Soybean Oil‐Based Polyurethane Networks: Shape‐Memory Effects and Surface Morphologies

Miao, Shida; Callow, Nicholas V.; Wang, Ping; Liu, Youyan; Su, Zhiguo; Zhang, Songping

doi:10.1007/s11746-013-2273-5

Cited by 36 publications

(17 citation statements)

References 28 publications

(37 reference statements)

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“…Comparing with reported results [54][55][56][57] , the present three polymers show a little stronger hydrophilicity. This result is attributed to the fact that phosphorus is a high electronegative element and P=O bond has a strong tendency to form hydrogen bond with water.…”

Section: Surface Propertiessupporting

confidence: 75%

Phosphorus-containing polymers from THPS. VII. Synthesis of phosphorus-containing trialkynes and their metal-free 1,3-dipolar cycloaddition reaction with azidated soybean-oil

et al. 2016

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A novel hydrolysis-resistant trialkynes, namely tris(prop-2-yn-1-yloxy methyl)phosphane oxide(TPOPO) was prepared from an environmental friendly tetrakis (hydroxymethyl) phosphonium sulfate (THPS). The chemical structure of TPOPO was characterized by FT-IR, NMR ( 1 H, 13 C, 31 P) and MS. The TPOPO underwent metal-free and solvent-free 1,3dipolar cycloaddition reaction with azidated soybean oil (AzSBO) with different alkyne/azide molar ratio. The gel contents of the cured polymers were higher than 95% and the char yields of polymers at 850℃ were over 16.4%. DMA analysis showed the glass transition temperatures were over 45.9 o C. The cured polymers showed high dielectric constant and dielectric loss for their high polarity.

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Section: Surface Propertiessupporting

confidence: 75%

Phosphorus-containing polymers from THPS. VII. Synthesis of phosphorus-containing trialkynes and their metal-free 1,3-dipolar cycloaddition reaction with azidated soybean-oil

et al. 2016

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“…At −18 °C, these groups may freeze benefitting the shape fixity; at 37 °C, the oscillation of these groups may contribute to the full shape recovery. The function of the pendant groups is also observed in soybean oil-based polyurethanes2728.…”

Section: Discussionmentioning

confidence: 86%

4D printing smart biomedical scaffolds with novel soybean oil epoxidized acrylate

Miao

Zhu

Castro

et al. 2016

Sci Rep

Self Cite

357

258

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Photocurable, biocompatible liquid resins are highly desired for 3D stereolithography based bioprinting. Here we solidified a novel renewable soybean oil epoxidized acrylate, using a 3D laser printing technique, into smart and highly biocompatible scaffolds capable of supporting growth of multipotent human bone marrow mesenchymal stem cells (hMSCs). Porous scaffolds were readily fabricated by simply adjusting the printer infill density; superficial structures of the polymerized soybean oil epoxidized acrylate were significantly affected by laser frequency and printing speed. Shape memory tests confirmed that the scaffold fixed a temporary shape at −18 °C and fully recovered its original shape at human body temperature (37 °C), which indicated the great potential for 4D printing applications. Cytotoxicity analysis proved that the printed scaffolds had significant higher hMSC adhesion and proliferation than traditional polyethylene glycol diacrylate (PEGDA), and had no statistical difference from poly lactic acid (PLA) and polycaprolactone (PCL). This research is believed to significantly advance the development of biomedical scaffolds with renewable plant oils and advanced 3D fabrication techniques.

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“…According to the functionalities of ethyl rhamnolipids, the polyurethanes are assumed to have crosslinked rhamnose residues as the backbone and fatty acid resides as the side chains. This structure is different from the common soybean oil‐based polyurethane networks where fatty acid residues are mostly involved in the backbone chains . Future study is warranted to more systematically examine how this basic structural difference may be used to impart unique/useful properties to the polyurethanes formed.…”

Section: Resultsmentioning

confidence: 92%

Ethyl rhamnolipids as a renewable source to produce biopolyurethanes

Miao

Callow

2014

Euro J Lipid Sci & Tech

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Responding to increasing environmental concerns, lipids are attractive feedstock to produce bio-based polyurethanes. In this study, ethyl rhamnolipids were used to synthesize polyurethanes by reacting with 1,6-hexane diisocyanate (HDI). Rhamnolipids were produced by microbial fermentation, providing a novel source for biopolyurethanes. FTIR and gel content analyses confirmed that the hydroxyl groups on rhamnose residues were reacted with isocyanates. DSC analysis revealed an adjustable glass transition temperature (Tg) from 19 to 50°C. Ethyl rhamnolipids are liquid at 50°C, presumably because rhamnose is connected with fatty acid at a mid-chain position and the unique structure decreases the tendency to crystallize. The liquid polyols were found to have good mixing and reaction properties. The study may inspire future synthesis of novel lipid-based polyols.Practical applications: Use of vegetable oil-based polyols for polyurethane production had been extensively investigated. However, synthesis of these polyols mostly involved introduction of petroleumbased chemicals such as methanol and 1,2-propanediol. Rhamnolipids are natural glycolipids. Using ethyl rhamnolipids to prepare polyurethanes provides an alternative, more renewable route. In addition, it inspires synthesis of vegetable oil polyols by introducing natural sugars.

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Soybean Oil‐Based Polyurethane Networks: Shape‐Memory Effects and Surface Morphologies

Cited by 36 publications

References 28 publications

Phosphorus-containing polymers from THPS. VII. Synthesis of phosphorus-containing trialkynes and their metal-free 1,3-dipolar cycloaddition reaction with azidated soybean-oil

Phosphorus-containing polymers from THPS. VII. Synthesis of phosphorus-containing trialkynes and their metal-free 1,3-dipolar cycloaddition reaction with azidated soybean-oil

4D printing smart biomedical scaffolds with novel soybean oil epoxidized acrylate

Ethyl rhamnolipids as a renewable source to produce biopolyurethanes

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