Cationic UV-cured coatings containing epoxidized soybean oil initiated by new onium salts containing tetrakis(pentafluorophenyl)gallate anion

Gu, Haiyan; Ren, Kun; Martin, Dustin; Marino, Thomas L.; Neckers, Douglas C.

doi:10.1007/bf02720164

Cited by 27 publications

(17 citation statements)

References 3 publications

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“…Epoxy compounds are known to undergo such reactions ( Figure 3) through an acid-catalyzed cationic mechanism. 6,7 Under the conditions used, it appears that reactions involving formation and subsequent hydrolysis of triphosphate ester to the di-and monoesters is taking place simultaneously with oligomerization.…”

Section: Sopeps With Different Phosphate Ester Contentmentioning

confidence: 97%

“…5 Epoxidized soybean oil (ESO, Figure 1), produced by reaction of soybean oil with peracetic acid, has been investigated as an epoxy resin in UV-cured coatings. 6,7 Thames and Yu have reported cationic UV-cured coatings of epoxide-containing soybean oils that provide corrosion resistance. 6 Recently, ESO has been an attractive option for use in high-solids, low-/zero-VOC thermal cure coatings, owing to its low viscosity, commercial availability, low cost, and numerous reactive oxirane groups.…”

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confidence: 98%

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Self-emulsifiable soybean oil phosphate ester polyols for low-VOC corrosion resistant coatings

Guo

Mannari

Patel

et al. 2006

J Coat. Technol. Res.

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A series of soybean oil phosphate ester polyols (SOPEP) was prepared by reaction of fully epoxidized soybean oil with phosphoric acid and simultaneous hydrolysis in the presence of a polar solvent. The polyols were characterized by determination of acid value, oxirane number, hydroxyl value, molecular weight (GPC), and FTIR spectra. These polyols with varying amounts of acid phosphate groups could be self-emulsified to form aqueous dispersions after neutralization with organic base. These aqueous dispersions showed varying degrees of stability and their appearance ranged from opaque dispersions to translucent to clear solutions. Waterborne coating compositions were prepared using these aqueous dispersions as principal components and their thermally cured film properties were studied. It was found that by careful selection and formulation, SOPEPs can be successfully used for low-VOC waterborne coating formulations. SOPEPs with 3.5% phosphate ester content showed visibly superior corrosion resistance properties. S oybean oil is the most readily available and one of the least expensive vegetable oils in the world. There is currently significant interest in the use of soybean oil as a component in printing inks, 1 as plasticizers, 2,3 and as stabilizers in the manufacture of plastic parts due to its environmentally friendly, biodegradable, and noncorrosive properties. Moreover, it is increasingly attractive to incorporate soybean oil into the making of water-dispersible polymers and resins for packaging films and curing agents used in surface coatings, 4 which are more energy conserving and environmentally desirable than solvent-based paints. 5 Epoxidized soybean oil (ESO, Figure 1), produced by reaction of soybean oil with peracetic acid, has been investigated as an epoxy resin in UV-cured coatings. 6,7 Thames and Yu have reported cationic UV-cured coatings of epoxide-containing soybean oils that provide corrosion resistance. 6 Recently, ESO has been an attractive option for use in high-solids, low-/zero-VOC thermal cure coatings, owing to its low viscosity, commercial availability, low cost, and numerous reactive oxirane groups.Our group has investigated direct incorporation of ESO into UV-cure systems as an additional epoxy component. 8 We also prepared soybean oil phosphate ester polyols (SOPEP, Figure 2) by careful hydrolysis of ESO with phosphoric acid as catalyst, and incorporated them into low VOC industrial bake coatings possessing improved adhesion properties due to the presence of the phosphate ester groups. 9,10 The authors investigated the effects of catalysts, solvents, and the amount of water on the hydrolysis of ESO. 11 Higher boiling hydroxylic solvents gave faster reactions and the water used in the hydrolysis of the phosphate triesters needs to be controlled to prevent hydrolyFigure 1-Epoxidized soybean oil. (15% saturates not shown.)

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Section: Sopeps With Different Phosphate Ester Contentmentioning

confidence: 97%

mentioning

confidence: 98%

Self-emulsifiable soybean oil phosphate ester polyols for low-VOC corrosion resistant coatings

Guo

Mannari

Patel

et al. 2006

J Coat. Technol. Res.

