4 4 oxydianiline

Manufactured by Merck Group

Sourced in United States

4,4'-oxydianiline is a chemical compound used as a raw material in the production of various materials and products. It is a white to off-white crystalline solid with a melting point of approximately 185-190°C. The compound serves as a precursor for the synthesis of other chemicals and materials, but a detailed description of its core function or intended use is not available while maintaining an unbiased and factual approach.

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4,4-oxydianiline (ODA)

14 protocols using 4 4 oxydianiline

Carbonized Polyimide Nanofiber Web Substrate

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Example 10

Poly(amic acid) (PAA) precursors for spinning were prepared by copolymerizing of pyromellitic dianhydride (Aldrich) and 4,4′-oxydianiline (Aldrich) in a mixed solvent of tetrahydrofurane/methanol (THF/MeOH, 8/2 by weight). The PAA solution was spun into fiber web using an electrostatic spinning apparatus. The apparatus consisted of a 15 kV DC power supply equipped with the positively charged capillary from which the polymer solution was extruded, and a negatively charged drum for collecting the fibers. Solvent removal and imidization from PAA were performed concurrently by stepwise heat treatments under air flow at 40° C. for 12 h, 100° C. for 1 h, 250° C. for 2 h, and 350° C. for 1 h. The thermally cured polyimide (PI) web samples were carbonized at 1,000° C. to obtain carbonized nanofibers with an average fibril diameter of 67 nm. Such a web can be used as a conductive substrate for an anode active material. We observe that the implementation of a network of conductive nanofilaments at the anode of a Li—Se cell can effectively suppress the initiation and growth of lithium dendrites that otherwise could lead to internal shorting.

US10629955B2. Selenium preloaded cathode for alkali metal-selenium secondary battery and production process (2020-04-21). Nanotek Instruments, Inc. [US]. Inventors: Hui He [US], Aruna Zhamu [US], Bor Z. Jang [US].

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Polyimide Nanofiber Substrate for Lithium-Sulfur Cells

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Example 8

Poly (amic acid) (PAA) precursors for spinning were prepared by copolymerizing of pyromellitic dianhydride (Aldrich) and 4,4′-oxydianiline (Aldrich) in a mixed solvent of tetrahydrofurane/methanol (THF/MeOH, 8/2 by weight). The PAA solution was spun into fiber web using an electrostatic spinning apparatus. The apparatus consisted of a 15 kV d.c. power supply equipped with the positively charged capillary from which the polymer solution was extruded, and a negatively charged drum for collecting the fibers. Solvent removal and imidization from PAA were performed concurrently by stepwise heat treatments under air flow at 40° C. for 12 h, 100° C. for 1 h, 250° C. for 2 h, and 350° C. for 1 h. The thermally cured polyimide (PI) web samples were carbonized at 1,000° C. to obtain carbonized nano-fibers with an average fibril diameter of 67 nm. Such a web can be used as a conductive substrate for an anode active material. We observe that the implementation of a network of conductive nano-filaments at the anode of a Li—S or room temperature Na—S cell can effectively suppress the initiation and growth of lithium or sodium dendrites that otherwise could lead to internal shorting.

US10158121B2. Flexible and shape-conformal cable-shape alkali metal-sulfur batteries (2018-12-18). Nanotek Instruments, Inc. [US]. Inventors: Aruna Zhamu [US], Hui He [US], Baofei Pan [US], Yu-Sheng Su [US], Bor Z Jang [US].

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Organic Synthesis of Aromatic Diamine Precursors

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Benzoin, sodium borohydride (NaBH₄, ≥98.0%), 4-nitrobenzoyl chloride (4-NBC, 98%), m ethanol (MeOH, ≥99.8%), tetrahydrofuran (THF, ≥99.9%), N,N’-dimethylacetamide (DMAc, ≥99.8%), pyromellitic dianhydride (PMDA), and 4,4′-oxydianiline (ODA) were purchased from Sigma-Aldrich Korea (Seoul, Korea). Solvents such as N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), N-methyl pyrrolidone (NMP), chloroform (CHCl₃), and ethanol were purchased from Junsei Chemical Co (Tokyo, Japan). As for 4,4-Diphthalic anhydride (6-FDA, ≥98.0%) and 10% palladium on carbon (Pd/C), they were purchased from Tokyo Chemical Industry Co. (TCI) (Tokyo, Japan). n-Hexane, ethyl acetate, and dichloromethane were purchased from Samchun Pure Chemicals (Pyeongtaek, Korea). Celite 545, which is a kind of diatomite whose main component is silica and is used to separate a catalyst from the reaction mixture, and γ-butyrolactone were purchased from Daejung (Siheung, Korea). The deionized water used in the experiments was purified by a Direct-Q^®3 water purification system (EMD Millipore) (Busan, Korea). All purchased chemical reagents were used without further purification.

