Organosoluble polyimides derived from asymmetric 2‐substituted‐and 2,2′,6‐trisubstituted‐4,4′‐oxydianilines

Chen, Jyh‐Chien; Wu, Jin-An; Chang, Hui‐Wen; Lee, Ching‐Yi

doi:10.1002/pi.4571

Cited by 9 publications

(10 citation statements)

References 34 publications

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“…30 It suggested that BADCy self-polymerized and gave a triazine structure (I). Absorption at 690 cm 21 belonged to carbon-carbon double bond of maleimide 31 weakened as the cure temperature rose, which implied that the homopolymerization of DOPO-BMI (II) or the co-curing of DOPO-BMI and BADCy occurred at high temperatures. According to the research of Lin 30 , the characteristic absorption at 1365 cm 21 may be presumably attributed to the pyrimidine structures (III) and the pyridine structures (IV) which are formed via the co-reaction of bismaleimide and cyanate resin.…”

Section: Article Wileyonlinelibrarycom/appmentioning

confidence: 97%

“…In this work, the unsymmetrical structure and the DOPO pendant group reduce the molecular symmetry of DOPO-BMI, thus reduce the crystallinity and improve the solubility of bismaleimide monomer in the low-boiling-point solvents, such as acetone, ethyl acetate, and tetrahydrofuran. For example, DOPO-BMI can facilely dissolve in acetone in high concentrations (>100 mg mL 21 ). The solubility results are summarized in Table I. DOPO-BMI shows a glass transition at about 1358C in the DSC curve ( Figure 3) without obviously melting exothermic peak.…”

Section: Solubility and Morphology Of Dopo-bmi Monomermentioning

confidence: 99%

“…In all cases, 32 scans at a resolution of 4 cm 21 were used to record the spectra ranging from 400 to 4000 cm 21 . Nuclear magnetic resonances were performed on a Bruker DMX500 with dimethyl sulfoxide-d 6 (DMSO-d 6 ) as solvent.…”

Section: Characterizationsmentioning

confidence: 99%

“…Otherwise, the solvent is considered insoluble, marked as "X" in Table I. The viscosity of prepared BT resins were carried out on a Thermofisher HAAKE MARS III rotary rheometer with a shear rate at 5 s 21 and a heating rate at 58C min 21 in the temperature range of 130-1808C.…”

Section: Characterizationsmentioning

confidence: 99%

“…Based on the structure-property relationship, the unsymmetrical molecular structure and bulky pendant group are helpful for improving the solubility of the molecules. [18][19][20][21] Chen et al reported a series of bismaleimides with a bulky phthalide group or unsymmetrical structure, which are soluble in organic solvents such as acetone, dichloromethane, and tetrahydrofuran. 22,23 9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) has usually been used to improve the thermal performance and flame retardancy of materials.…”

Section: Introductionmentioning

confidence: 98%

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High glass transition temperature bismaleimide‐triazine resins based on soluble amorphous bismaleimide monomer

Ren

Cheng

Kong

et al. 2015

J of Applied Polymer Sci

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A novel bismaleimide (DOPO-BMI) with unsymmetrical chemical structure and DOPO pendant group has been prepared. The particular molecular structure makes DOPO-BMI show an intrinsic amorphous state with a T g about 1358C and excellent solubility in most organic solvents, which is beneficial to the processability of bismaleimide composite materials. A series of bismaleimide-triazine (BT) resins have been prepared based on DOPO-BMI and 2,2-bis(4-cyanatophenyl)propane at various weight ratios. The prepared BT resins show outstanding solubility in organic solvent and low viscosity about 10-671 mPa s at 1808C. The cured BT resins exhibit high glass transition temperature (T g ) over 3168C. As the weight ratio of DOPO-BMI increases to 80% (BT80), the T g can rise to 3698C (tan d). The cured BT resins also show good thermal stability with the 5% weight loss temperature over 4008C under both nitrogen and air atmosphere.

