非异氰酸酯聚氨酯的合成
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摘要
由异氰酸酯和多元醇合成的传统聚氨酯具有优良性能而受到广泛应用,但传统聚氨酯同时也存在性能和安全等方面的缺点。由多环碳酸酯和多元胺合成而来的非异氰酸酯聚氨酯有望成为一种性能良好的绿色环保材料替代传统聚氨酯。本论文旨在选择了一条新型而有效的合成路线来制备非异氰酸酯聚氨酯。
1.使用双金属氰化物催化剂聚合环氧氯丙烷得到聚环氧氯丙烷醚,然后再和叔胺反应得到高分子季铵盐,制备下一步反应所需的高分子催化剂。核磁共振对反应产物进行结构分析。研究表明,环氧氯丙烷聚合反应的诱导期随着催化剂浓度的增加而减小,总的聚合反应时间也减小,聚合反应和季铵化反应最适宜的温度分别是110℃和90℃,三甲胺大量过量时能得到转化率比较高季铵盐,同时三甲胺作叔胺反应效果最好。
2.使用双金属氰化物催化剂对高活性聚醚进行封端反应,得到聚醚末端带有一定数量环氧氯丙烷的邻氯醇聚醚,然后再和氨水反应能得到端氨基聚醚。核磁共振图谱证实了最终反应产物的生成。实验中通过一系列的对比实验探讨了第二步反应的最佳条件,反应的最佳反应温度是110℃,反应最佳原料摩尔配比氨水:氯甲基=5:1,最佳反应时间为6h。
3.以季铵盐为相转移催化剂,碳酸氢盐离子与端邻氯醇聚醚在溶剂中反应得到端环碳酸酯聚醚,红外和核磁共振表征结果证实了环碳酸酯基团的生成。研究表明,溶剂的极性和相转移催化剂的分子结构影响着反应转化率。实验同时对不同阶段的产物做了粘度测定,同一分子量下粘度顺序为:端氯醇聚醚>端环碳酸酯聚醚>端羟基聚醚。
4.将三官能度端环碳酸酯聚醚与双官能度伯胺反应得到非异氰酸酯聚氨酯(NIPU),做谱图分析。研究表明:乙二胺形成的NIPU的玻璃化温度最高,力学性能最好,当环碳酸酯与伯胺的摩尔比为1:1时,得到物理和力学性能较好的NIPU。甲苯溶胀实验同时表明乙二胺形成的NIPU具有较大的交联密度。
Polyurethanes obtained from diisocyanates and diols are attractive and important chemical products with extensive application in various fields because of its excellent properties,but traditional polyurethane have some formidable defects such as toxicity, poor hydrolytic stability and insufficient permeability.New generation polyurethane, nonisocyanate polyurethane(NIPU),which shows lower permeability,higher chemical resistance and non-poisonous fabrication process compared with traditional polyurethane,is obtained from multifunctional cyclic carbonates and multifunctional primary polyamines.The synthesis route and conclusion are as follows:
1.The polymerization of epichlorohydrin was catalyzed by double metal cyanide (DMC),and then the polymer reacted with tertiary amine to give polymer quaternary ammonium salt.Different reaction conditions were discussed in this two-step reaction and the reaction products were confirmed by NMR analysis.The studies showed that: The induction period and total reaction time get shorter as the concentration of catalyst enhanced,the optimum time of polymerization and quaternization reaction are 110℃and 90℃,respectively.The suitable material ratio of chloromethyl and trimethylamine were 2.5,the cationic degree of polymer quaternary ammonium salt from trimethylamine was higher than that from triethylamine and pyridine.
2.A novel amine-terminated polyether(ATPE) was synthesized with two steps. The first was that vic-chlorohydrins-terminated polyether was obtained through high reactive polyether polyols reacting with epichlorohydrin catalyzed by(DMC).The second was that vic-chlorohydrins-terminated polyether(CHTPE) reacting with ammonia to form amine-terminated polyether.We found the rule of graft numbers of epichlorohydrin,and quantitative determined amine value of product to study the effect factors of reaction.Structure of product was signified by using ~1HNMR.When the optimal reaction temperature is 110℃,the ratio of raw is 5:1 and the reation time is 6h,the conversion of ATPE would reach about 90%.
3.The cyclocarbonate- terminated polyether(CCTPE) can be obtained by reacting CHTPE with alkali metal hydrocarbonate in the presence of quaternary ammonium catalysts.98%yield of CCTPE was obtained by optimizing reaction condition through choosing different catalysts,solvents,and reaction temperature.~1HNMR and FTIR spectra have been used to analyze target product. The research showed that:the polarity of solvent and the molecular weight and compatibility of phase transfer catalyst have a significant impact on conversion,the viscosity of different stage reaction product have been tested,the order was:CCTPE> CHTPE>HTPE.
4.Tri-functionality cyclocarboanate reacted with difunctional primary amine to afford crosslinking network nonisocyanate polyurethanes.All cured products were characterized for their thermal and mechanical properties to find out the effect of carbonate-to-amine ratio and type of amine.The research showed that:diethylamine based NIPU have the most excellent properties,and when carbonate-to-amine ratio is 1:1,the products have the most favorable overall performance.Swelling in toluene show that diethylamine based NIPU have the lowest value because of its highest crosslinking density.
1.使用双金属氰化物催化剂聚合环氧氯丙烷得到聚环氧氯丙烷醚,然后再和叔胺反应得到高分子季铵盐,制备下一步反应所需的高分子催化剂。核磁共振对反应产物进行结构分析。研究表明,环氧氯丙烷聚合反应的诱导期随着催化剂浓度的增加而减小,总的聚合反应时间也减小,聚合反应和季铵化反应最适宜的温度分别是110℃和90℃,三甲胺大量过量时能得到转化率比较高季铵盐,同时三甲胺作叔胺反应效果最好。
2.使用双金属氰化物催化剂对高活性聚醚进行封端反应,得到聚醚末端带有一定数量环氧氯丙烷的邻氯醇聚醚,然后再和氨水反应能得到端氨基聚醚。核磁共振图谱证实了最终反应产物的生成。实验中通过一系列的对比实验探讨了第二步反应的最佳条件,反应的最佳反应温度是110℃,反应最佳原料摩尔配比氨水:氯甲基=5:1,最佳反应时间为6h。
3.以季铵盐为相转移催化剂,碳酸氢盐离子与端邻氯醇聚醚在溶剂中反应得到端环碳酸酯聚醚,红外和核磁共振表征结果证实了环碳酸酯基团的生成。研究表明,溶剂的极性和相转移催化剂的分子结构影响着反应转化率。实验同时对不同阶段的产物做了粘度测定,同一分子量下粘度顺序为:端氯醇聚醚>端环碳酸酯聚醚>端羟基聚醚。
4.将三官能度端环碳酸酯聚醚与双官能度伯胺反应得到非异氰酸酯聚氨酯(NIPU),做谱图分析。研究表明:乙二胺形成的NIPU的玻璃化温度最高,力学性能最好,当环碳酸酯与伯胺的摩尔比为1:1时,得到物理和力学性能较好的NIPU。甲苯溶胀实验同时表明乙二胺形成的NIPU具有较大的交联密度。
Polyurethanes obtained from diisocyanates and diols are attractive and important chemical products with extensive application in various fields because of its excellent properties,but traditional polyurethane have some formidable defects such as toxicity, poor hydrolytic stability and insufficient permeability.New generation polyurethane, nonisocyanate polyurethane(NIPU),which shows lower permeability,higher chemical resistance and non-poisonous fabrication process compared with traditional polyurethane,is obtained from multifunctional cyclic carbonates and multifunctional primary polyamines.The synthesis route and conclusion are as follows:
1.The polymerization of epichlorohydrin was catalyzed by double metal cyanide (DMC),and then the polymer reacted with tertiary amine to give polymer quaternary ammonium salt.Different reaction conditions were discussed in this two-step reaction and the reaction products were confirmed by NMR analysis.The studies showed that: The induction period and total reaction time get shorter as the concentration of catalyst enhanced,the optimum time of polymerization and quaternization reaction are 110℃and 90℃,respectively.The suitable material ratio of chloromethyl and trimethylamine were 2.5,the cationic degree of polymer quaternary ammonium salt from trimethylamine was higher than that from triethylamine and pyridine.
