Poly(ether–ester)s containing azomethine group in the main chain were synthesized by solution polycondensation of 4,4′-bis(3-hydroxypropyloxy)-N-benzylidene aniline with adipoyl and terephthaloyl diacid chlorides. The synthesized poly(ether–ester)s were characterized by Fourier transform infrared and proton, and carbon-13 nuclear magnetic resonance spectroscopic techniques. Thermal properties were studied using thermogravimetric analysis (TGA) and differential scanning calorimetry. Thermal degradation kinetics of poly(ether–ester)s were characterized by TGA at various heating rates (5°C min−1, 10°C min−1, and 20°C min−1). The apparent activation energy for the degradation of both the polymers was determined by three different non-isothermal model-free kinetics methods (Friedmann, Flynn–Wall Ozawa, and Kissinger–Akahira–Sunose). The photoisomerization property was examined with ultraviolet (UV) spectroscopy, and the polymer PEE1 showed a rate of trans to cis isomerization ranging 10–20 s, whereas reverse process took around 100 min in solution. UV studies suggested that this material may be used in the field of rewritable applications.
ChengCFanRWangZ, et al.Tunable and weakly negative permittivity in carbon/silicon nitride composites with different carbonizing temperatures. Carbon2017; 125: 103–112.
2.
CuiXZhuGPanY, et al.Polydimethylsiloxane-titania nanocomposite coating: fabrication and corrosion resistance. Polymer2018; 138: 203–210.
3.
ZhangYZhaoMZhangJ, et al.Excellent corrosion protection performance of epoxy composite coatings filled with silane functionalized silicon nitride. J Polym Res2018; 25: 130.
4.
DongMLiQLiuH, et al.Thermoplastic polyurethane-carbon black nanocomposite coating: fabrication and solid particle erosion resistance. Polymer2018; 158: 381–390.
5.
WangZWeiRGuJ, et al.Ultralight, highly compressible and fire-retardant graphene aerogel with self-adjustable electromagnetic wave absorption. Carbon2018; 139: 1126–1135.
6.
WangLQiuHLiangC, et al.Electromagnetic interference shielding MWCNT-Fe3O4@ Ag/epoxy nanocomposites with satisfactory thermal conductivity and high thermal stability. Carbon2019; 141: 506–514.
7.
GuoJSongHLiuH, et al.Polypyrrole-interface-functionalized nano-magnetite epoxy nanocomposites as electromagnetic wave absorbers with enhanced flame retardancy. J Mater Chem C2017; 5: 5334–5344.
8.
GuoZXiePDangF, et al.Derived nickel/carbon nanocomposites with enhanced microwave absorption. J Mater Chem C2018; 6: 8812–8822.
9.
WuNLiuCXuD, et al.Enhanced electromagnetic wave absorption of three-dimensional porous Fe3O4/C composite flowers. ACS Sustain Chem Eng2018; 6:12471–12480.
10.
WangCMurugadossVKongJ, et al.Overview of carbon nanostructures and nanocomposites for electromagnetic wave shielding. Carbon2018; 140: 696–733.
11.
DuHZhaoCXLinJ, et al.Carbon nanomaterials in direct liquid fuel cells. Chem Rec2018; 18: 1365–1372.
12.
MarrsWPecersRRHStillRH. Copolyesters studies III. J Appl Polym Sci1979; 23: 1095–1194.
13.
ShenoyMAPereiraEAParikhPF. Aromatic polyesters based on bisphenol-A for liquid insulating systems: a synthetic approach. J Appl Polym Sci2005; 95: 606–614.
14.
MallakpourSRafieeZ. Synthesis and characterization of novel organo soluble thermal stable and optically active polyesters derived from 5-(2-phthalimidipropanoylamino) isophthalic acid. Polym J2007; 39: 1185.
15.
LiouGSHsiaoHMHuangHM, et al.Synthesis and photophysical properties of novel organo-soluble polyarylates bearing triphenylamine moieties. J Polym Res2007; 14: 191–199.
16.
NyeSASwintSA. Synthesis and characterization of polyarylates derived from 4, 4′-dihydroxy-meta-terphenyl and aromatic diacid chlorides. J Polym Sci A: Polym Chem1994; 32: 721–727.
17.
