Phthalonitrile cure reaction with aromatic diamines

Sastri, Satya B.; Keller, Teddy M.

doi:10.1002/(sici)1099-0518(199808)36:11<1885::aid-pola23>3.0.co;2-9

Cited by 171 publications

(124 citation statements)

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“…The exothermic transition peaked at 239°C and the enthalpy of cure was 179.3 J/g, which were a result of self-promoted curing reaction of the 3-APN monomer between the amino group and phthalonitrile units. For these phthalonitrile monomers [9][10][11][12][13][14][15][16][17][18][19][20][21], the polymerization reaction occurs through the nitrile groups of the phthalonitrile units in the presence of aromatic diamine curing agents and these exothermic transitions of the cure reaction peaked at 250-270°C. In addition, the maximum processing temperature was up to 425°C and the heat-treatment time was very long (> 10 h) due to the low reactivity of the phthalonitriles.…”

Section: Self-promoted Curing Properties Of 3-apn Monomer and Prepolymermentioning

confidence: 99%

“…Phthalonitrile-based monomers and oligomers containing a variety of linkages such as aromatic ether [10,20], sulfone [21], oligomeric aromatic ethercontaining units [11,12,14], oligomeric biphenyl ethernitrile units [22][23][24] and benzoxazine units [25,26] have been designed and synthesized. Then, greatly improved properties of these monomers and oligomers can be achieved by including a low complex melt viscosity and a broad processing window.…”

Section: Introductionmentioning

confidence: 99%

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Self-promoted curing phthalonitrile with high glass transition temperature for advanced composites

et al. 2012

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A novel self-promoted curing phthalonitrile monomer was synthesized via substitution reaction of 4-nitrophthalonitrile and 3-aminophenol at the presence of K 2 CO 3 in the dimethylsulfoxide solvent. The phthalonitrile was characterized by Fourier transform infrared spectra, nuclear magnetic resonance, gel permeation chromatography, differential scanning calorimetry, dynamic rheological analysis and thermal gravimetric analysis. The phthalonitrile monomer can be thermally polymerized with self-promoted curing behaviors. The prepolymerization reaction of the phthalonitrile prepolymer was investigated and the phthalonitrile prepolymer exhibited the desirable processing feature. With the curing process of low curing temperature and short curing time, the cured polymers exhibited high glass transition temperatures (241-270°C) and excellent thermal stabilities with the 5 % weight loss temperature (395-441°C). The novel phthalonitrile can be a good candidate as matrix for high performance polymeric materials.

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Section: Self-promoted Curing Properties Of 3-apn Monomer and Prepolymermentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Self-promoted curing phthalonitrile with high glass transition temperature for advanced composites

et al. 2012

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“…It is well known that phthalonitrile shows excellent reactivity and crosslinkable property [19,20]. Therefore, by introducing the phthalonitrile in the end of the PEN main chain, the PEN-Ph integrated the excellent performances of PEN [21][22][23][24][25] (high thermal stability, superior mechanical properties as well as good workability) and the crosslinkable property of the phthalonitrile, resulting in more excellent thermal properties and mechanical properties [26,27].…”

Section: Introductionmentioning

confidence: 99%

A novel single-component composite based on phthalonitrile end-capped polyarylene ether nitrile: crystallization and crosslinking

2015

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A novel single-component composite based on phthalonitrile end-capped polyarylene ether nitrile (PEN-Ph) was prepared successfully via hot compression. In the PENPh system, the crosslinking reactions and crystallization exist simultaneously, and the crystals are embedded in the crosslinked PEN-Ph matrix, which can work as reinforcement. Analysis of the Non-isothermal cold crystallization kinetics of the PEN-Ph system was performed by using differential scanning calorimetry (DSC), and the activation energy of the crystallization process is obtained to be 217.5 kJ·mol −1 . The DSC and SEM analysis provide the evidence for that there exists crosslinking reactions as well as crystallization behavior. However, the crosslinking reaction with excessive speed will restrict the crystallization behavior of the PEN-Ph. Furthermore, the DMA and mechanical measurements indicate that the glass transition temperature and mechanical properties are influenced by not only the crosslinking degree but also the crystallinity. The tensile strength of the single-component composite is 111.0 MPa, increased by about 10 MPa than that of amorphous PEN-Ph sheet.

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“…[1][2][3][4][5][6] Phthalonitrile monomers or oligomers with different structures have been synthesized and used for the preparation of phthalonitrile resins. [7][8][9][10][11][12][13][14][15][16] Polymerization of these monomers occurs through nitrile groups by an addition cure mechanism, leading to void-free cross-linked products such as triazine, phthalocyanine and isoindoline. 1,17 The formation of heterocyclic crosslinked structures increases the thermooxidative stability, as well as good mechanical properties.…”

Section: Introductionmentioning

confidence: 99%

New highly thermostable aromatic polyamides with pendant phthalonitrile groups

Carja¹,

Hamciuc²,

Hamciuc³

et al. 2012

Macromol. Res.

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A phthalonitrile-containing diamine monomer, 4,4'-diamino-4''-(3,4-dicyanophenoxy)-triphenylmethane, 1, was prepared, and its cure behavior was investigated. The diamine 1 was thermally polymerized at 250 o C even in absence of curing additives. The resulting resins exhibited exceptional high thermal and thermo-oxidative stability, with the 5% weight loss being above 500 o C and the char yield at 700 o C being over 62%, in air or inert atmosphere. New soluble aromatic polyamides derived from diamine 1, 2,2-bis[4-(4-aminophenoxy)phenyl]propane and terephthaloyl chloride were synthesized. They showed good solubility in organic solvents, film forming properties, and high thermal stability, with the decomposition temperature being above 400 o C. The kinetic processing of thermogravimetric data was carried out using differential and integral methods. Electrical properties of the polymer films were evaluated on the basis of dielectric constant and dielectric loss and their variation with frequency and temperature. The influence of the phthalonitrile content on the polymer properties was studied.

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Phthalonitrile cure reaction with aromatic diamines

Cited by 171 publications

References 0 publications

Self-promoted curing phthalonitrile with high glass transition temperature for advanced composites

Self-promoted curing phthalonitrile with high glass transition temperature for advanced composites

A novel single-component composite based on phthalonitrile end-capped polyarylene ether nitrile: crystallization and crosslinking

New highly thermostable aromatic polyamides with pendant phthalonitrile groups

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