New Polymer Syntheses, 112 (original) (raw)
Related papers
European Polymer Journal, 1993
Novel poly(amide imide)s (PAI) containing alkyl-substituted cyclohexylidene moieties were synthesized by conventional polycondensation of trimellitic anhydride chloride with novel aromatic diamines followed by chemical imidization using acetic anhydride and pyridine. The inherent viscosities of the resulting PAIs are relatively high and range from 71 to 112 mL g-1. The prepared PAIs show excellent thermal stability and good solubility. The glass transition temperatures (T g) measured by DSC are observed in the range of 312-342 8C. Furthermore, all the polymers are readily soluble in less hygroscopic organic solvents like cyclohexanone, c-butyrolactone as well as aprotic polar solvents. ZUSAMMENFASSUNG: Durch konventionelle Polykondensation von Trimellitsäureanhydridchlorid mit neuen aromatischen Diaminen und anschließender chemischer Imidisierung mit Acetanhydrid und Pyridin wurden neuartige Polyamidimide (PAI) mit alkylsubstituierten Cyclohexylidengruppen hergestellt. Die inhärenten Viskositäten der resultierenden PAI sind relativ hoch. Sie liegen im Bereich von 71 bis 112 mL g-1. Die synthetisierten PAI zeigen eine exzellente thermische Stabilität und gute Löslichkeit. Die mittels DSC bestimmten Glasübergangstemperaturen (T g) liegen zwischen 312 und 342 8C. Ferner sind alle diese Polymeren leicht in wenig hygroskopischen organischen Lösungsmitteln, wie Cyclohexanon oder c-Butyrolacton, sowie aprotischen polaren Lösungsmitteln löslich.
International Journal of Engineering Research and Technology (IJERT), 2013
https://www.ijert.org/synthesis-and-characterization-of-polyamides-from-diamine-containing-amide-linkages-in-the-main-chain https://www.ijert.org/research/synthesis-and-characterization-of-polyamides-from-diamine-containing-amide-linkages-in-the-main-chain-IJERTV2IS120862.pdf A novel aromatic diamine, N,N' bis-(4'-aminobenzoyl) benzene1,4 diamine (BABD) containing amide linkages in the main chain was synthesized and characterized by FT-IR, NMR (1H, 13C, DEPT 13C) and Mass spectrometry. A series of novel aromatic polyamides was synthesized from BABD and IPC/TPC in various mole proportions using low temperature solution polycondensation method. All the polyamides were obtained in very good yields and were characterized by FT-IR spectroscopy, viscosity measurements, solubility tests, differential scanning calorimetry (DSC), thermogravimeric analysis (TGA) and X-ray diffraction (XRD) techniques. The inherent viscosities (ηinh) of these polyamides were in the range 0.27-0.41 dL/g in DMAc at 30 ± 0.1 °C; indicating moderate to high molecular weight buildup. The polyamides showed solubility in aprotic polar solvents such as N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), dimethyl sulphoxide (DMSO) and N,N-dimethylformamide (DMF). The XRD results showed that the polyamides were partly crystalline. The glass transition temperature (T g) of these polyamides were in the range 234 to 244°C. The thermogravimeric analysis of all polymers showed no weight loss below 412 °C whereas the char yields at 900°C were in the range 15 to 60 % indicating high thermal stabilities of these polymers. Thus these polymers meet high temperature resistant requirements and could find applications as special materials in aerospace, military and microelectronics industries. The structure-property correlation among these polyamides is discussed.
2013
A novel aromatic diamine, N,N' bis-(4'-aminobenzoyl) benzene1,4 diamine (BABD) containing amide linkages in the main chain was synthesized and characterized by FT-IR, NMR (1H, 13C, DEPT 13C) and Mass spectrometry. A series of novel aromatic polyamides was synthesized from BABD and IPC/TPC in various mole proportions using low temperature solution polycondensation method. All the polyamides were obtained in very good yields and were characterized by FT-IR spectroscopy, viscosity measurements, solubility tests, differential scanning calorimetry (DSC), thermogravimeric analysis (TGA) and X-ray diffraction (XRD) techniques. The inherent viscosities (ηinh) of these polyamides were in the range 0.27-0.41 dL/g in DMAc at 30 ± 0.1 °C; indicating moderate to high molecular weight buildup. The polyamides showed solubility in aprotic polar solvents such as N-methyl-2-pyrrolidone (NMP), N,Ndimethylacetamide (DMAc), dimethyl sulphoxide (DMSO) and N,N-dimethylformamide (DMF). The XRD results showed that the polyamides were partly crystalline. The glass transition temperature (T g) of these polyamides were in the range 234 to 244°C. The thermogravimeric analysis of all polymers showed no weight loss below 412 °C whereas the char yields at 900°C were in the range 15 to 60 % indicating high thermal stabilities of these polymers. Thus these polymers meet high temperature resistant requirements and could find applications as special materials in aerospace, military and microelectronics industries. The structure-property correlation among these polyamides is discussed.
