Quaternary Ammonium Salts from Halogenated Alkyl Dimethylamines. II. The Polymerization of Gamma-Halogenopropyldimethylamines

Gibbs, C. F.; Littmann, Edwin R.; Marvel, C. S.

doi:10.1021/ja01329a046

Cited by 54 publications

(25 citation statements)

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“…The yellow oil was passed through a short basic alumina column with pentanes to yield a clear oil (4.5 g, 45%). 1 …”

Section: Synthesis Of Nn-bis(3-(dimethylamino)propyl) Cinnamamide (Cmentioning

confidence: 99%

“…The polymers were dissolved in methanol (80 wt.-% solids) and spun cast on cleaned quartz glass at 2 500 rpm for 30 s. In addition, the films were subsequently exposed to UV irradiation, and the cross-linking process was observed with an Ocean Optics USB2000 UV-Vis fiber optic spectrometer for qualitative analysis. 1 6.92 (sty), 5.78 (sty), 5.21 (sty), 4.43 (sty), 3.28 (8H per repeating unit, CH 2 N þ (CH 3 ) 2 CH 2 ), 3.03 (12H per repeating unit, CH 2 N þ (CH 3 ) 2 CH 2 ), 2.81 (12H, (CH 3 ) 2 -N-R 2 closest to chain end), 1.71 (8H per repeating unit, CH 2 CH 2 N þ (CH 3 ) 2 CH 2 CH 2 ), 1.33 (32H per repeating unit, (CH 2 ) 8 CH 2 CH 2 N þ (CH 3 ) 2 ). M n ¼ 9 400 g Á mol À1 from 1 H NMR spectroscopic interpretations.…”

Section: Synthesis Of Styrenic-functionalized 1212-ammonium Ionenementioning

confidence: 99%

“…[1] It is also possible to synthesize ionenes via step-growth polymerization of alkyl dihalides and ditertiary amines in a Menshutkin reaction (Scheme 1). [2] Rembaum et al used this strategy to synthesize ammonium ionenes with a variety of methylene spacers and explored their solution properties.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 12,12‐Ammonium Ionenes with Functionality for Chain Extension and Cross‐Linking via UV Irradiation

Williams

Barta

Ramirez

et al. 2009

Macro Chemistry & Physics

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A novel synthetic methodology for preparing chain‐extended and cross‐linked ionenes using UV irradiation is described. 12,12‐Ammonium ionenes were functionalized with either cinnamate or styrenic functionality at the chain ends and were subsequently exposed to UV irradiation. In addition, a novel copolymer (poly(cinDMPC‐co‐bocDMPC)) was mixed with the cinnamate‐functionalized 12,12‐ammonium ionene to prepare photo‐cross‐linked networks. The UV irradiation process was monitored via UV–Vis spectroscopy after each exposure. The chain‐extended 12,12‐ammonium ionene possessed superior tensile properties compared to the original 12,12‐ammonium ionene. Successful cross‐linking was confirmed with solubility testing of the thin films in methanol. The results indicated that photo‐cross‐linked 12,12‐ammonium ionenes offer potential in membrane technology applications.

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“…The yellow oil was passed through a short basic alumina column with pentanes to yield a clear oil (4.5 g, 45%). 1 …”

Section: Synthesis Of Nn-bis(3-(dimethylamino)propyl) Cinnamamide (Cmentioning

confidence: 99%

Section: Synthesis Of Styrenic-functionalized 1212-ammonium Ionenementioning

confidence: 99%

See 1 more Smart Citation

Synthesis of 12,12‐Ammonium Ionenes with Functionality for Chain Extension and Cross‐Linking via UV Irradiation

Williams

Barta

Ramirez

et al. 2009

Macro Chemistry & Physics

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“…The 15 N NMR spectrum showed two chemical shift peaks at δ: -342.9, -N(CH 3 ) 2 CH 2 CH 3 and -330.4, -N(CH 3 ) 3 .…”

