Moulded ophthalmic article

Details Moulded ophthalmic article Moulded ophthalmic article

1999-08-04

2000-12-26

Berman, Susan W.

Plastic and nonmetallic article shaping or treating: processes

Direct application of electrical or wave energy to work

Polymerizing, cross-linking, or curing

351159, 351160R, 523106, 522 84, 522 85, 522 86, 522 96, 522 97, 526312, 528 60, 528 65, C08G 1848, C08G 1481, C08F 250, C08F29906, G02B 104

Patent

active

061654086

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to specific branched polyurethane (meth)acrylates, processes for the production thereof, and moulded ophthalmic articles containing them, especially contact lenses.
Polymerisable urethane resins containing inorganic fillers, which are the reaction product of an ethylenically unsaturated polyisocyanate component with an ethylenically unsaturated polyol, and the thermal crosslinking of them into moulded articles, are already known e.g. from JP-A-3-210317. In addition, polymerisable resins which are the addition product of an unsaturated isocyanate with an amino-group-containing urethane are known e.g. from JP-A-7-292046. EP-A-0537877 discloses macromers which are obtainable e.g. by reacting a compound, which may be obtained from an ethylenically unsaturated isocyanate, a polyalkylene glycol and a diisocyanate, and which still has a free isocyanate group at its disposal, with a sugar derivative whose hydroxy groups are at least partly alkoxylated with an alkylene oxide, and also ophthalmic lenses that are obtainable from these macromers by crosslinking.
Now, surprisingly, new branched polyurethane (meth)acrylates have been found, which can be crosslinked in a particularly simple manner, e.g. directly from aqueous solution or solvent-free, to form moulded ophthalmic articles, such as contact lenses.
The present invention relates to ophthalmic mouldings, which are obtainable by crosslinking a prepolymer which is the copolymerisation product of --(CHY.sub.3 --CHY.sub.4 --O).sub.p --H (1) signifies hydrogen, one of radicals Y.sub.3 and Y.sub.4 is ethyl and the other is hydrogen, q is a number from 1 to 50, and n, m and p, independently of one another, are each a number from 0 to 100, wherein the sum of (n+m+p) is 5 to 100, aliphatic alcohol and x is a number.gtoreq.3, of formula (2) and a glycol, of formula (2), a dicarboxylic acid or a derivative thereof and a diol, and C.sub.5 -C.sub.8 -cycloalkane, which is substituted by.gtoreq.3 hydroxy groups, and an unsubstituted mono- and disaccharide, aliphatic-cycloaliphatic, aromatic or araliphatic di- or polyisocyanate and y is a number from 2 to 6, ##STR2## or an ethylenically unsaturated acid halide of formula ##STR3## wherein R.sub.3 is hydrogen or methyl, z and z1 independently of one another signify the number 0 or 1, B signifies C.sub.1 -C.sub.6 -alkylene, or phenylene or C.sub.7 -C.sub.12 -araikylene which is each unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, or a radical of formula ##STR4## B.sub.1 signifies linear or branched C.sub.2 -C.sub.12 -alkylene which is optionally interrupted by one or more oxygen atoms, B.sub.2 is C.sub.1 -C.sub.6 -alkylene and X signifies halogen, or presence of an additional vinylic comonomer.
In formula (1), n, m and p, independently of one another, preferably each denote a number from 0 to 50, whereby the sum of (n+m+p) is 8 to 50. Most preferably, n, m and p, independently of one another, each denote a number from 0 to 25, whereby the sum of (n+m+p) is 9 to 25. In formula (1'), q preferably signifies a number from 1 to 20.
The polyalkylene glycol according to (a) is e.g. a polyethylene glycol, polypropylene glycol, polyethylene glycol/polypropylene glycol block polymer, polyethylene glycol/polypropylene glycol/polybutylene glycol block polymer or a polytetrahydrofuran.
Preferred embodiments of the polyalkylene glycol according to (a) are represented by: another, are each a number from 0 to 100, preferably 0 to 50, and most preferably 0 to 25, and the sum of (n+m) is 5 to 100, preferably 8 to 50, most preferably 9 to 25. number from 5 to 100, preferably 8 to 50, most preferably 9 to 25.
R.sub.1 in formula (2) signifies e.g. the radical of an aliphatic polyol with 2 to 18, preferably 3 to 12, most preferably 3 to 8 carbon atoms. The variable x preferably signifies a number from 3 to 12, preferably a number from 3 to 8, most preferably a number from 3 to 6, and particularly preferably the number 3.
Examples of suitable polyhydroxy compounds of formula (2) are gly

REFERENCES:
patent: 5039458 (1991-08-01), Braatz et al.
patent: 5496496 (1996-03-01), Kajita et al.

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