US3414645A - Process for spinning wholly aromatic polyamide fibers - Google Patents

Process for spinning wholly aromatic polyamide fibers Download PDF

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US3414645A
US3414645A US376363A US37636364A US3414645A US 3414645 A US3414645 A US 3414645A US 376363 A US376363 A US 376363A US 37636364 A US37636364 A US 37636364A US 3414645 A US3414645 A US 3414645A
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fiber
percent
temperature
solution
water
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Jr Herbert S Morgan
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Monsanto Co
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Monsanto Co
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Priority to GB24982/65A priority patent/GB1106190A/en
Priority to DE19651494692 priority patent/DE1494692A1/de
Priority to LU48834D priority patent/LU48834A1/xx
Priority to IL23751A priority patent/IL23751A/xx
Priority to BE665638D priority patent/BE665638A/xx
Priority to NL6507885A priority patent/NL6507885A/xx
Priority to CH863265A priority patent/CH470443A/de
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    • D—TEXTILES; PAPER
    • D02—YARNS; MECHANICAL FINISHING OF YARNS OR ROPES; WARPING OR BEAMING
    • D02G—CRIMPING OR CURLING FIBRES, FILAMENTS, THREADS, OR YARNS; YARNS OR THREADS
    • D02G3/00—Yarns or threads, e.g. fancy yarns; Processes or apparatus for the production thereof, not otherwise provided for
    • D02G3/02—Yarns or threads characterised by the material or by the materials from which they are made
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
    • 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

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  • ABSTRACT OF THE DISCLOSURE The solution spinning of aromatic polyamides is improved by using a dry jet-wet spinning process wherein the polymer solution immediately after extrusion is led through a gaseous medium for a short distance, about A; to 1 /2 inches, before entering the coagulation bath.
  • This invention relates to a process for the preparation of high temperature resistant shaped and attenuated articles such as fibers, films, filaments, yarns and the like. More particularly, it relates to a process for the preparation of high strength thermally resistant fibers, filaments, films, and other shaped articles from Wholly aromatic polyamide compositions.
  • poly (m-phenylene isophthalamide) ⁇ Zigiigil poly-N,N-m-phenylenebis (m-benzamide terephthalamide 3,414,645 Patented Dec. 3, 1968 poly-N,N'-m-phenylenebis(m benzamide)-2,6-naphthylene dicarbonamide poly-N,N'-m-phenylenebis (m-b enzamide) -4,4' -biphenyldicarbonamide poly-4,4- bis (p-aminophenyl -2,2'-bithiazole is ophthalamide n L its all @J poly-2,5 bis(p-aminophenyl)1,3,4oxadiazole isophthalamide l'i t i ii I @-t fiQ poly-3,4'-diaminobenzanilide isophthalamide iii n L l and poly-4,4-diaminobenzanilide terephthalamide
  • Another object of the invention is to provide dense attenuated structures of unusually high crystallinity, orientation and thermal stability.
  • An additional object of the invention is to provide an improved modified Wet extrusion process for preparing wholly aromatic polyamide filaments, fibers, films and other shaped articles.
  • Yet another object is to provide a dry jet-wet spinning process for the production of wholly aromatic polyamides of improved zero strength temperatures, high birefringence thermal stability and tenacity.
  • a further object is to provide a process for spinning wholly aromatic polyamides which permits improved extraction of solvent and inorganic salts from the polymer solution.
  • the remaining sequential steps are orientation, washing, a finish application if desired, drying, and an additional thermal stretching step referred to herein as a hot draw.
  • utilization of this technique leads to much improved extraction of inorganic salts from the polymer solution, improved structural properties of the shaped objects, and excellent thermal stability.
  • the wholly aromatic polyamides of the invention may be prepared conveniently and preferably by combining an aromatic diacid chloride and an aromatic diamine in a lower alkylamide solvent to produce the desired polyamide and the byproduct, hydrogen chloride.
  • the hydrogen chloride must be neutralized or removed to prevent its harmful effects to the resulting articles.
