New Polymer Syntheses Part 60: A Facile Synthetic Route to Polyamides Based on Thieno[2,3-b]thiophene and Their Corrosion Inhibition Behavior
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摘要
Polyamides containing thieno[2,3-b]thiophene moiety were prepared via a simple polycondensation reaction of the diaminothieno[2,3-b]thiophene monomer 1 a with different kinds of diacid chlorides(including oxalyl, adipoyl, sebacoyl, isophthaloyl,terephthaloyl, 4,4′-azodibenzoyl, 3,3′-azodibenzoyl, p-phenylene diacryloyl) in the presence of Li Cl and NMP as a solvent through lowtemperature solution polycondensation. The chemical structures of model compound and synthesized polyamides were confirmed by FTIR, nuclear magnetic resonance spectroscopy(including ~1H-NMR and ~(13)C-NMR) and elemental analysis. In addition, the thermal stability, crystallinity structure and surface morphology of synthesized polyamides were characterized via thermogravametric analysis(TGA), wide-angle X-ray diffraction analysis(WAXD) and scanning electron microscopy(SEM). Also, the corrosion inhibition behavior of selected examples of polyamides was investigated; the inhibitive effect of the investigated polymers for carbon steel in 1.0 mol·L~(-1) HCl was studied using potentiodynamic polarization(PDP) and electrochemical impedance spectroscopy(EIS) methods. PDP results displayed that the polyamides containing thieno[2,3-b]thiophene moiety can be as mixed-type inhibitors. The inhibition efficiency(P, %) was found to be in the range from 67.13% to 96.01%. There is an increase in P by the synthesized polymers in comparison to the starting monomer.The adsorption of these polymers was found to obey Langmuir adsorption isotherm.
Polyamides containing thieno[2,3-b]thiophene moiety were prepared via a simple polycondensation reaction of the diaminothieno[2,3-b]thiophene monomer 1 a with different kinds of diacid chlorides(including oxalyl, adipoyl, sebacoyl, isophthaloyl,terephthaloyl, 4,4′-azodibenzoyl, 3,3′-azodibenzoyl, p-phenylene diacryloyl) in the presence of Li Cl and NMP as a solvent through lowtemperature solution polycondensation. The chemical structures of model compound and synthesized polyamides were confirmed by FTIR, nuclear magnetic resonance spectroscopy(including ~1H-NMR and ~(13)C-NMR) and elemental analysis. In addition, the thermal stability, crystallinity structure and surface morphology of synthesized polyamides were characterized via thermogravametric analysis(TGA), wide-angle X-ray diffraction analysis(WAXD) and scanning electron microscopy(SEM). Also, the corrosion inhibition behavior of selected examples of polyamides was investigated; the inhibitive effect of the investigated polymers for carbon steel in 1.0 mol·L~(-1) HCl was studied using potentiodynamic polarization(PDP) and electrochemical impedance spectroscopy(EIS) methods. PDP results displayed that the polyamides containing thieno[2,3-b]thiophene moiety can be as mixed-type inhibitors. The inhibition efficiency(P, %) was found to be in the range from 67.13% to 96.01%. There is an increase in P by the synthesized polymers in comparison to the starting monomer.The adsorption of these polymers was found to obey Langmuir adsorption isotherm.
Polyamides containing thieno[2,3-b]thiophene moiety were prepared via a simple polycondensation reaction of the diaminothieno[2,3-b]thiophene monomer 1 a with different kinds of diacid chlorides(including oxalyl, adipoyl, sebacoyl, isophthaloyl,terephthaloyl, 4,4′-azodibenzoyl, 3,3′-azodibenzoyl, p-phenylene diacryloyl) in the presence of Li Cl and NMP as a solvent through lowtemperature solution polycondensation. The chemical structures of model compound and synthesized polyamides were confirmed by FTIR, nuclear magnetic resonance spectroscopy(including ~1H-NMR and ~(13)C-NMR) and elemental analysis. In addition, the thermal stability, crystallinity structure and surface morphology of synthesized polyamides were characterized via thermogravametric analysis(TGA), wide-angle X-ray diffraction analysis(WAXD) and scanning electron microscopy(SEM). Also, the corrosion inhibition behavior of selected examples of polyamides was investigated; the inhibitive effect of the investigated polymers for carbon steel in 1.0 mol·L~(-1) HCl was studied using potentiodynamic polarization(PDP) and electrochemical impedance spectroscopy(EIS) methods. PDP results displayed that the polyamides containing thieno[2,3-b]thiophene moiety can be as mixed-type inhibitors. The inhibition efficiency(P, %) was found to be in the range from 67.13% to 96.01%. There is an increase in P by the synthesized polymers in comparison to the starting monomer.The adsorption of these polymers was found to obey Langmuir adsorption isotherm.
