Патент USA US2129964код для вставки
2,129,964 Patented Sept. 13, 1938 UNITED STATES v"Parr-zen" OFFICE 2,129,964 Azo DYEST‘UFFS' Hans Boos, Levérkusen-I.‘ G.-Werk, Germany, as signor to General’ Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application June 5, 1935, Serial No. 25,179. In Germany June 21, 1934 :3 Claims. D (Cl. 260-160) The present invention relates to new substan tive azo dyestuffs. I have found that new and valuble cotton dye stuffs can be obtained by combining l-aminoaryl 5-pyrazolone-3-carboxylic acids which may bear any substituents in the aryl nucleus, such as halo gen, alkyl, alkoxy, the sulfonic acid group, the carboxylic acid group, and the like, with the diazo benzoyl) -aminophenylurea - 3,3’ - disulfonic acid compounds obtainable from the aminobenzoyl amino compounds including the aminobenzoyl~ amino-benzoylamino compounds derived from di amino diphenylurea sulfonic acids, diamino stil bene sulfonic acids and dehydrothiotoluidine and its homologues, such as dehydrothioxylidine. azolone-3-carboxylic acid containing 56 grams of are dissolved in 2 litres of water and 11 grams of sodium carbonate, 13.8 grams of sodium nitrite are added thereto, and‘ the solution is poured into a mixture of 56 ccs. of 10-N hydrochloric acid, some water and ice. The diazotization is soon complete, and the mixture is introduced into a solution of 50 grams of 1-m-nitrophenyl-5-pyr sodium carbonate. The formation of the dye 1O stu? proceeds quickly, the dyestu? formed is re duced with sodium sul?de .at '70-80° C. and after this isolated in the usual manner and dried. In its free state it corresponds to the following formula: 15 00011 S 0:11 ' I /o \ NHI NH-ONMGNe-e r GHQ' CO COOH NH: 25 TO U! CO-———N S 03H As diazotization components suitable for the 30 purpose of the present invention there are men tioned by way of example di- (0-, m-, or p-amino benzoyl) -diaminodiphenylureadisulfonic acid, di (aminobenzoylaminobenzoyl) - diaminodiphenyl ureadisulfonic acid. My new dyestuffs are in form of their alkali metal salts generally yellow to orange powders dyeing the vegetable ?ber generally yellow to orange shades. The dyeings obtained with my new dyestu?s 40 can be after-treated with formaldehyde in the usual manner, whereby their fastness to washing is considerably improved. Further the new dye it dyes cotton a reddish yellow which can be dis charged to a pure white both with a neutral and 30 an alkaline reacting discharge paste. When diazotized and developed with l-phenyl-IS-meth ' yl-5-pyrazolone, a yellow fast to washing, with 18 naphthol an orange fast to washing is obtained. It may be mentioned that the non-diazotized 3-5 dyeings can be aftertreated with formaldehyde, whereby the fastness to washing is remarkably improved without unfavorably influencing the dis chargeability. - I claim: 1. Azodyestuffs after the general formula 40 SOaH stuffs can be diazotized in substance or on the 45 ?ber and developed with the usual developers. Compared with the known dyestu?s which are distinguished from my new dyestuffs by contain ing as coupling component l-aminophenyl-3 methyl-5-pyrazolone instead of a 1-aryl-5-pyr azo1one-3-carboxylic acid the new dyestuffs yield S 0311 somewhat more reddish shades of an improved dischargeability both with a neutral and alkaline wherein Py stands for the radical of a l-meta discharge paste. aminophenyl - 5 - pyrazolone - 3 - carboxylic acid, ‘ The invention is illustrated by the following examples, without being limited thereto: 55 45 Example 1.—64 grams of 4,4’-(di-p-amin0~ dyeing the vegetable ?ber yellow shades which can be discharged to a pure white both with a neutral and an alkaline reacting discharge paste. 50 2 ' ‘ 2,129,964 2. The dyestu? having in the free state the following formula: s 03H $005 5 NH NH—C 0- / stands for a radical of an aminobenzoyl compound of the gI'Oup consisting of aminobenzoyl diamino /°\ N=N—(|3H III , s NH; I 5 c 0 -—-N— 00 1 ' 1O 10 coon dyeing cotton reddish yellow shades which, when diphenylul‘ea ‘sulphonic acids and aminobenzoyl diazotized on the ?ber and developed with l- diaminostilbene sulphonic acids, and R’ means 1 phenyl - 3 - methyl - 5 - pyrazolone, yield meta—amin0pheny1- 5 —pyrazo1one - 3 — carboxylic shades fast to washing. 20 yellow _ acid, dyeing the vegetable ?ber generally yellow to 3. Disazodyestu?s of the formula 7 > orange shades which can be aftertreated with 20 N:N__R, R\ ' . N=N—R’ 25 wherein N: R formaldehyde or diazotized and developed. / \ HANS ROOS.