WO2000017169A1 - Procede de preparation d'un derive de carbamoyle n-alkyle ou n-aryle - Google Patents

Procede de preparation d'un derive de carbamoyle n-alkyle ou n-aryle Download PDF

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Publication number
WO2000017169A1
WO2000017169A1 PCT/NL1999/000589 NL9900589W WO0017169A1 WO 2000017169 A1 WO2000017169 A1 WO 2000017169A1 NL 9900589 W NL9900589 W NL 9900589W WO 0017169 A1 WO0017169 A1 WO 0017169A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
preparation
alkyl
caprolactam
coatings
Prior art date
Application number
PCT/NL1999/000589
Other languages
English (en)
Inventor
Jacobus Antonius Loontjens
Bartholomeus Johannes Margaretha Plum
Original Assignee
Dsm N.V.
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 Dsm N.V. filed Critical Dsm N.V.
Priority to AU60100/99A priority Critical patent/AU6010099A/en
Priority to JP2000574079A priority patent/JP2002526480A/ja
Priority to EP99969410A priority patent/EP1115709A1/fr
Publication of WO2000017169A1 publication Critical patent/WO2000017169A1/fr
Priority to US09/815,268 priority patent/US6448394B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D223/08—Oxygen atoms
    • C07D223/10—Oxygen atoms attached in position 2
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C08G18/8074—Lactams
    • 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
    • C08G2150/00—Compositions for coatings
    • C08G2150/20—Compositions for powder coatings
    • 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
    • C08G2390/00—Containers
    • C08G2390/40—Inner coatings for containers

