Патент USA US2134038код для вставки
Patented Oct. 25, 1938 ‘ ‘UNITED=STATES PATENT. ICE 5 ‘ MoNoAz0 DYESTUFFS » ' Richard 'Fleischhauer, F‘rankfort~on-the4Main; Fechenheim, Germany, assig'nor' to General > w v Aniline iWo'rks, Inc.,'_New York,; N. Y., aucoré " _' g’ poration _ of ; Delaware narrating‘. ‘Application October 16, 1936,, se rial No. 105,931. In Germany October 7:22, 1935 . . 3 Claims. This invention relates to valuable new mono azodyestu?‘s, more particularly to those of the general formula: i0 wherein X stands for a member selectedfrom the group consisting of hydrogen, alkyl, alkoxy». cyclohexyl and phenyl‘ andR stands for a mono cyclic radicle of the benzene series. ., ,7 I _‘ Y . The new dyestuifs are obtained by combining :15 the diazo compounds of aromatic amines of the generalformula; ' ‘ ' (01." 266L921. ‘ ' When the combination is performed in ‘the pres ence of another acid-binding agent such as for example sodium bicarbonate dyestuifs are ob tained which yield somewhat more reddish brown shades of similar properties. Instead of the above diazo component there may be used in an analogous manner other similar compounds such as for example: N- (4-aminophenyl) -N-methoxyacety1-aminoa cetic acid,‘ N-(é-amiriophenyl) - N - carbethoxy it aminoacetic. acid; N-(4-aminopheny1) -N-chloro acetyl-aminoacetic acid; N-(4-aminophenyl) éNphenoxyacetylearninoacetic acid; " N-(-4-amino phenyl) -N-benzoyl-aminoacetic acid, N-(4-ami nophenyl) -N-hexahydrobenzoyl—aminoac'etic ac ' id, N-(‘l-aminophenyl) -N-propionyl-aminoacetic acid, N- (4-amino-2-methylphenyl) -N-acetyl-am inoacetic acid or substituted derivatives thereof. . | COX (wherein X has the above signi?cation) with 2 By employing the corresponding amounts of these diazoilcomponents.instea'diof the above said N (4 >— aminophenyl) - N .- acetyl - aminoacetic ‘ acid aryl-amino-8-naphthol-6-sulfonic acids.’ , brown dyestuffs areobtained of quite analogous ' The diazo components employed for themanu facture of the dyestuffs of this invention may be‘ properties and partly distinguished by an'vin prepared for example in an analogous manner to creased fastness to light or by deeper brown the methods described in German Patents No. shades. Thus the dyestu? prepared by starting 25 152,012 and No. 154,556. Or they may be pre " from N- (é-aminophenyl) :N-benzoyl-aminoacetic pared by starting from nitro-aryl-glycines which I acid yields deeper brown shadesthan the dyestuff are acylated and reduced. . The new dyestuffs yield on animal ?bers brown shades of good fastness properties. They are dis tinguished from similar brown dyestuffs by a very good solubility and partly by a much better fast 9 prepared by starting from N-(4-aminophenyD N-acetyl-aminoacetic acid. Example 2 20.8 parts of N-(‘i-aminophenyl) -N-acetylami ness to ironing. The following examples illustrate, but do not noacetic acid are diazotized in the usual manner limit the invention, the parts being by weight. 35 parts of 2- (4'-vmethoxy-phenylamino) ~8-naph Example 1 and the diazo solution obtained is combined with 35 thol-?-sulfonic acid in the presence of an excess of sodium acetate. The dyestu?" formed is iso lated and dried. It forms a dark powder, easily inc-acetic acid are diazotized in the usual manner ' 4D and the diazo solution obtained is combined with soluble in water, dyeing wool deep violet-tinged brown shades of quite similar properties as the 35 parts of 2-(4’-methoxyphenylamino) -8-naph 20.8 parts of N-(4-aminophenyl) -N-acetyl-am thol-6-sulfonic acid in the presence of an excess of sodium carbonate. The dyestu? formed of the 45 formula: dyestuif obtained according to Example 1, but of a somewhat increased fastness to light. The diiference between the new product and the dyestu? obtained according to Example 1 45 50 COCHa HOaS/ is isolated by the addition of an acid and of sodi um chloride. It forms when dry a dark powder, very easily soluble in water, dyeing wool deep full brown shades of good fastness to ironing and 5 01 light and of good levelling power. 50 seems to be caused by the fact that a little amount of another dyestu? is produced beside the dye stu? the formula of which is given in Example 1, whereby the combination probably takes place in the 1-position of the coupling component. When 55 2,184,038 the amount of the sodium acetate employed is varied, more or less of the byproduct is formed and the properties of the dyestu? obtained may be altered thereby. Instead of the above coupling component there may also be employed in the foregoing examples 2-arylamino-8-naphthol-6-sulionic acids which dium chloride. It is when dry a dark powder. soluble in water, dyeing wool and silk very deep brown shades of good Iastness to ironing and of good levelling power. I claim: 1. The monoazo dyestu?s consisting substan tially .0! products of the general formula: OH may contain further substituents in their aryl radicle. Such coupling components are for ex-v ‘ ‘ ~ ' 10 ample: ' NH-B. (LO-X Z-phenylamino 8-naphthol-6-sulfonic acid,_ 2 (2'- methyl-phenylamino) -8-naphtho1-6-sulfonic acid, 2- (2’-methoxy-phenylamino) -8-- naphthol H018 wherein X standsfor a member selected from the 6-sulfonic acid, 2-(2',4’-dimethoxy-phenylami-r group consistingof hydrogen, alkyl, alkoxy, cyclo 15 no) -8-naphthol-6-sulfonic acid, 2-(2’,5’—dime thoxy-phenylamino)-8-naphthol-6<sulfonic acid, 2-(chloro-phenylamino) -8-naphthol # 6 -' sulfonic 20 acids, 2- (sulfo-phenylamino) -8-naphtho1-6-syul fonic acids, z-(carboxy-phenylamino)é8-naph thol-?-sulfonic acids. ' 15 hexyl and phenyl and R. stands for armonocyelic ‘radicle‘ of. the benzene series, which dyestuffs are easily soluble in water and yield on animal ?bers brown shades of good iastness properties. 2. A monoazo dyestu? consisting substantially 20 of a product of the formula: ' H NHOO on: 25 25 .HOIS which dyestu? represents a dark powder, soluble Ezamplevb‘ ' 30 10 3000-011, _ 'in water, dyeing wool and silk very deep brown > 19.4 parts of N-(4-aminophenyl) -N-.formy1-am— , shades of good fastness to ironing and of good lev elling power. 30 I inoacetic acid are diazotized in the usual manner ,' 3. A monoazo dyestu?.’ consisting substantially and the diazo solution obtained is allowed to run of a product of the formula: into a solution of 35 parts of 2- (4’—methoxy-phen 35 as NHOO cm COCH; which dyestu? represents a dark powder, very :10 ylamino)e8enaphthol-?-sulfonic acid containing easily soluble in water, dyeing wool deep full an excess of sodium bicarbonate. When the com bination is complete the dyestu? formed substan tially consisting of a product of the formula: brown shades of good fastness to light and iron ing and of good levelling power. 45 OH :15 so is isolated by the addition of an acid and of so 40 RICHARD FLEISCHVHAUER.