WO1998018984A1 - Process for making high tenacity aramid fibers - Google Patents
Process for making high tenacity aramid fibers Download PDFInfo
- Publication number
- WO1998018984A1 WO1998018984A1 PCT/US1997/019148 US9719148W WO9818984A1 WO 1998018984 A1 WO1998018984 A1 WO 1998018984A1 US 9719148 W US9719148 W US 9719148W WO 9818984 A1 WO9818984 A1 WO 9818984A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- filaments
- coagulating
- jetted
- overflowing
- coagulating liquid
- Prior art date
Links
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
- D01F6/60—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides
- D01F6/605—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides from aromatic polyamides
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
- D01D5/06—Wet spinning methods
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
- D01D5/08—Melt spinning methods
Definitions
- This invention relates to a process for making aramid fibers of especially high tenacity by means of a combination of process elements including particular spinneret capillary size, particular coagulating conditions, and particular drying tension.
- a process for making yarn of poly (p-phenylene terephthalate) having a tenacity of at least 28 gpd comprising the steps of: (a) extruding filaments of an acid solution containing at least 30 grams per 100 milliliters of acid of poly (p-phenylene terephthalamide) having an inherent viscosity of at least 4 , out of a spinneret and through a layer of inert noncoagulating fluid into a coagulating bath and then through a spin tube along with overflowing coagulating liquid; (b) jetting additional coagulating liquid symmetrically about the filaments in a downward direction forming an angle of 0° to 85° with respect to the filaments within about 2.0 milliseconds from the time the filaments enter the spin tube, (i) maintaining a ratio of the mass flow rate of combined overflowing and jetted coagulating liquid to mass flow rate of the filaments of greater than about 250, (ii) maintaining an average linear velocity of combined overflowing and jetted
- FIG. 1 is a cross-sectional view of an apparatus which can be used in practice of the process to make fibers useful in this invention.
- Yarns of the present invention have a tenacity of at least 28 gpd and can be made utilizing the device depicted in Fig. 1. These yarns are made, generally, in accordance with the process disclosed in United States Patent No. 3,767,756 utilizing poly(p- phenylene terephthalamide) (PPD-T) having an inherent viscosity of at least 4.0 dissolved in sulfuric acid having a concentration of at least 98%.
- PPD-T poly(p- phenylene terephthalamide)
- the PPD-T solution is extruded from a spinneret, through an air gap and into a coagulating bath.
- the spinneret has capillaries with a diameter of 0.051 millimeter (2.0 mils) or less. It has been found that capillaries of more than 0.051 millimeter (2 mils) yield fiber filaments which are believed to have poorer molecular orientation resulting in reduced strength and, therefore, not as strong as are made using capillaries of smaller diameter. As a practical matter, capillaries of less than about 0.025 millimeter (1 mil) are difficult to use and do not yield fibers of acceptable quality.
- Fig. 1 is a cross-sectioned view of a preferred coagulating bath 1.
- Bath 1 is a circular structure consisting of an insert disc 2 fitted into supporting structure 3.
- Supporting structure 3 includes inlet 4 for introduction of quench liquid 5 under pressure into distribution ring 6 which contains filler 7 suitable to enhance uniform delivery of quench liquid around the periphery of coagulating bath 1.
- Introduction of coagulating liquid to the bath may be from a peripheral manifold containing baffles or packing to provide uniform distribution and nonturbulent flow of coagulating liquid toward the orifice. In the case of a circular bath, the manifold can surround the bath.
- filler 7 may be glass beads, a series of screens, a honeycomb structure, sintered metal plates, or other similar device.
- quench liquid After passing through filler 7, the quench liquid passes through perforated plate or screen 8 and flows uniformly without appreciable turbulence or back mixing horizontally toward the center of bath 1 where quench liquid 5 contacts filaments 9 extruded from spinneret 10 whereby both quench liquid 5 and filaments 9 pass together through orifice 11 in a downward direction into spin tube 14.
