EP0623179B2 - High modulus polyester yarn for tire cords and composites - Google Patents

High modulus polyester yarn for tire cords and composites Download PDF

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Publication number
EP0623179B2
EP0623179B2 EP93901119A EP93901119A EP0623179B2 EP 0623179 B2 EP0623179 B2 EP 0623179B2 EP 93901119 A EP93901119 A EP 93901119A EP 93901119 A EP93901119 A EP 93901119A EP 0623179 B2 EP0623179 B2 EP 0623179B2
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EP
European Patent Office
Prior art keywords
yarn
drawn
undrawn
melting point
modulus
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP93901119A
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German (de)
English (en)
French (fr)
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EP0623179A1 (en
EP0623179B1 (en
Inventor
Peter Bryan Rim
Charles Jay Nelson
Yousef Mohajer
John Armstrong Young
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Honeywell International Inc
Performance Fibers Inc
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AlliedSignal Inc
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Application filed by AlliedSignal Inc filed Critical AlliedSignal Inc
Publication of EP0623179A1 publication Critical patent/EP0623179A1/en
Application granted granted Critical
Publication of EP0623179B1 publication Critical patent/EP0623179B1/en
Publication of EP0623179B2 publication Critical patent/EP0623179B2/en
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Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/62—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters

Definitions

  • This invention relates to polyethylene naphthalate (PEN) multifilament yarn and other yarns made from similarly rigid monomer combinations with extremely high modulus, good tenacity, and low shrinkage particularly useful for the textile reinforcement of tires.
  • the PEN yarn of this invention provides enhanced modulus and dimensional stability when compared to conventionally processed PEN yarns.
  • a process for production of the multi-filament PEN yarn is an aspect of this invention.
  • PET polyethylene terephthalate
  • the resulting yarn exhibits surprisingly high modulus and tenacity together with low shrinkage when compared to prior art yarns.
  • the invention also provides a drawn semicrystalline polyester multifilament yarn having Tg greater than 100°C and a melting point elevation of at least 9°C, which is obtained by drawing a polyester yarn having an undrawn birefringence of at least 0.030.
  • Fig. 1 represents a comparison of modulus at a tenacity of 6.2 g/d (54.7 mN/dtex) for the PEN yarns of Examples 1 and 2.
  • the polyester multifilament yarn of the present invention provides high modulus, high dimensional stability and good tenacity, characteristics which are extremely desirable when this material is incorporated as fibrous reinforcement into rubber composites such as tires.
  • PEN multifilament yarns or other yarns of polyester polymers made from similarly rigid monomer combinations can be used advantageously to reinforce two parts of a radial passenger tire, the carcass and the belt.
  • passenger tire carcasses are reinforced primarily by polyethylene terephthalate.
  • Two tire characteristics which are controlled by the carcass cord property of dimensional stability (modulus at a given shrinkage) are sidewall indentations and tire handling.
  • PEN multifilament yarns and other polyester yarns of this invention can also be used to reinforce the belts of radial passenger tires and the carcasses of radial truck tires.
  • steel is used for these applications since PET prossesses insufficient strength and modulus for a given cord diameter.
  • the high modulus of PEN relative to PET, and the additional modulus advantages of the PEN of this invention will make PEN an ideal material to be used as a steel substitute.
  • the polyethylene naphthalate yarn of the invention contains at least 90 mol percent polyethylene naphthalate.
  • the polyester is substantially all polyethylene naphthalate.
  • the polyester may incorporate as copolymer units minor amounts of units derived from one or more ester-forming ingredients other than ethylene glycol and 2,6 naphthylene dicarboxylic acid or their derivatives.
  • ester forming ingredients which may be copolymerized with the polyethylene naphthalate units include glycols such as 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, etc., and dicarboxylic acids such as terephthalic acid, isophthalic acid, hexahydroterephthalic acid, stilbene dicarboxylic acid, bibenzoic acid, adipic acid, sebacic acid, azelaic acid, etc.
  • glycols such as 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, etc.
  • dicarboxylic acids such as terephthalic acid, isophthalic acid, hexahydroterephthalic acid, stilbene dicarboxylic acid, bibenzoic acid, adipic acid, sebacic acid, azelaic acid, etc.
  • polyester yarns of the invention can be prepared to contain polyester polymer made from suitable combinations of rigid and flexible monomers providing the resulting polymer is melt-spinnable, is semi-crystalline, and has a Tg greater than 100°.
