Rapid Soybean Oil Copolymers Synthesis by Microwave‐Assisted Cationic Polymerization

Sacristán, Marta; Ronda, Juan C.; Galià, Marina; Cádiz, Virgínia

doi:10.1002/macp.200900571

Cited by 10 publications

(8 citation statements)

References 22 publications

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“…According to the literature, there are three main routes for the synthesis of polymers from plant oils. The first approach corresponds to the direct polymerization through the C=C bonds . Their presence allows the polymerization of the oils into solid polymeric materials either through free radical or cationic mechanisms .…”

Section: Introductionmentioning

confidence: 99%

Renewable thermoset copolymers from tung oil and natural terpenes

Sibaja

Sargent

Auad

2014

J of Applied Polymer Sci

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The cationic copolymerization of tung oil, limonene, and myrcene as comonomers, initiated by boron trifluoride, is presented and discussed in this work. Dynamic mechanical analysis revealed that all copolymers behave as thermosets. FTIR spectra for both copolymers, after extraction with dichloromethane, suggested that the major component of the insoluble fraction was reacted tung oil (a cross‐linked triglyceride network). Likewise, unreacted tung oil was found to be the main component of the soluble phase. Also, all the copolymers showed only one tan δ peak, indicating no phase separation. Glass transition temperature (Tg) increased with the myrcene content and decreased almost linearly as the limonene content increased. Furthermore, the Fox and Loshaek model showed a relatively good prediction of the Tg values of the polymers. The Young's modulus ranged from 33.8 to 4.7 MPa for all tested thermosets. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 41155.

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Section: Introductionmentioning

confidence: 99%

Renewable thermoset copolymers from tung oil and natural terpenes

Sibaja

Sargent

Auad

2014

J of Applied Polymer Sci

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“…Curing and postcuring conditions were established as 12 h at 80 C, 24 h at 140 C, and 12 h at 160 C according to previously reported studies. 7,15 The copolymers were obtained in essentially quantitative yields and appeared as dark brown rubbery materials at room temperature; they ranged from tough to very soft rubbers. The composition of the copolymers was studied by analysis of the results of overnight Soxhlet extractions with DCM as the solvent.…”

Section: Resultsmentioning

confidence: 99%

“…We previously described the cationic copolymerization of SOY, ST, and DVB under microwave irradiation with BF 3 ÁOEt 2 /MeOL as an initiator, and a comparison with conventional heating showed a great enhancement in the reaction rates. 15 In this way, the cationic copolymerization of the previous P-containing system was carried out under microwave irradiation with different power inputs and reaction times. Solid materials of an extremely fragile nature and poor mechanical integrity were obtained in all cases; the materials also contained high loadings of soluble fractions.…”

Section: Resultsmentioning

confidence: 99%

Phosphorus‐containing soybean‐oil copolymers: Cross‐metathesis of fatty acid derivatives as an alternative to phosphorus‐containing reactive flame retardants

Sacristán¹,

Ronda²,

Galià³

et al. 2011

J of Applied Polymer Sci

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Two different approaches to the creation of phosphorus-containing soybean-oil copolymers were investigated. First, two phosphorus-containing styrene (ST) derivatives, diphenyl styryl phosphine oxide and dimethylp-vinylbenzylphosphonate (STP2), where tested as comonomers in the cationic copolymerization of soybean oil (SOY), ST, and divinylbenzene (DVB), to obtain heterogeneous systems in all cases. To overcome this drawback, the crossmetathesis reaction of methyl 10-undecenoate and STP2 was carried out to link the phosphorus moiety to the vegetable-oil derivative. This second approach permitted the synthesis of a new reactive phosphorus-containing plant-oil derivative, which was incorporated into the soybean oil, ST, and DVB system. The cationic copolymerization was investigated, and the structure, thermal stability, and mechanical and flame-retardant properties of the resulting copolymers were studied. Thermosets with moderate glasstransition temperatures were obtained; this showed that the cross-metathesis reaction is a convenient way to produce oilcompatible monomers able to undergo homogeneous polymerization reactions. The resulting thermosets with 1% phosphorus had limiting oxygen index values about 24.0; this indicated an improvement in the fire-retardant properties of the soybean-oil-based copolymers.

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“…In this way, we explored the cationic copolymerization of soybean oil, ST, and DVB under microwave assistance [22] (Scheme 2). First, experiments were focused on the cationic polymerization of soybean oil with and without microwave irradiation to compare conversion in different conditions.…”

Section: Microwave Polymerizationmentioning

confidence: 99%

Vegetable oils as platform chemicals for polymer synthesis

Ronda

Lligadas

Galià

et al. 2011

Euro J Lipid Sci & Tech

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114

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Natural vegetable oils have been transformed in polymers following three main routes. The first is the direct polymerization through the double bonds of the fatty acid chain. The cationic copolymerization of soybean oil with styrene, divinylbenzene, and different amounts of styrenic monomers containing Si allows producing materials with improved mechanical and flame retardant properties. The second route is the functionalization of the triglyceride double bonds to introduce readily polymerizable groups: The singlet oxygen photoperoxidation-dehydration of the allylic positions of the high oleic sunflower oil allows producing enone-containing triglycerides that are chemically crosslinked with aromatic diamines through aza-Michael reactions. At high temperatures, this curing reaction proceeds through a complex mechanism leading to quinoline moieties. This new crosslinking approach can be also applied to aldehyde containing triglycerides. The third route consists of using plant oil-derived chemicals like 10-undecenoic acid to produce tailor made monomers. Acyclic diene metathesis polymerization has been applied to allyl 10-undecenoate, 10-[2 0 ,5 0 -bis(10-undecenoyloxy)phenyl]-9,10-dihydro-9-oxa-10-phospha-phenanthrene-10-oxide, and 1,3-bis(10-undecenoyl)glycerol to prepare a set of polyesters with different phosphorus and hydroxyl contents. Moreover thiol-ene ''click'' coupling of allyl 10-undecenoate with mercaptoethanol, 3-mercaptopropanoic acid, and 3-mercaptopropyltrimethoxysilane has been used to produce difunctional telechelic polyesters.

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Rapid Soybean Oil Copolymers Synthesis by Microwave‐Assisted Cationic Polymerization

Cited by 10 publications

References 22 publications

Renewable thermoset copolymers from tung oil and natural terpenes

Renewable thermoset copolymers from tung oil and natural terpenes

Phosphorus‐containing soybean‐oil copolymers: Cross‐metathesis of fatty acid derivatives as an alternative to phosphorus‐containing reactive flame retardants

Vegetable oils as platform chemicals for polymer synthesis

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