- the bottom of the bath may be contoured as illustrated by the areas indicated by A and B to facilitate uniform nonturbulent flow toward opening 11.
- An area about the orifice may also taper toward the orifice.
- the depth of the coagulating bath is no more than 20% of the bath width in the area of nonturbulent flow.
- a suitable bath width is about 6.35 cm (2.5 inches) in combination with an orifice having a diameter of 3.1 mm which has a tapered approach having a beginning diameter of about 12 mm.
- a suitable bath width is about 23 cm in combination with an orifice diameter of 9 mm which may have a tapered approach having a beginning diameter of about 28 mm.
- Insert disc 2 includes circular jet device 12 which operates similarly to the jet device disclosed in U.S. Pat. No, 4,298,565.
- Orifice 11 preferably has a lip 13, i.e., orifice 11 is of slightly smaller diameter than spin tube 14, to help keep filaments 9 from adhering to the walls of orifice 11 and spin tube 14.
- Quench liquid 5 is introduced through opening 15 through passageway 16 to one or more jet openings 17 whereby the quench liquid 5 passes along with filaments 9 and other quench liquid 5 in a downward direction through the spin tube to exit 18 toward a forwarding device (not shown) .
- the filaments are washed and/or neutralized and dried before wind-up of yarns produced by the process .
- the angle for the liquid directed by jet openings 17 in relation to the filaments is preferable for the angle ( ⁇ ) in the range of 0 to 85 degrees. While satisfactory results are also obtainable for ⁇ -90 degrees, this selection of theta, however, makes the process very critical to control and is, therefore, not as desirable in commercial operation. 30 degrees is a particularly suitable angle for use in a commercial production process. Jet openings 17 are located adjacent orifice 11 and direct the jetted coagulating fluid downwardly toward the filaments within about 2 milliseconds from the time the filaments enter the spin tube.
- the process provides the most improvement when the spinneret, spin orifice, jet and any extension of the spin tube are carefully aligned on the same axis and when the jet elements are carefully designed and aligned to provide perfectly symmetrical jetting about the threadlines. Any misalignment of jet elements or the lodging of any solid particles in jet openings so as to destroy symmetry can reduce or eliminate the improvements.
- Such symmetry may be provided from two or more jet orifices, or from slots symmetrically spaced with respect to the thread line.
- the flows of the overflowing coagulating liquid (Q ⁇ _) and jetted coagulating liquid (Q2) are controlled and are maintained constant to achieve the improvement in accordance with the present invention.
- the mass-flow ratio (R) of the mass-flow rate of the filaments is controlled to be greater than about 250. Preferably, the mass-flow ratio (R) is greater than about 300.
- flow-rate of overflowing coagulating fluid is controlled by adjustment of the depth of bath above orifice 11 (dimension h) by metering the inflow into the bath but also depends on the diameter of spin tube 14.
- Dimension h is ordinarily less than one inch (2.5 cm) and preferably about 0.5 inch (1.3 cm) . If h is too small, air will be drawn into spin tube 14 by the pumping action of the advancing filaments, and such is deleterious to both tensile properties and mechanical quality of the yarn produced. Thus, h must be great enough to assure no entrainment of gas bubbles . The above considerations lead to calculation of a suitable diameter of spin tube 14.
- the overflow rate of quench liquid (Q ⁇ _) through the orifice is greatly influenced by the moving threadline through the same orifice, this effect must also be taken into account.
- the overflow rate through a 9.5mm (0.375 in.) diameter orifice under a hydrostatic head of 15.9 mm (0.625 in.) is approximately 1.5 liter/min (0.4 gallons/min) in the absence of a moving threadline, and 8.7 liter/min (2.3 gallons/min) in the presence of a threadline of 1000 filaments of 1.5 denier per filament moving at 686 m/min. This is commonly attributed to the pumping effect of moving filaments through a layer of liquid due to boundary layer phenomena.
