WO1998015533A1 - Verfahren zur herstellung von 1,8-diaminonaphthalinen und ihrer derivate der 2,3-dihydroperimidine - Google Patents
Verfahren zur herstellung von 1,8-diaminonaphthalinen und ihrer derivate der 2,3-dihydroperimidine Download PDFInfo
- Publication number
- WO1998015533A1 WO1998015533A1 PCT/EP1997/005316 EP9705316W WO9815533A1 WO 1998015533 A1 WO1998015533 A1 WO 1998015533A1 EP 9705316 W EP9705316 W EP 9705316W WO 9815533 A1 WO9815533 A1 WO 9815533A1
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- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- formula
- optionally substituted
- butyl
- hydroxy
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3665—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/12—Perinones, i.e. naphthoylene-aryl-imidazoles
Definitions
- the invention relates to a process for the preparation of 1,8-diminonaphthahnes and their derivatives of 2,3-dihydroperimidines, a process for the preparation of their precursors and their use as starting material in the production of perinone and as a coupling component in the production of mono- or polyazo dyes.
- 466 805 are known or mono- or polyazo dyes with 2,3-dihydroperimidines as coupling components as are known, for example, from US Pat. No. 4,667,020 or US Pat. No. 4,122,027, starting from 1,8-dimonaphthalene
- Penins are produced by reacting 1,8-diminaphthalene cocks with aromatic di- or tetracarboxylic acids. 2,3-dihydroperimidines are made by
- dyes in particular the pen dyes, the latter being preferably used for coloring plastics, are high
- 1,8-diaminonaphthalenes are generally prepared by nitrating naphthalenes (DE-A 2 400 887) and subsequent reduction (DE-A-2 452 015).
- nitration already leads to isomer mixtures.
- nitration of 1 - Nitronaphthalene is a mixture of 40% 1,5-diamino-naphthalene and 60% 1,8-diamonaphthalene (Houben-Weyl, Methods of Organic
- the object of the present invention was therefore to provide a new process for preparing 1,8-diaminonaphthalenes and their derivatives, 2,3-dihydroperimidines, which no longer has the disadvantages mentioned above
- n a number from 0 to 6
- X can each have different or identical meanings as mentioned above,
- R 1 and R 2 independently of one another for hydrogen, alkyl, in particular optionally substituted C r C 4 alkyl, preferably methyl, ethyl, n-propyl, l-propyl, n-butyl, sec-butyl and tert-butyl, optionally substituted C 5 -C 7 cycloalkyl, in particular cyclohexyl, or
- R 1 and R 2 together with the C atom to which they are attached form an optionally substituted heterocyclic 5- or 6-ring which contains 1 to 3 identical or different heteroatoms from the group N, O and S.
- the carbonyl compound of the formula (III) used is preferably used in stoichiometric amounts, or in excess, based on the l-hydroxy-8-aminonaphthalene of the formula (II).
- a molar ratio of 1 1 to 2 1 is preferably chosen , preferably 1 1 to 1.5 1
- the alkali hydrogen sulfite, Ammonium sulfite, alkali sulfite or ammonium hydrogen sulfite is preferably used in stoichiometric amounts, based on the sum of the carbonyl compound (III) used and the hydroxyaminonaphthalene of the formula (II).
- 1 to 2 mol equivalents, based on 1 mol of the total amount of III and II, are preferably used.
- the reaction is preferably carried out at a
- the process according to the invention is generally carried out in water or an organic solvent or mixtures thereof, in particular in an aqueous medium, the water content preferably being at least 40% by weight, in particular 40 to 60% by weight.
- Suitable organic solvents are dioxane and dialkyl glycol ether.
- ammonia to the alkali hydrogen sulfite, ammonium sulfite, alkali sulfite or ammonium hydrogen sulfite used is preferably used in a molar ratio of 2: 1 to 5: 1.
- the l-hydroxy-8-aminonaphthalenes of the formula (II) are known, for example, from DE-A 55 404, DE-A 54 662 or DE-A 2 717 708.
- carbonyl compounds are aliphatic, cycloaliphatic or heterocyclic ketones and aldehydes such as acetone, butan-2-one, 3-methyl-butan-2-one, 3-pentanone or 4-methyl-3-pentanone. Ketones are particularly preferred.
