Crosslinkable polymers containing bonded photoinitiators

Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...

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522 84, 522 86, 522904, 522905, 522154, 523106, 264496, 524803, C08F21606, C08F 210, C08F 246, B29C 3508

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active

060110775

DESCRIPTION:

BRIEF SUMMARY
The invention relates to a novel process for the production of mouldings, in particular contact lenses, in which a crosslinkable polymer comprising units containing crosslinkable groups, units containing a bound photoinitiator and, if desired, units containing further modifiers is crosslinked in solution, and to mouldings, in particular contact lenses, which are obtainable by this process.
The present invention also relates to novel crosslinkable polymers which can be employed in the novel process, in particular those based on starting polymers containing functional groups, for example hydroxyl groups, on the polymer chain or functional groups, for example imino groups, in the polymer chain or functional groups bonded to the polymer skeleton via a bridge, where these functional groups allow covalent bonds to compounds containing a crosslinkable modifier group or another modifier group. These starting polymers are, in particular, polyhydroxyl compounds having a 1,2- and/or 1,3-diol structure, such as polyvinyl alcohol, or hydrolysed copolymers of vinyl acetate, for example copolymers with vinyl chloride, N-vinylpyrrolidone, etc.
The invention furthermore relates to crosslinked polymers, either homopolymers or copolymers, made from these novel crosslinkable polymers, to a process for the preparation of the novel crosslinkable polymers and the homopolymers and copolymers obtainable therefrom, to mouldings made from said homopolymers or copolymers, in particular contact lenses made from these homopolymers or copolymers, and to a process for the production of contact lenses using the said homopolymers or copolymers.
Contact lenses based on polyvinyl alcohol have already been disclosed. For example, EP 216 074 discloses contact lenses comprising polyvinyl alcohol containing (meth)acryloyl groups bonded via urethane groups. EP 189 375 describes contact lenses comprising polyvinyl alcohol crosslinked by means of polyepoxides.
Furthermore, some specific acetals containing crosslinkable groups have also already been disclosed. In this connection, we refer, for example, to EP 201 693, EP 215 245 and EP 211 432. EP 201 693 describes, inter alia, acetals of unbranched aldehydes having 2 to 11 carbon atoms carrying a terminal amino group which is substituted by a C.sub.3 -C.sub.24 olefinically unsaturated organic radical. This organic radical contains a functionality which withdraws electrons from the nitrogen atom, and furthermore the olefinically unsaturated functionality is polymerizable. EP 201 693 also claims products of the reaction of the acetals characterized above with a 1,2-diol, a 1,3-diol, a polyvinyl alcohol or a cellulose. However, such products are not described directly.
If one of the acetals of EP 201 693 is mentioned at all in connection with, for example, polyvinyl alcohol, as is the case, inter alia, in Example 17 of that patent application, the acetal which can be polymerized via its olefinic group is first copolymerized with, for example, vinyl acetate. The resultant copolymer is then reacted with polyvinyl alcohol, and an emulsion having a solids content of 37%, a pH of 5.43 and a viscosity of 11,640 cps is obtained.
However, none of these references describes or suggests the novel combination with which the starting polymer is derivatized, namely the combination of units containing a crosslinkable group, together with units containing a bound photoinitiator and in addition, if desired, further units containing additional modifiers.
The present invention relates, in particular, to crosslinkable polymers in which the linking of these units to the polymer backbone of the starting polymer is covalent and these groups are bound irreversibly. Suitable starting polymers are, in particular, any polymers based on polyhydroxyl compounds, in particular those having a 1,3-diol backbone, where a certain percentage of the 1,3-diol units has been modified to give a 1,3-dioxane containing, in the 2-position, a crosslinkable radical, a radical containing a bound photoinitiator and, if desired, a radical containin

REFERENCES:
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patent: 5332651 (1994-07-01), Dickinson et al.
patent: 5508317 (1996-04-01), Muller
patent: 5527925 (1996-06-01), Chabrecek et al.
Chemical Abstracts, vol. 99:176861q (1983).

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