2 CH.sub.2SO.sub.3 K 4,6 4-OPh H 5-CONH.sub.2 7-CH.sub.3 CH.sub.3 H H C.sub.6 H.sub.4-p-OSO.sub.3 K 6 4-NO.sub.2 H 4-CONHCH.sub.3 7-COCH.sub.3 CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 CH.sub.2 OPh 4 5-CN H 5-CH.sub.2 Ph 7-OCH.sub.3 H H H CH.sub.2 SO.sub. 2 NHPh 4 4-COCH.sub.3 H 5-CH.sub.2 SO.sub.3 K 7-SO.sub.3 Na CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.2 SO.sub.2 NHCH.sub.3 4 5-CH.sub.3 H 5-CH.sub.2 OSO.sub.3 K 7-OCH.sub.2 CH.sub.2 SO.sub.4 K CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-SO.sub.2 NHCH.sub.3 4 5-Ph H 5-C.sub.6 H.sub.4-p-SO.sub.3 K 7-OCH.sub.2 CH.sub.2 SO.sub.3 K CH.sub.3 CH.sub.3 H CH.sub.2 COOCH.sub.3 4 5-OCH.sub.3 H 5-CH.sub.2 CH.sub.2 OH 7-CH.sub.3 CH.sub.3 CH.sub.3 H CH.sub.2 SO.sub.2 N(CH.sub.3).sub.2 4 4,5-di-Br H 5-CH.sub.2 Cl 7-Ph CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-NHCOOCH.sub.3 4 5-COOH C.sub.4 H.sub.9n 6-C.sub.6 H.sub.4-p-Br 7-NO.sub.2 H H H CH.sub.2 CH.sub.2 CONH.sub.2 4 H H H 7-OCH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 C.sub.6 H.sub.4-p-CONHCH.sub.3 4 4-NO.sub.2 H 6-COCH.sub.3 7-NHCOCH.sub.3 CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-SCH.sub.3 4 4-CN H 6-NO.sub.2 7-NHSO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 H CH.sub.2 CH.sub.2 SCH.sub.3 4 5-COCH.sub.3 H 6-Cl 7-COOCH.sub.3 CH.sub.3 CH.sub.3 H CH.sub.2C.sub.6 H.sub.4-p-SCH.sub.3 4 4-COPh CH.sub.3 6-CN 7-COOH CH.sub.3 CH.sub.3 H CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 4 2,4-di-COOH CH.sub.3 5-NHSO.sub.2 CH.sub.3 7-Cl CH.sub.3 CH.sub.3 H CH.sub.2 SO.sub.2 Ph 4 4-OOCCH.sub.3 CH.sub.3 6-CH.sub.3 5,7-di-Br CH.sub.3 H H CH.sub.2 CH.sub.2 OSO.sub.3 K 4 4-NHCOCH.sub.3 CH.sub.3 6-OCH.sub.3 5,7-di-Br CH.sub.3 H H C.sub.6 H.sub.4-p-OSO.sub.3 K 4 4-NHCOPh CH.sub.3 6-Ph 5-OCH.sub.37-NHCOCH.sub.3 CH.sub.3 H H CH.sub.2 (C.sub.8 H.sub.4 O.sub.2 N) 5 4-CH.sub.2 CHCH.sub.2 H H 7-NHCOCH.sub.3 C.sub.2 H.sub.5 H H C.sub.2 H.sub.5 4 H CH.sub.3 H 7-OCPh C.sub.2 H.sub.5 H H C.sub.2 H.sub.5 4,6 4-CONH.sub.2 H H 7-CH.sub.2 CONHCH.sub.3 H H H H 6 3-SO.sub.2 NH.sub.2 H 4-COCH.sub.3 7-CH.sub.3 CON(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH.sub.3 Ph 6 4-SO.sub.2 NHCH.sub.3 H 4-NO.sub.2 7-CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 CH.sub.3 CH.sub.3 H C.sub.6 H.sub.11 6 4-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 H 4-Cl 7-CH.sub.2 SC.sub.2 H.sub.5 CH.sub.3 CH.sub.3 H CH.sub.2CHCH.sub.2 4 4-SO.sub.3 C.sub.6 H.sub.5 CH.sub.3 6-CN 7-CH.sub.2 SC.sub.6 H.sub.5 CH.sub.3 CH.sub.3 H CH.sub.2 OOCC.sub.2 H.sub.5 5 4-SCH.sub.3 CH.sub.3 4-NHSO.sub.2 CH.sub.3 7-CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-OOCCH.sub.3 4 2,4-di-SCN CH.sub.3 6-CH.sub.3 7-CH.sub.2 SO.sub.2 C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 