WO1999027169A1 - Materiaux retardateurs de flamme - Google Patents

Materiaux retardateurs de flamme Download PDF

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Publication number
WO1999027169A1
WO1999027169A1 PCT/EP1998/007007 EP9807007W WO9927169A1 WO 1999027169 A1 WO1999027169 A1 WO 1999027169A1 EP 9807007 W EP9807007 W EP 9807007W WO 9927169 A1 WO9927169 A1 WO 9927169A1
Authority
WO
WIPO (PCT)
Prior art keywords
flame
polymer
pipd
retardant
polymers
Prior art date
Application number
PCT/EP1998/007007
Other languages
English (en)
Other versions
WO1999027169A8 (fr
Inventor
Maurits Gerhard Northolt
Doetze Jakob Sikkema
Original Assignee
Akzo Nobel N.V.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Akzo Nobel N.V. filed Critical Akzo Nobel N.V.
Priority to EP98956905A priority Critical patent/EP1032729B1/fr
Priority to DE69829773T priority patent/DE69829773T2/de
Priority to PCT/EP1998/007007 priority patent/WO1999027169A1/fr
Publication of WO1999027169A1 publication Critical patent/WO1999027169A1/fr
Publication of WO1999027169A8 publication Critical patent/WO1999027169A8/fr

Links

Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/74—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polycondensates of cyclic compounds, e.g. polyimides, polybenzimidazoles