引文
1 Yang,H.H.“Aromatic high-strength fibers”,John Wiley&Sons,New York,1989.
2 Liou,G.S.;Yen,H.J.“Polyimides”,in:K.Matyjaszewski,M.Moller(eds.),“Polymer science:a comprehensive reference”,Elsevier Science,Amsterdam,2012,P.497-535.
3 Liaw,D.J.;Wang,K.L.;Huang,Y.C.;Lee,K.R.;Lai,J.Y.;Ha,C.S.Advanced polyimide materials:synthesis,physicalproperties and application.Prog.Polym.Sci.2012,37,907-974.
4 Hsiao,S.H.;Peng,S.C.;Kung,Y.R.;Leu,C.M.;Lee,T.M. Synthesis and electro-optical properties of aromatic polyamidesand polyimides.Eur.Polym.J.2015,73,50-60.
5 Levchik,S.V.;Weil,E.D.Combustion and fire retardancy ofaliphatic nylons.Polym.Int.2000,49,1033-1073.
6 Wang,Y.F.;Chen,T.M.;Li,Y.J.;Kitamura,M.;Sakurai,I.;Nakaya,T.Studies on syntheses and properties of novel polyamides containing phosphatidyl choline analogous moieties by interfacial polycondensation.J.Polym.Sci.,Part A:Polym.Chem.1997,35,3065-3074.
7 Ferrero,E.;Espeso,J.F.;de La Campa,J.G.;De Abajo,J.;Lozano,A.E.Synthesis and characterization of aromatic polyamides containing alkylphthalimido pendent groups.J.Polym.Sci.A:Polym.Chem.2002,40,3711-3724.
8 Chen,Y.;Wang,Q.Preparation,properties and characterization of halogen-free nitrogen-phosphorous flame- retarded glass fiber reinforced polyamide 6 composite.Polym.Degrad.Stab.2006,91,2003-2013.
9 Wang,Q.;Shi,W.Synthesis and thermal decomposition of a novel hyperbranched polyphosphate ester used for flame retardant system.Polym.Degrad.Stab.2006,91,1289-1294.
10 Liou,G.S.;Hsiao,S.H.;Ishida,M.;Kakimoto,M.;Imai,Y.Synthesis and characterization of novel soluble triphenylamine-containing aromatic polyamides based on N,N′-bis(4-aminophenyl)-N,N′-diphenyl-1,4-phynylene diamine.J.polym.Sci.,Part A:Polym.Chem.2002,40,2810-2818.
11 Chern,Y.T.;Wang,W.L.Synthesis and properties of new polyamides based on diamantine.Macromolecules 1995,28,5554-5560.
12 Liou,G.S.;Oishi,Y.;Kakimoto,M.A.;Imai,Y.Preparation and properties of aromatic polyamides from 2,2′-bibenzoic acid and aromatic diamines.J.Polym.Sci.,Part A:Polym.Chem. 1991,29,995-1000.
13 Cimecioglu,A.L.;Weiss,R.A.Synthesis and properties of polyamides of 3,3’-dimethyl naphthidine and its model compounds.J.Polym.Sci.,Part A.:Polym.Chem.1992,30,1051-1060.
14 Yang,C.P.;Lin,J.H.Preparation and properties of aromatic polyamides and polyimides derived from 3,3-bis[4-(4-amino phenoxy)phenyl]phthalide.J.Polym.Sci.,Part A:Polym.Chem.1994,32,423-433.
