Ciba-geigy Corporation

Ciba Specialty Chemicals Corporation

Ciba-geigy Ag

Rinaldo Husler

Werner Rutsch

Rudolf Kirchmayr

Kurt Dietliker

Manfred Rembold

Eginhard Steiner

Franciszek Sitek

Godwin Berner

Vincent Desobry

Harry Beyeler

Louis Felder

Martin Riediker

Kurt Meier

Reto Luisoli

Bernd Klingert

Rudolf Schwabe

Ivan Orban

Martin Holer

A novel process for the preparation of compounds of formula I ##STR1## by aminolysis of a p-halophenyl alkyl ketone of formula II ##STR2## with a cyclic amine of formula III ##STR3## in water at a temperature of at least 130.degree. C., in which formulae X is a halogen atom and R.sub.1, R.sub.2 and R.sub.3 are as claimed in claim 1, as well as the novel compounds of formula I and their use for the preparation of photoinitiators for the photopolymerisation of ethylenically unsaturated compounds.

Phenyl alkyl ketone substituted by cyclic amine and a process for the

The invention relates to a process for the preparation of polyalkylated aromatic carboxylic acids of formula I ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each independently of one another hydrogen, C.sub.1 -C.sub.20 alkyl, halogen or C.sub.5 -C.sub.8 cycloalkyl, with the proviso that at least two of the substituents R.sub.1, R.sub.2, R.sub.3, R.sub.4 or R.sub.5 are alkyl and/or cycloalkyl, by reacting corresponding aromatic hydrocarbons with carbon dioxide, which reaction is carried out observing special ratios of temperature and pressure. The invention furthermore relates to a one-pot process for the preparation of the corresponding acyl halides.

Process for the preparation of alkylated aromatic carboxylic acids and

Compounds of the formula I, II, III and IIIa ##STR1## in which Ar.sup.1 is an unsubstituted or substituted aromatic radical and at least one of the radicals R.sup.1 and R.sup.2 is an alkenyl, cycloalkenyl or arylmethyl group, are effective photoinitiators for photopolymerization of unsaturated compounds. They are particularly suitable for photocuring of pigmented systems.

.alpha.-aminoacetophenones as photoinitiators

Liquid highly active photoinitiators are obtained by dissolving a solid photoinitiator of the titanocene type in liquid photoinitiators of the acetal or ketal type. The liquid mixtures have a long dark storage stability.

Liquid photoinitiator mixtures

Titanocenes of the formula I ##STR1## in which R.sup.1 are cyclopentadienyl.sup..crclbar. groups and R.sup.2 and R.sup.3 are aromatic radicals which are substituted in both ortho-positions by fluorine and, in addition, are substituted by an acyloxy group are suitable as photoinitiators for the photopolymerization of ethylenically unsaturated compounds.

Oxygen-containing titanocenes, and the use thereof

Silylated acylphosphine oxides of formula I ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 are defined in the specification, are highly suitable as photoinitiators for the photopolymerization of compounds which can be polymerized by means of free radicals, namely ethylenically unsaturated compounds.

Silylated acylphosphine oxides

Propiophenones of the formula I ##STR1## in which R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl, --Si(CH.sub.3).sub.3, allyl or benzyl, R.sup.2 is hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.4 -alkyl which is substituted by C.sub.1 -C.sub.4 -alkoxy or --OH, --(CH.sub.2 --CH.sub.2 --O).sub.n --R.sup.5 where n is 2 to 20 and R.sup.5 is H or C.sub.1 -C.sub.4 -alkyl, --Si(CH.sub.3).sub.3, benzyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.4 -alkynyl or 2-tetrahydrofuranyl, or R.sup.1 and R.sup.2 together are a C.sub.1 -C.sub.6 -alkylidene radical or a C.sub.2 -C.sub.6 -alkylidene radical which is substituted by hydroxyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, a linear or branched C.sub.2 -C.sub.6 -alkanediyl radical, a benzylidene, cyclopentylidene or cyclohexylidene radical or a 2,2,2-trichloroethylidene, 2-furylmethylidene or dimethylsilylidene radical, R.sup.3 is phenyl which is unsubstituted or substituted by one or more --Cl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio radicals, and is also benzoylphenyl, phenoxyphenol or phenylthiophenyl, R.sup.4 is C.sub.1 -C.sub.4 -alkyl, or phenyl which is unsubstituted or substituted by one or more --Cl, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy radicals, and R.sup.5 is hydrogen or C.sub.1 -C.sub.4 -alkyl, or R.sup.4 and R.sup.5 together are a trimethylene or tetramethylene radical, and R.sup.6 is hydrogen, C.sub.1 -C.sub.4 -alkyl, --CCl.sub.3 or phenyl, subject to the condition that, if R.sup.2, R.sup.5 and R.sup.6 at the same time are hydrogen and R.sup.3 and R.sup.4 are at the same time phenyl, R.sup.1 must not be hydrogen or C.sub.1 -C.sub.4 -alkyl, also, if R.sup.3 and R.sup.4 at the same time are phenyl and R.sup.5 and R.sup.6 are at the same time hydrogen, R.sup.1 and R.sup.2 together must not be alkylidene or benzylidene, and also, if R.sup.3 and R.sup.4 at the same time are p-methoxyphenyl and R.sup.2, R.sup.5 and R.sup.6 are at the same time hydrogen, R.sup.1 must not be hydrogen, and, finally, if R.sup.2 and R.sup.6 at the same time are hydrogen and R.sup.3, R.sup.4 and R.sup.5 are at the same time phenyl, R.sup.1 must not be hydrogen, are valuable initiators for the photopolymerization of ethylenically unsaturated compounds.

Propionphenone derivatives as photoinitiators for photopolymerization

The photopolymerizable composition described contains

Photopolymerizable compositions containing aminoaryl ketone

Titanocenes containing two 5-membered cyclodienyl groups, for example cyclopentadienyl, and one or two 6-membered carbocyclic or 5- or 6-membered heterocyclic aromatic rings which are substituted by a fluorine atom in at least one of the two ortho-positions to the titanium-carbon bond and contain, as a further substituent, unsubstituted or substituted 1-pyrryl, are suitable as photoinitiators for radiation-induced polymerization of ethylenically unsaturated compounds.

Titanocenes, the use thereof, and N-substituted pyrroles

Compounds of the formula I ##STR1## in which n is 1-30 and X, Y, R, Ar.sup.1 and Ar.sup.2 are as defined in claim 1 can be prepared by reaction of a benzil dialkyl ketal with a diol. Depending on the molar ratio of the two reaction components, products having a different polycondensation degree n are obtained. the compounds can be used as photoinitiators.

Oligomeric benzil ketals and their use as photoinitiators

Novel alpha-aminoacetophenones as photoinitiators

Titanocenes of the formula I ##STR1## in which R.sup.1 are cyclopentadienyl.sup..crclbar. groups and R.sup.2 and R.sup.3 are aromatic radicals which are substituted in both ortho-positions by fluorine and, in addition, are substituted by a pyrrylalkyl group, amidoalkyl group or imidoalkyl group, are suitable as photoinitiators for the photopolymerization of ethylenically unsaturated compounds.

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Marly, Switzerland

Rinaldo Husler