5.18 - Chemistry and Technology of Polyamides

Polymer Science: a Comprehensive Reference: Volume 1-10

Volumn 1-10, Issue , 2012, Pages 431-467

  Rulkens, R ^a   Koning, C ^b  

^a DSM RESEARCH   (Netherlands)

^b EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Aliphatic polyamides; Amidation catalyst; Amorphous polyamides; Application; Block copolyetheramides; Characterization; Chemistry; Equilibrium; Hydrolytic polyamides; Mechanical properties; Polyamide blends; Process technology; Semiaromatic polyamides; Side reactions; Thermal properties

Indexed keywords

EID: 84884966121     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-444-53349-4.00147-3     Document Type: Chapter

References (188)

1. US Federal Trade Commission. The Textile Fiber Products Identification Act. 16 CFR Part 303.7.
2. M.I. Kohan (1995) Nylon Plastics Handbook. Munich, Vienna, New York: Hanser Publishers
3. S.M. Aharoni (1997) n-Nylons. Chichester, New York, Weinheim, Brisbane, Singapore, Toronto: Wiley
4. G.W. Becker and D. Braun (1998) Kunststoff Handbuch 3/4 Polyamide. München/Wien: Hanser Verlag
5. K. Marchildon (2011) Macromol. React. Eng. 5 22.
6. Document of the International Organization for Standardization, Polyamide (PA) moulding and extrusion materials-Part I: Description system and basis for specification, ISO 1874–1:2010.
7. American Society for Testing and Materials, Standard Specification for Polyphthalamide (PPA) Injection Molded Materials, ASTM International, D 5336-03, 2003.
8. A. Kinnane (2002) DuPont: From the Banks of the Brandywine to Miracles of Science. E.I. du Pont de Nemours and Company p 124
9. http://www.german-hosiery-museum.de/technik/garne/perlon German Hosiery Museum
10. M. Genas (1962) Angew. Chem. 74 535.
11. Vollbracht, L.; Veerman, T. J.; Akzo, N. V. U.S. Patent 4, 308, 374, 1981.
12. G. Bier (1969) Adv. Chem. Ser. 91 612.
13. S.I. Murahashi, T. Naota and E.J. Saito (1986) J. Amer. Chem. Soc. 108 7846.
14. N.M. Tran, F. Criere and H. Sekigushi (1981) Makromol. Chem. 182 2175.
15. H.R. Kricheldorf (2006) Angew. Chem. 118 5884.
16. S. Maier, T. Loontjens, B. Scholtens and R. Mülhaupt (2003) Angew. Chem. Int. Ed. 42 5094.
17. H. Sekiguchi (1984) K.J. Ivin, T. Saegusa (Eds) Ring Opening Polymerization Vol. 2 London: Elsevier Chapter 12
18. C. Giori and B.T. Hayes (1970) J. Polym. Sci. A-1 8 335.
19. D.D. Steppan, M.F. Doherty and M.F. Malone (1987) J. Appl. Polym. Sci. 33 2333.
20. J. Malluche, G.P. Hellmann, M. Hewel and H.J. Liedloff (2007) Polym. Eng. Sci. 47 1589.
21. E. Hellmann, J. Malluche and G.P. Hellmann (2007) Polym. Eng. Sci. 47 1600.
22. F. Wiloth (1958) Makromol. Chem. 27 37.
23. W. Zheng, K.B. McAuley, E.K. Marchildon and K.Z. Yao (2007) Can. J. Chem. Eng. 85 180.
24. C. Ayes (1954) J. Appl. Chem. 4 444.
25. L.F. Beste and R.C. Houtz (1952) J. Polym. Sci. 8 395.
26. K. Tai and T. Tagawa (1983) Ind. Eng. Chem. Prod. Res. Rev. 22 192.
27. S.M. Aharoni (1997) n-Nylons. Chichester, New York, Weinheim, Brisbane, Singapore, Toronto: Wiley p 357
28. M. Booij (1997) Sustainable Closed Loop System for Recycling of Carpet Materials. S. Sifniades, A.B. Levy, J.A.J. Hendrix (Eds) AlliedSignal Inc./DSM., WO/1997/020813, Brite Euram Report RECAM Project BE-95-1337, July 1, 1999; Press release DSM/AlliedSignal, 15 November 1999
29. D.D. Steppan, M.F. Doherty and M.F. Malone (1991) J. Appl. Polym. Sci. 42 1009.
30. M.A. Schaffer, E.K. Marchildon, K.B. McAuley and M.F. Cunningham (2000) J. Macromol. Sci. Rev. Macromol. Chem. Phys. C40 233.