  • Neutralization of the hydrogen chloride may be conveniently accomplished by adding an alkali, or alkaline earth, metal base to form a salt and water.
  • the polymers are further dissolved in the lower dialkylamide containing an amount of salt and water which is proportional to the amount of hydrogen chloride formed in the polymerization.
  • This amount of salt ranges from about 1 to 8 percent based on the solution weight of alkali or alkaline earth metal chloride.
  • These solutions may also be prepared by stirring previously washed salt-free polymer into a solvent consisting of a lower dialkylamide and from 1 to 8 percent of either an alkali or alkaline earth metal chloride or bromide at a temperature of 60 to 90 C. Although it is not absolutely essential it is preferred to add up to a total of 4 percent water to these dopes to improve their stability.
  • lower alkylamides such as dimethylformamide and dimethylacetamide containing up to 10% by weight of dissolved metal salts such as lithium chloride, lithium bromide, calcium chloride, potassium chloride, zinc chloride and similar salts are especially useful. Calcium chloride and lithium chloride are preferred.
  • Other solvents which may be used for spin solution preparation include trifiuoroacetic acid, dimethylsulfoxide, N-methyl-Z-pyrrolidone, and hexamethylphosphonic triamide. These solvents usually have their solvency power enhanced by adding the aforementioned salts to the spin solution. Additional solvents may be obtained by using mixtures of two or more of these solvents. Concentrated sulfuric acid may also be used.
  • the polymer solution may be extruded at temperatures of 30 to 120 C.
  • the polymer concentration may be increased or decreased within the preferred limits of 10 to 30 percent to provide a suitable solution viscosity.
  • the viscosity of a given concentration may be adjusted by heating or cooling the solution briefly at a point just prior to the extrusion orifices.
  • the spinnerette is preferably positioned with the face substantially parallel to the surface of the coagulation bath so that the extruded solution passes through a short gaseous space before entering the coagulation bath. It is normally a simple matter to adjust the jet to obtain the optimum distance and this distance will depend on the concentration, viscosity, temperature and other spinning solution conditions. Usually this distance will be from A; to 1 /2 inches, preferably about /2 an inch. However, this distance can be increased by taking precaution that adjacent polymer streams do not come in contact with and cohere to each other before entering the coagulation bath.
  • the temperature resistant wholly aromatic polyamides are conveniently spun from about 10 percent to about 30 percent solutions, preferably 12 to 20 percent solutions by weight, of the wholly aromatic polyamides having inherent viscosities of from about 0.6 to 3.0 or higher, and preferably above about 1.2 as measured at 30 C. as a 0.5% solution in dimethylacetamide containing 5% dissolved lithium chloride.
  • the spinning variables should be correlated so that less than one percent, if any, of the solvent based on the weight of the solution is evaporated into the gaseous medium from the extruded stream.
  • the inherent viscosity should range from about 2.0 to 2.4 or higher. Fiber of higher deniers (9 to 15 d.p.f.) may be conveniently formed from the higher molecular weight polymers. At this level of inherent viscosity the polyalkylene glycol coagulation bath is less efiicient resulting in sticking or fusion of filaments. In such cases an aqueous coagulation bath is preferred.
  • the polyalkylene glycol coagulation bath comprises a mixture of from about to water by weight, and from about 30% to 5% of a polyalkylene glycol.
  • polyalkylene glycol as used in the specification and claims refers to polyethers which may be derived from alkylene oxides or glycols and which may be rep esented by the formula HO(RO),,H in which R stands for an alkylene radical such as methylene, ethylene, propylene, and butylene, and n is an integer of at least 4.
  • the polyglycol may contain inert substituents, for example methoxypolyethylene glycol, and may consist of a mixture of polyalkylene glycols. These glycols have molecular weights of from about 200 to 6000, preferably 600 to 2000. Although wide variations in the spin bath temperatures are permitted, it is preferred that the temperature range from about 5 C. to 60 C., preferably from about C. to C.
