Browse > Article
http://dx.doi.org/10.7473/EC.2020.55.2.128

Overview of Hydrolysis : A Review Part I- Hydrolysis Mechanism  

Kim, Kwang-Jea (DTR VMS Italy S. r. l.)
Publication Information
Elastomers and Composites / v.55, no.2, 2020 , pp. 128-136 More about this Journal
Abstract
The hydrolysis mechanisms as well as the hydrolysis measurement technique and its practical applications in material manufacturing fields are revised. This chapter, Part 1, elaborates the theoretical aspects of the hydrolysis mechanism. Acid-catalyzed and base-catalyzed hydrolysis mechanisms are reviewed. The quantitative analysis method based on the SIM technique using py-GC-MS is reviewed. Examples of hydrolysis of alkoxysilane in elastomer composites currently used in the industry and hydrolysis of amine in plastic composites are shown. Moreover, Part 2 discusses the mechanical property changes in elastomer and plastic composites after hydrolysis.
Keywords
hydrolysis mechanism; characteristics; silane; polyamide; rubber; review;
Citations & Related Records
Times Cited By KSCI : 4  (Citation Analysis)
연도 인용수 순위
1 K. J. Kim and J. VanderKooi, "Moisture Effects on TESPDSilica/CB/SBR Compounds", Rubber Chem. Technol., 78, 84 (2005).   DOI
2 U. Goral, A. Hunsche, A. Muller, and H. G. Koban, "Investigations into the Silica/Silane Reaction System", Rubber Chem. Technol., 70, 608 (1997).   DOI
3 A. Hunsche, U. Goral, A. Muller, M. Knaack, T. Gobel, and Hurth, "Investigations concerning the reaction silica/organosilane and organosilane/polymer. Part 1: reaction mechanism and reaction model for silica/organosilane", Kautsch. Gummi Kunstat. 50, 881 (1997).
4 K. L. Mittal, Eds., Silane Coupling Agents, VSP, Utrechi (1992).
5 K. J. McNeil, J. A. DiCapri, D. A. Walsh, and R. F. Pratt, "Kinetics and mechanism of hydrolysis of a silicate triester, tris(2-methoxyethoxy)phenylsilane", J. Am. Chem. Soc., 102, 1859 (1980).   DOI
6 M. G. Vorokonov, V. P. Meleshkevisk, and Y. A. Yuzekelvski, "The Siloxane Bond", Plenum Press, New York (1978) p. 375-380.
7 E. R. Pohl, "Society of the plastics industry", Proc. 38th Annu. Tech. Conf. Reinforced Plastics/Composites Inst. Section 4-B (1983).
8 R. W. Taft, Jr., "Steric effects in Organic Chemistry", M. S. Newman, Eds., John Wiley, New York (1956), Ch. 13.
9 B. Arkles, J. R. Steinmetz, J. Zazyczny, and P. Metha, in: "Silanes and other coupling agents", K. L. Mittal, Eds., VSP, Utrechi (1992) p. 93.
10 U. Goral and A. Hunsche, "Advanced investigations into the silica/silane reaction system", Soc. Rubber Ind., 71, 549 (1998).   DOI
11 D. F. DeTar, "Effects of alkyl groups on rates of acyl-transfer reactions", J. Org. Chem., 45, 5166 (1980).   DOI
12 W. P. Jencks and K. Salvesen, "Equilibrium deuterium isotope effects on the ionization of thiol acids", J. Am. Chem. Soc., 93, 4433 (1971).   DOI
13 M. Prassas and L. L. Hench, "Ultrastructure Processing of Ceramics", L. Hench and D. Ulrich, Eds., John Wiley, New York (1984) p. 100.
14 K. W. Allen, in: "Silane Coupling Agents", K. L. Mittal, Eds., VSP, Utrechi (1992) p. 93.
15 B. D. Kay and R. A. Assink, "Sol-gel kinetics: II. Chemical speciation modeling", J. Non-Cryst. Solids, 104, 112 (1988).   DOI