31. M.A. Schaffer, K.B. McAuley, E.K. Marchildon and M.F. Cunningham (2007) Macromol. React. Eng. 1 563.
32. K. Katsuaki and M. Shinji (1968) Kobunshi Kagaku 25 318.
33. J. Malluche, G.P. Hellmann, M. Hewel and H.J. Liedloff (2007) Polym. Eng. Sci. 47 1589.
34. P. Gijsman, D. Tummers and K. Janssen (1995) Polym. Deg. Stab 49 121.
35. W. Dong and P. Gijsman (2010) Polym. Deg. Stab 95 1054.
36. Nijenhuis, A. J.; Serné, M.; De Brabander-Van den Berg, E. M. M.; Aberson, R. DSM NV, WO/1996/035739, 1996.
37. M.A. Dudley (1972) J. Appl. Polym. Sci. 16 493.
38. E. Jacobi, H. Schuttenberg and R.C. Schulz (1980) Makromol. Chem. Rapid Commun. 1 397.
39. E. Biagini, E. Cattiglia, E. Pedemonte and S. Russo (1983) Makromol. Chem. 184 1213.
40. H. Benoit, R. Rempp and A. Motsch (1967) J. Polym. Sci. B5 753.
41. C.A. Veith and R.E. Cohen (1989) Polymer 30 942.
42. M.K.K. Rao and P.G. Galanty (1995) M.I. Kohan (Eds) Nylon Plastics Handbook Munich, Vienna, New York: Hanser Chapter 13.3.1
43. H. Hoffmann (1998) G.W. Becker, D. Braun (Eds) Kunststoff Handbuch 3/4 Polyamide München/Wien: Hanser Chapter 2.2.3.1
44. http://www.shawfloors.com/Shaw-Environmental/Sustainability
45. A. Van Rooij (2007) The Company that Changed Itself. Amsterdam: Amsterdam University Press p 228
46. Eiermann, M. BASF AG, DE 19753301, 1999.
47. Achhammer, G.; Fuchs, E. BASF AG, U.S. Patent 5, 495, 016, 1996.
48. Lin, L.; Merrill, R. G. Allied Corporation Report, H-17183, 1983.
49. H.K. Reimschuessel (1977) Macromolecules 12 65.
50. E.D. Oliver (1968) SRI Process Econ. Rep No. 41
51. Y. Arai (1981) Polymer 22 273.
52. P.H. Hermans, D. Heikens and P.F. Van Velden (1958) J. Polym. Sci. 30 81.
53. H. Hoffmann (1998) G.W. Becker, D. Braun (Eds) Kunststoff Handbuch 3/4 Polyamide Hanser Verlag: München/Wien Chapter 2.2.3.2
54. W.H. Carothers (1931) Chem. Rev. 8 353.
55. G.B. Apgar and M.J. Koskoski (1986) R.B. Seymour, G.S. Kirshenbaum (Eds) High Performance Polymers: Their Origin and Development New York: Elsevier 55.
56. G.B. Apgar (1995) M.I. Kohan (Eds) Nylon Plastics Handbook Munich, Vienna, New York: Hanser Verlag Chapter 13.11
57. R. Aelion (1948) Ann. Chim. 3 5.
58. L. Notarbartolo (1958) Ind. Plast. Mod 10 44.
59. G. Wilke (1957) Angew. Chem. 69 397.
60. G.B. Apgar and M.J. Koskoski (1986) R.B. Seymour, G.S. Kirshenbaum (Eds) High Performance Polymers: Their Origin and Development New York: Elsevier 55-65.
61. K. Sporka (1991) R. Puffr, V. Kubanek (Eds) Lactam-Based Polyamides Vol. II Boca Raton, FL: CRC Press 73-90.
62. G. Strauss (1969) Chem. Eng. 76 106.
63. Kawakami, A.; Shimada, T.; Tsumiyama, T.; Yamaguchi, H. Ube Industries. U.S. Patent 5, 362, 448, 1994.
64. Feinauer, R.; Müller, K. A. Chemische Werke Hüls AG, DE 2152194, 1973.
65. Griehl, W.; Schaaf, S. Inventa AG, DE 1570774, 1972.
66. J. Kralicek, V. Kubanek and J. Kondelikova (1973) Chem. Prumysl. 23 401.
67. S.W. Shalaby, R.J. Fredericks and E.M. Pearce (1972) J. Polym. Sci. A-2 10 1699.
68. H.G. Elias and A. Fritz (1968) Makromol. Chem. 114 31.
69. J. Kralicek, V. Kubanek and J. Kondelikova (1973) Chem. Prumysl. 23 401.
70. R. Feldmann and R. Feinauer (1973) Angew. Makromol. Chem. 34 1.
71. Carothers, W. H.; Du, E. I. Pont de Nemours Company Inc., U.S. Patent 2, 071, 250, 1937.
72. Mori, H.; Davis, S. Chemical Economics Handbook (CEH) Marketing Research Report, Nylon Resins, April 2010.
73. J.M. Barineau (1995) M.I. Kohan (Eds) Nylon Plastics Handbook Munich, Vienna, New York: Hanser Publishers 490-518.
74. H. Hofmann and W. Alewelt (1998) G.W. Becker, D. Braun (Eds) Kunststoff Handbuch 3/4 Polyamide München/Wien: Hanser Verlag 71. and 72–73, respectively
75. Stahl, W. F. CEH-Marketing Research Report, Chem. Econ. Handbook; SRI International, 1993.
76. K. Weissmel and H.J. Arpe (1988) Industrielle Organische Chemie. 3rd ed. Weinheim: VCH Publishers
77. R.A. Smiley (2000) Hexamethylenediamine in: Ullman’s Encyclopedia of Industrial Chemistry Vol. A1 Wiley Publishers 209. http://onlinelibrary.wiley.com/doi/10.1002/14356007.a12_629 published on line 15.06
78. F. Ullmann (1985) 5th ed. Encyclopedia of Industrial Chemistry Vol. A1 Weinheim, Germany: VCH Publishers p 209
79. Teles, J. H.; Rossler, B.; Pinkos, R.; et al. BASF, U.S. Patent 7, 449, 606, 2008.
80. G.M. Bohlmann, R. Jokoi and Y. Sakuma (1993) Chemical Economic Handbook. Menlo Park, CA: SRI International
81. A. Kinnane (2002) DuPont: From the Banks of the Brandywine to Miracles of Science. E.I. du Pont de Nemours and Company p 124
82. M. Checken Rothe (1960) Makromol. Chem. 35 183.
83. N. Singletary, R.B. Bates, N. Jacobsen, et al. (2009) Macromolecules 42 2336.
84. V.A. Augstkalns (1995) M.I. Kohan (Eds) Nylon Plastics Handbook Munich, Vienna, New York: Hanser Publishers 17-23. Section 2.3.1
85. F. Fourné (1999) Synthetic Fibers Handbook. Hanser Publishers: Munich, Vienna, New York p 61
86. R. Greiner and P. Heather (1998) G.W. Becker, D. Braun (Eds) Kunststoff Handbuch 3/4 Polyamide München/Wien: Hanser Verlag 195-196. respectively 592