Definitions

  • the invention relates to a process for the preparation of an N-alkyl or N-aryl carbamoyl derivative, and m particular a blocked isocyanate.
  • a blocked isocyanate is a compound which contains an isocyanate with a blocking agent .
  • Bloc ed lsocyanates are used in tne preparation of polyurethanes ana polyurea.
  • a blocked isocyanate can in a stable manner be mixed with a polyol at temperatures of up to, for example, 150°C . Upon an increase in temperature, the blocking agent splits off from the isocyanate group, so that tne released isocyanate can react with the polyol that is present to form a polyurethane .
  • a process for the preparation of an N-alkyl or N-aryl carcamoyl derivative is disclosed in DE-A- 2712931.
  • an isocyanate is contacted with caprolactam, as a result of which a caprolactam- blocked isocyanate is formed.
  • a drawback of the process disclosed m DE- A-2712931 is that a reaction with isocyanate involves safety risks.
  • the aim of the invention is to provide a safer process.
  • fragments X in the form of XH are a lactam, oxime, imide or triazole.
  • An advantage of the process according to the invention is that a blocked isocyanate is formed in which no free isocyanate is present anymore.
  • a further advantage of the process according to the invention is that it can be used to prepare an N-alkyl or N-aryl carbamoyl derivative of which the nitrogen is secondary and the derivative is a lactam, oxime, imide or triazole. These are compounds that cannot be prepared via the known isocyanate route.
  • amines may be mono-, di-, tri-, polyammes or mixtures of these, Examples of di- and t ⁇ ammes are diamino octane, diamino nonane, diammo dodecane, trisammo nonane, diamino dioxydecane, diamino dioxododecane, bishexamethylene trisamme and Jeffamines.
  • Other suitable amines are oligomers, as reaction products of two components. Examples of oligomers are the reaction products of hexamethylene diamme with adipic acid, urea, carbonyl biscaprolactamate (CBC) and with 1 or 2 caprolactam molecules
  • An advantage of the process according to the invention for the preparation of blocked isocyanates on the basis of oligomeric amines is the fact that the fragments (X) , which are split off in the reaction between the carbonic acid derivative and the amine, can readily be removed from the reaction mixture as XH. This contrasts with the removal of the triethylamme salt that is released m the preparation of blocked isocyanates on the basis of phosgene and triethylamme .
  • Contacting an amme with the carbonic acid derivative can optionally be effected m a solvent.
  • this is done by dissolving the carbonic acid derivative according to formula I in a suitable first solvent.
  • Suitable solvents are generally non- protic solvents such as esters, ethers, cyclic carbonates, cyclic amides and hydrocarbons.
  • the amme, dissolved m a second solvent can slowly be added, with continuous stirring, to the solution of the carbonic acid derivative.
  • Second solvents are preferably also chosen from the same group of non-protic solvents.
  • the first and the second solvent are the same .
  • the mixture is stirred for some time at a temperature between room temperature and 150°C. Above 150°C the blocking agent can readily be split off. Stirring preferably takes place at a temperature between 50 and 100 °C, after which the N-alkyl or N-aryl carbamoyl derivative formed can be separated from the reaction mixture according to known techniques .
  • the product obtained by the process according to the invention can be very widely applied in technically different fields, both in thermosetting and in thermoplastic applications.
  • Examples are powder paint compositions, coating systems based on water or solvent and can or coil coating systems, inks, toners, film formers for glassfibre sizings, adhesives, hot melts and in rubber compositions.
  • Unmodified or partly modified polymers according to the invention can generally be used in powder paint compositions, in can or coil coating compositions and in solvent-based coating compositions.
  • thermosetting powder paints have a better resistance to chemicals than thermoplastic powder paints.
  • intensive efforts have for a long time been made to develop crosslinkers and polymers for thermosetting powder coatings.
  • a thermosetting powder paint binder composition generally contains more than 50 wt . % polymer and less than 50 wt . % crosslinker.
  • the product obtained according to the invention can be used in a powder paint composition as a crosslinker in combination with a hydroxyl functional polymer.
  • the hydroxyl functional polymer is preferably a polyester, a polyacrylate or a mixture of both.
  • the polyester has a hydroxyl number of between 20 and 100 mg of KOH/gram of resin and an acid number of less than 10 mg of KOH/gram of resin.
  • the polyacrylate has a hydroxyl number of between 40 and 150 mg of KOH/gram of resin and an acid number of less than 20 mg of KOH/gram of resin.
  • the weight ratio between the polymer containing hydroxyl groups and the crosslinker can be between about 95:5 and about 50:50, and preferably between 93:7 and 70:30. This ratio depends on, among other factors, the hydroxyl number of the polymer.
  • the hydroxyl functional polymers can be mixed with the blocked crosslinker by extrusion, for example, at a temperature of about 100 °C.
  • the curing takes place at temperatures of, for example, between about 130°C and about 170°C (in, for example, about 10- 40 minutes) , and preferably above about 150°C.
