WO2011069892A1 - Procédé de fabrication de polyamides - Google Patents

Procédé de fabrication de polyamides Download PDF

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Publication number
WO2011069892A1
WO2011069892A1 PCT/EP2010/068788 EP2010068788W WO2011069892A1 WO 2011069892 A1 WO2011069892 A1 WO 2011069892A1 EP 2010068788 W EP2010068788 W EP 2010068788W WO 2011069892 A1 WO2011069892 A1 WO 2011069892A1
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WO
WIPO (PCT)
Prior art keywords
range
diamines
dicarboxylic acids
mixture
stage
Prior art date
Application number
PCT/EP2010/068788
Other languages
German (de)
English (en)
Inventor
Faissal-Ali El-Toufaili
Philippe Desbois
Andreas Wollny
Sven Lawrenz
Christian Schmidt
Original Assignee
Basf Se
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 Basf Se filed Critical Basf Se
Priority to ES10787420.8T priority Critical patent/ES2639062T3/es
Priority to JP2012542460A priority patent/JP5709890B2/ja
Priority to CN201080055231.2A priority patent/CN102639602B/zh
Priority to US13/514,364 priority patent/US9315626B2/en
Priority to EP10787420.8A priority patent/EP2510044B1/fr
Publication of WO2011069892A1 publication Critical patent/WO2011069892A1/fr