15 Jadhav,J.Y.;Preston,J.;Krigbaum,W.R.Aromatic rigid chain copolymers.1.Synthesis,structure and solubility of phenyl-substituted para-linked aromatic random copolyamides.J.Polym.Sci.Part A:Polym.Chem.1989,27,1175-1195.
16 Delaviz,Y.;Gungor,A.;Mac Grath,J.E.;Gibson,H.W.Soluble phosphine oxide containing aromatic polyamides.Polymer 1993,34,210-213.
17 Takayangi,M.;Katoyse,T.n-substituted poly(p-phenylene terephthalamide).J.Polym.Sci.Part A:Polym.Chem.1981,19,1133-1145.
18 Itamura,S.;Yamada,M.;Tamura,S.;Matsumoto,T.;Kurosaki,T.Soluble polyimides with polyalicyclic structure.1.Polyimides from bicyclo[2.2.2]oct-7-ene-2-exo,3-exo,5-exo,6- exo-tetracarboxylic 2,3:5,6-dianhydrides.Macromolecules1993,26,3490-3493.
19 Bottino,F.A.;Pasquale,G.D.;Pollicino,A.;Scalia,L.Synthesis and characterization of new polyamides containing 6,6′methylenediquinoline units.Polymer 1998,39(20),4949-4954.
20 Morgan,P.“Condensation polymers by interfacial and solution method”,John Wiley&Sons,New York,1965.
21 Morgan,P.W.;Kwolek,S.L.Polyamides from phenylenediamines and aliphatic diacids.Macromolecules 1975,8(2),104-111.
22 Aly,K.I.;Hussein,M.A.Synthesis,characterization and corrosion inhibitive properties of new thiazole based polyamides containing diarylidenecyclohexanone moiety.Chinese J.Polym.Sci.2015,33(1),1-13.
23 Liou,G.S.;Maruyama,M.;Kakimoto,M.A.;Imai,Y.Preparation and properties of aromatic polyamides from 2,2′-bis(p-aminophenoxy)biphenyl or 2,2′-bis(p-aminophenoxy)-1,1′-binaphthyl and aromatic dicarboxylic acids.J.Polym.Sci.,Part A:Polym.Chem.1993,31,2499-2506.
24 Park,S.H.;Lee,J.W.;Suh,D.H.;Ju,S.Y.Synthesis and characteristics of novel polyamides having pendent N-phenyl imide groups.J.Macromol.Sci.A:Pure Appl.Chem.2001,38,513-525.
25 Sarjadi,M.S.;Yi,H.;Iraqi,A.;Lidzey,D.G.Theinothiophene units properties on the carbazole-based polymers for organic solar cell devices.Malaysian J.Analyt.Sci.2015,19(6),1205-1217.
26 Diez,A.S.;Saidman,S.;Garay,R.O.Synthesis of atheinothiophene conjugated polymer.Molecules 2000,5(3),555-556.
27 Aly,K.I.;Abdel Rahman,M.A.;Hussein,M.A.New polymer syntheses Part 53.Novel polyamides ofdiarylidenecycloalkanone containing azo groups in the polymer backbone:synthesis and characterization.Int.J.Polym.Mater.2010,59,553-569.
28 Chao,D.;He,L.;Berda,E.B.;Wang,S.;Jia,X.;Wang,C.Multifunction hyperbranched polyamide:synthesis and properties.Polymer 2013,54,3223-3229.
29 Faghihi,K.New polyamides based on bis(p-amidobenzoic acid)-p-phenylene diacrylic acid and hydantoin derivatives:synthesis and characterization.Turk.J.Chem.2008,32,75-86.
30 Bair,T.I.;Morgan,P.W.;Killian,F.L.Poly(1,4- phenyleneterephthalamides).polymerization and novel liquid- crystalline solutions.Macromolecules 1977,10(6),1396-1400.
31 Vogel,A.I.“Vogel’s textbook of practical organic Chemistry”.London,Longman Green 1,1967,p.464.
32 Aly,K.I.New polymer syntheses XXVIII.Synthesis and thermal behavior of new organometallic polyketones and copolyketones based on diferrocenylidenecyclohexanone.J.Appl.Polym.Sci.2004,94,1440-1448.
