Basf Aktiengesellschaft

Hans Baumann

Andreas Oberlinner

Klaus Grychtol

Hermann Kaack

Compounds which in the form of the free acids correspond to the formula ##STR1## where A is a radical of a diazo component or of an amine,

Azo dye 2:1-chromium complexes

A dye of the formula ##STR1## wherein R.sup.1 is is fluorine, chlorine, bromine, methyl, ethyl, cyano, carboxyl, nitro, tribfluoromethyl, methylsulfonyl, phenylsulfonyl, acetyl, C.sub.1 -C.sub.4 alkoxy, phenoxy, chlorophenoxy or benzoyl; R.sup.2 is hydrogen, chlorine, bromine, methyl, ethyl, C.sub.1 -C.sub.4 alkoxy, benzthiazol-2-yl, 6-methylbenzthiazol-2-yl, acetylamino, carboxyl aminosulfonyl, or aminocarbonyl; R.sup.3 is hydrogen chlorine, bromine or methyl; R.sup.5 is hydrogen, methyl, methoxy or ethoxy; and X is fluorohydroxyphosphonyl or dihydroxyphosphonyl. The dye of the present invention is useful in the dyeing of cellulose-containing material, polyamides and leather. The high tinctorial strength of the dyes and the very good lightfastness and wetfastness properties of the dyeings are particularly noteworthy.

Reactive pyrazole group containing monoazo dye

An unsymmetrical 1:2 chromium complex of a monoazo dyestuff and a disazo dyestuff which is non-fiber reactive and is free of sulfonamido and amino groups and which, in the form of the free acid has the formula: ##STR1## wherein A' is the radical of a 1-hydroxy-2-aminobenzene which is monosubstituted or disubstituted by chlorine, nitro, or sulfo, B' is a naphth-2-ol, resorcinol, p-(C.sub.1 -C.sub.6 -alkyl)-phenol, 1-phenol-3-methylpyrazol-5-one or acetoacetanilide radical, and the phenol group in the last two mentioned compounds can be substituted by C.sub.1 -C.sub.4 -alkyl C.sub.1 -C.sub.4 -alkoxy, chlorine or sulfo, K' is an unsubstituted or sulfo-substituted naphth-1-ol or naphth-2-ol radical, phenol which is substituted in the p-positioned by C.sub.1 -C.sub.6 -alkyl, an unsubstituted or sulfo-substituted 2-naphthylanime, and 1-phenol-3-methylpyrazol-5-one or an acetoactanilide radical, and the phenol group in the last two mentioned compounds can be substituted by C.sub.1 -C.sub.4 -alkoxy, chlorine or sulfo, and D' is the radical of a 1-hydroxy-2-aminobenzene or 1-amino-2-hydroxynaphthalene which is further substituted by nitro, sulfo or a mixture thereof. These dyes do not contain any fiber-reactive groups and are useful for dyeing various natural or synthetic nylon materials. In particular, the present dyes are useful for dying wool and leather. These dyes have good color strength, are high-hiding and have good fastness to washing and perspiration.

Unsymmetrical 1:2 chromium complex of a monoazo dyestuff and a disazo

Reactive dyes which in the form of the free acids correspond to the general formula ##STR1## where A is fluorine, chlorine or bromine,

Reactive bis-triazinyl stilbene dyes

Compounds of the general formula I ##STR1## where E is --CH.dbd. or --N.dbd., K is the radical of an amine or of a coupling component of the benzene, naphthalene, pyrazole, pyridine, pyrimidine, quinoline or isoquinoline series, or the radical of a 1,3-dicarbonyl compound which can be coupled, X is --O-- or --COO--, Y is --O--, --COO-- or --NH--, Z.sup.1 and Z.sup.2 independently of one another are unsubstituted or substituted alkyl or cycloalkyl, and one of them may furthermore be unsubstituted or substituted aryl, or Z.sup.1 and Z.sup.2 together with the nitrogen atom are a heterocyclic radical, and Z is unsubstituted or substituted C.sub.2 - or C.sub.3 -alkylene, from 1 to 4 sulfonic acid groups can be present and the rings A and B can be further substituted or can carry a fused benzene ring. The compounds of the present invention are suitable for dyeing or printing natural or synthetic N-containing materials, i.e., wool, leather or polyamide or polyurethane fibers, as wells as for coloring inks. The colored salts with amine bases are insoluble in water, but soluble in organic solvent. These colored salts can be used for dyeing organic liquids, resins or surface coatings, wood stains, paste for ball point pens, for coloring anodized aluminum, or for spin-dyeing, i.e., cellulose ester fibers for polyamide fibers.

