Bio-based thermoset alloys from epoxy acrylate,sesame oil- and castor oil-derived resins: Renewable alternatives to vinyl ester and unsaturated polyester resins

Abstract

This study deals with the synthesis of vegetable oil (VO)-derived formulated resins with high bio-based content (30–77%) as potential renewable alternatives to conventional fossil-based vinyl ester (VE) and unsaturated polyester (UP) resins. First, epoxy acrylate was synthesized from a commercial epoxy resin via acrylation with acrylic acid. Then, acrylated epoxidized sesame oil (AESSO) and maleated castor oil (MCO) were synthesized and spectrally characterized. Afterward, networks of VE, AESSO, and MCO or their binary blends were prepared. The curing trend of the resins was investigated by differential scanning calorimetry. According to thermal and thermomechanical analysis, all of the VO-based networks possessed slightly inferior properties compared to those of VE. However, the adhesion strength of the VO-based alloying systems was higher than that of their petroleum-based counterpart based on T-peel and lap shear tests. Overall, it was concluded that the bio-resourced alloys could be considered as good alternatives to VE and UP resins, and the novel bio-resin formulations may be designed for adhesives, the polymer–matrix composites, and surface coating applications.

Keywords

Vinyl ester sesame oil castor oil adhesive epoxidation acrylation

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References

Raquez

Deléglise

Lacrampe

. Thermosetting (bio)materials derived from renewable resources: a critical review. Prog Polym Sci 2010; 35: 487–509.

Ragauskas

Williams

Davison

. The path forward for biofuels and biomaterials. Science (80-) 2006; 311: 484–489.

Meier

Metzger

Schubert

. Plant oil renewable resources as green alternatives in polymer science. Chem Soc Rev 2007; 36: 1788–1802.

Zlatanic

Lava

Zhang

et al. Effect of structure on properties of polyols and polyurethanes based on different vegetable oils. J Polym Sci B Polym Phys 2004; 42: 809–819.

Sharma

Kundu

. Addition polymers from natural oils—a review. Prog Polym Sci 2006; 31: 983–1008.

Petrovic

. Polyurethanes from vegetable oils. Polym Rev 2008; 48: 109–155.

Miao

Wang

et al. Getable-oil-based polymers as future polymeric biomaterials. Acta Biomater 2014; 10: 1692–1704.

Sharmin

Zafar

Akram

et al. Recent advances in vegetable oils based environment friendly coatings: a review. Ind Crops Prod 2015; 76: 215–229.

Blayo

Gandini

Le Nest

. Chemical and rheological characterization of some vegetable oils derivates commonly used in printing inks. Ind Crops Prod 2001; 14: 155–167.

10.

Quinchia

Delgado

Franco

et al. Low-temperature flow behaviour of vegetable oil-based lubricants. Ind Crops Prod 2012; 37: 383–388.

11.

Hosney

Nadiem

Ashour

et al. Epoxidized vegetable oil and bio-based materials as PVC plasticizer. J Appl Polym Sci 2018; 135: 1–12.

12.

Yadav

Schmalbach

Kinaci

et al. Recent advances in plant-based vinyl ester resins and reactive diluents. Eur Polym J 2018; 98: 199–215.

13.

Gaur

Rai

JSP

. Rheological and thermal behaviour of vinyl ester resin. Eur Polym J 1993; 29: 1149–1153.

14.

Launikitis

. Vinyl ester resins. In: Lubin

(ed) Handbook of composites. 1st ed. Boston: Springer, 1982, pp. 38–49.

15.

Jaillet

Nouailhas

Boutevin

et al. Synthesis of novel bio-based vinyl ester from dicyclopentadiene prepolymer, cashew nut shell liquid, and soybean oil. Eur J Lipid Sci Technol 2016; 118: 1336–1349.

16.

Ratna

. Handbook of thermoset resins. 1st ed. London: Smithers, 2009.

17.

La Scala

Wool

. Property analysis of triglyceride-based thermosets. Polymer 2005; 46: 61–69.

18.

La Scala

Wool

. Fundamental thermo-mechanical property modeling of triglyceride-based thermosetting resins. J Appl Polym Sci 2013; 127: 1812–1826.

19.

Liu

Chen

Xie

et al. Soybean oil-based thermosets with N-vinyl-2-pyrrolidone as crosslinking agent for hemp fiber composites. Compos A Appl Sci Manuf 2016; 82: 1–7.

20.

Maassen

Meier

AMR

Willenbacher

. Unique adhesive properties of pressure sensitive adhesives from plant oils. Int J Adhes Adhes 2016; 64: 65–71.

21.

Aung

Yaakob

Kamarudin

et al. Synthesis and characterization of Jatropha (Jatropha curcas L.) oil-based polyurethane wood adhesive. Ind Crops Prod 2014; 60: 177–185.

22.

Fiorelli

Donizetti

Barrero

et al. Particulate composite based on coconut fiber and castor oil polyurethane adhesive: an eco-efficient product. Ind Crop Prod 2012; 40: 69–75.

