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Unlteosrates PATENT OFFICE' Patented Nov. 9, 1948 2,453,420 ‘ uNlTEosrATEs PATENT OFFICE‘ MORPHOLINE SALTS 0F SULFONATED AZO DYE‘ COMPONENTS AND THEIR. PREPARA-l HaroldlGfGreig, ‘Princeton, N. J., assignor to , ‘ Radio Corporation of America, a‘corporation‘ ‘ of Delaware . No Drawing. Application December 21, 1944, 3 Serial No. 569,264 , I 14 Claims. (01.260-247) . 1‘ “ 2 a . ‘The present invention relates to _morpholine ‘dye components, while they provide the desired salts of the sulfo acids‘ of cyclic organic com water solubility, have a number of disadvantages.‘ pounds having a sulfonic acid group linked to a Thus the sodium salts have a tendency when dried ring carbon atom thereof and tea process of ‘pro to darken, ‘ a phenomenon which ‘is particularly ducing the same. i “ “ ' ' “ ‘ " noticeable Where the component contains a ‘plu It is known that azo dyestuffs are‘prepared by; rality ‘of sulfonic acid groups. ‘ Suchdarkening . diazotizing an aromatic amine‘ and coupling the ‘ is apt to b‘e‘reflected in the ?nal color of the dye» resulting diazonium compound‘ with‘ an ‘azo cou stuff and may result in a distortion, of the shade. pling componentx‘The diazotizable amines em - of the dye. ployed are primary aromatic amines of the ben ‘(in the other hand, if it be desiredrto avoid the zene, naphthalene, anthracene and the like series. darkening, particularly whenutilizing the poly, The azo coupling componentaon the other hand, sulfonic‘ acids, by only partially neutralizing the.» are usually phenols or’compounds having a re component, if the component be employed in a active methylene group ‘such as pyrazjolones, ‘ ‘ dry composition, the acidity imparted to the com acetoacetic acid arylides and‘t‘he like, ‘ V‘ ‘ " ‘position may have a deleterious effect thereon. ‘The majority of the azo ,dye components are Assuming, ‘for instance, that the composition , not per se soluble in water. ,It is, therefore, cus contains a stabilized diazo amino compound and tomary practice‘ to ‘include in such ‘components, an incompletely neutralized sulfonated coupling, water-solubilizing groups, particularly sulfonio ‘component, thecomposition due to the acidity acid groups. The components are then utilized in -'¢ = of the coupling component is liable to decompo the form of the alkali metal, particularly the sition of the diazo amino compound with attend sodium salts. , . , , ant premature coupling. On the other hand, if The azo dyestuffs are utilized not only in the the composition contains a diazotizable amine, a dyeing of ?bers but also in other arts such as in nitrite and an incompletely neutralized ,sulfo color photography for the production of photo nated coupling component, the acidity thereof is graphic dyestuff images and in electrolytic‘ re apt to cause premature diazotization and cou cording methods for the formation‘ of dyestu?" pling. images. When using the ‘azo dyes in these var Again, in effecting neutralization of azo dye, ious arts, it is often desirable to produce the dyes components containing a plurality of sulfonic acid from compositions containing‘ the desired com 30 groups, it is necessary to utilize theexact amount ponents in the dry state. For instance, it has ‘ of alkali if the product is to be isolated by dry been recommended to employ a composition for ing, since otherwise the excess alkali remains in dyeing and printing comprising‘ a stabilized diazo the dry product. If the alkali be added in water amino compound and a coupling compound and solution to the product, the same becomes so to regenerate the diazonium compound for cou 35 soluble in water as to prevent efficient isolation pling by treating the composition with an acid. by the salting out method. It has also been suggested to provide a composi ‘I have now discovered that not only these, dis; , tion of a diazotizable amine,‘a nitrite and a cou advantages in ‘the sodium salts of sulfonated pling component to dissolve the same in water and cyclic organic azo dye components can be avoided to impregnate material ‘withthe composition for but ‘that, salts manifesting; properties not‘pos-ll use in facsimile recordings. When these pro sessed by__the sodium salts are obtained if ‘the posals are adopted, the compositions must meet sulfonated component be neutralized in whole or certain tests, For instance, they must’ ‘readily ‘ in part by means of morpholine. , 1 dissolve in water, they must be stable‘ prior to dis 45 ‘ The morpholine salts do not have the undesir solution in water, and particularly when utilized able tendency to darken possessed by the sodium in the formation of azo dyestufi images in pho salts. They can be prepared andisolated with- ‘ tography and in facsimile recording, they must . out difficulty since any excess of morpholine em provide a background stable to light and storage. ployed in the preparation of the salts can be The sodium salts of the sulfonic ‘acids of azo 50 volatilized I therefrom at low temperatures. , 2,453,430 3 It is accordingly an object of the present inven l-amino-2.4-disulfo-8-hydroxynaphthalene hav tion to‘ produce sulfonated cyclic organic com ing the formula pounds in which at least one of the sulfonic acid 0H NHZ groups is neutralized by morpholine. A further object of this invention is the prepa ration of sulfonated phenol in which at least one sulfonic acid group is neutralized by morpholine. A further object of this invention is a naphthol sulfonic acid in which at least one of the sulfonic acid groups is neutralized by morpholine. 10 A further object of this invention is a phenol 24amino-8-naphthol-6-sulfonic acid» . containing a plurality of sulfonic acid groups, 1-phenylamino-4-aminobenzene-2-sulfonic acid each of which is neutralized with morpholine. TliLamino-2-naphthol-4-sulfonic acid A further object of this invention. is naphthol _ 1;;-aminobenzenee3vi-sulionic‘ acid polysulfonic acids in which allof the sulfonic acid-a I531. 1:1,.-aminobenzene-4-sulfonic acid groups are neutralized with morpholine. 1é-amino42.5-dichlorobenzene-4esu1fonic acid . A‘ further object of this invention is a phenol, 1-methyl-2-aminobenzene-5-sulfonic acid containing a plurality of sulfonic acid groups-at, ‘ ;l-lmetliyb‘i-aminobenzene-Z-sulfonic acid least one of which is neutralized by morpholine 4t4"-diaminodiphenyl=-2.2'edisulfonic acid having and another an alkali such as an alkali metal or the formula ‘ an organic amine. ' ' Another object of this invention is chromo tropic acid the sulfonic acid groups of whichare; I neutralized by means of morpholine. s'oln, SIOaH ,The ‘morpholine salts of the cyclic organic 25 4.4,’ -diamino-3 .3 ’ -dimethyl-6.6' -disulfod,iphenyl compounds having a sulfonic acid group linked 1-naphthylamine-2—sulfonic acid. to a ‘ring’ carbon atom thereof can be simply pre 1-naphthylamine-4-sulfonic _ acid pared in 'a number of ways. For instance, the 1-naphthylamine-dsulfonic_ acid sulfonic acid may be slurried withan amount of Z-naphthylamine-l-sulfonic acid morpholine in excess of that theoretically re 2-naphthylamine,-5—sulfonic. acid, ‘ quired to neutralize the sulfonic acid groups pres 2-naphthylaminee3.6edisu1fonic, acid. ent ‘and suflicient to give a smooth, uniformly . 2-naphthylamine-5.7-disulfonic acid . wet paste. The excess of morpholine is then re 44.’ -'dia'minodiphenyl.-3.3f -disulfonic. acid, moved by volatilization at a temperature between 1-aminor2-nitrobenzene-4esulfonic_ acid" about 65 to ‘70° C. "In this way, all of the sill Z-aminodiphenyl-‘If-sulfonic acid,v fonic‘acid groups in the component are, neutral, 4.4,f -d_iamino.diphenylj-2esulfonic, acids ized by the morpholine. ‘ 4-aminodiplienylaminee2esu1ionic acid‘ , As an alternative, one mol of the sulfonic acid 1—naphthylamine-4éacetyl-amino-7ksulfonic acid. is‘ reacted with an amount of morpholine theoe 1 .4~diaminobenzene-6.-su1f onic _ acid, retically necessary to neutralize the sulfonic acid.‘ G-amino-1.—naphtho1-3-sulfonic acid. groups present, the reaction being effected in a 8-’amino.-1rnaphthol-2Ardisulfonic acid‘ closed vessel such as a ball mill by means of. which 8-amino,,-. l.-naphthol,-3.6-disulfonic . acid thorough mixing of the reactants can be‘ accom-. 3-amino-2-naphthol-7~sulfonic acid= plished. The reaction mixture is then dried at l-naphthylamine-3.6.8etrisulfonic. acid.v a low temperature such as that given ‘above. The ratio of the sulfonic acid to the morpholine and the - like: varies depending upon the particular sulfonic; Examples'of sulfonated cyclic organic coupling acid utilized and the results desired. If, for 'eX-H components the morpholine; salts or which are ample; the acid is a disulfonic acid and it is desired; cont‘einplated'by the present invention are: to neutralize only one sulfonic acid group, then 2-hydroxynaphthalene-6-sulfonic acid: one mol of the sulfonic acid is utilized for one 2#hydroxynaphthalene-8esulfonic acid‘ mol of morpholine. If, however, the disulfonic 1e.hydroxy.-.8 --,- aminomaphthalene-B?edisulfonic' acid is to be completely neutralized, then at least, acid : . - two mols of morpholine are used for each mol of a1.8-dihydroxyv-naphthalene-3;6-disulfonic acid, the acid. In a similar way, when using atri 55 1-hydroxy-naphthalene-3.6-disulfonic, acid: sulfonic acid, it is possible to neutralize one, two. 1-hydroxy->8;-~amino-naphthalene-ii?edisulfonio or all three of the acid groups present. acid havingthe formula Furthermore, by a proper proportioning of'the. reactants, the acids may be converted into mixed. ' NHz (‘3H salts of ' morpholine and another, neutralizing, 60 agent such as an alkali metal, i. e., sodium, potas sium or the like, or’ an organic amine such as an alkylamine, i. e., ethylamine, propylamine, butyl: amine, dimethylamine, diethylamine, and the like, an arylamine such as aniline, phenylmethylamine, orlthe’likesor an alkylolamine such as mono. 1-hydroxy-8-acetylamino naphthalene-ii?edisul ethanolamine, diethanolamine, triethanolamine, fonic acid propanolamine, dipropanolamine; dibutanol~ ‘ l-hydroxy-éleaminq naphthalene - 6.7‘- disulfonic, amine‘ and'the like.
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