33 Aly,K.I.;Kandeel,M.M.New Polymer Syntheses IV.Synthesis and characterization of new polyamides containing bis-benzthiazolyl sulphone units in the main chain.High perform.Polym.1996,8,307-314.
34 El-Shafei,A.K.;Abdel-Ghany,H.A.;Sultan,A.A.;El-Saghier,A.M.M.Synthesis of thieno(2,3-b)thiophene and related structures.Phosphorus,Sulfur,Silicon Relat.Elem.1992,73,15-25.
35 Comel,A.;Kirsch,G.Efficient one pot preparation of variously substituted thieno[2,3-b]thiophene.J.Heterocycl.Chem.2001,38,1167-1171.
36 Yamazaki,N.;Matsumoto,M.;Higashi,F.Studies on reactions of the N-phosphonium salts of pyridines.XIV.Wholly aromatic polyamides by the direct polycondensation reaction by using phosphites in the presence of metal salts.J.Polym.Sci.,Part A:Polym.Chem.1975,13,1373-1380.
37 Holmer,D.A.;Pickett,O.A.;Saunders,J.H.Melt polycondensation of 4,4′-diaminodiphenylmethane with aliphatic dibasic acids.J.Polym.Sci.,Part A:Polym.Chem.1972,10,1547-1552.
38 Li,C.H.;Chang,T.C.Studies on thermotropic liquid crystalline polymers Part II.Synthesis and properties of poly(azomethine-ether).Eur.Polym.J.1991,27(1),35-39.
39 Yang,R.X.;Wang,T.T.;Deng,W.Q.Extraordinary capability for water treatment achieved by a perfluorous conjugated microporous polymer.Sci.Rep.2015.
40 Aly,K.I.New polymer syntheses VIII.Synthesis,characterization and morphology of new unsaturated copolyesters based on dibenzylidenecycloalkanones.Polym.Int.1998,47,483-490.
41 Kim,S.;Pearce,E.M.;Kwei,T.K.Synthesis and degradation of cyano-containing aramids.Polym.Adv.Technol.1990,1,49-73.
42 El-Sayed,A.R.;Shaker,A.M.;Abd El-Lateef,H.M.Corrosion inhibition of tin,indium and tin-indium alloys by adenine or adenosine in hydrochloric acid solution.Corros.Sci. 2010,52,72-81.
43 Abd El-Lateef,H.M.Experimental and computational investigation on the corrosion inhibition characteristics of mild steel by some novel synthesized imines in hydrochloric acid Solutions.Corros.Sci.2015,92,104-117.
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2 Liou,G.S.;Yen,H.J.“Polyimides”,in:K.Matyjaszewski,M.Moller(eds.),“Polymer science:a comprehensive reference”,Elsevier Science,Amsterdam,2012,P.497-535.
3 Liaw,D.J.;Wang,K.L.;Huang,Y.C.;Lee,K.R.;Lai,J.Y.;Ha,C.S.Advanced polyimide materials:synthesis,physicalproperties and application.Prog.Polym.Sci.2012,37,907-974.
4 Hsiao,S.H.;Peng,S.C.;Kung,Y.R.;Leu,C.M.;Lee,T.M. Synthesis and electro-optical properties of aromatic polyamidesand polyimides.Eur.Polym.J.2015,73,50-60.
5 Levchik,S.V.;Weil,E.D.Combustion and fire retardancy ofaliphatic nylons.Polym.Int.2000,49,1033-1073.
6 Wang,Y.F.;Chen,T.M.;Li,Y.J.;Kitamura,M.;Sakurai,I.;Nakaya,T.Studies on syntheses and properties of novel polyamides containing phosphatidyl choline analogous moieties by interfacial polycondensation.J.Polym.Sci.,Part A:Polym.Chem.1997,35,3065-3074.
7 Ferrero,E.;Espeso,J.F.;de La Campa,J.G.;De Abajo,J.;Lozano,A.E.Synthesis and characterization of aromatic polyamides containing alkylphthalimido pendent groups.J.Polym.Sci.A:Polym.Chem.2002,40,3711-3724.
