DE903327C - Process for the production of insoluble brown azo dyes on fiber - Google Patents

Process for the production of insoluble brown azo dyes on fiber

Info

Publication number
DE903327C
DE903327C DEN4102A DEN0004102A DE903327C DE 903327 C DE903327 C DE 903327C DE N4102 A DEN4102 A DE N4102A DE N0004102 A DEN0004102 A DE N0004102A DE 903327 C DE903327 C DE 903327C
Authority
DE
Germany
Prior art keywords
brown
amino
azo dyes
fiber
production
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
Application number
DEN4102A
Other languages
German (de)
Inventor
Dr Werner Kirst
Dr Wilhelm Seidenfaden
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Priority to DEN4102A priority Critical patent/DE903327C/en
Application granted granted Critical
Publication of DE903327C publication Critical patent/DE903327C/en
Expired legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/68—Preparing azo dyes on the material

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Description

Verfahren zur Erzeugung unlöslicher brauner Azofarbstoffe auf der Faser Der Gegenstand des Patents 88q.491 sind Verfahren zur Herstellung unlöslicher wertvoller brauner Azofarbstoffe auf der Faser aus diazotiertem 4-Aminodiphenylamin oder seinen Substitutionsprodukten und 1,6- und 2, 7-Acylamino-oxynaphthalinen. Diese Verfahren eignen sich ferner zur Herstellung von Weiß- und Buntreserven unter einem braunen Fond.Process for producing insoluble brown azo dyes on the Fiber The subject of patent 88q.491 are processes for making insoluble valuable brown azo dyes on the fiber made from diazotized 4-aminodiphenylamine or its substitution products and 1,6- and 2,7-acylamino-oxynaphthalenes. These processes are also suitable for the production of white and colored reserves a brown fond.

Bei Weiterverfolgung des Erfindungsgedankens wurde nun gefunden, daß man ebenfalls zu wertvollen braunen Azofarbstoffen gelangt, wenn man die 1,6- bzw. 2, 7-Acylaminonaphthole durch 1,6- bzw. 2, 7-Triazinaminonaphthole, d. h. die Kondensationsprodukte aus 2, 4, 6-Trihalogen-i, 3; g-triazinen oder deren Umwandlungsprodukte, welche noch wenigstens ein austauschfähiges Halogen enthalten, mit i, 2 oder 3 Molekülen i, 6- und/oder 2, 7-Aminonaphthol ersetzt und die Entwicklung nach dem Hauptpatent mit diazotierten 4-Aminodiphenylaminen vornimmt.In pursuing the idea of the invention it has now been found that you also get to valuable brown azo dyes if you use the 1,6 resp. 2, 7-acylaminonaphthols by 1,6- or 2,7-triazineaminonaphthols, d. H. the condensation products from 2, 4, 6-trihalo-i, 3; g-triazines or their conversion products, which still contain at least one exchangeable halogen with 1, 2 or 3 molecules i, 6- and / or 2, 7-aminonaphthol replaced and the development according to the main patent with diazotized 4-aminodiphenylamines.

Die nach diesem Verfahren hergestellten Färbungen sind ebenfalls von besonderer Wasch- und Lichtechtheit. Sie sind den bekannten substantiven braunen Farbstoffen in ihren Eigenschaften bedeutend überlegen.The dyeings produced by this process are also from special wash and lightfastness. They are the well-known substantive brown ones Significantly superior to dyes in terms of their properties.

Das Verfahren eignet sich in gleicher Weise auch zur Erzeugung von Weiß- und Buntreserven unter einem braunen Fond und kann, wie im Patent 884 491 beschrieben, durchgeführt werden.The method is also suitable for generating White and colored reserves under a brown background and can, as in patent 884 491 described.

Im allgemeinen werden die zu dem vorliegenden Verfahren benötigten Produkte nach bekannten Verfahren hergestellt, und zwar durch Kondensation von i, 2 oder 3 Molekülen i, 6- und, `oder 2, 7-Aminonaphthol mit einem Molekül 2, 4, 6-Trihalogentriazin oder dessen Umwandlungsprodukten, welche noch wenigstens ein austauschfähiges Halogen enthalten. Die so erhaltenen Kondensationsprodukte stellen farblose bis schwach gefärbte, in verdünnter Natronlauge lösliche Körper dar.In general, those are required for the present process Products made by known processes, namely by condensation of i, 2 or 3 molecules i, 6- and, `or 2, 7-aminonaphthol with a Molecule 2, 4, 6-trihalotriazine or its conversion products, which still contain at least one exchangeable halogen. The condensation products thus obtained represent colorless to pale colored bodies soluble in dilute sodium hydroxide solution represent.

