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United States Patent Office Patented Mar 3,238,221 United States Patent Office Patented Mar. 1, 1966 1. 2 3,238,221 Aryl Sulfonamides suitable for the production of the TETRAAZAPORPHINE DYESTUFFS dyestuffs of Formula I are, for example, the following: Peter Schnitz, Cologne-Stammheim, and Detlef Delfs, NE Opiaden, Germany, assignors to Farbenfabriken Bayer Aktiengeseischaft, Leverkusen, Germany, a corporation 5 of Germany No Drawing. Filed June 5, 1961, Ser. No. 114,619 (D-on Claims priority, application Germany, June 11, 1960, NH F 31,440 3 Claims. (CI. 260-314.5) 10 : {D-onen The invention relates to new tetraazaporphine dye NH stuffs; more particularly it relates to tetrazaporphine dye stuffs of the general formula / 15 {D-onotor NE A x-N-AR -) (I) In this general formula A represents the residue of a tetraazaporphine dyestuff, in particular of a phthalo (D-Ionicator cyanine dyestuff which may be free of metal or which 20 NE may contain metal atoms, X stands for -CH2-, -SO or -CO-, R means hydrogen, a lower alkyl or hydroxy Substituted lower alkyl radical, Ar represents a residue of the benzene, diphenyl, diphenylamine, diphenyloxide NE 25 CHs or naphthalene series and Y stands for an optionally sub / stituted Sulfonamido or sulfonylamino group, in stands SONEICHN for an integer from 1 to 8. A particularly valuable class of dyestuffs among the Yo Hs compounds of the Formula I are those in which the NH Sulfonamido group Y corresponds to the general formula 30 -SO-NEI-R1-OSO32. (II) {D-onent or -so-N-R-R-R-oso.2 (III) NEI. R2 35 wherein R means an alkylene bridge having 2 or 3 car {Donounction bon atoms between -NH- and -OSOZ, Z is hydro CH3 gen or an alkali metal cation, R2 is a lower alkyl group, N CH4OH Rs represents an alkylene group having 2 to 3 carbon 40 / atoms between SO2NEICHN N CEO NH, and -R4 RA stands for -O-, -S- or 45 { X-so-HN-O In these aniline sulfonamides the sulfonamide group may R6 being hydrogen, R5-OSOZ or a lower alkyl group Stand in o- and preferably in the m- or p-position to the and R5 is a lower alkylene group having 2 to 3 carbon amino group. Among naphthylamine derivatives the fol atoms between -R4- and -OSO3Z. It is to be under lowing are to be mentioned: stpod that the residue Ar contains at least one substituent Y; it may also bear more than one of those sulfonamido SONECEO or sulfonylamino groups. It is an object of the present invention to provide new variable dyestuffs. Another object is the provision of 55 new dyestuffs which carry the substituents II or III, being able to undergo chemical linkage with hydroxyl group-containing materials, particularly cellulose-contain SONECEO ing textile materials. Still another object is the provision of dyestuffs which possess highly valuable fastness prop 60 HOECHNOS -NE erties. It is also an object of the invention to provide dyeings on cellulose-containing materials which, when dyed with the dyestuffs carrying substituents of the For mulae II and III, exhibit excellent fastness to wet process SONICEOH ing, such as to washing. 65 The aforesaid sulfonamide components may contain The new dyestuffs are obtainable by reacting phthalo further substituents such as halogen, nitro, alkyl, alkoxy, cyanine sulfonic acid chlorides or -carboxylic acid chlo Sulfonamide, Sulfone, carbonamide, free sulfonic acid and rides or chloromethyl compounds of phthalocyanines with carboxylic acid groups, and others. aryl-sulfonamides or sulfonylaminoaryl compounds, con Starting phthalocyanines which may be sulfochlorinated taining a primary or secondary amino group, the aryl 70 are metal-free as well as metal-containing phthalocyanines compounds belonging to the afore-mentioned series. of which there may be mentioned, for example, copper-, 3,238,221 3. 4. nickel-, cobalt-phthalocyanine, tetraphenyl-copper-phthal group-containing amine components of the aromatic or ocyanine, 5,5',5',5'-tetraphenyl-3,3,3',3'-tetramethyl aliphatic series. 4,4',4',4' - tetraaza-copper-phthalocyanine, tetrachloro The new dyestuffs are highly valuable compounds copper-phthalocyanine and other substitution products of which are suitable, inter alia, for the dyeing and print phthalocyanines; further starting components are copper ing of cotton and regenerated cellulose. If the dyestuffs phthalocyanine - 4-tetrasulfonic acid, copper phthalocya contain groupings which may react with hydroxyl group nine-3-tri-sulfonic acid, nickel phthalocyanine-3-disulfonic or polyamide group-containing materials with the forma acid, cobalt phthalocyanine-3-tri or -tetra-sulfonic acid, tion of chemical linkage, such as sulfonic acid-hydroxy tetraphenyl-copper phthalocyanine-tetrasulfonic acid or alkylamide-sulfuric acid semi-ester groups, haloalkyl -tetracarboxylic acid, nickel and copper mixed complexes O amino or haloacylamino