WO2019225422A1 - Résine de polyamide et procédé de production associé - Google Patents

Résine de polyamide et procédé de production associé Download PDF

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Publication number
WO2019225422A1
WO2019225422A1 PCT/JP2019/019255 JP2019019255W WO2019225422A1 WO 2019225422 A1 WO2019225422 A1 WO 2019225422A1 JP 2019019255 W JP2019019255 W JP 2019019255W WO 2019225422 A1 WO2019225422 A1 WO 2019225422A1
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acid
polyamide resin
unit derived
aminocyclohexyl
bis
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PCT/JP2019/019255
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English (en)
Japanese (ja)
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隆志 土井
大介 堂山
古谷　敏男
康弘 河内
倉知　幸一郎
知之 中川
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宇部興産株式会社
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Publication of WO2019225422A1 publication Critical patent/WO2019225422A1/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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/36—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino acids, polyamines and polycarboxylic acids

Definitions

  • the present invention relates to a polyamide resin and a method for producing the same.
  • Polyamide resins are widely used as clothing, industrial material fibers, or general-purpose engineering plastics because of their excellent characteristics and ease of molding. In recent years, with the expansion of the use of polyamide resin, required characteristics have been diversified. In particular, an amorphous or microcrystalline polyamide resin (nylon resin) excellent in strength and toughness is used in optical applications and industrial applications.
  • nylon resin amorphous or microcrystalline polyamide resin
  • an amorphous or microcrystalline polyamide resin (transparent polyamide resin) is produced using a diamine compound typified by bis- (3-methyl-4-aminocyclohexyl) methane and an aliphatic dicarboxylic acid.
  • a diamine compound typified by bis- (3-methyl-4-aminocyclohexyl) methane and an aliphatic dicarboxylic acid.
  • An object of the present invention is to provide an amorphous or microcrystalline polyamide resin having a high tensile elongation and tensile modulus (Young's modulus) and a method for producing the same.
  • a polyamide resin containing a unit derived from bis- (3-methyl-4-aminocyclohexyl) methane containing a predetermined isomer in a predetermined ratio is amorphous. Or it discovered that it was microcrystalline and showed high tensile elongation rate and tensile elasticity modulus (Young's modulus), and completed this invention.
  • the present invention Units derived from bis- (3-methyl-4-aminocyclohexyl) methane; A unit derived from a linear aliphatic dicarboxylic acid having 10 to 14 carbon atoms, a unit derived from an aromatic carboxylic acid and a unit derived from a lactam having 11 or 12 carbon atoms, or an aromatic carboxylic acid
  • a polyamide resin comprising a unit derived from the above and a unit derived from an aminocarboxylic acid having 11 or 12 carbon atoms,
  • the bis- (3-methyl-4-aminocyclohexyl) methane includes isomers, The ratio of the peak area of the isomer with the shortest retention time to the peak area of all units of the bis- (3-methyl-4-aminocyclohexyl) methane detected by gas chromatography is 25% or more and 33% or less. It is a certain polyamide resin and its manufacturing method.
  • an amorphous or microcrystalline polyamide resin having a high tensile elongation and tensile modulus (Young's modulus) and a method for producing the same.
  • 2 is a gas chromatograph showing an example of measurement results of gas chromatography of bis- (3-methyl-4-aminocyclohexyl) methane.
  • the polyamide resin of the present invention includes a unit derived from bis- (3-methyl-4-aminocyclohexyl) methane, a unit derived from a linear aliphatic dicarboxylic acid having 10 to 14 carbon atoms, or an aromatic carboxylic acid.
  • each component will be described in detail.
  • Bis- (3-methyl-4-aminocyclohexyl) methane (hereinafter sometimes abbreviated as MACM) has two amino groups. It is a diamine compound.
  • the ratio of the peak area of the isomer with the shortest retention time to the peak area of all units of MACM detected by gas chromatography is 25% or more and 33% of the MACM which is the base of the structural unit of the polyamide resin of the present invention It is as follows.
  • a high tensile elongation rate and a high tensile elastic modulus (Young's modulus) can be provided.
  • the unit derived from MACM contained in the polyamide resin of the present invention is the total isomer of the peak area of the peak A of the isomer with the shortest retention time as shown in the gas chromatograph of FIG. A compound occupying 25% to 33% of the peak area.
  • the polyamide resin of the present invention has a unit derived from a linear aliphatic dicarboxylic acid and a unit derived from MACM
  • the content of the unit derived from MACM is 40.0 to 60.0 mass%. %, And more preferably 48.0 to 58.0% by mass.
  • the content of the unit derived from the MACM is 25.0 to 56.0% by mass.
