EP2041340A2 - Polyoxadiazole composite fibers - Google Patents
Polyoxadiazole composite fibersInfo
- Publication number
- EP2041340A2 EP2041340A2 EP07796527A EP07796527A EP2041340A2 EP 2041340 A2 EP2041340 A2 EP 2041340A2 EP 07796527 A EP07796527 A EP 07796527A EP 07796527 A EP07796527 A EP 07796527A EP 2041340 A2 EP2041340 A2 EP 2041340A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- composite fiber
- polymer
- polyoxadiazole
- fiber
- flexible chain
- 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.)
- Withdrawn
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
- D01F6/88—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds
- D01F6/94—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds of other polycondensation products
-
- 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
- D01F8/00—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof
- D01F8/04—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers
-
- 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
- D01F8/00—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof
- D01F8/04—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers
- D01F8/12—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers with at least one polyamide as constituent
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
Definitions
- the present invention is directed to preparation of a polyoxadiazole composite fiber and articles produced therefrom.
- a need is present for a composite fiber comprising polyoxadiazole which exhibits dyeability and improved UV stability.
- the present invention is directed to a composite fiber comprising a polyoxadiazole polymer and a flexible chain non-polyoxadiazole polymer.
- the present invention relates to composite fibers of a polyoxadiazole and a flexible chain polymer and the preparation thereof.
- fiber is used herein interchangeably with “filament”, and means a relatively flexible, macroscopically homogeneous body having a high ratio of length to width across its cross- sectional area perpendicular to its length.
- the fiber cross section can be any shape, but is often somewhat circular.
- Fiber spun onto a bobbin in a package is referred to as continuous fiber. Fiber can be cut into short lengths called staple fiber. Fiber can be cut into even smaller lengths called floe. Multifilament yarns can be combined to form cords. Yarn can be intertwined and/or twisted.
- polyoxadiazole useful in this invention include any polyoxadiazole polymer which has suitable properties to allow it to be solution spun into a fiber from a solvent in which the second polymer can similarly be spun into a fiber can be used to produce composite fibers of this invention.
- the polyoxadiazole polymers are 1 ,3,4-polyoxadiazole polymers or copolymers. More preferably, the polyoxadiazole polymers including copolymers include but are not limited to polyoxadiazoles comprising the repeat units:
- the second polymer can be any polymer selected from known flexible chain polymers which include copolymers, but preferred polymers are those that form isotropic solutions in mineral acids, including chlorosulfonic acid and fluorosulfonic acid, particularly sulfuric acid.
- a highly preferred polymer for use in the isotropic solution is polyvinylpyrrolidone (PVP).
- PVP polyvinylpyrrolidone
- suitable polymers include aliphatic polyamides (e.g., 6-nylon, 6,6-nylon, and 6,12- nylon), polyaniline, polyether ketone ketone (PEKK), aromatic polyamides (MPD-I, MPD-I/T), and copolymers of PVP, such as PVP/VA(Vinyl Acetate).
- Polyoxadiazole polymers and flexible chain polymers can be combined in any ratio that allows the solution to be spun into a fiber.
- any ratio of polyoxadiazole polymer to flexible chain polymer can be spun into a fiber.
- One in the art will typically use the rule of mixtures to determine the ratio of the polymers that will produce a fiber with desired properties.
- each polymer will be present by weight in the amount of at least 2 percent in order to produce a measureable change in properties of the resulting composite fiber.
- Composite fibers of this invention can be spun by the process of continuously combining an isotropic polymer solution of a polyoxadiazole polymer and an isotropic solution of a second polymer to form a combined polymer solution; passing the combined polymer solution through at least one static mixer to form a spin dope; and extruding the spin dope through a spinneret to form a composite fiber.
- the process can further include passing the composite fiber through an air gap; contacting the composite/dope fiber with a quench solution to form a coagulated composite fiber; contacting the coagulated composite fiber with a wash solution; contacting the washed composite fiber with a neutralization solution to form a neutralized and washed composite fiber; drying the neutralized and washed composite fiber; and winding up the dried composite fiber.
- the dried composite fiber can be wound onto a bobbin on a windup device.
- the polyoxadiazole composite fibers exhibit improved dyeability over fibers of polyoxadiazole polymers alone.
- the composite fibers can be solution dyed using both basic or acidic dyes.
- Basic dyes or cationic dyes
- Cationic dyes such as Basacryl Red GL(Basic Red 29 by Color Index) are frequently used for this purpose because of the depth of the color it generates.
