WO2018147315A1 - Composition de résine polyamide conductrice - Google Patents

Composition de résine polyamide conductrice Download PDF

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Publication number
WO2018147315A1
WO2018147315A1 PCT/JP2018/004169 JP2018004169W WO2018147315A1 WO 2018147315 A1 WO2018147315 A1 WO 2018147315A1 JP 2018004169 W JP2018004169 W JP 2018004169W WO 2018147315 A1 WO2018147315 A1 WO 2018147315A1
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WO
WIPO (PCT)
Prior art keywords
polyamide resin
resin composition
mass
conductive
carbon
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Application number
PCT/JP2018/004169
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English (en)
Japanese (ja)
Inventor
久保田　修司
信宏 吉村
雄平 福本
和樹 岩村
Original Assignee
東洋紡株式会社
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 東洋紡株式会社 filed Critical 東洋紡株式会社
Priority to JP2018510895A priority Critical patent/JPWO2018147315A1/ja
Publication of WO2018147315A1 publication Critical patent/WO2018147315A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C08K7/06—Elements
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/20—Conductive material dispersed in non-conductive organic material
    • H01B1/24—Conductive material dispersed in non-conductive organic material the conductive material comprising carbon-silicon compounds, carbon or silicon

Definitions

  • the present invention relates to a conductive polyamide resin composition
  • a conductive polyamide resin composition comprising a polyamide resin, conductive carbon black, and an olefin resin. More specifically, the present invention is not only excellent in conductivity, but also has fuel resistance, particularly excellent fuel resistance against alcohol-containing fuel, and is suitable for a fuel tank cap and the like. It is about.
  • Polyamide resin has excellent chemical resistance against gasoline and other organic solvents and alkaline liquids, and has high fluidity, heat resistance, and creep resistance, so it is used as an exterior material for automobiles and parts in engine rooms. It has been.
  • carbon black and other materials are added to impart electrical conductivity, suppress the generation and charging of static electricity, and have a function that can be discharged in a relatively short time. .
  • the present invention was devised in view of the current state of the prior art described above, and its purpose is to provide not only excellent conductivity but also fuel resistance in a conductive polyamide resin composition in which carbon black is blended with a polyamide resin.
  • it has excellent fuel resistance against alcohol-containing fuels, and it can be molded into molded products with high fluidity, excellent moldability, and excellent impact resistance, such as fuel tank caps.
  • An object of the present invention is to provide a conductive polyamide resin composition capable of providing the above.
  • the present inventors have found that an ethylene- ⁇ olefin copolymer blended for imparting impact resistance and dispersing conductive carbon black is swollen by a fuel containing alcohol.
  • the inventors have found that the distance between the carbon particles of the conductive carbon black is widened to the extent that the loss of conductivity occurs, and that the oil absorption of the conductive carbon black is a major cause. Then, it discovered that the said subject could be achieved by mix
  • the fibrous carbon (D) is a carbon nanotube and / or a milled carbon fiber having a fiber length of 200 ⁇ m or less.
  • the conductive polyamide resin composition according to [1] or [2].
  • the conductive polyamide resin composition of the present invention has a small decrease in conductivity even in an environment where it comes into contact with a fuel containing alcohol such as methanol or ethanol, and is a fuel system part of an automobile, such as a fuel tank cap, strainer, filter, etc. Can be used for parts such as valves.
  • a fuel containing alcohol such as methanol or ethanol
  • a fuel system part of an automobile such as a fuel tank cap, strainer, filter, etc.
  • the present invention will be specifically described below.
  • the conductive polyamide resin composition of the present invention reacts with polyamide resin (A) 84 to 40% by mass, conductive carbon black (B) 5 to 30% by mass, polyamide resin end groups and / or main chain amide groups.
  • the conductivity of the conductive polyamide resin composition of the present invention is such that the initial volume resistivity of a flat plate (100 mm ⁇ 100 mm ⁇ 2 mm (thickness)) obtained by injection molding is 1 ⁇ 10 5 ⁇ ⁇ cm or less.
  • the initial volume resistivity is preferably 5 ⁇ 10 4 ⁇ ⁇ cm or less.
  • the lower limit of the initial volume resistivity is not particularly limited, but is about 5 ⁇ 10 3 ⁇ ⁇ cm depending on the raw materials used.
  • the conductivity of the conductive polyamide resin composition of the present invention can suppress a decrease in conductivity even in an environment in contact with an alcohol-containing fuel, and the volume resistivity after exposure to CM15 fuel for 168 hours is 1 ⁇ . 10 7 ⁇ ⁇ cm or less can be achieved.
  • the volume resistivity after exposure to CM15 fuel for 168 hours is preferably 1 ⁇ 10 6 ⁇ ⁇ cm or less, and more preferably 5 ⁇ 10 5 ⁇ ⁇ cm or less.
  • the lower limit of the volume resistivity after the exposure is not particularly limited, but is about 5 ⁇ 10 4 ⁇ ⁇ cm depending on the raw materials used.
  • the volume resistivity can be measured by the method described in the Examples section below.
  • the Charpy impact strength is preferably 2.5 KJ / m 2 or more.
  • the upper limit of the Charpy impact strength is not particularly limited, but is about 20 KJ / m 2 from the raw materials used.
  • the Charpy impact strength can be measured by the method described in the Examples section below.
  • the conductive polyamide resin composition of the present invention preferably has excellent fluidity, and the melt index (ISO 1133 method, 250 ° C., load 10 kg) is preferably 0.5 g / 10 min or more, more preferably 1 g / 10. Min. Or more, more preferably 2 g / 10 min or more, particularly preferably 3 g / 10 min or more.
  • the melt index can be adjusted to an optimum range by adjusting the amount of each component described later.
  • the upper limit of the melt index is not particularly limited, but is about 20 g / 10 minutes from the raw materials used.
  • the melt index can be measured by the method described in the Examples section below.
  • the polyamide resin (A) used in the present invention has an acid amide bond (—CONH—) in the molecule.
  • Copolymers or blends thereof diamines such as hexamethylenediamine, nonamethylenediamine, undecamethylenediamine, dodecamethylenediamine, metaxylylenediamine, and dicarboxylic acids such as terephthalic acid, isophthalic acid, adipic acid, and sebacic acid
  • diamines such as hexamethylenediamine, nonamethylenediamine, undecamethylenediamine, dodecamethylenediamine, metaxylylenediamine
  • dicarboxylic acids such as terephthalic acid, isophthalic acid, adipic acid, and sebacic acid
  • examples thereof include, but are not limited to, a polymer or copolymer obtained by polycondensation of styrene and a copolymer thereof, or a blend thereof. From the viewpoint of availability, polyamide 6 and polyamide 66 are preferable.
  • These polyamide resins preferably have a number average molecular weight of 7000 to 30,000. If the number average molecular weight is less than 7000, the toughness tends to decrease, and if it exceeds 30,000, the fluidity tends to decrease. In terms of relative viscosity (measured in a 98% sulfuric acid solution), 1.5 to 4.0 is preferable.
  • the content of the polyamide resin (A) is 84 to 40% by mass, more preferably 70 to 50% by mass. When the polyamide resin is less than 40% by mass, the morphology structure in which the polyamide resin should be a continuous phase becomes unstable in the microstructure of the molded article made of the conductive polyamide resin composition.
  • the conductive carbon black (B) used in the present invention is not particularly limited, and ketjen black, acetylene black, furnace black, channel black, and the like can be used. Among these, ketjen black is particularly preferable because it exhibits excellent conductivity with a small content.
  • the content of the conductive carbon black (B) is preferably 5 to 30% by mass although it depends on the intended degree of conductivity.
  • the content of the conductive carbon black (B) is preferably 15 to 30% by mass, and more preferably 20 to 30% by mass.
  • These conductive carbon blacks are preferably dispersed in an amount of 80% by mass or more of the content in the polyamide resin that forms the continuous phase of the conductive polyamide resin composition.
  • the kneading step is extremely important, and functional groups such as carboxyl groups and hydroxyl groups present on the surface of the carbon black particles are also important.
  • the functional group on the surface of the carbon black acts to increase the affinity with the polyamide resin, and it becomes easy to disperse in the continuous phase of the polyamide resin.
  • the kneading conditions and the functional group concentration on the surface of the carbon black are not particularly limited, and 80% by mass or more of the carbon black content in the molded product of the conductive polyamide resin composition is a continuous phase. It is important that it is dispersed in a certain polyamide resin. By such dispersion of carbon black, a composition having excellent conductivity having a volume resistivity of 1 ⁇ 10 5 ⁇ ⁇ cm or less can be obtained. Other physical property values are also good.
  • the ethylene- ⁇ olefin copolymer (C) having a functional group capable of reacting with the terminal group and / or the amide group of the main chain of the polyamide resin used in the present invention (hereinafter referred to as a modified ethylene- ⁇ olefin copolymer or a modified olefin)
  • a modified ethylene- ⁇ olefin copolymer or a modified olefin examples of the polymer that serves as a basic skeleton of ethylene / propylene copolymer, ethylene / propylene / diene copolymer, ethylene / butene-1 copolymer, and ethylene / octene-1 copolymer
  • examples thereof include, but are not limited to, a polymer, an ethylene / hexene-1 copolymer, an ethylene / 4-methylpentene-1 copolymer, and an ethylene / cyclic olefin copolymer.
  • the content of the modified ethylene- ⁇ -olefin copolymer (C) is 3 to 30% by mass.
  • the content of the modified ethylene- ⁇ -olefin copolymer (C) is preferably 3 to 25% by mass, more preferably 3 to 20% by mass, and further preferably 3 to 15% by mass.
  • the functional group capable of reacting with the terminal group of the polyamide resin and / or the amide group of the main chain in the modified ethylene- ⁇ -olefin copolymer (C) used in the present invention is an amino group or a carboxyl group which is a terminal group of the polyamide resin.
  • a group capable of reacting with an amide group of the main chain specifically, examples thereof include a carboxylic acid group, an acid anhydride group, an epoxy group, an oxadoline group, an amino group, and an isocyanate group.
  • An anhydride group is preferred because it is most reactive.
  • the amount of functional groups is natural, but the larger the reaction, the more the reaction with the polyamide resin proceeds, and the ethylene- ⁇ -olefin copolymer is dispersed with a finer particle size in the continuous phase of the polyamide resin. Improves impact resistance of objects.
  • the method for producing an ethylene- ⁇ -olefin copolymer having these functional groups includes a method of reacting the above-mentioned compound having a functional group in the step of producing the copolymer, a copolymer pellet and a compound having a functional group, etc. Although there is a method of mixing and kneading with an extruder or the like, the method is not limited thereto.
  • the modified ethylene- ⁇ -olefin copolymer (C) used in the present invention is preferably in the form of particles having an average particle diameter of 2 ⁇ m or less and having a morphological structure dispersed in a polyamide resin as a continuous phase.
  • the above morphological structure can be obtained by reacting the polyamide resin and the modified ethylene- ⁇ -olefin copolymer in the production process of the composition.
  • High impact characteristics can be obtained by finely dispersing the modified ethylene- ⁇ -olefin copolymer in the polyamide resin with an average particle size of 2 ⁇ m or less.
  • the fibrous carbon (D) used in the present invention is preferably a carbon nanotube and / or a milled carbon fiber having a fiber length of 200 ⁇ m or less.
  • the carbon nanotubes are not limited to these, but the number average fiber diameter is 30 nm or less, preferably 1 to 30 nm, more preferably 5 to 20 nm.
  • the length is preferably 0.1 to 10 ⁇ m, more preferably 0.2 to 8 ⁇ m, and still more preferably 0.2 to 5 ⁇ m.
  • Examples of such commercially available carbon nanotubes include VGCF (registered trademark) -X (number average fiber diameter 15 nm, non-linear shape) manufactured by Showa Denko KK, NC2100, NC2101, NC1100 manufactured by Nanosil, and Meijo Co., Ltd. Examples thereof include MWNT MTC (fiber diameter 10 to 40 nm) made of nanocarbon.
  • the milled carbon fiber is not limited to these, but the number average fiber length is preferably 200 ⁇ m or less. If the number average fiber length exceeds 200 ⁇ m, the dispersibility becomes insufficient, and thus the effect of improving the fuel resistance becomes small.
  • PANEX35 manufactured by ZOLTEK Co., etc. can be mentioned.
  • These fibrous carbons are preferably dispersed in an amount of 80% by mass or more of the content in the polyamide resin forming the continuous phase of the conductive polyamide resin composition.
  • the kneading step is extremely important.
  • the content of the fibrous carbon (D) is 1 to 20% by mass, preferably 1 to 15% by mass, more preferably 1.3 to 13% by mass. If the fibrous carbon (D) is less than 1% by mass, the effect of improving the fuel resistance is small, and if it exceeds 20% by mass, the impact resistance is lowered.
  • the morphology of the conductive polyamide resin composition of the present invention is extremely important.
  • the dispersion average particle diameter of the finely dispersed modified ethylene- ⁇ -olefin copolymer (C) can be 2 ⁇ m or less by constituting a continuous phase in which the polyamide resin (A) is a matrix and reacting with the polyamide resin.
  • the conductive carbon black (B) has a content of 80% by mass or more dispersed in the polyamide resin (A) which is a continuous phase depending on the functional groups present on the particle surface and the kneading conditions.