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Section: Article Wileyonlinelibrarycom/appmentioning

confidence: 97%

Section: Solubility and Morphology Of Dopo-bmi Monomermentioning

confidence: 99%

Section: Characterizationsmentioning

confidence: 99%

Section: Characterizationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

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High glass transition temperature bismaleimide‐triazine resins based on soluble amorphous bismaleimide monomer

Ren

Cheng

Kong

et al. 2015

J of Applied Polymer Sci

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Design and synthesis of organosoluble and transparent polyimides containing bulky substituents and noncoplanar structures

Huang

Pei

Wang³

et al. 2015

J of Applied Polymer Sci

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A new diamine monomer, 3,3 0 -diisopropyl-4,4 0 -diaminophenyl-4 00 -phenyltouene, was designed, synthesized, and then polymerized with five commercial dianhydrides to obtain a series of novel polyimides via a one-step method. The obtained polymers showed excellent solubility in most common solvents, even in low-boiling solvents, such as chloroform, dichloromethane, and tetrahydrofuran. They exhibited a high thermal stability with the glass-transition temperature in the range 262-3188C and 10% weight loss temperatures in the range 464-4888C under a nitrogen atmospheres. Meanwhile, these polymer films also displayed a high optical transparency with a cutoff wavelength in the range 305-365 nm; prominent mechanical properties with a tensile strength of 65.6-94.9 MPa, a Young's modulus of 1.6-2.8 GPa, and an elongation at break of 9.3-13.7%; a low dielectric constant in the range of 2.91-3.18 at 1 MHz; and an outstanding hydrophobicity with a contact angle above 90.68. V C 2015 Wiley Periodicals, Inc. J.Appl. Polym. Sci. 2016, 133, 43266.

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Synthesis and thermal, mechanical and gas permeation properties of aromatic polyimides containing different linkage groups

Sava¹,

Chişcă²,

Wolińska‐Grabczyk

et al. 2014

Polym. Int.

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Two series of aromatic polyimides containing various linkage groups based on 2,7-bis(4-aminophenoxy)naphthalene or 3,3 ′ -dimethyl-4,4 ′ -diaminodiphenylmethane and different aromatic dianhydrides, namely 4,4 ′ -(4,4 ′ -isopropylidenediphenoxy) bis(phthalic anhydride), 4,4 ′ -(hexafluoroisopropylidene)bis(phthalic anhydride), 3,3 ′ ,4,4 ′ benzophenonetetracarboxylic dianhydride, 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride and 4,4 ′ -(4,4 ′ -hexafluoroisopropylidenediphenoxy)bis (phthalic anhydride), were synthesized and compared with regard to their thermal, mechanical and gas permeation properties. All these polymers showed high thermal stability with initial decomposition temperature in the range 475-525 ∘ C and glass transition temperature between 208 and 286 ∘ C. Also, the polymer films presented good mechanical characteristics with tensile strength in the range 60-91 MPa and storage modulus in the range 1700-2375 MPa. The macromolecular chain packing induced by dianhydride and diamine segments was investigated by examining gas permeation through the polymer films. The relationships between chain mobility and interchain distance and the obtained values for gas permeability are discussed.

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Organosoluble polyimides derived from asymmetric 2‐substituted‐and 2,2′,6‐trisubstituted‐4,4′‐oxydianilines

Abstract: A concise method is reported for the preparation of asymmetric polyimides based on 2‐substituted‐ and 2,2′,6‐trisubstituted‐4,4′‐oxydianilines. Their structural asymmetry is evidenced using 1H NMR spectroscopy. Their solubility and thermal properties are reported.

Cited by 9 publications

References 34 publications

High glass transition temperature bismaleimide‐triazine resins based on soluble amorphous bismaleimide monomer

High glass transition temperature bismaleimide‐triazine resins based on soluble amorphous bismaleimide monomer

Design and synthesis of organosoluble and transparent polyimides containing bulky substituents and noncoplanar structures

Synthesis and thermal, mechanical and gas permeation properties of aromatic polyimides containing different linkage groups

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