US3717696A - Process for the preparation of polyamide-imide filaments - Google Patents

Process for the preparation of polyamide-imide filaments Download PDF

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US3717696A
US3717696A US00114082A US71769671A US3717696A US 3717696 A US3717696 A US 3717696A US 00114082 A US00114082 A US 00114082A US 71769671 A US71769671 A US 71769671A US 3717696 A US3717696 A US 3717696A
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temperature
filaments
imide
solution
process according
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Vincent Rochina
Pierre Allard
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Rhodiaceta SA
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Rhodiaceta SA
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61H—PHYSICAL THERAPY APPARATUS, e.g. DEVICES FOR LOCATING OR STIMULATING REFLEX POINTS IN THE BODY; ARTIFICIAL RESPIRATION; MASSAGE; BATHING DEVICES FOR SPECIAL THERAPEUTIC OR HYGIENIC PURPOSES OR SPECIFIC PARTS OF THE BODY
    • A61H33/00—Bathing devices for special therapeutic or hygienic purposes
    • A61H33/06—Artificial hot-air or cold-air baths; Steam or gas baths or douches, e.g. sauna or Finnish baths
    • A61H33/10—Devices on tubs for steam baths
    • 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
    • D01F6/74—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polycondensates of cyclic compounds, e.g. polyimides, polybenzimidazoles

Definitions

  • ABSTRACT Primary Examiner-Donald J. Arnold Assistant Examiner-James B. Lowe Attorney-Cushman, Darby & Cushman [5 7] ABSTRACT ,heated at a temperature higher than 160 C. up to about 240 C. at a constant length for 2 to 6 hours, and subsequently drawn at a drawing ratio of at least 3:1 at a temperature generally in the range of about 220 C. up to about 420 C.
  • the present invention relates to a process for the preparation of fibers from a polymer containing in the chain both amide and imide linkages derived from a tricarbonyl compound such as a tri-acid or acid-anhydride.
  • these filaments and fibers are made by a process which comprises extruding through a spinneret maintained at 60 to 180C in an evaporatory atmosphere, maintained at a temperature about or greater than the boiling point of the solvent, a solution in an organic polar solvent having an inherent viscosity greater than 0.4 and containing amide-imide linkages of the formula /Arl-oco and optionally also amide linkages of the formula represents a divalent aromatic, aliphatic, cycloaliphatic, or arylaliphatic radical, Ar represents a divalent aromatic radical (optically with a minor proportion of divalent aliphatic or cyclcaliphatic radicals), and Ar, represents a trivalent aromatic radical containing at least six carbon atoms; heating the filaments obtained to a temperature higher than 160 C; and drawing the filaments at a temperature higher than the temperature corresponding to the maximum in absolute value of the first derivative of the function expressing the variation of the maximum drawing tension as a function of the temperature, and preferably near
  • polyamide-imides can be obtained by reaction in substantially stoichiometric proportions in a polar organic solvent of at least one aromatic diisocyanate and an acid reactant containing at least an aromatic anhydride-acid and optionally also at least one di-acid which may be aromatic, aliphatic, cycloaliphatic, or acylaliphatic.
  • Suitable diisocyanates which can be used to obtain these polymers include, more particularly, monocyclic diisocyanates such as tolylene diisocyanate and the bicyclic preferably symmetrical, diisocyanates, such as diphenylmethane diisocyanate, diphenylpropane diisocyanate, and diphenylether diisocyanate.
  • An aliphatic or cycloaliphatic diisocyanate may optionally be added to the aromatic diisocyanate in minor proportions so as to improve certain properties of the polymer such as solubility, or the flexibility or elasticity of articles made from it.
  • the process of the present invention it is possible to use the polyamide-imide solution in the form in which it is obtained, or to separate the polymer so as to remove by-products formed in the course of the polycondensation, and then to re-dissolve the polymer before it is extruded.
  • Suitable polar organic solvents which can be used in the present invention include dimethylformamide, dimethylacetamide, hexamethylphosphotriamide, tetramethylenesulphone, and preferably N-methylpyrrolidone.
  • the polyamide-imides used in the present invention must have an inherent viscosity greater than 0.4, but preferably not greater than 1.6. This inherent viscosity is measured at 25 C. on an 0.5 percent weight for volume solution in the solvent used in the preparation of the polyamide-imide Polymers having an inherent viscosity from 0.8 to 1.4 are preferably used.
  • the polyamide-imide solutions used in the new process preferably have a viscosity of 300 to 6,000 poises at 25 C (measured with a Drage viscometer using speed II and mobile 47.2)
  • the solution has a viscosity from 1,500 to 3,000 poises to ensure stable spinning together with good filtration and easy transport of the solution.
  • the solution spun should contain a polymer concentration of 15 to 35 percent by weight and preferably 19 to 30 percent by weight, and it can also contain various adjuvants such as pigments and dulling agents.
  • the circuit through which the solution is fed to the head of the spinneret can be heated or not depending on the viscosity of the polymer solution.
  • the temperature of the feed circuit is kept at about ambient temperature.
  • the temperature of the solution on extrusion must be between and 180 C., and is preferably between 90 and 1 C.
  • the speed of spinning can vary within wide limits, and may be generally fixed between 100 and 400 meters per minute, preferably 150 to 200 meters per minute. This speed is chosen as a function of the titre of each filament and the number of strands spun.
  • the filaments contain from 5 to percent of solvent on leaving the evaporation chamber. If desired, the filaments maybe subjected, either in the spinning cell or immediately after leaving it, to a predrawing operation to a small degree before receiving the thermal treatment in accordance with the new process.
  • the filaments receive, a thermal treatment before being drawn.
  • This thermal treatment at a temperature higher than 160 C. can be carried out in an inert gas such as nitrogen or carbon dioxide or in a mixture of air and inert gas, optionally under reduced pressure. It can be effected using any appropriate apparatus.
  • the filament can be collected on metallic supports whichare then introduced into a zone heated to more than 160 C. This zone is preferably sealed and connected to an evacuation device so that the pressure in the zone can be'reduced.
  • the zone can also be provided with tuyeres so that air, nitrogen, carbon dioxide or another inert gas can be swept through the zone.
  • the thermal treatment can also be effected on heated rolls rotated at a speed such that the treatment can be carried out continuously. If desired, these rolls can be enclosed in a zone in which hot air or inert gas is circulated and optionally the pressure is reduced.
  • the thermal treatment is preferably carried out while the filaments are maintained at constant length.
  • This treatment causes in the polymer constituting the filaments physical and/or chemical modifications which cause the filaments to possess, after drawing, excellent mechanical properties.
  • the :solvent content of the filaments is reduced to the levels of the order of 3 percent or less. This reduction in solvent content is not, however, the
  • the duration of the heat treatment varies as a function of the temperature and the titre of the filaments. At l60 C., it lasts for at least 2 hours.
  • the filaments are drawn at a temperature higher than the temperature corresponding to the maximum value in absolute terms of the first derivative of the function expressing the variation of maximum drawing tension as a function of temperature.
  • the temperature of drawing should be close to or even greater than the temperature corresponding to the maximum algebraic value of the first derivative of said function expressing the maximum drawing tension as a function of temperature.
  • the polyamide-imide filaments and fibers obtained according to the invention have a good tensile strength of at least 30 g/tex, a low moisture absorption, a good dimensional stability, and a very good resistance to acids. They can be used for all usages where these qualities are particularly important, such as in medical and hospital use where good resistance to successive sterilizations is required, and for work garments for foundry workers, glass workers and chemists.
  • the following Examples illustrate the invention. In the Examples the percentages are by weight except where otherwise indicated.
  • the Drage viscosity is measured with a Drage viscometer using speed 11 and mobile 47.2.
  • the inherent viscosity is measured at 25 C. on a 0.5 percent weight for volume solution in N- methylpyrrolidone.
  • EXAMPLE 1 A 26.5 percent solution in N-methylpyrrolidone of a copolyamide-imide is obtained by reaction of diphenylmethanediisocyanate (50 molar parts), trimellitic anhydride (40 molar parts), and terephthalic acid (10 molar parts).
  • the Drage viscosity at 25 C. of this solution is 2,380 poises and the inherent viscosity of the polymer is 0.93.
  • the filaments leave the cell at a speed of meters per minute and are then taken up on a roll at a speed of meters per minute and finally wound up on a metallic support at a speed of meters perminute.
  • the filaments on the support are then introduced into a zone maintained at 240 C. containing nitrogen under reduced pressure, where they remain for 6 hours.
  • the pressure in the zone is periodically varied in the following manner: l-2 mm Hg for 45 minutes; 50 mm Hg for 15 minutes; and this alternation of pressures is maintained for the duration of the treatment.
  • the maximum drawing tension of the filaments during their passage through an oven heated successively to different temperatures is measured. For each temperature the tension of the filaments is measured just before rupture using a Rothschild tensiometer. The curve expressing the variation of this maximum drawing tension as a function of temperature is then drawn. It is shown in FIG. 1 of the accompanying drawings. The derivative of this curve at each point is then calcu lated and FIG. 2 shows that this derivative has a maximum absolute value at 220 C 4.75 and a maximum algebraic value at about 300 C. (+0.75).
  • the drawing temperature being higher than the temperature corresponding to the maximum absolute value of the curve expressing the rate of change of maximum drawing tension with temperature against the temperature, the rate of change being determined by measuring the slope of the curve of maximum drawing tension versus temperature. See FIGS. 1 and 2.
  • the filaments after the heat treatment, are introduced at a speed of 10 meters per minute into a tube, 1.5 meters long and 8 mm in diameter, heated electrically, in which it is drawn 4 times in air at 380 C.
  • the thread obtained has the following characteristics:
  • EXAMPLE 2 A 23.1 percent solution in N-methylpyrrolidone is prepared of a copolyamideimide obtained by reaction of diphenylmethane diisocyanate (50 molar parts), trimellitic anhydride (40 molar parts), and terephthalic acid (20 molar parts).
  • the Drage viscosity at 25 C. of this solution measured as described above is 1,840 poises.
  • the inherent viscosity of the polymer is 1.01.
  • This solution is extruded at a temperature of 1 10 C. through a spinneret having 60 orifices each 0.10 millimeters in diameter downwardly in a vertical spinning cell 7 meters long and 200 mm in diameter, the walls of which are maintained. at 245 C.
  • a current of hot air enters the upper part of the cell, and a mixture of air and solvent is withdrawn at the lower part of the cell.
  • 650 dtex thread is obtained at a speed of 150 meters per minute. Eight identical threads are combined and wound up at a rate of 20 Z turns per meter on a metallic support. The filaments on their support are treated for three hours at 240 C. under a pressure of 12 mm Hg. The thread then possesses the following characteristics:
  • the filaments are then drawn 3.3 times in air at 340 C. that is to say at a temperature higher than the temperature corresponding to the maximum algebraic value of the curve in FIG. 2, by passage through a tube 1 meter long and 8 mm in diameter, heated electrically, which they leave at a speed of 24 meters per minute.
  • the thread then possesses the following characteristics:
  • Example 1 They have the same qualities of moisture absorption, heat stability, dimensional stability and resistance to acids as the thread obtained in Example 1.
  • EXAMPLE 3 A 23.9 percent solution in N-methylpyrrolidone is prepared of a copolyamide-imide obtained by reaction of diphenylether diisocyanate (50 molar parts), trimellitic anhydride (20 molar parts), terephthalic acid (10 molar parts), and isophthalic acid (20 molar parts).
  • the Drage viscosity of this solution is 2,500 poises and the inherent viscosity of the polymer is 1.0.
  • This solution is extruded at a temperature of C. through a spinneret having 12 orifices each 0.1 mm in diameter into the same spinning cell and under the same conditions of temperature and circulation of air as in Example 1.
  • the filaments leave the spinning cell at a speed of 194 meters per minute and are taken up on a roll turning at 199 meters per minute and are finally wound up on a metallic support at a speed of 200 meters per minute.
  • Five identical threads are assembled and the wound assembly on the metallic support is introduced into a zone at 240 C. where it is treated as described in Example 1 for 6 hours.
  • the thread is drawn 3.8 times after the heat treatment in air at 320 C. in the same tube and at the same speed as in Example 1.
  • the thread obtained has the following characteristics:
  • EXAMPLE 4 A 19.3 percent solution in N-methylpyrrolidone is prepared of a copolyamide-imide obtained by reaction of diphenylether diisocyanate (50 molar parts) trimellitic anhydride (35 molar parts), terephthalic acid (7.5 molar parts), and isophthalic acid (7.5 molar parts).
  • the Drage viscosity of this solution is 2,080 poises, and the inherent viscosity of the polymer is '1 .32.
  • the solution is extruded at a temperature of 120 C. through a spinneret having 60 orifices each 0.15 mm in diameter, downwardly in the same spinning cell as in Example 1.
  • the thread produced leaves the cell at a speed of 148 meters per minute and then passes over a roll where it is taken up at a speed of 154 meters per minute. It is wound up on a metallic support at a speed of 156 meters per minute.
  • the thread on its support is then introduced'into a zone at 240 C. containing nitrogen under reduced pressure where it remains for six hours. During this treatment the pressure in the zone is periodically varied in the following manner: 1-2 mm Hg for 45 minutes; 50 mm Hg. for 15 minutes; and so on throughout the duration of the treatment.
  • the thread is then passed at a speed of 10 meters per minute through a tube 1.5 meters long and 8 mm in diameter, heated electrically, where it is drawn 4.86 times in air at 380 C. that is to say, at a temperature above the temperature corresponding to the maximum algebraic value of the curve of FIG. 4.
  • the thread obtained possesses the following characteristics:
  • EXAMPLE 6 A 21.8 percent solution in N-methylpyrrolidone is prepared of a copolyamide-imide obtained by reaction of diphenylmethane diisocyanate (50 molar parts), trimellitic anhydride (40 molar parts), and terephthalic acid (10 molar parts).
  • the Drage viscosity at 25 C. of this solution is 2,410 poises.
  • the inherent viscosity of the polymer is 1.19. This solution is extruded at a temperature of C.
  • a 60 filaments 600 dtex thread is obtained at a speed of meters per minute, having a dry tensile strength of 13 g/tex and a dry elongation at break of 90 percent. This thread is continuously treated for 50 seconds by passage over a group of two rollers turning at a speed of 40 meters per minute and having a surface temperature of 240 C.
  • the thread is fed at a speed of 10 meters per minute to a tube 1.5 meters long and 8 mm in diameter, heated electrically, in whiclr it is drawn 4.3 times in air at 400 C. It then has the following characteristics:
  • the thread obtained has the same qualities of water absorption, heat stability, dimensional stability and resistance to acids as the filament obtained in Example 1.
  • EXAMPLE 7 A 20.5 percent solution in N-methylpyrrolidone is prepared of a copolyamide-imide having an inherent viscosity of 1.28 obtained from the starting materials of Example 5. The Drage viscosity at 25 C. of this solution is 1,890 poises. This solution is extruded at a temperature of 150 C. through a spinneret having 90 orifices each 0.10 mm in diameter into a spinning cell 7 meters high, halving walls heated to 245 C. and traversed by a current of hot air entering in the upper part and leaving with solvent in the lower part. The filaments leave the cell at a speed of 150 meters per minute.
  • the thread obtained has the following characteristics:
  • the filament has the same qualities of moisture absorption, heat stability, dimensional stability and resistance to acids as the thread obtained'in Example 1.
  • filaments are collected at the rate of 150 m/minute and have a titre of 230 dtex, a tensile strength of 10 g/tex and an elongation at break of 90 percent.
  • These filaments are treated under tension for 3 hours at 240 C. under a pressure of 5 mm of mercury and then stretched in the ratio of 5.2 at 330 C.
  • the thread has a good resistance to acids.
  • EXAMPLE 9 A 21.5 percent solution of polymer in N-methylpyrrolidone is prepared, from a polyamide-imide as described in Example 8. The solution has a viscosity of 1,810 poises and the polymer has an intrinsic viscosity of 1.10. This solution is extruded through a spinneret having 12 0.25 mm diameter holes and kept at C. After passing through an evaporating atmosphere identical to that described in Example 8 the extruded filaments have a titre of 210 dtex/12 filaments. 5 threads are combined into a thread of 1,050 dtex which is treated for 3 hours at 240 C. under a pressure of 5 mm of mercury.
  • the thread is stretched in a 1 meter tube at 340 C, in a ratio of 4.9.
  • a thread having a titre of 215 dtex a tensile strength of 51 g/tex and 13 percent elongation at break is obtained. lts moisture absorption, heat stability and dimensional stability are identical with those of the filaments obtained in Example 8.
  • the thread displays the following properties:
  • Titre Tensile strength Elongation at break 106% The maximum drawing tension of the thread during its passage through an oven heated successively to different temperatures is measured. For each temperature the tension of the thread is measured just before break using a Rothschild tensiometer. The curve expressing the variation of this maximum drawing tension as a function of temperature is shown in FIG. 5. From this curve the derivative is calculated at each point and the derivative curve is shown in FIG. 6. It shows that the maximum absolute value of the derivative is at 220 C. (8.88) and the maximum algebraic value is about 300 C. (0.25).
  • the thread is stretched in a ratio of 4.5 in a 1 meter tube heated to 370 C.
  • the properties of the thread are then as follows:
  • EXAMPLE 1 1 then stretched on a plate: the maximum stretching ratio which can be achieved in practice at 330 C. is 3.6.
  • the 160 dtex thread obtained has a tensile strength of 35 gltex and an elongation at break of 12 percent. It presents the same qualities of moisture absorption, heat stability, dimensional stability and resistance to acids as the filament obtained in Example -10.
  • EXAMPLE 12 A 23 percent solution of polyamide-imide of intrinsic viscosity 0.98, prepared from diisocyanatodiphem ylether andtrimellitic. anhydride, has a viscosity of 2,350 poises. g
  • the thread collected at 150 m/minute, hasa gauge of 580 d/tex, atensile strength of 10 g/tex, an elongation at break of 70 percent and a solvent content of 16 percent.
  • the thread is stretched to a ratio of 3 at 365 C. in a 1 meter tube and has the following properties:
  • the thread only begins to decompose at about 475 C.
  • EXAMPLE 13 A 26 percent solution of a polyamide-imide of intrinsic viscosity 1.05 is prepared by reaction of trimellitic anhydride with diisocyanatodiphenyl-methane in N- methylpyrrolidone.
  • the threads collected are treated for 3 hours at 200 C. in a stream of nitrogen and then stretched to a ratio of 3.6 at 330 C; they then have the following properties:
  • Process for producing heat stable filaments and fibers which comprises extruding through a spinneret maintained at a temperature between 60 and 180 C in an evaporatory atmosphere maintained at a temperature near or above the boiling point of the solvent, a solution inan inert organic polar solvent selected from dimethyl-formamide, dimethylacetamide, hexamethylphosphotriamide, tetramethylene-sulphone and N-methylpyrrolidone of; a polymer having an inherent viscosity from 0.4 to 1.6 and consisting essentially of amide-imide linkages of the formula or of said amide-imide linkages and of amide linkages of the formula NH AR NH CO R CO in which R represent a divalent benzene radical, Ar represents a radical, in which I is an integer from 1 to 3, and Ar represents the radical heating the filaments obtained to improve the physical and mechanical properties of said polymer at a temperature higher than 160 C.
  • Process according to claim 1 which comprises extruding through a spinneret maintained at a temperature between 60 and 180 C. in an evaporatory atmosphere maintained at a temperature near or above the boiling point of the solvent, a solution, in an inert organic polar solvent selected from dimethylformamide, dimethylacetamide, hexamethylphosphotriamide, tetramethylenesulphone or N-methylpyrrolidone of a polymer having an inherent viscosity from 0.4 to 1.6 and consisting essentially of amide-imide linkages of the formula or of said amide-imide linkages and of amide linkages of the formula in which R represents a divalent benzene radical, Ar represents a radical, in which x is an integer from 1 to 3, and A i" represents the radical heating the filaments obtained to improve the physical and mechanical properties of said polymer at a temperature higher than 160 C. up to about 240 C. at
  • polyamide-imide solution has a viscosity of 300 to 6,000 poises at 25 C.
  • a process according to claim 1 wherein the evaporating atmosphere consists of hot air or inert gas, or both.

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  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pain & Pain Management (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Rehabilitation Therapy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Artificial Filaments (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polymerisation Methods In General (AREA)
US00114082A 1968-06-04 1971-02-09 Process for the preparation of polyamide-imide filaments Expired - Lifetime US3717696A (en)

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US (1) US3717696A (enrdf_load_stackoverflow)
AT (1) AT296488B (enrdf_load_stackoverflow)
BE (1) BE734016A (enrdf_load_stackoverflow)
BR (1) BR6909423D0 (enrdf_load_stackoverflow)
CA (1) CA934516A (enrdf_load_stackoverflow)
CH (1) CH516007A (enrdf_load_stackoverflow)
DE (1) DE1928435C3 (enrdf_load_stackoverflow)
DK (1) DK132450C (enrdf_load_stackoverflow)
ES (1) ES368044A1 (enrdf_load_stackoverflow)
FR (1) FR1603108A (enrdf_load_stackoverflow)
GB (1) GB1268267A (enrdf_load_stackoverflow)
LU (1) LU58789A1 (enrdf_load_stackoverflow)
NL (1) NL6908409A (enrdf_load_stackoverflow)
NO (1) NO131609C (enrdf_load_stackoverflow)
SE (1) SE360400B (enrdf_load_stackoverflow)
SU (1) SU392629A3 (enrdf_load_stackoverflow)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3862897A (en) * 1969-09-05 1975-01-28 Rhone Poulenc Sa Method of forming high elongation polymide-imide films
US3903058A (en) * 1971-08-12 1975-09-02 Rhone Poulenc Textile Process for making bright yarns
US4225686A (en) * 1979-07-19 1980-09-30 The Upjohn Company Blends of copolyimides with copolyamideimides
US4801502A (en) * 1983-03-09 1989-01-31 Chemiefaser Lenzing Aktiengesellschaft Non-flammable, high-temperature resistant polyimide fibers made by a dry spinning method
US5486412A (en) * 1988-02-26 1996-01-23 Lenzing Aktiengesellschaft Flame retardant high-temperature-resistant polyimide fibers and molded articles manufactured therefrom
US5681656A (en) * 1994-05-13 1997-10-28 Toyo Boseki Kabushiki Kaisha Polyamide-imide fibers for a bag filter
EP1911864A4 (en) * 2005-07-29 2010-03-31 Toyo Boseki POLYAMIDE-IMIDE FIBER, NONWOVEN FABRIC COMPRISING THE SAME, PROCESS FOR PRODUCING THE NONWOVEN FABRIC, AND SEPARATOR FOR ELECTRONIC COMPONENT

