EP0391170B1 - Process for dyeing paper - Google Patents
Process for dyeing paper Download PDFInfo
- Publication number
- EP0391170B1 EP0391170B1 EP90105512A EP90105512A EP0391170B1 EP 0391170 B1 EP0391170 B1 EP 0391170B1 EP 90105512 A EP90105512 A EP 90105512A EP 90105512 A EP90105512 A EP 90105512A EP 0391170 B1 EP0391170 B1 EP 0391170B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- paper
- dyes
- formula
- dyestuffs
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000004043 dyeing Methods 0.000 title description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- -1 phenylsulphonyl Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 229910006069 SO3H Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 17
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 2
- 229920001131 Pulp (paper) Polymers 0.000 description 2
- 229940037003 alum Drugs 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- ZBNARPCCDMHDDV-UHFFFAOYSA-N chembl1206040 Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N=NC3=CC=C(C=C3C)C=3C=C(C(=CC=3)N=NC=3C(=CC4=CC(=CC(N)=C4C=3O)S(O)(=O)=O)S(O)(=O)=O)C)=C(O)C2=C1N ZBNARPCCDMHDDV-UHFFFAOYSA-N 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000011121 hardwood Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/28—Colorants ; Pigments or opacifying agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/919—Paper
Definitions
- the present invention relates to a process for dyeing paper in blue tones with certain disazo dyes.
- Dyes which are suitable for dyeing paper in blue tones have long been known from the prior art (cf. e.g. C.I. Direct Blue, 23 850; C.I. Direct Blue, 24400).
- anionic disazo dyes which include can be used for dyeing and printing paper in red shades.
- FR-A-456 232 discloses certain disazo dyes which can be converted into trisazo dyes by reaction with a diazo component.
- substituents can in turn be substituted by substituents customary in dye chemistry, for example halogen, in particular Cl, OH, C1-C4alkoxy, acyloxy, for example acetoxy, C1-C4alkyl, SO3H, COOH.
- substituents customary in dye chemistry for example halogen, in particular Cl, OH, C1-C4alkoxy, acyloxy, for example acetoxy, C1-C4alkyl, SO3H, COOH.
- Alkyl preferably stands for optionally substituted C1-C Alkyl alkyl, aryl, preferably for optionally substituted phenyl and aralkyl preferably for optionally substituted benzyl.
- the dyes are prepared in a known manner by coupling diazotized azo dyes of the formula with coupling components of the formula
- X NH2
- the dyes are generally used in the form of their salts for dyeing, in particular the alkali salts (Li, Na, K), the ammonium salts, mono-, bis- or tris-C2-C4-alkyl-ammonium salts, in particular also the C2-C4- Alkanol-ammonium salts.
- alkali salts Li, Na, K
- ammonium salts mono-, bis- or tris-C2-C4-alkyl-ammonium salts, in particular also the C2-C4- Alkanol-ammonium salts.
- the radicals R5 can be the same or different.
- the dyes can also be used as concentrated, aqueous solutions.
- the blue paper dyeings obtained are notable for good light and wet fastness (bleeding fastness), as well as acid, alkali and alum fastness. Attention should also be drawn to the brilliance and clarity of the color tones. Furthermore, the combination behavior with suitable dyes is very good.
- a desiccant consisting of 60% wood pulp and 40% unbleached sulfite pulp is beaten in the Dutch and ground to a degree of grinding of 40 ° SR so that the dryness is slightly above 2.5%, and then adjusted to 2.5% dryness of the thick matter with water .
- bleached sulfite pulp is used to produce the thick stock and this thick stock is used for dyeing, blue paper dyeings and practically dye-free waste water are obtained by the above-mentioned processes.
Landscapes
- Paper (AREA)
- Coloring (AREA)
Description
Die vorliegende Erfindung betrifft ein Verfahren zum Färben von Papier in blauen Tönen mit bestimmten Disazofarbstoffen.The present invention relates to a process for dyeing paper in blue tones with certain disazo dyes.
Aus dem Stand der Technik sind bereits seit langem Farbstoffe bekannt, die zum Färben von Papier in blauen Tönen geeignet sind (vgl. z.B. C.I. Direct Blue, 23 850; C.I. Direct Blue, 24400).Dyes which are suitable for dyeing paper in blue tones have long been known from the prior art (cf. e.g. C.I. Direct Blue, 23 850; C.I. Direct Blue, 24400).
Aus EP-A-0 289 458 sind bestimmte anionische Disazofarbstoffe bekannt, die u.a. zum Färben und Bedrucken von Papier in roten Farbtönen verwendet werden können.From EP-A-0 289 458 certain anionic disazo dyes are known which include can be used for dyeing and printing paper in red shades.
Aus FR-A-456 232 sind bestimmte Disazofarbstoffe bekannt, die durch Umsetzung mit einer Diazokomponente in Trisazofarbstoffe überführt werden können.FR-A-456 232 discloses certain disazo dyes which can be converted into trisazo dyes by reaction with a diazo component.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zum Farben von Papier in blauen Tönen, das dadurch gekennzeichnet ist, daß man Farbstoffe der Formel
verwendet, worin
- X =
- H, OH, C₁-C₄-Alkoxy oder -NHR₃
- R₁ =
- H, C₁-C₄-Alkyl
- R₂, R₃ =
- H, Alkyl, Alkylcarbonyl, Alkylsulfonyl, Aryl, Arylcarbonyl, Arylsulfonyl, Aralkyl, Aralkylcarbonyl oder Aminocarbonyl,
used where
- X =
- H, OH, C₁-C₄ alkoxy or -NHR₃
- R₁ =
- H, C₁-C₄ alkyl
- R₂, R₃ =
- H, alkyl, alkylcarbonyl, alkylsulfonyl, aryl, arylcarbonyl, arylsulfonyl, aralkyl, aralkylcarbonyl or aminocarbonyl,
Die genannten Substituenten können ihrerseits durch in der Farbstoffchemie übliche Substituenten substituiert sein, beispielsweise Halogen, inbesondere Cl, OH, C₁-C₄-Alkoxy, Acyloxy, beispielsweise Acetoxy, C₁-C₄-Alkyl, SO₃H, COOH.Said substituents can in turn be substituted by substituents customary in dye chemistry, for example halogen, in particular Cl, OH, C₁-C₄alkoxy, acyloxy, for example acetoxy, C₁-C₄alkyl, SO₃H, COOH.
Alkyl steht vorzugsweise für gegebenenfalls substituiertes C₁-C₄-Alkyl, Aryl, vorzugsweise für gegebenenfalls substituiertes Phenyl und Aralkyl vorzugsweise für gegebenenfalls substituiertes Benzyl.Alkyl preferably stands for optionally substituted C₁-C Alkyl alkyl, aryl, preferably for optionally substituted phenyl and aralkyl preferably for optionally substituted benzyl.
Bevorzugte Farbstoffe I sind ganz generell solche mit
- R₁ =
- H, C₁-C₄-Alkyl
- R₂, R₃ =
- H, C₁-C₄-Alkyl, C₁-C₄-Alkylcarbonyl, C₁-C₄-Alkylsulfonyl, Aminocarbonyl, Phenylcarbonyl, Phenyl, Phenylsulfonyl, Benzylcarbonyl,
- X =
- H, C₁-C₂-Alkoxy, -NHR₃, OH
- R₁ =
- H, C₁-C₄ alkyl
- R₂, R₃ =
- H, C₁-C₄-alkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylsulfonyl, aminocarbonyl, phenylcarbonyl, phenyl, phenylsulfonyl, benzylcarbonyl,
- X =
- H, C₁-C₂ alkoxy, -NHR₃, OH
Bevorzugte Farbstoffe sind weiterhin solche der Formeln
worin
- R₁ - R₃
- die in Formel I angegebene Bedeutung haben,
- R₁
- vorzugsweise = H oder CH₃
- R₂, R₃
- vorzugsweise = H, COCH₃, COC₆H₅, C₆H₅
- R₄ =
- OH, OCH₃, OC₂H₅.
wherein
- R₁ - R₃
- have the meaning given in formula I,
- R₁
- preferably = H or CH₃
- R₂, R₃
- preferably = H, COCH₃, COC₆H₅, C₆H₅
- R₄ =
- OH, OCH₃, OC₂H₅.
Die Herstellung der Farbstoffe erfolgt in bekannter Weise durch Kupplung diazotierter Azofarbstoffe der Formel
mit Kupplungskomponenten der Formel
Für den Fall daß X = NH₂ verwendet man bei der Herstellung zweckmäßigerweise die entsprechenden Verbindungen V mit X = Acylamino, insbesondere -NHCOCH₃ und verseift nach erfolgter Kupplung.The dyes are prepared in a known manner by coupling diazotized azo dyes of the formula
with coupling components of the formula
In the event that X = NH₂, the appropriate compounds V with X = acylamino, in particular -NHCOCH₃, and saponified after coupling have been used in the preparation.
Die Farbstoffe werden im allgemeinen in Form ihrer Salze zum Färben eingesetzt, insbesondere der Alkalisalze (Li, Na, K), der Ammoniumsalze, Mono-, Bis- oder Tris-C₂-C₄-alkyl-ammoniumsalze, insbesondere auch der C₂-C₄-Alkanol-ammoniumsalze.The dyes are generally used in the form of their salts for dyeing, in particular the alkali salts (Li, Na, K), the ammonium salts, mono-, bis- or tris-C₂-C₄-alkyl-ammonium salts, in particular also the C₂-C₄- Alkanol-ammonium salts.
Bevorzugte Ammoniumsalze sind dabei solche mit dem Kation
worin
- R₅
- H, C₁-C₄-Alkyl, gegebenenfalls substituiert durch OH oder Hydroxy-C₁-C₄-alkoxy, insbesondere CH₃, C₂H₅, CH₂-CH₂-OH, CH₂-CH₂OCH₃, CH₂-CH₂-OCH₂-CH₂OH,
- R₆
- C₁-C₄-Hydroxyalkyl, C₁-C₄-Hydroxyalkoxy-alkyl, insbesondere CH₂-CH₂-OH, CH₂-CH₂OCH₃, CH₂-CH₂-OCH₂-CH₂-OH.
wherein
- R₅
- H, C₁-C₄-alkyl, optionally substituted by OH or hydroxy-C₁-C₄-alkoxy, in particular CH₃, C₂H₅, CH₂-CH₂-OH, CH₂-CH₂OCH₃, CH₂-CH₂-OCH₂-CH₂OH,
- R₆
- C₁-C₄-hydroxyalkyl, C₁-C₄-hydroxyalkoxy-alkyl, in particular CH₂-CH₂-OH, CH₂-CH₂OCH₃, CH₂-CH₂-OCH₂-CH₂-OH.
Die Reste R₅ können dabei gleich oder verschieden sein.The radicals R₅ can be the same or different.
Die Farbstoffe können auch als konzentrierte, wäßrige Lösungen eingesetzt werden.The dyes can also be used as concentrated, aqueous solutions.
Sie können nach allen in der Papierindustrie für substantive Farbstoffe gebräuchlichen Verfahren eingesetzt werden, insbesondere in der Masse- wie in der Oberflachenfärbung von Papier für geleimte und ungeleimte Sorten, ausgehend von gebleichten oder ungebleichten Zellstoff verschiedender Provenienz wie Nadel- oder Laubholz-sulfit und/oder -Sulfat-Zellstoff.They can be used in all processes used in the paper industry for substantive dyes, especially in the mass and surface coloring of paper for sized and unsized varieties, based on bleached or unbleached pulp of different provenances such as softwood or hardwood sulfite and / or -Sulfate pulp.
Die erhaltenen blauen Papierfärbungen zeichnen sich durch gute Licht- und Naßechtheit (Ausblutechtheit) sowie Säure-, Alkali- und Alaun-Echtheit aus. Auch auf die Brillanz und Klarheit der Farbtöne ist hinzuweisen. Ferner ist das Kombinationsverhalten mit geeigneten Farbstoffen sehr gut.The blue paper dyeings obtained are notable for good light and wet fastness (bleeding fastness), as well as acid, alkali and alum fastness. Attention should also be drawn to the brilliance and clarity of the color tones. Furthermore, the combination behavior with suitable dyes is very good.
Ein aus 60 % Holzschliff und 40 % ungebleichtem Sulfitzellstoff bestehender Trockenstoff wird im Holländer angeschlagen und bis zum Mahlgrad 40° SR gemahlen, so daß der Trockengehalt etwas über 2,5 % liegt, und anschließend mit Wasser auf 2,5 % Trockengehalt des Dickstoffs eingestellt.A desiccant consisting of 60% wood pulp and 40% unbleached sulfite pulp is beaten in the Dutch and ground to a degree of grinding of 40 ° SR so that the dryness is slightly above 2.5%, and then adjusted to 2.5% dryness of the thick matter with water .
200 Teile dieses Dickstoffs werden mit 5 Teilen einer 0,5 %igen wässrigen Lösung des Farbstoffs der Formel
versetzt, ca. 5 Minuten verrührt, 2 % Harzleim und 3 % Alaun (bezogen auf Trockenstoff) zugegeben und wiederum einige Minuten homogen verrührt. Man verdünnt dann die Masse mit ca. 500 Teilen Wasser und stellt hieraus in üblicher Weise durch Absaugen über einen Blattbildner Papierblätter her. Die Papierblätter weisen eine blaue Färbung auf. Das Abwasser ist praktisch farbstoffrei.200 parts of this thick matter are mixed with 5 parts of a 0.5% aqueous solution of the dye of the formula
added, stirred for about 5 minutes, 2% resin glue and 3% alum (based on dry matter) added and again stirred homogeneously for a few minutes. The mass is then diluted with about 500 parts of water and paper sheets are produced therefrom in a conventional manner by suction through a sheet former. The paper sheets are colored blue. The wastewater is practically dye-free.
Beim Färben ungeleimter Papiermasse unter sonst gleichen Färbebedingungen erhält man ebenfalls eine kräftige blaue Färbung mit praktisch farbstoffreiem Abwasser.When dyeing unsized paper pulp under otherwise identical dyeing conditions, a strong blue dyeing with practically dye-free waste water is also obtained.
