DE2721187C2 - Color-stable monoazo dye - Google Patents
Color-stable monoazo dyeInfo
- Publication number
- DE2721187C2 DE2721187C2 DE2721187A DE2721187A DE2721187C2 DE 2721187 C2 DE2721187 C2 DE 2721187C2 DE 2721187 A DE2721187 A DE 2721187A DE 2721187 A DE2721187 A DE 2721187A DE 2721187 C2 DE2721187 C2 DE 2721187C2
- Authority
- DE
- Germany
- Prior art keywords
- modification
- temperatures
- dye
- values
- aqueous suspension
- 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
Links
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title 1
- 238000012986 modification Methods 0.000 claims description 31
- 230000004048 modification Effects 0.000 claims description 25
- 239000007900 aqueous suspension Substances 0.000 claims description 7
- 229920003023 plastic Polymers 0.000 claims description 7
- 239000004033 plastic Substances 0.000 claims description 7
- 238000004040 coloring Methods 0.000 claims description 6
- 238000004043 dyeing Methods 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000002441 X-ray diffraction Methods 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 3
- 238000010586 diagram Methods 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- -1 dioxane Chemical compound 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 239000004117 Lignosulphonate Substances 0.000 description 1
- 240000002129 Malva sylvestris Species 0.000 description 1
- 235000006770 Malva sylvestris Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Classifications
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds
- C09B67/0029—Crystal modifications; Special X-ray patterns of azo compounds of monoazo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Artificial Filaments (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
(C2Hj)2NSC)2 (C 2 Hj) 2 NSC) 2
N(C2H4OH)2 N (C 2 H 4 OH) 2
NHCOCH,NHCOCH,
die das in Abb.l gezeigte Röntgenbeugungsdiagramm mit den charakteristischen Reflexen bei folgenden Glanzwinkeln Θ (CuK Λ-Strahlung) und den angegebenen Intensitäten hat.the X-ray diffraction diagram shown in Fig. 1 with the characteristic reflections in the following Glance angles Θ (CuK Λ radiation) and the specified intensities.
d-Werte
relative Intensitätd values
relative intensity
d-Werted values
relative Intensität
θ relative intensity
θ
d-Werte
relative Intensitätd values
relative intensity
Der Farbstoff der vorstehend genannten Formel kann nach bekannten Verfahren hergestellt werden, wobei er in der «-Modifikation anfällt, die unter den Li der Praxis des Färbens auftretenden Bedingungen, insbesondere beim Einfärben von Polyurethankunststoffen gemäß dem in DE-OS 24 26 171 beanspruchten Verfahren, keine genügende Stabilität besitzt Die «-Modifikation weist das in Abb.2 gezeigte Röntgenbeugungsdiagramm mit den charakteristischen Reflexen bei folgenden Glanzwinkeln θ (Cuk «-Strahlung) mit den angegebenen Intensitäten auf:The dye of the above formula can be prepared according to known processes, where it is obtained in the «modification, which falls under the Li in practice of the coloring conditions occurring, in particular when coloring polyurethane plastics according to The method claimed in DE-OS 24 26 171 does not have sufficient stability. The «modification has the X-ray diffraction diagram shown in Fig with the characteristic reflections at the following glancing angles θ (Cuk «radiation) with the specified intensities to:
Unter Färbebedingungen, wie hoher Temperatur und in Gegenwart von Färbereihilfsmitteln, ändert sich die ^-Modifikation hinsichtlich Kristallgröße und Kristallform praktisch nicht mehr, so daß die färberischen Eigenschaften und die Stabilität der Dispersion im Gegensatz zur «-Modifikation dabei nicht beeinträchtigt werden.Under dyeing conditions, such as high temperature and in the presence of dyeing auxiliaries, the changes ^ -Modification in terms of crystal size and crystal shape practically no longer, so that the coloring Properties and the stability of the dispersion, in contrast to the «modification, are not impaired will.
Beim Einfärben von Polyurethankunststoffen unter Ausbildung kovaienter Bindungen zwischen dem Farbstoff und der Isocyanatkomponente des Kunststoffes werden im Fall der Verwendung der «-Modifikation des Farbstoffes die technischen Eigenschaften des Kunststoffes (Elastizität, Steigzeit, Abbindezeit usw.) gegenüber einem nicht eingefärbten Kunststoff deutlich verändert, im Falle der Verwendung der »^-Modifikation« tritt eine solche Veränderung nicht auf.When coloring polyurethane plastics with the formation of covaient bonds between the dye and the isocyanate component of the plastic are, in the case of using the «modification of the The technical properties of the plastic (elasticity, rise time, setting time, etc.) significantly changed to a non-colored plastic, if the »^ modification« is used such a change does not occur.
Die neue färbestabile /^-Modifikation kann durch 10 bis ca. 60 Minuten langes Erhitzen, gegebenenfalls unter Druck, einer wäßrigen Suspension der «Modifikation auf Temperaturen von 60—150°C, vorzugsweise 80 -120° C, erbalten werden.The new color-stable / ^ -modification can be changed by 10 Heating, if necessary under pressure, of an aqueous suspension of the modification for up to about 60 minutes to temperatures of 60-150 ° C, preferably 80-120 ° C.
Die ^-Modifikation kann auch durch Erhitzen der «Modifikation in organischen Lösungsmitteln, wie Alkoholen, beispielsweise Äthanol oder Butanol, Äthern, wie Dioxan, oder Glykolen oder Glykoläthern, auf Temperaturen von 40° C bis etwa 120° C gegebenenfalls unter Druck oder aromatischen Kohlenwasserstoffen wie beispielsweise Chiorbenzol, Dichlorbenzol, Toluol, Xylol oder Benzol, erhalten werden. Außerdem kann die ^-Modifikation durch Trocknen der «-Modifikation bei Temperaturen von 100-120°C erhalten werden.The ^ modification can also be achieved by heating the «modification in organic solvents, such as Alcohols, for example ethanol or butanol, ethers such as dioxane, or glycols or glycol ethers, to temperatures of 40 ° C to about 120 ° C, if necessary under pressure or aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, Toluene, xylene or benzene. In addition, the ^ -modification can be obtained by drying the «-modification can be obtained at temperatures of 100-120 ° C.
4·) Die Umwandlung in die stabile ^-Modifikation findet auch durch Erhitzen der «-Modifikation in wäßriger Suspension unter Zusatz von wasserlöslichen organischen Lösungsmitteln, wie beispielsweise Alkoholen, wie Methanol, Äthanol, Butanol, Glykolen oder4 ·) The conversion into the stable ^ -modification takes place also by heating the modification in aqueous suspension with the addition of water-soluble organic compounds Solvents such as alcohols such as methanol, ethanol, butanol, glycols or
ίο Glykoläthern, Aceton oder Dimethylformamid, innerhalb eines Temperaturbereiches statt, dessen untere Grenze ca. 40° C ist und dessen obere Grenze durch die Zusammensetzung des Gemisches aus Wasser und organischem Lösungsmittel gegeben ist, 120°C jedoch nicht übersteigen soll.ίο glycol ethers, acetone or dimethylformamide, inside of a temperature range, the lower limit of which is approx. 40 ° C and the upper limit of which is the The composition of the mixture of water and organic solvent is given, however, 120 ° C should not exceed.
Eine weitere Möglichkeit zur Umwandlung der »«-Modifikation« die färbestabile »/^-Modifikation« besteht im mehrstündigen intensiven Durchmischen einer wäßrigen Suspension der »«-Modifikation« desAnother possibility for converting the "" modification "is the color-stable" / ^ modification " consists of several hours of intensive mixing of an aqueous suspension of the "" modification "of
W) Farbstoffes mit 1—20 Vol.-%, vorzugsweise 5—10 Vol.-% eines in Wasser nicht löslichen organischen Lösungsmittels wie beispielsweise Benzol, Chlorbenzol, Dichlorbenzol, Toluol oder Xylol bei Temperaturen zwischen 10 und 120°C, vorzugsweise zwischen 40 undW) dye with 1-20% by volume, preferably 5-10 % By volume of an organic solvent that is insoluble in water, such as benzene, chlorobenzene, Dichlorobenzene, toluene or xylene at temperatures between 10 and 120 ° C, preferably between 40 and
hi 90° C.hi 90 ° C.
