ES2648104T3 - Composición de xililendiamina y método de producción de resina de poliamida - Google Patents
Composición de xililendiamina y método de producción de resina de poliamida Download PDFInfo
- Publication number
- ES2648104T3 ES2648104T3 ES14791010.3T ES14791010T ES2648104T3 ES 2648104 T3 ES2648104 T3 ES 2648104T3 ES 14791010 T ES14791010 T ES 14791010T ES 2648104 T3 ES2648104 T3 ES 2648104T3
- Authority
- ES
- Spain
- Prior art keywords
- polyamide resin
- xylylenediamine
- production method
- xylylenediamine composition
- resin production
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 title abstract description 11
- 239000000203 mixture Substances 0.000 title abstract description 9
- 229920006122 polyamide resin Polymers 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- NXLACVVNHYIYJN-UHFFFAOYSA-N 1-phenyl-n-(1-phenylethyl)ethanamine Chemical compound C=1C=CC=CC=1C(C)NC(C)C1=CC=CC=C1 NXLACVVNHYIYJN-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- XMBOJPWGJXIBMM-UHFFFAOYSA-N 1-(3-methylphenyl)-n-[(3-methylphenyl)methyl]methanamine Chemical compound CC1=CC=CC(CNCC=2C=C(C)C=CC=2)=C1 XMBOJPWGJXIBMM-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5033—Amines aromatic
-
- 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
- C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic 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
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—Preparatory processes
-
- 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
- C08G69/28—Preparatory processes
- C08G69/30—Solid state polycondensation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Epoxy Resins (AREA)
Abstract
Una composición de xililendiamina que comprende xililendiamina y bis(metilbencil)amina, siendo un contenido de la bis(metilbencil)amina de 0,0005 a 0,1 partes en masa sobre la base de 100 partes en masa de la xililendiamina.
Description
completada la reacción, el catalizador se separó por filtración mediante un filtro de membrana (0,2 µm, fabricado por Merck Millipore), y el filtrado se sometió a una purificación por destilación, obteniendo así un destilado a una presión de 0,77 kPa a una temperatura de 174 a 176 °C. Se confirmó que el destilado resultante era bis(3-metilbencil)amina (pureza: 97 %) mediante CG-MS y 1H-RMN.
5
(Preparación de la composición de xililendiamina)
10 Se preparó una composición de xililendiamina de tal manera que un contenido de bis(3-metilbencil)amina fue de 0,001 partes en masa sobre la base de 100 partes en masa de m-xililendiamina.
(Producción de la resina de poliamida)
15 Se cargó un recipiente de reacción equipado con un agitador, un condensador parcial, un condensador total, un termómetro, un embudo de goteo, un tubo de entrada de nitrógeno y un troquel de hebras con 10 kg (68,43 moles) de ácido adípico (fabricado por Rhodia) y después de purgar a fondo con nitrógeno, el producto resultante se fundió adicionalmente con calor a 170 °C bajo una pequeña cantidad de corriente de nitrógeno mientras se agitaba el interior del sistema. Se añadieron gota a gota 9,273 kg de la composición de xililendiamina así obtenida (que
20 contenía 68,08 moles de m-xililendiamina) al ácido adípico fundido bajo agitación, y la temperatura interna se elevó continuamente a 240 °C durante 2,5 horas mientras se vertía el agua condensada formada en el exterior del sistema.
Una vez completada la adición gota a gota de la composición de xililendiamina, se aumentó la temperatura interna; en el momento en que la temperatura alcanzó 250 °C, el interior del recipiente de reacción fue evacuado; la
25 temperatura interna se elevó aún más y se continuó una reacción de policondensación en estado fundido a 255 °C durante 20 minutos. Posteriormente, el interior del sistema se presurizó con nitrógeno, y el polímero resultante se recogió del troquel de hebras y se granuló, obteniéndose así una resina de poliamida. La resina de poliamida resultante se sometió a las evaluaciones descritas anteriormente. Los resultados se muestran en la Tabla 1.
30 (Polimerización en fase sólida)
Además, se cargaron 500 g de la resina de poliamida descrita anteriormente en un matraz de tipo berenjena de 2 litros, y después de purgar a fondo con nitrógeno, la resina de poliamida se calentó en un baño de aceite a 190 °C durante 4 horas mientras se evacuaba, realizando así la polimerización en fase sólida. Como para la resina de
35 poliamida después de la polimerización en fase sólida, el valor IA se midió de la misma manera que se describió anteriormente. Los resultados se muestran en la Tabla 1.
40 Las composiciones de xililendiamina se prepararon de la misma manera que en el Ejemplo 1, excepto que en el Ejemplo 1, el contenido de la bis(3-metilbencil)amina en la composición de xililendiamina se cambió respectivamente como se muestra en la Tabla 1. Además, usando estas composiciones de xililendiamina, se produjeron resinas de poliamida y se sometieron a las evaluaciones descritas anteriormente. Los resultados se muestran en la Tabla 1.