H C.sub.6 H.sub.104-CH.sub.3 4 4-SO.sub.2 C.sub.6 H.sub.5 CH.sub.3 6-OCH.sub.3 7-C.sub.6 H.sub.3-o,-p-di-CN CH.sub.3 H H CH.sub.2 CH.sub.2(C.sub.4 H.sub.4 O.sub.2 N) 4 2-CHO4-CN CH.sub.3 6-Ph 7-C.sub.6 H.sub.2-o,-m,-p-tri-Cl CH.sub.3 H H CH.sub.2 CH.sub.2 NO.sub.2 4 4-CONHC.sub.2 H.sub.5 CH.sub.3 H 5,7-di-OSO.sub.3 NH(CH.sub.3).sub.3 CH.sub.3 H H C.sub.6 H.sub.4-p-NO.sub.2 4 4-CON(C.sub.2 H.sub.5).sub.2 H H 5,7-di-OSO.sub.3 Na CH.sub.3 H H CH.sub.2 NHOCCH.sub.3 4 3-C.sub.6 H.sub.11 H 6-SO.sub.3 Na 5,7-di-SO.sub.3 NH(CH.sub.3).sub.3 CH.sub.3 H H CH.sub.2 NHSO.sub.2 CH.sub.3 4 3-SC.sub.6 H.sub.5 H 6-SO.sub.3 Na 7-OSO.sub.3 NH(CH.sub.3).sub.3 CH.sub.3 H H C.sub.6 H.sub.4-p-NHOCCH.sub.3 4 4-NHSO.sub.2 C.sub.6 H.sub.5 H 6-OCH.sub.2 CH.sub.2 SO.sub.4 K 5,7-di-OSO.sub.3 Na CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-NHSO.sub.2 CH.sub.3 4 4-SC.sub.6 H.sub.11 H 6-OCH.sub.2 CH.sub.2 SO.sub.4 K 7-SC.sub.6 H.sub.11 H H H C.sub.6 H.sub.104-NHOCCH.sub.3 4 4-C.sub.6 H.sub.4-p-CH.sub.3 C.sub.2 H.sub.5 6-NHCOPh 7-C.sub.6 H.sub.4-p-CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 Cl 5 4-C.sub.6 H.sub.4-p-CH.sub.2 CHCH.sub.2 C.sub.2 H.sub.5 4-NHCOPh 7-C.sub.6 H.sub.4-p-CH.sub.2 CHCH.sub.2 CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-Br 6 4-OCH.sub.2 CH.sub.2 NO.sub.2 C.sub.2 H.sub.5 4-NHCOCH.sub.3 7-OCH.sub.2 CH.sub.2 NO.sub.2 CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-CN 6 2-CH.sub.2 NHCOCH.sub.3 C.sub.2 H.sub.5 4-OOCC.sub.2 H.sub.5 7-CH.sub.2 NHCOCH.sub.3 CH.sub.3 CH.sub.3 H CH.sub.2 CH.sub.2 CN 4 4-CH.sub.2 NHSO.sub.2 C.sub.2 H.sub.5 H 5-COOH 7-CH.sub.2 NHSO.sub.2 C.sub.2 H.sub.5 CH.sub.3 CH.sub.3 H CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 4,6 4-CH.sub.2 CH.sub.2 Cl H H 7-CH.sub.2 CH.sub.2 Cl CH.sub.3 CH.sub.3 H CH.sub.2 CH.sub. 2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 6 2,6-di-CH.sub.2 CN H H 5,7-di-CH.sub.2 CN CH.sub.3 H H CH.sub.2 Ph 6 4-CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 H 4-SO.sub.2 CH.sub.3 7-CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 CH.sub.3 H H CH.sub.2 C.sub.6 H.sub.11 4 4-CH.sub.2 C.sub.6 H.sub.5 H 6-CH.sub.2 C.sub.6 H.sub.5 7-COOH CH.sub.3 H H C.sub.6 H.sub.4-o-OH 4 4-CH.sub.2 C.sub.6 H.sub.11 C.sub.3 H.sub.7n 6-COOCH.sub.3 7-CH.sub.2 C.sub.6 H.sub.11 CH.sub.3 H H CH.sub.2 CH.sub.2 OH 4 4-CH.sub.2 CH(OH)CH.sub.2 OH C.sub.3 H.sub.7n 6-CHO 7-CH.sub.2 CH(OH)CH.sub.2 OH CH.sub.3 H H CH.sub.2 CH.sub.2-p-OSO.sub.3 K 4 4-CH.sub.2 CH.sub.2SO.sub.3 K H 6-CONH.sub.2 7-CH.sub.2 CH.sub.2SO.sub.3 K CH.sub.3 H H C.sub.6 H.sub.4-p-OSO.sub.3 K 4 4-CH.sub.2 OC.sub.6 H.sub.5 H 6-CONHCH.sub.3 7-CH.sub.2 OC.sub.6 H.sub.5 CH.sub.3 C.sub.2 H.sub. 5 C.sub.2 H.sub.5 CH.sub.2 OPh 4 4-CH.sub.2 OOCC.sub.6 H.sub.5 H 5-CH.sub.2 