Synthesis and properties of polyester imides based on 2,2-bis(4-hydroxyphenyl)propanedibenzoate-3,3ʹ,4,4ʹ-tetracarboxylic acid dianhydride

Furutani, Hiroyuki; Tsuji, Hiroyuki; Sogabe, Keisuke

doi:10.1038/pj.2017.24

Cited by 10 publications

(10 citation statements)

References 9 publications

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“…The reaction rate is dependent on the basicity of the amine and the electrophilicity of the anhydride carbonyl. A lower ε LUMO value for the dianhydride and a higher ε HOMO value for the diamine could roughly indicate higher reactivity of the monomers 31 . Thus, it could be deduced from Figure 2 that the three HPMDA dianhydrides might possess the increasing reactivities with the order of H‐PMDA (ccHPMDA) < H′′‐PMDA (ctHPMDA) < H′‐PMDA (ttHPMDA).…”

Section: Resultsmentioning

confidence: 94%

“…A lower ε LUMO value for the dianhydride and a higher ε HOMO value for the diamine could roughly indicate higher reactivity of the monomers. 31 Thus, it could be deduced from Figure 2 that the three HPMDA dianhydrides might possess the increasing reactivities with the order of H-PMDA (ccHPMDA) < H 00 -PMDA (ctHPMDA) < H 0 -PMDA (ttHPMDA). Similarly, the fluorene-containing FDAADA diamine might have inferior reactivity to that of the FDA diamine according to the results shown in Figure 3.…”

Section: Pi Resin Synthesis and Film Preparationmentioning

confidence: 95%

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Synthesis and characterization of semi‐alicyclic transparent polyimide films containing benzanilide and fluorene units with improved high‐temperature dimensional stability and low‐optical retardations

Ren,

He,

Wang

et al. 2023

J of Applied Polymer Sci

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Two solution‐processable semi‐alicyclic transparent polyimide (PI) films with improved high‐temperature dimensional stability and low‐optical retardations were prepared from the stereo‐isomeric alicyclic dianhydrides, 1S,2R,4S,5R‐hydrogenated pyromellitic dianhydride (ccHPMDA) and 1R,2S,4S,5R‐hydrogenated pyromellitic dianhydride (ctHPMDA) and an aromatic diamine, 9,9‐bis[4‐(4‐aminobenzamide)phenyl]fluorene (FDAADA), respectively. The alicyclic cyclohexane units in the dianhydride moiety endowed the derived PI‐1 (ccHPMDA‐FDAADA) and PI‐2 (ctHPMDA‐FDAADA) films good optical transparency, the rigid‐rod benzanilide units provided the PI films low coefficients of thermal expansion (CTE), and the fluorene units resulted in good solution processability and low‐optical retardations (Rth) for the PI films. The PI films exhibited the glass transition temperatures over 400°C and the CTE value of 33.2 × 10−6/K for PI‐1 and 29.0 × 10−6/K for PI‐2 in the temperature range of 50 ~ 250°C, respectively. In addition, the PI films showed good optical transparency in the ultraviolet–visible light region with the optical transmittances higher than 80% for PI‐1 film at the wavelength of 500 nm. The PI films exhibited the average refractive indices of 1.6505 for PI‐1 and 1.6485 for PI‐2 film, respectively. The birefringence values of the PI films were all lower than 0.01, resulting in the low‐optical anisotropies with the optical retardation (Rth) of 77 nm for PI‐1 film and 84 nm for PI‐2 film.

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Section: Resultsmentioning

confidence: 94%

Section: Pi Resin Synthesis and Film Preparationmentioning

confidence: 95%

Synthesis and characterization of semi‐alicyclic transparent polyimide films containing benzanilide and fluorene units with improved high‐temperature dimensional stability and low‐optical retardations

Ren,

He,

Wang

et al. 2023

J of Applied Polymer Sci

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“…It has been well established in the literature that the lowest unoccupied molecular orbital (LUMO) energy levels (ε LUMO ) of one dianhydride and the highest occupied molecular orbital (HOMO) energy levels (ε HOMO ) of one diamine were closely related with their polymerization reactivity due to the nucleophilic reaction nature for the formation of poly(amic acid) 35,36 . A lower ε LUMO value for the dianhydride and a higher ε HOMO value for the diamine could roughly indicate higher reactivity of the monomers 37 . In the current work, the ε LUMO and ε HOMO values of the monomers were calculated according to the density functional theory (DFT)/B3LYP methods with Gaussian 09 software using the 6‐311G(d, p) basis set 38 and the results are shown in Figure 3.…”

Section: Resultsmentioning

confidence: 99%

“…35,36 A lower ε LUMO value for the dianhydride and a higher ε HOMO value for the diamine could roughly indicate higher reactivity of the monomers. 37 In the current work, the ε LUMO and ε HOMO values of the monomers were calculated according to the density functional theory (DFT)/B3LYP methods with Gaussian 09 software using the 6-311G(d, p) basis set 38 2).…”

Section: Characterizationmentioning

confidence: 99%

Synthesis and properties of modified thermoplastic polyimide films with good dielectric properties at high frequency and enhanced thermal stability via incorporation of rigid ester and biphenyl structural units

