WO2023008365A1 - 全芳香族エーテルケトン樹脂組成物及びその製造方法、成形品、並びに当該樹脂組成物の溶融粘度の滞留安定性の向上方法 - Google Patents
全芳香族エーテルケトン樹脂組成物及びその製造方法、成形品、並びに当該樹脂組成物の溶融粘度の滞留安定性の向上方法 Download PDFInfo
- Publication number
- WO2023008365A1 WO2023008365A1 PCT/JP2022/028602 JP2022028602W WO2023008365A1 WO 2023008365 A1 WO2023008365 A1 WO 2023008365A1 JP 2022028602 W JP2022028602 W JP 2022028602W WO 2023008365 A1 WO2023008365 A1 WO 2023008365A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ether ketone
- wholly aromatic
- resin composition
- aromatic ether
- ketone resin
- Prior art date
Links
- -1 aromatic ether ketone Chemical class 0.000 title claims abstract description 97
- 239000011342 resin composition Substances 0.000 title claims abstract description 77
- 238000000034 method Methods 0.000 title claims abstract description 42
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 239000002253 acid Substances 0.000 claims abstract description 40
- 229920005989 resin Polymers 0.000 claims abstract description 35
- 239000011347 resin Substances 0.000 claims abstract description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000001139 pH measurement Methods 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 239000000843 powder Substances 0.000 claims abstract description 15
- 238000012360 testing method Methods 0.000 claims abstract description 13
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 239000000706 filtrate Substances 0.000 claims abstract description 11
- 230000014759 maintenance of location Effects 0.000 claims description 39
- 229920001643 poly(ether ketone) Polymers 0.000 claims description 24
- 239000000155 melt Substances 0.000 claims description 20
- 239000004696 Poly ether ether ketone Substances 0.000 claims description 13
- 229920002530 polyetherether ketone Polymers 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- 238000000465 moulding Methods 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- 238000001914 filtration Methods 0.000 abstract description 2
- 239000002585 base Substances 0.000 description 33
- 238000006116 polymerization reaction Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000005259 measurement Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 6
- 235000021317 phosphate Nutrition 0.000 description 6
- 229920001652 poly(etherketoneketone) Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 3
- 229920008285 Poly(ether ketone) PEK Polymers 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 3
- 235000019799 monosodium phosphate Nutrition 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 2
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000019837 monoammonium phosphate Nutrition 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229920006260 polyaryletherketone Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- HYOUHSBOGJQFMZ-UHFFFAOYSA-L P(=O)([O-])([O-])[O-].[PH4+].[Mg+2] Chemical compound P(=O)([O-])([O-])[O-].[PH4+].[Mg+2] HYOUHSBOGJQFMZ-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-L calcium bis(dihydrogenphosphate) Chemical compound [Ca+2].OP(O)([O-])=O.OP(O)([O-])=O YYRMJZQKEFZXMX-UHFFFAOYSA-L 0.000 description 1
- 229940062672 calcium dihydrogen phosphate Drugs 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 238000012668 chain scission Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- 235000019700 dicalcium phosphate Nutrition 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- QQFLQYOOQVLGTQ-UHFFFAOYSA-L magnesium;dihydrogen phosphate Chemical compound [Mg+2].OP(O)([O-])=O.OP(O)([O-])=O QQFLQYOOQVLGTQ-UHFFFAOYSA-L 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019691 monocalcium phosphate Nutrition 0.000 description 1
- 229910000401 monomagnesium phosphate Inorganic materials 0.000 description 1
- 235000019785 monomagnesium phosphate Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
-
- 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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group
- C08G2650/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group containing ketone groups, e.g. polyarylethylketones, PEEK or PEK
-
- 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
- C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
- C08K2003/3045—Sulfates
- C08K2003/3054—Ammonium sulfates
-
- 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
- C08K3/32—Phosphorus-containing compounds
- C08K2003/321—Phosphates
- C08K2003/322—Ammonium phosphate
-
- 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
- C08K3/32—Phosphorus-containing compounds
- C08K2003/321—Phosphates
- C08K2003/324—Alkali metal phosphate
Definitions
- the present invention provides a resin composition containing a wholly aromatic ether ketone such as polyether ketone, polyether ether ketone, or polyether ketone ether ketone ketone, a method for producing the same, a molded article obtained by molding the resin composition, and
- the present invention relates to a method for improving the retention stability of the melt viscosity of the resin composition.
- Wholly aromatic ether ketone resins are also known by the abbreviation PAEK (polyaryl ether ketone), PEEK (polyether ether ketone), PEK (polyether ketone), PEKK (polyether ketone ketone), PEKEKK (polyether ketone ether ketone ketone) etc. have been marketed as products. Since the wholly aromatic ether ketone resin generally has a high melting point (greater than 300°C), it must be heated to a high temperature for melting. However, at such high temperatures, there is a problem of lack of stability against thermal deterioration. Therefore, various measures have been taken to stabilize the molten state (see Patent Documents 1 and 2). The resin compositions described in Patent Documents 1 and 2 are stabilized against thermal oxidation in a molten state by adding a phosphate or a mixture of phosphates.
- the wholly aromatic ether ketone resin is known to increase in viscosity as the residence time elapses in the molten state. Such thickening is believed to be caused by oxidative cross-linking, generally associated with the very high processing temperatures (greater than 350° C.) of wholly aromatic ether ketone resins.
- Patent Documents 1 and 2 are intended to be stabilized against thermal oxidation in a molten state, but the increase or decrease in viscosity with the lapse of residence time may cause reactions between remaining reactive ends, oxidative cross-linking, There are many factors such as molecular chain elongation due to side reactions due to residual catalyst, molecular chain scission due to heat, oxygen, residual impurities, etc., and it is impossible to improve the retention stability of melt viscosity simply by stabilizing against thermal oxidation. can't.
- the present invention has been made in view of the above-described conventional problems, and its object is to provide a wholly aromatic ether ketone resin composition having excellent retention stability of melt viscosity, a method for producing the same, a molded article, and the resin composition To provide a method for improving the retention stability of the melt viscosity of
- the present inventors found that the retention stability of the melt viscosity can be improved by adjusting the pH of the wholly aromatic ether ketone resin composition to a predetermined range.
- the discovery led to the completion of the present invention.
- (1) contains (A) a wholly aromatic ether ketone resin and (B) a salt composed of an acid and a base, and has a pH of 6 to 8 as measured by the following pH measurement method; A wholly aromatic ether ketone resin composition, wherein the (A) wholly aromatic ether ketone resin is one or more selected from the group consisting of polyether ketone, polyether ether ketone, and polyether ketone ether ketone ketone.
- [pH measurement method] (a) After adding 5 mL of acetone to 10 g of the wholly aromatic ether ketone resin composition powder, 100 mL of pure water is added and the mixture is stirred for 10 minutes and then filtered.
- Wholly aromatic ether ketone resin composition containing (A) wholly aromatic ether ketone resin which is at least one selected from the group consisting of polyether ketone, polyether ether ketone, and polyether ketone ether ketone ketone A method for improving the retention stability of melt viscosity, A wholly aromatic ether ketone resin obtained by adding (B) a salt consisting of an acid and a base to the wholly aromatic ether ketone resin composition and adjusting the pH to 6 to 8 as measured by the following pH measurement method. A method for improving the retention stability of the melt viscosity of a composition.
- the present invention it is possible to provide a wholly aromatic ether ketone resin composition excellent in melt viscosity retention stability, a method for producing the same, a molded product, and a method for improving the melt viscosity retention stability of the resin composition. can.
- the wholly aromatic ether ketone resin composition of the present embodiment (hereinafter also simply referred to as "resin composition") comprises (A) a wholly aromatic ether ketone resin and (B) a salt composed of an acid and a base. include.
- the pH is 6 to 8 as measured by the following pH measuring method.
- the wholly aromatic ether ketone resin is one or more selected from the group consisting of polyether ketone, polyether ether ketone, and polyether ketone ether ketone ketone.
- the wholly aromatic ether ketone resin composition of the present embodiment has a pH adjusted to a range of 6 to 8 by (B) a salt composed of an acid and a base, the retention stability of the melt viscosity can be improved. can.
- the mechanism is presumed as follows.
- As the polymerization method of the wholly aromatic ether ketone resin there are two types of (1) nucleophilic aromatic substitution reaction and (2) Friedel-Crafts acylation reaction, but in the present embodiment, (1) It is intended for those that are polymerized by nucleophilic aromatic substitution reactions.
- polyetherketone, polyetheretherketone, and polyetherketoneetherketoneketone which are wholly aromatic etherketone resins, are polymerized by (1) a nucleophilic aromatic substitution reaction.
- a wholly aromatic ether ketone resin polymerized by a nucleophilic aromatic substitution reaction is polymerized at a high temperature (300° C. or higher) and under basic conditions using phenolic hydroxyl groups and aromatic halogen as reactive groups.
- a method of breaking the terminal balance and stopping the progress of polymerization by a terminal blocking reaction is generally employed (JP-A-61-138626). Alkali metal salts used as basic catalysts are removed by a post-polymerization water washing step.
- the polymerization reaction proceeds between the reactive ends during melt retention, increasing the molecular weight and thickening the viscosity from the polymerization mechanism. be done. Therefore, in the present embodiment, the pH of the resin composition is set within a predetermined range to suppress the reaction due to the terminal functional groups after polymerization, thereby improving the retention stability of the melt viscosity.
- the wholly aromatic resin composition of the present embodiment consists of polyetherketone (PEK), polyetheretherketone (PEEK), and polyetherketoneetherketoneketone (PEKEKK) as (A) wholly aromatic etherketone resin. It contains one or more selected from the group. These wholly aromatic ether ketone resins (1) exhibit basicity because they are polymerized by nucleophilic aromatic substitution reactions. From such a point of view, the pH of the wholly aromatic ether ketone resin itself is preferably 9-12.
- the wholly aromatic ether ketone resin is preferably polyether ketone (PEK).
