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Es PATENT OFFICE 2,342,662 MERCAPTO-Phthalocyanines

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Es PATENT OFFICE 2,342,662 MERCAPTO-Phthalocyanines Patented Feb. 29, 1944 2,342,662 UNITED STAT Es PATENT OFFICE 2,342,662 MERCAPTO-PHTHALOCYANINEs. Norman Hulton Haddock, Black?ey, Manchester, England, assignor to imperial Chemical Indus tries Limited, a corporation of Great Britain No Drawing. Application April 29, 1941, serial No. 390,912. In Great Britain May 13, 1940 1 Claims. (C. 8-3) This invention relates to novel textile dyes, amino compounds by converting the amino pigments and intermediates of the phthalo groups over the diazo derivatives into mercapto. cyanine Series. More particularly, this inven groups, by methods well known in the prior art. tion relates to mercapto compounds of the gen However, such known and synthetically prepared eral formula, Q- (SH), wherein a is a nu 5 aromatic mercapto compounds do not possess meral from 1 to 4, while Q stands for the radical sufficient substantivity to textiles and similarity of a phthalocyanine compound selected from the to commercial sulfur colors in dyeing properties group consisting of metal-free phthalocyanines to be useful as textile dyes. and metallic phthalocyanines of the benzene and It is known that substituents can be intro-3, naphthalene series, their homologs and substitu 0 duced into the phthalocyanine molecule, either tion derivatives, e. g., halogen, nitro, phenyl, by a direct Substitution process, such as for in phenoxy, benzoyl, etc.; and to sulfur-type dyes stance by halogenation or sulfonation, or by derivable therefrom by oxidation of the mer synthesizing phthalocyanines from substituted captO groupS. - w intermediates, such as aromatic substituted ni Compounds of the phthalocyanine series find 5 triles, ortho-dicarboxylic acids, or derivatives at present their greatest commercial use as valu thereof. However, the introduction of the mer able pigments for printing inks, paints and other capto or disulfide groups into a phthalocyanine pigmented coating compositions. It is known molecule has not heretofore been accomplished that the introduction of certain substituents, by any method described in the prior art. such as for instance sulfonic acid groups into the 20 This invention has as its object to prepare new phthalocyanine molecule, renders the products mercaptophthalocyanine derivatives which can Soluble in water and produces direct dyes which be applied to textiles in much the same way as can be used for textile and paper dyeing. How commercial sulfur colors, but which possess ever, such known water-soluble phthalocyanines much superior fastness properties and very de are deficient in exhausting properties, and the 23 sirable bright bluish-green to greenish-blue wash fastness and other fastness properties of shades, such as have not been obtained hereto the dyeings on Cotton are not entirely satisfac fore from any known commercial sulfur dye. A tory. further object of the invention is to utilize the It is known that many aromatic intermediates well known and outstanding tinctorial strength of the benzene and naphthalene series and some 30 and clarity of the pigment shade, shown by com heterocyclic compounds can be fused with sul pounds of the phthalocyanine series, for the dye fur and alkali polysulfides to give vattable dyes, ing and printing of cotton, wool and other come generally referred to as sulfur colors, which con mon fabric. A still further object is the prep tain sulfur atoms in the molecule, and which aration of intermediates of the phthalocyanine can be dissolved in diluted alkaline sodium sul 35 Series which possess one or several functional fide or hydrosulfite to give what appears to be groups not heretofore available in phthalocy a Solution of the alkali salt of a mercapto com anine compounds. These groups serve particu pound. From this solution (or vat) textiles are larly well for the introduction of very desirable dyed in various shades. When these dyeings are substituents into commercial phthalocyanines. exposed to the air or other oxidizing agents, the 40 These objects are accomplished by the follow Water-Soluble alkali salts are converted on the ing invention. It was discovered that mercapto fiberinto the original insoluble dye. While these compounds of the phthalocyanine series can be known sulfur dyes are comparatively inexpen obtained readily from the corresponding amino sive, and are therefore used to a great extent phthalocyanines by known methods, for instance for the dyeing of cotton and other fabric, they 45 by converting the amino compounds into the show, in general, quite inferior fastness proper- . diazo derivatives which in turn are converted ties and dull shades and they cannot be used to the xanthate esters, followed by hydrolysis at for commercial textile printing by