Ph 7-CH.sub.2 OOCC.sub.6 H.sub.5 H H H CH.sub.2 SO.sub.2 NHPh 4 5-CH.sub.2 COOCH.sub.3 H 5-CH.sub.2 SO.sub.3 K 7-CH.sub.2 COOCH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.2 SO.sub.2 NHCH.sub.3 4 4-C.sub.6 H.sub.4-p-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 H 6-CH.sub.2 OSO.sub.3 K 7-C.sub.6 H.sub.4-p-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-SO.sub.2 NHCH.sub.3 4 4-CH.sub.2 CH.sub.2 NHCOOCH.sub.3 H 6-C.sub.6 H.sub.4-p-SO.sub.3 K 7-CH.sub.2 CH.sub.2 NHCOOCH.sub.3CH.sub.3 CH.sub.3 H C.sub.2 COOCH.sub.3 4 4-CH.sub.2 NHCONHCH.sub.3 H 6-CH.sub.2 CH.sub.2 OH 7-CH.sub.2 NHCONHCH.sub.3 CH.sub.3 CH.sub.3 H CH.sub.2 SO.sub.3 N(CH.sub.3).sub.2 6 4-CH.sub.2 CONH.sub.2 H 4-CH.sub.2 Cl 7-CH.sub.2 CONH.sub.2 CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4 -p-NHCOOCH.sub.3 4 5-CH.sub.2 CONHCH.sub.3 C.sub.4 H.sub.9n 5-C.sub.6 H.sub.4-p-Br 7-CONH.sub.2 H H H CH.sub.2 CH.sub.2 CONH.sub.2 4 4-CH.sub.2 CON(CH.sub.3).sub.2 H H 7-SO.sub.2 NH.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 C.sub.6 H.sub.4-p-CONHCH.sub.3 4 4-CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 H 6-COCH.sub.3 7-SO.sub.2 NHCH.sub.3 CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-SCH.sub.3 4 4-CH.sub.2 SC.sub.2 H.sub.5 H 6-NO.sub.2 7-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 CH.sub.3 H CH.sub.2 CH.sub.2 SCH.sub.3 4,5 5-CH.sub.2 SC.sub.6 H.sub.5 H 6-Cl 7-SO.sub.3 C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 H CH.sub.2C.sub.6 H.sub.4-p-SCH.sub.3 6 4-CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 CH.sub.3 4-CN 7-SCH.sub.3 CH.sub.3 CH.sub.3 H CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 6 2,4-di-CH.sub.2 SO.sub.2 C.sub.6 H.sub.5 CH.sub.3 4-NHSO.sub. 2 CH.sub.3 5,7-di-SCN CH.sub.3 CH.sub.3 H CH.sub.2 SO.sub.2 Ph 4 4-C.sub.6 H.sub.3-o,-p-di-CN CH.sub.3 6-CH.sub.3 7-SO.sub.2 C.sub.6 H.sub.5 CH.sub.3 H H C.sub.6 H.sub.4-p-OSO.sub.3 K 4 4-C.sub.6 H.sub.2-o,-m,-p-tri-Cl CH.sub.3 6-OCH.sub.3 5-CHO7-CN CH.sub.3 H H C.sub.6 H.sub.4-p-OSO.sub.3 K 4 2,6-di-OSO.sub.3 Na CH.sub.3 6-Ph 7-CONHC.sub.2 H.sub.5 CH.sub.3 H H CH.sub.2 (C.sub.8 H.sub.4 O.sub.2 N) 4 H H 6-CH.sub.2 (C.sub.4 H.sub.4 O.sub.2 N) 7-CON(C.sub.2 H.sub.5).sub.2 CH.sub.3 H H C.sub.2 H.sub.5 4 H H 5-CH.sub.2 (C.sub.4 H.sub.3 O) 7-C.sub.6 H.sub.11 CH.sub.3 H H C.sub.2 H.sub.5 4 5-CH.sub.2 (C.sub.8 H.sub.4 O.sub.2 N) H H 7-SC.sub.6 H.sub.5 CH.sub.3 H H C.sub.2 H.sub.5 4 5-CH.sub.2 (C.sub.4 H.sub.3 O) H H 7-NHSO.sub.2 C.sub.6 H.sub.5 CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 C.sub.2 H.sub.5 2 4-OSO.sub.3 K H H 7-CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 H TABLE 3__________________________________________________________________________ ##STR7##Cinna-moylGroupPosi- Substituentstion