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Lazko biobased waterborne polyurethanes for coatings - poster - biopol 2017 vfinal
1.
BIOBASED WATERBORNE POLYURETHANES
FOR COATINGS Jevgenij Lazko, Loïc Poussard, Jérôme Mariage, Jean Marie Raquez, Philippe Dubois jevgenij.lazko@materianova.be Materia Nova, Laboratory of Polymeric and Composite Materials (SMPC), Avenue Copernic 1, 7000 Mons, Belgium Center of Innovation and Research in Materials & Polymers (CIRMAP), University of Mons (UMons), Place du Parc 23, 7000 Mons, Belgium Copyright : photo © Denis Lecuyer REFERENCES 1. K.L. Noble, Progress in Organic Coatings. 1997, 32, 131. 2. L. Poussard, J. Lazko, J. Mariage, J.M. Raquez, P. Dubois, Progress in Organic Coatings. 2016, 97, 175. 3. C. Fu, Z. Zheng, Z. Yang, Y. Chen, L. Shen, Progress in Organic Coatings. 2014, 77, 53. INTRODUCTION The evolution of the regulatory requirements relevant to health, safety and environment is currently driving research into finding new alternatives for polyurethane-based coatings. Development of waterborne polyurethanes (WPU) was undoubtedly a major technological advance that significantly reduced volatile organic compounds emissions [1]. Further sustainability improvements can be achieved replacing petro-based chemistry by renewable bio- based alternatives, using for instance polyols issued from abundant and low cost agro-industrial oils, and particularly of unsaturated ones. The selected polyols for the present studies were fatty dimer functionalized Veopur polyols, recently developed by Vandeputte Oleochemicals. HARD SEGMENT FUNCTIONALIZATION Due to the intrinsic hydrophobicity of plant oil-based polyols, the predominant strategy to obtain WPU consisted in hard segment functionalization: the incorporation of ionic hydrophilic segments directly into polymer backbone during the synthesis. Dimethylolpropionic acid (DMPA) neutralized with triethylamine (TEA) was the couple of charges improving amphiphilic properties used in our recent works about the synthesis of biobased WPU for coating applications and the influence of process parameters on their physicochemical, mechanical and thermal properties [2]. Characterizations showed that WPU formulations based on renewable polyol Veopur and H12MDI could be considered as promising materials for sustainable coatings. An appropriate choice of hard segment content might be used to meet specific requirements for various applications and supports (wood, metal, walls). ACKNOWLEDGEMENTS This research was supported by the Cornet Program in the frame of the “Cost-effective biopolymer interior coatings” Biocoat project (Convention n° 1317997). SOFT SEGMENT FUNCTIONALIZATION An alternative strategy, soft segment functionalization, consists on grafting charges directly on the biobased polyols. This functionalization brings new amphiphilic properties to the polyols, enhancing their hydrophilic character and eventually their dispersability in water. Such modified polyols may finally react with diisocyanates to form WPUs. In this respect, solvent-free UV-mediated thiol-ene grafting of mercapto-carboxylic acids on polyol might represent a sustainable environmentally friendly approach fully considering intrinsic chemical assets of unsaturated vegetal oils [3]. 0,511,522,533,54 [ppm] 86 % Veopur-MPTEA 34 % Veopur 2,42,52,62,72,82,933,1 2,42,52,62,72,82,933,1 Veopur 34 % 86 % MPTEA TEA Veopur-MPTEA 1H NMR spectra of the reference Veopur, MPA grafted Veopur and functionalized Veopur after neutralization with TEA. The soft-segment functionalization strategy recently investigated in Materia Nova Research Center consisted on grafting mercaptopropionic acid (MPA) on biobased polyol Veopur double bonds, using solvent-free UV mediated thiol-ene reaction performed in bulk. Grafted carboxylic moieties were then neutralized by TEA and, in the last step, this functionalized water dispersable polyol was finally polymerized with commercial water soluble polyisocyanates to form WPU. The influence of key process parameters on grafting efficiency was investigated, modification being followed by Iodometric titration and 1H NMR. The emphasis was also placed on the influence of grafting rate on water dispersability of functionalized polyols and coating properties of corresponding WPUs. HO O O HO O O HO O O HO O O COO - + HNEt3 S S COO - + HNEt3 NHCO O OCHN O COO - NHCO O HNEt3 + OCN NCO NHCO O OCHN O NHCO O OCHN O COO -OCN NCO HO OH COO HNEt3 + - HNEt3 + 2) Dispersion in water 3) Addition dispersable polyisocyanate 1) 50 wt% MEK, 80°C, 5h 2) Addition of water 3) MEK removal 1) Solvent-free photochemical thiol-ene grafting UV HS COOH NEt3 Biobased Polyol Hard segment ionic functionalization Soft segment ionic functionalization Waterborne Polyol Waterborne Polyurethanes
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