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Classifications

    • 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

Definitions

  • the invention relates to a process for the preparation of a polyamide based on dicarboxylic acids and diamines, in particular for the preparation of partially aromatic partially crystalline polyamides.
  • WO-A-2008/155281 already discloses a process for preparing polyamides which already comprises stages A), B), C) and E) of the present invention. This process leaves much to be desired in relation to the reaction procedure in the amine replenishment in the degassing extruder.
  • the present invention therefore an object of the invention to help the abovementioned disadvantages.
  • Diamines wherein the molar ratio of dicarboxylic acids to diamines is adjusted so that the output of step C) is a molar deficiency of dicarboxylic acids or diamines of 1 to 10 mol%, based on the other component,
  • step B) transferring the aqueous mixture from step A) into a continuously operated evaporator reactor, in which diamines and dicarboxylic acids are reacted at a temperature in the range from 100 to 370 ° C. and a pressure in the range from 1 to 50 bar,
  • step C) transferring the mixture from step B) into a separator which is operated at a temperature in the range from 100 to 370 ° C. and a pressure in the range from 1 to 50 bar, with removal of gaseous components,
  • step D) transferring the mixture from step C) together with diamine or dicarboxylic acid in an appropriate amount to compensate for the molar deficit in a tube reactor, which at a temperature in the range of 100 to 370 ° C and a pressure in the range of 1 up to 50 bar, for a residence time in the
  • step E) transferring the mixture from step D) into an extruder which is operated at a temperature in the range from 150 to 400 ° C. for a residence time in the course of rich from 10 seconds to 30 minutes, with removal of gaseous components through vents.
  • the inventive method allows the reduction of the viscosity of the polyamide prior to solid phase polycondensation and allows a reduction of the residence time at high temperature, whereby fewer side reactions such as triamine formation occur and thus the quality of the product is improved. It has been found in accordance with the invention that a procedure in which dicarboxylic acid or diamine is initially present in a deficit and this deficiency is compensated for entry into an extruder for postcondensation permits the production of particularly partially aromatic, partially crystalline polyamides having a high viscosity number.
  • the process is advantageous for the preparation of all high molecular weight polyamides, but has particular advantages when the monomer mixture in step A) from a dicarboxylic acid mixture of 60 to 88 wt .-% terephthalic acid and 12 to 40 wt .-% iso-phthalic acid, in which may also be replaced by other dicarboxylic acids up to 20 wt .-% of Dicarbonklaregemisches, and hexamethylenediamine, which may be replaced by other C2-C3o-diamines up to 20 wt .-%.
  • the inventive method comprises the sequence evaporator reactor-separator tube reactor, extruder, wherein in the evaporator reactor, an aqueous monomer mixture of dicarboxylic acids and diamines is performed.
  • the molar ratio of dicarboxylic acids to diamines is adjusted so that at the output of the subsequent separator stage, a molar excess of dicarboxylic acids or diamines of 1 to 10 mol%, based on the other component, is present. This can be achieved, for example, by providing a molar excess of dicarboxylic acid or diamine already when preparing the aqueous monomer mixture.
  • the evaporator reactor if after the evaporator reactor, a portion of the dicarboxylic acids or diamines is removed by evaporation from the reaction mixture, can also be started with equimolar amounts of dicarboxylic acids and diamines in the evaporator reactor, since there is a deficit of dicarboxylic acids or diamines after the separator.
  • the monomer ratio in stage A) is chosen so that at the outlet of stage C) there is a molar excess of dicarboxylic acids or diamines of from 1 to 10 mol%, based on the respective other component. For example, at 100 mol% dicarboxylic acids corresponding to 90 to 99 mol% diamines may be present at the end of step C).
  • the actual stoichiometry to be set in the aqueous monomer mixture depends on the type of monomers and can be determined by simple analysis of the mixture obtained from the separator in stage C).
  • the polyamide or polyamide oligomers obtained at the end of step C) can be analyzed with respect to the carboxyl end groups and amino end groups.
  • hexamethylenediamine is typically discharged in gaseous form downstream of the evaporator reactor.
  • step A an aqueous salt solution of the starting monomers is used since diamines and dicarboxylic acids form salts.
  • the monomer mixture preferably consists of 50 mol% of dicarboxylic acid mixture and 50 mol% of diamine or diamine mixture.
  • the dicarboxylic acid mixture consists of 60 to 88% by weight of terephthalic acid and 12 to 40% by weight of isophthalic acid.
  • up to 20% by weight of the dicarboxylic acid mixture can also be replaced by other dicarboxylic acids.
  • dicarboxylic acids are preferably 0 to 10 wt .-%, in particular 0 to 5 wt .-%. If one part of the dicarboxylic acid mixture is replaced by other dicarboxylic acids, the lower limit of the other component is preferably 0.5% by weight, in particular 1% by weight.
  • suitable dicarboxylic acids are, for example, adipic acid, pimelic acid, suberic acid, azelaic acid and sebacic acid and 7-sulfoisophthalic acid.