2.A novel amine-terminated polyether(ATPE) was synthesized with two steps. The first was that vic-chlorohydrins-terminated polyether was obtained through high reactive polyether polyols reacting with epichlorohydrin catalyzed by(DMC).The second was that vic-chlorohydrins-terminated polyether(CHTPE) reacting with ammonia to form amine-terminated polyether.We found the rule of graft numbers of epichlorohydrin,and quantitative determined amine value of product to study the effect factors of reaction.Structure of product was signified by using ~1HNMR.When the optimal reaction temperature is 110℃,the ratio of raw is 5:1 and the reation time is 6h,the conversion of ATPE would reach about 90%.
3.The cyclocarbonate- terminated polyether(CCTPE) can be obtained by reacting CHTPE with alkali metal hydrocarbonate in the presence of quaternary ammonium catalysts.98%yield of CCTPE was obtained by optimizing reaction condition through choosing different catalysts,solvents,and reaction temperature.~1HNMR and FTIR spectra have been used to analyze target product. The research showed that:the polarity of solvent and the molecular weight and compatibility of phase transfer catalyst have a significant impact on conversion,the viscosity of different stage reaction product have been tested,the order was:CCTPE> CHTPE>HTPE.
4.Tri-functionality cyclocarboanate reacted with difunctional primary amine to afford crosslinking network nonisocyanate polyurethanes.All cured products were characterized for their thermal and mechanical properties to find out the effect of carbonate-to-amine ratio and type of amine.The research showed that:diethylamine based NIPU have the most excellent properties,and when carbonate-to-amine ratio is 1:1,the products have the most favorable overall performance.Swelling in toluene show that diethylamine based NIPU have the lowest value because of its highest crosslinking density.
引文
[1]李绍雄,刘益军,等,聚氨酯树脂及其应用[M],北京:化学工业出版社.2002,184
[2]朱吕民,刘益军,等,聚氨酯泡沫塑料[M],第三版,北京:化学工业出版社.2005,133
[3]Angelar Austin,Global overview of the PU industry:Prospects and possibilities,UTECH EUPOPE 2006 Conference[C],Maastricht Netherlands,2006,28-30
[4]朱树新,开环聚合[M],北京:化学工业出版社.1987,48-57
[5]Jedlinski Z.,Zabski L.,Dobrzynski P.,Manufacture of Hydroxyl-Terminated Halogen Containing Oligomeric Polythers[P],PL 150506,1991
[6]Stewrt M.J.,Catalysts for Proliferation of Cyclic Ethers[P],WO9015092,1990
[7]黄家贤,丁伦汉,朱端慧,等,聚环氧氯丙烷的合成与表征[J],高等学校化学学报,1991,12(6):843-846
[8]张阿方,张鸿志,杨惠昌,等,三氟化硼引发四氢吠喃开环聚合反应机理[J],科学通报,1990.2:112-115
[9]郭焕萍,PU弹性体用环氧丙烷-四氢吠喃共聚醚二醇的生产[J],弹性体,1998,8(4):27-30
[10]JACK MILGROM,Method of making a polyether using a double metal cyanide complex compound[P],US patent,US3278457,1966
[11]B.Le-Khac,Highly active double metal cyanide catalysts[P],US patent,US5693584,1998
[12]HR Hinney,DS Wardius,Process for preparing metal cyanide complex catalyst[P],US patent,US5158922,1992
[13]JW Reisch,MM Martinez,M Raes,Process for purifying and end-capping polyols made using double metal cyanide catalysts,US patent,US5144093,1992
[14]G Combs,HR Hinney,PT Bowman,Process for rapid activation of double metal cyanide catalysts,US patent,US5783513,1998
[15]P Ooms,J Hofmann,C Steinlein,S Ehlers,Double metal cyanide catalysts for producing polyether polyols,US Patent,US6919293,2005.
[16]黄亦军,双金属氰化物络合物催化环氧烷烃开环聚合的研究[D],浙江,浙江大学,2002:102-105
[17]Oleg L.Figovsky,Leonid D.Shapovalov,Features of Reaction Amino-cyclocarboante for Production of New Type Nonisocyanate Polyurethane Coating[J],Macromol.Symp.,2002,187:325-332
[18]G Rokick,Aliphatic cyclic carbonates and spiroorthocarbonates as monomers[J],Prog.Polym Sci.,2000,25:259-342
[19]Bungo Ochiai,Yuriko Satoh,Takeshi Endo,Nucleophilic polyaddition in water based on chemo-selective reaction of cyclic carbonate with amine[J],Green Chemistry,2005,7:765-767
[20]张锁江,孙剑,成卫国,含水体系环碳酸酯的合成方法,CN101108843,2008
[21]H.S.Kim,J.J.Kim,H.Kim,et.al,Imidazolium zinc tetrahalide-catalyzed coupling reaction of CO_2 and ethylene oxide or propylene oxide[J],Journal of Catalysis,2003,220(1):44-46
[22]X.Lu,X.Feng,R.He,Catalytic formation of ethylene carbonates from supercritical carbon dioxide/ethylene oxide mixture with tetradentate Schiff-base complexes as catalyst [J],Applied Catalysis A,General.,2002,234(1-2):25-33
[23]M.Yoshida,M.Ihara,A Novel Methodology for the Synthesis of Cyclic Carbonates Based on the Palladium-Catalyzed Cascade Reaction of 4-Methoxycarbonyloxy-2-butyn-l-ols with Phenols,Involving a Novel Carbon Dioxide Elimination-Fixation Process[J],J.Am.Chem.Soc,2003,125(16):4874-4881
[24]Robert L.,Paddock,SonBinh T.Nguyen,Chiral(salen)Co~(Ⅲ) catalyst for the synthesis of cyclic carbonates[J],Chem.Commun.,2004,1622-1623
[25]N.Kihara,N.Hara,T.Endo,Catalytic activity of various salts in the reaction of 2,3-epoxypropyl phenyl ether and carbon dioxide[J],J.Org.Chem.,1993,58(23):6198-6202
[26]R.L.Addock,S.T.Nguyen,Chemical CO_2 Fixation:Cr~((Ⅲ)) Salen Complexes as Highly Efficient Catalysts for the Coupling of CO_2 and Epoxides[J],J.Am.Chem.Soc,2001,123(46):11498-11499
[27]Y.M.Shen,W.L.Duan,M.Shi,Chemical fixation of carbon dioxide catalyzed by Binaphthyldiamino Zn,Cu,and Co salen-type complexes[J],Chemlnform,2003,34(26):132-135
[28]H.S.Kim,J.J.Kim,B.G.Lee,O.S.Jung,et,al.,Well-Defined Highly Active Heterogeneous Catalyst System for the Coupling Reactions of Carbon Dioxide and Epoxides[J],Journal of Catalysis,2002,39:4096.
[29]D.Walther,M.Ruben,S.Rau,Carbon dioxide and metal centres:from reactions inspired by nature to reactions in compressed carbon dioxide as solvent[J],Coordination Chemistry Reviews,1999,182(1):67-100
[30]X.Lu,R.He,C.X.Bai,Synthesis of ethylene carbonate from supercritical carbon dioxide/ethylene oxide mixture in the presence of bifunctional catalyst[J],Journal of Molecular Catalysis.A,Chemical,2002,186(1-2):1 -11
[31]R.Srivastava,T.H.Bennur,D.Srinivas,Factors affecting activation and utilization of carbon dioxide in cyclic carbonates synthesis over Cu and Mn peraza macrocyclic complexes[J],Journal of Molecular Catalysis.A,Chemical,2005,226(2):199-205
[32]X..B.Lu,B.Liang,Y.J.Zhang,Y.Z.Tian,et.al,Zuschrift-Highly Active,Binary Catalyst Systems for the Alternating Copolymerization of CO_2 and Epoxides under Mild Conditions[J],Angew Chem Int Ed Engl.,2004,43(27):3574-3577.
