Poly(hydroxyurethane)s with diethyl tartrate-based amide backbone by an isocyanate-free route: Use as adhesives

Tryznowski, Mariusz; Gołofit, Tomasz; Świderska, Aleksandra

doi:10.1016/j.polymer.2018.04.041

Cited by 17 publications

(19 citation statements)

References 45 publications

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“…Adipic acid, the dicarboxylic acid component of 4f',c an be obtained from glucoset hrough biological pathways. [141] Recently,S ardon et al prepared 4l from a,a-diglycerol and DMC as model compound for studying the organocatalyzed formation of PHUs that led to the discovery of an ovel approachf or the synthesis of poly(hydroxyurea-urethane)s. [142] In as tudy exploring the synthesis PHUs in bulk and miniemulsion processes, [143] Cramaila nd co-workersp repared 4m by thiol-ene reaction between 1,4-butanethiol and 3d in the presence of 2,2-dimethoxy-2-phenylacetophenone under UV light. [132] UA was treated with GD, leadingt of ormation of a vicinal diol, and with diethylc arbonate (DEC), leading to 2i.…”

Section: Terminal Biscarbonatesmentioning

confidence: 99%

“…[141] This monomer was further treated with 4l to yield the corresponding PHU, whiche xhibited a highert hermal stability and tensile strengtht han comparable PHUs without amide groups. Diethyl tartrate was treated with an excesso fd iamine to yield an ew diaminom onomer containing amide groups.…”

Section: Adhesivesmentioning

confidence: 99%

“…In the continuationo fp reviousw ork, the same group applied 4l for the synthesis of PHUs adhesives by reactionwith diamines based on tartrate amides. [141] Recently,S ardon et al prepared 4l from a,a-diglycerol and DMC as model compound for studying the organocatalyzed formation of PHUs that led to the discovery of an ovel approachf or the synthesis of poly(hydroxyurea-urethane)s. [142] In as tudy exploring the synthesis PHUs in bulk and miniemulsion processes, [143] Cramaila nd co-workersp repared 4m by thiol-ene reaction between 1,4-butanethiol and 3d in the presence of 2,2-dimethoxy-2-phenylacetophenone under UV light.…”

Section: Terminal Biscarbonatesmentioning

confidence: 99%

“…Diethyl tartrate was treated with an excesso fd iamine to yield an ew diaminom onomer containing amide groups. [141] This monomer was further treated with 4l to yield the corresponding PHU, whiche xhibited a highert hermal stability and tensile strengtht han comparable PHUs without amide groups. Measurements of contact angles and calculation of surface and interface free energies indicated potentially high adhesion of the PHU to wood.A no verview of adhesion performances for as election of the discussed polymers is given in Table 2.…”

Section: Adhesivesmentioning

confidence: 99%

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Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization

et al. 2019

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Given the large amount of anthropogenic CO2 emissions, it is advantageous to use CO2 as feedstock for the fabrication of everyday products, such as fuels and materials. An attractive way to use CO2 in the synthesis of polymers is by the formation of five‐membered cyclic organic carbonate monomers (5CCs). The sustainability of this synthetic approach is increased by using scaffolds prepared from renewable resources. Indeed, recent years have seen the rise of various types of carbonate syntheses and applications. 5CC monomers are often polymerized with diamines to yield polyhydroxyurethanes (PHU). Foams are developed from this type of polymers; moreover, the additional hydroxyl groups in PHU, absent in classical polyurethanes, lead to coatings with excellent adhesive properties. Furthermore, carbonate groups in polymers offer the possibility of post‐functionalization, such as curing reactions under mild conditions. Finally, the polarity of carbonate groups is remarkably high, so polymers with carbonates side‐chains can be used as polymer electrolytes in batteries or as conductive membranes. The target of this Review is to highlight the multiple opportunities offered by polymers prepared from and/or containing 5CCs. Firstly, the preparation of several classes of 5CCs is discussed with special focus on the sustainability of the synthetic routes. Thereafter, specific classes of polymers are discussed for which the use and/or presence of carbonate moieties is crucial to impart the targeted properties (foams, adhesives, polymers for energy applications, and other functional materials).

