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Published in: Polymer Bulletin 8/2013

01-08-2013 | Original Paper

Effect of H12MDI isomer composition on mechanical and physico-chemical properties of polyurethanes based on amorphous and semicrystalline soft segments

Authors: Ainara Saralegi, Agustin Etxeberria, Borja Fernández-d’Arlas, Iñaki Mondragon, Arantxa Eceiza, M. Angeles Corcuera

Published in: Polymer Bulletin | Issue 8/2013

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Abstract

Two series of segmented thermoplastic polyurethanes were synthesized having 33 wt % hard segment based on 4,4′-dicyclohexyl methane diisocyanate with different transtrans isomer contents and 1,3-propanediol chain extender. The soft segments were based on poly(hexamethylene–pentamethylene carbonate)diol and poly(butylene sebacate)diol, amorphous and semicrystalline polyol, respectively. 4,4′-Dicyclohexyl methane diisocyanate with different transtrans isomer contents were obtained by fractional crystallization of commercial diisocyanate and were characterized by differential scanning calorimetry and nuclear magnetic resonance spectroscopy. 4,4′-Dicyclohexyl methane diisocyanate transtrans isomer lead to some interesting properties in the synthesized polyurethanes, due to the more ordered hard domains formed by packing of transtrans 4,4′-dicyclohexyl methane diisocyanate. Thereby, as 4,4′-dicyclohexyl methane diisocyanate transtrans isomer content increased, a better phase separated structure was observed.