Definitions

  • the invention pertains to flame-retardant materials, and to the use of said materials for the manufacture of flame-retardant composite material, non- woven material, fabric, film, foam, or paper.
  • spun fibers, films, foams, and injection-molded articles prepared from hydrates of polymers can be used for the manufacture of flame-retardant materials with a significant improvement over non-hydrated fibers, films, foams, or articles.
  • the fibers, films, foams, or injection-molded articles are preferably made of hydrates of hydroxy-containing polymers, more preferably hydroxy- containing rigid rod polymers, and, even more preferably, of hydrates of PIPD.
  • At least 50% of the rigid rod polymers according to the present invention is composed of recurring groups of pyridobisimidazole-2,6- diyl(2,5-dihydroxy-p-phenylene), while in the remaining groups the 2,5- dihydroxy-p-phenylene is replaced by an arylene which may be substituted or not and/or the pyridobisimidazole is replaced by benzobisimidazole, benzobisthiazole, benzobisoxazole, pyridobisthiazole, and/or pyridobis- oxazole.
  • arylene dicarboxylic acid such as isophthalic acid, terephthalic acid, 2,5-pyridine dicarboxylic acid, 2,6-naphthalene dicarboxylic acid, 4,4'-diphenyl dicarboxylic acid, 2,6-quinoline dicarboxylic acid, and 2,6-bis(4-carboxyphenyl)pyridobisimidazole.
  • the polymer of the present invention is brought to the form of its hydrate by spinning of a solution of the polymer in a suitable solvent (for instance, polyphosphoric acid) into water or dilute phosphoric acid, made into a film or foam in the presence of water by methods common in the art, or brought to the form of its hydrate by injection-molding the polymer into water.
  • a suitable solvent for instance, polyphosphoric acid
  • the fibers are not or only partially dehydrated and, preferably, are used as such without undergoing any dehydrating heat treatment at all.
  • the hydrate content of the fiber, film, foam, or injection-molded article is >10 wt.%, preferably >20 wt.%, at 21 °C and 65% RH (relative humidity).
  • the polymer can maximally contain one molecule water per hydroxy group (for PIPD 21.4 wt.%), and for fibers, films, and foams usually somewhat more because of water contained in the voids (for PIPD the maximum total water content is up to 25 wt.%).
  • the hydrated fibers, films, foams, and articles are not heat treated and are used as such for the manufacture of composites, fabrics, non-wovens, papers, and the like. Products obtainable from the polymers preferably are made with 100% hydrated polymers.
  • the preparation of the PIPD homopolymer can be carried out by the incorporation, with vigorous stirring, of the salt of 2,5-dihydroxyterephthalic acid and tetraaminopyridine into strong polyphosphoric acid followed by heating (see WO 94/25506).
  • the polymer is then precipitated in water using a spinning arrangement, and washed with an alkaline solution, such as ammonia.
  • the mixture obtained from the polymerization reaction can be used directly for spinning or extrusion into fibers, films, foams, or tapes without any further measures or additions to the mixture being required, and thereafter used in composites, fabrics, and the like.
  • the polymer is prepared and spun or extruded in one continuous process
  • films, foams, or tapes can be made directly from the composition, which is obtained from the solution resulting from the polymerization reaction.
  • These objects such as fibers, tapes, foams, or films can be applied either as such and, hence, consist of the polymer of the present invention, or they can be used in combination with similar objects made of another material.
  • products can be made which comprise the objects of the present invention in combination with other materials.
  • the products may be applied as reinforcement material in products which are used at high temperatures, or where the temperature can increase and where flame-retardancy is a required property.
  • the fibers may be cut and used as staple fiber or, when fibrillated, as pulp, for instance, in paper making.
  • the thermal stability and the flame-retardancy of the polymer of the present invention were found to be very good, with very low loss of the mechanical characteristics of the fibers made thereof.
  • the materials of this invention can be applied in fire barrier materials, such as suits worn by firemen and boundarymen aboard ships, battle helmets, flak vests, fire protection blankets, and the like.
  • fibers of the material of the present invention were tested using a Cone calorimeter. This test provides a good indication of several different characteristics, e.g., the peak heat release rate (PHRR), the time to ignition (TTI), the total specific extinction area (SEA), and the fire performance index (FPI).
  • PHRR peak heat release rate
  • TTI time to ignition
  • SEA total specific extinction area
  • FPI fire performance index
  • the polymer obtained from Example 2 with a polymer concentration of 14 wt.% was fed at a temperature of 195°C to a 0.6 m 1 metering pump by means of a 19 mm single screw extruder.
  • the polymer was passed through a 25 ⁇ m filter package and subsequently extruded at a throughput of 6.5 mVmin and a temperature of 205°C through a spinneret containing 40 spinning holes of a diameter of 100 ⁇ m.
  • Fibers were produced by a dry-jet-wet spinning technique, with water being used as the coagulation medium.
  • the air gap length was 20 mm, the draw ratio in the air gap 4.65.
  • the fibers were wound onto a bobbin, and washed with water for 48 hours, neutralized with ammonia, and washed again. These undried fibers (AS-PIPD) were used as such.
  • Example 3 Between 10.3 g and 11.5 g of a sample of AS-PIPD (PIPD as spun, hydrated PIPD), PIPD (non-hydrated PIPD), PBO-HM (high-modulus PBO), Twaron® (poly(p-phenyleneterephthalamide)), Nomex® (poly(m-phenylene- terephthalamide)), or PVC (polyvinylchloride with the stabilizers Phosflex 41 and zinc borate) was brought into a Cone calorimeter having a heat release of 75 kW/m 2 . The calorimeter has a heating mantle for constant heat transfer to a sample of standard size. A spark plug was used to generate sparks.
  • AS-PIPD PIPD as spun, hydrated PIPD
  • PIPD non-hydrated PIPD
  • PBO-HM high-modulus PBO
  • Twaron® poly(p-phenyleneterephthalamide)
  • Nomex® poly(m-phenylene-
  • the PHRR which gives the maximum heat release
  • the TTI which is the time the sample needs from the start of the test to continuously burn
  • the SEA which is the total extinction of light measured by a laser and a receiver during the test
  • the FPI which is the fire performance index obtained by the quotient of TTI/PHRR
  • the heat absorption of various PIPD samples was measured with a Setaram C80D calorimeter.
  • An open cell using 1 g of material and a scan rate of 0.2 °C/min yielded scans from 30 to 200°C.
  • the scans show the specific heat as a function of temperature and the absorption of heat due to the evaporation of water from the open cell.
  • the test samples contained AS-PIPD (hydrated PIPD as spun), ASd-PIPD (dried PIPD as spun), HT- PIPD (heat treated partially hydrated PIPD), or HTd-PIPD (heat treated dried PIPD).
  • AS-PIPD hydrated PIPD as spun
  • ASd-PIPD dried PIPD as spun
  • HT- PIPD heat treated partially hydrated PIPD
  • HTd-PIPD heat treated dried PIPD
  • the water content of the hydrate of the hydroxy-containing rigid rod polymer was determined as follows:
  • the mass (m b ) of a sample of the material is determined.
  • the sample is then dried at 150°C at ⁇ 0.133 kPa during 16 to 20 h, after which the dry mass (m a ) of the sample is determined immediately.
  • the water content is then calculated to be 100.(m -ma)/m b %.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Artificial Filaments (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