- PEKK polyether ketone ketone
- (B) a salt consisting of an acid and a base In the present embodiment, (B) a salt composed of an acid and a base (hereinafter also referred to as “component (B)”) is used to adjust the pH of the resin composition to 6-8.
- component (B) a salt composed of an acid and a base
- the pH is preferably 6-7, more preferably 7. In adjusting the pH of the resin composition to 6 to 8, two or more components (B) may be used.
- the pH of the mixture may be in the range of 4 to 9 even if the pH of at least one component is not 4 to 9.
- the acid and base from which component (B) is derived are not particularly limited as long as they can adjust the pH of the resin composition to 6-8.
- Acids from which component (B) is derived include phosphoric acid and sulfuric acid.
- Examples of the base from which the component (B) is derived include hydroxides of alkali metals such as sodium hydroxide, hydroxides of alkaline earth metals and magnesium such as calcium hydroxide and magnesium hydroxide, and ammonia. be done.
- Component (B) includes, for example, at least one phosphate, ammonium sulfate, etc. Among them, at least one phosphate is preferred.
- Phosphates include, for example, sodium dihydrogen phosphate, disodium hydrogen phosphate, potassium dihydrogen phosphate, dipotassium hydrogen phosphate, calcium dihydrogen phosphate, calcium hydrogen phosphate, magnesium dihydrogen phosphate, phosphorus
- sodium dihydrogen phosphate disodium hydrogen phosphate
- potassium dihydrogen phosphate dipotassium hydrogen phosphate
- calcium dihydrogen phosphate calcium hydrogen phosphate
- magnesium dihydrogen phosphate magnesium dihydrogen phosphate
- phosphorus Magnesium hydrogen phosphate, ammonium dihydrogen phosphate, diammonium hydrogen phosphate and the like can be mentioned.
- the content of component (B) may be set so that the resin composition has a pH of 6 to 8, and can be 200 to 2000 ppm.
- thermoplastic resins such as lubricants, release agents, antistatic agents, surfactants, flame retardants, or organic polymeric materials, inorganic or organic 1 or 2 or more of powdery or plate-like fillers can be added.
- the pH of the resin composition must be within the range of 6-8.
- the molded article of the present embodiment is obtained by molding the wholly aromatic ether ketone resin composition of the present embodiment described above.
- the molded product has excellent retention stability of melt viscosity, so it can be used stably in molding processes that are exposed to high temperatures for a long time, such as long-term continuous molding by injection molding and solid-phase extrusion that stays for a long time. becomes.
- the method for producing a molded article using the wholly aromatic ether ketone resin composition of the present embodiment is not particularly limited, and known methods can be employed.
- the wholly aromatic ether ketone resin composition of the present embodiment is put into an extruder, melt-kneaded and pelletized, and the pellets are put into an injection molding machine equipped with a predetermined mold and injection molded. can be made.
- the molded product of this embodiment can be suitably used for applications such as automobiles, aviation, heavy industry (steel, power plants), and electronic parts.
- ⁇ Method for producing wholly aromatic ether ketone resin composition In the method for producing a wholly aromatic ether ketone resin composition of the present embodiment, at least (A) the wholly aromatic ether ketone resin is combined with (B) at least one of an acid and a base, or a salt composed of an acid and a base. is added, and adjusted so that the pH obtained by measuring by the following pH measurement method is 6 to 8. [pH measurement method] (a) After adding 5 mL of acetone to 10 g of the wholly aromatic ether ketone resin composition powder, 100 mL of pure water is added and the mixture is stirred for 10 minutes and then filtered.
- At least (A) the wholly aromatic ether ketone resin is combined with (B) an acid and a base, or an acid and a base.
- the pH of the resin composition is adjusted to 6-8 by adding at least one salt.
- salt A is the same as the salt composed of an acid and a base contained in the resin composition of the present embodiment described above, so it will be described here. are omitted and only acids and bases are described below.
- the acid and base to be added in the manufacturing method of the present embodiment are selected in a combination that becomes the above salt A after neutralization.
- Salt A is sodium dihydrogen phosphate
- the acid and base are a combination of phosphoric acid and sodium hydroxide
- Salt A is sodium acetate
- the acid and base are a combination of acetic acid and sodium hydroxide.
- the amounts of acid and base to be added are set so that the pH of the salt produced after neutralization of the acid and base is in the same range as that of salt A described above.
- the method for improving the retention stability of the melt viscosity of the wholly aromatic ether ketone resin composition of the present embodiment comprises polyether ketone, polyether ether ketone, and A method for improving the retention stability of the melt viscosity of a wholly aromatic ether ketone resin composition containing (A) a wholly aromatic ether ketone resin which is at least one selected from the group consisting of polyether ketone ether ketone ketone.
- (B) a salt composed of an acid and a base is added to the wholly aromatic ether ketone resin composition, and the pH is adjusted to 6 to 8 by measuring by the following pH measuring method.
