Triaryl-methane dyestuffs

Our co-pending application No. 878,549 filed Nov. 20, 1969, now U.S. Pat. No. 3,647,349, (Le A 11833) describes and claims a new process for dyeing or printing shaped materials of polymers or copolymers of acrylonitrile or as.-dicyanoethylene, or of acid-modified aromatic polyesters. The process is characterized by using therefor a wide range of triaryl-methane compounds of which the formulae and numerous examples are given and described.
With very few exceptions the compounds to be used in said process are new, and the purpose of the present application is to classify and describe the new compounds and to claim them as new triaryl-methane dyestuffs, together with processes for producing the same. This is the subject matter of the present invention.
It is convenient, for the purpose of clarity, to classify the new dyestuffs in groups under separate formulae even though some dyestuffs may come within the scope of more than one formula.
It is also convenient, for the purpose of simplification, to use in different formulae the same symbols with different meanings given to them. This avoids undue multiplication of the number of different symbols used, while avoiding confusion because each particular formula will stand on its own with the symbols used therein specifically defined in relation only to such particular formula.
The following are the new dyestuffs, all according to the present invention:
GROUP 1
Triaryl-methane dyestuffs which are free from sulfonic acid and carboxylic acid groups and correspond to the general formula ##STR5## in which R stands for an alkyl, aralkyl, cycloalkyl or aryl radical; R.sub.1 stands for hydrogen or for an alkyl, aralkyl or cycloalkyl radical; R.sub.2 stands for an alkyl, aralkyl, cycloalkyl or aryl radical; R.sub.1 and R.sub.2 together with the nitrogen atom, or R.sub.1 or R.sub.2 with a carbon atom in the o-position in the ring A may form a heterocyclic ring; R.sub.3 stands for hydrogen, an alkyl, aralkyl, aryl, aralkoxy, aryloxy radical, a halogen substituent, a carboxylic acid ester, carbonamide, sulfonamide, cyano, nitro, alkylsulfonyl, aralkylsulfonyl, arylsulfonyl or acyl group; X stands for the radical of an anion; and the dyestuffs may contain one or more further substituents, with the exception of sulfonic acid and carboxylic acid groups, in the aliphatic, cycloaliphatic and aromatic radicals, including the phenylene radicals A, B and D. The phenylene ring A, B, and/or D may contain an annelated, ring, particularly a six-membered monocyclic radical, as for example, in a dyestuff of the formula ##STR6##
A particularly valuable selection of dyestuffs, free from sulfonic acid and carboxylic acid groups, within the scope of formula (I) corresponds to the formula ##STR7## in which R', R.sub.1 ' and R.sub.2 ' stand for optionally substituted lower alkyl radicals with 1 to 4 carbon atoms; R.sub.1 ' and R.sub.2 ' together with the nitrogen atom, or R.sub.1 ' or R.sub.2 ' with a carbon atom in the o-position of the phenylene ring A may form a heterocyclic ring; R.sub.3 ' stands for hydrogen or an alkyl radical with 1 to 4 carbon atoms; R.sub.4 stands for hydrogen, halogen, especially chlorine or bromine, or a C.sub.1 to C.sub.4 alkyl or alkoxy radical; X stands for the radical of an anion.
Another valuable selection of dyestuffs, free from sulfonic acid and carboxylic acid groups, within the scope of formula (I) corresponds to the formula ##STR8## in which R', R.sub.1 ', R.sub.3 ', R.sub.4 and X have the same meaning as in formula (Ia), and R.sub.5 stands for hydrogen or a lower alkyl radical.
GROUP 2
Triaryl-methane dyestuffs which are free from sulfonic acid and carboxylic acid groups and correspond to the general formula ##STR9## in which R stands for an alkyl or cycloalkyl radical; R.sub.1 stands for hydrogen, an alkyl, aralkyl, cycloalkyl or aryl radical; R.sub.2 stands for an alkyl, cycloalkyl, aralkyl or aryl radical, a halogen substituent or the cyano group; R.sub.1 and R.sub.2 together with the nitrogen atom or R.sub.1 or R.sub.2 with a carbon atom in the o-position in the ring A, may form a heterocyclic ring; R.sub.3 stands for hydrogen or an alkyl radical; R.sub.4 stands for an alkyl or cycloalkyl radical; X is the radical of an anion; and the dyestuffs may contain further substituents, with the exception of sulfonic acid and carboxylic acid groups, in the aliphatic, cycloaliphatic and aromatic radicals, including the phenylene radicals A, B and D illustrated in the formula. The phenylene ring A, B and/or D may contain an annelated ring, particularly a six-membered monocyclic radical, as, for example, in a dyestuff of the formula ##STR10##
A particularly valuable selection of dyestuffs, free from sulfonic acid and carboxylic acid groups, within the scope of formula (II) corresponds to the formula ##STR11## in which R', R.sub.1 ', and R.sub.4 ' stand for optionally substituted lower alkyl radicals with 1 to 4 carbon atoms; R.sub.2 ' stands for the methyl, ethyl, propyl and isopropyl group; R.sub.1 ' and R.sub.2 ' together with the nitrogen atom, or R.sub.1 ' or R.sub.2 ' with a carbon atom in the o-position in the ring A may form a heterocyclic ring; R.sub.3 ' stands for hydrogen or the methyl or ethyl group; R.sub.5 stands for hydrogen, a halogen substituent, especially chlorine or bromine, or a lower alkyl or alkoxy radical with 1 to 4 carbon atoms, and X is the radical of an anion.
Another valuable selection of dyestuffs free from sulfonic acid and carboxylic acid groups, within the scope of formula (II) corresponds to the formula ##STR12## in which R', R.sub.2 ', R.sub.3 ', R.sub.4 ', R.sub.5 and X have the same meaning as in formula (IIa), and R.sub.6 stands for hydrogen or a lower alkyl radical.
GROUP 3
Triaryl-methane dyestuffs which are free from sulfonic acid and carboxylic acid groups and correspond to the formula ##STR13## in which R stands for an alkyl or cycloalkyl radical; R.sub.1 stands for hydrogen or the methyl group; R.sub.2 stands for the methyl group, an aryl or cycloalkyl radical; R.sub.3 stands for hydrogen or an alkyl group; R.sub.4 stands for an alkyl or cycloalkyl group; R.sub.3 and R.sub.4 may also be linked to one another to form a carbocyclic ring; X stands for the radical of an anion; and the dyestuffs may contain further substituents, with the exception of sulfonic acid and carboxylic acid groups, in the aliphatic, cycloaliphatic and aromatic radicals, including the phenylene radicals A, B and D illustrated in the formula.
The phenylene ring A, B and/or D may contain an annelated ring, particularly a six-membered monocyclic radical, as, for example, in a dyestuff of the formula ##STR14##
A particularly valuable selection of dyestuffs, free from sulfonic acid and carboxylic acid groups, within the scope of formula (III) corresponds to the formula ##STR15## in which R' and R.sub.3 ' stand for optionally substituted lower alkyl radicals with 1 to 4 carbon atoms; R.sub.4 ' stands for hydrogen or a lower alkyl radical with 1 to 4 carbon atoms; R.sub.5 stands for hydrogen, a halogen substituent, especially chlorine and bromine, or a lower alkyl or alkoxy radical with 1 to 4 carbon atoms; and X stands for the radical of an anion.
Another valuable selection of dyestuffs, free from sulfonic acid and carboxylic acid groups, within the scope of formula (III) corresponds to the formula ##STR16## in which R', R.sub.3 ', R.sub.4 ', R.sub.5 and X have the same meaning as in formula (IIIa), and R.sub.6 stands for hydrogen or a lower alkyl radical.
GROUP 4
Triaryl-methane dyestuffs which are free from sulfonic acid and carboxylic acid groups and correspond to the general formula ##STR17## in which at least one of the radicals R stands for a halogen substituent, an alkyl or alkoxy group; the other radicals R stand for hydrogen, a halogen substituent, an alkyl or alkoxy group; R.sub.1 stands for hydrogen or the methyl group; R.sub.2 stands for the methyl group, an aryl or a cycloalkyl radical; X is the radical of an anion; and the dyestuffs may contain further substituents with the exception of sulfonic acid and carboxylic acid groups, in the aliphatic, cycloaliphatic and aromatic radicals, including the phenylene radicals A, B and D illustrated in the formula. The phenylene ring A, B and/or D may contain an annelated ring, particularly a six-membered monocyclic radical, as, for example, in a dyestuff of the formula ##STR18##
A particularly valuable selection of dyestuffs, free from sulfonic acid and carboxylic acid groups, within the scope of formula (IV) corresponds to the formula ##STR19## in which R' stands for an alkyl or alkoxy group with 1 to 4 carbon atoms or a halogen substituent, and X is the radical of an anion.
Another valuable selection of dyestuffs, free from sulfonic acid and carboxylic acid groups, within the scope of formula (IV) corresponds to the formula ##STR20## in which R' and X have the same meaning as in formula (IVa), and R" stands for an alkyl radical with 1 to 4 carbon atoms.
The new dyestuffs of Group 1 are obtainable by condensing, in the presence of acidic condensation agents, benzophenones of the general formula ##STR21## in which R and R.sub.3 have the same meaning as given in respect of the formula (I), or as given in respect of R' and R.sub.3 ' in the formulae (Ia) and (Ib), and the rings B and D may be further substituted as hereinbefore described, with aromatic amines of the formula ##STR22## in which R.sub.1 and R.sub.2 have the same meaning as given in respect of formula (I), or as given in respect of R.sub.1 ' and R.sub.2 ' in formula (Ia), or R.sub.1 has the meaning of R.sub.1 ' in formula (Ia) and R.sub.2 is hydrogen. The ring A may be further substituted as hereinbefore described. Starting components are selected which are free from sulfonic acid and carboxylic acid groups.
The new dyestuffs of Group 2 are obtainable by condensing, in the presence of acidic condensation agents, benzophenones of the general formula ##STR23## in which R and R.sub.4 have the same meaning as given in respect of formula (II) or as given in respect of R' and R.sub.4 ' in formulae (IIa) and (IIb), and the rings B and D may be further substituted as hereinbefore described, with aromatic amines of the general formula ##STR24## in which R.sub.1, R.sub.2 and R.sub.3 have the same meaning as in formula (II) or as given for R.sub.1 ', R.sub.2 ' and R.sub.3 ' in formula (IIa) or R.sub.1 is hydrogen and R.sub.2 and R.sub.3 have the same meaning as given for R.sub.2 ' and R.sub.3 ' in formula (IIa). Starting components are selected which are free from sulfonic acid and carboxylic acid groups.
The new dyestuffs of Group 3 are obtainable by condensing, in the presence of acidic condensation agents, benzophenones of the general formula ##STR25## in which R, R.sub.3 and R.sub.4 have the same meaning as given in respect of formula (III), or as given in respect of R', R.sub.3 ' and R.sub.4 ' in formula (IIIa), and the rings B and D may be further substituted as hereinbefore described, with aromatic amines of the general formula ##STR26## in which R.sub.1 and R.sub.2 have the same meaning as given in respect of formula (III), or are both CH.sub.3 groups, or one is CH.sub.3 and the other is hydrogen, and the ring A may be further substituted as hereinbefore described. Starting components are selected which are free from sulfonic acid and carboxylic acid groups.
The new dyestuffs of Group 4 are obtainable by condensing in the presence of acidic condensation agents, benzophenones of the general formula ##STR27## in which R has the same meaning as in formula (IV), and the rings B and D may be further substituted as hereinbefore described, with aromatic amines of the general formula ##STR28## in which R has the same meaning as given in formula (IV) and R.sub.1 and R.sub.2 have the same meaning as in formula (IV) or R.sub.1 and R.sub.2 are both CH.sub.3 or one is CH.sub.3 and the other is hydrogen. Starting components are selected which are free from sulfonic acid and carboxylic acid groups.
Examples of benzophenones of the formulae (V), (VII), (IX) and (XI), collectively, are the following: 4-methoxybenzophenone, 4-ethoxybenzophenone, 4-methoxy-2-methylbenzophenone, 4-phenoxybenzophenone, 4-methoxy-4'-methylbenzophenone, 4-methoxy-2',4'-dimethylbenzophenone, 4-methoxy-2',5'-dimethylbenzophenone, 4-methoxy-3',4'-dimethylbenzophenone, 4-methoxy-2',4',5'-trimethylbenzophenone, 4-methoxy-2'-chlorobenzophenone, 4-methoxy-3'-chlorobenzo-phenone, 4-methoxy-4'-chlorobenzophenone, 4-methoxy-2',5'-dichlorobenzophenone, 2,4-dimethoxybenzophenone, 2,4-dimethoxy-2',5'-dichlorobenzophenone, 2,4-dimethoxy-2'-chlorobenzophenone, 2,4-dimethoxy-4'-chlorobenzophenone, 2,4-dimethoxy-3'-chlorobenzophenone, 4-methoxy-2',4'-diisopropylbenzophenone, 4-methoxy-2',5'-diisopropylbenzo-phenone, 2,4-dimethoxy-2'-bromobenzophenone, 4-methoxy-2,4'-dimethylbenzophenone, 4-methoxy-2-methyl-2'-chlorobenzo-phenone, 4-methoxy-2-methyl-2'-bromobenzophenone, 4-methoxy-2'-bromobenzophenone, 4,4'-dimethoxybenzophenone, 4,4'-diethoxybenzophenone, 2,4,4'-trimethoxybenzophenone, 4-methoxy-4'-ethoxybenzophenone, 4-ethoxy-4'-propoxybenzo-phenone, 4,4'-dimethoxy-2-methylbenzophenone, 4,4'-dimethoxy-2 -chloro-5-methylbenzophenone, 4,4'-di-n-propoxybenzophenone, 4,4'-dimethoxy-3,3'-dimethylbenzophenone, 4-methoxy-4'-phenoxybenzophenone, 4,4'-di-n-butoxybenzophenone, 4,4'-dimethoxy-3,3'-diethylbenzophenone, 4,4'-dimethoxy-3,3'-dichlorobenzophenone, 3,4,4'-trimethoxybenzophenone, 4,4'-dimethoxy-3,5-dimethylbenzophenone, 4,4'-dimethoxy-3-methyl-5-chlorobenzophenone, 4-methoxy-4'-isopropoxy-benzophenone, 4,4'-dimethoxy-3-isopropylbenzophenone, 4,4'-dimethoxy-2-chlorobenzophenone, 4,4'-dimethoxy-3-chlorobenzophenone, 4,4'-dimethoxy-2-methyl-5-chloro-benzophenone, 4,4'-dimethoxy-2-chloro-3-methylbenzophenone, 4,4'-dimethoxy-3-methylbenzophenone, 4,4'-dimethoxy-2,5-dimethylbenzophenone, 2,4'-dimethoxybenzophenone, 3,4'-dimethoxybenzophenone, 4,2'-dimethoxy-2-chloro-3-methyl-benzophenone, 3-methoxy-4'-propoxybenzophenone, 4,4'-dimethoxy-2,3-dimethylbenzophenone, 4-methoxy-4'-isopropoxybenzophenone, 4-methoxy-4'-butoxybenzophenone, 4,4'-dimethoxy-3,5-diisopropylbenzophenone, 4,2'-dimethoxy-3-chlorobenzophenone, 4,2'-dimethoxy-2-chlorobenzophenone, 4,2'-dimethoxy-2-methyl-5-chlorobenzophenone, 4,2'-di-methoxy-2-chloro-5-methylbenzophenone, 4,3'-dimethoxy-2-methylbenzophenone, 4-methoxy-4'-propoxy-2-methylbenzo-phenone, 4-ethoxy-2'-methoxybenzophenone, 4-ethoxy-3'-methoxybenzophenone, 4,2',5'-trimethoxybenzophenone, 4,3,3'-trimethoxybenzophenone, 4,3,2'-trimethoxybenzophenone, 4,2'-dimethoxy-3-methylbenzophenone, 4,2'-dimethoxy-2-methylbenzophenone, 4,2'-dimethoxy-5'-methylbenzophenone, 4-propoxy-2'-methoxybenzophenone, 4-methoxy-4'-methyl-mercaptobenzophenone, 4-ethoxy-2-methylbenzophenone, 4-methoxy-2-methyl-6-ethylbenzophenone, 4-n-butoxy-2-methyl-benzophenone, 4-methoxy-3'-methylbenzophenone, 4-methoxy-4'-tert.-butylbenzophenone, 4-ethoxy-3'-methylbenzophenone, 4-methoxy-2,3'-dimethylbenzophenone, 4-methoxy-2-methyl-4'-tert.-butylbenzophenone, 4-methoxy-2'-methylbenzophenone, 4-ethoxy-2'-methylbenzophenone, 4-n-propoxy-2'-methylbenzo-phenone, 4-isopropoxy-2'-methylbenzophenone, 4-n-butoxy-2'-methylbenzophenone, 4-methoxy-2,2'-dimethylbenzophenone, 2,4-dimethoxy-3'-methylbenzophenone, 4-methoxy-4'-phenoxy-benzophenone, 2-methoxy-1-(4'-methoxybenzoyl)-naphthalene, 4,4'-dimethoxy-2-methyl-6-ethylbenzophenone, 4-methoxy-4'-cyclohexylbenzophenone, 4,4'-dicyclohexyloxybenzophenone and 2,4,4'-triethoxybenzophenone.
