DE1045414B - Process for the production of solid, durable diazonium compounds - Google Patents
Process for the production of solid, durable diazonium compoundsInfo
- Publication number
- DE1045414B DE1045414B DEF21268A DEF0021268A DE1045414B DE 1045414 B DE1045414 B DE 1045414B DE F21268 A DEF21268 A DE F21268A DE F0021268 A DEF0021268 A DE F0021268A DE 1045414 B DE1045414 B DE 1045414B
- Authority
- DE
- Germany
- Prior art keywords
- solid
- production
- diazonium compounds
- durable
- alkyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von festen, haltbaren Diazoniumverbindungen Gegenstand der Patentanmeldung F 21079 IVb/ 12 q, Zusatz zum Patent 1008 310, ist ein Verfahren zur Herstellung fester, haltbarer Diazoniumverbindungen, welches darin besteht, daß man p-Aminoazoverbindungen der allgemeinen Formel worin R Wasserstoff, ein Halogenatom, eine Alkyl-oder Alkoxygruppe bedeutet, in an sich bekannter Weise dianotiert und anschließend die entstandenen Diazoniumverbindungen in an sich bekannter Weise in fester Form abscheidet. Nach diesem Verfahren erhält man Diazoniumverbindungen, die infolge ihrer guten Löslichkeit und Haltbarkeit mit Vorteil zur Herstellung von unlöslichen Azofarbstoffen auf der Faser Verwendung finden können.Process for the production of solid, durable diazonium compounds The subject of patent application F 21079 IVb / 12 q, addendum to patent 1008 310, is a process for the production of solid, durable diazonium compounds, which consists in using p-aminoazo compounds of the general formula where R denotes hydrogen, a halogen atom, an alkyl or alkoxy group, is dianotized in a manner known per se and then the diazonium compounds formed are deposited in a manner known per se in solid form. This process gives diazonium compounds which, owing to their good solubility and durability, can advantageously be used for the production of insoluble azo dyes on the fiber.
Bei der Weiterverfolgung dieses Erfindungsgedankens wurde nun gefunden, daß man zu Diazoniumverbindungen von ähnlichen wertvollen Eigenschaften gelangt, wenn man p-Aminoazoverbindungen der allgemeinen Formel worin R Wasserstoff, ein Halogenatom, eine Alkyl-oder Alkoxygruppe und R' eine Alkyl- oder Alkoxygruppe bedeuten, dianotiert und in an sich bekannter Weise in fester Form abscheidet.In pursuing this inventive concept, it has now been found that diazonium compounds with similar valuable properties are obtained if p-aminoazo compounds of the general formula are used where R is hydrogen, a halogen atom, an alkyl or alkoxy group and R 'is an alkyl or alkoxy group, dianotized and deposited in solid form in a manner known per se.
Die neuen Diazoniumverbindungen können in bekannten Formen, beispielsweise als Diazoniumsulfate, Diazoniumchlorid-Chlorzinkdoppelsalze oder Diazoniumborfluorideabgeschieden werden. Sie sind in Wasser gut löslich und besitzen eine sehr gute Haltbarkeit. Der besondere technische Wert und die Beständigkeit der Verbindungen ist nicht von der Art ihrer Abscheidung abhängig, sondern durch die besondere Wirkung des Chloratoms bedingt, die auch bei Eintritt einer Alkyl- oder Alkoxygruppe erhalten bleibt.The new diazonium compounds can be in known forms, for example deposited as diazonium sulfates, diazonium chloride-chlorozinc double salts or diazonium borofluorides will. They are readily soluble in water and have a very good shelf life. The special technical value and the durability of the connections is not of depends on the way they are deposited, but rather on the special effect of the chlorine atom conditional, which is retained even when an alkyl or alkoxy group enters.