Lee J.S., Yan Y.Z., Park S.S., Ahn S.K, & Ha C.S. (2022). A Novel Diamine Containing Ester and Diphenylethane Groups for Colorless Polyimide with a Low Dielectric Constant and Low Water Absorption. Polymers, 14(21), 4504.

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Freeze-Dried Pickering HIPE Synthesis

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Pyromellitic dianhydride (PMDA) and 4,4′-oxydianiline (ODA) were purchased from Sigma-Aldrich (St. Louis, MO, USA). 1-Methyl-2-pyrrolidone (NMP), pyridine, acetic anhydride, triethylamine (TEA), and cyclohexane were purchased from DUKSAN (Ansan, Gyeonggi-do, Korea). Acetone was purchased from SK Chemicals (Seongnam, Korea). An aluminum mold with a cubic hole (20 mm × 20 mm × 20 mm) was made and used to freeze-dry the Pickering HIPEs.

Song I.H., Kim D.M., Choi J.Y., Jin S.W., Nam K.N., Park H.J, & Chung C.M. (2019). Polyimide-Based PolyHIPEs Prepared via Pickering High Internal Phase Emulsions. Polymers, 11(9), 1499.

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Synthesis of Polyimide Membranes

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The reagents 4, 4-oxydianiline (97%), 1, 2, 4, 5-benzenetetracarboxylic anhydride (97%), acetonitrile (99%), N,N-dimethylacetamide (DMAc), dimethylformamide (DMF), trizma–hydrochloric acid (Tris–HCl), polyvinylpyrrolidone (MW. 130000 g/mol), sulfadiazine (99%), and sulfamethazine (99%) were all obtained from Sigma-Aldrich, South Africa. All chemicals were of analytical grade and used without further purification. Deionized (ultra-pure) water purified at a resistivity of 18.2 MΩ/cm. A Milli-QTM system (Millipore) was used for preparation of all aqueous solutions.

Hamnca S., Chamier J., Grant S., Glass T., Iwuoha E, & Baker P. (2022). Spectroscopy, Morphology, and Electrochemistry of Electrospun Polyamic Acid Nanofibers. Frontiers in Chemistry, 9, 782813.

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Synthesis of Spirobisindane-Based Polyimides

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All
the starting materials including 4,5-dichlorophthalic
acid, potassium carbonate, potassium hydroxide, and the following
six diamines, namely, (i) 4,4′-oxydianiline, (ii) 4,4′-ethylenedianiline,
(iii) 1,5-diaminonaphthalene, (iv) 1,8-diaminonaphthalene, (v) 2,2′-biphenyldiamine,
and (vi) benzidine were all purchased from Sigma-Aldrich. 5,5′,6,6′-Tetrahydroxy-3,3,3′,3′-tetramethyl-1,1′-spirobisindane
was purchased from Alfa Aesar, Inc., Germany. The abovementioned chemicals
were used as received without further purification. All other reagents
and solvents such as formamide, 33% ammonium hydroxide, thionyl chloride, N,N-dimethylformamide (DMF), ethanol, hydrochloric
acid, acetic acid, acetic anhydride, toluene, anhydrous toluene, m-cresol, quinolone, methanol, and chloroform (CH₃Cl) were purchased from various commercial sources. The DMF dried
over molecular sieves (4 A, 1–2 mm beads) was also purchased
from Alfa Aesar, Germany, and stored under nitrogen.

Elmehalmey W.A., Azzam R.A., Hassan Y.S., Alkordi M.H, & Madkour T.M. (2018). Imide-Based Polymers of Intrinsic Microporosity: Probing the Microstructure in Relation to CO2 Sorption Characteristics. ACS Omega, 3(3), 2757-2764.

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Synthesis of Organic Compounds via Anhydrous Solvents

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N,N-dimethylacetamide anhydrous 99.8% (DMAc Anh), N,N-dimethylacetamide 99.5% (DMAc), N,N-dimethylformamide 99.5% (DMF), dimethylsulfoxide 99.0% (DMSO), dimethylsulfoxide-d₆ 99.8% (DMSO-d₆), N-methyl-2-pyrrolidinone 99.5% (NMP), 3,5-dinitrobenzoyl chloride 98.0%, 4,4′-oxydianiline 98.0% (ODA), Pd/C (10% w/w), pyridin-4-ylmethanoamine 98.0%, isophthaloyl chloride 98.0%, m ethyl iodide 98.0%, ethyl iodide 99%, buthyl iodide 99.0%, and hexyl iodide 99% were obtained from Sigma-Aldrich. Ethanol absolute 99.5%, n-hexane 99.5%, diethyl ether 99.5%, tetrahydrofuran 99.5% (THF), lithium bis(trifluoromethanesulfonyl)imide 98.0% (LiTFSI), and hydrazine (80% solution in water) were obtained from Merck. All solvents were purified by distillation under reduced pressure, except for DMAc Anh and DMSO-d₆, which were used directly, as were the liquid reagents. The chlorides used were recrystallized twice from n-hexane, and ODA was sublimated at 300 °C under vacuum (4 × 10⁻⁴ mbar).