  • the coagulation bath for polymers having an inherent viscosity of about 2.0 or higher, which is comprised of a mixture of from 0 to percent, preferably 0 to 10 percent of a dialkylamide in water, is highly effective even after a substantial concentration of metal salt builds up in the coagulation bath itself. It is convenient to provide fresh solvent-water mixture to the coagulation bath continuously while withdrawing continuously a portion of the bath containing solvent and metal salt concentrations thus maintaining an essentially constant environment for coagulation. In order to assure constant coagulating conditions in the bath, the solution is circulated and may be maintained at a preferred concentration by the continuous addition of fresh solution or water while continuously removing an equal proportion of the spent solution.
  • the temperature of the coagulation bath may be from 10 C. to C., preferably 15 C. to 25 C., during coagulation.
  • the wholly aromatic polyamide fibers of this invention have properties which permit their conversion by further processing into useful fibers with unique and novel properties.
  • the coagulation step in the process is followed by an orientation step in which the fiber may be relaxed or stretched from less than one to about four times its length in a conventional hot water or boiling water stretch bath at a temperature of from about 50 C. to 100 C.
  • the orientation of the fiber may include washing the fiber on the take up roller or first godet which Withdraws the fiber from the coagulation bath and advances it toward the hot water stretch bath. This extra aqueous wash is desirable when very high salt concentrations are present such as occur when highly insoluble polymers are being spun from salt containing solvents.
  • the fiber After orientation the fiber is washed with water at a temperature of 15 C. to 65 C., with higher wash temperatures used when shorter washing time is desired and lower wash temperatures when longer washing periods are desired to remove substantially all traces of solvent and salts.
  • the washed, oriented fiber is next passed through an optional aqueous finish bath where conventional lubricants and/or antistatic agents may be applied.
  • an antistatic type to control the static electricity has been found the most valuable. Without an antistatic agent the dried fibers tend to repel one another and may be ditficult to handle in further processing steps.
  • the fiber is dried in the conventional manner on steamheated cylindrical rolls or by any other suitable drying means.
  • the temperature is preferably maintained at from about 120 C. to 160 C.
  • the fiber may be preheated by passing over a heated draw pin or through a heated enclosure such as an oven, furnace, or hot block slot where the fiber is continuously conditioned at about 300 C. to 500 C., preferably 400 C. to 450 C.
  • the fiber is then drawn from one to four times over a heated surface such as a hot shoe type heater at about 300 C. to 450 C.
  • the fiber after drying may be advanced directly to the heated surface when a continuous spinning system is employed.
  • the fiber may, after hot drawing, be passed over a heated surface several times by the use of small roller guides.
  • the drawn (or drawn and heat stabilized) fiber is finally collected on bobbins using a conventional take-up device.
  • Suitable extraction agents which may be used include monohydroxy and polyhydroxy compounds such as methanol, ethanol, propanol, isopropanol, butanol, pentanol, ethylene glycol, propylene glycol, butylene glycol, glycerol, and mixtures of these compounds with up to 50 percent water.
  • Other extraction agents are polyalkylene glycols of 600 to 2000 molecular weight such as polyethylene glycol of 1000 molecular weight.
  • Amides such as dimethylacetamide, dimethylformamide, and urea mixed with 40 to 70% water may also be used.
  • Other agents include acetonitrile (CH CN). These extraction agents are preferred when the polymer inherent viscosity is below about 1.90 and the desired denier is 6 d.p.f. or higher.
  • FIGURE 1 is a side elevational view partly in section showing schematically an apparatus arrangement of the type which can be used in carrying out the process of the present invention.
  • FIGURE 2 shows a drawing of a photomicrograph cross-sectional view of fibers obtained by the dry jet- Wet spinning technique.
  • FIGURE 3 shows a drawing of a photomicrograph cross-sectional view of fibers obtained by a conventional wet spinning technique.
  • 1 is the polymer solution hold tank.
