The influence of the NCO/OH ratio and the 1,6-hexanediol/dimethylol propionic acid molar ratio on the properties of waterborne polyurethane dispersions based on 1,5-pentamethylene diisocyanate

Abstract

1,5-Pentamethylene diisocyanate, a novel aliphatic diisocyanate formed from bio-based 1,5-pentamethylenediamine, has been used as a hard segmented material to synthesize polyurethane. In this study, several waterborne polyurethane (WPU) dispersions have been successfully prepared by a prepolymer process from 1,5-pentamethylene diisocyanate poly(polyether) with different NCO/OH ratios and 1,6-hexanediol (HDO)/dimethylol propionic acid (DMPA) molar ratios. The Fourier transform infrared (FTIR) spectra, thermogravimetric analysis, differential scanning calorimetry, X-ray diffraction, and a mechanical tensile test were used to investigate the structures, thermal stability, phase separation, crystallinity, mechanical properties, and adhesive performance of the WPU dispersions. The FTIR results indicate that the degree of hydrogen bonding and the numbers of urea groups increase as the NCO/OH ratio and HDO/DMPA molar ratio increase. Furthermore, the phase separation increases and the thermal stability decreases as the NCO/OH ratio increases or the HDO/DMPA molar ratio decreases. Finally, WPU3.0-2.4 (NCO/OH=3, HDO/DMPA=2.4) exhibits a maximum tensile strength and shear strength, pointing to its possible use as an adhesive. These results could provide a very valuable reference for industrial applications of WPU.

Keywords

1,5-pentamethylene diisocyanate / polyurethane / water based

References

[1] Garcia-Pacios V, Costa V, Colera M, Martin-Martinez J M. Waterborne polyurethane dispersions obtained with polycarbonate of hexanediol intended for use as coatings. Progress in Organic Coatings, 2011, 71(2): 136–146

[2] Krol P, Krol B, Kozakiewicz J, Zapotoczny S, Pilch-Pitera B, Kozdra S. Composites prepared from polyurethanes modified with silicone-acrylic nanopowders. Progress in Organic Coatings, 2015, 81: 72–79

[3] Aznar A C, Pardini O R, Amalvy J I. Glossy topcoat exterior paint formulations using water-based polyurethane/acrylic hybrid binders. Progress in Organic Coatings, 2006, 55(1): 43–49

[4] Chattopadhyay D K, Raju K V S N. Structural engineering of polyurethane coatings for high performance applications. Progress in Polymer Science, 2007, 32(3): 352–418

[5] Fang C Q, Zhou X, Yu Q, Liu S L, Guo D G, Yu R E, Hu J B. Synthesis and characterization of low crystalline waterborne polyurethane for potential application in water-based ink binder. Progress in Organic Coatings, 2014, 77(1): 61–71

[6] Miao S D, Sun L J, Wang P, Liu R N, Su Z G, Zhang S P. Soybean oil-based polyurethane networks as candidate biomaterials: Synthesis and biocompatibility. European Journal of Lipid Science and Technology, 2012, 114(10): 1165–1174

[7] Udagama R, Degrandi-Contraires E, Creton C, Graillat C, McKenna T F L, Bourgeat-Lami E. Synthesis of acrylic-polyurethane hybrid latexes by miniemulsion polymerization and their pressure-sensitive adhesive applications. Macromolecules, 2011, 44(8): 2632–2642

[8] Ali A, Yusoh K, Hasany S F. Synthesis and physicochemical behaviour of polyurethane-multiwalled carbon nanotubes nanocomposites based on renewable castor oil polyols. Journal of Nanomaterials, 2014, 2014: 564384

[9] Ji D, Fang Z, He W, Zhang K, Luo Z Y, Wang T W, Guo K. Synthesis of soy-polyols using a continuous microflow system and preparation of soy-based polyurethane rigid foams. ACS Sustainable Chemistry & Engineering, 2015, 3(6): 1197–1204

[10] Bayer C. Das di-isocyanat-polyadditionsverfahren (Polyurethane). Angewandte Chemie, 1947, 59(9): 257–288 (in German)