  • the fibrous carbon (D) can be uniformly dispersed in the polyamide resin due to its affinity with the matrix polyamide resin, and can be close to the conductive carbon black (B) in the polyamide resin. It can contribute to the expression of electrical conductivity of objects. Since the fibrous carbon (D) and the conductive carbon black (B) are close to each other, it is possible to suppress a decrease in conductivity due to the fuel or the alcohol-containing fuel.
  • Conductive carbon black (B) and fibrous carbon (D) are previously dispersed in a polyamide resin (A), and then an ethylene- ⁇ olefin copolymer (C) having a reactive functional group capable of reacting with the polyamide resin. It is effective to formulate a conductive polyamide resin composition.
  • the conductive polyamide resin composition of the present invention includes copper, which is a weather resistance improving material used in ordinary polyamide resin compositions.
  • Oxides and / or alkali metal halides, light or heat stabilizers may contain phenolic antioxidants, phosphorus antioxidants, mold release agents, crystal nucleating agents, lubricants, pigments, dyes, and the like.
  • the conductive polyamide resin composition of the present invention preferably occupies 80% by mass or more and 90% by mass or more in total of the components (A), (B), (C) and (D). Is more preferable, and more preferably 95% by mass or more.
  • the conductive polyamide resin composition of the present invention cannot form a stable morphological structure simply by mixing each component and kneading with an extruder, and kneading by a special method is recommended.
  • a polyamide resin (A), conductive carbon black (B), and fibrous carbon (D) are melted and kneaded in a melt kneader (for example, a twin screw extruder, a melt reaction kettle, etc.) After carbon black and fibrous carbon are uniformly dispersed, the modified ethylene- ⁇ -olefin copolymer (C) and other additives as necessary are further melt-kneaded.
  • the polyamide conductive resin composition having the morphological structure of the present invention can be stably produced.
  • the production of the polyamide conductive resin composition of the present invention is not limited to such a specific blend and melt kneading method, and other blends and melt methods can be used as long as the above composition and morphology structure are obtained.
  • the composition of the present invention can be produced.
  • volume resistivity was measured with a digital multimeter (TR-6843, manufactured by Advantest Corp.) with terminals connected to both ends of the 100 mm ⁇ 100 mm ⁇ 2 mm (thickness) plate obtained by injection molding at right angles to the gate position. .
  • the measurement specimen was vacuum-dried at 70 ° C. for 12 hours and then seasoned in an atmosphere of 20 ° C. and 50% RH for 24 hours.
  • a frozen section was prepared from the center of a 100 mm ⁇ 100 mm ⁇ 2 mm (thickness) plate obtained by injection molding.
  • a frozen section having a cross section perpendicular to the resin flow direction of the sample was prepared, stained with 5% phosphotungstic acid aqueous solution for 30 minutes, After carbon deposition, the photo was taken with a JEM2010 transmission electron microscope manufactured by JEOL Ltd. at an acceleration voltage of 200 KV and a direct magnification of 5000 times. Subsequently, the average particle diameter was calculated
  • the diameter converted to a sphere was taken as the particle diameter. Conversion was made the average of the major axis and minor axis of the ellipse as the diameter of the sphere.
  • the conductive carbon black (B) is present in the continuous phase by counting the number of all carbon black particles in the photograph and the number of carbon black particles in the continuous phase with an image analyzer. The percentage% of the number of particles of the conductive carbon black (B) to be made was mass%.
  • the fibrous carbon (D) was distinguished from the conductive carbon black by the difference in shape (the fibrous carbon (D) was fibrous and the conductive carbon black (B) was particulate). Similar to the conductive carbon black (B), the location of the fibrous carbon (D) was determined by counting the number of fibrous materials.
  • Polyamide resin A-1: Toyobo Nylon T-840 (manufactured by Toyobo Co., Ltd., polyamide 6, relative viscosity 2.2) Conductive carbon black (B) B-1: Furnace Carbon 100 (manufactured by Lion Corporation) B-2: Ketjen Carbon EC (manufactured by Lion Corporation) Modified ethylene- ⁇ olefin copolymer (C) C-1: Modified Olefin Copolymer TAFMER (registered trademark) MH7020 (Mitsui Chemicals Co., Ltd.
  • Fibrous carbon D-1: Carbon nanotube manufactured by Nanocyl NC-7000 Diameter 10-15 nm, Length 1.5 ⁇ m D-2: Milled carbon fiber manufactured by ZOLTEK PANEX35 MF MF200 Average fiber length 150 ⁇ m D ': Carbon fiber PANEX35 average fiber length 6mm made by ZOTEK