groups, mono- or dichlorotri from 2 or 3 mols of phthalic acid (or its dinitrile or 1 azinyl or -pyrimidinyl groups, epoxide groups, sulfofluo amino-3-imino-isoindolenine) and 2 or 1 mol of pyridine ride groups, esterified hydroxyalkyl-sulfone groups and 2,3-dicarboxylic acid (or -dinitrile), dimethyl maleic acid the like, the products are preferably used in an aqueous dinitrile, 1,2-dicyano-3,6-dithiacyclohexene-1- or 1-phenyl solution which may be treated with alkaline reactive sub 3,5-diamino-triazole (1,2,4); in these phthalocyanines sul 5 stances such as alkali metal hydroxide or alkali metal fonic acid and carboxylic acid groups can be converted carbonate, or with compounds convertible into substances into the corresponding acid halide group by methods of alkaline reaction, such as alkali metal bicarbonate. known as such, e.g., by reaction with chlorosulfuric acid/ Further assistants may be added to the solution which, thionylchloride. Known chloromethyl phthalocyanines however, should not react with the dyestuffs in an unde are to be employed for producing the dyestuffs of Formula 20 sirable manner. Such additives are, for example, sur I wherein X stands for -CH-. face-active substances such as alkylsulfates, or substances The new dyestuffs can also be obtained by varied meth preventing migration of the dyestuff, or dyeing auxiliaries ods. Thus, for example, phthalocyanine-sulfonic acid or such as urea or inert thickeners such as oil-in-water emul -carboxylic acid chlorides may be reacted with primary sions, tragacanth, starch, alginate or methyl-cellulose. or secondary aromatic amines of the aforesaid series such 25 The solutions or pastes thus prepared are applied to as aniline, o-, m- or p-toluidine, chloraniline, N-methyl the material to be dyed, for example by padding in the aniline, N-hydroxyethylaniline, o-anisidine, aminodimeth foulard or by printing, and subsequently heated for some ylbenzene, N-cyanethylaniline, amino-diethylbenzene, 1 time to an elevated temperature, preferably to 40–150 or 2-aminonaphthalene, 4-aminodiphenyl, 4-aminodiphen C. Heating may be carried out in the hot flue, in a ylmethane, diphenylamine and the like, these sulfonic acid 30 Steaning apparatus, on heated rollers or by introduction or carboxylic acid arylides then sulfo-chlorinated in the into heated concentrated salt baths, singly as well as arylide radicals with, for example, chloro-sulfonic acid/ consecutively in any desired order. thionylchloride, and the sulfochlorides then reacted with If a padding or dyeing liquor is used without alkali, optional primary or secondary amines of the aliphatic, the dry material is subsequently passed through an alka araliphatic or aromatic series. 3 5 line solution to which common salt or Glauber salt is For the last-mentioned processes, there are to be con added. The addition of salt prevents the migration of sidered as amines among others: ammonia, methylamine, the dyestuff from the fibre. ethylamine, propylamine, butylamine, n-hexylamine, iso After fixation, the dyeing material is rinsed hot and, hexylamine, dodecylamine, stearylamine, N-methyl-ste if the purpose for which the dyed material is to be ap arylamine, dimethylamine, amines from first runnings of 40 plied requires, subsequently soaped, insufficiently fixed fatty acids, di-(2-ethyl-n-hexyl)-amine, ethanolamine, N dyestuff particles thus being removed. Dyeings of ex methyl-ethanolamine, diethanolamine, propanolamine, 2 cellent fastness to wetting are thus obtained. hydroxy-butylamine, 5-aminoethylsulfate, y-aminopropyl For printing hydroxyl group-containing materials, a sulfate, 3- or 4-aminobenzene-1-sulfonic acid-hydroxy printing paste is used which is prepared from the dye ethylamine or -1-sulfonylaminoethyl-hydrogensulfate, 3 45 Stuff Solution, a thickener Such as sodium alginate, and or 4-aminobenzene-1-(3-hydroxyethyl)-sulfone, benzyl a compound of alkaline reaction or splitting off alkali amine, N-methyl-benzylamine, cyclohexylamine, dicyclo upon heating such as sodium carbonate, potassium car hexylamine, N-methyl-N-hydroxy-ethyl - propylene - di bonate or Sodium bicarbonate, the printed material is amine-(1,3), N,N-dihydroxyethyl-propylene - diamine then rinsed and, if necessary, finally soaped. (1,3), N,N-dimethyl-propylene-diamine-(1,3), N-phenyl 50 Wool, silk and synthetic polyamide and polyurethane propylenediamine-(1,3), N-hydroxy-ethyl-ethylenediamine, materials such as fibres, filaments, yarns, etc., are pref N,N- or N,N'-dihydroxyethyl-ethylenediamine, piperazine, erably dyed from a neutral to acid bath. The dyeing N-hydroxyethyl-piperazine and the sulfates of the afore may be followed by a short alkaline treatment at, e.g., mentioned hydroxyalkylamines, morpholine, thiomorpho pH 6.5 to 8 thus improving the wet fastness
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