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Section: Terminal Biscarbonatesmentioning

confidence: 99%

Section: Adhesivesmentioning

confidence: 99%

Section: Terminal Biscarbonatesmentioning

confidence: 99%

Section: Adhesivesmentioning

confidence: 99%

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Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization

et al. 2019

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“…The high density of hydrogen bonds in PHUs makes them suitable for adhesive applications and tend to strongly improve their mechanical properties. [36][37][38] Despite the growing interest on PHUs development, several limitations slow however their expansion on an industrial scale. First, the kinetics of the aminolysis is quite low and PHUs are difficult to obtain in mild conditions.…”

Section: Introductionmentioning

confidence: 99%

Hybrid polyhydroxyurethanes: How to overcome limitations and reach cutting edge properties?

Ecochard

Caillol

2020

European Polymer Journal

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The restrictions on isocyanate substances have encouraged researchers to find alternative methods for the synthesis of Polyurethanes (PUs). New pathways have been designed with focus on non-hazardous and eco-friendly substances. The reaction of cyclic carbonates and amines has appeared as the most promising substitute for the synthesis of Non-Isocyanate Polyurethanes (NIPUs). The obtained Polyhydroxyurethanes (PHUs) have been deeply studied these last decades to offer the best solutions in the substitution of isocyanates in PUs synthesis. Strong efforts have been paid to understand key parameters for the synthesis of PHUs and to design new architectures. However, some limitations in terms of kinetics, conversion and molar masses still remain and impede PHUs expansion. Therefore, this review aims to detail the recent progress that has been made on a new strategy, the hybrid PHUs. The characteristics of additional reactants such as a high reactivity, a low viscosity or the ability to reach higher conversions can be combined with the properties of PHUs in hybrid networks. Other functional groups such as acrylates, methacrylates, epoxies, alkenes or siloxanes give access to new designs and materials with higher performances. Hence, the different strategies to perform hybrid PHUs are discussed and detailed. The main strategies employed are the co-polymerization in one-step, the synthesis of prepolymers with various architectures and the synthesis of organic/inorganic and composite PHUs. Furthermore, a short overview of reprocessable PHUs is given as another outlook for PHU development.

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Moisture Curable Hybrid Polyhydroxyurethanes from Sugar‐Derived Dicarbonates

Younes

Marić

2021

Macro Materials & Eng

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A new set of polyhydroxyurethanes (PHUs) is synthesized from bio‐based sorbitol bicarbonate (SBC) and mannitol bicarbonate (MBC). The synthesized dicarbonates are polymerized with two long chain diamines, telelechelic amine terminated poly(propylene glycol) (PPG), and poly(dimethylsiloxane) (PDMS). Despite the high melting points of SBC and MBC, PHU prepolymers are prepared in bulk at moderate temperatures of 60–100 °C. The structural and thermal properties of the resulting PHUs are qualitatively and quantitatively characterized in order to evaluate them as potential sealants and adhesives, and they are end‐capped with moisture curing agents and left to cure at ambient conditions (22 °C and 20–30% humidity) with the curing processes monitored rheologically. The chemical stability of the novel partially sustainable hybrid PHUs (HPHUs) in pure water is investigated to check the viability of applying them outdoors. Only SBC or MBC‐PDMS HPHUs are found to be hydrophobic with water contact angles of 105° and 109°, respectively, but they are brittle. Small and wide‐angle X‐ray scattering of these water‐resistant films show that they are potentially composed of three different phases due to microphase separation: the PDMS matrix, a hard segments phase, and a third phase mixing the PDMS diamine end‐segments and some dissolved hard segments.

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Poly(hydroxyurethane)s with diethyl tartrate-based amide backbone by an isocyanate-free route: Use as adhesives

Cited by 17 publications

References 45 publications

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization

Hybrid polyhydroxyurethanes: How to overcome limitations and reach cutting edge properties?

Moisture Curable Hybrid Polyhydroxyurethanes from Sugar‐Derived Dicarbonates

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Poly(hydroxyurethane)s with diethyl tartrate-based amide backbone by an isocyanate-free route: Use as adhesives

Cited by 17 publications

References 45 publications

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO2 Utilization

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO2 Utilization

Hybrid polyhydroxyurethanes: How to overcome limitations and reach cutting edge properties?

Moisture Curable Hybrid Polyhydroxyurethanes from Sugar‐Derived Dicarbonates

Contact Info

Product

Resources

About

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization