DE1940685B2 - DISPERSION DYES OF THE AMINOPYRAZOLE SERIES, PROCESS FOR THEIR MANUFACTURING AND USE - Google Patents

DISPERSION DYES OF THE AMINOPYRAZOLE SERIES, PROCESS FOR THEIR MANUFACTURING AND USE

Info

Publication number
DE1940685B2
DE1940685B2 DE19691940685 DE1940685A DE1940685B2 DE 1940685 B2 DE1940685 B2 DE 1940685B2 DE 19691940685 DE19691940685 DE 19691940685 DE 1940685 A DE1940685 A DE 1940685A DE 1940685 B2 DE1940685 B2 DE 1940685B2
Authority
DE
Germany
Prior art keywords
dyes
parts
manufacturing
aminopyrazole
dispersion dyes
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.)
Granted
Application number
DE19691940685
Other languages
German (de)
Other versions
DE1940685C3 (en
DE1940685A1 (en
Inventor
Hans-Jürgen Dr. 6718 Grünstadt; Mayer Kurt Dr. 6700 Ludwigshafen; Küpper Gerhard Dr. 6800 Mannheim; Armbrust Herbert 6718 Grünstadt Sturm
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.)
BASF SE
Original Assignee
Badische Anilin and Sodafabrik 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
Priority to BE754401D priority Critical patent/BE754401A/en
Application filed by Badische Anilin and Sodafabrik AG filed Critical Badische Anilin and Sodafabrik AG
Priority to DE19691940685 priority patent/DE1940685C3/en
Priority to CH406873A priority patent/CH553840A/en
Priority to FR7027978A priority patent/FR2057082B1/fr
Priority to GB3817870A priority patent/GB1310564A/en
Priority to JP6934370A priority patent/JPS4812403B1/ja
Publication of DE1940685A1 publication Critical patent/DE1940685A1/en
Publication of DE1940685B2 publication Critical patent/DE1940685B2/en
Application granted granted Critical
Publication of DE1940685C3 publication Critical patent/DE1940685C3/en
Expired legal-status Critical Current

Links

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
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D06P1/18—Azo 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
    • E—FIXED CONSTRUCTIONS
    • E04—BUILDING
    • E04B—GENERAL BUILDING CONSTRUCTIONS; WALLS, e.g. PARTITIONS; ROOFS; FLOORS; CEILINGS; INSULATION OR OTHER PROTECTION OF BUILDINGS
    • E04B5/00—Floors; Floor construction with regard to insulation; Connections specially adapted therefor
    • E04B5/44—Floors composed of stones, mortar, and reinforcing elements

Landscapes

  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Electromagnetism (AREA)
  • Civil Engineering (AREA)
  • Structural Engineering (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Description

ίο Die Erfindung betrifft wertvolle neue Mono.;/
farbstoffe der Aminop> ra/olreihe der allgemei!·
F(U meiίο The invention relates to valuable new mono.; /
dyes of the aminop> ra / oil series in general!
F (U mei

in der X ein ChIiM- oder Bromatom oiler eine C.irboniClliow-. '/arhoiiihoXN-. Nitro- oderC\an- -'■ gruppe und Y ein Wasserstoff. Chlor- oder Bromatom ist.in the X a ChIiM- or Bromatom oiler one C.irboniClliow-. '/ arhoiiihoXN-. Nitro or C \ an- '■ group and Y is hydrogen. Is chlorine or bromine atom.

2. Farbstoffe geni;ilC\nspruch 1 der aligemeinen F'ormel2. Dyes geni; ilC \ nspruch 1 of the general Formula

κ Νκ Ν

N-N-

IFNIFN

1111th

O1NO 1 N

--N--N--N - N

FNFN

in der X1 eine Carbomethoxv-. Carboathow- oder in der X ein Chlor- oder Bromalom oder eine ( ari·- melhoxy-. Carboathoxy-. Nitro- oder Cyangnspp.- und Y ein Wasserstoff-, Chlor- oder Bromatom sind Diazokomnonenten zur Herstellung der ncu.hin the X 1 a carbomethoxv-. Carboathow or in which X is a chlorine or bromine or a (ari · melhoxy, carboathoxy, nitro or cyangnspp.- and Y is a hydrogen, chlorine or bromine atom are diazo components for the production of the ncu.h

Farbstoffe sind z.B. 2-Cyan-4-nitrani!in. ?.-C\a,·.Dyes are e.g. 2-cyan-4-nitrani! In. ? .- C \ a, ·.