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“…SBO-based materials such as acrylated SBO and ESBO have been investigated in UV-curable materials. 7,[22][23][24] However, no previous research has been found on the utilization of SBO in thiol-ene photochemistry. The incorporation of SBO into thiol-ene-based materials is expected to provide bio-renewable, lower cost, UV-curable materials with interesting properties and little or no environmental impact.…”

Section: Introductionmentioning

confidence: 99%

“…1) are important starting materials for the development and production of biobased industrial products such as adhesives, coatings, plasticizers, lubricants, and composites. 2,[7][8][9][10][11][12][13][14] Curing of polymers by radiation is an efficient way to turn suitable liquid, low viscosity reactive materials into solid materials having good properties, for applications such as coatings, inks, adhesives, and dental materials. 15,16 Curing by light (either visible or ultraviolet, UV) is a form of radiation curing and is also known as photopolymerization.…”

Section: Introductionmentioning

confidence: 99%

Soy-based UV-curable thiol–ene coatings

et al. 2010

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Novel soy-based thiols and enes were synthesized and characterized. Then, soy-based thiol-ene UV-curable coatings were formulated and their coating physiochemical properties were investigated in detail. The use of biorenewable resources, combined with environmentally friendly UV-curable technology, provides a ''green + green'' solution to the stricter regulations in the coatings industry. Novel soy-based thiols and enes were synthesized through the Lewis acid-catalyzed ring opening reaction of epoxidized soybean oil with multifunctional thiols or hydroxyl functional allyl compounds. FTIR and NMR confirmed the formation of the target compounds. The soy-based thiols and enes were formulated with petrochemicalbased enes and thiols, respectively, to make thiol-ene UV-curable coatings. Typical coating film properties, thermal properties, and photopolymerization kinetics of these coatings were studied. Soy-based thiol-ene coatings having lower functionality thiols and enes have poor UV curability and coating properties, which was attributed to the lower crosslink density. Soybased thiols and enes with higher functionality can be UV-cured in combination with petrochemical-based enes or thiols even without the presence of free radical photoinitiators. Better coating film properties were obtained from these higher functionality thiol-ene systems that were toughened by commercial hyperbranched acrylates.

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“…There are relatively a few types of cationic polymerizable monomers and oligomers available for UV-curable coatings, which accounts for only about 8% of all UV-coatings in industry. [3] Cycloaliphatic epoxides are the most widely used epoxides for cationic UV-curable coatings. Cycloaliphatic epoxides provide coatings with fast curing speed, excellent weatherability, scratch and abrasion resistance, and excellent adhesion to a variety of substrate, as well as good hardness.…”

Section: Introductionmentioning

confidence: 99%

UV‐Curable Cycloaliphatic Epoxide Based on Modified Linseed Oil: Synthesis, Characterization and Kinetics

Zou

Soucek

2005

Macro Chemistry & Physics

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Summary: Linseed oil was derivitized with 1,3‐butadiene via a Diels‐Alder reaction. The cycloaddition adduct was then epoxidized using a hydrogen peroxide/quaternary ammonium tetrakis(diperoxotungsto) phosphate system. The cyclohexene derivitized linseed oil (CLO) and the epoxidized cyclohexene derivatized linseed oil (ECLO) were characterized by 1H NMR, 13C NMR, and FT‐IR. In addition, 2D NMR measurements (COSY) were performed on CLO and ECLO to identify the cyclohexyl structures. Molecular weight was determined by ESI‐MS and GPC. The ECLO was photo‐polymerized using UV‐light, and the kinetics of the photo‐curing reactions was evaluated by real‐time FT‐IR and photo‐DSC. All the characterizations supported the successful introduction of cyclohexyl structure to the backbone of linseed oil directly and indirectly. Real‐time FT‐IR and photo‐DSC indicated the slightly improved reactivity of ECLO.Ideal structure of cyclohexene linseed oil (CLO).imageIdeal structure of cyclohexene linseed oil (CLO).

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Cationic UV-cured coatings containing epoxidized soybean oil initiated by new onium salts containing tetrakis(pentafluorophenyl)gallate anion

Cited by 27 publications

References 3 publications

Self-emulsifiable soybean oil phosphate ester polyols for low-VOC corrosion resistant coatings

Self-emulsifiable soybean oil phosphate ester polyols for low-VOC corrosion resistant coatings

Soy-based UV-curable thiol–ene coatings

UV‐Curable Cycloaliphatic Epoxide Based on Modified Linseed Oil: Synthesis, Characterization and Kinetics

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