Synthesis and properties of polyester imides based on 2,2-bis(4-hydroxyphenyl)propanedibenzoate-3,3ʹ,4,4ʹ-tetracarboxylic acid dianhydride

Evidence for the Higgs boson, for which the Nobel Prize in physics was awarded in 2013, was discovered by the European Organization for Nuclear Research (CERN) in 2012, using the Large Hadron Collider (LHC). PIXEO BP-S exhibited superior resistance to both radiation and cryogenics and this polymer played a crucial role in the operation of the LHC, thus contributing to the Higgs boson discovery. Herein, we report the synthesis and characterization of various polyester imides for a cryogenic and radiation-resistant polyimide adhesive tape. These polyester imides (3) were synthesized from 2,2-bis(4-hydroxyphenyl)propanedibenzoate-3,3ʹ,4,4ʹ-tetracarboxylic acid anhydride (ESDA) and various diamines (1a–1l). All polymers showed high solubility in various solvents, especially 3a, which was synthesized from ESDA and 4,4ʹ-bis(3-aminophenoxy)diphenyl sulfone and dissolved even in ether solvents such as dioxane and dioxolane. Dynamic mechanical analysis and X-ray diffraction studies indicated that the excluded volume of the polyester imides had a length of 150 A, and that this volume affected the thermoplastic properties and solubilities of the polymers. The degree of imidization of 3a dissolved in dimethyl sulfoxide was examined by 1H-Nuclear magnetic resonance(NMR) imaging utilizing a 15N-enriched amine model compound in conjunction with 1H–15N heteronuclear single quantum coherence 2-dimensional NMR and was found to be 99.5%. PIXEO BP-S tape used for Large Hadron Collider and its chemical structure.