- the invention further relates to a process for the preparation of 1,8-diamino-naphthalenes of the formula (IV)
- n and X have the meaning given above, which is characterized in that 2,3-dihydroperimidines of the formula (I), preferably those obtained by the process according to the invention, are hydrolyzed in the presence of an acidic catalyst in an aqueous medium
- acidic catalysts which can be mentioned are hydrochloric acid, acetic acid, sulfuric acid, propionic acid or lactic acid.
- Preferred acidic catalysts are hydrochloric and / or sulfuric acid
- Water or a mixture of water and a water-miscible solvent is preferably used as the aqueous medium for the process according to the invention for the preparation of the compounds (IV).
- the water content is preferably more than 70% by weight.
- the water-miscible solvent is preferably methanol, ethanol, isopropanol, n-propanol, n-butanol, glycols such as ethylene glycol and diethylene glycol, acetone, glycol ether and lactones, lactams or mixtures thereof
- Examples of ⁇ -butyrolactam, ⁇ -valerolactam, ⁇ -caprolactam and their N-substituted derivatives, such as N-methyl- ⁇ -butyrolactam, are suitable lactams.
- suitable lactones are ⁇ -butyrolactone, ⁇ -valerolactone and ⁇ -valerolactone .
- the hydrolysis of 2,3-dihydroperimidine according to the invention is preferably carried out at a temperature of 80-140 ° C., optionally under pressure, for example in an autoclave
- 2,3-dihydroperimidine prepared by the process according to the invention directly without intermediate isolation by acidification to hydrolyze the reaction solution or suspension to a pH less than 7, in particular a pH of 1 to 5, preferably 1 to 3, by means of an organic or inorganic acid to give 1,8-diaminonaphthalene of the formula (IV).
- the invention further relates to a process for the preparation of l-hydroxy-8-aminonaphthalenes of the formula (II)
- the mixtures of alcohol and alkali used in particular alkali hydroxides, such as NaOH or KOH, can optionally also contain water, preferably in amounts of about 0.1 to about 10% by weight, based on the total weight of the mixture.
- Suitable alcohols are, for example, monohydric or polyhydric alcohols and their ethers with at least one OH group.
- Examples include C r C 8 alkanols, polyhydric alcohols such as glycol and its mono-C, -C 4 -alkyl ethers such as methyl glycol, ethyl glycol, propyl glycol, isopropyl glycol, butyl glycol, propylene glycol, tetramethylene glycol, pentamethylene glycol, hexamethylene glycol and their mono -C 1 -C 4 alkyl ether, further Reaction products of ethylene glycol or propylene glycol with ethylene oxide and / or propylene oxide, in particular those with 5 to 15 mol ethylene oxide and / or propylene oxide, for example diethylene glycol, triethylene glycol, tetraethylene glycol and preferably polyethylene glycol or polypropylene glycol with molecular weights of about 300 to 600 g / mol.
- polyhydric alcohols such as glycol and its mono-C, -C 4 -alkyl ethers
- the process is preferably carried out in such a way that, for 1 part by weight of sulfonic acid of the formula (V), for example 1.5 to 20 parts by weight, preferably 2.0 to 8 parts by weight of the respective alcohol and 0.4 to 10 parts by weight, preferably 1.0 to 3.0 parts by weight of potassium hydroxide or sodium hydroxide can be used.
- sulfonic acid of the formula (V) for example 1.5 to 20 parts by weight, preferably 2.0 to 8 parts by weight of the respective alcohol and 0.4 to 10 parts by weight, preferably 1.0 to 3.0 parts by weight of potassium hydroxide or sodium hydroxide can be used.
- reaction temperatures are preferably from 70 to 200 ° C., when polyglycols are used, preferably from 140 to 190 ° C.
