Hoechst Aktiengesellschaft

Wilfried Sahm

Gunter Rosch

Erich Schinzel

Hartmut Heise

Ernst Hille

Gerhart Schneider

Peter Hess

Franz Konig

Eberhard Ritter

Anton Horn

Wolfgang Schiller

Bernd Leibmann

Dieter Morler

Hans Walter Bucking

When continuously reacting an aqueous solution of 5-aminobenzimidazolone-(2) or a salt thereof with diketene then 5-acetoacetylamino-benzimidazolone is obtained in a smooth and safe reaction without foaming. The product results in high space-time yield and excellent quality.

Process for the manufacture of 5-acetoacetylamino-benzimidazolone

Novel azmoethines are obtained when reacting a tertiary amine with an aromatic aldehyde or ketone having in orthoposition an activated methoxy group. These azomethines are capable of ring closure to yield a benzofurane and said tertiary amine. The benzofuranes are optical brighteners tranquilizers or intermediates for optical brighteners, fluorescent dyestuffs, scintiallators, sensibilizers for electrophotographic coatings.

Heterocyclic azomethines

5-Acetoacetylamino benzimidazolone-(2) is obtained in high yield and excellent purity by reacting diketene with the aqueous solution of a salt of 5-amino-benzimidazolone-(2) and an acid having a pKa value of 1 to 7, preferably in the presence of an antioxidant and/or a reducing agent.

Process for the preparation of 5-acetoacetylamino-benzimidazolone

Novel azomethines are obtained when reacting a tertiary amine with an aromatic aldehyde or ketone having in orthoposition an activated methoxy group. These azomethines are capable of ring closure to yield a benzofurane and said tertiary amine. The benzofuranes are optical brighteners, tranquilizers or intermediates for optical brighteners, fluorescent dyestuffs, scintillators, sensibilizers for electrophotographic coatings.

Aromatic azomethines

Condensation of a benzofuran, which is substituted in 2-position by a carboxylic acid hydrazide group bound to the benzofuran nucleus via a bridgemember being in conjugation with the double bonds of the benzofuran, with a benzofuran-2-carboxylic acid halide yields a bisacyl hydrazide which is capable of oxdiazol ring closure while splitting off water. The so-obtained oxdiazoles are optical brighteners, especially for polyester materials.

Benzofuran derivatives, process for preparing them and their use as

New bisbenzofuranes which are connected by a direct bond or a bridgemember being in conjugation with the double bonds of the furane nuclei are obtained by intra- or intermolecular condensation reactions. The products are useful as optical brighteners, especially for detergents.

Benzofuran derivatives process for their preparation and their use as

1,3-Butadienes which are substituted at both terminal carbon atoms with phenyl, naphthyl, theinyl or furyl groups or one benzoxazolyl group are useful as optical brighteners for detergents. The butadienes, some of which are known, can be obtained by HORNER syntheses.

Optical brighteners

Novel azomethines are obtained when reacting a tertiary amine with an aromatic aldehyde or ketone having in orthoposition an activated methoxy group. These azomethines are capable of ring closure to yield a benzofurane and said tertiary amine. The benzofuranes are optical brighteners tranquilizers or intermediates for optical brighteners, fluorescent dyestuffs, scintiallators, sensibilizers for electrophotographic coatings.

Process for the preparation of benzofuran compounds

Benzofuran compounds of the formula ##SPC1## Wherein E is a bivalent bridging member of the formula ##SPC2## S is hydrogen, halogen, lower alkyl, carboxy, sulfo, cyano, lower carboalkoxy, carbonamido, lower mono- or dialkyl carbonamido, sulfonic acid lower alkyl ester, sulfonamido, lower mono- or dialkyl sulfonamido or phenyl; P, Q, T and U are hydrogen or halogen, lower alkyl, lower alkoxy, phenyl, carboxy, cyano, lower carboalkoxy, lower carbo-alkoxy substituted by a member selected from the group consisting of lower alkoxy, lower dialkylamino and lower trialkyl ammonium, carbonamido, lower mono- or di-alkyl carbonamido, sulfo, sulfonic acid lower alkyl ester, sulfonamido or lower mono- or dialkyl sulfonamido or P and Q together or T and U together are lower alkylene or an annellated phenyl ring, and n is 1 to 3. These compounds can be synthetized by a condensation reaction of the corresponding carboxylic acid derivative with an ortho-aminophenol or by HORNER or similar syntheses forming said bridging member. The products are optical brighteners.

Benzofuran derivatives

1,3-BUTADIENES CONTAINING AT LEAST ONE TERMINAL 2-BENZOFURANYL GROUP ARE OBTAINABLE BY HORNER syntheses. The products are optical brighteners.

Butadiene derivatives, process for their preparation and their use as

Peracylated aliphatic polyamines are useful as activators for inorganic peroxo compounds, i.e., they set free the available oxygen of the peroxo compounds in aqueous solutions at temperatures below 80.degree.C and are thus useful as additives to detergents especially inasmuch as they are compatible with usual detergent brighteners.

Peracylated polyamines compatible with optical brighteners as activators

Novel benzofuran containing a benzimidazolyl group are obtained by reacting a benzofuran containing a carboxylic acid halide group with either an ortho-phenylene diamine or an ortho-nitro-aniline derivative, in the latter case reducing the nitro intermediate to the corresponding (aminophenyl)-amide and splitting off water by closing the imidazole ring. The products are optical brighteners, especially for acrylonitrile polymers.

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Kelkheim (Taunus), Germany

Wilfried Sahm