Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | ||||||
{[ item.p_purity ]} | {[ item.pr_size ]} | Inquiry |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]} |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]} | {[ item.pr_usastock ]} | in stock Inquiry - | {[ item.pr_chinastock ]} | {[ item.pr_remark ]} in stock Inquiry - | Login | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
Preparation and properties of bisphenol A polyetherketoneketone based phthalonitrile resins
Loren C. Brown ; Tyler J. Richardson ; Clair F. Lusk , et al. J. Appl. Polym. Sci.,2024,141(11):e55080. DOI: 10.1002/app.55080
More
Abstract: A promising high temperature phthalonitrile (PN) resin composed of a polyetherketoneketone (PEKK) core bridged by two bisphenol A linkers and end capped with PN groups is presented. This PEKK-PN resin was characterized via differential scanning calorimetry, thermogravimetric analysis, proton nuclear magnetic resonance spectroscopy, scanning electron microscopy, dynamic mechanical analysis, attenuated total reflection Fourier transform infrared, and rheometry. The PEKK-PN resin was evaluated with two different compositions containing 1) 70:30 PEKK-PN to bisphenol A PN (n?=?0) and 2) pure PEKK-PN. The 70:30 PEKK-PN resin was mixed with bis[4-(3-aminophenoxy)phenyl]sulfone and exhibited a melt viscosity of 271?cP, much lower than the 657?cP viscosity of the pure PEKK-PN mixture. Void-free PEKK-PN polymers were easily prepared by degassing and curing up to 380°C, resulting in fully crosslinked networks exhibiting thermal stability above 500°C and a 75% char yield. Additionally, the cured PEKK-PN polymer samples displayed good mechanical integrity retaining 50% stiffness at 300°C. This combination of properties suggests these new PEKK-PN resins are excellent materials for high temperature thermosets in composite applications.
Keywords: bisphenol A ; phthalonitrile ; resin ; thermoset
Purchased from AmBeed: 31643-49-9 ; 108464-88-6
CAS No. : | 31643-49-9 | MDL No. : | MFCD00040301 |
Formula : | C8H3N3O2 | Boiling Point : | - |
Linear Structure Formula : | (NC)2C6H3NO2 | InChI Key : | NTZMSBAAHBICLE-UHFFFAOYSA-N |
M.W : | 173.13 | Pubchem ID : | 97443 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 | UN#: | N/A |
Hazard Statements: | H302-H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | 1) A three-necked flask was charged with 103.9 g (600 mmo 1) of 4-nitro phthalonitrile, 800 mL of dimethyl sulfoxideAfter the powder was dissolved, 91.0 g (660 mmol) of potassium carbonate and 46.0 g (660 mmol) of sodium nitrite were added and heated at reflux to 160 C for 5 hours. After cooling to room temperature, the mixture was poured into a large amount of water, A yellow solid was precipitated and evacuated at 110 C and dried in vacuo to give 73.3 g of 4-hydroxy phthalonitrile in 85% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium carbonate; In dimethyl sulfoxide; | EXAMPLE 8 Preparation of 1,2-bis-(3,4-dicyanophenoxy)-3-fluorobenzene 3.60 g (0.02 moles plus 0.14 g excess) of 4-nitrophthalonitrile was dissolved in 50 ml anhydrous DMSO in a 100 ml three-necked flask fitted with a magnetic stirrer bar under nitrogen. 