  • Additives such as for example fillers, catalysts, curing agents, flow agents and/or stabilizers and, if required, pigments, can be added to the coating systems, preferably before the extrusion.
  • Suitable polyesters can be obtained via customary preparation methods from carboxylic acids or equivalents thereof.
  • carboxylic acids or equivalents thereof The use of mainly aromatic carboxylic acids is preferred. Examples include phthalic acid, isophthalic acid, terephthalic acid, pyromellitic acid, trimellitic acid, 3,6-di- chlorophthalic acid, tetrachlorophthalic acid and, in so far as available, equivalents like anhydrides, acid chlorides or lower alkyl esters thereof.
  • the carboxylic acid component comprises at least 50 wt.%, and preferably at least 70 mol%, isophthalic acid and/or terephthalic acid.
  • the diol component of the polyester is an aliphatic diol .
  • the alcohol component preferably contains
  • the polycarboxylic acids applied can be cycloaliphatic and/or acyclic polycarooxylic acids.
  • examples include cyclohexane dicarboxylic acid, tetrahydrophthalic acid, hexahydroendomethylene tetrahydrophthalic acid, azelamic acid, sebacic acid, decane dicarboxylic acid, adipic acid, succinic acid and maleic acid.
  • the amount of cycloaliphatic and/or acyclic polycarboxylic acid can be up to about 30 mol%, and preferably up to about 20 mol%, relative to the total of carboxylic acids. Hydroxycarboxylic acids and/or, optionally, lactones can also be used.
  • Examples include 12 -hydroxylstearic acid, epsilon caprolactone and hydroxypivalic ester of neopentyl glycol.
  • Monocarboxylic acids can also be added in minor amounts, for example less than 5% by weight, during the preparation. Examples include oenzoic acid, ter . -butylbenzoic acid, hexanydrobenzoic acid and saturated aliphatic monocarboxylic acids.
  • the polyesters can be prepared by este ⁇ fication or transesterification known to those skilled m the art.
  • customary catalysts can be used. Examples include dibutyl tin oxide or tetrabutyl titanate.
  • the preparation conditions and the COOH/OH ratio are chosen so that a polyester resin having the desired hydroxyl number and acid number is obtained, for example a hydroxyl number of between about 20 and about 100 mg of KOH/gram of resin and an acid, number of less than about 10 mg of KOH/gram of resin.
  • polyesters are based on about 40-100 mol% isophthalic acid and about 0-60 mol% terephthalic acid as dicarboxylic acids (wherein the quantities of isophthalic acid and terephthalic acid together amount to 100 mol%) .
  • the amount of isophthalic acid is more than 60 mol%.
  • the polyester can also be based on more than two dicarboxylic acids.
  • the hydroxyl functional acrylate resin can be, for example, based on hydroxyl (meth) acrylate, hydroxypropyl (meth) acrylate and methyl (meth) acrylate .
  • the resin can also be based on (meth) acrylic acid and alkyl esters of (meth) acrylic . Examples include ethyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, n-propyl (meth) acrylate, isobutyl (meth) acrylate, ethylhexyl acrylate and/or cyclohexyl (meth) acrylate . Vinyl compounds such as, for example, styrene can also be used
  • the glass transition temperature (Tg) of the product obtained by process according to the invention lies between 10 and 150°C, preferably between 50 C C and 110°C, depending on the selected starting materials and the molecular weight.
  • thermosetting powder coatings in general and the chemical reactions for curing powder paints to form cured coatings are described by Misev in Powder Coatings, Chemistry and
  • thermosetting binder composition is generally defined as the resinous part of the powder paint consisting of polymer and crosslinker.
  • the usual additives can be used in the binder composition and in the powder paint system according to the invention, such as for example pigments, fillers, degassing agents, flow agents and stabilizers.
  • Suitable pigments are for example inorganic pigments, such as for example titanium dioxide, zinc sulphide, iron oxide and chromium oxide, and also organic pigments such as for example azo compounds.
  • Suitable fillers are for example metal oxides, silicates, carbonates and sulphates.
  • UV stabilizers such as quinones, (sterically hindered) phenolic compounds, phosphonites , phosphites, thioethers and HALS compounds (hindered amine light stabilizers) can for example be used as stabilizers.
  • degassing agents are benzoin and.cyclohexane dimethanol bisbenzoate.
  • the flow agents include for example polyalkylacrylates , fluorohydrocarbons and silicone fluids.
  • Other suitable additives are for example additives for improving tribocharging, such as sterically hindered tertiary amines that are described in EP-B-371528.
  • Powder paints according to the invention can be applied in the usual manner, for example by electrostatically spraying the powder onto an earthed substrate and curing the coating by exposing it to heat at a suitable temperature for a sufficient length of time.
  • the applied powder can for example be heated in a gas oven, an electric oven or with the aid of infrared radiation.
  • Thermosetting powder paint compositions intended for industrial applications are described in a general sense in Powder Coatings, Chemistry and Technology, Misev, pages 141-173 (1991) .
  • compositions according to the present invention can be used in powder paints for use on, for example, metal, wooden and plastic substrates.
  • the coatings are also suitable for use in the automotive industry for coating parts and accessories.
  • thermosetting powder coatings As is evident from, for example, 'Resins and curing agents for thermosetting powder coatings'
