Alcoholysis of epoxidized polyisoprenes by direct opening of oxirane rings with alcohol derivatives 2. Study on epoxidized 1,4-polyisoprene

Derouet, Daniel; Brosse, Jean‐Claude; Challioui, Allal

doi:10.1016/s0014-3057(00)00267-6

Cited by 22 publications

(14 citation statements)

References 15 publications

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“…[5][6][7][8] Epoxide or oxirane is an ether in which the oxygen atom is incorporated into the C@C bond to form a three-membered ring. [12][13][14] ENR is a pH sensitive polymer and favors neutral pH. The carbons in an epoxide are very reactive electrophile thus able to react with a variety of nucleophile.…”

Section: Introductionmentioning

confidence: 99%

“…10 In practice, the oxirane ROR is a common reaction during the preparation of ENR. 13 The ring opening reaction of epoxide using acid treatments is preferred due to their simplicity and low cost. 11 Thus, this reaction offers opportunities to functionalize ENR with other reactive substances, fillers, or polymers.…”

Section: Introductionmentioning

confidence: 99%

“…13 C-NMR suggests the fixation of alkyl (R) i.e., acetate group to the epoxide carbon via ester linkage and formation of hydroxyl groups in the polymer chains. 1 H-NMR revealed that 19.56% of epoxide was ring-opened from the total amount of the epoxide unit in ENR-50 and this was supported by Fourier Transform Infrared (FTIR) spectroscopy.…”

mentioning

confidence: 99%

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A structural study of epoxidized natural rubber (ENR‐50) ring opening under mild acidic condition

Hamzah

Bakar

Dahham

et al. 2016

J of Applied Polymer Sci

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A structural study of ring opening reaction of purified epoxidized natural rubber (ENR) with acetic acid was conducted using the NMR techniques and its thermal characteristic was evaluated with Thermal gravimetry/Differential Thermal Gravimetry (TG/DTG) and Differential Scanning Calorimetry (DSC) analyses. 1 H-NMR revealed that 19.56% of epoxide was ring-opened from the total amount of the epoxide unit in ENR-50 and this was supported by Fourier Transform Infrared (FTIR) spectroscopy. 13 C-NMR suggests the fixation of alkyl (R) i.e., acetate group to the epoxide carbon via ester linkage and formation of hydroxyl groups in the polymer chains. The attachment location of R occurred at both most (") and least (#) hindered carbons of the epoxide. The TG/DTG results of acid treated ENR-50 showed three decomposition steps at 235-338, 338-523, 523-627 8C due to the presence of the polymer chains mixture, i.e., ring-opened and intact epoxide of ENR-50. This increases the T g value of acid treated ENR-50 at 24.6 8C as compared to purified ENR-50 at 217.7 8C.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A structural study of epoxidized natural rubber (ENR‐50) ring opening under mild acidic condition

Hamzah

Bakar

Dahham

et al. 2016

J of Applied Polymer Sci

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“…This is the likely reason why there is very limited number of reports in the literature on homogenous (liquid-liquid phase) or semi-heterogeneous (liquid-solid phase) reaction condition involving chitosan and ENR. Furthermore, ENR is known to undergo ring-opening and double bond cleavage reactions [20][21][22][23][24][25]. To date, there is no report on the stability of the microstructure of ENR in conditions with different concentrations of acid.…”

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confidence: 99%

Preparation and characterization of biopolymers comprising chitosan-grafted-ENR via acid-induced reaction of ENR50 with chitosan

Haris¹,

Raju²

2014

Express Polym. Lett.

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This paper describes the first detailed tailored-approach for the preparation of biopolymers comprising chitosan (CTS) grafted onto the backbone of epoxidized natural rubber (CTS-g-ENR). In a typical experiment, appropriate amount of CTS and AlCl3•6H2O was added to a specified amount of ENR50 (ENR with about 50% epoxy content) dissolved in a dual-solvent consisting of 1,4-dioxane and water (97.5:2.5% v/v) and the resulting mixture refluxed with continuous stirring for 6 hours. Nuclear magnetic resonance (NMR) spectral analysis of a biocomposite, CTS-g-ENR-P1, revealed that its epoxy content is 22.36% which is considerably lower than 44.93% as determined for ENR50-control (ENR50 derivative obtained under similar experimental condition but in the absence of CTS). This means that the grafting of CTS onto the backbone of ENR had occurred. The revelation is affirmed by the presence of the characteristic absorption bands of CTS and ENR, and the appearance of new bands at 1219, 902 and 733 cm–1 in the Fourier transform infrared (FTIR) spectrum of CTS-g-ENR-P1. Further evidence that CTS had been successfully grafted onto the backbone of ENR can be deduced and described in this paper from the data obtained by means of Differential Scanning Calorimetric analysis, Thermogravimetric analysis and Variable Pressure Scanning Electron Microscopy

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“…They have focused on the study of solubility parameter, glass transition temperature and activation energy for gas permeation through epoxidized membrane of the block copolymer. The epoxidation studies related to the addition of nucleophilic reagents such as acid, amine and alcohol onto epoxidized polydiene were performed by Soutif et al 17 , Jayawardana et al 18 and Derouet et al 19 respectively. In addition, epoxidized styrene/butadiene block copolymers were used as templates for preparing nanostructured thermosets by Elena Serrano et al 20 .…”

Section: Introductionmentioning

confidence: 99%

Investigations into Morphology and Mechanical Properties of Epoxidized Polystyrene/Polybutadiene/Polystyrene (SBS) Triblock Copolymer

Pandit

Youssef

Saiter

et al. 2013

J. Nepal Chem. Soc.

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An architecturally asymmetric polystyrene-block-polybutadiene-block-polystyrene (SBS) triblock copolymer possessing lamellar morphology was subjected to different degrees of epoxidation with performic acid generated in situ by the reaction between hydrogen peroxide and formic acid. The effect of the chemical modification on morphology and mechanical behaviour of the block copolymer was investigated by means of different techniques such as electron microscopy, Fourier transform Infrared (FTIR) spectroscopy, tensile testing and differential scanning calorimetry (DSC). It was found that the microphase separation behaviour and hence the mechanical properties of the materials can be drastically altered via epoxidation of the diene block of the styrene/diene triblock copolymers.

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Alcoholysis of epoxidized polyisoprenes by direct opening of oxirane rings with alcohol derivatives 2. Study on epoxidized 1,4-polyisoprene

Cited by 22 publications

References 15 publications

A structural study of epoxidized natural rubber (ENR‐50) ring opening under mild acidic condition

A structural study of epoxidized natural rubber (ENR‐50) ring opening under mild acidic condition

Preparation and characterization of biopolymers comprising chitosan-grafted-ENR via acid-induced reaction of ENR50 with chitosan

Investigations into Morphology and Mechanical Properties of Epoxidized Polystyrene/Polybutadiene/Polystyrene (SBS) Triblock Copolymer

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