Unprecedented Adhesive Performance of Propylene-Based Hydroxyl-Functionalized Terpolymers

Kruszynski, Jakub; Nowicka, Weronika; Bouyahyi, Miloud; Liu, Yingxin; Yang, Lanti; Różański, Artur; Anbuchezhian, Nithish; Jasińska-Walc, Lidia; Duchateau, Robbert

doi:10.1021/acsapm.3c00566

Cited by 4 publications

(1 citation statement)

References 60 publications

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“…Moreover, the NPP proved to retain better adhesion strength for the glass for a long time even in water and would thus be suitable for practical applications underwater. The better adhesion may be attributed to functional groups forming dynamic crosslinks based on hydrogen bonding [14], Van der Waals interactions existing among the adhesive molecules and the adhesive/substrate interface [15], and intermolecular π-π interactions of phenyl of NPA [10]. The high hydrophobicity of the phenyl group is responsible for the enhancement of cohesion strength underwater.…”

Section: Practical Applicationsmentioning

confidence: 99%

Fabrication and Applications of Pentaerythritol Tetrakis(3-Mercaptopropionate) Addition to N-Phenylacrylamide Based on Thiol-Ene Click Reaction

Ding,

shen

2024

Preprint

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Thiol/ene free-radical reactions are highly effective when compared with complicated synthesis methods and precise sequence control. Investigation of mercapto-olefins for N-phenylacrylamide (NPA) by thiol/ene free-radical mechanism has not been reported so far. Herein, we report the thiol/ene free-radical reaction of N-phenylacrylamide (NPA)/pentaerythritol tetra(3-mercaptopropionate) (PETMP) by ultraviolet irradiation to give the final product (abbreviation: NPP). The preliminary applications of the NPP were also explored including photoluminescence, adhesive, and thermoresponsive. The adhesion of the NPP has been validated in various substrates. Moreover, it has a strong ability to stick to glass surfaces, even when submerged in water for an extended time. The better adhesion may be attributed to functional groups forming dynamic crosslinks based on hydrogen bonding, van der Waals interactions, and π-π interactions and high hydrophobicity of the phenyl group. This strategy opens an avenue for NPA by thiol-ene click reaction.

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Section: Practical Applicationsmentioning

confidence: 99%

Fabrication and Applications of Pentaerythritol Tetrakis(3-Mercaptopropionate) Addition to N-Phenylacrylamide Based on Thiol-Ene Click Reaction

Ding,

shen

2024

Preprint

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Functionalized Polyolefins Produced by Post-Metallocenes; High Added Value Materials, but Can They Be Produced Efficiently?

Szot,

Chakraborty,

Bouyahyi

et al. 2024

Macromolecules

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Randomly functionalized polyolefins produced by catalysis have received increasing attention owing to their welldefined molecular structures, uniform distribution, and variety in types of functionalities. Herein, we investigate the scalability of the production of hydroxyl-functionalized propylene copolymers via a high temperature solution polymerization process using aluminum trialkyls as passivating agents. Initially, we evaluated the impact of (i) the type of passivating agent (triethylaluminum versus triisobutylaluminum) and (ii) the distance between the hydroxyl and olefin functionality within the functionalized comonomer on the catalytic activity and the functional comonomer incorporation efficiency. Both the functional comonomer's chain length and the type of trialkylaluminum passivating agent have a profound effect on the incorporation efficiency. Subsequently, deeper insight into the origin of the catalyst poisoning by trialkylaluminum-passivated hydroxyl-functionalized comonomers reveals that catalyst deactivation solely happens after incorporation of the functional comonomer and not by coordination of the oxygen of the functional comonomers present in the reaction system. During recycling of dialkylaluminum alkenolates by means of distillation, the occurrence of carbo-and/or hydroalumination side reactions were noticed, triggered by the presence of dialkylaluminum hydrides formed by thermolysis of excess aluminum trialkyls. Exchanging aluminum trialkyls by dialkylaluminum alkoxides as scavengers solved this problem. Modeling studies revealed the impact of the higher nuclearity of trialkylaluminum-passivated hydroxyl-functionalized comonomers on their incorporation efficiency. Addition of a saturated alcohol significantly improved the incorporation efficiency of the functional comonomer, thus bringing the scalability (i.e., enhance the productivity and cost-efficiency) of the copolymerization process a step closer.

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Functionalized Polypropylenes: A Copolymerization and Postmodification Platform

Evans,

Casale,

Morris

et al. 2024

Macromolecules

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Functional polypropylenes (FPs) are regarded as versatile building blocks for next-generation materials; however, their development has been stymied due to current synthetic limitations. Here, we report a diverse range of functionalized polypropylenes prepared via a two-step copolymerization−postmodification strategy. Solution-phase copolymerization of propylene and 11-bromo-1-undecene using C 2 , C 1 , and C s -symmetric catalysts-afforded poly(propylene)-co-(11-bromo-1-undecene), with tunable comonomer incorporation levels, up to 15.5 mol %, with a range of tacticities (iso-, syndio-, and atactic) and a wide molecular weight span (4−212 kg mol −1 ). The latent electrophilic reactivity of the pendent bromide has been utilized in one of three general synthetic routes, enabling the incorporation of an array of polar substituents through the formation of a series of covalent connections (C−O, C−N, C−S, C−P, and C−C). The resulting FPs display distinctly altered bulk and surface properties, compared to polypropylene: improved thermal stability and adhesion to metal, altered wettability, and latent reactivity. This strategy allows access to FPs with both high molecular weight and chosen tacticity, taking advantage of well-developed metallocene catalysts and classical organic substitution chemistry.

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Unprecedented Adhesive Performance of Propylene-Based Hydroxyl-Functionalized Terpolymers

Cited by 4 publications

References 60 publications

Fabrication and Applications of Pentaerythritol Tetrakis(3-Mercaptopropionate) Addition to N-Phenylacrylamide Based on Thiol-Ene Click Reaction

Fabrication and Applications of Pentaerythritol Tetrakis(3-Mercaptopropionate) Addition to N-Phenylacrylamide Based on Thiol-Ene Click Reaction

Functionalized Polyolefins Produced by Post-Metallocenes; High Added Value Materials, but Can They Be Produced Efficiently?

Functionalized Polypropylenes: A Copolymerization and Postmodification Platform

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