  • coatings based on a solvent or water are not related to thermosetting powder paints, for powder paints must meet requirements relating to, for example, the melting point of the binder, the rheological properties, the reactivity and the stability, that do not apply to v wet' coatings. If the molecular weight, the viscosity and the glass transition temperature of the hydroxyl functional polymers are adapted through the choice of monomers, these polymers, in combination with the crosslinker according to the invention, can - surprisingly - also be used as starting compound for solvent- or water- based coatings .
  • the product obtained by the process according to the invention is applied as a crosslinker in a binder system for a coil coating or for a can coating.
  • Suitable binder systems in these applications are hydroxyl functional polymers such as polyesters or polyacrylates.
  • Suitable solvents in these applications are esters or hydrocarbons.
  • the catalysts which can be used in coil or can coatings are well known from polyurethane chemistry. Examples of catalysts are Sn catalysts.
  • Coil coatings can be obtained via commonly known processes as described for example in "Coil Coatings” by Joseph E. Gaske (Federation of Societies for Coatings Technology, February 1987, pp. 7-19).
  • the curing conditions and additives can be chosen to depend on the desired peak metal temperature (PMT) and the nature and thickness of the substrate.
  • the curing time will generally be between about 20 and about 70 seconds at temperatures of between about 250 °C and about 400°C and a PMT of between 204 °C and 249°C.
  • Suitable substrates include for example steel, tin-plated steel and aluminium.
  • the coil coatings according to the invention are suitable for use as primer and as top coat and can for example be used as coating for household equipment such as fridges, freezers, microwave ovens, ovens and boilers, as coating for caravans and as coating for facade cladding.
  • the resin composition according to the invention also yields good results in the can coating industry, in which the desired layer thickness is generally thinner and in which the curing conditions differ from the conditions in the preparation of coil coatings .
  • Can coatings can be obtained via processes of the kind described in for example Organic Coatings - Science and Technology, Volume 2: Applications, Properties and Performance 1 by Z.W. Wicks et al . (Wiley-Interscience, 1994, pp. 284-290).
  • the curing conditions and additives can be selected to depend on the desired application and the nature and thickness of the substrate.
  • the curing time will generally lie between a few seconds and tens of minutes at temperatures of between about 100°C and about 220°C.
  • Suitable substrates include for example steel, tin-plated steel (ETP, Electrolytic Tin Plate) , chrpmium-plated steel (ECCS, Electrolytic Chromium- Chromium oxide Steel) and aluminium.
  • ETP Electrolytic Tin Plate
  • ECCS Electrolytic Chromium- Chromium oxide Steel
  • the coatings according to the invention are suitable for use as interior and exterior coatings and can be used for example as coatings for beer cans, cans for other beverages ( ' 2 and 3 piece ' ) , spray cans , can ends, tubes, drums, cigar boxes and fish cans (the so- called 'drawn-redrawn (DRD) ' , 'draw-wall ironed (DWI) ' cans) . They can be used in pigmented or in unpigmented compositions.
  • DDD 'drawn-redrawn
  • DWI 'draw-wall ironed
  • the use of the exterior coating is important primarily from a decorative viewpoint, for giving the substrate a saleable appearance. It protects the metal from corrosion and the coating also serves as a label.
  • the interior coating is mainly intended on the one hand to protect the contents of the can against the influences of the metal and on the other to protect the metal against the contents of the can.
  • the type of monomers to be used to prepare the polyester, the crosslinkers and the curing conditions can be chosen to depend on the desired use.
  • the systems according to the invention can be used in pigmented an in unpigmented compositions . If so desired, the usual additives such as pigments, fillers, stabilizers, dispersing agents, flow-promoting agents and defoaming agents can be added to the binder system according to the invention.
  • Caprolactam-blocked tris (isocyanato-ethyl) amine proved to be a coloured oil and was obtained in a yield of 99%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un procédé de préparation d'un dérivé de carbamoyle N-alkyle ou N-aryle d'après lequel on met une amine en contact avec un dérivé d'acide carbonique selon la formule générale (I), dans laquelle les fragments X sous la forme de XH sont lactame, oxime, imide ou triazole. L'invention concerne notamment la préparation d'un isocyanate bloqué conformément à un procédé qui n'utilise pas d'isocyanate. L'invention concerne aussi l'utilisation dans un revêtement du dérivé de carbamoyle N-alkyle ou N-aryle préparé selon le procédé de l'invention.
PCT/NL1999/000589 1998-09-24 1999-09-21 Procede de preparation d'un derive de carbamoyle n-alkyle ou n-aryle WO2000017169A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU60100/99A AU6010099A (en) 1998-09-24 1999-09-21 Process for the preparation of an n-alkyl or n-aryl carbamoyl derivative
JP2000574079A JP2002526480A (ja) 1998-09-24 1999-09-21 Ｎ−アルキルまたはｎ−アリールカルバモイル誘導体の製造方法
EP99969410A EP1115709A1 (fr) 1998-09-24 1999-09-21 Procede de preparation d'un derive de carbamoyle n-alkyle ou n-aryle
US09/815,268 US6448394B1 (en) 1998-09-24 2001-03-23 Process for the preparation of an N-alkyl or N-aryl carbamoyl derivative