- reaction mixture is preferably cooled and, for example, with an alcohol
- the invention further relates to a process for the preparation of perinone dyes of the formula (VI)
- an ortho-phenylene, ortho-naphthylene, peri (1,8) naphthylene, or an arylene of more than two, which may be substituted by n identical or different substituents Y, means benzene rings, where the arylene residues, which have more than two benzene rings fused together, are bridged in the ortho or corresponding to a peri position in the naphthylene,
- XC j -C ß alkyl halogen, nitro, chlorosulfonyl, aryloxysulfonyl, hydroxy, alkoxy, acyloxy, an optionally substituted by alkyl or aryl
- Aminosulfonyl or a fused-on cycloaliphatic or heterocyclic ring,
- n is a number between 0 and 6
- n is a number between 0 and 6
- X can each have different or the same meaning as defined above, and n is greater than 1
- Y can each have different or identical meanings as mentioned above,
- the reaction can be carried out directly by melting together aquimolar amounts of the component of the formulas (I) and (VII) at temperatures from 50 ° C. to 220 ° C., preferably at 120 to 180 ° C., or more advantageously in a solvent at temperatures of 20 ° C to 220 ° C, preferably at 50 to 180 ° C, optionally carried out under pressure, wherein the water of reaction can be removed by distillation
- Suitable solvents are, for example, chlorobenzene, o-dichlorobenzene, trichlorobenzene, xylene, dimethylformamide, N-methylpyrrohdon, N-methyl- ⁇ -butyro-lactam, ⁇ -valerolactam, glacial acetic acid, propionic acid, phenol, cresols, phenoxyethanol, glycols and their mono - And dialkyl ethers, alcohols, for example methanol, ethanol, i-propanol, water and aqueous solvents, such as, for example, dilute sulfuric acid, dilute hydrochloric acid, dilute acetic acid, methanesulfonic acid, glycolic acid, lactic acid or propionic acid
- reaction can be carried out with the addition of an acidic catalyst
- Suitable catalysts include zinc chloride, p-toluenesulfonic acid, hydrochloric acid, sulfuric acid, organic acids and others
- —C 6 H 5 here and also in the following represents phenyl, Y fluorine, chlorine, bromine, -N0 2 , -OH, -OCH, -NH 2 , chlorosulfonyl, -NHCOCH ⁇ ,
- m is a number between 0 and 4 and
- n is a number between 0 and 5
- n and m are 0
- the invention also relates to a process for the preparation of the penin dyes of the formula (VI), characterized in that a 1,8-diminonaphthalene of the formula (IV) obtained by the process according to the invention instead of the 2,3-dihydrope ⁇ m ⁇ d ⁇ ns of the formula (I) described above is used under the same conditions
- the invention also relates to a process for the mass coloring of plastics using the Penon dyes obtained by the process according to the invention and the plastics colored therewith
- bulk colors are understood in particular to be processes in which the dye is incorporated into the molten plastic mass, for example under
- thermoplastics for example vinyl polymers, polyesters and polyamides
- Suitable vinyl polymers are polystyrene, styrene-acrylate copolymers, styrene-butadiene copolymers, styrene-butadiene-acrylonitrile terpolymers, polymethacrylate and others Polyesters which are also suitable are polyethylene terephthalates, polycarbonates and cellulose esters
- Polystyrene, styrene copolymers, polycarbonates and polymethacrylate are preferred. Polystyrene is particularly preferred
- the high-molecular compounds mentioned can be present individually or in mixtures, as plastic masses or melts
- the dyestuffs according to the invention are used in finely divided form, although dispersants can not be used
- the dyes (VI) are used after the polymerization, they are mixed or ground dry with the plastic granulate and this mixture is plasticized and homogenized, for example on mixing rollers or in screws. However, the dyes can also be added to the molten mass and homogeneously distributed by stirring The material pre-colored in this way is then processed as usual, for example by spinning to form bristles, thread, etc. or by extrusion or by injection molding to give molded parts
- the dyes of the formula (VI) are resistant to polymerization catalysts, in particular peroxides, it is also possible to add the dyes to the monomeric starting materials and then to polymerize them in the presence of polymerization catalysts.
- the dyes are preferably dissolved in or with the monomeric components mixed them intimately
- the dyes of the formula (VI) are preferably used for coloring the polymers mentioned in amounts of 0.0001 to 1% by weight, in particular 0.01 to 0.5% by weight, based on the amount of polymer
- pigments that are insoluble in the polymers such as titanium dioxide
- Titanium dioxide can be used in an amount of 0.01 to 10% by weight, preferably 0.1 to 5% by weight, based on the amount of polymer
- the process according to the invention gives transparent or covered brilliant dyeings with good heat resistance and good light and weather fastness
- the invention further relates to the use of the 2,3-dihydroperimidines of the formula (I) obtained by the process according to the invention as a coupling component for the preparation of mono- or polyazo dyes, as are known, for example, from US Pat. No. 4,667,020.