Examples of aromatic amines of the formulae (VI), (VIII), (X) and (XII), collectively, are the following: dimethylaniline, diethylaniline, di-n-propylaniline, di-n-butylaniline, N-methyl-N-.beta.-hydroxyethylaniline, N-butyl-N-.beta.-hydroxyethylaniline, N,N-dihydroxyethylaniline, N,N-di-.beta.-chloro-ethylaniline, N-methyl-N-.beta.-cyanoethylaniline, N-methyl-N-.beta.-chloroethylaniline, N-ethyl-N-.beta.-chloroethyl-aniline, N-butyl-N-.beta.-chloroethylaniline, N-ethyl-N-.beta.-dimethylaminoethylaniline, N,N-bis-.alpha.,.beta.-dihydroxypropyl-aniline, N-methyl-N-benzylaniline, N-ethyl-N-benzylaniline, N,N-dibenzylaniline, N-methyldiphenylamine, N-methyl-N-(4-ethoxyphenyl)-aniline, N-phenylmorpholine, 2-methyl-N, N-dimethylaniline, 3-methyl-N,N-dimethylaniline, 3-chloro-N,N-dimethylaniline, 3-chloro-N,N-diethylaniline, 3-methyl-N-ethyl-N-benzylaniline, 3-methyl-N,N-dibenzyl-aniline, 3-methyl-N-ethyl-N-.beta.-hydroxyethylaniline, 3-methyl-N-ethyl-N-.beta.-dimethylaminoethylaniline, 3-methyl-N, N-dihydroxyethylaniline, 3-nitro-N,N-diethylaniline, 3-hydroxy-N,N-dimethylaniline, 3-hydroxy-N,N-diethylaniline, 3-ethoxy-N,N-diethylaniline, 2-methyl-5-hydroxy-N,N-di-methylaniline, N,N-diisopropylaniline, 3-methoxy-N,N-dimethylaniline, 3-methoxy-N,N-diethylaniline, 2-methyl-5-methoxy-N,N-dimethylaniline, N-methyl-N-.beta.-methoxyethyl-aniline, N,N-di-.beta.-methoxyethylaniline, N-methyl-N-isobutyl-aniline, N-methyl-N-isopropylaniline, N-ethyl-N-isopropyl-aniline, N-isopropyl-N-isobutylaniline, N-methyl-N-ethylaniline, N-methyl-N-propylaniline, N-ethyl-N-propylaniline, N-propyl-N-isopropylaniline, 1-dimethylaminonaphthalene, 1-diethylaminonaphthalene, N-ethyl-N-.beta.-hydroxyethylaniline, 3-methyl-N-ethyl-N-.beta.-chloroethylaniline, 3-methyl-N-ethyl-N-.beta.-cyanoethylaniline, 3-ethoxy-N,N-diethylaniline, 2-ethoxy-N-.beta.-cyanoethylaniline, 2-methyl-N-.beta.-cyanoethylaniline, 2-methyl-N-benzylaniline, 2-methyl-N-methylaniline, 2-methyl-N-ethylaniline, N-butylaniline, N-isobutylaniline, N-.beta.-cyanoethylaniline, N-.beta.-chloroethylaniline, N-benzyl-aniline, N-.beta.-cyanoethyl-2-ethylaniline, 2,3-dimethyl-N-.beta.-cyanoethylaniline, 2,5-dimethyl-N-.beta.-cyanoethylaniline, 2-hydroxy-N-.beta.-cyanoethylaniline, 3-methyl-N-ethylaniline, 3-methyl-N-butylaniline, N-.beta.-hydroxyethylaniline, tetrahydroquinoline, 2-methyl-2,3-dihydroindole, 1,2,3,3-tetramethylindoline, 1-phenyl-3-methylpyrazoline, 1,3-dimethylpyrazoline, 1,3-diphenylpyrazoline, 2,3-dimethyl-N-methylaniline, 2,5-dimethyl-N-methylaniline, N-methyl-N-cyclohexylaniline, N-methyldiphenylamine, N-methyl-N-(4-methyl-phenyl)-aniline, N-methyl-N-(4-chlorophenyl)-aniline, N-methyl-N-(4-bromophenyl)-aniline, 2-methyl-N,N-dimethyl-aniline, N-methyl-N-(3-methyl-phenyl)-aniline and N-methyl-N-(3-methoxy-phenyl)-aniline.
Suitable acidic condensation agents are, for example, phosphorus oxychloride, phosphorus pentoxide, thionyl chloride, phosgene, zinc chloride, aluminum chloride, tin chloride, sulfuric acid or phosphoric acid.
The reaction can be carried out in the presence or absence of an inert solvent. Suitable solvents are, for example, chlorobenzene, o-dichlorobenzene, toluene, xylene, benzene, ligroin, dioxan, cyclohexane, carbon tetrachloride, chloroform or ethylene chloride.
In general, the reaction is carried out at an elevated temperature, for example, at 30.degree.-160.degree. C. preferably at 40.degree.-120.degree. C.
According to another process, the new dyestuffs can be prepared by oxidation of the corresponding leuco compounds which, of course, have the same formulae as those hereinbefore given and described under the headings of Groups 1 to 4, subject to the modification that ##STR29## is replaced by ##STR30##
The oxidation is preferably carried out by means of suitable dehydrogenating or oxidizing agents, preferably in an acidic medium, for example in acetic acid, dilute sulfuric acid, dilute hydrochloric acid or in mixtures of these acids, Water-miscible organic solvents, such as alcohol, dimethylformamide or acetonitrile, may be added to improve the solubility. Suitable dehydrogenating or oxidizing agents are the agents usually applied in triphenyl-methane chemistry, for example, iron (III) or copper (II) salts, their complex compounds, alkali metal dichromates, lead (IV) oxide and its salts, such as lead tetracetate, nitrous acid, peroxide compounds, such as potassium persulfate, hydrogen peroxide, as well as atmospheric oxygen, possibly with the addition of oxygen-transferring catalysts, such as metal ions.
The leuco compounds to be oxidized can be prepared by condensing benzohydrol compounds having the same formulae as formulae (V), (VII), (IX) and (XI) subject to the modification that ##STR31## is replaced by ##STR32## with the various aromatic amines that have hereinbefore been described.
The anionic radicals X.sup.(-) may be inorganic as well as organic ions; examples are, Cl.sup.-, Br.sup.-, I.sup.-, CH.sub.3 SO.sub.4.sup.-, C.sub.2 H.sub.5 SO.sub.4.sup.-, p-toluene-sulfonate, HSO.sub.4.sup.-, benzene-sulfonate, p-chlorobenzene-sulfonate, phosphate, acetate, formate, propionate, oxalate, lactate, maleinate, crotonate, tartrate, citrate, NO.sub.3.sup.-, perchlorate, ZnCl.sub.3.sup.-. The type of anionic radical is of no importance for the properties of the dyestuffs, provided they are substantially colorless radicals which do not impair the solubility of the dyestuffs in an undesirable manner.
The new dyestuffs are valuable and can be used for the dyeing and printing of materials consisting of leather, tanned cotton, cellulose acetate, synthetic superpolyamides and -polyurethanes as well as for the dyeing of lignin-containing fibers, such as coco, jute and sisal. They are further suited for the production of writing liquids, stamp-pad inks, pastes for ball point pens, and they can be used in offset printing. Above all, they are well suited for the dyeing and printing of materials, especially flocks, fibers, filaments, ribbons, and woven or knitted fabrics, consisting completely or in part of acrylonitrile polymers and copolymers, as.-dicyanoethylene, or acidmodified aromatic polyesters or superpolyamides.
Acrylonitrile copolymers are, for example, copolymers of acrylonitrile with other vinyl compounds, such as vinyl chloride, vinylidene chloride, vinyl fluoride, vinyl acetate, vinyl pyridine, vinyl imidazole, vinyl alcohol, acrylic and methacrylic acid esters and amides, and as.-dicyanoethylene.
Acid-modified aromatic polyesters are, for example, poly-condensation products of sulfo-terephthalic acid and ethylene glycol, i.e. polyethylene glycol terephthalates containing sulfonic acid groups (type DACRON 64 of E. I. du Pont de Nemours & Company), such as are described in Belgian Patent Specification No. 549,179 and U.S. Pat. No. 2,893,816. Acid-modified superpolyamides are, for example, sulpho group-containing superpolyamides (type Dye I of Monsanto Company and BCF Nylon Carpet Yarn type 844 of E. I. du Pont de Nemours and Company).
Dyeing of acrylonitrile polymers and copolymers, as.-dicyanoethylene and acid-modified aromatic polyesters can be carried out from a weakly acidic bath; the material is expediently introduced into the dyebath at 40.degree.-60.degree. C. and dyeing is then performed at boiling temperature. It is also possible to dye under pressure at temperatures above 100.degree. C. Moreover, the dyestuffs can be added to spinning solutions serving for the production of fibers containing polyacrylonitrile, or they can be applied to the unstretched fiber. It is accordingly to be understood that the expression "dyeing of shaped materials" as used herein includes the dyeing of what will be used to produce the shaped material.
The dyeings which can be obtained according to the invention are characterized by vivid, predominantly red and violet shades of very good fastness to light and washing. The good affinity of the dyestuffs and their good fastness to cross-dyeing in an acetic acid and sulfuric acid medium should be emphasized.
The dyestuffs can be used individually or in mixtures. When materials of polyacrylonitrile are dyed, mixtures frequently show a higher strength of color.
With anionic precipitation agents, such as alumina, tannin, phosphotungstic (molybdic) acids, the dyestuffs form pigments which are fast to light and can be used to advantage in paper printing.
The following Examples are given for the purpose of illustrating the invention and its usefulness. Parts by volume are related to parts by weight as are milliliters to grams.

EXAMPLE 1
24.2 Parts by weight 2,4-dimethoxy-benzophenone are added to 35 parts by weight phosphorus oxychloride, and 14.9 parts by weight diethyl-aniline are subsequently introduced whereupon the temperature slightly rises. 15 Parts by weight phosphorus pentoxide are then added, and the reaction mixture is slowly heated to 100.degree. C. After stirring for 5 hours, the warm melt is poured into 800 parts by weight of water; and the dark-red solution is mixed with 10 parts by weight of a 50% aqueous zinc chloride solution. After stirring for several hours, the dyestuff of the formula ##STR33## crystallizes in the form of the zinc chloride double salt. It is filtered off with suction and further purified by dissolving it in 10% acetic acid and precipitation with a 50% aqueous zinc chloride solution. Materials of polyacrylonitrile are dyed with this dyestuff in a bluish red shade of outstanding fastness to light.
EXAMPLE 2
27.2 Parts by weight 2,4,4'-trimethoxybenzophenone are added to 35 parts by weight phosphorus oxychloride, and 14.9 parts by weight diethyl-aniline are then added whereupon the temperature slightly rises. 15 Parts by weight phosphorus pentoxide are then added and the reaction mixture is slowly heated to 100.degree. C. After stirring for 5 hours, the warm melt is poured into 800 parts by weight of water and the dark-red solution is mixed with 10 parts by weight of a 50% aqueous zinc chloride solution. After stirring for several hours, the dyestuff of the formula ##STR34## crystallizes in the form of the zinc chloride double salt. It is filtered off with suction and further purified by dissolving it in 10% acetic acid and precipitation with a 50% aqueous zinc chloride solution. Materials of polyacrylonitrile are dyed with this dyestuff in a reddish Bordeaux shade of outstanding fastness to light.
EXAMPLE 3
27.0 Parts by weight 4,4'-diethoxy-benzophenone and 12.1 parts by weight, N,N-dimethyl-aniline are introduced into 30 parts by volume phosphorus oxychloride, and 14 parts by weight phosphorus pentoxide are added; the temperature rises up to 130.degree. C. as soon as the reaction has started upon heating on a water bath. Heating on the boiling water bath is continued for 2 hours, and the melt is then poured into 500 parts by volume of water. The dyestuff resin which is precipitated after the addition of zinc chloride is separated and reprecipitated from water with the addition of some glacial acetic acid. Complete precipitation is again carried out with zinc chloride. The dyestuff of the formula ##STR35## is isolated in the form of the zinc chloride double salt by filtering off with suction, and dried in a vacuum at 50.degree. C. Materials of polyacrylonitrile are dyed with this dyestuff in a strongly bluish red shade of outstanding fastness to light.
EXAMPLE 4
27.2 Parts by weight 2,4,4'-trimethoxy-benzophenone are added to 35 parts by weight phosphorus oxychloride, and 12.1 parts by weight dimethyl-aniline are subsequently introduced whereupon the temperature slightly rises. 15 Parts by weight phosphorus pentoxide are then added, and the reaction mixture is slowly heated to 100.degree. C. After stirring for 5 hours, the warm melt is poured into 800 parts by weight of water, the drak-red solution is mixed with 15 parts by weight of a 50% aqueous zinc chloride solution, and the dyestuff resin is separated. It is dissolved in 1200 parts by volume of water, the solution is clarified with active charcoal, and the dyestuff of the formula ##STR36## is precipitated in the form of the zinc chloride double salt. Materials of polyacrylonitrile are dyed with this dyestuff in a reddish Bordeaux shade of outstanding fastness to light.
Similar valuable dyeings are obtained with dyestuffs which have been prepared in the manner described above from the benzophenones and aromatic amines set out in the following Table.
