Properties and degradation of castor oil-based fluoridated biopolyurethanes with different lengths of fluorinated segments

Li, Jia‐Wun; Cheng, Yi-Hsien; Lee, Hsun-Tsing; Tsen, Wen‐Chin; Chiu, Chih‐Wei; Suen, Maw‐Cherng

doi:10.1039/c9ra04654b

Cited by 11 publications

(11 citation statements)

References 48 publications

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“…The C 1s peak of the worn steel surface lubricated by castor oil alone is divided into three peaks for the C−C bond, C−O bond, and C�O bond (located at 284.8, 286.4, and 287.6 eV, respectively). 15,32 These species are supposed to be derived from the alkyl chain and functional oxygen-containing groups of castor oil. The O 1s peak is divided into two peaks located at 531.4 and 533.0 eV, indexed to O�C and O−C bonds, respectively.…”

Section: Tribological Propertiesmentioning

confidence: 99%

“…The O 1s peak is divided into two peaks located at 531.4 and 533.0 eV, indexed to O�C and O−C bonds, respectively. 15,32 For castor oil containing 0.5% P(MOP-PA), a new C 1s peak with a contribution of 6.4% emerges at 291.6 eV, and this C 1s signal is derived from the π−π* satellite peak of the benzene ring of P(MOP-PA). 33 According to the XPS analysis, it can be inferred that P(MOP-PA) is adsorbed and accumulates on the sliding steel surface, improving the tribological performance of castor oil.…”

Section: Tribological Propertiesmentioning

confidence: 99%

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Controllable Synthesis and Synergistic Antioxidation Mechanism of Poly(p-methoxyphenol-phenylamine) in Biodegradable Vegetable-Based Lubricating Oils

Miao

et al. 2022

Ind. Eng. Chem. Res.

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Poly(p-methoxyphenol-phenylamine) (P(MOP-PA)), a binary copolymer of a phenol and an aromatic amine, was synthesized by liquidphase copolymerization. The tribological properties and antioxidation behavior of the as-synthesized P(MOP-PA) in castor oil and soybean oil were investigated, and its antioxidation mechanism was discussed based on theoretical calculations. The results show that the introduction of P(MOP-PA) into the two kinds of base stocks improves their antioxidation performance at elevated temperatures and reduces friction and wear under pin-on-disk and four-ball sliding tests. In addition, the intramolecular coordination of P(MOP-PA) is responsible for the reduction in the activation energy of hydrogen atom transfer and the stabilization of nitrogen free radicals, which contributes to improving the antioxidation ability of P(MOP-PA).

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Section: Tribological Propertiesmentioning

confidence: 99%

Section: Tribological Propertiesmentioning

confidence: 99%

Controllable Synthesis and Synergistic Antioxidation Mechanism of Poly(p-methoxyphenol-phenylamine) in Biodegradable Vegetable-Based Lubricating Oils

Miao

et al. 2022

Ind. Eng. Chem. Res.

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“…[1][2][3] However, the soft-segment diols, hard-segment diisocyanates, and chain extenders lead to environmental pollution owing to their low biodegradability. With the rising awareness about the environmental challenges associated with the difficult-to-decompose plastics, 4 the application of degradable materials has received a widespread attention. 5,6 For instance, degradable segments can be included during the PU synthesis to increase degradability.…”

Section: Introductionmentioning

confidence: 99%

“…9 In addition, PCL is easily processable in the conventional melt processing equipment. 4 PCL is a highly biocompatible and biodegradable material and finds use in numerous biological applications such as wound dressing, implants, scaffolds, and so forth. [10][11][12][13] Waterborne PU (WPU), a resin used in adhesives, has emerged as a functional waterborne adhesive due to its nonpolluting, safe, and reliable nature, along with optimal compatibility and possibilities to modify the structure.…”

Section: Introductionmentioning

confidence: 99%

Biodegradable cationic waterborne polyurethanes from poly(caprolactone)diol and trimethylol propane monooleate

