Synthesis and characterization of poly(methacrylates) containing spiroacetal and norbornene moieties in side chain

✍ Scribed by Ali Pourjavadi; Bibi Fatemeh Mirjalili

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 203 KB
• Volume: 77
• Category: Article
• ISSN: 0021-8995
• DOI: 10.1002/(sici)1097-4628(20000705)77:1<30::aid-app5>3.0.co;2-s

✦ Synopsis

A four-step synthetic strategy was applied to achieve novel methacrylic monomers. 5-Norbornene-2,2-dimethanol was prepared from a Diels-Alder reaction of cyclopentadiene and acrolein, followed by the treatment of the adduct with an HCHO/ KOH/MeOH solution. The resulting 1,3-diol (1) was then acetalized with different aromatic aldehydes having OH groups on the ring to produce four spiroacetal derivatives. The reaction of methacryloyl chloride with the phenolic derivatives led to four new methacrylic monomers that were identified spectrochemically (mass, FTIR, 1 H-NMR, and 13 C-NMR spectroscopy). Free radical solution polymerization was used to prepare novel spiroacetal-norbornene containing polymethacrylates, which were characterized by FTIR and 1 H-NMR spectroscopy and differential scanning calorimetry and thermogravimetric thermal analysis. Gel permeation chromatography was performed to determine molecular weight averages and polydispersity. The polymethacrylate having naphthalenic nuclei was recognized to be the highest molecular weight polymer (M n ϭ 12144, inh ϭ 0.80 dL/g) with the highest thermal stability. All the polymers showed good solubility in a variety of common organic solvents.