Functional soybean oil-based polyols as sustainable feedstocks for polyurethane coatings

Alagi, Prakash; Ghorpade, Ravindra V.; Jang, Jeong Hyeon; Patil, Chandrashekhar K.; Jirimali, Harishchandra D.; Gite, Vikas V.; Hong, Sung Chul

doi:10.1016/j.indcrop.2018.01.041

Cited by 65 publications

(32 citation statements)

References 57 publications

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“…Polyurethanes are one of the most versatile polymers because isocyanates react with several chemical groups; this provides a way to obtain a full spectrum of applications, such as adhesives, insulation foams, coatings, and biomedical devices . Rigid polyurethane foams (rPUFs) represent a material of choice for improving the energy efficiency of buildings.…”

Section: Introductionmentioning

confidence: 99%

Highly functional lactic acid ring‐opened soybean polyols applied to rigid polyurethane foams

Herrán

Amalvy

Chiacchiarelli

2019

J of Applied Polymer Sci

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We synthesized polyols with high hydroxyl functionalities (F OH s), between 9.0 and 12.6, and characterized them with differential scanning calorimetry, thermogravimetric analysis, and size exclusion chromatography after we parametrically studied the ringopening reaction of epoxidized soybean oil with lactic acid (LA) as a function of the reaction temperature and lactic acid equivalent fraction (f LA ). An increase of only 20 C in the reaction temperature (from 80 to 100 C) caused changes in the hydroxyl number (+17.8%), F OH (-25%), viscosity (-14.0%), and oligomeric content (-24.1%). f LA mostly affected the ring-opening yield, and only for f LA values above 0.4 was possible to achieve values higher than 80%. Rigid polyurethane foams (rPUFs) were synthesized and characterized with scanning electron microscopy, dynamic mechanical analysis (DMA), and compressive mechanical tests. rPUFs with a very high specific compressive strength (7.8 kPa kg -1 m 3 ) were synthesized solely with biobased soybean oil. DMA revealed a compromised relationship between the specific compressive strength and its temperature dependence. To increase the first one, the most relevant method was to increase F OH . Instead, to increase the latter one, the OH number had to be maximized.

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Section: Introductionmentioning

confidence: 99%

Highly functional lactic acid ring‐opened soybean polyols applied to rigid polyurethane foams

Herrán

Amalvy

Chiacchiarelli

2019

J of Applied Polymer Sci

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“…Nevertheless, the obtained ETOFAs can be considered as a suitable raw material for bio-polyol synthesis as they exhibit relatively high oxirane oxygen content of 2.21 mmol/g or 3.54% of oxirane oxygen. 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 The chemical structures of ETOFAs and possible side reaction products, as well as their average molecular mass, are depicted in Figure 2. Side reaction formation is clearly seen in SEC analysis when neat TOFAs are compared with ETOFAs (Figure 2.).…”

Section: Characterization Of Synthesized Tofa-based Bio-polyolsmentioning

confidence: 99%

“…Nevertheless, the obtained ETOFAs can be considered as a suitable raw material for bio-polyol synthesis as they exhibit relatively high oxirane oxygen content of 2.21 mmol/g or 3.54% of oxirane oxygen. 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 The main characteristics of synthesized TOFA-based bio-polyols, such as hydroxyl value, viscosity, acid value, moisture content, density, number average functionality, average molar mass, and polydispersity, are summarized in Table 4. The synthesized TOFA bio-polyols have a relatively high OH value that is necessary and typical for polyols to be used for rigid PU foam development.…”

Section: Characterization Of Synthesized Tofa-based Bio-polyolsmentioning

confidence: 99%

“…TOFAs have a high content of unsaturation and this allows converting the carbon-carbon double bonds relatively easily to more useful functional groups [16]. One such easily introducible functional groups in unsaturated compounds are hydroxyl groups which are essential for producing polyurethanes (PUs) by polycondensation reaction between diverse hydroxyl groups containing compounds (polyols) and isocyanates [2,4,[17][18][19].…”

Section: Introductionmentioning

confidence: 99%

“…In recent years, a variety of methods to obtain polyols from plant oils have been studied, including: epoxidation and oxirane ring-opening [2,4,[26][27][28][29][30][31][32][33][34][35][36][37][38]; hydroformylation and hydrogenation [2,4,16,36,37,39]; ozonolysis [2,4,16,36,37]; air oxidation [16,40]; dihydroxylation [16]; thiol-ene coupling [4,19,37,[41][42][43]; transesterification and transamidation [4,20,[26][27][28]37,38,44,45], and photochemical epoxidation (Schenck-ene reaction) [46][47][48]. However, nearly all of the published papers about polyol synthesis from plant oils are focused just on low or medium functionality/hydroxyl value polyol synthesis.…”

Section: Introductionmentioning

confidence: 99%

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High Functionality Bio-Polyols from Tall Oil and Rigid Polyurethane Foams Formulated Solely Using Bio-Polyols

et al. 2020

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High-quality rigid polyurethane (PU) foam thermal insulation material has been developed solely using bio-polyols synthesized from second-generation bio-based feedstock. High functionality bio-polyols were synthesized from cellulose production side stream—tall oil fatty acids by oxirane ring-opening as well as esterification reactions with different polyfunctional alcohols, such as diethylene glycol, trimethylolpropane, triethanolamine, and diethanolamine. Four different high functionality bio-polyols were combined with bio-polyol obtained from tall oil esterification with triethanolamine to develop rigid PU foam formulations applicable as thermal insulation material. The developed formulations were optimized using response surface modeling to find optimal bio-polyol and physical blowing agent: c-pentane content. The optimized bio-based rigid PU foam formulations delivered comparable thermal insulation properties to the petro-chemical alternative.

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Recent Trends in Waterborne and Bio‐Based Polyurethane Coatings for Corrosion Protection

Luna

2022

Adv Materials Inter

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polyurethanes. Different approaches have been identified for the realization of green PUs, which include-but are not limited to-renewability of the starting materials, sustainability of the synthesis itself, isocyanate-free formulations, and reduction of VOC emissions by limiting the use of organic solvents. [4] In particular, the present review deals with recent researches on two classes of green PUs, namely waterborne and bio-based formulations, focusing on their application as coatings to protect metal surfaces from corrosion. As such, manuscripts specifically addressing the synthesis and/or standard chemicophysical characterization of newly proposed formulations were not considered here. Readers interested in the synthetic aspects of green PUs can refer to recent comprehensive reviews on the topic. [5][6][7][8][9] In the following the recent relevant literature published since 2015 is critically reviewed, highlighting the main strategies pursued to develop reliable and highly performing anticorrosion coatings based on waterborne and bio-based PUs. Then, the collected data on their protective performances are discussed. Waterborne CoatingsWaterborne polyurethanes (WB-PUs) stepped out in the early 1990s driven by the increasingly strict environmental legislation in North America and Europe. [3] The use of sole water evidently solves the issue related to the huge VOC emission associated with traditional solvent-based coatings. In addition, the presence of water as one of the components removes the possibility of any toxic unreacted isocyanate in the system. [9] The introduction of hydrophilic groups in the formulation is essential to guarantee the stability of WB-PU dispersions. [10] On the other hand, it also detrimentally impacts the waterresistance of the resulting coating, hampering the full exploitation of this class of materials for anticorrosion purposes. Playing with the rich PU chemistry is clearly one possible way to tailor the coating properties, including water resistance and thus anticorrosion ability. [11][12][13] Both the polyol and the diisocyanate used for polyurethane synthesis can indeed be properly selected to maximize the coating protective efficacy. In this perspective, Li et al. found that a balanced polyether/polyester polyol ratio is optimal for anticorrosion applications. [12] Yu et al., instead, focused on the role of the diisocyanate structure, highlighting that the protective ability of WB-PU synthesized with 4,4′-dicyclohexylmethane diisocyanate outperforms Polyurethanes (PUs) have been extensively exploited for the production of protective coatings thanks to the versatility of their chemistry, which allows to adjust the coating properties depending on the final application. In the last decade, the concerns on the negative impact on the environment and human health of traditional petroleum-based and solvent-borne PUs have fostered the research on more environmentally friendly alternatives. This review article provides an overview of the recent approaches that have been profitably pu...

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Functional soybean oil-based polyols as sustainable feedstocks for polyurethane coatings

Cited by 65 publications

References 57 publications

Highly functional lactic acid ring‐opened soybean polyols applied to rigid polyurethane foams

Highly functional lactic acid ring‐opened soybean polyols applied to rigid polyurethane foams

High Functionality Bio-Polyols from Tall Oil and Rigid Polyurethane Foams Formulated Solely Using Bio-Polyols

Recent Trends in Waterborne and Bio‐Based Polyurethane Coatings for Corrosion Protection

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