Man erhält die ^-Modifikation ferner durch Erhitzen einer wäßrigen Suspension der «-Modifikation unter Zusatz von anionischen, kationischen oder nichtioni-The ^ modification is also obtained by heating an aqueous suspension of the "modification with the addition of anionic, cationic or non-ionic
sehen oberflächenaktiven Verbindungen bei Temperaturen von 60 bis etwa 1000C. Hierfür geeignete oberflächenaktive Verbindungen sind beispielsweise diisobutylnaphtalinsulfonsaures Na'rium, das Anlagerungsprodukt von 25 Mol Äthylenoxid an 1 Mol Steaiylalkonol, ein Gemisch aus Alkyl-dimethylbenzylammoniumchloriden, ein Fettsäurepolyglykolester oder tertiäre organische Phosphorsäureester des Anlagerprodukts von 2 Mol Äthylenoxid an 1 MoI Laurylalkohol. see surfactant compounds at temperatures of 60 to about 100 0 C. To this end, suitable surface-active compounds are, for example diisobutylnaphtalinsulfonsaures Na'rium, the adduct of 25 moles of ethylene oxide to 1 mol of Steaiylalkonol, a mixture of alkyl dimethylbenzylammonium chlorides, a fatty acid or tertiary organic organophosphate the Anlagerprodukts of 2 moles of ethylene oxide to 1 mole of lauryl alcohol.
Schließlich kann die ^-Modifikation dadurch erhalten werden, daß man die «-Modifikation unter Zusatz üblicher Dispergiermittel, wie beispielsweise alkylierte Naphtalinsulfonsäuren, Polyvinylsulfonate, Kondensationsprodukte aus Naphthaiinsuifonsäure und Formaldehyd oder aus Phenol und Formaldehyd, Alkalisaize von Ligninsulfonaten oder Sulfitcelluloseablauge, bei Temperaturen von etwa 80 - 90° C mahlt.Finally, the ^ modification can be obtained through this be that the modification with the addition of conventional dispersants, such as alkylated Naphthalene sulfonic acids, polyvinyl sulfonates, condensation products from naphthalene sulfonic acid and formaldehyde or from phenol and formaldehyde, alkali metal from lignosulphonates or sulphite cellulose waste liquor Grinds temperatures of around 80 - 90 ° C.
Die ^-Modifikation wird beispielsweise durch Filtrieren von der flüssigen Phase abgetrennt und einem bekannten Finish unter Zusatz von Dispergiermitteln, wie beispielsweise alkylierten Naphthalinsulfonsäuren, Polyvinylsulfonaten, Kondensationsprodukten aus Naphthaiinsuifonsäure und Formaldehyd oder aus Phenol und Formaldehyd, Alkalisalzen von Ligninsulfo naten oder Sulfitcellulosenablauge, bei den üblicher Temperaturen, die 60°C nicht übersteigen, unterworfen Für die Feinverteilung eignen sich die üblicher Vorrichtungen, wie beispielsweise Kugelmühlen odei Sandmühlen.The ^ modification is made, for example, by filtering separated from the liquid phase and given a known finish with the addition of dispersants, such as, for example, alkylated naphthalene sulfonic acids, polyvinyl sulfonates, condensation products Naphthalene sulfonic acid and formaldehyde or from phenol and formaldehyde, alkali salts of lignin sulfo naten or sulphite cellulose waste liquor, at the usual temperatures, which do not exceed 60 ° C, subjected The usual devices, such as, for example, ball mills or odei, are suitable for fine distribution Sand mills.