[33]Keiichi Tomishige,Hiroaki Yasuda,Yuichi Yoshida,et.al.,Catalytic performance and properties of ceria based catalysts for cyclic carbonate synthesis from glycol and carbon dioxide[J],Green.Chem.2004,6:206-214
[34]G.Rokicki,W.Kuran,Cyclic Carbonates Obtained by Reactions of Alkali Metal Carbonates with Epihalohydrins[J],Bull.Chem.Soc.Jpn.,1984,57(6):1662-1666
[35]Gabriel Rokickil,Witold Kuran,Barbara Pogorzelska-Marciniak,Cyclic carbonates from carbon dioxide and oxiranes[J],Monatshefte fur Chemie,1984,115(2):205-214
[36]Gabriel Rokicki,Witold Kuran,Cyclic Carbonates Obtained by Reactions of Alkali Metal Carbonates with Epihalohydrins[J],Bulletin of the Chemical Society of Japan,1984,57(6):1662-1666
[37]Ratzenhofer,M.,Kisch,H.Angew.,Metal-Catalyzed Synthesis of Cyclic Carbonates from Carbon Dioxide and Oxiranes[J],Angewandte Chemie International Edition in English,1980,19(4):317-318
[38]Akio Baba,Takashi Nozaki Haruo Matsuda,Carbonate Formation from Oxiranes and Carbon Dioxide Catalyzed by Organotin Halide-Tetraalkylphosphonium Halide Complexes[J],Bulletin of the Chemical Society of Japan,1987,60(4):1552-1554
[39]Xiao-Bing Lu,Ying-Ju Zhang,Bin Liang,et.al,Chemical fixation of carbon dioxide to cyclic carbonates under extremely mild conditions with highly active bifunctional catalysts[J],Journal of Molecular Catalysis A:Chemical,2004,210(1-2):31-34
[40]X.Lu,J.Xiu,R.He,K.Jin,et.al,Chemical fixation of CO_2 to ethylene carbonate under supercritical conditions:continuous and selective[J],Applied Catalysis A,General,2004,275(1-2):73-78
[41]Y.Du,F.Cai,D.L.Kong,et.al,Organic solvent-free process for the synthesis of propylene carbonate from supercritical carbon dioxide and propylene oxide catalyzed by insoluble ion exchange resins[J],Green Chem.,2005,7:518-523
[42]H.Yasuda,L.N.He,T.Takahashi,T.Sakakura,Non-halogen catalysts for propylene carbonate synthesis from CO_2 under supercritical conditions[J],Applied Catalysis A,General,2006,298(10):177-180
[43]H.Yasuda,L.N.Hen,T.Sakakura,Cyclic Carbonate Synthesis from Supercritical Carbon Dioxide and Epoxide over Lanthanide Oxychloride[J],Journal of Catalysis,2002,209(2):547-550
[44]Jin-Quan Wang,Xiao-Dong,et.al,Solventless Synthesis of Cyclic Carbonates from Carbon Dioxide and Epoxides Catalyzed by Silica-Supported Ionic Liquids under Supercritical Conditions[J],Catalysis Communications,2007,8(2):167-172
[45]T.Nishikubo,A.Kameyama,J.Yamashita,etal,Insoluble Polystyrene-Bound Quaternary Onium Salt Catalysts for the Synthesis of Cyclic Carbonate by the Reaction of Oxiranes with Carbon Dioxide[J],Journal of polymer science,1993,31(4):939-947
[46]John H.Clements,Reactive Applications of Cyclic Alkylene Carbonates[J],Industrial and Engineering Chemistry Research,2003,42:663-674
[47]Blank N,Figovsky O.,Nonisocyanate polyurethane glues for jointing reinforced plastics,Proceedings of International Adhesion Symposium[C],Tokyo,Japan,1994.p.87
[48]Figovsky oleg,Shapovalov leonid,Blank nelly,et,al.,Cyclocarbonate Groups Containing Hydroxyamine Oligomers From Epoxycyclocarbonates[P],WO0042033,2004
[49]Figovsky Oleg,Shapovalov Leonid,Preparation of Oligomeric Cyclocarbonates And Their Use In Ionisocyanate Or Hybrid Nonisocyanate Polyurethanes[P],WO03028644,2003
[50]Burk R.M.,ROOF M.B.,A safe and efficient method for conversion of 1,2-and 1,3-diols to cyclic carbonates utilizing triphosgene[J],Tetrahedron Lett.,1993,34(3):395-398
[51]Okutsu,Munenao,Kitsuki,Tomohito.Preparation of cyclic carbonate esters from I,2-diols and carbonated esters[P],JP2004168674,2004
[52]Fukumura,Takanori,Hayashi,Hidetoshi,Nontoxic preparation of alicyclic carbonates from alicyclic diols and difluorodiamines[P],JP 2004315445,2004
[53]C.Venturello,R.,D'aloisio.ACOnvenient Synthesis of 1,2-Alkanediyl Carbonates[J],Synthesis,1985,1:33-34
[54]James A.Kenar,Ian D.Tevis.Convenient Preparation of fatty ester cyclic carbonate[J],European Journal of Lipid Science and Technology,2005,107(2):135-137
[55]Carlson WW,Cretcher LH,Hydroxyalkylation with Cyclic Alkylene Esters:Synthesis of Hydroxyethylapocupreine[J],J Am Chem Soc.1947,69(8):1952-1956
[56]Yoshino T,Inaba S,Ishido Y.Synthetic Studies by the Use of Carbonates:The Condensation Reactions of Ethylene Carbonate with a Variety of Phenols Catalyzed by Lithium Hydride or Tetraethylammonium Halides[J],Bull Chem Soc Jpn.1973,46(2):553-556
[57]Rokicki G,Pawlicki J,Kuran W.,Poly(ether-carbonate)s from Diphenolates,Cyclic Carbonates,and Dihalo Compounds[J],Polymer Journal,1985,13(3):509-516
[58]Rokicki G.,cyclic dicarbonates as new monomers for the synthesis of poly(hydroxy ether) s[J],Die Makromolekulare Chemie,1985;186(2):331-337
[59]Baizer MM,Clark JR,Smith E.,Monocarbamates of 1,2-Dihydroxy-3-aryloxypropanes[J],J Org Chem.,1957,22(12):1596-1599
[60]El-Giamal MF,Schulz RC,Ober einige Copolyurethane ausgehend von Piperazin[J],Colloid & Polymer Science,1978,256(3):1435-1536.
[61]Burgel T,Fedtke M.,Reactions of cyclic carbonates with amines:Model studies for curing process[J],Polym Bull.,1991,27(2):171-177
[62]Burgel T,Fedtke M.,Epoxy resins with cyclic carbonate structures[J],Polym Bull.,1993,30(1):61-68
[63]Kihara N,Kushida Y,Endo T.,Optically active poly(hydroxyurethane)s derived from cyclic carbonate and L-lysine derivatives[J],Polym Sci Part A:Polym Chem 1996;34(11):2173-2179
[64]Rokicki G,Lewandowski M.,Epoxy resins modified by carbon dioxide[J],Angew Makromol Chem 1987;148(1):53-66
[65]Rokicki G,Wojciechowski C,Epoxy resins modified by carbon dioxide[J],J Appl Polym Sci 1990,41(3-4):647-659
[66]Rokicki G.,Synthesis of poly(hydroxyurethanes) from diepoxides,carbon dioxide,and diamines[J],Polimery,1989,34(4):304-147
[67]Rokicki G,Lazinski R.,Polyamines containing P-hydroxyurethane linkages as curing agents for epoxy resin[J],Die Angewandte Makromolekulare Chemie,1989,170(1):211-225.