______________________________________Dyestuff from 4-methoxybenzo- Shade on polyacrylo-phenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline "N-methyl-N-.beta.-cyanoethylaniline strongly bluish redN-ethyl-N-.beta.-hydroxyethylaniline "di-n-propylaniline "N-ethyl-N-benzylaniline "3-methoxy-N,N-diethylaniline dull red3-methyl-N,N-dimethylaniline bluish Bordeaux3-methyl-N-ethyl-N-benzylaniline reddish violetN-butyl-N-.beta.-chloroethylaniline ruby2-methyl-N,N-dimethylaniline bluish redN,N-diisopropylaniline redN-methyldiphenylamine reddish violet1-dimethylaminonaphthalene bluish redN-ethyl-N-dimethylaminoethylaniline bluish pinkN,N-di-.beta.-chloroethylaniline strongly bluish redN-ethyl-N-.beta.-chloroethylaniline "N-methyl-2-methylaniline redN-ethyl-2-methylaniline yellowish redN-isobutylaniline redN-butyl-3-methylaniline bluish BordeauxN-benzyl-2-methylaniline bluish redN-.beta.-cyanoethyl-2-ethoxyaniline rubyN-.beta.-cyanoethyl-2-methylaniline redN-.beta.-cyanoethyl-2-ethylaniline redN-phenylmorpholine ruby1,2,3,3-tetramethylindoline red1-phenyl-3-methylpyrazoline reddish violet1,3-diphenylpyrazoline reddish blue______________________________________
______________________________________Dyestuff from 4-ethoxybenzo- Shade on polyacrylo-phenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish redN-methyl-N-.beta.-cyanoethylaniline strongly bluish redN-ethyl-N-.beta.-hydroxyethylaniline strongly bluish red3-methyl-N-ethyl-N-.beta.-chloroethyl-aniline red-violet3-methyl-N-ethyl-N-.beta.-cyanoethylaniline reddish violetdi-n-propylaniline bluish redN-ethyl-N-benzylaniline ruby3-methoxy-N,N-diethylaniline bluish red3-methyl-N,N-dimethylaniline strongly bluish redN,N-diisopropylaniline redN-methyldiphenylamine red-violetN-methyl-N-4-ethoxyphenylaniline reddish violet1-dimethylaminonaphthalene strongly bluish red2-ethoxy-N-.beta.-cyanoethylaniline ruby2-methyl-N-.beta.-cyanoethylaniline bluish redN-phenylmorpholine ruby1,2,3,3-tetramethylindoline bluish red1-phenyl-3-methylpyrazoline reddish violet______________________________________
______________________________________Dyestuff from 4-phenoxybenzo- Shade on polyacrylo-phenone and nitrile______________________________________dimethylaniline yellowish red3-methyl-N,N-dimethylaniline reddish BordeauxN-methyl-N-4-ethoxyphenylaniline reddish violet2-methoxy-N-cyanoethylaniline bluish red1,2,3,3-tetramethylindoline yellowish red1-phenyl-3-methylpyrazoline strongly bluish Bordeaux______________________________________
______________________________________Dyestuff from 2-methyl-4-methoxy- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline strongly yellowish reddiethylaniline strongly yellowish reddi-n-propylaniline yellowish redN-methyl-N-.beta.-hydroxyethylaniline redN-ethyl-N-.beta.-hydroxyethylaniline redN-butyl-N-.beta.-chloroethylaniline redN-methyl-N-.beta.-cyanoethylaniline redN-ethyl-N-benzylaniline red3-methyl-N,N-dimethylaniline Bordeaux, reddish3-methyl-N-ethyl-N-benzylaniline Bordeaux3-methyl-N-ethyl-N-.beta.-cyanoethylaniline Bordeaux3-methoxy-N,N-diethylaniline strongly yellowish red2-methyl-N-methylaniline yellowish scarlet2-methyl-N-ethylaniline yellowish scarlet2-methyl-N-cyanoethylaniline strongly yellowish redN-.beta.-hydroxyethylaniline yellowish red2-methyl-N-benzylaniline strongly yellowish red2-ethyl-N-.beta.-cyanoethylaniline yellowish red2,3-dimethyl-N-.beta.-cyanoethylaniline rubytetrahydroquinoline reddish orange1,2,3,3-tetramethylindoline strongly yellowish redN-phenylmorpholine red1-phenyl-3-methylpyrazoline Bordeaux1,3-diphenylpyrazoline strongly reddish blueN-ethyl-N-.beta.-dimethylamino-ethyl-aniline bluish redN-n-propyl-o-toluidine yellowish scarletN-i-propyl-o-toluidine yellowish scarletN-n-butyl-o-toluidine strongly yellowish red.alpha.-anilino-isobutyric acid-methylester strongly yellowish red______________________________________
______________________________________Dyestuff from 2-methyl-4-ethoxy- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline yellowish reddiethylaniline "di-n-propylaniline redN-methyl-N-.beta.-cyanoethylaniline somewhat bluish redN-methyl-N-.beta.-hydroxyethylaniline redN-ethyl-N-benzylaniline yellowish red3-methoxy-N,N-diethylaniline strongly yellowish red2-methyl-N-methylaniline scarlet2-methyl-N-ethylaniline scarlet2-methyl-N-.beta.-cyanoethylaniline bluish scarletN-isobutylaniline reddish orange2-ethyl-N-.beta.-cyanoethylaniline strongly yellowish red2-methyl-N-benzylaniline scarlet1,2,3,3-tetramethylindoline strongly yellowish redN-phenylmorpholine red.alpha.-anilino-isobutyric acid-methylester clear somewhat yellowish red______________________________________
______________________________________Dyestuff from 2-methyl-4-butoxybenzo- Shade on Polyacrylo-phenone and nitrile______________________________________dimethylaniline yellowish reddiethylaniline "di-n-propylaniline redN-methyl-N-.beta.-cyanoethylaniline bluish redN-methyl-N-.beta.-hydroxyethylaniline redN-ethyl-N-benzylaniline somewhat bluish red2-methyl-N-methylaniline reddish orange2-methyl-N-ethylaniline yellowish scarlet2-methyl-N-.beta.-cyanoethylaniline strongly yellowish red2-ethyl-N-.beta.-cyanoethylaniline yellowish redN-isobutylaniline strongly yellowish red1,2,3,3-tetramethylindoline strongly yellowish redN-phenylmorpholine red3-ethoxy-N,N-diethylaniline strongly yellowish red______________________________________
______________________________________Dyestuff from 2,4-dimethoxybenzo- Shade on polyacrylo-phenone and nitrile______________________________________dimethylaniline bluish reddi-n-propylaniline strongly bluish redN-methyl-N-.beta.-cyanoethylaniline BordeauxN-methyl-N-.beta.-hydroxyethylaniline bluish red3-methyl-N,N-dimethylaniline strongly bluish red2-methyl-N-ethylaniline red2-methyl-N-.beta.-cyanoethylaniline bluish red2-methyl-N-benzylaniline strongly bluish red1,2,3,3-tetramethylindoline redN-phenylmorpholine Bordeaux1,3-diphenylpyrazoline reddish dark-blue______________________________________
______________________________________Dyestuff from 4-methoxy-2'-chloro- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline yellowish reddiethylaniline yellowish redN-ethyl-N-chloroethylaniline redN-butyl-N-.beta.-chloroethylaniline somewhat bluish redN-methyldiphenylamine red-violet3-methyl-N,N-dimethylaniline reddish Bordeaux3-methyl-N-ethylaniline bluish reddi-n-propylaniline bluish redN-methyl-N-.beta.-hydroxyethylaniline bluish redN-methyl-N-.beta.-cyanoethylaniline strongly bluish red3-ethoxy-N,N-diethylaniline redN-ethyl-N-benzylaniline strongly bluish redN-butylaniline scarletN-isobutylaniline strongly yellowish redN-.beta.-cyanoethylaniline yellowish red2-methyl-N-methylaniline strongly yellowish red2-methyl-N-ethylaniline strongly yellowish red2-methyl-N-.beta.-cyanoethylaniline bluish red2-ethyl-N-.beta.-cyanoethylaniline red2-methyl-N-benzylaniline red1,2,3,3-tetramethylindoline strongly yellowish redN-phenylmorpholine strongly bluish red1,3-diphenylpyrazoline bluish violet1-phenyl-3-methylpyrazoline bluish Bordeaux.alpha.-anilino-isobutyric acid-methylester clear redN-n-butyl-o-toluidine strongly yellowish redN-ethyl-2-chloroaniline strongly bluish redN-ethyl-o-anisidine red______________________________________
______________________________________Dyestuff from 4-ethoxy-2'-chloro- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline reddiethylaniline bluish reddi-n-propylaniline "N-methyl-N-.beta.-hydroxyethylaniline strongly bluish redN-methyl-N-.beta.-cyanoethylaniline "N-ethyl-N-benzylaniline "3-ethoxy-N,N-diethylaniline strongly yellowish redN-butylaniline strongly yellowish redN-isobutylaniline strongly yellowish redN-.beta.-cyanoethylaniline red2-methyl-N-methylaniline strongly yellowish red2-methyl-N-ethylaniline strongly yellowish red2-methyl-N-benzylaniline bluish red2-methyl-N-.beta.-cyanoethylaniline red2-ethyl-N-.beta.-cyanoethylaniline "1,2,3,3-tetramethylindoline strongly yellowish redN-phenylmorpholine strongly bluish red1,3-diphenylpyrazoline strongly bluish violet1-phenyl-3-methylpyrazoline Bordeaux______________________________________
______________________________________Dyestuff from 4-methoxy-4'-chloro- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline "______________________________________
______________________________________Dyestuff from 4-methoxy-2',5'-di- Shade on polyacrylo-chlorobenzophenone and nitrile______________________________________dimethylaniline yellowish reddiethylaniline yellowish red______________________________________
______________________________________Dyestuff from 4-methoxy-2'-bromo- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline yellowish reddiethylaniline yellowish redN-methyl-N-.beta.-chloroethylaniline somewhat bluish red______________________________________
______________________________________Dyestuff from 4-methoxy-2'-methyl- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline yellowish reddiethylaniline yellowish reddi-n-propylaniline redN-methyl-N-.beta.-cyanoethylaniline bluish redN-methyl-N-.beta.-hydroxyethylaniline bluish redN-butyl-N-.beta.-chloroethylaniline bluish redN-ethyl-N-benzylaniline bluish red3-methyl-N,N-dimethylaniline Bordeaux3-methyl-N-ethyl-N-.beta.-chloroethyl-aniline bluish Bordeaux3-methyl-N-ethyl-N-.beta.-cyanoethylaniline bluish Bordeauxdiphenylamine red-violet3-ethoxy-N,N-diethylaniline strongly yellowish redN-n-butylaniline yellowish scarletN-isobutylaniline scarletN-benzylaniline scarlet2-methyl-N-methylaniline scarlet2-methyl-N-ethylaniline scarlet2-methyl-N-benzylaniline strongly bluish scarlet2-methyl-N-.beta.-cyanoethylaniline bluish scarletdi-n-propylaniline redN-ethyl-N-.beta.-dimethylamino-ethyl-aniline strongly bluish redn-butylaniline clear strongly yellowish redisobutylaniline strongly yellowish redN-cyanoethylaniline somewhat yellowish redN-methyl-o-toluidine clear strongly yellowish redN-ethyl-o-toluidine clear strongly yellowish redN-n-butyl-o-toluidine strongly yellowish redN-cyanoethyl-o-toluidine redN-cyanoethyl-2-ethylaniline red______________________________________
______________________________________Dyestuff from 4-methoxy-2'-methyl- Shade on polyacrylo-benzophenone and nitrile______________________________________2-ethyl-N-.beta.-cyanoethylaniline bluish scarlet2,5-dimethyl-N-.beta.-cyanoethylaniline bluish Bordeaux2-methyl-2,3-dihydroindole yellowish scarlet1,2,3,3-tetramethylindoline strongly yellowish redN-phenylmorpholine bluish red1-phenyl-3-methylpyrazoline strongly bluish Bordeaux1,3-diphenylpyrazoline reddish blueN-methyldiphenylamine bluish rubyN-methyl-4-ethoxyphenylaniline strongly bluish BordeauxN-ethyl-N-.beta.-dimethylamino-ethyl-aniline bluish pinkN-n-propyl-o-toluidine yellowish redN-i-propyl-o-toluidine strongly yellowish redN-n-butyl-o-toluidine strongly yellowish redN-ethyl-2-ethylaniline strongly yellowish red.alpha.-anilino-isobutyric acid-methylester clear redN-ethyl-2-chloroaniline bluish redN-ethyl-o-anisidine redN-cyanoethyl-o-anisidine ruby2-methylaminobenzoic acid-methylester redN-n-butyl-m-phenetidine strongly yellowish red______________________________________
______________________________________Dyestuff from 4-ethoxy-2'-methyl- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline yellowish reddiethylaniline yellowish reddi-n-propylaniline somewhat bluish redN-methyl-N-.beta.-cyanoethylaniline strongly bluish redN-methyl-N-.beta.-hydroxyethylaniline strongly bluish redN-butyl-N-.beta.-chloroethylaniline strongly bluish redN-ethyl-N-benzylaniline strongly bluish red3-methyl-N,N-dimethylaniline bluish ruby3-methyl-N-ethyl-N-.beta.-chloroethyl-aniline bluish Bordeaux3-methyl-N-ethyl-N-.beta.-cyanoethyl-aniline bluish Bordeaux3-ethoxy-N,N-diethylaniline strongly yellowish redN-n-butylaniline scarletN-benzylaniline bluish scarlet2-methyl-N-methylaniline scarlet2-methyl-N-ethylaniline scarlet2-methyl-N-benzylaniline red2-methyl-N-.beta.-cyanoethylaniline red2-ethyl-N-.beta.-cyanoethylaniline red2,5-dimethyl-N-.beta.-cyanoethylaniline bluish ruby2-methyl-2,3-dihydroindole reddish orange1,2,3,3-tetramethylindoline strongly yellowish redN-phenylmorpholine strongly bluish red1-phenyl-3-methylpyrazoline strongly bluish Bordeaux1,3-diphenylpyrazoline strongly reddish violetN-methyldiphenylamine bluish BordeauxN-ethyl-N-.beta.-dimethylaminoethyl-aniline strongly bluish redN-i-propyl-o-toluidine yellowish redN-ethyl-2-ethylaniline yellowish red.alpha.-anilino-isobutyric acid-methylester clear redN-ethyl-o-anisidine bluish redN-cyanoethyl-o-anisidine Bordeaux2-methylaminobenzoic acid-methylester redN-n-butyl-m-phenetidine strongly yellowish red______________________________________
______________________________________Dyestuff from 4-n-propoxy-2'-methyl- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish reddi-n-propylaniline bluish redN-methyl-N-.beta.-cyanoethylaniline strongly bluish redN-methyl-N-.beta.-hydroxyethylaniline strongly bluish red3-ethoxy-N,N-diethylaniline strongly yellowish redN-n-butylaniline scarletN-isobutylaniline bluish scarletN-.beta.-hydroxyethylaniline bluish redN-benzylaniline yellowish red2-methyl-N-methylaniline bluish scarlet2-methyl-N-ethylaniline red2-methyl-N-cyanoethylaniline bluish red2-ethyl-N-.beta.-cyanoethylaniline bluish red2-methyl-N-benzylaniline scarlet2-methyl-2,3-dihydroindole yellowish scarlet1,2,3,3-tetramethylindoline yellowish redN-phenylmorpholine strongly bluish red1-phenyl-3-methylpyrazoline red-violet1,3-diphenylpyrazoline reddish blueN-n-butyl-o-toluidine yellowish redN-ethyl-2-ethylaniline somewhat yellowish redN-ethyl-2-chloroaniline strongly bluish red.alpha.-anilino-isobutyric acid-methylester clear somewhat bluish red______________________________________
______________________________________Dyestuff from 4-isopropoxy-2'- Shade on polyacrylo-methylbenzophenone and nitrile______________________________________dimethylaniline yellowish reddiethylaniline reddish orangedi-n-propylaniline red2-methyl-N-methylaniline yellowish orange2-methyl-N-ethylaniline orange______________________________________
______________________________________Dyestuff from 4-n-butoxy-2'- Shade on polyacrylo-methylbenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish reddi-n-propylaniline bluish redN-methyl-N-.beta.-hydroxyethylaniline strongly bluish redN-methyl-N-.beta.-cyanoethylaniline strongly bluish red3-ethoxy-N,N-diethylaniline yellowish redN-n-butylaniline scarletN-isobutylaniline scarletN-benzylaniline bluish scarlet2-methyl-N-methylaniline strongly yellowish red2-methyl-N-ethylaniline scarlet2-methyl-N-.beta.-cyanoethylaniline bluish red2-ethyl-N-.beta.-cyanoethylaniline bluish red2-methyl-N-benzylaniline bluish red2-methyl-2,3-dihydroindole yellowish scarlet1,2,3,3-tetramethylindoline yellowish redN-phenylmorpholine strongly bluish red1-phenyl-3-methylpyrazoline red-violet1,3-diphenylpyrazoline bluish violetN-n-butyl-o-toluidine yellowish redN-ethyl-2-chloroaniline strongly bluish red.alpha.-anilino-isobutyric acid-methylester somewhat bluish red______________________________________
______________________________________Dyestuff from 4-methoxy-3'-methyl- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish reddi-n-propylaniline bluish redN-methyl-N-.beta.-hydroxyethylaniline bluish redN-methyl-N-.beta.-cyanoethylaniline strongly bluish red2-methyl-N-methylaniline yellowish red2-methyl-N-ethylaniline yellowish red2-methyl-N-benzylaniline red2-methyl-N-.beta.-cyanoethylaniline red2-ethyl-N-.beta.-cyanoethylaniline red2,5-dimethyl-N-.beta.