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WO2004058885A1 - Composition de resine a base de polyoxymethylene destinee a des grilles de haut-parleur - Google Patents

Composition de resine a base de polyoxymethylene destinee a des grilles de haut-parleur Download PDF

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Publication number
WO2004058885A1
WO2004058885A1 PCT/KR2003/002913 KR0302913W WO2004058885A1 WO 2004058885 A1 WO2004058885 A1 WO 2004058885A1 KR 0302913 W KR0302913 W KR 0302913W WO 2004058885 A1 WO2004058885 A1 WO 2004058885A1
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WIPO (PCT)
Prior art keywords
parts
weight
polyoxymethylene resin
resin
composition
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.)
Ceased
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PCT/KR2003/002913
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English (en)
Inventor
Yong-Seon Park
Mok-Keun Lim
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kolon Industries Inc
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Kolon Industries Inc
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 Kolon Industries Inc filed Critical Kolon Industries Inc
Priority to AU2003289582A priority Critical patent/AU2003289582A1/en
Publication of WO2004058885A1 publication Critical patent/WO2004058885A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L59/00—Compositions of polyacetals; Compositions of derivatives of polyacetals
    • C08L59/04—Copolyoxymethylenes
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/08—Stabilised against heat, light or radiation or oxydation

Definitions

  • the present invention relates to polyoxymethylene resin compositions, and more specifically, to a polyoxymethylene resin composition suitable for use in the speaker grille of automobiles obtained through a long and twisting injection path, which is advantageous in terms of color consistency even though being exposed to light, non-glossiness, and high flowability.
  • a polyoxymethylene resin (hereinafter, abbreviated to 'POM resin') has high mechanical strength, and is superior in rigidity, creep resistance, chemical resistance, and sliding characteristics.
  • 'POM resin' has high mechanical strength, and is superior in rigidity, creep resistance, chemical resistance, and sliding characteristics.
  • the above resin has been widely utilized as a representative engineering resin in industrial fields, including automobile parts, and electric and electronic parts.
  • surface colors change and cracks are generated due to the low weather resistance of the resin per se. Therefore, there is required improvement of weather resistance of the resin.
  • discoloration is regarded as being worse, rather than the reduction of physical properties.
  • the attractive exterior parts require non-glossiness, because such property provides high quality, in addition to a courteous and generous feeling, and functions to prevent sunlight from being reflected so as to decrease stimulation to the naked eye.
  • the exterior parts should have better outer appearance and need external decorations.
  • the resin since the injection path of the molten resin to prepare such exterior parts is lengthened, the resin should have high flowability.
  • molded articles have drastically decreased strength. Typically represented by the molded article, there is a speaker grille used for automobiles.
  • end products may be easily broken, due to low impact strength.
  • a resin having a medium viscosity is used to improve the flowability.
  • the composition obtained by the above methods is disadvantageous in terms of drastically reduced mechanical properties of the POM resin, in particular, strength and elastic module, and low thermal stability upon molding.
  • an inorganic filler such as calcium carbonate, calcium silicate, clay or talc
  • a POM resin Japanese Patent Laid-open Publication No. Sho. 64- 54053
  • the used inorganic filler has a particle size of 5 ⁇ m or more, resulting in significantly lowered dispersibility and non-glossiness of the POM resin.
  • a polyoxymethylene resin is mixed with specific sorbitan fatty acid ester, a triazine- and hindered phenol-based light stabilizer, a polyoxyalkylene resin, an inorganic filler having a particle size of 5 ⁇ m or less, and divalent aliphatic alcohol, whereby the resultant polyoxymethylene resin composition is suitable for use in speak grille, with a melt index of 30-60 g/10 min, preferably 40-50 g/10 min, a surface glossiness of 20% or less, and a concentration of residual formaldehyde of 20 ppm or less.
  • a polyoxymethylene resin composition for use in the speaker grille comprising (a) 100 parts by weight of a polyoxymethylene resin, (b) 0.1-3 parts by weight of sorbitan fatty acid ester, and (c) 0.1-5.0 parts by weight of polyalkyleneglycol or alkylenepolyether-ester block copolymer, with a melt index of 30-60 g/lOmin, and preferably, 40-50 g/10 min, a surface glossiness of 20% or less, and a concentration of residual formaldehyde not more than 20 ppm.
  • a polyoxymethylene resin composition for a speaker grille consisting mainly of a polyoxymethylene resin, with sorbitan fatty acid ester and polyalkyleneglycol or alkylenepolyether-ester block copolymer as essential components.
  • the POM resin is preferably an oxymethylene homopolymer or an oxymethylene copolymer containing at least one oxyalkylene unit of 2-8 carbon atoms in an oxymethylene unit-containing polymer main chain.
  • the oxymethylene homopolymer is preferably an oxymethylene homopolymer stabilized by substituting an ester group or an ether group for an unstable hydroxy terminal.
  • the oxymethylene homopolymer is prepared by polymerizing anhydrous formaldehyde in an organic solvent containing organic amine, an organic or inorganic compound, metal hydroxide and a basic polymerization catalyst, to prepare a polymer, which is then washed and heated in the presence of sodium acetate, to obtain an acetylated terminal thereof, but is not particularly limited thereto.
  • the oxymethylene copolymer is prepared, but is not particularly limited to, by dissolving trioxane as a cyclic oligomer of formaldehyde and at least one of cyclic ethers as a copolymerizable component in cyclohexane or benzene, followed by bulk polymerization in the presence of a polymerization catalyst selected from the group consisting of boron trifluoride, boron trifluoride hydrate, a coordinated compound of boron trifluoride with an oxygen atom or diboron atom-containing organic compound, and mixtures thereof, and then decomposing and eliminating an unstable terminal of the polymer.
  • a polymerization catalyst selected from the group consisting of boron trifluoride, boron trifluoride hydrate, a coordinated compound of boron trifluoride with an oxygen atom or diboron atom-containing organic compound, and mixtures thereof, and then decomposing and eliminating an unstable terminal of the polymer.
  • the cyclic ether component is pre- mixed with the polymerization catalyst and then placed into a self-cleaning type stirrer, followed by adding a deactiviating agent to the polymer to remove catalytic activity from the polymer and then decomposing and eliminating the unstable terminal of the polymer, thereby obtaining a desired polymer.
  • sorbitan fatty acid ester is commercially available, and is exemplified by Tech-Lube, purchased from Technique Product Co. Ltd., USA. Sorbitan fatty acid ester is used in an amount of 0.1-3 parts by weight, and preferably, 0.3-2 parts by weight, based on 100 parts by weight of the POM resin. If the amount is less than 0.1 parts by weight, the molten resin has low flowability. Meanwhile, if the amount exceeds 3 parts by weight, improvements become insignificant. Further, upon molding, large quantities of gas are generated, and thus, it is difficult to perform a molding process. Also, preparation costs increase, therefore negating economic benefits.
  • polyalkyleneglycol functions to prevent cracks from occurring on the surfaces of molded articles, and is used in the amount of 0.1-5 parts by weight, based on 100 parts by weight of the POM resin. When the amount is less than 0.1 parts by weight, adding effects of the above component are not exhibited. Whereas, if the amount exceeds 5 parts by weight, physical properties decrease and a harmful gas is generated upon molding.
  • the polyalkyleneglycol suitable for use in the polyoxymethylene resin composition is preferably polyethyleneglycol having a number average molecular weight of 5,000-50,000. If the number average molecular weight of polyethyleneglycol is smaller than 5,000, whitening phenomenon occurs on the surface of the molded article.
  • alkylenepolyether-ester block copolymer is used to obtain higher functionality, instead of polyalkyleneglycol.
  • the alkylenepolyether-ester block copolymer is a block copolymer comprising a hard segment composed a butylene terephthalate unit and a soft segment composed of a poly(ethylene oxide)terephthalate unit.
  • the dicarboxylic acid component constituting the hard segment comprises terephthalic acid alone, or 70 mol% or more of terephthalic acid alone, or 70 mol% or more of terephthalic acid and 30 mol% or less of aromatic dicarboxylic acid selected from the group consisting of isophthalic acid, phthalic acid, naphthalene-2,6-dicarboxylic acid, diphenyl-4,4' -dicarboxylic acid, 3- sulfoneisophthalic acid, and mixtures thereof, and alicyclic dicarboxylic acid selected from the group consisting of oxalic acid, succinic acid, adipic acid, azellic acid, sebacic acid, dodecanoic acid, dimer acid, and mixtures thereof.
