US 4,792,632 A · Bisacylphosphine oxides, the preparation and use thereof

Abstract

Bisacylphosphine oxides of the general formula ##STR1## wherein R.sup.1 stands, for example, for a straight-chain or branched C.sub.1-18 alkyl radical, a cyclohexyl, cyclopentyl, phenyl, naphthyl, or biphenylyl radical, a cyclopentyl, cyclohexyl, phenyl, naphthyl, or biphenylyl radical substituted by F, Cl, Br, I, C.sub.1 -C.sub.12 alkyl and/or C.sub.1 -C.sub.12 alkoxyl, or an S or N-containing 5-membered or 6-membered heterocyclic ring, and R.sup.2 and R.sup.3, which are the same or different, stand for a cyclohexyl, cyclopentyl, phenyl, naphthyl, or biphenylyl radical, a cyclopentyl, cyclohexyl, phenyl, naphthyl, or biphenylyl radical substituted by F, Cl, Br, I, C.sub.1-4 alkyl and/or C.sub.1-4 alkoxyl, or an S or N-containing 5-membered or 6-membered heterocyclic ring; or R.sup.2 and R.sup.3 are joined to form a ring which contains from 4 to 10 carbon atoms and which may be substituted by 1 to 6 C.sub.1-4 alkyl radicals. The compounds are prepared by oxidation of the corresponding bisacylphosphines. The compounds are suitable for use as initiators for the photopolymerization of compounds containing ethylenically unsaturated bonds.

Claims10

Dependent claims

A method of polymerizing a photopolymerizable composition comprising adding a bisacylphosphine oxide having the formula ##STR4## wherein R.sup.1 stands for a straight-chain or branched C.sub.1-18 alkyl radical, a cyclohexyl, cyclopentyl, phenyl, naphthyl, or biphenyl radical,

a cyclopentyl, cyclohexyl, phenyl, naphthyl or biphenylyl radical substituted by F, Cl, Br, I, C.sub.1 -C.sub.12 alkyl and/or C.sub.1 -C.sub.12 alkoxyl,
an S or N-containing 5-membered or 6-membered heterocyclic ring, or
a radical of the formula:
##STR5## wherein n is 1 or 2, and
R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are H, C.sub.1-4 alkyl, C.sub.1-4 alkoxyl, F, Cl or Br;
R.sup.2 and R.sup.3, which are the same or different, stand for a cyclohexyl, cyclopentyl, phenyl, naphthyl, or biphenylyl radical
a cyclopentyl, cyclohexyl, phenyl, naphthyl or biphenylyl radical substituted by F, Cl, Br, I, C.sub.1-4 alkyl and/or C.sub.1-4 alkoxyl, or
an S or N-containing 5-membered or 6-membered heterocyclic ring;
or
R.sup.2 and R.sup.3 are joined to form a ring containing 4 to 10 carbon atoms and being optionally substituted by 1 to 6 C.sub.1-4 alkyl radicals as a photoinitiator to a photopolymerizable composition and exposing the thus obtained mixture to light.

7 more elements

A photopolymerizable composition comprising a bisacylphosphine oxide having the formula ##STR6## wherein R.sup.1 stands for a straight-chain or branched C.sub.1-18 alkyl radical, a cyclohexyl, cyclopentyl, phenyl, naphthyl, or biphenyl radical,

a cyclopentyl, cyclohexyl, phenyl, naphthyl or biphenylyl radical substituted by F, Cl, Br, I, C.sub.1 -C.sub.12 alkyl and/or C.sub.1 -C.sub.12 alkoxyl,
an S or N-containing 5-membered or 6-membered heterocyclic ring, or
a radical of the formula:
##STR7## wherein n is 1 or 2, and
R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are H, C.sub.1-4 alkyl, C.sub.1-4 alkoxyl, F, Cl, or Br;
R.sup.2 and R.sup.3, which are the same or different, stand for a cyclohexyl, cyclopentyl, phenyl, naphthyl, or biphenylyl radical
a cyclopentyl, cyclohexyl, phenyl, naphthyl or biphenylyl radical substituted by F, Cl, Br, I, C.sub.1-4 alkyl and/or C.sub.1-4 alkoxyl, or
an S or N-containing 5-membered or 6-membered heterocyclic ring;
or
R.sup.2 and R.sup.3 are joined to form a ring containing 4 to 10 carbon atoms and being optionally substituted by 1 to 6 C.sub.1-4 alkyl radicals and at least one polymerizable monomer selected from the group consisting of acrylic acid or methacrylic acid or esters thereof with C.sub.1-20 monohydric alcohols or polyhydric alcohols;
acrylic or methacrylic derivatives of bisphenol A;
alkanediol diacrylates or alkanediol dimethacrylates, diacrylates or dimethacrylates of bis-hydroxymethyl tricyclo [5.2.1.0..sup.2,6 ]-decane;
reaction products of diisocyanates and hydroxyalkyl(meth)acrylates;
adducts of diisocyanates and 2,2-propane-bis-3-(4-phenoxy)-1,2-hydroxypropane-1-methacrylate;
adducts of isocyanates and methacroyl alkyl ethers;
adducts of isocyanates and methacroyl alkoxybenzoles;
adducts of isocyanates and methacroyl alkoxycycloalkanes;
aromatic vinyl compounds;
styrene or derivatives thereof;
.alpha.-alkyl derivatives of styrene;
unsaturated polyesters prepared by the reaction of .alpha.,.beta.-unsaturated dicarboxylic acids in mixture with saturated dicarboxylic acids.

18 more elements

Dependencies are inferred from the claim text.

Bisacylphosphine oxides, the preparation and use thereof

Life of this patent

Bisacylphosphine oxides, the preparation and use thereof

Life of this patent

Abstract

Claims10