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Dispersion Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne une composition de résine polyamide conductrice qui permet de mouler un article moulé qui présente non seulement d'excellentes propriétés de conduction, mais qui combine également une résistance au carburant, particulièrement une excellente résistance au carburant vis-à-vis d'un carburant comprenant de l'alcool, qui est dotée également d'une fluidité élevée et d'une excellente aptitude au moulage, et qui se révèle d'une excellente résistance aux chocs. Cette composition de résine polyamide conductrice comprend : 84 à 40% en masse d'une résine polyamide (A) ; 5 à 30% en masse d'un noir de carbone conducteur (B) ; 3 à 30% en masse d'un copolymère éthylène – αoléfine qui possède un groupe fonctionnel réactif réagissant avec un groupe terminal et/ou un groupe amide de chaîne principale de la résine polyamide ; et 1 à 20% en masse d'un carbone fibreux.
PCT/JP2018/004169 2017-02-09 2018-02-07 Composition de résine polyamide conductrice WO2018147315A1 (fr)

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JP2018510895A JPWO2018147315A1 (ja) 2017-02-09 2018-02-07 導電性ポリアミド樹脂組成物

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JP2017-022170 2017-02-09
JP2017022170 2017-02-09

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WO2018147315A1 true WO2018147315A1 (fr) 2018-08-16

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006510763A (ja) * 2002-12-19 2006-03-30 ランクセス ドイチュラント ゲゼルシャフト ミット ベシュレンクテル ハフツング カーボンブラックおよびカーボンナノファイバーを含有する導電性の熱可塑性樹脂
JP2007507562A (ja) * 2003-09-29 2007-03-29 ゼネラル・エレクトリック・カンパニイ 導電性熱可塑性組成物、製造方法、及びかかる組成物から導かれる物品
WO2009151145A1 (fr) * 2008-06-10 2009-12-17 宇部興産株式会社 Nouvelle composition de résine de polyamide et produit contenant de la résine de polyamide
WO2010122886A1 (fr) * 2009-04-20 2010-10-28 三菱化学株式会社 Composition conductrice de résine thermoplastique, compositions conductrices de résine polyamide et film conducteur de polyamide
WO2012098840A1 (fr) * 2011-01-17 2012-07-26 株式会社クラレ Composition de résine et article moulé la contenant
WO2013061650A1 (fr) * 2011-10-28 2013-05-02 宇部興産株式会社 Composition de résine polyamide

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006510763A (ja) * 2002-12-19 2006-03-30 ランクセス ドイチュラント ゲゼルシャフト ミット ベシュレンクテル ハフツング カーボンブラックおよびカーボンナノファイバーを含有する導電性の熱可塑性樹脂
JP2007507562A (ja) * 2003-09-29 2007-03-29 ゼネラル・エレクトリック・カンパニイ 導電性熱可塑性組成物、製造方法、及びかかる組成物から導かれる物品
WO2009151145A1 (fr) * 2008-06-10 2009-12-17 宇部興産株式会社 Nouvelle composition de résine de polyamide et produit contenant de la résine de polyamide
WO2010122886A1 (fr) * 2009-04-20 2010-10-28 三菱化学株式会社 Composition conductrice de résine thermoplastique, compositions conductrices de résine polyamide et film conducteur de polyamide
WO2012098840A1 (fr) * 2011-01-17 2012-07-26 株式会社クラレ Composition de résine et article moulé la contenant
WO2013061650A1 (fr) * 2011-10-28 2013-05-02 宇部興産株式会社 Composition de résine polyamide

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