Non-isocyanate urethane linkage formation using l-lysine residues as amine sources

Soares, Ana M. S.; Araújo, Alexandra Maria Dantas de Castro; Olsen, Bradley D.; Machado, A. V.

doi:10.1007/s00726-019-02770-x

Cited by 5 publications

(5 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An interesting renewable source for making the cyclic carbonates is diglycerol. Diglycerol dicarbonate (DGC), explored extensively in the literature for different PHU formulations, − is derived from glycerol, which is a byproduct obtained from the hydrolysis of biomass wastes, the methanolysis of triglycerides, and the production of biodiesel . The worldwide annual production of glycerol has drastically increased in the past decade, and predictions showed that the production of glycerol was 6 times higher than the demand in 2020, making it an abundant raw material for the synthesis of PHUs. , Furthermore, DGC has a melting point of around 65 °C, , so bulk polyadditions are possible at moderate temperatures.…”

Section: Introductionmentioning

confidence: 99%

Bio-based Thermoplastic Polyhydroxyurethanes Synthesized from the Terpolymerization of a Dicarbonate and Two Diamines: Design, Rheology, and Application in Melt Blending

Younes

Marić

2021

Macromolecules

View full text Add to dashboard Cite

The terpolymerization of bio-based diglycerol dicarbonate (DGC) and Priamine 1074 is conducted with aminopropyl terminated polydimethylsiloxane (M n = 1000 g/ mol, PDMS) or 1,10-diaminodecane (DAD). Depending on DGC contents and PDMS/Priamine 1074 ratios, the resulting amorphous thermoplastic polyhydroxyurethanes (TPHUs) present random or block copolymer-like segmented structures. These TPHUs exhibit nanophase separation of small interdomain spacing (3−3.5 nm) mainly caused by DGC. As for DAD, it introduces crystallinity (8%) and chain ordering into the TPHU structure as observed from X-ray measurements. Some PDMS-based TPHUs are blended with PLA, and the blends are found to be partially miscible as they exhibit two T g 's, and their estimated relative energy differences (RED), calculated from Hoftyzer−Van Krevelen's group contribution method, are nearly unity. Based on the type of hydrogen bonding interactions and the extent of immiscibility (RED) of each of the blends, the TPHUs find potential applications as toughening agents and/or plasticizers for PLA.

show abstract

Section: Introductionmentioning

confidence: 99%

Bio-based Thermoplastic Polyhydroxyurethanes Synthesized from the Terpolymerization of a Dicarbonate and Two Diamines: Design, Rheology, and Application in Melt Blending

Younes

Marić

2021

Macromolecules

View full text Add to dashboard Cite

show abstract

“…Its worldwide annual production has increased over 200% between the years 2000 and 2010, and it was predicted that by the year 2020, its production would be 6 times more than the demand, , which makes it an abundant raw material for the preparation of new sustainable HPHU sealants and adhesives. Many studies have characterized diglycerol dicarbonate (DGC)-based PHUs prepared from diamines of different chain lengths. − As for the diamines, bio-based and petrochemical ones are available, and this work uses both with more attention given to poly(dimethylsiloxane) diamines expected to give PHUs with high value-added end properties …”

Section: Introductionmentioning

confidence: 99%

Study of Moisture-Curable Hybrid NIPUs Based on Glycerol with Various Diamines: Emergent Advantages of PDMS Diamines

Younes

Price

Dandurand³

et al. 2020

ACS Omega

View full text Add to dashboard Cite

A sol/gel curing method is used in this work to synthesize hybrid partially bio-based polyhydroxyurethanes (PHUs) from dicarbonates derived from glycerol and various diamines. The method consists of end-capping the PHU prepolymers with moisture-sensitive groups, so sealants and adhesives can be produced from partially sustainable hybrid PHUs (HPHUs), similar to their preparation from end-capped conventional polyurethanes. Diglycerol dicarbonate (DGC) is synthesized and polymerized with different diamines of various chain lengths, and the resulting structural and thermal properties of the PHUs are qualitatively and quantitively characterized. This characterization led to two potential candidates: PHU 4, made of DGC and a poly(propylene glycol) diamine, and PHU 10, prepared from DGC and a poly(dimethylsiloxane) diamine. These polymers, with respective relative number-average molecular weights of 3200 and 7400 g/mol, are end-capped and left to cure under ambient lab conditions (22 °C and 40–50% humidity), and the curing processes are monitored rheologically. Notably, moisture curing does not require any catalyst. The chemical stability of the resulting hybrid PHUs (HPHUs) 4 and 10 in pure water is investigated to check the viability of applying them under outdoor conditions. Only HPHU 10 is found to be resistant to water and shows hydrophobicity with a contact angle of 109°. Tensile tests are conducted on HPHU 10 samples cured under lab conditions for a week and others cured for another week while being immersed in water. The mechanical properties, tensile strength and elongation at break, improve with the samples cured in water, indicating the high-water repellency of HPHU 10.

show abstract

“…Indeed, elastin-like protein (ELP) and lactoglobulin (BLG) formed from whey protein as model proteins were reacted with BCC as described in Scheme 52. [157] There were four renewable and reprocessable PHU networks with crosslink density generated from two biobased polyfunctional carbonates, CSBO and SEC by Sumeng Hu and co-workers. DMA data reveal that CSBO-based PHU networks manifested multiple melt-state recycling steps under mild ChemistrySelect condition (110 °C, 30-40 min), as complete recovery of characteristics with crosslink density comparable to the first moulded samples.…”

Section: Synthetic Route To Obtain Nipu Under Catalytic Pathwaymentioning

confidence: 99%

“…have involved in generation of urethane linkages using lysine moiety to form five‐membered biscyclic carbonate (BCC) and reacted with protected lysine tripeptide, and heptapeptide. Indeed, elastin‐like protein (ELP) and lactoglobulin (BLG) formed from whey protein as model proteins were reacted with BCC as described in Scheme 52 [157] …”

Section: Synthetic Route To Obtain Nipu Under Catalytic Pathwaymentioning

confidence: 99%

Catalyzed and Non‐catalyzed Synthetic Approaches to Obtain Isocyanate‐free Polyurethanes

Chelike

Andavan

2023

ChemistrySelect

View full text Add to dashboard Cite

By reactions of both catalyzed and non-catalyzed pathway, we attempt to show that the synthetic route of non-isocyanate polyurethanes (NIPU) is developed quite recently. The advancement of sustainable, bio-renewable, impermeable and moisture-insensitive NIPU has started to contribute its role in academia and industry. In case of NIPU formulation, polycondensation of dicarbonate with diamine precursors as well as waste-free polyaddition of multifunctional cyclic carbonates with diamines via ring-opening polymerization. Obviously, since the hydroxyl groups (both primary and secondary hydroxyl group) arisen in NIPU is employed to reveal fairly different attributes compared to trivial polyurethanes (PU). The advantage of NIPU comprises of the role of carbon dioxide and renewable feedstock, while various cyclic carbonates obtained to react with diamine substrates to incorporate desired physicochemical and mechanical properties. Indeed, NIPU are noted to be non-toxic, biodegradable and exhibit remarkable properties. In this review, we account the imperative strategies employed in developing essential sustainable NIPU have been discussed in detail.

show abstract

Non-isocyanate urethane linkage formation using l-lysine residues as amine sources

Abstract: Non-isocyanate urethane linkage formation using L-lysine residues as amine sources, Amino Acids

Cited by 5 publications

References 35 publications

Bio-based Thermoplastic Polyhydroxyurethanes Synthesized from the Terpolymerization of a Dicarbonate and Two Diamines: Design, Rheology, and Application in Melt Blending

Bio-based Thermoplastic Polyhydroxyurethanes Synthesized from the Terpolymerization of a Dicarbonate and Two Diamines: Design, Rheology, and Application in Melt Blending

Study of Moisture-Curable Hybrid NIPUs Based on Glycerol with Various Diamines: Emergent Advantages of PDMS Diamines

Catalyzed and Non‐catalyzed Synthetic Approaches to Obtain Isocyanate‐free Polyurethanes

Contact Info

Product

Resources

About