WO2014016753A1 - Procédé de production d'une fibre de nylon comprenant un fluoropolymère - Google Patents

Procédé de production d'une fibre de nylon comprenant un fluoropolymère Download PDF

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Publication number
WO2014016753A1
WO2014016753A1 PCT/IB2013/056002 IB2013056002W WO2014016753A1 WO 2014016753 A1 WO2014016753 A1 WO 2014016753A1 IB 2013056002 W IB2013056002 W IB 2013056002W WO 2014016753 A1 WO2014016753 A1 WO 2014016753A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
fluoropolymer
salt solution
preparing
nylon fiber
Prior art date
Application number
PCT/IB2013/056002
Other languages
English (en)
Inventor
Serkan BAS
Original Assignee
Kordsa Global Endustriyel Iplik Ve Kord Bezi Sanayi Ve Ticaret Anonim Sirketi
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 Kordsa Global Endustriyel Iplik Ve Kord Bezi Sanayi Ve Ticaret Anonim Sirketi filed Critical Kordsa Global Endustriyel Iplik Ve Kord Bezi Sanayi Ve Ticaret Anonim Sirketi
Publication of WO2014016753A1 publication Critical patent/WO2014016753A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C08G69/28—Preparatory processes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
    • D01D1/00—Treatment of filament-forming or like material
    • D01D1/02—Preparation of spinning solutions
    • 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
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/10—Other agents for modifying properties
    • 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
    • D01F6/90—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 polyamides
    • 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
    • D01F6/90—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 polyamides
    • D01F6/905—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 polyamides of aromatic polyamides