Chin-PingYRuel-ShinCYuC. Preparation and characterization of organosoluble polyimides based on 1,1-bis[(3,4-aminophenoxy)phenyl]cyclohexane and commercial aromatic dianhydrides. J Appl Polym Sci2001; 62: 2750–2759.
18.
IwanASekD. Processable polyazomethines and polyketanils: from aerospace to light emitting diodes and other advanced applications. Prog Polym Sci2008; 33: 289–345.
19.
BeckerRSRichneyWF. Photochromic anils mechanisms and products of photoreactions and thermal reactions. J Am Chem Soc1967; 89: 1298–1302.
20.
LiCHChangTC. Thermotropic liquid crystalline polymer. III. Synthesis and properties of poly(amide-azomethine-ester). J Appl Polym Sci A1991; 29: 361–367.
21.
YangCJJenekheSA. Conjugated aromatic poly (azomethins) I. Characterization of Structure, electronic spectra and processing of thin films from soluble complexes. Chem Mater1991; 3: 878–887.
22.
GrigorasMCatanescuCO. Imine oligomers and polymers. Journal of Macromolecular Science, Part C: Polymer Reviews2004; 44: 131–173.
23.
lwanASekDRannouP, et al.Synthesis, characterization and optical properties of oligoketanils containing carbon-carbon double bond in the main chain. Synthetic2004; 143: 331–339.
D’AlelioGFCrivelloJVSchoenigRK, et al.Polymeric Schiff bases. I. The synthesis and evaluation of polymeric Schiff bases prepared by Schiff base exchange reactions. J Macromol Sci A1967; 7: 1161–1249.
26.
YangCJJenekheSA. Conjugated aromatic polyamines. 2. Synthesis, structure and properties of new aromatic polyazomethines. Macromolecules1995; 28: 1180–1196.
27.
YenHJLiouG. Novel blue and red electrochromic poly(azomethine ether)s based on electroactive triphenylamine moieties. Org Electron2010; 11: 299–310.
28.
CabralesLAbidiN. On the thermal degradation of cellulose in cotton fibers. J Therm Anal Calorim2010; 102: 485–491.
29.
WhiteJECatalloWJLegendreBL. Biomass pyrolysis kinetics: a comparative critical review with relevant agricultural residue case studies. J Anal Appl Pyrolysis2011; 91: 1–33.
30.
SahaBGhoshalAK. Model-free kinetics analysis of waste PE sample. Thermochim Acta2006; 451: 27–33.
31.
VyazovkinSBurnhamAKCriadoJM, et al.ICTAC kinetics committee recommendations for performing kinetic computations on thermal analysis data. Thermochim Acta2011; 520: 1–19.
32.
VyazovkinSWightCA. Model-free and model-fitting approaches to kinetic analysis of isothermal and non-isothermal data. Thermochim Acta1999; 340: 53–68.
33.
VyazokvinS. Computational aspects of kinetic analysis: part C. The ICTAC kinetics project the light at the end of the tunnel. Thermochim Acta2000; 355: 155–163.
34.
VyazovkinSWightC. Kinetics of thermal decomposition of cubic ammonium perchlorate. Chem Mater1999; 11: 3386–3393.
35.
VyazovkinSDollimoreD. Linear and nonlinear procedures in isoconversional computations of the activation energy of nonisothermal reactions in solids. J Chem Inf Model1996; 36: 42–45.
36.
ViniRMurugavelSC. Synthesis, photoisomerization properties and thermal degradation kinetics of polyesters containing azomethine moiety in the main chain. J Polym Mater2017; 34: 783–796.
37.
ViniRThenmozhiSMurugavelSC. Synthesis, characterization and thermal degradation kinetics of azomethine-based halogen-free flame-retardant polyphosphonates. High Perform Polym2019; 31: 86–96.
38.
PerrinDDArmaregoWLF. Purification of laboratory chemicals. New York: Pergamon, 1988.
39.
FurnissBSHennafordAJSmithPWG, et al.Vogel’s textbook of practical organic chemistry. Singapore: Pearson Education, 2004.
40.
FriedmanHL. Kinetics of thermal degradation of char-forming plastics from thermogravimetry: application to a phenolic plastic. J Polym Sci Part C1965; 6: 183–195.
41.