Bonardd S., Ángel A., Norambuena Á., Coll D., Tundidor-Camba A, & Ortiz P.A. (2021). Novel Polyelectrolytes Obtained by Direct Alkylation and Ion Replacement of a New Aromatic Polyamide Copolymer Bearing Pyridinyl Pendant Groups. Polymers, 13(12), 1993.

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Synthesis and Characterization of Lithium-Ion Battery Separator

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Pyromellitic dianhydride (PMDA, 97%), 4,4′-oxydianiline (ODA, 97%), and N,N-dimethylformamide (DMF, 99.5%) were purchased from Sigma-Aldrich. The commercially available polyethylene (PE) membranes were obtained from Toray Tonen Chemical Corp. (Japan) and served as the reference separators for the Li-ion batteries. Conductive materials [NCM523, (L&F Co., Ltd., South Korea), SGO-5 (SEC Carbon, Japan), and Super P (IMERYS, France)] and a binder (PVDF, Kureha, Japan) were used to prepare a cathode of coin cells, while a mixture of A-graphite (Showa Denko, Japan), Super P, and PVDF were used to prepare a carbon-based anode electrode. The PuriEL electrolyte containing 1.1 M of LiPF₆ in a mixture of ethylene carbonate (EC), dimethyl carbonate (DMC), and diethyl carbonate (DEC) (1 : 1: 1 v%) solution was used as purchased (Soulbrain Co. Ltd., South Korea). Stainless steel cases (SUS Cr2032) were obtained from Wellcos Corporation (South Korea) and used to assemble the coin cells.

Hou J., Jang W., Kim S., Kim J.H, & Byun H. (2018). Rapid formation of polyimide nanofiber membranes via hot-press treatment and their performance as Li-ion battery separators. RSC Advances, 8(27), 14958-14966.

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Nanographene-Montmorillonite Composite Synthesis

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Nanographene sheets of 98.48% purity were purchased from Angstron Materials, Dayton, OH, USA. The graphene sheets were 70–100 nm thick, with a lateral dimension of 2–7 µm. Montmorillonite organomodified Cloisite 30B clay of 100–200 nm thickness and 2–13 µm length was purchased from Southern Clay Products, Inc., Gonzales, TX, USA. Ammonium ion (III) was used in the Cloisite 30B, as the exchange cation is methyl, octadecyl, and bis-2-hydroxyethyl ammonium ion. 4,4-oxydianiline (ODA-98% purity), pyromellitic dianhydride (PMDA-99% purity) and N-methyl-pyrrolidone (NMP-99% purity) were purchased from Sigma Aldrich, St. Louis, MO, USA.

Akinyi C, & Iroh J.O. (2023). Thermal Decomposition and Stability of Hybrid Graphene–Clay/Polyimide Nanocomposites. Polymers, 15(2), 299.

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Thermal-Stable Polymer Dielectrics for High-Power Electronics

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Unless otherwise noted, commercially available reagents were used without further purification. The BOPP and the heat-resistant polymer dielectrics polyetherimide (PEI, T_g ≈ 217 °C), fluorene polyester (FPE, T_g ≈ 320 °C) and polyethersulfone (PES, T_g ≈ 218 °C) were provided by PolyK technologies. The BOPP is capacitor grade film with the thickness of 4.8 μm. The polyimide (PI, T_g ≈ 360 °C) was synthesized from the raw materials pyromellitic dianhydride (PMDA) and 4,4′-oxydianiline (ODA), both of which were purchased from Sigma-Aldrich.
The three kinds of molecular semiconductors ITIC (2,2′-[[6,6,12,12-Tetrakis(4-hexylphenyl)-6,12-dihydrodithieno[2,3-d:2′,3′-d′]-s-indaceno[1,2-b:5,6-b′]dithiophene-2,8-diyl]bis[methylidyne(3-oxo-1H-indene-2,1(3H)-diylidene)]]bis[propanedinitrile]), PCBM ([6,6]-Phenyl C61 butyric acid methyl ester), DPDI (2,2′,9,9′-Tetrakis(1-pentylhexyl)-[5,5′-bianthra[2,1,9-def:6,5,10-d′e′f′]diisoquinoline]-1,1′,3,3′,8,8′,10,10′(2H,2′H,9H,9′H)-octone) were all purchased from Sigma-Aldrich.
The chemical structures of the dielectric polymers and the molecular semiconductors are shown in Supplementary Fig. 29.

Yuan C., Zhou Y., Zhu Y., Liang J., Wang S., Peng S., Li Y., Cheng S., Yang M., Hu J., Zhang B., Zeng R., He J, & Li Q. (2020). Polymer/molecular semiconductor all-organic composites for high-temperature dielectric energy storage. Nature Communications, 11, 3919.

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