-cyanoethylaniline bluish Bordeaux1,2,3,3-tetramethylindoline redN-phenylmorpholine strongly bluish red1,3-diphenylpyrazoline strongly bluish redN-isopropyl-o-toluidine redN-ethyl-2-ethylaniline red.alpha.-anilino-isobutyric acid-methylester clear bluish redN-ethyl-o-anisidine Bordeaux______________________________________
______________________________________Dyestuff from 4-ethoxy-3'-methyl- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish reddi-n-propylaniline strongly bluish redN-methyl-N-.beta.-cyanoethylaniline strongly bluish redN-methyl-N-.beta.-hydroxyethylaniline strongly bluish red2-methyl-N-methylaniline yellowish red2-methyl-N-ethylaniline yellowish red2-methyl-N-benzylaniline bluish red2-methyl-N-.beta.-cyanoethylaniline red2-ethyl-N-.beta.-cyanoethylaniline bluish red2,3-dimethyl-N-.beta.-cyanoethylaniline bluish red1,2,3,3-tetramethylindoline bluish redN-phenylmorpholine strongly bluish red1,3-diphenylpyrazoline bluish redN-isopropyl-o-toluidine red.alpha.-anilino-isobutyric acid-methylester clear bluish red______________________________________
______________________________________Dyestuff from 4-methoxy-4'-methyl- Shade on polyacrylo-benzophenone and nitrile______________________________________2-ethyl-N-.beta.-cyanoethylaniline red2,3-dimethyl-N-.beta.-cyanoethylaniline strongly bluish Bordeaux2-methyl-N-.beta.-cyanoethylaniline bluish redN-phenylmorpholine bluish ruby1,2,3,3-tetramethylindoline red-Bordeaux.alpha.-anilino-isobutyric acid-methylester clear bluish redN-ethyl-o-anisidine ruby______________________________________
______________________________________Dyestuff from 4-methoxy-2',4'- Shade on polyacrylo-dimethylbenzophenone and nitrile______________________________________dimethylaniline reddiethylaniline redN-ethyl-N-.beta.-chloroethylaniline BordeauxN,N-di-.beta.-chloroethylaniline bluish redN-ethyl-N-benzylaniline bluish redN-methyldiphenylamine bluish BordeauxN-methyl-N-4-ethoxyphenylaniline strongly bluish Bordeaux3-methyl-N,N-dimethylaniline bluish redN,N-di-n-propylaniline bluish redN-methyl-N-.beta.-hydroxyethylaniline bluish redN-methyl-N-.beta.-cyanoethylaniline strongly bluish red3-ethoxy-N,N-diethylaniline yellowish red2-methyl-N-methylaniline scarlet2-methyl-N-ethylaniline bluish scarlet2-methyl-N-.beta.-cyanoethylaniline redN-n-butylaniline yellowish scarletN-isobutylaniline strongly yellowish red2-methyl-N-benzylaniline yellowish red2-ethyl-N-.beta.-cyanoethylaniline red1,2,3,3-tetramethylindoline yellowish redN-phenylmorpholine bluish red______________________________________
______________________________________Dyestuff from 4-methoxy-3',4-'- Shade on polyacrylo-dimethylbenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish redN-ethyl-N-.beta.-chloroethylaniline bluish redN-butyl-N-.beta.-chloroethylaniline bluish redN-methyldiphenylamine strongly bluish Bordeaux3-methyl-N,N-dimethylaniline bluish Bordeaux2-ethyl-N-.beta.-cyanoethylaniline red2,3-dimethyl-N-.beta.-cyanoethylaniline bluish Bordeaux2-methyl-N-methylaniline red2-methyl-N-ethylaniline red2-methyl-N-.beta.-cyanoethylaniline redN-isobutylaniline red1,2,3,3-tetramethylindoline bluish red.alpha.-anilino-isobutyric acid-methylester clear red______________________________________
______________________________________Dyestuff from 4-methoxy-2',5'- Shade on polyacrylo-dimethylbenzophenone and nitrile______________________________________dimethylaniline yellowish reddiethylaniline yellowish redN-ethyl-N-.beta.-chloroethylaniline redN-methyldiphenylamine bluish BordeauxN-methyl-N-4-ethoxyphenylaniline red-violet3-methyl-N,N-dimethylaniline reddish Bordeaux______________________________________
______________________________________Dyestuff from 4-methoxy-2',4',5'- Shade on polyacrylo-trimethylbenzophenone and nitrile______________________________________dimethylaniline reddiethylaniline redN-ethyl-N-.beta.-chloroethylaniline bluish redN-isobutylaniline strongly yellowish red2-methyl-N-methylaniline strongly yellowish red2-methyl-N-ethylaniline strongly yellowish red2-methyl-N-.beta.-cyanoethylaniline red2-methyl-N-benzylaniline red2-ethyl-N-.beta.-cyanoethylaniline yellowish red2,3-dimethyl-N-.beta.-cyanoethylaniline bluish ruby2,5-dimethyl-N-.beta.-cyanoethylaniline Bordeauxtetrahydroquinoline strongly yellowish red2-methyl-2,3-dihydroindole strongly yellowish red1,2,3,3-tetramethylindoline yellowish red1,3-diphenylpyrazoline reddish bluedi-n-propylaniline bluish redN-ethyl-N-.beta.-dimethylamino-ethyl-aniline bluish redN-n-propyl-o-toluidine yellowish redN-i-propyl-o-toluidine yellowish redN-n-butyl-o-toluidine somewhat yellowish redN-ethyl-2-ethylaniline scarlet.alpha.-anilino-isobutyric acid-methylester strongly bluish scarletN-ethyl-o-anisidine strongly bluish red2-methylaminobenzoic acid-methylester red______________________________________
______________________________________Dyestuff from 4-methoxy-diethyl- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish reddi-n-propylaniline bluish redN-methyl-N-.beta.-cyanoethylaniline strongly bluish redN-methyl-N-.beta.-hydroxyethylaniline bluish redN-n-butyl-N-.beta.-chloroethylaniline rubyN-ethyl-N-benzylaniline strongly bluish red3-ethoxy-N,N-diethylaniline strongly yellowish redN-isobutylaniline strongly yellowish redN-benzylaniline yellowish red2-methyl-N-methylaniline strongly yellowish red2-methyl-N-ethylaniline strongly yellowish red2-methyl-N-.beta.-cyanoethylaniline yellowish red2-ethyl-N-.beta.-cyanoethylaniline yellowish red2-methyl-N-benzylaniline red1,2,3,3-tetramethylindoline yellowish redN-phenylmorpholine bluish red______________________________________
______________________________________Dyestuff from 4-methoxy-2',4'- Shade on polyacrylo-diisopropylbenzophenone and nitrile______________________________________dimethylaniline reddiethylaniline reddi-n-propylaniline bluish redN-methyl-N-.beta.-chloroethylaniline bluish redN-ethyl-N-.beta.-chloroethylaniline bluish redN-butyl-N-.beta.-chloroethylaniline strongly bluish red5-methyl-N-ethyl-N-.beta.-chloroethyl-aniline bluish Bordeaux2-methyl-N-methylaniline strongly yellowish red2-methyl-N-.beta.-cyanoethylaniline red______________________________________
______________________________________Dyestuff from 4-methoxy-2',5'- Shade on polyacrylo-diisopropylbenzophenone and nitrile______________________________________dimethylaniline reddiethylaniline bluish red______________________________________
______________________________________Dyestuff from 4-methoxy-4'-tert.- Shade on polyacrylo-butylbenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline strongly bluish reddi-n-propylaniline rubyN-methyl-N-.beta.-cyanoethylaniline strongly bluish redN-methyl-N-.beta.-hydroxyethylaniline rubyN-n-butyl-N-.beta.-chloroethylaniline rubyN-ethyl-N-benzylaniline strongly bluish red3-ethoxy-N,N-diethylaniline red-Bordeaux2-methyl-N-methylaniline bluish red2-methyl-N-ethylaniline red2-methyl-N-.beta.-cyanoethylaniline bluish redN-n-butylaniline yellowish redN-isobutylaniline yellowish redN-benzylaniline yellowish red2-methyl-N-benzylaniline red2-ethyl-N-.beta.-cyanoethylaniline red1,2,3,3-tetramethylindoline bluish red______________________________________
______________________________________Dyestuff from 2-methyl-4-methoxy- Shade on polyacrylo-2'-chlorobenzophenone and nitrile______________________________________dimethylaniline yellowish reddiethylaniline yellowish redN-methyl-N-.beta.-chloroethylaniline redN-ethyl-N-.beta.-chloroethylaniline yellowish redN-butyl-N-.beta.-chloroethylaniline red3-methyl-N,N-dimethylaniline yellowish red______________________________________
______________________________________Dyestuff from 2-methyl-4-methoxy- Shade on polyacrylo-2'-bromobenzophenone and nitrile______________________________________dimethylaniline strongly yellowish reddiethylaniline yellowish redN-ethyl-N-.beta.-chloroethylaniline yellowish red3-methyl-N-ethyl-N-.beta.-chloroethyl-aniline red-Bordeaux3-methyl-N,N-dimethylaniline yellowish red______________________________________
______________________________________Dyestuff from 2,2'-dimethyl-4- Shade on polyacrylo-methoxybenzophenone and nitrile______________________________________dimethylaniline strongly yellowish reddiethylaniline strongly yellowish reddi-n-propylaniline strongly yellowish redN-methyl-N-.beta.-hydroxyethylaniline redN-methyl-N-.beta.-cyanoethylaniline bluish red2-methyl-N-methylaniline reddish orange2-methyl-N-ethylaniline reddish orange2-methyl-N-.beta.-cyanoethylaniline scarlet2-ethyl-N-.beta.-cyanoethylaniline bluish scarlet2,5-dimethyl-N-.beta.-cyanoethylaniline strongly bluish red2-methyl-N-benzylaniline scarlet1,2,3,3-tetramethylindoline strongly reddish orangeN-phenylmorpholine red1-phenyl-2-methylpyrazoline bluish ruby1,3-diphenylpyrazoline strongly reddish blueN-methyldiphenylamine bluish ruby______________________________________
______________________________________Dyestuff from 2,3'-dimethyl-4- Shade on polyacrylo-methoxybenzophenone and nitrile______________________________________dimethylaniline strongly yellowish reddiethylaniline yellowish reddi-n-propylaniline yellowish redN-methyl-N-.beta.-cyanoethylaniline redN-methyl-N-.beta.-hydroxyethylaniline red2-methyl-N-methylaniline yellowish scarlet2-methyl-N-ethylaniline yellowish scarlet2-methyl-N-benzylaniline scarlet2-methyl-N-.beta.-cyanoethylaniline scarlet2-ethyl-N-.beta.-cyanoethylaniline bluish scarlet2,5-dimethyl-N-.beta.-cyanoethylaniline strongly bluish red1,2,3,3-tetramethylindoline strongly yellowish redN-phenylmorpholine bluish red1-phenyl-3-methylpyrazoline bluish ruby1,3-diphenylpyrazoline strongly reddish dark-blueN-methyldiphenylamine Bordeaux______________________________________
______________________________________Dyestuff from 2,4'-dimethyl-4- Shade on polyacrylo-methoxybenzophenone and nitrile______________________________________dimethylaniline yellowish reddiethylaniline redN-methyl-N-.beta.-chloroethylaniline redN-n-butyl-N-.beta.-chloroethylaniline red3-methyl-N-ethyl-N-.beta.-chloroethylaniline Bordeauxdi-n-propylaniline red2-methyl-N-methylaniline yellowish scarlet2-methyl-N-ethylaniline strongly yellowish red2-methyl-N-benzylaniline yellowish red2-methyl-N-.beta.-cyanoethylaniline yellowish red2-ethyl-N-.beta.-cyanoethylaniline bluish scarlet2,5-dimethyl-N-.beta.-cyanoethylaniline strongly bluish red1,2,3,3-tetramethylindoline yellowish redN-phenylmorpholine bluish ruby1-phenyl-3-methylpyrazoline bluish Bordeaux1,3-diphenylpyrazoline strongly reddish blue______________________________________
______________________________________Dyestuff from 2-methyl-4-methoxy- Shade on polyacrylo-4'-tert.-butylbenzophenone and nitrile______________________________________dimethylaniline reddiethylaniline reddi-n-propylaniline bluish redN-methyl-N-.beta.-cyanoethylaniline bluish redN-methyl-N-.beta.-hydroxyethylaniline bluish red3-ethoxy-N,N-diethylaniline yellowish red2-methyl-N-methylaniline scarlet2-methyl-N-ethylaniline scarlet2-methyl-N-.beta.-cyanoethylaniline bluish scarletN-n-butylaniline yellowish scarletN-isobutylaniline yellowish scarlet2-ethyl-N-.beta.-cyanoethylaniline strongly yellowish red2-methyl-N-benzylaniline scarlet______________________________________
______________________________________Dyestuff from 4-ethoxy-2',4'-di- Shade on polyacrylo-methylbenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline reddi-n-propylaniline bluish red2-methyl-N-methylaniline strongly yellowish red2-methyl-N-ethylaniline strongly yellowish red2-methyl-N-benzylaniline yellowish red2-methyl-N-.beta.-cyanoethylaniline red2-ethyl-N-.beta.-cyanoethylaniline yellowish redN-n-butylaniline strongly yellowish redN-isobutylaniline strongly yellowish red.alpha.-anilino-isobutyric acid-methylester clear red______________________________________
______________________________________Dyestuff from 4-ethoxy-2',4',5'- Shade on polyacrylo-trimethylbenzophenone and nitrile______________________________________dimethylaniline reddiethylaniline reddi-n-propylaniline bluish red2-methyl-N-methylaniline strongly yellowish red2-methyl-N-ethylaniline strongly yellowish red2-methyl-N-.beta.-cyanoethylaniline yellowish red______________________________________
______________________________________Dyestuff from 4-ethoxy-4'-tert.- Shade on polyacrylo-butylbenzophenone and nitrile______________________________________dimethylaniline strongly bluish reddiethylaniline strongly bluish reddi-n-propylaniline strongly bluish redN-isobutylaniline yellowish red2-methyl-N-methylaniline bluish red2-methyl-N-ethylaniline red2-methyl-N-.beta.-cyanoethylaniline redN-methyl-N-.beta.-hydroxyethylaniline strongly bluish redN-methyl-N-.beta.-cyanoethylaniline strongly bluish red1,2,3,3-tetramethylindoline bluish redN-phenylmorpholine ruby1,3-diphenylpyrazoline reddish blue.alpha.-anilino-isobutyric acid-methylester bluish red______________________________________
______________________________________Dyestuff from 2,4-dimethoxy-2'- Shade on polyacrylo-chlorobenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline strongly bluish redN-methyl-N-.beta.-chloroethylaniline reddish BordeauxN-ethyl-N-.beta.-chloroethylaniline reddish BordeauxN-butyl-N-.beta.-chloroethylaniline Bordeaux3-chloro-N,N-dimethylaniline currant-grey3-methyl-N,N-dimethylaniline bluish Bordeaux______________________________________
______________________________________Dyestuff from 2,4-dimethoxy-4'- Shade on polyacrylo-chlorobenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline red-BordeauxN-ethyl-N-.beta.-chloroethylaniline reddish Bordeaux______________________________________
______________________________________Dyestuff from 2,4-dimethoxy-2',5'- Shade on polyacrylo-dichlorobenzophenone and nitrile______________________________________dimethylaniline red-Bordeauxdiethylaniline red-BordeauxN-ethyl-N-.beta.-chloroethylaniline reddish Bordeaux______________________________________
______________________________________Dyestuff from 2,4-dimethoxy-2'- Shade on polyacryl-bromobenzophenone and nitrile______________________________________dimethylaniline reddish Bordeauxdiethylaniline reddish BordeauxN-methyl-N-.beta.-chloroethylaniline bluish rubyN-ethyl-N-.beta.-chloroethylaniline Bordeaux______________________________________
______________________________________Dyestuff from 2,4-dimethoxy-3'- Shade on polyacrylo-methylbenzophenone and nitrile______________________________________dimethylaniline strongly bluish reddiethylaniline strongly bluish reddi-n-propylaniline strongly bluish redN-methyl-N-.beta.-cyanoethylaniline Bordeaux2-methyl-N-.beta.-cyanoethylaniline strongly bluish red2-methyl-N-benzylaniline bluish red1,2,3,3-tetramethylindoline redN-phenylmorpholine red1,3-diphenylpyrazoline reddish blue______________________________________
______________________________________Dyestuff from 4-methoxy-4'- Shade on polyacrylo-phenoxybenzophenone and nitrile______________________________________dimethylaniline dull reddiethylaniline dull reddi-n-propylaniline reddish Bordeaux3-chloro-N,N-diethylaniline reddish grey3-ethoxy-N,N-diethylaniline bluish red3-methyl-N,N-dimethylaniline strongly bluish Bordeaux2-methyl-N-.beta.-cyanoethylaniline red2-ethoxy-N-.beta.-cyanoethylaniline Bordeaux______________________________________
______________________________________Dyestuff from 2,4'-dimethoxy- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline reddiethylaniline bluish reddi-n-propylaniline bluish reddi-n-butylaniline bluish redN-methyl-N-.beta.hydroxyethylaniline bluish redN-methyl-N-.beta.-cyanoethylaniline strongly bluish redN-butyl-N-.beta.-chloroethylaniline bluish redN-methyl-N-benzylaniline red-BordeauxN-ethyl-N-benzylaniline red-BordeauxN,N-dibenzylaniline strongly bluish BordeauxN-phenylmorpholine red-Bordeaux3-chloro-N,N-diethylaniline bluish violet3-ethoxy-N,N-diethylaniline yellowish redN,N-diisopropylaniline yellowish redN-methyl-N-isopropylaniline redN-methyl-N-isobutylaniline bluish redN-ethyl-N-isopropylaniline bluish redN-isopropyl-N-isobutylaniline red-BordeauxN-methyl-N-ethylaniline yellowish redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline bluish redN-propyl-N-isopropylaniline bluish red2-methyl-N-methylaniline yellowish red2-methyl-N-.beta.-cyanoethylaniline bluish red2-ethyl-N-.beta.-cyanoethylaniline red2,5-dimethyl-N-.beta.-cyanoethylaniline bluish ruby2-methyl-N-benzylaniline red1,2,3,3-tetramethylindoline yellowish red1-phenyl-3-methylpyrazoline strongly bluish Bordeaux1,3-diphenylpyrazoline reddish blue______________________________________
______________________________________Dyestuff from 2-methoxy-4'- Shade on polyacrylo- ethoxybenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish reddi-n-propylaniline bluish reddi-n-butylaniline strongly bluish redN-methyl-N-.beta.-hydroxyethylaniline bluish redN,N-diisopropylaniline redN-methyl-N-isopropylaniline bluish redN-methyl-N-isobutylaniline bluish redN-ethyl-N-isopropylaniline bluish redN-isopropyl-N-isobutylaniline strongly bluish redN-methyl-N-ethylaniline bluish redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline strongly bluish redN-propyl-N-isopropylaniline strongly bluish redN-phenylmorpholine strongly bluish red1,2,3,3-tetramethylindoline red1,3-diphenylpyrazoline reddish blue2-methyl-N-ethylaniline yellowish red2-methyl-N-.beta.-cyanoethylaniline bluish red______________________________________
______________________________________Dyestuff from 2-methoxy-4'- Shade on polyacrylo- propoxybenzophenone and nitrile______________________________________dimethylaniline reddiethylaniline bluish reddi-n-propylaniline bluish reddi-n-butylaniline strongly bluish redN-methyl-N-.beta.-hydroxyethylaniline bluish redN-methyl-N-isopropylaniline bluish red -N-ethyl-N-isopropylaniline bluish redN-isopropyl-N-isobutylaniline strongly bluish redN-methyl-N-ethylaniline redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline bluish redN-propyl-N-isopropylaniline bluish red______________________________________
______________________________________Dyestuff from 2,4'-dimethoxy-2'- Shade on polyacrylo- chlorobenzophenone and nitrile______________________________________dimethylaniline reddish browndiethylaniline yellow-browndi-n-propylaniline yellow-browndi-n-butylaniline yellow-brownN-methyl-N-.beta.-hydroxyethylaniline yellowish brick-redN-methyl-N-isobutylaniline orange-brown______________________________________
______________________________________Dyestuff from 2,4'-dimethoxy-3'- Shade on polyacrylo- chlorobenzophenone and nitrile______________________________________dimethylaniline yellowish reddiethylaniline yellowish reddi-n-propylaniline yellowish reddi-n-butylaniline yellowish redN-methyl-N-.beta.-hydroxyethyl- aniline redN,N-diisopropylaniline yellowish scarletN-methyl-N-isopropylaniline yellowish redN-methyl-N-isobutylaniline yellowish redN-methyl-N-ethylaniline yellowish redN-methyl-N-propylaniline yellowish redN-ethyl-N-propylaniline yellowish redN-propyl-N-isopropylaniline yellowish red______________________________________
______________________________________Dyestuff from 2,4'-dimethoxy-2'- Shade on polyacrylo- methylbenzophenone and nitrile______________________________________dimethylaniline strongly yellowish reddiethylaniline yellowish reddi-n-propylaniline yellowish reddi-n-butylaniline redN-methyl-N-.beta.-hydroxyethylaniline redN-methyl-N-isopropylaniline yellowish redN-ethyl-N-isopropylaniline yellowish redN-propyl-N-isopropylaniline yellowish redN-methyl-N-ethylanine yellowish redN-propyl-N-methylaniline yellowish redN-ethyl-N-propylaniline yellowish redN-isopropyl-N-isobutylaniline redN-methyl-N-isobutylaniline yellowish red2-methyl-N-methylaniline yellowish scarlet2-methyl-N-ethylaniline yellowish scarlet2-methyl-N-.beta.-cyanoethylaniline red2-methyl-N-benzylaniline yellowish redN-methyl-N-.beta.-cyanoethylaniline bluish red______________________________________
______________________________________Dyestuff from 2,4'-dimethoxy-3'- Shade on polyacrylo- methylbenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish reddi-n-propylaniline bluish reddi-n-butylaniline strongly bluish redN-methyl-N-.beta.-hydroxyethylaniline strongly bluish redN,N-diisopropylaniline red______________________________________
______________________________________Dyestuff from 2,4'-dimethoxy-5- Shade on polyacrylo- methylbenzophenone and nitrile______________________________________dimethylaniline reddiethylaniline bluish reddi-n-propylaniline red-Bordeaux______________________________________
______________________________________Dyestuff from 2,4'-dimethoxy-2'- Shade on polyacrylo- methyl-5'-chlorobenzophenone and nitrile______________________________________dimethylaniline strongly yellowish reddiethylaniline yellowish scarletdi-n-propylaniline strongly yellowish reddi-n-butylaniline strongly yellowish redN-methyl-N-.beta.-hydroxyethylaniline yellowish redN,N-diisopropylaniline reddish orangeN-methyl-N-isopropylaniline strongly yellowish redN-ethyl-N-isopropylaniline strongly yellowish redN-propyl-N-isopropylaniline strongly yellowish redN-methyl-N-ethylaniline strongly yellowish redN-methyl-N-propylaniline strongly yellowish redN-ethyl-N-propylaniline strongly yellowish redN-methyl-N-isobutylaniline strongly yellowish redN-isopropyl-N-isobutylaniline yellowish red______________________________________
______________________________________Dyestuff from 2,4'-dimethoxy-2'- Shade on polyacrylo- chloro-5'-methylbenzophenone and nitrile______________________________________dimethylaniline yellowish brick-reddiethylaniline yellow-browndi-n-butylaniline red-brownN-methyl-N-.beta.-hydroxyethylaniline strongly yellowish redN-methyl-N-isopropylaniline yellowish brick-redN-methyl-N-isobutylaniline brick-red______________________________________
______________________________________Dyestuff from 2,4'-dimethoxy-4,6- Shade on polyacrylo- dimethylbenzophenone and nitrile______________________________________dimethylaniline reddiethylaniline reddi-n-propylaniline yellowish BordeauxN-methyl-N-.beta.-hydroxyethylaniline bluish redN-methyl-N-.beta.-cyanoethylaniline strongly bluish redN,N-diisopropylaniline strongly yellowish redN-methyl-N-isopropylaniline redN-methyl-N-isobutylaniline redN-ethyl-N-isopropylaniline redN-isopropyl-N-isobutylaniline bluish red______________________________________
______________________________________Dyestuff from 2,4'-dimethoxy-2'- Shade on polyacrylo- chloro-3'-methylbenzophenone and nitrile______________________________________dimethylaniline strongly yellowish brick reddiethylaniline yellowish brick-reddi-n-propylaniline brick-reddi-n-butylaniline brick-redN-methyl-N-.beta.-hydroxyethylaniline yellowish redN-methyl-N-.beta.-cyanoethylaniline redN-methyl-N-benzylaniline bluish red3-ethoxy-N,N-diethylaniline reddish orangeN,N-diisopropylaniline reddish orangeN-methyl-N-isobutylaniline strongly yellowish red______________________________________
______________________________________Dyestuff from 3,4'-dimethoxybenzo- Shade on polyacrylo- phenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish red -di-n-propylaniline red-Bordeauxdi-n-butylaniline red-BordeauxN-methyl-N-.beta.-hydroxyethylaniline bluish redN,N-di-.beta.-hydroxyethylaniline bluish redN-methyl-N-.beta.cyanoethylaniline strongly bluish redN-butyl-N-.beta.-chloroethylaniline strongly bluish redN-methyl-N-benzylaniline red-BordeauxN-ethyl-N-benzylaniline strongly bluish redN,N-dibenzylaniline rubyN-methyldiphenylamine bluish BordeauxN-methyl-N-4-ethoxyphenylaniline strongly bluish BordeauxN-phenylmorpholine strongly bluish red3-methyl-N-ethyl-N-benzylaniline strongly bluish Bordeaux3-ethoxy-N,N-diethylaniline redN-methyl-N-.beta.-methoxyethylaniline bluish redN-methyl-N-isopropylaniline bluish redN-ethyl-N-isopropylaniline bluish redN-propyl-N-isopropylaniline bluish redN-methyl-N-ethylaniline bluish redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline red-BordeauxN-methyl-N-isobutylaniline bluish redN-isopropyl-N-isobutylaniline strongly bluish redN-n-butylaniline strongly yellowish redN-isobutylaniline strongly yellowish redN-.beta.-cyanoethylaniline red2-methyl-N-methylaniline strongly yellowish red2-methyl-N-ethylaniline yellowish red2-methyl-N-.beta.-cyanoethylaniline bluish red2-ethyl-N-.beta.-cyanoethylaniline red2-methyl-N-benzylaniline red1,2,3,3-tetramethylindoline red.alpha.-anilino-isobutyric acid-methylester strongly bluish red______________________________________
______________________________________Dyestuff from 3-methoxy-4'- Shade on polyacrylo- ethoxybenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish reddi-n-propylaniline strongly bluish reddi-n-butylaniline strongly bluish redN-methyl-N-.beta.-hydroxyethylaniline bluish redN,N-diisopropylaniline redN-methyl-N-isopropylaniline bluish redN-ethyl-N-isopropylaniline bluish redN-propyl-N-isopropylaniline strongly bluish redN-methyl-N-ethylaniline bluish redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline strongly bluish redN-methyl-N-isobutylaniline red-BordeauxN-isopropyl-N-isobutylaniline strongly bluish red2-methyl-N-methylaniline yellowish red2-methyl-N-ethylaniline red2-methyl-N-.beta.-cyanoethylaniline bluish red2-ethyl-N-.beta.-cyanoethylaniline bluish red1,2,3,3-tetramethylindoline bluish red______________________________________
______________________________________Dyestuff from 3-methoxy-4'-propoxy- Shade on polyacrylo- benzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish reddi-n-propylaniline bluish reddi-n-butylaniline strongly bluish redN-methyl-N-.beta.-hydroxyethylaniline bluish redN,N-di-.beta.-hydroxyethylaniline strongly bluish redN-butyl-N-.beta.-chloroethylaniline strongly bluish redN-methyl-N-isopropylaniline bluish redN-ethyl-N-isopropylaniline strongly bluish redN-propyl-N-isopropylaniline strongly bluish redN-methyl-N-ethylaniline bluish redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline bluish redN-methyl-N-isobutylaniline bluish redN-isopropyl-N-isobutylaniline strongly bluish red______________________________________
______________________________________Dyestuff from 3,4'-dimethoxy-2'- Shade on polyacrylo- methylbenzophenone and nitrile______________________________________dimethylaniline strongly yellowish reddiethylaniline yellowish reddi-n-propylaniline yellowish reddi-n-butylaniline yellowish redN-methyl-N-.beta.-hydroxyethylaniline bluish redN-methyl-N-isopropylaniline strongly yellowish redN-methyl-N-ethylaniline yellowish redN-propyl-N-methylaniline yellowish redN-ethyl-N-propylaniline yellowish redN-propyl-N-isopropylaniline yellowish red2-methyl-N-methylaniline reddish orange2-methyl-N-ethylaniline reddish orange2-methyl-N-.beta.-cyanoethylaniline strongly yellowish red2-ethyl-N-.beta.-cyanoethylaniline yellowish red1,2,3,3-tetramethylindoline reddish orange______________________________________
______________________________________Dyestuff from 2,5,4'-trimethoxy- Shade on polyacrylo- benzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish reddi-n-propylaniline strongly bluish reddi-n-butylaniline strongly bluish redN-methyl-N-.beta.-hydroxyethylaniline strongly bluish redN,N-diisopropylaniline yellowish red______________________________________
______________________________________Dyestuff from 3,4,3'-trimethoxy- Shade on polyacrylo- benzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish red______________________________________
______________________________________Dyestuff from 3,4,2'-trimethoxy- Shade on polyacrylo- benzophenone and nitrile______________________________________dimethylaniline strongly bluish reddiethylaniline strongly bluish reddi-n-propylaniline strongly bluish reddi-n-butylaniline rubyN-methyl-N-.beta.-hydroxyethylaniline rubyN-methyl-N-isopropylaniline strongly bluish red______________________________________
______________________________________Dyestuff from 2-methoxy-1-(4'- Shade on polyacrylo-methoxy-benzoyl)-naphthalene and nitrile______________________________________dimethylaniline red-Bordeauxdiethylaniline red-Bordeauxdi-n-propylaniline reddish Bordeaux2-methyl-N-.beta.-cyanoethylaniline red-Bordeaux______________________________________
______________________________________Dyestuff from 2-ethoxy-1-(4'- Shade on polyacrylo-methoxy-benzoyl)-naphthalene and nitrile______________________________________dimethylaniline reddish Bordeauxdiethylaniline reddish Bordeauxdi-n-propylaniline Bordeaux______________________________________
______________________________________Dyestuff from 2-butoxy-1-('- Shade on polyacrylo-methoxy-benzoyl)-naphthalene and nitrile______________________________________dimethylaniline reddish Bordeauxdiethylaniline reddish Bordeauxdi-n-propylaniline Bordeaux______________________________________
______________________________________Dyestuff from 2-methyl-4-n-propoxy- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline yellowish reddiethylaniline strongly yellowish redN-methyl-2-methylaniline strongly yellowish redN-ethyl-2-methylaniline scarletdi-n-propylaniline yellowish redN-cyanoethyl-2-methylaniline yellowish redN-methyl-N-.beta.-cyanoethylaniline bluish red3-ethoxy-N-,N-diethylaniline strongly yellowish red2-methyl-N-benzylaniline strongly yellowish redN-methyl-N-.beta.-hydroxyethylaniline bluish red______________________________________
______________________________________Dyestuff from 3,4-dimethoxybenzo- Shade on polyacrylo- phenone and nitrile______________________________________N-isobutylaniline yellowish red2-methyl-N-benzylaniline bluish redN-phenylmorpholine strongly bluish redN-cyanoethylaniline bluish red______________________________________
______________________________________Dyestuff from 3,4 -dimethoxy-2'- Shade on polyacrylo- methylbenzophenone and nitrile______________________________________dimethylaniline strongly bluish reddiethylaniline strongly bluish reddi-n-propylaniline strongly bluish red2-methyl-N-methylaniline red2-methyl-N-ethylaniline bluish redn-butylaniline redisobutylaniline somewhat bluish red______________________________________
______________________________________Dyestuff from 4-methoxy-2',5'-di- Shade on polyacrylo- methylbenzophenone and nitrile______________________________________di-n-propylaniline bluish redN-methyl-N-.beta.-cyanoethylaniline strongly bluish redN-n-butyl-N-.beta.-chloroethylaniline rubyN-methyl-N-.beta.-hydroxyethylaniline bluish redN-n-butylaniline reddish orangeN-isobutylaniline strongly yellowish red2-methyl-N-methylaniline strongly yellowish red2-methyl-N-ethylaniline strongly yellowish red2-methyl-N-.beta.-cyanoethylaniline yellowish red2-methyl-N-benzylaniline yellowish red2-ethyl-N-.beta.-cyanoethylaniline red1,2,3,3-tetramethylindoline yellowish brick-redN-phenylmorpholine strongly bluish red______________________________________
______________________________________Dyestuff from 2-methyl-4-methoxy-2'- Shade on polyacrylo- chlorobenzophenone and nitrile______________________________________di-n-propylaniline yellowish red3-ethoxy-N,N-diethylaniline reddish orange2-methyl-N-methylaniline reddish orange2-methyl-N-ethylaniline strongly yellowish red2-methyl-N-.beta.-cyanoethylaniline yellowish red2-methyl-N-benzylaniline yellowish redN-n-butylaniline strongly reddish orangeN-isobutylaniline reddish orange______________________________________
______________________________________Dyestuff from 3,4'-dimethoxy-3'- Shade on polyacrylo- bromobenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish reddi-n-propylaniline strongly bluish reddiisopropylaniline bluish reddi-n-butylaniline strongly bluish redN-methyl-N-ethylaniline bluish redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline bluish red______________________________________
______________________________________Dyestuff from 2,4-dimethoxy-3' - Shade on polyacrylo- methylbenzophenone and nitride______________________________________dimethylaniline strongly bluish reddiethylaniline strongly bluish reddi-n-propylaniline strongly bluish redN-methyl-N-.beta.cyanoethylaniline Bordeaux2-methyl-N-.beta.-cyanoethylaniline strongly bluish red2-methyl-N-benzylaniline bluish red1,2,3,3-tetramethylindoline redN-phenylmorpholine red1,3-diphenylpyrazoline reddish blue______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy- Shade on polyacrylo- benzophenone and nitrile______________________________________diethylaniline red-BordeauxN-methyldiphenylamine strongly bluish BordeauxN-methyl-N-4-ethoxyphenyl- currant-blueaniline3-methyl-N-ethyl-N-chloroethyl-aniline currantdi-n-propylaniline strongly bluish reddi-n-butylaniline reddish BordeauxN-methyl-N-hydroxyethylaniline bluish redN-butyl-N-hydroxyethylaniline strongly bluish redN,N-dihydroxyethylaniline strongly bluish redN-methyl-N-.beta.-cyanoethylaniline bluish redN-butyl-N-.beta.-chloroethylaniline strongly bluish redN-ethyl-N-dimethylaminoethyl- strongly bluish redanilineN,N-bis-.alpha.,.beta.-dihydroxyethyl- strongly bluish redanilineN-methyl-N-benzylaniline strongly bluish redN-ethyl-N-benzylaniline bluish redN,N-dibenzylaniline strongly bluish redN-phenylmorpholine Bordeaux3-methyl-N,N-dimethylaniline currant3-chloro-N,N-dimethylaniline currant-blue3-chloro-N,N-diethylaniline reddish black3-methyl-N-ethyl-N-benzylaniline currant-blue3-methyl-N-ethyl-N-.beta.-hydroxyethyl- currantaniline3-methyl-N,N-di-.beta.-hydroxyethyl- currantaniline3-ethoxy-N,N-diethylaniline Bordeaux1-dimethylaminonaphthalene bluish Bordeaux1-diethylaminonaphthalene strongly bluish BordeauxN,N-diisopropylaniline red3-methoxy-N,N-diethylaniline reddish BordeauxN-methyl-N-.beta.-methoxyethyl- red-BordeauxanilineN,N-di-.beta.-methoxyethylaniline red-BordeauxN-methyl-N-isobutylaniline red-BordeauxN-methyl-N-isopropylaniline bluish redN-ethyl-N-isopropylaniline strongly bluish redN-isopropyl-N-isobutylaniline Bordeaux2-methyl-N-methylaniline bluish red2-methyl-N-ethylaniline redN-n-butylaniline bluish redN-isobutylaniline yellowish red2-methyl-N-benzylaniline redN-.beta.-cyanoethylaniline red2-methyl-N-.beta.-cyanoethylaniline redN-benzylaniline yellowish red2-ethyl-N-.beta.-cyanoethylaniline red2,3-dimethyl-N-.beta.-cyanoethyl- Bordeauxaniline2,5-dimethyl-N-.beta.-cyanoethyl- Bordeauxaniline2-ethoxy-N-.beta. -cyanoethylanaline Bordeaux2-hydroxy-N-.beta.-cyanoethylaniline Bordeaux2-methyl-2,3-dihydroindole red1,2,3,3-tetramethylindoline strongly bluish red1-phenyl-3-methylpyrazoline currant-blue1,3-diphenylpyrazoline dark-blueN-methyl-N-ethylaniline bluish redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline bluish redN-propyl-N-isopropylaniline bluish red.alpha.-anilino-isobutyric acid- strongly bluish scarletmethylesterN-n-propyl-o-toluidine somewhat bluish redN-i-propyl-o-toluidine bluish redN-n-butyl-o-toluidine somewhat bluish redN-ethyl-2-ethylaniline redN-ethyl-2-chloroaniline redN-ethyl-o-anisidine bluish Bordeaux______________________________________
______________________________________Dyestuff from 4-methoxy 4'- Shade on polyacrylo- ethoxybenzophenone and nitrile______________________________________dimethylaniline red-Bordeauxdiethylaniline red-Bordeauxdi-n-propylaniline reddish Bordeauxdi-n-butylaniline reddish BordeauxN-methyl-N-.beta.-hydroxyethylaniline bluish redN-methyl-N-.beta.-cyanoethylaniline bluish redN-butyl-N-.beta.-chloroethylaniline strongly bluish red3-ethoxy-N,N-diethylaniline red-BordeauxN,N-diisopropylaniline redN-methyl-N-isopropylaniline red-BordeaxN-methyl-N-isobutylaniline red-BordeauxN-ethyl-N-isopropylaniline reddish BordeauxN-isopropyl-N-isobutylaniline Bordeaux2-methyl-N-methylaniline bluish red2-methyl-N-ethylaniline redN-isobutylaniline red2-methyl-N-.beta.-cyanoethylaniline yellowish redN-n-butylaniline bluish redN-benzylaniline yellowish red2-methyl-N-benzylaniline red2-ethyl-N-.beta.-cyanoethylaniline yellowish red2,3-dimethyl-N-.beta.-cyanoethylaniline BordeauxN-phenylmorpholine reddish Bordeaux1,2,3,3-tetramethylindoline red-BordeauxN-methyl-N-ethylaniline red-BordeauxN-ethyl-N-propylaniline red-BordeauxN-methyl-N-propylaniline red-BordeauxN-propyl-N-isopropylaniline red-BordeauxN-n-butyl-o-toluidine somewhat bluish red______________________________________
______________________________________Dyestuff from 4-methoxy-4'-n- Shade on polyacrylo- propoxybenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish reddi-n-propylaniline bluish reddi-n-butylaniline bluish reddiisopropylaniline bluish redN-methyl-N-isopropylaniline strongly bluish redN-methyl-N-isobutylaniline red-BordeauxN-ethyl-N-isopropylaniline bluish redN-isopropyl-N-isobutylaniline BordeauxN-methyl-N-ethylaniline bluish redN-ethyl-N-propylaniline bluish redN-methyl-N-propylaniline bluish redN-propyl-N-isopropylaniline strongly bluish red______________________________________
______________________________________Dyestuff from 4-methoxy-4'-iso- Shade on polyacrylo- propoxybenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline strongly bluish reddi-n-propylaniline strongly bluish reddi-n-butylaniline red-BordeauxN-methyl-N-.beta.-cyanoethylaniline bluish redN,N-diisopropylaniline redN,N-di-.beta.-methoxyethylaniline red-BordeauxN-methyl-N-isopropylaniline bluish redN-methyl-N-isobutylaniline bluish redN-ethyl-N-isopropylaniline strongly bluish redN-isopropyl-N-isobutylaniline strongly bluish redN-methyl-N-ethylaniline strongly bluish redN-methyl-N-propylaniline strongly bluish redN-ethyl-N-propylaniline strongly bluish redN-propyl-N-isopropylaniline reddish Bordeaux______________________________________
______________________________________Dyestuff from 4-methoxy-4'-n- Shade on polyacrylo- butoxybenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish reddi-n-propylaniline strongly bluish reddi-n-butylaniline rubyN-methyl-N-.beta.hydroxyethylaniline bluish redN,N-diisopropylaniline bluish redN-methyl-N-isopropylaniline bluish redN-methyl-N-isobutylaniline red-BordeauxN-ethyl-N-isopropylaniline strongly bluish redN-isopropyl-N-isobutylaniline reddish BordeauxN-methyl-N-ethylaniline bluish redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline strongly bluish redN-propyl-N-isopropylaniline reddish Bordeauxisobutylaniline somewhat bluish redN-methyl-o-toluidine somewhat bluish redN-ethyl-o-toluidine somewhat bluish red______________________________________
______________________________________Dyestuff from 4-methoxy-4'- Shade on polyacrylo-phenoxybenzophenone and nitrile______________________________________dimethylaniline dull reddiethylaniline "di-n-propylaniline reddish Bordeaux3-chloro-N,N-diethylaniline reddish grey3-ethoxy-N,N-diethylaniline bluish red3-methyl-N,N-dimethylaniline strongly bluish Bordeaux2-methyl-N-.beta.-cyanoethylaniline red2-ethoxy-N-.beta.-cyanoethylaniline Bordeaux______________________________________
______________________________________Dyestuff from 4,4'-diethoxy- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline strongly bluish reddiethylaniline "N-methyl-N-.beta.-hydroxyethylaniline red-BordeauxN-butyl-N-.beta.-hydroxyethylaniline strongly bluish redN,N-di-.beta.-hydroxyethylaniline red-BordeauxN-butyl-N-.beta.-chloroethylaniline reddish BordeauxN-methyldiphenylamine strongly bluish BordeauxN-methyl-N-4-ethoxyphenylaniline currant-greyN-methyl-N-isopropylaniline reddish BordeauxN-methyl-N-isobutylaniline very strongly bluish redN-ethyl-N-isopropylaniline reddish BordeauxN-isopropyl-N-isobutylaniline "N-methyl-N-ethylaniline strongly bluish redN-methyl-N-propylaniline "N-ethyl-N-propylaniline "N-propyl-N-isopropylaniline reddish Bordeaux3-ethoxy-N,N-diethylaniline "2-methyl-N-methylaniline bluish red2-methyl-N-ethylaniline redN-isobutylaniline "2-methyl-N-.beta.-cyanoethylaniline "N-n-butylaniline bluish redN-benzylaniline yellowish red2-methyl-N-benzylaniline red2-ethyl-N-.beta.-cyanoethylaniline yellowish red2,3-dimethyl-N-.beta.-cyanoethylaniline BordeauxN-phenylmorpholine Bordeaux1,2,3,3-tetramethylindoline ruby______________________________________
______________________________________Dyestuff from 4-ethoxy-4'- Shade on polyacrylo-propoxybenzophenone and nitrile______________________________________2-methyl-N-methylaniline red2-methyl-N-ethylaniline "N-isobutylaniline "N-.beta.-cyanoethylaniline "2-methyl-N-.beta.-cyanoethylaniline "______________________________________
______________________________________Dyestuff from 4,4'-di-n-propoxy- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline bluish red3-chloro-N,N-diethylaniline grey2-methyl-N-.beta.-cyanoethylaniline red______________________________________
______________________________________Dyestuff from 4,4'-di-n-butoxy- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline strongly bluish reddi-n-propylaniline Bordeaux______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-2- Shade on polyacrylo-chlorobenzophenone and nitrile______________________________________Dimethylaniline reddiethylaniline "di-n-propylaniline bluish reddi-n-butylaniline "N-methyl-N-.beta.-hydroxyethylaniline "N,N-di-.beta.-hydroxyethylaniline "N-methyl-N-.beta.-cyanoethylaniline "N-butyl-N-.beta.-chloroethylaniline "N-methyl-N-benzylaniline "N-ethyl-N-benzylaniline "N,N-dibenzylaniline strongly bluish redN-methyldiphenylamine bluish BordeauxN-methyl-N-4-ethoxyphenylaniline strongly bluish BordeauxN-phenylmorpholine bluish red3-ethoxy-N,N-diethylaniline yellowish redN,N-diisopropylaniline "N-methyl-N-.beta.-methoxyethylaniline bluish redN-methyl-N-isopropylaniline redN-methyl-N-isobutylaniline bluish redN-ethyl-N-isopropylaniline "N-isopropyl-N-isobutylaniline red-BordeauxN-methyl-N-ethylaniline redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline "N-propyl-N-isopropylaniline "isobutylaniline somewhat yellowish redN-methyl-o-toluidine "N-ethyl-o-toluidine "N-cyanoethyl-o-toluidine red1,2,3,3-tetramethylindoline "______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-3- Shade on polyacrylo-chlorobenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline "di-n-propylaniline strongly bluish reddi-n-butylaniline "N-methyl-N-.beta.-hydroxyethylaniline bluish redN,N-di-.beta.-hydroxyethylaniline strongly bluish redN-butyl-N-.beta.-chloroethylaniline "N-methyl-N-benzylaniline strongly bluish redN-phenylmorpholine "3-ethoxy-N,N-diethylaniline bluish redN,N-diisopropylaniline redN-methyl-N-.beta.-methoxyethylaniline strongly bluish redN-methyl-N-isopropylaniline bluish redN-methyl-N-isobutylaniline strongly bluish redN-ethyl-N-isopropylaniline "N-isopropyl-N-isobutylaniline reddish BordeauxN-methyl-N-ethylaniline bluish redN-methyl-N-propylaniline "N-ethyl-N-propylaniline strongly bluish redN-propyl-N-isopropylaniline "______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-3,3'- Shade on polyacrylo-dichlorobenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline strongly bluish red______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-2- Shade on polyacrylo-methylbenzophenone and nitrile______________________________________dimethylaniline reddiethylaniline bluish reddi-n-propylaniline 41di-n-butylaniline "N-methyl-N-.beta.-hydroxyethylaniline "N,N-di-.beta.-hydroxyethylaniline "N-methyl-N-.beta.-cyanoethylaniline redN-butyl-N-.beta.-chloroethylaniline bluish redN-methyl-N-benzylaniline "N-ethyl-N-benzylaniline bluish redN,N-dibenzylaniline "N-phenylmorpholine "3-methyl-N-ethyl-N-hydroxyethyl-aniline strongly bluish Bordeaux3-ethoxy-N,N-diethylaniline yellowish redN,N-diisopropylaniline "N-methyl-N-.beta.-methoxyethylaniline bluish redN,N-.beta.-methoxyethylaniline "N-methyl-N-isopropylaniline redN-methyl-N-isobutylaniline bluish redN-ethyl-N-isopropylaniline "N-isopropyl-N-isobutylaniline "N-methyl-N-ethylaniline "N-methyl-N-propylaniline "N-ethyl-N-propylaniline "N-propyl-N-isopropylaniline "2-methyl-N-methylaniline yellowish red2-methyl-N-ethylaniline "2-methyl-N-.beta.-cyanoethylaniline "N-isobutylaniline "N-.beta.-cyanoethylaniline "2-hydroxy-N-.beta.-cyanoethylaniline bluish redN-benzylaniline yellowish red2-methyl-N-benzylaniline red2-ethyl-N-.beta.-cyanoethylaniline "2,3-dimethyl-N-.beta.-cyanoethylaniline Bordeaux2,5-dimethyl-N-.beta.-cyanoethylaniline "1- phenyl-3-methylpyrazoline strongly bluish Bordeaux1,2,3,3-tetramethylindoline red3-methyl-N-ethyl-N-.beta.-chloroethyl-aniline Bordeaux______________________________________
______________________________________Dyestuff from 2-methyl-4-methoxy- Shade on polyacrylo-4'-propoxybenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline "di-n-propylaniline "di-n-butylaniline "N-methyl-N-.beta.-hydroxyethylaniline "N-methyl-N-isopropylaniline redN-methyl-N-isobutylaniline bluish redN-ethyl-N-isopropylaniline "N-isopropyl-N-isobutylaniline "N-methyl-N-ethylaniline "N-methyl-N-propylaniline "N-ethyl-N-propylaniline "N-propyl-N-isopropylaniline ".beta.-anilino-isobutyric acid-methylester clear redN-ethyl-o-anisidine strongly bluish red______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-3- Shade on polyacrylo-methylbenzophenone and nitrile______________________________________dimethylaniline red-Bordeauxdiethylaniline "di-n-propylaniline reddish Bordeauxdi-n-butylaniline "N-methyl-N-.beta.-hydroxyethylaniline red-BordeauxN,N-di-.beta.-hydroxyethylaniline strongly bluish redN-methyl-N-.beta.-cyanoethylaniline bluish redN-butyl-N-.beta.-chloroethylaniline reddish BordeauxN-ethyl-n-benzylaniline "N,N-dibenzylaniline strongly bluish redN-phenylmorpholine reddish BordeauxN,N-diisopropylaniline red-BordeauxN-methyl-N-isopropylaniline bluish redN-methyl-N-isobutylaniline red-BordeauxN-ethyl-N-isopropylaniline strongly bluish redN-isopropyl-N-isobutylaniline BordeauxN-methyl-N-ethylaniline red-BordeauxN-methyl-N-propylaniline reddish BordeauxN-ethyl-N-propylaniline "N-propyl-N-isopropylaniline red-Bordeauxn-butylaniline redisobutylaniline bluish red.beta.-anilino-isobutyric acid-methylester redN-methyl-o-toluidine bluish redN-ethyl-o-toluidine somewhat bluish redN-cyanoethyl-o-toluidine redN-cyanoethyl-2-ethylaniline somewhat bluish red1,2,3,3-tetramethylindoline Bordeaux1,3-diphenylpyrazoline blue-green______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-2- Shade on polyacrylo-methyl-5-chlorobenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline bluish reddi-n-propylaniline bluish reddi-n-butylaniline bluish redN-methyl-N-.beta.-hydroxyethylaniline bluish redN-butyl-N-.beta.-hydroxyethylaniline bluish redN,N-di-.beta.-hydroxyethylaniline strongly bluish redN-methyl-N-.beta.-cyanoethylaniline bluish redN-butyl-N-.beta.-chloroethylaniline bluish redN-methyl-N-benzylaniline red-BordeauxN-ethyl-N-benzylaniline bluish redN-methyldiphenylamine bluish BordeauxN-methyl-N-4-ethoxyphenylaniline strongly bluish BordeauxN-phenylmorpholine strongly bluish red3-ethoxy-N,N-diethylaniline yellowish redN,N-diisopropylaniline yellowish redN-methyl-N-.beta.-methoxyethylaniline strongly bluish redN,N-di-.beta.