R.sub.1 on D R.sub.5 on A R.sub.1 on C R.sub.3 R.sub.7__________________________________________________________________________4 H H H H H H4 4-NO.sub.2 H 5-COCH.sub.3 6-CH.sub.3 CH.sub.3 Ph4 4-CN H 5-NO.sub.2 6-COCH.sub.3 C.sub.2 H.sub.5 C.sub.6 H.sub.114 5-COCH.sub.3 H 6-Cl 6-OCH.sub.3 H CH.sub.2CHCH.sub.24 4-COPh CH.sub.3 6-CN 6-SO.sub.3 Na H CH.sub.2 OOCC.sub.2 H.sub.55 2,4-di-COOH CH.sub.3 4-NHSO.sub.2 CH.sub.3 6-OCH.sub.2 CH.sub.2 SO.sub.4 K H C.sub.6 H.sub.4 -p-OOCCH.sub.36 4-OOCCH.sub.3 CH.sub.3 4-CH.sub.3 6-OCH.sub.2 CH.sub.2 SO.sub.4 K H C.sub.6 H.sub.104-CH.sub .36 4-NHCOCH.sub.3 CH.sub.3 4-OCH.sub.3 6-CH.sub.3 H CH.sub.2 CH.sub.2 (C.sub.4 H.sub.4 O.sub.2 N)4,6 4-NHCOPh CH.sub.3 5-Ph 6-Ph CH.sub.3 CH.sub.2 CH.sub.2 NO.sub.24 4-C.sub.2 H.sub.5 CH.sub.3 H 6-NO.sub.2 CH.sub.3 C.sub.6 H.sub.4 -p-NO.sub.26 4-Ph H H 6-OCH.sub.3 CH.sub.3 CH.sub.2 NHOCCH.sub.34 4-OSO.sub.3 K H H H H CH.sub.2 CH.sub.2 SO.sub.3 K4 2,5-di-Cl H 5-SO.sub.3 Na 6-NHCOCH.sub.3 C.sub.2 H.sub.5 CH.sub.2 NHSO.sub.2 CH.sub.34 2-Cl4-SO.sub.2 CH.sub.3 H 5-SO.sub.3 Na 6-NHSO.sub.2 CH.sub.3 CH.sub.3 C.sub.6 NHSO.sub.2 CH.sub.34 4-NHSO.sub.2 CH.sub.3 H 6-OCH.sub.2 CH.sub.2 SO.sub.4 K 6-COOCH.sub.3 CH.sub.3 C.sub.6 H.sub.4 -p-NHSO.sub.2 CH.sub.34 4-COOCH.sub.3 H 6-OCH.sub.2 CH.sub.2 SO.sub.4 K 6-COOH H C.sub.6 H.sub.104-NHOCCH .sub.34 2-OCH.sub.3 C.sub.2 H.sub.5 5-NHCOPh 6-Cl CH.sub.3 CH.sub.2 CH.sub.2 Cl5 4-OC.sub.2 H.sub.5 C.sub.2 H.sub.5 4-NHCOPh 5,6-di-Br C.sub.2 H.sub.5 C.sub.6 H.sub.4 -p-Br6 4-SO.sub.3 Na C.sub.2 H.sub.5 4-NHCOCH.sub.3 5,6-di-Br H C.sub.6 H.sub.4 -p-CN6 2-SO.sub.3 Na C.sub.2 H.sub.5 4-OOCC.sub.2 H.sub.5 5-OCH.sub.36-NHCOCH.sub.3 H CH.sub.2 CH.sub.2 CN4 2-OCH.sub.34-SO.sub.3 K H 5-COOH 6-CH.sub.2 OOCCH.sub.3 H CH.sub.2 CH.sub.2 OC.sub.2 H.sub.56 4-OCH.sub.2 CH.sub.2 OSO.sub.3 K H H 6-CH.sub.2 Cl H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.54,6 2-SO.sub.3 Na5-Cl H H 6-CN H CH.sub.2 Ph6 4-Cl H 4-SO.sub.2 CH.sub.3 6-OOCCH.sub.3 CH.sub.3 CH.sub.2 C.sub. 6 H.sub.114 4-OH H 6-CF.sub.3 5-COOH CH.sub.3 C.sub.6 H.sub.4 -o-OH4 4-CH.sub.2 OOCCH.sub.3 C.sub.3 H.sub.7n 6-COOCH.sub.3 5-OH CH.sub.3 CH.sub.2 CH.sub.2 OH4 4-SO.sub.3 K C.sub.3 H.sub.7n 6-CHO 5-CH.sub.2 CHCH.sub.2 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2SO.sub. 3 K4 4-OPh H 6-CONH.sub.2 6-CH.sub.3 CH.sub.3 C.sub.6 H.sub.4 -p-OSO.sub.3 K4 4-NO.sub.2 H 6-CONHCH.sub.3 6-COCH.sub.3 CH.sub.3 CH.sub.2 OPh4 5-CN H 6-CH.sub.2 Ph 6-OCH.sub.3 H CH.sub.2 SO.sub.2 NHPh4 4-COCH.sub.3 H 6-CH.sub.2 SO.sub.3 K 6-SO.sub.3 Na CH.sub.3 CH.sub.2 SO.sub.2 NHCH.sub.34 5-CH.sub.3 H 6-CH.sub.2 OSO.sub.3 K 6-OCH.sub.2 CH.sub.2 SO.sub.4 K H C.sub.6 H.sub.4 -p-SO.sub.2 NHCH.sub.34 5-Ph H 5-C.sub.6 H.sub.4 -p-SO.sub.3 K 6-OCH.sub.2 CH.sub.2 SO.sub.3 K H CH.sub.2 