New Phosphonated Methacrylates: Synthesis, Photocuring and Study of their Thermal and Flame‐Retardant Properties

Abstract

In this work, a new methacrylate phosphonate monomer synthesis was described according to two routes: firstly, by condensation of methacrylic acid with a phosphonate epoxide and secondly by an esterification between methacryloyl chloride and a phosphonate diol. The photoinduced polymerization of this new monomer was studied as a function of reaction temperature. The optimal conversion of the photopolymerization was 81% for temperatures below 60 °C. Above 60 °C, the existence of a thermal polymerization leads to a decrease in the apparent photochemical yield. This new monomer is less reactive than the commercial dimethacrylate polyether of Bisphenol A we have used for copolymerization. Mechanical and thermal properties of the final copolymers were studied as a function of methacrylate phosphonate monomer content. Tg of the copolymers reaches a maximum when the phosphorus content is about 2%. The addition of phosphorus leads to an improvement of the thermal and flame‐retardant properties. Thus, addition of 2% phosphorus allows us to decrease the degradation rate, to increase the amount of remaining residue after combustion up to 12%, and finally to increase the Limiting Oxygen Index (LOI) from 16.8 (0% P) to 21.4 (2% P).

Novel phosphorilated flame retardant thermosets: epoxy–benzoxazine–novolac systems

“…Of all the organo-phosphorous compounds which can be used as flame-retardants, the phosphorus monomers bearing P-C bonds are preferred [11]. In a previous paper, we studied the synthesis and polymerization of a novel glycidyl phosphinate, 10-(9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide)-2,3-epoxypropyl (DOPO-Gly) [12].…”

Synthesis of novel copolymers obtained from acceptor/donor radical copolymerization of phosphonated allyl monomers and maleic anhydride

“…Hence FR additives having higher M w should allow reducing this phenomenon. A wide range of phosphorus‐containing polymers were synthesized and used as FR additives of polymeric materials 8–10. Phosphorus‐containing allyl monomers have also attracted much interest.…”

“…A wide range of phosphorus-containing polymers were synthesized and used as FR additives of polymeric materials. [8][9][10] Phosphorus-containing allyl monomers have also attracted much interest. We have recently developed 11,12 the synthesis of polymers from radical polymerization of 2-R-5-ethyl-5-(allyloxymethyl)-2-oxo-1,3,2-dioxaphosphorinane (Scheme 1).…”

Microfluidic Lithography to Create Dynamic Gradient SAM Surfaces for Spatio‐temporal Control of Directed Cell Migration

“…Hydrogen bromide, tetrabromodibenzo‐ p ‐dioxin and tetramoromdibenzofuran may be released during combustion, causing corrosion and suspected toxicity. In contrast, phosphorus‐containing compounds1–12 provide powerful flame retardancy by covering the outer layer of polymers with a non‐flammable char during combustion. The solid phase flame retardant mechanism makes them environmentally friendly compounds.…”