Die neuen Verbindungen können, mit den gebräuchlichen Einstellmitteln vermischt, zu haltbaren Färbesalzen verarbeitet werden, die zur Herstellung von unlöslichen Azofarbstoffen auf der Faser Verwendung finden können. Die als Ausgangsmaterial für das vorliegende Verfahren dienenden, in der Literatur noch nicht beschriebenen p-Aminoazoverbindungen können nach bekannten Methoden! erhalten werden, beispielsweise durch Kuppeln von dianotierten o-Nitranilin oder dessen durch ein Halogenatom, eine Alkyl- oder Alkoxygruppe substituierten Derivaten mit durch eine Alkyl-oder Alkoxygruppe substituierten Chloranilin-N-methansulfonsäuren, die in p-Stellung zur Aminogruppe keinen Substituenten enthalten, und anschließende Abspaltung der Methansulfonsäureg ruppe. . Beispiel 30,7 Gewichtsteile 4-Amino-2-chlor-5-methoxy-2'-mitro-1,1'-azobenzol (Schmelzpunkt 222° C), erhältlich durch Kuppeln von dianotiertem o-Nitranilin mit 4-Chlor-2-anisidin-N-methansulfonsäure und anschließende hydrolytische Abspaltung der Methansulfonsäuregruppe, werden mit 7 Gewichtsteilen Natriumnitrit in der üblichen Weise in überschüssiger verdünnter Salzsäure dianotiert. Nach Verdünnen der Lösung mit 35° C warmen Wassers auf 3000 Volumteile und Abtrennung geringer Mengen unlöslicher Nebenprodukte durch Filtration wird durch Zugabe von 10 Gewichtsteilen 96o/oiger Schwefelsäure und 500 Gewichtsteilen Natriumbisulfat das saure Diazo-iumsulfat der Aminoazoverbindung in Form geiblicher, nadelförmiger Kristalle abgeschieden. Der kristalline Niederschlag wird abgesaugt und bei mäßiger Temperatur getrocknet. Das so erhaltene Produkt ist in Wasser gut löslich und weist bei Temperaturen bis zu 40° C eine sehr gute Haltbarkeit auf.The new connections can, with the usual adjustment means mixed, processed into durable coloring salts that are used in the production of insoluble azo dyes on the fiber can be used. The as the starting material used for the present process, not yet described in the literature p-Aminoazoverbindungen can by known methods! can be obtained, for example by coupling dianotated o-nitroaniline or its through a halogen atom, a Alkyl or alkoxy group-substituted derivatives with by an alkyl or alkoxy group substituted chloroaniline-N-methanesulfonic acids, which are in the p-position to the amino group contain no substituents, and subsequent cleavage of the Methanesulfonsäureg group. . Example 30.7 parts by weight of 4-amino-2-chloro-5-methoxy-2'-mitro-1,1'-azobenzene (Melting point 222 ° C), obtainable by coupling dianotized o-nitroaniline with 4-chloro-2-anisidine-N-methanesulfonic acid and subsequent hydrolytic cleavage the methanesulphonic acid group, with 7 parts by weight of sodium nitrite in the usual Way dianotized in excess dilute hydrochloric acid. After diluting the solution with 35 ° C warm water to 3000 parts by volume and separation of small amounts of insoluble By-products by filtration is obtained by adding 10 parts by weight of 96% Sulfuric acid and 500 parts by weight of sodium bisulfate, the acidic diazo-ium sulfate Aminoazo compound deposited in the form of yellowish, needle-shaped crystals. Of the crystalline precipitate is filtered off with suction and dried at a moderate temperature. That product obtained in this way is readily soluble in water and has a Temperatures has a very good shelf life up to 40 ° C.
In derselben Weise lassen sich die nachstehenden Aminoazoverbindungen in guter Ausbeute in ihre Diazoniumverbindungem überführen, die, in bekannter Weise abgeschieden,- ebenfalls eine sehr gute Haltbarkeit besitzen: 4-Amino-3-chlor-6-methyl-2'-nitro-1,1-azobenzol (Schmelzpunkt 131° C), 4- Amino -3-chlor-4',6-dimethyl-2'-nitro-1,1'-azobenzol (Schmelzpunkt 175°C), 4-Amino-2-chlor-5-methoxy-4'-methyl-2'-nitro-1,1'-azobenzol (Schmelzpunkt 219° C), 4-Amino-2,4'-dichlor-5-methoxy-2'-nitro-1,1'-azobenzol (Schmelzpunkt 224° C).The following aminoazo compounds can be prepared in the same manner convert them in good yield into their diazonium compounds, in a known manner deposited, - also have a very good shelf life: 4-amino-3-chloro-6-methyl-2'-nitro-1,1-azobenzene (Melting point 131 ° C.), 4- amino -3-chloro-4 ', 6-dimethyl-2'-nitro-1,1'-azobenzene (melting point 175 ° C), 4-amino-2-chloro-5-methoxy-4'-methyl-2'-nitro-1,1'-azobenzene (melting point 219 ° C), 4-amino-2,4'-dichloro-5-methoxy-2'-nitro-1,1'-azobenzene (melting point 224 ° C).