(vehloM-nitranilin. Z-Cyan-o-broni^-nilranilin. 2.< >Dichtor - 4 - nitranilin. 2.6 - Dibrorn ■■ 4 - niiranilin.(vehloM-nitraniline. Z-Cyan-o-broni ^ -nilraniline. 2. < > Dichtor - 4 - nitroaniline. 2.6 - Dibrorn ■■ 4 - niiraniline.

2 - Chlor - 6 - brom -4 - mti anilin, 2 - Carbomethov, 4 - nitranilin. 2 - Carboathoxy - 4 - nitranilin oder 2-Carbomethoxy-6-brom-4-nitrantlin.2 - chlorine - 6 - bromine -4 - mti aniline, 2 - carbomethov, 4 - nitroaniline. 2 - Carboathoxy - 4 - nitroaniline or 2-Carbomethoxy-6-bromo-4-nitrantline.

Von besonderer technischer Bedeutung sind Farbstoffe der allgemeinen FormelDyes of the general formula are of particular industrial importance

Cyaiigruppe und Y1 ein Wasserstoff-. Chlor- oder Bromatom ist.
3. Farbstoff gemäß Anspruch 1 und 2 der F'ormelCyaiigruppe and Y 1 is a hydrogen. Is chlorine or bromine atom.
3. Dyestuff according to claim 1 and 2 of the formula

BrBr

O, NO, N

x,x,

-Ν---Ν-Ν --- Ν

Q1N--<Q 1 N - <

cncn

IFN ■■-· N
' N 'IFN ■■ - · N
'N'

Y1 Y 1

U2N . NU 2 N. N

4. Verfahren zur Herstellung von Farbstoffen der im Anspruch I angegebenen F'ormel. dadurch gekennzeichnet, daß man Diazoverbindungen von Aminen der allgemeinen Formel4. A process for the preparation of dyes of the formula specified in claim I. through this characterized in that one diazo compounds of amines of the general formula

(VN-(VN-

mit l-Phenvl-5-aminopyrazol kuppelt, wobei X in der X, eine Carbomelhoxy-. Carboathoxy- oder Cyangruppe und Y1 ein Wasserstoff-, Chlor oder Bromatom sind.
Die neuen Farbstoffe sind Gelb bis Orange undcoupling with l-phenvl-5-aminopyrazole, where X is in the X, a carbomelhoxy-. Carboathoxy or cyano and Y 1 are hydrogen, chlorine or bromine.
The new dyes are yellow to orange and

(*> eignen sich zum Färben von synthetischen, linearen Polyestern sowohl nach der Carrier- als auch nach der HT-Methode. Man erzielt dabei Färbungen mit ausgezeichneten Echtheiten.(*> are suitable for dyeing synthetic, linear Polyesters using both the carrier and the HT method. One achieves staining with excellent fastness properties.

Gegenüber nächstvergleichbaren aus der deutschenCompared to the next comparable from the German

fts Patentschrift 1 282 212 bekannten Farbstoffen zeichnen sich die neuen Farbstoffe durch besseres Ziehvermögen und besseren Farbaufbau aus. Bei der Ähnlichkeit der Farbstoffe war dieses Verhalten über-fts patent specification 1 282 212 draw known dyes the new dyes are characterized by better drawability and better color structure. In the Similarity of the dyes, this behavior was

laschend. Gegenüber Farbstoffen, die in der britischen Patentschrift ί 034 489 beschrieben sind, haben die neuen Farbstoffe unvorhersehbare Vorteile in der Lichtechtheit.lapping. Compared to dyes that are described in British patent ί 034 489, the new dyes unpredictable advantages in the Lightfastness.

