Bio-based multifunctional fatty acid methyl esters as reactive diluents in coil coatings

Nameer, Sameer; Deltin, Tomas; Sundell, Per‐Erik; Johansson, Mats

doi:10.1016/j.porgcoat.2019.105277

Cited by 20 publications

(13 citation statements)

References 31 publications

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“…The presence of the three monomers in the resulting copolymers was confirmed by 1 H NMR spectra of the precipitated polymers of entries 1 to 3 (Figure 1, A2, and A3). The precipitated polymers showed all the expected signals of the P(BA-co-MMA-co-GCMA).…”

Section: Resultsmentioning

confidence: 75%

“…Yield was calculated with the obtained mass of the precipitated polymer divided by the total mass of the reagents (yield = 64%). The resulting polymer was analyzed by 1 TAEA were added and the viscous solution was mixed with a vortex mixer. Then the solution is quickly transferred to a rectangular aluminum pan, which it was introduce to the oven at 80 °C for 2 h. The resulting materials were analyzed by FTIR, TGA, DSC and DMA.…”

Section: Thermogravimetric Analyses (Tga)mentioning

confidence: 99%

“…Indeed, coatings have many uses such as protection and safety, corrosion prevention, decorative finishing or surfaces cleanliness. Thus, the improvement of the coating materials, the ease of their application, their adhesion and their cost as well as their manufacturing from renewable and sustainable resources [1] are major issues nowadays. Organic coatings meet many of these characteristics and are therefore widely used in the coating industry today.…”

Section: Introductionmentioning

confidence: 99%

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Glycerol carbonate methacrylate: A cross-linking agent for hydroxyurethane-acrylate coatings

Morales‐Cerrada

Boutevin

Caillol

2021

Progress in Organic Coatings

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Poly(meth)acrylates are well-known commodity polymers widely used for coating applications due to easy production, low cost and interesting properties such as their relatively high thermal stability, resistance to breakage and transparency. Some of these properties can be improved by cross-linking, therefore an additional functionalization is necessary. Carbonate group allowed reaction with amines to generate a urethane linkage without the use of toxic and harmful isocyanates. We have synthesized (meth)acrylic copolymers functionalized with cyclic carbonates groups using butyl acrylate (BA), methyl methacrylate (MMA) and glycerol carbonate methacrylate (GCMA) as comonomers to obtain cross-linkable polymers. Different ratios of BA and MMA have been used in order to evaluate the effect on the thermomechanical properties. The cross-linking was performed with tris(2-aminoethyl)amine at 80°C during 2h and was quantitative. The cross-linked hydroxyurethane acrylate copolymers were fully characterized and were used as coatings on glass and steel. The ease of the application and curing process as well as the adhesion strength tests showed that these cross-linked copolymers are promising materials as coating on glass and steel.

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Section: Resultsmentioning

confidence: 75%

Section: Thermogravimetric Analyses (Tga)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Glycerol carbonate methacrylate: A cross-linking agent for hydroxyurethane-acrylate coatings

Morales‐Cerrada

Boutevin

Caillol

2021

Progress in Organic Coatings

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“…LimDiEp is used as a solvent and in epoxy resins as a reactive diluent, MeOle and MeLin can be obtained by the transesterification of vegetable oils such as olive, palm, rapeseed, corn, sesame, soybean, and sunflower [78][79][80]. The epoxidized vegetable oils/FAMES may be used as solvents in the cosmetic and pharmaceutical industries, as reactive diluents [81], PVC plasticizers and stabilizers [79,82,83], in detergents [84] and UV-curable coatings [85], and to produce biodegradable lubricants [86,87] and polyols, which are important raw materials for the synthesis of polyesters and polyurethanes [79,[88][89][90].…”

Section: Epoxidation Of Biomass-derived Olefinsmentioning

confidence: 99%

A 5-(2-Pyridyl)tetrazolate Complex of Molybdenum(VI), Its Structure, and Transformation to a Molybdenum Oxide-Based Hybrid Heterogeneous Catalyst for the Epoxidation of Olefins