16 M. J. Moore, "Mold makers make anti-dumping plea to ITC", Rubber Plast. News, June 3, 2002, p. 14.
17 F. D. Osterholtz and E. P. Pohl, in: "Silane Coupling Agents", K. L. Mittal, Eds., VSP, Utrechi (1992) p. 93.
18 J. Y. Lee and K. J. Kim, "MEG effects on hydrolysis of polyamide 66/glass fiber composites and mechanical property changes", Molecules, 24, 755 (2019).   DOI
19 D. Forsstrom and B. Terselius, "Thermo oxidative stability of polyamide 6 films I. Mechanical and chemical characterization", Polym. Degrad. Stab., 67, 69 (2000).   DOI
20 J. Rohrer, Rubber World, 252, 4 (2015).
21 W. H. Carothers and G. J. Berchet, "Studies on polymerization G and ring formation. VIII. Amids from ${\varepsilon}$-aminocaproic acid", J. Am. Chem. Soc., 52, 5289 (1930).   DOI
22 W. Y. Jung and J. I. Weon, "Characterization of Thermal Degradation of Polyamide 66 Composite: Relationship between Lifetime Prediction and Activation Energy", Polymer(Korea), 36, 712 (2012).
23 J. H. Park, W. N. Kim, I. H. Kwon, S. H. Lim, M. B. Ko, and C. R. Choe, "Effects of Processing Conditions of Injection Molding on the Microstructure of Long Fiber Reinforced Nylon Composites", Polymer(Korea), 23, 681 (1999).   DOI
24 B. S. Yoon, D. J. Woo, M. H. Suh, and S. H. Lee, "A study on the Ternary GF/PA/PP Composites Manufactured by Using Pre-impregnated Glass Fiber", Polymer(Korea), 24, 701 (2000).
25 B. J. Holland and J. N. Hay, "Thermo oxidative stability of polyamide 6 films I. Mechanical and chemical characterization", Polym. Int., 49, 943 (2000).   DOI
26 C. H. Do, E. M. Pearce, and B. J. Bulkin, "FT-IR spectroscopic study on the thermal and thermal oxidative degradation of nylons", J. of Polym. Sci.: Part A: Polym. Chem., 25, 2409 (1987).
27 U. S. Ishiaku, H. Hamada, M. Mizoguchi, W. S. Chow, and Z. A. Mohd Ishak, "The effect of ambient moisture and temperature conditions on the mechanical properties of glass fiber/carbon fiber/nylon 6 sandwich hybrid composites consisting of skin-core morphologies", Polym. Composites, 26, 52 (2005).   DOI
28 A. Valle's-Lluch, W. Camacho, A. Ribes-Greus, and S. Karlsson, "Microwave-assisted synthesis of new optically active poly(ester-imide)s containing N,N'-(pyromellitoyl)-bis-L-phenylalanine moieties", J. Appl. Polym. Sci., 85, 2211-2216 (2002).   DOI
29 M. A. Schaffer, K. B. McAuley, E. K. Marchildon, and M. F. Cunningham, "Thermal degradation kinetics of nylon 66: Experimental study and comparison with model predictions", Macromol. React. Eng., 1, 563 (2007).   DOI
30 R. P. Singh, S. M. Desai, and G. Pathak, "Thermal decomposition kinetics of photooxidized nylon 66", J. Appl. Polym. Sci., 87, 2146 (2003).   DOI
31 S. V. Levchik, E. D Weil, and M. Lewin, "Thermal decomposition of aliphatic nylons", Polym. Int., 48, 532 (1999).   DOI
32 Z. A. Alothman, M. M. Alam, and M. Naushad, "Heavy toxic metal ion exchange kinetics: Validation of ion exchange process on composite cation exchanger nylon 6,6 Zr(IV) phosphate", J. Indus. Eng. Chem., 19, 956 (2013).   DOI
33 W. H. Jang and J. S. Go, Korean Soc. Ind. Eng. Chem., 10, 1136 (1999).
34 B. Y. Shin, M. H. Ha, and D. H. Han, "Morphological, rheological, and mechanical properties of polyamide 6/polypropylene blends compatibilized by electron-beam irradiation in the presence of a reactive agent", Materials, 9, 342 (2016).   DOI
35 B. D. Viers, Polymer Data Handbook, Oxford University Press, Oxford, 1999.
36 R. K. Gupta, E. Kennel, K. J. Kim, 材料科學與應用進展:聚合物納米復合材料手冊(導讀版), Science Press, Beijing, 2011. ISBN: 978-7-03-032137-4 (2011).
37 R. van Mullekom, D. Joachimi, A. Karbach, P. Persigehl, and M. De Bock, "Molding compositions and their use", U.S. Patent 20050043443 (2005).
38 D. Joachimi, H. Schlte, W. Littek, and J. Kadelka, "Highly viscous polyamide for use in extrusion blow molding", U.S. Patent 20,030,092,822 (2003).
