环氧树脂改性小桐子蛋白基胶粘剂的制备机理及热性能分析
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摘要
以ECH(环氧氯丙烷)作为EP(环氧树脂)的模型化合物、氨基酸[如Ser(丝氨酸)、Glu(谷氨酸)或Ala-Gln(L-丙氨酰-L-谷氨酰胺)等]作为小桐子蛋白的模型化合物,通过模型化合物间的反应来研究EP改性小桐子蛋白基胶粘剂的反应机理。研究结果表明:ECH与3种氨基酸(如Ser、Glu和Ala-Gln)中的游离氨基都能发生取代反应,但与羧基和羟基之间无明显的反应(不排除参与后期固化反应的可能);就3种氨基酸(如Ser、Glu和Ala-Gln)中的氨基与ECH的反应产物(反应程度依次减小)而言,前者主要是N-2取代物,而后两者主要是N-1取代物。小桐子蛋白基胶粘剂的固化温度和热稳定性均高于大豆蛋白基胶粘剂。
With ECH(epoxy chloropropane)as model compound of EP(epoxy resin),some amino acids[suchas Ser(serine),Glu(glutamic acid)or Ala-Gln(L-alanyl-L-glutamine)] as model compounds of jatropha curcas,the reaction mechanism of EP modified jatropha curcas protein-based adhesive was investigated by reactionbetween model compounds.The research results showed that the replace reaction between ECH and free-amino inthree amino acids(such as Ser,Glu or Ala-Gln)could be happened,but the reactions among ECH,carboxyl groupsand hydroxyl groups were not obvious which groups may participate in the latter curing reaction.For reactionproducts between ECH and free-amino in three amino acids(such as Ser,Glu or Ala-Gln)which reaction degreewas successively decreased,the former is mainly N-2 substituendum,but the latter both are mainly N-1 substituendum.The curing temperature and thermal stability of jatropha curcas protein-based adhesive were morethan those of soy protein-based adhesive.
With ECH(epoxy chloropropane)as model compound of EP(epoxy resin),some amino acids[suchas Ser(serine),Glu(glutamic acid)or Ala-Gln(L-alanyl-L-glutamine)] as model compounds of jatropha curcas,the reaction mechanism of EP modified jatropha curcas protein-based adhesive was investigated by reactionbetween model compounds.The research results showed that the replace reaction between ECH and free-amino inthree amino acids(such as Ser,Glu or Ala-Gln)could be happened,but the reactions among ECH,carboxyl groupsand hydroxyl groups were not obvious which groups may participate in the latter curing reaction.For reactionproducts between ECH and free-amino in three amino acids(such as Ser,Glu or Ala-Gln)which reaction degreewas successively decreased,the former is mainly N-2 substituendum,but the latter both are mainly N-1 substituendum.The curing temperature and thermal stability of jatropha curcas protein-based adhesive were morethan those of soy protein-based adhesive.
引文
[1]PIZZI A.Recent developments in eco-efficent bio-based adhesives for wood bonding:opportunities and issues[J].Journal of Adhesion Science and Technology,2006,20(8):829-846.
[2]吴义强,李新功,左迎峰,等.农林剩余物无机人造板研究进展[J].林业工程学报,2016,1(1):8-15.
[3]陈焱,石爱民,刘丽,等.木材用植物蛋白胶粘剂蛋白质改性与性能改善研究进展[J].粮食与油脂,2017,42(2):125-129.
[4]吴志刚,雷洪,杜官本.大豆蛋白基胶粘剂研究与应用发展现状[J].粮食与油脂,2015,28(11):1-5.
[5]张俊,杜官本,席雪冬.单宁树脂砂轮片制备及氧化铝在树脂中的分形分布[J].林业工程学报,2016,1(1):88-92.
[6]郝海霞,吴志刚,雷洪,等.3种处理方式对小桐子蛋白基胶粘剂性能的影响[J].西南林业大学学报,2016,36(1):136-139.
[7]JIN CN,ZHANG SC,PANG JY,etal.Plywoodwithsoyproteinacrylate hybrid adhesive[J].Advanced Materials Research,2014,884-885:108-111.
[8]HE Z Q,CHENG H N,KLASSON T K.Effects of particle Size on the morphology and water-and thermo-resistance of washed cottonseed meal-based wood adhesives[J].Polymers,2017,9(12):675.
