A new dihydroxy monomer, 1-(2-hydroxypyridin-3-yl)-3-(2-(2-hydroxypyridin-3-yl)-1,3-dioxo-isoindoline-5-carbonyl)thiourea, with preformed trimellitic anhydride chloride-derived imide ring, pyridine and C=S moieties was synthesized. This compound was exploited to prepare three heteroaromatic poly(thiourea-imide-ester)s (PTIEs) by polycondensation with various diacid chlorides. Structural analysis of polymers was carried out by Fourier transformation infrared and nuclear magnetic resonance spectroscopy. PTIEs were readily soluble in polar solvents such as N,N-dimethylacetamide, dimethylformamide, dimethyl sulfoxide and N-methylpyrrolidone. Inherent viscosity and gel permeation chromatography measurements revealed high molar mass (140 × 102 to 101 × 102). One of the polymers showed crystalline behavior according to x-ray diffraction. Thermogravimetric analysis and differential scanning calorimetry were adopted for the thermal analysis of the polymers. Novel aromatic PTIEs possess high weight loss temperature (T10) in the range 524–536°C and glass transition temperature of about 223–230°C.
CarothersWHVan NattaFJ.Studies on polymerization and ring formation. III. Glycol esters of carbonic acid. J Am Chem Soc1930; 52(1): 314–326.
2.
MarrsWPetersRHStillRH. Copolyester studies. III. Melt-spinning, drawing and mechanical properties of tetramethylene terepthalate-tetramethylene sebacate copolymer fibers. J Appl Polym Sci1979; 23(4): 1095–1104.
3.
ShenoyMAPereiraEAParikhPF. Aromatic polyester based on bisphenol-A for liquid insulating systems: a synthetic approach. J Appl Polym Sci2005; 95(3): 606–614.
HsiaoSHChenWT.Syntheses and properties of aromatic polyimides based on 1,1-bis4-(4-aminophenoxy)phenyl]-1-phenyl-2,2,2-trifluoroethane and 1,1-bis[4-(4-amino-phenoxy)phenyl]-1-phenylethane. J Polym Res2003; 10(2): 95–103.
10.
YangCPHsiaoFZ. Synthesis and properties of polyimides based on an ether ketone diamine, 4,4'-bis(4-aminophenoxy)benzophenone. J Polym Res2003; 10(3): 181–193.
11.
BrumaMFitchJWCassidyPE. Hexafluoroisopropylidene-containing polymers for high performance applications. J Macromol Sci Rev Macromol Chem Phys1996; C36: 119–159.
12.
HamciucCHamciucEBrumaM. New fluorinated poly(1,3,4-oxadiazole-ether-imide)s. Polymer2005; 46(16): 5851–5859.
13.
SerbezeanuDVlad-BubulacTHamciucC. New phosphorus-containing copoly(ester-amide-imide) synthesis and characterization. Mater Plastic2011; 48(1): 7–11.
14.
PetreusOVlad-BubulacTHamciucC. New polyesterimides containing bulky, cyclic phosphorus groups. High Perform Polym2008; 20(6): 588–600.
15.
SerbezeanuDVlad-BubulacTHamciucC. Synthesis and characterization of new aromatic-aliphatic poly(ester-imide)s containing phosphorus. Rev Roum Chim2010; 55(10): 667–672.
16.
KulkarniSMDidgikarMRChaudhariRVKulkarniSM. Synthesis of polyesteramides by palladium-catalyzed carbonylation-polycondensation of aromatic diiodides and amino alcohols. J Mol Catal A: Chem2004; 207(2): 97–106.
17.
BruchMBurgathALoontjensTLhauptR. Synthesis and characterization of polyesteramides derived from an oxazoline-functional alcohol and dicarboxylic acid anhydrides. J Polym Sci A: Polym Chem1999; 37(16): 3367–3376.
18.
MadhraMKSalunkeAKBanerjeeS. Synthesis and properties of fluorinated polyimides, derived from novel 2,6-bis(3’-trifluoromethyl-p-aminobiphenyl-ether)pyridine and 2,5-bis(3’-trifluoromethyl-p-aminobiphenyl ether)thiophene. Macromol Chem Phys2002; 203(9): 1238–1245.
TamamiBYeganehH. Preparation and properties of novel polyimides derived from 4-aryl-2,6-bis(4-amino phenyl)pyridine. J Polym Sci A: Polym Chem2001; 39(21): 3826–3831.
21.
LiuJGWangLFYangHXLiYFYangS. Synthesis and characterization of new polybenzimidazopyrrolones derived from pyridine-bridged aromatic and dianhydrides. J Polym Sci A: Polym Chem2004; 42(8): 1845–1856.
22.
YangHXLiYFLiuJGYangSYYinDXZhouLC. Synthesis and properties of new polymerized monomer reactants matrix resins of pyrrolone-benzimidazole copolymers containing pyridine unit. J Appl Polym Sci2004; 91(6): 3981–3990
WangCChenSZhaoS. Inhibition effect of AC-treated mixed self-assembled film of phenylthiourea and 1-dodecanethiol on copper corrosion. J Electrochem Soc2004; 151(1): B11–B15.
25.
DehriIOzcanM. The effect of temperature on the corrosion of mild steel in acidic media in the presence of some sulphur-containing organic compounds. Mater Chem Phys2006; 98(2): 316–323.
26.
SabaaMWMohamedRRYassinAA. Organic thermal stabilizers for rigid poly(vinyl chloride) VIII. Phenylurea and phenylthiourea derivatives. Polym Degrd Stab2003; 81(1): 37–45.
27.
YoganarasimhanSRSoodRK. Semiconductivity of thiourea. Philosoph Mag1970; 22(179): 1075–1080.
28.
HariAMillerBL. Rapid and efficient synthesis of 2-amino-4H-benzothiazines. Org Lett2000; 2(23): 3667–3670.
29.
YuSCHouSChanWK. Synthesis and properties of polyamides and polyesters on the basis of 2,2‘-bipyridine-5,5′-dicarboxylic acid and the corresponding polymer-ruthenium complexes. Macromolecules2000; 33(9): 3259−3273.
30.
OgoshiTItohHKimKMChujoY. Synthesis of organic-inorganic polymer hybrids having interpenetrating polymer network structure by formation of ruthenium-bipyridyl complex. Macromolecules2002; 35(11): 334–338.
31.
KumamotoKMisawaYTokitaSKubobYKotsukiaH. High-pressure-promoted condensation of isothiocyanates with aminopyridines: efficient synthesis of pyridine–thiourea conjugates as building blocks for hydrogen-bonding receptors. Tetrahed Lett2002; 43(6): 1035–1038.
32.
BehniafarHGhorbaniH. New heat stable and processable poly(amideeethereimide)s derived from 5-(4-trimellitimidophenoxy)-1-trimellitimido naphthalene and various diamines. Polym Degrad Stab2008; 93(3): 608–617.
33.
VlaseTVlaseGDocaNIliaG. Thermo-oxidative degradation of polymers containing phosphorus in the main chain. High Perform Polym2010; 22(7): 863–875.
