WO2004096881A1 - Matériau résinique pour article formé à section transversale profilée - Google Patents

Matériau résinique pour article formé à section transversale profilée Download PDF

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Publication number
WO2004096881A1
WO2004096881A1 PCT/JP2004/006327 JP2004006327W WO2004096881A1 WO 2004096881 A1 WO2004096881 A1 WO 2004096881A1 JP 2004006327 W JP2004006327 W JP 2004006327W WO 2004096881 A1 WO2004096881 A1 WO 2004096881A1
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WO
WIPO (PCT)
Prior art keywords
resin material
material according
section
mol
polyoxymethylene copolymer
Prior art date
Application number
PCT/JP2004/006327
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English (en)
Japanese (ja)
Inventor
Hidetoshi Okawa
Daisaku Ikeda
Original Assignee
Polyplastics Co., Ltd.
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 Polyplastics Co., Ltd. filed Critical Polyplastics Co., Ltd.
Priority to JP2005505955A priority Critical patent/JPWO2004096881A1/ja
Publication of WO2004096881A1 publication Critical patent/WO2004096881A1/fr

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    • 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
    • C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
    • 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

Definitions

  • the present invention relates to a resin material which is made of a specific polyoxymethylene copolymer and has excellent mechanical properties and is suitable for producing a molded article having a good irregular cross-sectional shape, and a molded article thereof.
  • a profile extrusion molding method is known as a technique for molding a resin material into a long body having a complicated cross-sectional shape.
  • Such a profile extrusion molding method is performed, for example, as follows. That is, the resin material is heated, melted and kneaded by an extruder and extruded through a die for profile extrusion provided at the extruder outlet. It is cooled and solidified while shaping into a shape to obtain the desired extruded molded product. At this time, by appropriately changing the shape or sizing means of the profile extrusion die or sizing die, it is possible to obtain profile extrusion products having various cross-sectional shapes.
  • a polyoxymethylene resin having a polymer skeleton composed mainly of repeating oxymethylene units is known to have high crystallinity and to be excellent in rigidity, strength, chemical resistance, solvent resistance, and the like. Because of its high crystallization speed and fast molding cycle, it is widely used as an injection molding material in the field of mechanical parts for automobiles and electrical equipment.
  • polyoxymethylene resin has excellent properties, but polyoxymethylene resin has high crystallinity, high crystallization speed, and large molding shrinkage.
  • drawdown occurs or distortion occurs due to shrinkage during cooling and solidification, and the product is deformed, and it is extremely difficult to form a desired cross-sectional shape.
  • profile extrusion molding using a polyoxymethylene resin has hardly been performed in the past, and such behavior in the profile extrusion molding of a polyoxymethylene resin is based on the polyoxymethylene resin described above. Due to such essential properties as described above, it was considered difficult to improve it to one suitable for profile extrusion, and it has hardly been studied.
  • a hollow extruded product for a pen tip having an ink flow path is known (for example, Japanese Patent Application Laid-Open No. 59-22749). No. 8 and Japanese Patent Application Laid-Open No. H08-142465).
  • the techniques disclosed in these documents are characterized by the selection of materials in consideration of the performance of the pen tip, and are particularly useful for profile extrusion, especially for profiles with complex cross-sections and for profiles with large cross-sections.
  • No disclosure is made of a polyoxymethylene resin material that can be particularly effectively applied to the above. Disclosure of the invention
  • An object of the present invention is to solve the above problems and provide a resin material comprising a polyoxymethylene copolymer capable of efficiently producing a deformed cross-section molded article having small distortion and excellent dimensional accuracy. It is in.
  • the present inventors have conducted intensive studies in order to achieve the above object, and as a result, using a resin material made of a specific polyoxymethylene copolymer having a controlled crystallization rate, improved the profile extrusion processability, The present inventors have found that an excellent molded product with little distortion can be obtained, and have reached the present invention.
