Advances in the Production of Poly(ethylene naphthalate) Fibers

References

• Cook , J. G. , Huggill , H. P. W. and Lowe , A. R. Manufacture of new highly polymeric linear esters and the production of filaments, fibres and the like therefrom . GB Patent 604073 . 1948 . (Imperial Chemical Industries Ltd.)
   Google Scholar
• Jager , J. , Juijn , J. A. , van den Heuvel , C. J. M. and Huijts , R. A. 1995 . Poly(ethylene‐2,6‐naphthalenedicarboxylate) fiber for industrial applications . J. Appl. Polym. Sci. , 57 : 1429 – 1440 .
   Google Scholar
• Ward , I. M. , Wilding , M. A. and Brody , H. 1976 . The mechanical properties and structure of poly(m‐methylene terephthalate) fibers . J. Polym. Sci. Polym. Phys. Ed. , 14 : 263 – 274 .
   Web of Science ®Google Scholar
• Hockenberger , A. S. , Koral , S. and Wilding , M. A. 2005 . Recovery from strain and shrinkage measurements of poly(m‐methylene terephthalate) and poly(ethylene 2,6‐naphthalate) fibers . Text. Res. J. , 75 : 111 – 116 .
   Web of Science ®Google Scholar
• http://www.bp.com/liveassets/bp_internet/globalbp/STAGING/global_assets/downloads/pdfs/acetyls_aromatics_pta/N_14_Fiber.pdf (accessed Jan. 2007)
   Google Scholar
• Shima , T. , Yamashiro , S. , Yoshimura , M. , Kuratsuji , T. , Fujimoto , I. , Kato , Y. and Maeda , K. Rubber articles reinforced with filaments . US Patent 3616832 . 1971 . (Teijin Ltd.)
   Google Scholar
• Shima , T. , Yamashiro , S. , Yoshimura , M. , Kobayashi , T. , Kuratsuji , T. and Inata , H. Improved polyester filaments and their production . GB Patent 1325107 . 1973 . (Teijin Ltd.)
   Google Scholar
• Kawase , S. , Maeda , K. , Kumakawa , S. and Kuratsuji , T. Tires . US Patent 3929180 . 1975 . (Teijin Ltd.)
   Google Scholar
• Hamana , I. , Fujiwara , Y. and Kumakawa , S. Method of producing a polyethylene‐2,6‐naphthalate yarn . GB Patent 1445464 . 1976 . (Teijin Ltd.)
   Google Scholar
• Hamana , I. , Fuziwara , Y. and Kumakawa , S. Process for spinning naphthalate polyester fibers . US Patent 4000239 . 1976 . (Teijin Ltd.)
   Google Scholar
• Hamana , I. , Fujiwara , Y. and Kumakawa , S. Novel naphthalate polyester fibers, and their end uses . US Patent 4001479 . 1977 . (Teijin Ltd.)
   Google Scholar
• Shima , T. , Yamashiro , S. , Yoshimura , M. , Kobayashi , T. , Kuratsuji , T. and Inata , H. Process for preparing heat‐resistant aromatic polyester filaments . US Patent 4026973 . 1977 . (Teijin Ltd.)
   Google Scholar
• Sakellarides , S. L. 2004 . “ Poly(ethylene naphthalate) (PEN) ” . In Encyclopedia of Polymer Science and Technology Vol. 11 , 88 – 113 . John Wiley & Sons, Inc .
   Google Scholar
• Callander , D. D. 2003 . “ Properties and applications of poly(ethylene 2,6‐naphthalene), its copolyesters and blends ” . In Modern Polyesters: Chemistry and Technology of Polyesters and Copolyesters Edited by: Scheirs , J. and Long , T. E. 323 – 334 . John Wiley & Sons, Inc .
   Google Scholar
• Lillwitz , L. D. 2001 . Production of dimethyl‐2,6‐naphthalenedicarboxylate: precursor to polyethylene naphthalate . Appl. Catal. A‐Gen. , 221 : 337 – 358 .