Verwendet man gebleichten Sulfitzellstoff zur Herstellung des Dickstoffs und setzt diesen Dickstoff zur Färbung ein, so erhält man nach den oben angegebenen Verfahren blaue Papierfärbungen und praktisch farbstofffreies Abwasser.If bleached sulfite pulp is used to produce the thick stock and this thick stock is used for dyeing, blue paper dyeings and practically dye-free waste water are obtained by the above-mentioned processes.
Verwendet man an Stelle des in Beispiel A genannten Farbstoffs die folgenden Farbstoffe (2) bis (73), so erhält man ebenfalls blaue Papierfärbungen mit praktisch farbstoffreiem Abwasser.
Claims (4)
- Process for the colouring of paper in blue hues, characterized in that dyestuffs of the formula
X is H, OH, C₁-C₄-alkoxy or -NHR₃R₁ is H, C₁-C₄-alkylR₂, R₃ are H, alkyl, alkylcarbonyl, alkylsulphonyl, aryl, arylcarbonyl, arylsulphonyl, aralkyl, aralkylcarbonyl or aminocarbonyl. - Process according to Claim 1, characterized by the use of dyestuffs of the formula of Claim 1 in whichR₁ is H, C₁-C₄-alkyl,R₂, R₃ are H, C₁-C₄-alkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylsulphonyl, aminocarbonyl, phenylcarbonyl, phenyl, phenylsulphonyl, benzylcarbonyl,it being possible for the phenyl rings to be substituted by SO₃H or COOH,X is H, C₁-C₂-alkoxy, -NHR₃,the dyestuffs having at least 3 sulpho groups in the naphthalene rings.
- Process according to Claims 1 and 2, characterized by the use of dyestuffs of the formula
and
- Paper coloured by the process of Claims 1-3.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3910923 | 1989-04-05 | ||
| DE3910923A DE3910923A1 (en) | 1989-04-05 | 1989-04-05 | METHOD FOR DYING PAPER |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0391170A1 EP0391170A1 (en) | 1990-10-10 |
| EP0391170B1 true EP0391170B1 (en) | 1993-11-10 |
Family
ID=6377860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90105512A Expired - Lifetime EP0391170B1 (en) | 1989-04-05 | 1990-03-23 | Process for dyeing paper |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5034017A (en) |
| EP (1) | EP0391170B1 (en) |
| JP (1) | JPH02289198A (en) |
| DD (1) | DD299326A5 (en) |
| DE (2) | DE3910923A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2104881T3 (en) * | 1991-09-26 | 1997-10-16 | Ciba Geigy Ag | PROCEDURE FOR DYING PAPER WITH DIAZOIC DYES. |
| US5198022A (en) * | 1991-10-25 | 1993-03-30 | Lexmark International, Inc. | Waterfast dye and aqueous ink |
| DE19638891A1 (en) * | 1996-09-23 | 1998-03-26 | Bayer Ag | Process for dyeing cellulosic materials with disazo dyes |
| DE19846098A1 (en) * | 1998-10-07 | 2000-04-13 | Bayer Ag | Disazo dyes |
| JP5322463B2 (en) * | 2008-03-11 | 2013-10-23 | 公立大学法人大阪府立大学 | Azo dichroic dye |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR456232A (en) * | 1912-06-12 | 1913-08-20 | Societe Leopold Cassella & C G M B H | Process for the preparation of trisazo dyes |
| US4724001A (en) * | 1985-05-14 | 1988-02-09 | Canon Kabushiki Kaisha | Disazoic dye and recording liquid containing the same |
| DE3887561D1 (en) * | 1987-04-27 | 1994-03-17 | Ciba Geigy | Anionic disazo dyes. |
| JPH07119378B2 (en) * | 1989-01-27 | 1995-12-20 | キヤノン株式会社 | Recording liquid and ink jet recording method using the same |
-
1989
- 1989-04-05 DE DE3910923A patent/DE3910923A1/en not_active Withdrawn
-
1990
- 1990-03-21 US US07/497,371 patent/US5034017A/en not_active Expired - Lifetime
- 1990-03-23 EP EP90105512A patent/EP0391170B1/en not_active Expired - Lifetime
- 1990-03-23 DE DE90105512T patent/DE59003396D1/en not_active Expired - Fee Related
- 1990-03-29 JP JP2079081A patent/JPH02289198A/en active Pending
- 1990-04-04 DD DD90339432A patent/DD299326A5/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US5034017A (en) | 1991-07-23 |
| DD299326A5 (en) | 1992-04-09 |
| DE59003396D1 (en) | 1993-12-16 |
| JPH02289198A (en) | 1990-11-29 |
| EP0391170A1 (en) | 1990-10-10 |
| DE3910923A1 (en) | 1990-10-11 |
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