桐油基紫外光固化材料体系构建的研究进展
|
摘要
桐油基紫外光固化材料体系具有成膜速度快、固化温度低、污染小和可再生等优点,发展利用空间很大。利用桐油分子长链含有共轭双键的化学结构特征,可以对其进行化学改性,构建桐油基紫外光固化材料体系。本文综述了近年来桐油基紫外光固化材料体系的研究进展。首先简要介绍了桐油的化学结构与应用,然后着重论述了通过Diels-Alder反应来构建的桐油基紫外光固化材料体系的研究现状,还探讨了其他化学改性桐油构建紫外光固化体系的方法和固化效果。文章最后展望了桐油基紫外光固化材料体系的研究及应用前景。
The tung oil-based UV-curable materials systems have displayed wide application potential by virtue of the advantages including fast film formation,less pollution and reproducibility.They can be constructed by modifying tung oil-based on the long chain conjugation in its molecules.This review is concerned with the research progress of tung oil-based UV-curable materials systems in recent years.It starts with a brief introduction about the chemical structure and application of tung oil,and subsequently provides an elaborate description upon the current research status of constructing tung oil-based UV-curable materials systems constructed via Diels-Alder reactions and other chemical modification methods.Finally,the paper ends with a prospective discussion for research and application of the UV-curable material system in the future.
The tung oil-based UV-curable materials systems have displayed wide application potential by virtue of the advantages including fast film formation,less pollution and reproducibility.They can be constructed by modifying tung oil-based on the long chain conjugation in its molecules.This review is concerned with the research progress of tung oil-based UV-curable materials systems in recent years.It starts with a brief introduction about the chemical structure and application of tung oil,and subsequently provides an elaborate description upon the current research status of constructing tung oil-based UV-curable materials systems constructed via Diels-Alder reactions and other chemical modification methods.Finally,the paper ends with a prospective discussion for research and application of the UV-curable material system in the future.
引文
1 Zhang C,Garrison T F,Madbouly S A,et al.Recent advances in vegetable oil-based polymers and their composites[J].Progress in Polymer Science,2017,71:91.
2 Tathe D S,Jagtap R N.Biobased reactive diluent for UV-curable urethane acrylate oligomers for wood coating[J].Journal of Coatings Technology&Research,2015,12(1):187.
3 Zhong C,Cao Y,Li B,et al.Biofuels in China:Past,present and future[J].Biofuels Bioproducts&Biorefining,2010,4(3):326.
4 Greenfield J.Tung oil[J].Journal of the American Oil Chemists Society,1959,36(11):565.
5 Bickford W G,DupréE F,Mack C H,et al.The infrared spectra and the structural relationships between alpha-and beta-eleostearic acids and their maleic anhydride adducts[J].Journal of the American Oil Chemists Society,1953,30(9):376.
6 Biermann U,Butte W,Eren T,et al.Regio-and stereoselective diels-alder additions of maleic anhydride to conjugated triene fatty acid methyl esters[J].European Journal of Organic Chemistry,2007,2007(23):3859.
7 Yoshimura Y.Kinetics of reactions of methylα-eleostearate with cresols[J].Journal of Polymer Science.Part A:Polymer Chemistry,1988,26(5):1343.
8 Yoshimura Y.Kinetics of reaction of methylα-eleostearate with phenol[J].Journal of Polymer Science,Part A:Polymer Chemistry,1986,24(3):469.
9 Yuan C,Zhao X,Shao L,et al.Preparation and properties of Tung oil-based polyurethane[J].Transactions of Tianjin University,2014,20(4):273.
10 Meiorin C,Mosiewicki M A,Aranguren M I.Ageing of thermosets based on tung oil/styrene/divinylbenzene[J].Polymer Testing,2013,32(2):249.
11 Humar M,Lesar B.Efficacy of linseed-and tung-oil-treated wood against wood-decay fungi and water uptake[J].International Biodeterioration&Biodegradation,2013,85(7):223.
12 Liu C,Dai Y,Wang C,et al.Phase-separation dominating mechanical properties of a novel tung-oil-based thermosetting polymer[J].Industrial Crops&Products,2013,43(5):677.