  • the diamine component used is hexamethylenediamine, which may be replaced by other C2-C3o-diamines up to 20% by weight.
  • hexamethylenediamine which may be replaced by other C2-C3o-diamines up to 20% by weight.
  • their minimum amount is preferably 0.5 wt .-%, in particular at least 1 wt .-%.
  • Suitable further diamines are, for example, tetramethylenediamine, octamethylenediamine, decamethylenediamine and dodecamethylenediamine and m-xylylenediamine, bis (4-aminophenyl) methane, bis (4-aminophenyl) propane-2,2 and bis (4-aminocyclohexyl) methane or mixtures thereof - from.
  • step B) the aqueous mixture from step A) is transferred to a continuously operated evaporator reactor in which diamines and dicarboxylic acids are at a temperature in the range of 100 to 370 ° C, preferably 200 to 340 ° C, and a pressure in the range of 1 be reacted to 50 bar, preferably 5 to 30 bar.
  • the evaporator reactor can be designed in any suitable manner.
  • stage B may, for example, be tube-bundle reactors, as described in EP-A-0 129 195. It is preferably a vertical tube reactor which is flowed through from above to below.
  • the residence time in stage B) is preferably 0.2 to 10 minutes, more preferably 1 to 5 minutes.
  • the evaporator reactor is followed by a separator, which is operated at a temperature of 100 to 370 ° C, preferably 200 to 340 ° C.
  • the pressure in the separator is preferably 1 to 50 bar, more preferably 5 to 30 bar.
  • the residence time in stage C) is preferably 1 to 45 minutes, more preferably 2 to 15 minutes.
  • gaseous components in particular water and volatile monomers are separated. For example, when using the preferred monomer mixture described above about 1 to 10% of the originally used diamine hexamethylenediamine are separated together with water vapor. This gaseous mixture can then be subjected to a distillation or rectification, wherein water vapor is removed overhead and a diamine / water mixture in the bottom is obtained.
  • step C water vapor and volatile dicarboxylic acids or diamines are separated, which are subsequently separated by distillation, whereby an aqueous condensate enriched in dicarboxylic acids or diamines is recycled to one or both of steps A) and B).
  • the proportion of diamines released by the evaporation, which are recycled to the process, can also be used to adjust the deficit of diamines.
  • stage C The separator of stage C) is followed by a tubular reactor in stage D), into which the mixture from stage C) is passed together with diamine or dicarboxylic acid in an amount suitable for offsetting the molar deficit.
  • the tube reactor is operated at a temperature in the range of 150 to 400 ° C, preferably 200 to 370 ° C and adjusted to a residence time in the range of 10 seconds to 30 minutes, preferably 2 seconds to 10 minutes.
  • the tube reactor of stage D) is followed by an extruder in stage E) into which the mixture from stage D) is passed.
  • the extruder is at a temperature in the range from 150 to 400 ° C, preferably operated at 200 to 370 ° C and set to a residence time in the range of 10 seconds to 30 minutes, preferably 2 seconds to 2 minutes.
  • gaseous components are removed through degassing.
  • Suitable extruders with degassing stages are known in the art. It can be used according to the invention preferably twin-screw extruder, which may be co-rotating or counter-rotating twin-screw extruder.
  • twin-screw extruder which may be co-rotating or counter-rotating twin-screw extruder.
  • stage D diamine or dicarboxylic acid are metered in, depending on whether there is a deficiency of diamine or dicarboxylic acid after stage C).
  • the amount suitable for offsetting the molar deficit can be determined by simple experiments, it being possible to determine the carboxyl end group content and amino end group content in the polyamide obtained after the extruder. If initially worked with a deficiency of diamines, in step D) preferably so much diamine is added that increases the amino end group content by at least 20 mmol / kg.
  • the amino end group content at the end of step D) is preferably 30 to 250 mmol / kg, more preferably 50 to 100 mmol / kg or 40 to 220 mmol / kg. Addition in other stages of the method according to the invention is also possible.
  • the extrusion can also be followed by a solid phase postcondensation and a granulation step.
  • the polyamides obtained according to step E) preferably have a viscosity number in the range from 20 to 200, more preferably from 40 to 80, in particular when using the preferred monomer mixture described above.
  • another diamine can also be added in step D), for example dicycan.
  • further additives at different points in the process, such as oxazolines, hyperbranched polymers having amino or carboxyl groups and other additives.
  • the additives can be supplied, for example, before or after a discharge pump following the evaporator reactor, as coldfeed or hotfeed in the separator.
  • polyamides have a glass transition temperature in the range of 1 10 to 150 ° C and a melting point in the range of 280 to 320 ° C. They preferably have a crystallinity of more than 20% and are therefore not transparent.
  • the polyamides which can be prepared according to the invention are suitable, for example, for vehicle or automobile applications, for example for interior lining of passenger compartments, for dashboards, for covers of valve housings, for mounting bases of blower and fan motors, for base plates for control, for exhaust gas recirculation components, for example.
  • connection modules such as turbo aggregates or turbo diesel units such as intercooler housing
  • turbo aggregates or turbo diesel units such as intercooler housing
  • connections for the interpretation of the throttle body of gasoline and diesel engines, for gasoline and oil-bearing systems or those that can come into contact with it
  • connections for the interpretation of the throttle body of gasoline and diesel engines, for gasoline and oil-bearing systems or those that can come into contact with it
  • vehicle electrical system or vehicle electronics for example in the form of connections and connectors for electric tronic control systems
  • electrical, electrical and electronic applications eg for connectors, collector holders in electric motors, impellers in vacuum cleaners, switching elements and relays, and electrical and electronic components, in particular those which are mounted using soldering tape technology, for drinking water, heating , Sanitary and bathing applications, eg for pipes, gaskets, valves, fittings and containers, for domestic use, eg for household appliances such as coffee and espresso machines, white goods such as dishwashers and washing machines as well as dryers or kitchen showers, for the medical technology application
  • the plant for the continuous production of high-temperature resistant polyamides from diamines (hexamethylenediamine, HMD) and dicarboxylic acids consists of the following functional groups:
  • the reaction solution is prepared from the diamines, dicarboxylic acids, regulators and water in the batch preparation in the stirred tank and transferred to the storage tank. From the template by means of feed pump via the heater, the reaction solution in the Head of the vertical evaporator reactor dosed.
  • the monomers with elimination of water (polycondensation) to the low molecular weight precursor.
  • the exiting mixture of precursor, vaporous solution and reaction water and part of the unreacted diamines and diacids is passed into the adjoining separator. There, the polymer melt separates from the vaporous fractions.
  • the discharged vapor streams are passed to the rectification column and irrigated with cold water.
  • Diamines which are obtained in the form of aqueous solution in the bottom are pumped and pumped back after separation of the now solidified polymer particles via filters to the reaction solution before the evaporator reactor.
  • the polymer melt from the separator is passed to a tube reactor and enriched with amine. Via a control valve, the melt is metered from the tube reactor to the extruder, and the remaining water is outgassed. Strands discharged polymer is cooled with water and granulated.
  • the batch solution is pumped via a feed pump, heated at 95 ° C, to the evaporator reactor.
  • the evaporator reactor consists of 10 tubes with a diameter of 33.6 mm and 4000 mm in length.
  • the filling consists of 5mm Raschig rings with center bar.
  • the evaporator reactor is protected on the inlet side with a safety valve. postcondensation
  • the downstream separator serves for the phase separation of the mixture of prepolymer and water vapor, which flows into the apparatus via an inlet pipe.
  • the separator has a length of 1800 mm and an inner diameter of 300 mm, with the last 250 mm tapered.
  • the inlet pipe is arranged eccentrically laterally. With the help of this downwardly open tube, the phase mixture is entered in the half of the separator near the wall.
  • the precipitator In order to keep the prepolymer molten, the precipitator is heated with Diphyl via a double jacket. The vapors leave the apparatus via the vapor line in the lid in the direction of the column of diamine rectification. Since this system is under pressure (20 bar), a small amount of water remains dissolved in the polyamide melt.
  • the polyamide melt is fed via a control valve to the degassing extruder.
  • Diamine recycling The vapors are introduced into an unheated rectification column. There they are washed in countercurrent with water. In this case, water-soluble oligomers are discharged with the wash water from the column.
  • the control of the pressure in the column via a steam-heated control valve at the top of the column. Through the hood, the column is raining. Below the column is a stationary measurement via differential pressure. In the column, the organic fractions from the vapors are washed out by sprinkling. From the circulation of the column bottom (about 1000 l / h), the precipitated portion is returned to the product stream before the evaporator reactor.
  • the recirculation amount is about 40 l / h.
  • the top stream of the column is discharged. This top stream (about 70 kg / h) contains all the water and a small amount of diamine (0.3-0.5%). The diamine, because it is removed from the reaction, must be considered as a loss.
  • Degassing and granulation A discharge valve regulates the constant product flow to the extruder.
  • the extruder is a ZDSK 57.
  • the screw is sealed to the rear by means of a coldfeed dosage of 2 kg / h granules.
  • the in the polymer melt contained water over a forward and a backward degassing.
  • the polymer melt is granulated with underwater granulation technology. Examples 1 to 5
  • Saline was pumped in the evaporator reactor at the product exit temperature and pressure (see table).
  • the product temperature and pressure can be taken from the table.
  • Metaxylenediamine (MXD) was metered into the tube reactor.
  • the polymer melt was extruded at 320 ° C and granulated and then annealed as shown in the table.
  • AEG amino end group content

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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)
  • Polyamides (AREA)

Abstract

La présente invention concerne un procédé de fabrication d'un polyamide à base d'acides dicarboxyliques et de diamines, ce procédé présentant les étapes suivantes : A) préparation d'un mélange aqueux de monomères à base d'acides dicarboxyliques et de diamines, le rapport molaire des acides dicarboxyliques aux diamines étant réglé de telle sorte qu'à la sortie de l'étape C), on a un déficit molaire d'acides dicarboxyliques ou de diamines de 1 à 10 % en moles, par rapport à l'autre composant respectif, B) transfert du mélange aqueux provenant de l'étape A) dans un réacteur évaporateur fonctionnant de façon continue, dans lequel des diamines et des acides dicarboxyliques sont mis à réagir à une température se situant dans la plage de 100 à 370°C et à une pression se situant dans la plage de 1 à 50 bar, C) transfert du mélange provenant de l'étape B) dans un séparateur, qui est mis en service à une température se situant dans la plage de 100 à 370°C et à une pression se situant dans la plage de 1 à 50 bar, avec séparation des composants gazeux, D) transfert du mélange provenant de l'étape C) conjointement avec de la diamine ou de l'acide dicarboxylique dans une quantité appropriée pour la compensation du déficit molaire dans un réacteur tubulaire, qui est mis en service à une température se situant dans la plage de 100 à 370°C et à une pression se situant dans la plage de 1 à 50 bar, pendant un temps de séjour se situant dans la plage de 10 secondes à 30 minutes, E) transfert du mélange provenant de l'étape D) dans une extrudeuse, qui est mis en service à une température se situant dans la plage de 150 à 400°C, pendant un temps de séjour se situant dans la plage de 10 secondes à 30 minutes, avec élimination des composants gazeux par des ouvertures de dégazage.
PCT/EP2010/068788 2009-12-08 2010-12-03 Procédé de fabrication de polyamides WO2011069892A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
ES10787420.8T ES2639062T3 (es) 2009-12-08 2010-12-03 Proceso para la preparación de poliamidas
JP2012542460A JP5709890B2 (ja) 2009-12-08 2010-12-03 ポリアミドの製造方法
CN201080055231.2A CN102639602B (zh) 2009-12-08 2010-12-03 制备聚酰胺的方法
US13/514,364 US9315626B2 (en) 2009-12-08 2010-12-03 Process for preparing polyamides
EP10787420.8A EP2510044B1 (fr) 2009-12-08 2010-12-03 Procédé de fabrication de polyamides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP09178358 2009-12-08
EP09178358.9 2009-12-08

Publications (1)

Publication Number Publication Date
WO2011069892A1 true WO2011069892A1 (fr) 2011-06-16

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PCT/EP2010/068788 WO2011069892A1 (fr) 2009-12-08 2010-12-03 Procédé de fabrication de polyamides

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US (1) US9315626B2 (fr)
EP (1) EP2510044B1 (fr)
JP (1) JP5709890B2 (fr)
CN (1) CN102639602B (fr)
ES (1) ES2639062T3 (fr)
WO (1) WO2011069892A1 (fr)

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US8796365B2 (en) 2007-06-28 2014-08-05 Basf Se Thermoplastic molding materials comprising organic black pigments
US8906992B2 (en) 2007-06-22 2014-12-09 Basf Se Molding compositions comprising polyaryl ether with improved surface quality
CN104603178A (zh) * 2012-09-03 2015-05-06 巴斯夫欧洲公司 通过缩聚反应制备聚酰胺的方法
US9051432B2 (en) 2009-04-03 2015-06-09 Basf Se Method for producing low-chlorine polybiphenyl sulfone polymers
US9056961B2 (en) 2009-11-20 2015-06-16 Basf Se Melamine-resin foams comprising hollow microbeads
US9428613B2 (en) 2010-09-10 2016-08-30 Basf Se Process for producing polyamide that is stable during processing
US9962889B2 (en) 2009-07-08 2018-05-08 Basf Se Method for producing fiber-reinforced composite materials from polyamide 6 and copolyamides made of polyamide 6 and polyamide 12
WO2022248262A1 (fr) 2021-05-26 2022-12-01 Basf Se Procédé de préparation de polyamides

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JP6349583B2 (ja) 2013-01-31 2018-07-04 ディーエスエム アイピー アセッツ ビー．ブイ． ジアミン／ジカルボン酸塩およびそれらのポリアミドの調製方法
TWI648311B (zh) * 2013-01-31 2019-01-21 Ｄｓｍ智慧財產有限公司 二胺／二甲酸鹽以及其聚醯胺之製備方法
CN104129880B (zh) * 2013-05-01 2018-11-23 英威达纺织（英国）有限公司 用于从聚酰胺合成工艺回收水的方法和系统
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JP2013513005A (ja) 2013-04-18
US20120245308A1 (en) 2012-09-27
EP2510044B1 (fr) 2017-05-31
EP2510044A1 (fr) 2012-10-17
JP5709890B2 (ja) 2015-04-30

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