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United States Patent Office Patented Jan. 23, 1951 2,539,178 UNITED STATES PATENT OFFICE 2,539,178 METALLIZED AZO DYESTUFF AND PROCESS OF PRODUCING THE SAME Heinrich Hugo Bestehorn, Easton, Pa., assignor to General Aniline & Film Corporation, New York, N. Y., a corporation of Delaware No Drawing. Application November 6, 1947, Serial No. 784,507 2 Claims. (C. 260-148) 1 2 The present invention relates to new metallized contemplated herein, are obtained by coupling a azo dyestuffs and to a method for their pro diazotized amine of the benzene or naphthalene duction. Series free from Substituents ortho to the azo It is rather standard procedure in the dyestuff group with a hydroxy bearing coupling compo art to increase the fastness properties of a ZO nent capable of coupling under alkaline con dyestuffs by subjecting these dyestuffs to metal ditions in ortho position to said hydroxyl group. lization, either in Substance or on the fiber. It xamples of suitable primary amines for use has always been the impression of the art that in the preparation of the involved dyestuffs are: in order to effect this result, the azo dyes treated should have in o-position to and on Opposite n-Nitroaniline sides of the azo bridge, groupS Such as hydroxyi, p-Nitroaniline amino, carboxy, and the like, capable of cooperat N-acetyl-p-phenylenediamine ing with the metallizing agents employed to effect N-amino-o-cresol ethyl ether the desired chelation. Inasmuch as the number p-Amino phenol of azo dyes having the desired groups on opposite 5 Sulfanilic acid sides of the azo bridge and in o-position thereto Aniline are comparatively few in number, the very ad p-Toluidine vantageous metallizing process for increasing the m-Chloroaniline fastness of the dyes has been fairly limited. m-Nitroaniline It has now been ascertained, quite contrary to 20 (3-Naphthylamine the assumptions of the art, that azo dyes con 2-naphthylamine-5-sulfonic acid taining a hydroxyl group on One side of the azo 2-naphthylamine-6-sulfonic acid bridge in o-position thereto but no groups ortho Benzidine, to the azo bridge on the opposite side thereof and the like. can be completely chelated by treating said azo The coupling components are chiefly those of dyes with a metallizing agent in an alkaline So the class of phenols, naphthols and pyrazolones. lution in the presence of an oxidizing agent, Suitable coupling components are, for example: peroxidic in character. By this treatment an activation of the non-hydroxyl carrying side of B-Resorcylic acid the azo compound is brought about so that the 30 (3-Naphthol condensed System of Chelate rings forms over Naphthionic acid the azo bridge, Strengthening the compound to 1-naphthol-4-sulfonic acid the same extent as where the azo dyes utilized 1-naphthol-4.7-disulfonic acid contain chelating groups in Ortho position on 1-naphthol-5-Sulfonic acid both sides of the azo bridge. Thus, it has been 1-naphthol-3,6-disulfonic acid discovered that the azo dyes metallized by the H-acid present method have the Same fastness to light G-acid as that exhibited by azo dyes containing two Acetyl H-acid chelating groups in ortho position to the azo Benzoyl H-acid bridge. Inasmuch as the criterion for complete 40 K-acid chelation is the light fastness of the metalized (8-Hydroxy naphthoic acid dyes, the comparability of this property in the Dichlorbenzoyl K acid old dyes and those under consideration estab R-acid lishes a priori that the degree and extent of Schaeffer's acid chelation involved in both instances is equivalent. 45 2-naphthol-3.6.8-trisulfonic acid The azo dyes produced by the aforementioned The urea of 2-amino-5-naphthol-7-sulfonic acid method and the method of producing such dyes 1-phenyl-3-methyl-5-pyrazolone constitute the purposes and objects of the present 1-p-sulfophenyl-3-carboxy-5-pyrazolone, invention. The azo dyes, the metallization of which is 50 and the like, 2,589,178 3 4. The process is not only operative with mono of water at 15° C. Seventy-eight ml. of per azo dyes but also with poly-azo dyes, either bis-, formic acid (obtained from 57 ml. of 30% hy tris- or tetra-azo dyes. drogen peroxide, mixed with 21 ml. of 90% formic As illustrative of the mono-azo dye, capable of acid) are gradually added to the dye solution undergoing metallization by my method refer along with 40 to 50 grams of soda in Solution to ence may be made to those derived from the maintain the mixture continuously alkaline. following arylamines and coupling components: The temperature is raised to 30 C. and 144 m). of 25% copper sulfate Solution (CuSO4.5H2O) are Arylamines Coupling Components added. The color of the mixture changes from 0 red to red-violet. After 2 hours no further deep m-nitro-aniline. B-resorcylic acid. ening of shade occurs. The mixture is filtered chromotropic acid. and the paste dried in the usual manner. A dye REEN -acetyl-p-phenylenediamine---- R-acid. N-acetyl-p-phenylenediamine---- acetyl F-acid. Stuff is obtained which dyes cotton a brownish g-naphthylamine ---------------- finaphthol. Bordeaux. The light-fastness, as expressed in 2-naphthylamine-5-stillonicM-anillo-o-cresol ethyl ether----- acid. 1-naphthol-4-sulfonicRacid. acid. fadeometer hours, is 5 times as good as that of 2-naphthylamine-6-sulfonic acid.