Synthesis and characterization of imide oligomers end-capped with 4-(phenylethynyl)phthalic anhydrides

Johnston, Jay A.; Li, F.M.; Harris, Frank W.; Takekoshi, T.

doi:10.1016/0032-3861(94)90745-5

Cited by 82 publications

(49 citation statements)

References 7 publications

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“…Many investigators have utilized a variety of analytical methods to examine the imidization and/or cure of ethynylor phenylethynyl-terminated imide polymers, including, for example, FTIR [19,24,35], DSC [19,23,36], thermogravimetric analysis (TGA) [23], high performance liquid chromatography (HPLC) [4], and solid-state 13 C nuclear magnetic resonance (NMR) [37] methods. Nonetheless, each of the approaches has limitations.…”

Section: Imidization and Cure Reaction Of Peti-5 Impregnated Glass Famentioning

confidence: 99%

Phenylethynyl-terminated polyimide, exfoliated graphite nanoplatelets, and the composites: an overview

Cho

Drzal²

2016

Carbon letters

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In efforts to characterize and understand the properties and processing of phenylethynylterminated imide (LaRC PETI-5, simply referred to as PETI-5) oligomers and polymers as a high-temperature sizing material for carbon fiber-reinforced polymer matrix composites, PETI-5 imidization and thermal curing behaviors have been extensively investigated based on the phenylethynyl end-group reaction. These studies are reviewed here. In addition, the use of PETI-5 to enhance interfacial adhesion between carbon fibers and a bismaleimide (BMI) matrix, as well as the dynamic mechanical properties of carbon/BMI composites, are discussed. Reports on the thermal expansion behavior of intercalated graphite flake, and the effects of exfoliated graphite nanoplatelets (xGnP) on the properties of PETI-5 matrix composites are also reviewed. The dynamic mechanical and thermal properties and the electrical resistivity of xGnP/PETI-5 composites are characterized. The effect of liquid rubber amine-terminated poly(butadiene-co-acrylonitrile) (ATBN)-coated xGnP particles incorporated into epoxy resin on the toughness of xGnP/epoxy composites is examined in terms of its impact on Izod strength. This paper provides an extensive overview from fundamental studies on PETI-5 and xGnP, as well as applied studies on relevant composite materials.Key words: polyimide, exfoliated graphite nanoplatelets, carbon fiber, composite, properties Phenylethynyl-Terminated Imide PolymerPolyimides have been extensively used in the electronics industry [1] as coatings, films, or adhesives and also in composite applications [2] as a primary or secondary structural material. When incorporated with organic or inorganic fibers, including carbon fibers and glass fibers, they can potentially be applied as a sizing material for high-temperature uses. In advanced applications, one of the most desirable advantages of polyimides, especially the aromatic polyimides, is their excellent high-temperature performance. Their thermal characteristics, including high temperature stability and cure behavior, are critical to successful processing and to the final properties of the resulting polyimide. For aerospace and aircraft applications, advanced polymer materials must successfully maintain their properties at high service temperatures over a long exposure time [3][4][5].The important parameters influencing the heat resistance of a polymeric material are its glass transition temperature (T g ), melting point (T m ), thermal stability, and etc., which may depend on its thermal history. Accordingly, polymers that are used to fulfill such high temperature performance should exhibit a high T g or T m and have excellent thermal stability. Even though some polyimides meet the high temperature requirement, their uses have been limited due to processing difficulties, such as poor solubility in common solvents, the release of volatiles, brittleness, and high processing temperature [6,7].Aromatic polyimides, especially acetylene or ethynyl-terminated polyimides, have been extensiv...