87. Heinz, H. D.; Al Sayed, A.; Dujardin, R. Bayer AG, DE 3934711A, 1991.
88. Hurley, J.; Goetz, W.; Blinne, G. BASF, EP 520219A3, 1992.
89. Heinz, H. D.; Al Sayed, A.; Döring, J.; et al. EP 473032A, 1992.
90. Carothers, W. H. DuPont, U.S. Patent 2, 130, 948, 1938.
91. R.J. Gaymans, T.E.C. Utteren, J.W.A. Van den Berg and J. Schuyer (1977) J. Polym. Sci. Polym. Chem. Ed 15 537.
92. R.G. Beaman and C.R. Cramer (1956) J. Polym. Sci. 21 223.
93. E. Roerdink, P.J. de Jong and J.M.M. Warnier (1985) Polymer 26 1582.
94. Bongers, A. J. P.; Roerdink, E. DSM, EP 0254367, 1988.
95. Suverkropp, G. H.; Nieuwkamp, J. G. M.; Stamicarbon, B. V. EP 0016482, 1980.
96. T. Yamanobe, Y. Kurihara, H. Uehara and T. Komoto (2007) J. Mol. Struct 829 80.
97. S. León, C. Alemán, M. Bermúdez and S. Muñoz-Guerra (2000) Macromolecules 33 8756.
98. E.D.T. Atkins, M. Hill, S.K. Hong, et al. (1992) Macromolecules 25 917.
99. S. Eltink (1998) G.W. Becker, D. Braun (Eds) Kunststoff Handbuch 3/4 Polyamide München/Wien: Hanser 576.
100. M.I. Kohan (1995) M.I. Kohan (Eds) Nylon Plastics Handbook Munich, Vienna, New York: Hanser 556.
101. G.H. Hargreaves and L.N. Owen (1947) J. Chem. Soc. 753.
102. H. Hopf, A. Müller and F. Wenger (1954) Die Polyamide. Springer Verlag: Berlin, Göttingen, Heidelberg p 68
103. http://www.dsm.com/nl_NL/html/dep/news_items/ecopaxx_pr.htm Press release on the introduction of EcoPaXX®
104. O. Schickh, F. Urbanek and H. Metzger (1963) Z. Naturforsch 18b 980.
105. Scholten, H.; Marcy, G. Chemische Werke Hüls AG, DE 2044105, 1972.
106. C. Koning, L. Teuwen, R. De Jong, et al. (1999) High Perf. Polym 11 387.
107. Evonik Science Newsletter. www.corporate.evonik.com Element 31, p 11
108. J. Heidarian, N.M. Ghasem and W.M.A. Wan Daud (2004) J. Appl. Polym. Sci. 92 2504.
109. C.R. Frihart (2004) Int. J. Adhes. Adhesives 24 415.
110. X.D. Fan, Y.D. Deng, J. Waterhouse and P. Pfromm (1998) J. Appl. Polym. Sci. 68 305.
111. M. Hewel (1995) M.I. Kohan (Eds) Nylon Plastics Handbook Munich, Vienna, New York: Hanser Publishers 365.
112. http://plasticsportalasia.net/wa/plasticsAP~en_GB/portal/show/content/literature/ultramid http://www.basf.com via product finder/Ultramid/Ultramid Europe/Download Bruchures It can also be found via
113. E.D. Harvey and F.J. Hybart (1970) J. Appl. Polym. Sci. 14 2133.
114. J.M. Stouffer, H.W. Starkweather, B.S. Hsiao, et al. (1996) Polymer 37 1217.
115. Palmer R. J.; Martens, M. M. E.I. DuPont de Nemours, WO Patent 2, 010, 014, 810, 2010.
116. Rapra review reports, Report 121, Polyamides as Engineering Thermoplastic Materials, by I.B. Page, I. B., Vol. 11, 1, 2000 (ISSN: 0889–3144).
117. C. Koning, L. Teuwen, R. De Jong, et al. (1999) High Perf. Polym 11 387.
118. S.M. Aharoni (1997) n-Nylons. Chichester, New York, Weinheim, Brisbane, Singapore, Toronto: Wiley Chapter 1.3
119. D.D. Coffman, G.J. Berchet, W.R. Peterson and E.W. Spanagel (1947) J. Polym. Sci. 2 306.
120. J.L. Koenig and M.C. Agboatwalla (1968) J. Macromol. Sci. Phys. B2 391.
121. Koning, C. E.; Noordover, B. A. J.; et al. Unpublished results and personal communication with Prof. P. Smith, ETH Zürich.