-- 6-Inaphthol. the original dye. p-toluidine----------------------- 1-methyl-3-phenyl-5-pyrazolone. aniline.--------------------------- 1-p -sulfo-phenyl-3-carboxy-5- Eacample 2 B-naphthylamine-----------------1-naphthol-4,7-disulfonicpyrazolone. acid.. The known dyestuff of the following constitu - 20 tion OE OE NH COO. ON The following illustrate satisfactory poly-azo is dyed on cotton, diazotized on the fiber and de dyes: Veloped with 2-naphthol, yielding on the fiber the red dyestuff: Arylamine - - - - - Coupling Component 0 2 mols of sulfanilic acid----------- 1 mol of 3-naphthol. ' - - 2 mols of aniline.---------------- -- 1 Imol of the urca from 2-amino-5- naphthol-7-sulfonic acid. 2 mols m-acetamino-aniline----...- 1 mol of the urea from 2-amino-5- aphthol--sulfonicR acid. of 8-naphthol. ) 1 Inolsing of the example disazo (afterdye of hydroly the pre- 2 i SS). OH O3S- NE For effecting metallization of the azo dyes, the dyes either in substance or on the fiber are heated ) =N gh CO with an alkaline solution of the metallizing agent, and the oxidizing agent. The metallizing agents are those usually employed, such as the Salts of copper, nickel, cobalt, chromium, and the OS like. Preferably the sulfates of copper, nickel and cobalt are utilized, whereas with chromium, 45 best results are obtained with the formate. Into the developer bath, after complete devel The oxidizing agents are, as stated, of peroxidic oping, are added, for a 10-gram piece of cotton, character. Suitable oxidizing agents are: 10 ml. of a 6% hydrogen peroxide solution and 5 ml. of a 40% copper sulfate solution Hydrogen peroxide 50 (CuSO4.5H2O). After heating to 60-80° C. for Sodium perborate about 20 minutes, the red color has changed to Ammonium persulfate a deep, full blue. The new dyestuff, perfected PotaSSium perphosphate on the fiber, has very good fastness to light and Per-formic acid Washing. Per-propionic acid 55 The literature has already mentioned the pos Per-butyric acid Sibility of forming one-sided, chelate rings on Per-benzoic acid, azo dyes involving a single hydroxyl group. These and the like. It has been found that metalliza compounds, however, are of no technical value tion proceeds most satisfactorily when the ox for the reason that the strengthening of the azo idizing agent is one of the aforesaid oxygen car bridge by a complete chelate ring extending over rying fatty acids, and their use is therefore rec the azo bridge is not accomplished. As a con ommended. sequence, such dyes have not found technical ap The temperature to which the compositions plication since their light fastness is improved to are heated to effect metallization varies, but a negligible extent, if at all, by such metalliza usually ranges from about 30 to about 100° C. (5 tion. The procedure of the prior art in this re The following examples serve to illustrate the Spect is completely at odds with the present invention but it is to be understood that the in method wherein the azo bridge is strengthened Vention is not restricted thereto. by a complete chelate ring yielding dyes of the Same light fastness as those obtained by the Eacample 1 usual metallizing procedures involving a plural One-seventh of a gram-mol of the disazo dye ity of groups Ortho to the azo bridge. stuff obtained by coupling 2 mols of diazotized Various modifications of the invention will oc aniline with 1 mol of the urea of 2-amino-5- cur to operators in this field, and I therefore do naphthol-7-sulfonic acid in the presence of soda, not intend to be limited in the patent granted in the usual manner, is resludged in 2000 parts s except as necessitated by the appended claims, 2,589,178 5 6 claim: temperature of 30° C. in an aqueous alkaline 1. The process of metallizing azo dyes which solution in the presence of copper sulfate and comprises heating an azo dye derived from a di performic acid. azotized amine selected from the class consisting 6. The dyestuff obtained according to the proc of those of the benzene and 3-naphthalene series 5 ess of claim 1. and free from substituent groups in the ortho 7.
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