脱氢枞酸基甲基丙烯酸酯单体的合成和表征

doi:10.3969/j.issn.0253-2417.2017.04.013

Abstract

Abstract: 2-Methacryloyloxyisopropanol ester of dehydroabietic acid (DAGMA) was synthesized by esterification of dehydroabietic acid and glycidyl methacrylate. The effects of reaction time, reaction temperature, amount and type of catalyst on the yield of dehydroabietic acid derived monomer were investigated. The resulting product was then characterized by FT-IR, ¹H NMR, ¹³C NMR, DSC and GPC respectively. The results showed that the optimal conditions for the reaction were as follows:triethylamine as catalyst at an amount of 2% of dehydroabietic acid, reaction time 5 h, reaction temperature 120℃, and the esterification rate was about 85%. DSC test showed that in the presence of initiator AIBN, the suitable conditions for synthesis of DAGMA was n(DA):n(GMA) 1:1. It showed that DAGMA could be polymerized in the presence of initiator. The weight average molecular weight(M_w) of the asprepared homopolymer was 23 900, the number average molecular weight(M_n) was 12 254, and its glass transition temperature was around 62.61℃.

Key words: dehydroabietic acid, glycidyl methacrylate, 2-methacryloyloxyisopropanol ester of dehydroabietic acid, characterization

CLC Number:

TQ351

LIU Shaofeng, LU Chuanwei, WANG Chunpeng, CHU Fuxiang, WANG Jifu. Synthesis and Characterization of 2-Methacryloyloxyisopro-panol Ester of Dehydroabietic Acid[J]. Chemistry and Industry of Forest Products, 2017, 37(4): 89-94.

References

[1] 王基夫,林明涛,王春鹏,等.松香基甲基丙烯酸酯单体的合成和聚合活性分析[J].林产化学与工业,2011,31(6):20-24. WANG J F,LIN M T,WANG C P,et al.Synthesis and characterization of (β-methacryloyloxy) ethyl ester of dehydroabietic acid[J].Chemistry and Industry of Forest Product,2011,31(6):20-24.
[2] MAITI S,RAY S S,KUNDU A K.Rosin:A renewable resource for polymers and polymer chemicals[J].Progress in Polymer Science,1989,14(3):297-338.
[3] 孔振武,夏建陵,黄焕.松香的精细化工利用(Ⅱ)——松香在高分子材料中的应用[J].林产化工通讯,2002,36(5):21-28. KONG Z W,XIA J L,HUANG H.Fine chemical use of rosin (Ⅱ):Application of rosin in polymeric materials[J].Journal of Chemical Industry of Forest Products,2002,36(5):21-28.
[4] 宋湛谦.松香的精细化工利用(Ⅰ)——松香的组成与性质[J].林产化工通讯,2002,(04):29-33. SONG Z Q.Fine chemical use of rosin (Ⅰ):Composition and properties of rosin[J].Journal of Chemical Industry of Forest Products,2002,36(4):29-33.
[5] WANG J,YAO K,KORICH A L,et al.Combining renewable gum rosin and lignin:Towards hydrophobic polymer composites by controlled polymerization[J].Journal of Polymer Science Part A:Polymer Chemistry,2011,49(17):3728-3738.
[6] YAO K,TANG C.Controlled polymerization of next-generation renewable monomers and beyond[J].Macromolecules,2013,46(5):1689-1712.
[7] YU J,LIU Y,LIU X,et al.Integration of renewable cellulose and rosin towards sustainable copolymers by ‘grafting from’ ATRP[J].Green Chemistry,2014,16(4):1854-1864.
[8] ZhENG Y,YAO K,LEE J,et al.Well-defined renewable polymers derived from gum rosin[J].Macromolecules,2010,43(14):5922-5924.
[9] LEWIS J,HEDRICK G.Vinyl esters of rosin[J].Journal of Polymer Science Part A-1:Polymer Chemistry,1966,4(8):2026-2027.
[10] 白丽娟,张晓丽,蓝虹云,等.功能化松香丙烯醇酯聚合物吸附分离银杏黄酮[J].化学与生物工程,2007,24(3):24-26. BAI L J,ZHANG X L,LAN H Y,et al.Adsorption and separation of Ginkgo biloba flavone by functional polymer of rosin allyl alcohol ester[J].Chemistry & Bioengineering,2007,24(3):24-26.
[11] 陈春红,段文贵,李行任,等.松香烯丙醇酯的合成研究[J].林产化学与工业,2007,27(5):57-61. CHEN C H,DUAN W G,LI X R,et al.Synthesis of rosin allyl alcohol ester[J].Chemistry and Industry of Forest Products,2007,27(5):57-61.
[12] 林明涛,储富祥,马丽,等.歧化松香(丙烯酸-2-羟基乙基酯)酯的合成[J].林产化学与工业,2006,26(4):43-47. LIN M T,CHU F X,MA L,et al.Study on the synthesis of disproportionated rosin (2-hydroxyethyl acrylate) ester[J].Chemistry and Industry of Forest Products,2206,26(4):43-47.
[13] 王基夫,吴红,林明涛,等.松香基紫外光固化功能单体的合成和表征[J].涂料工业,2009,39(7):13-15,20. WANG J F,WU H,LIN M T,et al.Synthesis and characterization of rosin-based UV curable functional monomer[J].Paint & Coatings Industry,2009,39(7):13-15,20.
[14] 王基夫,林明涛,储富祥,等.脱氢枞酸(β-丙烯酰氧基乙基)酯的合成和表征[J].精细化工,2008,25(11):1135-1139. WANG J F,LIN M T,CHU F X,et al.Synthesis and characterization of (2-acryloyloxy) ethyl ester of dehydroabietic acid[J].Fine Chemical,2008,25(11):1135-1139.
[15] 王基夫,林明涛,储富祥,等.脱氢枞酸烯丙基酯的合成和表征[J].生物质化学工程,2008,42(3):1-4. WANG J F,LIN M T,CHU F X,et al.Synthesis and characterization of allyl ester of dehydroabietic acid[J].Biomass Chemical Engineering,2008,43(3):1-4.
[16] 俞娟,王利军,刘少锋,等.脱氢枞酸基ATRP引发剂的合成与表征[J].林产化学与工业,36(2):87-93. YU J,WANG L J,LIU S F,et al.Synthesis and characterization of dehydroabietic acid derived ATRP initiator[J].Chemistry and Industry of Forest Products,2016,36(2):87-93.
[17] 任鹏,余彩莉,王孝磊,等.松香和甲基丙烯酸缩水甘油酯酯化反应研究[J].化学研究与应用,2014,26(3):427-431. REN P,YU C L,WANG X L,et al.Study on esterification of rosin and glycidyl methacrylate[J].Chemical Research and Application,2014,26(3):427-431.
[18] 刘雁.歧化松香的制备与脱氢枞酸的提纯研究[D]:南宁:广西大学硕士学位论文,2004. LIU Y.Study on the preparation of disproportionated rosin and purification of dehydroabietic acid from disproportionated rosin[D].Nanning:Master Degree Thesis of Guangxi University,2004.

Synthesis and Characterization of 2-Methacryloyloxyisopro-panol Ester of Dehydroabietic Acid

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