Definitions

  • the present invention relates to a method for producing nylon fiber comprising fluoropolymer which enables the fluoropolymers such as PTFE (polytetrafluoroethylene), PFA (perfluoroalkoxide), MFA (monofluoroalkoxide), poly(ethylene-co-tetrafluoroethylene) (ETFE), fluorinated ethylene propylene (FEP) to be transformed into nylon fibers that can be drawn more easily and have lower friction coefficient by adding them into nylon.
  • fluoropolymers such as PTFE (polytetrafluoroethylene), PFA (perfluoroalkoxide), MFA (monofluoroalkoxide), poly(ethylene-co-tetrafluoroethylene) (ETFE), fluorinated ethylene propylene (FEP)
  • Nylon is one of the engineering plastics which have several industrial applications. Nylon has wide area of usage because of its excellent mechanical properties. In addition to this, water absorption of nylon rises up to 8% by weight. The said property causes the mechanical properties of nylon such as modulus and breaking strength to decrease. The chemical resistance of the nylon is also low. Nylon 6.6 deteriorates under UV light and becomes yellow. In order to improve the deficiencies of nylon, the fluoropolymers which have high resistance to moist, light and chemicals can be used as additives by blending with nylon. Furthermore, fatigue resistance of fluoropolymers is better than that of nylon. However, in the methods used today the fluoropolymer particles cannot be dispersed in the nylon homogenously.
  • United States Patent US20050100733 discloses the production of polyester fibers comprising fluoropolymer.
  • the said document discloses melting the fluoropolymer particles in polyester and spinning them as fiber.
  • the objective of the present invention is to provide a method for producing nylon fiber comprising fluoropolymer to enhance the mechanical properties of the nylon.
  • a further objective of the present invention is to provide a method for producing nylon fiber comprising fluoropolymer wherein the fluoropolymers are dispersed in nylon homogenously.
  • Another objective of the present invention is to provide a method for producing nylon fiber comprising fluoropolymer which comprises mixing water based chemicals and thus is environmental friendly.
  • Figure 1 is the view of the flowchart of a method for producing nylon comprising fluoropolymer.
  • a method for producing nylon comprising fluoropolymer (10) is developed to fulfill the objective of the present invention comprises the steps of
  • first amine monomer composition is prepared by using at least one amine from the group comprising aliphatic, alicyclic and aromatic diamines (11).
  • the amine monomer composition is prepared by using at least one of ethylenediamine, trimethylenediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, decamethylenediamine, undecamethylenediamine, dodecamethylenediamine, tridecamethylenediamine, hexadecamethylenediamine, octadecamethylenediamine, 2,2,4- or 2,4,4-trimethylhexamethylenediamine, cyclohexanediamine, methylcyclohexanediamine, 1,3 or 1,4- bis(aminomethyl)cyclohexane, isophoronedia
  • carboxylic acid monomer composition is prepared by using at least one carboxylic acid from the group comprising aliphatic, alicyclic and aromatic dicarboxylic acid monomer for reacting with the amine monomer (12).
  • carboxylic acid monomer composition is prepared by using at least one of malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebasic acid, undecanedioic acid, dodecanedioic acid, hexadecanedioic acid, hexadecendioic acid, octadecanedioic acid, octadecenedioic acid, eicosandioic acid, eicosendioic acid, docosandioic acid, diglycolic acid, 2,2,4-trimethyladipic acid, 1,4-cyclohexanedicarboxylic acid,
  • the prepared monomer compositions are dissolved in a solvent (13).
  • a solvent In the preferred embodiment of the invention, methanol is used as the solvent.
  • the said solution comprised of amine and dicarboxylic acid monomers is stirred and the salt formation is enabled (14).
  • the solution is kept at room temperature.
  • the solvent of the solution is removed (15).
  • Water is added on the salt remaining after the solvent is removed, and salt solution is prepared (16).
  • the prepared salt solution comprises 40-60% salt by weight.
  • water dispersion of fluoropolymer is added into the prepared salt solution (17).
  • at least one of the polymers such as PTFE (polytetrafluoroethylene), PFA (perfluoroalkoxide), MFA (monofluoroalkoxide), poly(ethylene-co-tetrafluoroethylene) (ETFE), fluorinated ethylene propylene (FEP) is used as fluoropolymer.
  • the amount of the solid present in the fluoropolymer water dispersion added inside the solution is in the range of 40-60% by weight, and the size of the particle is in the range of 40-200 nm.
  • the amount of the added fluoropolymer inside the final nylon is in the range of 0.5-25% by weight.
  • teflon (PTFE) is used as fluoropolymer.
  • Chemical additive enhancing the thermal stability of the final product is added inside the salt solution reinforced with fluoropolymer (18).
  • one or more than one copper compound is added inside the solution in order to enhance the thermal stability of the final product.
  • the temperature is raised to a certain range and the amide groups are formed (19).
  • the temperature is brought to a range of 270-320°C.
  • the amide groups are formed in the determined temperature range, and depending on this the molecular weight of the nylon comprised of amide groups is increased, and the water of the salt solution is removed from the medium (20).
  • water is withdrawn from the reactor until the amount of the water will be less than 0.1%.
  • the relative viscosity is kept in the range of 60-100 by withdrawing water (20).
  • the nylon added with fluoropolymer remaining after the water is removed is spinned and wound (21). In one embodiment of the invention the winding speed is 1000-6000 m/min.
  • the said invention involves dispersing fluoropolymers inside the nylon homogenously and extruding fiber from the said composition. Since the said composition involves mixing the water based chemicals, it makes it possible to use a more environmental friendly fiber production method.
  • fluoropolymers By adding fluoropolymers into the nylon fiber, chemical and thermal strength of the nylon fibers can be enhanced. Poor UV resistance of aromatic nylons such as aramid (Kevlar) can be improved by adding fluoropolymers. It is known that the strength of the nylon decreases when moist is absorbed on the surface of the nylon. Unlike nylon, the fluoropolymers are materials that do not hold moisture. For this reason, adding fluoropolymers to nylon improves the resistance of nylon against water.
  • the strength of the nylon can be preserved better independent from the time and climate conditions. Furthermore, by adding fluoropolymers into the nylon, fatigue resistance, abrasion resistance and the flexibility can be increased, besides the friction coefficients and the inflammableness can be decreased. Since fluoropolymer added nylon fibers are more resistant to stain and dirt, fluoropolymer added nylon fibers have wider area of use. The said fibers are used in medicine, surgical suture, outdoor applications, components being subjected to high friction and many other different areas.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Mechanical Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Polyamides (AREA)

Abstract

La présente invention concerne un procédé de production d'une fibre de nylon comprenant un fluoropolymère, lequel procédé comprend les étapes consistant à préparer une composition de monomère d'amine (11), à préparer une composition de monomère d'acide carboxylique (12), à dissoudre les monomères dans un solvant (13), à obtenir une diamine et des diacides formant le sel (14), à retirer le solvant (15), à préparer la solution saline (16) en ajoutant de l'eau, à ajouter un fluoropolymère dans la solution saline (17), à ajouter des produits chimiques augmentant la stabilité thermique (18), à former des groupes amides avec l'augmentation de la température (19), à retirer l'eau de la solution saline (20), à extruder le nylon fondu et à l'enrouler (21); ce qui permet aux fluoropolymères tels que le PTFE (polytétrafluoroéthylène), le PFA (perfluoroalkoxide), le MFA (monofluoroalkoxide), le poly(éthylène-co-tétrafluoroéthylène) (ETFE), l'éthylène-propylène fluoré (FEP) d'être transformés en fibres de nylon qui peuvent être tirées plus facilement et qui sont dotées d'un coefficient de frottement inférieur.
PCT/IB2013/056002 2012-07-26 2013-07-22 Procédé de production d'une fibre de nylon comprenant un fluoropolymère WO2014016753A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR201208748 2012-07-26
TR2012/08748 2012-07-26

Publications (1)

Publication Number Publication Date
WO2014016753A1 true WO2014016753A1 (fr) 2014-01-30

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2013/056002 WO2014016753A1 (fr) 2012-07-26 2013-07-22 Procédé de production d'une fibre de nylon comprenant un fluoropolymère

Country Status (1)

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WO (1) WO2014016753A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111575824A (zh) * 2020-06-15 2020-08-25 徐毓敏 一种高含氟聚酯纤维及其制备方法

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1129074A (en) * 1966-04-04 1968-10-02 Ici Ltd Polyamides
US3947424A (en) * 1974-07-31 1976-03-30 E. I. Du Pont De Nemours And Company Polyamidation process
US4159286A (en) 1977-05-24 1979-06-26 Allied Chemical Corporation Nucleated nylon/PTFE compositions
JPH0226919A (ja) * 1988-07-15 1990-01-29 Toray Ind Inc 低摩擦特性と防汚性に優れた繊維
US20030226347A1 (en) 2002-01-30 2003-12-11 Rory Smith Synthetic fiber rope for an elevator
US20050100733A1 (en) 2003-08-15 2005-05-12 Foss Manufacturing Co., Inc. Synthetic fibers modified with PTFE to improve performance
US20060154058A1 (en) * 2002-10-01 2006-07-13 William Neuberg Method of making synthetic melt spun fibres with polytetrafluoroethylene
JP2007254909A (ja) * 2006-03-22 2007-10-04 Unitica Fibers Ltd 蓄熱保温繊維

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1129074A (en) * 1966-04-04 1968-10-02 Ici Ltd Polyamides
US3947424A (en) * 1974-07-31 1976-03-30 E. I. Du Pont De Nemours And Company Polyamidation process
US4159286A (en) 1977-05-24 1979-06-26 Allied Chemical Corporation Nucleated nylon/PTFE compositions
JPH0226919A (ja) * 1988-07-15 1990-01-29 Toray Ind Inc 低摩擦特性と防汚性に優れた繊維
US20030226347A1 (en) 2002-01-30 2003-12-11 Rory Smith Synthetic fiber rope for an elevator
US20060154058A1 (en) * 2002-10-01 2006-07-13 William Neuberg Method of making synthetic melt spun fibres with polytetrafluoroethylene
US20050100733A1 (en) 2003-08-15 2005-05-12 Foss Manufacturing Co., Inc. Synthetic fibers modified with PTFE to improve performance
JP2007254909A (ja) * 2006-03-22 2007-10-04 Unitica Fibers Ltd 蓄熱保温繊維

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111575824A (zh) * 2020-06-15 2020-08-25 徐毓敏 一种高含氟聚酯纤维及其制备方法

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