Japanese Lacquer-A Super Durable Coating (Proposed Structure and Expanded Application)

Kumanotani, Ju

doi:10.1007/978-1-4613-3503-0_15

Cited by 16 publications

(9 citation statements)

References 13 publications

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“…Urushi (oriental lacquer) is a traditional natural resin in East Asia that is tapped from the lacquer tree ( Toxicodendron vernicifluum ). , Urushi-coated wooden wares, called urushiwares (or lacquer wares), are now highly prized for their artistic value. Urushiwares are also in daily use because of their superior physical and chemical properties .…”

Section: Introductionmentioning

confidence: 99%

Biobased Coatings Based on Eugenol Derivatives

Watanabe

Takahashi

Kihara

et al. 2018

ACS Appl. Bio Mater.

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We have fabricated plant-based coating materials using urushiol analogues that were synthesized via a simple threestep route from eugenol (4-allyl-2-methoxyphenol), an allylsubstituted guaiacol. To mimic the chemical structure of urushiol, the allyl chain of eugenol was substituted with alkyl thiols by a thiol−ene reaction. The guaiacol backbone was modified to a catechol backbone through a silylation/desilylation reaction. Uniform thin films were obtained on various substrates by spincoating a solution of the urushiol analogues and iron(II) acetate. The physical and chemical properties of these films were comparable to those of urushiol thin films, and the adhesion, mechanical strength, and antioxidant properties were superior. The hydrophobicity and Young's modulus of the film increased with the increase in the alkyl chain length. Because various functional units can be introduced to the catechol backbone, our method could be used to fabricate environmentally sustainable, multifunctional, high-performance coatings from eugenol.

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Section: Introductionmentioning

confidence: 99%

Biobased Coatings Based on Eugenol Derivatives

Watanabe

Takahashi

Kihara

et al. 2018

ACS Appl. Bio Mater.

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“…Urushi (oriental lacquer) is a traditional natural curing resin obtained from the sap of the lacquer tree (Toxicodendron vernicifluum). The main component of urushi sap is urushiol (60–65% in the sap), a mixture of structurally similar catechol derivatives that have unsaturated double bonds in their long alkyl side chain. , Urushi is cured in two steps. The first step is the oxidative reaction of the catechol moiety of urushiol to form oligomers.…”

Section: Introductionmentioning

confidence: 99%

Biobased Polymer Coating Using Catechol Derivative Urushiol

et al. 2016

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We have investigated the mechanism of the superior mechanical robustness of coated thin films of the catechol derivative urushiol. We synthesized hydrogenated urushiol (h-urushiol) by hydrogenating the double bonds in the long alkyl side chain of urushiol, and the physical properties of thin films of mixtures of urushiol and h-urushiol were evaluated. Atomic force microscopy observations revealed that these coated thin films have a homogeneous surface with no phase separation, regardless of the h-urushiol content, arising from the similarity of the chemical structures. The films showed good adhesive properties because the adhesion originates from the catechol structure. In contrast, curing time depended strongly upon the h-urushiol content. The curing of the h-urushiol thin film took 12 h, whereas the urushiol thin film was cured within 10 min. Moreover, the strain-induced elastic buckling instability for mechanical measurements test and the bulge test confirmed that the increase in the h-urushiol content decreased the mechanical strength. Because the double bonds in the urushiol side chain contribute to forming the highly cross-linked structure, the lack of double bonds in h-urushiol resulted in the slow curing and low mechanical strength. Interestingly, the mechanical robustness started to increase over 80 mol % h-urushiol. The saturated long alkyl side chain of h-urushiol faced the surface, and the regular structure of the uniform side chain may improve the mechanical properties of the coated film. Our results will help to develop biomimetic catechol-based coatings.

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“…16−18 Urushiol is the main chemical component of the sap of urushi (lacquer tree) and has a long alkyl side chain bearing unsaturated double bonds. 19,20 We found that both the flexibility of the alkyl chain and the reactivity of the unsaturated double bonds play an important role in enhancing the robustness of the urushiol coating. Although our results suggest that urushiol is a promising plant-based raw material, its large scale use as an industrial coating material has been restricted because of limited production and high costs.…”

Section: ■ Introductionmentioning

confidence: 96%

“…A wide range of catecholic and phenolic derivatives has been shown to exist in nature. For example, 3,4-dihydroxyphenylalanine residues form an adhesive protein in mussels that exhibits superior adhesive properties in water. , In addition, catechol derivatives have attracted significant attention as biomimetic adhesives and coating materials. − Because the catechol molecule itself has a poor formability and unsuitable mechanical properties for practical use, the catechol unit is often attached as a pendant group in artificial polymers, − or alternatively, metal complexes can be formed to improve the mechanical properties of catechol-based materials. , Indeed, we previously reported that thermal curing of the thin film of urushiol (i.e., a 3-substituted-catecol) with iron(II) acetate produces a green coating with a superior mechanical strength. − Urushiol is the main chemical component of the sap of urushi (lacquer tree) and has a long alkyl side chain bearing unsaturated double bonds. , We found that both the flexibility of the alkyl chain and the reactivity of the unsaturated double bonds play an important role in enhancing the robustness of the urushiol coating. Although our results suggest that urushiol is a promising plant-based raw material, its large scale use as an industrial coating material has been restricted because of limited production and high costs.…”

Section: Introductionmentioning

confidence: 99%

Photocurable Urushiol Analogues Bearing Methacryloxy-Containing Side chains

et al. 2019

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Photocurable urushiol analogues were synthesized using eugenol (an ingredient of clove oil) as the starting material. Photo-induced radical polymerization with 2,2dimethoxy-2-phenylacetophenone as a photo-initiator took place in the film prepared from the urushiol analogue-bearing methacryloxy groups at the ends of their side chains. Successful polymerization was confirmed by infrared spectroscopy measurements of the film before and after photoirradiation. Strain-induced elastic buckling instability for mechanical measurement tests revealed that the Young's moduli of the photo-irradiated samples were 4−5 times higher than the films without photo-irradiation. This was attributed to the formation of a highly cross-linked structure through polymerization of the methacrylic moieties and oxidative polymerization of the catechol moieties. Photo-induced surface texturing was also performed for the films prepared on a substrate using a photomask. Negative-tone patterns were successfully obtained after development by soaking in cyclohexanone over several minutes. The preparation of such patterned surfaces was of particular relevance as the obtained surface can serve as a scaffold for cell adhesion, protein immobilization, and the immobilization of other chemicals with spatial disposition.

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Japanese Lacquer-A Super Durable Coating (Proposed Structure and Expanded Application)

Cited by 16 publications

References 13 publications

Biobased Coatings Based on Eugenol Derivatives

Biobased Coatings Based on Eugenol Derivatives

Biobased Polymer Coating Using Catechol Derivative Urushiol

Photocurable Urushiol Analogues Bearing Methacryloxy-Containing Side chains

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