US 4,162,162 AGranted

Derivatives of aryl ketones and p-dialkyl-aminoarylaldehydes as visible sensitizers of photopolymerizable compositions

AssigneeE. I. Du Pont de Nemours and Company

InventorThomas E. Dueber

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Abstract

This invention relates to new photopolymerizable compositions. More particularly, this invention pertains to photopolymerizable compositions containing photodissociable initiators in combination with selected sensitizers derived from aryl ketones and p-dialkylaminoarylaldehydes that absorb in the visible region of the spectrum.

Claims17

Dependent claims

A photopolymerizable composition comprising an admixture of

(1) at least one non-gaseous ethylenically unsaturated compound having a boiling point above 100.degree. C. at normal atmospheric pressure and being capable addition polymerization;
(2) at least one 2,4,5-triarylimidazolyl dimer consisting of two lophine radicals bound together by a single convalent bond;
and
(3) a sensitizing amount of an arylylidene aryl ketone compound of the formulae:
##STR56## wherein:
A, B, D, E are carbon atoms or one may be solely a nitrogen atom:
R.sub.1 is H, OH or CH.sub.3 O;
R.sub.2 is H, OH, CH.sub.3 O or N(R.sub.6).sub.2 ;
R.sub.3 is H, OH or CH.sub.3 O;
a is 0 or 1;
Z is >C.dbd.O, CHOH, >C(CH.sub.3).sub.2, --CH.sub.2 --.sub.b, wherein b is 1, 2 or 3, ##STR57## wherein R' is H, phenyl, or Z is linked with R.sub.4 where Z is ##STR58## and R.sub.4 is --O-- or >N--CH.sub.3 a being O;
R.sub.4 is H, CH.sub.3, OH, CH.sub.3 O;
R.sub.5 is H or R.sub.5 +R.sub.7 is --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --O--CH.sub.2 CH.sub.2 --;
R.sub.6 is H or R.sub.6 +R.sub.7 is --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --O--CH.sub.2 CH.sub.2 --;
and
R.sub.7 is CH.sub.3, --(CH.sub.2).sub.n --CH.sub.3 where n is 1 to 5, --CH.sub.2 CH.sub.2 --Cl, --CH.sub.2 CH.sub.2 OH, CH.sub.2 CH.sub.2 OCH.sub.3 ;
##STR59## wherein:
A, B, D are carbon atoms or one may be solely a nitrogen atom;
R.sub.1 is H, CH.sub.3, --OCH.sub.2 CH.sub.2 OR, wherein R is H, CH.sub.3, --CH.sub.2 CH.sub.2 OR' wherein R' is CH.sub.3 or CH.sub.3 CH.sub.2 --;
R.sub.2 is H, CH.sub.3, OH or CH.sub.3 O;
R.sub.3 is H, OH, CH.sub.3 O, CH.sub.3, F, Br, CN or N(R.sub.9).sub.2 ;
R.sub.2 +r.sub.3 is --O--CH.sub.2 --O--;
R.sub.4 is H, CH.sub.3 or CH.sub.3 O;
R.sub.5 is H, CH.sub.3, --OCH.sub.2 CH.sub.2 OR, wherein R is H, CH.sub.3, --CH.sub.2 CH.sub.2 OR' wherein R' is CH.sub.3 or CH.sub.3 CH.sub.2 --;
R.sub.6 is H, CH.sub.3 or phenyl;
R.sub.7 is H, CH.sub.3, OH or CH.sub.3 O;
R.sub.8 is H;
R.sub.8 +r.sub.10 is --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --OCH.sub.2 CH.sub.2 ;
R.sub.9 is H, R.sub.9 +R.sub.10 is --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --OCH.sub.2 CH.sub.2 --;
and
R.sub.10 is CH.sub.3, --CH.sub.2 --.sub.n CH.sub.3 wherein n is 1 to 5;
and ##STR60## wherein G is ##STR61## --O--, or --S--;
R.sub.1 is H, CH.sub.3 or --OCH.sub.3, and
R.sub.2 is CH.sub.3 or --CH.sub.2 CH.sub.3,
the ketone having its maximum absorption in the range of 350 to 550 nm.

