Participation of propargyl moiety in Butler's cyclopolymerization process

Ali, Shaikh A.; Al‐Muallem, Hasan A.

doi:10.1016/j.polymer.2004.09.067

Cited by 8 publications

(3 citation statements)

References 21 publications

(41 reference statements)

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“…With two propargyl units no cyclopolymerization or cyclocopolymerization with sulfur dioxide could be observed. With one allyl and one propargyl, groups could be cyclopolymerized with sulfur dioxide to give linear and water-soluble macromolecules, with a five-membered cyclic structure embedded in the polymer chain . Amide-based systems, in a slight variation of the main design reported in Figure , have also been reported to cyclopolymerize, to afford five- or six-membered rings repeating units. − …”

Section: Radical Cyclopolymerizationmentioning

confidence: 99%

Cyclopolymerizations: Synthetic Tools for the Precision Synthesis of Macromolecular Architectures

2018

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Monomers possessing two functionalities suitable for polymerization are often designed and utilized in syntheses directed to the formation of cross-linked macromolecules. In this review, we give an account of recent developments related to the use of such monomers in cyclopolymerization processes, in order to form linear, soluble macromolecules. These processes can be activated by means of radical, ionic, or transition-metal mediated chain-growth polymerization mechanisms, to achieve cyclic moieties of variable ring size which are embedded within the polymer backbone, driving and tuning peculiar physical properties of the resulting macromolecules. The two functionalities are covalently linked by a "tether", which can be appropriately designed in order to "imprint" elements of chemical information into the polymer backbone during the synthesis and, in some cases, be removed by postpolymerization reactions. The two functionalities can possess identical or even very different reactivities toward the polymerization mechanism involved; in the latter case, consequences and outcomes related to the sequence-controlled, precision synthesis of macromolecules have been demonstrated. Recent advances in new initiating systems and polymerization catalysts enabled the precision syntheses of polymers with regulated cyclic structures by highly regio- and/or stereoselective cyclopolymerization. Cyclopolymerizations involving double cyclization, ring-opening, or isomerization have been also developed, generating unique repeating structures, which can hardly be obtained by conventional polymerization methods.

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Section: Radical Cyclopolymerizationmentioning

confidence: 99%

Cyclopolymerizations: Synthetic Tools for the Precision Synthesis of Macromolecular Architectures

2018

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“…It has been examined if the propargyl group could be involved in Butler's cyclopolymerization process [133,134] . Monomer 269 , containing two propargyl groups, did not undergo homo‐ or copolymerization with SO 2 , while monomer 270 , having a propargyl and one allyl group, gave water‐soluble homo‐ 271 and copolymer 272 .…”

Section: Synthesis and Applications Of Ph‐responsive Cyclopolymersmentioning

confidence: 99%

Stimuli‐Responsive Macromolecular Architecture by Butler Cyclopolymerizations: Synthesis and Applications

Ali

Al‐Muallem

Mazumder

2022

The Chemical Record

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This article reviews the synthesis of polyzwitterions (PZs) (poly-carboxybetaines, -phosphonobetaines, and -sulfobetaines) having multiple pH-responsive centers. The synthesis follows the Butler cyclopolymerization protocol involving a multitude of diallylammonium salts and their copolymerization with SO 2 and maleic acid. The PZs have been transformed into cationic-, anionic-polyelectrolytes, and polyampholytes under the influence of pH. Particular attention is given to the application of these polymers as antiscalants, mild steel corrosion inhibitors, components in constructing Aqueous Two-Phase Systems (ATPSs), and membrane modifiers. The ATPSs could be used to separate various biomolecules, including proteins. Many amphiphilic polymers incorporating a few mol % hydrophobic monomers have shown enhanced viscosities and could be suitable for applications in oil fields. The progress of applying Butler cyclopolymerization in reversible addition-fragmentation chain transfer (RAFT) chemistry has been discussed. Future works are expected to focus on RAFT cyclopolymerization to construct block copolymers.

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“…Alkyne group is not known to participate in the cyclopolymerization process [25]. However, recent study by us demonstrated the participation of propargyl moiety in Butler's cyclopolymerization process [26].…”

Section: Synthesis Solubility and Spectroscopy Of Homopolymersmentioning

confidence: 99%

Cyclopolymers from N,N-diallyl-N-propargyl-(12-N′-formylamino)-1-dodecylammonium chloride and their use as inhibitors for mild steel corrosion

et al. 2012

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A dodecanediamine (DDA)-based new monomer, N,N-diallyl-N-propargyl-(12-N 0 -formylamino)-1-dodecylammonium chloride, on homo-and co-cyclopolymerization (with SO 2 ) afforded cationic polyelectrolytes, which on acidic hydrolysis of the formyl group gave water-soluble polyelctrolytes. One of the allyl groups undergoes cyclopolymerization with either the propargyl or the other allyl group in competing pathways; the incorporation of the allyl group is found to be faster than the propargyl unit by a ratio of 4:1. Both the monomer and its precursor as well as the polymers were used to study the corrosion inhibition of mild steel by gravimetric and electrochemical methods in acidic and saline media at 60°C. The inhibitor molecules (at a concentration of 200 ppm) exhibited inhibition efficiencies (%IE) in the ranges 81-99 % in 1 M HCl, 97-98 % in 4 M HCl, 87-93 % in 7.7 M HCl, 68-91 % in 0.5 M H 2 SO 4 , and 84-92 % in 3.5 % NaCl. There is a considerable increase in the IEs by the monomers and polymers in comparison to the parent 1,12-DDA.

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Participation of propargyl moiety in Butler's cyclopolymerization process

Cited by 8 publications

References 21 publications

Cyclopolymerizations: Synthetic Tools for the Precision Synthesis of Macromolecular Architectures

Cyclopolymerizations: Synthetic Tools for the Precision Synthesis of Macromolecular Architectures

Stimuli‐Responsive Macromolecular Architecture by Butler Cyclopolymerizations: Synthesis and Applications

Cyclopolymers from N,N-diallyl-N-propargyl-(12-N′-formylamino)-1-dodecylammonium chloride and their use as inhibitors for mild steel corrosion

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