[68]Schwenk E,Synthesis of Polyesters from Dicarboxylic Acid Anhydrides and Epoxides or Cyclic Carbonates of Diols[J],Makromol Chem.,1962,51:53-57
[69]Tarbell DS.,Carboxylic carbonic anhydrides and related compounds[J],Acc Chem Res.,1969,2(10):296-300
[70]Kenneth R.Carter,Richard A.DiPietro,Martha 1.Sanchez,et.al,Polyimide Nanofoams Based on Ordered Polyimides Derived from Poly(amic alkyl esters):PMDA/4-BDAF[J],Chem.Mater.,1997,9(1):105-118.
[71]Vogdanis L,Martens B,Uchtmann H,et,al.,Synthetic and thermodynamic investigations in the polymerization of ethylene carbonate[J],Die Makromolekulare Chemie,1990,191(3):465-472
[72]Soga K,Hosoda S,Tazuke Y,et.al,Polymerization of propylene carbonate[J],Polym Sci Part A:Polym Chem.,1977,15(1):219-229
[73]Vogdanis L,Heitz W.,Carbon dioxide as a monomer and the polymerization of ethylene carbonate[J],Makromol Chem,Rapid Commun 1986,7:543-547
[74]Kuran W.,Listos T.,Copolymerization of epoxides and five-membered cyclic carbonates in the presence of zinc coordination catalysts[J],Makromol Chem 1992,193(4):945-956
[75]Penco M.,Donetti R.,Mendichi R.,et,al.,New poly(ester-carbonate) multi-block copolymers based on poly(lactic-glycolic acid) and poly(ε-caprolactone) s egments[J],Macromol Chem Phys.,1998,199(8):1737-1745
[76]Harris RF.,Molecular weight advancement of poly(ethylene ether carbonate) polyols[J],J Appl Polym Sci.,1989,38(3):463-476
[77]Harris RF,McDonald LA.,Structural features of poly(alkylene ether carbonate) diols and intermediates formed during their preparation[J],Appl Polym Sci 1989,37(6):1491-1511
[78]C D Diakoumakos,D L Kotzev.Non-Isocyanate-Based Polyurethanes Derived upon the Reaction of Amines with Cyclocarbonate Resins[J],Macromol.Symp.2004,216(1):37-46.
[79]O L Figovsky,Hybrid nonisocyanate polyurethane network polymers and composites formed therefrom[P],USPatent,US6120905,2000.
[80]Pathiraja A.Gunatillake,Gordon F.Meijs,Simon J.,et.al,Synthesis and characterization of a series of poly(alkylene carbonate) macrodiols and the effect of their structure on the properties of polyurethanes[J],Journal of Applied Polymer Science,1998,69(8):1621-1633
[81]Garipov,Sysoev,Mikheev et.al,Reactivity of Cyclocarbonate Groups in Modified Epoxy-Amine Compositions[J],Doklady Akademii Nauk,2003,393(1):61-64
[82]Dean C.Webster,Allen L.Crain,Synthesis and applications of cyclic carbonate functional polymers in thermosetting coatings[J],Progress in Organic Coatings,2000,40(1):275-282
[83]Shuichi Matsumura,Yasuyuki Soeda,Kazunobu Toshima,Perspectives for synthesis and production of polyurethanes and related polymers by enzymes directed toward green and sustainable chemistry[J],Appl Microbiol Biotechnol.,2006,70(1):12-20
[84]Robson F.Storey,Douglas C.Hoffman,Formation of Poly(ethylene ether carbonate) Diols:Proposed Mechanism and Kinetic Analysis[J],Macromolecules 1992,25:5369-5382
[85]Oguz Turunc,Nilhan Kayaman-Apohan.M.,Vezir Kahraman,et.al,Nonisocyanate based polyurethane/silica nanocomposites and their coating performance[J],J Sol-Gel Sci Technol.,2008,47:290-299
[86]I.V.Stroganov,V.F.Strogano.Peculiarities of Structurization and Properties of Nonisocyanate Epoxyurethane Polymers[J],Polymer Science,Ser.C,2007,49(3):258-263.
[87]Thomas Burgel,Manfred Fedtke,Reactions of cyclic carbonates with amines:Model studies for curing process[J],Polymer Bulletin,1991,27(2):171-177
[88]Thomas B.Lirgel,Manfred Fedtke,Michael Franzke,Reaction of cyclic carbonates with amines:Linear telechelic oligomers[J],Polymer Bulletin,1993,30(2):155-162
[89]Nobuhiro Kihara,Takeshi Endo,Synthesis and Properties of Poly(hydroxyurethane) s[J],Journal of Polymer Science:Part A:Polymer Chemistry,1993,31(11):2765-2773
[90]Akane Suzuki,Daisuke Nagai,Bungo Ochiai,et.al,Facile Synthesis and Crosslinking Reaction of Trifunctional Five-Membered Cyclic Carbonate and Dithiocarbonate[J],Journal of Polymer Science:Part A:Polymer Chemistry,2004,42(23):5983-5989
[91]Hidetoshi Tomita,Fumio Sanda,Takeshi Endo,Structural Analysis of Polyhydroxyurethane Obtained by Polyaddition of Bifunctional Five-Membered Cyclic Carbonate and Diamine Based on the Model Reaction[J],Journal of Polymer Science:Part A:Polymer Chemistry,2001,39(6):851-859
[92]Hidetoshi Tomita,Fumio Sanda,Takeshi Endo,Model Reaction for the Synthesis of Polyhydroxyurethanes from Cyclic Carbonates with Amines:Subsistent Effect on the Reactivity and Selectivity of Ring-Opening Direction in the Reaction of Five-Membered Cyclic Carbonates with Amine[J],Journal of Polymer Science:Part A:Polymer Chemistry,2001,39(6):3678-3685
[93]Bungo Ochiai,Shoko Inoue,Akeshi Endo,Salt Effect on Polyaddition of Bifunctional Cyclic Carbonate and Diamine[J],Journal of Polymer Science:Part A:Polymer Chemistry,2005,43(24):6282-6286
[94]Hidetoshi Tomita,Fumio Sanda,Takeshi Endo,Polyaddition Behavior of bis(Five-and Six-Membered Cyclic Carbonate)s with Diamine[J],Journal of Polymer Science:Part A:Polymer Chemistry,2001,39(6):860-867
[95]Hidetoshi Tomita,Fumio Sanda,Takeshi Endo,Polyaddition of Bis(seven-membered cyclic carbonate) with Diamines:A Novel and Efficient Synthetic Method for Polyhydroxyurethanes[J],Journal of Polymer Science:Part A:Polymer Chemistry,2001,39(23):4091-4100
[96]Hidetoshi Tomita,Fumio Sanda,Takeshi Endo,Polyaddition of Bis(cyclic thiocarbonate) with Diamines:Novel Efficient Synthetic Method of Polyhydroxythiourethanes[J],Macromolecules,2001,34:727-733
[97]Zhenrong Li,Yuhua Zhao,Shirun Yan,et,al.Catalytic Synthesis of Carbonated Soybean Oil[J],Catal Lett.,2008,123(3):246-251
[98]Tamami B,Sohn S,Wilkes GL.Incorporation of carbon dioxide into soybean oil and subsequent preparation and studies of nonisocyanate polyurethane networks[J],J Appl Polym Sci.,2004,92(2):883-889
[99]Wilkes GL,Sohn S,Tamami B,Nonisocyanate polyurethane materials,and their preparation from epoxidized soybean oils and related epoxidized vegetable oils,incorporation of carbon dioxide into soybean oil,and carbonation of vegetable oils[P],US.Patent,US7045577,2006
[100]Doll KM,Erhan SZ,The improved synthesis of carbonated soybean oil using supercritical carbon dioxide at a reduced reaction time[J],Green Chemistry,2005,7:849
[101]Arzuchowski PG,Kowalska MJ,Ryszkowska J,Rokicki G,Epoxy resin modified with soybean oil containing cyclic carbonate groups[J],J Appl Polym Sci.,2006,102(4):2904-2910
[102]Ivan Javni,Doo Pyo Hong,Zoran S.Petrovic,Soy-Based Polyurethanes by Nonisocyanate Route,Journal of Applied Polymer Science[J],2008,108(6):3867-3875
[103]Pawel G Parzuchowski,Magdalena Jurczyk-Kowalska,et.al,Epoxy Resin Modified with Soybean Oil Containing Cyclic Carbonate Groups[J],Journal of Applied Polymer Science,2006,102(4):2904-2914
[104]郭祥峰,贾丽华,阳离子表面活性剂及应用[M],北京:化学工业出版社,2002:159
[105]Kawabata N,Capture of micro-organisms and viruses by pyridinium-type polymers and application to biotechnology and water purification[J],Progress in polymer science,1992,17:1-34
[106]Sarkar J S,Cosper D R.,Application of enzymes and flocculants for enhancing the freeness of paper making pu!p[P],US.Patent,US5169497,1992
[107]Richardson P F.,Ellyn G,Bhupati R.,et.al,Acrylamide diallyl dimethyl ammonium chloride copolymers as improved dewatering acids for mineral processing[P],US.Patent,US 4673511,1987.
