Synthesis and properties of polyimides derived from 9,10‐dialkyloxy‐1,2,3,4,5,6,7,8‐octahydro‐2,3,6,7‐anthracenetetracarboxylic 2,3:6,7‐dianhydrides

Kim, Yong Seok; Jung, Jin Chul

doi:10.1002/pola.10248

Cited by 17 publications

(10 citation statements)

References 25 publications

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“…This observation is reasonable because the presence of the pentadecyl chain leads to the formation of layered structures. It is well known that polymers with flexible long chains strongly tend to form layered crystalline structures in the solid state …”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of polyetherimides containing multiple ether linkages and pendent pentadecyl chains

2015

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4-(4-(4-(4-Aminophenoxy)-2-pentadecylphenoxy)phenoxy)aniline (APPPA) was synthesized starting from cashew nut shell liquid-derived bisphenol, i.e. 4-(4-hydroxyphenoxy)-3-pentadecylphenol, by nucleophilic substitution reaction with 4-chloronitrobenzene followed by reduction of the formed 4-(4-nitrophenoxy)-1-(4-(4-nitrophenoxy)phenoxy)-2pentadecylbenzene. Three new polyetherimides containing multiple ether linkages and pendent pentadecyl chains were synthesized by one-step high-temperature solution polycondensation of APPPA in m-cresol with three aromatic dianhydrides, i.e. 3,3 ′ ,4,4 ′ -oxydiphthalic anhydride, 4,4 ′ -(hexafluoroisopropylidene)diphthalic anhydride and 3,3 ′ ,4,4 ′ -biphenyltetracarboxylic dianhydride. Inherent viscosities and number-average molecular weights of the polyetherimides were in the ranges 0.66-0.70 dL g −1 and 17 100-29 700 g mol −1 (gel permeation chromatography, polystyrene standards), respectively, indicating the formation of reasonably high molecular weight polymers. The polyetherimides were soluble in organic solvents such as chloroform, dichloromethane, tetrahydrofuran, pyridine, m-cresol, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and dimethylsulfoxide, and could be cast into transparent, flexible and tough films from their solutions in chloroform. The polyetherimides exhibited glass transition temperatures (T g ) in the range 113-131 ∘ C. The lowering of T g could be attributed to the combined influence of flexibilizing ether linkages and pentadecyl chains which act as 'packing-disruptive' groups. The temperature at 10% weight loss (T 10 ), determined from thermogravimetric analysis in nitrogen atmosphere, was in the range 460-470 ∘ C demonstrating good thermal stability. The virtues of solubility and large gap between T g and T 10 mean that the polyetherimides containing pendent pentadecyl chains have possibilities for both solution as well as melt processability.

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Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of polyetherimides containing multiple ether linkages and pendent pentadecyl chains

2015

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“…Polyimides with aromatic side groups or trifluoromethyl usually keep their inherent high thermal stability, for example, polyimides containing phenyls or naphthyls are stable up to 519 °C and ones containing trifluoromethyls are stable up to 500 °C . However, polyimides containing aromatic heterocyclic groups or linear alkyls often display relatively low thermal stability, for example, polyimides with side pyridyl showed an obvious decomposition at around 300 °C, and ones with –C 12 H 25 started to decompose at about 400 °C . This can be attributed to the low thermal stability of pyridinyl and linear alkyls themselves.…”

Section: The Effects Of Side Groups On Physical Properties Of Polyimidesmentioning

confidence: 70%

“…However, the thermal stability of polyimides was dramatically destroyed due to the poor thermal stability of long linear alkyls. For example, polyimides prepared from diamine 16 with –C 15 H 31 (Scheme ), diamine 17 with –C 4 H 9 , diamine 18 with –C 8 H 17 , and diamine 19 with –C 12 H 25 (Scheme ) exhibited a different solubility in organic solvents . With increasing the length of linear side alkyl groups, the solubility of corresponding polyimides are improved gradually.…”