8 Chen,Y.;Wang,Q.Preparation,properties and characterization of halogen-free nitrogen-phosphorous flame- retarded glass fiber reinforced polyamide 6 composite.Polym.Degrad.Stab.2006,91,2003-2013.
9 Wang,Q.;Shi,W.Synthesis and thermal decomposition of a novel hyperbranched polyphosphate ester used for flame retardant system.Polym.Degrad.Stab.2006,91,1289-1294.
10 Liou,G.S.;Hsiao,S.H.;Ishida,M.;Kakimoto,M.;Imai,Y.Synthesis and characterization of novel soluble triphenylamine-containing aromatic polyamides based on N,N′-bis(4-aminophenyl)-N,N′-diphenyl-1,4-phynylene diamine.J.polym.Sci.,Part A:Polym.Chem.2002,40,2810-2818.
11 Chern,Y.T.;Wang,W.L.Synthesis and properties of new polyamides based on diamantine.Macromolecules 1995,28,5554-5560.
12 Liou,G.S.;Oishi,Y.;Kakimoto,M.A.;Imai,Y.Preparation and properties of aromatic polyamides from 2,2′-bibenzoic acid and aromatic diamines.J.Polym.Sci.,Part A:Polym.Chem. 1991,29,995-1000.
13 Cimecioglu,A.L.;Weiss,R.A.Synthesis and properties of polyamides of 3,3’-dimethyl naphthidine and its model compounds.J.Polym.Sci.,Part A.:Polym.Chem.1992,30,1051-1060.
14 Yang,C.P.;Lin,J.H.Preparation and properties of aromatic polyamides and polyimides derived from 3,3-bis[4-(4-amino phenoxy)phenyl]phthalide.J.Polym.Sci.,Part A:Polym.Chem.1994,32,423-433.
15 Jadhav,J.Y.;Preston,J.;Krigbaum,W.R.Aromatic rigid chain copolymers.1.Synthesis,structure and solubility of phenyl-substituted para-linked aromatic random copolyamides.J.Polym.Sci.Part A:Polym.Chem.1989,27,1175-1195.
16 Delaviz,Y.;Gungor,A.;Mac Grath,J.E.;Gibson,H.W.Soluble phosphine oxide containing aromatic polyamides.Polymer 1993,34,210-213.
17 Takayangi,M.;Katoyse,T.n-substituted poly(p-phenylene terephthalamide).J.Polym.Sci.Part A:Polym.Chem.1981,19,1133-1145.
18 Itamura,S.;Yamada,M.;Tamura,S.;Matsumoto,T.;Kurosaki,T.Soluble polyimides with polyalicyclic structure.1.Polyimides from bicyclo[2.2.2]oct-7-ene-2-exo,3-exo,5-exo,6- exo-tetracarboxylic 2,3:5,6-dianhydrides.Macromolecules1993,26,3490-3493.
19 Bottino,F.A.;Pasquale,G.D.;Pollicino,A.;Scalia,L.Synthesis and characterization of new polyamides containing 6,6′methylenediquinoline units.Polymer 1998,39(20),4949-4954.
20 Morgan,P.“Condensation polymers by interfacial and solution method”,John Wiley&Sons,New York,1965.
21 Morgan,P.W.;Kwolek,S.L.Polyamides from phenylenediamines and aliphatic diacids.Macromolecules 1975,8(2),104-111.
22 Aly,K.I.;Hussein,M.A.Synthesis,characterization and corrosion inhibitive properties of new thiazole based polyamides containing diarylidenecyclohexanone moiety.Chinese J.Polym.Sci.2015,33(1),1-13.
23 Liou,G.S.;Maruyama,M.;Kakimoto,M.A.;Imai,Y.Preparation and properties of aromatic polyamides from 2,2′-bis(p-aminophenoxy)biphenyl or 2,2′-bis(p-aminophenoxy)-1,1′-binaphthyl and aromatic dicarboxylic acids.J.Polym.Sci.,Part A:Polym.Chem.1993,31,2499-2506.