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3939116A (en) * 1973-05-14 1976-02-17 Exxon Research And Engineering Company Self-supported, oriented high-performance films having minimal thermal distortion properties
CN114717681B (zh) * 2022-05-27 2024-06-14 南通博联材料科技有限公司 一种耐高温、阻燃聚酰胺酰亚胺基长丝及其绿色制备和原位增强方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3260691A (en) * 1963-05-20 1966-07-12 Monsanto Co Coating compositions prepared from condensation products of aromatic primary diamines and aromatic tricarboxylic compounds
US3314923A (en) * 1963-11-26 1967-04-18 Bayer Ag Process for preparing imide containing polyisocyanates
US3415782A (en) * 1964-03-30 1968-12-10 Du Pont Formation of polypyromellitimide filaments

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3260691A (en) * 1963-05-20 1966-07-12 Monsanto Co Coating compositions prepared from condensation products of aromatic primary diamines and aromatic tricarboxylic compounds
US3314923A (en) * 1963-11-26 1967-04-18 Bayer Ag Process for preparing imide containing polyisocyanates
US3415782A (en) * 1964-03-30 1968-12-10 Du Pont Formation of polypyromellitimide filaments

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3862897A (en) * 1969-09-05 1975-01-28 Rhone Poulenc Sa Method of forming high elongation polymide-imide films
US3903058A (en) * 1971-08-12 1975-09-02 Rhone Poulenc Textile Process for making bright yarns
US4225686A (en) * 1979-07-19 1980-09-30 The Upjohn Company Blends of copolyimides with copolyamideimides
US4801502A (en) * 1983-03-09 1989-01-31 Chemiefaser Lenzing Aktiengesellschaft Non-flammable, high-temperature resistant polyimide fibers made by a dry spinning method
US5486412A (en) * 1988-02-26 1996-01-23 Lenzing Aktiengesellschaft Flame retardant high-temperature-resistant polyimide fibers and molded articles manufactured therefrom
US5681656A (en) * 1994-05-13 1997-10-28 Toyo Boseki Kabushiki Kaisha Polyamide-imide fibers for a bag filter
EP1911864A4 (en) * 2005-07-29 2010-03-31 Toyo Boseki POLYAMIDE-IMIDE FIBER, NONWOVEN FABRIC COMPRISING THE SAME, PROCESS FOR PRODUCING THE NONWOVEN FABRIC, AND SEPARATOR FOR ELECTRONIC COMPONENT

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CA934516A (en) 1973-10-02
SE360400B (enrdf_load_stackoverflow) 1973-09-24
DE1928435B2 (de) 1979-02-01
LU58789A1 (enrdf_load_stackoverflow) 1970-01-14
SU392629A3 (enrdf_load_stackoverflow) 1973-07-27
DE1928435C3 (de) 1979-09-20
DK132450B (da) 1975-12-08
NO131609C (enrdf_load_stackoverflow) 1975-06-25
NO131609B (enrdf_load_stackoverflow) 1975-03-17
AT296488B (de) 1972-02-10
DK132450C (da) 1976-06-08
DE1928435A1 (de) 1969-12-11
NL6908409A (enrdf_load_stackoverflow) 1969-12-08
FR1603108A (enrdf_load_stackoverflow) 1971-03-22
BE734016A (enrdf_load_stackoverflow) 1969-12-03
ES368044A1 (es) 1971-05-01
CH516007A (fr) 1971-11-30
BR6909423D0 (pt) 1973-04-05
GB1268267A (en) 1972-03-29

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