Synthesis of thermally crosslinkable fluorine‐containing poly(arylene ether ketone)s—II. Propargyl ether terminated poly(arylene ether ketone)s

Kimura, Kunio; Nishichi, Ai; Yamashita, Yuhiko

doi:10.1002/pat.476

Cited by 11 publications

(9 citation statements)

References 25 publications

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“…Ethynyl groups can offer a combination of properties, unavailable with other functional groups, such as long shelf life in air, low moisture absorption, low crosslinking temperature and excellent mechanical properties for a cured material . In addition, terminal ethynyl groups are able to react with aryl or vinyl halides through a copper‐ or palladium‐mediated Sonogashira reaction, which is widely employed in synthesizing natural products, or building macrocyclic compounds and supramolecular chemicals .…”

Section: Introductionmentioning

confidence: 99%

Soluble and crosslinkable poly(phthalazinone ether ketone)s with pendent terminal ethynyl groups: synthesis, characterization and click modification

Wang

Zong

et al. 2015

Polymer International

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New poly(phthalazinone ether ketone)s (PPEKs) with pendent terminal ethynyl groups were synthesized by the aromatic nucleophilic substitution (S N Ar) polycondensation reaction of a new bisphenol monomer, 2-(3-ethynylphenyl)hydroquinone, with 4-(4 ′ -hydroxyphenyl)phthalazin-1(2H)-one and 4,4 ′ -bis(4-fluorophenyl) ketone, followed by click modification reaction with 1-azidopyrene. Fourier transform infrared and NMR spectral data of the model compound indicated that the terminal ethynyl groups were stable in S N Ar reaction conditions, thus allowing the synthesis of the desired polymers. The PPEKs obtained with glass transition temperature (T g ) in the range 152-245 ∘ C were amorphous, characterized by wide-angle X-ray diffraction, and dissolved in organic solvent to cast into transparent and flexible films. Differential scanning calorimetry results indicated that the curing reaction of the terminal ethynyl groups of the copolymers took place upon heating to 250 ∘ C. The T g of cured PPEKs was increased to about 260 ∘ C. They also exhibited excellent thermal stability with 5% weight loss temperatures ranging from 448 to 527 ∘ C in various atmospheres. The PPEKs with pendent terminal ethynyl groups were subsequently functionalized with pyrene through click reaction. A dilute chloroform solution displayed a red-shifted emission profile.

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Section: Introductionmentioning

confidence: 99%

Soluble and crosslinkable poly(phthalazinone ether ketone)s with pendent terminal ethynyl groups: synthesis, characterization and click modification

Wang

Zong

et al. 2015

Polymer International

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“…Propargyl ether resin appeared to be a very attractive candidate for epoxy resin in advanced composites, electronics, adhesives, and coatings. Therefore, propargyl‐containing polymers, such as bis propargyl ether bisphenol, propargyl ether novolak, polybenzoxazines, polyarylether ketones as well as poly‐phthalimide and other materials were synthesized, and the thermal properties of the resins were also investigated. However, the processability and solubility of the propargyl‐containing resins were less studied.…”

Section: Introductionmentioning

confidence: 99%

Novel propargylether‐terminated monomers containing pyridine and phenyl pendent group: Synthesis, cure, and properties

Yang

Zhou

2014

J of Applied Polymer Sci

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Two novel propargylether-terminated resins containing pyridine and bulky phenyl pendent group were prepared from propargyl bromide and different diphenols, and highly thermal stable polymers were obtained by the thermal cure of the monomers. The chemical structures of these novel monomers were well confirmed by FTIR, 1 H-NMR and elemental analysis. Curing and thermal behavior of the resins were investigated using differential scanning calorimetry (DSC) and dynamic thermogravimetry in argon atmosphere. DSC curves of these two monomers showed a single endothermic peak corresponding to the conformation of chromene ring and homopolymerization of the chromene ring. The temperature at 5% weight loss (T d5 ) was higher than 440 C under argon and the highest glass transition temperature (T g ) reached 362 C. The rheological behavior and solubility of the monomer were also investigated. The monomers showed excellent flow-ability, broad processing window, and great solubility. These results showed that the two resins could be ideal candidates for high-temperature resistant resins. V C 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 40469.

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“…The propargyloxy groups present in polymers are known to undergo un‐catalyzed crosslinking via sigmatropic thermal rearrangement to form 2H‐1‐benzopyran (2H‐chromenes) rings which then undergo polymerization to yield network structures (Supporting Information Figure S5). Furthermore, crosslinking reaction involving propargyloxy group proceeds without the evolution of small volatile compounds and provides void‐free clear films and coatings . In view of these characteristics, it was of interest to study thermal crosslinking reaction of (co)polyesters containing pendant propargyloxy groups.…”

Section: Resultsmentioning

confidence: 93%

“…Furthermore, crosslinking reaction involving propargyloxy group proceeds without the evolution of small volatile compounds and provides void-free clear films and coatings. 53 In view of these characteristics, it was of interest to study thermal crosslinking reaction of (co)polyesters containing pendant propargyloxy groups.…”

Section: Non-isothermal Curing Studies By Dscmentioning

confidence: 99%

Thermally Crosslinkable and Chemically Modifiable Aromatic Polyesters Possessing Pendant Propargyloxy Groups

Verma

Maher

Nagane

et al. 2018

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

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New aromatic (co)polyesters containing pendant propargyloxy groups were synthesized by phase transfer‐catalyzed interfacial polycondensation of 5‐(propargyloxy)isophthaloyl chloride (P‐IPC) and various compositions of P‐IPC and isophthaloyl chloride with bisphenol A. FTIR and NMR spectroscopic data, respectively, revealed successful incorporation of pendant propargyloxy groups into (co)polyesters and formation of (co)polyesters with desired compositions. (Co)polyesters exhibited good solubility in common organic solvents such as chloroform, dichloromethane, and tetrahydrofuran and could be cast into transparent, flexible, and tough films from chloroform solution. Inherent viscosities and number average molecular weights of (co)polyesters were in the range 0.77–1.33 dL/g and 43,600–118,000 g/mol, respectively, indicating the achievement of reasonably high‐molecular weights. The 10% weight loss temperatures of (co)polyesters were in the range 390–420 °C, demonstrating their good thermal stability. (Co)polyesters exhibited Tg in the range 146–170 °C and Tg values decreased with increase in mol % incorporation of P‐IPC. The study of non‐isothermal curing by DSC indicated thermal crosslinking of (co)polyesters via propargyloxy groups. The utility of pendant propargyloxy group was demonstrated by post‐modification of the selected copolyester with 1‐(4‐azidobutyl)pyrene, 9‐(azidomethyl)anthracene, and azido‐terminated poly(ethyleneglycol) monomethyl ether via copper(I)‐catalyzed Huisgen 1,3‐dipolar cycloaddition reaction. FTIR and 1H NMR spectra confirmed that click reaction was quantitative. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 588–597

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Synthesis of thermally crosslinkable fluorine‐containing poly(arylene ether ketone)s—II. Propargyl ether terminated poly(arylene ether ketone)s

Cited by 11 publications

References 25 publications

Soluble and crosslinkable poly(phthalazinone ether ketone)s with pendent terminal ethynyl groups: synthesis, characterization and click modification

Soluble and crosslinkable poly(phthalazinone ether ketone)s with pendent terminal ethynyl groups: synthesis, characterization and click modification

Novel propargylether‐terminated monomers containing pyridine and phenyl pendent group: Synthesis, cure, and properties

Thermally Crosslinkable and Chemically Modifiable Aromatic Polyesters Possessing Pendant Propargyloxy Groups

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