Ciba Specialty Chemicals Corporation

Merck Patent Gesellschaft MIT Beschrankter Haftung

Ciba-geigy Corporation

Manfred Kohler

David G Leppard

Jorg Ohngemach

Eike Poetsch

Dieter Dorsch

Rudolf Eidenschink

Jurgen Gehlhaus

Gerhard Greber

Ljubomir Misev

Hans Ludwig Hirsch

Konrad Dorfner

Andreas Valet

Gebhard Hug

Gregor Wehner

Werner Rutsch

Michael Romer

Claus P Herz

Ronald Salathe

Thomas Lloyd James

Nils Hock

Compounds of the formula I ##STR1## in which R.sub.1 and R.sub.2 independently of one another are, for example, a group of the formula II ##STR2## R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 independently of one another are, for example, hydrogen, C.sub.1 -C.sub.12 alkyl, OR.sub.8, SR.sub.9, NR.sub.10 R.sub.11, halogen or phenyl; R.sub.8, R.sub.9, R.sub.10, R.sub.11 independently of one another are, for example, hydrogen or C.sub.1 -C.sub.12 alkyl; R.sub.12 is, for example, C.sub.1 -C.sub.8 alkyl; R.sub.13 is, for example, C.sub.1 -C.sub.12 alkyl; R.sub.14 is, for example, hydrogen; Y is C.sub.1 -C.sub.12 alkylene, C.sub.4 -C.sub.8 alkenylene, C.sub.4 -C.sub.8 alkynylene or cyclohexylene, or is phenylene or C.sub.4 -C.sub.40 alkylene interrupted one or more times by --O--, --S-- or --NR.sub.15 --, or Y is a group of the formula III, IV, V, VI, VII, VIII, IX, X or XI ##STR3## Y.sub.1 is as defined for Y with the exception of the formula V; R.sub.15 is hydrogen, C.sub.1 -C.sub.12 alkyl or phenyl; and R.sub.16 is hydrogen, CH.sub.2 OH or C.sub.1 -C.sub.4 alkyl; and mixtures of these compounds with further photoinitiators are suitable for photopolymerizing compounds having ethylenically unsaturated double bonds.

Non-volatile phenylglyoxalic esters

Compounds of the formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 independently of one another are hydrogen, halogen, C.sub.1 -C.sub.20 alkyl, cyclopentyl, cyclohexyl, C.sub.2 -C.sub.12 alkenyl, C.sub.2 -C.sub.18 alkyl which is interrupted by one or more oxygen atoms, or are phenyl-substituted C.sub.1 -C.sub.4 alkyl, or are phenyl which is unsubstituted or is mono- or disubstituted by C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy with the provisos that at least one of the radicals R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 is other than hydrogen and that, if R.sub.1 and R.sub.2 are methyl, R.sub.3 and R.sub.6 are not methyl, and mixtures of such compounds with .alpha.-hydroxy ketones, benzophenones and .alpha.-amino ketones, are suitable as photoinitiators.

Alkylphenylbisacylphosphine oxides and photoinitiator mixtures

Alkoxyphenyl-substituted bisacylphosphine oxides of the formula I ##STR1## in which R.sub.1 and R.sub.2 are identical or different and are a radical of the formula II ##STR2## n which R.sub.4 and R.sub.5 independently of one another are C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.12 alkoxy,

Alkoxyphenyl-substituted bisacylphosphine oxides

Molecular complex compounds comprising a mono-, bis- or trisacylphosphine oxide compound with an .alpha.-hydroxy ketone compound are suitable as photoinitiators for the photopolymerization of free-radically polymerizable compounds.