Zur Herstellung der für das vorliegendeVerfahren benötigten Ausgangsstoffe kommen nicht nur das I, 6- und 2, 7-Aminonaphthol in Frage, sondern auch deren Abkömmlinge, bei denen eines der H-Atome der Aminogruppe durch eine Alkyl-, Aralkyl-, Aryl- oder Cycloalkylgruppe ersetzt ist. Beispielsweise seien genannt I-N-Methyl-amino-6-oxynaphthalin, 2-N-Benzyl-amino-7-oxynaphthalin und 2-N-Phenyl-amino-7-oxynaphthalin. Als für die Kondensation geeignete Abkömmlinge des I, 3, 5-Triazins werden beispielsweise folgende genannt: 2, 4, 6-Trichlor-i, 3, 5-triazin, 2, 4, 6-Tribrom - I, 3, 5 - triazin, 2 - Phenylamino - 4, 6 - dichlorh 3, 5-triazin, 2, 4-Diphenylamino-6-chlor-r, 3, 5-triazin, 2-(2'-Methyl-5'-chlorphenyl-I')-amino-4, 6-dichlor-I, 3, 5-tnazin, 2-(Naphthyl-2')-amino-4, 6-dichlor-I, 3, 5-trzazin, 2-Phenoxy-4, 6-dichlor-I, 3, 5-triazin, 2 - N - Methyl- N - phenyl- amino -4 - cyclohexylamino-6-brom-I, 3, 5-triazin, 2-Benzylamino-4-äthoxy-6-chlor-I, 3, 5-triazin.For the preparation of the starting materials required for the present process not only the I, 6- and 2, 7-aminonaphthol come into question, but also their derivatives, in which one of the H atoms of the amino group is replaced by an alkyl, aralkyl, aryl or Cycloalkyl group is replaced. Examples include I-N-methyl-amino-6-oxynaphthalene, 2-N-benzyl-amino-7-oxynaphthalene and 2-N-phenyl-amino-7-oxynaphthalene. As for that Derivatives of 1,3,5-triazine which are suitable for condensation are, for example, the following named: 2, 4, 6-trichloro-i, 3, 5-triazine, 2, 4, 6-tribromo - I, 3, 5 - triazine, 2 - phenylamino - 4, 6 - dichloro 3, 5-triazine, 2, 4-diphenylamino-6-chloro-r, 3, 5-triazine, 2- (2'-methyl-5'-chlorophenyl-I ') - amino-4, 6-dichloro-1, 3, 5-tnazine, 2- (naphthyl-2') - amino-4, 6-dichloro-1, 3, 5-trzazine, 2-phenoxy-4, 6-dichloro-1, 3, 5-triazine, 2 - N - methyl N - phenyl amino -4 - cyclohexylamino-6-bromo-1, 3, 5-triazine, 2-benzylamino-4-ethoxy-6-chloro-I, 3, 5-triazine.

Weitere erfindungsgemäße Kombinationen zur Herstellung brauner Töne, die ebenfalls weiß und bunt reserviert werden können, werden beispielsweise in folgender Übersicht angeführt Azokomponente 1 C Cy steht für N N Diazokomponente Farbton (I l N Cy - OH] 4-Amino-diphenylamin dunkles rot- stickiges Braun HN --@@Y@, OH Cy - 4-Amino-4'-methoxydiphenylamin dunkles Braun 3 H N = _OH] Cy = ` 4-Amino-4'-methoxydiphenylamin Braun NH H N -@@@- OH] Cy - 4-Amino-3-methoxydiphenylamin Dunkelbraun 2 NH Cy - N H - 0 H 4-Amino-diphenylamin rotstickiges Braun Azokomponente C Cy / steht für \\ N N Diazokomponente Farbton 1I -C C- \ 1177 N Cy-NH OH 4-Amino-3-methoxy-4'-methyl- Braun diphenylamin N H -->I2 CH, N H-#_ I_\ ,Cl Cy / 4-Amino-4'-methoxydiphenylamin Braun HN!@@@ \-OH 12 -NH-' Cy - 4-Amino-diphenylamin Braun OH J, @-NH _D Cy - 4-Amino-2'-chlordiphenylamin rotstichiges Dunkelbraun OH_, NH Cy = < 4-Amino-3-äthoxydiphenylamin Braun NH OH -2 dito 4, 4'-Diamino-diphenylamin Braun Cy-HN -c 4-Amino-4'-methoxydiphenylamin Braun NH--< @ /] 2 'OH Azokomponente C Cy'@ steht für - Diazakomponente Farbton N N -C C- N Cy-HN OH N H 4-Amino-diphenylamin rotstichiges Braun OH Cy - H N I \-OH] 4-Amino-4'-methoxydiphenylamin Braun NH OH NH--@ @--CHa @--I Cy - H N @@- O H 4-Amino-3-methoxydiphenylamin rotstickiges Braun N H OH CH;, CH, N Cy - HN -1 /'\@@- OH 4-Amino-4'-methoxydiphenylamin Braun NH - O H Further combinations according to the invention for producing brown tones, which can also be reserved for white and colored, are listed, for example, in the following overview Azo component 1 C. Cy stands for NN diazo component shade (I l N Cy - OH] 4-amino-diphenylamine dark red stuffy brown HN - @@ Y @, OH Cy - 4-Amino-4'-methoxydiphenylamine dark brown 3 HN = _OH] Cy = `4-Amino-4'-methoxydiphenylamine brown NH HN - @@@ - O H] Cy - 4-Amino-3-methoxydiphenylamine Dark brown 2 NH Cy - NH - 0 H 4-amino-diphenylamine red sticky Brown Azo component C. Cy / stands for \\ NN diazo component shade 1I -C C- \ 1177 N Cy-NH OH 4-amino-3-methoxy-4'-methyl brown diphenylamine NH -> I2 CH, N H - # _ I_ \, Cl Cy / 4-Amino-4'-methoxydiphenylamine Brown HN! @@@ \ -OH 12th -NH- ' Cy - 4-amino-diphenylamine brown OH J, @ -NH _D Cy - 4-Amino-2'-chlorodiphenylamine reddish Dark brown OH_, NH Cy = <4-amino-3-ethoxydiphenylamine brown NH OH -2 ditto 4,4'-diamino-diphenylamine brown Cy-HN -c 4-Amino-4'-methoxydiphenylamine brown NH - < @ / ] 2 'OH Azo component C. Cy '@ stands for - Diaza component shade NN -C C- N Cy-HN OH Red-tinged NH 4-amino-diphenylamine Brown OH Cy - H N I \ -OH] 4-amino-4'-methoxydiphenylamine brown NH OH NH - @ @ - CHa @ - I Cy - HN @@ - OH 4-Amino-3-methoxydiphenylamine red nitrogen Brown NH O H CH ;, CH, N Cy - HN - 1 / ' \ @@ - OH 4-Amino-4'-methoxydiphenylamine Brown NH - OH

Claims (2)

PATENTANSPRÜCHE: i. Weitere Ausbildung des Verfahrens zur Erzeugung unlöslicher brauner Azofarbstoffe auf der Faser gemäß Patent 898 735, dadurch gekennzeichnet, daß die Farbstoffe aus diazotiertem 4-Aminodiphenylamin oder seinen Substitutionsprodukten und i, 6-bzw. 2, 7-Triazinaminooxynaphthalinen nach bekannten Verfahren erzeugt werden. PATENT CLAIMS: i. Further development of the process for producing insoluble brown azo dyes on the fiber according to Patent 898 735, characterized in that the dyes are made from diazotized 4-aminodiphenylamine or its substitution products and i, 6 or. 2, 7-Triazinaminooxynaphthalinen are produced by known processes. 2. Verfahren gemäß Anspruch i, dadurch gekennzeichnet, daß man zur Erzeugung von Weiß- und Bunteffekten auf braunem Grunde die Ware mit Alkalisalzen von i, 6- bzw. 2, 7-Triazinaminooxynaphthalinen imprägniert und sie hierauf gemäß den Ansprüchen 2 bis 2-des Haupt- patentes weiterverarbeitet. 5
2. The method according to claim i, characterized in that the goods are impregnated with alkali salts of i, 6- or 2, 7-triazinaminooxynaphthalenes and they are used to produce white and colored effects on a brown background then according to claims 2 to 2 of the main patents processed. 5
DEN4102A 1951-07-01 1951-07-01 Process for the production of insoluble brown azo dyes on fiber Expired DE903327C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEN4102A DE903327C (en) 1951-07-01 1951-07-01 Process for the production of insoluble brown azo dyes on fiber

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEN4102A DE903327C (en) 1951-07-01 1951-07-01 Process for the production of insoluble brown azo dyes on fiber

Publications (1)

Publication Number Publication Date
DE903327C true DE903327C (en) 1954-02-04

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEN4102A Expired DE903327C (en) 1951-07-01 1951-07-01 Process for the production of insoluble brown azo dyes on fiber

Country Status (1)

Country Link
DE (1) DE903327C (en)

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