Linear and macrocyclic water soluble polyacylhydrazones and their utilisation in coatings

Daines, Alison M.; Robinson, Hannah; Glenny, Mark; Williams, D. Bradley G.; Hinkley, Simon F.R.

doi:10.1016/j.porgcoat.2018.04.019

Cited by 8 publications

(21 citation statements)

References 43 publications

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“…NMR spectral data provided evidence for the synthesis of DiLevDEG/ADH, being in good agreement with the reference spectra supplied by Daines. 127 In particular, the carbonyl and methyl regions of the never terminated with the free hydrazide, and the signal for C1 was never observed in the 13 C NMR spectrum of DiLevDEG/ADH. 128 Likewise, C1 was absent from the 13 C NMR spectrum of DiLevDEG/ADH prepared in the current study.…”

Section: Polyacylhydrazone: Dilevulinoyl Diethylene Glycol (Dilevdeg)/adipic Acid Dihydrazide (Adh)mentioning

confidence: 97%

“…Consequently, the aqueous DiLevDEG/ADH polymer solution was used to substitute 30-50% w/w of the crosslinking resin in an acrylic paint, and the resultant coating performed well in standard industry tests for gloss, adherence, and hardness and displayed moderate water resistance. 127 The group noted that the acylhydrazone functionality (-C(=O)-NH-N=CR-) of…”

Section: Polyacylhydrazone: Dilevulinoyl Diethylene Glycol (Dilevdeg)/adipic Acid Dihydrazide (Adh)mentioning

confidence: 99%

“…The project developed out of the work by our research group in which the DiLevDEG/ADH polyacylhydrazone replaced 30-50% w/w of the acrylic resin in a commercial coating, producing a more environmentally friendly paint with functionality capable of Cu(II)-chelation (Figure 2.2). 127 Continuing from this research, it was hypothesised that the DiLevDEG/ADH-substituted paint could charge itself with Cu(II) from an aqueous solution and, thus, become antifouling. In the current work, testing of this hypothesis was designed to be completed in two stages: 1) DiLevDEG/ADH would be synthesised and its Cu(II)-coordination demonstrated, and 2) DiLevDEG/ADH would be formulated into the commercial acrylic paint and evaluated for Cu(II)-loading and antimicrobial activity after exposure to an aqueous solution of Cu(II).…”

Section: Summary and Future Workmentioning

confidence: 99%

“…could be explored. 127 in our research group, the DiLevDEG/ADH polyacylhydrazone was used to substitute a proportion of the crosslinking resin, classified as high molecular weight, in a commercial acrylic paint. Acrylic polymers display exceptional strength, flexibility, gloss, clarity, and weather and chemical resistance, leading to their widespread use.…”

Section: Summary and Future Workmentioning

confidence: 99%

“…In the aforementioned, foundational work by Daines et al 127 The workflow for the second stage of assessments is outlined in Figure 3.4. Initially, the commercial acrylic and DiLevDEG/ADH polyacylhydrazone/acrylic (DAp/acr) paints were formulated, and the bottoms of wells or vials were coated with the paints.…”

Section: Polyacylhydrazone Dilevdeg/adh-substituted Resin In a Commercial Acrylic Paintmentioning

confidence: 99%

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Selective Metal Coordination in Antifouling Coatings

