The synthesis and cationic polymerization of novel monomers from renewable sources

Crivello, James V.; Narayan, Ramesh; Bratslavsky, S. A.; Yang, Bo

doi:10.1002/masy.19961070109

Cited by 17 publications

(17 citation statements)

References 12 publications

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“…Faster drying times can be achieved by using radiation curing . Several modified oils such as epoxidized oil, epoxy norbornene oil, and acrylated oil have been developed. Naturally occurring epoxidized vegetable oils such as vernonia oil have been studied as reactive diluents .…”

Section: Introductionmentioning

confidence: 99%

Modified soybean oil as a reactive diluent: Synthesis and characterization

Nalawade

Mehta

Pugh

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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Soybean oil was modified in two steps: (1) conjugation of soybean oil and (2) Diels‐Alder addition with 3‐(trimethoxysilyl)propyl methacrylate, 2,2,2‐trifluoroethyl methacrylate and triallyl ether acrylate. The structures were characterized using 1H NMR, 13C NMR, 13C‐1H gradient heteronuclear single quantum coherence (gHSQC) NMR spectroscopy, and MALDI‐TOF mass spectrometry. The 13C‐1H gHSQC NMR spectra helped confirm the formation of a cyclohexene ring in all reactions, indicating a Diels‐Alder addition. The diluent efficiency of modified soybean oil was evaluated in long oil alkyd formulation. Triallyl ether functionalized soybean oil resulted in the highest reduction in the viscosity of the alkyd formulations. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 3045–3059

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Section: Introductionmentioning

confidence: 99%

Modified soybean oil as a reactive diluent: Synthesis and characterization

Nalawade

Mehta

Pugh

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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“…They have been used as received from the plants as air‐drying linseed oils or as parts of resins such as alkyds. Fatty acids have also been chemically modified to be able to polymerize in ways other than oxidative crosslinking, such as the cationic polymerization of epoxidized vegetable oil 2–4. Drawbacks, such as low reactivity, polydispersity (a mixture of different fatty acids normally exist in a vegetable oil), and poor long‐term durability, have limited their use in favor of synthetic polymers as coating resins.…”

Section: Introductionmentioning

confidence: 99%

Thiol–ene coupling reaction of fatty acid monomers

Samuelsson

Jönsson

Brinck

et al. 2004

J. Polym. Sci. A Polym. Chem.

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The reactivities and reaction rates of the thiol–ene coupling reaction of 2‐ethyl‐(hydroxymethyl)‐1,3‐propanediol trimercapto acetate and 2‐ethyl‐(hydroxymethyl)‐1,3‐propanediol trimercapto propionate with two common unsaturated fatty acid methyl esters (methyl oleate and methyl linoleate) were evaluated. The reactions were monitored with real‐time IR and 1H NMR, which both showed that the mercapto acetate was more reactive than the mercapto propionate. Both thiols were more prone to add to the monounsaturated methyl oleate than to methyl linoleate, which contained two unconjugated double bonds. According to bond energy calculations, the thiol hydrogen of mercapto acetate was somewhat more difficult to abstract than the hydrogen of mercapto propionate. Consequently, the formed SC bond in the acetate case was stronger than in the propionate case, and so the equilibrium was more shifted toward the addition products. The real‐time IR measurements also showed that the cis unsaturation in methyl oleate isomerized much more quickly than that in methyl linoleate, and this also had an impact on the overall addition rate of the thiols because a trans unsaturation was more reactive than a cis unsaturation. The higher isomerization rates in the oleate systems, compared with those of the linoleate systems, was suggested to be due to a more restricted rotation along the CC bond of the reacted unsaturation in linoleate. This study showed the importance of trans unsaturations in obtaining reasonable reaction rates in thiol–ene reactions with fatty acid derivatives. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 6346–6352, 2004

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“…[8] Epoxidized seed oils are also used as binders for cationic UV-curable coatings and inks. [9,10] However, epoxidized seed oils are also associated with slow cationic cure rates. [11] Linseed oil has also been modified by reacting with cyclopentadiene to form a partially norbornylized product, which can be used as a reactive diluent.…”

Section: Introductionmentioning

confidence: 99%

Epoxidation of partially norbornylized linseed oil

Chen

Soucek

Simonsick

et al. 2002

Macromol. Chem. Phys.

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Epoxidation of linseed oil was performed with peracetic acid formed in situ by the reaction of hydrogen peroxide and acetic acid in the presence of Amberlite 120H as catalyst, and toluene as solvent. Some variables were evaluated as temperature and the molar ratio and solution of aqueous hydrogen peroxide (30 and 50 wt%) for obtaining a maximum of yield and conversion of epoxidized oil. The characterization of conversion of double bonds (DB) to epoxy ring, the relative percentage of epoxidation and selectivity, were performed by 1 H-NMR and FTIR-HART. The conditions rendered a maximum epoxidation of 93.4%, a conversion or double bonds of 97% and a selectivity of 96.3% were obtained at 80°C, employing a molar ratio 1:1.5 of double bonds (DB) to H 2 O 2 (50 wt%), 1:0.5 of DB to acetic acid, and 25 wt% of catalyst, in only 50 min and with a good reproducibility (±1.1%).

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The synthesis and cationic polymerization of novel monomers from renewable sources

Cited by 17 publications

References 12 publications

Modified soybean oil as a reactive diluent: Synthesis and characterization

Modified soybean oil as a reactive diluent: Synthesis and characterization

Thiol–ene coupling reaction of fatty acid monomers

Epoxidation of partially norbornylized linseed oil

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