COOCH.sub.34 5-OCH.sub.3 H 5-CH.sub.2 CH.sub.2 OH 6-CH.sub.3 H CH.sub.2 SO.sub.2 N(CH.sub.3).sub.24 4,5-di-Br H 5-CH.sub.2 Cl 6-Ph H C.sub.6 H.sub.4 -p-NHCOOCH.sub.34 5-COOH C.sub.4 H.sub.9n 6-C.sub.6 H.sub.4 -p-Br 6-NO.sub.2 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 CONH.sub.24 H H H 6-OCH.sub.3 C.sub.2 H.sub.5 C.sub.6 H.sub.4 -p--CONHCH.sub.34 4-NO.sub.2 H 6-COCH.sub.3 6-NHCOCH.sub.3 CH.sub.3 C.sub.6 H.sub.4 -p-SCH.sub.34 4-CN H 6-NO.sub.2 6-NHSO.sub.2 CH.sub.3 C.sub.3 H.sub.7n CH.sub.2 CH.sub.2 SCH.sub.34 5-COCH.sub.3 H 6-Cl 6-COOCH.sub.3 H CH.sub.2C.sub.6 H.sub.4 -p-SCH.sub.34 4-COPh CH.sub.3 5-CN 6-COOH CH.sub.3 CH.sub.2 SO.sub.2 C.sub.2 H.sub.54 2,4-di-COOH CH.sub.3 5-NHSO.sub.2 CH.sub.3 8-Cl H CH.sub.2 SO.sub.2 Ph4 4-OOCCH.sub.3 CH.sub.3 5-CH.sub.3 5,6-di-Br H CH.sub.2 CH.sub.2 OSO.sub.3 K4 4-NHCOCH.sub.3 CH.sub.3 5-OCH.sub.3 5,6-Di-Br H C.sub.6 H.sub.4 - p-OSO.sub.3 K4 4-NHCOPh CH.sub.3 6-Ph 5-OCH.sub.36-NHCOCH.sub.3 H CH.sub.2 (C.sub.8 H.sub.4 O.sub.2 N)5 4-CH.sub.2 CHCH.sub.2 H H 6-NHCOCH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.54,6 H CH.sub.3 H 6-OCPh C.sub.2 H.sub.5 C.sub.2 H.sub.56 4-CONH.sub.2 H H 6-CH.sub.2 CONHCH.sub.3 H H6 3-SO.sub.2 NH.sub.2 H 4-COCH.sub.3 6-CH.sub.2 CON(CH.sub.3).sub.2 CH.sub.3 Ph4 4-SO.sub.2 NHCH.sub.3 H 5-NO.sub.2 6-CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 C.sub.2 H.sub.5 C.sub.6 H.sub.114 4-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 H 6-Cl 6-CH.sub.2 SC.sub.2 H.sub.5 H CHCHCH.sub.24 4-SO.sub.3 C.sub.6 H.sub.5 CH.sub.3 6-CN 6-CH.sub.2 SC.sub.6 H.sub.5 H CH.sub.2 OOCC.sub.2 H.sub.55 4-SCH.sub.3 CH.sub.3 4-NHSO.sub.2 CH.sub.3 6-CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 H C.sub.6 H.sub.10 -p-OOCCH.sub.36 2,4-di-SCN CH.sub.3 4-CH.sub.3 6-CH.sub.2 SO.sub.2 C.sub.6 H.sub.5 H C.sub. 6 H.sub.104-CH.sub.34 4-SO.sub.2 C.sub.6 H.sub.5 CH.sub.3 6-OCH.sub.3 6-C.sub.6 H.sub.3 -o, -p-di-CN H CH.sub.2 CH.sub.2(C.sub. 4 H.sub.4 O.sub.2 N)4 2-CHO4-CN CH.sub.3 6-Ph 6-C.sub.6 H.sub.2 -o,m,p-tri-Cl CH.sub.3 CH.sub.2 CH.sub.2 NO.sub.24 4-CONHC.sub.2 H.sub.5 CH.sub.3 H 6,8-di-OSO.sub.3 NH(CH.sub.3).sub.3 CH.sub.3 C.sub.6 H.sub.4 -p-NO.sub.24 4-CON(C.sub.2 H.sub.5).sub.2 H H 5,6-di-OSO.sub.3 Na CH.sub.3 CH.sub.2 NHOCCH.sub.34 3-C.sub.6 H.sub.11 H 5,6-di-SO.sub.3 Na 5,6-di-OSO.sub.3 Na C.sub.2 H.sub.5 CH.sub.2 NHSO.sub.2 CH.sub.34 3-SC.sub.6 H.sub.5 H 6-SO.sub.3 Na 5,6-di-SO.sub.3 NH(CH.sub.3).sub.3 CH.sub.3 C.sub.6 H.sub.4 -p-NHOCCH.sub.34 3-SC.sub.6 H.sub.5 H 6-SO.sub.3 Na 5,6-di-SO.sub.3 NH(CH.sub.3).sub.3 CH.sub.3 C.sub.6 H.sub.4 -p-NHOCCH.sub.34 4-NHSO.sub.2 C.sub.6 H.sub.5 H 6-OCH.sub.2 CH.sub.2 SO.sub.4 K 5,6-di-OSO.sub. 3 Na CH.sub.3 C.sub.6 H.sub.4 -p-NHSO.sub.2 CH.sub.34 4-SC.sub.6 H.sub.11 H 5-OCH.sub.2 CH.sub.2 