Neue Monomere auf Quinolinonbasis für die Entwicklung hochbrechender Polymere für die Ophthalmologie

Es wurden in dieser Arbeit acht neue hochbrechende Monomere dargestellt. Von diesen besitzen sieben Monomere Seitengruppen, in denen Quinolinonderivate (Q1-Q7) zur Brechungsindexerhöhung verwendet werden. Bei diesen Monomeren wurde das Substitutionsmuster am Quinolinon, der Spacer, der das Quinolino...

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Bibliographic Details
Main Author: Helmstetter, Simon Thomas
Contributors: Hampp, Norbert (Prof. Dr.) (Thesis advisor)
Format: Doctoral Thesis
Published: Philipps-Universität Marburg 2016
Online Access:PDF Full Text
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In this work eight novel high refractive index monomers were synthesized. Seven of them contain Quinolinone-derivates Q1 - Q7, in order to increase refractive indices in their side-chain. These monomers vary in substitution of the quinolinone, spacer and polymerizable group. Furthermore, a monomer containing a chromen-2-one (S1) in its side-chain was synthesized So far, no monomers of this structure containing quinolinone or chromen-2-one are known for ophthalmic application. Homopolymers were confected of the new monomers, having refractive indices up to n(D) = 1.685. Glass transition-temperatures of the homopolymers were beyond the figure of merit for intraocular lens application, ABBE-numbers also understate requirements. Therefore, copolymers of the new monomers were synthesized. By examination of the properties of binary copolymers linear, correlations between percentage of monomers and refractive index respectively glass-transition temperature were found. For ABBE-number an approximately linear correlation between ABBE-number and percentage of the monomers was found. These relations were used in order to calculate properties of ternary copolymers. Mixtures were determined which provide suitable materials for manufacturing of intraocular lenses. Two of these mixtures were chosen, and the polymers synthesized and characterized. Predicted values for refractive index were very precise, for glass-transition temperature satisfactory and for ABBE-number sufficient. Especially prediction of ABBE-number was not optimal. Therefore a more sophisticated method for its prediction was developed. The use of this method enables reliable prediction of ABBE-number. Moreover, both materials were examined concerning absorption, light stability and glistening. Material M1, containing Q1, possesses a good light stability, does not show glistening and is transparent at visible wavelengths. Its refractive index is n(D) = 1.592, glass-transition-temperature T(g) = 24 °C and ABBE-number ν(ABBE) = 28. This is why the specifications of an IOL-material were not achieved. M2, containing Q2, fulfills all requirements concerning n(D), T(g), und ν(ABBE), but its light stability and glistening-behavior exclude the use of M2 as a material for IOLs. Proposals were made in order to rectify the deficits of M1. Also for monomer Q2 suggestions were made in order to enable its use as a monomer for IOL manufacture. In conclusion Q1 can be seen as a new monomer for ophthalmic application. Hereby a new application for the Quinolinone-structure was found.