[108]Mcneely Gerald Willard,Fibres,yarns,textile materials,foils and similar products with improved properties[P],EP0120316,1984.
[109]李蔚,季铵盐型阳离子抗静电剂的概况及发展趋势[J],国际纺织导报,2007,11:68-71
[110]Kuran W.,Coordination polymerization of heterocyclic and heterounsaturated monomers[J],Progress in Polymer Science,1998,23:919-992
[111]Kuyper J.Boxhoorn,Hexacyanometallate salts used as alkene-oxide polymerization catalysts and molecular sieves[J],Journal of Catalysis,1987,105(1):163-174
[112]高和军,段明,胡星琪,许桂利,等,一种新型阳离子型高分子絮凝剂的合成[J],广州化工,2007,35(1):31-34
[113]甄丽丽,邵常东,张剑,等,阳离子聚合物杀菌剂的合成研究[J],精细石油化工进展2001,2(12):18-20
[114]谢瑜,张昌辉,徐旋,聚合季铵盐阳离子表面活性剂的合成和性能研究[J],日用化学品科学,2008,31(2):21-24
[115]王瑛,孙立伟,王萍,等,新型聚季铵盐的合成、表征及其性能测试[J],应用化工,2008,37(2):149-152
[116]Terayama H.,Method of colloid titration(a new titration between polymer ions)[J],J.Polym Sci.,1952,8(2):243-253
[117]侯斯健,哈润华,二烯丙基二甲基氯化铵—丙烯酰胺反相乳液聚合的动力学特征研究[J],高分子学报,1995,3(5):349-354
[118]王正辉,胡星琪,三甲基烯丙基氯化铵—丙烯酰胺共聚物的合成与结构表征[J],高分子材料科学与工程,1995,11(1):24-28
[119]吴立传,余爱芳,张敏,等,调节剂存在下双金属氰化络合催化剂催化环氧丙烷聚合的动力学[J],高分子学报,2004,1(1):98-102
[120]刘立峰,姜志国,周亨近,等,新型端氨基聚醚的合成[J],北京化工大学学报,2005,32(1):103-105
[121]Michael Cuscurida,et al,Polyamines by amination of polyamino initiated polyoxyalkylene glycols[P].U.S.Patent4992590,1991
[122]Oleg L.Figovsky,et al,Nonisocyanate Polyurethane:Synthesis,Nano-structuring and Application[C].International Scientific and Technical Conference Polymer 2005
[123]Constantinos D.Diakoumakos,Dimiter L,Kotzev.Non-isocyanate-Basd Polyuerthanes Deriverd upon the Reaction of Amines with Cyclocarbonate Resins[J],Macromolecular Symposia,2004,216(1):37-46
[124]颜吉校,端伯氨基氧化丙烯聚醚的合成与应用进展[J].浙江化工工业,2007,38(1):12-14
[125]郁维铭,端氨基聚醚的合成方法及其应用[J],聚氨酯工业,2002,17(1):1-5
[126]郑嘉杰,宁健,王晓,等,聚醚酯多元醇及其制备方法[P].CN101024684,2007
[127]Adkins,Rick L.,Polyether polyols containing pendant amine groups and a process for their preparation[P].EP1600468,2005
[128]孙曼灵,郑高锋,胺类环氧同化剂胺值测定方法的探讨[J],热固性树脂,2006,21(2):30-35
[129]叶美君,聚酰胺树脂中胺值的测定[J],绝缘材料通讯,1996,4:31-33
[130]殷宁,亢茂青,冯月兰,等,聚醚-酯嵌段共聚物改性微孔聚氨酯弹性体性能的研究,弹性体[J],2003,16(3):17-22
[2]朱吕民,刘益军,等,聚氨酯泡沫塑料[M],第三版,北京:化学工业出版社.2005,133
[3]Angelar Austin,Global overview of the PU industry:Prospects and possibilities,UTECH EUPOPE 2006 Conference[C],Maastricht Netherlands,2006,28-30
[4]朱树新,开环聚合[M],北京:化学工业出版社.1987,48-57
[5]Jedlinski Z.,Zabski L.,Dobrzynski P.,Manufacture of Hydroxyl-Terminated Halogen Containing Oligomeric Polythers[P],PL 150506,1991
[6]Stewrt M.J.,Catalysts for Proliferation of Cyclic Ethers[P],WO9015092,1990
[7]黄家贤,丁伦汉,朱端慧,等,聚环氧氯丙烷的合成与表征[J],高等学校化学学报,1991,12(6):843-846
[8]张阿方,张鸿志,杨惠昌,等,三氟化硼引发四氢吠喃开环聚合反应机理[J],科学通报,1990.2:112-115
[9]郭焕萍,PU弹性体用环氧丙烷-四氢吠喃共聚醚二醇的生产[J],弹性体,1998,8(4):27-30
[10]JACK MILGROM,Method of making a polyether using a double metal cyanide complex compound[P],US patent,US3278457,1966
[11]B.Le-Khac,Highly active double metal cyanide catalysts[P],US patent,US5693584,1998
[12]HR Hinney,DS Wardius,Process for preparing metal cyanide complex catalyst[P],US patent,US5158922,1992
[13]JW Reisch,MM Martinez,M Raes,Process for purifying and end-capping polyols made using double metal cyanide catalysts,US patent,US5144093,1992
[14]G Combs,HR Hinney,PT Bowman,Process for rapid activation of double metal cyanide catalysts,US patent,US5783513,1998
[15]P Ooms,J Hofmann,C Steinlein,S Ehlers,Double metal cyanide catalysts for producing polyether polyols,US Patent,US6919293,2005.
