WO2002085968A1 - Verfahren zur herstellung von polyamiden - Google Patents
Verfahren zur herstellung von polyamiden Download PDFInfo
- Publication number
- WO2002085968A1 WO2002085968A1 PCT/EP2002/003278 EP0203278W WO02085968A1 WO 2002085968 A1 WO2002085968 A1 WO 2002085968A1 EP 0203278 W EP0203278 W EP 0203278W WO 02085968 A1 WO02085968 A1 WO 02085968A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- nitrile
- polyamides
- aminocapronitrile
- polyamide
- Prior art date
Links
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
- C08G69/38—Polyamides prepared from aldehydes and polynitriles
-
- 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
- C08G69/04—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
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/14—Lactams
- C08G69/16—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
Definitions
- the present invention relates to a process for the preparation of polyamides in a water-containing reaction mixture which contains a nitrile selected from 6-aminocapronitrile and adiponitrile, characterized in that a nitrile which has been flowed through in the liquid state with a gas which is inert to the nitrile, and polyamides obtainable by such a process.
- US 2,245,129 describes the production of polyamides from an amino nitrile.
- polycaprolactam polyamide 6, nylon 6
- 6-aminocapronitrile polycaprolactam
- polyhexamethylene adipamide polyamide 66, nylon 66
- adiponitrile hexamethylene diamine
- No. 4,436,898 describes (column 4, lines 4-8) that 2-cyanocyclopentylimine, which leads to gel formation and discoloration, can form intramolecularly in the production of polyamide from adiponitrile, hexamethylenediamine and water from the adiponitrile.
- 2-cyanocyclopentylimine which leads to gel formation and discoloration
- polyamide from adiponitrile hexamethylenediamine and water from the adiponitrile.
- Imino functions arise from which, through intramolecular reaction with an amino group, cycles or through hydrolysis, keto groups are formed, which also lead to discoloration.
- thermally stable polyamides can be obtained from 6-aminocapronitrile and water by using certain catalysts in the polymerization.
- cyclic compounds can thus arise intramolecularly from 6-aminocapronitrile or adipodinitrile, which lead to an undesirable discoloration of the polyamide.
- the present invention was based on the object of providing a process for the preparation of polyamides from water-containing reaction mixtures which contain a nitrile selected from 6-aminocapronitrile and adiponitrile, which in a technically simple and economical manner converts to a less discolored polyamide the polymerization and, in addition, in the case of water-containing reaction mixtures which contain 6-aminocapronitrile, leads to a polyamide which shows no increase in discoloration during the extraction, and to polyamides obtainable by such a process.
- a nitrile selected from 6-aminocapronitrile and adiponitrile is used.
- 6-aminocapronitrile and adiponitrile and processes for their preparation are known per se, for example from the prior art recognized at the outset.
- the molten nitrile can be used in pure form.
- the lower temperature is determined by the melting point of the nitrile (melting point 6-aminocapronitrile: -34 ° C; melting point adiponitrile: + 1 ° C).
- melting point 6-aminocapronitrile -34 ° C
- melting point adiponitrile + 1 ° C.
- the upper temperature is determined by the decomposition of the nitrile and the vapor pressure at the respective temperature, with larger amounts of the nitrile being taken along with the gas flowing through as the temperature increases.
- a temperature of at most 50, in particular at most 30 ° C. is advantageous.
- the nitrile can be used together with a liquid diluent.
- Suitable liquid diluents are inorganic compounds, such as water, or organic compounds, such as -C 4 -alkanols, for example methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol, s-butanol, such as ether, for example dioxane, such as aromatics, for example toluene, o-xylene, m-xylene, p-xylene, or mixtures thereof, such as water-C 1 -C 4 -alkanol mixtures, for example water-ethanol mixtures, preferably water.
- -C 4 -alkanols for example methanol, ethanol, n-propanol, n-butanol, i-butanol, s-butanol, such as ether, for example dioxane, such as aromatics, for example toluene, o-xy
- the lower temperature ⁇ is determined by the melting point of the mixture.
- a temperature of at least 10, in particular at least 20 ° C. above the melting point of the mixture is preferred.
- the upper temperature is determined by the decomposition of the mixture and the vapor pressure at the respective temperature, with larger quantities of the mixture being carried along with the gas flowing through as the temperature increases.
- a temperature of at most 50, in particular at most 30 ° C. is advantageous.
- the lower pressure should be at least the vapor pressure of the pure
- the pressure should advantageously be 0.1 kPa, in particular 1 kPa, above the vapor pressure at the selected temperature.
- a nitric gas flows through the nitrile.
- inert gases are considered which do not cause any chemical changes in the nitrile to be flowed through as a result of a reaction between nitrile and gas.
- such gases can contain impurities that are not inert to the nitrile. It goes without saying that the lower the content of such impurities in the inert gas, the better the advantageous effect of the process according to the invention.
- the inert gas can flow through the nitrile in the range from 0.01 to 100, preferably from 0.1 to 40, in particular from 1 to 15 m 3 gas / hour / m 3 nitrile.
- the inert gas can flow through the nitrile in the range from 1 to 200, preferably from 5 to 150, in particular from 10 to 80 minutes.
- the areas mentioned are understood as the sum of the times of the intervals. A longer time is not critical in itself.
- the nitrile can be stored for weeks using the method according to the invention without the advantage according to the invention being lost.
- Shorter periods of time than those according to the advantageous embodiment can also be selected. According to previous observations, a further advantageous effect can be achieved in such a case by further application of the method according to the invention.
- the flow through of the nitrile with the inert gas can be carried out in reactors known per se for the reaction of gases with liquids, for example tanks, stirred tanks, loop reactors, tubular reactors, bubble columns, reaction columns, thin-film reactors, gas-liquid bioreactors, with those for such Reactors known to supply gases in liquids, simple dipping, that is to say inlet pipes, or filter candles, are also carried out, for example from: Ullmann's Encyclopedia of Industrial Chemistry, 5th Ed., Vol B4, VCH Verlagsgesellschaft mbH, Weinheim , 1992, pp. 167-337 and pp. 381-433, or Ullmann's Encyclopedia of Industrial Chemistry, 5th Ed., Vol B2, VCH Verlagsgesellschaft mbH, Weinheim, 1988, pp. 25-31.
- reactors known per se for the reaction of gases with liquids for example tanks, stirred tanks, loop reactors, tubular reactors, bubble columns, reaction columns, thin-film reactors, gas-liquid bioreactor
- the inert gas contains droplets of the nitrile after flowing through the nitrile
- these droplets can be removed from the inert gas by means of devices known per se, for example by means of droplet separators, fiber filters, swirl layer filters, fixed bed filters, fluid bed filters, cyclones, electrical separation, scrubbers, such as they are described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 5th Ed., Vol B2, VCH Verlagsgesellschaft mbH, Weinheim, 1988, pp. 13-15 - 13-25, or, for example, by means of the conversion of gases with liquids, for example from Ullmann's Encyclopedia of Industrial Chemistry, 5th Ed., Vol B, VCH Verlagsgesellschaft mbH, Weinheim, 1992, pp.
- tanks as a reactor and the supply of the inert gas by means of an inlet pipe come into consideration.
- the nitrile obtainable by the process according to the invention can be used in the form of a water-containing reaction mixture for the production of polyamides by processes known per se. which, wherein the nitrile used in the known processes is replaced by the nitrile obtained according to the present process. According to previous observations, the parameters known for such methods can be adopted unchanged. Any advantageous adaptation of such methods to the nitrile obtainable according to the present method can easily be determined by a person skilled in the art by means of a few simple preliminary tests.
- Polyamides are understood to mean homopolymers, copolymers, mixtures and grafts of synthetic long-chain polyamides which, as an essential component, have recurring amide groups in the main polymer chain.
- examples of such polyamides are nylon 6 (polycaprolactam), nylon 6,6 (polyhexamethylene adipamide), nylon 4,6 (polytetramethylene adipamide). These polyamides are known to have the generic name nylon.
- Such polyamides can advantageously be obtained by methods known per se from monomers selected from 6-aminocapro-nitrile or a, preferably equimolar, mixture of adipodi- nitriol and hexamethylene diamine, or mixtures thereof.
- a monomer selected from 6-aminocapronitrile or a, preferably equimolar, mixture of adipodinitriol and hexamethylenediamine, or mixtures thereof can be used together with other monomers capable of forming polyamides, such as lactams, omega-aminocarboxylic acids, omega Aminocarboxylic acid nitriles, omega-amino carboxylic acid amides, omega-amino carboxylic acid salts, omega-amino carboxylic acid esters, equimolar mixtures of diamines and dicarboxylic acids, dicarboxylic acid / diamine salts, dinitriles and diamines or mixtures of such monomers.
- monomers capable of forming polyamides such as lactams, omega-aminocarboxylic acids, omega Aminocarboxylic acid nitriles, omega-amino carboxylic acid amides, omega-amino carboxylic acid salts, omega-
- Monomers or oligomers of C - to C 2 o - amino acid amides such as 6-aminocaproic acid amide, 11-aminoundecanoic acid amide and their dimers, trimers, tetramers, pentamers or hexamers,
- Esters preferably C 1 -C 4 alkyl esters, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl ester, from C 2 to Co -, preferably C - to Cig - aminocarboxylic acids, such as 6-aminocaproic acid esters, for example methyl 6-aminocaproate, 11-aminoundecanoic acid esters, for example methyl 11-aminoundecanoate,
- C - to C 2 o ⁇ * preferably C 2 - to C 14 - aliphatic dicarboxylic acid or its mono- or dinitriles, such as sebacic acid, dodecanedioic acid, adipic acid, sebacic acid dinitrile or decanoic acid dinitrile,
- Cs - to C 2 o " ⁇ * preferably Cs - to C 12 - aromatic dicarboxylic acid or its derivatives, for example chlorides, such as 2,6-naphthalenedicarboxylic acid, preferably isophthalic acid or terephthalic acid,
- C 9 - to C 0 - preferably C 9 - to Cia - arylaliphatic dicarboxylic acid or its derivatives, for example chlorides, such as o-, m- or p-phenylenediacetic acid,
- C 2 - to C 2 o - preferably C - to C 14 - aliphatic dicarboxylic acid or its mono- or dinitriles, such as sebacic acid, dodecanedioic acid, adipic acid, sebaconitrile or decanoic dinitrile,
- Ca - to C 0 - preferably Ca - to C ⁇ - aromatic dicarboxylic acid or its derivatives, for example chlorides, such as 2,6-naphthalenedicarboxylic acid, preferably isophthalic acid or terephthalic acid,
- Cg - to C 2 o ⁇ preferably Cg - to Cis - arylaliphatic dicarboxylic acid or its derivatives, for example chlorides, such as o-, m- or p-phenylenediacetic acid,
- Monomers or oligomers of a C 7 to C 0 preferably Ca to Cig arylaliphatic diamine, such as m- or p-xylylenediamine,
- C 6 - to C 2 o - preferably C 6 - to Cio - aromatic dicarboxylic acid or its derivatives, for example chlorides, such as 2, 6-naphthalenedicarboxylic acid, preferably isophthalic acid or terephthalic acid, as well as their dimers, trimers, tetramers, pentamers or hexamers,
- Cg - to Co preferably Cg - to -C 8 - arylaliphatic dicarboxylic acid or its derivatives, for example chlorides, such as o-, m- or p-phenylenediacetic acid,
- one or more chain regulators can be used in the production of the polyamides.
- Suitable chain regulators are advantageously compounds which have one or more, such as two, amino groups reactive in the formation of polyamide or one or more, such as two, carboxyl groups reactive in the formation of polyamide.
- Chain regulators which can advantageously be monocarboxylic acids, such as alkane carboxylic acids, for example acetic acid, propionic acid, such as benzene or naphthalene monocarboxylic acid, for example benzoic acid, dicarboxylic acids, such as C 4 -C ⁇ oalkanedicarboxylic acid, for example adipic acid, azelaic acid, sebacic acid, dodecanedioic acid, C 5 -C 8- cycloalkanedicarboxylic acids, for example cyclohexane-1,4-dicarboxylic acid, benzene- or naphthalenedicarboxylic acid, for example terephthalic acid, isophthalic acid,
- monocarboxylic acids such as alkane carboxylic acids, for example acetic acid, propionic acid, such as benzene or naphthalene monocarboxylic acid, for example benzoic acid
- Naphthalene-2, 6-dicarboxylic acid C 2 - to C 2 o - / preferably C 2 - to C ⁇ 2 - alkylamines, such as cyclohexylamine, C 6 - to C 2 o - preferred as Cg - to Cio ⁇ aromatic monoamines, such as aniline, or C - to Co -, preferably Cs - to Ci ⁇ - arylaliphatic monoamines, such as benzylamine, diamines, such as C 4 -C ⁇ o-alkanediamines, for example hexamethylenediamine.
- a chain regulator can advantageously be used in amounts of at least 0.01 mol%, preferably at least 0.05 mol%, in particular at least 0.2 mol%, based on 1 mol of acid amide groups of the polyamide.
- a chain regulator can advantageously be used in amounts of at most 1.0 mol%, preferably at most 0.6 mol%, in particular at most 0.5 mol%, based on 1 mol of acid amide groups of the polyamide.
- the polymerization or polycondensation is carried out by the process according to the invention in the presence of at least one pigment.
- Preferred pigments are titanium dioxide, it being possible for titanium dioxide to be present in the anatase modification, rutile modification or anatase-rutile modification mixture, or coloring compounds of an inorganic or organic nature.
- the pigments are preferably added in an amount of 0 to 5 parts by weight, in particular 0.02 to 2 parts by weight, based in each case on 100 parts by weight of polyamide.
- the pigments can be fed to the reactor with the starting materials or separately therefrom.
- polyamides obtainable by the process according to the invention can be processed according to the processes customary for polyamides into geometric structures, such as threads, fibers, flat structures and moldings, the lower tendency to discoloration of the polyamides according to the invention also being effective here.
- the discoloration is defined by the APHA number.
- the APHA number is determined in the manner described in Examples 20 as the difference in the extinction of a polyamide solution in formic acid at 470 nm and 600 nm. The lower the APHA number, the less discoloration of the polyamide.
- Polyamides obtainable by the process according to the invention which are essentially based on adiponitrile and hexamethylenediamine, preferably have an APHA number of less than 15, in particular less than 5.
- Polyamides obtainable by the process according to the invention which are essentially based on 6-aminocapronitrile, preferably have an APHA number of less than 15, in particular less than 5.
- the absorbance E of the polyamide solution is measured in a 5 cm cell at a wavelength of 470 nm (E 470 ) and 600 nm (E ⁇ 00 ) against formic acid.
- the APHA number (in Pt-Co units) is then determined as follows:
- the polyamides were prepared using a mixture of 6-aminocapronitrile (6-ACN) and deionized water.
- the 6-aminocapronitrile-water mixture was stored in a 2 1 batch tank provided with a lance suitable for introducing gas and fed via a piston pump to an apparatus according to FIG. 1 of DE-A-19804023.
- the first process stage (1) with an empty volume of 1 liter and an inner length of 1000 mm was carried out with extruded titanium dioxide granules, which according to: Ertl, Knözinger, Weitkamp: "Handbook of heterogeneous catalysis", VCH Weinheim, 1997; Page 98ff.
