Poly(methyl methacrylate)s containing pendant octamethylcalix[4]pyrrole subunits were prepared and demonstrated to be capable of extracting tetrabutylammonium chloride and fluoride salts from aqueous media.

Fishing for KF: Potassium fluoride and chloride salts can be extracted from aqueous media using poly(methyl methacrylate)s containing pendant calix[4]pyrrole and crown ether groups (see picture). These polymers are able to extract these salts much more efficiently than calixpyrrole, crown ether, linked crown ether calixpyrrole monomers, polymers containing either recognition unit, or poly(methyl methacrylate) controls.

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SYNOPSISCyclohexanone-formaldehyde and acetophenone-formaldehyde resin were in situ modified with phenol, Bisphenols, and substituted acetophenones. Furthermore, acetophenoneformaldehyde, cyclohexanon-formaldehyde, and in situ-modified resins were modified with anhydrides such as acetic anhydride, maleic anhydride, dodecenylsuccinic anhydride, 3,434'-biphenyltetracarboxylic dianhydride, and 4,4'-oxydiphtalic anhydride. Modification of these resins with hydroxyl amine, semicarbazide, and phenyl hydrazine were also studied. Melting points, solubilities in organic solvents, FTIR, and NMR spectrum of the modified resins were determined. 0 1996 John Wiley & Sons, Inc. I NTRO DU CTI 0 NModification of cyclohexanone-formaldehyde resin and acetophenone-formaldehyde resin have been previously studied.'.' Hydroxyl groups were reacted with acetyl chloride, benzoyl chloride, phatalic anhydride, and carbonyl groups with hydroxylamine, semicarbazide, and phenylhydrazine.Furthermore, in situ modification of acetophenone-formaldehyde resin was carried out using phen01,~ p-c~mylphenol,~ p-cresol? and Bisphenols' as the modifier compounds. Cyclohexanone-formaldehyde resin was also in situ modified using methyl isobutyl ketone: methyl ethyl ketone,6 methyl cyclohexanone: acetaldehyde,6 propion-aldehyde,6 cinnamaldehyde,6 di~ynadiamide,~ arninotria~ine,~ and phen01.~ In this work, cyclohexanone-formaldehyde resin (CF resin) and acetophenone-formaldehyde resin (AF resin) were modified during resin preparation by the addition of a modifier compound/formaldehyde mixture to the polymerization media. Modifier compounds were phenol, l,l-di(4-hydroxy phenyl)cyclododecane, 1 -phenyl-1,l -di( 4-hydroxy phenyl)etan, 2,4-dichloroacetophenone, and 4-bromoacetophenone. AF resin, in situ-modified AF res-* To whom correspondence should be addressed. ins, and in situ-modified CF resins were modified via their hydroxyl, phenolic hydroxyl, and carbonyl groups. EXPERIMENTALIR spectra were recorded on a Jasco FTIR-5300 Fourier transform infrared spectrometer. 'H-NMR spectra were obtained for the CDC13 solution on a Bruker AC (200 MHz). GPC chromatograms were obtained using a Knauer M64 instrument equipped with a differential refractometer. The preparations of these resins were carried out as described previously.

SYNOPSISPreparation of in situ-modified cyclohexanone-formaldehyde and acetophenoneformaldehyde resins with compounds such as diphenols, melamine, andp-toluene sulfonamide were studied.Modification of acetophenoneformaldehyde resins with hydroxylamine, semicarbazide, phenylhydrazine, phthalic anhydride, and acetic anhydride was also studied. Melting points, solubilities in organic solvents, and FI?R and NMEt spectra of modified resins were determined. I NTRO D UCTlO NModification of cyclohexanone-formaldehyde resin via its hydroxyl and carbonyl groups has been previously studied.' Hydroxyl groups were reacted with acetyl chloride, benzoyl chloride, phthalic anhydride, and carbonyl groups with hydroxylamine, semicarbazide, and phenylhydrazine.In situ modification of acetophenone resin has been studied previously. The modifier compounds were phenol, p -cumylphenol, and p -cres01.~ The resulting resins were used for adhesives and binders.Modified cyclohexanone / formaldehyde resins were also prepared using MEK, MIBK, methylcyclohexanone, acetaldehyde, propionaldehyde, and cinnamaldehyde. These resins were used as binders for self-hardening molds.5In this work, cyclohexanone-formaldehyde and acetophenone-formaldehyde resins were modified during the preparation by the addition of a modifier compound/ formaldehyde mixture to the polymerization media. Compounds that react with formaldehyde in basic media were used as modifier compounds. These were melamine, resorcinol, p -toluene sulfonamide, bisphenol-A, and bisphenol-C.Modification of the acetophenone-formaldehyde resin via hydroxyl and carbonyl groups and reaction

ABSTRACT:A new class of dimethyl formamide (DMF)-and acetone-soluble conducting pyrrole-ketonic resin copolymers has been developed. This was accomplished by oxidatively polymerizing pyrrole monomer by Ce(IV) salt in the presence of methyl ethyl ketone formaldehyde resin (MEKF-R). The resulting copolymers were readily dissolved in DMF and acetone. These products were characterized by FTIR and UV-visible spectroscopy, conductivity, four-probe conductivity, viscosity, and DSC measurements.

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