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Bridged phosphorylated diamines: Synthesis, thermal stability and flame retarding properties in epoxy resins

: Klinkowski, Cristoph; Wagener, Sebastian; Ciesielski, Michael; Döring, Manfred


Polymer degradation and stability 106 (2014), pp.122-128
ISSN: 0141-3910
European Meeting on Fire Retardancy and Protection of Materials <14, 2013, Lille>
Journal Article, Conference Paper
Fraunhofer LBF ()
synthesis; thermal stability; flame retarding property; epoxy resin; stability

The synthesis of different phosphorylated m-phenylenediamines is described. In this context a new synthetic pathway to 10-chloro-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO-Cl) is reported. The reactivities of DOPO-C1 and 10-chloro-9,10-dihydro-9-oxa-10-phosphaphenanthrene (DOP-Cl) towards amines have been compared. Decomposition properties of the pure compounds have been determined by thermogravimetric analysis (TGA) and indicate a relationship between the chemical environment around the phosphorus atom and the thermostability of the corresponding compound. All substances were incorporated into the epoxy novolac resin system DEN438/DICY/Fenuron. Thermal as well as flame retarding properties of the cured epoxy resins have been investigated by differential scanning analysis (DSC) and UL-94 test. The changes of the glass transition temperature (T-g) and the decomposition temperature of the cured epoxy resins are small compared to the pure epoxy resin. The synthesized 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO), 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-sulfide (DOPS), diphenylphosphine sulfide (Ph2PO) and 5,5dimethyl-1,3,2-dioxaphosphinane 2-sulfide (DDPS) derivatives exhibit a pronounced flame retardant effect in DEN438/DICY/Fenuron.