• Elastomers and Composites
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• v.59 no.3
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• pp.91-96
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• 2024

A novel aromatic polyimide containing the 4-tert-butyl group was prepared from 4-tert-butyl-1,2-phenylene bis(4-aminobenzoate) and 4,4'-(hexafluoroisopropylidene)diphthalic anhydride (6FDA). 4-tert-Butyl-1,2-phenylene bis(4-aminobenzoate) was synthesized from 4-tert-butyl catechol and 4-nitrobenzoyl chloride. The poly(amic acid) was transformed into a polyimide via chemical imidization. The polyimide was soluble in N-methyl-2-pyrrolidone (NMP) and could be cast into a flexible and transparent film. The thermal stability of the polyimide was decreased slightly due to the pendant tertbutyl group.

• Elastomers and Composites
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• v.58 no.1
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• pp.26-31
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• 2023

Aromatic diamine containing ortho catenation and methyl group was synthesized from 4-methyl catechol and 4-nitrobenzoyl chloride. Subsequently, a poly(amic acid) was prepared by reacting 4-methyl-1,2-phenylene bis(4-aminobenzoate) with 4,4'-hexafluoroisopropylidenediphthalic anhydride (6FDA). The resulting poly(amic acid) was transformed into a polyimide through chemical imidization. The polyimide formed was soluble in N-methyl-2-pyrrolidone (NMP) and could be cast into a flexible, transparent film. Furthermore, the polyimide exhibited a 5% weight loss at 380 ℃ in the nitrogen atmosphere.

• Applied Chemistry for Engineering
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• v.17 no.2
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• pp.217-222
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• 2006

Polyimides have been investigated extensively and used widely over the past three decades because of their high performance properties such as excellent thermal, mechanical, and electrical properties. Polyimides are difficult to be processed because of the aromatic moieties, imide group, and insoluble nature in most organic solvents. The soluble polyimides were synthesized from 2,2,-bis(3-amino-4-hydroxyphenyl) hexafluoropropane (BAPAF) and 3,3,-diamino-4,4-dihydroxybyphenyl (HAB) as aromatic diamines and 4,4-(hexafluoroisopropylidene)diphthalic dianhydride (6FDA), pyromellitic dianhydride (PMDA), 4,4-oxydiphthalic dianhydride (OPDA), 3,3,4,4-benzophenone tetracarboxylic dianhydride (BTDA) and 3,3,4,4-diphenylsulfone tetracarboxylic dianhydride (DSDA) as aromatic dianhydrides. The polyimides were characterized by NMR, FR-IR, TGA and the dielectric constant of the obtained polyimides was calculated from storage of electro-capacity. A novel photosensitive polyimide was synthesized by the reaction of polyimide, containing hydroxyl group and methacryloyl chloride using triethylamine. The good micro-pattern was obtained with photosensitive polyimide from the photolithographic technique.

• Bulletin of the Korean Chemical Society
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• v.22 no.5
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• pp.451-452
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• 2001

• Macromolecular Research
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• v.14 no.3
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• pp.300-305
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• 2006

The chemical structure of a semi-aromatic polyimide-I, which was prepared by the chemical imidization of cyclopentanetetracarboxylic dianhydride and 2,2-bis(4-aminophenyl)hexafluoropropane, was characterized by $^{13}C-NMR$ spectroscopy. The chemically imidized polyimide-I was used for the preparation of a photosensitive polyimide (PSPI) through the addition of benzophenone and benzophenone oxime hexamethylene diurethane (BOHD), a photobase generator containing oxime-urethane groups. The polyimide-I film containing benzophenone and BOHD was not soluble in 2.38 wt% tetrabutylammonium hydroxide solution in $H_2O$. However, it became soluble following irradiation with 310 nm UV light. A positive tone image with a resolution of $5{\mu}m$ was obtained with this PSPI, having sensitivity($D_c$) of $1.2J/cm^2$ and contrast(${\gamma}_p$) of 1.08. Thus, a polyimide, which is not intrinsically photosensitive, can become photosensitive through the addition of a photobase generator containing oxime-urethane groups as a photosensitive compound.

• Proceedings of the Membrane Society of Korea Conference
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• 1993.10a
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• pp.7-12
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• 1993

Preparation of asymmetric polyimide membranes by the phase inversion process was investigated to develop ultrafiltration, reverse osmosis and pervaporation membranes for organic solutions, using a commercially available solvent-soluble polymaide. The influences of the various factors such as the composition of a cast solution, casting conditions, gelating solutions and others on membrane structure and performance were studied in detail, and it was made clear that a wide variety of asymmetric polyimide membranes ranging from UF to RO for organic solutions could be prepared from the aromatic polyimide used. It was also found that the chemical stability and separation performance of the asymmetric polyimide membranes could be improved by annealing in a liquid or a vacuum at above 200$\circ$. The membrane annealed at 300$\circ$ in a vacuum exhibited the separation factor $\alpha(H_2O/EtOH)$ of 900 with the flux of 1.0 kg/$m^2\cdot h$ at 60$\circ$C for an aqueous ethanol solution of 95 vol%.

• Macromolecular Research
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• v.17 no.12
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• pp.976-986
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• 2009

With the study goal of firstly elucidating the anisotropic interactions between oriented polymer chain segments and liquid crystal (LC) molecules, and secondly of determining the contributions of the chemical components of the polymer segments to the film surface topography, LC alignment, pretilt, and anchoring energy, we synthesized three dianhydrides, 1,4-bis(4'-t-butylphenyl)pyromellitic dianhydride (BBPD), 1,4-bis(4'-trimethylsilylphenyl)pyromellitic dianhydride(BTPD), and 2,2'-bis(4"-tert-butylphenyl)-4,4',5,5'-biphenyltetracarboxylic dianhydride (BBBPAn), and a series of their organosoluble polyirnides, BBPD-ODA, BBPD-MDA, BBPD-FDA, BTPD-FDA, and BBBPAn-FDA, which contain the diamines 4,4'-oxydianiline (ODA), 4,4'-methylenediamine (MDA), and 4,4'-(hexafluoroisopropylidene)dianiline (FDA). All the polyimides were determined to be positive birefringent polymers, regardless of the chemical components. Although all the rubbed polyimide films exhibited microgrooves which were created by rubbing process, the film surface topography varied depending on the polyimides. In all the rubbed films, the polymer chains were unidirectionally oriented along the rubbing direction. However, the degree of in-plane birefringence in the rubbed film varied depending on the polyimides. The rubbing-aligned polymer chains in the polyimide films effectively induced the alignment of nematic LCs along their orientation directors by anisotropic interactions between the preferentially oriented polymer chain segments and the LCs. The azimuthal and polar anchoring energies of the LCs ranged from $0.45{\times}10^{-4}\;-\;1.37{\times}10^{-4}\;J/m^2$ and from $0.86{\times}10^{-5}\;-\;4.26{\times}10^{-5}\;J/m^2$, respectively, depending on the polyimides. The pretilt angles of the LCs were in the range $0.10-0.62^{\circ}$. In summary, the soluble aromatic polyimides reported here are promising LC alignment layer candidates for the production of advanced LC display devices.

• Macromolecular Research
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• v.14 no.1
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• pp.1-33
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• 2006

Polyimides (PIs) exhibit excellent thermal stability, mechanical, dielectric, and chemical resistance properties due to their heterocyclic imide rings and aromatic rings on the backbone. Due to these advantageous properties, PIs have found diverse applications in industry. Most PIs are insoluble because of the nature of the high chemical resistance. Thus, they are generally used as a soluble precursor polymer, which forms complexes with solvent molecules, and then finally converts to the corresponding polyimides via imidization reaction. This complexation with solvent has caused severe difficulty in the characterization of the precursor polymers. However, significant progress has recently been made on the detailed characterization of PI precursors and their imidization reaction. On the other hand, much research effort has been exerted to reduce the dielectric constant of PIs, as demanded in the microelectronics industry, through chemical modifications, as well as to develop high performance, light-emitting PIs and liquid crystal (LC) alignment layer PIs with both rubbing and rubbing-free processibility, which are desired in the flat-panel display industry. This article reviews this recent research progresses in characterizing PIs and their precursors and in developing low dielectric constant, light-emitting, and LC alignment layer PIs.

• Applied Chemistry for Engineering
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• v.10 no.7
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• pp.979-984
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• 1999

Aromatic soluble polyimides were synthesized from 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane and various dianhydrides such as pyromelltic dianhydride(PMDA), 3,3',4,4'-benzophenone tetracarboxylic dianhydride(BTDA), and 4,4'-(hexafluoroisopropylidene)-bis(phthalic anhydride)(6FDA). Polyimides prepared by thermal imidization were insoluble in common organic solvents (acetone, MNP, DMAc, DMSO, THF, and DMF) but those prepared by chemical imidization were soluble. The difference of solubility was explained by esterification between hydroxyl group and $CH_3COO^-$ from acetic anhydride used as a dehydration agent in chemical imidization. Glass transition temperatures of polyimides by thermal method were higher than those by chemical method. All of the polyimides are stable up to $300^{\circ}C$ regardless of the sample preparation. The x-ray diffraction patterns showed that all polyimides were amorphrous.

• Polymer(Korea)
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• v.28 no.4
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• pp.314-320
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• 2004

Soluble aromatic polyimides bearing 4-(4-oxyalkyleneoxystyryl)- pyridines (ethylene and hexylene) as photoreactive side groups were synthesized and characterized. The photoreactive polymers were soluble in various polar organic solvents and their films were easily formed by solution casting. The photoreactivities of the polymers in the film state were approximately 64% at an exposure energy of 1.5 J/$\textrm{cm}^2$. Transmittances of the polymer films were about 85% after annealing at 20$0^{\circ}C$. Therefore, these polymers can be evaluated to be photoreactive polyimides with good transparency and solubility. The dichroic ratios of the polymers with ethylene and hexylene groups as the alkylene spacers were 0.023 and 0.026, respectively. The order parameters of 4'-pentyl-4-bipheny1carbonitrile as a liquid crystal (LC) in the film cells of the former and latter polymers were 0.50 and 0.52, respectively. These results indicate that the polymers show the effect of alkylene spacer on the photoalignments. The LC in the film cells of the polymers was perpendicularly oriented to the electric vector of the linear polarized UV light (LPUVL).