39 L. Huang, Q. Pei, Q. Yuan, H. Li, F. Cheng, and J. Ma, "Brittle-ductile transition in PP/EPDM blends: effect of notch radius", Polymer, 44, 3125 (2003).   DOI
40 S. M. Kim and K. J. Kim, "Effects of Moisture and Temperature on Recrystallization and Mechanical Property Improvement of PA66/GF Composite", Polymer(Korea), 39, 880 (2015).   DOI
41 S. C. Tjong, W. D. Li, and R. K. Y.Li, "Impact toughening behaviour of quaternary PP/HDPE/EPDM/EP blends", Eur. Polm. J., 34, 755 (1998).   DOI
42 K. J. Kim, "Overview of Hydrolysis: A Review Part IIHydrolysis Application", Elast. Compos., (in print)
43 R. P. Lattimer, "Direct analysis of polypropylene compounds by thermal desorption and pyrolysis-mass spectrometry", J. Anal. Appl. Pyrolysis, 26, 65 (1993).   DOI
44 K. J. Kim and J. Vanderkooi, "Reactive Batch Mixing for Improved Silica-Silane Coupling", Int. Polym. Process., 19, 364 (2004).   DOI
45 J. Y. Lee and K. J. Kim, "Measurement of degree of hydrolysis of a PA66/GF composite using a py-GC/MS analysis", Elast. Compos., 52, 59 (2017).   DOI
46 G. Montaudo and C. Puglisi, Thermal Degradation Mechanisms in Condensation Polymers, in Developments in Polymer Degradation, N. Grassie, Ed. Applied Science, London, 1987.
47 G. Montaudo and C. Puglisi, Thermal Degradation of Condensation Polymers, in Comprehensive Polymer Science, Pergamon Press, Oxford, 1992.
48 H.-J. Dussel, H. Rosen, and D. O. Hummel, "Feldionen- und Elektronenstoss-Massenspektrometrie von Polymeren und Copolymeren, 5. Aliphatische und aromatische Polyamide und Polyimide", Makromol. Chem., 177, 2343 (1976).   DOI
49 P. R. Hornsby, J. Wang, R. Rothon, G. Jackson, G. Wilkinson, and K. Cossick, "Thermal decomposition behaviour of polyamide fire-retardant compositions containing magnesium hydroxide filler", Polym. Degrad. Stab., 51, 235 (1996).   DOI
50 H. Ohtani, I. Nagaya, Y. Sugimura, and S. Tsuge, "Studies on thermal degradation of aliphatic polyamides by pyrolysisglass capillary chromatography", J. Anal. Appl. Pyrol., 4, 117 (1982).   DOI
51 D. H. MacKerron and R. P. Gordon, "Minor products from the pyrolysis of thin films of poly(hexamethylene adipamide)", Polym. Degrad. Stab., 12, 277 (1985).   DOI
52 G. Montaudo and R. P. Lattimer, Mass Spectrometry of Polymers, CRC Press, Boca Raton London Washington, 2001.
53 E. Lissi, "Entropic control of chemiluminescent reactions", J. Am. Chem. Soc., 98, 3386 (1976).   DOI
54 N. Chaupart, G. Serpe, and J. Verdu, "Molecular weight distribution and mass changes during polyamide hydrolysis", Polymer, 39, 1375 (1998).   DOI
55 S. M. Kim and K. J. Kim, "Effects of accelerator on silica vs. carbon black filled natural rubber compounds", Polymer(Korea), 37, 269 (2013).   DOI
56 J. L. White and K. J. Kim, Thermoplastic and Rubber Compounds Technology and Physical Chemistry, Hanser Publisher, Munich, Cincinnati (2008) ISBN-13: 978-3-446-40980-4
57 R. K. Gupta, E. Kennel, and K. J. Kim, Polymer Nanocomposites Handbook, CRC Press, Boca Raton, ISBN: 9780849397776, ISBN 10: 0849397774, 2009.
58 E. P. Plueddemann, Silane Coupling Agents, Plenum Press, New York, 1982.
59 K. J. Kim and J. VanderKooi, "Moisture Effects on Improved Hydrolysis Reaction for TESPT and TESPD-Silica Compounds", Composite Interfaces, 11, 471 (2004).   DOI
60 K. J. Kim and J. VanderKooi, "Temperature Effects of Silane Coupling on Moisture Treated Silica Surface", J. Appl. Polym. Sci., 95, 623 (2005).   DOI
61 A. S. Hashim, B. A. Zahare, Y. Ikeda, and S. K. Ohjiya, "The Effect of Bis(3-Triethoxysilylpropyl) Tetrasulfide on Silica Reinforcement of Styrene-Butadiene Rubber", Rubber Chem. Technol., 78, 289 (1998).