Section: Copolymerization Of Vinylbenzyltrialkylammonium Chloride Andmentioning

confidence: 99%

“…Polymeric quaternary ammonium salts obtained from the reaction of bromodialkylamines of the general structure X(CH 2 ) n N(CH 3 ) 2 where X was chlorine or bromine and n was 4, 5, 6, or 7 was investigated by Littman and Marvel as early as 1929 [2][3][4] (Equation 1). Kein and Brenneisen in 1941 [5], and later Ritter [6] synthesized a series of linear polyquaternary ammonium compounds based on the Menshutkin reaction [7,[8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

POLYCATIONIC SALTS. 4. 2-IONENE OLIGOMER DERIVATIVES OF STYRENE AND THEIR POLYMERIZATION¹

Zarras

Vogl

2000

Journal of Macromolecular Science, Part A

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The synthesis of 2-ionene oligomers was attempted by a sequential Menshutkin reaction to build the unimer, dimer and trimer 2ionene oligomers. The unimer was successfully synthesized in excellent yields with the remaining reactive dimethylamino unit for further reaction. The reaction with vinylbenzyl chloride gave in nearly quantitative yield vinylbenzyl-2-ionene halide. It was successfully polymerized and copolymerized. However, the dimer and trimer of the 2-ionene oligomers were synthesized but could not be isolated in pure form from the reaction mixtures produced during this reaction.

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Synergistic Computational‐Experimental Approach to Improve Ionene Polymer‐Based Functional Hydrogels

Bachl

Zanuy

López-Pérez

et al. 2014

Adv Funct Materials

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The manifold applications of ionene‐based materials such as hydrogels in daily life, biomedical sciences, and industrial processes are a consequence of their unique physical and chemical properties, which are governed by a judicious balance between multiple non‐covalent interactions. However, one of the most critical aspects identified for a broader use of different polyelectrolytes is the need of raising their gelation efficiency. This work focuses on surfactant‐free ionene polymers 1−3 containing DABCO and N,N′‐(x‐phenylene)dibenzamide (x = ortho‐/meta‐/para‐) linkages as model systems to develop a combined computational‐experimental approach to improve the hydrogelation through a better understanding of the gelation mechanism. Molecular dynamics simulations of isomeric ionenes 1–3 with explicit water molecules point out remarkable differences in the assembly of the polymeric chains in each case. Interchain regions with high degree of hydration (i.e., polymer···water interactions) and zones dominated by polymer···polymer interactions are evident in the case of ortho‐ (1) and meta‐ (2) isomeric ionenes, whereas domains controlled by polymer···polymer interactions are practically inexistent in 3. In excellent agreement, ortho‐ionene 1 provides experimentally the best hydrogels with unique features such as thixotropic behavior and dispersion ability for single‐walles carbon nanotubes.

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Quaternary Ammonium Salts from Halogenated Alkyl Dimethylamines. II. The Polymerization of Gamma-Halogenopropyldimethylamines

Cited by 54 publications

References 0 publications

Synthesis of 12,12‐Ammonium Ionenes with Functionality for Chain Extension and Cross‐Linking via UV Irradiation

Synthesis of 12,12‐Ammonium Ionenes with Functionality for Chain Extension and Cross‐Linking via UV Irradiation

POLYCATIONIC SALTS. 4. 2-IONENE OLIGOMER DERIVATIVES OF STYRENE AND THEIR POLYMERIZATION¹

Synergistic Computational‐Experimental Approach to Improve Ionene Polymer‐Based Functional Hydrogels

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Quaternary Ammonium Salts from Halogenated Alkyl Dimethylamines. II. The Polymerization of Gamma-Halogenopropyldimethylamines

Cited by 54 publications

References 0 publications

Synthesis of 12,12‐Ammonium Ionenes with Functionality for Chain Extension and Cross‐Linking via UV Irradiation

Synthesis of 12,12‐Ammonium Ionenes with Functionality for Chain Extension and Cross‐Linking via UV Irradiation

POLYCATIONIC SALTS. 4. 2-IONENE OLIGOMER DERIVATIVES OF STYRENE AND THEIR POLYMERIZATION1

Synergistic Computational‐Experimental Approach to Improve Ionene Polymer‐Based Functional Hydrogels

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POLYCATIONIC SALTS. 4. 2-IONENE OLIGOMER DERIVATIVES OF STYRENE AND THEIR POLYMERIZATION¹