45
10
Claims (1)
-
imagen1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013095708 | 2013-04-30 | ||
| JP2013095705 | 2013-04-30 | ||
| JP2013095705 | 2013-04-30 | ||
| JP2013095708 | 2013-04-30 | ||
| PCT/JP2014/060346 WO2014178270A1 (ja) | 2013-04-30 | 2014-04-09 | キシリレンジアミン組成物及びポリアミド樹脂の製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2648104T3 true ES2648104T3 (es) | 2017-12-28 |
Family
ID=51843405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14791010.3T Active ES2648104T3 (es) | 2013-04-30 | 2014-04-09 | Composición de xililendiamina y método de producción de resina de poliamida |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9562144B2 (es) |
| EP (1) | EP2993198B1 (es) |
| JP (1) | JP5700177B1 (es) |
| KR (1) | KR101563250B1 (es) |
| CN (1) | CN104812803B (es) |
| AU (1) | AU2014260891A1 (es) |
| BR (1) | BR112015025512A2 (es) |
| ES (1) | ES2648104T3 (es) |
| MX (1) | MX2015014887A (es) |
| PH (1) | PH12015502352A1 (es) |
| RU (1) | RU2650891C2 (es) |
| SG (1) | SG11201508864YA (es) |
| TW (1) | TWI502026B (es) |
| WO (1) | WO2014178270A1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6098391B2 (ja) * | 2013-06-21 | 2017-03-22 | 三菱瓦斯化学株式会社 | ポリアミド樹脂の製造方法 |
| CN116323848A (zh) * | 2020-10-15 | 2023-06-23 | 三菱瓦斯化学株式会社 | 环氧树脂固化剂、环氧树脂组合物、涂料以及粘接剂 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11158370A (ja) | 1997-11-25 | 1999-06-15 | Yasuhara Chemical Co Ltd | ポリアミド用結晶核剤およびポリアミド組成物 |
| JP5017756B2 (ja) * | 2001-07-16 | 2012-09-05 | 三菱瓦斯化学株式会社 | 高純度メタキシリレンジアミンの製造方法 |
| JP4843876B2 (ja) | 2001-07-19 | 2011-12-21 | 三菱瓦斯化学株式会社 | キシリレン基含有ポリアミド樹脂 |
| JP2005132736A (ja) * | 2003-10-28 | 2005-05-26 | Mitsubishi Gas Chem Co Inc | 高品位キシリレンジアミンの製造方法 |
| CN101379021B (zh) * | 2006-02-01 | 2011-12-28 | 巴斯夫欧洲公司 | 纯苯二甲胺(xda)的制备方法 |
| EP1857434B1 (en) * | 2006-05-18 | 2009-11-11 | Mitsubishi Gas Chemical Company, Inc. | Method for producing xylylenediamine |
| JP2008050403A (ja) * | 2006-08-22 | 2008-03-06 | Mitsubishi Gas Chem Co Inc | 酸素吸収性樹脂 |
| WO2010143668A1 (ja) * | 2009-06-09 | 2010-12-16 | 三菱瓦斯化学株式会社 | ポリアミド樹脂組成物及び成形品 |
| JP2011236285A (ja) * | 2010-05-07 | 2011-11-24 | Mitsubishi Gas Chemical Co Inc | 酸素吸収樹脂組成物の製造方法 |
| EP2444458A4 (en) * | 2009-06-15 | 2015-08-19 | Mitsubishi Gas Chemical Co | HYDROGEN ABSORBENT RESIN COMPOSITION |
| SG179119A1 (en) * | 2009-09-14 | 2012-05-30 | Mitsubishi Gas Chemical Co | Flame-retardant polyamide resin composition |
-
2014
- 2014-04-09 ES ES14791010.3T patent/ES2648104T3/es active Active
- 2014-04-09 KR KR1020157011932A patent/KR101563250B1/ko active IP Right Grant
- 2014-04-09 EP EP14791010.3A patent/EP2993198B1/en active Active
- 2014-04-09 WO PCT/JP2014/060346 patent/WO2014178270A1/ja active Application Filing
- 2014-04-09 AU AU2014260891A patent/AU2014260891A1/en not_active Abandoned
- 2014-04-09 SG SG11201508864YA patent/SG11201508864YA/en unknown
- 2014-04-09 JP JP2014536055A patent/JP5700177B1/ja active Active
- 2014-04-09 MX MX2015014887A patent/MX2015014887A/es active IP Right Grant
- 2014-04-09 CN CN201480003141.7A patent/CN104812803B/zh active Active
- 2014-04-09 RU RU2015146550A patent/RU2650891C2/ru active
- 2014-04-09 US US14/648,006 patent/US9562144B2/en active Active
- 2014-04-09 BR BR112015025512A patent/BR112015025512A2/pt not_active IP Right Cessation
- 2014-04-29 TW TW103115390A patent/TWI502026B/zh active
-
2015
- 2015-10-09 PH PH12015502352A patent/PH12015502352A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112015025512A2 (pt) | 2017-07-18 |
| SG11201508864YA (en) | 2015-11-27 |
| AU2014260891A1 (en) | 2015-11-05 |
| KR20150063564A (ko) | 2015-06-09 |
| MX2015014887A (es) | 2016-03-07 |
| CN104812803B (zh) | 2016-08-17 |
| RU2015146550A (ru) | 2017-06-01 |
| CN104812803A (zh) | 2015-07-29 |
| JP5700177B1 (ja) | 2015-04-15 |
| EP2993198B1 (en) | 2017-09-27 |
| EP2993198A4 (en) | 2016-12-14 |
| TW201500460A (en) | 2015-01-01 |
| WO2014178270A1 (ja) | 2014-11-06 |
| JPWO2014178270A1 (ja) | 2017-02-23 |
| US20160039993A1 (en) | 2016-02-11 |
| RU2650891C2 (ru) | 2018-04-18 |
| TWI502026B (zh) | 2015-10-01 |
| US9562144B2 (en) | 2017-02-07 |
| KR101563250B1 (ko) | 2015-10-26 |
| EP2993198A1 (en) | 2016-03-09 |
| PH12015502352A1 (en) | 2016-02-22 |
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