大豆油脂肪酸多酯的制备及其对PVC增塑性能研究

doi:10.3969/j.issn.0253-2417.2019.05.007

Abstract

Abstract: Epoxidized soybean oil methyl ester (ESAO) was prepared by epoxy reaction and then followed by transesterification using soybean oil as starting material. Then, soybean oleic acid polyester (SF-PE) was prepared by one-pot reaction with ESAO, acetic acid and acetic anhydride. The purity of ESAO was more than 96% by GC analysis, and the structures of products were characterized by IR, ¹H NMR and ¹³C NMR. It was proved that epoxidation, ring opening and esterification occurred and SF-PE was successfully synthesized. The thermal stability of SF-PE was better than ESAO according to TG analysis. The mechanical properties, dynamic mechanical properties (DMA) and TG of PVC samples prepared with SF-PE, ESAO, epoxy soybean oil (ESO) and epoxy fatty acid methyl ester (EFAM) as plasticizers were compared and analyzed. The tensile strength and hardness of PVC samples were 19 MPa and 90.2 HD when the dosage of SF-PE was 50% of the weight of resin. The comprehensive mechanical properties of PVC samples were optimized, and the glass transition temperature (T_g) was 26.4℃. Its low temperature resistance is superior to ESO, and its thermal stability is similar to ESAO, superior to EFAM, but inferior to ESO.

Key words: soybean oleic acid polyester, oil-based plasticizer, mechanical properties, epoxidized soybean oil methyl ester(ESAO), transesterification

CLC Number:

FENG Guodong, JIA Puyou, TANG Huimin, ZHANG Meng, HU Yun, ZHOU Yonghong. Preparation of Soybean Oil Fatty Acid Polyester and Its Plasticity for Polyvinyl Chloride(PVC)[J]. Chemistry and Industry of Forest Products, 2019, 39(5): 50-58.

References

[1] QIAN B Z.Analysis on the development of high-grade plasticizers in China (1)[J]. Shanghai Chemical Industry, 2016, 141(3):32-37. 钱伯章.我国高档增塑剂发展趋势分析(一)[J].上海化工, 2016, 141(3):32-37.
[2] QIAN B Z.Analysis on the development of high-grade plasticizers in China (2)[J]. Shanghai Chemical Industry, 2016, 141(4):36-41. 钱伯章.我国高档增塑剂发展趋势分析(二)[J].上海化工, 2016, 141(4):36-41.
[3] SHI W C.Toxicity and ralated restricted laws and regulations for plasticizers[J]. Plastic Additives, 2010(3):6-10. 石万聪.增塑剂的毒性及相关限制法规[J].塑料助剂, 2010(3):6-10.
[4] DESMOND T, KUM K, NEON G.Palm oil-based compound as environmentally friendly plasticizer for poly(vinyl chloride)[J]. Journal of Vinyl & Additive Technology, 2016, 22(1):80-87.
[5] GAMAGE K, AHMED S.Oligomeric isosorbide esters as alternative renewable resource plasticizers for PVC[J]. Journal of Applied Polymer Science, 2011, 121:823-838.
[6] SINADINOVIĆ-FIŠER S, JANKOVIĆ M, BOROTA O.Epoxidation of castor oil with peracetic acid formed in situ in the presence of an ion exchange resin[J]. Catalysis Today, 2014, 223(15):148-156.
[7] LÜ Z Y, WANG K Y, ZENG G F, et al.Synthesis and performance of C₂₂-tricarboxylic dibutyl-monomethyl ester[J]. Chemical Industry and Engineering Progress, 2014, 33(7):1875-1879. 吕宗莹, 王克英, 曾桂凤, 等.C₂₂-三元酸二丁一甲酯增塑剂的合成及其性能[J].化工进展, 2014, 33(7):1875-1879.
[8] JIA P Y, ZHANG M, HU L H, et al.Green plasticizers derived from soybean oil for poly(vinyl chloride) as a renewable resource material[J]. Korean Journal of Chemical Engineering, 2016, 33(3):1080-1087.
[9] HE W, FANG Z, JI D, et al.Epoxidation of soybean oil by continuous micro-flow system with continuous separation[J]. Organic Process Research & Development, 2013, 17(9):1137-1141.
[10] BHAKTI M, KATHALEWAR M, SABNIS A.Diester based on castor oil fatty acid as plasticizer for poly(vinyl chloride)[J]. Journal of Applied Polymer Science 2014, 131(11):40357.
[11] LI M, LI S H, XIA J L, et al.Tung oil based plasticizer and auxiliary stabilizer for poly(vinyl chloride)[J]. Materials & Design, 2017, 122:366-375.
[12] FENG G D, HU L H, MA Y, et al.An efficient bio-based plasticizer for poly (vinyl chloride) from waste cooking oil and citric acid:Synthesis and evaluation in PVC films[J]. Journal of Cleaner Production, 2018, 189(10):334-343.
[13] FENG G D, MA Y, HU L H, et al.Preparation and application of high performance bio-based PVC plasticizer[J]. Polymer Materials Science & Engineering, 2018, 34(6):15-21. 冯国东, 马艳, 胡立红, 等.高性能生物基聚氯乙烯增塑剂的制备与应用[J].高分子材料科学与工程, 2018, 34(6):15-21.
[14] JIANG P P, LU Y, FEI L Y.Technical questions of epoxidized soybean oil and its application in PVC[J]. Plastic Additives, 2006(1):28-32. 蒋平平, 卢云, 费柳月.环氧大豆油的生产技术及其在PVC中的应用[J].塑料助剂, 2006(1):28-32.
[15] HOLSER R A.Transesterification of epoxidized soybean oil to prepare epoxy methyl esters[J]. Industrial Crops and Products, 2008, 27(1):130-132.
[16] LI X Q.Synthesis of a non-toxic plasticizer epoxy methyl fatty acid ester[J]. Plastic Additives, 2011(3):27-30. 李祥庆.无毒增塑剂环氧脂肪酸甲酯的合成[J].塑料助剂, 2011(3):27-30.
[17] SHI R P, JIANG P P, SHI S Q.Epoxidized synthesis of nontoxic and environmental-friendly plasticizer from soy acidic oil methyl esters[J]. China Oils and Fats, 2008, 33(6):36-39. 史润萍, 蒋平平, 施赛泉.大豆酸化油甲酯环氧化合成无毒环保型增塑剂[J].中国油脂, 2008, 33(6):36-39.
[18] SHI W C, SHI Z B, JIANG P P.Plasticizers and Their Applications[M]. Beijing:Chemical Industry Press, 2002:534-545. 石万聪, 石志博, 蒋平平.增塑剂及其应用[M].北京:化学工业出版社, 2002:534-545.
[19] FENG G D, HU Y, JIA P Y, et al.Influence of a nitrogen-containing oil-based plasticizer on mechanical, thermal stability and fire performance of plasticized poly(vinyl chloride) and study of its mechanism of flame retardancy with Py-GC/MS[J]. Industrial Crops and Products, 2015, 77:883-894.
[20] SMALL P A.Some factors affecting the solubility of polymers[J]. Journal of Applied Chemistry, 1953, 3:71-80.

Preparation of Soybean Oil Fatty Acid Polyester and Its Plasticity for Polyvinyl Chloride(PVC)

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