  • Polymer solution is pumped via pump 2 through filter 3 composed of two layers of nylon, one layer of flannel, jet holder 4, and out of the spinnerette 5.
  • the spinnerette is adjusted to the desired temperature by circulating a Warm fluid through the jet holder.
  • the jet is normally of 10 to holes, each hole being 3-20 mils in diameter.
  • the jet face is preferably positioned parallel to the surface of the coagulation bath 7.
  • the polymer solution is extruded downward and enters the coagulation bath passing under spacer bar 6 positioned below the surface of the bath directly beneath the jet.
  • the partially coagulated fiber continues an additional distance in the bath, emerges and passes over the first godet rolls 8.
  • First godet rolls 8 may have a dip bath containing a solvent extraction agent through which the freshly coagulated yarn is further extracted before being drawn.
  • the fiber is then fed through a hot or boiling water stretch bath 9 and over the draw wash rolls 10 where the fiber is washed with hot water.
  • the fiber then passes through a finish bath 11 and on to drying rolls 12. After thorough drying is accomplished the fiber is fed directly over the hot pin 13 and is drawn by rolls 15 over shoe 14.
  • the pin is normally set at a temperature about 50 C. above the shoe temperature to insure adequate preheating of the yarn. If an oven is used as the preheater, the temperature within the oven should be 50100 C. greater than the shoe temperature. Alternately the yarns may be preheated only with the drier rolls.
  • the drawn yarn is collected on bobbin 16 using a conventional take-up device.
  • FIGURES 2 and 3 the contrast of fiber cross-sections clearly shows the advantage of the process of the invention.
  • the dry jet-wet spun fibers of FIGURE 2 have excellent clear internal structure, whereas those of FIGURE 3, of wet spun fibers, contain numerous voids.
  • Percent water 90-100 99 Percent solvent 10-0 1 Spin bath temp., C" 10-30 25 First godet speed, f.p m 12-150 34 Orientation stretch 88-2. 80X 2.10X Wash water temp., 15- 60 Finish Finish concentration, percent by weight 0. -10 0 2.0 Washer to drier stretch 0.95-1.00 1. 0X Drier roll temp., C... 120-160 150 Drier speed, Lp 13-420 71. 2 Preheater oven temp 300-500 450 Shoe temp., C 300-450 375 Hot draw ratio 1. 0-4. 0X 1. 70X Final Speed, f.p.m 16. 3-714 121 1 An article and/or lubricant.
  • the maximum operable hot draw is dependent upon the orientation stretch ratio.
  • the total draw from spinnerette or jet face to final takeup godet will vary from about 2.0x to 12.0 T
  • Example II The polymer-solvent system employed in Example I was heated to C. and used with a 10 hole, 5 mil spinnerette for wet spinning in to a 55 C. aqueous spin bath. After an immersion of 23 inches in the spin bath the fiber was advanced by drawing rolls which stretched the fiber 1.13 times in the spin bath. From the spin bath the fiber was subjected to an orientation stretch of 2.25 in a boiling water bath. The fiber was next advanced to a set of washer rolls and washed with 55 C. water. After washing a 5 percent antistatic finish dispersion was applied from an aqueous finish bath. After application of the finish the fiber was advanced over heated drier rolls, at a temperature of 135 C. where it was drawn an additional 1.16 times and simultaneously dried.
  • EXAMPLE III The polymer-solvent system employed in Example I was spun as shown in FIGURE 1 under the conditions prescribed in Table 1. The properties of the fiber are shown in Table 2.
  • Example IV The conditions employed in Example III were followed in Example IV with the exception that the polymer employed was poly N,N-m-phenylenebis (m-benzamide) 4,4-biphenyldicarbonamide. The preparation of this polymer is described in Ser. No. 222,930 previously mentioned. The properties of the fiber obtained are shown in Table 2.
  • Example V The conditions employed in Example III were followed in this example with the polymer used being poly N,N'- m phenylenebis(m benzamide) terephthala-mide. The preparation of this polymer is described in Ser. No. 222,932. The properties of the fiber obtained are shown in Table 2.