Azo compound and an azomethine compound and having a tertiary N-dative

Reactive dyes which in the form of the free acids correspond to the general formula ##STR1## where R.sup.1 is hydrogen, chlorine, bromine, methyl or hydroxysulfonyl, R.sup.2 is chlorine, bromine or phenyl, or is C.sub.1 -C.sub.4 -alkoxy which is unsubstituted or substituted by hydroxyl, C.sub.1 -C.sub.4 -alkoxy or phenoxy, or is phenoxy or naphthoxy which are unsubstituted or substituted by C.sub.1 -C.sub.10 -alkyl and X is fluorine, chlorine or bromine, are exceptionally suitable for dyeing hydroxyl-containing material, e.g. cellulose or leather.

Triazinyl reactive dyes containing a 1-naphtol-4,8-disulfonic acid

1:2 Chromium complexes of arylazo-azamethines of the general formula ##STR1## where A is a naphthalene or benzene radical which may be monosubstituted or polysubstituted by alkyl, alkoxy or halogen.

1:2 Chromium complex dyes containing sulfonic acid groups

Dye intermediates of the formula ##STR1## where R.sup.1 is hydrogen, alkyl of 1 to 12 carbon atoms, phenyl which is unsubstituted or substituted by alkyl of 1 to 4 carbon atoms, methoxy, ethoxy, chlorine or bromine, or phenylalkyl of 7 to 10 carbon atoms, R.sup.2 is hydrogen or R.sup.1 and R.sup.2 together are dimethylene, trimethylene or tetramethylene, which are unsubstituted or substituted by alkyl of 1 to 12 carbon atoms, R.sup.3 and R.sup.5 are hydrogen, alkyl of 1 to 12 carbon atoms, cyano-, chlorine-, methoxy- or ethoxy-substituted alkyl of 2 to 4 carbon atoms, cycloalkyl of 5 to 7 carbon atoms, phenylalkyl of 7 to 10 carbon atoms or trimethylene which is unsubstituted or substituted by 1 to 3 methyl and is bonded to the carbon atom in the 6-position or 6'-position of the benzene ring, R.sup.4 and R.sup.6 are alkyl of 1 to 12 carbon atoms, cyano-, chlorine-, methoxy- or ethoxy-substituted alkyl of 2 to 4 carbon atoms, phenylalkyl of 7 to 10 carbon atoms, phenyl which is unsubstituted or substituted by alkyl of 1 to 4 carbon atoms, chlorine or bromine, or trimethylene bonded to the carbon atom in the 8-position or 8'-position of the benzene ring, or one or both of the groups ##STR2## are a pyrrolidine, piperidine, morpholine, thiomorpholine, N'-alkylpiperazine (alkyl being of 1 to 4 carbon atoms) or isoindoline radical, and the substituents R.sup.3, R.sup.4, R.sup.5 and R may be identical or different and the rings A and A' may be substituted by alkyl of 1 to 3 carbon atoms. The dye intermediates give deep bluish-green to green colorations with electron-attracting substances and may be used for the manufacture of pressure-sensitive recording materials.

7,7'-Diamino derivatives of 2,2'-spirodibenzopyranes

Dye intermediates of the formula ##STR1## where R.sup.1 is hydrogen, alkyl of 1 to 12 carbon atoms, phenyl which is unsubstituted or substituted by alkyl of 1 to 4 carbon atoms, methoxy, ethoxy, chlorine or bromine, or phenylalkyl of 7 to 10 carbon atoms, R.sup.2 is hydrogen or R.sup.1 and R.sup.2 together are dimethylene, trimethylene or tetramethylene, which are unsubstituted or substituted by alkyl of 1 to 12 carbon atoms, R.sup.3 and R.sup.5 are hydrogen, alkyl of 1 to 12 carbon atoms, cyano-, chlorine-, methoxy- or ethoxy-substituted alkyl of 2 to 4 carbon atoms, cycloalkyl of 5 to 7 carbon atoms, phenylalkyl of 7 to 10 carbon atoms or trimethylene which is unsubstituted or substituted by 1 to 3 methyl and is bonded to the carbon atom in the 6-position or 6'-position of the benzene ring, R.sup.4 and R.sup.6 are alkyl of 1 to 12 carbon atoms, cyano-, chlorine-, methoxy- or ethoxy-substituted alkyl of 2 to 4 carbon atoms, phenylalkyl of 7 to 10 carbon atoms, phenyl which is unsubstituted or substituted by alkyl of 1 to 4 carbon atoms, chlorine or bromine, or trimethylene bonded to the carbon atom in the 8-position or 8'-position of the benzene ring, or one or both of the groups ##STR2## are a pyrrolidine, piperidine, morpholine, thiomorpholine, N'-alkylpiperazine (alkyl being of 1 to 4 carbon atoms) or iso-indoline radical, and the substituents R.sup.3, R.sup.4, R.sup.5 and R.sup.6 may be identical or different and the rings A and A' may be substituted by alkyl of 1 to 3 carbon atoms. The dye intermediates give deep bluish-green to green colorations with electron-attracting substances and may be used for the manufacture of pressure-sensitive recording materials.

A 1:2 cobalt complex of the formula ##STR1## and its alkali metal salts and ammonium salts and methods of preparing the same are disclosed. On wool and nylons, the compounds give yellow dyeings which exhibit good wetfastness and very good lightfastness.

Sulfo, chloro phenolazoacetoacetylbenzamide dyes

Metal complex compounds which in the form of the free acids correspond to the formula I ##STR1## where A is an aliphatic, carbocyclic or heterocyclic radical, E is an aliphatic or carbocyclic radical, B is a cyano, acyl, substituted sulfonyl, carboxylic acid ester or carboxamide radical, or B and E together with the carbon atoms by which they are linked may be an alicyclic or heterocyclic radical, F is an aliphatic, carbocylic or heterocyclic radical, L is --O--, --COO--, ##STR2## n is 1, 2, 3 or 4, Y is .dbd.CH-- or .dbd.N-- and Z is ##STR3## or the radical of a coupling component, alkyl being of 1 to 4 carbon atoms, and R is hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aryl or acyl and R.sup.1 and R.sup.2 are substituents conventionally present in dyes. The compounds of the formula I give fast dyeings on natural polyamides and synthetic nylons.

Chromium complex dyestuffs for natural polyamides and synthetic nylons

2:1-chromium complex dyes of the formula: ##STR1## in which: A is the radical of a carbocyclic diazo component with a complex-forming hydroxy or carboxy group adjacent to the azo bridge;

Unsymmetrical 1:2-chromium complexes containing an azo and an azomethine

Spirodipyrans of the formula ##STR1## where A is the radical of a fused benzene ring or 2,1-naphthalene ring, the rings being unsubstituted or substituted by alkyl, alkoxy, nitro, chlorine, bromine or carbalkoxy,

Spirodipyrans

A pressure-sensitive recording material which comprises a substrate bearing a dye-forming component and a binder. The dye-forming component is a spirodipyran of the formula ##STR1## where A is the radical of a fused benzene or naphthalene ring (which rings may or may not be substituted), R.sup.1 is alkyl of 1 to 16 carbon atoms, substituted or unsubstituted phenyl or phenalkyl of 7 to 10 carbon atoms, R.sup.2 is H or together with R.sup.1 is a trimethylene or tetramethylene bridge which is unsubstituted or substituted by from 1 to 3 alkyl, R.sup.3 is benzyl or .beta.-phenylethyl and R.sup.4 is benzyl, .beta.-phenylethyl or substituted or unsubstituted phenyl, or R.sup.3 is alkyl of 1 to 4 carbon atoms and R.sup.4 is substituted or unsubstituted phenyl or R.sup.3 is benzyl and R.sup.4 is .beta.-cyanoethyl. The recording materials give violet to bluish green colorations (copies) only on paper coated with an electron acceptor.

Pressure-sensitive recording material

An azo compound useful in copying processes of the formula ##STR1## where R.sup.1 is hydrogen or alkyl of 1 to 4 carbon atoms, R.sup.2 and R.sup.3 are each alkyl of 1 to 4 carbon atoms, or one of the radicals R.sup.1, R.sup.2 and R.sup.3 is unsubstituted phenyl or phenyl substituted by alkyl of 1 to 4 carbon atoms, methoxy or ethoxy, and A denotes ##STR2## where R.sup.4 and R.sup.5 are each hydrogen; alkyl of 1 to 8 carbon atoms which may be substituted by hydroxy, alkoxy, halogen or alkoxycarbonyl; cyanoethyl; alkylcarbonyl with 1 to 3 carbon atoms in the alkyl; cyclohexyl; phenalkyl of 7 to 10 carbon atoms; or substituted or unsubstituted phenyl, or R.sup.4 is N,N-dialkylaminoalkyl or N,N-bisphenalkylaminoalkyl, or the group ##STR3## is a 5-membered or 6-membered saturated heterocyclic ring which may contain an --O-- or --S-- group as ring member, Y is hydroxy, alkyl, alkoxy, chlorine, bromine or alkylcarbonylamino, n is 0, 1 or 2, R.sup.6 and R.sup.7 are each hydrogen, alkyl of 1 to 4 carbon atoms, cyclohexyl or unsubstituted phenyl or phenyl substituted by alkyl or alkoxy, and Z is hydrogen, hydroxy, methoxy, ethoxy or a sulfonic acid group. The light absorption of the yellow to orange colored compounds (I) is displaced, upon protonation of the compounds, by 150 to 200 nm toward the longer wavelength range, i.e. the salts are violet to blue in color. The compounds (I) are suitable for the production of pressure-sensitive n.c.r. papers.

Growing community of inventors

Wachenheim, Germany

Hans Baumann