New diethyl phosphonoalkyl acrylates and their reactivity in copolymerization

Boutevin, Bernard; Hamoui, Bachar; Parisi, Jean-Pierre

doi:10.1007/bf00343056

Cited by 17 publications

(9 citation statements)

References 8 publications

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“…As shown by Hamoui and co-workers [9][10][11] the addition of thioethylene glycol HS(CH 2 ) 2 OH or thioglycolic acid HSCH 2 CO 2 H on the double bond of diethyl allyl phosphate leads to mono adducts with yields close to 90%. The reactions were carried out under inert atmosphere with THF reflux in the presence of isobutyronitrile (AIBN).…”

Section: Introductionmentioning

confidence: 91%

New alkylated and perfluoroalkylated phosphonic acids: Synthesis, adhesive and water-repellent properties on aluminum substrates

Essahli

Asri

Boulahna

et al. 2006

Journal of Fluorine Chemistry

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Section: Introductionmentioning

confidence: 91%

New alkylated and perfluoroalkylated phosphonic acids: Synthesis, adhesive and water-repellent properties on aluminum substrates

Essahli

Asri

Boulahna

et al. 2006

Journal of Fluorine Chemistry

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“…One of the methods of incorporating phosphorus functionality into polymers is the polymerization and copolymerization of phosphorus‐containing vinyl monomers. For example, vinyl and allyl phosphonates have been synthesized and used as comonomers in addition polymers 12–17. Another approach to phosphorus‐containing polymers is simple modifications of polymers with phosphorus‐containing groups, such as those through the phosphorylation of poly(vinyl alcohol), cellulose, and polydienes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and copolymerization of new phosphorus‐containing acrylates

Avcı

Albayrak

2003

J. Polym. Sci. A Polym. Chem.

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Two phosphorus-containing acrylate monomers were synthesized from the reaction of ethyl ␣-chloromethyl acrylate and t-butyl ␣-bromomethyl acrylate with triethyl phosphite. The selective hydrolysis of the ethyl ester monomer with trimethylsilyl bromide (TMSBr) gave a phosphonic acid monomer. The attempted bulk polymerizations of the monomers at 57-60°C with 2,2Ј-azobisisobutyronitrile (AIBN) were unsuccessful; however, the monomers were copolymerized with methyl methacrylate (MMA) in bulk at 60°C with AIBN. The resulting copolymers produced chars on burning, showing potential as flame-retardant materials. Additionally, ␣-(chloromethyl)acryloyl chloride (CMAC) was reacted with diethyl (hydroxymethyl)phosphonate to obtain a new monomer with identical ester and ether moieties. This monomer was hydrolyzed with TMSBr, homopolymerized, and copolymerized with MMA. The thermal stabilities of the copolymers increased with increasing amounts of the phosphonate monomer in the copolymers. A new route to highly reactive phosphorus-containing acrylate monomers was developed. A new derivative of CMAC with mixed ester and ether groups was synthesized by substitution, first with diethyl (hydroxymethyl)phosphonate and then with sodium acetate. This monomer showed the highest reactivity and gave a crosslinked polymer. The incorporation of an ester group increased the rate of polymerization. The relative reactivities of the synthesized monomers in photopolymerizations were determined and compared with those of the other phosphorouscontaining acrylate monomers. Changing the monomer structure allowed control of the polymerization reactivity so that new phosphorus-containing polymers with desirable properties could be obtained.

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“…[17] In works concerning styrenic organophosphonated monomers, the Arbusov reaction between a halogenated alkyl styrene and a trialkyl phosphite has also been described. [18][19][20] Another method consists of reacting a dialkylphosphite with an isocyanate. [21] In previous studies, [22,23] we have realized the synthesis of a phosphonated dimethacrylate monomer bearing thioether functions.…”

Section: Introductionmentioning

confidence: 99%

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

Youssef¹,

Lecamp²,

Khatib³

et al. 2003

Macro Chemistry & Physics

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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).

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New diethyl phosphonoalkyl acrylates and their reactivity in copolymerization

Cited by 17 publications

References 8 publications

New alkylated and perfluoroalkylated phosphonic acids: Synthesis, adhesive and water-repellent properties on aluminum substrates

New alkylated and perfluoroalkylated phosphonic acids: Synthesis, adhesive and water-repellent properties on aluminum substrates

Synthesis and copolymerization of new phosphorus‐containing acrylates

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

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