Ciba-Geigy Corporation

Ciba Specialty Chemicals Corporation

Alain C Rochat

Abul Iqbal

Jin Mizuguchi

Johannes Pfenninger

Olof Wallquist

Luigi Cassar

Max Jost

Edward E Jaffe

Gerald Giller

Remy Jeanneret

Jean Rody

Zhimin Hao

Fridolin Babler

Ian J Fletcher

Leonardo Guglielmetti

Abul Igbal

Nancy Schl&ouml;der-Tebaldi

Preparation of alkylthio- and/or arylthio-substituted diketo-diaryl-pyrrolopyrroles

A process for the preparation of compounds of formula I ##STR1## by reacting a pyrrolopyrrole of formula ##STR2## wherein X.sub.1 is a group selected from ##STR3## X.sub.2 is a group selected from ##STR4## or has the same meaning as X.sub.1, with a secondary amine of formula ##STR5## in the molar ratio 1:2, in the presence of an anhydrous dipolar aprotic solvent and of an amount 0.1 to 15 times in excess of stoichiometric proportion, based on the amine of formula III, of an anhydrous organic base, in the temperature range from 50.degree. to 230.degree. C. and under a pressure from 0 to 10 bar. The substituents R.sub.1 to R.sub.8, Y and Hal are as defined in claim 1. The compounds of formula I are especially suitable for use as photoconductive substances.

Process for the preparation of aminated diketobis (aryl or

A coated material comprising a substrate which is coated with a layer of a pyrrolopyrrole of formula I ##STR1## wherein R.sub.1 and R.sub.2 may be 4-pyridyl and X.sub.1 and X.sub.2 are O, said compound of formula I being at least partially in the form of a salt of a strong acid, is suitable for use as an optical recording material and, owing to its electrical conductivity and photoconductivity, as antistatically treated material, as sensor, photoreceptor and solar battery.

Process for storing information and a material having information

A process for storing information in an organic recording layer which, when treated locally with an organic solvent in accordance with the input of information, is able to change its absorption spectrum and/or its photoconductivity such that information can be produced or stored at the treated areas of said layer, wherein the organic solvent is solid at room temperature and is present in the recording layer, or by decomposition of a solid organic precursor which is present in the recording layer, and said solvent is vaporized or melts by the action of laser beams in accordance with the input of information, or said precursor is decomposed by the action of laser beams in accordance with the input of information. The stored information can be read out with a photodetector in the visible or near NIR range or with a built-in electrode system.

Process for storing information with high storage density

Coated material and the use thereof

Novel electrochromic compositions based on diketopyrrolopyrroles

Electrochromic compositions based on diketopyrrolopyrroles

Process for the storage of information in an organic recording layer which, as the result of local treatment of its surface with an organic solvent in accordance with the shape of the information to be marked can alter its absorption spectrum and/or its photoconductivity in such a way that information is produced and stored respectively at the treated areas of this layer. The information thus stored can be read off visually, by means of a micro-reader or by means of an incorporated electrode system.

Process for the storage of information in an organic recording layer

##STR1## wherein A and B independently of one another are carbocyclic or heterocyclic aromatic radicals, acyclic or cyclic aliphatic radicals or araliphatic radicals, Q is a divalent carbocyclic or heterocyclic aromatic, acyclic or cyclic aliphatic or araliphatic radical, E is a direct bond or a group --CO-- or --CS-- and X is a group --SR or --NRR', wherein R and R' independently of one another are hydrogen, carbocyclic or heterocyclic aromatic radicals, acyclic or cyclic aliphatic radicals or araliphatic radicals and R' can additionally be a group --O--halogen or --Q--EY--(C.sub.1 -C.sub.5 -alkyl), wherein Y is O or S, or R and R' form a 5-membered or 6-membered heterocyclic radical with the N atom to which they are bonded. Pyrrolopyrroles of this type are suitable for coloring high-molecular organic material to give intensely colored, brilliant and transparent colorations with good general fastness properties, and for use in photoelectric recording materials as photoconductive substances.

Monoketopyrrolopyrroles

Pigment compositions

Process for the preparation of brominated pyrrolo-[3,4-c]pyrrole pigments by bromination of a pyrrolo-[3,4-c]-pyrrole or of a mixture of different pyrrolo-[3,4-c]-pyrroles of the formula I ##STR1## with an amount of a brominating agent which supplies 0.5 to 70 equivalents of bromine, with or without a solvent, and subsequent isolation of the brominated pyrrolo-[3,4-c]-pyrrole by removal of the excess brominating agent and, if appropriate, the solvent by customary methods. The desired brominated pyrrolo-[3,4-c]pyrroles are obtained directly in a high yield by this process. Reference is made to claim 1 in respect of the meaning of substituents A, B and Z.

Process for the preparation of brominated pyrrolo-[3,4-c]-pyrroles and

1,4-diketopyrrolo[3,4-c]pyrrole pigments

Process for mass-coloring high molecular weight organic material, which comprises using a compound of the formula I ##STR1## in which one of R.sub.1 and R.sub.2 and one of R.sub.3 and R.sub.4 are, independently of each other, hydrogen, C.sub.1 -C.sub.12 -alkyl or benzyl and the other two radicals are, independently of each other, unsubstituted or halogen-, trifluoromethyl-, cyano-, C.sub.1 -C.sub.12 -alkyl-, --OR.sub.5 -, --SR.sub.5 -, --COR.sub.6 - or --SO.sub.2 R.sub.6 -substituted phenyl, biphenyl or naphthyl or a 5- or 6-membered aromatic heterocyclic ring containing one or more identical or different hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur without or with one or two fused-on benzene rings, R.sub.5 is hydrogen or C.sub.1 -C.sub.12 -alkyl, R.sub.6 is C.sub.1 -C.sub.12 -alkyl, and X and Y are independently of each other hydrogen, halogen or cyano. The invention also relates to new pyridoquinolones of the formula I. The colorings obtained with (I) have a yellow hue, a very high tinctorial strength which does not significantly change even in the event of prolonged processing and residence times, high saturation, high dispersibility, good overpainting, migration, wet, rub, light and weather resistance and in particular excellent heat stability.

Pyridoquinolone derivatives

The invention relates to a process for the preparation of pyrrolo[3,4-c]pyrroles of formula (1) ##STR1## wherein each of R.sub.1 and R.sub.2 independently of the other is an alkyl or aralkyl group or an isocyclic or heterocyclic aromatic radical, which process comprises reacting an ester of formula (2) or (3) ##STR2## with a nitrile of the formula R.sub.2 CN, in which formulae each of R and R' independently of the other is an alkyl or aryl group, and R.sub.1 and R.sub.2 are as defined above, in the presence of a strong base in an organic solvent. The invention also relates to compounds of formula (8) ##STR3## wherein R.sub.3 is an alkyl or aralkyl group or an ortho-substituted isocyclic or heterocyclic aromatic radical and R.sub.4 is an alkyl or aralkyl group or an isocyclic or heterocyclic aromatic radical. The pyrrolopyrroles obtained are valuable pigments for coloring compounds of high molecular weight such as plastics and lacquers in yellow to red shades of excellent fastness properties.

Process for the preparation of pyrrolo (3,4-c) pyrroles

Compounds of formula (1) ##STR1## wherein A and B are identical or different alkyl, aralkyl or cycloalkyl groups or carbocyclic or heterocyclic aromatic radicals, R.sub.1 and R.sub.2 are hydrogen atoms or substituents which do not impart solubility in water, are particularly suitable as photoconductive substances.

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Fribourg, Switzerland

Alain C Rochat