Robinson¹

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<p>Marine biofouling is the accumulation of biological material (e.g. microorganisms, soft- and hard-fouling organisms) on the surface of an object submerged in seawater, and it remains a worldwide problem for shipping industries. The fouling of ship hulls results in a reduction of speed and manoeuvrability due to frictional drag, as well as increased fuel consumption and accelerated corrosion, and the exorbitant expenses and losses of efficiency attributed to biofouling have prompted the development of antifouling coatings. Current antifouling paints use copper as a biocidal agent, but copper-based paints are increasingly being banned due to environmental concerns about the non-target effects of leached copper. This project aims to circumvent these concerns and tightening regulations via a revolutionary concept: the development of marine antifouling paints that incorporate Cu(II)-selective ligands to draw the biocidal ingredient (i.e. Cu(II)) from seawater. A multistage strategy emerged for the development of this technology. First, criteria were established for the project’s ideal ligand, and ligands were synthesised or selected based on these criteria. Second, the ligands were incorporated in coatings through covalent modification of the paint binder or additives. Third, methodology was developed and implemented to test each coating’s ability to coordinate and retain Cu(II), as well as its subsequent ability to prevent microfouling by marine bacteria. The suitability of two ligand classes was assessed: acylhydrazones and tetraaza macrocycles, specifically cyclen. Unlike the acylhydrazones, cyclen met the established criteria and was initially evaluated as a curing agent and/or surface-modifier in a two-pack epoxy system with resin Epikote™ 235. However, the Cu(II)-loading by these coatings was relatively low, being at most ~0.05% w/w, and the modification of silica, a common paint additive, with cyclen was explored as an alternative formulation route. The method for the functionalisation of silica with cyclen was optimised, and the maximum Cu(II)-loading achieved by the product was 2.60% w/w. The cyclen-functionalised silica was incorporated on the surface of an epoxy coating, and a bacterial adherence assay was developed to assess the cellular attachment of marine bacterium Vibrio harveyi to this coating, which was found to be undeterred. Yet, the development of the strategy and testing methodology by which the project’s goals may be achieved provides a solid foundation for future work.</p>

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Section: Polyacylhydrazone: Dilevulinoyl Diethylene Glycol (Dilevdeg)/adipic Acid Dihydrazide (Adh)mentioning

confidence: 97%

Section: Polyacylhydrazone: Dilevulinoyl Diethylene Glycol (Dilevdeg)/adipic Acid Dihydrazide (Adh)mentioning

confidence: 99%

Section: Summary and Future Workmentioning

confidence: 99%

Section: Summary and Future Workmentioning

confidence: 99%

Section: Polyacylhydrazone Dilevdeg/adh-substituted Resin In a Commercial Acrylic Paintmentioning

confidence: 99%

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Selective Metal Coordination in Antifouling Coatings

Robinson¹

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Towards Sustainable Materials: A Review of Acylhydrazone Chemistry for Reversible Polymers

Ramimoghadam,

Eyckens,

Evans

et al. 2024

Chemistry A European J

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Transitioning towards a circular economy, extensive research has focused on dynamic covalent bonds (DCBs) to pave the way for more sustainable materials. These bonds enable debonding and rebonding on demand, as well as facilitating end‐of‐life recycling. Acylhydrazone/hydrazone chemistry offers a material with high stability under neutral and basic conditions making it a promising candidate for materials research, though the material is susceptible to acid degradation. However, this degradation under acidic conditions can be exploited, making it widely applicable in self‐healing and biomedical fields, with potential for reprocessing and recycling. This review highlights studies exploring the reversibility of acylhydrazone/hydrazone bonds in various polymers, altering their properties, and utilizing them in applications such as self‐healing, reprocessing, and recycling. The review also focuses on how the mechanical properties are affected by the presence of dynamic linkages, and methods to improve the mechanical performance.

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Water‐Soluble (Poly)acylhydrazones: Syntheses and Applications

Caillaud

Ladavière

2022

Macro Chemistry & Physics

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Acylhydrazone-based (macro)molecules display an increasingly broad spectrum of applications, from small therapeutic molecules and metal-ions probes to self-healing films and biorelevant dynamic polymers. The acylhydrazone function is indeed of prime interest since its unique design combines hydrogen bonds, pH-dependent reversibility, ability to undergo molecular exchanges, and a possible polyvalency. However, a key parameter of its use in aqueous media is the associated water-solubility of the resulting (macro)molecule. This property can indeed become a limitation for applications requiring high concentrations or no organic cosolvent. This review first focuses on describing the acylhydrazone function, its properties, and its relevancy in dynamic combinatorial chemistry. Then it details the synthesis strategies (molecular design, cosolvent, reaction conditions) reported in the literature to ensure a sufficient solubilization of both single-bond and multiple-bond acylhydrazone (macro)molecules, together with their various applications.

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Linear and macrocyclic water soluble polyacylhydrazones and their utilisation in coatings

Cited by 8 publications

References 43 publications

Selective Metal Coordination in Antifouling Coatings

Selective Metal Coordination in Antifouling Coatings

Towards Sustainable Materials: A Review of Acylhydrazone Chemistry for Reversible Polymers

Water‐Soluble (Poly)acylhydrazones: Syntheses and Applications

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