- the orifice size i.e., diameter of cross-sectional area is suitably selected.
- the flow-rate of jetted coagulating liquid ( ⁇ >2) is preferably controlled by metered pumping through a jet opening of selected size.
- the minor cross-sectional dimension of the jet (e.g., hole diameter or flow width) is generally in the range of 0.05 to 2.5 mm (2 to 100 mils). It is desirable for the flow-rate and the jet opening to be such that the axial velocity of the jetted coagulating liquid exceeds at least about 50% of that of the yarn being processed and preferably should exceed at least about 80% of the yarn velocity to prevent dragging of the threadline which results in a decrease in tenacity.
- the axial velocity of jetted coagulating liquid should not greatly exceed 200% of that of the yarn being processed and preferably does not exceed about 150% of the yarn velocity to prevent buffeting the threadline which can result in a reduction in measured yarn tenacity. It is therefore necessary to employ a suitable jetted liquid flow-rate and jet openings or slots which provide the mass-flow ratio of combined coagulating liquid to filament mass of greater than about 250, preferably greater than about 300, and the momentum ratio of jetted to overflowing coagulating liquids of greater than about 6.0 which also provide a suitable velocity for the jetted coagulating liquid in relation to yarn speed.
- the average linear velocity of the combined coagulating liquids in the spin tube is maintained at a velocity less than the velocity of the filaments exiting from the spin tube. This prevents a loss of yarn tenacity due to "looping" of filaments in the yarn and possible process continuity problems due to the absence of sufficient tension before the feed rolls.
- the present invention is useful for a wide range of spinning speeds and is particularly useful for spinning speeds of at least 300 m/min and preferably at least about 350 m/min although higher spinning speeds do result in a reduction in tenacity when compared with lower spinning speeds. While the advantages is tenacity produced by the process of the invention continue to increase with both increasing mass-flow ratio (R) and momentum ratio ( ⁇ ) and thus can compensate for tenacity decreases due to continued increases in spinning speed, it is believed that mass- flow ratios (R) of above 5000 and momentum ratios ( ⁇ ) above 50 will not yield any further significant improvement and will not be economically attractive for technical production, especially heavy deniers such as 1500 denier.
- the fibers once spun and passed through the coagulating bath, are washed and dried to complete the manufacture . Fibers must be thoroughly washed to remove all traces of acid and eliminate acid-related fiber degradation.
- Water alone or combinations of water and alkaline solutions can be used for fiber washing.
- a convenient method for washing is to spray the threadline, as it leaves the coagulating bath on rolls, with aqueous alkaline solutions (e.g. saturated NaHC0 3 or 0.05 N NaOH), to reduce the acid content to about 0.01% (on a dry fiber basis) .
- aqueous alkaline solutions e.g. saturated NaHC0 3 or 0.05 N NaOH
- the fibers can conveniently be dried on heated rolls (e.g. 160°C) .
- the preferred washing method for this invention is to wash the fibers with a spray and pass them continuously to dryer rolls maintained at about 150 °C.
- One important element of the process of this invention involves drying the fibers under high tension of from about 3.0 to 7.0 grams per denier (gpd). Drying tensions of less than about 3.0 gpd result in fibers which have reduced molecular orientation resulting in reduced strength and drying tensions of greater than 7.0 gpd cause excessive threadline breakage and related operational difficulties. Drying tensions of about 3.0 to 5.0 gpd are particularly preferred.
- Tenacity is reported as breaking stress divided by linear density. Modulus is reported as the slope of the initial stress/strain curve converted to the same units as tenacity. Elongation is the percent increase in length at break. Both tenacity and modulus are first computed in g/denier units which, when multiplied by 0.8826, yield dN/tex units. Each reported measurement is the average of 10 breaks. Denier is the weight, in grams, of 9000 meters and dtex is the weight, in grams, of 10,000 meters of yarn or filament.
