Thermally Stable, Transparent, Pressure-Sensitive Adhesives from Epoxidized and Dihydroxyl Soybean Oil

Ahn, B. Kollbe; Kraft, Stefan; Wang, D.; Sun, Xiuzhi Susan

doi:10.1021/bm200188u

Cited by 134 publications

(139 citation statements)

References 31 publications

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“…1) and silane-protected methacrylates (2 in Supplementary Fig. 1) were synthesized on the basis of the previously reported silane protection of eugenol 14 , epoxidation 31,32 and acrylation 33 of the alkene group, followed by ultraviolet radical polymerization ( Supplementary Fig. 1).…”

Section: Methodsmentioning

confidence: 99%

Surface-initiated self-healing of polymers in aqueous media

et al. 2014

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Polymeric materials that intrinsically heal at damage sites under wet or moist conditions are urgently needed for biomedical and environmental applications [1][2][3][4][5][6] . Although hydrogels with self-mending properties have been engineered by means of mussel-inspired metal-chelating catechol-functionalized polymer networks 7-10 , biological self-healing in wet conditions, as occurs in self-assembled holdfast proteins in mussels and other marine organisms 11,12 , is generally thought to involve more than reversible metal chelates. Here we demonstrate self-mending in metal-free water of synthetic polyacrylate and polymethacrylate materials that are surface-functionalized with mussel-inspired catechols. Wet self-mending of scission in these polymers is initiated and accelerated by hydrogen bonding between interfacial catechol moieties, and consolidated by the recruitment of other non-covalent interactions contributed by subsurface moieties. The repaired and pristine samples show similar mechanical properties, suggesting that the triggering of complete self-healing is enabled underwater by the formation of extensive catechol-mediated interfacial hydrogen bonds.All polymeric materials suffer damage in the course of their functional lifetimes. Few, if any, completely heal at damage sites. Despite recent progress in the design of self-mending polymeric materials based on crack-activated crosslinking 1 , light 2 , heat 3 or other external stimuli 4 , these remain less than perfectly healed, and, in the case of polymers in wet environments, self-healing technologies are even more limited than those engineered for dry conditions. Mussel adhesive holdfasts exhibit significant self-healing capabilities 11,12 , although the molecular mechanisms involved are poorly understood. Notwithstanding this, the selfmending adhesion and cohesion of isolated dopa (3,4-dihydroxyphenyl-L-alanine)-containing adhesive proteins were shown to rely critically on maintaining dopa in an acidic and reducing environment 13,14 . Significantly different conditions are required to recapitulate the self-healing cohesion of tris-dopa-Fe 3+ -mediated complexes in proteins and polymers [7][8][9]15 . Such results increasingly suggest the importance of dopa, but also its subtle and diverse interfacial reactivity vis-à-vis the traditional and still widely held view that dopa, and catechols generally, function primarily as crosslinkers after their 2-electron oxidation to quinones 16 . To better assess the contribution of catechol to polymer selfhealing in a reducing (pH 3), metal-free wet environment, we prepared a material from common, water-insoluble synthetic acrylic polymers having a catechol-functionalized surface. These materials are completely self-healing in a process initiated by catecholmediated interfacial hydrogen bonding, and consolidated by followup interactions (for example, hydrophobic and steric) after a brief compression (∼6 × 10 4 Pa). The crucial and robust roles played by

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Section: Methodsmentioning

confidence: 99%

Surface-initiated self-healing of polymers in aqueous media

et al. 2014

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“…Compared with traditional PSAs, it has excellent thermal stability, transparency, and peel strength (Ahn et al, 2011). Moreover, the results from soybean oil-based PSA showed great potential to replace petro-based PSAs, such as flexible electronics and medical device.…”

Section: Properties Of Adhesivesmentioning

confidence: 99%

Environmental effects and economic analysis of adhesives: a review of life cycle assessment (LCA) and techno-economic analysis (TEA)

Yang¹,

Rosentrater²

2015

2015 ASABE International Meeting

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In this paper, adhesives made either from fossil fuels or biological sources were examined. The purpose of this review was to investigate the development, processing, and production of bio-adhesives, especially key information about environmental and economic impacts of these types of adhesives. Specifically, the literature was reviewed in terms of life cycle assessment (LCA) and techno-economic analysis (TEA) in order to evaluate the environmental effects, economic performance and potential market acceptance. Several key parameters for life cycle analysis will be compared, such as resource consumption, ecosystem quality and human health; As for TEA, capital costs, operational costs, and unit costs will be explored, as well as the breakeven points. Underlying issues in LCA and TEA will be discussed, and we will examine areas needed for improvement for emerging biobased adhesives.

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“…Vegetable oil, no matter from which source, is generally composed of various triglycerides, the presence of unsaturated bonds making it possible to prepare vegetable oil-based polymeric materials [10][11][12][13][14][15][16][17][18][19][20][21]. As for the preparation of sustainable PU, different types of vegetable oils, including soybean oil, rapeseed oil, corn oil, palm oil, and sunflower oil, have been exploited as raw materials.…”

Section: Introductionmentioning

confidence: 99%

Thermoplastic Polyurethanes Stemming from Castor Oil: Green Synthesis and Their Application in Wood Bonding

Yang

et al. 2017

Coatings

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Abstract:We report an efficient and green approach to synthesize a linear castor oil-based polyurethane (CPU) without using any solvent or catalyst. Diol monomers were first synthesized by the aminolysis reaction between castor oil and diamines; this was accomplished within 6 h at 130 • C. Polymerization of the diols and isocyanate was further confirmed by Fourier transform infrared (FTIR), 1 H-nuclear magnetic resonance ( 1 H-NMR), and gel permeation chromatography analyses. The resultant CPUs showed a good thermal stability with an initial degradation temperature higher than 300 • C, and their mechanical and wood bonding property can be modulated by the structures of diamine. In addition, the CPUs possessed a satisfying water resistance property with the water absorption amount lower than 2%. The green conversion of castor oil to thermoplastic polyurethane affords new opportunities in bio-based industries.

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Thermally Stable, Transparent, Pressure-Sensitive Adhesives from Epoxidized and Dihydroxyl Soybean Oil

Cited by 134 publications

References 31 publications

Surface-initiated self-healing of polymers in aqueous media

Surface-initiated self-healing of polymers in aqueous media

Environmental effects and economic analysis of adhesives: a review of life cycle assessment (LCA) and techno-economic analysis (TEA)

Thermoplastic Polyurethanes Stemming from Castor Oil: Green Synthesis and Their Application in Wood Bonding

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