Hoechst Aktiengesellschaft

Rudiger Erckel

Gunter Rosch

Dieter Gunther

Heinz Probst

Raimund Franz

Horst Fruhbeis

Thomas Martini

Erich Schinzel

Rolf Woernle

Theodor Riehm

Hans-Matthias Deger

Helmut Eckes

Merten Schlingmann

Erwin Schmidt

Wolfram Fritsche-Lang

Gert-Wolfhard Von Rymon Lipinski

Richard Bicker

Peter Jurges

Gu Rosch

Polysaccharides built up from anhydroglucose are obtained when glucose or carbohydrates containing glucose as the monomer structural unit are condensed with polyhydric alcohols in hydrogen fluoride. The products may be used as water binding agents and water retaining agents, especially for dietetic foodstuffs.

Process for the preparation of water-soluble polysaccharides, the

The semi-continuous process according to the invention for hydrolyzing cellulose-containing material (substrate) with gaseous hydrogen fluoride comprises sorption and subsequent desorption of HF in a total of n steps. The substrate is divided into n batches in n reactors (1a, 1b, 1c, . . . ); each batch passes through the n process steps in one reactor (1a, . . . ). Initially, sorption is carried out in the first to the (n/2)th step by the action of HF-inert gas mixtures, having an HF concentration which increases from sorption step to sorption step, at a temperature above the boiling point of HF. Subsequently, desorption is brought about in the ((n/2)+1)th to nth step by treating with heated HF-inert gas mixtures having an HF concentration which decreases from desorption step to desorption step; n is an even number from 4 to 12 and the n steps each take place in the same time segments (periods). The sequence of steps is displaced by one period from each batch to the next batch. During each period, the batch in the first step is connected to the batch in the last step and the batch in the second step with the batch in the penultimate step and the batch in the (n/2)th step with the batch in the ((n/2)+1)th step, by HF-inert gas circulations.

Process for hydrolyzing cellulose-containing material with gaseous

Coumarin compounds of the general formula (1) ##STR1## in which A denotes an oxygen atom or a grouping &gt;N--R in which R represents a hydrogen atom or an alkyl radical of 1 to 18 carbon atoms which may be substituted by fluorine, chlorine or bromine atoms or by alkoxy.sub.C.sbsb.1.sub.-C.sbsb.4, dialkyl.sub.C.sbsb.1.sub.-C.sbsb.4 -amino, --SO.sub.2 --N(alkyl.sub.C.sbsb.1.sub.-C.sbsb.4).sub.2 or cyano groups or a cycloaliphatic, aromatic or heterocyclic radical which may be substituted by fluorine, chlorine or bromine atoms or by alkyl.sub.C.sbsb.1.sub.-C.sbsb.4, alkoxy.sub.C.sbsb.1.sub.-C.sbsb.4, hydroxyl, cyano, sulfonamide or --SO.sub.2 --N--(alkyl.sub.C.sbsb.1.sub.-C.sbsb.4).sub.2 groups, X denotes an oxygen atom or a grouping .gtoreq.N--R' in which R' represents a hydrogen atom or an alkyl.sub.C.sbsb.1.sub.-C.sbsb.18 carbonyl, alkoxy.sub.C.sbsb.1.sub.-C.sbsb.4 carbonyl, alkyl.sub.C.sbsb.1.sub.-C.sbsb.4 carbamoyl or alkyl.sub.C.sbsb.1.sub.-C.sbsb.4 sulfonyl group or an aryl, arylcarbonyl, arylcarbamoyl or arylsulfonyl radical which may be substituted by fluorine, chlorine or bromine atoms or by alkyl or alkoxy groups of 1 to 4 carbon atoms each or by cyano groups, Y denotes a hydrogen atom or a cyano or an alkyl.sub.C.sbsb.1.sub.-C.sbsb.4 carboxylate group, an aryl, arylsulfonyl or --CO--O--aryl radical which may be substituted by fluorine, chlorine or bromine atoms or by alkyl or alkoxy groups of 1 to 4 carbon atoms, or by nitro, methylenedioxy, amino, monoalkyl.sub.C.sbsb.1.sub.-C.sbsb.4 amino or dialkyl.sub.C.sbsb.1.sub.-C.sbsb.4 amino groups or by a benzoxazolyl radical, or a heterocyclic radical which may be quaternized and which may be substituted by fluorine, chlorine or bromine atoms or by alkyl or alkoxy groups of 1 to 4 carbon atoms, or by nitro, phenyl, alkyl.sub.C.sbsb.1.sub.-C.sbsb.4 phenyl, alkoxy.sub.C.sbsb.1.sub.-C.sbsb.4 phenyl, cyano, methylenedioxy or alkyl.sub.C.sbsb.1.sub.-C.sbsb.4 carboxylate groups, and Z denotes a hydrogen atom or an alkyl.sub.C.sbsb.1.sub.-C.sbsb.4 carboxylate or cyano group, a process for their preparation, and their use for dyeing or printing synthetic fiber materials, in particular polyester fibers.