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF21268A DE1045414B (en) | 1956-09-19 | 1956-09-19 | Process for the production of solid, durable diazonium compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF21268A DE1045414B (en) | 1956-09-19 | 1956-09-19 | Process for the production of solid, durable diazonium compounds |
Publications (1)
Publication Number | Publication Date |
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DE1045414B true DE1045414B (en) | 1958-12-04 |
Family
ID=7089999
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF21268A Pending DE1045414B (en) | 1956-09-19 | 1956-09-19 | Process for the production of solid, durable diazonium compounds |
Country Status (1)
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DE (1) | DE1045414B (en) |
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5616443A (en) | 1993-08-05 | 1997-04-01 | Kimberly-Clark Corporation | Substrate having a mutable colored composition thereon |
US5643356A (en) | 1993-08-05 | 1997-07-01 | Kimberly-Clark Corporation | Ink for ink jet printers |
US5645964A (en) | 1993-08-05 | 1997-07-08 | Kimberly-Clark Corporation | Digital information recording media and method of using same |
US5681380A (en) | 1995-06-05 | 1997-10-28 | Kimberly-Clark Worldwide, Inc. | Ink for ink jet printers |
US5733693A (en) | 1993-08-05 | 1998-03-31 | Kimberly-Clark Worldwide, Inc. | Method for improving the readability of data processing forms |
US5782963A (en) | 1996-03-29 | 1998-07-21 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5837429A (en) | 1995-06-05 | 1998-11-17 | Kimberly-Clark Worldwide | Pre-dyes, pre-dye compositions, and methods of developing a color |
US5855655A (en) | 1996-03-29 | 1999-01-05 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5865471A (en) | 1993-08-05 | 1999-02-02 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms |
US5885337A (en) | 1995-11-28 | 1999-03-23 | Nohr; Ronald Sinclair | Colorant stabilizers |
US5891229A (en) | 1996-03-29 | 1999-04-06 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6017661A (en) | 1994-11-09 | 2000-01-25 | Kimberly-Clark Corporation | Temporary marking using photoerasable colorants |
US6033465A (en) | 1995-06-28 | 2000-03-07 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
US6099628A (en) | 1996-03-29 | 2000-08-08 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6211383B1 (en) | 1993-08-05 | 2001-04-03 | Kimberly-Clark Worldwide, Inc. | Nohr-McDonald elimination reaction |
US6228157B1 (en) | 1998-07-20 | 2001-05-08 | Ronald S. Nohr | Ink jet ink compositions |
US6265458B1 (en) | 1998-09-28 | 2001-07-24 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6277897B1 (en) | 1998-06-03 | 2001-08-21 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6294698B1 (en) | 1999-04-16 | 2001-09-25 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6331056B1 (en) | 1999-02-25 | 2001-12-18 | Kimberly-Clark Worldwide, Inc. | Printing apparatus and applications therefor |
US6368395B1 (en) | 1999-05-24 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Subphthalocyanine colorants, ink compositions, and method of making the same |
US6368396B1 (en) | 1999-01-19 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
US6486227B2 (en) | 2000-06-19 | 2002-11-26 | Kimberly-Clark Worldwide, Inc. | Zinc-complex photoinitiators and applications therefor |
US6503559B1 (en) | 1998-06-03 | 2003-01-07 | Kimberly-Clark Worldwide, Inc. | Neonanoplasts and microemulsion technology for inks and ink jet printing |
US6524379B2 (en) | 1997-08-15 | 2003-02-25 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2633461A (en) * | 1950-03-27 | 1953-03-31 | Naphtol Chemie Offenbach | Diazonium compounds |
-
1956
- 1956-09-19 DE DEF21268A patent/DE1045414B/en active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2633461A (en) * | 1950-03-27 | 1953-03-31 | Naphtol Chemie Offenbach | Diazonium compounds |
Cited By (40)
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US6120949A (en) | 1993-08-05 | 2000-09-19 | Kimberly-Clark Worldwide, Inc. | Photoerasable paint and method for using photoerasable paint |
US6060200A (en) | 1993-08-05 | 2000-05-09 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms and methods |
US6211383B1 (en) | 1993-08-05 | 2001-04-03 | Kimberly-Clark Worldwide, Inc. | Nohr-McDonald elimination reaction |