122. N.A. Jones, E.D.T. Atkins, M.J. Hill, et al. (1996) Macromolecules 29 6011.
123. S.J. Cooper, M. Coogan, N. Everall and I. Priestnall (2001) Polymer 42 10119.
124. N.A. Jones, E.D.T. Atkins, M.J. Hill, et al. (1997) Polymer 38 2689.
125. S.J. Cooper, M. Coogan, N. Everall and I. Priestnall (2001) Polymer 42 10119.
126. J. Hirschinger, H. Miura, K.H. Gardner and A.D. English (1990) Macromolecules 23 2153.
127. K. Tashiro and Y. Yoshioka (2004) Polymer 45 6349.
128. C. Ramesh, A. Keller and S.J.E.A. Eltink (1994) Polymer 35 2483.
129. http://www.arcopolimeri.com/multimedia/prodotti/pdf/43.pdf Internal data base DSM Engineering Plastics
130. Gabler, R. W. R. Grace & Co, CH480381, 1969.
131. Schmid, E.; Bonaduz, G. W.; E.M.S. Inventa AG, DE 2642244, 1977.
132. Nielinger, W.; Neuray, D.; Brassat, B. Bayer AG, DE 2743515, 1979.
133. Pagilagan, R. U., DuPont Corp., EP 0053876, 1980.
134. Rulkens R., Crombach R. C. B. DSM IP Assets B.V., U.S. Patent 6, 747, 120, 2004.
135. T.F. Novitsky, C.A. Lange, L.J. Mathias, et al. (2010) Polymer 51 2417.
136. Hewel, M. EMS AG, EP 1988113, 2008.
137. W. Götz and E. Roerdink (1998) G.W. Becker, D. Braun (Eds) Kunststoff Handbuch 3/4 Polyamide Hanser: München/Wien 806.
138. Oka, H. Kuraray Co., EP 0659799, 1995.
139. Cao, M. Jinfa Technology Dev. Co., CN Patent 101, 456, 949, 2007.
140. Buflaud, T.; Blondel, P.; Lefrebvre, T. Arkema, FR Patent 2, 934, 865, 2010.
141. P.W. Morgan and S.L. Kwolek (1975) Macromolecules 8 104.
142. K. Saotome and H. Komoto (1966) J. Polym. Sci. A 4 1463.
143. Ayuba, S.; Ishii, K.; Kanda, T.; et al. Mitsubishi Gas Chemical Company, WO Patent 2010032692A1, 2010.
144. http://canplastics.com/news/solvay-and-mitsubishi-gas-chemical-join-forces-for-high-temperature-bio-polymers/1000390131/ Press release Solvay, 25.10.2010
145. M. Hewel (1995) M.I. Kohan (Eds) Nylon Plastics Handbook New York: Hanser 372-373.
146. W. Götz and E. Roerdink (1998) G.W. Becker, D. Braun (Eds) Kunststoff Handbuch 3/4 Polyamide München/Wien: Hanser Verlag 804.