Die auf diese Weise erhaltenen flüssigen odei pulverförmigen Präparationen der stabilen jS-Modifikationen eignen sich im Gegensatz zu vergleichbarer Präparationen der «Modifikation uneingeschränkt zurr Färben von Textilmaterialien aus Celluloseestern odei synthetischen linearen Polyestern, wie Polyäthylengly kolterephthalat, bei Temperaturen zwischen 100 unc 2200C. Die stabilen Zubereitungen flocken in wäßrigerr Medium und bei Einwirkung hoher Temperaturen nichi aus, was besonders für die Färbung von Wickelkörpern beispielsweise Kreuzspulen, von Bedeutung ist unc ergeben bessere Prüferergebnisse bei unterschiedlicher Färbereitests.The thus obtained liquid Odei powdered preparations of stable jS modifications are in contrast to comparable preparations of the "modification fully lashing dyeing textile materials from Celluloseestern Odei synthetic linear polyesters, such Polyäthylengly kolterephthalat, at temperatures between 100 unc 220 0 C. Stable preparations do not flocculate in an aqueous medium and when exposed to high temperatures, which is particularly important for the dyeing of wound bobbins, for example cheeses, and gives better test results in different dyeing readiness tests.
Die »^-Modifikation« des genannten Farbstoffes kann insbesondere zum Einfärben von Polyurethan-Kunststoffen gemäß den Beispielen 1 bis 8 der DE-OS 24 26 171 verwendet werden.The "^ modification" of the dye mentioned can be used in particular for coloring polyurethane plastics according to Examples 1 to 8 of DE-OS 24 26 171 can be used.
Hierzu 2 Blatt ZeichnungenFor this purpose 2 sheets of drawings
Claims (4)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2721187A DE2721187C2 (en) | 1977-05-11 | 1977-05-11 | Color-stable monoazo dye |
| IT7823199A IT7823199A0 (en) | 1977-05-11 | 1978-05-09 | COLOR STABLE MONOAZO DYE. |
| JP5415278A JPS5410333A (en) | 1977-05-11 | 1978-05-09 | Monoazo dyestuff being stable under dyeing condition |
| BE187556A BE866907A (en) | 1977-05-11 | 1978-05-10 | ELECTROSTATIC FILTRATION PROCESS AND DEVICE FOR GAS CLEANING |
| FR7813917A FR2390477A1 (en) | 1977-05-11 | 1978-05-10 | Stable, alpha-form mono:azo dyestuff - for polyurethane(s) and cellulose ester and polyester textiles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2721187A DE2721187C2 (en) | 1977-05-11 | 1977-05-11 | Color-stable monoazo dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2721187B1 DE2721187B1 (en) | 1978-11-23 |
| DE2721187C2 true DE2721187C2 (en) | 1979-07-26 |
Family
ID=6008624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2721187A Expired DE2721187C2 (en) | 1977-05-11 | 1977-05-11 | Color-stable monoazo dye |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5410333A (en) |
| BE (1) | BE866907A (en) |
| DE (1) | DE2721187C2 (en) |
| FR (1) | FR2390477A1 (en) |
| IT (1) | IT7823199A0 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62238393A (en) * | 1986-04-07 | 1987-10-19 | Nippon Light Metal Co Ltd | Method for electroplating aluminum material |
-
1977
- 1977-05-11 DE DE2721187A patent/DE2721187C2/en not_active Expired
-
1978
- 1978-05-09 JP JP5415278A patent/JPS5410333A/en active Pending
- 1978-05-09 IT IT7823199A patent/IT7823199A0/en unknown
- 1978-05-10 BE BE187556A patent/BE866907A/en not_active IP Right Cessation
- 1978-05-10 FR FR7813917A patent/FR2390477A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5410333A (en) | 1979-01-25 |
| FR2390477A1 (en) | 1978-12-08 |
| BE866907A (en) | 1978-11-10 |
| IT7823199A0 (en) | 1978-05-09 |
| DE2721187B1 (en) | 1978-11-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8339 | Ceased/non-payment of the annual fee |