Functionalized photoinitiators, macromers thereof, and the use thereof
AssigneeCiba-Geigy Corporation
InventorsPeter Chabrecek, Dieter Lohmann
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Abstract
Compounds of formula I: ##STR1## are disclosed. The compounds are photoinitiators which can be functionalized by means of ethylenic groups or can be bonded to H-active substances, in order, for example, to modify surfaces by means of photopolymerizable substances. The compounds are especially useful in the manufacture of contact lenses.
Claims7
A material comprising (a) an inorganic or organic substrate to whose surface is bonded (b) as photoinitiator, at least one compound of the formula I ##STR47## in which X is O;
- Y is O, NH or NR.sub.6 ;
- Y.sub.1 is O;
- Y.sub.2 is --O--, --O--(O)C--, --C(O)--O-- or --O--C(O)--O--;
- each n, independently of one another, is 0 or 1;
- R is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy or C.sub.1 -C.sub.12 alkyl-NH--;
- R.sub.1 and R.sub.2, independently of one another, are H, linear or branched, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 hydroxyalkyl or C.sub.6 -C.sub.10 aryl, or two groups R.sub.1 --(Y.sub.1).sub.n -- together are --(CH.sub.2).sub.x -- or the R.sub.1 --(Y.sub.1).sub.n -- and
- R.sub.2 --(Y.sub.1).sub.n -- groups together form a radical of the formula:
- ##STR48## R.sub.3 is a direct bond or linear or branched C.sub.1 -C.sub.8 alkylene, which is unsubstituted or substituted by --OH and/or is uninterrupted or interrupted by one or more --O--, --O--C(O)-- or --O--C(O)--O-- groups;
- R.sub.4 is branched C.sub.3 -C.sub.18 alkylene, C.sub.6 -C.sub.10 arylene, which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.5 alkoxy, C.sub.7 -C.sub.18 aralkylene which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.8 cycloalkylene which is substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.8 cycloalkylene-C.sub.y H.sub.2y -- which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or --C.sub.y H.sub.2y --C.sub.3 -C.sub.8 cycloalkylene-C.sub.y H.sub.2y -- which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
- each R.sub.5, independently of one another, has the same meaning as R.sub.4 or is linear C.sub.3 -C.sub.18 alkylene;
- R.sub.6 is linear or branched C.sub.1 -C.sub.6 alkyl;
- x is an integer from 3 to 5;
- y is an integer from 1 to 6;
- and
- R.sub.a and R.sub.b, independently from one another, are H, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, benzyl or phenyl;
- with the provisos:
- that n in the --(Y.sub.1).sub.n --R.sub.1 groups is 0 if R.sub.2 is H;
- that at most two Y.sub.1 radicals in the --(Y.sub.1).sub.n -- groups in the formula I are O and n in the other --(Y.sub.1).sub.n -- groups is 0;
- that at most one Y.sub.1 is the --(Y.sub.1).sub.n -- groups in the formula Ia is O and n in the other --(Y.sub.1).sub.n -- groups is 0,
- that R.sub.4 provides different reactivity to the two NCX groups, and
- that n in the --(Y.sub.2).sub.n -- group is 0 if R.sub.3 is a direct bond;
- which is covalently bonded to the substrate via O atoms, S atoms, N--C.sub.1 --C.sub.6 alkyl groups or NH groups and the isocyanate group of the photoinitiators.
A contact lens comprising (a) a transparent, organic base material containing functional groups, and (b) a thin surface coating comprising (b1) at least one photoinitiator of the formula I and (b2) a graft polymer formed by photopolymerization of a non-volatile or low-volatility olefin.
Dependencies are inferred from the claim text.