UV curable soybean‐oil hybrid systems based on thiol‐acrylate and thiol‐ene‐acrylate chemistry

Zhang, Dandan; Zhang, D. D.; Liang, Hongbo; Bu, Jiang; Xiong, Lei; Huang, Shengmei

doi:10.1002/app.42095

Cited by 19 publications

(9 citation statements)

References 26 publications

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“…Comparing with reported results [54][55][56][57] , the present three polymers show a little stronger hydrophilicity. This result is attributed to the fact that phosphorus is a high electronegative element and P=O bond has a strong tendency to form hydrogen bond with water.…”

Section: Surface Propertiessupporting

confidence: 75%

Phosphorus-containing polymers from THPS. VII. Synthesis of phosphorus-containing trialkynes and their metal-free 1,3-dipolar cycloaddition reaction with azidated soybean-oil

et al. 2016

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A novel hydrolysis-resistant trialkynes, namely tris(prop-2-yn-1-yloxy methyl)phosphane oxide(TPOPO) was prepared from an environmental friendly tetrakis (hydroxymethyl) phosphonium sulfate (THPS). The chemical structure of TPOPO was characterized by FT-IR, NMR ( 1 H, 13 C, 31 P) and MS. The TPOPO underwent metal-free and solvent-free 1,3dipolar cycloaddition reaction with azidated soybean oil (AzSBO) with different alkyne/azide molar ratio. The gel contents of the cured polymers were higher than 95% and the char yields of polymers at 850℃ were over 16.4%. DMA analysis showed the glass transition temperatures were over 45.9 o C. The cured polymers showed high dielectric constant and dielectric loss for their high polarity.

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Section: Surface Propertiessupporting

confidence: 75%

Phosphorus-containing polymers from THPS. VII. Synthesis of phosphorus-containing trialkynes and their metal-free 1,3-dipolar cycloaddition reaction with azidated soybean-oil

et al. 2016

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“…Nevertheless, the obtained contact angle values are comparable to acrylated vegetable oil based photocured coatings. For instance, epoxidized soybean oil was reacted with acrylic acid and the coatings prepared therefrom exhibited a water CA of 75° . On the other hand, when methacrylated soybean oil was used in a photocurable composition at ~30%, the CA was found to be as 90° …”

Section: Resultsmentioning

confidence: 99%

“…Real‐time infrared technique is a useful and widely used method to monitor the curing profile of photocurable materials . The photopolymerization kinetics of the tung oil and ISTMP based coatings were monitored by following the change of the band intensity of the olefinic double bond at around 3010 cm −1 .…”

Section: Resultsmentioning

confidence: 99%

Fully bio‐based thiol‐ene photocured thermosets from isosorbide and tung oil

Şeker

Çakmakçı

2020

Journal of Polymer Science

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Direct preparation of coatings from neat vegetable oils without any pretreatment or modification is an elegant way of demonstrating the potential of renewable sources and it is also in line with the principles of Green Chemistry.In this work, photocured coatings were prepared from tung oil (TO), hazelnut oil (HN), and isosorbide. First, a dithiol derivative of isosorbide (ISTMP) was synthesized and then mixed with TO, HN, and a cationic photoinitiator. For comparison, formulations were also prepared by using two different commercial thiol compounds. Coating formulations were applied onto glass substrates and cured under UV light where oxidative polymerization and photoinitiated thiol-ene addition reactions took place concomitantly. Double bond conversion percentages, thermal degradation properties, water contact angles, and surface hardness of the coatings were determined. Furthermore, a model reaction between ISTMP and oleic acid was performed to prove that ISTMP reacts with the fatty acid. ISTMP containing formulation displayed a fast initial double bond conversion and its water contact angle value was found as 88 ± 3 . Rigid and thermally stable isosorbide ring improved both the thermal properties and the surface hardness of the coatings.

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“…Acrylated epoxidized soybean oil was selected as the main monomer in this study because soybean oil is one of the most widely used vegetable oils in coatings and is considered an abundant and a low-cost feedstock (Sharma and Kundu, 2006). Moreover, acrylates are more reactive than epoxy-based monomers in UV curing (Malinauskas et al, 2013) and acrylated epoxidized soybean oil-based photocross-linked polymers showed promising properties for various applications (Kim et al, 2010;Liu et al, 2018;Miao et al, 2016;Zhang et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Photoresins based on acrylated epoxidized soybean oil and benzenedithiols for optical 3D printing

Miezinyte

Ostrauskaitė

Rainosalo

et al. 2019

RPJ

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Purpose The purpose of this paper is the design and investigation of novel acrylated epoxidized soybean oil-based photocurable systems as candidate materials for optical 3D printing. Design/methodology/approach Aromatic dithiols, benzene-1,3-dithiol or benzene-1,4-dithiol, were used as cross-linking agents of acrylated epoxidized soybean oil in these systems. Kinetics of photocross-linking was investigated by real-time photorheometry using two different photoinitiators, 2, 2-dimethoxy-2-phenylacetophenone or 2-hydroxy-2-methylpropiophenone, in different quantities. The effect of the initial composition on the rate of photocross-linking, mechanical, thermal properties and swelling of obtained polymers was investigated. Findings The rate of photocross-linking was higher, more cross-links and shorter polymer chains between cross-linking points of the network were formed when benzene-1,4-dithiol and 2, 2-dimethoxy-2-phenylacetophenone were used in compositions. The higher yield of insoluble fraction, glass transition temperatures and values of compressive modulus were obtained when benzene-1,3-dithiol and 2, 2-dimethoxy-2-phenylacetophenone were used in compositions. Originality/value This is the first study of acrylated epoxidized soybean oil-based thiol-ene system by real-time photorheometry. The designed novel photocurable systems based on acrylated epoxidized soybean oil and benzenedithiols are promising renewable photoresins for rapid optical 3D printing on demand.

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UV curable soybean‐oil hybrid systems based on thiol‐acrylate and thiol‐ene‐acrylate chemistry

Cited by 19 publications

References 26 publications

Phosphorus-containing polymers from THPS. VII. Synthesis of phosphorus-containing trialkynes and their metal-free 1,3-dipolar cycloaddition reaction with azidated soybean-oil

Phosphorus-containing polymers from THPS. VII. Synthesis of phosphorus-containing trialkynes and their metal-free 1,3-dipolar cycloaddition reaction with azidated soybean-oil

Fully bio‐based thiol‐ene photocured thermosets from isosorbide and tung oil

Photoresins based on acrylated epoxidized soybean oil and benzenedithiols for optical 3D printing

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