Designed Monomers and Polymers
Novel aromatic aliphatic diacid monomer, 4 4ʹ bis(4-carboxy methylene) biphenyl was synthesized via friedel craft acylation with acetic anhydride followed by willgerodot reaction and used in the preparation of polyamides by direct polycondensation using the Yamazaki phosphorylation reaction with commercial aromatic diamines. These polyamides were obtained in good yield with moderate-to-high-molecular-weight build up as evidenced by inherent viscosities in the range of 0.52-0.96 dlg−1. The XRD studies showed that all the polyamides were amorphous in nature and these polymers dissolved in polar aprotic solvents such as N-methyl-2-pyrrolidone(NMP),N, N-dimethylsulfoxide(DMSO), N,N-dimethyl formamide (DMF) and N,N-dimethyl acetamide. The resulting polyamides were characterized by inherent viscocity measurements, FT-IR, 1H NMR and 13C NMR spectroscopy, solubility, thermogravimetry, X-ray diffraction studies. These polyamides had glass transition temperatures between 210°C and 261°C, and their temperatures at a 10% weight loss were 620 to 710°C and 497 to 597°C in nitrogen and air atmospheres, respectively, which indicates thermally stable polymers.
Journal of Polymer Science Part A: Polymer Chemistry, 1998
Aromatic polyamides with azomethine groups present in the polymer with-Cl,-OCH 3 ,-N(CH 3) 2 and-OH substitutions in the pendent benzylidene rings were synthesized through polycondensation of new aromatic dicarboxylic acids with aromatic diamines using the phosphorylation technique in DMF. Direct polymerization of the monomers benzylidenamino phenyl 2,5-dicarboxylic acid (M1), 4-hydroxy benzylidenamino phenyl 2,5-dicarboxylic acid (M2), 4-methoxy benzylidenamino phenyl 2,5-dicarboxylic acid (M3), 4-chloro benzylidenamino phenyl 2,5-dicarboxylic acid (M4) and (N,N-dimethylamino) benzylidenamino phenyl 2,5-dicarboxylic acid (M5) was carried out with commercial diamines, 4,4-methylenedianilene and 4,4-diaminobiphenyl, at 140 • C. FT-IR and 1 H-NMR spectroscopic analysis were used to characterize the monomers and polymers. The inherent viscosity values of polyamides are in the range 0.39-0.68. Due to the substitutions in the pendent benzylidene rings, the polymers show enhanced solubility. The thermal stability of the polyamides was evaluated using thermogravimetric analysis, and the thermogravimetric curves show the dependence of thermal stability on the nature of the substitutions in the benzylidene rings.
Structure and Molecular Dynamics in Renewable Polyamides from Dideoxy–Diamino Isohexide
Macromolecules, 2012
The chemical structure, the conformation, and the flexibility of the polymer chain fragments present in the polyamides synthesized from 2,5-diamino-2,5-dideoxy-1,4;3,6dianhydrosorbitol, 1,4-diaminobutane, and either sebacic or brassylic acid have been studied by liquid-state 2D NMR spectroscopy viz. correlation spectra (COSY) and heteronuclear multiple-bond correlation spectra (gHMBC), by 13 C cross-polarization/magic-angle spinning (CP/MAS) NMR, by X-ray scattering, and by FT-IR spectroscopy. The presence of 2,5-diamino-2,5-dideoxy-1,4;3,6-dianhydrosorbitol in the crystal phase of the polyamides was probed by wide-angle X-ray diffraction (WAXD), FT-IR, and solid-state 13 C NMR. The incorporation of dideoxy−diamino isohexide into the backbone of PA 4.10 or PA 4.13 induces formation of gauche type conformers and gives rise to pseudohexagonal packing of the polymer chains in these semicrystalline copolymers. The experimental determination of the polymer chain structure combined with ab initio calculations revealed the presence of three most abundant diaminoisosorbide (DAIS) conformers. The combination of the 13 C chemical shifts of these three conformers could explain all experimental resonances in the region of 50−90 ppm. WAXD and DSC analysis show that the crystallinity, and hence the physical properties of the investigated compositions, can be tailored by the content of the bicyclic diamine in the backbone of the polyamides.