  • the content is preferably 29 to 53% by mass, more preferably 35.0 to 48.0% by mass.
  • the linear aliphatic dicarboxylic acid is a compound having 10 to 14 carbon atoms.
  • the linear aliphatic dicarboxylic acid having 10 to 14 carbon atoms include sebacic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, and tetradecanedioic acid.
  • carboxylic acids examples include acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, capric acid, pelargonic acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, Aliphatic monocarboxylic acids such as myristoleic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, arachidic acid, behenic acid and erucic acid; alicyclic monocarboxylic acids such as cyclohexanecarboxylic acid and methylcyclohexanecarboxylic acid, benzoic acid Aromatic monocarboxylic acids such as acid, toluic acid, ethylbenzoic acid, and phenylacetic acid; malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid,
  • the content of units derived from the above linear aliphatic dicarboxylic acid is preferably 40 to 60% by mass, and more preferably 42 to 52% by mass.
  • a unit derived from an aromatic carboxylic acid and a unit derived from a lactam having 11 or 12 carbon atoms The polyamide resin of the present invention is replaced with a unit derived from the above-mentioned linear aliphatic dicarboxylic acid. And a unit derived from a lactam having 11 or 12 carbon atoms.
  • aromatic carboxylic acids aromatic dicarboxylic acids such as isophthalic acid, terephthalic acid, phthalic acid, m- / p-xylylene dicarboxylic acid, 1,4- / 2,6- / 2,7-naphthalenedicarboxylic acid, etc. Of these, one or a combination of two or more can be used.
  • Aromatic monocarboxylic acids such as benzoic acid, toluic acid, ethylbenzoic acid, and phenylacetic acid can also be added.
  • the polyamide resin of the present invention When having a unit derived from an aromatic carboxylic acid and a unit derived from a lactam having 11 or 12 carbon atoms, the polyamide resin of the present invention has a content of units derived from an aromatic carboxylic acid of 15.
  • the content is preferably 0 to 35.0% by mass, more preferably 17.0 to 32.0% by mass, and even more preferably 20 to 30% by mass.
  • examples of the lactam having 11 or 12 carbon atoms include laurolactam and undecane lactam. Among these, it is preferable to use laurolactam.
  • the polyamide resin of the present invention preferably has a content of the unit derived from the above lactam of 10 to 60% by mass.
  • the content is more preferably 15 to 53% by mass, and further preferably 25 to 40% by weight.
  • a unit derived from an aromatic carboxylic acid and a unit derived from an aminocarboxylic acid having 11 or 12 carbon atoms The polyamide resin of the present invention comprises a unit derived from the above linear aliphatic dicarboxylic acid, or an aromatic carboxylic acid.
  • a unit derived from an aromatic carboxylic acid and a unit derived from an aminocarboxylic acid having 11 or 12 carbons are used instead of the unit derived from an acid and the unit derived from a lactam having 11 or 12 carbons. You may have.
  • aromatic carboxylic acid 3. Those described in the above can be used.
  • the polyamide resin of the present invention has a content of the unit derived from the aromatic carboxylic acid, The content is preferably 15.0 to 35.0% by mass, more preferably 17.0 to 32.0% by mass, and further preferably 20 to 30% by mass.
  • the aminocarboxylic acid having 11 or 12 carbon atoms examples include 11-aminoundecanoic acid and 12-aminododecanoic acid. Of these, 12-aminododecanoic acid is preferably used.
  • the polyamide resin of the present invention has a content of the unit derived from the aminocarboxylic acid of 10 to 60% by mass. It is preferably 15 to 53% by mass, more preferably 25 to 40% by weight.
  • the polyamide resin of the present invention may have a unit derived from a compound (monomer) other than the above.
  • a monomer other than the above the content of units derived from the monomer is preferably 5% by mass or less.
  • the polyamide resin of the present invention is produced by a known batch production method or continuous production method.
  • Production equipment includes known polyamide resins such as batch-type reaction kettles, one-tank or multi-layer continuous reaction devices, tubular continuous reaction devices, kneading reaction extruders such as single-screw kneading extruders, twin-screw kneading extruders, etc. Manufacturing equipment can be used.
  • known methods such as melt polymerization, solution polymerization and solid phase polymerization can be used. These polymerization methods can be used alone or in appropriate combination.
  • each of the above raw materials and water are charged into a pressure vessel and polycondensed under pressure in a temperature range of 150 to 350 ° C. in a sealed state, and then the pressure is reduced to 150 to 350 ° C. under atmospheric pressure or reduced pressure.
  • the target polyamide resin can be produced by carrying out a polymerization reaction in the temperature range to increase the molecular weight.