Abstract

L'invention concerne un matériau retardateur de flamme préparé à partir d'hydrates de polymères pouvant s'utiliser pour la fabrication de matériaux retardateurs de flamme, tels que des composites, des tissus, des non-tissés, des films, des mousses, et du papier, avec une amélioration notable par rapport aux matériaux non hydratés. On utilisera de préférence des hydrates de polymères contenant hydroxy, et idéalement des polymères baguette rigides entièrement hydratés, notamment des fibres de PIPD entièrement hydratés.
PCT/EP1998/007007 1997-11-21 1998-10-26 Materiaux retardateurs de flamme WO1999027169A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP98956905A EP1032729B1 (fr) 1997-11-21 1998-10-26 Materiaux retardateurs de flamme
DE69829773T DE69829773T2 (de) 1997-11-21 1998-10-26 Flammhemmende materialien
PCT/EP1998/007007 WO1999027169A1 (fr) 1997-11-21 1998-10-26 Materiaux retardateurs de flamme

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP97203642 1997-11-21
EP97203642.0 1997-11-21
PCT/EP1998/007007 WO1999027169A1 (fr) 1997-11-21 1998-10-26 Materiaux retardateurs de flamme

Publications (2)

Publication Number Publication Date
WO1999027169A1 true WO1999027169A1 (fr) 1999-06-03
WO1999027169A8 WO1999027169A8 (fr) 2000-09-14

Family

ID=26070334

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/007007 WO1999027169A1 (fr) 1997-11-21 1998-10-26 Materiaux retardateurs de flamme

Country Status (2)

Country Link
EP (1) EP1032729B1 (fr)
WO (1) WO1999027169A1 (fr)

