Ciba-geigy Corporation

Werner Rutsch

Rinaldo Husler

Rudolf Kirchmayr

Kurt Dietliker

Manfred Rembold

Franciszek Sitek

Godwin Berner

Joseph E Babiarz

Vincent Desobry

Glen T Cunkle

Rinaldo H Usler

Paul A Odorisio

Mario Slongo

Max Hunziker

Manfred Kohler

Roger Meuwly

Christopher G Demmer

Gebhard Hug

Roger G Hall

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.

A-aminoacetophenones as photoinitiators

.alpha.-aminoacetophenones as photoinitiators

N,N,N',N'-Tetrasubstituted 1,4-diamino-2-butenes where the substituents are alkyl, cycloalkyl, aralkyl, aryl or mixtures thereof provide effective antioxidant protection to lubricants and/or synthetic polymers.

Substituted 1,4-diamino-2-butene stabilizers and stabilized compositions

Substituted 1,4-diamino-2-butene stabilizers

Bisacylphosphine sulfides of formula I ##STR1## wherein R.sub.1 is unsubstituted C.sub.1 -C.sub.18 or C.sub.1 -C.sub.8 alkyl which is substituted by phenyl, --CN, C.sub.1 -C.sub.12 alkoxy or halogen, C.sub.2 -C.sub.18 alkenyl, unsubstituted C.sub.5 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.8 cycloalkyl which is substituted by C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy or halogen, unsubstituted C.sub.6 -C.sub.12 aryl or C.sub.6 -C.sub.12 aryl which is substituted by halogen, C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.12 alkoxy, or a 5- or 6-membered aromatic heterocyclic radical which contains oxygen, sulfur and/or nitrogen and is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, and

Bisacylphosphine sulfides

Compounds of the formula I ##STR1## in which at least one of the radicals R.sub.1, R.sub.2 and R.sub.3 is a substituted alkyl radical or cycloalkyl radical, or R.sub.1 and R.sub.2 together with the phosphorus atom form a monocyclic or tricyclic ring, are effective photoinitiators for the photopolymerization of ethylenically unsaturated compounds.

Mono- and di-acylphosphine oxides

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

N,N,N',N'-Tetrasubstituted 1,4-diamino-2-butynes or N,N-disubstituted propargylamines where the substituents are alkyl, cycloalkyl, phenylalkyl, aryl or mixtures thereof provide effective antioxidant protection to lubricants and/or synthetic polymers.

Substituted 1,4-diamino-2-butyne or propargylamine as stabilizers for

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

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

Compounds of the formula ##STR1## in which a is 1, 2, or 3, R.sup.1 is an uncharged, carbocyclic or heterocyclic aromatic ring, unsubstituted or substituted, R.sup.2 is an unsubstituted or substituted cyclopentadienyl or indenyl anion, and .vertline.X.vertline..sup.a- is an a-valent anion, are suitable for use as latent curing catalysts for two-component polyurethane coatings which are activated by irradiation with actinic light or by heating.

Process for curing polyurethane coatings and compositions

Novel alpha-aminoacetophenones as photoinitiators

O-Alkenyl substituted hydroxylamines of formula I ##STR1## where R.sub.1 and R.sub.2 are independently hydrogen, alkyl, alkenyl, aryl or phenylalkyl, and R.sub.3 to R.sub.7 are independently hydrogen, alkyl or substituted alkyl are very effective process stabilizers for polymeric systems providing melt flow stabilization and resistance to discoloration during processing at elevated temperatures as well as effective stabilizers for lubricant compositions.

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Fribourg, Switzerland

Werner Rutsch