- Dyes are usually soluble in most of organic solvent and in aqueous medium, but dyeability was tested in aqueous medium.
- Slight acidity(pH of 4-6) is required to achieve level dyeing with basic dyes. Without being bound to any theory it is believed that improved dyeability of the composite fiber is due to a diffusive channel created by chain mobility of the flexible chain polymer.
- polyoxadiazole composite fibers typically improved over fibers of polyoxadiazole alone.
- Polyoxadiazole fibers alone when exposed to a Xenon lamp for 20 hours typically do not exhibit measureable tenacity.
- Composite fibers of polyoxadiazoles having at least 2 percent by weight of the second polymer when exposed to UV radiation using a Xenon lamp for 20 hours can retain measureable tenacity.
- polyoxadiazole composite fibers contain a sufficient amount of the second polymer to retain greater than 20 percent of their tenacity after 20 hours of exposure to a Xenon lamp.
- polyoxadiazole composite fibers contain a sufficient amount of the second polymer to retain greater than 35 percent of their tenacity after 20 hours of exposure to a Xenon lamp. Most preferably, polyoxadiazole composite fibers contain a sufficient amount of the second polymer to retain greater than 50 percent of their tenacity after 20 hours of exposure to a Xenon lamp.
- Each polymer solution and/or the combined stream can contain additives such as anti-oxidants, lubricants, ultra-violet screening agents, colorants and the like which are commonly incorporated. All percentages are by weight unless otherwise indicated.
- a polyoxadiazole copolymer was prepared by mixing 86.885 grams (0.668 moles) solid hydrazine sulfate, 88.74grams (0.534 moles) of solid terephthalic acid, and 22.18 grams (0.133 moles) of solid isophthalic acid were mixed and blended together in a mixer for 30 min. To this blended mixture of solids was added a first addition of 30% Oleum, 534 grams Oleum (2.001 moles of SO3) at 25 degrees Celsius.
- the mixture was mechanically stirred at 25 degrees Celsius for 15 minutes to dissolve the solids and form a solution.
- the solution was then heated to 120 degrees Celsius with mechanical stirring until a constant torque (constant viscosity) was observed on the mixer (60 minutes).
- the fiber sample prepared the same way except that low molecular weight PVP(K-30 with a weight average molecular weight of about 60,000) instead of K-90, was also dyed deep with Basacryl Red GL(a basic dye).
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/486,243 US20080014440A1 (en) | 2006-07-13 | 2006-07-13 | Polyoxadiazole composite fibers |
PCT/US2007/014973 WO2008008185A2 (en) | 2006-07-13 | 2007-06-27 | Polyoxadiazole composite fibers |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2041340A2 true EP2041340A2 (en) | 2009-04-01 |
Family
ID=38779507
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP07796527A Withdrawn EP2041340A2 (en) | 2006-07-13 | 2007-06-27 | Polyoxadiazole composite fibers |
Country Status (9)
Country | Link |
---|---|
US (1) | US20080014440A1 (en) |
EP (1) | EP2041340A2 (en) |
JP (1) | JP2009542935A (en) |
KR (1) | KR20090031431A (en) |
CN (1) | CN101490320B (en) |
BR (1) | BRPI0713241A2 (en) |
CA (1) | CA2655858A1 (en) |
MX (1) | MX2009000354A (en) |
WO (1) | WO2008008185A2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2784545C1 (en) * | 2022-05-24 | 2022-11-28 | Общество с ограниченной ответственностью Научно-производственная фирма "Термостойкие изделия" (ООО НПФ "Термостойкие изделия" | Method for producing polyoxadiasole threads |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7528217B2 (en) | 2006-10-06 | 2009-05-05 | E.I. Du Pont De Nemours And Company | Polymers and fibers formed therefrom |
DE102008027499A1 (en) | 2008-06-10 | 2009-12-17 | Gkss-Forschungszentrum Geesthacht Gmbh | Production of composites from polyoxadiazole polymers |
