Oligomeric ricinoleic acid synthesis with a recyclable catalyst and application to preparing non-isocyanate polyhydroxyurethane

Ren, Fang‐Yu; You, Fangtian; Gao, Song; Xie, Wei-Hang; He, Liang‐Nian; Li, Hongru

doi:10.1016/j.eurpolymj.2021.110501

Cited by 15 publications

(8 citation statements)

References 53 publications

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“…It is long a pursuit to synthesize PUs via isocyanate-free routes [ 3 ]. The polyaddition of polyfunctional cyclic carbonates with amines affords a class of new polymers, i.e., polyhydroxyurethane (PHU) which has a structure similar to PU [ 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 ]. Compared with the traditional PUs, there are additional side hydroxyl groups adjacent to the carbamate groups along with the main chain of PHU.…”

Section: Introductionmentioning

confidence: 99%

Nanocomposites of Polyhydroxyurethane with POSS Microdomains: Synthesis via Non-Isocyanate Approach, Morphologies and Reprocessing Properties

Liu¹,

Hang²,

Mei³

et al. 2022

Polymers

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In this contribution, we reported the synthesis of a novel trifunctional POSS cyclic carbonate [POSS-3(5CC)]. With a difunctional five-member cyclic carbonate and a trifunctional polyetheramine as the precursor, the nanocomposites of polyhydroxyurethane (PHU) with POSS were synthesized. Transmission electron microscopy (TEM) showed that the nanocomposites of PHUs with POSS were microphase-separated; the spherical POSS microdomains via POSS-POSS interactions were generated with the size of 20~40 nm in diameter. After the introduction of POSS microdomains, the nanocomposites displayed improved thermal and mechanical properties. More importantly, the nanocomposites still displayed the reprocessing properties of vitrimers.

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Section: Introductionmentioning

confidence: 99%

Nanocomposites of Polyhydroxyurethane with POSS Microdomains: Synthesis via Non-Isocyanate Approach, Morphologies and Reprocessing Properties

Liu¹,

Hang²,

Mei³

et al. 2022

Polymers

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“…8,9 PHUs have been obtained mostly from cyclic carbonates of highly unsaturated vegetable oils such as soybean, linseed, and sunflower. 10 However, there are few reports about cyclic carbonates from castor oil. 11,12 Recently, PHUs were obtained from cyclic carbonate monomers synthesized from glycerol carbonate, jojoba oil, and castor oil.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a new bifunctional molecule based on castor oil and CO₂ useful for polyurethanes

Cortés

Echeverri

Gomez

et al. 2022

J of Applied Polymer Sci

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A new bifunctional biobased molecule, the carbonated methyl ester of ricinoleic acid maleate (CME‐RAM), useful for polyurethanes, was obtained from castor oil and CO2. This molecule bears carbonate and maleate functionalities that can participate, respectively, in aza‐Michael and aminolysis reactions. Maleate moieties are strong Michael acceptors and they were introduced into the fatty molecule using mild conditions. The synthetic steps include maleinization of castor oil followed by the simultaneous esterification and transesterification at 60°C. The subsequent stages were the epoxidation with acidic resins and the carbonation with CO2. The best results for epoxidation were obtained using Amberlite IR‐120 as catalyst at 48°C (84% conversion of double bonds). The carbonation of the oxirane ring with CO2 at 130°C, 6 MPa CO2 and 6 h reaction afforded 98% conversion of epoxides. It was demonstrated that aza‐Michael reaction of maleate groups was faster than aminolysis of carbonate groups, using hexylamine as a model molecule. CME‐RAM was oligomerized with ethylenediamine and used in the formulation of a conventional rigid polyurethane. Petrochemical polyol and isocyanate can be partially replaced by this bio‐based oligomer, producing a rigid material with a high percentage of green component and good mechanical properties.

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“…55,56 Castor-based PUs were obtained through a non-isocyanate route using oligomeric ricinoleic acid (ORA) with variable average polymerization degrees depending on the catalytic conditions. 57 Following esterification, epoxidation, cycloaddition with CO 2 , and subsequent curing with diamine, ORA intermediates allow the generation of various PHUs with various mechanical and thermal characteristics. Ricinoleic acid-based NIPUs were also obtained using aliphatic diamine, incorporating octa(aminopropyl) polyhedral oligomeric silsesquioxane (OAP-POSS).…”

Section: Fully Biobased Polyestermentioning

confidence: 99%

CO₂-derived non-isocyanate polyurethanes (NIPUs) and their potential applications

Turnaturi,

Zagni,

Patamia

et al. 2023

Green Chem.

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Oligomeric ricinoleic acid synthesis with a recyclable catalyst and application to preparing non-isocyanate polyhydroxyurethane

Cited by 15 publications

References 53 publications

Nanocomposites of Polyhydroxyurethane with POSS Microdomains: Synthesis via Non-Isocyanate Approach, Morphologies and Reprocessing Properties

Nanocomposites of Polyhydroxyurethane with POSS Microdomains: Synthesis via Non-Isocyanate Approach, Morphologies and Reprocessing Properties

Synthesis of a new bifunctional molecule based on castor oil and CO₂ useful for polyurethanes

CO₂-derived non-isocyanate polyurethanes (NIPUs) and their potential applications

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Oligomeric ricinoleic acid synthesis with a recyclable catalyst and application to preparing non-isocyanate polyhydroxyurethane

Cited by 15 publications

References 53 publications

Nanocomposites of Polyhydroxyurethane with POSS Microdomains: Synthesis via Non-Isocyanate Approach, Morphologies and Reprocessing Properties

Nanocomposites of Polyhydroxyurethane with POSS Microdomains: Synthesis via Non-Isocyanate Approach, Morphologies and Reprocessing Properties

Synthesis of a new bifunctional molecule based on castor oil and CO2 useful for polyurethanes

CO2-derived non-isocyanate polyurethanes (NIPUs) and their potential applications

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Product

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Synthesis of a new bifunctional molecule based on castor oil and CO₂ useful for polyurethanes

CO₂-derived non-isocyanate polyurethanes (NIPUs) and their potential applications