Crosslinked polymers containing ester or amide groups

Details Crosslinked polymers containing ester or amide groups Crosslinked polymers containing ester or amide groups

1997-07-30

1998-12-15

Smith, Jeffrey T.

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

522144, C08F 800, C08F 248

Patent

active

058498419

DESCRIPTION:

BRIEF SUMMARY
The invention relates to a novel process for the production of mouldings, in particular contact lenses, in which a water-soluble, crosslinkable polymer containing, in particular ester-linked or amide-linked crosslinkable acrylate groups is crosslinked, preferably in aqueous solution, and to mouldings, in particular contact lenses, which are obtainable by this process.
The present invention also relates to novel water-soluble, 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 water-soluble, crosslinkable polymers, to a process for the preparation of the novel water-soluble, 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.
By contrast, the present invention relates to water-soluble, crosslinkable polymers which are based on a starting polymer (polymer backbone) which has a functional group which is capable of reacting with an azalactone with ring opening, such as, in particular, an alcoholic hydroxyl group or an amino group, and which preferably have a 1,3-diol, 1,3-amine, 1,3-imine or 1,4-imine skeleton, a certain percentage of these skeleton units being modified to form an ester or amide containing a crosslinkable (alkyl)acrylic acid radical.
The novel crosslinkable, water-soluble polymer is, in particular, a derivative of a polyvinyl alcohol, polyethyleneimine or polyvinylamine having a mean molecular weight of at least about 2000 which comprises from about 0.5 to about 80%, based on the number of hydroxyl groups in the polyvinyl alcohol or the number of imine or amine groups in the polyethyleneimine or polyvinylamine respectively, of units of the formula III or IIIa ##STR2## in which R.sub.1 and R.sub.2 embody amino acid radicals and are, independently of one another, hydrogen, a C.sub.1 -C.sub.8 alkyl group, an aryl group, or a cyclohexyl group, where these groups are unsubstituted, monosubstituted or polysubstituted; CH.sub.3 group, and
In a preferred embodiment, R.sub.4 is --O--, i.e. an ester link. Particular preference is gi

REFERENCES:
patent: 4347198 (1982-08-01), Ohkada et al.
patent: 4670506 (1987-06-01), Goldenberg et al.
patent: 4978713 (1990-12-01), Goldenberg
patent: 5508317 (1996-04-01), Muller

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