Unsaturated polyamides. Studies on synthesis, properties, and crosslinking
Angewandte Makromolekulare Chemie, 1983
A few unsaturated polyamides were prepared by thionyl chloride activated low temperature polycondensation and solution polymerization of fumaric, adipic, isophthalic, and terephthalic acid or their diacid chloride derivatives with 1 ,S-bis-(3-aminophenyl)-l,4-pentadiene-3-one. The polymers were characterized by nitrogen analysis and IR spectroscopy. The solution, thermal, and electrical properties of the polymers were studied. The polymers were found to be soluble in polar solvents. The solubility parameter of the polymers were calculated from Small's group contributions which agreed well with the experimental values. The polymers readily underwent crosslinking reaction when heated alone or preferably in the presence of a suitable free radical catalyst. The crosslinked polymers were found to be insoluble in polar solvents and possessed higher thermal stability compared with the virgin polymers. The swelling behaviour of the polymers were studied in detail and the molecular weight between two crosslinked junctions were also found out. X-ray diffraction and dielectric properties of the crosslinked polymers were also reported. ZUSAMMENFASSUNG: Es wurden einige ungesattigte Polyamide durch mit Thionylchlorid aktivierte Niedertemperatur-Polykondensation und Losungspolymerisation von Fumar-, Adipin-, Isophthal-und Terephthalsaure oder ihrer Disaurechloridderivate mit 1,5-Bis-(3aminophenyl)penta-l,4-dien-3-on hergestellt. Die Polymeren wurden durch Stickstoffanalyse und IR-Spektroskopie charakterisiert. Es wurden die Losungs-, thermischen-und elektrischen Eigenschaften dieser Polymeren untersucht. Es zeigte sich, daf3 die Polymeren in polaren Losungsmitteln loslich sind. Die Ldslichkeitsparameter dieser Polymeren wurden nach Small aus den Gruppeninkrementen berechnet und stimmen gut mit den experimentellen Werten uberein. Die Polymeren gingen eine Vernetzungsreaktion ein, wenn sie allein oder vorzugsweise in Gegenwart eines geeig-* Correspondence author.
Die makromolekulare Chemie, 1974
Aromatic isocyanatocarboxylic acid chlorides (1 a-i) reacted with stoichiometrical quantities of dimethyl sulfoxide in ether to yield poly(N-carb0xyanhydride)s (5) which were converted into polyamides (6) by heating them at elevated temperatures. Isocyanatocarboxylic acid chlorides also reacted with water to produce polyamides 6. The reaction paths were followed by quantitative analysis of carbon dioxide evolved, by measurement of IR spectra, and by thermal analysis of the polymers. ZUSAMMENFASSUNG: Aromatische Isocyanatocarbonsaurechloride (1 a-i) reagieren mit stochiometrischen Mengen von Dimethylsulfoxid in Ather und ergeben Poly(N-carboxyanhydride) (5), diedurch Erhitzen auf hohere Temperaturen in Polyamide (6) iiberfuhrt werden. Isocyanatocarbonsaurechloride reagieren ebenso mit Wasser unter Bildung von Pol yamiden 6. Der Reaktionsweg wurde durch quantitative Analyse des gebildeten Kohlendioxids verfolgt sowie mit Hilfe der IR-Spektren und durch thermische Analyse der Polymeren.
Preparation of polyamides via the phosphorylation reaction. VIII
Journal of Polymer Science: Polymer Chemistry Edition, 1984
Synopsis 4,4'-Diaminobenzanide (DAB) was reacted with diacids via the Yamazaki phosphorylation reaction to yield simple polyamides and random copolyamides. The use of DAB was found to promote polycondensation because DAB contains a preformed amide linkage which minimizes the amounts of by-products formed. It also maximizes polymer solubility since the monomer is unsymmetrical. The order of the inherent viscosity values of the polymers obtained from DAB by reaction with different diacids, isophthalic > aliphatic > terephthalic, was found to parallel polymer solubility in the reaction medium. The inherent viscosity of the polyamide based on terephthalic acid, DAB-T, was increased greatly by copolymerization, isophthalic acid being more effective than an aliphatic diacid in this regard. None of the polymers formed a thermotropic nematic phase, but the copolymer having an equimolar ratio of terephthalic and adipic acid formed anisotropic solutions in 100% sulfuric acid at polymer concentrations exceeding 40%. Strong films were cast from such solutions.