DE1227589B - Process for the preparation of a pigment dye - Google Patents
Process for the preparation of a pigment dyeInfo
- Publication number
- DE1227589B DE1227589B DEF39402A DEF0039402A DE1227589B DE 1227589 B DE1227589 B DE 1227589B DE F39402 A DEF39402 A DE F39402A DE F0039402 A DEF0039402 A DE F0039402A DE 1227589 B DE1227589 B DE 1227589B
- Authority
- DE
- Germany
- Prior art keywords
- dicarboxylic acid
- anhydride
- preparation
- naphthylene
- condensed
- 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.)
- Pending
Links
- 239000000049 pigment Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- DMEPVFSJYHJGCD-UHFFFAOYSA-N 3,5-dimethylbenzene-1,2-diamine Chemical compound CC1=CC(C)=C(N)C(N)=C1 DMEPVFSJYHJGCD-UHFFFAOYSA-N 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000000740 bleeding effect Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MHQULXYNBKWNDF-UHFFFAOYSA-N 3,4-dimethylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1C MHQULXYNBKWNDF-UHFFFAOYSA-N 0.000 description 1
- XSZYBMMYQCYIPC-UHFFFAOYSA-N 4,5-dimethyl-1,2-phenylenediamine Chemical compound CC1=CC(N)=C(N)C=C1C XSZYBMMYQCYIPC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005406 washing Methods 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/12—Perinones, i.e. naphthoylene-aryl-imidazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coloring (AREA)
Description
Int. CL:Int. CL:
C09bC09b
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Deutsche Kl.: 22 e-7/02 German class: 22 e- 7/02
Nummer: 1227 589Number: 1227 589
Aktenzeichen: F 39402IV c/22 eFile number: F 39402IV c / 22 e
Anmeldetag: 4. April 1963Filing date: April 4, 1963
Auslegetag: 27. Oktober 1966Opening day: October 27, 1966
Es wurde gefunden, daß man einen zum Färben von Kunststoffen aller Art sehr gut geeigneten Pigmentfarbstoff erhält, wenn man die beispielsweise nach dem Verfahren der deutschen Patentschrift 1 005 969 erhältliche Naphthoylenbenzimidazol-r,8'-dicarbonsäure bzw. deren Anhydrid von folgender FormelIt has been found that one is very suitable for coloring plastics of all kinds Pigment dye is obtained, for example, by the process of the German patent 1,005,969 available naphthoylenebenzimidazole-r, 8'-dicarboxylic acid or their anhydride of the following formula
IlIl
Cn
C' Cn
C '
Il οIl ο
:O:O
Verfahren zur Herstellung eines
PigmentfarbstoffesMethod of making a
Pigment
Anmelder:Applicant:
Farbwerke Hoechst AktiengesellschaftFarbwerke Hoechst Aktiengesellschaft
vormals Meister Lucius & Brüning, Frankfurt/M.formerly Master Lucius & Brüning, Frankfurt / M.
Als Erfinder benannt:Named as inventor:
Dr. Wilhelm Eckert, Frankfurt/M.-Höchst;Dr. Wilhelm Eckert, Frankfurt / M.-Höchst;
Dr. Otto Fuchs, Frankfurt/M.-SchwanheimDr. Otto Fuchs, Frankfurt / M.-Schwanheim
mit 1 Mol l,3-Dimethyl-4,5-diaminobenzol bei Anoder Abwesenheit von organischen Lösungs- bzw. Verdünnungsmitteln oder Wasser kondensiert und das erhaltene Isomerengemisch nach an sich bekannten Verfahren, wie sie beispielsweise in den deutschen Patentschriften 536 911, 538 314 und 567 210 beschrieben sind, in seine Cis- und Transform trennt.with 1 mol of 1,3-dimethyl-4,5-diaminobenzene in the presence or absence of organic solutions or Diluents or water condensed and the mixture of isomers obtained according to known methods Process as described, for example, in German patents 536 911, 538 314 and 567 210 are described in its cis and transform separates.
Der Farbstoff kann mit dem gleichen Ergebnis auch durch Kondensation von Naphthoylen-5,7-dimethylbenzimidazol-l',8'-dicarbonsäure bzw. deren Anhydrid mit ortho-Phenylendiamin hergestellt werden. Er hat die folgende Zusammensetzung:The dye can also be obtained by condensing naphthoylene-5,7-dimethylbenzimidazole-l ', 8'-dicarboxylic acid with the same result or their anhydride can be produced with ortho-phenylenediamine. It has the following composition:
F,8'-dicarbonsäure bzw. deren Anhydrid mit 1,2-Dimethyl-4,5-diaminobenzol bzw. l,2-Dimethyl-3,4-diaminobenzol erhalten werden und die folgende Formeln besitzen:F, 8'-dicarboxylic acid or its anhydride with 1,2-dimethyl-4,5-diaminobenzene or 1,2-dimethyl-3,4-diaminobenzene and have the following formulas:
N*N *
Il ^-xIl ^ -x
/C y-tc / C yt c
;cOf ; c of
o-O-
Der neue Farbstoff wird zweckmäßig in geeigneter Weise in Feinverteilung gebracht und eignet sich sehr gut als Pigment in der Druckfarben- und Lackindustrie, zum Echtfärben von weichmacherhaltigem Polyvinylchlorid, ferner in sogenannten Einbrennlacken. Er besitzt bei sehr klarem Rotton eine große Farbstärke und sehr gute Lichtechtheit, in den Lösungsmitteln Alkohol, Benzol, Butylacetat und Aceton eine sehr gute bis ausgezeichnete Lösungsmittelechtheit und ferner eine einwandfreie Ausblutechtheit. In diesen wichtigen Eigenschaften ist das erfindungsgemäß herstellbare Produkt den isomeren Farbstoffen deutlich überlegen, die durch Kondensation von Naphthoylen - benzimidazol-/N-^^V-CHg CH3 The new dye is appropriately finely divided and is very suitable as a pigment in the printing inks and coatings industry, for the fast dyeing of plasticized polyvinyl chloride, and also in so-called stoving enamels. With a very clear red shade, it has great color strength and very good lightfastness, in the solvents alcohol, benzene, butyl acetate and acetone it has very good to excellent solventfastness and, furthermore, perfect resistance to bleeding. In these important properties, the product which can be prepared according to the invention is clearly superior to the isomeric dyes obtained by condensation of naphthoylene - benzimidazole- / N - ^^ V-CHg CH 3
CH3 CH 3
N -< V- CH3 N - <V - CH 3
Diese isomeren Farbstoffe bluten im Gegensatz zu dem neuen Farbstoff deutlich in ungefärbtes Polyvinylchlorid aus und besitzen daher kein praktisches Interesse.These isomeric dyes, in contrast to the new dye, clearly bleed into uncolored one Polyvinyl chloride and therefore have no practical interest.
Gewichtsteile Naphthoylen - benzimidazoll',8'-dicarbonsäure und 12 Gewichtsteile 1,3-Dimethyl-4,5-diaminobenzol werden in 600 Volumteilen Eisessig etwa 5 Stunden zum Sieden erhitzt, das Gemisch wird heiß abgesaugt, mit etwas heißem Eisessig, dann mit Wasser gewaschen und getrocknet.Parts by weight of naphthylene benzimidazoll ', 8'-dicarboxylic acid and 12 parts by weight of 1,3-dimethyl-4,5-diaminobenzene are heated to boiling in 600 parts by volume of glacial acetic acid for about 5 hours, the mixture is filtered off with suction while hot, washed with a little hot glacial acetic acid, then with water and dried.
609 7O8B57609 7O8B57
Die Umsetzung kann mit dem gleichen Ergebnis auch in Wasser durchgeführt werden.The reaction can also be carried out in water with the same result.
