- Synthesis and characterization of highly fluorinated poly(phthalazinone ether)s based on AB-type monomers
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Four different fluorinated methyl- and phenyl-substituted 4-(4-hydroxyphenyl)-2-(pentafluorophenyl)-phthalazin-1(2H)-ones, AB-type phthalazinone monomers, have been successfully synthesized by nucleophilic addition-elimination reactions of methyl- and phenyl-substituted 2-((4-hydroxy)benzoyl)benzoic acid with 1-(pentafluorophenyl)hydrazine. Under mild reaction conditions, the AB-type monomers underwent self-condensation polymerization reactions successfully and gave fluorinated poly(phthalazinone ether)s with high molecular weights. Detailed structural characterization of the AB-type monomers and fluorinated polymers was determined by 1H NMR, 19F NMR, FTIR, and GPC. The solubility, thermal properties, mechanical properties, water contact angles, and optical absorption of the polymers were evaluated. The polymers had high Tgs varying from 337 to 349 °C and decomposition temperatures (Td, 25 wt %) above 409 °C. Tough, flexible films were cast from THF and chloroform solutions. The films showed excellent tensile strengths ranging from 70 to 85 MPa with good hydrophobicities with water contact angles higher than 95.5 °C. The polymers had absorption edges below 340 nm and very low absorbance per cm at higher wavelengths 500-2500 nm. These results indicate that the polymers are promising as high performance materials, for example, membranes and hydrophobic materials.
- Li, Xiuhua,Gao, Yan,Long, Qiang,Hay, Allan S.
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p. 1761 - 1770
(2014/05/20)
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- Polymers derived from phenolphthaleins
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Homopolymers and copolymers with high Tg's are produced from phthalazones which in turn are produced from phenolphthalein as a readily available starting material; the homopolymers may be represented by formula (IX): STR1 wherein R1 and R2, which may be the same or different, are selected from hydrogen, fluorine, phenyl and fluorophenyl, each m, which may be the same or different, is an integer of 0, 1, 2, 3 or 4, and n is an integer of 2 to 200. Novel phenyl substituted phenolphthaleins and novel hydroxybenzoylbenzoic acids, as well as novel phthalazones, all of which may be employed in the preparation of homopolymers and copolymers of the invention, are also provided.
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- SYNTHESIS AND REACTIVITY OF 2-AROYLBENZOIC ACIDS. PART I. 2-BENZOIC ACID
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Selective Friedel-Crafts 2-carboxybenzoylation of 2-biphenylol with phthalic anhydride led to formation of 2-benzoic acid (1); other isomers were not present.Several chemical methods were involved to investigate reactivity of acid 1.Compound 1 and its derivatives were analyzed with TLC, UV-VIS, IR, 1H NMR and MS methods.
- Ruminski, Jan K.,Mokhtar, Hassan M.
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p. 995 - 1005
(2007/10/02)
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