Poly-unsaturated carbohydrate derivatives, polymers thereof and

Details Poly-unsaturated carbohydrate derivatives, polymers thereof and Poly-unsaturated carbohydrate derivatives, polymers thereof and

1997-04-04

1999-08-17

Szekely, Peter A.

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

Synthetic resins

Processes of preparing a desired or intentional composition...

264 11, 52623823, 536 172, 536 179, 536103, 5361231, 53612313, 560159, 560222, 564 59, C07H 1502, C07H26504

Patent

active

059394668

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to polymerisable derivatives of carbohydrates comprising a carbohydrate radical and more than one radically polymerisable hydrocarbon group which is linked optionally via a spacer to the carbohydrate radical, to copolymers, branched polymers, block copolymers, graft copolymers and polymeric networks thereof, to capsules, fibres, films and coatings having water-binding and biocompatible properties, and to moulded articles, for example contact lenses or biomedicinal articles, comprising the mentioned polymers, as well as to processes for the preparation of the mentioned polymers and articles.
Moulded articles, for example contact lenses, or coatings for biomedicinal articles having water-binding and biocompatible properties place high demands on the material used. The search for suitable starting materials for the preparation of such products, which are mentioned by way of example, is therefore of great importance.
JP 4 316 594 describes, for example, a methacrylate that is linked to a carbohydrate in which from 50 to 100% of the hydrogen atoms of the amino or hydroxy groups preferably have been esterified by aromatic hydrocarbons. Those compounds can be polymerised, but they are then used as a stationary phase in chromatography, especially for the separation of chiral compounds.
A carbohydrate derivative, for example isomannitol dimethacrylate, is described in Angew. Makromol. Chemie 123/124, 241 (1984) as a cross-linking agent for polymeric networks, especially to control the water content in polyhydroxyethyl methacrylate (poly-HEMA) hydrogels. Those hydrogels are used in the manufacture of contact lenses.
European Patent 331 633 describes hydrophilic monomers carrying one or more polymerisable or reactive groups that are each bonded via a divalent group to a mono- or poly-valent hydrophilic group. The number and nature of the polymerisable or reactive groups and the nature of the hydrophilic group determine the properties of a product produced therefrom. As a preferred compound there is disclosed, for example, a polyvinyl alcohol (PVA) modified by 2-isocyanatoethyl methacrylate (IEM). Although carbohydrates are mentioned as hydrophilic groups, they are not specifically disclosed. The mentioned monomers are, for example, suitable for the manufacture of contact lenses.
It has now been found that unprotected carbohydrate derivatives can be reacted with unsaturated compounds, especially isocyanates, to form polysubstituted derivatives. As a result of such a reaction, new unsaturated carbohydrate derivatives modified by at least two polymerisable ligands are isolated. The resulting poly-unsaturated carbohydrate derivatives are especially suitable for use as cross-linking agents in the synthesis of polymers. They can also be converted into polymers having a high carbohydrate content. Such polymers are to be understood as being especially copolymers and block copolymers and also graft copolymers, especially branched and crosslinked polymerisates, which can be obtained, for example, by radical polymerisation or photopolymerisation.
Accordingly, the present invention relates to a compound of formula (I) selected from a mono-, di- or tri-saccharide, an oligosaccharide, a cyclodextrin (CD) and an anhydrosaccharide, or of a conventional derivative of the mentioned saccharides; twice, and the remaining Y are --O--.
R.sup.1 is, for example, alkenyl, vinylphenyl or vinylbenzyl in the form of a radically polymerisable group having preferably from 2 to 12 carbon atoms. Examples of alkenyl are vinyl, allyl, 1-propen-2-yl, 1-buten-2- or -3- or -4-yl, 2-buten-3-yl, and the isomers of pentenyl, hexenyl, octenyl, decenyl, undecenyl and dodecenyl. R.sup.1 contains preferably from 2 to 12 and more especially from 2 to 8 carbon atoms. In a preferred meaning, R.sup.1 within the scope of this invention is alkenyl having from 2 to 4 carbon atoms.
The diradical R is, for example, lower alkylene, arylene, a saturated bivalent cycloaliphatic group having from 6 to 10 carbon atoms, alkylenearylene, arylenea

REFERENCES:
patent: 4451629 (1984-05-01), Tanaka et al.
patent: 5690953 (1997-11-01), Molock et al.

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