WO2014007948A2 (en) * | 2012-06-15 | 2014-01-09 | E. I. Du Pont De Nemours And Company | Flame resistant spun staple yarns made from blends of fibers derived from sulfonated naphthalene polyoxadiazole polymers |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD279509A1 (en) * | 1989-01-16 | 1990-06-06 | Schwarza Chemiefaser | METHOD FOR STABILIZING NITROGEN-CONTAINING POLYMERS |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4839776B1 (en) * | 1970-10-08 | 1973-11-27 | ||
JPS4929298B1 (en) * | 1970-12-16 | 1974-08-02 | ||
JPS518414B2 (en) * | 1971-11-04 | 1976-03-16 | ||
GB1529360A (en) * | 1975-10-13 | 1978-10-18 | Ici Ltd | Polyarylene-oxadiazole bonded structures |
US4054633A (en) * | 1976-05-13 | 1977-10-18 | Monsanto Company | Process for continuously preparing shaped articles of aromatic oxadiazole or aromatic oxadiazole/N-alkylhydrazide polymers from monomer solutions |
GB1589615A (en) * | 1977-01-25 | 1981-05-13 | Ici Ltd | Production of oriented fibrillar products |
US4132757A (en) * | 1977-12-27 | 1979-01-02 | Monsanto Company | Twist efficiency of oxadiazole/hydrazide yarn |
US5057600A (en) * | 1987-10-09 | 1991-10-15 | The Dow Chemical Company | Process for forming an article comprising poly(etheretherketone) (PEEK) type polymers |
JP3804097B2 (en) * | 1996-03-29 | 2006-08-02 | 東レ株式会社 | Support stockings with excellent wearing comfort |
DE10040897B4 (en) * | 2000-08-18 | 2006-04-13 | TransMIT Gesellschaft für Technologietransfer mbH | Nanoscale porous fibers of polymeric materials |
-
2006
- 2006-07-13 US US11/486,243 patent/US20080014440A1/en not_active Abandoned
-
2007
- 2007-06-27 CN CN2007800265937A patent/CN101490320B/en not_active Expired - Fee Related
- 2007-06-27 WO PCT/US2007/014973 patent/WO2008008185A2/en active Application Filing
- 2007-06-27 BR BRPI0713241-7A patent/BRPI0713241A2/en not_active Application Discontinuation
- 2007-06-27 EP EP07796527A patent/EP2041340A2/en not_active Withdrawn
- 2007-06-27 MX MX2009000354A patent/MX2009000354A/en unknown
- 2007-06-27 KR KR1020097001306A patent/KR20090031431A/en not_active Application Discontinuation
- 2007-06-27 JP JP2009519446A patent/JP2009542935A/en active Pending
- 2007-06-27 CA CA002655858A patent/CA2655858A1/en not_active Abandoned
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD279509A1 (en) * | 1989-01-16 | 1990-06-06 | Schwarza Chemiefaser | METHOD FOR STABILIZING NITROGEN-CONTAINING POLYMERS |
Non-Patent Citations (1)
Title |
---|
KUMMERLOWE C ET AL: "Polymer blends of poly(p-phenylene 1,3,4-oxadiazole) and poly(p-phenylene terephthalamide): morphology and mechanical behaviour", POLYMER, ELSEVIER SCIENCE PUBLISHERS B.V, GB, vol. 34, no. 8, 1 April 1993 (1993-04-01), pages 1677 - 1683, XP024120481, ISSN: 0032-3861, [retrieved on 19930401] * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2784545C1 (en) * | 2022-05-24 | 2022-11-28 | Общество с ограниченной ответственностью Научно-производственная фирма "Термостойкие изделия" (ООО НПФ "Термостойкие изделия" | Method for producing polyoxadiasole threads |
Also Published As
Publication number | Publication date |
---|---|
WO2008008185A2 (en) | 2008-01-17 |
KR20090031431A (en) | 2009-03-25 |
CN101490320B (en) | 2011-11-23 |
US20080014440A1 (en) | 2008-01-17 |
BRPI0713241A2 (en) | 2012-04-17 |
JP2009542935A (en) | 2009-12-03 |
MX2009000354A (en) | 2009-01-27 |
CN101490320A (en) | 2009-07-22 |
WO2008008185A3 (en) | 2008-05-02 |
CA2655858A1 (en) | 2008-01-17 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20090115 |
|
AK | Designated contracting states |
Kind code of ref document: A2 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC MT NL PL PT RO SE SI SK TR |
|
AX | Request for extension of the european patent |
Extension state: AL BA HR MK RS |
|
DAX | Request for extension of the european patent (deleted) | ||
RBV | Designated contracting states (corrected) |
Designated state(s): DE FR GB IT NL |
|
17Q | First examination report despatched |
Effective date: 20091105 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 20100316 |