-methoxyethylaniline bluish redN-methyl-N-isopropylaniline bluish redN-methyl-N-isobutylaniline bluish redN-ethyl-N-isopropylaniline bluish redN-isopropyl-N-isobutylaniline strongly bluish redN-methyl-N-ethylaniline bluish redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline bluish redN-propyl-N-isopropylaniline bluish red______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-2- Shade on polyacrylo-chloro-3-methylbenzophenone and nitrile______________________________________dimethylaniline reddiethylaniline reddi-n-propylaniline red-Bordeauxdi-n-butylaniline bluish redN-methyl-N-.beta.-hydroxyethylaniline red-BordeauxN,N-di-.beta.-hydroxyethylaniline bluish redN-methyl-N-.beta.-cyanoethylaniline red-BordeauxN-butyl-N-.beta.-chloroethylaniline bluish redN-methyl-N-benzylaniline bluish red3-ethoxy-N,N-diethylaniline yellowish redN,N-diisopropylaniline redN-methyl-N-.beta.-methoxyethylaniline bluish redN-methyl-N-isopropylaniline redN-methyl-N-isobutylaniline redN-ethyl-N-isopropylaniline bluish redN-isopropyl-N-isobutylaniline bluish redN-methyl-N-ethylaniline redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline bluish redN-propyl-N-isopropylaniline red-Bordeaux______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-2- Shade on polyacrylo-chloro-5-methylbenzophenone and nitrile______________________________________dimethylaniline reddiethylaniline reddi-n-propylaniline bluish reddi-n-butylaniline bluish redN-methyl-N-.beta.-hydroxyethylaniline bluish redN,N-di-.beta.-hydroxyethylaniline strongly bluish redN-methyl-N-.beta.-cyanoethylaniline bluish redN-butyl-N-.beta.-chloroethylaniline strongly bluish redN-methyl-N-benzylaniline strongly bluish redN-methyldiphenylamine bluish Bordeaux3-methyl-N,N-dimethylaniline bluish Bordeaux3-chloro-N,N-dimethylaniline currant-blue3-methyl-N-ethyl-N-.beta.-hydroxyethyl-aniline strongly bluish Bordeaux3-ethoxy-N,N-diethylaniline yellowish redN,N-diisopropylaniline yellowish red2-methyl-5-methoxy-N,N-dimethyl-aniline granateN-methyl-N-.beta.-methoxyethylaniline red-BordeauxN,N-di-.beta.-methoxyethylaniline strongly bluish redN-methyl-N-isopropylaniline bluish redN-methyl-N-isobutylaniline red-BordeauxN-ethyl-N-isopropylaniline bluish redN-isopropyl-N-isobutylaniline BordeauxN-methyl-N-ethylaniline redN-methyl-N-propylaniline redN-ethyl-N-propylaniline bluish redN-propyl-N-isopropylaniline strongly bluish redN-ethyl-2-methylaniline yellowish red2-methyl-N-.beta.-cyanoethylaniline red______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-3- Shade on polyacrylo-chloro-5-methylbenzophenone and nitrile______________________________________dimethylaniline red-Bordeauxdiethylaniline red Bordeaux______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-2,3- Shade on polyacrylo-dimethylbenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline "di-n-propylaniline "di-n-butylaniline "N-methyl-N-.beta.-hydroxyethylaniline "N,N-diisopropylaniline redN-methyl-N-isopropylaniline bluish redN-methyl-N-isobutylaniline "N-ethyl-N-isopropylaniline "N-isopropyl-N-isobutylaniline strongly bluish redN-methyl-N-ethylaniline bluish redN-methyl-N-propylaniline "N-ethyl-N-propylaniline "N-propyl-N-isopropylaniline strongly bluish redisobutylaniline red.alpha.-anilino-isobutyric acid-methylester clear yellowish redN-methyl-o-toluidine redN-ethyl-o-toluidine somewhat yellowish redN-cyanoethyl-o-toluidine redN-cyanoethyl-2-ethylaniline somewhat bluish red______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-2,5- Shade on polyacrylo-dimethylbenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline "di-n-propylaniline red-Bordeauxdi-n-butylaniline bluish redN-methyl-N-.beta.-hydroxyethylaniline red-BordeauxN,N-di-.beta.-hydroxyethylaniline bluish redN-methyl-N-.beta.-cyanoethylaniline red-BordeauxN-butyl-N-.beta.-chloroethylaniline bluish redN-methyl-N-benzylaniline bluish redN-ethyl-N-benzylaniline strongly bluish red3-ethoxy-N,N-diethylaniline red-BordeauxN-methyl-N-.beta.-methoxyethylaniline bluish redN-methyl-N-isopropylaniline "N-methyl-N-isobutylaniline red-BordeauxN-ethyl-N-isopropylaniline bluish redN-isopropyl-N-isobutylaniline red-BordeauxN-methyl-N-ethylaniline bluish redN-methyl-N-propylaniline strongly bluish redN-ethyl-N-propylaniline red-BordeauxN-propyl-N-isopropylaniline "N-n-butylaniline somewhat yellowish redisobutylaniline red.alpha.-anilino-isobutyric acid-methylester. "N-methyl-o-toluidine "N-ethyl-o-toluidine "N-cyanoethyl-o-toluidine "N-cyanoethyl-2-ethylaniline "______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-3,3'- Shade on polyacrylo-dimethylbenzophenone and nitrile______________________________________dimethylaniline red-Bordeauxdiethylaniline "di-n-propylaniline BordeauxN-methyl-N-.beta.-cyanoethylaniline bluish redN-methyl-N-.beta.-hydroxyethylaniline BordeauxN-methyl-N-benzylaniline red-Bordeaux3-ethoxy-N,N-diethylaniline bluish redN,N-diisopropylaniline strongly bluish redN,N-di-.beta.-methoxyethylaniline red-BordeauxN-methyl-N-isopropylaniline reddish BordeauxN-methyl-N-isobutylaniline "N-ethyl-N-isopropylaniline "N-isopropyl-N-isobutylaniline BordeauxN-methyl-N-ethylaniline strongly bluish redN-methyl-N-propylaniline reddish BordeauxN-ethyl-N-propylaniline reddish BordeauxN-propyl-N-isopropylaniline Bordeaux2-methyl-N-.beta.-cyanoethylaniline bluish red______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-3,5- Shade on polyacrylo-dimethylbenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline strongly bluish reddi-n-propylaniline "di-n-butylaniline "N-methyl-N-.beta.-hydroxyethylaniline "N-butyl-N-.beta.-hydroxyethylaniline "N,N-di-.beta.-hydroxyethylaniline "N-methyl-N-.beta.-cyanoethylaniline bluish redN-butyl-N-.beta.-chloroethylaniline strongly bluish redN-methyl-N-benzylaniline "N-ethyl-N-benzylaniline "N-phenylmorpholine "3-methyl-N,N-dimethylaniline strongly bluish Bordeaux3-methyl-N-ethyl-N-.beta.-hydroxyethyl-aniline "3-ethoxy-N,N-diethylaniline Bordeaux3-methoxy-N,N-dimethylaniline red-BordeauxN,N-diisopropylaniline redN-methyl-N-isopropylaniline bluish redN-methyl-N-isobutylaniline strongly bluish redN-ethyl-N-isopropylaniline "N-isopropyl-N-isobutylaniline "N-methyl-N-ethylaniline bluish redN-methyl-N-propylaniline strongly bluish redN-ethyl-N-propylaniline strongly bluish redN-propyl-N-isopropylaniline red-Bordeaux______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-2- Shade on polyacrylo-methyl-6-ethylbenzophenone and nitrile______________________________________2-methyl-N-methylaniline strongly yellowish red2-methyl-N-ethylaniline "1,2,3,3-tetramethylindoline "1,3-diphenylpyrazoline reddish bluedimethylaniline reddiethylaniline "di-n-propylaniline bluish redN-methyl-N-.beta.-cyanoethylaniline strongly bluish redN-methyl-N-.beta.-hydroxyethylaniline bluish red______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-3,3'- Shade on polyacrylo-diethylbenzophenone and nitrile______________________________________dimethylaniline strongly bluish reddiethylaniline ruby______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-3-iso- Shade on polyacrylo-propylbenzophenone and nitrile______________________________________dimethylaniline red-Bordeauxdiethylaniline "di-n-propylaniline reddish Bordeauxdi-n-butylaniline BordeauxN-methyl-N-.beta.-hydroxyethylaniline red-BordeauxN,N-di-.beta.-hydroxyethylaniline "N-methyl-N-.beta.-cyanoethylaniline red-BordeauxN-butyl-N-.beta.-chloroethylaniline "N-methyl-N-benzylaniline "N-ethyl-N-benzylaniline reddish BordeauxN-methyldiphenylamine strongly bluish BordeauxN-methyl-N-4-ethoxyphenylaniline currant-greyN-phenylmorpholine reddish Bordeaux3-methyl-N,N-dimethylaniline currant3-ethoxy-N,N-diethylaniline reddish BordeauxN,N-diisopropylaniline red-BordeauxN-methyl-N-.beta.-methoxyethylaniline "N-methyl-N-isopropylaniline strongly bluish redN-methyl-N-isobutylaniline red-BordeauxN-ethyl-N-isopropylaniline strongly bluish redN-isopropyl-N-isobutylaniline BordeauxN-methyl-N-ethylaniline red-BordeauxN-methyl-N-propylaniline red-BordeauxN-ethyl-N-propylaniline reddish BordeauxN-propyl-N-isopropylaniline "______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-3,5- Shade on polyacrylo-diisopropylbenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylanilie "N-methyl-N-.beta.-hydroxyethylaniline strongly bluish redN-methyl-N-isobutylaniline "______________________________________
______________________________________Dyestuff from 2,4,4'-trimethoxy- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline reddish Bordeauxdiethylaniline "di-n-propylaniline Bordeauxdi-n-butylaniline "N-butyl-N-.beta.-chloroethylaniline BordeauxN-ethyl-N-.beta.-dimethylaminoethyl-aniline "N-methyl-N-isopropylaniline "N-ethyl-N-isopropylaniline "N-propyl-N-isopropylaniline "N-methyl-N-ethylaniline reddish BordeauxN-methyl-N-propylaniline "N-ethyl-N-propylaniline BordeauxN-methyl-N-isobutylaniline "______________________________________
______________________________________Dyestuff from 3,4,4'-trimethoxy- Shade on polyacrylo-benzophenone and nitrile______________________________________dimethylaniline reddish Bordeauxdiethylaniline Bordeauxdi-n-propylaniline "di-n-butylaniline "N-methyl-N-.beta.-hydroxyethylaniline "N,N-di-.beta.-hydroxyethylaniline "N-methyl-N-.beta.-cyanoethylaniline reddish BordeauxN-butyl-N-.beta.-chloroethylaniline BordeauxN-methyl-N-benzylaniline "N-ethyl-N-benzylaniline "N,N-dibenzylaniline bluish BordeauxN-methyldiphenylamine strongly bluish BordeauxN-methyl-N-4-ethoxyphenylaniline currant-greyN-phenylmorpholine Bordeaux3-ethoxy-N,N-diethylaniline "N,N-diisopropylaniline bluish redN,N-di-.beta.-methoxyethylaniline BordeauxN-methyl-N-isopropylaniline strongly bluish redN-methyl-N-isobutylaniline BordeauxN-ethyl-N-isopropylaniline strongly bluish redN-isopropyl-N-isobutylaniline bluish BordeauxN-methyl-N-ethylaniline reddish BordeauxN-methyl-N-propylaniline BordeauxN-ethyl-N-propylaniline "N-propyl-N-isopropylaniline "n-butylaniline redisobutylaniline "N-cyanoethylaniline somewhat bluish red.alpha.-anilino-isobutyric acid-methylester bluish redN-methyl-o-toluidine "N-ethyl-o-toluidine somewhat bluish redN-cyanoethyl-o-toluidine "1,3-diphenylpyrazoline greenish dark-blueN-phenylmorpholine Bordeaux1,2,3,3-tetramethylindoline "______________________________________
______________________________________Dyestuff from dimethylaniline Shade on polyacrylo-and nitrile______________________________________4-methoxy-4'-ethoxy-2,5-dimethyl-benzophenone bluish red4-methoxy-4'-ethoxy-2-methylbenzo-phenone red4-methoxy-4'-ethoxy-2-chlorobenzo-phenone "4-methoxy-4'-ethoxy-2'-methylbenzo-phenone red4-methoxy-4'-ethoxy-2'-methyl-5'-chlorobenzophenone bluish red4-methoxy-4'-ethoxy-2'-chloro-5'-methylbenzophenone red4-methoxy-5'-ethoxy-2'-chloro-benzophenone "4-methoxy-4'-propoxy-2'-methyl-benzophenone bluish red4-methoxy-4'-ethoxy-2-chloro-5-methylbenzophenone red3,4,5,4'-tetramethoxybenzophenone red-Bordeaux2,4,6,4'-tetramethoxybenzophenone strongly bluish red2,3,4,4'-tetramethoxybenzophenone bluish red4-methoxy-4'-isobutoxybenzophenone "4-ethoxy-4'-n-propoxybenzophenone "4-methoxy-4'-ethoxybenzophenone red-Bordeaux4-methoxy-4'-n-propoxybenzophenone bluish red4-methoxy-4'-isopropoxybenzophenone "4-methoxy-4'-n-butoxybenzophenone "4,4'-di-n-propoxybenzophenone "4,4'-di-n-butoxybenzophenone "2-methyl-4-methoxy-4'-propoxy-benzophenone "4,4'-dimethoxy-2-chlorobenzophenone red4,4'-dimethoxy-3-chlorobenzophenone bluish red4,4'-dimethoxy-3,3'-dichlorobenzo-phenone "4,4'-dimethoxy-2-methylbenzophenone red4,4'-dimethoxy-3-methylbenzophenone red-Bordeaux4,4'-dimethoxy-2-methyl-5-chloro-benzophenone bluish red4,4'-dimethoxy-2-chloro-3-methyl-benzophenone red4,4'-dimethoxy-2-chloro-5-methyl-benzophenone red4,4'-dimethoxy-3-chloro-5-methyl-benzophenone red-Bordeaux4,4'-dimethoxy-2,3-dimethylbenzo-phenone bluish red4,4'-dimethoxy-2,5-dimethylbenzo-phenone bluish red4,4'-dimethoxy-3,3'-dimethylbenzo-phenone red-Bordeaux4,4'-dimethoxy-3,5-dimethylbenzo-phenone bluish red4,4'-dimethoxy-2-bromobenzophenone red4,4'-dimethoxy-3-bromobenzophenone bluish red4,4'-dimethoxy-2-methyl-6-ethylbenzo-phenone red4,4'-dimethoxy-3,3'-diethylbenzo-phenone strongly bluish red4,4'-dimethoxy-3-isopropylbenzo-phenone red-Bordeaux4,4'-dimethoxy-3,5-diisopropylbenzo-phenone bluish red3,4,4'-trimethoxybenzophenone reddish Bordeaux______________________________________
______________________________________Dyestuff from 2-methyl-N-methyl- Shade on polyacrylo-aniline and nitrile______________________________________4-methoxy-4'-ethoxybenzophenone bluish red4,4'-diethoxybenzophenone bluish red4-ethoxy-4'-propoxybenzophenone red4,4'-di-n-propoxybenzophenone red______________________________________
______________________________________ Shade on polyacrylo-Dyestuff from dimethylaniline and nitrile______________________________________4-methoxy-4,'-ethoxy-2,5-dimethylbenzo-phenone bluish red4-methoxy-4'-ethoxy-2-methylbenzo-phenone red4-methoxy-4'-ethoxy-2-chlorobenzo-phenone "4-methoxy-4'-ethoxy-2'-methylbenzo-phenone "4-methoxy-4'-ethoxy-2'-methyl-5'-chlorobenzophenone bluish red4-methoxy-4'-ethoxy-2'-chloro-5'methylbenzophenone red4-methoxy-4'-ethoxy-2'-chlorobenzo-phenone "4-methoxy-'propoxy-2'-methylbenzo-phenone bluish red4-methoxy-4'-ethoxy-4-chloro-5-methylbenzophenone red3,4,5,4'-tetramethoxybenzophenone red-Bordeaux2,4,6,4'-tetramethoxybenzophenone strongly bluish red2,3,4,4'-tetramethoxybenzophenone bluish red4-methoxy-4'-isobutoxybenzophenone bluish red4-ethoxy-4'-n-propoxybenzophenone "______________________________________
______________________________________Dyestuff from N-methyldiphenylamine Shade on polyacrylo-and nitrile______________________________________4-methoxy-4'-ethoxybenzophenone bluish Bordeaux4,4'-diethoxybenzophenone strongly bluish Bordeaux4,4'-di-n-propoxybenzophenone strongly bluish Bordeaux4,4'-di-n-butoxybenzophenone "______________________________________
______________________________________Dyestuff from N-methyl-N-4-ethoxy- Shade on polyacrylo-phenylaniline and nitrile______________________________________4-methoxy-4'-ethoxybenzophenone currant4,4'-diethoxybenzophenone currant-grey4,4'-di-n-propoxybenzophenone bluish currant______________________________________
______________________________________Dyestuff from 3-methyl-N,N-dimethyl- Shade on polyacrylo-aniline and nitrile______________________________________4,4'-dimethoxybenzophenone currant4,4'-dimethoxy-2-chloro-5-methyl-benzophenone bluish Bordeaux4,4'-dimethoxy-3,5-dimethylbenzo-phenone bluish Bordeaux4,4'-dimethoxy-3-isopropylbenzo-phenone currant______________________________________
______________________________________Dyestuff from 3-chloro-N,N-dimethyl- Shade on polyacrylo-aniline and nitrile______________________________________4,4'-dimethoxybenzophenone currant-blue4,4'-dimethoxy-2-chloro-5-methyl-benzophenone currant-blue4,4'-dimethoxy-3,5-dimethylbenzo-phenone strongly bluish Bordeaux______________________________________
______________________________________Dyestuff from N-methyldiphenyl- Shade on polyacrylo-amine and nitrile______________________________________4,4'-dimethoxy-2-chlorobenzophenone bluish Bordeaux4,4'-dimethoxy-2-methyl-5-chloro-benzophenone bluish Bordeaux4,4'-dimethoxy-2-chloro-5-methyl-benzophenone bluish Bordeaux4,4'-dimethoxy-3-isopropylbenzo-phenone strongly bluish Bordeaux3,4,4'-trimethoxybenzophenone strongly bluish Bordeaux______________________________________
______________________________________Dyestuff from N-methyl-N-(4-ethoxy- Shade on polyacrylo-phenyl)-aniline and