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL1010175A NL1010175C2 (nl) 1998-09-24 1998-09-24 Werkwijze voor de bereiding van N-alkylcarbamoylderivaat.
NL1010175 1998-09-24

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US09/815,268 Continuation US6448394B1 (en) 1998-09-24 2001-03-23 Process for the preparation of an N-alkyl or N-aryl carbamoyl derivative

Publications (1)

Publication Number Publication Date
WO2000017169A1 true WO2000017169A1 (fr) 2000-03-30

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PCT/NL1999/000589 WO2000017169A1 (fr) 1998-09-24 1999-09-21 Procede de preparation d'un derive de carbamoyle n-alkyle ou n-aryle

Country Status (5)

Country Link
EP (1) EP1115709A1 (fr)
JP (1) JP2002526480A (fr)
AU (1) AU6010099A (fr)
NL (1) NL1010175C2 (fr)
WO (1) WO2000017169A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001040178A1 (fr) * 1999-12-02 2001-06-07 Dsm N.V. Procede de preparation d'un derive d'acide carboxylique
NL1020029C2 (nl) * 2002-02-21 2003-08-25 Dsm Nv Werkwijze voor de bereiding van ethylenisch onverzadigde verbindingen met lactam-geblokte isocyanaatgroepen, alsmede de bereiding en toepassing daarvan.
WO2004046156A1 (fr) * 2002-11-20 2004-06-03 Dsm Ip Assets B.V. Agent de couplage de silane, procede servant a preparer cet agent, son utilisation dans un composite ou sur un substrat, nanoparticules et leur utilisation dans un revetement
WO2017051291A1 (fr) * 2015-09-21 2017-03-30 Colormatrix Holdings, Inc. Matières polymères
CN110589868A (zh) * 2019-09-04 2019-12-20 湖北三宁化工股份有限公司 己内酰胺硫酸酯制备高纯硫酸盐并副产己内酰胺的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1415730A (en) * 1972-10-13 1975-11-26 Cassella Farbwerke Mainkur Ag Preparation of substituted ureas
DE2712931A1 (de) * 1977-03-24 1978-09-28 Veba Chemie Ag Isocyanuratgruppen - und endstaendig- blockierte isocyanatgruppen - enthaltende verbindungen
DE2830206A1 (de) * 1978-07-10 1980-01-24 Huels Chemische Werke Ag Blockierte diisocyanate, ihre herstellung sowie ihre verwendung als vernetzungsmittel

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1415730A (en) * 1972-10-13 1975-11-26 Cassella Farbwerke Mainkur Ag Preparation of substituted ureas
DE2712931A1 (de) * 1977-03-24 1978-09-28 Veba Chemie Ag Isocyanuratgruppen - und endstaendig- blockierte isocyanatgruppen - enthaltende verbindungen
DE2830206A1 (de) * 1978-07-10 1980-01-24 Huels Chemische Werke Ag Blockierte diisocyanate, ihre herstellung sowie ihre verwendung als vernetzungsmittel

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001040178A1 (fr) * 1999-12-02 2001-06-07 Dsm N.V. Procede de preparation d'un derive d'acide carboxylique
NL1020029C2 (nl) * 2002-02-21 2003-08-25 Dsm Nv Werkwijze voor de bereiding van ethylenisch onverzadigde verbindingen met lactam-geblokte isocyanaatgroepen, alsmede de bereiding en toepassing daarvan.
WO2003070704A1 (fr) * 2002-02-21 2003-08-28 Dsm Ip Assets B.V. Procede de preparation de composes ethyleniquement insatures par des groupes isocyanate a blocage lactame
WO2004046156A1 (fr) * 2002-11-20 2004-06-03 Dsm Ip Assets B.V. Agent de couplage de silane, procede servant a preparer cet agent, son utilisation dans un composite ou sur un substrat, nanoparticules et leur utilisation dans un revetement
WO2017051291A1 (fr) * 2015-09-21 2017-03-30 Colormatrix Holdings, Inc. Matières polymères
CN107922632A (zh) * 2015-09-21 2018-04-17 彩色矩阵控股公司 聚合材料
US10815341B2 (en) 2015-09-21 2020-10-27 Colormatrix Holdings, Inc. Polymeric materials
CN110589868A (zh) * 2019-09-04 2019-12-20 湖北三宁化工股份有限公司 己内酰胺硫酸酯制备高纯硫酸盐并副产己内酰胺的方法

Also Published As

Publication number Publication date
NL1010175C2 (nl) 2000-03-27
EP1115709A1 (fr) 2001-07-18
JP2002526480A (ja) 2002-08-20
AU6010099A (en) 2000-04-10

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