[11] Kong X H, Liu G G, Curtis J M. Characterization of canola oil based polyurethane wood adhesives. International Journal of Adhesion and Adhesives, 2011, 31(6): 559–564

[12] Moubarik A, Allal A, Pizzi A, Charrier F, Charrier B. Characterization of a formaldehyde-free cornstarch-tannin wood adhesive for interior plywood. European Journal of Wood and Wood Products, 2010, 68(4): 427–433

[13] Tenorio-Alfonso A, Sanchez M C, Franco J M. Preparation, characterization and mechanical properties of bio-based polyurethane adhesives from isocyanate-functionalized cellulose acetate and castor oil for bonding wood. Polymers, 2017, 9(12): 132

[14] Geurink P J A, Scherer T, Buter R, Steenbergen A, Henderiks H. A complete new design for waterborne 2-pack PUR coatings with robust application properties. Progress in Organic Coatings, 2006, 55(2): 119–127

[15] Melchiors M, Sonntag M, Kobusch C, Jurgens E. Recent developments in aqueous two-component polyurethane (2K-PUR) coatings. Progress in Organic Coatings, 2000, 40(1-4): 99–109

[16] Lai X J, Li X R, Wang L, Shen Y D. Synthesis and characterizations of waterborne polyurethane modified with 3-aminopropyltriethoxysilane. Polymer Bulletin, 2010, 65(1): 45–57

[17] Lu Y S, Larock R C. Soybean oil-based, aqueous cationic polyurethane dispersions: Synthesis and properties. Progress in Organic Coatings, 2010, 69(1): 31–37

[18] Zhou X, Li Y, Fang C Q, Li S J, Cheng Y L, Lei W Q, Meng X J. Recent advances in synthesis of waterborne polyurethane and their application in water-based ink: A review. Journal of Materials Science and Technology, 2015, 31(7): 708–722

[19] Sharma V, Kundu P P. Condensation polymers from natural oils. Progress in Polymer Science, 2008, 33(12): 1199–1215

[20] Garcia-Pacios V, Jofre-Reche J A, Costa V, Colera M, Martin-Martinez J M. Coatings prepared from waterborne polyurethane dispersions obtained with polycarbonates of 1,6-hexanediol of different molecular weights. Progress in Organic Coatings, 2013, 76(10): 1484–1493

[21] Lee S K, Kim B K. High solid and high stability waterborne polyurethanes via ionic groups in soft segments and chain termini. Journal of Colloid and Interface Science, 2009, 336(1): 208–214

[22] Yang J, Gao Y L, Li J H, Ding M M, Chen F, Tan H, Fu Q. Synthesis and microphase separated structures of polydimethylsiloxane/polycarbonate-based polyurethanes. RSC Advances, 2013, 3(22): 8291–8297

[23] Cakic S M, Ristic I S, Cincovitc M M, Nikolic N C, Nikolic L B, Cvetinov M J. Synthesis and properties biobased waterborne polyurethanes from glycolysis product of PET waste and poly(caprolactone) diol. Progress in Organic Coatings, 2017, 105: 111–112

[24] Somani K P, Kansara S S, Patel N K, Rakshit A K. Castor oil based polyurethane adhesives for wood-to-wood bonding. International Journal of Adhesion and Adhesives, 2003, 23(4): 269–275

[25] Yoon S S, Kim S C. Modification of aqueous polyurethane dispersions by polybutadiene. Journal of Applied Polymer Science, 2005, 95(5): 1062–1068

[26] Liu N, Zhao Y H, Kang M Q, Wang J W, Wang X K, Feng Y L, Yin N, Li Q F. The effects of the molecular weight and structure of polycarbonatediols on the properties of waterborne polyurethanes. Progress in Organic Coatings, 2015, 82: 46–56

[27] Du H, Zhao Y H, Li Q F, Wang J W, Kang M Q, Wang X K, Xiang H W. Synthesis and characterization of waterborne polyurethane adhesive from MDI and HDI. Journal of Applied Polymer Science, 2008, 110(3): 1396–1402

