Synthesis and Characterization of Photosensitive Phosphorus Based Polymers Containing α,β-Unsaturated Ketones in the Main Chain

• Published in: Journal of macromolecular science. Part A, Pure and applied chemistry Pure and applied chemistry, 2005-12, Vol.42 (12), p.1589-1602
• Main Authors: Kaniappan, K., Murugavel, S. C.
• Format: Article
• Language: English
• Subjects: Applied sciences; Exact sciences and technology; Inorganic and organomineral polymers; interfacial polymerization; phosphorus containing; photocrosslinking; photosensitive polymers; Physicochemistry of polymers; polycondensation; Preparation
• ISSN: 1060-1325; 1520-5738
• DOI: 10.1080/10601320500246636

1,3-Bis(4-hydroxyphenyl)propenone (BHPP) and 3-(4-hydroxy-3-methoxy phenyl)-1-(4-hydroxyphenyl)propenone (HMPHPP) were used as monomers for preparing photosensitive phosphorus containing polyesters. The photosensitive monomers BHPP and HMPHPP were prepared respectively by refluxing 4-hydroxybenzaldehyde and 3-methoxy-4-hydroxybenzaldehyde with 4-hydroxy acetophenone. The polyesters were synthesized by interfacial polycondensation of photosensitive diols with N-phenylphosphoramidic dichloride using hexadecyltrimethyl ammonium bromide (HDTMAB) as phase-transfer catalyst. Copolymers were also prepared by incorporating terephthaloyl chloride in the polymer backbone. The synthesized monomers and polymers were characterized by UV, FT-IR and 1 H, 13 C and 31 P-NMR spectroscopic techniques. The resulting polymers had inherent viscosities in the range of 0.15-0.51 dL/g and showed good solubility in polar organic solvents. The thermal properties of the polymers were studied by thermogravimetric analysis and differential scanning calorimetry under nitrogen atmosphere. The TGA data revealed that the 10% weight loss occurs at 275-320°C and all the synthesized polymers showed high char residues. DSC studies indicate that these polymers possess T g in the range of 48 to 64°C. The photosensitive property of the polymers in film and solution state was investigated by ultraviolet spectroscopy. The effect of incorporation of terephthaloyl unit on photocrosslinking and thermal properties of the polymers was also studied.