OzawaTA. A new method of analysing thermogravimetric data. Bull Chem Soc Jpn1965; 38: 1881–1886.
42.
YeiDRFuHKChenWY, et al.Synthesis of a novel benzoxazine monomer-intercalated montmorillonite and the curing kinetics of polybenzoxazine/clay hybrid nanocomposites. J Polym Sci B Polym Phys2006; 44: 347–358.
AkahiraTSunoseT. Method of determining activation deterioration constant of electrical insulating materials. Res Rep Chiba Inst Technol (Sci Technol)1971; 17: 22–31.
45.
RaghuAVJeongHMKimJH, et al.Synthesis and characterization of novel polyurethanes based on 4-{(4-hydroxyphenyl) iminomethyl} phenol. Macromol Res2008; 16: 194–199.
46.
BalajiKMurugavelSC. Investigation on dual properties of photosensitive thermotropic liquid crystalline poly(benzylidene-ether)s containing alkanones and methylene spacers in the main chain. J Polym Sci A Polym Chem2012; 50: 1696–1706.
47.
LathaGMurugavelSC. Synthesis and characterization of cardo poly(ether-ester)s containing 1,1-bis (4-hydroxyphenyl) cyclohexane in the main chain. Polym Bull2016; 73: 3237–3253.
48.
StilleJKCambellTW. Condensation monomers. New York: Wiley, 1988.
49.
MuthusamyAMurugavelSC, Photoreactive polymers containing α, β-unsaturated carbonyl group in the main chain. High Perform Polym2006; 18: 227–240.
50.
SilversteinRMWebsterFX. Spectroscopic identification of organic compounds, 6th ed. New York: Wiley, 2002.
51.
HeWJiangYYLuytAS, et al.Synthesis and degradation kinetics of a novel polyester containing bithiazole rings. Thermochim Acta2011; 525: 9–15.
52.
BalajiKMurugavelSC. Synthesis and characterization of photosensitive poly(ether ester)s containing α,β-unsaturated ketone moieties in the main chain derived from 2,6-bis[4-(3-hydroxypropyloxy)-3-methoxybenzylidene]cyclohexanone. J Appl Polym Sci2011; 120: 3141–3150.
53.
Van KrevelenDW. Some basic aspects of flame resistance of polymeric materials. Polymer1975; 16: 615–620.
54.
Van KrevelenDW. Properties of polymers. New York: Elsevier, 1990.
55.
StarinkMJ. The determination of activation energy from linear heating rate experiments: a comparison of the accuracy of isoconversion methods. Thermochim Acta2003; 404: 163–176.
56.
CriadoJMPerez-MaquedaLASanchez-JimenezPE. Dependence of the pre-exponential factor on temperature. J Therm Anal Calorim2005; 82: 671–675.
57.
BoonchomB. Kinetics and thermodynamic properties of the thermal decomposition of manganese dihydrogenphosphate dehydrate. J Chem Eng Data2008; 53: 1533–1538.
58.
VyazovkinSLesnikovichAL. An approach to the solution of the inverse kinetic problem in the case of complex process. Part I: methods employing a series of thermodynamical curves. Thermochim Acta1990; 165: 273–280.
59.
VyazovkinSGoryachkoVJLenikovichAI. An approach to the solution of the inverse kinetic problem in the case of complex processes. Part III: parallel independent reactions. Thermochim Acta1992; 197: 41–51.
60.
VyazovkinS. Conversion dependence of activation energy for model DSC curves of consecutive reactions. Thermochim Acta1994; 236: 1–13.
61.
VyazovkinSLinertW. Kinetic analysis of reversible thermal decomposition of solids. Int J Chem Kinet1995; 27: 73–84.
62.
BalamuruganRKannanP. Photoisomerization behaviour of bis-benzylidene and 1,3,4-oxadiazole based liquid crystalline polyesters, J Appl Polym Sci2010; 116: 1902–1912.
63.
Wei-Guang DiauE. A new trans-to-cis photoisomerization mechanism of azobenzene on the S1(n, π*) surface. J Phys Chem A2004; 108: 950–956.
64.
NatarajanMMurugavelSC. Synthesis, characterization and photo-switching properties of azobenzene mesogen containing poly(ether-ester)s from cashew nut shell liquid. J Polym Res2018; 25: 78.