Liu

Shen

Zhang

et al. 2021

J of Applied Polymer Sci

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Biodegradable cationic waterborne polyurethanes (WPUs) were successfully prepared using poly(caprolactone) diol as the soft segment. To improve the mechanical performance, adhesive strength and water resistance of the WPU films, different amounts of trimethylol propane monooleate (TMPM) containing biodegradable long-branched aliphatic chains were incorporated in the PU structure. The T-peel strength of WPU-3 reached 42.8 N/25 mm, which was about 324% higher than that of WPU (10.1 N/25 mm) without TMPM. On the other hand, the elongation at break of WPU-5 was 811%. On enhancing the TMPM content from 0 to 7.8 wt %, the surface tension decreased from 53.6 to 41.5 mN/m and the water contact angle of the WPU films increased from 52.4 to 81.0 , whereas the water absorption was observed to decrease from 15.6% to 9.6%. The fracture mechanism of the WPU films transformed from the brittle failure to the ductile fracture. The experiment results showed the cationic WPU modified by TMPM displayed excellent film-forming property flexibility and adhesion, the surface tension of WPU dispersion and crystallinity of the resulting film were significantly reduced. For the first time, a biodegradable cationic WPU has been prepared by modification with TMPM, which can be employed for constructing the eco-friendly biodegradable cationic WPUs.

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“…It is often considered as a green polymer on account of its biocompatibility and biodegradability by microorganisms [33,34]. Besides, PCL is an easily processable and completely biodegradable synthetic material that can be used with conventional melt processing equipment [35]. Indeed, PCL has been applied in a wide range of fields such as food packaging and biomedical devices [33,36,37].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Properties of Biobased, Cationic, Waterborne Polyurethanes Dispersions from Castor Oil and Poly (Caprolactone) Diol

Chen

Shen

et al. 2021

Applied Sciences

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Biobased cationic waterborne polyurethanes (WPUs) were prepared using isophorone diisocyanate (IPDI), N-methyl diethanolamine (N-MDEA), polycaprolactone (PCL) diol, hydrochlotic acid (HCl), and 1,4-butanediol (BDO). To improve the mechanical performance and adhesive strength of the waterborne polyurethane films, different amounts of castor oil (CO) acting as a cross-linking agent were incorporated in the polyurethane structure. The structures of the waterborne polyurethanes were assessed by Fourier-transform infrared spectroscopy (FTIR). The combination of CO had a positive effect on the dispersion and stability properties of WPUs. WPUs containing higher content of CO demonstrated a remarkable enhancement in homogeneity among particles. The stable aqueous dispersion was obtained even when N-MDEA loading was as low as 3.2 wt%; a bonus of this low hydrophilic moiety was the excellent adhesive strength, whose T-peel strength could reach up to 36.8 N/25 mm, about 114% higher than that of WPU (17.2 N/25 mm) without any CO content. The elongation at break of CO7.40%-WPU was 391%. In addition, the fracture mechanism of the waterborne polyurethane films transformed from the brittle failure to the ductile fracture. The experiment results showed the CO-modified WPUs displayed excellent film-forming property, flexibility, and adhesion, which can be employed for constructing the eco-friendly, biodegradable, cationic, waterborne polyurethanes.

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Properties and degradation of castor oil-based fluoridated biopolyurethanes with different lengths of fluorinated segments

Abstract: To develop a durable, biodegradable polymer, this study successfully synthesized a castor-oil-based prepolymer by using methylene diphenyl diisocyanate as a hard segment, polycaprolactone as a soft segment, and castor oil as a functional monomer.

Cited by 11 publications

References 48 publications

Controllable Synthesis and Synergistic Antioxidation Mechanism of Poly(p-methoxyphenol-phenylamine) in Biodegradable Vegetable-Based Lubricating Oils

Controllable Synthesis and Synergistic Antioxidation Mechanism of Poly(p-methoxyphenol-phenylamine) in Biodegradable Vegetable-Based Lubricating Oils

Biodegradable cationic waterborne polyurethanes from poly(caprolactone)diol and trimethylol propane monooleate

Preparation and Properties of Biobased, Cationic, Waterborne Polyurethanes Dispersions from Castor Oil and Poly (Caprolactone) Diol

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