  • aromatic dicarboxylic acid selected from the group consisting of isophthalic acid, phthalic acid, naphthalene-2,6-dicarboxylic acid, diphenyl-4,4' -dica
  • the diol component constituting the hard segment is composed mainly of 1,4-buthanediol. That is, the diol component comprises 1,4-butanediol alone, or 50 moP/o or more of 1,4-butanediol and 50 mol% or less of a copolymerizable component selected from the group consisting of ethyleneglycol, diethyleneglycol, propyleneglycol, 1,6-hexanediol, 1,10-decanediol, 1,4- dihydroxymethyl cyclohexane, bis(4-hydroxyethoxyphenyl)methane, neopentylglycol, and mixtures thereof.
  • a copolymerizable component selected from the group consisting of ethyleneglycol, diethyleneglycol, propyleneglycol, 1,6-hexanediol, 1,10-decanediol, 1,4- dihydroxymethyl cyclohexane, bis(
  • the dicarboxylic acid constituting the soft segment includes mainly terephthalic acid.
  • the dicarboxylic acid of the soft segment includes terephthalic acid alone, or 70 moP/o or more of terephthalic acid and 30 moP/o or less of dicarboxylic acid as the copolymerizable component, as in the dicarboxylic acid of the hard segment.
  • the copolymerizable component used for the soft segment may include dicarboxylic acid as in the hard segment.
  • Poly(ethylene oxide)glycol constituting the poly(ethylene oxide)terephthalate unit of the soft segment is exemplified by poly(ethylene oxide)glycol having a number average molecular weight of 800-20,000.
  • poly(ethylene oxide)glycol having a number average molecular weight of 5,000-15,000 is used, and more preferably, poly(ethylene oxide)glycol having a number average molecular weight of 8,000-10,000 is used in view of compatibility with the POM resin. If the number average molecular weight is smaller than 800, the prevention effects of surface cracks become insignificant. Meanwhile, if the number average molecular weight is larger than 20,000, compatibility with the butyl terephthalate unit of the hard segment becomes inferior, and thus, the uniform polyether-ester block copolymer cannot be prepared.
  • the poly(ethylene oxide)carboxylate unit constitutes 40- 85 wt%, and preferably, 70-85 wt% in the polyether-ester block copolymer.
  • the amount of the poly(ethylene oxide)carboxylate unit is larger than 85 wt%, it is difficult to polymerize the polyether-ester block copolymer, and also, the mechanical strength of the resulting composition decreases.
  • the preparation of the polyether-ester block copolymer is not particularly limited and accords to known methods.
  • the polyether-ester block copolymer is prepared by introducing (a) terephthalic acid (or dimethyl terephthalate), (b) 1,4-butanediol and (c) poly(ethylene oxide)glycol into a reaction container equipped with a rectification column, followed by esterification or transesterification under atmospheric pressure or increased pressure and then polymerization under atmospheric pressure or decreased pressure.
  • the polyether-ester block copolymer is prepared by adding (a) terephthalic acid (or dimethyl terephthalate), (b) 1,4-butanediol and (c) poly(ethylene oxide)glycol to an oligomer, followed by polymerization under atmospheric pressure or reduced pressure.
  • the polyoxymethylene resin composition of the present invention further includes an inorganic filler, a benzotriazine- and/or steric hindered amine-based light stabilizer, and divalent aliphatic alcohol, as selective additives.
  • the preferable inorganic filler is selected from the group consisting of talc, clay, mica, wollastinite, asbestos, glass bead, and mixtures thereof, which has a particle size of 5 ⁇ m or less.
  • the inorganic filler which is partially or entirely treated with an amino silane coupling agent, is preferably used.
  • talc and clay function to increase non-glossiness of the surface when being added to the POM resin.
  • the inorganic filler is used in the amount of 1-5 parts by weight, and preferably, 2-4 parts by weight, based on 100 parts by weight of the POM resin. If the amount is less than 1 part by weight, surface glossiness increases. On the other hand, if the amount is larger than 5 parts by weight, mechanical strength, in particular, impact strength, decreases.
  • the light stabilizer is exemplified by benzotriazine-based stabilizers, such as 2-[2-hydroxy-3,5-bis( ⁇ , ⁇ -dimethylbenzyl)phenyl]benzotriazyl, 2-(3,5- dibutyl-2-hydroxyphenyl)benzotriazyl, 2-(4,6-diphenyl-l,3,5-triazin-2-yl)-5- [(hexyl)oxy] -phenol, and 2-(2-hydroxy-benzotriazol-2-yl)-4,6-bis (1-ethyl-l- phenylethyl)phenol; and steric hindered amine-based stabilizers, such as 4- acetoxy-2,2,6,6-tetramethylpiperidine, 4-stearoyloxy-2,2,6,6- tetramethylpiperidine, 4-acryloyloxy-2,2,6,6-tetramethylpiperidine, 4-methoxy- 2,2,6, 6-tetramethylpiperidine, 4-benz
  • the above light stabilizer may be used alone or in mixtures thereof.
  • the light stabilizer is used in the form of a mixture of the benzotriazine-based stabilizer and the steric hindered amine-based stabilizer.
  • the light stabilizer is used in the amount of 0.01-5 parts by weight, and preferably, 0.05-3 parts by weight, based on 100 parts by weight of the POM resin. If the amount is smaller than 0.01 parts by weight, the resultant composition is low in light stability. Whereas, if the amount is larger than 5 parts by weight, the above component may be deposited as a white powder phase on the surface of the POM resin.
  • the divalent aliphatic alcohol reacts with formaldehyde generated by heat aging of the POM resin, and thus, functions to prevent a secondary decomposition due to the formaldehyde. As well, the alcohol component acts to remove formaldehyde generated upon processing through the reaction with formaldehyde, thereby decreasing the amount of formaldehyde in the molded article, thus reducing the offensive odor attributed to formaldehyde.
  • the divalent fatty acid alcohol is exemplified by glyceryl monostearate, or pentaerythritol fatty acid ester. Instead of the divalent fatty acid alcohol, polyamide copolymer having a melting point less than 190°C may be used.
  • the divalent aliphatic alcohol is used in the amount of 0.01-5.0 parts by weight, based on 100 parts by weight of the POM resin.
  • the use of the divalent aliphatic alcohol less than 0.01 parts by weight results in insignificant adding effects, whereas the use of the divalent aliphatic alcohol larger than 5 parts by weight results in drastically decreased physical properties and the generation of gas, thus negating economic benefits.
  • an additive known in the art may be added to the present composition in the range of not harming the purposes of the present invention.
  • the resulting polyoxymethylene resin composition has a melt index of 30-60 g/10 min, and in particular, 40-50 g/10 min, which can be used to prepare a speaker grille.
  • the articles molded from the above composition have a surface glossiness of 20% or less.
  • satin-embossed processing or leather grain embossing is performed to improve the feel of the interior parts.
  • the embossed surface acts to decrease the surface glossiness of the POM resin.
  • automobile manufacturing companies have evaluated residual formaldehyde causing the offensive odor in molded articles, of an interior material of automobiles. The offensive odor is typically evaluated by using the olfactory sense of various persons.
  • the offensive odor can be eliminated by reducing the amount of residual formaldehyde. From the experiments, it can be found that the amount of formaldehyde not more than 20 ppm leads to virtually no offensive odor from formaldehyde in molded articles and during the molding. Thereby, the resin composition can be prepared to have the concentration of residual formaldehyde of 20 ppm or less in the molded articles.
  • the polyoxymethylene resin composition prepared by the present invention is evaluated according to the following properties.
  • a dumbbell-shaped test piece according to ASTM D638 and a 80x80x3 mm square plate were injection molded under the conditions of cylinder temperature of 190°C, a mold temperature of 80°C and a molding cycle of 20 sec, by use of an injection molding machine having a 60 ton injection capability.
  • a low viscosity polyoxymethylene resin (Kocetal K700 having a melt index of 27g/10min, purchased from KTP Co. Ltd., Korea) was dried at 80°C for
  • the resin composition was sufficiently dried, and a test piece for measurement of various physical properties was injection molded at 190°C and measured for mechanical properties and weather resistance.
  • Each component (based on 100 parts by weight of the polyoxymethylene resin) in polyoxymethylene resin compositions of examples and comparative examples prepared according to the above procedure are shown in Table 1, below.
  • the results of the measured properties are given in Table 2, below.
  • E-1 2-(4,6-diphenyl-l,3,5-triazin-2-yl)-5-[(hexyl)oxy]-phenol
  • E-2 bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate
  • D-l Talc having an average particle size of 4 ⁇ m
  • D-2 Clay having an average particle size of 4 ⁇ m
  • Polyalkyleneglycol is polyethyleneglycol having a number average molecular weight of 10,000.
  • the present invention provides a polyoxymethylene resin composition, which can be usefully applied for molded articles of fields requiring weather resistance and low glossiness, and high flowability, for example, interior parts of automobiles, such as speaker grilles, air conditioner parts and various clips and buttons, mechanical parts, electric and electronic parts, office instruments such as computer, building pipes, and general goods.