SO.sub.4 K 6-SC.sub.6 H.sub.11 H C.sub.6 H.sub.104-NHOCCH .sub.34 4-C.sub.6 H.sub.4 -p-CH.sub.3 C.sub.2 H.sub.5 6-NHCOPh 6-C.sub.6 H.sub.4 -p-CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.3 Cl5 4-C.sub.6 H.sub.4 -p-CH.sub.2 CHCH.sub.2 C.sub.2 H.sub.5 4-NHCOPh 6-C.sub.6 H.sub.4 -p-CH.sub.2 CHCH.sub.2 C.sub.2 H.sub.5 C.sub.6 H.sub.4 -p-Br6 4-OCH.sub.2 CH.sub.2 NO.sub.2 C.sub.2 H.sub.5 4-NHCOCH.sub.3 6-OCH.sub.2 CH.sub.2 NO.sub.2 H C.sub.6 H.sub.4 -p-CN4 2-CH.sub.2 NHCOCH.sub.3 C.sub.2 H.sub.5 6-OOCC.sub.2 H.sub.5 6-CH.sub.2 NHCOCH.sub.3 H CH.sub.2 CH.sub.2 CN4 4-CH.sub.2 NHSO.sub.2 C.sub.2 H.sub.5 H 6-COOH 6-CH.sub.2 NHSO.sub.2 C.sub.2 H.sub.5 H CH.sub.2 CH.sub.2 OC.sub.2 H.sub.54 4-CH.sub.2 CH.sub.2 Cl H H 6-CH.sub.2 CH.sub.2 Cl H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.54,6 2,6-di-CH.sub.2 CN H H 5,6-di-CH.sub.2 CN H CH.sub.2 Ph6 4-CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 H 4-SO.sub.2 CH.sub.3 6-CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 CH.sub.3 CH.sub.2 C.sub.6 H.sub.116 4-CH.sub.2 C.sub.6 H.sub.5 H 4-CH.sub.2 C.sub.6 H.sub.5 6-COOH CH.sub.3 C.sub.6 H.sub.4 -o-OH4 4-CH.sub.2 C.sub.6 H.sub.11 C.sub.3 H.sub.7n 6-COOCH.sub.3 6-CH.sub.2 C.sub.6 H.sub.11 CH.sub.3 CH.sub.2 CH.sub.2 OH4 4-CH.sub.2 CH(OH)CH.sub.2 OH C.sub.3 H.sub.7n 6-CHO 6-CH.sub.2 CH(OH)CH.sub.2 OH C.sub.2 H.sub.5 CH.sub.2 CH.sub.2SO.sub. 3 K4 4-CH.sub.2 CH.sub.2SO.sub.3 K H 5-CONH.sub.2 6-CH.sub.2 CH.sub.2SO.sub.3 K CH.sub.3 C.sub.6 H.sub.4 -p-OSO.sub.3 K4 4-CH.sub.2 OC.sub.6 H.sub.5 H 5-CONHCH.sub.3 6-CH.sub.2 OC.sub.6 H.sub.5 CH.sub.3 CH.sub.2 OPh4 4-CH.sub.2 OOCC.sub.6 H.sub.5 H 5-CH.sub.2 Ph 6-CH.sub.2 OOCC.sub.6 H.sub.5 H CH.sub.2 SO.sub.2 NHPh4 5-CH.sub.2 COOCH.sub.3 H 6-CH.sub.2 SO.sub.3 K 5-CH.sub.2 COOCH.sub.3 CH.sub.3 CH.sub.2 SO.sub.2 NHCH.sub.34 4-C.sub.6 H.sub.4 -p-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 H 6-CH.sub.2 OSO.sub.3 K 6-C.sub.6 H.sub.4 -p-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 H C.sub.6 H.sub.4 -p-SO.sub.2 NHCH.sub.34 4-CH.sub.2 CH.sub.2 NHCOOCH.sub.3 H 6-C.sub.6 H.sub.4 -p-SO.sub.3 K 6-CH.sub.2 CH.sub.2 NHCOOCH.sub.3 H CH.sub.2 COOCH.sub.34 4-CH.sub.2 NHCONHCH.sub.3 H 6-CH.sub.2 CH.sub.2 OH 6-CH.sub.2 NHCONHCH.sub.3 H CH.sub.2 SO.sub.2 N(CH.sub.3).sub.24 4-CH.sub.2 CONH.sub.2 H 6-CH.sub.2 Cl 6-CH.sub.2 CONH.sub.2 H C.sub.6 H.sub.4 -p-NHCOOCH.sub.34 5-CH.sub.2 CONHCH.sub.3 C.sub.4 H.sub.9n 6-C.sub.6 H.sub.4 -p-Br 6-CONH.sub.2 C.sub. 2 H.sub.5 CH.sub.2 CH.sub.2 CONH.sub.24 4-CH.sub.2 CON(CH.sub.3).sub.2 H H 6-SO.sub.2 NH.sub.2 C.sub.2 H.sub.5 C.sub.6 H.sub.4 -p-CONHCH.sub.34 4-CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 H 5-COCH.sub.3 6-SO.sub.2 NHCH.sub.3 CH.sub.3 C.sub.6 H.sub.4 -p-SCH.sub.34 4-CH.sub.2 SC.sub.2 H.sub.5 H 