Poly(ether ether ketone)s and Poly(ether sulfones) with Pendent Adamantyl Groups

Mathias, Lon J.; Lewis, Charles; Wiegel, Kurt N.

doi:10.1021/ma960012y

Cited by 40 publications

(21 citation statements)

References 22 publications

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“…In particular, cardo typed aromatic diols, which contain a bulky group such as fluorene, 6,8 or adamantane [9][10][11] moiety in the center of the monomer structure, have been widely employed to produce corresponding PAEs which show good solubility and high optical transparency without any decrease of thermal stability. It also has been reported that the incorporation of trifluoromethyl, sulfonyl, ketone, and/or ether moieties between benzene rings activates aromatic halide monomers and consequently accelerates a nucleophilic displacement reaction by generating aromatic diphenolate ions from the aromatic diols and results in a high molecular weight polymer during the polycondensation.…”

Section: -5mentioning

confidence: 99%

Synthesis of Cardo Based Poly(arylene ether)s for Flexible Plastic Substrates and Their Properties

Kim

Kwon

Han

2011

Bulletin of the Korean Chemical Society

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New poly(arylene ether)s (PAEs) with both transparency and heat-resistance were prepared by a polycondensation of FBPODS, an ordered-sequence aromatic dihalide, and cardo typed aromatic diols containing fluorene and/or adamantane moiety and also non-cardo typed 1,5-naphthalene diol. The resulting polymers had their glass transition temperatures ranged from 202 to 247 o C. Based on TGA data, they exhibited excellent thermal stabilities, showing 5% weight loss at 434-487 o C. They had low thermal expansion coefficients of 58-59 ppm at temperature range of 50-200 o C as well as good mechanical properties with moduli of 1757-2143 MPa. The optical transmittance for the PAE films was over 70% at 550 nm, except for the PAE that contains naphthalene moiety (30% at 550 nm). They also showed water uptake of about 0.68% regardless of their chemical compositions. Therefore, the newly developed PAEs show strong potential as plastic substrates for flexible devices for display, solar cell and e-paper.

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Section: -5mentioning

confidence: 99%

Synthesis of Cardo Based Poly(arylene ether)s for Flexible Plastic Substrates and Their Properties

Kim

Kwon

Han

2011

Bulletin of the Korean Chemical Society

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“…18,19 Monomer Synthesis 4-(1-Adamantyl)-1,3-benzenediol 4-(1-adamantyl)-1,3-benzenediol was synthesized by an improved version of a method previously reported. 20 In a typical reaction, 1-bromoadamantane (26.95 g, 0.125 mol) and 1,3-benzenediol (20.65 g, 0.184 mol) were made to react in benzene (180 mL) at 90°C for 15 h. The reaction mixture was cooled to room temperature, and the adamantyl-substituted resorcinol crystallized from the solution. The solid was filtered off and washed several times with hexane and hot water to remove unreacted reagents, and the resulting adamantyl compound was recrystallized from toluene to give 23 …”

Section: Experimental Materialsmentioning

confidence: 99%

Synthesis and characterization of new soluble aromatic polyamides based on 4-(1-adamantyl)-1, 3-bis(4-aminophenoxy)benzene

Espeso

Campa

Lozano

et al. 2000

J. Polym. Sci. A Polym. Chem.

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“…are important high performance engineering thermoplastics due to their excellent properties such as high mechanical strength and high thermo‐oxidative and chemical stability. Therefore they find applications in aviation, spacecraft, automobiles, medical devices, gas separation membranes, ultrafiltration, fuel cells, electronic/electrical industries etc …”

Section: Introductionmentioning

confidence: 99%

“…Except for aromatic poly(ether sulfone)s, the applications of other commercially important poly(arylene ether)s are somewhat restricted due to difficulties in processing as well as synthesis which can be attributed to their poor organosolubility because of high crystallinity which originates from high chain packing density. Various approaches have been employed towards the enhancement of solubility and processability of poly(ether ketone)s by inclusion of meta ‐linkages, flexible linkages or bulky pendent groups via the utilization of appropriately designed bisphenols …”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of poly(arylene ether)s based on 3‐pentadecyl 4,4'‐biphenol

Tawade

Shaligram

Valsange

et al. 2016

Polymer International

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A new biphenol, 3-pentadecyl 4,4 ′ -biphenol, was synthesized starting from 3-pentadecylphenol and was polycondensed with 4,4 ′ -difluorobenzophenone, 1,3-bis(4-fluorobenzoyl)benzene and bis(4-fluorophenyl)sulfone to obtain poly(arylene ether)s with biphenylene linkages in the backbone and pendent pentadecyl chains. Inherent viscosities and number-average molecular weights (M n ) of the poly(arylene ether)s were in the range 0.50 − 0.81 dL g −1 and 2.2 × 10 4 − 8.3 × 10 4 , respectively. Detailed NMR spectroscopic studies of the poly(arylene ether)s indicated the presence of constitutional isomerism which existed because of the non-symmetrical structure of 3-pentadecyl 4,4 ′ -biphenol. The poly(arylene ether)s readily dissolved in common organic solvents such as dichloromethane, chloroform and tetrahydrofuran and could be cast into tough, transparent and flexible films from their chloroform solutions. The poly(arylene ether)s exhibited T g values in the range 35-60 ∘ C which are lower than that of reference poly(arylene ether)s without pentadecyl chains. The 10% decomposition temperatures (T 10 ) of the poly(arylene ether)s were in the range 410-455 ∘ C indicating their good thermal stability. A gas permeation study of poly(ether sulfone) containing pendent pentadecyl chains revealed a moderate increase in permeability for helium, hydrogen and oxygen. However, there was a large increase in permeability for carbon dioxide which could be attributed to the internal plasticization effect of pendent pentadecyl chains.

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Poly(ether ether ketone)s and Poly(ether sulfones) with Pendent Adamantyl Groups

Cited by 40 publications

References 22 publications

Synthesis of Cardo Based Poly(arylene ether)s for Flexible Plastic Substrates and Their Properties

Synthesis of Cardo Based Poly(arylene ether)s for Flexible Plastic Substrates and Their Properties

Synthesis and characterization of new soluble aromatic polyamides based on 4-(1-adamantyl)-1, 3-bis(4-aminophenoxy)benzene

Synthesis and properties of poly(arylene ether)s based on 3‐pentadecyl 4,4'‐biphenol

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