147. Mao, J.; Durchholz, M.; Biermann, M. Cognis IP Management GmbH, WO Patent 2, 009, 068, 242, 2009.
148. W. Wang, X. Wang, R. Li, B. Liu, E. Wang and Y. Zhang (2009) J. Appl. Polym. Sci. 114 2036.
149. E.D. Harveym and F.J. Hybart (1971) Polymer 12 711.
150. R.J. Gaymans, S. Aalto and F.H.J. Maurer (1989) J. Polym. Sci. 27 423.
151. Yamamoto, S. Mitsui Petrochemical Industries Ltd., EP 0449466, 1991.
152. O.B. Edgar and R. Hill (1952) J. Polym. Sci. 8 1.
153. A.J. Yu and R.D. Evans (1960) J. Polym. Sci. 42 249.
154. Schmid, E.; Thullen, H. Inventa AG, DE 4122211, 1993.
155. G. Deleens, P. Foy and E. Marechal (1977) Eur. Polym. J 13 337.
156. G. Deleens, P. Foy and E. Marechal (1977) Eur. Polym. J 13 343.
157. G. Deleens, P. Foy and E. Marechal (1977) Eur. Polym. J 13 353.
158. S. Muncu, K. Burzin, R. Feldmann and R. Feinauer (1978) Angew. Makromol. Chem. 74 49.
159. F. Baumann (1998) G.W. Becker, D. Braun (Eds) Kunststoff Handbuch 3/4 Polyamide München/Wien: Hanser Chapter 8
160. Dite, S. A. Ato Chimie, NL 7809006, 1979.
161. Burzin, K.; Mumcu, S.; Feldmann, R.; et al. Chemische Werke Hüls, DE 2712987, 1978.
162. Foy, P.; Jungblut, C.; Deleens, G. Atochem, DE 2523991, 1988.
163. Deleens, G.; Ferlampin, J.; Gonnet, M. Ato Chimie S.A., DE 2837687, 1979.
164. Liedlof, H. J. EMS Inventa AG, DE 3428404, 1985.
165. Foy, P.; Kern, R. Ato Chimie, DE 2632120, 1977.
166. Tanaka, C.; Kondou, M.; Yamamoto, Y. Toray Industries Inc., EP 163902, 1985.
167. M. Xie and Y. Camberlin (1986) Makromol. Chem. 187 383.
168. S.W. Shalaby, E.M. Pearce and H.K. Reimschuessel (1973) Pap. Meet. Am. Chem. Soc. Div Org. Coat. Plast. Chem. 33 640.
169. Panoch, H. J.; Mumcu, S. Chemische Werke Hüls, DE 2932234, 1981.
170. Suzuki, Y.; Nakamura, M.; Aochiama, A. Asahi Kasei, EP 221188, 1987.
171. Tanaka, C.; Chita, A.; Nakashima, S.; Shimobu, N. Toray Industries Inc., DE 3145998, 1982.
172. Tanaka, C.; Nakashima, S.; Kon Dou, M. Toray Industries Inc., EP 95893, 1983.
173. Cohen, J.L.; Sikkema, D.J.; Van Berkel, R.W.M. Akzo NVNL 8101262, 1981 (Chem. Abstr. 1983, 98, 5124).
174. R.J. Gaymans, P. Schwering and J.L. De Haan (1989) Polymer 30 974.
175. Gaymans, R. J.; Roerdink, E.; Schwering, P. J.; Walch, E. Stamicarbon B.V., EP 360311, 1990.
176. G. Deleens (1990) G. Legge (Eds) Thermoplastic Elastomers München/Vienna/New York: Hanser Verlag 215-239.
177. http://www.pebax.com/sites/pebax/en/properties/mechanical _properties1
178. C.E. Koning, M. Van Duin, C. Pagnoulle and R. Jérôme (1998) Progr. Polym. Sci. 23 707.
179. Borggreve, R. J. M. Toughening of Polyamide 6; Thesis University of Twente, 1988.
180. B. Majumdar, H. Keskkula, D.R. Paul and N.G. Harvey (1994) Polymer 35 4263.
181. Internal data collected at DSM Research.
182. A. Verma, B.L. Deopura and A.K. Sengupta (1986) J. Appl. Polym. Sci. 31 747.
183. K.N. Bhaumik, B.L. Deopura and V.K. Srivastava (1992) Int. J. Polym. Mater. 18 71.
184. T.S. Ellis (1989) Macromolecules 22 742.
185. T.S. Ellis (1991) Polymer 32 489.
186. F. Rybnikar and P.H. Geil (1992) J. Appl. Polym. Sci. 46 797.
187. A.M. Kotliar (1981) J. Polym. Sci. Macromol. Rev. 16 367.
188. M. Nase, B. Langer, S. Schumacher and W. Grellmann (2009) J. Appl. Polym. Sci. 111 2245.