• Elastomers and Composites
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• v.46 no.4
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• pp.295-303
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• 2011

A series of new aromatic polyhydroxyamides (PHAs) containing imide ring were prepared by direct polycondensation reaction of imide-diacids and two types of bis(o-aminophenol)s including 3,3'-dihydroxybenzidine and 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane. The polymers were characterized by FT-IR, FT-NMR, DSC and TGA. The inherent viscosities of the PHAs measured at $35^{\circ}C$ in DMAC solution were in the range of 0.49-1.13 dL/g. PHA 2 and 3, except PHA 1, were soluble in polar solvents such as DMAc, DMF and NMP. PHA 4, 5, and 6 containing 6F group showed a higher solubility in less polar solvents. But the polybenzoxazoles (PBOs,) were insoluble in a variety of solvents except partially soluble in sulfuric acid. The PBO 1, 2 and 3 showed maximum weight loss temperature in the range of $650-656^{\circ}C$ and relatively high char yields in the range of 57.4-61.9 % under a nitrogen atmosphere. These results suggested that the introduction of imide or diimide ring in the main chain was effective in improving the thermal stability of PHAs and PBOs.

• Proceedings of the Membrane Society of Korea Conference
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• 1997.10a
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• pp.39-45
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• 1997

Introduction : Polyimides are one of the most important classes of the high performance polymers due to their excellent electrical, thermal, and high-temperature mechanical properties. But their uses are limited because of their poor solubility. Most polyimide derivatives are processed in the form of polyamic acids, which are subsequently converted into the imide structures.Recently, it has been found that the soluble polyimides with large molecular weight sufficient to application. For enhancing processability, the majority of approaches have involved the following factors. As much as, the separation of the imide ring along the back-bone, that is to say, reducing the density of imide ring in the repeat structure. The introduction of bulky substituents along the back-bone, in order to enhance the free volume of main-chain. The incorporation of flexible or thermally stable linkages in the main-chain, reducing the packing force. The disruption of symmetry or recurrence regularity through copolymerization in order to reduce crystallnity.The objectives of this investigation are the synthesis and characterization of soluble polyimides as membrane materials by the single-step polymerization and the preparation of the asymmetric polyimide membrane by using phase inversion technique. In the present study, three series of polyimide derivatives are synthesized; H series is homopolyimides, A series is prepared from single dianhydride and two diamines, B series is yielded from two dianhydrides and a diamine. The dope solution was directly prepared from the PI solution via one step polymerization from monomers.

• Elastomers and Composites
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• v.51 no.3
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• pp.195-205
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• 2016

A series of aromatic poly(hydroxyamide)s (PHAs) containing varying oligo(oxyethylene) substituents and 1,3-phenylene imide ring unit in the main chain were synthesized by the direct polycondensation reaction. The inherent viscosities of the PHAs exhibited in the range of 0.89~1.12 dL/g in DMAc or DMAc/LiCl solution. The PH-2~5 copolymers were easily soluble in strong aprotic solvents: DMAc, NMP, DMSO etc. and the PH-5 copolymer was soluble in less polar solvents such as m-creasol and pyridine with LiCl salt on heating. However, all PBOs were quite insoluble in other solvents, but only partially soluble in sulfuric acid. All copolymers (PH-2~5) could afford the flexible and tough films by solution casting. We identified that the PHAs were converted to the PBOs by the thermal cyclization reaction in the range of $200{\sim}380^{\circ}C$. The 10% weight loss temperatures and char yields of the PBOs were recorded in the range of $382{\sim}647^{\circ}C$ and 38.7~73.1% values at $900^{\circ}C$. The tensile strength and initial modulus of the PH-5 in the copolmers showed the highest values of 2.46 GPa and 49.55 MPa, respectively. The LOI values of the PHAs were in the range 26.6~29.0%, and increased with increasing 1,3-phenylene imide ring unit.

• Fibers and Polymers
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• v.2 no.2
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• pp.92-97
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• 2001

New film forming aromatic poly(amide-imide)s containing isoindoloquinazolinedione (IQ) unit in the backbone chain (polymer XIV) have been successfully synthesized by preparing prepolymers of poly(amic acid-carbonamide). followed by subsequent thermal cyclization of the prepolymers. 4,4-Diamino-3-carbamoylbenzanilide (DACB) V has been synthesized by reduction of 3-carbamoyl-4-amino-4-nitrobenzanilide IV. The prepolymers of poly(amic-acid-carbonamide) (polymers VII and VIII) which exhibit viscosities ranging from 1.4 to 1.7 dl/g have been prepared by a condensation polymerization of monomers such as BPDA, ODA, and DACB. Polymer XIV has been obtained by thermal cyclization of the polymers VII and VIII. During the thermal cyclization reaction, imide ring structure was first introduced and then transformed to the structure of IQ unit. The thermal degradation rate of the resultant polymers were influenced by the cleavage of amide bond but the final char yield was comparable to that of poly(BPDA-ODA).

• Elastomers and Composites
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• v.43 no.1
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• pp.39-48
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• 2008

Peel strength of epoxy adhesives can be increased by adding some amounts of XNBR. In this case, thermal resistance of the adhesive will be decreased by decrease of glass transition temperature of the adhesive. Epoxy resin modified with siloxane-imide was synthesized to improve thermal resistance and peel strength of the adhesive, after that the properties of modified epoxy resin were compared with the commercial epoxy resin. When 5% XNBR was added to 30% modified epoxy resin, this adhesive showed 0.42 N/mm of peel strength and $155^{\circ}C$ of glass transition temperature. These properties are enough compared to the required properties by the industry, i.e., 0.3 N/mm and $150^{\circ}C$, respectively. Weight loss of the modified epoxy resin by the treatment of nitric acid and 0.1N NaOH was reduced, but weight gain by the humid condition was increased by the presence of benzene ring and imide ring. 30% modified epoxy resin blended with 5% XNBR showed 220% improvement in tensile strength and elongation compared to the case of common epoxy resin. This is due to the flexibility of the siloxane in the modified epoxy resin.

• Bulletin of the Korean Chemical Society
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• v.24 no.3
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• pp.357-362
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• 2003

The pathway producing imide ring closure during the thermal imidization of poly(amic acid) (PAA) was investigated in detail using a new analytical method, two-dimensional (2D) Raman correlation spectroscopy. The signs of the cross peaks in synchronous spectra provided evidence of the thermal imidization of PAA into PI as the heating temperature increased. The signs of the cross peaks in asynchronous spectra suggested that the imide-related modes changed prior to the amide or carboxylic mode, which indicates that cyclization occurred before the amide proton was abstracted.

• Textile Coloration and Finishing
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• v.7 no.4
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• pp.39-44
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• 1995

A study has been made about some correlations in the chemical cyclization of precursors, poly(ether-amide-amic acid)s by treating in solution a mixture of acetic anhydride and pyridine in the presence of 4,4-dimethyl formamide, with the poly(ether-amic acid)s being respectively reacted between trimellitic anhydride chloride and 3 kinds of diamines, i.e., 4,4'-bis(m-aminophenoxy) benzophenone, 2,2'-bis[4-(m-aminophenoxy) phenyl] propane and 4,4'-bis(m-aminophenoxy) diphenyl sulfone. The cyclization of imide ring in the poly(ether-amide-amic acid)s may be regarded as an intramolecular acylation of amide group by o-carboxyl group. As a result of this reseach, the effects on the conversion to poly(ether-amide-imide)s have been found by changing the ratio of cosolvents in the cyclization mixture.

• Applied Chemistry for Engineering
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• v.3 no.1
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• pp.179-187
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• 1992

Poly(styrene-co-maliec anhydride) was reacted with aromatic amines such as aniline, p-toluidine, and p-chloroaniline in 10% (w/w) DMF solution to convert maleic anhydride units into maleimides. Optimum reaction conditions for cyclodehydration step of imide ring formation were : (a) reaction temp. of $80^{\circ}C$ (b) mole ratios of cyclodehydration agents : anhydride units in SMA/acetic anhydride/sodium acetate/triethyl amine= 1.0/2.0/0.2/1.1. $T_g$of SMI(imide modified SMA) was increased with increasing degree of imidization, but $T_g$leveled off in the early stage of imide content. And $T_g$of SMI was increased with the following order of amines used for imidization reagents : aniline < p-toluidine < p-chloroaniline.

• Bulletin of the Korean Chemical Society
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• v.32 no.spc8
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• pp.3074-3080
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• 2011

We synthesized three novel poly(norbornene bisimide)s by ring opening metathesis polymerization (ROMP) and subsequent hydrogenation. Their thermal, mechanical and optical properties were investigated with TGA, DMA, UV-Vis spectrometer, and optical reflectometer. The new polymers showed high glass transition temperatures over $260^{\circ}C$ and good thermal stability with 5% wt-loss temperature higher than $390^{\circ}C$. When solvent casted, they yielded optically transparent and dimensionally stable films with a relatively low coefficient of thermal expansion of about 50 ppm $K^{-1}$. Therefore, the bisimide moieties substantially enhanced thermal and dimensional stabilities, as compared with normal ROMP-prepared polynorbornene films. Though the water uptake was increased to 0.6 wt-%, this water uptake is still considerably lower than that for polyethersulfones (1.4 wt-%) or polyimides (2.0 wt-%). Hence, the new poly(norbornene bisimide)s may become attractive candidates for flexible substrates of optoelectronic devices such as displays and photovoltaic solar cells.

• Bulletin of the Korean Chemical Society
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• v.27 no.10
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• pp.1542-1548
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• 2006

Maleimide modified epoxy compounds were prepared by reacting N-(4-hydroxyphenyl) maleimide (HPM) with diglycidylether of bisphenol-A. Triphenylphosphine was used as catalyst and methylethylketone as solvent. The resulting compound possessed both the oxirane ring and maleimide group. The curing reaction of the maleimide epoxy compound with amine curing agents such as 1-(2-aminoethyl) piperazine (AEP) and 5-amino-1,3,3-trimethylcyclohexane methylamine isophorone diamine, IPDA) were studied. Incorporation of maleimide groups in the epoxy resin provides cyclic imide structure and high cross-linking density to the cured resins. The cured samples were found to have good thermal stability, chemical resistance (acid/alkali/solvent) and water absorption resistance.