Oxidation of drying oils containing non-conjugated and conjugated double bonds catalyzed by a cobalt catalyst

Oyman, Z.O.; Ming, Weihua; Linde, R. van der

doi:10.1016/j.porgcoat.2005.06.004

Cited by 114 publications

(97 citation statements)

References 13 publications

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“…In addition, it was suggested that the depletion of the conjugated bonds is mostly associated with addition reactions of radical intermediates (such as RO ‚ and ROO ‚ ) to the double bonds, as also noted by Muizebelt and co-workers [15]. It was further shown that the rate of change of the peak intensity of the (initial) cis-C=CH stretching vibration vs. time is quite similar to the one observed in solvent-borne (SB) paints [16], which led to the conclusion that, in WB paints, the type of reactivity induced by the cobalt soap emulsion is similar to that in SB paints [14].…”

Section: Cobalt Soapssupporting

confidence: 53%

Manganese and Iron Catalysts in Alkyd Paints and Coatings

Hage¹,

Böer²,

Maaijen³

2016

Inorganics

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Many paint, ink and coating formulations contain alkyd-based resins which cure via autoxidation mechanisms. Whilst cobalt-soaps have been used for many decades, there is a continuing and accelerating desire by paint companies to develop alternatives for the cobalt soaps, due to likely classification as carcinogens under the REACH (Registration, Evaluation, Authorisation and Restriction of Chemicals) legislation. Alternative driers, for example manganese and iron soaps, have been applied for this purpose. However, relatively poor curing capabilities make it necessary to increase the level of metal salts to such a level that often coloring of the paint formulation occurs. More recent developments include the application of manganese and iron complexes with a variety of organic ligands. This review will discuss the chemistry of alkyd resin curing, the applications and reactions of cobalt-soaps as curing agents, and, subsequently, the paint drying aspects and mechanisms of (model) alkyd curing using manganese and iron catalysts.

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Section: Cobalt Soapssupporting

confidence: 53%

Manganese and Iron Catalysts in Alkyd Paints and Coatings

Hage¹,

Böer²,

Maaijen³

2016

Inorganics

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“…Oyman et al used Raman spectroscopy to compare changes in the abundance of double bonds during oxidation of linseed and tung oils. For linseed oil, the abundance of the non-conjugated double bond decreased as the oxidation proceeded and non-conjugated double bonds converted to conjugated double bonds (Oyman et al 2005a). In contrast, the abundance of the conjugated double bonds in tung oil decreased during oxidation, and, after 90 h of an experimental run, only a small peak signified the residual amount of conjugated trans double bond left (Oyman et al 2005a).…”

Section: Spectroscopic Techniquesmentioning

confidence: 96%

“…For linseed oil, the abundance of the non-conjugated double bond decreased as the oxidation proceeded and non-conjugated double bonds converted to conjugated double bonds (Oyman et al 2005a). In contrast, the abundance of the conjugated double bonds in tung oil decreased during oxidation, and, after 90 h of an experimental run, only a small peak signified the residual amount of conjugated trans double bond left (Oyman et al 2005a). By means of a Raman spectrometer, Muik et al analysed aldehydes and epoxy compounds, such as trans-9,10-and cis-9,10- epoxystearic acids as the oxidation products of oleic acid (Muik et al 2005).…”

Section: Spectroscopic Techniquesmentioning

confidence: 99%

“…The properties of drying alkyd paints vary depending on the type and amount of unsaturated fatty acid employed in preparing the paint formulations (Oyman et al 2005a). The primary remaining components of both the drying and non-drying alkyd resins include alcohols (polyols), such as pentaerythritol or glycerol, and dicarboxylic acid anhydrides, such as phthalic and maleic anhydrides.…”