  • the water used for polycondensation is preferably ion-exchanged water or distilled water from which oxygen has been removed, and the amount used is generally 1 to 150 per 100 parts by weight of the raw material constituting the polyamide resin. Parts by weight.
  • raw material diamine and dicarboxylic acid may be charged in a pressure vessel as they are, or an approximately equal mol of diamine and dicarboxylic acid may be mixed and dissolved in water or alcohol, and a produced nylon salt may be used. good.
  • the high molecular weight polyamide resin is extracted from the pressure vessel, cooled with water, and then pelletized. In addition, when unreacted monomer etc. remain in the obtained pellet, unreacted monomer etc. may be removed by hot water washing
  • the molecular weight of the polyamide resin of the present invention is preferably in the range of 1.0 to 4.0, expressed in terms of relative viscosity ( ⁇ r) measured by the method described in JIS K6920-2, preferably 1.2 to 2. A range of 5 is more preferable.
  • the weight average molecular weight Mw of the polyamide resin of the present invention is preferably 15000 to 80000, and more preferably 20000 to 50000.
  • the number average molecular weight Mn of the polyamide resin of the present invention is preferably 10,000 to 40,000, and more preferably 12,000 to 35,000.
  • phosphoric acid When polymerizing the polyamide resin of the present invention, phosphoric acid, phosphorous acid, hypophosphorous acid, polyphosphoric acid, trisodium phosphate, sodium dihydrogen phosphate, phosphoric acid, if necessary, for promoting polymerization and preventing deterioration.
  • Disodium hydrogen, sodium phosphite, sodium hypophosphite and the like can be added.
  • the addition amount of these phosphorus compounds is usually 1 to 3000 ppm with respect to the polyamide resin to be obtained.
  • molecular weight regulators include amines such as laurylamine, stearylamine, hexamethylenediamine, and metaxylylenediamine, acetic acid, benzoic acid, hexanedioic acid, isophthalate for molecular weight regulation and melt viscosity stabilization during molding processing.
  • Carboxylic acids such as acid and terephthalic acid can be added. The amount of these molecular weight regulators used varies depending on the reactivity of the molecular weight regulator and the polymerization conditions, but is appropriately determined so that the relative viscosity of the finally obtained polyamide resin falls within the above range.
  • the polyamide resin of the present invention is added with a heat stabilizer, an ultraviolet absorber, a light stabilizer, an antioxidant, an antistatic agent, a tackifier, a sealing property improver, an antifogging agent.
  • a heat stabilizer an ultraviolet absorber, a light stabilizer, an antioxidant, an antistatic agent, a tackifier, a sealing property improver, an antifogging agent.
  • Agents, mold release agents, impact resistance improvers, plasticizers, pigments, dyes, fragrances, reinforcing materials and the like can be added.
  • the molded article of the polyamide resin of the present invention is, for example, an automobile member such as a fuel tube, an air tube, a fuel auxiliary tank, a vapor canister, a quick connector, a fan, a clip, a fastener, an engine cover, a radiator tank, an air duct hose, an armrest, and a gear.
  • the molded article of the polyamide resin of the present invention includes various molded products, sheets, films, pipes, tubes, monofilaments, fibers, containers, etc., for which conventional polyamide resins have been used, such as automobile members, computers and related equipment, optical equipment members. It can be used for a wide range of applications such as electrical / electronic equipment, information / communication equipment, precision equipment, civil engineering / building supplies, medical supplies, and household goods.
  • the properties of the polyamide resin were measured by the following method.
  • the weight average molecular weight and the number average molecular weight were analyzed by GPC (Gel Permeation Chromatography).
  • the reaction apparatus used was Tosoh HLC-8320GPC, and the column used was Tosoh TSKgel Super AW3000 and TSKgel Super AW5000.
  • the developing solvent was 10 mM-TFA Na salt-containing trifluoroethanol, which was passed through the column at 40 ° C. and 0.3 mL / min.
  • As an analysis sample 20 ⁇ L of a solution in which about 10 mg of sample was dissolved in about 30 ml of trifluoroethanol was injected into the GPC apparatus.
  • PMMA was used as a calibration curve.
  • Glass transition point The glass transition point was measured by DSC (Differential Scanning Calorimetry DSC7020 manufactured by SII Nano Technology).
  • MeOH is added to the hydrolysis solution to prepare a MeOH solution of about 10 wt% -MACM.
  • the solution is injected into a gas chromatograph and analyzed.
  • the isomer ratio of the hydrolyzed MACM coincides with the isomer ratio of MACM used as a raw material.
  • the ratio of the peak area of the isomer with the shortest retention time to the peak area of all isomers was 31.8%, 31.0%, and 27.0%, respectively. Further, when the MACM before purification was also analyzed by gas chromatography, the ratio of the peak area of the isomer with the shortest retention time to the peak area of all isomers was 29.6%.
  • the MACM manufactured by ALDRICH before purification is indicated as M-0
  • the MACM for the first distillation is indicated as M-1
  • the MACM for the residue in the kettle is indicated as M-2.
  • the ratio of the peak area of the isomer with the shortest retention time to the peak area of all isomers was 34.2% and 30.1%, respectively. Met.
  • the MACM of the first distillation fraction is indicated as M-3
  • the MACM manufactured by BASF before purification is indicated as M-4.
  • the temperature was raised to 270 ° C. while adjusting the pressure in the autoclave to be 2.0 MPa or less, and then polymerization was performed at 270 ° C. for 2 hours.
  • the pressure was returned to normal pressure, and the polymerization at 270 ° C. was continued.
  • the polymerized polyamide resin was extracted as a strand from the autoclave, passed through distilled water, and then pelletized by a pelletizer. This pellet was dried under reduced pressure at 100 ° C. for 12 hours to obtain a polyamide resin.
  • Example 2 A polyamide resin was produced by polymerization and pelletization under the same production conditions as in Example 1 except that M-1 was used instead of M-0 as bis- (3-methyl-4-aminocyclohexyl) methane.
  • Example 3 A polyamide resin was produced by polymerization and pelletization under the same production conditions as in Example 1 except that M-2 was used instead of M-0 as bis- (3-methyl-4-aminocyclohexyl) methane.
  • Example 4 A polyamide resin was produced by polymerization and pelletization under the same production conditions as in Example 1 except that M-3 was used instead of M-0 as bis- (3-methyl-4-aminocyclohexyl) methane.
  • Example 5 In a 1 L autoclave, isophthalic acid (manufactured by Wako Pure Chemical Industries): 73.32 g, bis- (3-methyl-4-aminocyclohexyl) methane (M-0): 106.22 g, laurolactam (manufactured by Ube Emus): 90. 97 g, benzoic acid: 0.93 g, 50% H 3 PO 2 aqueous solution: 0.06 g, and distilled water: 14.67 g were added. Thereafter, the inside of the autoclave was purged with nitrogen.
  • isophthalic acid manufactured by Wako Pure Chemical Industries
  • M-0 bis- (3-methyl-4-aminocyclohexyl) methane
  • laurolactam manufactured by Ube Emus
  • the temperature was raised to 220 ° C. while adjusting the pressure in the autoclave to be 2.0 MPa or less, and then polymerization was performed at 220 ° C. for 2 hours.
  • the pressure was returned to normal pressure, the temperature was raised to 270 ° C., the polymerization was continued at 270 ° C., and the polymerization was terminated when a predetermined molecular weight was reached (about 1 hour).
  • the polymerized polyamide resin was extracted as a strand from the autoclave, passed through distilled water, and then pelletized by a pelletizer. This pellet was dried under reduced pressure at 100 ° C. for 12 hours to obtain a polyamide resin.
  • Example 6 A polyamide resin was produced by polymerization and pelletization under the same production conditions as in Example 5 except that M-1 was used instead of M-0 as bis- (3-methyl-4-aminocyclohexyl) methane.
  • Example 7 A polyamide resin was produced by polymerization and pelletization under the same production conditions as in Example 5 except that M-2 was used instead of M-0 as bis- (3-methyl-4-aminocyclohexyl) methane.
  • Example 8 A polyamide resin was produced by polymerization and pelletization under the same production conditions as in Example 5 except that M-3 was used instead of M-0 as bis- (3-methyl-4-aminocyclohexyl) methane.
  • the pressure was returned to normal pressure, and the polymerization at 270 ° C. was continued.
  • the polymerized polyamide resin was extracted as a strand from the autoclave, passed through distilled water, and then pelletized by a pelletizer. This pellet was dried under reduced pressure at 100 ° C. for 12 hours to obtain a polyamide resin.
  • the pressure was returned to normal pressure, the temperature was raised to 270 ° C., the polymerization was continued at 270 ° C., and the polymerization was terminated when a predetermined molecular weight was reached (about 1 hour).
  • the polymerized polyamide resin was extracted as a strand from the autoclave, passed through distilled water, and then pelletized by a pelletizer. This pellet was dried under reduced pressure at 100 ° C. for 12 hours to obtain a polyamide resin.
  • Tables 1 and 2 show the physical property measurement results of the polyamide resins obtained in each Example and each Comparative Example.
  • the ratio of the peak area of the isomer with the shortest retention time to the peak area of all isomers is indicated as the occupied area ratio A.
  • all the polyamide resins obtained in each Example and each Comparative Example were transparent.
  • the polyamide resin of each example showed higher tensile elongation and higher tensile elastic modulus than the comparative example produced under the same conditions.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
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  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
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Abstract

L'invention concerne une résine de polyamide ayant un allongement à la traction et un module d'élasticité en traction (module de Young) élevés; et un procédé de production de celle-ci. La résine de polyamide selon la présente invention est une résine de polyamide contenant des unités dérivées de bis-(3-méthyl-4-aminocyclohexyl)méthane, des unités dérivées d'acide gras dicarboxylique à chaîne droite en C10-14, ou des unités dérivées d'un acide carboxylique aromatique et des unités dérivées d'un lactame en C11 ou 12, ou des unités dérivées d'un acide carboxylique aromatique et des unités dérivées d'un acide aminocarboxylique en C11 ou 12. Le bis-(3-méthyl-4-aminocyclohexyl)méthane contient un isomère, et la surface de pic de l'isomère avec le temps de rétention le plus court par rapport à la surface de pic de toutes les unités du bis-(3-méthyl-4-aminocyclohexyl)méthane détecté par chromatographie en phase gazeuse se situe dans la plage de 25 % à 33 %, inclus.
PCT/JP2019/019255 2018-05-23 2019-05-15 Résine de polyamide et procédé de production associé WO2019225422A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220267519A1 (en) * 2018-10-03 2022-08-25 Arkema France Improved method for the production of transparent polyamides

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09137057A (ja) * 1995-09-12 1997-05-27 Ems Inventa Ag 照明システム用レンズ
JP2001310999A (ja) * 2000-03-01 2001-11-06 Ems Chemie Ag 耐応力き裂性を改善した無色の高透明性ポリアミドブレンド
JP2009525362A (ja) * 2006-01-31 2009-07-09 エーエムエス−ヒェミー・アクチェンゲゼルシャフト ポリアミド成形配合物および透明かつ熱蒸気殺菌性成形物品または押出物を製造するためのその使用。
JP2015522689A (ja) * 2012-07-20 2015-08-06 ローディア オペレーションズ 新規ポリアミド、その調製方法およびその使用
JP2016079286A (ja) * 2014-10-16 2016-05-16 住友電気工業株式会社 透明ポリアミド樹脂組成物及び透明ポリアミド樹脂架橋成型体

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09137057A (ja) * 1995-09-12 1997-05-27 Ems Inventa Ag 照明システム用レンズ
JP2001310999A (ja) * 2000-03-01 2001-11-06 Ems Chemie Ag 耐応力き裂性を改善した無色の高透明性ポリアミドブレンド
JP2009525362A (ja) * 2006-01-31 2009-07-09 エーエムエス−ヒェミー・アクチェンゲゼルシャフト ポリアミド成形配合物および透明かつ熱蒸気殺菌性成形物品または押出物を製造するためのその使用。
JP2015522689A (ja) * 2012-07-20 2015-08-06 ローディア オペレーションズ 新規ポリアミド、その調製方法およびその使用
JP2016079286A (ja) * 2014-10-16 2016-05-16 住友電気工業株式会社 透明ポリアミド樹脂組成物及び透明ポリアミド樹脂架橋成型体

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220267519A1 (en) * 2018-10-03 2022-08-25 Arkema France Improved method for the production of transparent polyamides

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