超支化表面活性剂的合成及性能评价
|
摘要
以二乙醇胺与顺丁烯二酸酐为原料合成了超支化不饱和聚(酰胺-酯)(HP)。通过琥珀酸单十二酰胺磺酸与HP端羟基的酯化反应得到阴-非离子型超支化表面活性剂(HPSA),用FTIR、~1HNMR和GPC对其结构进行了表征,并对HPSA的临界胶束浓度、表/界面张力、润湿性能、高温高盐下抗老化性能、乳化性能及驱油能力进行了测定。结果表明:HPSA具有较低的临界胶束质量浓度(0.162 g/L)、较好的表/界面活性(γ_(CMC)=25.1 mN/m,δ_(CMC)=0.077 mN/m)及抗老化性能[ρ(NaCl)=2×10~(5 )mg/L,150℃时,老化15 d表面张力约为25 mN/m]。润湿性能结果表明:HPSA具有较好的润湿性能以及润湿反转性能。乳化性能结果说明:HPSA乳化性能与十二烷基磺酸钠相当,但其乳化抗盐能力[ρ(Na Cl)=8×10~(4 )mg/L,ρ(CaCl_2)=1×10~(4 )mg/L]较十二烷基磺酸钠优异。填砂管驱油实验结果表明:注入体积为0.5PV时,0.3 g/L的HPSA可在水驱基础上提高采收率约5.3%。HPSA可以作为高温高盐油田驱油剂使用。
Diethanolamine and maleic anhydride were used to synthesize hyperbranched unsaturated poly(amide-ester)(HP).Then,HP reacted with succinic acid monolauramide sulfonic acid to prepare anionic-nonionic hyperbranched surfactant HPSA.The structure of HPSA was characterized by FTIR~1HNMR and GPC.The critical micelle concentration(CMC),surface/interfacial tension(SFT/IFT),wetting properties,anti-aging properties under high temperature and high salt,emulsifying property and oil displacement efficiency of HPSA were measured.The results showed that HPSA had a CMC of 0.162 g/L good surface/interfacial activity(γ_(CMC)=25.1 mN/m,δ_(CMC)=0.077 mN/m).Under high temperature(150℃)and high salt[ρ(NaCl)=2×10~5mg/L],the surface tension was about 25 mN/m after aging 15 days.Besides HPSA showed good wetting properties and wetting reversal properties.Moreover,the emulsification performance of HPSA was comparable with sodium dodecyl sulfonate,but its emulsification performance under high salt(ρ(NaCl)=8×10~(4 )mg/L,ρ(Ca Cl_2)=1×10~(4 )mg/L)was better than that of sodium dodecyl sulfonate.The core flow test indicated that 0.3 g/LHPSA improved the enhance oil recovery(EOR)abou5.3%on the basis of water flooding when the injection volume was 0.5 PV.HPSA was suitable to high temperature and high salinity oil field as a new oil-displacing agent.
Diethanolamine and maleic anhydride were used to synthesize hyperbranched unsaturated poly(amide-ester)(HP).Then,HP reacted with succinic acid monolauramide sulfonic acid to prepare anionic-nonionic hyperbranched surfactant HPSA.The structure of HPSA was characterized by FTIR~1HNMR and GPC.The critical micelle concentration(CMC),surface/interfacial tension(SFT/IFT),wetting properties,anti-aging properties under high temperature and high salt,emulsifying property and oil displacement efficiency of HPSA were measured.The results showed that HPSA had a CMC of 0.162 g/L good surface/interfacial activity(γ_(CMC)=25.1 mN/m,δ_(CMC)=0.077 mN/m).Under high temperature(150℃)and high salt[ρ(NaCl)=2×10~5mg/L],the surface tension was about 25 mN/m after aging 15 days.Besides HPSA showed good wetting properties and wetting reversal properties.Moreover,the emulsification performance of HPSA was comparable with sodium dodecyl sulfonate,but its emulsification performance under high salt(ρ(NaCl)=8×10~(4 )mg/L,ρ(Ca Cl_2)=1×10~(4 )mg/L)was better than that of sodium dodecyl sulfonate.The core flow test indicated that 0.3 g/LHPSA improved the enhance oil recovery(EOR)abou5.3%on the basis of water flooding when the injection volume was 0.5 PV.HPSA was suitable to high temperature and high salinity oil field as a new oil-displacing agent.
引文
[1]Cheng H X,Wang S G,Yang J T,et al.Synthesis and self-assembly of amphiphilic hyperbranched polyglycerols modified with palmitoylchloride[J].Journal of Colloid&Interface Science 2009,337(1):278-284.
[2]Wang Xuechuan(王学川),Li Xinmiao(李新苗),Qiang Taotao(强涛涛).Synthesis and characterization of alkylarylsulfonate hyperbranched polymer surfactant[J].Textile Auxiliaries(印染助剂),2013,30(6):12-14.
[3]Patrizio R,Broekhuis A A,Picchioni F,et al.Polymeric surfactants for enhanced oil recovery:A review[J].Journal of Petroleum Science and Engineering,2016,145:723-733.
[4]Kou Y,Wan A,Tong S,et al.Preparation,characterization and modification of hyperbranched polyester-amide with core molecules[J].Reactive&Functional Polymers,2007,67(10):955-965.
[5]Elrehim M A,Said S,Ghoneim A,et al.Dielectric properties of hyperbranchedpolyesteramide with long alkyl chain end groups[J].Macromolecular Symposia,2007,254(1):1-8.
[6]Zhang Z,Xu G,Wang F,et al.Demulsification by amphiphilic dendrimer copolymers[J].Journal of Colloid&Interface Science,2005,282(1):1-4.
