Synthesis of non-isocyanate polyurethanes and their application in radiation-curable aerospace coatings

Zareanshahraki, Forough; Asemani, H.R.; Skuza, J. R.; Mannari, Vijay

doi:10.1016/j.porgcoat.2019.105394

Cited by 50 publications

(38 citation statements)

References 28 publications

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“…These can subsequently react with polyfunctional acrylates via Michael addition or by reaction with acrylate-functionalized epoxides, methacryloylchloride or methacrylic anhydride to form acrylic oligourethanes. [13][14][15][16] In a recent advance, our group introduced a noniscocyanate route to difunctional hydroxyurethane methacrylates (HUMA) prepared by reacting difunctional amines with cyclic carbonate methacrylate, which is readily available via the chemical fixation of carbon dioxide with glycidyl methacrylate (see Figures 1, 2). The ring opening of the cyclic carbonate with amine accounts for the formation of both primary and secondary hydroxy groups in β-position to the urethane group.…”

Section: Introductionmentioning

confidence: 99%

Functionalized acrylic polyhydroxy urethanes as molecular tool box for photocurable thermosets and 3D printing

Buchheit

Bruchmann

Stoll

et al. 2021

Journal of Polymer Science

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Liquid urethane (meth)acrylates represent attractive components of photocurable thermosets for applications ranging from coatings and adhesives to 3D printing. Herein we tailor liquid polyfunctional urethane methacrylates (UMA) derived from acrylic polyhydroxy urethanes. Cyclic carbonate methacrylates react with diamines to form dihydroxy-functional urethane dimethacrylates. In an "onepot" process the hydroxy groups are functionalized either by reaction with 2-isocyanatoethyl methacrylate (IEMA) or by esterification with methacrylic anhydride (MAA) and acetic anhydride (AA). The hydroxy group esterification substantially lowers the resin viscosity (26-156 Pa•s). Hydroxy functionalization with IEMA and MAA affords tetrafunctional methacrylates. The corresponding photo-cured thermosets exhibit higher crosslinking density and improved stiffness as reflected by increasing the Young's modulus from 2900 to 3700 MPa combined with increasing the glass temperature from 135 to 204 C. Hence, this facile molecular UMA design enables to control functionality and thermoset properties over a wide range and meets the demands of 3D printing applications.

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Section: Introductionmentioning

confidence: 99%

Functionalized acrylic polyhydroxy urethanes as molecular tool box for photocurable thermosets and 3D printing

Buchheit

Bruchmann

Stoll

et al. 2021

Journal of Polymer Science

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“…36 Zareanshahraki et al and Assumption and Mathias also described UV-curable hybrid PHUs via methacrylated amine-and alcohol-terminated NIPUs. 37,38 Schimpf et al synthesized methacrylate-terminated resins by reacting multifunctional amines with methacrylated glycerol carbonate. 39 PHU-siloxane hybrids PHUs can also be combined with siloxane-based chemistries to form hybrid network structures (Fig.…”

Section: Phu-acrylic Hybridsmentioning

confidence: 99%

“…The coatings were tested against military specifications and demonstrated good water resistance, lowtemperature flexibility and fuel resistance but delaminated when immersed in lubricating oil. 37 Figovsky et al evaluated bio-based HNIPUs as sealants and coatings and found improved performance over non-modified compositions. 49 Lambeth and Rizvi evaluated PHU-epoxy hybrids for adhesion where it was demonstrated that the hybrids significantly outperformed a model amine-epoxy formulation in lap shear tests.…”

Section: Applicationsmentioning

confidence: 99%

Progress in hybrid non‐isocyanate polyurethanes

Lambeth

2020

Polymer International

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This mini review highlights recent advances in the field of non-isocyanate polyurethanes with an emphasis on hybrid chemistries that combine cyclic carbonate aminolysis with other step-growth and chain-growth reactions. The origins of hybrid nonisocyanates polyurethanes, different types of reaction chemistries and synthetic strategies are discussed. In addition, applications where combining different types of chemistries are advantageous are emphasized.

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“…During the synthesis and use of paints, a considerable amount of detrimental vapors are released from organic-based raw materials [1]. Such vapors can be reduced in the coating industry by Ultraviolet (UV) curing technology [2]. UV-curable coatings compared with the traditional ways have remarkable benefits such as low energy consumption, a higher pace in the curing process and no need to a solvent [3][4][5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of three novel silane-based carboxylic acids for application in methacrylated epoxy-based oligomers and their ability in the UV curable hybrid coatings

Naghash

Kolahdoozan

Ranjbar

2021

Preprint

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In this study, bromoacetic acid was reacted with 3-(mercaptopropyl) trimethoxy silane (MPTS) and trimethoxy silyl propyl thioacetic acid (TSTA) was produced. Also, bromoacetic acid was reacted with 3-(triethoxysilyl) propylamine (APTS), and triethoxysilyl propylamino acetic acid (TSPA) was synthesized. Finally, from a reaction between trimellitic anhydride (TMA) and APTS, trimellitylimidopropyl triethoxysilane (TMIS) resulted. In all reactions mentioned above, a carboxylic acid head and a trialkoxy silane tail including reactants were obtained. Furthermore, hybrid coatings based on methacrylated bisphenol A epoxy (MBAE) and synthesized carboxylic acids were obtained by photopolymerization. Polycarbonate substrates were utilized for preparation of transparent hybrid films. Then, the solvent resistance, hardness, gel content as well as the adhesion of coatings were measured as physical and mechanical properties. According to the obtained results, these properties of hybrid coatings improved with the increase in alkoxysilanes and sol–gel precursor contents. The surface morphology was characterized by scanning electron microscopy (SEM). The results showed that silica particles were not dispersed homogenously at the molecular level in the hybrid system. Also, the thermogravimetric analysis results indicated that alkoxysilanes enhanced the thermal oxidative stability of the hybrid coatings.

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Synthesis of non-isocyanate polyurethanes and their application in radiation-curable aerospace coatings

Cited by 50 publications

References 28 publications

Functionalized acrylic polyhydroxy urethanes as molecular tool box for photocurable thermosets and 3D printing

Functionalized acrylic polyhydroxy urethanes as molecular tool box for photocurable thermosets and 3D printing

Progress in hybrid non‐isocyanate polyurethanes

Synthesis of three novel silane-based carboxylic acids for application in methacrylated epoxy-based oligomers and their ability in the UV curable hybrid coatings

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