- Tensile properties for yarns are measured at 24°C and 55% relative humidity after conditioning under the test conditions for a minimum of 14 hours. Before testing, each yarn is twisted to a 1.1 twist multiplier (for example, nominal 1500 denier yarn is twisted about 0.8 turn/centimeter) . Each twisted specimen has a test length of 25.4 cm and is elongated 50% per minute (based on the original unstretched length) using a typical recording stress/strain device.
- the twist multiplier (TM) of a yarn is defined as:
- Tensile properties for yarns are different from and lower than tensile properties for individual filaments and such values for yarns cannot successfully and accurately be estimated from filament values.
- Momentum is defined as the product of the mass-rate and the velocity of flow. Calculation of momentum ratio is described in the aforementioned U.S. Pat. No.
- Q! is the flow rate of overflowing liquid Q2 is the flow rate of jetted liquid d ⁇ _ is the inner diameter of the spin tube d2 is the minor dimension of the jet opening ⁇ is the acute angle between the jetted liquid and the threadline.
- the ratio ⁇ is independent of the units selected.
- poly (par - phyenylene terephthalamide) (PPD-T) having an inherent viscosity of about 6.3 dL/g before solutioning and about 5.5 dL/g in fiber form was spun into apparatus as illustrated in U.S. Patent No. 4,340,559 using tray G.
- the diameter of the spin tube was 0.76 cm (0.3 inch) and jets of 0.21 and 0.42 millimeters (8 and 16 mils) were employed with an angle of 30 degrees between the jetted stream and the threadline.
- the solvent employed in making spin dope was about 100.1% sulfuric acid and the concentration of polymer in the spin dope of about 19.4 wt.%.
- the spinnerets of 0.051 and 0.064 millimeters (2.0 and 2.5 mils) were employed.
- the number of capillaries of spinnerets employed included 133, 266, 400, 500, 560 and 666 capillaries.
- the air-gap, i.e., the distance of filament travel from the exit face of the spinneret to the first contact with coagulating liquid, was about 0.635 cm (0.25 inch).
- the coagulating liquid was maintained at about 3°C.
- Yarn tensions of about 1.0 gpd during washing and neutralization were employed for all of the examples described below.
- Examples of the invention utilized a mass- flow ratio (R) of 325 to 1680, along with spinnerets with capillaries of 0.051 millimeter.
- the yarns were dried under tension of greater than 2 grams per denier and the yarns had linear densities of 160 to 1500 denier.
- Comparative examples utilized the same polymer and the same spinning apparatus under the same conditions, except that the mass-flow ratios, the momentum ratios, the drying tensions, and the spinneret capillary sizes were different as shown in TABLE 1.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Mechanical Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Spinning Methods And Devices For Manufacturing Artificial Fibers (AREA)
- Artificial Filaments (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69719351T DE69719351T2 (en) | 1996-10-25 | 1997-10-22 | METHOD FOR PRODUCING HIGH-STRENGTH ARAMID FIBERS |
EP97913738A EP0934434B1 (en) | 1996-10-25 | 1997-10-22 | Process for making high tenacity aramid fibers |
EA199900408A EA001176B1 (en) | 1996-10-25 | 1997-10-22 | Process formaking high tenacity aramid fibers |
KR19997003607A KR100431679B1 (en) | 1996-10-25 | 1997-10-22 | Process for Making High Tenacity Aramid Fibers |
JP52057798A JP3888645B2 (en) | 1996-10-25 | 1997-10-22 | Method for producing high-strength aramid fiber |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US2945296P | 1996-10-25 | 1996-10-25 | |
US60/029,452 | 1996-10-25 | ||
US08/950,250 US5853640A (en) | 1997-10-14 | 1997-10-14 | Process for making high tenacity aramid fibers |
US08/950,250 | 1997-10-14 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1998018984A1 true WO1998018984A1 (en) | 1998-05-07 |
WO1998018984A9 WO1998018984A9 (en) | 1998-08-20 |
Family
ID=26704957
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1997/019148 WO1998018984A1 (en) | 1996-10-25 | 1997-10-22 | Process for making high tenacity aramid fibers |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP0934434B1 (en) |
JP (1) | JP3888645B2 (en) |
KR (1) | KR100431679B1 (en) |
CN (1) | CN1076405C (en) |
DE (1) | DE69719351T2 (en) |
EA (1) | EA001176B1 (en) |
WO (1) | WO1998018984A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008055130A2 (en) * | 2006-10-31 | 2008-05-08 | E. I. Du Pont De Nemours And Company | Process and apparatus for the production of yarn |
WO2010094620A1 (en) | 2009-02-17 | 2010-08-26 | Teijin Aramid B.V. | Method for producing a filament yarn from an aromatic polyamide |
Families Citing this family (17)
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DE60216617T2 (en) * | 2001-08-11 | 2007-09-27 | Lenzing Ag | Precipitation bath, and process using this precipitation bath |
ES2339262T3 (en) * | 2004-06-25 | 2010-05-18 | Toray Industries, Inc. | THREAD SET FOR DRY-MOISTURE AND DEVICE AND METHOD TO PRODUCE FIBER MAKING. |
WO2007004848A1 (en) * | 2005-07-06 | 2007-01-11 | Kolon Industries, Inc | Aromatic polyamide filament and method of manufacturing the same |
US7976943B2 (en) * | 2007-10-09 | 2011-07-12 | E. I. Du Pont De Nemours And Company | High linear density, high modulus, high tenacity yarns and methods for making the yarns |
KR101050860B1 (en) | 2008-03-31 | 2011-07-20 | 코오롱인더스트리 주식회사 | Para aramid fiber |
CN102644127A (en) * | 2008-03-31 | 2012-08-22 | 可隆工业株式会社 | Para-aramid fiber |
KR100930204B1 (en) * | 2008-06-27 | 2009-12-07 | 주식회사 코오롱 | Aramide fiber and method for manufacturing the same |
RU2516154C2 (en) * | 2008-08-29 | 2014-05-20 | Тейджин Арамид Б.В. | Method of manufacturing multitude of highly strong, high-modulus threads from aromatic polyamide |
KR101192918B1 (en) | 2010-12-27 | 2012-10-18 | 코오롱인더스트리 주식회사 | Method for manufacturing Aramid fiber |
EP2663676B1 (en) * | 2011-01-13 | 2015-12-16 | E. I. du Pont de Nemours and Company | Copolymer fibers and yarns and processes for making same |
KR101394653B1 (en) | 2012-10-18 | 2014-05-12 | 주식회사 효성 | Aromatic polyamide multi filament having high-strength and process for preparing the same |
KR101959209B1 (en) * | 2013-06-28 | 2019-03-19 | 코오롱인더스트리 주식회사 | Method of manufacturing aramid fiber |
CN103498207B (en) * | 2013-10-21 | 2016-05-18 | 中蓝晨光化工研究设计院有限公司 | A kind of solidification forming device that is applicable to dry spray-wet spinning manufacture aramid IIII fiber |
CN105671659B (en) * | 2016-04-08 | 2018-04-06 | 中芳特纤股份有限公司 | A kind of coagulating bath accelerator for para-aramid fiber high speed spinning |
CN108486678B (en) * | 2018-04-28 | 2020-08-28 | 义乌华鼎锦纶股份有限公司 | Preparation method of graphene/polyamide 6 composite fiber |
CN109537074A (en) * | 2018-12-28 | 2019-03-29 | 中国纺织科学研究院有限公司 | Coagulation forming device for cellulose spinning |
CN110747524B (en) * | 2019-11-26 | 2022-04-15 | 中芳特纤股份有限公司 | Coagulating bath device for para-aramid dry-jet wet spinning and spinning method thereof |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US4340559A (en) * | 1980-10-31 | 1982-07-20 | E. I. Du Pont De Nemours And Company | Spinning process |
EP0357017A2 (en) * | 1988-08-30 | 1990-03-07 | E.I. Du Pont De Nemours And Company | Improved coagulating process for filaments |
US5173236A (en) * | 1991-03-08 | 1992-12-22 | E. I. Du Pont De Nemours And Company | Method for spinning para-aramid fibers of high tenacity and high elongation at break |
US5330698A (en) * | 1993-04-19 | 1994-07-19 | E. I. Du Pont De Nemours And Company | Process for making high elongation PPD-T fibers |
-
1997
- 1997-10-22 KR KR19997003607A patent/KR100431679B1/en not_active IP Right Cessation
- 1997-10-22 JP JP52057798A patent/JP3888645B2/en not_active Expired - Fee Related
- 1997-10-22 CN CN97199148A patent/CN1076405C/en not_active Expired - Fee Related
- 1997-10-22 EA EA199900408A patent/EA001176B1/en not_active IP Right Cessation
- 1997-10-22 WO PCT/US1997/019148 patent/WO1998018984A1/en active IP Right Grant
- 1997-10-22 EP EP97913738A patent/EP0934434B1/en not_active Expired - Lifetime
- 1997-10-22 DE DE69719351T patent/DE69719351T2/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4340559A (en) * | 1980-10-31 | 1982-07-20 | E. I. Du Pont De Nemours And Company | Spinning process |
EP0357017A2 (en) * | 1988-08-30 | 1990-03-07 | E.I. Du Pont De Nemours And Company | Improved coagulating process for filaments |
US5173236A (en) * | 1991-03-08 | 1992-12-22 | E. I. Du Pont De Nemours And Company | Method for spinning para-aramid fibers of high tenacity and high elongation at break |
US5330698A (en) * | 1993-04-19 | 1994-07-19 | E. I. Du Pont De Nemours And Company | Process for making high elongation PPD-T fibers |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008055130A2 (en) * | 2006-10-31 | 2008-05-08 | E. I. Du Pont De Nemours And Company | Process and apparatus for the production of yarn |
WO2008055130A3 (en) * | 2006-10-31 | 2008-09-25 | Du Pont | Process and apparatus for the production of yarn |
EP2489765A1 (en) * | 2006-10-31 | 2012-08-22 | E. I. du Pont de Nemours and Company | Apparatus for the production of yarn |
CN101755080B (en) * | 2006-10-31 | 2012-12-05 | 纳幕尔杜邦公司 | Process and apparatus for the production of yarn |
US8419989B2 (en) | 2006-10-31 | 2013-04-16 | Magellan Systems International Llc | Process and apparatus for the production of yarn |
KR101378290B1 (en) | 2006-10-31 | 2014-03-25 | 마젤란 시스템즈 인터내셔날, 엘엘시 | Process and apparatus for the production of yarn |
WO2010094620A1 (en) | 2009-02-17 | 2010-08-26 | Teijin Aramid B.V. | Method for producing a filament yarn from an aromatic polyamide |
US8871124B2 (en) | 2009-02-17 | 2014-10-28 | Teijin Aramid B.V. | Method for producing a filament yarn from an aromatic polyamide |
Also Published As
Publication number | Publication date |
---|---|
EA001176B1 (en) | 2000-10-30 |
KR20000052793A (en) | 2000-08-25 |
EP0934434B1 (en) | 2003-02-26 |
DE69719351T2 (en) | 2003-10-30 |
EP0934434A1 (en) | 1999-08-11 |
DE69719351D1 (en) | 2003-04-03 |
JP3888645B2 (en) | 2007-03-07 |
EA199900408A1 (en) | 1999-10-28 |
CN1076405C (en) | 2001-12-19 |
KR100431679B1 (en) | 2004-05-17 |
CN1234839A (en) | 1999-11-10 |
JP2002515949A (en) | 2002-05-28 |
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