- pH measurement method (a) After adding 5 mL of acetone to 10 g of the wholly aromatic ether ketone resin composition powder, 100 mL of pure water is added and the mixture is stirred for 10 minutes and then filtered. (b) 0.1 mL of pure water is added dropwise to the residue produced by volatilizing the liquid component of the filtrate obtained in (a) above. (c) The temperature is set at 25° C., and pH is measured by bringing pH test paper into contact with the pure water dripped onto the residue in (b) above.
- the pH is set within a predetermined range to suppress the reaction due to the terminal functional group after polymerization and improve the retention stability of the melt viscosity.
- I am planning That is, by setting the pH of the resin composition within a predetermined range, the retention stability of the melt viscosity can be improved. Therefore, in the method for improving the retention stability of the present embodiment, (B) a salt composed of an acid and a base is added, and the pH obtained by measuring by the pH measurement method is adjusted to 6 to 8 to melt. Viscosity retention stability can be improved.
- the wholly aromatic ether ketone resin is one or more selected from the group consisting of polyether ketone, polyether ether ketone, and polyether ketone ether ketone ketone. , the details of which are as described above, so the description thereof is omitted here.
- a salt composed of an acid and a base is also as described in the description of the wholly aromatic ether ketone resin composition of the present embodiment, so description thereof will be omitted here.
- the description of the wholly aromatic ether ketone resin composition of the present embodiment described above also applies to the preferred examples and content range of each component.
- each raw material component shown in Table 1 was blended at the ratio shown in Table 1 to obtain a powder of a wholly aromatic ether ketone resin composition.
- (B) a salt composed of an acid and a base was added in the form of an aqueous solution (solvent: distilled water, concentration: 2000 ppm/mL). Details of each raw material component used are shown below.
- melt viscosity [(complex viscosity at 30 minutes)/(complex viscosity at 5 minutes)] ⁇ 100 (I) [Measurement condition] Plate diameter: 25mm Gap distance: 1000 ⁇ m Measurement temperature: 400°C Measurement mode: Vibration Measurement atmosphere: Nitrogen Measurement time: 5 to 30 minutes Measurement range: 100 rad/s Strain: 3%
- Tables 1 and 2 show that Examples 1 to 6, in which the pH of the wholly aromatic ether ketone resin composition was in the range of 6 to 8, are all excellent in melt viscosity retention stability. In contrast, Comparative Examples 1 to 5, in which the pH range of the wholly aromatic ether ketone resin composition was outside the range of 6 to 8, were inferior in melt viscosity retention stability.
Landscapes
- 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)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
(1)(A)全芳香族エーテルケトン樹脂と、(B)酸と塩基とからなる塩と、を含み、下記pH測定法により測定して得られるpHが6~8であり、
前記(A)全芳香族エーテルケトン樹脂が、ポリエーテルケトン、ポリエーテルエーテルケトン、及びポリエーテルケトンエーテルケトンケトンからなる群より選ばれる1種以上である、全芳香族エーテルケトン樹脂組成物。
[pH測定法]
(a)全芳香族エーテルケトン樹脂組成物の粉末10gに、アセトン5mLを添加した後、純水100mlを添加して10分間撹拌し、その後ろ過する。
(b)前記(a)により得られたろ液の液体成分を揮発させて生じた残渣に純水を0.1mL滴下する。
(c)温度を25℃とし、前記(b)において残渣に滴下した純水にpH試験紙を接触させてpHを測定する。
[pH測定法]
(a)全芳香族エーテルケトン樹脂組成物の粉末10gに、アセトン5mLを添加した後、純水100mlを添加して10分間撹拌し、その後ろ過する。
(b)前記(a)により得られたろ液の液体成分を揮発させて生じた残渣に純水0.1mLを滴下する。
(c)温度を25℃とし、前記(b)において残渣に滴下した純水にpH試験紙を接触させてpHを測定する。
前記全芳香族エーテルケトン樹脂組成物に、(B)酸と塩基とからなる塩を添加して、下記pH測定法により測定して得られるpHを6~8とする、全芳香族エーテルケトン樹脂組成物の溶融粘度の滞留安定性の向上方法。
[pH測定法]
(a)全芳香族エーテルケトン樹脂組成物の粉末10gに、アセトン5mLを添加した後、純水100mlを添加して10分間撹拌し、その後ろ過する。
(b)前記(a)により得られたろ液の液体成分を揮発させて生じた残渣に純水0.1mLを滴下する。
(c)温度を25℃とし、前記(b)において残渣に滴下した純水にpH試験紙を接触させてpHを測定する。
本実施形態の全芳香族エーテルケトン樹脂組成物(以下、単に「樹脂組成物」とも呼ぶ。)は、(A)全芳香族エーテルケトン樹脂と、(B)酸と塩基とからなる塩とを含む。
そして、下記pH測定法により測定して得られるpHが6~8である。また、(A)全芳香族エーテルケトン樹脂は、ポリエーテルケトン、ポリエーテルエーテルケトン、及びポリエーテルケトンエーテルケトンケトンからなる群より選ばれる1種以上である。
[pH測定法]
(a)全芳香族エーテルケトン樹脂組成物の粉末10gに、アセトン5mLを添加した後、純水100mlを添加して10分間撹拌し、その後ろ過する。
(b)(a)により得られたろ液の液体成分を揮発させて生じた残渣に純水0.1mLを滴下する。
(c)温度を25℃とし、(b)において残渣に滴下した純水にpH試験紙を接触させてpHを測定する。
全芳香族エーテルケトン樹脂の重合方法としては、(1)求核芳香族置換反応及び(2)フリーデル・クラフツ・アシル化反応の2種類が挙げられるが、本実施形態においては、(1)求核芳香族置換反応により重合されるものを対象としている。すなわち、(A)全芳香族エーテルケトン樹脂である、ポリエーテルケトン、ポリエーテルエーテルケトン、及びポリエーテルケトンエーテルケトンケトンはいずれも(1)求核芳香族置換反応により重合される。(1)求核芳香族置換反応により重合される全芳香族エーテルケトン樹脂は、フェノール性水酸基と芳香族ハロゲンを反応性基として高温(300℃以上)、塩基性条件下で重合される。重合停止には、末端封止反応により末端バランスを崩し重合の進行を止める方法が一般的に採用される(特開昭61-138626号公報)。塩基性触媒として用いられるアルカリ金属塩は重合後の水による洗浄工程により取り除かれる。末端封止反応の反応率が低い、塩基性触媒の残存といった条件が重なると、溶融滞留した際に反応性末端同士で重合反応が進行し分子量が増大し、増粘することが重合メカニズムから考えられる。そこで、本実施形態においては、樹脂組成物のpHを所定の範囲内とすることで重合後の末端の官能性基による反応を抑制して溶融粘度の滞留安定性の向上を図っている。
以下に、本実施形態の全芳香族エーテルケトン樹脂組成物の各成分について詳述する。
本実施形態の全芳香族樹脂組成物は、(A)全芳香族エーテルケトン樹脂として、ポリエーテルケトン(PEK)、ポリエーテルエーテルケトン(PEEK)、及びポリエーテルケトンエーテルケトンケトン(PEKEKK)からなる群より選ばれる1種以上を含む。それらの全芳香族エーテルケトン樹脂は、(1)求核芳香族置換反応により重合されることから塩基性を呈する。そのような観点から、全芳香族エーテルケトン樹脂自体のpHは9~12であることが好ましい。(A)全芳香族エーテルケトン樹脂としては、ポリエーテルケトン(PEK)であることが好ましい。
本実施形態において(B)酸と塩基とからなる塩(以下、「(B)成分」とも呼ぶ。)は、樹脂組成物のpHを6~8とするために用いられる。樹脂組成物のpHが8を超えると、溶融粘度が滞留によって増加してしまい、pHが6未満であると、溶融粘度が滞留によって低下してしまうため、溶融粘度の滞留安定性に劣る。当該pHは6~7が好ましく、7がより好ましい。なお、樹脂組成物のpHを6~8にするに当たり、(B)成分は2種以上を用いてもよい。
(B)成分としては、例えば、リン酸塩のうちの少なくとも1種、硫酸アンモニウム等が挙げられ、中でも、リン酸塩のうちの少なくとも1種が好ましい。リン酸塩としては、例えば、リン酸二水素ナトリウム、リン酸水素二ナトリウム、リン酸二水素カリウム、リン酸水素二カリウム、リン酸二水素カルシウム、リン酸水素カルシウム、リン酸二水素マグネシウム、リン酸水素マグネシウム、リン酸二水素アンモニウム、リン酸水素二アンモニウム等が挙げられる。
本実施形態においては、必要に応じて、熱可塑性樹脂に対する一般的な添加剤、例えば、滑剤、離型剤、帯電防止剤、界面活性剤、難燃剤、又は、有機高分子材料、無機若しくは有機の粉体状、板状の充填材等を1種又は2種以上添加することができる。ただし、他の成分を添加する場合であっても、樹脂組成物のpHが6~8の範囲内となることが必要となる。
本実施形態の成形品は、以上の本実施形態の全芳香族エーテルケトン樹脂組成物を成形してなる。当該成形品は、溶融粘度の滞留安定性に優れるため、射出成形による長時間連続成形や、長時間滞留する固相押出等、高温に長時間暴露されるような成形加工でも安定して使用可能となる。
本実施形態の全芳香族エーテルケトン樹脂組成物の製造方法は、少なくとも(A)全芳香族エーテルケトン樹脂に対して、(B)酸及び塩基、又は酸と塩基とからなる塩の少なくとも1種を添加し、下記pH測定法により測定して得られるpHが6~8となるように調整する。
[pH測定法]
(a)全芳香族エーテルケトン樹脂組成物の粉末10gに、アセトン5mLを添加した後、純水100mlを添加して10分間撹拌し、その後ろ過する。
(b)(a)により得られたろ液の液体成分を揮発させて生じた残渣に純水0.1mLを滴下する。
(c)温度を25℃とし、(b)において残渣に滴下した純水にpH試験紙を接触させてpHを測定する。
本実施形態の全芳香族エーテルケトン樹脂組成物の溶融粘度の滞留安定性の向上方法(以下、「滞留安定性の向上方法」と省略する。)は、ポリエーテルケトン、ポリエーテルエーテルケトン、及びポリエーテルケトンエーテルケトンケトンからなる群より選ばれる1種以上である(A)全芳香族エーテルケトン樹脂を含む全芳香族エーテルケトン樹脂組成物の溶融粘度の滞留安定性の向上方法である。そして、全芳香族エーテルケトン樹脂組成物に、(B)酸と塩基とからなる塩を添加して、下記pH測定法により測定して得られるpHを6~8とする。
[pH測定法]
(a)全芳香族エーテルケトン樹脂組成物の粉末10gに、アセトン5mLを添加した後、純水100mlを添加して10分間撹拌し、その後ろ過する。
(b)前記(a)により得られたろ液の液体成分を揮発させて生じた残渣に純水0.1mLを滴下する。
(c)温度を25℃とし、前記(b)において残渣に滴下した純水にpH試験紙を接触させてpHを測定する。
各実施例・比較例において、表1に示す各原料成分を表1に示す割合でブレンドし、全芳香族エーテルケトン樹脂組成物の粉末を得た。なお、(B)酸と塩基とからなる塩は、水溶液(溶媒:蒸留水、濃度:2000ppm/mL)にして添加した。
使用した各原料成分の詳細を以下に示す。
・ポリエーテルケトン(PEK)
特開2009-227961号公報に記載される製造方法に従って重合し、ポリエーテルケトンの粉末を得た。得られたポリエーテルケトンの粉末のpHは10であった。
なお、全芳香族エーテルケトン樹脂のpHは、後述する全芳香族エーテルケトン樹脂組成物のpH測定法と同様にして測定した。
・リン酸二水素ナトリウム(2水和物);pH:4
・リン酸水素二ナトリウム(無水);pH:9
・リン酸三ナトリウム(12水和物);pH:12
・リン酸二水素カリウム;pH:4
・リン酸水素二カリウム;pH:9
・リン酸二水素アンモニウム;pH:4
・硫酸アンモニウム;pH:4
(1)pH
各実施例・比較例において得られた全芳香族エーテルケトン樹脂組成物の粉末10gに、アセトン5mLを添加した後、純水100mlを添加して10分間撹拌し、その後ろ過した。得られたろ液の液体成分を揮発させて生じた残渣に純水0.1mLを滴下した。温度を25℃とし、残渣に滴下した純水にpH試験紙を接触させてpHを測定した。測定したpHを表1及び表2に示す。
各実施例・比較例において得られた全芳香族エーテルケトン樹脂組成物の粉末を、140℃で9時間乾燥後、SUS304製の円形金型(外径:50mm、内径:21mm、厚み:2mm)の中央部に0.8g計量し、真空加熱プレス装置((株)井元製作所製)を用いて、以下の成形条件でプレス成形し、測定用試験片を得た。
[成形条件]
加熱板温度:400℃
予熱時間:3分
プレス圧力:10ton
プレス時間:30秒
溶融粘度の保持率(%)=[(30分時点の複素粘度)/(5分時点の複素粘度)]×100・・・(I)
[測定条件]
プレート径:25mm
ギャップ間隔:1000μm
測定温度:400℃
測定モード:振動
測定雰囲気:窒素
測定時間:5~30分
測定範囲:100rad/s
ひずみ:3%
各実施例・比較例において算出した溶融粘度の保持率に基づき評価した。すなわち、溶融粘度の保持率が95~105%の場合を「良好」とし、95%未満もしくは105%以上の場合を「不良」として評価した。評価結果が「良好」の場合、溶融粘度の滞留安定性に優れることを示す。評価結果を表1及び表2に示す。
Claims (7)
- (A)全芳香族エーテルケトン樹脂と、(B)酸と塩基とからなる塩と、を含み、下記pH測定法により測定して得られるpHが6~8であり、
前記(A)全芳香族エーテルケトン樹脂が、ポリエーテルケトン、ポリエーテルエーテルケトン、及びポリエーテルケトンエーテルケトンケトンからなる群より選ばれる1種以上である、全芳香族エーテルケトン樹脂組成物。
[pH測定法]
(a)全芳香族エーテルケトン樹脂組成物の粉末10gに、アセトン5mLを添加した後、純水100mlを添加して10分間撹拌し、その後ろ過する。
(b)前記(a)により得られたろ液の液体成分を揮発させて生じた残渣に純水0.1mLを滴下する。
(c)温度を25℃とし、前記(b)において残渣に滴下した純水にpH試験紙を接触させてpHを測定する。 - 前記(B)酸と塩基とからなる塩のpHが4~9である、請求項1に記載の全芳香族エーテルケトン樹脂組成物。
- 前記(A)全芳香族エーテルケトン樹脂が、ポリエーテルケトンである、請求項1又は2に記載の全芳香族エーテルケトン樹脂組成物。
- 前記(B)酸と塩基とからなる塩が、リン酸塩のうちの少なくとも1種である、請求項1~3のいずれか1項に記載の全芳香族エーテルケトン樹脂組成物。
- 請求項1~4のいずれか1項に記載の全芳香族エーテルケトン樹脂組成物を成形してなる成形品。
- 少なくとも(A)全芳香族エーテルケトン樹脂に対して、(B)酸及び塩基、又は酸と塩基とからなる塩の少なくとも1種を添加し、下記pH測定法により測定して得られるpHが6~8となるように調整する、全芳香族エーテルケトン樹脂組成物の製造方法。
[pH測定法]
(a)全芳香族エーテルケトン樹脂組成物の粉末10gに、アセトン5mLを添加した後、純水100mlを添加して10分間撹拌し、その後ろ過する。
(b)前記(a)により得られたろ液の液体成分を揮発させて生じた残渣に純水0.1mLを滴下する。
(c)温度を25℃とし、前記(b)において残渣に滴下した純水にpH試験紙を接触させてpHを測定する。 - ポリエーテルケトン、ポリエーテルエーテルケトン、及びポリエーテルケトンエーテルケトンケトンからなる群より選ばれる1種以上である(A)全芳香族エーテルケトン樹脂を含む全芳香族エーテルケトン樹脂組成物の溶融粘度の滞留安定性の向上方法であって、
前記全芳香族エーテルケトン樹脂組成物に、(B)酸と塩基とからなる塩を添加して、下記pH測定法により測定して得られるpHを6~8とする、全芳香族エーテルケトン樹脂組成物の溶融粘度の滞留安定性の向上方法。