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Literature
1.
go back to reference Król P (2007) Synthesis methods, chemical structures and phase structures of linear polyurethanes. Properties and applications of linear polyurethanes in polyurethane elastomers, copolymers and ionomers. Prog Mater Sci 52:915–1015. doi:10.1016/j.pmatsci.2006.11.001 CrossRef Król P (2007) Synthesis methods, chemical structures and phase structures of linear polyurethanes. Properties and applications of linear polyurethanes in polyurethane elastomers, copolymers and ionomers. Prog Mater Sci 52:915–1015. doi:10.​1016/​j.​pmatsci.​2006.​11.​001 CrossRef
2.
go back to reference Meier-Westhues U (2007) Polyurethanes: coatings, adhesives and sealants. Vincentz Network GmbH & Co KG, Hannover Meier-Westhues U (2007) Polyurethanes: coatings, adhesives and sealants. Vincentz Network GmbH & Co KG, Hannover
3.
go back to reference Thomson T (2004) Polyurethanes as specialty chemicals. Principles and applications. CRC Press, West Newbury, MACrossRef Thomson T (2004) Polyurethanes as specialty chemicals. Principles and applications. CRC Press, West Newbury, MACrossRef
4.
go back to reference Randall D, Lee S (2003) The polyurethanes book. Wiley, London Randall D, Lee S (2003) The polyurethanes book. Wiley, London
5.
go back to reference Fernández-d’Arlas B, Ramos JA, Saralegi A, Corcuera M, Mondragon I, Eceiza A (2012) Molecular engineering of elastic and strong supertough polyurethanes. Macromolecules 45:3436–3443. doi:10.1021/ma300397e CrossRef Fernández-d’Arlas B, Ramos JA, Saralegi A, Corcuera M, Mondragon I, Eceiza A (2012) Molecular engineering of elastic and strong supertough polyurethanes. Macromolecules 45:3436–3443. doi:10.​1021/​ma300397e CrossRef
9.
go back to reference McDevitt TC, Woodhouse KA, Hauschka SD, Murry CE, Stayton PS (2003) Spatially organized layers of cardiomyocytes on biodegradable polyurethane films for myocardial repair. J Biomed Mater Res A 66:586–595. doi:10.1002/jbm.a.10504 CrossRef McDevitt TC, Woodhouse KA, Hauschka SD, Murry CE, Stayton PS (2003) Spatially organized layers of cardiomyocytes on biodegradable polyurethane films for myocardial repair. J Biomed Mater Res A 66:586–595. doi:10.​1002/​jbm.​a.​10504 CrossRef
10.
11.
go back to reference Vermette P, Griesser HJ, Laroche G, Guidoin R (2001) Biomedical applications of polyurethanes (Tissue Engineering Intelligence Unit). Landes Bioscience, Austin, TX Vermette P, Griesser HJ, Laroche G, Guidoin R (2001) Biomedical applications of polyurethanes (Tissue Engineering Intelligence Unit). Landes Bioscience, Austin, TX
12.
15.
go back to reference Yilgor I, Yilgor E, Das S, Wilkes GL (2009) Time-dependent morphology development in segmented polyetherurea copolymers based on aromatic diisocyanates. J Polym Sci B 47:471–483. doi:10.1002/polb.21652 CrossRef Yilgor I, Yilgor E, Das S, Wilkes GL (2009) Time-dependent morphology development in segmented polyetherurea copolymers based on aromatic diisocyanates. J Polym Sci B 47:471–483. doi:10.​1002/​polb.​21652 CrossRef
17.
go back to reference Guelcher SA, Gallagher KM, Didier JE, Klinedinst DB, Doctor JS, Goldstein AS, Wilkes GL, Beckman EJ, Hollinger JO (2005) Synthesis of biocompatible segmented polyurethanes from aliphatic diisocyanates and diurea diol chain extenders. Acta Biomater 1:471–484. doi:10.1016/j.actbio.2005.02.007 CrossRef Guelcher SA, Gallagher KM, Didier JE, Klinedinst DB, Doctor JS, Goldstein AS, Wilkes GL, Beckman EJ, Hollinger JO (2005) Synthesis of biocompatible segmented polyurethanes from aliphatic diisocyanates and diurea diol chain extenders. Acta Biomater 1:471–484. doi:10.​1016/​j.​actbio.​2005.​02.​007 CrossRef
18.
go back to reference Shelke NB, Sairam M, Halligudi SB, Aminabhavi TM (2007) Development of transdermal drug-delivery films with castor-oil-based polyurethanes. J Appl Polym Sci 103:779–788. doi:10.1002/app.25070 CrossRef Shelke NB, Sairam M, Halligudi SB, Aminabhavi TM (2007) Development of transdermal drug-delivery films with castor-oil-based polyurethanes. J Appl Polym Sci 103:779–788. doi:10.​1002/​app.​25070 CrossRef
20.
go back to reference Choi SJ, Lee JH, Lee YH, Hwang DY, Kim HD (2011) Synthesis and properties of polyurethane-urea-based liquid bandage materials. J Appl Polym Sci 121:3516–3524. doi:10.1002/app.34135 CrossRef Choi SJ, Lee JH, Lee YH, Hwang DY, Kim HD (2011) Synthesis and properties of polyurethane-urea-based liquid bandage materials. J Appl Polym Sci 121:3516–3524. doi:10.​1002/​app.​34135 CrossRef
23.
go back to reference Solís-Correa RE, Vargas-Coronado R, Aguilar-Vega M, Cauich-Rodríguez JV, San Román J, Marcos A (2007) Synthesis of HMDI-based segmented polyurethanes and their use in the manufacture of elastomeric composites for cardiovascular applications. J Biomater Sci 18:561–578. doi:10.1163/156856207780852488 CrossRef Solís-Correa RE, Vargas-Coronado R, Aguilar-Vega M, Cauich-Rodríguez JV, San Román J, Marcos A (2007) Synthesis of HMDI-based segmented polyurethanes and their use in the manufacture of elastomeric composites for cardiovascular applications. J Biomater Sci 18:561–578. doi:10.​1163/​1568562077808524​88 CrossRef
26.
go back to reference Seneker SD, Born L, Schmelzer HG, Eisenbach CD, Fischer K (1992) Diisocyanato dicyclohexylmethane: structure/property relationships of its geometrical isomers in polyurethane elastomers. Colloid Polym Sci 270:543–548. doi:10.1007/BF00658285 CrossRef Seneker SD, Born L, Schmelzer HG, Eisenbach CD, Fischer K (1992) Diisocyanato dicyclohexylmethane: structure/property relationships of its geometrical isomers in polyurethane elastomers. Colloid Polym Sci 270:543–548. doi:10.​1007/​BF00658285 CrossRef
27.
go back to reference Wong S, Frisch KC, Byrne CA, Mack DP, Schneider NS (1984) Structure–property relationships of transparent aliphatic polyurethane elastomers from the geometric isomers of methylene bis(4-cyclohexyl isocyanate). Adv Urethane Sci Tec 9:77–101 Wong S, Frisch KC, Byrne CA, Mack DP, Schneider NS (1984) Structure–property relationships of transparent aliphatic polyurethane elastomers from the geometric isomers of methylene bis(4-cyclohexyl isocyanate). Adv Urethane Sci Tec 9:77–101
30.
go back to reference Adhikari R, Gunatillake PA, Meijs GF, McCarthy SJ (1999) The effect of diisocyanate isomer composition on properties and morphology of polyurethanes based on 4,4′-dicyclohexyl methane diisocyanate and mixed macrodiols (PDMS-PHMO). J Appl Polym Sci 73:573–582. doi:10.1002/(SICI)1097-4628(19990725)73:4<573 CrossRef Adhikari R, Gunatillake PA, Meijs GF, McCarthy SJ (1999) The effect of diisocyanate isomer composition on properties and morphology of polyurethanes based on 4,4′-dicyclohexyl methane diisocyanate and mixed macrodiols (PDMS-PHMO). J Appl Polym Sci 73:573–582. doi:10.​1002/​(SICI)1097-4628(19990725)73:​4<573 CrossRef
31.
go back to reference Byrne CA, Mack DP, Sloan JM (1985) A study of aliphatic polyurethane elastomers prepared from diisocyanate isomer mixtures. Rubber Chem Technol 58:985–996. doi:10.5254/1.3536109 CrossRef Byrne CA, Mack DP, Sloan JM (1985) A study of aliphatic polyurethane elastomers prepared from diisocyanate isomer mixtures. Rubber Chem Technol 58:985–996. doi:10.​5254/​1.​3536109 CrossRef
32.
go back to reference Saralegi A, Rueda L, Fernández-d’Arlas B, Mondragon I, Eceiza A, Corcuera MA (2013) Thermoplastic polyurethanes from renewable resources: effect of soft segment chemical structure and molecular weight on the morphology-final properties. Polym Int 62:106–115. doi:10.1002/pi.4330 CrossRef Saralegi A, Rueda L, Fernández-d’Arlas B, Mondragon I, Eceiza A, Corcuera MA (2013) Thermoplastic polyurethanes from renewable resources: effect of soft segment chemical structure and molecular weight on the morphology-final properties. Polym Int 62:106–115. doi:10.​1002/​pi.​4330 CrossRef
33.
go back to reference Eceiza A, Zabala J, Egiburu JL, Corcuera MA, Mondragon I, Pascault JP (1999) Reaction kinetics of tolyl isocyanate with polyhexamethylene–pentamethylene carbonate diol. Eur Polym J 35:1949–1958. doi:10.1016/S0014-3057(98)00295-X CrossRef Eceiza A, Zabala J, Egiburu JL, Corcuera MA, Mondragon I, Pascault JP (1999) Reaction kinetics of tolyl isocyanate with polyhexamethylene–pentamethylene carbonate diol. Eur Polym J 35:1949–1958. doi:10.​1016/​S0014-3057(98)00295-X CrossRef
34.
go back to reference Fernandez d’Arlas B, Rueda L, Stefani PM, de la Caba K, Mondragon I, Eceiza A (2007) Kinetic and thermodynamic studies of the formation of a polyurethane based on 1,6-hexamethylene diisocyanate and poly(carbonate-co-ester)diol. Thermochim Acta 459:94–103. doi:10.1016/j.tca.2007.03.021 CrossRef Fernandez d’Arlas B, Rueda L, Stefani PM, de la Caba K, Mondragon I, Eceiza A (2007) Kinetic and thermodynamic studies of the formation of a polyurethane based on 1,6-hexamethylene diisocyanate and poly(carbonate-co-ester)diol. Thermochim Acta 459:94–103. doi:10.​1016/​j.​tca.​2007.​03.​021 CrossRef
35.
36.
go back to reference Semsarzadeh MA, Navarchian AH (2003) Effects of NCO/OH ratio and catalyst concentration on structure, thermal stability, and crosslink density of poly(urethane–isocyanurate). J Appl Polym Sci 90:963–972. doi:10.1002/app.12691 CrossRef Semsarzadeh MA, Navarchian AH (2003) Effects of NCO/OH ratio and catalyst concentration on structure, thermal stability, and crosslink density of poly(urethane–isocyanurate). J Appl Polym Sci 90:963–972. doi:10.​1002/​app.​12691 CrossRef
37.