- reaction mixture was concentrated with. Neutralized sulfuric acid, filtered off the product and washed with water.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU47063/97A AU4706397A (en) | 1996-10-10 | 1997-09-29 | Method for producing 1,8-diaminonaphthalines and their 2,3-dihydroperimidine derivatives |
JP10517136A JP2001501667A (ja) | 1996-10-10 | 1997-09-29 | 1,8―ジアミノナフタレンおよびその誘導体の2,3―ジヒドロペリミジンの製造法 |
EP97909326A EP0932603A1 (de) | 1996-10-10 | 1997-09-29 | Verfahren zur herstellung von 1,8-diaminonaphthalinen und ihrer derivate der 2,3-dihydroperimidine |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1996141689 DE19641689A1 (de) | 1996-10-10 | 1996-10-10 | Verfahren zur Herstellung von 1,8-Diaminonaphthalinen und ihrer Derivate der 2,3-Dihydroperimidine |
DE19641689.2 | 1996-10-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998015533A1 true WO1998015533A1 (de) | 1998-04-16 |
Family
ID=7808307
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1997/005316 WO1998015533A1 (de) | 1996-10-10 | 1997-09-29 | Verfahren zur herstellung von 1,8-diaminonaphthalinen und ihrer derivate der 2,3-dihydroperimidine |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0932603A1 (de) |
JP (1) | JP2001501667A (de) |
AU (1) | AU4706397A (de) |
DE (1) | DE19641689A1 (de) |
TW (1) | TW438865B (de) |
WO (1) | WO1998015533A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2521195A1 (de) * | 2011-03-15 | 2012-11-07 | Basf Se | Tetraazaperopyrene-Verbindungen und deren Verwendung als n-Halbleiter |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102421855A (zh) * | 2009-04-22 | 2012-04-18 | 德司达染料德国有限责任公司 | 用于聚合物着色的染料,其制备及其用途 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1296290B (de) * | 1964-04-16 | 1969-05-29 | Basf Ag | Verfahren zur Herstellung von Farbstoffen der Phthaloperinonreihe |
EP0406812A2 (de) * | 1989-07-03 | 1991-01-09 | Hercules Incorporated | Verfahren zur Herstellung von NiNi-Diakyl- 1,8-Naphthalendiamin |
-
1996
- 1996-10-10 DE DE1996141689 patent/DE19641689A1/de not_active Withdrawn
-
1997
- 1997-09-15 TW TW86113352A patent/TW438865B/zh active
- 1997-09-29 JP JP10517136A patent/JP2001501667A/ja active Pending
- 1997-09-29 AU AU47063/97A patent/AU4706397A/en not_active Abandoned
- 1997-09-29 WO PCT/EP1997/005316 patent/WO1998015533A1/de not_active Application Discontinuation
- 1997-09-29 EP EP97909326A patent/EP0932603A1/de not_active Withdrawn
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1296290B (de) * | 1964-04-16 | 1969-05-29 | Basf Ag | Verfahren zur Herstellung von Farbstoffen der Phthaloperinonreihe |
EP0406812A2 (de) * | 1989-07-03 | 1991-01-09 | Hercules Incorporated | Verfahren zur Herstellung von NiNi-Diakyl- 1,8-Naphthalendiamin |
Non-Patent Citations (1)
Title |
---|
R.ALDER ET AL.: "PREPARATION OF A RANGE OF N-TETRASUBSTITUTED 1,8-DIAMINONAPHTALENES.", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1., vol. 11, 1981, LETCHWORTH GB, pages 2840 - 2847, XP002052258 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2521195A1 (de) * | 2011-03-15 | 2012-11-07 | Basf Se | Tetraazaperopyrene-Verbindungen und deren Verwendung als n-Halbleiter |
Also Published As
Publication number | Publication date |
---|---|
DE19641689A1 (de) | 1998-04-16 |
AU4706397A (en) | 1998-05-05 |
EP0932603A1 (de) | 1999-08-04 |
TW438865B (en) | 2001-06-07 |
JP2001501667A (ja) | 2001-02-06 |
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