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US 5,612,391 AGranted
Functionalized photoinitiators, macromers thereof, and the use thereof for contact lens
AssigneeCiba-Geigy Corporation
InventorsPeter Chabrecek, Dieter Lohmann
Life of this patent
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Abstract
Contact lenses formed from 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.
Claims13
A contact lens, comprising:
- (a) an oligomer or polymer containing H-active groups, --OH and/or --NH-- bonded to the oligomer or polymer backbone, either via a bridge group selected from the group consisting of --(C.sub.1 -C.sub.4 alkylene-O)--, --(C.sub.2 -C.sub.10 alkylene-NH)-- and --C(O)--(CHOH).sub.r --CH.sub.2 --O-- where r is 0-4, or directly bonded, or containing H-active --NH-- groups bonded in the oligomer or polymer backbone, some or all of whose H atoms in the H-active groups have been substituted by radicals of formula IV:
- ##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 (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 by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 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;
- 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 of 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 in the --(Y.sub.1).sub.n -- groups in the formula Ia is O and n in the other --(Y.sub.1).sub.n -- group 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;
- and
- (b) a thin outer coating, on at least part of the oligomer or polymer surface, of a graft polymer formed by photopolymerization of a non-volatile or low-volatility olefin.
20 more elements
Dependencies are inferred from the claim text.