go back to reference Coleman MM, Lee KH, Skrovanek DJ, Painter PC (1986) Hydrogen bonding in polymers. 4. Infrared temperature studies of a simple polyurethane. Macromolecules 19:2149–2157. doi:10.1021/ma00162a008 CrossRef Coleman MM, Lee KH, Skrovanek DJ, Painter PC (1986) Hydrogen bonding in polymers. 4. Infrared temperature studies of a simple polyurethane. Macromolecules 19:2149–2157. doi:10.​1021/​ma00162a008 CrossRef
39.
go back to reference Teo L, Chen C, Kuo JF (1997) Fourier transform infrared spectroscopy study on effects of temperature on hydrogen bonding in amine-containing polyurethanes and poly(urethane-urea)s. Macromolecules 30:1793–1799. doi:10.1021/ma961035f CrossRef Teo L, Chen C, Kuo JF (1997) Fourier transform infrared spectroscopy study on effects of temperature on hydrogen bonding in amine-containing polyurethanes and poly(urethane-urea)s. Macromolecules 30:1793–1799. doi:10.​1021/​ma961035f CrossRef
40.
go back to reference Fernández d’Arlas B, Rueda L, de la Caba K, Mondragon I, Eceiza A (2008) Microdomain composition and properties differences of biodegradable polyurethanes based on MDI and HDI. Polym Eng Sci 48:519–529. doi:10.1002/pen.20983 CrossRef Fernández d’Arlas B, Rueda L, de la Caba K, Mondragon I, Eceiza A (2008) Microdomain composition and properties differences of biodegradable polyurethanes based on MDI and HDI. Polym Eng Sci 48:519–529. doi:10.​1002/​pen.​20983 CrossRef
41.
go back to reference Rueda-Larraz L, Fernández d’Arlas B, Tercjak A, Ribes A, Mondragon I, Eceiza A (2009) Synthesis and microstructure-mechanical property relationships of segmented polyurethanes based on a PCL–PTHF–PCL block copolymer as soft segment. Eur Polym J 45:2096–2109. doi:10.1016/j.eurpolymj.2009.03.013 CrossRef Rueda-Larraz L, Fernández d’Arlas B, Tercjak A, Ribes A, Mondragon I, Eceiza A (2009) Synthesis and microstructure-mechanical property relationships of segmented polyurethanes based on a PCL–PTHF–PCL block copolymer as soft segment. Eur Polym J 45:2096–2109. doi:10.​1016/​j.​eurpolymj.​2009.​03.​013 CrossRef
42.
go back to reference Koberstein JT, Russell TP (1986) Simultaneous SAXS–DSC study of multiple endothermic behaviour in polyether-based polyurethane block copolymers. Macromolecules 19:714–720. doi:10.1021/ma00157a039 CrossRef Koberstein JT, Russell TP (1986) Simultaneous SAXS–DSC study of multiple endothermic behaviour in polyether-based polyurethane block copolymers. Macromolecules 19:714–720. doi:10.​1021/​ma00157a039 CrossRef
43.
go back to reference Saiani A, Daunch WA, Verbeke H, Leenslag JW, Higgins JS (2001) Origin of multiple melting endotherms in a high hard block content polyurethane. 1. Thermodynamic investigation. Macromolecules 34:9059–9068. doi:10.1021/ma0105993 CrossRef Saiani A, Daunch WA, Verbeke H, Leenslag JW, Higgins JS (2001) Origin of multiple melting endotherms in a high hard block content polyurethane. 1. Thermodynamic investigation. Macromolecules 34:9059–9068. doi:10.​1021/​ma0105993 CrossRef
44.
go back to reference Saiani A, Rochas C, Eeckhaut G, Daunch WA, Leenslag JW, Higgins JS (2004) Origin of multiple melting endotherms in a high hard block content polyurethane. 2. Structural investigation. Macromolecules 37:1411–1421. doi:10.1021/ma034604 CrossRef Saiani A, Rochas C, Eeckhaut G, Daunch WA, Leenslag JW, Higgins JS (2004) Origin of multiple melting endotherms in a high hard block content polyurethane. 2. Structural investigation. Macromolecules 37:1411–1421. doi:10.​1021/​ma034604 CrossRef
45.
go back to reference Saiani A, Novak L, Rodier G, Eeckhaut G, Leenslag JW, Higgins JS (2007) Origin of multiple melting endotherms in a high hard block content polyurethane: effect of annealing temperature. Macromolecules 40:7252–7262. doi:10.1021/ma070332p CrossRef Saiani A, Novak L, Rodier G, Eeckhaut G, Leenslag JW, Higgins JS (2007) Origin of multiple melting endotherms in a high hard block content polyurethane: effect of annealing temperature. Macromolecules 40:7252–7262. doi:10.​1021/​ma070332p CrossRef
46.
49.
go back to reference Bagdi K, Molnár K, Wacha A, Bóta A, Pukánszky B (2011) Hierarchical structure of phase-separated segmented polyurethane elastomers and its effect on properties. Polym Int 60:529–536. doi:10.1002/pi.3003 CrossRef Bagdi K, Molnár K, Wacha A, Bóta A, Pukánszky B (2011) Hierarchical structure of phase-separated segmented polyurethane elastomers and its effect on properties. Polym Int 60:529–536. doi:10.​1002/​pi.​3003 CrossRef
Metadata
Title
Effect of H12MDI isomer composition on mechanical and physico-chemical properties of polyurethanes based on amorphous and semicrystalline soft segments
Authors
Ainara Saralegi
Agustin Etxeberria
Borja Fernández-d’Arlas
Iñaki Mondragon
Arantxa Eceiza
M. Angeles Corcuera
Publication date
01-08-2013
Publisher
Springer Berlin Heidelberg
Published in
Polymer Bulletin / Issue 8/2013
Print ISSN: 0170-0839
Electronic ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-013-0930-3

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