• Title/Summary/Keyword: hexafluoroisopropylidene

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Synthesis of Polyimides Derived from 2,2-Bis[4-(4-aminobenzoyl)phenoxy]hexafluoropropane and Aromatic Dianhydrides (2,2-Bis[4-(4-nitrobenzoyl)phenoxy]hexafluoropropane과 방향족 이무수물을 사용한 폴리이미드의 합성)

  • Park, Jung Hye;Ahn, Byung Hyun
    • Applied Chemistry for Engineering
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    • v.27 no.1
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    • pp.50-55
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    • 2016
  • Aromatic diamines containing hexafluoroisopropylidene and ester moiety were synthesized from 4,4'-hexafluoroisopropylidene diphenol and nitrobenzoyl chloride. The reaction of aromatic diamines with hexafluoroisopropylidene phthalicdianhydride (6FDA) or pyromellitic dianhydride (PMDA) gave four kinds of poly(amic acid)s. Their inherent viscosities ranged from 0.196 to 0.346 dL/g. Poly(amic acid)s were converted to polyimides by thermal imidization. The glass transition temperatures ($T_g$) of polyimides were between 241 and $289^{\circ}C$. The 5% weight loss temperatures were recorded in the range of $430{\sim}492^{\circ}C$. The tensile strength of polyimide films were measured as 29.84~64.38 MPa.

Second-Order Optical Nonlinearity of a Polyamide derived from 4,$4^{\prime}$-[Hexafluoroisopropylidene]dianiline and 4-[N,N-Bis(2-carboxyethyl)] amino-$4^{\prime}$-nitrostilbene

  • 김영운;진정일
    • Bulletin of the Korean Chemical Society
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    • v.19 no.7
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    • pp.738-742
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    • 1998
  • A new polyamide was prepared from 4,4'-(hexafluoroisopropylidene)di-aniline and 4-[NN-bis(2-carboxyethyl)] amino-4'-nitrostilbene. This polymer was cast into thin films by spin coating cyclohexanone solution. After being poled, the electro-optic coefficients of electrode poled polymer films were measured by the reflection measurement technique using an incident laser beam of 1.3 Jim. The film poled at the field strength of 1.2 V/μm exhibited the electro-optic coefficient (r33) of 5.9 pm/V. The relaxation behavior of the poled polymer film was compared with other reported polymers bearing the same NLO chromophores. Due to stiff and highly polar nature of the backbone and also due to formation of interchain hydrogen bonds, this polymer reveals a slower relaxation characteristics. The polymer is amorphous and soluble in various organic solvents.

Syntheses of Colorless and Transparent Copolyimides and Comparison of the Properties of Their Copolyimides (무색 투명 폴리이미드 공중합체의 합성 및 물성 비교)

  • Ju, Jieun;Chang, Jin-Hae
    • Polymer(Korea)
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    • v.39 no.2
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    • pp.275-280
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    • 2015
  • Two series of copolyimides (Co-PIs) were prepared by reacting 4,4'-(hexafluoroisopropylidene) diphthalic anhydride (6FDA) and 1,2,4,5-benzentetra carboxylic dianhydride (pyromellitic dianhydride) (PMDA), as dianhydrides based on 4,4'-biphthalic anhydride (BPA) and 2,2'-bis(trifluoromethyl)benzidine (TFB) by using thermal- and chemical imidizations. Co-PIs films with different dianhydride monomer compositions were compared in terms of their thermal properties and optical transparencies. The addition of PMDA was more effective than the addition of 6FDA for improving the thermal properties. Meanwhile, 6FDA is more effective in optical transparencies.

Synthesis of Polyimide Derived from 4-Methyl-1,2-phenylene Bis(4-aminobenzoate) and 4,4'-Hexafluoroisopropylidenediphthalic Anhydride

  • Byung Hyun Ahn
    • 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.

Preparation and Properties of Soluble Polyimide with Methacryloyl Group (Methacryloyl기를 함유한 가용성 폴리이미드의 합성과 감광 특성)

  • Yoon, Keun-byoung;Son, Hyung-jun;Lee, Dong-ho
    • 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.

The Change of Properties and Synthesis of Soluble Polyimides Based on 2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane (2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane을 이용한 용해성 폴리이미드의 합성과 특성변화)

  • Kim, Han-Sung;Ha, Soon-Hyo;Chun, Kyoung-Yong;Han, Hak-Soo;Joe, Yung-il
    • 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.