23.

Park

Jin

Lee

. Effect of biodegradable epoxidized castor oil on physicochemical and mechanical properties of epoxy resins. Macromol Chem Phys 2004; 205: 2048–2054.

24.

Mistri

Routh

Ray

et al. Green composites from maleated castor oil and jute fibres. Ind Crops Prod 2011; 34: 900–906.

25.

Ray

Ghorui

Bandyopadhyay

et al. New materials from maleated castor oil/epoxy resin blend reinforced with fly ash. Ind Eng Chem Res 2012; 51: 2603–2608.

26.

Karami

Nademi

Zohuriaan-Mehr

et al. An efficient fully bio-based reactive diluent for epoxy thermosets: 2-[(oxiran-2-ylmethoxy) methyl] furan versus a petroleum-based counterpart. J Appl Polym Sci 2017; 134: 44957.

27.

Moazzen

Zohuriaan-Mehr

Jahanmardi

et al. Toward poly(furfuryl alcohol) applications diversification: novel self-healing network and toughening epoxy–novolac resin. J Appl Polym Sci 2018; 135: 45921.

28.

Karami

Zohuriaan-Mehr

Rostami

. Bio-based thermo-healable non-isocyanate polyurethane DA network in comparison with its epoxy counterpart. J CO2 Util 2017; 18: 294–302.

29.

Karami

Zohuriaan-Mehr

Rostami

. Biobased Diels-Alder engineered network from furfuryl alcohol and epoxy resin: preparation and mechano-physical characteristics. Chemistry Select 2018; 3: 12099–12105.

30.

Esmaeili

Zohuriaan-Mehr

Salimi

et al. Tannic acid derived non-isocyanate polyurethane networks: synthesis, curing kinetics, antioxidizing activity and cell viability. Thermochim Acta 2018; 664: 64–72.

31.

Yamini

Shakeri

Zohuriaan-Mehr

et al. Cyclocarbonated lignosulfonate as a bio-resourced reactive reinforcing agent for epoxy biocomposite: from natural waste to value-added bio-additive. J CO2 Util 2018; 24: 50–58.

32.

Ghasri

Jahandideh

Kabiri

et al. Glycerol-lactic acid star-shaped oligomers as efficient biobased surface-modifiers for improving superabsorbent polymer hydrogels. Polym Adv Technol 2018; 30: 390–399.

33.

Musik

Milchert

. Selective epoxidation of sesame oil with peracetic acid. Mol Catal 2017; 433: 170–174.

34.

Khot

Lascala

Can

et al. Development and application of triglyceride-based polymers and composites. J Appl Polym Sci 2001; 82: 703–723.

35.

Bueno-Ferrer

Garrigs

Jimnez

. Characterization and thermal stability of poly(vinyl chloride) plasticized with epoxidized soybean oil for food packaging. Polym Degrad Stab 2010; 95: 2207–2212.

36.

Saremi

Tabarsa

Shakeri

et al. Epoxidation of soybean oil. Sch Res Libr Ann Biol Res 2012; 3: 4254–4258.

37.

Habib

Bajpai

. Synthesis and characterization of acrylated epoxidized soybean oil for UV cured coatings. Chem Chem Technol 2011; 5: 317–326.

38.

Khot

Wool

. New sheet molding compound resins from soybean oil. I. Synthesis and characterization. Polymer 2005; 46: 71–80.

39.

Malik

Choudhary

Varma

. Effect of oxirane groups on curing behavior and thermal stability of vinyl ester resins. J Appl Polym Sci 2001; 82: 416–423.

40.

Lligadas

Ronda

Galià

et al. Synthesis and characterization of polyurethanes from epoxidized methyl oleate based polyether polyols as renewable resources. J Polym Sci A Polym Chem 2006; 44: 634–645.

41.

Altuna

Espósito

Ruseckaite

et al. Thermal and mechanical properties of anhydride-cured epoxy resins with different contents of biobased epoxidized soybean oil. J Appl Polym Sci 2011; 120: 789–798.

42.

Sahoo

Mohanty

Nayak

. Synthesis and characterization of bio-based epoxy blends from renewable resource based epoxidized soybean oil as reactive diluent. Chin J Polym Sci 2014; 33: 137–152.

43.

Mcneill

Sadeghi

SMT

. Thermal stability and degradation mechanisms of poly (acrylic acid) and its salts: part 1—poly (acrylic acid). Polym Degrad Stab 1990; 29: 233–246.

44.

May

Wang

Akid

. Effects of the addition of inorganic nanoparticles on the adhesive strength of a hybrid solgel epoxy system. Int J Adhes Adhes 2010; 30: 505–512.

45.

Zhai

Ling

et al. The effect of nanoparticles on the adhesion of epoxy adhesive. Mater Lett 2006; 60: 3031–3033.

46.

Anderson

DeVries

. Treatise on adhesion and adhesives. 1st ed. New York: Marcel, 1989.

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