US20080014440A1 - Polyoxadiazole composite fibers - Google Patents
Polyoxadiazole composite fibers Download PDFInfo
- Publication number
- US20080014440A1 US20080014440A1 US11/486,243 US48624306A US2008014440A1 US 20080014440 A1 US20080014440 A1 US 20080014440A1 US 48624306 A US48624306 A US 48624306A US 2008014440 A1 US2008014440 A1 US 2008014440A1
- Authority
- US
- United States
- 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.)
- Abandoned
Links
- 239000000835 fiber Substances 0.000 title claims abstract description 68
- 239000002131 composite material Substances 0.000 title claims abstract description 47
- 229920000642 polymer Polymers 0.000 claims abstract description 55
- 229920001577 copolymer Polymers 0.000 claims description 9
- 229910052724 xenon Inorganic materials 0.000 claims description 8
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000004677 Nylon Substances 0.000 claims description 6
- 229920001778 nylon Polymers 0.000 claims description 6
- 229920001652 poly(etherketoneketone) Polymers 0.000 claims description 4
- 239000004760 aramid Substances 0.000 claims description 2
- 229920003235 aromatic polyamide Polymers 0.000 claims description 2
- 229920000767 polyaniline Polymers 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000007787 solid Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- WMAVHUWINYPPKT-UHFFFAOYSA-M (e)-3-methyl-n-[(e)-(1-methyl-2-phenylindol-1-ium-3-ylidene)amino]-1,3-thiazol-2-imine;chloride Chemical compound [Cl-].C12=CC=CC=C2N(C)C(C=2C=CC=CC=2)=C1N=NC=1SC=C[N+]=1C WMAVHUWINYPPKT-UHFFFAOYSA-M 0.000 description 4
- 239000000981 basic dye Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 1
- 239000004953 Aliphatic polyamide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229920003231 aliphatic polyamide Polymers 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 229910000377 hydrazine sulfate Inorganic materials 0.000 description 1
- 239000012493 hydrazine sulfate Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000010494 opalescence Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
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 floc. Multifilament yarns can be combined to form cords. Yarn can be intertwined and/or twisted.
- spin refers to the extrusion of a polymer solution through a spinneret.
- 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 polyvinylpyrrolidione (PVP).
- PVP polyvinylpyrrolidione
- 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.
- 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.
- a polyoxadiazole copolymer was prepared by mixing 86.885 grams (0.668 moles) solid hydrazine sulfate, 88.74 grams (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).
- low molecular weight PVP K-30 with a weight average molecular weight of about 60,000
- 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)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/486,243 US20080014440A1 (en) | 2006-07-13 | 2006-07-13 | Polyoxadiazole composite fibers |
| KR1020097001306A KR20090031431A (ko) | 2006-07-13 | 2007-06-27 | 폴리옥사다이아졸 복합 섬유 |
| BRPI0713241-7A BRPI0713241A2 (pt) | 2006-07-13 | 2007-06-27 | fibra compósita e artigo |
| JP2009519446A JP2009542935A (ja) | 2006-07-13 | 2007-06-27 | ポリオキサジアゾール複合繊維 |
| PCT/US2007/014973 WO2008008185A2 (en) | 2006-07-13 | 2007-06-27 | Polyoxadiazole composite fibers |
| CN2007800265937A CN101490320B (zh) | 2006-07-13 | 2007-06-27 | 聚*二唑复合纤维 |
| CA002655858A CA2655858A1 (en) | 2006-07-13 | 2007-06-27 | Polyoxadiazole composite fibers |
| MX2009000354A MX2009000354A (es) | 2006-07-13 | 2007-06-27 | Fibras compuestas de polioxadiazol. |
| EP07796527A EP2041340A2 (en) | 2006-07-13 | 2007-06-27 | Polyoxadiazole composite fibers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/486,243 US20080014440A1 (en) | 2006-07-13 | 2006-07-13 | Polyoxadiazole composite fibers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20080014440A1 true US20080014440A1 (en) | 2008-01-17 |
Family
ID=38779507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/486,243 Abandoned US20080014440A1 (en) | 2006-07-13 | 2006-07-13 | Polyoxadiazole composite fibers |
Country Status (9)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090306265A1 (en) * | 2008-06-10 | 2009-12-10 | Gkss-Forschungszentrum Geesthacht Gmbh | Production of composites made of polyoxadiazole polymers |