Section: Introductionmentioning

confidence: 99%

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Low temperature oxidation of linseed oil: a review

et al. 2012

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This review analyses and summarises the previous investigations on the oxidation of linseed oil and the self-heating of cotton and other materials impregnated with the oil. It discusses the composition and chemical structure of linseed oil, including its drying properties. The review describes several experimental methods used to test the propensity of the oil to induce spontaneous heating and ignition of lignocellulosic materials soaked with the oil. It covers the thermal ignition of the lignocellulosic substrates impregnated with the oil and it critically evaluates the analytical methods applied to investigate the oxidation reactions of linseed oil. Initiation of radical chains by singlet oxygen ( 1 Δ g ), and their propagation underpin the mechanism of oxidation of linseed oil, leading to the self-heating and formation of volatile organic species and higher molecular weight compounds. The review also discusses the role of metal complexes of cobalt, iron and manganese in catalysing the oxidative drying of linseed oil, summarising some kinetic parameters such as the rate constants of the peroxidation reactions. With respect to fire safety, the classical theory of self-ignition does not account for radical and catalytic reactions and appears to offer limited insights into the autoignition of lignocellulosic materials soaked with linseed oil. New theoretical and numerical treatments of oxidation of such materials need to be developed. The self-ignition induced by linseed oil is predicated on the presence of both a metal catalyst and a lignocellulosic substrate, and the absence of any prior thermal treatment of the oil, which destroys both peroxy radicals and singlet O 2 sensitisers. An overview of peroxyl chemistry included in the article will be useful to those working in areas of fire science, paint drying, indoor air quality, biofuels and lipid oxidation.

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“…Since similar 1 H-NMR spectra can be observed for SO and its derivatives apart from the intensity difference in the double bonds and epoxy region, only the spectra of LO and its derivatives are shown here. Assignments for signals based on the partly epoxidized LO in the range of δ = 0-6 ppm are displayed in Table 1 [9,[32][33][34]. As characteristic signals of ELO ® , the epoxy groups are observed at 2.85-3.21 ppm region.…”

Section: Durabilitymentioning

confidence: 99%

The reactivity of linseed and soybean oil with different epoxidation degree towards vinyl acetate and impact of the resulting copolymer on the wood durability

Jebrane¹,

Cai²,

Sandström³

et al. 2017

Express Polym. Lett.

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Abstract. Linseed (LO) and soybean oil (SO) were in-situ epoxidized with peracetic acid to produce different degree of epoxidized LO and epoxidized SO. For comparison purpose, commercial epoxidized linseed oil (ELO ® ) and epoxidized soybean oil (ESO ® ) were also included in the study. The effect of epoxidation degree on the copolymerization reaction between epoxidized oils and vinyl acetate (VAc) was investigated. Results showed that a copolymer can be formed between VAc and epoxidized LO with high epoxy content, while no reaction occurred between VAc and SO or its epoxidized derivatives. As the most reactive monomer among the studied oils, the epoxidized LO with highest epoxy content (i.e. ELO ® ) was mixed with VAc and then impregnated into the wood using three different ELO ® /VAc formulations either as solution or as emulsions. After curing, the impact of the resulting copolymer issued from the three tested formulations on the wood durability was evaluated. Results showed that the formulation comprising VAc, ELO ® , H 2 O, K 2 S 2 O 8 and alkaline emulsifier (Formulation 3) can significantly improve wood's durability against white rot-(Trametes versicolor) and brown rot fungi (Postia placenta and Coniophora puteana). Treated wood of 8% weight percentage gain (WPG) was sufficient to ensure decay resistance against the test fungi with less than 5% mass loss.

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Oxidation of drying oils containing non-conjugated and conjugated double bonds catalyzed by a cobalt catalyst

Cited by 114 publications

References 13 publications

Manganese and Iron Catalysts in Alkyd Paints and Coatings

Manganese and Iron Catalysts in Alkyd Paints and Coatings

Low temperature oxidation of linseed oil: a review

The reactivity of linseed and soybean oil with different epoxidation degree towards vinyl acetate and impact of the resulting copolymer on the wood durability

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