[9]GUO M R,WANG G R.Milk protein polymer and its application in environmentally safe adhesives[J].Polymers,2016,8(9):324.
[10]QU P,HUANG H Y,WU G F,et al.The effect of hydrolyzed soy protein isolate on the structure and biodegradability of urea-formaldehyde adhesives[J].Journal of Adhesion Science and Technology,2015,29(6):502-517.
[11]QU P,HUANG H Y,WU G F,et al.Hydrolyzed soy protein isolates modified urea-formaldehyde resins as adhesives and its biodegradability[J].Journal of Adhesion Science and Technology,2015,29(21):2381-2398.
[12]JI N,LONG J,ZHENG H Y,et al.Phenolic resin modified soybean protein adhesive[J].Advanced Materials Research,2011,236-238:3-7.
[13]张亮亮,徐曼,胡新宇,等.EGCG-Cu络合物与牛血清蛋白相互作用研究[J].林业工程学报,2017,2(5):46-50.
[14]邱盈盈,张越,李城,等.改性豆基蛋白胶粘剂的制备及应用[J].中国胶粘剂,2012,21(6):27-30.
[15]陈敏智,周晓燕,陈燕.纳米改性大豆蛋白基复合材料研究进展[J].林业工程学报,2015,29(6):2-6.
[16]LEI H,DU G,WU Z,et al.Cross-linked soy-based wood adhesives for plywood[J].International Journal of Adhesion and Adhesives,2014,50:199-203.
[17]GAO Q,SHI S Q,ZHANG S F,et al.Soybean meal-based adhesive enhanced by MUF resin[J].Journal of Applied Polymer Science,2012,125(5):3676-3681.
[18]吴志刚,杜官本,雷洪,等.UFC和大豆蛋白制备环保型脲醛树脂研究[J].林业工程学报,2016,1(1):31-36.
[19]CHEN N R,ZHENG P T,ZENG Q Z,et al.Characterization and performance of soy-based adhesives cured with epoxy resin[J].Polymers,2017,9(10):514.
[20]WU Z G,LEI H,CAO M,et al.Soy-based adhesive crosslinked by melamine glyoxal and epoxy resin[J].Journal of Adhesion Science and Technology,2016,30(19):2120-2129.
[21]雷洪,吴志刚,杜官本,等.交联改性大豆蛋白胶胶合板的工艺及湿剪切强度研究[J].木材工业,2013,27(2):8-11.
[22]WU Z,LEI H,DU G.Disruption of soy-based adhesive treated by Ca(OH)2and Na OH[J].Journal of Adhesion Science and Technology,2013,27(20):1-7.
[23]LI C C,LI H Y,ZHANG S F,et al.Preparation of reinforced soy protein adhesive using silane coupling agent as an enhancer[J].Bio Resources,2014,9(3):5448-5460.
[24]雷文,杨涛,王考将,等.环氧树脂改性大豆基木材胶粘剂的制备与表征[J].大豆科学,2010,29(1):118-120.
[25]FRIHART C R,SATORI H.Soy flour dispersibility and performance as wood adhesive[J].Journal of Adhesion Science and Technology,2013,27(18-19):2043-2052.
[26]FRIHART C R,LORENZ L.Protein Modifiers Generally provide limited improvement in wood bond strength of soy flour adhesives[J].Forest Products Journal,2013,63(3-4):138-142.
[27]LI J J,LUO J,LI X N,et al.Soybean meal-based wood adhesive enhanced by ethylene glycol diglycidyl ether and diethylenetriamine[J].Industrial Crops and Products,2015,74:613-618.
[28]XU F J,DONG Y M,ZHANG W,et al.Preparation of cross-linked soy protein isolate-based environmentallyfriendly films enhanced by PTGE and PAM[J].Industrial Crops and Products,2015,67:373-380.
[29]WU Z G,XI X D,LEI H,et al.Soy-based adhesive crosslinked by phenolformaldehyde glutaraldehyde[J].Polymers,2017,9(5):169.
[30]LEI H,WU Z G,CAO M,et al.Study on the soy proteinbased wood adhesive modified by hydroxymethyl phenol[J].Polymers,2016,8(7):256-265.