Families Citing this family (2)
| 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 |
| EP2861789B1 (en) * | 2012-06-15 | 2020-09-09 | DuPont Safety & Construction, Inc. | Flame resistant spun staple yarns made from blends of fibers derived from sulfonated naphthalene polyoxadiazole polymers |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UST969008I4 (en) * | 1977-01-25 | 1978-04-04 | Imperial Chemical Industries Limited | Production of oriented fibrillar products |
| US4091159A (en) * | 1975-10-13 | 1978-05-23 | Imperial Chemical Industries Limited | Bonded structures |
| US5057600A (en) * | 1987-10-09 | 1991-10-15 | The Dow Chemical Company | Process for forming an article comprising poly(etheretherketone) (PEEK) type polymers |
| US5922830A (en) * | 1996-03-29 | 1999-07-13 | Toray Industries, Inc. | Highly hygroscopic polyamide fiber, and production and application thereof |
| US6790528B2 (en) * | 2000-08-18 | 2004-09-14 | Transmit Gesellschaft Fuer Technologietransfer Mbh | Production of polymer fibres having nanoscale morphologies |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4839776B1 (enrdf_load_stackoverflow) * | 1970-10-08 | 1973-11-27 | ||
| JPS4929298B1 (enrdf_load_stackoverflow) * | 1970-12-16 | 1974-08-02 | ||
| JPS518414B2 (enrdf_load_stackoverflow) * | 1971-11-04 | 1976-03-16 | ||
| 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 |
| US4132757A (en) * | 1977-12-27 | 1979-01-02 | Monsanto Company | Twist efficiency of oxadiazole/hydrazide yarn |
| DD279509A1 (de) * | 1989-01-16 | 1990-06-06 | Schwarza Chemiefaser | Verfahren zur stabilisierung von stickstoff enthaltenden polymeren |
-
2006
- 2006-07-13 US US11/486,243 patent/US20080014440A1/en not_active Abandoned
-
2007
- 2007-06-27 BR BRPI0713241-7A patent/BRPI0713241A2/pt not_active Application Discontinuation
- 2007-06-27 KR KR1020097001306A patent/KR20090031431A/ko not_active Withdrawn
- 2007-06-27 JP JP2009519446A patent/JP2009542935A/ja active Pending
- 2007-06-27 EP EP07796527A patent/EP2041340A2/en not_active Withdrawn
- 2007-06-27 MX MX2009000354A patent/MX2009000354A/es unknown
- 2007-06-27 CA CA002655858A patent/CA2655858A1/en not_active Abandoned
- 2007-06-27 WO PCT/US2007/014973 patent/WO2008008185A2/en active Application Filing
- 2007-06-27 CN CN2007800265937A patent/CN101490320B/zh not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4091159A (en) * | 1975-10-13 | 1978-05-23 | Imperial Chemical Industries Limited | Bonded structures |
| UST969008I4 (en) * | 1977-01-25 | 1978-04-04 | Imperial Chemical Industries Limited | Production of oriented fibrillar products |
| US5057600A (en) * | 1987-10-09 | 1991-10-15 | The Dow Chemical Company | Process for forming an article comprising poly(etheretherketone) (PEEK) type polymers |
| US5922830A (en) * | 1996-03-29 | 1999-07-13 | Toray Industries, Inc. | Highly hygroscopic polyamide fiber, and production and application thereof |
| US6790528B2 (en) * | 2000-08-18 | 2004-09-14 | Transmit Gesellschaft Fuer Technologietransfer Mbh | Production of polymer fibres having nanoscale morphologies |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090306265A1 (en) * | 2008-06-10 | 2009-12-10 | Gkss-Forschungszentrum Geesthacht Gmbh | Production of composites made of polyoxadiazole polymers |
| EP2133385A2 (de) | 2008-06-10 | 2009-12-16 | Gkss-Forschungszentrum Geesthacht Gmbh | Herstellung von Komositen aus Polyxadiazol-Polymeren |
| DE102008027499A1 (de) | 2008-06-10 | 2009-12-17 | Gkss-Forschungszentrum Geesthacht Gmbh | Herstellung von Kompositen aus Polyoxadiazol-Polymeren |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008008185A2 (en) | 2008-01-17 |
| KR20090031431A (ko) | 2009-03-25 |
| CN101490320B (zh) | 2011-11-23 |
| JP2009542935A (ja) | 2009-12-03 |
| CN101490320A (zh) | 2009-07-22 |
| CA2655858A1 (en) | 2008-01-17 |
| BRPI0713241A2 (pt) | 2012-04-17 |
| MX2009000354A (es) | 2009-01-27 |
| EP2041340A2 (en) | 2009-04-01 |
| WO2008008185A3 (en) | 2008-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: E. I. DU PONT DE NEMOURS AND COMPANY, DELAWARE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:LEE, KIU-SEUNG;HARTZLER, JON DAVID;REEL/FRAME:018258/0941;SIGNING DATES FROM 20060824 TO 20060907 |
|
| STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |