Chemical modification of polydienic elastomers by organophosphorated reagents

Derouet, Daniel; Brosse, Jean‐Claude; Cauret, Laurent; Morvan, Frédérique; Mulder‐Houdayer, Stéphanie

doi:10.1002/app.11669

Cited by 11 publications

(9 citation statements)

References 12 publications

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“…The ENRs with 20, 35, and 50 mol% epoxide (denoted by ENR20, ENR35, and ENR50, respectively) were synthesized in‐house via in situ performic epoxidation according to the methods outlined by Heping et al and Derouet et al . That is, the H 2 O 2 /isoprene unit molar ratios 0.20, 0.35, and 0.50 were used to prepare ENR20, ENR35, and ENR50, respectively.…”

Section: Methodsmentioning

confidence: 99%

Nanosilica‐reinforced Epoxidized natural rubber nanocomposites: Effect of Epoxidation level on morphological and mechanical properties

et al. 2015

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Epoxidized natural rubbers (ENRs) with three different epoxide contents (i.e., 20, 35, and 50 mol% indicated as ENR20, ENR35, and ENR50, respectively) were prepared. They were then reinforced with 3‐methyacryloxypropyl trimethoxysilane‐modified nanosilica (MPTS‐SiO2). Influence of epoxide level in ENR molecules on morphological, mechanical, and dynamic mechanical properties of the ENR nanocomposites was investigated. The scanning electron microscopy results revealed larger agglomerates of SiO2 were found in the ENR composites with higher epoxide content. Furthermore, the strength and moduli of the ENR nanocomposites increased with increasing epoxide content. However, the optimal tensile strength and elongation at break were observed in the nanocomposites with the intermediate level of epoxide contents. The correlation between the strength properties and the interfacial silica‐matrix adhesion indicated that the maximum interfacial adhesion of the nanocomposites was observed in the nanocomposite with ENR35. Also, DMA results indicated stronger interaction between ENR35 and MPTS‐SiO2 due to higher storage modulus. POLYM. COMPOS., 38:1151–1157, 2017. © 2015 Society of Plastics Engineers

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Section: Methodsmentioning

confidence: 99%

Nanosilica‐reinforced Epoxidized natural rubber nanocomposites: Effect of Epoxidation level on morphological and mechanical properties

et al. 2015

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“…33 Formic acid and hydrogen peroxide were used in equimolar amounts. The amount of hydrogen peroxide was calculated according to the following relation:…”

Section: Epoxidation Of Nr Latexmentioning

confidence: 99%

Physical and mechanical properties of poly(methyl methacrylate)‐grafted natural rubber synthesized by methyl methacrylate photopolymerization initiated by N,N‐diethyldithiocarbamate functions previously created on natural rubber chains

Derouet

Tran

Leblanc

2009

J of Applied Polymer Sci

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Well-defined poly(methyl methacrylate) (PMMA)-grafted natural rubbers (NRs) were prepared to study the structure-property relationships. Syntheses were achieved by the photopolymerization of methyl methacrylate initiated by N,N-diethyldithiocarbamate groups created beforehand in side positions on the NR chains. With this procedure, good control of the graft density and PMMA content could be obtained. Thermal, morphological, and mechanical properties of NR-g-PMMA copolymers were studied as a function of the NR/PMMA composition and graft density. NR-g-PMMAs containing 15-80% grafted PMMA showed characteristics of heterogeneous materials (characterized by two glass-transition temperatures, those of PMMA and NR, in differential scanning calorimetry). Under these conditions, they developed the morphology of thermoplastic elastomers with PMMA nodules dispersed in the rubber matrix when the PMMA content was near 20%; conversely, they developed the morphology of softened thermoplastics with rubber nodules dispersed in PMMA when the PMMA content was near 80%. Graft copolymers containing about 20% PMMA remained essentially rubbery, but they were already different from pure NR. On the other hand, the thermal stability of NR wash improved after the introduction of PMMA grafts onto NR chains.

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“…To verify the ability of DBP to react with oxirane rings of epoxidized rubber in latex medium, the results obtained in these conditions were compared with those obtained in organic solvent 10, 13. In dichloromethane and without an external catalyst, DBP reacts quickly with partially epoxidized 1,4‐polyisoprene: epoxidized units are totally consumed after only 3 h (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…This modification is important due to the great reactivity of oxirane rings toward nucleophilic reagents. For example, reactions with amine,5 carboxylic acid,6, 7 alcohol,8, 9 and phosphoric acid derivatives,10, 11 have been studied on epoxidized polyisoprene in solution.…”

Section: Introductionmentioning

confidence: 99%

Chemical modification of polydienes in latex medium: Study of epoxidation and ring opening of oxiranes

Derouet

Mulder‐Houdayer

Brosse

2004

J of Applied Polymer Sci

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Referring to previous work carried out in organic solvents, a study of the action of nucleophilic reagents on epoxidized units of 1,4-epoxidized polyisoprene (synthetic polyisoprene or natural rubber) was performed in latex medium. Among the considered reagents, dialkylphosphate and ammonium diethyldithiophosphate demonstrated the ability to add under these reaction conditions on epoxidized units according to a SN2 substitution with an oxirane ring-opening mechanism. A systematic study was performed with dibutylphosphate that was shown to be very reactive. Grafting of phosphorated groups along polyisoprene chains was carried out via reaction of the acidic function (P-OH) of the phosphate with oxirane rings previously created on a 1,4-polyisoprene backbone. The prominent role of latex pH on the reaction was shown.

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Chemical modification of polydienic elastomers by organophosphorated reagents

Cited by 11 publications

References 12 publications

Nanosilica‐reinforced Epoxidized natural rubber nanocomposites: Effect of Epoxidation level on morphological and mechanical properties

Nanosilica‐reinforced Epoxidized natural rubber nanocomposites: Effect of Epoxidation level on morphological and mechanical properties

Physical and mechanical properties of poly(methyl methacrylate)‐grafted natural rubber synthesized by methyl methacrylate photopolymerization initiated by N,N‐diethyldithiocarbamate functions previously created on natural rubber chains

Chemical modification of polydienes in latex medium: Study of epoxidation and ring opening of oxiranes

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