5-NO.sub.2 6-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 C.sub.3 H.sub.7n C.sub.2 CH.sub.2 SCH.sub.34 5-CH.sub.2 SC.sub.6 H.sub.5 H 5-Cl 6-SO.sub.3 C.sub.6 H.sub.5 H CH.sub.2C.sub.6 H.sub.4 -p-SCH.sub.34 4-CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 CH.sub.3 5-CN 6-SCH.sub.3 CH.sub.3 CH.sub.2 SO.sub.2 C.sub.2 H.sub.54,5 2,4-di-CH.sub.2 SO.sub.2 C.sub.6 H.sub.5 CH.sub.3 6-NHSO.sub.2 CH.sub.3 5,6-di-SCN H CH.sub.2 SO.sub.2 Ph6 4-C.sub.6 H.sub.3 -o, -p-di-CN CH.sub.3 4-CH.sub.3 6-SO.sub.2 C.sub.6 H.sub.5 H CH.sub.2 CH.sub.2 OSO.sub.3 K4 4-C.sub.6 H.sub.2 -o, -m, -p-tri-Cl CH.sub.3 5-OCH.sub.3 5-CHO-6-CN H C.sub.6 H.sub.4(C.sub.8 H.sub.4 O.sub.2 N)4 H H 6-CH.sub.2 (C.sub.4 H.sub.4 O.sub.2 N) 6-CON(C.sub.2 H.sub.5).sub.2 H C.sub.2 H.sub.54 H H 6-CH.sub.2 (C.sub.4 H.sub.3 O) 6-C.sub.6 H.sub.11 H C.sub.2 H.sub.54 5-CH.sub.2 (C.sub.8 H.sub.4 O.sub.2 N) H H 6-SC.sub.6 H.sub.5 H C.sub.2 H.sub.54 5-CH.sub.2 (C.sub.4 H.sub.3 O) H H 6-NHSO.sub.2 C.sub.6 H.sub.5 H C.sub.2 H.sub.5__________________________________________________________________________

The invention has been described in detail with particular reference to preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention.

Claims

1. A dye having the structure: ##STR8## wherein the A ring is unsubstituted or substituted in any positions not occupied by cinnamoyl groups; R.sub.5 is H or alkyl; and each R.sub.1 and each A ring substituent is selected from alkyl, alkenyl or 2-6 carbon atoms, aryl, cyclohexyl, alkoxy, halogen, hydroxy, alkylsulfonyl, cyano, carbamoyl, alkanoyl, alkanoyloxy, aroyl, alkoxycarbonyl, sulfamoyl, alkylsulfamoyl, dialkylsulfamoyl, alkanoylamino, SO.sub.3 C.sub.6 H.sub.5, amino, alkylthio, thiocyano, arylsulfonyl, formyl, alkylcarbamoyl, dialkylcarbamoyl, NO.sub.2, --SO.sub.3 M, --OSO.sub.3 M, --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, --NO.sub.2, alkanoylamino, alkylsulfonylamino, 1-(2-pyrrolidono), halogen, cyano, alkoxy, aryl, cyclohexyl, hydroxy, --SO.sub.3 M, --OSO.sub.3 M, aryloxy, furyl, aroyloxy, alkoxycarbonyl, --SO.sub.2 N-(alkyl).sub.2, --NHCOO-alkyl, --NHCONH-alkyl, glutarimido, phthalimido, CONH.sub.2, CONH-alkyl, CON(alkyl).sub.2, alkoxyalkoxy, alkylthio, arylthio, alkylsulfonyl, and arylsulfonyl, wherein M is selected from H.sup.+, NH.sub.4.sup.+, Na.sup.+, K.sup.+, and the colorless cations of sulfuric or sulfonic acid salts of trimethylamine, triethylamine, tri(2-hydroxyethyl)amine, di(2-hydroxyethyl)amine, or N,N-dimethylaniline; and the coupler C.sup.1 is selected from ##STR9## wherein each R.sub.1 is as defined above; R.sub.2 and R.sub.7 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.sub.1 groups; and R.sub.3, R.sub.4 and R.sub.8 are each selected from hydrogen and alkyl.