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Section: Imidization and Cure Reaction Of Peti-5 Impregnated Glass Famentioning

confidence: 99%

Phenylethynyl-terminated polyimide, exfoliated graphite nanoplatelets, and the composites: an overview

Cho

Drzal²

2016

Carbon letters

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“…[15] The earliest synthesis of oligomers with the same structures of AFR-PEPA-N was reported by Johnston et al in 1994. [16] 4-(Phenylethynyl)phthalic anhydride (PEPA) end-capped 6FDA/ 1,4-diaminobenzene ( p-PDA) oligomer was synthesized together with a series of phenylethynyl end-capped imide oligomers for possible use as an adhesive. Since then, some studies on mechanical properties and thermooxidative stabilities of cured AFR-PEPA-N polyimides have been performed.…”

Section: Full Papermentioning

confidence: 99%

Phenylethynyl End‐Capped Fluorinated Imide Oligomer AFR‐PEPA‐N: Morphology and Processibility Characteristics

Murphy

Lincoln

et al. 2007

Macro Materials & Eng

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Two phenylethynyl phthalic anhydride‐capped imide oligomers, AFR‐PEPA‐2 and AFR‐PEPA‐8, with molecular weights of 1 601 and 4 699 g · mol−1, respectively, were synthesized and characterized. The AFR‐PEPA‐N oligomers show higher glass transition temperatures and higher thermal decomposition temperatures than phenylethynyl‐terminated imide PETI‐5. After curing for 1 h at 390 °C, AFR‐PEPA‐2 and AFR‐PEPA‐8 have Tgs of 370 and 358 °C, respectively. AFR‐PEPA‐N oligomers demonstrated lower minimum complex melt viscosities than PETI‐5 due to the presence of CF3 group in the backbone structure. 1 601 g · mol−1 AFR‐PEPA‐2 imide oligomer has a complex melt viscosity of 10 Pa · s at 340 °C, and 4 699 g · mol−1 AFR‐PEPA‐8 imide oligomer has a complex melt viscosity of 227 Pa · s at 371 °C. AFR‐PEPA‐N film's crystal morphology was observed using polarized optical microscopy and the AFR‐PEPA‐8 oligomer did not show crystallinity. AFR‐PEPA‐2 film exhibits semicrystalline behavior and the crystallinity does not disappear until the film is cured above 375 °C.

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“…National Starch's Thermid IP-600 is an acetyleneterminated thermoset that has enhanced solubility, as it is an isoimide that thermally converts to imide when cured (142,143). The highest temperature matrix resin/structural adhesives were those based on phenylacetylene (phenylethynyl) (94,144,145). NASA's PETI (phenylethynyl-terminated imide) series consist of systems that cure at temperatures above 320 • C (100-103,146-149).…”

Section: Synthesis Of Polyimides Using Imide-containing Monomersmentioning

confidence: 99%

Polyimides

Bryant¹

2002

Encyclopedia of Polymer Science and Technology

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Polyimides are a class of high performance polymers that contain an imide group, defined as an sp 3 nitrogen bonded to two adjacent carbonyls. This imide structure is most commonly found as part of a five‐ or six‐membered ring. Polyimides are noted for their mechanical properties, chemical resistance, and dielectric strength. They exist as thermoplastics and thermosets. Polyimides are used as hot melt adhesives, matrix resins for composites, dielectric films, photoimageable coatings, flex circuits, foams, wire insulation, thin‐walled tubing, molding resins, and high performance bushings and seals. Products that compete with polyimides for niche applications include aerospace epoxies (Dow, Ciba, and Shell), cyanate resins (Dow), polysulfones (Solvay), filled polycarbonates and polyesters (Dow, Amoco, and GE), polybenzimidazoles (Hoechst‐Celanese), and some high T g filled phenolics. Although polyimides command a premium price, their versatility, reliability, and demonstrated performance make them suitable for use in high performance applications where failure and replacement costs are high.

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Synthesis and characterization of imide oligomers end-capped with 4-(phenylethynyl)phthalic anhydrides

Cited by 82 publications

References 7 publications

Phenylethynyl-terminated polyimide, exfoliated graphite nanoplatelets, and the composites: an overview

Phenylethynyl-terminated polyimide, exfoliated graphite nanoplatelets, and the composites: an overview

Phenylethynyl End‐Capped Fluorinated Imide Oligomer AFR‐PEPA‐N: Morphology and Processibility Characteristics

Polyimides

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