13 Fang S,Zhang H,Zhang B,et al.A study of Tung-oil-lime putty—A traditional lime based mortar[J].International Journal of Adhesion&Adhesives,2014,48(48):224.
14 Mosiewicki M A,Casado U,Marcovich N E,et al.Moisture dependence of the properties of composites made from tung oil based polyurethane and wood flour[J].Journal of Polymer Research,2012,19(2):1.
15 Li M,Li S,Xia J,et al.Tung oil based plasticizer and auxiliary stabilizer for poly(vinyl chloride)[J].Materials&Design,2017,122:366.
16 Wang M,Song X,Jiang J,et al.Plasticization and thermal behavior of hydroxyl and nitrogen rich group-containing tung-oil-based ester plasticizers for PVC[J].New Journal of Chemistry,2017,42(4):2422.
17 Qi D H,Yang K,Zhang D,et al.Experimental investigation of a turbocharged CRDI diesel engine fueled with Tung oil-diesel-ethanol microemulsion fuel[J].Renewable Energy,2018,113:1201.
18 Li H,Cui Y,Li Z,et al.Fabrication of microcapsules containing dual-functional tung oil and properties suitable for self-healing and self-lubricating coatings[J].Progress in Organic Coatings,2018,115:164.
19 Escouvois M.From vegetable oils to polyurethanes:Synthetic routes to polyols and main industrial products[J].Polymer Reviews,2012,52(1):38.
20 Wang Z X,Wang J L,Gu L Z.Synthesis and characterization of tung oil-based waterborne polyurethane[J].Paint&Coatings Industry,2012,42(7):49(in Chinese).王正祥,王建龙,顾丽争.桐油基水性聚氨酯的合成与表征[J].涂料工业,2012,42(7):49.
21 Li Y,Wang M,Zhou Y.Research on characterization and reaction mechanism of the phenolic resin binary modified by boric acid&tung oil[J].Guangdong Chemical Industry,2010,37(6):5(in Chinese).李屹,王满力,周元康.硼酸-桐油双改性酚醛树脂的表征及反应机理研究[J].广东化工,2010,37(6):5.
22 Sharma V,Das L,Pradhan R C,et al.Physical properties of tung seed:An industrial oil yielding crop[J].Industrial Crops&Products,2011,33(2):440.
23 Huang J,Yuan T,Ye X,et al.Study on the UV curing behavior of tung oil:Mechanism,curing activity and film-forming property[J].Industrial Crops&Products,2018,112:61.
24 Zhang H Z,Zhou H Y,Wang J X.Synthesis,characterization and UV curable property of acrylate modified tung oil-based emulsifier[J].Chemical Industry&Engineering Progress,2017,36(10):3860(in Chinese)张海召,周宏勇,王家喜,等.丙烯酸酯改性桐油基乳化剂的合成、表征及光固化性能[J].化工进展,2017,36(10):3860.
25 Liu C,Liu Z,Tisserat B H,et al.Microwave-assisted maleation of tung oil for bio-based products with versatile applications[J].Industrial Crops&Products,2015,71:185.
26 Huang Y,Ye G,Yang J.Synthesis and properties of UV-curable acrylate functionalized tung oil based resins via,Diels-Alder reaction[J].Progress in Organic Coatings,2015,78:28.
27 Huang Y,Pang L,Wang H,et al.Synthesis and properties of UVcurable tung oil based resins via,modification of Diels-Alder reaction,nonisocyanate polyurethane and acrylates[J].Progress in Organic Coatings,2013,76(4):654.
28 Tan X L,Deng J R,Luo S,et al.Preparation and properties of tung oil-based waterborne UV-curable resin[J].Fine Chemicals,2016,33(8):862(in Chinese).谭湘璐,邓剑如,罗赛,等.桐油基水性光固化树脂的合成及性能[J].精细化工,2016,33(8):862.
29 Thames S F,Subramanian R.Cationic ultraviolet curable coatings from Chinese melon oil and tung oil[J].Macromolecules New Frontiers,1998,2:1011.
30 Wu J,Zhang T,MaG,et al.Synthesis of a tung oil-rosin adduct via the diels-alder reaction:Its reaction mechanism and properties in an ultraviolet-curable adhesive[J].Journal of Applied Polymer Science,2013,130(6):4201.
31 Yang X,Li S,Xia J,et al.Novel renewable resource-based UVcurable copolymers derived from myrcene and tung oil:Preparation,characterization and properties[J].Industrial Crops&Products,2015,63:17.
32 Thanamongkollit N,Miller K,Soucek M D.Synthesis of UV-curable tung oil and UV-curable tungoil based alkyd[J].Progress in Organic Coatings,2012,73(4):425.
33 Chittavanich P,Miller K,Soucek M D.A photo-curing study of a pigmented UV-curable alkyd[J].Progress in Organic Coatings,2012,73(4):392.
34 Zhou J,Liu Y,Hu Y,et al.Synthesis of novel urushiol-like compounds from tung oil using silica-supported phosphotungstic heteropoly acid catalyst[J].Industrial Crops&Products,2016,94:424.
35 Zhou C,Hu Y,Yang Z,et al.Facile synthesis and characterization of urushiol analogues from tung oil via ultraviolet photocatalysis[J].Progress in Organic Coatings,2018,120:240.
36 Yan M,Lin F,et al.Dynamics of hyperbranched polymers derived from acrylated epoxidized soybean oil[J].Polymer,2017,125:117.
37 Zhang H,Zhao T Y,Ben Newland,et al.Catechol functionalized hyperbranched polymers as biomedical materials[J].Progress in Polymer Science,2018,78:47.
38 Wang A,Xu H,Zhou Q,et al.A new all-solid-state hyperbranched star polymer electrolyte for lithium ion batteries:Synthesis and electrochemical properties[J].Electrochimica Acta,2016,212:372.
39 Yan D,Gao C,Frey H.Hyperbranched polymers:Synthesis,properties,and applications[M].America:Wiley,2011:415.
40 Mirshahi F,Bastani S,Sari M G.Studying the effect of hyperbranched polymer modificationon the kinetics of curing reactions and physical/mechanical properties of UV-curable coatings[J].Progress in Organic Coatings,2016,90:187.
41 Andjelkovic D,Lu Y,Kessler M,et al.Novel rubbers from the cationic copolymerization of soybean oils and dicyclopentadiene,2-mechanical and damping properties[J].Macromolecular Materials&Engineering,2009,294(8):472.
42 Smith M,Payne A,Edwards K,et al.Effect ofmicrowave cure on the thermo-mechanical properties of tung oil-based/carbon nanotube composites[J].Coatings,2015,5:557.
43 Ni J,Feng G,Meng Z,et al.Reinforced lubrication of vegetable oils with graphene additive in tapping ADC12aluminum alloy[J].International Journal of Advanced Manufacturing Technology,2018,94(1-4):1.
44 Wei S,Choy S,Cheng H,et al.Preparation and modification of water-blown porous biodegradable polyurethane foams with palm oilbased polyester polyol[J].Industrial Crops&Products,2017,97:65.
45 Chen M,Zhong M,Johnson J.Light-controlled radical polymerization:Mechanisms,methods,and applications[J].Chemical Reviews,2016,116:10167.
2 Tathe D S,Jagtap R N.Biobased reactive diluent for UV-curable urethane acrylate oligomers for wood coating[J].Journal of Coatings Technology&Research,2015,12(1):187.
3 Zhong C,Cao Y,Li B,et al.Biofuels in China:Past,present and future[J].Biofuels Bioproducts&Biorefining,2010,4(3):326.
4 Greenfield J.Tung oil[J].Journal of the American Oil Chemists Society,1959,36(11):565.
5 Bickford W G,DupréE F,Mack C H,et al.The infrared spectra and the structural relationships between alpha-and beta-eleostearic acids and their maleic anhydride adducts[J].Journal of the American Oil Chemists Society,1953,30(9):376.
6 Biermann U,Butte W,Eren T,et al.Regio-and stereoselective diels-alder additions of maleic anhydride to conjugated triene fatty acid methyl esters[J].European Journal of Organic Chemistry,2007,2007(23):3859.
7 Yoshimura Y.Kinetics of reactions of methylα-eleostearate with cresols[J].Journal of Polymer Science.Part A:Polymer Chemistry,1988,26(5):1343.
