Soluble polyimides from unsymmetrical diamine containing benzimidazole ring and trifluoromethyl pendent group

Choi, Hyungsam; Chung, Il-Moon; Hong, Ki-Sang; Park, Jin Young; Kim, Sang Youl

doi:10.1016/j.polymer.2008.04.019

Cited by 94 publications

(53 citation statements)

References 41 publications

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“…[6][7][8] Significant synthetic efforts in the area of high-performance polymers have been focused on improving the processability and solubility of PIs through the design and synthesis of new monomers. Various structural modifications can be made to the PI backbone to modify the polymer properties, such as insertion of flexible linkages on the main chain, 9-13 use of noncoplanar 14 or asymmetric monomers [15][16][17][18][19] and incorporation of pendant groups in the polymer backbone, [20][21][22][23][24][25][26][27][28][29] with results including lower interchain interactions or a reduced polymer chain stiffness. Depending on the type and amount of structural modifications, melting temperatures can be lowered and solubility improved, resulting in processable materials.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and identification of organosoluble polyimides: thermal, photophysical and chemiluminescence properties

Ghaemy

Nasab

2010

Polym J

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Novel fluorescent polyimides (PIs) were prepared from a new diamine, 4-(4-(4-amino-2-(4,5-diphenyl-1H-imidazol-2-yl) phenoxy)phenoxy)-3-(4,5-diphenyl-1H-imidazol-2-yl)benzenamine, and three tetracarboxylic dianhydrides. The new symmetrical diamine was successfully synthesized by the nucleophilic substitution reaction of hydroquinone with 2-(2-chloro-5-nitrophenyl)-4, 5-diphenyl-1H-imidazole (I). The PIs synthesized here are amorphous and soluble in polar aprotic solvents and demonstrate the ability to form films; their inherent viscosities ranged from 43 to 82 ml g À1 . The PIs had suitable thermal stability and relatively high T g values (245-274 1C), 10% weight loss temperatures in excess of 500 1C and char yields at 600 1C in air up to 62%. The PIs show emission in the solid state and in dilute (0.20 g per 100 ml) N,N-dimethyl acetamide solution at 431-464 nm with photoluminescence (PL) quantum yields in the range of 11-25%. The chemiluminescence activity of PIs in the presence of peroxyoxalate was also investigated. Polymer Journal (2010) 42, 648-656; doi:10.1038/pj.2010.57; published online 30 June 2010Keywords: fluorescent; polyimides; solubility; synthesis; thermal stability INTRODUCTION Aromatic polyimides (Pls) generally possess excellent thermal, mechanical, electrical and chemical properties. Therefore, they have been used in many applications such as electronics, coatings and adhesives, composite materials and membranes. 1-3 However, these polymers are difficult to process because of their high glass transition temperatures (T g ) or high melting temperatures (T m ) and their limited solubility in organic solvents. 4,5 Considerable efforts have been made to improve the solubility and melting processability of PIs while maintaining their desired properties. 6-8 Significant synthetic efforts in the area of high-performance polymers have been focused on improving the processability and solubility of PIs through the design and synthesis of new monomers. Various structural modifications can be made to the PI backbone to modify the polymer properties, such as insertion of flexible linkages on the main chain, 9-13 use of noncoplanar 14 or asymmetric monomers [15][16][17][18][19] and incorporation of pendant groups in the polymer backbone, 20-29 with results including lower interchain interactions or a reduced polymer chain stiffness. Depending on the type and amount of structural modifications, melting temperatures can be lowered and solubility improved, resulting in processable materials. Introducing bulky pendant substituents and heteroaromatic rings into PI chains has been considered to be an efficient method to provide not only enhanced solubility but also good thermal and thermo-oxidative stability. 22 The rigidity based on the

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Section: Introductionmentioning

confidence: 99%

Synthesis and identification of organosoluble polyimides: thermal, photophysical and chemiluminescence properties