Zur Herstellung der neuen Farbstoffe kann man Diazoverbindungen von Aminen der allgemeinen FormelTo prepare the new dyes one can use diazo compounds of amines of the general formula

O1N-:O 1 N-:

NH, vermindertem Druck bei 60 C getrocknet. Man erhäli 9.0 Teile des Farbstoffs der FormelNH, dried at 60 ° C. under reduced pressure. 9.0 parts of the dye of the formula are obtained

O, N-O, N-

ClCl

CNCN

nach bekannten Methoden mit l-Phenyl-5-aminopvrazol kuppeln.according to known methods with l-phenyl-5-aminopvrazole couple.

In den folgender Beispielen beziehen sich Angaben über Teile und Prozent.', sofern nicht anders vertnerkt. auf das Gewicht.In the following examples, data relate to about parts and percent. ', unless otherwise stated. on weight.

Beispiel 1example 1

8.46 Teile 2-C'yan-4-nitro-6-brom;:nilin ((1.035 Mol) werden bei 10 bis 15 C in 41 Teile konzentrierte Schwefelsäure eingetragen. Sobald das Amin gelöst ist. kühlt man auf 5 C ab und fügt allmählich 30 Teile eines Fisessig-Propionsäure-Gemischcs (17 : 3) zu.8.46 parts of 2-cyano-4-nitro-6-bromo;: niline ((1.035 mol) concentrated sulfuric acid is introduced into 41 parts at 10 to 15 C. Once the amine is dissolved is. It is cooled to 5 ° C. and 30 parts of a mixture of acetic acid and propionic acid (17: 3) are gradually added.

Dann werden hei ü Dis 5 C langsam 1J Teile Nitrosylschwefelsäure zugegeben und 3 Si .,nden bei dieser Temperatur gerührt. Anschließend gib! man die Diazolösung zu einer gekühlten Lösur^ von 5,8 Teilen (0.035 Mol) l-Phenyl-5-amino-pyrazol in 150 Teilen Methanol und 50 Teilen Wasser. Nach beendeter Zugabe hält man 1 Stunde bei 0 bis 5 C, saugt den ausgefallenen Farbstoff ab, wäscht mit Wasser neutral und trocknet bei 60 C unter vermindertem Druck.Then hei ü Dis 5 are C 1 slowly added and J parts of nitrosylsulfuric 3 Si. Nd stirred at this temperature. Then give! the diazo solution is added to a cooled solution of 5.8 parts (0.035 mol) of l-phenyl-5-aminopyrazole in 150 parts of methanol and 50 parts of water. After the addition has ended, the mixture is kept at 0 to 5 ° C. for 1 hour, the dyestuff which has precipitated out is filtered off with suction, washed neutral with water and dried at 60 ° C. under reduced pressure.

Man erhält 13.7 Teile des Farbstoffs der Formel13.7 parts of the dye of the formula are obtained

4040

4545

der auf Polyesterfasern ebenfalls sehr echte Orangefärbungen ergibt.which also gives very real orange colorations on polyester fibers.

Analog der angegebenen Arbeitsweise erhält man mit den Diazokomponenten der nachstehenden Tabelle Farbstoffe, die Polyester-Textilmaterial im angegebenen Farbton färben.The diazo components in the table below are obtained analogously to the procedure given Dyes containing polyester textile material in the specified Color shade.

der Polyesterfasern in klaren Orangetönen mit allgemein sehr guten Echtheiten färbt.of polyester fibers in clear orange tones with general dyes very good fastness properties.

Beispiel 2Example 2

5,9 Teile 2-C"yan-4-nitro-6-chlor-anilin (0,03 Mol) werden wie im Beispiel 1 beschrieben diazoticrt. Die Diazolösung wird dann langsam bei 0 bis 5" C zu der Lösung von 4,8 Teilen l-Phenyl-5-amino-pyrazol (0,03 Mol) in 100 Teilen Methanol und 50 Teilen Wasser zugegeben. Man hält 1 Stunde bei dieser Temperatur. Dann wird der ausgefallene Farbstoff mit Wasser neutral gewaschen und unter5.9 parts of 2-C "yan-4-nitro-6-chloro-aniline (0.03 mol) are diazotized as described in Example 1. The Diazo solution is then slowly added at 0 to 5 "C to the solution of 4.8 parts of 1-phenyl-5-aminopyrazole (0.03 mol) in 100 parts of methanol and 50 parts of water were added. You hold 1 hour at this Temperature. Then the precipitated dye is washed neutral with water and washed under