Section: The Effects Of Side Groups On Physical Properties Of Polyimidesmentioning

confidence: 95%

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Polyimides with side groups: Synthesis and effects of side groups on their properties

Lee

Huang

Yan

2016

J. Polym. Sci. Part A: Polym. Chem.

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Polyimides are a class of well‐known high‐performance polymers combined the excellent mechanical, electrical, and thermal properties and widely applied in many high‐tech fields. Traditional polyimides can only be processed in the state of soluble intermediates with a hazardous step of cyclodehydration and elimination of a nonvolatile polar solvent. Therefore, a great effort has been devoted to the development of soluble polyimides that can be processed in the full imidation state. The incorporation of side groups into the polyimide backbone is an efficient approach to resolve above problems with a little sacrifice of its inherent merits. The subtle variation of side groups in polyimide backbones has allowed researchers to tune their final properties. In particular, some special side groups can endow polyimides the specific property or functionality to broaden their application fields. In this article, we summarize the synthesis of polyimides with side groups in recent 20 years and further discuss the effect of side groups on their physical and specific properties. The future research directions of polyimides with side groups are also discussed. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 533–559

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“…The path for synthesis of monomer MPBB is illustrated in Scheme . First 1,4‐di(4‐methyloxy)phenyloxy‐2,3,5,6‐tetramethylbenzene (MPD) was prepared in DMF by the Ullmann nucleophilic substitution reaction of 1,4‐dibromo‐2,3,5,6‐tetramethylbenzene with 4‐(methyloxy)phenol using CuCl as activator21 and K 2 CO 3 as HBr absorber and then the four methyl groups of MPD's central benzene ring was monobrominated under CCl 4 reflux with excess NBS in the presence of catalytic amount of BPO as free radical initiator 22. Even though the Ullmann reaction is long known,21 we achieved only 55% yield and we found that the addition of CuCl and K 2 CO 3 in two portions is critical in achieving the 55% yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of new alicyclic polyimides by Diels‐Alder polymerization

Shin

Kim

et al. 2007

J of Applied Polymer Sci

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Four new alicyclic poly{arylene-9,10-di[4-(methyloxy)phenyloxy]-1, 2,3,4,5,6,7,3,6, were prepared at 808C in the presence of NaI in DMSO by the in situ Diels-Alder polymerization of 1,4-bis[4-(methyloxy)phenyloxy]-2,3,6,7-tetrakis(bromomethyl)benzene (MPBB) with four arylenebismaleimides (AMIs). The stereochemical isomerisms measured for the model compound DPAI and MDA-PI by HETCOR spectroscopy and 1 H-NMR spectroscopy, respectively, revealed that DPAI and APIs presumably have only one trans-bis-endo-configuration. Inherent viscosities of APIs varied in the 0.20-0.41 dL/g range. Solubility tests revealed that in spite of the alicyclic units incorporated the APIs were only marginally soluble in polar organic solvents. In TGA in N 2 the APIs began to decompose at temperatures higher than 3808C, revealing two-step pyrolysis behavior. 4-(Methyloxy)-phenyloxy side groups were believed to degrade in the lower temperature range. In DSC and wide-angle X-ray diffractometry APIs all appeared completely amorphous and in UV-Vis spectroscopy both DPAI and APIs were transparent at wavelengths longer than 375 nm.

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Synthesis and properties of polyimides derived from 9,10‐dialkyloxy‐1,2,3,4,5,6,7,8‐octahydro‐2,3,6,7‐anthracenetetracarboxylic 2,3:6,7‐dianhydrides

Cited by 17 publications

References 25 publications

Synthesis and characterization of polyetherimides containing multiple ether linkages and pendent pentadecyl chains

Synthesis and characterization of polyetherimides containing multiple ether linkages and pendent pentadecyl chains

Polyimides with side groups: Synthesis and effects of side groups on their properties

Synthesis of new alicyclic polyimides by Diels‐Alder polymerization

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