   Google Scholar
• Hu , B. , Ottenbrite , R. M. and Siddiqui , J. A. 2003 . “ Biaxially oriented poly(ethylene 2,6‐naphthalene) films: manufacture, properties and commercial applications ” . In Modern Polyesters: Chemistry and Technology of Polyesters and Copolyesters Edited by: Scheirs , J. and Long , T. E. 335 – 339 . John Wiley & Sons, Inc .
   Google Scholar
• Chem Systems . 2000 . 2,6‐Dimethylnaphthalene (2,6‐DMN) . PERP Report, Oct. ,
   Google Scholar
• Parkinson , G. 2000 . A cheaper route to high‐purity 2,6‐dimethyl naphthalene . Chem. Eng. , 107 : 17
   Google Scholar
• http://www.bp.com/liveassets/bp_internet/globalbp/STAGING/global_assets/downloads/pdfs/acetyls_aromatics_pta/N_17_PEN_Homopolymer_Prep.pdf (accessed Jan. 2007)
   Google Scholar
• Duh , B. 2007 . Solid‐state polymerization of poly(ethylene 2,6‐naphthalate) . J. Appl. Polym. Sci. , 103 : 1075 – 1084 .
   Google Scholar
• Duh , B. Process for crystallization of polyethylene naphthalate . US Patent 4963644 . 1990 . (The Goodyear Tire & Rubber Co.)
   Google Scholar
• Duh , B. Process for the crystallization of polyethylene naphthalate prepolymers and the solid stating of those crystallized prepolymers . US Patent 5750644 . 1998 . (Shell Oil Co.)
   Google Scholar
• Duh , B. Process for the crystallization of polyethylene naphthalate prepolymers and the solid stating of those crystallized prepolymers . US Patent 5744578 . 1998 . (Shell Oil Co.)
   Google Scholar
• Tonelli , A. E. 2002 . PET versus PEN: what difference can a ring make? . Polymer , 43 : 637 – 642 .
   Google Scholar
• http://www.bp.com/liveassets/bp_internet/globalbp/STAGING/global_assets/downloads/pdfs/acetyls_aromatics_pta/N_9_General_Polym_Prop.pdf (accessed Jan. 2007)
   Google Scholar
• Buchner , S. , Wiswe , D. and Zachmann , H. G. 1989 . Kinetics of crystallization and melting behaviour of poly(ethylene naphthalene‐2,6‐dicarboxylate) . Polymer , 30 : 480 – 488 .
   Web of Science ®Google Scholar
• Mencik , Z. 1967 . Crystal structure of polycondensate of naphthalene‐2,6‐dicarboxylic acid with ethylene glycol . Chem. Prum. , 17 : 78 – 81 .
   Google Scholar
• Nakamae , K. , Nishino , T. , Tada , K. , Kanamoto , T. and Ito , M. 1993 . Elastic modulus of the crystalline regions of poly(ethylene‐2,6‐naphthalate) . Polymer , 34 : 3322 – 3324 .
   Web of Science ®Google Scholar
• Thistlethwaite , T. , Jakeways , R. and Ward , I. M. 1988 . The crystal modulus and structure of oriented poly(ethylene terephthalate) . Polymer , 29 : 61 – 69 .
   Google Scholar
• Zachmann , H. G. , Wiswe , D. , Gehrke , R. and Riekel , C. 1985 . Characterization of polymers with specific properties by means of synchrotron radiation . Die Makromolekulare Chemie , 12 : 175 – 188 . (suppl)
   Google Scholar
• Liu , J. , Sidoti , G. , Hommema , J. A. , Geil , P. H. , Kim , J. C. and Cakmak , M. 1998 . Crystal structures and morphology of thin‐film, melt‐crystallized, and polymerized poly(ethylene naphthalate) . J. Macromol. Sci., Pt B‐Phys. , B37 : 567 – 586 .
   Web of Science ®Google Scholar
• Miyata , K. , Kikutani , T. and Okui , N. 1997 . Fiber structure formation in ultra‐high‐speed melt spinning of poly(ethylene 2,6‐naphthalene dicarboxylate) . J. Appl. Polym. Sci. , 65 : 1415 – 1427 .
   Web of Science ®Google Scholar
• Vasanthan , N. and Salem , D. R. 1999 . Structural and conformational characterization of poly(ethylene 2,6‐naphthalate) by infrared spectroscopy . Macromolecules , 32 : 6319 – 6325 .