[pH測定法]
(a)全芳香族エーテルケトン樹脂組成物の粉末10gに、アセトン5mLを添加した後、純水100mlを添加して10分間撹拌し、その後ろ過する。
(b)前記(a)により得られたろ液の液体成分を揮発させて生じた残渣に純水0.1mLを滴下する。
(c)温度を25℃とし、前記(b)において残渣に滴下した純水にpH試験紙を接触させてpHを測定する。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2023509841A JP7332837B2 (ja) | 2021-07-30 | 2022-07-25 | 全芳香族エーテルケトン樹脂組成物及びその製造方法、成形品、並びに当該樹脂組成物の溶融粘度の滞留安定性の向上方法 |
CN202280052993.XA CN117769584A (zh) | 2021-07-30 | 2022-07-25 | 聚芳醚酮树脂组合物及其制造方法、成型品以及该树脂组合物的熔融粘度的滞留稳定性的提高方法 |
EP22849426.6A EP4372053A1 (en) | 2021-07-30 | 2022-07-25 | Wholly aromatic ether ketone resin composition, method for producing same, molded article, and method for improving residence stability of melt viscosity of said resin composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2021125542 | 2021-07-30 | ||
JP2021-125542 | 2021-07-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2023008365A1 true WO2023008365A1 (ja) | 2023-02-02 |
Family
ID=85086937
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2022/028602 WO2023008365A1 (ja) | 2021-07-30 | 2022-07-25 | 全芳香族エーテルケトン樹脂組成物及びその製造方法、成形品、並びに当該樹脂組成物の溶融粘度の滞留安定性の向上方法 |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP4372053A1 (ja) |
JP (1) | JP7332837B2 (ja) |
CN (1) | CN117769584A (ja) |
TW (1) | TW202313844A (ja) |
WO (1) | WO2023008365A1 (ja) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61138626A (ja) | 1984-12-05 | 1986-06-26 | インペリアル ケミカル インダストリーズ パブリツク リミテイド カンパニー | 熱可塑性芳香族ポリエーテルケトン及びその製造方法 |
JPH03227320A (ja) * | 1990-01-30 | 1991-10-08 | Toyobo Co Ltd | 芳香族ポリエーテルケトン、その製造法、成形品 |
JPH04500088A (ja) * | 1988-08-05 | 1992-01-09 | レイケム・コーポレイション | ポリ(アリーレンエーテルケトン)の安定化 |
JP2009227961A (ja) | 2008-03-24 | 2009-10-08 | Gharda Chemicals Ltd | モノマーでありフェノラートであるポリエーテルケトンの製造方法 |
JP2018520258A (ja) | 2015-07-22 | 2018-07-26 | アルケマ フランス | 溶融状態で安定なポリ(アリーレン−エーテル−ケトン)(paek)から製造される組成物 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4593061A (en) * | 1985-03-29 | 1986-06-03 | Raychem Corporation | Stabilized poly(aryl ether ketone) compositions |
US4748227A (en) * | 1986-04-25 | 1988-05-31 | Amoco Corporation | Process for preparing poly(aryl ether)ketones using a sodium carbonate/organic acid salt catalyst |
DE3731607A1 (de) * | 1987-09-19 | 1989-03-30 | Hoechst Ag | Stabilisierte, aromatische polyetherketone enthaltende mischung und deren verwendung zur herstellung von formteilen |
JPH04272924A (ja) * | 1991-02-27 | 1992-09-29 | Nkk Corp | 芳香族ポリエーテルケトンおよびその製造方法 |
-
2022
- 2022-07-25 JP JP2023509841A patent/JP7332837B2/ja active Active
- 2022-07-25 CN CN202280052993.XA patent/CN117769584A/zh active Pending
- 2022-07-25 WO PCT/JP2022/028602 patent/WO2023008365A1/ja active Application Filing
- 2022-07-25 EP EP22849426.6A patent/EP4372053A1/en active Pending
- 2022-07-27 TW TW111128116A patent/TW202313844A/zh unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61138626A (ja) | 1984-12-05 | 1986-06-26 | インペリアル ケミカル インダストリーズ パブリツク リミテイド カンパニー | 熱可塑性芳香族ポリエーテルケトン及びその製造方法 |
JPH04500088A (ja) * | 1988-08-05 | 1992-01-09 | レイケム・コーポレイション | ポリ(アリーレンエーテルケトン)の安定化 |
JPH03227320A (ja) * | 1990-01-30 | 1991-10-08 | Toyobo Co Ltd | 芳香族ポリエーテルケトン、その製造法、成形品 |
JP2009227961A (ja) | 2008-03-24 | 2009-10-08 | Gharda Chemicals Ltd | モノマーでありフェノラートであるポリエーテルケトンの製造方法 |
JP2018520258A (ja) | 2015-07-22 | 2018-07-26 | アルケマ フランス | 溶融状態で安定なポリ(アリーレン−エーテル−ケトン)(paek)から製造される組成物 |
JP2018520257A (ja) | 2015-07-22 | 2018-07-26 | アルケマ フランス | ポリ(アリーレン−エーテル−ケトン)(paek)から製造された組成物を安定化させる方法 |
Also Published As
Publication number | Publication date |
---|---|
CN117769584A (zh) | 2024-03-26 |
EP4372053A1 (en) | 2024-05-22 |
JP7332837B2 (ja) | 2023-08-23 |
JPWO2023008365A1 (ja) | 2023-02-02 |
TW202313844A (zh) | 2023-04-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR101598792B1 (ko) | 폴리아릴렌설피드 수지의 제조 방법 및 폴리아릴렌설피드 수지 조성물 | |
EP3144337B1 (en) | Method for producing polyamide | |
CN102822281A (zh) | 包含聚芳硫醚的聚合物熔体 | |
WO2015156363A1 (ja) | ポリアミド樹脂組成物 | |
WO2015098748A1 (ja) | ポリアリーレンスルフィド樹脂組成物およびそれからなる成形品 | |
CN112795014A (zh) | 一种芳族砜聚合物及其制备方法和应用 | |
JP7332837B2 (ja) | 全芳香族エーテルケトン樹脂組成物及びその製造方法、成形品、並びに当該樹脂組成物の溶融粘度の滞留安定性の向上方法 | |
KR20200091802A (ko) | 폴리(페닐렌 에테르)의 제조방법 및 이에 의해 제조된 폴리(페닐렌 에테르) | |
US4939237A (en) | Preparation of high viscosity nylon with P catalyst composition | |
JP7332840B1 (ja) | 全芳香族エーテルケトン樹脂組成物及びその成形品、並びにリン系安定剤 | |
JPS59155425A (ja) | エポキシ樹脂用潜触媒または促進剤およびその製造方法 | |
EP4006079A1 (en) | Polyarylene ether ketone resin, manufacturing method therefor, and molded body | |
JP6337971B2 (ja) | ポリフェニレンスルフィド樹脂組成物およびその製造方法 | |
EP3904424A1 (en) | Poly(arylene ether ketone) resin, production method for same, and molded article | |
JP2015199873A (ja) | 強化高分子量ポリアミド樹脂組成物 | |
EP0064039B2 (en) | Use of an ethylene polymer composition for the production of film | |
JPS5974123A (ja) | ポリアリ−レンエ−テルの製造法 | |
CN116640440B (zh) | 一种低析出红磷阻燃玻纤增强尼龙及其制备方法和应用 | |
JP2018104609A (ja) | 一液型熱硬化性樹脂組成物およびその硬化物 | |
JP7310350B2 (ja) | メタンスルホン酸の精製方法、及び精製されたメタンスルホン酸の使用方法 | |
JPH02194054A (ja) | 高温下における色相の安定なポリアリーレンサルファイド樹脂組成物 | |
WO2013164855A2 (en) | Stable polyetherketones thermoplastic polymer | |
JP2717566B2 (ja) | 色相の安定化されたポリアリーレンサルファイド樹脂組成物 | |
US1046420A (en) | Plastic composition and method of preparing the same. | |
JP4017721B2 (ja) | ポリアミド粒状物の製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
ENP | Entry into the national phase |
Ref document number: 2023509841 Country of ref document: JP Kind code of ref document: A |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 22849426 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 202280052993.X Country of ref document: CN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2022849426 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: 2022849426 Country of ref document: EP Effective date: 20240213 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |