Effects of Catalyst Type and Reaction Parameters on One-Step Acrylation of Soybean Oil

Zhang, Pei; Xin, Junna; Zhang, Jinwen

doi:10.1021/sc400206t

Cited by 39 publications

(52 citation statements)

References 43 publications

(47 reference statements)

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“…[4,5] Especially, its derivatives epoxidized soybean oil (ESO) and acrylated epoxidized soybean oil (AESO) have been widely applied in the UV curable coatings. [6,7] However, due to the flexible long aliphatic chain of soybean oil, as much as 50% or more petroleum-based rigid compounds, such as styrene [8,9], acrylate acid [10] and divinylbenzene [11,12], are necessary to make its mechanical or thermal properties acceptable for end use.…”

Section: Introductionmentioning

confidence: 99%

Soybean oil-based UV-curable coatings strengthened by crosslink agent derived from itaconic acid together with 2-hydroxyethyl methacrylate phosphate

Dai

Liu

et al. 2016

Progress in Organic Coatings

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Section: Introductionmentioning

confidence: 99%

Soybean oil-based UV-curable coatings strengthened by crosslink agent derived from itaconic acid together with 2-hydroxyethyl methacrylate phosphate

Dai

Liu

et al. 2016

Progress in Organic Coatings

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“…In order to estimate the acrylation degree of ACSO, the hydroxyl values were determined and compared with the theoretical values. The number of acrylate groups per triglyceride molecule was determined by 1 H NMR . The results are listed in Table .…”

Section: Resultsmentioning

confidence: 99%

Development of acrylated soybean oil‐based UV‐curable coatings with high impact strength from low viscosity oligomer

Liu

Lü

2017

J of Applied Polymer Sci

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In recent years, more and more attention has been paid to bio‐based materials due to their sustainability and environmental friendliness. The combination of biomass and ultraviolet (UV) curing technology can reduce the dependence on petroleum products and emissions of volatile organic compounds. In this article, a new environment‐friendly UV‐curable coating with good performances was successfully prepared from acrylated soybean oil (ACSO). ACSO was obtained at low temperature without catalyst and inhibitor by reacting soybean oil‐based polyol with acryloyl chloride and characterized by Fourier transform infrared spectroscopy and nuclear magnetic resonance. It was found that the UV‐curable oligomer of ACSO had lower viscosity and better ductility, compared to acrylated epoxidized soybean oil (AESO). The properties of UV‐cured films prepared by ACSO were studied and compared with films from AESO. The results showed that the ACSO‐based films were significantly improved in the adhesion and impact resistance. Furthermore, the addition of styrene could enhance the hardness and impact resistance of films. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 45698.

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“…Wool et al described and studied the kinetic of an acid-catalyzed acrylation of epoxidized oils with acrylic acid (Scheme 11a) [139]. A more sustainable direct acrylation of soybean oil with acrylic acid using boron trifluoride etherate catalyst was reported by Zhang et al (Scheme 11b) [140,141]. The recovery and recycling of both the catalyst and excess of acrylic acid was also studied.…”

Section: Other Polymerization Strategies: Insertion Of a Polymerizablmentioning

confidence: 99%

Sustainable Synthetic Approaches for the Preparation of Plant Oil‐Based Thermosets

Llevot

2016

J Americ Oil Chem Soc

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a more sustainable future. Due to an ever-increasing population on our planet and industrial developments, a major focus is on energy and fuel supply, as well as chemical and polymer production. In search for alternatives to the finite fossil feedstocks, the renewability and structural diversity of biomass makes it an excellent candidate [1][2][3][4][5][6]. Especially in polymer science, the use of renewable resources has been intensively investigated and discussed in several reviews over the last years [7][8][9][10][11]. Amongst biomass, vegetable oils constitute a platform of aliphatic hydrocarbons, particularly studied as polymer precursors due to their good availability, low price, inherent biodegradability and potential for chemical modifications [12][13][14][15][16]. Vegetable oils are composed of triglycerides, which consist of three fatty acid chains esterified with glycerol. Fatty acids vary in their chain length, as well as degree and location of their unsaturations. The fatty acid structures of the plant oils discussed in this review are shown in Scheme 1 and the composition of these oils displayed in Table 1. The fatty acid composition of the triglycerides, depending on the plant origin, influences their properties significantly [14]. Well-defined fatty acids can be recovered after hydrolysis of triglycerides and further separation and purification [17]. The latter can be transformed into difunctional monomers for the synthesis of a broad range of thermoplastic polymers [18]. However, this additional step decreases the sustainability of the synthesis. Thus, the direct polymerization of poly-functional vegetable oils into thermoset polymers represents a "greener" approach towards polymeric materials.Thermosets are cross-linked polymeric materials known for their good thermomechanical properties and chemical resistance. The production of these polymers represents ~20% of the total annual polymer production [19]. Thermosets can be synthesized in different chemical ways and the production of biobased thermosets has been recently Abstract The good availability and high degree of functionalization possibilities of plant oils entitles them to be one of the most intensively studied renewable resources, especially in polymer science. However, in line with the principles of green chemistry, the use of renewable resources should be accompanied with catalytic procedures, comparably less or non-toxic chemicals, as well as reduction of waste and energy consumption to achieve an overall sustainable process. In this review, these aspects are addressed using the example of plant oil-based thermoset materials, which bear the advantage, in terms of sustainability, of not requiring a separation or purification step prior to polymerization. The direct homopolymerization of plant oils, as well as copolymerization, exclusively with other renewable resources, are highlighted. The sustainability of the synthesis of a broad range of thermosets including epoxy resins, polyurethane networks, polybenzoxazines and unsaturated poly...

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Effects of Catalyst Type and Reaction Parameters on One-Step Acrylation of Soybean Oil

Cited by 39 publications

References 43 publications

Soybean oil-based UV-curable coatings strengthened by crosslink agent derived from itaconic acid together with 2-hydroxyethyl methacrylate phosphate

Soybean oil-based UV-curable coatings strengthened by crosslink agent derived from itaconic acid together with 2-hydroxyethyl methacrylate phosphate

Development of acrylated soybean oil‐based UV‐curable coatings with high impact strength from low viscosity oligomer

Sustainable Synthetic Approaches for the Preparation of Plant Oil‐Based Thermosets

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