   Google Scholar
• Dorlitz , H. and Zachmann , H. G. 1997 . Molecular mobility in poly(ethylene‐2,6‐naphthalene dicarboxylate) as determined by means of deuteron NMR . J. Macromol. Sci., Pt B‐Phys. , B36 : 205 – 219 .
   Google Scholar
• Blanton , T. N. 2002 . An X‐ray diffraction study of poly(ethylene‐2,6‐naphthalate), PEN . Powder Diffr. , 17 : 125 – 131 .
   Google Scholar
• Ulcer , Y. and Cakmak , M. 1996 . Effect of annealing on the structure of injection‐molded Pen . J. Appl. Polym. Sci. , 62 : 1661 – 1678 .
   Web of Science ®Google Scholar
• Cakmak , M. and Kim , J. C. 1997 . Structure development in high‐speed spinning of polyethylene naphthalate (PEN) fibers . J. Appl. Polym. Sci. , 64 : 729 – 747 .
   Google Scholar
• Sadanobu , J. and Inata , H. 1998 . “ The properties of poly(ethylene naphthalate) (PEN) and its application ” . In Science and Technology of Polymers and Advanced Materials Edited by: Prasad , P. N. , Mark , J. E. , Kandil , S. H. and Kafafi , Z. H. 141 – 151 . New York : Plenum Press .
   Google Scholar
• Rim , P. B. , Nelson , C. J. , Mohajer , Y. and Young , J. A. High modulus polyester yarn for tire cords and composites . US Patent 5397527 . 1995 . (AlliedSignal Inc.)
   Google Scholar
• Bang , Y. H. , Kwon , I. H. , Lee , D. J. , Lee , J. and Park , C. M. Polyethylene‐2,6‐naphthalate fiber having high tenacity, low shrinkage and excellent workability, and manufacturing method thereof by high velocity spinning method and radial in to out quenching method . KR Patent 20050003122 . 2005 . (Hyosung Co.)
   Google Scholar
• Bang , Y. H. , Kwon , I. H. , Lee , D. J. and Lee , J. Polyethylene‐2,6‐naphthalate fiber having high tenacity and low shrinkage, and manufacturing method thereof by low velocity spinning method and radial in to out quenching method . KR Patent 20050003125 . 2005 . (Hyosung Co.)
   Google Scholar
• Wu , G. , Liu , M. , Li , X. N. and Cuculo , J. A. 2000 . Structure development and physical properties achieved in the drawing and/or annealing of PEN fibers . J. Polym. Sci. Pt. B‐Polym. Phys. , 38 : 1424 – 1435 .
   Google Scholar
• van den Heuvel , C. J. M. and Klop , E. A. 2000 . Relations between spinning, molecular structure and end‐use properties of polyethylene naphthalate tire yarns . Polymer , 41 : 4249 – 4266 .
   Google Scholar
• Kumakawa , S. , Hamana , I. and Fujiwara , Y. Polyethylene naphthalate fiber and its production . JP Patent 4735318 . 1972 . (Teijin Ltd.)
   Google Scholar
• Naphthalate polyester fibres . GB Patent 1384581 . 1975 . Teijin Ltd
   Google Scholar
• Kumakawa , S. , Hamana , I. and Fujiwara , Y. Polyethylene naphthalate fiber and its production . JP Patent 524651 . 1977 . (Teijin Ltd.)
   Google Scholar
• Ito , M. , Honda , K. and Kanamoto , T. 1992 . Two‐stage drawing of poly(ethylene 2,6‐naphthalate) . J. Appl. Polym. Sci. , 46 : 1013 – 1023 .
   Web of Science ®Google Scholar
• Nagai , A. and Kuroda , T. Naphthalate polyester fiber and its production . JP Patent 4194021 . 1992 . (Teijin Ltd.)
   Google Scholar
• Nagai , A. and Kuroda , T. Polyethylene naphthalate fiber and its production . JP Patent 4352811 . 1992 . (Teijin Ltd.)
   Google Scholar
• Nagai , A. , Saiki , N. and Kuroda , T. Polyethylene naphthalate yarn . JP Patent 5163612 . 1993 . (Teijin Ltd.)
