Патент USA US2113029код для вставки
‘Patented Apr. 5, 1938 i r 2,113,029; auaozc isms . _.~ " Eugene A. Marhush', Jersey City, N. 1.. neither to " Pharma ‘Chemical Corporation, New- York, N.- Y.. a-corporation oi’ New York ‘ - 'No Application January25,gl934,_p Serial No. 708,31956 .' 4 Claims. My invention relates to new coloring compounds (Cl. 8-5) Example 2 and refers particularly to coloring compounds Eleven parts of the. sodium salt of 4-chlor-2 which are valuable for the printing or dyeing of diazo-inuno-proline-anisol, 9 parts acetoacetylr cellulose ?bers. naphthylamine are “thoroughly mixed and they mixture employed as follows: ' The compounds of my invention are obtainable by combining diazo compounds of aromatic mono 5 Two parts of the above mixture are dissolved arnines and their substitution products, but which , in '7 parts water; 1/2 part ammonium ricinoleate, do not contain a sulfonic group, with the aceto— 11/2 parts caustic soda solution 30 Bé., 2% parts acetyl-naphthylamines having the formula 10 Cellosolve or denatured alcohol and the resulting 10 solution thickened to a paste with 15 parts starch 00-011‘ _ _ gum tragacanth. This paste is printed on'the cotton cloth, and hung up to dry. The printed ~ Hr-CONHR cloth may be developed immediately ‘after dry ing, or the dried printed cloth stored until re -15 in which R is'a naphthalene ring which may con tain ethoxy, alkyl,._halogen, or nitro group, or 15 groups, but not a solubilizing acid group such as quired by the printer. The developing is accom plished- by placing the cloth in an ager :and steam- ' _ __carboxylic. or sulionic groups. ing in the presence of acetic or formic acid vapor The. acetoacetyl-naphthylaniines may be pro- _ for ?ve minutes. It is then soaped hot, rinsed well and dried. 20 Where the use of an ager is inconvenient. the duced by condensing the naphthylamines, or their 20 substituted compounds, with an alkyl-aceto . acetate, as methyl-acetoacetate and ethyl-aceto acetate. developing may be done by immersing the printed ' cloth in a warm bath of, a mixture of acetic and formic acids in the presence of Glauber’s salt. This developing bath is heated until the shades‘ 25' have reached maximum iullness. Furthermore, - The compounds of my invention may be pro duced either in substance or upon the fiber, the latter being capable of accomplishment by im 2 pregnating the fiber with ' they . acetoacetyl the printed material may be padded with the acid naphthylamine compound and then treating the mixture using the well known padding method ' thus impregnated ?ber with the diazo compound, after which the material is dried with heat, rinsed, or by mixing the diam-compounds in their stabi 3O ing the stabilized form-oi one oi the compounds the applied mixture with an acid reaction, I-give the following as one method for the pro duction of one of the compounds of my invention in substance: Example 1 of my invention upon the ?ber'z- . Example av One mole of chlor-anisol-diazo-imino-alpha Fifteen parts 01’ para-amlno-acetanilid are amine are suspended in 500 parts of water at 40° 0., and a cold solution containing '1 parts of caus tic soda is added. This solution is then cooled to 8° C. by addition of ice and neutralized or made slightly acid with dilute acetic acid. '15 parts of sodium acetate solution in 500 parts of water are then added. acetyl-naphthylamine are thoroughly mixed to gether, printed upon the ?ber and developed as described in Example 2. Other stabilized forms of my compounds may be employed instead of alpha-pyrrolidine car boxylic acid such as those produced from amino— sulfo-benzoic acid‘, methyl-glycocoll, diglycol 45 amine, amino-pyridine-carboxylic acid. Among theshade's oi colors producibie by my invention, I mention the, following; The diazotized para-amino-acetanilid solution 50 is then added slowly to the solution of aceto acetyl-p-naphthylamine under continuous agita- ‘ 5 washed well to neutrality with water and dried. I give the following as one method of develop ing one of the compounds of my invention upon 80 the ?ber:— _ . I pyrrolidine-carboxylic acid and one mole of aceto diazotized in the usual manner and neutralized with a solution of sodium acetate. 40 Twenty-six parts of acetoacetyl-p-naphthyl tion and the whole stirred for about two hours. Three parts of a sodium hydroxide solution are then added to itv very slowly and agitated for another hour. The insoluble color is then ?ltered, .30, ‘soaped, washed well and dried. ' I, give the following as one method of employ lized form with the acetoacetyl naphthylainine compound, applying it to the ?ber‘ and treating Diazotized amine - Coupling component Shade 50 2,6 dichloro-aniline .............. -_ Acetolaacgyl-c-na'ph- Yellow. y e. , ' > p-Nitro-toluidine ............... -. AcetoaoetyM-mphe thylamine. Do. - ' , ' p-Amino-phonyl-benzyl-ether...... Aoetoacetyl-a-naph- Greenlah thylamino. v, ~ Chloranisidino ............... .4... Aoetoecetyl-chlor-? ‘ ' naphthylamine. Chloranisidine ................. .'.. 'Acetoacetyl-c-naph, thylaminc. llow. ' ‘ 0.‘. , ~‘ Do. I I do not limit myself to the particular chemi ' - 2 2,118,029 cals, quantities, times, temperatures or steps of a basic paste. containing a water-soluble diazo procedure as set forth as these are given simply as a means for clearly explaining my invention. What I claim is: imino derivative of 3-chlor,-_6_-methoxyaniline and 1. The method of dyeing a cellulosic material which comprises impregnating the material with a basic paste containing awater-soluble diazo-imin‘o ‘ derivative'of aniline and a non-substantive aceto acetyl-naphthylamine and subjecting the im- ’ 10 pregnated material at elevated temperature to the action of a mild acid. ‘ 2. Themethod of dyeing a cellulosic material which comprises impregnating the material with a non-substantive acetoacetyl - naphthylamine and subjecting the impregnated material at ele vated temperature to the action of a mild acid. ‘3; A cellulosic textile fabric dyed with the cou pling product of a diazotized aniline and a non substantive aceto-acetyl-naphthylamine. 4. A cellulosic textile fabric dyed with the cou pling product of a diazotized 3-chior-6-methow aniline and a non-substantive aceto-acetyi naphthylamlne. . EUGENE A. MARKUBH.