[16]黄亦军,双金属氰化物络合物催化环氧烷烃开环聚合的研究[D],浙江,浙江大学,2002:102-105
[17]Oleg L.Figovsky,Leonid D.Shapovalov,Features of Reaction Amino-cyclocarboante for Production of New Type Nonisocyanate Polyurethane Coating[J],Macromol.Symp.,2002,187:325-332
[18]G Rokick,Aliphatic cyclic carbonates and spiroorthocarbonates as monomers[J],Prog.Polym Sci.,2000,25:259-342
[19]Bungo Ochiai,Yuriko Satoh,Takeshi Endo,Nucleophilic polyaddition in water based on chemo-selective reaction of cyclic carbonate with amine[J],Green Chemistry,2005,7:765-767
[20]张锁江,孙剑,成卫国,含水体系环碳酸酯的合成方法,CN101108843,2008
[21]H.S.Kim,J.J.Kim,H.Kim,et.al,Imidazolium zinc tetrahalide-catalyzed coupling reaction of CO_2 and ethylene oxide or propylene oxide[J],Journal of Catalysis,2003,220(1):44-46
[22]X.Lu,X.Feng,R.He,Catalytic formation of ethylene carbonates from supercritical carbon dioxide/ethylene oxide mixture with tetradentate Schiff-base complexes as catalyst [J],Applied Catalysis A,General.,2002,234(1-2):25-33
[23]M.Yoshida,M.Ihara,A Novel Methodology for the Synthesis of Cyclic Carbonates Based on the Palladium-Catalyzed Cascade Reaction of 4-Methoxycarbonyloxy-2-butyn-l-ols with Phenols,Involving a Novel Carbon Dioxide Elimination-Fixation Process[J],J.Am.Chem.Soc,2003,125(16):4874-4881
[24]Robert L.,Paddock,SonBinh T.Nguyen,Chiral(salen)Co~(Ⅲ) catalyst for the synthesis of cyclic carbonates[J],Chem.Commun.,2004,1622-1623
[25]N.Kihara,N.Hara,T.Endo,Catalytic activity of various salts in the reaction of 2,3-epoxypropyl phenyl ether and carbon dioxide[J],J.Org.Chem.,1993,58(23):6198-6202
[26]R.L.Addock,S.T.Nguyen,Chemical CO_2 Fixation:Cr~((Ⅲ)) Salen Complexes as Highly Efficient Catalysts for the Coupling of CO_2 and Epoxides[J],J.Am.Chem.Soc,2001,123(46):11498-11499
[27]Y.M.Shen,W.L.Duan,M.Shi,Chemical fixation of carbon dioxide catalyzed by Binaphthyldiamino Zn,Cu,and Co salen-type complexes[J],Chemlnform,2003,34(26):132-135
[28]H.S.Kim,J.J.Kim,B.G.Lee,O.S.Jung,et,al.,Well-Defined Highly Active Heterogeneous Catalyst System for the Coupling Reactions of Carbon Dioxide and Epoxides[J],Journal of Catalysis,2002,39:4096.
[29]D.Walther,M.Ruben,S.Rau,Carbon dioxide and metal centres:from reactions inspired by nature to reactions in compressed carbon dioxide as solvent[J],Coordination Chemistry Reviews,1999,182(1):67-100
[30]X.Lu,R.He,C.X.Bai,Synthesis of ethylene carbonate from supercritical carbon dioxide/ethylene oxide mixture in the presence of bifunctional catalyst[J],Journal of Molecular Catalysis.A,Chemical,2002,186(1-2):1 -11
[31]R.Srivastava,T.H.Bennur,D.Srinivas,Factors affecting activation and utilization of carbon dioxide in cyclic carbonates synthesis over Cu and Mn peraza macrocyclic complexes[J],Journal of Molecular Catalysis.A,Chemical,2005,226(2):199-205
[32]X..B.Lu,B.Liang,Y.J.Zhang,Y.Z.Tian,et.al,Zuschrift-Highly Active,Binary Catalyst Systems for the Alternating Copolymerization of CO_2 and Epoxides under Mild Conditions[J],Angew Chem Int Ed Engl.,2004,43(27):3574-3577.
[33]Keiichi Tomishige,Hiroaki Yasuda,Yuichi Yoshida,et.al.,Catalytic performance and properties of ceria based catalysts for cyclic carbonate synthesis from glycol and carbon dioxide[J],Green.Chem.2004,6:206-214
[34]G.Rokicki,W.Kuran,Cyclic Carbonates Obtained by Reactions of Alkali Metal Carbonates with Epihalohydrins[J],Bull.Chem.Soc.Jpn.,1984,57(6):1662-1666
[35]Gabriel Rokickil,Witold Kuran,Barbara Pogorzelska-Marciniak,Cyclic carbonates from carbon dioxide and oxiranes[J],Monatshefte fur Chemie,1984,115(2):205-214
[36]Gabriel Rokicki,Witold Kuran,Cyclic Carbonates Obtained by Reactions of Alkali Metal Carbonates with Epihalohydrins[J],Bulletin of the Chemical Society of Japan,1984,57(6):1662-1666
[37]Ratzenhofer,M.,Kisch,H.Angew.,Metal-Catalyzed Synthesis of Cyclic Carbonates from Carbon Dioxide and Oxiranes[J],Angewandte Chemie International Edition in English,1980,19(4):317-318
[38]Akio Baba,Takashi Nozaki Haruo Matsuda,Carbonate Formation from Oxiranes and Carbon Dioxide Catalyzed by Organotin Halide-Tetraalkylphosphonium Halide Complexes[J],Bulletin of the Chemical Society of Japan,1987,60(4):1552-1554
[39]Xiao-Bing Lu,Ying-Ju Zhang,Bin Liang,et.al,Chemical fixation of carbon dioxide to cyclic carbonates under extremely mild conditions with highly active bifunctional catalysts[J],Journal of Molecular Catalysis A:Chemical,2004,210(1-2):31-34
[40]X.Lu,J.Xiu,R.He,K.Jin,et.al,Chemical fixation of CO_2 to ethylene carbonate under supercritical conditions:continuous and selective[J],Applied Catalysis A,General,2004,275(1-2):73-78
[41]Y.Du,F.Cai,D.L.Kong,et.al,Organic solvent-free process for the synthesis of propylene carbonate from supercritical carbon dioxide and propylene oxide catalyzed by insoluble ion exchange resins[J],Green Chem.,2005,7:518-523
[42]H.Yasuda,L.N.He,T.Takahashi,T.Sakakura,Non-halogen catalysts for propylene carbonate synthesis from CO_2 under supercritical conditions[J],Applied Catalysis A,General,2006,298(10):177-180
[43]H.Yasuda,L.N.Hen,T.Sakakura,Cyclic Carbonate Synthesis from Supercritical Carbon Dioxide and Epoxide over Lanthanide Oxychloride[J],Journal of Catalysis,2002,209(2):547-550
[44]Jin-Quan Wang,Xiao-Dong,et.al,Solventless Synthesis of Cyclic Carbonates from Carbon Dioxide and Epoxides Catalyzed by Silica-Supported Ionic Liquids under Supercritical Conditions[J],Catalysis Communications,2007,8(2):167-172
[45]T.Nishikubo,A.Kameyama,J.Yamashita,etal,Insoluble Polystyrene-Bound Quaternary Onium Salt Catalysts for the Synthesis of Cyclic Carbonate by the Reaction of Oxiranes with Carbon Dioxide[J],Journal of polymer science,1993,31(4):939-947
[46]John H.Clements,Reactive Applications of Cyclic Alkylene Carbonates[J],Industrial and Engineering Chemistry Research,2003,42:663-674
[47]Blank N,Figovsky O.,Nonisocyanate polyurethane glues for jointing reinforced plastics,Proceedings of International Adhesion Symposium[C],Tokyo,Japan,1994.p.87
[48]Figovsky oleg,Shapovalov leonid,Blank nelly,et,al.,Cyclocarbonate Groups Containing Hydroxyamine Oligomers From Epoxycyclocarbonates[P],WO0042033,2004
[49]Figovsky Oleg,Shapovalov Leonid,Preparation of Oligomeric Cyclocarbonates And Their Use In Ionisocyanate Or Hybrid Nonisocyanate Polyurethanes[P],WO03028644,2003
[50]Burk R.M.,ROOF M.B.,A safe and efficient method for conversion of 1,2-and 1,3-diols to cyclic carbonates utilizing triphosgene[J],Tetrahedron Lett.,1993,34(3):395-398
[51]Okutsu,Munenao,Kitsuki,Tomohito.Preparation of cyclic carbonate esters from I,2-diols and carbonated esters[P],JP2004168674,2004
[52]Fukumura,Takanori,Hayashi,Hidetoshi,Nontoxic preparation of alicyclic carbonates from alicyclic diols and difluorodiamines[P],JP 2004315445,2004
[53]C.Venturello,R.,D'aloisio.ACOnvenient Synthesis of 1,2-Alkanediyl Carbonates[J],Synthesis,1985,1:33-34
[54]James A.Kenar,Ian D.Tevis.Convenient Preparation of fatty ester cyclic carbonate[J],European Journal of Lipid Science and Technology,2005,107(2):135-137
[55]Carlson WW,Cretcher LH,Hydroxyalkylation with Cyclic Alkylene Esters:Synthesis of Hydroxyethylapocupreine[J],J Am Chem Soc.1947,69(8):1952-1956
[56]Yoshino T,Inaba S,Ishido Y.Synthetic Studies by the Use of Carbonates:The Condensation Reactions of Ethylene Carbonate with a Variety of Phenols Catalyzed by Lithium Hydride or Tetraethylammonium Halides[J],Bull Chem Soc Jpn.1973,46(2):553-556
[57]Rokicki G,Pawlicki J,Kuran W.,Poly(ether-carbonate)s from Diphenolates,Cyclic Carbonates,and Dihalo Compounds[J],Polymer Journal,1985,13(3):509-516
[58]Rokicki G.,cyclic dicarbonates as new monomers for the synthesis of poly(hydroxy ether) s[J],Die Makromolekulare Chemie,1985;186(2):331-337
[59]Baizer MM,Clark JR,Smith E.,Monocarbamates of 1,2-Dihydroxy-3-aryloxypropanes[J],J Org Chem.,1957,22(12):1596-1599
[60]El-Giamal MF,Schulz RC,Ober einige Copolyurethane ausgehend von Piperazin[J],Colloid & Polymer Science,1978,256(3):1435-1536.
[61]Burgel T,Fedtke M.,Reactions of cyclic carbonates with amines:Model studies for curing process[J],Polym Bull.,1991,27(2):171-177
[62]Burgel T,Fedtke M.,Epoxy resins with cyclic carbonate structures[J],Polym Bull.,1993,30(1):61-68
[63]Kihara N,Kushida Y,Endo T.,Optically active poly(hydroxyurethane)s derived from cyclic carbonate and L-lysine derivatives[J],Polym Sci Part A:Polym Chem 1996;34(11):2173-2179
[64]Rokicki G,Lewandowski M.,Epoxy resins modified by carbon dioxide[J],Angew Makromol Chem 1987;148(1):53-66
[65]Rokicki G,Wojciechowski C,Epoxy resins modified by carbon dioxide[J],J Appl Polym Sci 1990,41(3-4):647-659
[66]Rokicki G.,Synthesis of poly(hydroxyurethanes) from diepoxides,carbon dioxide,and diamines[J],Polimery,1989,34(4):304-147
[67]Rokicki G,Lazinski R.,Polyamines containing P-hydroxyurethane linkages as curing agents for epoxy resin[J],Die Angewandte Makromolekulare Chemie,1989,170(1):211-225.
[68]Schwenk E,Synthesis of Polyesters from Dicarboxylic Acid Anhydrides and Epoxides or Cyclic Carbonates of Diols[J],Makromol Chem.,1962,51:53-57
[69]Tarbell DS.,Carboxylic carbonic anhydrides and related compounds[J],Acc Chem Res.,1969,2(10):296-300
[70]Kenneth R.Carter,Richard A.DiPietro,Martha 1.Sanchez,et.al,Polyimide Nanofoams Based on Ordered Polyimides Derived from Poly(amic alkyl esters):PMDA/4-BDAF[J],Chem.Mater.,1997,9(1):105-118.
[71]Vogdanis L,Martens B,Uchtmann H,et,al.,Synthetic and thermodynamic investigations in the polymerization of ethylene carbonate[J],Die Makromolekulare Chemie,1990,191(3):465-472
[72]Soga K,Hosoda S,Tazuke Y,et.al,Polymerization of propylene carbonate[J],Polym Sci Part A:Polym Chem.,1977,15(1):219-229
[73]Vogdanis L,Heitz W.,Carbon dioxide as a monomer and the polymerization of ethylene carbonate[J],Makromol Chem,Rapid Commun 1986,7:543-547
[74]Kuran W.,Listos T.,Copolymerization of epoxides and five-membered cyclic carbonates in the presence of zinc coordination catalysts[J],Makromol Chem 1992,193(4):945-956
[75]Penco M.,Donetti R.,Mendichi R.,et,al.,New poly(ester-carbonate) multi-block copolymers based on poly(lactic-glycolic acid) and poly(ε-caprolactone) s egments[J],Macromol Chem Phys.,1998,199(8):1737-1745
[76]Harris RF.,Molecular weight advancement of poly(ethylene ether carbonate) polyols[J],J Appl Polym Sci.,1989,38(3):463-476
[77]Harris RF,McDonald LA.,Structural features of poly(alkylene ether carbonate) diols and intermediates formed during their preparation[J],Appl Polym Sci 1989,37(6):1491-1511
[78]C D Diakoumakos,D L Kotzev.Non-Isocyanate-Based Polyurethanes Derived upon the Reaction of Amines with Cyclocarbonate Resins[J],Macromol.Symp.2004,216(1):37-46.
[79]O L Figovsky,Hybrid nonisocyanate polyurethane network polymers and composites formed therefrom[P],USPatent,US6120905,2000.
[80]Pathiraja A.Gunatillake,Gordon F.Meijs,Simon J.,et.al,Synthesis and characterization of a series of poly(alkylene carbonate) macrodiols and the effect of their structure on the properties of polyurethanes[J],Journal of Applied Polymer Science,1998,69(8):1621-1633
[81]Garipov,Sysoev,Mikheev et.al,Reactivity of Cyclocarbonate Groups in Modified Epoxy-Amine Compositions[J],Doklady Akademii Nauk,2003,393(1):61-64
[82]Dean C.Webster,Allen L.Crain,Synthesis and applications of cyclic carbonate functional polymers in thermosetting coatings[J],Progress in Organic Coatings,2000,40(1):275-282
[83]Shuichi Matsumura,Yasuyuki Soeda,Kazunobu Toshima,Perspectives for synthesis and production of polyurethanes and related polymers by enzymes directed toward green and sustainable chemistry[J],Appl Microbiol Biotechnol.,2006,70(1):12-20
[84]Robson F.Storey,Douglas C.Hoffman,Formation of Poly(ethylene ether carbonate) Diols:Proposed Mechanism and Kinetic Analysis[J],Macromolecules 1992,25:5369-5382
[85]Oguz Turunc,Nilhan Kayaman-Apohan.M.,Vezir Kahraman,et.al,Nonisocyanate based polyurethane/silica nanocomposites and their coating performance[J],J Sol-Gel Sci Technol.,2008,47:290-299
[86]I.V.Stroganov,V.F.Strogano.Peculiarities of Structurization and Properties of Nonisocyanate Epoxyurethane Polymers[J],Polymer Science,Ser.C,2007,49(3):258-263.