   Google Scholar
• Shimada , T. and Hayashi , K. Production of naphthalate polyester fiber . JP Patent 4119119 . 1992 . (Toyobo Co., Ltd.)
   Google Scholar
• Shima , T. , Yamashiro , S. , Yoshimura , M. , Kuratsuji , T. , Fujimoto , I. , Kato , Y. and Maeda , K. Fiber‐reinforced rubber products . JP Patent 5266 . 1977 . (Teijin Ltd.)
   Google Scholar
• Nagai , A. , Minamisono , K. and Kuroda , T. Production of high‐strength polyethylene naphthalate fiber . JP Patent 6128810 . 1994 . (Teijin Ltd.)
   Google Scholar
• Terasaka , F. and Yamauchi , T. Polyethylene naphthalate fiber and its production . JP Patent 10088422 . 1998 . (Teijin Ltd.)
   Google Scholar
• Kumakawa , S. and Komoriya , T. Polyester fiber . JP Patent 62156312 . 1987 . (Teijin Ltd.)
   Google Scholar
• Nagai , A. , Matsui , Y. and Kuroda , T. Polyethylene naphthalate fiber excellent in thermal stability and its production . JP Patent 6184815 . 1994 . (Teijin Ltd.)
   Google Scholar
• Kumakawa , S. , Hamana , I. and Fujiwara , Y. Spinning of poly(ethylene 2,6‐naphthalenedicarboxylate) fibers . JP Patent 5046923 . 1975 . (Teijin Ltd.)
   Google Scholar
• Kwon , I. H. , Bang , Y. H. , Lee , J. , Lee , D. J. and Lee , I. H. High tenacity polyethylene‐2,6‐naphthalate fibers . US Patent Application y20050148756 . 2005 .
   Google Scholar
• Cho , E. L. , Choi , S. J. and Lee , J. High strength polyethylene naphthalate fiber . US Patent 6511747 . 2003 . (Hyosung Co.)
   Google Scholar
• Choi , S. M. and Lee , J. High tenacity and low shrinkage polyethylene‐2,6‐naphthalate fiber and manufacturing method thereof . KR Patent 20030076014 . 2003 . (Hyosung Co.)
   Google Scholar
• Bang , Y. H. , Kwon , I. H. and Lee , D. J. Uniform high tenacity polyethylene‐2,6‐naphthalate fiber and manufacturing method thereof . KR Patent 20040071908 . 2004 . (Hyosung Co.)
   Google Scholar
• Bang , Y. H. , Kim , C. and Kwon , I. H. High‐performance radial tire using polyethylene‐2,6‐naphthalate fiber that improves fatigue resistance and shape stability . KR Patent 20050012445 . 2005 . (Hyosung Co.)
   Google Scholar
• Bang , Y. H. , Kwon , I. H. , Lee , D. J. and Lee , J. High tenacity polyethylene‐2,6‐naphthalate fiber and manufacturing method thereof injecting high temperature air to yarn . KR Patent 20050003117 . 2005 . (Hyosung Co.)
   Google Scholar
• Lee , D. J. , Lee , J. and Sim , D. S. High strength polyethylene‐2,6‐naphthalate fiber and production th0ereof . KR Patent 20020056713 . 2002 . (Hyosung Co.)
   Google Scholar
• Bang , Y. H. , Kwon , I. H. , Lee , D. J. and Lee , J. Polyethylene‐2,6‐naphthalate fiber having high tenacity and excellent physical properties, and manufacturing method thereof by high velocity spinning method . KR Patent 20050003116 . 2005 . (Hyosung Co.)
   Google Scholar
• Hamana , I. , Fujiwara , Y. and Kumakawa , S. Heat‐resistant polyethylene naphthalate fiber . JP Patent 4864222 . 1973 . (Teijin Ltd.)
   Google Scholar
• Kumakawa , S. , Hamana , I. and Fujiwara , Y. Reinforcing agents for rubbers . JP Patent 5016739 . 1975 . (Teijin Ltd.)
   Google Scholar
• Wu , G. , Li , Q. C. and Cuculo , J. A. 2000 . Fiber structure and properties of poly(ethylene‐2,6‐naphthalate) obtained by high‐speed melt spinning . Polymer , 41 : 8139 – 8150 .
   Web of Science ®Google Scholar
• Miyata , K. , Ito , H. , Kikutani , T. and Okui , N. 1998 . Effect of liquid isothermal bath in high‐speed melt spinning of poly (ethylene 2,6‐naphthalene dicarboxylate) . Sen‐I Gakkaishi , 54 : 661 – 671 .
   Google Scholar
• van den Heuvel , C. J. M. , de Weijer , A. P. , Middeljans , H. and Heuvel , H. M. Multifilament yarn of polyethylene naphthalate and method for producing said yarn . US Patent 5466525 . 1995 . (Akzo Nobel N.V.)
   Google Scholar
• van den Heuvel , C. J. M. , de Weijer , A. P. , Middeljans , H. and Heuvel , H. M. Process of making multifilament yarn, monofilament or film of polyethylene naphthalate . US Patent 5618480 . 1997 . (Akzo Nobel N.V.)
   Google Scholar
• Matsui , M. , Murase , Y. , Ohwaki , S. , Iohara , K. and Miyamoto , T. 1996 . Ultra‐high speed spinning of poly(ethylene 2,6‐naphtalenedicarboxylate) (PEN) . Kobunshi Ronbunshu , 53 : 294 – 301 .
   Google Scholar
• Kang , Y. A. , Kim , K. H. , Cho , H. K. and Kikutani , T. 2005 . Effect of low‐temperature annealing on dimensional stability of poly(ethylene 2,6‐naphthalene dicarboxylate) fibers melt‐spun at high speed . J. Appl. Polym. Sci. , 95 : 212 – 218 .
   Google Scholar
• Suzuki , A. , Kuwabara , T. and Kunugi , T. 1998 . Application of a zone‐drawing and zone‐annealing method to poly(ethylene‐2,6‐naphthalate) fibres . Polymer , 39 : 4235 – 4241 .
   Google Scholar
• Suzuki , A. and Koide , C. 2000 . High‐performance poly(ethylene‐2,6‐naphthalate) fiber prepared by high‐tension annealing . J. Appl. Polym. Sci. , 38 : 61 – 67 .
   Google Scholar
• Bang , Y. H. , Kwon , I. H. , Lee , D. J. and Lee , J. High tenacity polyethylene‐2,6‐naphthalate fiber having excellent mechanical properties and thermal properties, and manufacturing method thereof . KR Patent 20050003119 . 2005 . (Hyosung Co.)
   Google Scholar
• Fujimoto , K. , Iohara , K. , Ohwaki , S. and Murase , Y. 1991 . Superstructure in ultrahigh speed spun fibers of poly(ethylene terephthalate) . J. Appl. Polym. Sci. , 42 : 1509 – 1517 .
   Google Scholar
• Carr , P. L. , Zhang , H. P. and Ward , I. M. 1996 . The production and properties of poly(ethylene naphthalate‐2,6‐dicarboxylate) monofilaments . Polym. Adv. Technol. , 7 : 39 – 46 .
   Google Scholar
• Mezghani , K. and Spruiell , J. E. 1998 . High speed melt spinning of poly(L‐lactic acid) filaments . J. Polym. Sci. Pt. B‐Polym. Phys. , 36 : 1005 – 1012 .
   Web of Science ®Google Scholar
• Wu , G. , Li , H. W. , Wu , Y. Q. and Cuculo , J. A. 2002 . Structure and property studies of poly(trimethylene terephthalate) high‐speed melt spun fibers . Polymer , 43 : 4915 – 4922 .
   Google Scholar
• Huijts , R. A. and Peters , S. M. 1994 . The relation between molecular orientation and birefringence in PET and PEN fibres . Polymer , 35 : 3119 – 3121 .
   Google Scholar
• Miyata , K. , Ito , H. , Kikutani , T. and Okui , N. 1999 . Structural change of high‐speed spun poly(ethylene 2,6‐naphthalene dicarboxylate) fibers with annealing . Sen‐I Gakkaishi , 55 : 542 – 551 .
   Google Scholar
• Suzuki , A. , Nakamura , Y. and Kunugi , T. 1999 . Microstructure and mechanical properties of hot‐air drawn poly(ethylene‐2,6‐naphthalate) fibers . Polymer , 40 : 5043 – 5049 .
