Autoxidized Oleic Acid Bifunctional Macro Peroxide Initiators for Free Radical and Condensation Polymerization. Synthesis and Characterization of Multiblock Copolymers

Hazer, Baki̇; Ayyıldız, Elif; Eren, Melike; Canbay, Hale Seçilmiş; Ashby, Richard D.

doi:10.1007/s10924-019-01536-6

Cited by 12 publications

(4 citation statements)

References 56 publications

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“…It was too high for the obtained polymer. This may be purified by fractional precipitation to remove the low molar mass of residues [36,37]. In the presence of TBHPO and TEPA initiators, chain session or chain degradation could possibly take place.…”

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confidence: 99%

Improvement of Thermal and Mechanical Properties of Vietnam Deproteinized Natural Rubber via Graft Copolymerization with Methyl Methacrylate

Nguyễn

Duy

Anh

et al. 2020

International Journal of Polymer Science

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In this study, we investigated the improvement of the thermal and mechanical properties of Vietnam deproteinized natural rubber (DPNR) via graft copolymerization of methyl methacrylate (MMA). The graft copolymerization was achieved successfully in latex stage using tert-butyl hydroperoxide (TBHPO) and tetra-ethylenepentamine (TEPA) as radical initiators at 30°C. By grafting with various MMA feeds and initiator concentration of 6.6×10−5 mol/g-rubber, the highest grafting efficiency and conversion were achieved at MMA of 15 wt.% per kg of rubber, 68% and 90%, respectively. The structure of grafted copolymers was characterized by 1H NMR, FTIR-ATR, and GPC, and thermal properties were investigated through DSC and TGA measurements. These showed that graft copolymers were more stable and rigid than DPNR. Storage modulus (G′) of graft copolymer was found to double that of DPNR, which contributed to the formation of graft copolymer. After sulfur vulcanization, the mechanical properties of DPNR-graft-PMMA, such as tensile strength, tear strength, and hardness, were improved significantly. Curing behaviors of the graft copolymers were found to be remarkably better than virgin DPNR.

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confidence: 99%

Improvement of Thermal and Mechanical Properties of Vietnam Deproteinized Natural Rubber via Graft Copolymerization with Methyl Methacrylate

Nguyễn

Duy

Anh

et al. 2020

International Journal of Polymer Science

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“…From the DSC analyses of the copolymers we saw that the T g decreased with increasing modified oleic acid molar content in the copolymer, since this is closely associated with the final chemical structure of the random copolymer chains. It is reasonable to expect that the plasticising effect of the oleic acid acrylate comonomer influences the molecular mobility of the active species, leading to a reduction in the T g of copolymers 47 – 49 . This property may potentially prove to be beneficial for a wood consolidant as plasticisers are known to increase the free volume of polymer chains, enabling them to be more flexible and move more easily 48 , 50 .…”

Section: Resultsmentioning

confidence: 99%

Comparative hydrodynamic characterisation of two hydroxylated polymers based on α-pinene- or oleic acid-derived monomers for potential use as archaeological consolidants

Cutajar

Machado

Crucitti

et al. 2022

Sci Rep

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The Oseberg Viking ship burial is one of the most extensive collections of Viking wooden artefacts ever excavated in Norway. In the early twentieth century, many of these artefacts were treated with alum in order to preserve them, inadvertently leading to their current degraded state. It is therefore crucial to develop new bioinspired polymers which could be used to conserve these artefacts and prevent further disintegration. Two hydroxylated polymers were synthesised (TPA6 and TPA7), using α-pinene- and oleic acid-derived monomers functionalised with an acrylate moiety. Characterisation using biomolecular hydrodynamics (analytical ultracentrifugation and high precision viscometry) has shown that these polymers have properties which would potentially make them good wood consolidants. Conformation analyses with the viscosity increment (ν) universal hydrodynamic parameter and ELLIPS1 software showed that both polymers had extended conformations, facilitating in situ networking when applied to wood. SEDFIT-MSTAR analyses of sedimentation equilibrium data indicates a weight average molar mass Mw of (3.9 ± 0.8) kDa and (4.2 ± 0.2) kDa for TPA6 and TPA7 respectively. Analyses with SEDFIT (sedimentation velocity) and MultiSig however revealed that TPA7 had a much greater homogeneity and a lower proportion of aggregation. These studies suggest that both these polymers—particularly TPA7—have characteristics suitable for wood consolidation, such as an optimal molar mass, conformation and a hydroxylated nature, making them interesting leads for further research.

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“…Three double bonds containing linolenic acid oxidize faster than two double bonds containing linoleic acid (18:2) and one double bond containing oleic acid and ricinoleic acid. Two weeks' autoxidation is enough to obtain high viscous linseed oil with high content linolenic acid (three double bonds; 18:3; Hazer & Ashby, 2023) while four months are needed to obtain oligomerized oleic acid (18:1; Hazer et al, 2017; Hazer et al, 2019) and ricinoleic acid with one double bond (18:1; Hazer & Eren, 2019).…”

Section: Autoxidationmentioning

confidence: 99%

Macro peroxide initiators based on autoxidized unsaturated plant oils: Block/graft copolymer conjugates for nanotechnology and biomedical applications

Hazer

2023

J Americ Oil Chem Soc

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The autoxidation of unsaturated fatty acids and their esters is one of the most important reactions in food and biological systems. Autoxidation is a type of reaction between air oxygen and unsaturated plant oils. This reaction starts with a hydrogen abstraction on the methylene group adjacent double bond, leaving a radical onto the carbon atom. Molecular oxygen attacks this radical leading to produce peroxide and hydroperoxide derivatives of the oligomerized unsaturated plant oils. Because peroxide groups thermally cleave to produce free radicals, hydroperoxide derivatives of unsaturated plant oil oligomers can be used in the free radical polymerization of vinyl monomers leading to the related block/graft copolymers. The obtained copolymers combined with the biodegradable natural plant oil gain superior properties such as biodegradability and softness. In this review article, the in vitro autoxidation of well‐known unsaturated plant oils‐soybean oil, linseed oil, and castor oil and some related unsaturated fatty acids‐oleic acid, linoleic acid, and ricinoleic acid was carried out under atmospheric conditions with or without exposing white light. Because the autoxidized unsaturated oil/fatty acids contain peroxide/hydroperoxide groups (they are referred to as macro peroxide initiators) that they are used in the free radical polymerization of vinyl monomers to obtain block/graft copolymers. The improved polymerization conditions, characterization, and applications of the obtained products will be discussed.

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Autoxidized Oleic Acid Bifunctional Macro Peroxide Initiators for Free Radical and Condensation Polymerization. Synthesis and Characterization of Multiblock Copolymers

Cited by 12 publications

References 56 publications

Improvement of Thermal and Mechanical Properties of Vietnam Deproteinized Natural Rubber via Graft Copolymerization with Methyl Methacrylate

Improvement of Thermal and Mechanical Properties of Vietnam Deproteinized Natural Rubber via Graft Copolymerization with Methyl Methacrylate

Comparative hydrodynamic characterisation of two hydroxylated polymers based on α-pinene- or oleic acid-derived monomers for potential use as archaeological consolidants

Macro peroxide initiators based on autoxidized unsaturated plant oils: Block/graft copolymer conjugates for nanotechnology and biomedical applications

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