Synthesis and properties of fluorinated non-isocyanate polyurethanes coatings with good hydrophobic and oleophobic properties

Wu, Zhijun; Tang, Liuyan; Dai, Jingtao; Qu, Jinqing

doi:10.1007/s11998-019-00195-5

Cited by 32 publications

(18 citation statements)

References 28 publications

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“…Fluorinated cyclic carbonates (up to 3 wt %) were added to a PHU formulation by Wu et al 69 to increase the hydrophobic behavior of the coatings after curing at 120 °C. These coatings displayed water contact angles of 107° and provided good stain and corrosion resistances to tin substrates.…”

Section: Approaches For the Preparation Of Nipu-based Adhesives And C...mentioning

confidence: 99%

Poly(hydroxyurethane) Adhesives and Coatings: State-of-the-Art and Future Directions

Gomez-Lopez

Panchireddy

Grignard

et al. 2021

ACS Sustainable Chem. Eng.

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Polyurethane (PU) adhesives and coatings are widely used to fabricate high-quality materials due to their excellent properties and their versatile nature, which stems from the wide range of commercially available polyisocyanate and polyol precursors. This polymer family has traditionally been used in a wide range of adhesive applications including the bonding of footwear soles, bonding of wood (flooring) to concrete (subflooring), in the automotive industry for adhering different car parts, and in rotor blades, in which large surfaces are required to be adhered. Moreover, PUs are also frequently applied as coatings/paints for automotive finishes and can be applied over a wide range of substrates such as wood, metal, plastic, and textiles. One of the major drawbacks of this polymer family lies in the use of toxic isocyanate-based starting materials. In the context of the REACH regulation, which places restrictions on the use of substances containing free isocyanates, it is now urgent to find greener routes to PUs. While non-isocyanate polyurethanes (NIPUs) based on the polyaddition of poly(cyclic carbonate)s to polyamines have emerged in the past decade as greener alternatives to conventional PUs, their industrial implementation is at an early stage of development. In this review article, recent advances in the application of NIPUs in the field of adhesives and coatings are summarized. The article also draws attention to the opportunities and challenges of implementing NIPUs at the industrial scale.

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Section: Approaches For the Preparation Of Nipu-based Adhesives And C...mentioning

confidence: 99%

Poly(hydroxyurethane) Adhesives and Coatings: State-of-the-Art and Future Directions

Gomez-Lopez

Panchireddy

Grignard

et al. 2021

ACS Sustainable Chem. Eng.

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“…Several researchers have reported their exploratory work on this topic. Generally, there were two non-isocyanates routes for the synthesis of polyurethanes [ 12 , 13 , 14 , 15 , 16 , 17 ]. The first one is the preparation of polyurethane by addition reaction of binary cyclic carbonate and binary amine.…”

Section: Introductionmentioning

confidence: 99%

A Non-Isocyanate Route to Poly(Ether Urethane): Synthesis and Effect of Chemical Structures of Hard Segment

et al. 2022

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A series of non-isocyanate poly(ether urethane) (PEU) were prepared by an environmentally friendly route based on dimethyl carbonate, diols and a polyether. The effect of the chemical structure of polyurethane hard segments on the properties of this kind of PEU was systematically investigated in this work. Polyurethane hard segments with different structures were first prepared from hexamethylene di-carbamate (BHC) and different diols (butanediol, hexanediol, octanediol and decanediol). Subsequently, a series of non-isocyanate PEU were obtained by polycondensation of the polyurethane hard segments with the polyether soft segments (PTMG2000). The PEU were characterized by GPC, FT-IR, 1H NMR, DSC, WAXD, SAXS, AFM and tensile testing. The results show that the urea groups generated by the side reaction affect the degree of crystallization of hard segments by influencing the hydrogen bonding of the hard segments molecular chains. The degree of hard segment crystallization, in turn, affects the thermal and mechanical properties of the polymer. The urea group content is related to the carbon chain length of the diol used for the synthesis of hard segments. When butanediol is applied to synthesize hard segment, the hard segment of the resulting PEU is unable to crystallize. Therefore, the tensile strength and modulus of elasticity of butanediol-based PEU is lowest among three, though it possesses the highest urea group content. When longer octanediol or decanediol is applied to synthesize the hard segment, the hard segments in the resulting polyether-based polyurethane are crystallizable and the resulting PEU possesses higher tensile strength.

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“…Ring opening pathways use cyclic carbamates or ureas that are then polymerized through transcarbamoylation under high temperatures (Scheme 1c) and polyaddition pathways use cyclic carbonates as precursors for polyurethanes (Scheme 1d). 8,9 Most of these isocyanate-free routes have their drawbacks, for example in the formation of isocyanates in-situ (Scheme 1a), acyl azides are used as precursor which are also harmful substances. The polycondensation route (Scheme 1b) releases side-products during curing which limits industrial usage, which in the case of ring-opening is limited by the high temperatures required (Scheme 1c).…”

Section: Introductionmentioning

confidence: 99%

Isocyanate-free Polyurea Synthesis via Ru-Catalyzed Car-bene Insertion into the N‒H Bonds of Urea

Zwart

Laan

Leeuwen

et al. 2022

Preprint

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Polyureas have widespread applications due to their unique material properties. Due to the toxicity of isocyanates, sus-tainable isocyanate-free routes to prepare polyureas is a field of active research. Current routes to isocyanate-free poly-ureas focus on constructing the urea moiety in the final polymerizing step. In this study we present a new isocyanate-free method to produce polyureas by Ru-catalyzed carbene insertion into the N‒H bonds of urea itself in combination with a series of bis-diazo compounds as carbene precursors. The mechanism was investigated by kinetics and DFT studies, re-vealing the rate determining step to be nucleophilic attack of a Ru-carbene moiety by urea. This study paves the way to use transition-metal catalyzed reactions in alternative routes to polyureas.

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Synthesis and properties of fluorinated non-isocyanate polyurethanes coatings with good hydrophobic and oleophobic properties

Cited by 32 publications

References 28 publications

Poly(hydroxyurethane) Adhesives and Coatings: State-of-the-Art and Future Directions

Poly(hydroxyurethane) Adhesives and Coatings: State-of-the-Art and Future Directions

A Non-Isocyanate Route to Poly(Ether Urethane): Synthesis and Effect of Chemical Structures of Hard Segment

Isocyanate-free Polyurea Synthesis via Ru-Catalyzed Car-bene Insertion into the N‒H Bonds of Urea

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