  • rigid monomers include dicarboxylic acids such as 2,6-naphthalene dicarboxylic acid, 2,7-naphthalene dicarboxylic acid, diphenyl dicarboxylic acid, stilbene dicarboxylic acid and terephthalic acid; dihydroxy compounds such as hydroquinone, biphenol, p-xylene glycol, 1,4 cyclohexanedimethanol, neopentylene glycol; and hydroxycarboxylic acid such as P-hydroxybenzoic acid and 7-hydroxy- ⁇ -naphthoic acid.
  • Examples of flexible monomers include dicarboxylic acids such as oxalic acid, succinic acid, adipic acid, sebacic acid, and dihydroxy compounds such as ethylene glycol, 1,3 propanediol, 1,4 butanediol, 1,6 hexanediol. It is important that the thermal stability of the polymer above its melting point be sufficient to allow melt processing without excessive degradation.
  • the multi-filament yarn of the present invention commonly possesses a denier per filament of about 1 to 20 (e.g. about 3 to 10), and commonly consists of about 6 to 600 continuous filaments (e.g. about 20 to 400 continuous filaments).
  • the denier per filament and the number of continuous filaments present in the yarn may be varied widely as will be apparent to those skilled in the art.
  • the fibers are particularly suited for use in environments where elevated temperatures (e.g. 100°C) are encountered. Not only does the filamentary material provide enhanced modulus but it undergoes a very low degree of shrinkage for a high modulus fibrous thermoplastic.
  • L T ((L-5) 4 /T 5.16 ) 1000 L-5 or LASE-5 is a measure of modulus defined as load in g/d at 5% elongation.
  • the materials of this invention have L T at least 25. If L-5 is not measurable because of yarn elongations less than 5% the yarns will be pre-relaxed at elevated temperatures before testing to increase elongation beyond 5%.
  • Shrinkage values were determined in accordance with ASTM D885 after one minute at 177°C employing a constraining force of 0.05 g/denier (0.44 mN/dtex).
  • the melt-spinnable polyester is supplied to an extrusion spinnerette at a temperature above its melting point and below the temperature at which the polymer degrades substantially.
  • the residence time at this stage is kept to a minimum and the temperature should not rise above 350°C, preferably 320°C.
  • the extruded filaments then traverse a conventional yarn solidification zone where quench air impinges on the spun yarn thereby freezing in desirable internal structural features and preventing the filaments from fusing to one another.
  • the solidification zone preferably comprises (a) a retarded cooling zone comprising a gaseous atmosphere heated at a temperature to at least 150°C, preferably 150 to 500°C, and (b) a cooling zone adjacent to said retarded cooling zone wherein said yarn is rapidly cooled and solidified in a blown air atmosphere.
  • the key to the current process is to adjust processing conditions to achieve a highly oriented undrawn yarn of birefringence at least 0.03 and an elevated melting point of 1-25°C, preferably 3-23°C.
  • PEN a melting point of 265 to 290°C, preferably 268 to 288°C must be achieved.
  • One skilled in the art can achieve this by adjusting the following conditions: length and temperature of the retarded cooling zone adjacent to the spinnerette, diameter of the spinnerette holes, method of blowing the quench, quench air velocity, and drawdown in the solidification zone.
  • the speed of withdrawal of the yarn from the solidification zone is an important parameter affecting the stress on the spun fiber, and should be adjusted to yield the desired characteristics.
  • the spun yarn is then drawn by conventional means in either a continuous or non-continuous process to yield a drawn yarn with Tg greater than 100°C and a melting point elevation at least 9°C, preferably 9 to 15°C.
  • tenacity at least 6.5 g/d (57.4 mN/dtex), preferably at least 7.5 g/d (66.2 mN/dtex); dimensional stability (EASL + shrinkage) of less than 5%; and shrinkage of 4% or less.
  • a PEN undrawn yarn was produced by extruding 32 filaments through a spinnerette with orifices of length 0.042 inches (0.107cm) and of width 0.021 inches (0.053 cm) at a thruput of 23.2 cc/min.
  • the filaments were solidified in an air quenching column and taken up at winder speeds of 305 m/min.
  • PEN yarns were produced by extruding seven filaments through a spinnerette with orifices of length 0.036 inches (0.091 cm) and width of 0.016 inches (0.041 cm) at a thruput of 9.6 cm 3 /min.
  • the filaments were solidified in an air quenching column and taken up at winder speeds ranging from 770-5000 m/min. These yarns were drawn in two stages using a heating plate in draw zone two.
  • the undrawn yarn properties, drawn yarn properties, and drawing conditions are summarized in Table II.
  • Example II The undrawn yarns of Example II spun at 770 m/min and 4000 m/min were drawn to their ultimate limit.
  • the 770 m/min sample was drawn in one stage using an oven in the draw zone and the 4000 m/min sample was drawn in two stages using a heated plate in the second draw zone.
  • PEN yarns were produced by extruding seven filaments through a spinnerette with orifices of length 0.069 inches and width 0.030 inches at a thruput of 9.6 cc/min. The filaments were solidified in an air quenching column and taken up at winder speeds ranging from 410 m/min to 2500 m/min. The properties of these yarns are summarized in Table IV.
  • TAKE-UP SPEED 410 770 1200 1600 2000 2500 ⁇ n 0.178 0.154 0.192 0.232 0.233 0.226