[28] Barszczewska-Rybarek I M. Characterization of urethane-dimethacrylate derivatives as alternative monomers for the restorative composite matrix. Dental Materials, 2014, 30(12): 1336–1344

[29] Hidesaki T, Natsuji A, Nakagawa T, Kuwamura G, Hasegawa D, Yamasaki S, Sato K, Takeuchi H. US Patent, 20130079486A1, 2013-5-28

[30] Głowinska E, Datta J. Bio polyetherurethane composites with high content of natural ingredients: Hydroxylated soybean oil based polyol, bio glycol and microcrystalline cellulose. Cellulose (London, England), 2016, 23(1): 581–592

[31] Fu H, Liu K, Yan C, Chen W, Wang Y. Phase morphology and mechanical properties of aliphatic waterborne polyurethane-ureas: Effect of 1,6-hexamethylene diisocyanate (HDI)/isophorone diisocyanate (IPDI) ratio. Polymers & Polymer Composites, 2015, 23(3): 141–150

[32] Che J H, Cheon J M, Chun J H, Park C C, Lee Y H, Kim H D. Preparation and properties of emulsifier-/solventfree slightly crosslinked waterborne polyurethaneacrylic hybrid emulsions for footwear adhesives (III)-effect of trimethylol propane (TMP)/ethylene diamine (EDA) content. Journal of Adhesion Science and Technology, 2017, 31(17): 1872–1887

[33] Gallego R, Arteaga J F, Vaencia C, Diaz M J, Franco J M. Gel-like dispersions of HMDI-cross-linked lignocellulosic materials in castor oil: Toward completely renewable lubricating grease formulations. ACS Sustainable Chemistry & Engineering, 2015, 3(9): 2130–2141

[34] Yilgor I, Yilgor E, Das S, Wilkes G L. Time-dependent morphology development in segmented polyetherurea copolymers based on aromatic diisocyanates. Journal of Polymer Science. Part B, Polymer Physics, 2009, 47(5): 471–483

[35] Zhang Y L, Shao L S, Liu B, Wang F, Wang Y H. Effect of molecular weight of liquid polysulfide on water and organic solvent resistances of waterborne polyurethane/polysulfide copolymer. Progress in Organic Coatings, 2017, 112: 219–224

[36] Wang C B, Cooper S L. Morphology and properties of segmented polyether polyurethaneureas. Macromolecules, 1983, 16(5): 775–786

[37] Garcia-Pacios V, Costa V, Colera M, Martin-Martinez J M. Affect of polydispersity on the properties of waterborne polyurethane dispersions based on polycarbonate polyol. International Journal of Adhesion and Adhesives, 2010, 30(6): 456–465

[38] Zhang Y F, Zhou H W, Wang L, Jiang W Y, Soucek M D, Yi Y. Preparation and characterization of castor oil-based waterborne polyurethane crosslinked with 2-amino-2-(hydroxymethyl)-1,3-propanediol. Journal of Applied Polymer Science, 2017, 134(47): 134

[39] Zhou X, Fang C Q, Yu Q, Yang R, Xie L, Cheng Y L, Li Y. Synthesis and characterization of waterborne polyurethane dispersion from glycolyzed products of waste polyethylene terephthalate used as soft and hard segment. International Journal of Adhesion and Adhesives, 2017, 74: 49–56

[40] Gao Z Z, Peng J, Zhong T H, Sun J, Wang X B, Yue C. Biocompatible elastomer of waterborne polyurethane based on castor oil and polyethylene glycol with cellulose nanocrystals. Carbohydrate Polymers, 2012, 87(3): 2068–2075

[41] Pechar T W, Wilkes G L, Zhou B, Luo N. Characterization of soy-based polyurethane networks prepared with different diisocyanates and their blends with petroleum-based polyols. Journal of Applied Polymer Science, 2007, 106(4): 2350–2362

RIGHTS & PERMISSIONS

Higher Education Press and Springer-Verlag GmbH Germany, part of Springer Nature