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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)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne une composition de résine à base de polyoxyméthylène, comprenant une résine de polyoxyméthylène, des esters d'acides gras de sorbitane, des copolymères blocs d'ester polyéther d'alkylène ou polyalkylèneglycol, pouvant être appliqués de façon utile à des articles moulés de domaines nécessitant une résistance aux conditions climatiques et une faible brillance, ainsi qu'une aptitude élevée à l'écoulement, par exemple, des parties internes d'automobile, telles que des grilles de haut-parleur, des parties d'air conditionné et divers boutons et pinces, des parties mécaniques, des parties électriques et électroniques, des instruments de bureau tels que un ordinateur, des conduites de construction, ainsi que des biens d'ordre général.
PCT/KR2003/002913 2002-12-31 2003-12-30 Composition de resine a base de polyoxymethylene destinee a des grilles de haut-parleur Ceased WO2004058885A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003289582A AU2003289582A1 (en) 2002-12-31 2003-12-30 Polyoxymethylene resin composition for speaker grille

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20020088059A KR100553396B1 (ko) 2002-12-31 2002-12-31 자동차의 스피커 그릴용 폴리옥시메틸렌 수지 조성물
KR10-2002-0088059 2002-12-31

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WO2004058885A1 true WO2004058885A1 (fr) 2004-07-15

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013060520A (ja) * 2011-09-13 2013-04-04 Asahi Kasei Chemicals Corp 寸法安定性に優れるポリアセタール樹脂成形体

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH024849A (ja) * 1988-06-22 1990-01-09 Toray Ind Inc ポリアセタール樹脂組成物
JPH04168144A (ja) * 1990-10-31 1992-06-16 Toray Ind Inc ポリアセタール樹脂組成物
US5212222A (en) * 1991-02-04 1993-05-18 Polyplastics Co., Ltd. Melt-stable recyclable carbon black-laden polyacetal resin molding compositions and molded articles formed of the same
JPH1160893A (ja) * 1997-08-21 1999-03-05 Polyplastics Co ポリオキシメチレン組成物
US6391956B1 (en) * 1998-02-24 2002-05-21 Asahi Kasei Kabushiki Kaisha Polyoxymethylene resin composition

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH024849A (ja) * 1988-06-22 1990-01-09 Toray Ind Inc ポリアセタール樹脂組成物
JPH04168144A (ja) * 1990-10-31 1992-06-16 Toray Ind Inc ポリアセタール樹脂組成物
US5212222A (en) * 1991-02-04 1993-05-18 Polyplastics Co., Ltd. Melt-stable recyclable carbon black-laden polyacetal resin molding compositions and molded articles formed of the same
JPH1160893A (ja) * 1997-08-21 1999-03-05 Polyplastics Co ポリオキシメチレン組成物
US6391956B1 (en) * 1998-02-24 2002-05-21 Asahi Kasei Kabushiki Kaisha Polyoxymethylene resin composition

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013060520A (ja) * 2011-09-13 2013-04-04 Asahi Kasei Chemicals Corp 寸法安定性に優れるポリアセタール樹脂成形体

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Publication number Publication date
KR100553396B1 (ko) 2006-02-16
AU2003289582A1 (en) 2004-07-22
KR20040061765A (ko) 2004-07-07

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