Poly(thioether imide)s via chloro-displacement polymerization

Mathias, Lon J.; Cei, Gustavo; Johnson, Randy A.; Yoneyama, Mitsuru

doi:10.1007/bf00294146

Cited by 8 publications

(3 citation statements)

References 4 publications

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“…FPIs (FPI-1 to FPI-8) were synthesized by nucleophilic substitution reaction. 19 –25 The typical procedure adopted for the synthesis of FPI-1 was as follows. Into a 100-mL round-bottomed flask fitted with a Dean–Stark trap, diol monomer IVa (0.01 mol), 30 mL of dry NMP, 20 mL of toluene and anhydrous potassium carbonate (0.022 mol) were added.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of diol monomers and organosoluble fluorinated polyimides with low dielectric

Saritha

Thiruvasagam

2015

High Performance Polymers

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Four diimide–diol monomers were synthesized from 4,4′-(hexafluoroisopropylidene)diphthalic dianhydride and aminophenol/aminonaphthol. The structures of the monomers were characterized by spectroscopic analysis. A series of fluorinated polyimides (FPI-1 to FPI-8) were synthesized from these new diols and 4,4′-difluorobenzophenone/4,4′-dichlorodiphenyl sulphone, through nucleophilic displacement reaction. The FPIs were characterized by Fourier transform infrared spectroscopy, proton nuclear magnetic resonance, X-ray diffraction, thermogravimetry, differential scanning calorimetry, solution viscosity, solubility test, and dielectric properties test. FPIs were amorphous and showed good solubility due to the presence of >C(CF3)2 unit and flexible groups in the polyimides backbone. These FPIs also showed good thermal stability and the 10% weight loss occurred in the range 353–505°C. The limiting oxygen index values of FPIs were in the range of 31.5–39.1 and such FPIs can be used as self-extinguishing polymers. These FPIs have a dielectric constant in the range of 3.10–4.23 and can be used as high temperature electrical insulation materials.

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Section: Methodsmentioning

confidence: 99%

Synthesis of diol monomers and organosoluble fluorinated polyimides with low dielectric

Saritha

Thiruvasagam

2015

High Performance Polymers

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“…Thiruvasagam recently synthesized polyetherimides by aromatic nucleophilic substitution reactions from AB-type monomers containing both phenolate salt and nitrophthalimide [42,43]. As early as in 1995, Mathias LJ attempted to synthesize poly(thioether imide)s from N-(p-mercaptophenyl)-4-chlorophthalimide (AB monomer); nevertheless, this kind of polyimide was only soluble in sulfuric acid and flexible films could not be obtained because of low molecular weight and limited flexibility of polymer backbone itself [44]. As far as we know, most researchers are focused on the work of polyetherimides from selfcondensation of AB-type monomers; only very few are concerned about polythioetherimides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of high performance poly(thioether imide)s via aromatic nucleophilic substitution reaction of isomeric AB-type monomers

2015

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A series of isomeric poly(thioether imide)s (PTIs) containing thioether linkages were prepared by aromatic nucleophilic substitution reaction of isomeric N-(4-mercaptophenyl)-3-chlorophthalimide and/or N-(4-mercaptophenyl)-4-chlorophthalimide. The inherent viscosities of these polymers were in the range of 0.38-0.42 dL/g. The glass transition temperature increased with increasing the content of 3-substituted phthalimide unit in the polymer backbone. The 5 % weight loss temperatures of isomeric PTIs (a-e) were 506-531°C in nitrogen and 509-536°C in air, respectively. The isomeric PTIs (b-d) films exhibited good mechanical properties with tensile strength of about 90 MPa, elongation at break of more than 6.0 %, and tensile moduli of more than 2.2 GPa. The storage moduli of PTIs (b-d) almost completely maintained at about 2.0 GPa before reaching the corresponding glass transition temperatures. It is noted that the minimum melt viscosity of these polymers decreased with increasing the content of unsymmetrical 3-and 4-substituted phthalimide unit.

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“…In the literature, to our knowledge, some pioneering works have been performed on PTEIs, such as the PTEIs based on 3,3',4,4'-thiodiphenyltetracarboxylic dianhydride [8], those based on diamine-terminated oligo(phenylene thioether)s [9], and those derived from chloro-displacement polymerization of substituted phthalimides and thiolates [10]. The applications include high temperature adhesives for bonding steels [11], high temperature composites [12] and gas separation membranes [13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Thermal Properties of Polythioetherimides Derived from 4,4'-[p-Thiobis(phenylenesulfanyl)]Diphthalic Anhydride and Various Aromatic Diamines

Liu

Shibasaki

Ando

et al. 2007

High Performance Polymers

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An asymmetrical aromatic diamine, 1-(4'-aminophenoxy)-4-(4'-aminophenylenesulfanyl) benzene (OSDA) was synthesized. A series of polythioetherimides (PTEIs) were prepared from a thioether-bridged aromatic dianhydride 4,4'-[ p-thiobis(phenylenesulfanyl)]diphthalic anhydride (3SDEA) and various aromatic diamines having ether or thioether linkages between phenylene rings by a two-step polycondensation procedure via their soluble poly(amic acid) (PAA) precursors. Medium to high molecular weight PAAs were obtained with inherent viscosities near or higher than 1.0 dL g-1, which is high enough to afford flexible and tough PTEI films except for PI-2 (3SDEA-134APB) and PI-6 (3SDEA- m2SPDA) derived from meta-ether-substituted diamines. PI-2 and PI-6 showed some extent of crystallinity compared to the amorphous natures of the other polymers. The PTEI films exhibit good resistance to organic solvents except for PI-3 (3SDEA-133APB), which is soluble in N-methyl-2-pyrrolidinone (NMP) and sulfuric acid at room temperature. The PTEI films show good thermal stability with the 5% weight loss temperatures being above 480°C both in nitrogen and in air. The glass transition temperatures of the PTEIs are in the range of 155—191°C, which are lower than those of the commercial polyetherimides due to their plural thioether linkages in the main chains.

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Poly(thioether imide)s via chloro-displacement polymerization

Cited by 8 publications

References 4 publications

Synthesis of diol monomers and organosoluble fluorinated polyimides with low dielectric

Synthesis of diol monomers and organosoluble fluorinated polyimides with low dielectric

Synthesis and characterization of high performance poly(thioether imide)s via aromatic nucleophilic substitution reaction of isomeric AB-type monomers

Synthesis and Thermal Properties of Polythioetherimides Derived from 4,4'-[p-Thiobis(phenylenesulfanyl)]Diphthalic Anhydride and Various Aromatic Diamines

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