Nunes

Gomes

et al. 2021

Catalysts

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There is a considerable practical interest in discovering new ways to obtain organomolybdenum heterogeneous catalysts for olefin epoxidation that are easier to recover and reuse and display enhanced productivity. In this study, the complex salt (H2pytz)[MoO2Cl2(pytz)] (1) (Hpytz = 5-(2-pyridyl)tetrazole) has been prepared, structurally characterized, and employed as a precursor for the hydrolysis-based synthesis of a microcrystalline molybdenum oxide/organic hybrid material formulated as [MoO3(Hpytz)] (2). In addition to single-crystal X-ray diffraction (for 1), compounds 1 and 2 were characterized by FT-IR and Raman spectroscopies, solid-state 13C{1H} cross-polarization (CP) magic-angle spinning (MAS) NMR, and scanning electron microscopy (SEM). Compounds 1 and 2 were evaluated as olefin epoxidation catalysts using the model reaction of cis-cyclooctene (Cy8) with tert-butyl hydroperoxide (TBHP), at 70 °C, which gave 100% epoxide selectivity up to 100% conversion. While 1 behaved as a homogeneous catalyst, hybrid 2 behaved as a heterogeneous catalyst and could be recovered for recycling without showing structural degradation or loss of catalytic performance over consecutive reaction cycles. The substrate scope was broadened to monoterpene DL-limonene (Lim) and biobased unsaturated fatty acid methyl esters, methyl oleate (MeOle), and methyl linoleate (MeLin), which gave predominantly epoxide products.

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“…In particular, unsaturated oleochemicals show enormous potential as double bonds allow versatile functionalizations, one of which is epoxidation. Epoxidation of fatty acids and fatty acid derivatives is highly relevant for forming biobased epoxy compounds, which can be applied in plasticizers, , lubricants, coatings, polyols, polyurethanes, and many more.…”

Section: Introductionmentioning

confidence: 99%

Curse and Blessing–The Role of Water in the Homogeneously Ru-Catalyzed Epoxidation of Technical Grade Methyl Oleate

Vondran

Pela

Palczewski

et al. 2021

ACS Sustainable Chem. Eng.

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A homogeneous Ru-catalyst was investigated toward its potential recycling in methyl oleate epoxidation under mild conditions using hydrogen peroxide as a green oxidant. The literature-known catalyst complex, in situ formed from ruthenium acetylacetonate and dipicolinic acid, offers excellent selectivity toward epoxidation of technical grade (91.5%) methyl oleate. The resulting product methyl 9,10-epoxy stearate exhibits versatile applications. It is used industrially as a biobased epoxide for plasticizers and lubricants, or it can be further processed into polyurethanes. In this work, we first report a concept for homogeneous catalyst recycling, including extraction of the epoxide into an organic phase. Particular emphasis was on the effect of water, as it would accumulate due to recycling of the aqueous catalyst phase and replenishment of hydrogen peroxide prior to each recycling run. Consequently, mass transfer limitations needed to be addressed. By a combined extraction-distillation technique, we report the first sufficient homogeneous catalyst recycling strategy for Ru-catalyzed epoxidation of methyl oleate. Removal of water and separation of epoxide allowed for a ∑TON of 1243 after seven recycling runs with 97% selectivity toward epoxide and a TTON of 1384 after 13 runs, respectively, while catalyst leaching into the product phase was negligibly small. Moreover, pervaporation using a poly(vinyl alcohol) membrane was investigated as a promising technique for both removal of water and retention of the catalyst showing very promising results.

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Bio-based multifunctional fatty acid methyl esters as reactive diluents in coil coatings

Cited by 20 publications

References 31 publications

Glycerol carbonate methacrylate: A cross-linking agent for hydroxyurethane-acrylate coatings

Glycerol carbonate methacrylate: A cross-linking agent for hydroxyurethane-acrylate coatings

A 5-(2-Pyridyl)tetrazolate Complex of Molybdenum(VI), Its Structure, and Transformation to a Molybdenum Oxide-Based Hybrid Heterogeneous Catalyst for the Epoxidation of Olefins

Curse and Blessing–The Role of Water in the Homogeneously Ru-Catalyzed Epoxidation of Technical Grade Methyl Oleate

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