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006105230A1 (fr) * 2005-03-28 2006-10-05 E. I. Du Pont De Nemours And Company Procede de production de fil de polyarene-azole
WO2006104974A1 (fr) 2005-03-28 2006-10-05 E.I. Du Pont De Nemours And Company Procede de production de polymere de polyareneazole
WO2006105227A1 (fr) * 2005-03-28 2006-10-05 E. I. Du Pont De Nemours And Company Procede thermique destine a augmenter les viscosites inherentes des polyarene-azole
WO2006105228A1 (fr) * 2005-03-28 2006-10-05 E. I. Du Pont De Nemours And Company Polymeres a viscosite inherente elevee et fibres de ceux-ci
WO2007070813A1 (fr) * 2005-12-16 2007-06-21 E. I. Du Pont De Nemours And Company Tissu confortable en pipd et articles fabriques a partir de ce tissu
WO2007073540A1 (fr) * 2005-12-16 2007-06-28 E.I. Du Pont De Nemours And Company Vêtements présentant des propriétés thermiques composés d'un tissu de revêtement extérieur tolérant aux rayonnements uv comprenant des fibres de polypyridobisimidazole et de polybenzobisoxazole
WO2007073539A1 (fr) * 2005-12-16 2007-06-28 E.I. Du Pont De Nemours And Company Vêtements présentant des propriétés thermiques composés d'un tissu de revêtement extérieur comprenant des fibres pipd et aramides
WO2007076263A1 (fr) * 2005-12-16 2007-07-05 E. I. Du Pont De Nemours And Company Vetements a performances thermiques comprenant un tissu d'enveloppe externe resistant au blanchiment de fibres de polypyridobisimidazole et de polybenzobisoxazole
WO2007076270A2 (fr) * 2005-12-16 2007-07-05 E. I. Du Pont De Nemours And Company Vetements comprenant un tissus d'enveloppe exterieure de haute resistance et de tres haut rendement thermique, fait en fibres de polybenzimidazole et de polypyridobisimidazole
WO2007076333A2 (fr) * 2005-12-21 2007-07-05 E. I. Du Pont De Nemours And Company Papier comprenant du pulpe pipd et processus de fabrication correspondant
WO2007076259A2 (fr) * 2005-12-16 2007-07-05 E.I. Du Pont De Nemours And Company Vetements comprenant un tissus d'enveloppe exterieure souple de tres haut rendement thermique en fibres de polybenzimidazole et de polypyridobisimidazole
WO2007076258A2 (fr) * 2005-12-16 2007-07-05 E. I. Du Pont De Nemours And Company Tissus faits à partir d'un mélange de fibres de polypyridobisimidazole et de fibres cellulosiques ignifugées, et articles ainsi obtenus
WO2007076332A3 (fr) * 2005-12-21 2007-08-30 Du Pont Pulpe de polypyridobisimidazole a liaison spontanee et processus de fabrication correspondant
WO2007076343A3 (fr) * 2005-12-21 2007-09-27 Du Pont Floculat de poly(pyridobisimidazole) fibrille
WO2007075576A3 (fr) * 2005-12-21 2007-10-04 Du Pont Pate comprenant du polypyridobisimidazole et d'autres polymeres, et ses methodes de fabrication
WO2007145673A2 (fr) * 2005-12-08 2007-12-21 E. I. Du Pont De Nemours And Company Couche non tissée sans matrice de fibres courtes de polypyridazole
JP2008534749A (ja) * 2005-03-28 2008-08-28 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 金属粉末を使用する固有粘度が高いポリアレンアゾールの製造法
JP2009521621A (ja) * 2005-12-21 2009-06-04 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー Ｐｉｐｄフロックを含んでなる紙およびその製造方法
US7683122B2 (en) 2005-03-28 2010-03-23 E. I. Du Pont De Nemours And Company Processes for increasing polymer inherent viscosity
US7776246B2 (en) 2005-03-28 2010-08-17 E. I. Du Pont De Nemours And Company Process for the production of polyarenazole yarn
US7851584B2 (en) 2005-03-28 2010-12-14 E. I. Du Pont De Nemours And Company Process for preparing monomer complexes
US7888457B2 (en) 2005-04-01 2011-02-15 E. I. Du Pont De Nemours And Company Process for removing phosphorous from a fiber or yarn
US7906615B2 (en) 2005-03-28 2011-03-15 Magellan Systems International, Llc Process for hydrolyzing polyphosphoric acid in a spun yarn
US7906613B2 (en) 2005-03-28 2011-03-15 Magellan Systems International, Llc Process for removing cations from polyareneazole fiber
US7968030B2 (en) 2005-03-28 2011-06-28 E.I. Du Pont De Nemours And Company Hot surface hydrolysis of polyphosphoric acid in spun yarns
US7968029B2 (en) 2005-03-28 2011-06-28 E. I. Du Pont De Nemours And Company Processes for hydrolysis of polyphoshoric acid in polyareneazole filaments
US7977453B2 (en) 2005-03-28 2011-07-12 E. I. Du Pont De Nemours And Company Processes for hydrolyzing polyphosphoric acid in shaped articles
US8202965B2 (en) 2005-03-28 2012-06-19 E.I. Du Pont De Nemours And Company Fusion free hydrolysis of polyphosphoric acid in spun multifilament yarns
US8298375B2 (en) * 2005-12-21 2012-10-30 E I Du Pont De Nemours And Company Friction papers comprising PIPD fiber
CN103588703A (zh) * 2013-11-29 2014-02-19 中蓝晨光化工研究设计院有限公司 一种2，3，5，6-四氨基吡啶磷酸盐的制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994025506A1 (fr) * 1993-04-28 1994-11-10 Akzo Nobel N.V. Polymere en tige rigide a base de pyridobisimidazole

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994025506A1 (fr) * 1993-04-28 1994-11-10 Akzo Nobel N.V. Polymere en tige rigide a base de pyridobisimidazole