  • Example VI The conditions employed in Example I were followed in Example VI with the following exceptions.
  • the polymer poly(m-phenylene isophthalamide), was prepared in accordance with U.S. 3,006,899 to give a dimethylacetamide solution containing 20 percent polymer and 3 percent lithium chloride with a viscosity of 5,760 poises at 25 C.
  • the solution was heated to C.
  • the spinning speed was 132 f.p.m., jet stretch 4.58 and the fibers were drawn 5.62 times over a hot shoe adjusted to 325 C.
  • Table 2 The properties of this fiber are shown in Table 2.
  • EXAMPLE VII A solution containing 1 8 percent of poly-3,4'-diaminobenzanilide isophthalamide in dimethylacetamide containing 3 percent dissolved lithium chloride was prepared.
  • jet stretch for the wet spinning technique was 1.38
  • a jet stretch of 7.3x was obtainable.
  • the ability to spin with this increased latitude in jet stretch makes the dry jet-wet spinning process more flexible and convenient to employ than the wet spinning system. It also facilitates a higher degree of orientation and crystallinity in the finish fiber, and enables a much wider range of fiber denier tobe spun conveniently.
  • Refractive index (and birefringence) data are not reproducible due to the presence of large voids and a granular structure.
  • birefringence data were obtained by measuring the parallel and perpendicular refractive indices in plane cross-polarized light using the Becke line technique. Birefringence is calculated from the refractive indices.
  • Zero strength temperature test was determined by heating a yarn at 0.1 gram per denier load in a nitrogen atmosphere. The temperature was raised at a rate of 5 C. per minute until the sample broke. The temperature at which the sample broke was taken as the zero strength temperature.
  • the dry jet-wet spun fiber was void free and is much preferred over the highly voided structures shown in FIGURE 3.
  • the distance from the face of the spinnerette to the point along the thread line where the fiber appeared to be coagulated or delustered was approximately 7 inches. This same point was observed only 0.5 inch from the spinnerette face with the fiber when wet spun.
  • Example XI The spinning conditions employed in Example X were repeated with the exception that the maximum jet stretch was determined for both the dry jet-wet spinning and wet spinning techniques.
  • the maximum jet stretch is defined as the maxi-mum stretch which may be applied between the spinerette face and the first advancing rolls without causing the breaking of filaments.
  • the maximum EXAMPLE XIII TABLE 3 Dry heat Example shrinkage at (percent) 1 The dry heat shrinkage was obtained by measuring the decrease in a 20 cm. length of yarn after five minute contact with a heated metal surface. The percent shrinkage was calculated from the change in length.
  • EXAMPLE XIV A solution was prepared containing 20 percent of poly N,N-m-phenylenebis(m-benzamide) terephthalamide (with an inherent viscosity of 1.92), 3 percent lithium chloride, 1 percent water and 76 percent dimethylacetamide. Additional lithium chloride was added to increase the concentration to 6 percent lithium chloride.
  • the solution was heated to 80 C. and spun as in Example III with the following exceptions.
  • the coagulation bath was comprised of 80 percent water and 20 percent polyethylene glycol of 1000 average molecular weight at a temperature of 20 C.
  • the fiber was given a preliminary wash on the first godet after emerging from the coagulation bath and prior to the orientation stretch. Spinning stability was good and a 5.1 d.p.f. fiber was obtained with a tenacity of 5.0 g.p.d., 29.1 percent elongation, modulus of 82 g./d. and a zero strength temperature of 511 C.
  • EXAMPLE XVI A solution of poly N,N-m-phenylenebis(m-benzamide) 2,6-naphthylene dicarbonamide was prepared and spun as in Example XIV. A 2.2 d.p.f. fiber with a tenacity of 7.0 g.p.d., elongation of 16.6 percent, modulus of 118 g.p.d. and a zero strength temperature of 506 C. was obtained.