62 S. M. Kim and K. J. Kim, "Hydrolysis resistance and mechanical property changes of glass fiber filled polyketone composites upon glass fiber concentration", Elast. Compos., 52, 1 (2017).   DOI
63 M. H. Cohen and D. Turnbull, "Molecular Transport in Liquids and Glasses", J. Chem. Phys., 31, 1164 (1959).   DOI
64 C. A. Kumins and T. K. Kwei, Free volume and other Theories, in Diffusion in polymers edited by J. Crank and G.S Park, 1968.
65 P. Moy and F. E. Karasz, "Epoxy-water interactions", Polym. Eng. Sci., 20, 315 (1980).   DOI
66 I. Merdas, F. Thominette, A. Tcharkhtchi, and J. Verdu, "Factors governing water absorption by composite matrices", Compos. Sci. Technol., 62, 487 (2002).   DOI
67 I. Merdas, F. Thominette, A. Tcharkhtchi, and J. Verdu, Compos. Sci. Technol., 62, 487 (2002).   DOI
68 R. Puffr and J. Sebenda, "On the structure and properties of polyamides. XXVII. The mechanism of water sorption in polyamides", J. Polym. Sci. Part C Polym. Symp., 16, 79 (1967).   DOI
69 L. Razumovskii, V. Markin, and G. Y. Zaikov, "Sorption of water by aliphatic polyamides. Review", Polym. Sci. USSR, 27, 751 (1985).   DOI
70 X. Colin and J. Verdu, Humid Ageing of Organic Matrix Composites, in Durability of Composites in a Marine Environment, vol. 208, P. Davies and Y. D. S. Rajapakse, Eds. Dordrecht: Springer Netherlands, 2014.
71 M. Akay, "Moisture absorption and its influence on the tensile properties of glass-fibre reinforced polyamide 6,6", Polym. Polym. Compos., 2, 349 (1994).
72 H. H. G. Jellinek and S. R. Dunkle, Degradation and Stabilization of Polymers, Elsevier, New York, 1983.
73 N. Sombatsompop and K. Chaochanchaikul, "Effect of moisture content on mechanical properties, thermal and structural stability and extrudate texture of poly(vinyl chloride)/wood sawdust composites", Polym. Int., 53, 1210 (2004).   DOI
74 H. K. Reimschuessel, "Relationships on the effect of water on glass transition temperature and young's modulus of nylon 6", J. Polym. Sci. Polym. Chem. Ed., 16, 1229 (1978).   DOI
75 B. Jacques, M. Werth, I. Merdas, F. Thominette, and J. Verdu, "Hydrolytic ageing of polyamide 11. 1. Hydrolysis kinetics in water", Polymer, 43, 6439 (2002).   DOI
76 J. L. Thomason, "Structure-property relationships in glass-reinforced polyamide, Part 3: Effects of hydrolysis ageing on the dimensional stability and performance of short glass-fiber-reinforced polyamide 66", Polym. Compos., 28, 344 (2007).   DOI
77 M. Kohan, Nylon Plastics Handbook, Hanser/Gardner, New York, 1995.
78 A. Lasagabaster, M. J. Abad, L. Barral, and A. Ares, "FTIR study on the nature of water sorbed in polypropylene (PP)/ethylene alcohol vinyl (EVOH) films", Eur. Polym. J., 42, 3121 (2006).   DOI
79 E. S. Goncalves, L. Poulsen, and P. R. Ogilby, "Mechanism of the temperature-dependent degradation of polyamide 66 films exposed to water", Polym. Degrad. Stab., 92, 1977 (2007).   DOI
80 D. H. Mackerron and R. P. Gordon, "Minor products from the pyrolysis of thin films of poly(hexamethylene adipamide)", Polym. Degrad. Stab., 12, 277 (1985).   DOI
81 J. L. Thomason, "The influence of fibre length, diameter and concentration on the impact performance of long glass-fibre reinforced polyamide 6,6", Compos. Part A-Appl. Sci. Manuf., 40, 114 (2009).   DOI