Molecular complex compounds of acylphosphine oxide and .alpha.-hydroxy

Coreactive photoinitiators

A photopolymerizable composition comprising (a) at least one ethylenically unsaturated photopolymerizable compound, and (b) alkoxyphenyl-substituted bisacylphosphine oxides of the formula I ##STR1## in which R.sub.1 and R.sub.2 are identical or different and are a radical of the formula II ##STR2## in which R.sub.4 and R.sub.5 independently of one another are C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.12 alkoxy, and R.sub.6, R.sub.7 and R.sub.8 independently of one another are hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy or halogen, R.sub.3 is a radical of the formula III ##STR3## in which R.sub.9 is C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl, naphthyl, phenyl-C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.12 alkenyl, --CF.sub.3 or ##STR4## or R.sub.9 is a radical of the formula IV or V ##STR5## in which X is for example C.sub.1 -C.sub.16 alkylene, C.sub.4 -C.sub.12 alkenylene or is xylylene, R.sub.10 is for example hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.12 alkenyl, cyclopentyl, cyclohexyl, phenyl with 1 or 2 C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy groups, or is C.sub.1 -C.sub.4 alkoxy, R.sub.11 is hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.12 alkenyl, cyclopentyl, cyclohexyl, phenyl, or is C.sub.1 -C.sub.4 alkoxy, or is a radical of the formula VI ##STR6## or R.sub.9 and R.sub.11, in the formula III together are ethylene, --CH.sub.2 CR.sub.14 R.sub.15 -- or --C(CH.sub.3).sub.2 CH.dbd.CH--, or R.sub.10 and R.sub.11, together with the atoms to which they are attached, for example form a benzene ring, R.sub.12 is hydrogen or C.sub.1 -C.sub.4 alkoxy, R.sub.13 is C.sub.1 -C.sub.4 alkyl, R.sub.14 and R.sub.15 independently of one another are hydrogen, C.sub.1 -C.sub.8 alkyl, phenyl or --CH.sub.2 OR.sub.13, or R.sub.14 and R.sub.15, together with the carbon atom to which they attached, form a C.sub.5 -C.sub.6 cycloalkyl ring, Y is for example a single bond, --CR,.sub.6 R.sub.17 -- or --CH.dbd.CH--, R.sub.16 is hydrogen, methyl or ethyl, R.sub.17 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.18 is hydrogen, C.sub.1 -C.sub.12 alkyl or phenyl, and m is a number from 2-12, with the proviso that if the radical --OR.sub.9 in the formula III is in the p-position of the phenyl ring and R.sub.9 is methyl, at least one of the radicals R.sub.10, R.sub.11 and R.sub.12 is not hydrogen, are suitable for the photopolymerization of compounds containing ethylenically unsaturated bonds.

Photopolymerizable compositions comprising alkoxyphenyl-substituted

Dimeric bisacylphosphines, oxides and sulfides

Acylphosphine oxides

Ethylenically unsaturated polymerisable compounds can be cured with daylight or with light sources equivalent to daylight by using as hardener a photoinitiator of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.12 alkyl, cyclopentyl, cyclohexyl, unsubstituted phenyl, naphthyl or biphenyl,

Daylight curing compositions containing bisacylphosphine oxide

Coreactive photoinitators

Compounds of the formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.18 alkyl, cyclopentyl or cyclohexyl, and R.sub.2 and R.sub.3, independently of one another, are phenyl which is unsubstituted or monosubstituted to tetrasubstituted by halogen, C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy, with the proviso that R.sub.1 is not decyl if R.sub.2 and R.sub.3 are chlorine-substituted phenyl, are suitable for the photopolymerisation of compounds containing ethylenically unsaturated double bonds.

Photopolymerizable compositions containing an alkylbisacylphosphine oxide

Compounds of the formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.18 alkyl, cyclopentyl or cyclohexyl, and R.sub.2 and R.sub.3, independently of one another, are phenyl which is unsubstituted or monosubstituted to tetrasubstituted by halogen, C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy, with the proviso that R.sub.1 is not decyl if R.sub.2 and R.sub.3 are chlorine-substituted phenyl, are suitable for the photopolymerization of compounds containing ethylenically unsaturated double bonds.

Alkylbisacylphosphine oxides

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

A radiation curable composition contains as light stabiliser a UV absorber of formula I ##STR1## wherein R is hydrogen or C.sub.1 -C.sub.18 alkyl, R.sub.1 and R.sub.2 are each independently of the other H, OH, C.sub.1 -C.sub.12 alkyl, halogen or halomethyl,

Growing community of inventors

Freiburg, Germany

Manfred Kohler