Zur Trennung des erhaltenen Isomerengemisches in seine Cis- und Transform werden 30 Gewichtsteile des obigen Produktes bei Raumtemperatur in 134 Gewichtsteile Äthanol (90°/0ig) und 44,8 Gewichtsteile gepulvertes Ätzkali eingetragen und etwa 3 Stunden auf 75 0C erhitzt. Nach dem Abkühlen auf etwa 300C wird das ausgeschiedene schwachgelbgefärbte Produkt abgesaugt. Nach dem Absaugen und Waschen mit einer alkoholischen Kalilauge wird der schwer- bzw. unlösliche Teil, der die Transform darstellt, in auf 70 bis 800C erhitztes Wasser eingetragen, etwa 1 Stunde bei dieser Temperatur gehalten, abgesaugt, neutral gewaschen und getrocknet. Der erhaltene Pigmentfarbstoff färbt nach entsprechender Feinverteilung weichmacherhaltiges Polyvinylchlorid sowie Druckfarben und Lacke in klaren roten Tönen, die sich durch sehr gute Echtheitseigenschaften, insbesondere sehr gute Lichtechtheit, Lösungsmittelechtheit und Ausblutechtheit, auszeichnen.For the separation of the isomer mixture obtained into its cis and trans form of 30 parts by weight are added to the above product at room temperature in 134 parts by weight of ethanol (90 ° / 0 strength) and 44.8 parts by weight of powdered potassium hydroxide and heated for about 3 hours at 75 0 C. After cooling to about 30 ° C., the pale yellow product which has separated out is filtered off with suction. After suctioning off and washing with an alcoholic potassium hydroxide solution, the sparingly or insoluble part, which represents the transform, is introduced into water heated to 70 to 80 ° C., kept at this temperature for about 1 hour, suctioned off, washed neutral and dried. The pigment dye obtained, after appropriate fine division, dyes plasticized polyvinyl chloride as well as printing inks and lacquers in clear red shades which are distinguished by very good fastness properties, in particular very good light fastness, solvent fastness and bleeding fastness.
Die in dem Filtrat enthaltene Cisform kann durch Verdünnen mit Wasser, Erhitzen auf etwa 8O0C, Absaugen, Neutralwaschen und Trocknen gewonnen werden. Sie stellt ein bordo- bis violettgefärbtes Produkt dar.The Cisform contained in the filtrate can be obtained by dilution with water, heating derived to about 8O 0 C, filtration with suction, washed until neutral, and drying. It is a bordo to purple colored product.
Claims (2)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF39402A DE1227589B (en) | 1963-04-04 | 1963-04-04 | Process for the preparation of a pigment dye |
| CH396064A CH449822A (en) | 1963-04-04 | 1964-03-26 | Process for the preparation of a pigment dye |
| GB1411664A GB1067044A (en) | 1963-04-04 | 1964-04-06 | Pigment dyestuff of the naphthalene tetracarboxylic acid bis-(benzimidazole) series and process for its manufacture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF39402A DE1227589B (en) | 1963-04-04 | 1963-04-04 | Process for the preparation of a pigment dye |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1227589B true DE1227589B (en) | 1966-10-27 |
Family
ID=7097755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF39402A Pending DE1227589B (en) | 1963-04-04 | 1963-04-04 | Process for the preparation of a pigment dye |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH449822A (en) |
| DE (1) | DE1227589B (en) |
| GB (1) | GB1067044A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE517195C (en) * | 1928-06-19 | 1931-02-26 | I G Farbenindustrie Akt Ges | Process for the preparation of Kuepen dyes |
-
1963
- 1963-04-04 DE DEF39402A patent/DE1227589B/en active Pending
-
1964
- 1964-03-26 CH CH396064A patent/CH449822A/en unknown
- 1964-04-06 GB GB1411664A patent/GB1067044A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE517195C (en) * | 1928-06-19 | 1931-02-26 | I G Farbenindustrie Akt Ges | Process for the preparation of Kuepen dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1067044A (en) | 1967-04-26 |
| CH449822A (en) | 1968-01-15 |
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