Syntheses and properties of fluorinated polyamides and poly(amide imide)s based on 9,9-bis[4-(4-amino-2-trifluromethylphenoxy)phenyl]fluroene, aromatic dicarboxylic acids, and various monotrimellitimides and bistrimellitimides

Yang, Chin‐Ping; Su, Yu‐Yang; Hsu, Mei-Yuan

doi:10.1007/s00396-005-1440-0

Cited by 35 publications

(17 citation statements)

References 16 publications

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“…25 Sulfonated fluorinated polyamides containing pyridine moiety[23].The higher optical transparency of these polymers is attributed to the presence of the pendant 4-trifluoromethylphenyl substituents in the polymer backbone. This fact was attributed to the antioxidating actions of the sulfonyl group[53]. These PAs showed lower dielectric constants, in the range of 3.40-3.51 (1 MHz), than commercial Nylatron (approximately 3.7 at 1 MHz).…”

mentioning

confidence: 94%

Fluorinated Polyamides

Bandyopadhyay

Bera

Banerjee

2015

Handbook of Specialty Fluorinated Polymers

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confidence: 94%

Fluorinated Polyamides

Bandyopadhyay

Bera

Banerjee

2015

Handbook of Specialty Fluorinated Polymers

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“…Very recently, we reported the synthesis of a magnetic nanoparticle‐supported bidentate phosphine palladium (II) complex [Fe 3 O 4 @SiO 2 ‐2P‐PdCl 2 ] and its successful application to the carbonylative polycondensation of aromatic diiodides with ether ketone units, aromatic diamines bearing pyridine groups, and carbon monoxide leading to novel aromatic poly (ether ketone amide)s containing 4‐aryl‐2,6‐diphenylpyridine units . It has been demonstrated that the incorporation of fluorinated groups into polyamide backbones can provide not only enhanced solubility but also improved electrical and dielectric performance . Recently, the synthesis of fluorinated polyamides containing cardo structures has attracted considerable interest because of their excellent combined properties .…”

Section: Introductionmentioning

confidence: 99%

“…It has been demonstrated that the incorporation of fluorinated groups into polyamide backbones can provide not only enhanced solubility but also improved electrical and dielectric performance . Recently, the synthesis of fluorinated polyamides containing cardo structures has attracted considerable interest because of their excellent combined properties . Bandyopadhyay and Banerjee reported the synthesis of spiro [fluorene‐9,9′‐xanthene] containing fluorinated poly (ether amide)s by polycondensation of 2′,7′‐bis‐[2″‐trifluoromethyl 4″‐(4″‐aminophenyl)phenoxy] spiro [fluorene‐9,9′‐xanthene] with different aromatic diacids .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new fluorinated aromatic poly (ether ketone amide)s containing cardo structures by a heterogeneous palladium‐catalyzed carbonylative polycondensation

Liu

Zou

Zhang

et al. 2018

Polymers for Advanced Techs

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New fluorinated aromatic poly (ether ketone amide)s containing cardo structures were prepared by a heterogeneous palladium‐catalyzed polycondensation of fluorinated aromatic diiodides with ether ketone units, aromatic diamines containing cardo groups, and CO. Polymerizations were conducted in N,N‐dimethylacetamide at 120°C using 6 mol% of magnetic nanoparticles‐supported bidentate phosphine palladium (II) complex [Fe3O4@SiO2‐2P‐PdCl2] as catalyst and 1,8‐diazabicyclo[5,4,0]‐7‐undecene as base and resulted in fluorinated cardo poly (ether ketone amide)s with inherent viscosities up to 0.75 dL/g. All the polymers were readily soluble in many organic solvents and could afford transparent, flexible, and strong films by solution casting. These polymers showed good thermal stability with the glass transition temperature of 237°C–258°C, the temperature at 5% weight loss of 462°C–477°C in nitrogen. These polymer films also exhibited good mechanical properties, excellent electrical and dielectric performance, and high optical transparency. The incorporation of bulky fluorinated groups and cardo structures into polymer backbone has played an important role in the improvement of solubility, dielectric performance, and optical properties. Importantly, the heterogeneous palladium catalyst can easily be recovered from the reaction mixture by simply applying an external magnet and recycled up to 7 times without significant loss of catalytic activity.

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“…13,14 Recently, some efforts have been made on preparing fluorinated aramids, especially the trifluoromethyl (CF 3 )-containing poly(ether amide)s (PEAs). [15][16][17][18] It has been proved that the incorporation of bulky -CF 3 moieties into polyamide backbones resulted in great benefits for improving polymer solubility and optical transparency, as well as electrical and dielectric performance, which was attributed to the low polarizability of the C-F bond and the increase in free volume. 19,20 Recent studies demonstrated that the introduction of both flexible ether linkages and bulky naphthalene units into the polymer chains can enhance the solubility and processability of aramids, without any significant reduction in thermal stability.…”

Section: Introductionmentioning

confidence: 99%

Fluorinated ortho-linked polyamides derived from non-coplanar 1,1′-thiobis(2-naphthol): synthesis and characterization

Shockravi¹,

Javadi²,

Abouzari‐Lotf

2011

Polym J

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A novel sulfide-bridged bis(ether amine) monomer containing bulky trifluoromethyl and naphthyl substituents, 1,1¢-thiobis[2-(4-amino-2-trifluoromethylphenoxy)naphthalene], was synthesized from the halogen displacement of 2-chloro-5-nitrobenzotrifluoride with 1,1¢-thiobis(2-naphthol) in the presence of potassium carbonate, followed by the palladium on activated carbon-catalyzed reduction of bis(ether nitro) intermediate, 1,1¢-thiobis[2-(4-nitro-2-trifluoromethylphenoxy)naphthalene], with hydrazine hydrate in refluxing ethanol. New series of fluorinated poly(ether amide)s (PEA-1-8) were synthesized from bis(ether amine) with various commercially available aromatic diacids (1-8) via a direct polycondensation method with triphenyl phosphite and pyridine. The resulting polymers had inherent viscosities, ranging from 0.61 to 0.93 dl g -1 . All the polymers showed outstanding solubility and could be easily dissolved in amide-type polar aprotic solvents (for example, N-methyl-2-pyrrolidone, dimethyl sulfoxide and N,N-dimethylacetamide (DMAc)), and even dissolved in less polar solvents (for example, pyridine, tetrahydrofuran and chloroform). In addition, these polymers could be cast into transparent, flexible and tough films from DMAc solutions. The glasstransition temperatures were recorded between 209 and 251 1C, and 10% weight loss temperatures were in excess of 470 1C in nitrogen and 450 1C in air atmosphere. Moreover, these PEAs exhibited low refractive indices (n¼1.5614-1.5813), birefringence (D¼0.0055-0.0097) and dielectric constants (e¼2.68-2.75).

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Syntheses and properties of fluorinated polyamides and poly(amide imide)s based on 9,9-bis[4-(4-amino-2-trifluromethylphenoxy)phenyl]fluroene, aromatic dicarboxylic acids, and various monotrimellitimides and bistrimellitimides

Cited by 35 publications

References 16 publications

Fluorinated Polyamides

Fluorinated Polyamides

Synthesis of new fluorinated aromatic poly (ether ketone amide)s containing cardo structures by a heterogeneous palladium‐catalyzed carbonylative polycondensation

Fluorinated ortho-linked polyamides derived from non-coplanar 1,1′-thiobis(2-naphthol): synthesis and characterization

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