US5645964A (en) | 1993-08-05 | 1997-07-08 | Kimberly-Clark Corporation | Digital information recording media and method of using same |
US6127073A (en) | 1993-08-05 | 2000-10-03 | Kimberly-Clark Worldwide, Inc. | Method for concealing information and document for securely communicating concealed information |
US5683843A (en) | 1993-08-05 | 1997-11-04 | Kimberly-Clark Corporation | Solid colored composition mutable by ultraviolet radiation |
US5733693A (en) | 1993-08-05 | 1998-03-31 | Kimberly-Clark Worldwide, Inc. | Method for improving the readability of data processing forms |
US6054256A (en) | 1993-08-05 | 2000-04-25 | Kimberly-Clark Worldwide, Inc. | Method and apparatus for indicating ultraviolet light exposure |
US5643701A (en) | 1993-08-05 | 1997-07-01 | Kimberly-Clark Corporation | Electrophotgraphic process utilizing mutable colored composition |
US5643356A (en) | 1993-08-05 | 1997-07-01 | Kimberly-Clark Corporation | Ink for ink jet printers |
US5865471A (en) | 1993-08-05 | 1999-02-02 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms |
US5858586A (en) | 1993-08-05 | 1999-01-12 | Kimberly-Clark Corporation | Digital information recording media and method of using same |
US6060223A (en) | 1993-08-05 | 2000-05-09 | Kimberly-Clark Worldwide, Inc. | Plastic article for colored printing and method for printing on a colored plastic article |
US6066439A (en) | 1993-08-05 | 2000-05-23 | Kimberly-Clark Worldwide, Inc. | Instrument for photoerasable marking |
US5908495A (en) | 1993-08-05 | 1999-06-01 | Nohr; Ronald Sinclair | Ink for ink jet printers |
US5616443A (en) | 1993-08-05 | 1997-04-01 | Kimberly-Clark Corporation | Substrate having a mutable colored composition thereon |
US6342305B1 (en) | 1993-09-10 | 2002-01-29 | Kimberly-Clark Corporation | Colorants and colorant modifiers |
US6017661A (en) | 1994-11-09 | 2000-01-25 | Kimberly-Clark Corporation | Temporary marking using photoerasable colorants |
US6235095B1 (en) | 1994-12-20 | 2001-05-22 | Ronald Sinclair Nohr | Ink for inkjet printers |
US6063551A (en) | 1995-06-05 | 2000-05-16 | Kimberly-Clark Worldwide, Inc. | Mutable dye composition and method of developing a color |
US5681380A (en) | 1995-06-05 | 1997-10-28 | Kimberly-Clark Worldwide, Inc. | Ink for ink jet printers |
US5837429A (en) | 1995-06-05 | 1998-11-17 | Kimberly-Clark Worldwide | Pre-dyes, pre-dye compositions, and methods of developing a color |
US6033465A (en) | 1995-06-28 | 2000-03-07 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
US6168655B1 (en) | 1995-11-28 | 2001-01-02 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5885337A (en) | 1995-11-28 | 1999-03-23 | Nohr; Ronald Sinclair | Colorant stabilizers |
US5855655A (en) | 1996-03-29 | 1999-01-05 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6168654B1 (en) | 1996-03-29 | 2001-01-02 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6099628A (en) | 1996-03-29 | 2000-08-08 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5782963A (en) | 1996-03-29 | 1998-07-21 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5891229A (en) | 1996-03-29 | 1999-04-06 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6524379B2 (en) | 1997-08-15 | 2003-02-25 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
US6277897B1 (en) | 1998-06-03 | 2001-08-21 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6503559B1 (en) | 1998-06-03 | 2003-01-07 | Kimberly-Clark Worldwide, Inc. | Neonanoplasts and microemulsion technology for inks and ink jet printing |
US6228157B1 (en) | 1998-07-20 | 2001-05-08 | Ronald S. Nohr | Ink jet ink compositions |
US6265458B1 (en) | 1998-09-28 | 2001-07-24 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6368396B1 (en) | 1999-01-19 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
US6331056B1 (en) | 1999-02-25 | 2001-12-18 | Kimberly-Clark Worldwide, Inc. | Printing apparatus and applications therefor |
US6294698B1 (en) | 1999-04-16 | 2001-09-25 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6368395B1 (en) | 1999-05-24 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Subphthalocyanine colorants, ink compositions, and method of making the same |
US6486227B2 (en) | 2000-06-19 | 2002-11-26 | Kimberly-Clark Worldwide, Inc. | Zinc-complex photoinitiators and applications therefor |
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