24 Park,S.H.;Lee,J.W.;Suh,D.H.;Ju,S.Y.Synthesis and characteristics of novel polyamides having pendent N-phenyl imide groups.J.Macromol.Sci.A:Pure Appl.Chem.2001,38,513-525.
25 Sarjadi,M.S.;Yi,H.;Iraqi,A.;Lidzey,D.G.Theinothiophene units properties on the carbazole-based polymers for organic solar cell devices.Malaysian J.Analyt.Sci.2015,19(6),1205-1217.
26 Diez,A.S.;Saidman,S.;Garay,R.O.Synthesis of atheinothiophene conjugated polymer.Molecules 2000,5(3),555-556.
27 Aly,K.I.;Abdel Rahman,M.A.;Hussein,M.A.New polymer syntheses Part 53.Novel polyamides ofdiarylidenecycloalkanone containing azo groups in the polymer backbone:synthesis and characterization.Int.J.Polym.Mater.2010,59,553-569.
28 Chao,D.;He,L.;Berda,E.B.;Wang,S.;Jia,X.;Wang,C.Multifunction hyperbranched polyamide:synthesis and properties.Polymer 2013,54,3223-3229.
29 Faghihi,K.New polyamides based on bis(p-amidobenzoic acid)-p-phenylene diacrylic acid and hydantoin derivatives:synthesis and characterization.Turk.J.Chem.2008,32,75-86.
30 Bair,T.I.;Morgan,P.W.;Killian,F.L.Poly(1,4- phenyleneterephthalamides).polymerization and novel liquid- crystalline solutions.Macromolecules 1977,10(6),1396-1400.
31 Vogel,A.I.“Vogel’s textbook of practical organic Chemistry”.London,Longman Green 1,1967,p.464.
32 Aly,K.I.New polymer syntheses XXVIII.Synthesis and thermal behavior of new organometallic polyketones and copolyketones based on diferrocenylidenecyclohexanone.J.Appl.Polym.Sci.2004,94,1440-1448.
33 Aly,K.I.;Kandeel,M.M.New Polymer Syntheses IV.Synthesis and characterization of new polyamides containing bis-benzthiazolyl sulphone units in the main chain.High perform.Polym.1996,8,307-314.
34 El-Shafei,A.K.;Abdel-Ghany,H.A.;Sultan,A.A.;El-Saghier,A.M.M.Synthesis of thieno(2,3-b)thiophene and related structures.Phosphorus,Sulfur,Silicon Relat.Elem.1992,73,15-25.
35 Comel,A.;Kirsch,G.Efficient one pot preparation of variously substituted thieno[2,3-b]thiophene.J.Heterocycl.Chem.2001,38,1167-1171.
36 Yamazaki,N.;Matsumoto,M.;Higashi,F.Studies on reactions of the N-phosphonium salts of pyridines.XIV.Wholly aromatic polyamides by the direct polycondensation reaction by using phosphites in the presence of metal salts.J.Polym.Sci.,Part A:Polym.Chem.1975,13,1373-1380.
37 Holmer,D.A.;Pickett,O.A.;Saunders,J.H.Melt polycondensation of 4,4′-diaminodiphenylmethane with aliphatic dibasic acids.J.Polym.Sci.,Part A:Polym.Chem.1972,10,1547-1552.
38 Li,C.H.;Chang,T.C.Studies on thermotropic liquid crystalline polymers Part II.Synthesis and properties of poly(azomethine-ether).Eur.Polym.J.1991,27(1),35-39.
39 Yang,R.X.;Wang,T.T.;Deng,W.Q.Extraordinary capability for water treatment achieved by a perfluorous conjugated microporous polymer.Sci.Rep.2015.
40 Aly,K.I.New polymer syntheses VIII.Synthesis,characterization and morphology of new unsaturated copolyesters based on dibenzylidenecycloalkanones.Polym.Int.1998,47,483-490.
41 Kim,S.;Pearce,E.M.;Kwei,T.K.Synthesis and degradation of cyano-containing aramids.Polym.Adv.Technol.1990,1,49-73.
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