  • EXAMPLE XVII A solution of percent of 2.38 inherent viscosity poly N,N-m-phenylenebis(m-benzamide) 2,6-naphthalene dicarbonamide in dimethylacetamide containing 5 percent dissolved lithium chloride was spun under the conditions set forth in Table 1. The fiber was given a 3.14 jet stretch, 2.55 X orientation stretch and finally hot drawn 1.27 at 350 C. The tensile properties of the fiber were 11.6 d.p.f., 5.86 g.p.d. tenacity, 14.10 percent elongation and a modulus of 134.0 g.p.d.
  • EXAMPLE XVIII This example shows various dehydrating or solvent extraction agents which are useful in improving the spinning of polymers of the general formula IHN/ ⁇ -E NH Na salt ill LU l l @1
  • Samples of poly-N,N'-m-phenylenebis(m-benzamide) terephthalamide of 1.90 inherent viscosity were spun under the conditions described in Table 1, except that the orientation bath temperature was lowered to about C. with the addition of a dip bath on the first godet using the following solvent extraction agents:
  • Fibers with such properties are particularly useful in shaped articles which find applications in uses requiring exposure to elevated temperatures.
  • fibers, filaments and other shaped articles they are useful in applications such as electrical insulations, industrial filters, conveyor belts tire cord, heat resistant parachutes, protective clothing and the like.
  • a process for the preparation of shaped articles from wholly aromatic polyamide solutions comprising the steps of:
  • a process for the preparation of fibers from wholly aromatic polyamide solutions containing from 10 to 30 percent polyamide by solution weight and having an inherent viscosity of from about 1.2 to 2.0 comprising the steps of:
  • a process for the preparation of poly N,N'-mphenylenebis (m-benzamide) 2,6 naphthylenedicarbonamide fibers comprising the steps of:
  • A- process for the preparation of poly-N,N'-mphenylenebis(m-benzamide)terephthalamide fibers comprising the steps of:
  • cent to 10 percent of the solvent (7) and subjecting the fiber to a hot draw by advancing (3) withdrawing the thus-formed fiber from the cothe fiber through a preheater oven at a temperature agulating bath; of from 200 C. to 450 C. then over a shoe heated (4) passing the fiber through a wash liquid comprising to a temperature of from 300 C. to 450 C. while boiling water while stretching same from 0.88 to stretching the fiber from 1 to 4 times its length.
  • a process for the preparation of poly(m-phenylgaseous evaporative medium comprising air in which eneisophthalamide) fibers comprising the steps of: 3 only a small amount of the solvent is evaporated (1) extruding a solution of 15 to 22 percent by solufrom th tr a as a gas;
  • tion weight of poly(rn-phenyleneisophthalamide) (2) directing the stream through the air for a distance dissolved in a solvent comprising 85 to 98 percent (11- of 1A inch to 1 inch and into a, coagulating bath cornmethylacetamide, 1 to 10 percent lithium chloride prising 90 percent to 99 percent of water and 1 perand 1 to 5 percent water in a downward direction cent to 10 percent of the solvent;
  • agulating bath (7) and subjecting the fiber to a hot draw by advanc- P s g th r through a wash liquid comprising the fiber through a preheater oven at a temperaing boiling water while stretching same from 0.88 t e of fro 300 C t 450 c h over a h to 2.80 times its length to orient the polymer moleheated to a temperature of from 300 C. to 450 C.
  • a wholly aromatic polyamide fiber produced acfrom 40 C. to 80 C.;
  • a process for the preparation of p0ly-N,N-rnphenylenebis (m-benzamide) terephthalamide, fibers of at least 6 d.p.f. comprising the steps of:
  • a process for the preparation of poly-3,4'-diamino- 6O benzanilide isophthalamide fibers comprising the steps coslty above about dls solved m a f of: comprising to percent dimethylacetamide, 1

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US376363A 1964-06-19 1964-06-19 Process for spinning wholly aromatic polyamide fibers Expired - Lifetime US3414645A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
US376363A US3414645A (en) 1964-06-19 1964-06-19 Process for spinning wholly aromatic polyamide fibers
GB24982/65A GB1106190A (en) 1964-06-19 1965-06-14 Novel process for spinning heat resistant polyamide fibers
LU48834D LU48834A1 (xx) 1964-06-19 1965-06-15
DE19651494692 DE1494692A1 (de) 1964-06-19 1965-06-15 Verfahren zur Herstellung von geformten Gegenstaenden aus Loesungen von vollstaendig aromatischen Polyamiden
IL23751A IL23751A (en) 1964-06-19 1965-06-17 Process for spinning heat resistant fibers
BE665638D BE665638A (xx) 1964-06-19 1965-06-18
NL6507885A NL6507885A (xx) 1964-06-19 1965-06-18
CH863265A CH470443A (de) 1964-06-19 1965-06-21 Verfahren zur Herstellung von geformten Gebilden, insbesondere Fasern aus Polyamiden

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US376363A US3414645A (en) 1964-06-19 1964-06-19 Process for spinning wholly aromatic polyamide fibers

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CH (1) CH470443A (xx)
DE (1) DE1494692A1 (xx)
GB (1) GB1106190A (xx)
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Cited By (163)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1929713A1 (de) * 1968-06-12 1970-02-12 Du Pont Anisotrope Spinnloesungen von aromatischen Polyamiden
US3523151A (en) * 1967-11-07 1970-08-04 Celanese Corp Ultra-stable polymers of bbb type,articles such as fibers made therefrom,and high temperature process for forming such polymers and articles
US3541199A (en) * 1968-10-23 1970-11-17 Celanese Corp Process for improving the tensile properties of polybenzimidazole fiber or yarn
US3619453A (en) * 1969-11-03 1971-11-09 Celanese Corp Wet spinning process for the production of polybenzimidazole filaments
US3671542A (en) * 1966-06-13 1972-06-20 Du Pont Optically anisotropic aromatic polyamide dopes
DE2219703A1 (de) 1971-04-28 1972-11-09 E.I. Du Pont De Nemours And Co., Wilmington, Del. (V.St.A.) Polyamidfasern und -folien und Verfahren zur Herstellung derselben
DE2219646A1 (de) * 1971-04-28 1972-11-09 E.I. du Pont de Nemours and Co., Wilmington, Del. (V.StA.) Polyamidfaser und Verfahren zur Herstellung derselben
US3725523A (en) * 1971-08-03 1973-04-03 Du Pont Process for extracting and drawing a tow
US3760054A (en) * 1969-09-08 1973-09-18 Du Pont Process for preparing porous aromatic polyamide fibers
US3869429A (en) * 1971-08-17 1975-03-04 Du Pont High strength polyamide fibers and films
US3869430A (en) * 1971-08-17 1975-03-04 Du Pont High modulus, high tenacity poly(p-phenylene terephthalamide) fiber
US3886251A (en) * 1967-04-11 1975-05-27 Furukawa Electric Co Ltd Method for forming polyoxadiazole series resin solution into shaped articles
US3888965A (en) * 1970-04-20 1975-06-10 Du Pont Method of increasing the initial modulus and reducing the orientation angle of undrawn poly (para-benzamide) fibers
US3947538A (en) * 1970-10-22 1976-03-30 Imperial Chemical Industries, Ltd. Process for uniformily drawing a tow of filaments
US3963664A (en) * 1972-05-26 1976-06-15 Teijin Limited Method of preparing aromatic polyamide solutions
US3985934A (en) * 1974-07-26 1976-10-12 The Upjohn Company Polyimide fiber having a serrated surface and a process of producing same
US4029835A (en) * 1975-01-16 1977-06-14 Mitsubishi Rayon Co., Ltd. Heat resistant sheet
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GB1106190A (en) 1968-03-13
DE1494692A1 (de) 1969-10-30
BE665638A (xx) 1965-12-20
CH470443A (de) 1969-03-31
LU48834A1 (xx) 1965-08-26
IL23751A (en) 1969-04-30

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