Hoechst Celanese Corporation

American Hoechst Corporation

Other

Anthony J Corso

Thomas S Phillips

Fritz Meininger

Hans H Steuernagel

Kathleen M Colavito

Glenn A Thompson

A process for the preparation of isomerically pure sulfonic acids of 2-aminonaphthalenes having a fiber reactive substituent of the formula --(SO.sub.2 X) wherein X is --CH.sub.2 --CH.sub.2 --Z and Z is a substituent such as thiosulfato, phosphato or sulfato. The process comprises a first step of acylating the amino group of the substituted 2-aminonaphthalene to form a N-acyl derivative of the formula, R--CO--NH--A--SO.sub.2 X wherein A represents a naphthalene nucleus. The N-acyl derivative is then sulfonated to provide an essentially isomerically pure sulfonic acid derivative of the formula R--CO--NH--A(--SO.sub.2 X, --SO.sub.3 H). Depending upon the position of the --SO.sub.2 X group in the starting material, the sulfonation reaction product will have one of the following isomeric ring positions for the sulfonyl and sulfo groups, respectively; 5:7 or 7:5 or 6:8 or 8:6. Exemplary products are 2-acetylamino-5-(beta-sulfatoethylsulfonyl)-naphthalene-7-sulfonic acid or 2-acetylamino-7-(beta-sulfatoethylsulfonyl)-naphthalene-5-sulfonic acid or 2-acetylamino-6-(beta-sulfatoethylsulfonyl)-naphthalene-8-sulfonic acid or 2-acetylamino-8-(beta-sulfatoethylsulfonyl)-naphthalene-6-sulfonic acid. The latter aminonaphthalene sulfonic acid having 2-8-6 substitution is an important starting material for the preparation of fiber reactive dyes; the former three are not. New monoazo and disazo dyes or their metal complexes may be prepared from the 2,6,8; 2,5,7; and 2,7,5 isomers by diacylating, diazotizing and coupling them with coupling components selected from an unsubstituted or substituted benzene, naphthylene, acetoacetic acid arylide, arylamide, pyazolone or pyridone.

Process for the regiospecific sulfonation of sulfonyl substituted

This invention is directed to new water-soluble, monoazo dyes having the following general formula: ##STR1## in which: X and Y are independently selected from the group consisting of: ##STR2## R, R.sub.1, R.sub.2 are independently selected from H, lower alkyl of one to four carbons and sulfonated lower alkyl;

Water-soluble, monoazo dyes containing a ureido group and two sulfonyl

A water-soluble fiber-reactive red dyestuff is disclosed which, in its free acid form, has the formula ##STR1## wherein X is --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Z wherein Z is --OH, --Cl, --Br, --OSO.sub.3 H, --SSO.sub.3 H, --OPO.sub.3 H.sub.2, --O.sub.2 CCH.sub.3, --O.sub.2 CCH.sub.2 CH.sub.3 or --N(lower alkyl).sub.2. Liquid compositions of said dyestuff are also disclosed. This dyestuff yields brilliant red shades on cellulosic materials having excellent fastness properties and superior color yield and build up.

Fiber-reactive red azo dyestuff

This invention is that of an improved process for preparing 1:1 copper complex disazo compounds which comprises treating a disazo compound of the following general formula (2): ##STR1## wherein: M is hydrogen or the equivalent monovalent or divalent metal and

Process for the preparation of the copper complex disazo compounds from

This invention is directed to mixtures of water-soluble, fiber reactive yellow dyestuffs which exhibit superior build-up and color properties over those properties obtained with the individual components of the mixtures. The dyestuffs disclosed herein have the following general formula in their free acid form: ##STR1## wherein R is lower alkyl, lower alkoxy or hydrogen and wherein X is --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Z wherein Z is --OH, --Cl, --Br, --OSO.sub.3 H, --SSO.sub.3 H, OPO.sub.3 H.sub.2 or --N(R.sub.1).sub.2, and wherein R.sub.1 is lower alkyl or hydrogen.

Water-soluble vinyl sulfonyl-type reactive monoazo yellow dyestuffs

Water-soluble vinyl sulfonyl-type reactive monoazo yellow dyestuff

An aqueous, liquid fiber-reactive dye composition which is stable to decomposition is disclosed. The composition consists essentially of 5 to 45% by weight of a water-soluble, fiber-reactive dyestuff having from 1 to 3 .beta.-sulfatoethylsulfonyl (--SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H) groups, or a mixture of such dyestuffs; 0 to 10% by weight of water-soluble inert inorganic salt; and 45 to 95% by weight of water. Said liquid dye composition must have a pH of about 2.5 to about 4.5 and must be substantially free of buffer substances. The liquid dye composition may be stored for long periods of time at 0.degree. to 50.degree. C. with substantially reduced decomposition to the vinylsulfonyl dye form.

Stable aqueous liquid composition of reactive dyes containing

A method of directly producing copperized azo-dyestuffs of predetermined inorganic salt content is disclosed wherein an ortho, ortho'-dihydroxyazo-dyestuff is reacted with about one molar equivalent of a copper (II) compound consisting of from 1.0 to 0.1 molar equivalent of a non-salt-forming copper compound selected from CuCO.sub.3.Cu(OH).sub.2, 2CuCO.sub.3.Cu(OH).sub.2, Cu(OH).sub.2, CuO and mixtures thereof, and correspondingly from 0 to 0.9 molar equivalent of a salt-forming copper (II) compound selected from CuSO.sub.4, CuCl.sub.2 and Cu(NO.sub.3).sub.2. The disclosed method provides standard strength copperized dyestuff compositions at increased yields and without the need to precipitate the product from the reaction solution.

Method of forming copper complexes of azo-dyestuffs using

An improved process for selectively N-acylating hydroxy-amino-arylsulfonic acids is disclosed wherein the hydroxy-amino-arylsulfonic acid is dissolved in water by treatment with an alkaline lithium salt, such as lithium hydroxide, and the acylation is conducted while maintaining the pH at about 3-6. The N-acyl-hydroxy-amino-arylsulfonic acids are useful as dyestuff precursors.

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Coventry, RI, United States of America

Anthony J Corso