nitrile______________________________________4,4'-dimethoxy-2-chlorobenzophenone strongly bluish Bordeaux4,4'-dimethoxy-2-methyl-5-chloro-benzophenone strongly bluish Bordeaux4,4'-dimethoxy-3-isopropylbenzo-phenone currant-grey3,4,4'-trimethoxybenzophenone currant-grey______________________________________
______________________________________Dyestuff from 2-methyl-N-methyl- Shade on polyacrylo-aniline and nitrile______________________________________4,4'-dimethoxybenzophenone bluish red4,4'-dimethoxy-2-methyl-6-ethyl-benzophenone strongly yellowish red______________________________________
______________________________________Dyestuff from 3-methoxy-N,N-dimethyl- Shade on polyacrylo-aniline and nitrile______________________________________4,4'-dimethoxy-2-chlorobenzo-phenone yellowish red4,4'-dimethoxy-3,5-dimethylbenzo-phenone red-Bordeaux4,4'-dimethoxy-3,3'-dimethylbenzo-phenone bluish red______________________________________
______________________________________Dyestuff from 2-methyl-5-methoxy-N,N- Shade on polyacrylo-dimethylaniline and nitrile______________________________________4,4'-dimethoxy-2-chloro-5-methylbenzo-phenone granate______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-2- Shade on polyacrylo-bromobenzophenone and nitrile______________________________________diethylaniline reddi-n-propylaniline bluish reddiisopropylaniline yellowish reddi-n-butylaniline bluish redN-methyl-N-ethylaniline redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline "isobutylaniline somewhat yellowish redN-methyl-o-toluidine yellowish redN-ethyl-o-toluidine somewhat yellowish redN-cyanoethyl-o-toluidine somewhat bluish red1,2,3,3-tetramethylindoline "______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-3- Shade on polyacrylo-bromobenzophenone and nitrile______________________________________diethylaniline bluish reddi-n-propylaniline "N,N-diisopropylaniline reddi-n-butylaniline strongly bluish redN-methyl-N-ethylaniline bluish redN-methyl-N-propylaniline "N-ethyl-N-propylaniline "______________________________________
______________________________________Dyestuff from 4-methoxy-4'-ethoxy- Shade on polyacrylo-2-methylbenzophenone and nitrile______________________________________diethylaniline bluish reddi-n-propylaniline "diisopropylaniline yellowish reddi-n-butylaniline bluish redN-methyl-N-ethylaniline "N-methyl-N-propylaniline "N-ethyl-N-propylaniline "______________________________________
______________________________________Dyestuff from 4-methoxy-4'-ethoxy- Shade on polyacrylo-2,5-dimethylbenzophenone and nitrile______________________________________diethylaniline bluish reddi-n-propylaniline red-Bordeauxdi-n-butylaniline "N-methyl-N-ethylaniline bluish red______________________________________
______________________________________Dyestuff from 4-methoxy-4'-ethoxy- Shade on polyacrylo-2-chlorobenzophenone and nitrile______________________________________diethylaniline reddi-n-propylaniline bluish redN-methyl-N-ethylaniline redN-methyl-N-propylaniline "N-ethyl-N-propylaniline bluish red.alpha.-anilino-isobutyric acid-methylester somewhat bluish redisobutylaniline redN-methyl-o-toluidine "N-ethyl-o-toluidine "N-cyanoethyl-o-toluidine somewhat bluish redN-cyanoethyl-2-ethylaniline "______________________________________
______________________________________Dyestuff from 4-methoxy-4'-ethoxy- Shade on polyacrylo-2'-methylbenzophenone and nitrile______________________________________diethylaniline bluish reddi-n-propylaniline "di-n-butylaniline "N-methyl-N-ethylaniline redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline "isobutylaniline redN-methyl-o-toluidine "N-ethyl-o-toluidine "N-cyanoethyl-o-toluidine "N-n-propyl-o-toluidine "N-i-propyl-o-toluidine "N-n-butyl-o-toluidine ".alpha.-anilino-isobutyric acid-methylester strongly bluish scarlet1,2,3,3-tetramethylindoline bluish red______________________________________
______________________________________Dyestuff from 4-methoxy-4'-ethoxy- Shade on polyacrylo-2'-methyl-5'-chlorobenzophenone and nitrile______________________________________diethylaniline bluish reddi-n-propylaniline "N-methyl-N-ethylaniline "N-methyl-N-propylaniline "N-ethyl-N-propylaniline "______________________________________
______________________________________Dyestuff from 4-methoxy-4'-ethoxy-2'- Shade on polyacrylo-chlorobenzophenone and nitrile______________________________________diethylaniline reddi-n-propylaniline bluish redN-methyl-N-ethylaniline redN-methyl-N-propylaniline "N-ethyl-N-propylaniline bluish red______________________________________
______________________________________Dyestuff from 4-methoxy-4'-ethoxy- Shade on polyacrylo-2'-chloro-5'-methylbenzophenone and nitrile______________________________________diethylaniline reddi-n-propylaniline bluish redN-methyl-N-ethylaniline redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline "______________________________________
______________________________________Dyestuff from 4-methoxy-4'-n-propoxy- Shade on polyacrylo-2'-methylbenzophenone and nitrile______________________________________diethylaniline bluish reddi-n-propylaniline "N-methyl-N-ethylaniline redN-methyl-N-propylaniline "N-ethyl-N-propylaniline bluish red______________________________________
______________________________________Dyestuff from 4-methoxy-4'-ethoxy- Shade on polyacrylo-2-chloro-5-methylbenzophenone and nitrile______________________________________diethylaniline reddi-n-propylaniline bluish redN-methyl-N-ethylaniline redN-methyl-N-propylaniline "N-ethyl-N-propylaniline bluish red______________________________________
______________________________________Dyestuff from 3,4,5,4'-tetramethoxy- Shade on polyacrylo-benzophenone and nitrile______________________________________diethylaniline red-Bordeaux______________________________________
______________________________________Dyestuff from 2,4,6,4'-tetramethoxy- Shade on polyacrylo-benzophenone and nitrile______________________________________diethylaniline strongly bluish red______________________________________
______________________________________Dyestuff from 2,3,4,4'-tetramethoxy- Shade on polyacrylo-benzophenone and nitrile______________________________________diethylaniline bluish reddi-n-propylaniline strongly bluish red______________________________________
______________________________________Dyestuff from 4-methoxy-4'-iso- Shade on polyacrylo-butoxybenzophenone and nitrile______________________________________diethylaniline strongly bluish red.alpha.-anilino-isobutyric acid-methylester clear redN-ethyl-o-anisidine Bordeaux______________________________________
______________________________________Dyestuff from 4-ethoxy-4'-n- Shade on polyacrylo-propoxybenzophenone and nitrile______________________________________diethylaniline bluish reddi-n-propylaniline strongly bluish reddiisopropylaniline bluish reddi-n-butylaniline strongly bluish redN-methyl-N-ethylaniline bluish redN-methyl-N-propylaniline bluish redN-ethyl-N-propylaniline strongly bluish red______________________________________
______________________________________Dyestuff from 4-n-propoxy-2'- Shade on polyacrylo-chlorobenzophenone and nitrile______________________________________dimethylaniline bluish reddiethylaniline somewhat bluish reddi-n-propylaniline bluish redN-methyl-N-.beta.-cyanoethylaniline clear rubyn-butylaniline yellowish redisobutylaniline "N-methyl-o-toluidine "N-ethyl-o-toluidine "N-cyanoethyl-o-toluidine bluish red1,2,3,3-tetramethylindoline yellowish redN-phenylmorpholine strongly bluish red______________________________________
______________________________________Dyestuff from 4-n-butoxy-2'- Shade on polyacrylo-chlorobenzophenone and nitrile______________________________________dimethylaniline somewhat bluish reddiethylaniline reddi-n-propylaniline somewhat bluish redN-methyl-N-.beta.-cyanoethylaniline ruby3-diethylaminophenetole strongly yellowish redisobutylaniline yellowish redN-methyl-o-toluidine somewhat yellowish redN-ethyl-o-toluidine redN-cyanpoethyl-o-toluidine bluish redN-benzyl-o-toluidine somewhat bluish redN-phenylmorpholine red-Bordeaux1,2,3,3-tetramethylindoline yellowish red1,3-diphenylpyrazoline strongly bluish violet______________________________________
______________________________________Dyestuff from 4-methoxy-4'-iso- Shade on polyacrylo-butoxybenzophenone and nitrile______________________________________diethylaniline strongly bluish red.alpha.-anilino-isobutyric acid-methylester clear redN-ethyl-o-anisidine Bordeaux______________________________________
______________________________________Dyestuff from 4,4'-dimethoxy-2- Shade on polyacrylo-methyl-5-isopropylbenzophenone and nitrile______________________________________isobutylaniline red.alpha.-anilino-isobutyric acid-methylester bluish redN-methyl-o-toluidine redN-ethyl-o-toluidine "N-cyanoethyl-o-toluidine somewhat bluish redN-cyanoethyl-2-ethylaniline "______________________________________
______________________________________Dyestuff from 3,4-dimethoxy-2'- Shade on polyacrylo-chlorobenzophenone and nitrile______________________________________dimethylaniline strongly bluish reddiethylaniline strongly bluish reddi-n-propylaniline reddish Bordeaux3-diethylaminophenetole yellowish brick-redn-butylaniline bluish redisobutylaniline somewhat bluish redN-methyl-o-toluidine redN-cyanoethyl-o-toluidine strongly bluish redN-ethyl-o-toluidine somewhat bluish redN-cyanoethyl-2-ethylaniline ruby1,2,3,3-tetramethylindoline red______________________________________
______________________________________Dyestuff from 3,4-dimethoxy-2'- Shade on polyacrylo-bromobenzophenone and nitrile______________________________________dimethylaniline strongly bluish reddiethylaniline strongly bluish reddi-n-propylaniline Bordeaux3-diethylaminophenetole brick-redn-butylaniline somewhat bluish redisobutylaniline somewhat bluish redN-methyl-o-toluidine yellowish redN-ethyl-o-toluidine yellowish redN-cyanoethyl-o-toluidine strongly bluish red1,1,3,3-tetramethylindoline red______________________________________
______________________________________Dyestuff from 4-phenoxy-2'- Shade on polyacrylo-chlorobenzophenone and nitrile______________________________________N-methyl-o-toluidine orangeN-ethyl-o-toluidine orangedimethylaniline strongly reddish orangediethylaniline strongly yellowish reddi-n-propylaniline strongly yellowish red______________________________________
______________________________________Dyestuff from 4-phenoxy-2'- Shade on polyacrylo-methylbenzophenone and nitrile______________________________________dimethylaniline yellowish scarletdiethylaniline yellowish scarletdi-n-propylaniline strongly yellowish redmethyl-cyanoethylaniline somewhat yellowish redmethyl-hydroxyethylaniline somewhat yellowish redN-butyl-.beta.-chloroethylaniline somewhat yellowish redN-ethyl-N-.beta.-dimethylaminoethyl-aniline strongly bluish redN,N-dimethyl-m-toluidine yellowish redN-ethyl-N-.beta.-dimethylaminoethyl-m-toluidine BordeauxN-ethyl-N-benzyl-m-toluidine strongly bluish redN,N-dimethyl-m-phenetidine orangeN-methyl-diphenylamine Bordeauxn-butylaniline somewhat reddish orangeisobutylaniline somewhat reddish orange.alpha.-anilino-isobutyric acid-methylester yellowish scarletN-cyanoethylaniline yellowish scarletN-benzylaniline yellowish scarletN-methyl-o-toluidine somewhat reddish orangeN-ethyl-o-toluidine somewhat reddish orangeN-isopropyl-o-toluidine somewhat reddish orangeN-n-butyl-o-toluidine somewhat reddish orangeN-cyanoethyl-o-toluidine yellowish scarletN-cyanoethyl-2-ethylaniline yellowish scarletN-benzyl-o-toluidine scarletN-n-butyl-m-toluidine brownish redN-ethyl-2-ethylaniline orangeN-ethyl-2-chloroaniline bluish redN-ethyl-o-anisidine strongly yellowish red1,2,3,3-tetramethylindoline somwhat reddish orangeN-phenylmorpholine somewhat yellowish red______________________________________
______________________________________Dyestuff from .alpha.-anilino-isobutyric Shade on polyacrylo-acid-methylester and nitrile______________________________________2,4'-dimethoxy-benzophenone bluish red2-methoxy-4'-ethoxy-benzophenone bluish red2,4'-dimethoxy-3'-methyl-benzophenone strongly bluish red2-methoxy-4'-propoxy-benzophenone strongly bluish red2,4'-dimethoxy-2'-methyl-5'-chloro- clear stronglybenzophenone yellowish red2,4'-dimethoxy-2'-chloro-benzophenone copper-red2,4'-dimethoxy-2'-chloro-5'-methyl-benzophenone yellowish red2,5,4'-trimethoxy-benzophenone strongly bluish red2,4,6,4'-tetramethoxy-benzophenone strongly bluish red4,4'-diethoxybenzophenone clear red4-ethoxy-4'-propoxybenzophenone red4-methoxy-4'-isopropoxybenzophenone clear yellowish red4,4'-dimethoxy-3,3'-dimethyl-benzophenone clear red4,4'-dimethoxy-3,5-dimethyl- clear somewhatbenzophenone bluish red4,4'-dimethoxy-3,5-diisopropyl-benzophenone bluish red4,4'-dimethoxy-3-chlorobenzophenone strongly bluish red4,4'-dimethoxy-3-bromobenzophenone somewhat bluish red4,4'-dimethoxy-2-methylbenzophenone clear yellowish red4-methoxy-4'-propoxy-2'-methyl-benzophenone red4,4'-dimethoxy-2-methyl-5-chloro-benzophenone clear red4-methoxy-4'-ethoxy-2'-methyl-5'-chlorobenzophenone clear red4-methoxy-4'-ethoxy-2'-chloro-benzophenone bluish red4,4'-dimethoxy-2-chloro-3-methyl-benzophenone somewhat bluish red4,4'-dimethoxy-2-chloro-5-methyl-benzophenone red4-methoxy-4'-ethoxy-2'-chloro-5'-methylbenzophenone bluish red4-methoxy-4'-ethoxy-2-chloro-5-methylbenzophenone bluish red______________________________________
EXAMPLE 5
A stamp-pad ink yielding strong prints is prepared from 2 parts by weight of the triphenyl-methane dyestuff the preparation of which is described in Example 1, 60 parts by weight glycerol, 20 parts by weight of water and 20 parts by weight of spirits.
EXAMPLE 6
East Indian bastard skin which has been prepared for dyeing in the usual way is dyed in a liquor ratio of 1:10 with 1% of the dyestuff which is described in Example 1 and has previously been pasted with the same amount of 30% acetic acid, in a drum at 40.degree. C. for 45 minutes. The leather is finished in known manner. A bluish red dyeing of good fastness properties is obtained.
EXAMPLE 7
A stamp-pad ink yielding strong prints is produced from 2 parts by weight of the triphenyl-methane dyestuff the preparation of which is described in Example 2, 60 parts by weight glycerol, 20 parts by weight of water and 20 parts by weight of spirits.
EXAMPLE 8
East Indian bastard skin which has been prepared for dyeing in the usual way is dyed in a liquor ratio of 1:10 with 1% of the dyestuff which is described in Example 2 and has previously been pasted with the same amount of 30% acetic acid, in a drum at 40.degree. C. for 45 minutes. The leather is finished in known manner. A bluish red dyeing of good fastness properties is obtained.
EXAMPLE 9
A stamp-pad ink yielding strong prints is produced from 2 parts by weight of the triphenyl-methane dyestuff the preparation of which is described in Example 3, 60 parts by weight glycerol, 20 parts by weight of water and 20 parts by weight of spirit.
EXAMPLE 10
East Indian bastard skin which has been prepared for dyeing in the usual way is dyed in a liquor ratio of 1:10 with 1% of the dyestuff which is described in Example 3 and has previously been pasted with the same amount of 30% acetic acid, in a drum at 40.degree. C. for 45 minutes. The leather is finished in the usual manner. A bluish red dyeing of good fastness properties is obtained.

Number	Date	Country
1811652	Nov 1968	DEX
1811336	Nov 1968	DEX
1811338	Nov 1968	DEX
1811337	Nov 1968	DEX

Triaryl-methane dyestuffs

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