Design and preparation of thermoplastic polyimides with high transmittance based on 4,4′-(4,4′-isopropyldiphenoxy)bis(phthalic anhydride) (BPADA)

Wu, Gaojie; Wang, Zichen; Zi, Yucheng; Qi, Shengli; Tian, Guofeng; Wu, Dezhen

doi:10.1016/j.eurpolymj.2022.111798

Cited by 11 publications

(4 citation statements)

References 26 publications

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“…The TPI derived from fluoro-containing dianhydride, 4,4′-(hexafluoroisopropyl)diphthalic anhydride (6FDA) and the POSS-containing diamine showed the good optical transparency in the visible light region (wavelength: 380~780 nm) at the thickness of 216 μm. Wu and coworkers reported the TPIs with good optical transparency based on the copolymerization of 4,4′-(4,4′-isopropyldiphenoxy)bis(phthalic anhydride) (BPADA), 6FDA, 1,2,3,4-cyclobutanetetracarboxylic dianhydride (CBDA) and the fluoro-containing diamine 2,2-bis(trifluoromethyl)benzidine (TFMB) [17]. The developed TPI sheets showed the optical transmittance over 80% at the wavelength of 650 nm at the thickness from 110 to 150 μm.…”

Section: Introductionmentioning

confidence: 99%

Preparation and properties of semi-alicyclic thermoplastic polyimide sheets from stereoisomeric hydrogenated pyromellitic dianhydrides and fluorinated diamine

Qi,

He,

Han

et al. 2024

J Polym Res

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Two semi-alicyclic thermoplastic polyimides (PI) have been prepared from stereoisomeric hydrogenated pyromellitic dianhydrides, including 1S,2R,4S,5R-hydrogenated pyromellitic dianhydride (ccHPMDA or H-PMDA) and 1R,2S,4S,5R-hydrogenated pyromellitic dianhydride (ctHPMDA or Hʹʹ-PMDA) and a fluorine-containing diamine, 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane (BDAF), respectively.The derived PI-1 (ccHPMDA-BDAF) and PI-2 (ctHPMDA-BDAF) resins were easily soluble in polar aprotic solvents, such as N-methyl-2-pyrrolidinone (NMP) and N,N-dimethylacetamide (DMAc) and meanwhile they also exhibited good thermoplasticities. Thus, the PI films (thickness: ~25 μm) and sheets (thickness: ~3 mm) were separately prepared from the PI solutions in DMAc and the PI powders, respectively. The stereoisomeric effects in the ccHPMDA-derived PI-1 and the ct-HPMDA-derived PI-2 apparently affected the melt-flowability of the polymers. PI-2 exhibited lower melting viscosities than that of the PI-1 counterpart. The PI sheets exhibited obviously reduced optical transparency compared with those of the PI films; however better optical transparency than those of the common thermoplastic PI sheets. For example, PI-2 sheet showed the optical transmittance value at the wavelength of 760 nm (T760) of 69.6%, which was 19.5% lower than that of the analogous PI-2 film (T760=89.1%), however 50.3% and 65.7% higher than those of the commercially available PI-ref1 sheet (T760=19.3%) derived from 3,3ʹ,4,4ʹ-oxydiphthalic dianhydride (ODPA) and 4,4ʹ-oxydianiline (ODA) and the PI-ref2 sheet (T760=3.9%, Aurum ® PL450C, Mitsui Chem. Co, Ltd., Japan), respectively.Meanwhile, the PI-1 and PI-2 sheets showed the heat deflection temperatures (HDT) of 261.0 o C and 265.0 o C, respectively, which were obviously higher than those of the referenced PIs. At last, the PI sheets exhibited good mechanical properties, including high flexural strength (130.0~132.0 MPa), flexural modulus (2.87~2.96 GPa), compression strength (124.4~149.3 MPa), compression modulus (1.49~1.59 GPa), and impact strength (129.0~139.6 KJ/m 2 ).