[31]LIANG J K,WU Z G,LEI H,et al.The reaction between furfuryl alcohol and model compound of protein[J].Polymers,2017,9(12):711.
[32]王敏,薛永强,崔子祥.环氧氯丙烷碱催化水解反应的研究[J].应用化工,2010,39(1):49-51.
[33]彭燕.氨基酸与环氧化合物反应的研究[D].济南:山东轻工业学院,2006.
[34]雷洪,吴志刚,席雪冬,等.处理工艺对大豆蛋白基胶粘剂的影响[J].森林与环境学报,2016,36(2):246-251.
[35]XIE J J,LI N,ZENG N.Preparation and its properties of the urea modified soy protein isolate adhesives[J].Advanced Materials Research,2012,580:481-484.
[36]吴志刚.蛋白基胶粘剂交联改性及机理研究[D].北京:北京林业大学,2016.
[37]顾蓉,穆宝宁,郭康权.魔芋粉-壳聚糖-聚乙烯醇共混胶粘剂的流变模型[J].农业工程学报,2014,30(1):278-284.
[38]王洪艳,李琴,袁少飞,等.两种大豆蛋白胶的化学结构分析[J].林业工程学报,2015,29(1):90-93.
[39]孙恩惠,黄红英,武国峰,等.大豆蛋白基生物质胶粘剂的合成及热力学性能[J].林产化学与工业,2015,35(2):147-153.
[40]迟光伟.利用麻疯树种子制备生物柴油及胶粘剂的研究[D].桂林:广西大学,2011.
[2]吴义强,李新功,左迎峰,等.农林剩余物无机人造板研究进展[J].林业工程学报,2016,1(1):8-15.
[3]陈焱,石爱民,刘丽,等.木材用植物蛋白胶粘剂蛋白质改性与性能改善研究进展[J].粮食与油脂,2017,42(2):125-129.
[4]吴志刚,雷洪,杜官本.大豆蛋白基胶粘剂研究与应用发展现状[J].粮食与油脂,2015,28(11):1-5.
[5]张俊,杜官本,席雪冬.单宁树脂砂轮片制备及氧化铝在树脂中的分形分布[J].林业工程学报,2016,1(1):88-92.
[6]郝海霞,吴志刚,雷洪,等.3种处理方式对小桐子蛋白基胶粘剂性能的影响[J].西南林业大学学报,2016,36(1):136-139.
[7]JIN CN,ZHANG SC,PANG JY,etal.Plywoodwithsoyproteinacrylate hybrid adhesive[J].Advanced Materials Research,2014,884-885:108-111.
[8]HE Z Q,CHENG H N,KLASSON T K.Effects of particle Size on the morphology and water-and thermo-resistance of washed cottonseed meal-based wood adhesives[J].Polymers,2017,9(12):675.
[9]GUO M R,WANG G R.Milk protein polymer and its application in environmentally safe adhesives[J].Polymers,2016,8(9):324.
[10]QU P,HUANG H Y,WU G F,et al.The effect of hydrolyzed soy protein isolate on the structure and biodegradability of urea-formaldehyde adhesives[J].Journal of Adhesion Science and Technology,2015,29(6):502-517.
[11]QU P,HUANG H Y,WU G F,et al.Hydrolyzed soy protein isolates modified urea-formaldehyde resins as adhesives and its biodegradability[J].Journal of Adhesion Science and Technology,2015,29(21):2381-2398.
[12]JI N,LONG J,ZHENG H Y,et al.Phenolic resin modified soybean protein adhesive[J].Advanced Materials Research,2011,236-238:3-7.
[13]张亮亮,徐曼,胡新宇,等.EGCG-Cu络合物与牛血清蛋白相互作用研究[J].林业工程学报,2017,2(5):46-50.
[14]邱盈盈,张越,李城,等.改性豆基蛋白胶粘剂的制备及应用[J].中国胶粘剂,2012,21(6):27-30.
[15]陈敏智,周晓燕,陈燕.纳米改性大豆蛋白基复合材料研究进展[J].林业工程学报,2015,29(6):2-6.
[16]LEI H,DU G,WU Z,et al.Cross-linked soy-based wood adhesives for plywood[J].International Journal of Adhesion and Adhesives,2014,50:199-203.
