3,3',4,4'-Benzophenone tetracarboxylic dianhydride

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3,3',4,4'-Benzophenone tetracarboxylic dianhydride
Names
IUPAC name
5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.017.590 Edit this at Wikidata
EC Number
  • 219-348-1
UNII
  • InChI=1S/C17H6O7/c18-13(7-1-3-9-11(5-7)16(21)23-14(9)19)8-2-4-10-12(6-8)17(22)24-15(10)20/h1-6H
    Key: VQVIHDPBMFABCQ-UHFFFAOYSA-N
  • C1=CC2=C(C=C1C(=O)C3=CC4=C(C=C3)C(=O)OC4=O)C(=O)OC2=O
Properties
C17H6O7
Molar mass 322.228 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3,3’,4,4’-Benzophenone tetracarboxylic dianhydride (BTDA) is chemically, an aromatic organic acid dianhydride. It may be used to cure epoxy-based powder coatings. It has the CAS Registry Number of 2421-28-5 and a European Community number 219-348-1. It is REACH and TSCA registered. The formula is C17H6O7 with a molecular weight of 322.3.[1][2]

Uses

Its use in epoxy powder coatings is slightly unusual in that many epoxy coatings are designed to be fairly close to a stoichiometric curing ratio. BDTA cured materials benefit from having the stoichiometry closer to 0.65 rather than 1.[3] It is also used to synthesize polyimides. These have good flexibility because of the carbonyl and keto groups which increase the molecular distancing between the imide rings. This improves the solubility.[4][5] The resultant product when combined with nano-technology produces composites with enhanced heat stability properties.[6] BTDA has also been used to synthesize other molecules and is thus a reactive ingredient in its own right.[7][8][9][10]

References

  1. ^ PubChem. "Benzophenone-3,3',4,4'-tetracarboxylic dianhydride, 98%". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-08-11.
  2. ^ "Benzophenone-3,3′,4,4′-tetracarboxylic dianhydride". SigmaAldrich.
  3. ^ "Toward High Glass-Transition Temperatures in Epoxy Powder Coatings Based on BTDA®". American Coatings Association. Retrieved 2023-07-24.
  4. ^ F. Röhrscheid "Carboxylic Acids, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a05_249
  5. ^ Faghihi, Khalil; Ashouri, Mostafa; Hajibeygi, Mohsen (2013-10-25). "High Temperature and Organosoluble Poly(amide-imide)s Based on 1,4-Bis[4-aminophenoxy]butane and Aromatic Diacids by Direct Polycondensation: Synthesis and Properties". High Temperature Materials and Processes. 32 (5): 451–458. doi:10.1515/htmp-2012-0164. ISSN 2191-0324. S2CID 97696111.
  6. ^ Pooladian, Baharak; Alavi Nikje, Mir Mohammad (2018-12-12). "Preparation and Characterization of Novel Poly(Urethane-Imide) Nanocomposite Based on Graphene, Graphene Oxide and Reduced Graphene Oxide". Polymer-Plastics Technology and Engineering. 57 (18): 1845–1857. doi:10.1080/03602559.2018.1434669. ISSN 0360-2559. S2CID 103771291.
  7. ^ Lu, Yun Hua; Wang, Bing; Xiao, Guo Yong; Hu, Zhi Zhi (2012). "Synthesis of 1,4-Bis(3-amino-5-trifluoromethylphenoxy)Benzene and Properties of the Polyimide Film Therefrom". Advanced Materials Research. 581: 297–300. doi:10.4028/www.scientific.net/AMR.581-582.297. ISSN 1662-8985. S2CID 96413460.
  8. ^ Yu, Yang-Yen; Chien, Wen-Chen; Wu, Tsung-Heng; Yu, Hui-Huan (2011-12-30). "Highly transparent polyimide/nanocrystalline-titania hybrid optical materials for antireflective applications". Thin Solid Films. 38th International Conference on Metallurgical Coatings and Thin Films (ICMCTF 2011). 520 (5): 1495–1502. Bibcode:2011TSF...520.1495Y. doi:10.1016/j.tsf.2011.08.002. ISSN 0040-6090.
  9. ^ Devaraju, Naga Gopi; Kim, Eung Soo; Lee, Burtrand I (2005-09-01). "The synthesis and dielectric study of BaTiO3/polyimide nanocomposite films". Microelectronic Engineering. 82 (1): 71–83. doi:10.1016/j.mee.2005.06.003. ISSN 0167-9317.
  10. ^ Ding, Fan-Chun; Hsu, Shan-hui; Chiang, Wen-Yen (2008-07-05). "Synthesis of a new photoreactive gelatin with BTDA and HEMA derivatives". Journal of Applied Polymer Science. 109 (1): 589–596. doi:10.1002/app.28025.
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