Cited By (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7968030B2 (en) 2005-03-28 2011-06-28 E.I. Du Pont De Nemours And Company Hot surface hydrolysis of polyphosphoric acid in spun yarns
US7683122B2 (en) 2005-03-28 2010-03-23 E. I. Du Pont De Nemours And Company Processes for increasing polymer inherent viscosity
WO2006105227A1 (fr) * 2005-03-28 2006-10-05 E. I. Du Pont De Nemours And Company Procede thermique destine a augmenter les viscosites inherentes des polyarene-azole
WO2006105228A1 (fr) * 2005-03-28 2006-10-05 E. I. Du Pont De Nemours And Company Polymeres a viscosite inherente elevee et fibres de ceux-ci
CN101238164B (zh) * 2005-03-28 2012-10-03 纳幕尔杜邦公司 制备聚芳并唑聚合物的方法
US8263221B2 (en) 2005-03-28 2012-09-11 Magellan Systems International, Llc High inherent viscosity polymers and fibers therefrom
US8202965B2 (en) 2005-03-28 2012-06-19 E.I. Du Pont De Nemours And Company Fusion free hydrolysis of polyphosphoric acid in spun multifilament yarns
JP2008534749A (ja) * 2005-03-28 2008-08-28 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 金属粉末を使用する固有粘度が高いポリアレンアゾールの製造法
US7671171B2 (en) 2005-03-28 2010-03-02 E. I. Du Pont De Nemours And Company Processes for preparing high inherent viscosity polyareneazoles using metal powders
WO2006104974A1 (fr) 2005-03-28 2006-10-05 E.I. Du Pont De Nemours And Company Procede de production de polymere de polyareneazole
WO2006105230A1 (fr) * 2005-03-28 2006-10-05 E. I. Du Pont De Nemours And Company Procede de production de fil de polyarene-azole
US7906613B2 (en) 2005-03-28 2011-03-15 Magellan Systems International, Llc Process for removing cations from polyareneazole fiber
US7906615B2 (en) 2005-03-28 2011-03-15 Magellan Systems International, Llc Process for hydrolyzing polyphosphoric acid in a spun yarn
US7977453B2 (en) 2005-03-28 2011-07-12 E. I. Du Pont De Nemours And Company Processes for hydrolyzing polyphosphoric acid in shaped articles
US7851584B2 (en) 2005-03-28 2010-12-14 E. I. Du Pont De Nemours And Company Process for preparing monomer complexes
US7776246B2 (en) 2005-03-28 2010-08-17 E. I. Du Pont De Nemours And Company Process for the production of polyarenazole yarn
US7754846B2 (en) 2005-03-28 2010-07-13 E. I. Du Pont De Nemours And Company Thermal processes for increasing polyareneazole inherent viscosities
US7968029B2 (en) 2005-03-28 2011-06-28 E. I. Du Pont De Nemours And Company Processes for hydrolysis of polyphoshoric acid in polyareneazole filaments
US7683157B2 (en) 2005-03-28 2010-03-23 E.I. Du Pont De Nemours And Company Process for the production of polyarenazole polymer
US7888457B2 (en) 2005-04-01 2011-02-15 E. I. Du Pont De Nemours And Company Process for removing phosphorous from a fiber or yarn
US8051494B2 (en) 2005-12-08 2011-11-08 E.I. Du Pont De Nemours And Company Matrix free non-woven layer of polypyridazle short fiber
WO2007145673A2 (fr) * 2005-12-08 2007-12-21 E. I. Du Pont De Nemours And Company Couche non tissée sans matrice de fibres courtes de polypyridazole
JP2009520113A (ja) * 2005-12-08 2009-05-21 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー マトリックスを含まないポリピリダゾール短繊維の不織層
WO2007145673A3 (fr) * 2005-12-08 2008-06-12 Du Pont Couche non tissée sans matrice de fibres courtes de polypyridazole
WO2007073539A1 (fr) * 2005-12-16 2007-06-28 E.I. Du Pont De Nemours And Company Vêtements présentant des propriétés thermiques composés d'un tissu de revêtement extérieur comprenant des fibres pipd et aramides
WO2007073540A1 (fr) * 2005-12-16 2007-06-28 E.I. Du Pont De Nemours And Company Vêtements présentant des propriétés thermiques composés d'un tissu de revêtement extérieur tolérant aux rayonnements uv comprenant des fibres de polypyridobisimidazole et de polybenzobisoxazole