[87]Thomas Burgel,Manfred Fedtke,Reactions of cyclic carbonates with amines:Model studies for curing process[J],Polymer Bulletin,1991,27(2):171-177
[88]Thomas B.Lirgel,Manfred Fedtke,Michael Franzke,Reaction of cyclic carbonates with amines:Linear telechelic oligomers[J],Polymer Bulletin,1993,30(2):155-162
[89]Nobuhiro Kihara,Takeshi Endo,Synthesis and Properties of Poly(hydroxyurethane) s[J],Journal of Polymer Science:Part A:Polymer Chemistry,1993,31(11):2765-2773
[90]Akane Suzuki,Daisuke Nagai,Bungo Ochiai,et.al,Facile Synthesis and Crosslinking Reaction of Trifunctional Five-Membered Cyclic Carbonate and Dithiocarbonate[J],Journal of Polymer Science:Part A:Polymer Chemistry,2004,42(23):5983-5989
[91]Hidetoshi Tomita,Fumio Sanda,Takeshi Endo,Structural Analysis of Polyhydroxyurethane Obtained by Polyaddition of Bifunctional Five-Membered Cyclic Carbonate and Diamine Based on the Model Reaction[J],Journal of Polymer Science:Part A:Polymer Chemistry,2001,39(6):851-859
[92]Hidetoshi Tomita,Fumio Sanda,Takeshi Endo,Model Reaction for the Synthesis of Polyhydroxyurethanes from Cyclic Carbonates with Amines:Subsistent Effect on the Reactivity and Selectivity of Ring-Opening Direction in the Reaction of Five-Membered Cyclic Carbonates with Amine[J],Journal of Polymer Science:Part A:Polymer Chemistry,2001,39(6):3678-3685
[93]Bungo Ochiai,Shoko Inoue,Akeshi Endo,Salt Effect on Polyaddition of Bifunctional Cyclic Carbonate and Diamine[J],Journal of Polymer Science:Part A:Polymer Chemistry,2005,43(24):6282-6286
[94]Hidetoshi Tomita,Fumio Sanda,Takeshi Endo,Polyaddition Behavior of bis(Five-and Six-Membered Cyclic Carbonate)s with Diamine[J],Journal of Polymer Science:Part A:Polymer Chemistry,2001,39(6):860-867
[95]Hidetoshi Tomita,Fumio Sanda,Takeshi Endo,Polyaddition of Bis(seven-membered cyclic carbonate) with Diamines:A Novel and Efficient Synthetic Method for Polyhydroxyurethanes[J],Journal of Polymer Science:Part A:Polymer Chemistry,2001,39(23):4091-4100
[96]Hidetoshi Tomita,Fumio Sanda,Takeshi Endo,Polyaddition of Bis(cyclic thiocarbonate) with Diamines:Novel Efficient Synthetic Method of Polyhydroxythiourethanes[J],Macromolecules,2001,34:727-733
[97]Zhenrong Li,Yuhua Zhao,Shirun Yan,et,al.Catalytic Synthesis of Carbonated Soybean Oil[J],Catal Lett.,2008,123(3):246-251
[98]Tamami B,Sohn S,Wilkes GL.Incorporation of carbon dioxide into soybean oil and subsequent preparation and studies of nonisocyanate polyurethane networks[J],J Appl Polym Sci.,2004,92(2):883-889
[99]Wilkes GL,Sohn S,Tamami B,Nonisocyanate polyurethane materials,and their preparation from epoxidized soybean oils and related epoxidized vegetable oils,incorporation of carbon dioxide into soybean oil,and carbonation of vegetable oils[P],US.Patent,US7045577,2006
[100]Doll KM,Erhan SZ,The improved synthesis of carbonated soybean oil using supercritical carbon dioxide at a reduced reaction time[J],Green Chemistry,2005,7:849
[101]Arzuchowski PG,Kowalska MJ,Ryszkowska J,Rokicki G,Epoxy resin modified with soybean oil containing cyclic carbonate groups[J],J Appl Polym Sci.,2006,102(4):2904-2910
[102]Ivan Javni,Doo Pyo Hong,Zoran S.Petrovic,Soy-Based Polyurethanes by Nonisocyanate Route,Journal of Applied Polymer Science[J],2008,108(6):3867-3875
[103]Pawel G Parzuchowski,Magdalena Jurczyk-Kowalska,et.al,Epoxy Resin Modified with Soybean Oil Containing Cyclic Carbonate Groups[J],Journal of Applied Polymer Science,2006,102(4):2904-2914
[104]郭祥峰,贾丽华,阳离子表面活性剂及应用[M],北京:化学工业出版社,2002:159
[105]Kawabata N,Capture of micro-organisms and viruses by pyridinium-type polymers and application to biotechnology and water purification[J],Progress in polymer science,1992,17:1-34
[106]Sarkar J S,Cosper D R.,Application of enzymes and flocculants for enhancing the freeness of paper making pu!p[P],US.Patent,US5169497,1992
[107]Richardson P F.,Ellyn G,Bhupati R.,et.al,Acrylamide diallyl dimethyl ammonium chloride copolymers as improved dewatering acids for mineral processing[P],US.Patent,US 4673511,1987.
[108]Mcneely Gerald Willard,Fibres,yarns,textile materials,foils and similar products with improved properties[P],EP0120316,1984.
[109]李蔚,季铵盐型阳离子抗静电剂的概况及发展趋势[J],国际纺织导报,2007,11:68-71
[110]Kuran W.,Coordination polymerization of heterocyclic and heterounsaturated monomers[J],Progress in Polymer Science,1998,23:919-992
[111]Kuyper J.Boxhoorn,Hexacyanometallate salts used as alkene-oxide polymerization catalysts and molecular sieves[J],Journal of Catalysis,1987,105(1):163-174
[112]高和军,段明,胡星琪,许桂利,等,一种新型阳离子型高分子絮凝剂的合成[J],广州化工,2007,35(1):31-34
[113]甄丽丽,邵常东,张剑,等,阳离子聚合物杀菌剂的合成研究[J],精细石油化工进展2001,2(12):18-20
[114]谢瑜,张昌辉,徐旋,聚合季铵盐阳离子表面活性剂的合成和性能研究[J],日用化学品科学,2008,31(2):21-24
[115]王瑛,孙立伟,王萍,等,新型聚季铵盐的合成、表征及其性能测试[J],应用化工,2008,37(2):149-152
[116]Terayama H.,Method of colloid titration(a new titration between polymer ions)[J],J.Polym Sci.,1952,8(2):243-253
[117]侯斯健,哈润华,二烯丙基二甲基氯化铵—丙烯酰胺反相乳液聚合的动力学特征研究[J],高分子学报,1995,3(5):349-354
[118]王正辉,胡星琪,三甲基烯丙基氯化铵—丙烯酰胺共聚物的合成与结构表征[J],高分子材料科学与工程,1995,11(1):24-28
[119]吴立传,余爱芳,张敏,等,调节剂存在下双金属氰化络合催化剂催化环氧丙烷聚合的动力学[J],高分子学报,2004,1(1):98-102
[120]刘立峰,姜志国,周亨近,等,新型端氨基聚醚的合成[J],北京化工大学学报,2005,32(1):103-105
[121]Michael Cuscurida,et al,Polyamines by amination of polyamino initiated polyoxyalkylene glycols[P].U.S.Patent4992590,1991
[122]Oleg L.Figovsky,et al,Nonisocyanate Polyurethane:Synthesis,Nano-structuring and Application[C].International Scientific and Technical Conference Polymer 2005
[123]Constantinos D.Diakoumakos,Dimiter L,Kotzev.Non-isocyanate-Basd Polyuerthanes Deriverd upon the Reaction of Amines with Cyclocarbonate Resins[J],Macromolecular Symposia,2004,216(1):37-46
[124]颜吉校,端伯氨基氧化丙烯聚醚的合成与应用进展[J].浙江化工工业,2007,38(1):12-14
[125]郁维铭,端氨基聚醚的合成方法及其应用[J],聚氨酯工业,2002,17(1):1-5
[126]郑嘉杰,宁健,王晓,等,聚醚酯多元醇及其制备方法[P].CN101024684,2007
[127]Adkins,Rick L.,Polyether polyols containing pendant amine groups and a process for their preparation[P].EP1600468,2005
[128]孙曼灵,郑高锋,胺类环氧同化剂胺值测定方法的探讨[J],热固性树脂,2006,21(2):30-35
[129]叶美君,聚酰胺树脂中胺值的测定[J],绝缘材料通讯,1996,4:31-33
[130]殷宁,亢茂青,冯月兰,等,聚醚-酯嵌段共聚物改性微孔聚氨酯弹性体性能的研究,弹性体[J],2003,16(3):17-22