Synthesis and Aqueous Solution Behavior of Novel pH Responsive, Zwitterionic Cyclocopolymers

Thomas, David B.; Armentrout, R. Scott; McCormick, Charles L.

doi:10.1021/bk-2001-0780.ch006

Cited by 4 publications

(3 citation statements)

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“…Recently, our group ,− and others ,,, have reported various zwitterion-containing polymers derived from diallylammonium monomers (Figure ). A series of cyclocopolymers based on the copolymerization of N , N -diallyl- N , N -dimethylammonium chloride ( 3 ) or N , N -diallyl- N -methylamine ( 4 ) with 3-( N , N -diallyl- N -methylammonio)propanesulfonate ( 5 ) have been synthesized and extensively characterized. ,− These monomers undergo photochemically induced cyclopolymerization, yielding the five-membered rings common to diallylammonium salts .…”

Section: Introductionmentioning

confidence: 97%

“…A series of cyclocopolymers based on the copolymerization of N , N -diallyl- N , N -dimethylammonium chloride ( 3 ) or N , N -diallyl- N -methylamine ( 4 ) with 3-( N , N -diallyl- N -methylammonio)propanesulfonate ( 5 ) have been synthesized and extensively characterized. ,− These monomers undergo photochemically induced cyclopolymerization, yielding the five-membered rings common to diallylammonium salts . In earlier communications, we reported preliminary studies of copolymers based on 3 and the pH responsive monomer 4-( N , N -diallyl- N -methylammonio)butanoate ( 2 ). , Herein we present the full synthetic details and polymer characterization as well as the electrolyte and pH-responsive solution behavior of the resulting copolymers. The viscosity response is compared to analogous polymers containing sulfobetaine mer units ( 5 ).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization, and Aqueous Solution Behavior of Electrolyte- and pH-Responsive Carboxybetaine-Containing Cyclocopolymers

et al. 2003

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A novel pH-and salt-responsive carboxybetaine monomer, 4-(N,N-diallyl-N-methylammonio)butanoate (2), was prepared and cyclocopolymerized with the cationic monomer N,N-diallyl-N,Ndimethylammonium chloride (3) in 0.5 M NaCl aqueous solution (pH ) 7.0) using 2-hydroxy-1-[4-(hydroxyethoxy)phenyl]-2-methyl-1-propanone (Irgacure 2959) as the free-radical photoinitiator. The molar feed ratio of 2:3 was varied from 100:0 to 0:100 with the total monomer concentration held constant at 2.5 M. Cyclopolymerization to five-membered ring structures common to diallylammonium salts was confirmed by 13 C NMR spectroscopy. Reactivity ratio studies indicate that 2 and 3 copolymerize in a nearly ideal fashion (r1 ) 0.86, r2 ) 0.99). Weight-average molecular weights and second virial coefficients vary from (6.0 to 12.8) × 10 4 g mol -1 and (1.62 to 5.36) × 10 -4 mL mol g -2 , respectively. Dilute solution viscosity behavior depends on copolymer composition, ionic strength, and pH. Copolymers with a large excess charge exhibit typical polyelectrolyte behavior, while those with balanced charge exhibit "antipolyelectrolyte" behavior reported for zwitterionic (co)polymers. The polymers studied here are closely analogous cyclocopolymers we prevoiusly reported containing sulfobetaine mer units. 25 Unlike solutions of sulfobetaine-containing polymers, soltuions of poly(2-co-3) remain soluble at very low ionic strength even up to 100% incorporation of 2. Additionally, while the sulfobetaine systems are insensitive to pH, solutions of poly(2-co-3) exhibit a pH-dependent viscosity. All the copolymers have an apparent pKa of ∼3.6. Copolymers with 2 incorporations of 28 mol % and above have viscosity responsiveness between pH values of 2.5 and 4.5. The maximum pH response was achieved for solutions of poly(2-co-3) containing 37 and 56 mol % of the carboxybetaine monomer 2. † Paper No. 98 in a series entitled "Water-Soluble Polymers".

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Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Aqueous Solution Behavior of Electrolyte- and pH-Responsive Carboxybetaine-Containing Cyclocopolymers

et al. 2003

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“…Introduction. Poly(aminostyrenes) (PAM's) are potentially versatile polymers. − The presence of the amine functionality allows the formation of hydrophilic polymers through quaternization or protonation, the introduction of chromophores 1c or other functional groups, the formation of metal complexes, and the convenient formation of graft copolymers . Because of the acidity of primary or secondary amino groups relative to benzylic anions, only anionic polymerizations of the PAM's with tertiary or protected amino groups are possible.…”

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Kinetically Controlled Regioselective Formation of a Tail-to-Tail Dimer Dianion of 4-(N,N-Dimethylamino)styrene

Warner

Hogen‐Esch

2002

Macromolecules

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Preconcentration and spectrophotometric determination of polyDADMAC in treated water by in situ co-precipitation with naphthalene

Mwangi

Ngila

Ndungu

et al. 2014

Physics and Chemistry of the Earth, Parts A/B/C

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Synthesis and Aqueous Solution Behavior of Novel pH Responsive, Zwitterionic Cyclocopolymers

Cited by 4 publications

References 24 publications

Synthesis, Characterization, and Aqueous Solution Behavior of Electrolyte- and pH-Responsive Carboxybetaine-Containing Cyclocopolymers

Synthesis, Characterization, and Aqueous Solution Behavior of Electrolyte- and pH-Responsive Carboxybetaine-Containing Cyclocopolymers

Kinetically Controlled Regioselective Formation of a Tail-to-Tail Dimer Dianion of 4-(N,N-Dimethylamino)styrene

Preconcentration and spectrophotometric determination of polyDADMAC in treated water by in situ co-precipitation with naphthalene

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