8 Yoshimura Y.Kinetics of reaction of methylα-eleostearate with phenol[J].Journal of Polymer Science,Part A:Polymer Chemistry,1986,24(3):469.
9 Yuan C,Zhao X,Shao L,et al.Preparation and properties of Tung oil-based polyurethane[J].Transactions of Tianjin University,2014,20(4):273.
10 Meiorin C,Mosiewicki M A,Aranguren M I.Ageing of thermosets based on tung oil/styrene/divinylbenzene[J].Polymer Testing,2013,32(2):249.
11 Humar M,Lesar B.Efficacy of linseed-and tung-oil-treated wood against wood-decay fungi and water uptake[J].International Biodeterioration&Biodegradation,2013,85(7):223.
12 Liu C,Dai Y,Wang C,et al.Phase-separation dominating mechanical properties of a novel tung-oil-based thermosetting polymer[J].Industrial Crops&Products,2013,43(5):677.
13 Fang S,Zhang H,Zhang B,et al.A study of Tung-oil-lime putty—A traditional lime based mortar[J].International Journal of Adhesion&Adhesives,2014,48(48):224.
14 Mosiewicki M A,Casado U,Marcovich N E,et al.Moisture dependence of the properties of composites made from tung oil based polyurethane and wood flour[J].Journal of Polymer Research,2012,19(2):1.
15 Li M,Li S,Xia J,et al.Tung oil based plasticizer and auxiliary stabilizer for poly(vinyl chloride)[J].Materials&Design,2017,122:366.
16 Wang M,Song X,Jiang J,et al.Plasticization and thermal behavior of hydroxyl and nitrogen rich group-containing tung-oil-based ester plasticizers for PVC[J].New Journal of Chemistry,2017,42(4):2422.
17 Qi D H,Yang K,Zhang D,et al.Experimental investigation of a turbocharged CRDI diesel engine fueled with Tung oil-diesel-ethanol microemulsion fuel[J].Renewable Energy,2018,113:1201.
18 Li H,Cui Y,Li Z,et al.Fabrication of microcapsules containing dual-functional tung oil and properties suitable for self-healing and self-lubricating coatings[J].Progress in Organic Coatings,2018,115:164.
19 Escouvois M.From vegetable oils to polyurethanes:Synthetic routes to polyols and main industrial products[J].Polymer Reviews,2012,52(1):38.
20 Wang Z X,Wang J L,Gu L Z.Synthesis and characterization of tung oil-based waterborne polyurethane[J].Paint&Coatings Industry,2012,42(7):49(in Chinese).王正祥,王建龙,顾丽争.桐油基水性聚氨酯的合成与表征[J].涂料工业,2012,42(7):49.
21 Li Y,Wang M,Zhou Y.Research on characterization and reaction mechanism of the phenolic resin binary modified by boric acid&tung oil[J].Guangdong Chemical Industry,2010,37(6):5(in Chinese).李屹,王满力,周元康.硼酸-桐油双改性酚醛树脂的表征及反应机理研究[J].广东化工,2010,37(6):5.
22 Sharma V,Das L,Pradhan R C,et al.Physical properties of tung seed:An industrial oil yielding crop[J].Industrial Crops&Products,2011,33(2):440.
23 Huang J,Yuan T,Ye X,et al.Study on the UV curing behavior of tung oil:Mechanism,curing activity and film-forming property[J].Industrial Crops&Products,2018,112:61.
24 Zhang H Z,Zhou H Y,Wang J X.Synthesis,characterization and UV curable property of acrylate modified tung oil-based emulsifier[J].Chemical Industry&Engineering Progress,2017,36(10):3860(in Chinese)张海召,周宏勇,王家喜,等.丙烯酸酯改性桐油基乳化剂的合成、表征及光固化性能[J].化工进展,2017,36(10):3860.
25 Liu C,Liu Z,Tisserat B H,et al.Microwave-assisted maleation of tung oil for bio-based products with versatile applications[J].Industrial Crops&Products,2015,71:185.
