USRE19527E - Azo dyestuff and process of making - Google Patents

Description

Reissued Apr. 9, 1935 UNITED STATES PATENTS OFFICE 19,527 AZO DYESTUFF AND PROCESS orv MAKING SAME August Leopold Laska and Arthur Zitscher, f-

fenbach -,0'n the Main, Germany, assignors to I. G. Farbenindustrie Aktiengesellschalt, Frankfort-on-the-Main, Germany No Drawing. Original No. 1,457,114, dated May 29, 1923, Serial No. 611,503, January 8, 1923. Application for reissue August 28, 1932, Serial 3 (,laims.

aromatic amine in which the nucleus may be substituted by one ormore substituents selected from the group consisting of halogen, alkyl, alkoxy and nitro groups but which does not contain any group causing solubility, such as the sulfonic acid or carboxylic acid group, with an othro-alkoxyarylide of the 2, 3-hydroxynaphthoic acid of the general formula:

, COAQHQ Alkyl wherein the nucleus R may be substituted by a substituent selected from the group consisting of halogen, alkyl, alkoxy and nitro groups.

The new dyestuiis are represented by the general formula:

wherein the nuclei R and R1 may be substituted by substituents selected from the group consisting of halogen, alkyl, alkoxy and nitro groups.

The dyestuffs can be used for the production of color lakes of an excellent fastness to light and give, when produced on the fiber, orange to red and Bordeaux shades of asingularfastness tolight, they are when dry, orange to red and brownish powders, insoluble in water, soluble in sulfuric acid to a violet to green solution yielding upon reduction with stannous chloride an amine and an ortho-alkoxyarylamide'of the l-amino-2-hydroxy-3-naphthoic acid. 1

The invention is illustrated by the following examples:

1'. A diazo-solution, prepared in the usual manner from 16.2 parts of 2,5-dichloroaniline, is poured, while stirring well, into an aqueous suspension of 30.7 parts of ortho-anisidide of the 2,3-

hydroxynaphthoic acid, prepared by dissolving it in dilute caustic soda lye and precipitating with dilute acetic acid. The dyestuff separates in brightly reddish flakes, it is filtered, when the combination is complete, washed until neutral and advantageously used in the form of a paste. Mixed with the usual substrata it forms color lakes of an excellent fastness to light.

The dyestufi has the following structural formula:

CHI.

Instead of ortho-anisidide we may use orthophenetidide of the 2,3-hydroxynaphthoic acid.

2. PRODUCTION OF THE DYESTUFFS ON II-IE FIBER Padding bath 10 rams of ortho-anisidide of 2,3-hydroxynapht oic acid are well stirred with 20 cc. of caustic soda lye of 34 B. and 20 cc. of Turkey red oil, dissolved with 200 cc. of hot water and made up to 1 liter.

The cotton goods, which are impregnated with this solution, are well wrung out and then developed in the following:

3 grams of 4-chloro-1,2-toluidine are diazotized in the usual manner, the solution is diluted with cold water to I liter, neutralized with sodium acetate and 50 grams of common salt are added.

The dyed goods are rinsed, as usually, with cold and warm water, then soaped, while boiling well, rinsed again and dried.

Printing-directions Printing-color 4500 cc. of the diazo solution,

4000 grams of tragacanth thickening 1:20, 1000 cc; of aluminium sulfate 1:1, I

500 ec.-. of sodium: acetate 1 :1, 1 a.

by a substituent selected from the group consisting of halogen, alkyl, alkoxy and nitro groups.

2. The water-insoluble azo dyestuffs of the general formula: I

10 After printing the goods are dried-at 40 (Lto 5p? 0., soaped with a warm and fbly alkalifieso'lii x tion of soap and rinsed with hot water.

The following table gives the-tints o r =number of the dyestuffs, prepared according to the" present: 6 ONH@ process, and of the color lakes obtained there from: m -1 Diazo compiflifidofz r I Combined with: Shades:

1 3-chloroaniline Ortho-anisidide of 2 fi-liydroxynaphthoic acid--- Orange. 2 2-ch1oroaniline. a o Yellowish red. 3 2, -dicl1loroaniline Yellowish red. 4 4-chloro-l, 2-toluidine. Red. 5 5-chlol'0-1; 2-toluldin Blulsli'red 6 6'chloro-1, Z-toluidin ed. 7 Yellowish red. 8 Bluish red. 9 Bordeaux 10 Red. 11 Yellowish red 12 Bordeaux. 13 Bordeaux. 14 Bordeaux. 15 3-nitro-l, 4-toluidiue Red.

16 40hl0lO-2-filti'0B-l1llltl8; Y Bluish red. 17 Dianisidine Reddish blue. 18 Ortho-phenetole-azo-a]pha-naphtliylamine Black. 19 4-cl1loro-l, 2-toluidine d- 20 5-cl1loro-l, 2-toluidine Bluish red. 21 fi-chloro-l, 2-toluidine Red; 22 2-chloro-l, 4-toluidine Red. 23 3-chloro-1, 4 toliiidine. Red. 24 4-chl0ro-2-nitroan1line: Bluish red. 25 4-chloro-l, 2-anisidine- Bordeaux. 26 5-chloro-1, 2-anisidine. Reddisli Bordeaux. 27 4-nitro-l, z-anisidine Bluish red. 28 E-nitro-l, Z-toluidine Red. 29 3-nitro l, 4=toluidjne Reddish Bordeaux. 30 m-aminoazptoluene Like garnet. 31 5chloro-1, 2-toluid1'ne. Bluish red. 32 6-chloro-1, 2-toluidilge Yellowish red. 33 4-chloro-l, Z-aniSidln. Bordeaux. 34 3-nitrol, 4-to1uidine Bordeaux. 35 S-nitro-l, 4-to1uidine. Bluish red. V 36 5'-nitro-1, 2-anisldine; Reddish Bordeaux. 37 2, 5-dichlofoaniline Yellowish red. 3s 3-nitro-l, 4-toluidine 'Blui s'h red. 39 5-nitro-l, 2-toluidin 0.; Bordeaux. 40 2, S-diChIoib-aniline. 2, Flo-5ydroxynaphthoyl-3-ammo-l, 4-creso1ethyl- Yellowlsh red.

' e er. 41 3-nitro-l, 4-toluidine'. do Bluish red. 42 5-nitro-1, 2-toluidine. do Bluish red. 43 4-nitro-l 2-anisidine. Red.

44 4-"chloio-l, 2-anlsidine 'Bluish red. 45 2, .5-dichloroaniline; Brownish orange.

Since an object of the present invention is; to provide dyestuffs of goodfastness properties, which dyestuffs are insoluble. in water and all kalies, it is to be understood 'tl'mt the aromatic nuclei of the general formulae appearing in the appended claims do not contain any substituents which are known to render organic compounds soluble in water or alkaliesand to tend to depreciate the fastness of the dyestuffs to alkalies. Substituents of this kind are} for instance, the sulfonic acid and the earboxylic acid group.-

1. The water-insoluble 'a'zo" dyestuffs of the general formula: I 1 Y wherein the nuclei R aiid fumayue substituted oo-NH OCH;

suorus'r LEQPOLDV ARTHUR ZITSCHER.