5555

6060

Beispielexample

ni;t 7t-komponenteni; t 7t component

-C7 V-NH,-C 7 V-NH,

CN
ClCN
Cl

O,N-O, N-

/y/ y

V-NH2 V-NH 2

O1N —O 1 N -

O, NO, N

COOCH,COOCH,

NH,NH,

O, NO, N

I arbton auf Poi\esterI arbton on poi \ ester

GeiborangeGeiborange

GelboranueYellow orange

GeiborangeGeiborange

GeiborangeGeiborange

GelborangeYellow orange

GelborangeYellow orange

GelborangeYellow orange

Claims (1)

Pak ntansprüehe:Package claims: 1. Dispersionsfarbstoffe der Aminopy ra/olreihe der allgemeinen Formel1. Disperse dyes of the aminopyra / ol series the general formula O1NO 1 N -N-N-N-N H, NH, N 1!1! und Y die im Anspruch ! angegebenen Bed;: Iungen haben.and Y those in the claim! specified Bed ;: Have boys. ;~ Vei werdung der Farbstoffe der im Ansprud aiiüeüchenen Formel /um Farben von Tev.
material aus polyestern.; ~ Avoidance of the dyes of the formula, which is aiiüeächenen in the claim, / around the colors of Tev.
material made of polyesters.
DE19691940685 1969-08-09 1969-08-09 Disperse dyes of the amino pyrazole series, process for their manufacture and use Expired DE1940685C3 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE754401D BE754401A (en) 1969-08-09 AMINOPYRAZOLIC SERIES DISPERSED DYES
DE19691940685 DE1940685C3 (en) 1969-08-09 1969-08-09 Disperse dyes of the amino pyrazole series, process for their manufacture and use
CH406873A CH553840A (en) 1969-08-09 1970-07-16 PROCESS FOR THE PREPARATION OF DISPERSION DYES OF THE AMINOPYRAZOLE SERIES.
FR7027978A FR2057082B1 (en) 1969-08-09 1970-07-29
GB3817870A GB1310564A (en) 1969-08-09 1970-08-07 Disperse dyes of the aminopyrazole series
JP6934370A JPS4812403B1 (en) 1969-08-09 1970-08-10

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19691940685 DE1940685C3 (en) 1969-08-09 1969-08-09 Disperse dyes of the amino pyrazole series, process for their manufacture and use

Publications (3)

Publication Number Publication Date
DE1940685A1 DE1940685A1 (en) 1971-02-18
DE1940685B2 true DE1940685B2 (en) 1973-04-05
DE1940685C3 DE1940685C3 (en) 1973-10-31

Family

ID=5742437

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19691940685 Expired DE1940685C3 (en) 1969-08-09 1969-08-09 Disperse dyes of the amino pyrazole series, process for their manufacture and use

Country Status (6)

Country Link
JP (1) JPS4812403B1 (en)
BE (1) BE754401A (en)
CH (1) CH553840A (en)
DE (1) DE1940685C3 (en)
FR (1) FR2057082B1 (en)
GB (1) GB1310564A (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5145511U (en) * 1974-10-02 1976-04-03
JPS5148510U (en) * 1974-10-08 1976-04-12
JPS5297310U (en) * 1976-01-20 1977-07-21
JPS5297309U (en) * 1976-01-20 1977-07-21
JPS53120029U (en) * 1977-03-02 1978-09-25
JPS5654387Y2 (en) * 1977-03-07 1981-12-18
JPS5843657Y2 (en) * 1977-12-21 1983-10-03 ヤンマーディーゼル株式会社 Internal combustion engine intake system
JPS61185616U (en) * 1985-05-13 1986-11-19

Also Published As

Publication number Publication date
BE754401A (en) 1971-02-04
JPS4812403B1 (en) 1973-04-20
DE1940685C3 (en) 1973-10-31
FR2057082A1 (en) 1971-05-07
FR2057082B1 (en) 1974-07-12
GB1310564A (en) 1973-03-21
DE1940685A1 (en) 1971-02-18
CH553840A (en) 1974-09-13

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Legal Events

Date Code Title Description
C3 Grant after two publication steps (3rd publication)
E77 Valid patent as to the heymanns-index 1977
EHV Ceased/renunciation