The use of a star-shaped trifunctional acyl chloride for the preparation of polyamide thin film composite membranes

Evelien Maaskant, Wouter Vogel, Theo J. Dingemans, Nieck E. Benes* (Corresponding Author)

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

5 Citations (Scopus)
72 Downloads (Pure)

Abstract

A star-shaped trifunctional acyl chloride bearing ether linkages was synthesized as an alternative to the commonly used trimesoyl chloride (TMC) in the preparation of polyamide thin film composite membranes (TFC). Although this star-shaped acyl chloride has the same functionality as TMC, it is larger in size and its acyl chloride groups are less reactive due to the electron donating ether linkages. In this work, we prepared TFC membranes by the interfacial polymerization of both this star-shaped acyl chloride and TMC with either one of the two structural isomers: m-phenylenediamine (MPD) or p-phenylenediamine (PPD). No strong effect was observed of the substitution pattern of the aromatic diamine on the membrane formation with TMC, due to the high reactivity of the acyl chloride groups of TMC. In contrast, the use of this star-shaped acyl chloride results in significant differences in the properties of the formed TFC membrane depending on the use of MPD or PPD. Where TMC-MPD membranes are well-known for their excellent retention, we could not obtain defect-free membranes prepared from MPD and this star-shaped triacyl chloride (Rrosebengal<77%). The use of PPD instead of MPD, however, did result in defect-free membranes (Rrosebengal>97%) with an acceptable clean water permeance (2.5 L m−2 h−1 bar−1).

Original languageEnglish
Pages (from-to)321-328
Number of pages8
JournalJournal of membrane science
Volume567
Early online date20 Sep 2018
DOIs
Publication statusPublished - 1 Dec 2018

Fingerprint

Composite membranes
Nylons
Polyamides
Stars
Chlorides
chlorides
membranes
Membranes
stars
Thin films
preparation
composite materials
thin films
Ethers
Bearings (structural)
Isomers
Substitution reactions
linkages
Polymerization
Ether

Keywords

  • Interfacial polymerization
  • Monomer reactivity
  • Polyamide
  • Thin film composite

Cite this

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title = "The use of a star-shaped trifunctional acyl chloride for the preparation of polyamide thin film composite membranes",
abstract = "A star-shaped trifunctional acyl chloride bearing ether linkages was synthesized as an alternative to the commonly used trimesoyl chloride (TMC) in the preparation of polyamide thin film composite membranes (TFC). Although this star-shaped acyl chloride has the same functionality as TMC, it is larger in size and its acyl chloride groups are less reactive due to the electron donating ether linkages. In this work, we prepared TFC membranes by the interfacial polymerization of both this star-shaped acyl chloride and TMC with either one of the two structural isomers: m-phenylenediamine (MPD) or p-phenylenediamine (PPD). No strong effect was observed of the substitution pattern of the aromatic diamine on the membrane formation with TMC, due to the high reactivity of the acyl chloride groups of TMC. In contrast, the use of this star-shaped acyl chloride results in significant differences in the properties of the formed TFC membrane depending on the use of MPD or PPD. Where TMC-MPD membranes are well-known for their excellent retention, we could not obtain defect-free membranes prepared from MPD and this star-shaped triacyl chloride (Rrosebengal<77{\%}). The use of PPD instead of MPD, however, did result in defect-free membranes (Rrosebengal>97{\%}) with an acceptable clean water permeance (2.5 L m−2 h−1 bar−1).",
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The use of a star-shaped trifunctional acyl chloride for the preparation of polyamide thin film composite membranes. / Maaskant, Evelien; Vogel, Wouter; Dingemans, Theo J.; Benes, Nieck E. (Corresponding Author).

In: Journal of membrane science, Vol. 567, 01.12.2018, p. 321-328.

Research output: Contribution to journalArticleAcademicpeer-review

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T1 - The use of a star-shaped trifunctional acyl chloride for the preparation of polyamide thin film composite membranes

AU - Maaskant, Evelien

AU - Vogel, Wouter

AU - Dingemans, Theo J.

AU - Benes, Nieck E.

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N2 - A star-shaped trifunctional acyl chloride bearing ether linkages was synthesized as an alternative to the commonly used trimesoyl chloride (TMC) in the preparation of polyamide thin film composite membranes (TFC). Although this star-shaped acyl chloride has the same functionality as TMC, it is larger in size and its acyl chloride groups are less reactive due to the electron donating ether linkages. In this work, we prepared TFC membranes by the interfacial polymerization of both this star-shaped acyl chloride and TMC with either one of the two structural isomers: m-phenylenediamine (MPD) or p-phenylenediamine (PPD). No strong effect was observed of the substitution pattern of the aromatic diamine on the membrane formation with TMC, due to the high reactivity of the acyl chloride groups of TMC. In contrast, the use of this star-shaped acyl chloride results in significant differences in the properties of the formed TFC membrane depending on the use of MPD or PPD. Where TMC-MPD membranes are well-known for their excellent retention, we could not obtain defect-free membranes prepared from MPD and this star-shaped triacyl chloride (Rrosebengal<77%). The use of PPD instead of MPD, however, did result in defect-free membranes (Rrosebengal>97%) with an acceptable clean water permeance (2.5 L m−2 h−1 bar−1).

AB - A star-shaped trifunctional acyl chloride bearing ether linkages was synthesized as an alternative to the commonly used trimesoyl chloride (TMC) in the preparation of polyamide thin film composite membranes (TFC). Although this star-shaped acyl chloride has the same functionality as TMC, it is larger in size and its acyl chloride groups are less reactive due to the electron donating ether linkages. In this work, we prepared TFC membranes by the interfacial polymerization of both this star-shaped acyl chloride and TMC with either one of the two structural isomers: m-phenylenediamine (MPD) or p-phenylenediamine (PPD). No strong effect was observed of the substitution pattern of the aromatic diamine on the membrane formation with TMC, due to the high reactivity of the acyl chloride groups of TMC. In contrast, the use of this star-shaped acyl chloride results in significant differences in the properties of the formed TFC membrane depending on the use of MPD or PPD. Where TMC-MPD membranes are well-known for their excellent retention, we could not obtain defect-free membranes prepared from MPD and this star-shaped triacyl chloride (Rrosebengal<77%). The use of PPD instead of MPD, however, did result in defect-free membranes (Rrosebengal>97%) with an acceptable clean water permeance (2.5 L m−2 h−1 bar−1).

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