  • the present invention comprises, in a polymer chain mainly composed of repeating oxymethylene units, 1.5 to 10 mol of oxyalkylene units represented by the following general formula (1) per 100 mol of oxymethylene units, and a melt index (190 ° C.) It is a resin material composed of a polyoxymethylene copolymer having a load of 2160 g) of 0.3 to 20 g / 10 minutes and suitable for producing molded articles having an irregular cross section.
  • R 2 is hydrogen, an alkyl group having 1 to 8 carbon atoms, selected from an organic group having an organic group, phenyl group, phenylene Le radicals having alkyl Le group having 1 to 8 carbon atoms, R 2 May be the same or different, and m represents an integer of 2 to 6.
  • the present invention also provides an application for producing a molded article having an irregular cross section of the above resin material and a method for producing a molded article having an irregular cross section including molding the above resin material. Detailed description of the invention
  • the resin material of the present invention comprises a polyoxymethylene unit containing 1.5 to 10 mol of oxyalkylene units represented by the above general formula (1) per 100 mol of oxymethylene units in one chain of a polymer mainly composed of repeating oxymethylene units. It consists of a polymer.
  • the ratio of the oxyalkylene unit represented by the general formula (1) must be 1.5 to 10 mol per 100 mol of the oxymethylene unit, and is preferably oxymethylene. It is preferably 2 to 8 mol per 100 mol of unit, particularly preferably 2 to 5 mol per 100 mol of oxymethylene unit.
  • the proportion of the oxyalkylene unit represented by the general formula (1) is reduced, the crystallization rate of the polyoxymethylene copolymer is increased, and when extruding a molded article having an irregular cross section, a die of an extruder is used.
  • the molten resin extruded through is shaped into a desired cross-sectional shape by a sizing die and solidified before being cooled, so that a desired shape cannot be obtained. Also, due to the high solidification rate, the strain in the molded product generated during the solidification process becomes large, so that a deformed shape may be formed. Conversely, when the proportion of the oxyalkylene unit represented by the general formula (1) is increased, the crystallinity of the polyoxymethylene copolymer decreases, and the molded article made of such a copolymer has a high strength and elastic modulus. Etc. are low.
  • the polyoxymethylene copolymer used in the present invention has a melt index (Ml) of 0.3 to 20 g // 10 measured at 190 ° C under a load of 2160 g according to ASTM D-1238. Min., Preferably 0.5 to 10 g / 10 min, particularly preferably 0.5 to 5 g / 10 min. If the melt index (M l) is too small, the load during the melt extrusion process will increase, making extrusion difficult. Conversely, if the melt index (M l) becomes too large, the resin will be cut down due to the resin opening. It becomes unstable.
  • the method for producing the above-mentioned polyoxymethylene copolymer used in the present invention is not particularly limited.
  • the polymerization apparatus any of known apparatuses such as a batch type and a continuous type can be used.
  • the introduction ratio of the oxyalkylene unit represented by the general formula (1) is adjusted by the amount of the comonomer to be copolymerized.
  • the melt index (Ml) can be adjusted by the amount of a chain transfer agent used during polymerization, for example, methylal or the like.
  • the melt index of the obtained copolymer decreases as the amount of the chain transfer agent added decreases, and increases as the amount increases.
  • the melt index is affected by impurities such as water and methanol contained in the raw material monomer and comonomer, and the type, shape, size, and polymerization conditions of the polymerization machine. It is difficult to unambiguously determine the absolute amount of chain transfer agent required to obtain the copolymer, and the chain transfer is performed so that the desired melt index is obtained while trying to produce the copolymer. Increase or decrease the amount of agent added.
  • Examples of the cyclic ether compound or cyclic formal compound used as a comonomer include ethylene oxide, propylene oxide, butylene oxide, styrene oxide, oxetane, tetrahydrofuran, trioxepane, 1,3-dioxolan, propylene glycol formal, diethylene glycol formal, Examples include triethylene glycol formal, 1,4-butanediol formal, 1,5-pentanediol formal, 1,6-hexanediol formal, among which ethylene oxide, 1,3-dioxolan, diethylene glycol formal, 1,4-butanediol formal is preferred.
  • the polyoxymethylene copolymer used in the present invention may have a branched or crosslinked structure.
  • a small amount of a monofunctional or bifunctional or higher glycidyl compound other than those described above is added and copolymerized. It may be polymerized.
