Polysiloxane-polyol macromers, their preparation and their use

Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...

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523106, 523107, 525 542, 5253265, 5262382, 52623823, 526301, 526302, 526304, 528 32, G02B 104, C08G 7742

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060433280

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BRIEF SUMMARY
The present invention describes a polysiloxane-polyol macromer which is uninterrupted or interrupted by a bivalent structural element and furthermore carries at least one polymerizable segment on a polyol segment; a polymer comprising a polymerization product of at least one macromer according to the invention and, if appropriate, of at least one vinylic comonomer; intermediates; processes for the preparation of a macromer and a polymerization product; moldings, contact lenses, corneal implants or biomedical articles of a polymerization product; and furthermore the use of a macromer according to the invention or of a polymer prepared therefrom for coating a substrate.
JP 62/068820 and JP 63/139 106 (Kao Corporation) describe a polymer which consists of a polysiloxane which carries at least one primary amino group and via which the polysiloxane is modified with a sugar residue. These modified polysiloxanes are recommended as additives for hair care products.
WO 83/01617 (Minnesota Mining) describes, inter alia, a macromer which is a methacrylic or acrylamidoacyl derivative of a polysiloxane. Such siloxane derivatives are said to be useful as coatings for films.
EP 362 145 (Ciba-Geigy) describes a contact lens which is produced by reaction of a polydialkylsiloxane prepolymer containing terminal isocyanate with a polydialkylsiloxane-di- or -polyalkanol.
R. Stadler et al. (Macromolecules 28, 17-24 (1995)) describe polysiloxanes with pendent gluconamide or maltoheptaonamide groups, their synthesis starting, for example, from the corresponding peracylated N-allylaldonamides, which are added onto an Si--H group of a corresponding polysiloxane by hydrosilylation using a rhodium or platinum catalyst.
Biocompatible polysiloxane-containing polymers are still desired. Polysiloxanes which have, for example, the following specific properties are particularly desirable: toughness, mechanical damping, slow mechanical relaxation, permeability to oxygen and resistance to deposits of proteins, lipids and salts, and a certain hydrophilicity.
The problem described has been achieved with the preparation of polymerizable macromers which contain free hydroxyl groups. Macromers which are built up, for example, from an amino-alkylated polysiloxane which is derivatized with at least one polyol component containing an unsaturated polymerizable side chain are disclosed.
Polymers can be prepared on the one hand from the macromers according to the invention by homopolymerization. The macromers mentioned furthermore can be mixed and polymerized with one or more hydrophilic and/or hydrophobic comonomers. A special property of the macromers according to the invention is that they function as the element which controls microphase separation between selected hydrophilic and hydrophobic components in a crosslinked end product. The hydrophilic/hydrophobic microphase separation is in the region of less than 300 nm. The macromers are preferably crosslinked at the phase boundaries between, for example, an acrylate comonomer on the one hand and an unsaturated polymerizable side chain of polyols bonded to polysiloxane on the other hand, by covalent bonds and additionally by reversible physical interactions, for example hydrogen bridges. These are formed, for example, by numerous amide or urethane groups. The continuous siloxane phase which exists in the phase composite has the effect of producing a surprisingly high permeability to oxygen.
The present invention relates to a macromer comprising at least one section of the formula (I) ##STR1## in which (a) is a polysiloxane segment, (b) is a polyol segment which contains at least 4 C atoms, each X.sub.2 independently of the other is a bivalent radical which contains at least one carbonyl group, and in which contains at least one carbonyl group; compound.
A polysiloxane segment (a) is derived from a compound of the formula (III) ##STR2## in which n is an integer from 5 to 500; 99.8-25% of the radicals R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 independently of one another are alkyl and 0.

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