2. A dye of claim 1 wherein the coupler C.sup.1 is ##STR10## wherein R.sub.1, R.sub.2, and R.sub.7 are as defined therein.

3. A dye of claim 1 wherein the coupler C.sup.1 is ##STR11## wherein R.sub.1, R.sub.3, R.sub.4, R.sub.7, and R.sub.8 are as defined therein.

4. A dye of claim 1 wherein the coupler C.sup.1 is ##STR12## wherein R.sub.1, R.sub.3, and R.sub.7 are as defined therein.

5. A dye according to claim 1 wherein: the A ring is unsubstituted or substituted with 1-3 substituents independently selected from methoxycarbonyl, .beta.-hydroxyethylcarbamoyl, CF.sub.3, NO.sub.2, alkanoyl, alkylsulfonyl, alkoxy, .beta.-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 --SO.sub.3 M or --SO.sub.4 M, cyclohexylalkyl, cyclohexylalkyl substituted with --SO.sub.3 M or --SO.sub.4 M, alkoxy, and alkanoylamino; R.sub.2 is H, alkyl, aralkyl, alkyl or aralkyl substituted with --SO.sub.3 M or --SO.sub.4 M, cyclohexylalkyl, cyclohexylalkyl substituted with --SO.sub.3 M or --SO.sub.4 M; R.sub.7 is H, alkyl, aralkyl, aralkyl substituted with --SO.sub.3 M or --SO.sub.4 M, cyclohexylalkyl, cyclohexylalkyl substituted with --SO.sub.3 M or --SO.sub.4 M, 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 --SO.sub.3 M or --SO.sub.4 M, cyclohexylalkyl, cyclohexylalkyl substituted with --SO.sub.3 M or --SO.sub.4 M, --SO.sub.3 Na, --SO.sub.3 K, --SO.sub.3 N.sup.+ H(CH.sub.3).sub.3, halogen, --SO.sub.4 Na, --SO.sub.4 K, --SO.sub.4 N.sup.+ H(CH.sub.3).sub.3, alkyl, alkoxy, --COOH, and --OH; R.sub.3, R.sub.4 and R.sub.8 are H or alkyl; and R.sub.5 is hydrogen.

6. A dye according to claim 1 wherein: the cinnamoyl ring is unsubstituted or substituted with halogen, COOH, OH, or SO.sub.3 M; ring A is unsubstituted or substituted with alkyl, halogen, CN, alkoxy, COOalkyl, CONH.sub.2 ; alkanoylamino, CONHalkylene--SO.sub.4 M, hydroxyethylcarbamoyl, or CONHalkyl; and wherein, in an aniline coupler each substituent R.sub.1 is a methyl, methoxy or acetamido group or a chlorine atom, each R.sub.2 is hydrogen, a methyl or ethyl group, or a sulfonated cyclohexyl or benzyl group and each R.sub.7 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 --SO.sub.3 M, and wherein in a tetrahydroquinoline coupler R.sup.1 and R.sup.3 are methyl groups, each of R.sub.4 and R.sub.8 is hydrogen or a methyl group, and R.sub.7 is an ethyl group or a group of formula CH.sub.2 CH.sub.2 OCOCH.sub.3 or CH.sub.2 CH.sub.2 OSO.sub.3 M.

7. A dye according to claim 1 wherein the coupler C.sup.1 is selected from those of the formula ##STR13## wherein R.sub.2 is alkyl, R.sub.7 is H, alkyl or alkyl substituted with OSO.sub.3 M or SO.sub.3 M, and the phenyl ring is substituted with 1 or 2 groups independently selected from alkyl, alkoxy and alkanoylamino.

8. A dye according to claim 1 wherein ring A is unsubstituted or substituted with 1 or 2 substituents independently selected from cyano, halogen, alkyl, alkoxy and acylamido.

9. A dye according to claim 1 having the formula ##STR14##

10. A dye according to claim 1 having the formula ##STR15##

11. A dye according to claim 1 having the formula ##STR16##