conventional elevated temperatures. These alkali-soluble vat dye methods, since the presence of free sul mercapto compounds are readily oxidized by air fur or sulfides in the printing paste renders the 50 or other oxidizing agents to form water-insolu same unsatisfactory to be printed from engraved ble disulfides. These dyes can be redissolved in copper cylinders which are stained by such sul aqueous Sodium sulfide solution, forming a vat fur compounds. from which textiles can be dyed much in the It is known that one or several mercapto or disulfide groups can be introduced into aromatic sis finalsame bluish-greenmanner as commercial or greenish-blue sulfur colors.dyeings Theob 2 2,842,862 tained from these products on cellulosic material Berichte der deutschen Chemischen Giesellschaft, show outstanding fastness to washing and light 1890, volume 23, page 738) and alkali metal and are, in general, equal in fastness properties thiosulfates (see Die Methoden der organischen and clarity of shade to the best known anthra Chemie, Houben, 1924, volume 4, page 628). quinone vat dyes. The dyeings are discharge In its broadest aspects, this invention includes able to good whites by steaming after treatment the manufacture of sulfur-containing, dyestuffs with dimethyl (sulfobenzyl) phenyl ammonium by the oxidation of mercaptophthalocyanines, chloride, sodium hydroxide and sodium formal however obtained, and also the use of these mer dehyde sulfoxylate solutions. The new sulfur captophthalocyanines as intermediates for novel containing dyes may also be used for printing O dyes Suitable for pigmentation purposes or deco on textiles by conventional printing methods ration of textiles or the coloring of frasoline, oils, which are used for the printing of anthraquinone plastic masses and similar material. and indigoid vat dyes, preferably by the glucose I have further found that the intermediate caustic soda method. products in the manufacture of the above-men The new mercapto compounds, obtained by 5 tioned sulfur dyestuffs, namely, the phthalocya this invention, also serve as intermediates for nine xanthate esters or thiocyanophthalocya the preparation of desirable new pigments and nines, can themselves be applied to cellulosic ma colored compounds such as thioglycolic acids, terial from Sodium sulfide solution according to thioethers, thioesters, and other products which the usual practice with sulfur dyestuffs. By this can be obtained by replacement of the reactive 20 procedure the phthalocyanine Xanthate esters or hydrogen (attached to the sulfur atom) by vari thiocyanophthalocyanines become hydrolysed in ous aliphatic or aromatic radicals. the sodium Sulfide Solution to mercaptophthalo Instead of starting with the amino-phthalo cyanines. Thus by the dyeing technique usual cyanines, one or more mercapto groups can also with sulfur dyestuffs there are produced on the be introduced into the phthalocyanine molecule 25 fiber, the same sulfur dyestuffs, to the production by replacing hydrogen or halogen atoms in in substance of which the aforementioned process phthalocyanines by sulfur, whereby disulfides relates. In this way also, there are obtained dye are formed which may be treated with alkaline ings with the properties which have already been reducing agents to give the corresponding mer described. Accordingly, the present invention re capto compounds. Thus, chlorinated copper 3) lates not only to the manufacture by the afore phthalocyanine reacts under suitable conditions. said process of Sulfur dyestuffs in Substance but (for instance when treated in pyridine solution also to their production on the fiber, that is on with alkali polysulfides) to give disulfide deriva the cellulosic material, directly by application tives which are similar in dyeing properties to the thereto of the intermediate products in the man . mercapto compounds obtained from amino cop 35 ufacture process, which are phthalocyanine per phthalocyanines. Xanthate esters and thiocyanophthalocyanines. The amino-phthalocyanines, which serve as the . The above special feature of this inveption is preferred starting materials for the products of being described in further detail and claimed in a this invention, are obtainable by the methods de copending application, filed by me as a continua scribed in British Patent 529,847. They are pref O tion-in-part of the instant application, Ser. No. erably made by subjecting 4-nitro-phthalimide, 482,822, filed April 12, 1943. or mixtures of 4-nitro-phthalimide together with The invention is further illustrated, but not unsubstituted phthalimide in molecular proport intended to be limited, by the following examples, tions (in ratios of 1:3, 2:2, or 3:1), to the usual in which the parts are by weight. fusion with metal salts in the presence of urea 45 and ammonium molybdate, followed by reduc Eacample
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