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Synthesis and Property of Colorless Polyimide and Its Nanocomposite for Plastic Display Substrate (유연성 디스플레이 기판 소재용 투명성 폴리이미드의 합성 및 그의 나노복합화에 대한 연구)

  • Ma Seung Lac;Kim Yong Seok;Lee Jae Heung;Kim Jung Su;Kim Insun;Won Jong Chan
    • Polymer(Korea)
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    • v.29 no.2
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    • pp.204-210
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    • 2005
  • We describe a colorless, transparent polyimide films for plastic display substrate which should have heat resistance, roll-to-roll processability and low CTE (coefficient of thermal expansion) property. Colorless polyimides were synthesized from 3,3',4,4'-oxydiphthalic anhydride (ODPA) 4,4'-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) and diamines such as sulfonyldianiline, aminophenoxybenzene (TPE-p, TPE-q, TPE-r) and bis[4-(3-aminophen oxy)phenyl] sulfone (m-BAPS). Their optical properties were measured by UV spectrophotometer, colormeter and hazemeter. We prepared polyimide/organophilic layered silicate nanocomposite to improve dimension stability. These colorless polyimide films showed UV transmittance by the level upper $89\%$, at 440 nm and excellent optical property having the value under yellow index (YI)=7. In addition, polyimide nanocomposite films also showed an improvement of CTE value as decreased according to the amount of layered silicate contents.

Pervaporation Separation of Trace Dicholoromethane from Water Using Fluorinated Polysiloxaneimide do Membranes (불소계 폴리실록산이미드 공중합체막을 이용한 저농도 Dichloromethane 수용액의 투과증발)

  • Kim, Jeong-Hoon;Chang, Bong-Jun;Lee, Soo-Bok
    • Membrane Journal
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    • v.17 no.3
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    • pp.184-190
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    • 2007
  • This study reports on the pervaporation separation of a volatile organic compound(VOC), dichloromethane(DCM) from water using fluorinated copolysiloxaneimide membranes. The copolysiloxaneimide membranes were prepared from 4,4'-(hexafluoroisopropylidene)diphthalic anhydride(6FDA) and two diamines(polysiloxane diamine(SIDA), 2-(perfluorohexyl)ethyl-3,5-diaminobenzene(PFDAB)). By varying the ratio of flexible polysiloxane diamine(SIDA)/rigid fluorinated aromatic diamine(PFDAB) from 0/100 to 100/0 mol%, five copolysiloxaneimide membranes were prepared success- fully. The pervaporation properties of DCM/water were examined in terms of two diamine monomer ratio at room temperature and the feed composition of 0.05 wt% in water. It was found that the increase in SIDA content led to high permeation flux and pervaporation selectivity towards DCM by the enhanced sorption/sorption selectivity and diffusion coefficient/diffusion selectivity due to the increased hydrophobicity and fractional free volume.

Comparison of Colorless and Transparent Polyimide Films with Various Amine Monomers (다양한 아민 단량체를 이용한 무색 투명 폴리이미드 필름의 특성비교)

  • Kim, Youngmin;Chang, Jin-Hae
    • Applied Chemistry for Engineering
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    • v.23 no.3
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    • pp.266-270
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    • 2012
  • A series of polyimide was prepared by reacting 4,4'-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) as the anhydride monomer and 2,2'-bis(trifluoromethyl)benzidine (TFB), 2,2'-bis(3-aminophenyl)hexafluoropropane (BAFP), 2,2'-bis(3- amino- 4-methylphenyl) hexafluoropropane (BAMF), bis(3-aminophenyl)sulfone (APS), p-xylyenediamine (p-XDA), or m-xylyenediamine (m-XDA) as the amine monomer in N,N-dimethylacetamide (DMAc). Colorless and transparent polyimide (PI) films were obtained by casting the poly(amic acid)s (PAAs) solution at various heat treatment temperatures. The thermal properties of the PI films were examined using differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and thermomechanical analysis (TMA) and the mechanical properties were investigated using universal tensile machine (UTM), Their optical transparencies were also investigated using ultraviolet-visible (UV-vis.) spectrophotometry and colorimetry. The yellow index (YI) and coefficient of thermal expansion (CTE) values of all PIs were in the range 0.98~2.76 and 25.73~55.23 $ppm/^{\circ}C$, respectively.

Analysis of Thermal Imidization Kinetics of 6FDA-BAPP Polyimide in Relation with Solvent Evaporation (6FDA-BAPP 폴리이미드 열축합 반응에서의 잔류용매에 따른 이미드화거동 연구)

  • Lee, Eun-Young;Hwang, Tae-Seon;Nam, Jae-Do
    • Polymer(Korea)
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    • v.36 no.4
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    • pp.448-454
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    • 2012
  • A poly(amic acid) (PAA) was prepared by reaction of 4,4'-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) and 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluropropane (BAPP) in N,N-dimethylacetamide (DMAc). The cast films of the synthesized PAA were thermally treated at different temperatures to create polyimide (PI) films. The heat treatment temperature varied between 80 and $230^{\circ}C$ to investigate the imidization index in relation with the solvent evaporation rates. The progress of PAA imidization was examined using a thermogravimetric analyzer (TGA) and a Fourier transform infrared spectroscope (FTIR) at various time and temperature. The experimental results showed that the imidization index was fast at the initial stage in the presence of solvent, DMAc, reaching the final imidization. When the imidization temperature is high over $200^{\circ}C$, the imidization index decreased because the solvent was evaporated too fast.