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Artificial Filaments (AREA)
  • Tires In General (AREA)
  • Yarns And Mechanical Finishing Of Yarns Or Ropes (AREA)
EP93901119A 1992-01-21 1992-12-22 High modulus polyester yarn for tire cords and composites Expired - Lifetime EP0623179B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US82279992A 1992-01-21 1992-01-21
US822799 1992-01-21
PCT/US1992/011063 WO1993014252A1 (en) 1992-01-21 1992-12-22 High modulus polyester yarn for tire cords and composites

Publications (3)

Publication Number Publication Date
EP0623179A1 EP0623179A1 (en) 1994-11-09
EP0623179B1 EP0623179B1 (en) 1996-09-04
EP0623179B2 true EP0623179B2 (en) 2001-02-14

Family

ID=25237011

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93901119A Expired - Lifetime EP0623179B2 (en) 1992-01-21 1992-12-22 High modulus polyester yarn for tire cords and composites

Country Status (12)

Country Link
EP (1) EP0623179B2 (ja)
JP (1) JP2629075B2 (ja)
CN (1) CN1051586C (ja)
AU (1) AU3331293A (ja)
BR (1) BR9207038A (ja)
CA (1) CA2126328C (ja)
DE (1) DE69213474T3 (ja)
ES (1) ES2091589T5 (ja)
MX (1) MX9300142A (ja)
TR (1) TR28032A (ja)
TW (1) TW224960B (ja)
WO (1) WO1993014252A1 (ja)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4320593A1 (de) * 1993-06-22 1995-01-05 Akzo Nobel Nv Multifilament-Garn aus Polyäthylennaphthalat und Verfahren zu seiner Herstellung
KR100402839B1 (ko) * 2001-05-10 2003-10-22 주식회사 효성 고강력 폴리에틸렌 나프탈레이트 섬유
DE10140774B4 (de) * 2001-08-20 2004-08-12 Metzeler Automotive Profile Systems Gmbh Formschlauch
WO2005019509A1 (en) * 2003-08-22 2005-03-03 Hyosung Corporation High tenacity polyethylene-2,6-naphthalate fibers
JP4616658B2 (ja) * 2005-01-31 2011-01-19 帝人ファイバー株式会社 不織布
JP4928308B2 (ja) * 2007-02-28 2012-05-09 帝人ファイバー株式会社 産業資材用ポリエチレンナフタレート繊維とその製造方法
BRPI0813803A2 (pt) * 2007-07-03 2014-12-30 Gates Corp Correia de transmissão de energia
CN101978104B (zh) 2008-03-31 2013-01-02 可隆工业株式会社 未被拉伸的聚对苯二甲酸乙二醇酯(pet)纤维、被拉伸的pet纤维以及包含被拉伸的pet纤维的轮胎帘线
FR2971188B1 (fr) 2011-02-03 2013-03-08 Michelin Soc Tech Renfort composite gaine d'une couche de polymere auto-adherente au caoutchouc
FR2971187B1 (fr) * 2011-02-03 2013-03-08 Michelin Soc Tech Renfort composite gaine d'une couche de polymere auto-adherente au caoutchouc
CN102851782B (zh) * 2011-06-30 2016-05-04 上海杰事杰新材料(集团)股份有限公司 一种用于轮胎骨架材料的聚酰胺工业丝及其制造方法
JP2017053060A (ja) * 2015-09-08 2017-03-16 株式会社ブリヂストン Ｐｅｆ原糸の製造方法、ｐｅｆ原糸及びタイヤ
CN112281272A (zh) * 2020-10-15 2021-01-29 联新（开平）高性能纤维有限公司 一种超高强度尺寸稳定性聚酯帘子布经纱及其制备方法和应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3564835A (en) † 1969-03-12 1971-02-23 Du Pont High tenacity tire yarn
US4026973A (en) † 1973-08-31 1977-05-31 Teijin Limited Process for preparing heat-resistant aromatic polyester filaments
JPS62156312A (ja) † 1985-12-26 1987-07-11 Teijin Ltd ポリエステル系繊維
WO1990000638A1 (en) † 1988-07-05 1990-01-25 Allied-Signal Inc. Dimensionally stable polyester yarn for high tenacity treated cords