Ghaemy

Nasab

2010

Polym J

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“…It seems that the chain structure of phenylethynylcarbonyl terminated imide compound which r1E9 2 5 E9 3FRT r1E9 2 5 E9 3FRT Figure 11. DMA curves of (a) phenylethynylcarbonyl terminated imide compound (PECI-APB) and (b) epoxy resin (EP) has more planar shape than epoxy resin affected the CTE more than the glass transition temperature of the polymer [19].…”

Section: Dma Analysis Of Phenylethynylcarbonyl Terminated Imide Compoundmentioning

confidence: 99%

Synthesis and characterization of phenylethynylcarbonyl terminated novel thermosetting imide compound

Kimura¹,

Ohtsuka²,

Matsumoto³

et al. 2013

Express Polym. Lett.

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Abstract. Phenylethynyl terminated novel imide compound based on 1,3-bis(3-aminophenoxy)benzene (APB) and phenylethynyl trimellitic anhydride (PETA) were prepared. The curing behavior of phenylethynyl terminated imide compound was investigated by differential scanning calorimetry and Fourier transform infrared spectrometry. The curing reaction of phenylethynylcarbonyl end group completed at 220°C, and proceeded much faster than that of phenylethynyl end group. Glass transition temperature of the thermosetting resin from phenylethynylcarbonyl terminated novel imide compound determined by dynamic mechanical analysis was almost the same as that of o-cresolnovolac type epoxy resin. In addition, the thermosetting resin from phenylethynylcarbonyl terminated novel imide compound exhibited excellent thermal and dimensional stabilities. These excellent properties of these phenylethynyl terminated imide compound might be due to the incorporation of alkene group or aromatic ring substitutes in the backbones, which might enhance the chain interaction (molecular packing) and reduce the molecular chain mobility.

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“…[3] Given these processing problems, a great deal of research on aromatic polyamides and polyimides has been conducted to increase their processability with minimal effects on the thermal stability and to improve their specific properties over the last few decades. [4][5][6][7][8] For example, polyamides and polyimides containing trifluoromethyl groups show a high modulus, a low thermal expansion coefficient as well as good solubility, [9][10][11][12][13][14][15][16][17][18][19][20][21] and the incorporation of heterocyclic units into polyimide chains increases the glass transition temperature and thermal stability. [22][23][24][25][26][27] Also, soluble polyamides and polyimides containing crosslinkable pendent groups represent useful methods in many applications.…”

Section: Introductionmentioning

confidence: 99%

New soluble polyamides and polyimides containing polar functional groups: pendent pyrazole rings with amino and cyano groups

Kim

Lee

et al. 2016

Designed Monomers and Polymers

Self Cite

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A series of aromatic polyamides and polyimides containing pendent pyrazole rings with amino and cyano groups were prepared from a new monomer, 1-(2,4-diaminophenyl)-3-phenyl-4-cyano-5-aminopyrazole, which was prepared from (chloromethylene)propanedinitrile and 2,4-dinitrophenyl hydrazine with two steps. In addition, model compounds were synthesized and characterized by elemental analyses, Fourier transform infrared (FTIR), and nuclear magnetic resonance (NMR) spectroscopy. The amino and cyano groups on the pyrazole ring were not affected during the polymerization process. The synthesized polymers, with intrinsic viscosities of 0.33-0.53 dL/g, were soluble in various organic solvents. They showed no T g values before degradation, and the 5% weight loss temperature of the polyamides and the polyimides occurred at approximately 420 and 470 °C, respectively. They also underwent no thermal transitions, such as degradation or crosslinking, up to 440 °C in spite of the presence of pendent amino and cyano groups.

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Soluble polyimides from unsymmetrical diamine containing benzimidazole ring and trifluoromethyl pendent group

Cited by 94 publications

References 41 publications

Synthesis and identification of organosoluble polyimides: thermal, photophysical and chemiluminescence properties

Synthesis and identification of organosoluble polyimides: thermal, photophysical and chemiluminescence properties

Synthesis and characterization of phenylethynylcarbonyl terminated novel thermosetting imide compound

New soluble polyamides and polyimides containing polar functional groups: pendent pyrazole rings with amino and cyano groups

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