- the strand granules consisted of 100% Ti0 2 , which was present in the so-called anatase modification, and had a strand length between 2 and 14 mm, a strand thickness of approx. 2 mm and a specific surface area of 110 m 2 / g.
- a 2 liter separating tank was used as the second stage (2).
- the third stage (3) with an empty volume of 1 liter and an inner length of 1000 mm was filled with the titanium dioxide extrudate described in process stage (1).
- the reaction mixture could still be mixed with water from a receiver (see FIG. 1 mentioned).
- the fourth stage (4) again consisted of a separating vessel (volume 5 liters), from which the polymer melt produced was drawn out in the form of a strand with the aid of a gear pump (A).
- a 6-aminocapronitrile-water mixture with the composition according to Table 1 was stored under nitrogen for two hours in the batch kettle and nitrogen was passed through the mixture over the lance for two hours.
- the throughput D given in Table 1 is the mass flow of the reaction mixture from the batch boiler through the first process stage.
- the water throughput WZ in the third process stage is based on the throughput of the reaction mixture in the first process stage and is given in percent.
- the pressures and temperatures in the four stages are summarized in Table 1.
- the polyamide obtained from the fourth stage was dried in a vacuum drying cabinet at 3 kPa and 70 ° C. for 24 hours.
- Example 2 The procedure was as in Example 1, with the exception that the polyamide was extracted by heating 100 parts by weight of polyamide in 400 parts by weight of deionized water at a temperature of 100 ° C. for 32 hours under reflux and with nitrogen blanketing Removal of the water was gently dried and dried in a vacuum drying cabinet at 3 kPa and 70 ° C for 24 hours.
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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
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2003-7012347A KR20030094292A (ko) | 2001-03-23 | 2002-03-20 | 폴리아미드의 제조 방법 |
JP2002583494A JP2004526847A (ja) | 2001-03-23 | 2002-03-20 | ポリアミドの製造 |
BR0207858-9A BR0207858A (pt) | 2001-03-23 | 2002-03-20 | Processo para a preparação de poliamidas, e, poliamida |
CA002440856A CA2440856A1 (en) | 2001-03-23 | 2002-03-20 | Method of producing polyamides |
MXPA03007639A MXPA03007639A (es) | 2001-03-23 | 2002-03-20 | Procedimiento para la obtencion de poliamidas. |
EP02735165A EP1383822A1 (de) | 2001-03-23 | 2002-03-20 | Verfahren zur herstellung von polyamiden |
US10/472,147 US20040097692A1 (en) | 2001-03-23 | 2002-03-20 | Method of producing polyamides |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10114690A DE10114690A1 (de) | 2001-03-23 | 2001-03-23 | Verfahren zur Herstellung von Polyamiden |
DE10114690.6 | 2001-03-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002085968A1 true WO2002085968A1 (de) | 2002-10-31 |
Family
ID=7679005
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/003278 WO2002085968A1 (de) | 2001-03-23 | 2002-03-20 | Verfahren zur herstellung von polyamiden |
Country Status (12)
Country | Link |
---|---|
US (1) | US20040097692A1 (de) |
EP (1) | EP1383822A1 (de) |
JP (1) | JP2004526847A (de) |
KR (1) | KR20030094292A (de) |
CN (1) | CN1208370C (de) |
AR (1) | AR042587A1 (de) |
BR (1) | BR0207858A (de) |
CA (1) | CA2440856A1 (de) |
DE (1) | DE10114690A1 (de) |
MX (1) | MXPA03007639A (de) |
TW (1) | TW593430B (de) |
WO (1) | WO2002085968A1 (de) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2245129A (en) * | 1935-01-02 | 1941-06-10 | Du Pont | Process for preparing linear polyamides |
US4568736A (en) * | 1984-09-17 | 1986-02-04 | The Standard Oil Company | Preparation of polyamide from omega-aminonitrile with oxygen containing phosphorus catalyst |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2234129A (en) * | 1940-08-03 | 1941-03-04 | Pfeil William Carl | Ice cutting device |
US4436898A (en) * | 1982-04-20 | 1984-03-13 | Davy Mckee Aktiengesellschaft, Borsigalle | Preparation of spinnable polyamide from dinitrile, diamine, H2 O with P containing catalyst |
DE19513940A1 (de) * | 1994-07-14 | 1996-01-18 | Inventa Ag | Verfahren zur Herstellung von Vorkondensaten teilkristalliner oder amorpher, thermoplastisch verarbeitbarer teilaromatischer Polyamide bzw. Copolyamide |
DE19804033A1 (de) * | 1998-02-02 | 1999-08-05 | Basf Ag | Kontinuierliches Verfahren zur Herstellung von Polyamiden aus Aminonitrilen |
DE19808407A1 (de) * | 1998-02-27 | 1999-09-09 | Basf Ag | Herstellung von Polyamiden durch Reaktivdestillation |
DE19962573A1 (de) * | 1999-12-23 | 2001-07-05 | Basf Ag | Verfahren zur Herstellung von Polyamiden |
DE10033544A1 (de) * | 2000-07-11 | 2002-01-24 | Basf Ag | Kontinuierliches Verfahren zur Herstellung von Polyamiden aus Aminonitrilen |
-
2001
- 2001-03-23 DE DE10114690A patent/DE10114690A1/de not_active Withdrawn
-
2002
- 2002-03-04 TW TW091103918A patent/TW593430B/zh not_active IP Right Cessation
- 2002-03-19 AR ARP020100985A patent/AR042587A1/es active IP Right Grant
- 2002-03-20 BR BR0207858-9A patent/BR0207858A/pt not_active IP Right Cessation
- 2002-03-20 EP EP02735165A patent/EP1383822A1/de not_active Withdrawn
- 2002-03-20 MX MXPA03007639A patent/MXPA03007639A/es unknown
- 2002-03-20 CN CNB028071123A patent/CN1208370C/zh not_active Expired - Fee Related
- 2002-03-20 CA CA002440856A patent/CA2440856A1/en not_active Abandoned
- 2002-03-20 KR KR10-2003-7012347A patent/KR20030094292A/ko not_active Application Discontinuation
- 2002-03-20 US US10/472,147 patent/US20040097692A1/en not_active Abandoned
- 2002-03-20 JP JP2002583494A patent/JP2004526847A/ja not_active Withdrawn
- 2002-03-20 WO PCT/EP2002/003278 patent/WO2002085968A1/de not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2245129A (en) * | 1935-01-02 | 1941-06-10 | Du Pont | Process for preparing linear polyamides |
US4568736A (en) * | 1984-09-17 | 1986-02-04 | The Standard Oil Company | Preparation of polyamide from omega-aminonitrile with oxygen containing phosphorus catalyst |
EP0227866A1 (de) * | 1984-09-17 | 1987-07-08 | The Standard Oil Company | Katalytisches Verfahren zur Herstellung von Polyamiden aus omega-Aminonitrilen |
Also Published As
Publication number | Publication date |
---|---|
DE10114690A1 (de) | 2002-09-26 |
MXPA03007639A (es) | 2003-12-04 |
CN1208370C (zh) | 2005-06-29 |
CA2440856A1 (en) | 2002-10-31 |
JP2004526847A (ja) | 2004-09-02 |
EP1383822A1 (de) | 2004-01-28 |
TW593430B (en) | 2004-06-21 |
CN1498238A (zh) | 2004-05-19 |
AR042587A1 (es) | 2005-06-29 |
BR0207858A (pt) | 2004-03-23 |
KR20030094292A (ko) | 2003-12-11 |
US20040097692A1 (en) | 2004-05-20 |
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