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3616832A (en) * 1968-12-24 1971-11-02 Teijin Ltd Rubber articles reinforced with filaments
JPS5615321B2 (ja) * 1973-09-20 1981-04-09
FR2271315B1 (ja) * 1973-10-19 1976-10-01 Teijin Ltd
JP2861335B2 (ja) * 1990-08-31 1999-02-24 東洋紡績株式会社 ナフタレートポリエステル繊維の製造方法
JP2954391B2 (ja) * 1991-05-22 1999-09-27 帝人株式会社 ポリエチレンナフタレート繊維およびその製造方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3564835A (en) † 1969-03-12 1971-02-23 Du Pont High tenacity tire yarn
US4026973A (en) † 1973-08-31 1977-05-31 Teijin Limited Process for preparing heat-resistant aromatic polyester filaments
JPS62156312A (ja) † 1985-12-26 1987-07-11 Teijin Ltd ポリエステル系繊維
WO1990000638A1 (en) † 1988-07-05 1990-01-25 Allied-Signal Inc. Dimensionally stable polyester yarn for high tenacity treated cords

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
ChemieFasern, May 1971, pp. 379-384 †
ChemieFasern/Textilindustrie, June 1985, page 411 †
DERWENT ABSTRACT NO 1975-76346W & JP-A-S50-46923 + COMPLETE ENGLISH TRANSLATION †
H. Kuchlin, Physik-Formeln und -Gesetze, Chapter 18.1,page 181, 1977 †
Journal of Polymer Science, vol. 12, 2905-2915, 1974 †
JP-A-62-156312 + complete English translation †

Also Published As

Publication number Publication date
TR28032A (tr) 1995-12-11
DE69213474T3 (de) 2001-08-23
JP2629075B2 (ja) 1997-07-09
WO1993014252A1 (en) 1993-07-22
EP0623179A1 (en) 1994-11-09
CN1051586C (zh) 2000-04-19
DE69213474T2 (de) 1997-02-06
EP0623179B1 (en) 1996-09-04
DE69213474D1 (de) 1996-10-10
CA2126328A1 (en) 1993-07-22
MX9300142A (es) 1994-07-29
TW224960B (ja) 1994-06-11
CA2126328C (en) 2002-05-21
CN1078508A (zh) 1993-11-17
AU3331293A (en) 1993-08-03
ES2091589T3 (es) 1996-11-01
ES2091589T5 (es) 2001-05-16
BR9207038A (pt) 1995-12-05
JPH06511293A (ja) 1994-12-15

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