32 more elements

Dependencies are inferred from the claim text.

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Abstract

A photopolymerizable composition comprising an admixture of

(1) at least one non-gaseous ethylenically unsaturated compound having a boiling point above 100.degree. C. at normal atmospheric pressure and being capable addition polymerization;
(2) at least one 2,4,5-triarylimidazolyl dimer consisting of two lophine radicals bound together by a single convalent bond;
and
(3) a sensitizing amount of an arylylidene aryl ketone compound of the formulae:
##STR56## wherein:
A, B, D, E are carbon atoms or one may be solely a nitrogen atom:
R.sub.1 is H, OH or CH.sub.3 O;
R.sub.2 is H, OH, CH.sub.3 O or N(R.sub.6).sub.2 ;
R.sub.3 is H, OH or CH.sub.3 O;
a is 0 or 1;
Z is >C.dbd.O, CHOH, >C(CH.sub.3).sub.2, --CH.sub.2 --.sub.b, wherein b is 1, 2 or 3, ##STR57## wherein R' is H, phenyl, or Z is linked with R.sub.4 where Z is ##STR58## and R.sub.4 is --O-- or >N--CH.sub.3 a being O;
R.sub.4 is H, CH.sub.3, OH, CH.sub.3 O;
R.sub.5 is H or R.sub.5 +R.sub.7 is --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --O--CH.sub.2 CH.sub.2 --;
R.sub.6 is H or R.sub.6 +R.sub.7 is --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --O--CH.sub.2 CH.sub.2 --;
and
R.sub.7 is CH.sub.3, --(CH.sub.2).sub.n --CH.sub.3 where n is 1 to 5, --CH.sub.2 CH.sub.2 --Cl, --CH.sub.2 CH.sub.2 OH, CH.sub.2 CH.sub.2 OCH.sub.3 ;
##STR59## wherein:
A, B, D are carbon atoms or one may be solely a nitrogen atom;
R.sub.1 is H, CH.sub.3, --OCH.sub.2 CH.sub.2 OR, wherein R is H, CH.sub.3, --CH.sub.2 CH.sub.2 OR' wherein R' is CH.sub.3 or CH.sub.3 CH.sub.2 --;
R.sub.2 is H, CH.sub.3, OH or CH.sub.3 O;
R.sub.3 is H, OH, CH.sub.3 O, CH.sub.3, F, Br, CN or N(R.sub.9).sub.2 ;
R.sub.2 +r.sub.3 is --O--CH.sub.2 --O--;
R.sub.4 is H, CH.sub.3 or CH.sub.3 O;
R.sub.5 is H, CH.sub.3, --OCH.sub.2 CH.sub.2 OR, wherein R is H, CH.sub.3, --CH.sub.2 CH.sub.2 OR' wherein R' is CH.sub.3 or CH.sub.3 CH.sub.2 --;
R.sub.6 is H, CH.sub.3 or phenyl;
R.sub.7 is H, CH.sub.3, OH or CH.sub.3 O;
R.sub.8 is H;
R.sub.8 +r.sub.10 is --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --OCH.sub.2 CH.sub.2 ;
R.sub.9 is H, R.sub.9 +R.sub.10 is --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --OCH.sub.2 CH.sub.2 --;
and
R.sub.10 is CH.sub.3, --CH.sub.2 --.sub.n CH.sub.3 wherein n is 1 to 5;
and ##STR60## wherein G is ##STR61## --O--, or --S--;
R.sub.1 is H, CH.sub.3 or --OCH.sub.3, and
R.sub.2 is CH.sub.3 or --CH.sub.2 CH.sub.3,
the ketone having its maximum absorption in the range of 350 to 550 nm.

32 more elements