Benzo[de]pyrano[3,2-g]isoquinoline derivatives useful as dyestuffs

A continuous process for hydrolyzing cellulose-containing material (substrate) with gaseous hydrogen fluoride, HF is sorbed by the substrate at a temperature above its boiling point in n sorption steps and thereafter the sorbed HF is removed from the substrate by heating in n desorption steps. The number n of sorption steps and of desorption steps is identical and the reaction steps mentioned each occur in reactors which are separated from one another in a gas-tight manner. After introduction into the first sorption reactor (1a), the substrate passes consecutively through gas-tight valves into the second (1a) . . . nth sorption reactor and from the latter, optionally via a hold-up reactor (2) into the first, second, . . . nth desorption reactor (3a) and is removed from the nth desorption reactor (3a). The streams of HF gas, which contain an inert carrier gas in addition to HF, are circulated between the first (1a) or second (1b) or . . . (n-1)th or nth sorption reactor and the nth (3a) or (n-1)th (3b) . . . or second or first desorption reactor respectively.

The continuous process for hydrolyzing cellulose-containing material (substrate) is carried out by sorption of gaseous HF in a sorption reaction (1) and subsequent desorption in n steps, which are carried out in n reactors which are separated from one another in a gas-tight manner. The substrate is introduced via a gas-tight valve into the sorption reactor (1), passes through this and then reaches consecutively, through gas-tight valves, a hold-up reactor (2) and the first (3c), second (3b), . . . nth desporption reactor, from which it is then removed. The desorption is carried out in each case by the action of one of the n inert gas streams on the substrate at different temperatures, the particular inert gas stream being enriched with the HF being liberated during desorption. The gas streams, which are enriched to different extents with HF, are allowed to act on the substrate in the sorption reactor (1) in such a manner that the gas streams of low HF concentration act on a substrate having a zero or low concentration of HF and thereafter the gas streams of higher HF concentration act on substrate having higher HF concentration. The total gas stream (8a) produced from the individual gas streams leaves, after completion of sorption, the sorption reactor (1) largely freed of HF and is either conveyed to the desorption steps after dividing up into individual gas streams or it initially passes through the last desorption step (3a) and is thereafter divided up and passed to the other desorption steps in order, after passing through the latter, to be returned to the sorption reactor (1).

Mixtures of optical brighteners consisting of from (a) 0.98 to 0.50 part by weight of a mixture consisting of from 0.05 to 0.95 part by weight of a brightener of the series of the benzoxazolyl-stilbenes and of from 0.95 to 0.05 part by weight of a brightener of the series of the aryltriazoles and (b) of from 0.02 to 0.5 part by weight of a brightener of the series of the bis-benzoxazolyl-stilbenes or of the bis-benzothiazolyl-stilbenes.

Mixtures of optical brighteners and their use for the optical brightening

Mixtures of optical brighteners consisting of 5 to 95% by weight of a compound of the formula ##STR1## in which A denotes a o- or p-cyanophenyl group, and 95 to 5% by weight of one or more further optical brighteners.