[17]GAO Q,SHI S Q,ZHANG S F,et al.Soybean meal-based adhesive enhanced by MUF resin[J].Journal of Applied Polymer Science,2012,125(5):3676-3681.
[18]吴志刚,杜官本,雷洪,等.UFC和大豆蛋白制备环保型脲醛树脂研究[J].林业工程学报,2016,1(1):31-36.
[19]CHEN N R,ZHENG P T,ZENG Q Z,et al.Characterization and performance of soy-based adhesives cured with epoxy resin[J].Polymers,2017,9(10):514.
[20]WU Z G,LEI H,CAO M,et al.Soy-based adhesive crosslinked by melamine glyoxal and epoxy resin[J].Journal of Adhesion Science and Technology,2016,30(19):2120-2129.
[21]雷洪,吴志刚,杜官本,等.交联改性大豆蛋白胶胶合板的工艺及湿剪切强度研究[J].木材工业,2013,27(2):8-11.
[22]WU Z,LEI H,DU G.Disruption of soy-based adhesive treated by Ca(OH)2and Na OH[J].Journal of Adhesion Science and Technology,2013,27(20):1-7.
[23]LI C C,LI H Y,ZHANG S F,et al.Preparation of reinforced soy protein adhesive using silane coupling agent as an enhancer[J].Bio Resources,2014,9(3):5448-5460.
[24]雷文,杨涛,王考将,等.环氧树脂改性大豆基木材胶粘剂的制备与表征[J].大豆科学,2010,29(1):118-120.
[25]FRIHART C R,SATORI H.Soy flour dispersibility and performance as wood adhesive[J].Journal of Adhesion Science and Technology,2013,27(18-19):2043-2052.
[26]FRIHART C R,LORENZ L.Protein Modifiers Generally provide limited improvement in wood bond strength of soy flour adhesives[J].Forest Products Journal,2013,63(3-4):138-142.
[27]LI J J,LUO J,LI X N,et al.Soybean meal-based wood adhesive enhanced by ethylene glycol diglycidyl ether and diethylenetriamine[J].Industrial Crops and Products,2015,74:613-618.
[28]XU F J,DONG Y M,ZHANG W,et al.Preparation of cross-linked soy protein isolate-based environmentallyfriendly films enhanced by PTGE and PAM[J].Industrial Crops and Products,2015,67:373-380.
[29]WU Z G,XI X D,LEI H,et al.Soy-based adhesive crosslinked by phenolformaldehyde glutaraldehyde[J].Polymers,2017,9(5):169.
[30]LEI H,WU Z G,CAO M,et al.Study on the soy proteinbased wood adhesive modified by hydroxymethyl phenol[J].Polymers,2016,8(7):256-265.
[31]LIANG J K,WU Z G,LEI H,et al.The reaction between furfuryl alcohol and model compound of protein[J].Polymers,2017,9(12):711.
[32]王敏,薛永强,崔子祥.环氧氯丙烷碱催化水解反应的研究[J].应用化工,2010,39(1):49-51.
[33]彭燕.氨基酸与环氧化合物反应的研究[D].济南:山东轻工业学院,2006.
[34]雷洪,吴志刚,席雪冬,等.处理工艺对大豆蛋白基胶粘剂的影响[J].森林与环境学报,2016,36(2):246-251.
[35]XIE J J,LI N,ZENG N.Preparation and its properties of the urea modified soy protein isolate adhesives[J].Advanced Materials Research,2012,580:481-484.
[36]吴志刚.蛋白基胶粘剂交联改性及机理研究[D].北京:北京林业大学,2016.
[37]顾蓉,穆宝宁,郭康权.魔芋粉-壳聚糖-聚乙烯醇共混胶粘剂的流变模型[J].农业工程学报,2014,30(1):278-284.
[38]王洪艳,李琴,袁少飞,等.两种大豆蛋白胶的化学结构分析[J].林业工程学报,2015,29(1):90-93.
[39]孙恩惠,黄红英,武国峰,等.大豆蛋白基生物质胶粘剂的合成及热力学性能[J].林产化学与工业,2015,35(2):147-153.
[40]迟光伟.利用麻疯树种子制备生物柴油及胶粘剂的研究[D].桂林:广西大学,2011.