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Section: Introductionmentioning

confidence: 99%

Preparation and properties of semi-alicyclic thermoplastic polyimide sheets from stereoisomeric hydrogenated pyromellitic dianhydrides and fluorinated diamine

Qi,

He,

Han

et al. 2024

J Polym Res

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“…1,2 To overcome this issue, thermoplastic polyimide (TPI) is developed for adhesion application. 1,[3][4][5][6] In general, desirable TPI can be achieved by introducing flexible linkages, 4,[7][8][9] bulky side groups, 10,11 twisted noncoplanar structure [12][13][14][15][16][17] or asymmetric structure, 14,18 or copolymerization. 6,16,18,19 However, too soft linkage would enhance the movability of the polymer chain, leading to poor heat resistance and mechanical properties.…”

Section: Introductionmentioning

confidence: 99%

“…1,[3][4][5][6] In general, desirable TPI can be achieved by introducing flexible linkages, 4,[7][8][9] bulky side groups, 10,11 twisted noncoplanar structure [12][13][14][15][16][17] or asymmetric structure, 14,18 or copolymerization. 6,16,18,19 However, too soft linkage would enhance the movability of the polymer chain, leading to poor heat resistance and mechanical properties. Also, the strategy of bulky side groups always results in weakened intermolecular charge transfer complex (CTC) interaction, and thus undesirable dimensional stability.…”

Section: Introductionmentioning

confidence: 99%

Thermoplastic polyimide with good comprehensive performance based on carbazole groups and short flexible linkages

Du,

Chen,

Guo

et al. 2024

Journal of Polymer Science

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Thermoplastic polyimides (TPIs) can meet the requirements of advanced electronic packaging such as flexible copper clad laminate (FCCL) applied under extreme conditions, attributed to their excellent thermal stability, mechanical properties, electrical insulation and chemical resistance. With the increasing demands for electronic devices, such as applications in high‐frequency communication, it is highly desirable to develop high‐performance TPI with good thermoplasticity, thermal stability, mechanical properties and dielectric properties. However, there is a trade‐off between thermoplasticity and other properties. Herein, we introduce an effective strategy to afford TPIs with good performance by copolymerization of a diamine monomer consisted of a coplanar aromatic carbazole group and a short flexible linkage methylene group. On the one hand, short flexible linkages help improve the flexibility of polymer chains and are not too much to enable small‐scale molecular motions below Tg. On the other hand, coplanar aromatic donor groups benefit to strong charge transfer complex (CTC) interaction and π‐π stacking interaction. Based on this strategy, the resultant TPI possesses good thermoplasticity with a proper Tg of 348 °C. Meanwhile, it preserves a low coefficient thermal expansion of 48 ppm K−1, low dielectric constant/dielectric loss factor of 3.27/0.0073 at 10 GHz, and tensile strength of ca. 78 MPa.

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“…[3][4][5][6] Many efforts have been made to improve the thermoplasticity with storage modulus dropping exceeding 1000 MPa over T g , 5,7,8 including enhancing the flexibility of polymer chains, 5,[9][10][11] weakening intra-/inter-molecular interactions, 7,8,[12][13][14][15][16] and breaking the symmetric structure to some extent. 7,14,17 However, with the increasing demands for electronic devices in high-frequency communication, high-performance TPIs with low dielectric constant (D k )/dielectric loss factor (D f ) at high frequency are also highly desirable.…”

Section: Introductionmentioning

confidence: 99%

Thermoplastic polyimide with low dielectric properties enabled by the 2,2′‐spirobifluorene group

Jian,

Lu,

Zhang

et al. 2024

J of Applied Polymer Sci

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Thermoplastic polyimides (TPIs) have melt‐processability and adhesive ability, besides the intrinsic advantages of polyimides. To meet the requirements of applications in high‐frequency communication, TPIs with low dielectric constant (Dk)/dielectric loss factor (Df) at high frequency are also desirable. Enhancing the rigidity of polymer chains and simultaneously intermolecular interaction are effective ways to ensure low Dk/Df, which also benefit to heat resistance. However, it is not conducive to thermoplasticity, due to limited movement of polymer chains. To balance the trade‐off between them, we introduce noncoplanar 2,2′‐spirobifluorene groups to modify the rigidity of polymer chains and regulate the twist between electron‐donor moieties (diamine units) and electron‐acceptor moieties (dianhydride units). It leads to rigid polymer chains, which benefits to good heat resistance and dielectric properties. Meanwhile, the resultant irregular chain structure is difficult to crystallize, which results in thermoplasticity.

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Design and preparation of thermoplastic polyimides with high transmittance based on 4,4′-(4,4′-isopropyldiphenoxy)bis(phthalic anhydride) (BPADA)

Cited by 11 publications

References 26 publications

Preparation and properties of semi-alicyclic thermoplastic polyimide sheets from stereoisomeric hydrogenated pyromellitic dianhydrides and fluorinated diamine

Preparation and properties of semi-alicyclic thermoplastic polyimide sheets from stereoisomeric hydrogenated pyromellitic dianhydrides and fluorinated diamine

Thermoplastic polyimide with good comprehensive performance based on carbazole groups and short flexible linkages

Thermoplastic polyimide with low dielectric properties enabled by the 2,2′‐spirobifluorene group

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