Mixtures of optical brighteners

Pyridine is prepared by ammoxidation (=reaction with oxygen or an oxygen-containing gas and ammonia, if appropriate in the presence of steam) of cyclopentadiene in the presence of a tellurium-free silica gel catalyst, .gamma.-Al.sub.2 O.sub.3 catalyst and/or aluminum silicate catalyst, which is preferably also doped with transition metal oxides and/or the oxides of gallium and/or indium and, if appropriate, also contains trivial quantities of further customary additives. The surface area of the catalyst should be between about 75 and 800 m.sup.2 /g and the pore volume between about 0.2 and 2 cm.sup.3 /g, and the reaction temperature should be between about 200.degree. and 400.degree. C. The pyridine formed in the process is free from picolines and higher homologs.

Process for the preparation of pyridine

Mixtures of optical brighteners consisting of 5 to 95 parts by weight of a mixture consisting of 0 to 80% by weight of the compound of the formula 1 ##STR1## 20 to 100% by weight of the compound of the formula 2 ##STR2## and 0 to 80% by weight of the compound of the formula 3 ##STR3## and 95 to 5% by weight of one or more other optical brighteners.

Triazolyl stilbene compounds of the formula ##STR1## wherein A is a benzene or naphthalene ring optionally substituted by non-chromophoric substituents and B is a substituted 1,2,4-oxdiazole (3) or 1,3,5-oxdiazole (2) group, as well as a procedure for their manufacture and their use as optical brighteners.

Novel stilbene compounds: process for their manufacture and their use as

Compounds of the formula ##STR1## wherein X is O or S, R.sub.1 and R.sub.2 each are hydrogen, fluorine, chlorine, phenyl, alkyl, alkoxy, dialkylamino, trialkylammonium, acylamino or optionally functionally modified carboxy or sulfo groups, two adjacent radicals R.sub.1 and R.sub.2 optionally forming together a phenylene, a lower alkylene or a 1,3-dioxapropylene group; and A is a group of the formulae ##STR2## in which R.sub.3 is an alpha-, beta- or gamma-pyridyl, pyridyl-methylene, thiophenyl, furanyl, benzofuranyl, pyrazinyl, pyrimidinyl or pyridazinyl group. These compounds, which are suitable as optical brighteners, are prepared by reaction of a compound of the formula ##STR3## with a compound of the formula

Novel stilbene compounds and process for the manufacture thereof

Process for the manufacture of bis-benzoxazolyl-stilbene compounds which comprises the chlorination in an inert organic solvent of benzoxazolyl-stilbene carboxylic acid, addition of a solution of an aminophenol in an aprotic, dipolar solvent to the acid chloride thus obtained and subsequent cyclization in the presence of an acid catalyst of the acyl compound obtained.

Process for the manufacture of bis-benzoxazolyl-stilbene compounds

Mixture of optical brighteners consisting of from 0.5 to 0.95 part by weight of a brightener of the series of the benzoxazolyl-stilbenes and of from 0.95 to 0.05 part by weight of a brightener of the series of the aryltriazoles.

Diamino-1,3-5-triazinylstilbene compounds of the formula ##STR1## in which R.sub.1 and R.sub.2 may be identical or different and represent each hydrogen or non chromophoric radicals selected from the group consisting of fluorine or chlorine atoms, phenyl, alkyl, lower alkoxy, lower dialkylamino, lower trialkylammonium, acyl amino or optionally functionally modified carboxy or sulfo groups, or two vicinal radicals, R.sub.1 and R.sub.2 denote together lower alkylene, a fused benzo ring or 1,3-dioxypropylene, the rings A and B having optionally further non chromophoric substituents, and X is O or S. These compounds are good optical brighteners and are prepared by reacting a 4'-cyano-4-benzoxazolyl- or 4'-cyano-4-benzthiazolylstilbene compound with dicyanoamide or with urea and ammonia.

Diamino-1,3,5-triazinylstilbene compounds and process for preparing same

Benzimidazo-[1,2-a]-quinolines of the formula ##STR1## In the solid and dissolved state, the compounds of the invention are strongly fluorescing from reddish-blue to red, depending on the substitution. The compounds can be used as optical brighteners and as fluorescent dyestuffs. Furthermore they are valuable intermediates for the preparation of optical brighteners and fluorescing dyestuffs. They are distinguished by a very good fastness to light.

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Eppstein, Germany

Rudiger Erckel