1.28 g (0.01 moles) of <strong>[363-52-0]3-fluorocatechol</strong> (Aldrich) was added to the mixture followed by 5 g of anhydrous potassium carbonate. The mixture was stirred at room temperature for 24 hours. The workup was as described in Example 5 and yielded 3.04 g of off-white crystals of the title compound (80percent theoretical yield). The product had the formula: STR15 The melting point was 198.5°-199.5° C. The elemental analysis for C22 H9 FN4 O2 was calc.: C, 69.47percent; H, 2.36percent; N, 14.73percent; found: C, 69.47percent; H, 2.34percent; N, 14.80percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE I; (p-Hydroxymethy-m-Methoxy Phenoxy)-4-Phthalonitrile Intermediate; To a 500 milliliter round bottom flask equipped with magnetic stir and nitrogen inlet was charged 42.1 grams of 4-hydroxy-3-methoxybenzyl alcohol (MW=154), 33.5 grams of potassium carbonate (MW=138), and 330 grams of ?dry? DMSO (in molecular sieve). The contents were heated in a 90 C. oil bath for about 1 hour. Thereafter, 41.9 grams of 4-nitrophthalonitrile (MW=173; obtained from TCI America, Portland, Oreg.) was added. The content were heated and stirred for 3 hours, after which a reverse phase TCL with methanol as the mobile phase was run which showed that no starting material remained in the reaction mixture (the Rfs were close). The contents were then poured into 1 liter of deionized water. The product precipitated out as a large chunk, which was filtered and collected. Infrared spectroscopy and TLC of the product indicated that none starting material, nitrophthalonitrile, remained. Then product was combined with methylene chloride and sonicated. Most of the solids dissolved. The mixture was then filtered and the filtrant was run through a silica plug. After the solvent was evaporated, about 59.3 grams of product was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere; | To a 100 mL, three-necked flask fitted with a thermometer, a Dean-Stark trap with condenser, and a nitrogen inlet were added 1,3-dihydroxypyrimidine (5.00 g, 44.6 mmol), 4-nitrophthalonitrile (15.83 g, 91.4 mmol), powdered anhydrous K2CO3 (13.0 g, 94.2 mmol), and N,N-dimethylformamide (DMF) (100 mL). The resulting mixture was heated at 80 C. for 6-8 h. The mixture was allowed to cool to ambient temperature and poured into a 5% aqueous HCl solution resulting in the precipitation of a solid. The material was broken up and collected using a Buechner funnel. The white solid was washed with 200 mL of a 5% aqueous KOH solution, with 200 mL of distilled water until neutral, with 200 mL of a 5% aqueous HCl solution, and finally with 200 mL of water until neutral. The solvent was removed in vacuo and the solid was vacuum dried to yield the heteroaromatic phthalonitrile (14.4 g, 90% yield). IR [cm-1]: delta 3058 (CCH), 2231 (C?N), 1610 (CN), 1589 (CC), 1491 (aromatic), 1281 (CH3), 1248 (C-O), 1173 (C-O), 970 (C-O), 834 (aromatic). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 12h;Inert atmosphere; | 3-methoxybenzoate (5.89 g, 0.03 mol) were dissolved inanhydrous DMF (60 mL) and anhydrous K2CO3 (13.82 g,0.1 mol) was added in portions during 30 min. The reactionmixture was stirred for 12 h at 80 C. After filtering the reactionmixture, the residue was extracted with CH2Cl2 andH2O and then was dried by rotary evaporation. After removalof the solvent, the crude product was purified by columnchromatography using silica gel and CHCl3:MeOH (15:1) aseluent to give 2, a white solid. Yield: 6.22 g (96 %). 1HNMR(500 MHz,DMSO-d6): d 8.07 (d, 1H, Ar-H), 7.75 (s, 1H, Ar-H), 7.69 (s, 1H, Ar-H), 7.67 (d, 1H, Ar-H), 7.35 (m, 2H, Ar-H), 4.37 (m, 2H, -CH2O-), 3.81 (s, 3H, Ar-OCH3), 1.35 (t,3H, -CH3). 13C NMR (126 MHz, DMSO-d6): d 164.42,159.98, 150.37, 144.59, 135.58, 128.18, 122.26, 121.77,120.96, 120.46, 116.03, 115.27, 114.75, 113.47, 107.66,60.45, 55.45, 13.30. HRMS (EI?): (m/z) = calcd for322.0953, found: 322.0955. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 85℃; | The compound of the following formula (C) was synthesized in the following manner.42.6 g of 1,1-bis (4'-hydroxyphenyl) -cyclododecane and 150 mL of dimethylformamide were placed in a 500 mL flask (3 mL) Neck round bottom flask) and stirred at room temperature.After stirring, 41.9 g of 4-nitrophthalonitrile was further added, and 50 g of DMF was added and dissolved by stirring.50.2 g of potassium carbonate was added together with 50 g of DMF, and the temperature was raised to 85 DEG C with stirring.After cooling to room temperature, the cooled reaction solution was neutralized and precipitated by pouring into a 0.2N hydrochloric acid aqueous solution. The precipitate was filtered and washed with water.The filtered product was dried in a vacuum oven at 100 for one day to remove water and residual solvent to obtain the target product.NMR analysis of the target product was carried out using an apparatus (Agilent 500 MHz NMR device) (solvent: DMSO (d6)) and the result is shown in FIG. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium carbonate; In N,N-dimethyl-formamide; at 85℃; for 5h; | Compound PN 1 of the following formula A was synthesized by a nitro displacement reaction. Specifically,4-hexylresorcinol (19.4 g) and 100 ml of DMF (dimethyl formamide) were placed in a 500 ml flask (3 neck round bottom flask) and stirred at room temperature. To the mixture, 34.6 g of 4-nitrophthalinitrile represented by the following formula (C) was added, and 50 g of DMF was further added, followed by stirring and dissolution. 41.5 g of potassium carbonate was added together with 50 g of DMF, and the temperature was raised to 85 while stirring.Reacted for about 5 hours,After cooling to room temperature, the cooled reaction solution was neutralized and precipitated by pouring into a 0.2 N aqueous hydrochloric acid solution. The precipitate was filtered and washed with water. The filtered product was dried in a vacuum oven at 100 for one day to remove water and residual solvent to obtain compound PN 1 of formula A in a yield of 85% by weight. The NMR analysis results for the compound of formula A are shown in Figure 1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.451 g; 0.098 g | With potassium carbonate; 3-Hydroxypropionitrile; In N,N-dimethyl-formamide; at 40℃; for 99h;Inert atmosphere; Molecular sieve; | 3-hydroxypropanenitrile (6.3 g, 88.63 mmol) was dissolved indry DMF (125 mL) under nitrogen and 4-nitrophthalonitrile(5.08 g, 29.36 mmol) and molecular sieve 4? (10.80 g) wereadded. After stirring for 2 h, finely ground anhydrous potassiumcarbonate (13.50 g, 97.831 mmol) was added in portionsduring 3 h with efficient stirring. The reaction mixturewas stirred at 40 C under nitrogen for 96 h. The mixturewas then poured in to ice-water (300 g). The precipitate wasfiltered off, washed with water until neutral and dried. Thecrude product was extracted with chloroform (450 mL).The combined organic extracts were washed with water anddried with anhydrous Na2SO4 and evaporated to dryness.The resulting product was washed with water and thendried, yield 4,40-oxydiphthalonitrile (3) 0,098 g. The singlecrystals were obtained in DMF at room temperature viaslow evaporation. The other filtrate was acidified to pH 3with HCl and filtered off and washed with water until neutraland then dried, yield 4-hydroxyphthalonitrile (4)2.451 g. It was not necessary to purify the product more.The spectral specifications of 4,4’-oxydiphthalonitrile (3)and 4-hydroxyphthalonitrile (4) were consistent with literaturevalues.[27-32] |
[ 288251-96-7 ]
2-Isobutyl-5-nitrobenzonitrile
Similarity: 0.94
[ 288251-96-7 ]
2-Isobutyl-5-nitrobenzonitrile
Similarity: 0.94
[ 288251-96-7 ]
2-Isobutyl-5-nitrobenzonitrile
Similarity: 0.94