Amine–quinone polyimides

Han, Mijeong; Nikles, David E.

doi:10.1002/pola.10027

Cited by 8 publications

(5 citation statements)

References 18 publications

(24 reference statements)

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“…It is observed that the lap‐shear strength increases from 134.3 to 189.5 MPa when the BB content is increased from 0 to 4 wt%. This result can be attributed to the addition of hydrophobic BB into the epoxy resins which increases the adhesion of the aluminum–epoxy systems through chemical interaction, mediated by the quinone molecule free electrons to the outer orbital of the metal surface through chemisorption 9–11, 20. A similar observation was made with quinone‐amine polyurethanes obtained from toluene diisocyanate, polytetrahydrofuran, and amine‐quinone monomer 21…”

Section: Resultsmentioning

confidence: 54%

“…The curing agent was 4,4′‐diaminodiphenyl methane (DDM), purchased from Aldrich. BB was synthesized as described in recent work 9, 12. Dimethylacetamide (DMAc) as a solvent for BB was supplied from Aldrich.…”

Section: Methodsmentioning

confidence: 99%

“…Poly(amine‐quinone)s have a great affinity toward metal and glass surfaces and are active enough to displace water from wet, rusted, and steel surfaces, due to chemisorption induced by the quinone and imino moieties 9, 10. The several families of amine‐quinone polymers, such as poly(amine‐quinone)s, amine‐quinone polyimides, and amine‐quinone polyurethanes, are synthesized and used as corrosion protection for metal coatings 11–13.…”

Section: Introductionmentioning

confidence: 99%

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Fracture and adhesion behaviors of epoxy resins modified with poly(amine‐quinone)

Jin

Han

Park

2006

Polymer International

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An amine-quinone monomer, i.e. 2,5-bis(4,4 -methylenedianiline)-1,4-benzoquinone (BB), was synthesized by the Michael addition of 4,4 -diaminodiphenyl methane with 1,4-benzoquinone. To evaluate the effect of BB content on the glass transition temperature (T g ) and crosslinking density (ρ) of cured diglycidyl ether of bisphenol A (DGEBA)/BB systems, storage modulus and loss factor measurements were obtained using dynamic mechanical analysis. The mechanical properties of the systems were determined in terms of the fracture toughness, impact strength, and adhesion strength. As a result, the ρ values of the systems were found to decrease systematically as the BB content increased. The fracture toughness and adhesion strength of the systems increased with increasing BB content. These results indicate that the addition of BB into epoxy resins increases the free volume of the epoxy network and absorbs the deformation energy, resulting in an improvement of the mechanical properties of the DGEBA/BB systems.

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Section: Resultsmentioning

confidence: 54%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Fracture and adhesion behaviors of epoxy resins modified with poly(amine‐quinone)

Jin

Han

Park

2006

Polymer International

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“…More water can easily permeate into this phase due to its less highly cross-linked structure. This leads to a lower T g [12,13]. The higher cross-linked phase had a higher T g and was characterized as the less plasticized phase [14].…”

Section: Neat Epoxy Resinmentioning

confidence: 99%

Dynamic mechanical study of epoxy, epoxy/glass, and glass/epoxy/wood hybrid composites aged in various media

et al. 2008

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It was proposed and subsequently established that wrapping of red oak wood crossties with epoxy impregnated glass fiber composites will impart longer service life and better stiffness and strength characteristics to these hybrid ties than conventional ones and will help them better withstand environmental extremes. The objective was to understand the degrading effects of aqueous (distilled water), saline (NaCl), acidic (HCl), and alkaline (NaOH) solutions, as well as accelerated aging and freeze/thaw cycling environments on the dynamic and static mechanical properties of these hybrid materials (i.e., wood, wrapped with fiber reinforced resin) and their components. Also micrographs of composite samples, obtained through scanning electron microscopy (SEM), were studied to determine the failure mechanism of composite specimens aged in different environments. Results showed that immersion in aging media lowered the glass transition temperature (T g ) and enhanced apparent phase separation in the samples because of polymer plasticization. In water immersion, the T g and the stiffness increased with time owing to continued resin curing. At ambient temperature, sustained load had little effect on the mechanical behavior of the aged samples. The extent of degradation was the least for samples aged in salt solution. Soaking in room-temperature acid solution was most damaging to pure red oak wood samples. Sixcycle aging did not damage the neat resin or the hybrid samples, whereas it damaged pure wood specimens.Therefore, the composite wrapping around the wood core of the hybrid sample protected it sufficiently, thereby preventing damage to the hybrid specimen during the aging process. FIG. 7. SEM micrograph of glass/epoxy composite soaked in 5 M NaOH solution at room temperature for 5 months (a) cross-section surface (b) fracture surface. FIG. 8. SEM micrograph of glass/epoxy composite soaked in 1 M HCl solution at room temperature for 5 months (a) cross-section surface (b) fracture surface.

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“…Aromatic polyimide (PI) material, possessing excellent comprehensive properties, has been wildly applicated in aviation, aerospace, 1 automobile, electrical appliances, 2 micro‐electronics, 3 separation membranes 4 and other fields 5 . Due to its stable aromatic heterocyclic structure, PI presents remarkable temperature resistance (−269 ~ 400°C), excellent thermal and chemical stability, 6 outstanding mechanical properties, 7 radiation resistance and other significant characteristics 8,9 . At present, the traditional synthesis method is that the precursor polyamide acid (PAA) has to be synthesized with high molecular weight to get high performance, 10,11 which generated high viscosity in solution, therefore restricting the subsequent processing, especially when PI is used in coatings, 12 films, 13 adhesives and photoresists 14 …”

Section: Introductionmentioning

confidence: 99%

Functionalized polyimide based on mercaptoacetic acid locking imine reaction: Synthesis and coating application

Cao

Wang

et al. 2021

Journal of Polymer Science

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To meet the high requirements for polyimide (PI) manufacturing process without sacrificing material performance, a new type fabrication method for PI is proposed here. Based on the classical Kapton system, functionalized precursor polyamide acid (MPAA) resin solution with high solid content, low viscosity and high relative molecular weight was obtained via mercaptoacetic acid locking imine (MALI) reaction, and a series of linear Mali‐Polyimide (MPI) films were prepared and their properties were well investigated. The results showed that MPIs have relatively excellent thermal stability (Td5%: 598 ~ 601°C), good heat resistance (Tg: 277 ~ 278 °C) and high adhesion strength. This work emphasizes the possibility and potential of MALI reaction in PI synthesis and is expected to be applied in coating and adhesive field.

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Amine–quinone polyimides

Cited by 8 publications

References 18 publications

Fracture and adhesion behaviors of epoxy resins modified with poly(amine‐quinone)

Fracture and adhesion behaviors of epoxy resins modified with poly(amine‐quinone)

Dynamic mechanical study of epoxy, epoxy/glass, and glass/epoxy/wood hybrid composites aged in various media

Functionalized polyimide based on mercaptoacetic acid locking imine reaction: Synthesis and coating application

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