High performance polyimides with good solubility and optical transparency formed by the introduction of alkyl and naphthalene groups into diamine monomers

Li, Tianyun; Huang, Hui; Wang, Lei; Chen, Yongming

doi:10.1039/c7ra07142f

Cited by 44 publications

(24 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Three kinds of pendant naphthalene‐containing diamines with –H, –CH 3 , or –CH(CH 3 ) 2 groups substituted at the ortho ‐positions of the aniline ring (BAN‐1, BAN‐2, and BAN‐3) were obtained through a one‐pot electrophilic substitution reaction of aldehyde I and aniline II, as shown in Scheme . Almost colorless PI films (λ 0 below 400 nm and T % > 84% at 450 nm) were obtained from the polymerization of BAN‐2 and BAN‐3 with commercial dianhydrides ODPA, BPDA, and 6FDA.…”

Section: Recent Design Approaches To Prepare Cpismentioning

confidence: 99%

See 1 more Smart Citation

Recent Trends on Transparent Colorless Polyimides with Balanced Thermal and Optical Properties: Design and Synthesis

Tapaswi

2019

Macro Chemistry & Physics

170

155

View full text Add to dashboard Cite

Recently, colorless and transparent plastic substrates with high glass transition temperature and suitable thermo‐mechanical properties are in high demand in optoelectronic device industries, due to their various optical applications. Colorless polyimides (CPIs) exhibit both high thermo‐mechanical stability as well as high transparency that are suitable for optoelectronic applications. The most recent (2010–2018) developments on CPIs, in terms of design and synthesis of new monomers and their effects on the thermo‐optical properties of the obtained CPIs, are reviewed in this article.

show abstract

Section: Recent Design Approaches To Prepare Cpismentioning

confidence: 99%

Section: Recent Design Approaches To Prepare Cpismentioning

confidence: 99%

Recent Trends on Transparent Colorless Polyimides with Balanced Thermal and Optical Properties: Design and Synthesis

Tapaswi

2019

Macro Chemistry & Physics

170

155

View full text Add to dashboard Cite

show abstract

“…The polycondensation proceeds through a one-stage mechanism, the imidization being performed employing microwave heating [119] or with the help of additional chemical initiators [120]. At the same time, microwaves can be used only to perform the cyclization of the PAA precursors obtained by conventional methods.…”

Section: Synthesis Of Pis In Microwave Conditionsmentioning

confidence: 99%

New High-Performance Materials: Bio-Based, Eco-Friendly Polyimides

Rusu¹,

Abadie²

2021

Polyimide for Electronic and Electrical Engineering Applications

View full text Add to dashboard Cite

The development of high-performance bio-based polyimides (PIs) seems a difficult task due to the incompatibility between petrochemical-derived, aromatic monomers and renewable, natural resources. Moreover, their production usually implies less eco-friendly experimental conditions, especially in terms of solvents and thermal conditions. In this chapter, we touch some of the most significant research endeavors that were devoted in the last decade to engineering naturally derived PI building blocks based on nontoxic, bio-renewable feedstocks. In most cases, the structural motifs of natural products are modified toward amine functionalities that are then used in classical or nonconventional methods for PI synthesis. We follow their evolution as viable alternatives to traditional starting compounds and prove they are able to generate eco-friendly PI materials that retain a combination of high-performance characteristics, or even bring some novel, enhanced features to the field. At the same time, serious progress has been made in the field of nonconventional synthetic and processing options for the development of PI-based materials. Greener experimental conditions such as ionic liquids, supercritical fluids, microwaves, and geothermal techniques represent feasible routes and reduce the negative environmental footprint of PIs' development. We also approach some insights regarding the sustainability, degradation, and recycling of PI-based materials.

show abstract

“…The research hotspots of the new soluble PIs have also given us available inspirations for molecular structure design. [36][37][38][39] Based on the above viewpoints, we introduced a tetrafluorostyrol structure into the triphenylmethane type backbone to synthesize a novel fluorine-containing and heat cross-linkable diamine monomer 4,4 0 -diamino-4 00 -(2,3,5,6-tetra-fluoro-4-ethylenephenoxy) triphenylmethane (DFPTM) with high temperature resistance and high light transmittance. Figure S1 illustrates the preparation of DFPTM, first, 4-hydroxy benzaldehyde and aniline were catalyzed by protonic acid to obtain the intermediate 4,4 0 -diamino-4 00 -hydroxy triphenylmethane (DHTM), which was then combined with 2,3,4,5,6-pentafluorostyrol to produce the target monomer via a nucleophilic substitution.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of novel colorless and thermostable polyimides containing cross‐linkable bulky tetrafluorostyrol pendant group and organosoluble triphenylmethane backbone structure

Yan

Zhang

et al. 2020

Journal of Polymer Science

View full text Add to dashboard Cite

A colorless and high temperature resistant fluorinated polyimide (PI) film based on a novel cross‐linkable diamine monomer 4,4′‐diamino‐4″‐(2,3,5,6‐tetrafluoro‐4‐ethylenephenoxy) triphenylmethane (DFPTM) was successfully prepared. The special triphenylmethane backbone and the bulky tetrafluorostyrol pendant group in DFPTM gave the PI material eximious solubility in organic solvents, high tensile properties, good thermal stability, and excellent optical transparency (cutoff wavelength for 331 nm and light transmittance above 94% at 450 nm). Furthermore, the styryl could initiate self‐crosslinking reaction to form a dense three‐dimensional network structure by thermal curing. Hence, the cross‐linked PI film showed superior combination property (including excellent resistance to solvents). It's Tg increased by 57.1–306.0°C, the 5% thermal weight‐loss temperature improved by 10.2% to 500.0°C, and the tensile strength enhanced by 17.5% to 39.7 MPa. Moreover, after thermal curing, the cross‐linked PI attained a lower elongation at break from 8.1 to 3.9%, and the thermal expansion coefficient reduced from 82.2 to 68.8 ppm/°C without obvious loss of optical transparency (cutoff wavelength for 347 nm and light transmittance remained 93.0% at 450 nm).

show abstract

High performance polyimides with good solubility and optical transparency formed by the introduction of alkyl and naphthalene groups into diamine monomers

Abstract: Highly soluble and optically transparent polyimides with excellent thermal stability were prepared by the introduction of alkyl and naphthalene groups into a single diamine monomer under microwave-assisted polymerization.

Cited by 44 publications

References 21 publications

Recent Trends on Transparent Colorless Polyimides with Balanced Thermal and Optical Properties: Design and Synthesis

Recent Trends on Transparent Colorless Polyimides with Balanced Thermal and Optical Properties: Design and Synthesis

New High-Performance Materials: Bio-Based, Eco-Friendly Polyimides

Synthesis and properties of novel colorless and thermostable polyimides containing cross‐linkable bulky tetrafluorostyrol pendant group and organosoluble triphenylmethane backbone structure

Contact Info

Product

Resources

About