Silylated acylphosphine oxides
AssigneeCiba-Geigy Corporation
InventorsWerner Rutsch, Rinaldo Husler
Life of this patent
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Abstract
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.
Claims15
A photopolymerisable composition comprising
- (a) at least one ethylenically unsaturated, photopolymerisable compound and
- (b) as photoinitiator at least one compound of the formula I ##STR52## in which R.sub.1 is the ##STR53## R.sub.2 is as defined for R.sub.1, it being possible for R.sub.1 and R.sub.2 as ##STR54## to be identical or different, or R.sub.2 is C.sub.1 -C.sub.18 alkyl, phenyl-, C.sub.1 -C.sub.12 alkoxy- or halogen-substituted C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.18 alkenyl, unsubstituted or C.sub.1 -C.sub.12 alkyl-, C.sub.1 -C.sub.12 alkoxy-, phenyl- or halogen-substituted C.sub.5 -C.sub.8 cycloalkyl, unsubstituted or halogen-, C.sub.1 -C.sub.12 alkyl- or C.sub.1 -C.sub.12 alkoxy-substituted C.sub.6 -C.sub.12 aryl, an aromatic, O-, S- and/or N-containing 5- or 6-membered heterocyclic radical, which may be substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.12 alkoxy, phenoxy or benzyloxy, and, if R.sub.2 is a ##STR55## R.sub.6 can link the silicon atoms to form 6-, 7- or 8-membered rings, in which case ##STR56## or R.sub.1 and R.sub.2, together with the --P.dbd.O group, can form a 4-membered ring of the formula ##STR57## R.sub.3 is C.sub.1 -C.sub.18 alkyl, halogen-, phenyl- or C.sub.1 -C.sub.12 alkoxy-substituted C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.6 alkenyl, unsubstituted or C.sub.1 -C.sub.12 alkyl-, C.sub.1 -C.sub.12 alkoxy- or halogen-substituted C.sub.5 -C.sub.8 cycloalkyl, unsubstituted or C.sub.1 -C.sub.12 alkyl-, C.sub.1 -C.sub.12 alkoxy-, C.sub.2 -C.sub.12 alkoxyalkyl-, C.sub.1 -C.sub.4 alkylthio- or halogen-substituted C.sub.6 -C.sub.12 aryl, or a 5- or 6-membered, aromatic, O-, S- and/or N-containing heterocyclic radical, which may be substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, and R.sub.4, R.sub.5 and R.sub.6, independently of one another, are hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.12 alkoxy or unsubstituted or C.sub.1 -C.sub.8 alkyl-substituted phenyl, at least two of the radicals R.sub.4, R.sub.5 and R.sub.6 being other than hydrogen.
A compound of the formula Ia ##STR70## in which R.sub.1 is the ##STR71## R.sub.2 is as defined for R.sub.1, it being possible for R.sub.1 and R.sub.2 as ##STR72## to be identical or different, or R.sub.2 is C.sub.1 -C.sub.18 alkyl, phenyl-, C.sub.1 -C.sub.12 alkoxy- or halogen-substituted C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.18 alkenyl, unsubstituted or C.sub.1 -C.sub.12 alkyl-, C.sub.1 -C.sub.12 alkoxy-, phenyl- or halogen-substituted C.sub.5 -C.sub.8 cycloalkyl, unsubstituted or halogen-, C.sub.1 -C.sub.12 alkyl- or C.sub.1 -C.sub.12 alkoxy-substituted C.sub.6 -C.sub.12 aryl, an aromatic, O-, S- and/or N-containing 5- or 6-membered heterocyclic radical, which may be substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.12 alkoxy, phenoxy or benzyloxy, and, if R.sub.2 is a ##STR73## R.sub.6 can link the silicon atoms to form 6-, 7- or 8-membered rings, in which case ##STR74## or R.sub.1 and R.sub.2, together with the --P.dbd.O group, can form a 4-membered ring of the formula ##STR75## R.sub.3 ' is C.sub.1 -C.sub.18 alkyl, halogen-, phenyl- or or C.sub.1 -C.sub.12 alkoxy-substituted C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.6 alkenyl, unsubstituted or C.sub.1 -C.sub.12 alkyl-, C.sub.1 -C.sub.12 alkoxy- or halogen-substituted C.sub.5 -C.sub.8 cycloalkyl, unsubstituted or C.sub.1 -C.sub.12 alkyl-, C.sub.1 -C.sub.12 alkoxy-, C.sub.2 -C.sub.12 alkoxyalkyl-, C.sub.1 -C.sub.4 alkylthio- or halogen-substituted C.sub.6 -C.sub.12 aryl, or a 5- or 6-membered, aromatic, O-, S- and/or N-containing heterocyclic radical, which may be substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, and R.sub.4, R.sub.5 and R.sub.5, independently of one another, are hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.12 alkoxy or unsubstituted or C.sub.1 -C.sub.8 alkyl-substituted phenyl, at least two of the radicals R.sub.4, R.sub.5 and R.sub.6 being other than hydrogen,
- with the provisos that (1) if R.sub.1 and R.sub.2 are identical and R.sub.4, R.sub.5 and R.sub.6 have the same meanings and are methyl or ethyl, R.sub.3 ' is not C.sub.1 -C.sub.5 alkyl, phenyl, methylphenyl, methoxyphenyl or halophenyl and (2) if R.sub.3 ' is methyl, R.sub.4, R.sub.5 and R.sub.6 in the radical R.sub.1 are not simultaneously ethyl.
Dependencies are inferred from the claim text.