WO2007076259A3 (fr) * 2005-12-16 2007-12-27 Du Pont Vetements comprenant un tissus d'enveloppe exterieure souple de tres haut rendement thermique en fibres de polybenzimidazole et de polypyridobisimidazole
WO2007070813A1 (fr) * 2005-12-16 2007-06-21 E. I. Du Pont De Nemours And Company Tissu confortable en pipd et articles fabriques a partir de ce tissu
WO2007076258A3 (fr) * 2005-12-16 2008-03-06 Du Pont Tissus faits à partir d'un mélange de fibres de polypyridobisimidazole et de fibres cellulosiques ignifugées, et articles ainsi obtenus
CN101330842B (zh) * 2005-12-16 2012-03-28 纳幕尔杜邦公司 包含高强度耐极热性聚苯并咪唑和聚吡啶并双咪唑纤维外层面料的服装
WO2007076263A1 (fr) * 2005-12-16 2007-07-05 E. I. Du Pont De Nemours And Company Vetements a performances thermiques comprenant un tissu d'enveloppe externe resistant au blanchiment de fibres de polypyridobisimidazole et de polybenzobisoxazole
US7820567B2 (en) * 2005-12-16 2010-10-26 E. I. Du Pont De Nemours And Company Fabrics made from a blend of polypyridobisimidazole/flame-retardant treated cellulose fibers and articles made therefrom
WO2007076270A3 (fr) * 2005-12-16 2007-09-27 Du Pont Vetements comprenant un tissus d'enveloppe exterieure de haute resistance et de tres haut rendement thermique, fait en fibres de polybenzimidazole et de polypyridobisimidazole
WO2007076270A2 (fr) * 2005-12-16 2007-07-05 E. I. Du Pont De Nemours And Company Vetements comprenant un tissus d'enveloppe exterieure de haute resistance et de tres haut rendement thermique, fait en fibres de polybenzimidazole et de polypyridobisimidazole
WO2007076259A2 (fr) * 2005-12-16 2007-07-05 E.I. Du Pont De Nemours And Company Vetements comprenant un tissus d'enveloppe exterieure souple de tres haut rendement thermique en fibres de polybenzimidazole et de polypyridobisimidazole
WO2007076258A2 (fr) * 2005-12-16 2007-07-05 E. I. Du Pont De Nemours And Company Tissus faits à partir d'un mélange de fibres de polypyridobisimidazole et de fibres cellulosiques ignifugées, et articles ainsi obtenus
JP2009521621A (ja) * 2005-12-21 2009-06-04 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー Ｐｉｐｄフロックを含んでなる紙およびその製造方法
JP2009521620A (ja) * 2005-12-21 2009-06-04 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー Ｐｉｐｄパルプを含んでなる紙およびその製造方法
WO2007076332A3 (fr) * 2005-12-21 2007-08-30 Du Pont Pulpe de polypyridobisimidazole a liaison spontanee et processus de fabrication correspondant
WO2007076343A3 (fr) * 2005-12-21 2007-09-27 Du Pont Floculat de poly(pyridobisimidazole) fibrille
WO2007076333A3 (fr) * 2005-12-21 2007-08-30 Du Pont Papier comprenant du pulpe pipd et processus de fabrication correspondant
WO2007075576A3 (fr) * 2005-12-21 2007-10-04 Du Pont Pate comprenant du polypyridobisimidazole et d'autres polymeres, et ses methodes de fabrication
WO2007076333A2 (fr) * 2005-12-21 2007-07-05 E. I. Du Pont De Nemours And Company Papier comprenant du pulpe pipd et processus de fabrication correspondant
US7727358B2 (en) 2005-12-21 2010-06-01 E.I. Du Pont De Nemours And Company Pulp comprising polypyridobisimidazole and other polymers and methods of making same
US8137506B2 (en) 2005-12-21 2012-03-20 E. I. Du Pont De Nemours And Company Paper comprising PIPD pulp and process for making same
US8298375B2 (en) * 2005-12-21 2012-10-30 E I Du Pont De Nemours And Company Friction papers comprising PIPD fiber
US8444814B2 (en) * 2005-12-21 2013-05-21 Mikhail R. Levit Paper comprising PIPD floc and process for making the same
KR101359868B1 (ko) 2005-12-21 2014-02-06 이 아이 듀폰 디 네모아 앤드 캄파니 피브릴화 폴리피리도비스이미다졸 플록
KR101426882B1 (ko) 2005-12-21 2014-08-06 이 아이 듀폰 디 네모아 앤드 캄파니 폴리피리도비스이미다졸 펄프의 제조 방법
KR101380526B1 (ko) * 2005-12-21 2014-04-11 이 아이 듀폰 디 네모아 앤드 캄파니 폴리피리도비스이미다졸 펄프 및 이의 제조 방법
CN103588703A (zh) * 2013-11-29 2014-02-19 中蓝晨光化工研究设计院有限公司 一种2，3，5，6-四氨基吡啶磷酸盐的制备方法
CN103588703B (zh) * 2013-11-29 2015-08-05 中蓝晨光化工研究设计院有限公司 一种2,3,5,6-四氨基吡啶磷酸盐的制备方法

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