Solvent and catalyst-free synthesis of sunflower oil based polyurethane through non-isocyanate route and its coatings properties

Doley, Simanta; Dolui, S. K.

doi:10.1016/j.eurpolymj.2018.03.030

Cited by 102 publications

(126 citation statements)

References 40 publications

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“…Conversion of ELO into CLO was not possible to be measured by NMR because of the peaks at ~2.8 and ~4.6 ppm were too small to be calculated by the software MesterNova. Relevant reports has been checked, and all of them report the conversions just by titration method …”

Section: Resultsmentioning

confidence: 99%

Linseed oil‐based reactive diluents preparation to improve tetra‐functional epoxy resin properties

Rad

Karami

Zohuriaan‐Mehr

et al. 2019

Polymers for Advanced Techs

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Two kinds of bio-resourced reactive diluents have been synthesized from linseed oil.The prepared epoxidized linseed oil (ELO) and the cyclocarbonated linseed oil (CLO) were separately blended with a petroleum-based tetra-functional epoxy resin (TGDDM) to improve its processability and to overcome the brittleness of the thermoset network therefrom. The linseed oil modifications were spectrally established, and processability improvement of the resin blends was rheologically confirmed. The curing of samples was studied by differential scanning calorimetry, and their mechanical properties (ie, tensile, flexural, fracture toughness, and adhesion) were investigated as well. Scanning electron microscopy images were obtained to reconfirm the toughness improvement of the modified thermosets. In contrast of the epoxidized soybean oil (ie, the most conventionally studied bio-based reactive diluent), ELO and CLO had no negative effects on the thermoset material characteristics. They improved properties such as tensile strength (up to 43.2 MPa), fracture toughness (1.1 MPa m 1/2 ), and peel-adhesion strength (4.5 N/25 mm). It was concluded that ELO and CLO were efficient reactive diluents to be used in formulations of polymer composites, surface coatings, and structural adhesives based on epoxy resins.

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Section: Resultsmentioning

confidence: 99%

Linseed oil‐based reactive diluents preparation to improve tetra‐functional epoxy resin properties

Rad

Karami

Zohuriaan‐Mehr

et al. 2019

Polymers for Advanced Techs

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“…The use of these substrates in PHUs chemistry is regarded as valuable strategy to preparep artially or entirely bio-based polymers, depending on the origin of the diamines employed. [183] The carbonation reaction wasc arried out in as olvent-less reaction at 120 8C( above the meltingp oint of the substrate) under 50 bar CO 2 for 12 hwith TBAB as catalyst. [179] The reaction was carried out by using an organocatalytic binary system formed of 1,3-bis(hydroxyhexafluoroisopropyl)benzene (2.5 mol %) as ah ydrogen bond donor to activate the epoxide and TBAB( 2.5 mol %) as an ucleophile.…”

Section: Monomers With Multiple 5cc Moietiesmentioning

confidence: 99%

“…[182] Doley and Dolui used epoxidized sunflower oil (ESFO) for the preparation of 6c-ESFO as ac omponent of bio-based PHUs. [183] The carbonation reaction wasc arried out in as olvent-less reaction at 120 8C( above the meltingp oint of the substrate) under 50 bar CO 2 for 12 hwith TBAB as catalyst.…”

Section: Monomers With Multiple 5cc Moietiesmentioning

confidence: 99%

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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“…Compared to traditional PUs, these new PUs have hydroxyl groups, so they are called polyhydroxyurethanes (PHUs). [13][14][15][16][17][18][19][20][21] Fleischer et al 15 investigated catalytic carbon dioxide fixation by carbonation of glycerol, trimethylolpropane, and pentaerythritol glycidyl ether, followed by curing with citric acid amino amides in the presence of cellulose carbonate. [10][11][12] Among all the cyclic carbonates, fivemembered bis(cyclic carbonate)s have stable performance and are the most widely studied.…”

Section: Introductionmentioning

confidence: 99%

Preparation of five‐membered bis(cyclic carbonate)s at atmospheric pressure for polyhydroxyurethane coatings

Dai

Tang

et al. 2019

J of Applied Polymer Sci

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Cyclic carbonates reacted with diamines or polyamines have been proposed as a greener and safer method to prepare free isocyanate polyurethane coatings. Here, five kinds of bis(cyclic carbonate)s (TDC: toluene bis(cyclic carbonate), MDC: 4,4 0diphenylmethane bis(cyclic carbonate), IPDC: isophorone bis(cyclic carbonate), HMDC: 4,4 0 -methylenebis(cyclohexyl cyclic carbonate), HDC: hexamethylene bis(cyclic carbonate)) were prepared by reacting glycerol carbonate with diisocyanate under atmospheric pressure. Their structures were verified by 1 H-NMR and 13 C-NMR. These difunctional cyclic carbonates were then reacted with several amines to prepare new polyhydroxyurethane (PHU) coatings, and the film properties were tested. It was found that PHUs based on aromatic and alicyclic structures including TDC, MDC, IPDC, and HMDC displayed high hardness but had poor flexibility and impact resistance, whereas PHUs based on aliphatic structures such as HDC exhibited good flexibility and impact resistance and low hardness. When the length of the alkyl groups in the amine curing agents increased, the impact resistance and flexibility of the PHUs increased, but their pencil hardness decreased. PHUs from TDC, MDC, and IPDC had excellent chemical resistance, but the PHUs from HMDC and HDC had less chemical resistance. Some films displayed excellent properties including 4H pencil hardness, 100 cm kg impact resistance, and excellent flexibility. Some PHUs exhibited good thermal stability, with T 5% values all above 242 C.

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Solvent and catalyst-free synthesis of sunflower oil based polyurethane through non-isocyanate route and its coatings properties

Cited by 102 publications

References 40 publications

Linseed oil‐based reactive diluents preparation to improve tetra‐functional epoxy resin properties

Linseed oil‐based reactive diluents preparation to improve tetra‐functional epoxy resin properties

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

Preparation of five‐membered bis(cyclic carbonate)s at atmospheric pressure for polyhydroxyurethane coatings

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Solvent and catalyst-free synthesis of sunflower oil based polyurethane through non-isocyanate route and its coatings properties

Cited by 102 publications

References 40 publications

Linseed oil‐based reactive diluents preparation to improve tetra‐functional epoxy resin properties

Linseed oil‐based reactive diluents preparation to improve tetra‐functional epoxy resin properties

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

Preparation of five‐membered bis(cyclic carbonate)s at atmospheric pressure for polyhydroxyurethane coatings

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Product

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