[7]Qiang T T,Bu Q Q,Huang Z F,et al.Synthesis and characterization of hyperbranched-linear surfactants[J].Journal of Surfactants and Detergents,2014,17(2):215-221.
[8]Kasza G,Gyulai G,Abraham A,et al.Amphiphilichyper branched polyglycerols in a newrole as highly efficient multifunctional surfaceactive stabilizers for poly(lactic/glycolic acid)nanoparticles[J].RSC Advances 2017,7(8)4348-4352.
[9]Ferreira C C,Teixeira G T,Lachtera E R,et al.Partially hydrophobizedhyper branched polyglycerols as non-ionicreactive shale inhibitors for water-based drilling fluids[J].Applied Clay Science,2016,132/133:122-132.
[10]Zheng Xingneng(郑性能),Ye Zhongbin(叶仲斌),Ye Zhengrong(叶正荣),et al.Synthesis of oil-displacing agent with dendritic molecules and its evaluation[J].Xinjiang Petroleum Geology(新疆石油地质),2009,30(5):637-640.
[11]Zheng Yancheng(郑延成),Han Dong(韩冬),Yang Puhua(杨普华),et al.Progress in the investigation of sulfonate surfactants[J].Fine Chemicals(精细化工),2005,22(8):578-582.
[12]Yan D,Gao C.Hyperbranched polymers made from A2 and BB’2typemonomers.1.Polyaddition of 1-(2-aminoethyl)piperazine to divinylsulfone[J].Macromolecules,2000:33:7693-7699.
[13]Ministry of Petroleum Industry of the People's Republic of China(中华人民共和国石油工业部).GB/T264-1983(1991):Petroleum productsdetermination of acid number(石油产品酸值测定方法)[S].Standards Press of China,1983.
[14]Li F(李凡).Synthesis and study on the self-assembly properties of surface active hydrophobically associating polymer[D].Jingzhou:Petroleum Engineering College Yangtze University,2017:25.
[15]Wang Yefei(王业飞),Zhao Fulin(赵福麟).The salt tolerance of nonionic-anionic surfactants[J].Oilfield Chemistry(油田化学),1999,16(4):336-340.
[16]Hodyson P K G,Stewart N J,Grant C E,et al.Alkylethoxyethane sulfonate:Two techniques for improving syntetic conversions[J].Journal of the American Oil Chemists’Society,1990,67(11):730-732.
[2]Wang Xuechuan(王学川),Li Xinmiao(李新苗),Qiang Taotao(强涛涛).Synthesis and characterization of alkylarylsulfonate hyperbranched polymer surfactant[J].Textile Auxiliaries(印染助剂),2013,30(6):12-14.
[3]Patrizio R,Broekhuis A A,Picchioni F,et al.Polymeric surfactants for enhanced oil recovery:A review[J].Journal of Petroleum Science and Engineering,2016,145:723-733.
[4]Kou Y,Wan A,Tong S,et al.Preparation,characterization and modification of hyperbranched polyester-amide with core molecules[J].Reactive&Functional Polymers,2007,67(10):955-965.
[5]Elrehim M A,Said S,Ghoneim A,et al.Dielectric properties of hyperbranchedpolyesteramide with long alkyl chain end groups[J].Macromolecular Symposia,2007,254(1):1-8.
[6]Zhang Z,Xu G,Wang F,et al.Demulsification by amphiphilic dendrimer copolymers[J].Journal of Colloid&Interface Science,2005,282(1):1-4.
[7]Qiang T T,Bu Q Q,Huang Z F,et al.Synthesis and characterization of hyperbranched-linear surfactants[J].Journal of Surfactants and Detergents,2014,17(2):215-221.
[8]Kasza G,Gyulai G,Abraham A,et al.Amphiphilichyper branched polyglycerols in a newrole as highly efficient multifunctional surfaceactive stabilizers for poly(lactic/glycolic acid)nanoparticles[J].RSC Advances 2017,7(8)4348-4352.
[9]Ferreira C C,Teixeira G T,Lachtera E R,et al.Partially hydrophobizedhyper branched polyglycerols as non-ionicreactive shale inhibitors for water-based drilling fluids[J].Applied Clay Science,2016,132/133:122-132.
[10]Zheng Xingneng(郑性能),Ye Zhongbin(叶仲斌),Ye Zhengrong(叶正荣),et al.Synthesis of oil-displacing agent with dendritic molecules and its evaluation[J].Xinjiang Petroleum Geology(新疆石油地质),2009,30(5):637-640.
[11]Zheng Yancheng(郑延成),Han Dong(韩冬),Yang Puhua(杨普华),et al.Progress in the investigation of sulfonate surfactants[J].Fine Chemicals(精细化工),2005,22(8):578-582.
[12]Yan D,Gao C.Hyperbranched polymers made from A2 and BB’2typemonomers.1.Polyaddition of 1-(2-aminoethyl)piperazine to divinylsulfone[J].Macromolecules,2000:33:7693-7699.
[13]Ministry of Petroleum Industry of the People's Republic of China(中华人民共和国石油工业部).GB/T264-1983(1991):Petroleum productsdetermination of acid number(石油产品酸值测定方法)[S].Standards Press of China,1983.
[14]Li F(李凡).Synthesis and study on the self-assembly properties of surface active hydrophobically associating polymer[D].Jingzhou:Petroleum Engineering College Yangtze University,2017:25.
[15]Wang Yefei(王业飞),Zhao Fulin(赵福麟).The salt tolerance of nonionic-anionic surfactants[J].Oilfield Chemistry(油田化学),1999,16(4):336-340.
[16]Hodyson P K G,Stewart N J,Grant C E,et al.Alkylethoxyethane sulfonate:Two techniques for improving syntetic conversions[J].Journal of the American Oil Chemists’Society,1990,67(11):730-732.