  • the polyoxymethylene copolymer obtained by polymerization is subjected to catalyst deactivation treatment, removal of unreacted monomers, washing and drying of the polymer, stabilization of unstable terminal portions, etc., followed by various stabilizers And then put to practical use by performing stabilization treatment and the like by blending the same.
  • Representative stabilizers include hindered phenol compounds, nitrogen-containing compounds, hydroxides of alkali or alkaline earth metals, inorganic acid salts, carboxylate salts, and the like.
  • the polyoxymethylene copolymer thus obtained and used in the present invention preferably has an amount of hemiformal terminal groups detected by ⁇ -NMR of 0 to 4 mmol / kg, particularly preferably 0 to 2 imol. / kg. If the amount of the hemiformal terminal group exceeds 4 ol / kg, problems such as foaming due to decomposition of the polymer may occur during melt processing.
  • impurities, particularly water, in the total amount of monomers and comonomer to be subjected to the polymerization be 20 ppm or less, particularly preferably 10 ppm or less.
  • such a polyoxymethylene copolymer may contain, as necessary, general additives for thermoplastic resins, for example, coloring agents such as dyes and pigments, lubricants, nucleating agents, One or more types of release agents, antistatic agents, surfactants, or organic polymer materials, inorganic or organic fibrous, platy, or granular fillers are used for the purpose of the present invention. It can be added within a range that does not inhibit. '
  • an irregular extrusion method is usually used.
  • the manufacture of a molded article having an irregular cross section is basically performed as follows. That is, after the resin is heated and melted in an extruder having a single-screw or twin-screw, the molten resin is extruded from an extrusion die (die) having a predetermined shape and shaped into a target shape in a sizing process. Both are solidified by a cooling process, taken up, and cut to a desired length as necessary to obtain a long molded body.
  • the shape of the extrusion die can be any shape design other than the round shape, and can be similar to the cross-sectional shape of the final product. Different cross-sectional shapes can be used.
  • a sizing process is performed in a sizing step to shape the molten resin extruded from the extrusion die into a desired shape.
  • External sizing and internal sizing are known as sizing methods, but the external sizing method is the mainstream, and the vacuum sizing method is often used.
  • the resin whose shape has been adjusted by sizing is cooled and solidified by a water tank, a water shower, air cooling, etc., to obtain a desired product. Cooling can be performed simultaneously with sizing, and prior to sizing, pre-cooling can be performed to the extent that the molten resin does not solidify.
  • the cross-sectional shape of the resulting molded article having an irregular cross-section includes open shapes such as L-shape, U-shape, E-shape, and T-shape, hollow shapes such as cylinders and square tubes, and ribs in hollow shapes. Either the provided shape with hollow ribs or a composite shape obtained by mixing these shapes is possible.
  • open shapes such as L-shape, U-shape, E-shape, and T-shape
  • hollow shapes such as cylinders and square tubes
  • ribs in hollow shapes Either the provided shape with hollow ribs or a composite shape obtained by mixing these shapes is possible.
  • the molded article having an irregular cross section obtained by using the resin material comprising the polyoxymethylene copolymer of the present invention has high strength, high elastic modulus, solvent resistance, heat resistance, flex fatigue resistance and the like. There are various applications utilizing the excellent characteristics. Since the processed product is in a continuous form, it can be used by appropriately cutting it according to the purpose. For example, it can be used for rails, pipes, various building materials, and various other uses. BRIEF DESCRIPTION OF THE FIGURES
  • FIG. 1 is a sectional view showing the shape of a die used in the example.
  • FIG. 2 is a diagram showing the shape of the vacuum sizing used in the example, (a) is a sectional view, and (b) is a side view.
  • Example 1 is a sectional view showing the shape of a die used in the example.
  • FIG. 2 is a diagram showing the shape of the vacuum sizing used in the example, (a) is a sectional view, and (b) is a side view.
  • Example 1 is a sectional view showing the shape of a die used in the example.
  • FIG. 2 is a diagram showing the shape of the vacuum sizing used in the example, (a) is a sectional view, and (b) is a side view.
  • Example 2 is a diagram showing the shape of the vacuum sizing used in the example, (a) is a sectional view, and (b) is a side view.
  • a paddle was attached using a continuous mixing reactor consisting of a barrel that has a jacket through which a heat (cool) medium passes and a cross section of two circles partially overlapping, and a rotary shaft with paddles. While rotating the rotating shafts at 150 rpm, add liquid trioxane, cyclic ether or cyclic formal as a comonomer, further add methylal as a molecular weight regulator, and 50 ppm of boron trifluoride as a catalyst (based on all monomers). was continuously supplied to a polymerization machine to perform bulk polymerization. Table showing the water content of trioxane used, the type of comonomer, and the amount of methylal (ratio to total monomer weight)
  • the water content of each comonomer was less than 10 ppm.
  • the target value of the melt index of the obtained copolymer was 2.0 in Examples 1 to 3 and 5 to 7, 1.5 in Example 4, and 9.0 in Example 8, and the amount of methylal was added. Fine adjustment was made within the range shown in Table 1.
  • the reaction product discharged from the polymerization machine was immediately passed through a crusher, and was added to a 60 ° C aqueous solution containing 0.05% by weight of triethylamine to deactivate the catalyst. Further, after separation, washing and drying, a crude polyoxymethylene copolymer was obtained. Table 2 shows the properties of the obtained copolymer.
  • triethyl was added to 100 parts by weight of the crude polyoxymethylene copolymer.
  • 4 parts by weight of a 5% by weight aqueous solution of amine, and 0.3 parts by weight of pentaerythristyl-tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] are added, and a twin screw extruder is added.
  • a twin screw extruder is added.
  • 210 ° C. to remove unstable parts.
  • the resin is melt-plasticized by an extruder at a cylinder-set temperature of 200 ° C.
  • a die with the cross-sectional shape shown in Fig. 1 (The unit of the number in the figure is mm
  • the resin is passed through the vacuum sizing dies (the unit of the number in the figure is mm) as shown in Fig. 2 while cooling and cooling to form a "U-shaped" rail shape. I got something.
  • Table 2 shows the results evaluated by the evaluation method described below.
  • Polyoxymethylene (co) polymers not specified in the present invention as shown in Table 2 were prepared in the same manner as in Examples except that the amount of comonomer used or the amount of methylal as shown in Table 1 was changed.
  • the target value of the melt index was 2.0 in Comparative Examples 1-3 and 27.0 in Comparative Example 4, and the amount of methylal added was finely adjusted within the range shown in Table 1.
  • addition of methylal was not performed in order to obtain a copolymer having a small melt index.
  • the obtained (co) polymer was subjected to a stabilization treatment and the like in the same manner as in the examples, and was further subjected to profile extrusion to obtain a molded product.
  • Table 2 shows the results of evaluation using the evaluation method described below.
  • Example 3 Polymerization was carried out in the same manner as in Example 1 except that n-butyldaricidyl ether was added as a copolymerization component together with 1,3-dioxolane, and the branched structure was as shown in Table 3. To obtain a crude polyoxymethylene copolymer. Further, after performing the same processing as in Example 1, a molded product having an irregular cross section was manufactured to obtain a "U-shaped" rail-shaped molded product. Table 3 shows the results evaluated by the evaluation method described later.
  • the polymer used for evaluation of physical properties was dissolved in hexafluoroisopropanol d2, and ' ⁇ -NMR measurement was performed. It was quantified from the peak area corresponding to each unit.
  • the damage ij of the copolymer unit is shown in terms of mol ratio per lOOmol of oxymethylene unit.
  • the polymer used for the evaluation of physical properties was dissolved in hexafluoroisopropanol d2, and-NMR measurement was performed. It was quantified from the peak area corresponding to each end.
  • Copolymerization component Methylal amount Monomer (water content (ppm)) Comonomer (ppm)
  • Example 1 TOX (13) DO 300-500
  • Example 2 TOX (15) DO 300-500
  • Example 3 TOX (15) DO 300-500
  • Example 5 TOX (110) DO 300-500
  • Example 6 TOX (14) BDF 300-500
  • Example 7 TOX (13) EGF
  • Example 8 TOX (16) DO 500 to 800 Comparative Example 1 TOX (13) DO 300 to 500 Comparative Example 2 TOX (13) DO 300--500 Comparative Example 3 TOX (14) ⁇ + 300 to 500 Comparative Example 4 TOX ( 14) DO 1000-Lake 0 Comparative Example 5 TOX (13) DO 0
  • EGF ethylene glycol formal
  • Example 5 (CH 2 CH 2 0) 2.2 2.0 52 Gas generation, slight foaming
  • Example 6 (CH 2 CH 2 CH 2 CH 2 0) 2.2 2.1 0.2 3 Good
  • Comparative Example 4 (CH 2 CH 2 0) 2.2 27 0.2 1 • Difficult to process due to low resin viscosity Comparative Example 5 (CH 2 CH 20 ) 2.2 0.2 0.2 1 Extruder negative due to resin viscosity

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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)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Extrusion Moulding Of Plastics Or The Like (AREA)
  • Polyethers (AREA)

Abstract

La présente invention concerne un matériau résinique qui comprend un copolymère polyoxyméthylène renfermant une chaîne polymère composée principalement d'un motif récurrent oxyméthylène et contenant une unité oxyalkylène spécifique dans une quantité de 1,5 à 10 moles pour 100 moles de l'unité oxyméthylène, et possédant un indice de fluidité (à 190°, charge de 2160g) de 0,3 à 20g/10 min., lequel matériau résinique convient à la production d'un article formé à section transversale profilée. Le matériau résinique de l'invention permet de produire un article formé à section transversale profilée comprenant une résine de polyoxyméthylène, et il présente en outre une contrainte réduite et une excellente précision dimensionnelle.
PCT/JP2004/006327 2003-05-01 2004-04-30 Matériau résinique pour article formé à section transversale profilée WO2004096881A1 (fr)

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JP2003126385 2003-05-01

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008126523A (ja) * 2006-11-21 2008-06-05 Polyplastics Co ポリオキシメチレン樹脂製異形押出成形品の製造方法
JP2009097580A (ja) * 2007-10-15 2009-05-07 Ube Nitto Kasei Co Ltd 多孔チューブ及びその製造方法

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09239856A (ja) * 1996-03-14 1997-09-16 Asahi Chem Ind Co Ltd ポリアセタール系樹脂による成形部品
JPH09278983A (ja) * 1996-04-12 1997-10-28 Polyplastics Co ポリアセタール樹脂組成物並びにその成形品
JPH11124422A (ja) * 1997-08-22 1999-05-11 Polyplastics Co ポリアセタール樹脂の連続製造方法
JPH11279245A (ja) * 1998-03-30 1999-10-12 Polyplastics Co ポリアセタール樹脂の製造方法
JP2000119357A (ja) * 1998-08-12 2000-04-25 Asahi Chem Ind Co Ltd ポリオキシメチレン共重合体の製造方法及びポリオキシメチレン共重合体組成物
JP2000129080A (ja) * 1998-10-21 2000-05-09 Asahi Chem Ind Co Ltd グラフト化ポリオキシメチレン樹脂
JP2000169668A (ja) * 1998-12-02 2000-06-20 Polyplastics Co ポリアセタール樹脂組成物ならびにそれからなる成形品
JP2001089545A (ja) * 1999-09-24 2001-04-03 Asahi Kasei Corp ポリアセタール樹脂成形体
JP2004137415A (ja) * 2002-10-21 2004-05-13 Mitsubishi Engineering Plastics Corp ポリアセタール樹脂製押出し成形品

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09239856A (ja) * 1996-03-14 1997-09-16 Asahi Chem Ind Co Ltd ポリアセタール系樹脂による成形部品
JPH09278983A (ja) * 1996-04-12 1997-10-28 Polyplastics Co ポリアセタール樹脂組成物並びにその成形品
JPH11124422A (ja) * 1997-08-22 1999-05-11 Polyplastics Co ポリアセタール樹脂の連続製造方法
JPH11279245A (ja) * 1998-03-30 1999-10-12 Polyplastics Co ポリアセタール樹脂の製造方法
JP2000119357A (ja) * 1998-08-12 2000-04-25 Asahi Chem Ind Co Ltd ポリオキシメチレン共重合体の製造方法及びポリオキシメチレン共重合体組成物
JP2000129080A (ja) * 1998-10-21 2000-05-09 Asahi Chem Ind Co Ltd グラフト化ポリオキシメチレン樹脂
JP2000169668A (ja) * 1998-12-02 2000-06-20 Polyplastics Co ポリアセタール樹脂組成物ならびにそれからなる成形品
JP2001089545A (ja) * 1999-09-24 2001-04-03 Asahi Kasei Corp ポリアセタール樹脂成形体
JP2004137415A (ja) * 2002-10-21 2004-05-13 Mitsubishi Engineering Plastics Corp ポリアセタール樹脂製押出し成形品

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008126523A (ja) * 2006-11-21 2008-06-05 Polyplastics Co ポリオキシメチレン樹脂製異形押出成形品の製造方法
JP2009097580A (ja) * 2007-10-15 2009-05-07 Ube Nitto Kasei Co Ltd 多孔チューブ及びその製造方法

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CN100371363C (zh) 2008-02-27
JPWO2004096881A1 (ja) 2006-07-13
CN1784441A (zh) 2006-06-07

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