   Google Scholar
• Chae , H. G. , Chae , D. W. , Kim , B. C. and Seo , S. W. 2002 . Enhancement of the dimensional stability of poly(ethylene2,6‐naphthalene dicarboxylate) filament by multistep zone annealing spinning . J. Appl. Polym. Sci. , 83 : 916 – 922 .
   Google Scholar
• Murakami , S. , Yamakawa , M. , Tsuji , M. and Kohjiya , S. 1996 . Structure development in the uniaxial‐drawing process of poly(ethylene naphthalate) . Polymer , 37 : 3945 – 3951 .
   Web of Science ®Google Scholar
• Cakmak , M. and Lee , S. W. 1995 . Molecular mechanism of neck formation in uniaxially stretched poly(ethylene naphthalate) films . Polymer , 36 : 4039 – 4054 .
   Web of Science ®Google Scholar
• Huijts , R. A. and Devries , A. J. 1993 . Mechanical‐behavior of poly(ethylene 2,6‐naphthalene‐dicarboxylate) (PEN) fibers near the glass‐rubber transition‐temperature . Int. J. Polym. Mater. , 22 : 231 – 236 .
   Web of Science ®Google Scholar
• Iizuka , N. and Yabuki , K. 1995 . High‐speed spinning of poly(ethylene naphthalate)—Relation between neck‐like deformation and fiber structure formation . Sen‐I Gakkaishi , 51 : 463 – 469 .
   Google Scholar
• Nagai , A. , Murase , Y. , Kuroda , T. , Matsui , M. , Mitsuishi , Y. and Miyamoto , T. 1995 . Fiber properties of poly(ethylene 2,6‐naphthalenedicarboxylate) obtained by high speed spinning . Sen‐I Gakkaishi , 51 : 470 – 477 .
   Google Scholar
• Kawahara , Y. , Yoshioka , T. , Tsuji , M. , Kikutani , T. , Sugiura , K. and Ogawa , S. 2002 . Morphology of high‐speed spun poly(ethylene‐2,6‐naphthalene dicarboxylate) fiber and its structural changes by the treatment in supercritical carbon dioxide fluid . J. Macromol. Sci.‐Phys. , B41 : 177 – 184 .
   Google Scholar
• Cakmak , M. , Wang , Y. D. and Simhambhatla , M. 1990 . Processing characteristics, structure development, and properties of uni and biaxially stretched poly(ethylene 2,6‐naphthalate) (PEN) films . Polym. Eng. Sci. , 30 : 721 – 733 .
   Web of Science ®Google Scholar
• Haberkorn , H. , Hahn , K. , Breuer , H. , Dorrer , H.‐D. and Matthies , P. 1993 . On the neck‐like deformation in high‐speed spun polyamides . J. Appl. Polym. Sci. , 47 : 1551 – 1579 .
   Web of Science ®Google Scholar
• Nagai , A. , Murase , Y. , Kuroda , T. , Matsui , M. , Mitsuishi , Y. and Miyamoto , T. 1995 . Structural change of crystal modifications of poly (ethylene 2,6‐naphthalenedicarboxylate) fiber obtained by high speed spinning . Sen‐I Gakkaishi , 51 : 478 – 483 .
   Google Scholar
• Flory , P. J. 1956 . Statistical thermodynamics of semi‐flexible chain molecules . Proc. Roy. Soc. London A , 234 : 60 – 73 .
   Web of Science ®Google Scholar
• Cheng , S. Z. D. and Wunderlich , B. 1988 . Glass transition and melting behavior of poly(ethylene‐2,6‐naphthalenedicarboxylate) . Macromolecules , 21 : 789 – 797 .
   Web of Science ®Google Scholar
• Jakeways , R. , Klein , J. L. and Ward , I. M. 1996 . The existence of a mesophase in poly(ethylene naphthalate) . Polymer , 37 : 3761 – 3762 .
   Google Scholar
• Saw , C. K. , Menczel , J. , Choe , E. W. and Hughes , O. R. 1997 . Mesophase in drawn PEN fibers . SPE Antec , 2 : 1610 – 1617 .
   Google Scholar