Han,

Qi,

Zhi

et al. 2024

Polymers for Advanced Techs

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A series of ester‐ and fluoro‐containing thermoplastic polyimide (PI) films, PEsI‐1 ~ PEsI‐4 have been prepared by the two‐step thermal imidization procedure via the soluble poly(amic acid) (PEsAA) precursors from the copolymerization of four monomers, including the dianhydrides of bisphenol A dibenzoate‐3,3′,4,4′‐tetracarboxylic acid dianhydride (TMBPA) and 3,3′, 4,4′‐biphenyl tetracarboxylic acid dianhydride (BPDA) and the diamine monomers of 4‐aminophenyl‐4′‐ aminobenzoate (APAB) and 2,2′‐bis(trifluoromethyl)‐4,4′‐diamino biphenyl (TFMB) in the polar aprotic solvent of N‐methyl‐2‐pyrrolidinone (NMP). The PI films obtained from the high‐temperature dehydration of the PEsAA solutions exhibited the good thermal stabilities with the glass transition temperatures (Tg) over 269°C, the 5% weight loss temperatures (T5%) higher than 480°C, and the linear coefficients of thermal expansion (CTE) values in the range of 17.7 × 10−6/K–33.6 × 10−6/K in the temperature range of 50–250°C. Meanwhile, the PI films showed good thermoplasticity in the dynamic mechanical analysis (DMA) tests, in which the storage modulus of the PI films dropped sharply in the temperature range of glass transition of the polymers. At last, the PI films exhibited the good dielectric properties with the breakdown voltages (Vb) over 5200 V, the dielectric strength (Ds) higher than 210 V/μm, the dielectric constants (Dk) in the range of 3.26 ~ 3.32 at the frequency of 10 GHz, and the dielectric dissipation factors (Df) of 0.0038 ~ 0.0047. Compared with the commonly used PEsI‐ref film for high‐frequency flexible copper clad laminates (FCCL), the currently developed PI films exhibited the obviously increased Tg values, decreased CTE values, and comparable dielectric properties.

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“…The reaction rate is dependent on the basicity of the amine, the electrophilicity of the anhydride carbonyl, and the basicity of the solvent 36 . Thus, a lower ε LUMO value for the dianhydride and a higher ε HOMO value for the diamine could roughly indicate higher reactivity of the monomers 37 . As could be seen from Figure 3 that the alicyclic dianhydrides exhibited the ε LUMO values of −2.09 V for CBDA and −1.89 V for DMCBDA, respectively, indicating the higher reactivity of the former.…”

Section: Resultsmentioning

confidence: 99%

Preparation and characterization of photo‐decomposable ester‐containing semi‐alicyclic polyimide alignment layers for potential applications in in‐plane switching thin‐film transistor liquid crystal display devices

Zhi

Wang²,

Jia³

et al. 2022

Polymers for Advanced Techs

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Poly(amic acid)s (PAAs) alignment agents have been prepared from the alicyclic dianhydrides, including 1,2,3,4‐cyclobutanetetracarboxylic dianhydride (CBDA, I), 1,3‐dimethyl‐1,2,3,4‐cyclobutanetetracarboxylic dianhydride (DMCBDA, II), and ester‐linked aromatic diamines, including 4‐aminophenyl‐4′‐aminobenzoate (APAB, a) and bis(4‐aminophenyl)terephthalate (BPTP, b), respectively. The derived PAAs, including PAA‐Ia (CBDA‐APAB), PAA‐Ib (CBDA‐BPTP), and PAA‐IIa (DMCBDA‐APAB) exhibited the preferable molecular weights, while the PAA‐IIb (DMCBDA‐BPTP) showed the low one due to the low polymerization reactivity both for the DMCBDA dianhydride and the BPTP diamine. All the PAA solutions except PAA‐IIb were adopted as the alignment components to fabricate liquid crystal (LC) minicells with a mode of in‐plane switching (IPS). The polyimides (PI) alignment layers derived from the thermal dehydration reaction of the PAA precursors at 230°C for 30 min showed good alignments effects to the LC molecules, which exhibited the pretilt angles (θp) from 0.09 to 0.15° after being exposed by the linear polarized ultraviolet light sources with the wavelength of 254 nm. In addition, the PI alignment layers afforded good optoelectronic features to the minicells, including the voltage holding ratio values over 97% at room temperature, and the residual direct circuit voltages lower than 1.0 V. The anchoring energy results indicated that the PI‐IIa (DMCBDA‐APAB) alignment layer showed the highest interaction with the LC molecules, and thus exhibited the highest threshold voltage (Vth) in the voltage‐transmittance (V‐T) measurements for the minicells.

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Synthesis and properties of polyester imides based on 2,2-bis(4-hydroxyphenyl)propanedibenzoate-3,3ʹ,4,4ʹ-tetracarboxylic acid dianhydride

Cited by 10 publications

References 9 publications

Synthesis and characterization of semi‐alicyclic transparent polyimide films containing benzanilide and fluorene units with improved high‐temperature dimensional stability and low‐optical retardations

Synthesis and characterization of semi‐alicyclic transparent polyimide films containing benzanilide and fluorene units with improved high‐temperature dimensional stability and low‐optical retardations

Synthesis and properties of modified thermoplastic polyimide films with good dielectric properties at high frequency and enhanced thermal stability via incorporation of rigid ester and biphenyl structural units

Preparation and characterization of photo‐decomposable ester‐containing semi‐alicyclic polyimide alignment layers for potential applications in in‐plane switching thin‐film transistor liquid crystal display devices

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