F. Jeanneaux

Perfluoroalkylated amphiphiles with a morpholinophosphate or a dimorpholinophosphate polar head group

Some previously synthesized (perfluoroalkyl)alkyldimorpholinophosphates, CnF2n+1CmH2mOP(O)- [N(CH2CH2)2O]2, were found remarkably to stabilize heat sterilizable water-in-fluorocarbon reverse emulsions and to have a strong proclivity to self-aggregate into microtubular assemblies when dispersed in water. This series has now been extended in order to allow structure–property relationships to be established and product optimization to be achieved. A new series of even more fluorophilic compounds consisting in bis[(perfluoroalkyl)alkyl]monomorpholinophosphates, (CnF2n+1CmH2mO)2P(O)N(CH2CH2)2O, was also synthesized. Preliminary surfactant activity and biocompatibility data are presented and compared to data obtained with non-fluorinated analogues.

The preparation of 1-hydroperfluorohexyne, octyne and decyne

Abstract 1-hydroperfluoroalkynes (RFCCH, RF  C4F9, C6F13, C8F17) were prepared from the corresponding alkenes by a multistep process involving bromination, dehydrobromination and debromination reactions. The influence of the perfluorinated chains length on chemical reactivity is illustrated by the important changes in experimental procedure, with respect to the lower terms, needed for the bromination and debromination steps. Physical data are reported for compounds RFCBr2CH2Br, RFCBrCHBr and RFCCH.

Preparation and evaluation of branched bis(F-alkyl)ethenes as O2/CO2 carriers for blood substitutes

Abstract Bis( F -butyl)ethene has proved to be a promising candidate oxygen-carrier for blood substitutes on the basis of the following criteria 1,2 : purity, definition and industrial feasibility; O 2 /CO 2 dissolving capacity; chemical and biological inertness; expiratory rate. The stability of its emulsions, when Pluronic F-68 and yolk phospholipids are used as surfactants, is comparable to that of Fluosol-DA. The issue on which most efforts must now be focussed in achieving second-generation blood substitutes is the improvement of their long-term stability. A new homologous series of bis( F -alkyl)ethenes, having one or two F -isopropyl chains, has been prepared in out search for the optimum compromise between emulsion stability (which is known to increase with the total number of carbon atoms) and excretion rate (which is negatively affected by this factor, but was shown to be improved by branching) 2 . These compounds were prepared in a high state of purity by addition of F -alkyl iodides to 1- F -alkylethenes followed by dehydroiodation. The trans isomer is formed almost exclusively. Their resistance towards chemical, biomimetic and biological agents, and physicochemical and biological characteristics, including preliminary data on emulsion stability and excretion rate, will be discussed.