26 Huang Y,Ye G,Yang J.Synthesis and properties of UV-curable acrylate functionalized tung oil based resins via,Diels-Alder reaction[J].Progress in Organic Coatings,2015,78:28.
27 Huang Y,Pang L,Wang H,et al.Synthesis and properties of UVcurable tung oil based resins via,modification of Diels-Alder reaction,nonisocyanate polyurethane and acrylates[J].Progress in Organic Coatings,2013,76(4):654.
28 Tan X L,Deng J R,Luo S,et al.Preparation and properties of tung oil-based waterborne UV-curable resin[J].Fine Chemicals,2016,33(8):862(in Chinese).谭湘璐,邓剑如,罗赛,等.桐油基水性光固化树脂的合成及性能[J].精细化工,2016,33(8):862.
29 Thames S F,Subramanian R.Cationic ultraviolet curable coatings from Chinese melon oil and tung oil[J].Macromolecules New Frontiers,1998,2:1011.
30 Wu J,Zhang T,MaG,et al.Synthesis of a tung oil-rosin adduct via the diels-alder reaction:Its reaction mechanism and properties in an ultraviolet-curable adhesive[J].Journal of Applied Polymer Science,2013,130(6):4201.
31 Yang X,Li S,Xia J,et al.Novel renewable resource-based UVcurable copolymers derived from myrcene and tung oil:Preparation,characterization and properties[J].Industrial Crops&Products,2015,63:17.
32 Thanamongkollit N,Miller K,Soucek M D.Synthesis of UV-curable tung oil and UV-curable tungoil based alkyd[J].Progress in Organic Coatings,2012,73(4):425.
33 Chittavanich P,Miller K,Soucek M D.A photo-curing study of a pigmented UV-curable alkyd[J].Progress in Organic Coatings,2012,73(4):392.
34 Zhou J,Liu Y,Hu Y,et al.Synthesis of novel urushiol-like compounds from tung oil using silica-supported phosphotungstic heteropoly acid catalyst[J].Industrial Crops&Products,2016,94:424.
35 Zhou C,Hu Y,Yang Z,et al.Facile synthesis and characterization of urushiol analogues from tung oil via ultraviolet photocatalysis[J].Progress in Organic Coatings,2018,120:240.
36 Yan M,Lin F,et al.Dynamics of hyperbranched polymers derived from acrylated epoxidized soybean oil[J].Polymer,2017,125:117.
37 Zhang H,Zhao T Y,Ben Newland,et al.Catechol functionalized hyperbranched polymers as biomedical materials[J].Progress in Polymer Science,2018,78:47.
38 Wang A,Xu H,Zhou Q,et al.A new all-solid-state hyperbranched star polymer electrolyte for lithium ion batteries:Synthesis and electrochemical properties[J].Electrochimica Acta,2016,212:372.
39 Yan D,Gao C,Frey H.Hyperbranched polymers:Synthesis,properties,and applications[M].America:Wiley,2011:415.
40 Mirshahi F,Bastani S,Sari M G.Studying the effect of hyperbranched polymer modificationon the kinetics of curing reactions and physical/mechanical properties of UV-curable coatings[J].Progress in Organic Coatings,2016,90:187.
41 Andjelkovic D,Lu Y,Kessler M,et al.Novel rubbers from the cationic copolymerization of soybean oils and dicyclopentadiene,2-mechanical and damping properties[J].Macromolecular Materials&Engineering,2009,294(8):472.
42 Smith M,Payne A,Edwards K,et al.Effect ofmicrowave cure on the thermo-mechanical properties of tung oil-based/carbon nanotube composites[J].Coatings,2015,5:557.
43 Ni J,Feng G,Meng Z,et al.Reinforced lubrication of vegetable oils with graphene additive in tapping ADC12aluminum alloy[J].International Journal of Advanced Manufacturing Technology,2018,94(1-4):1.
44 Wei S,Choy S,Cheng H,et al.Preparation and modification of water-blown porous biodegradable polyurethane foams with palm oilbased polyester polyol[J].Industrial Crops&Products,2017,97:65.
45 Chen M,Zhong M,Johnson J.Light-controlled radical polymerization:Mechanisms,methods,and applications[J].Chemical Reviews,2016,116:10167.
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |