CH532646A - Stabilized disazo dyes - contg polyalkyleneoxyamines useful for dyeing polymers, leather and paper - Google Patents

Stabilized disazo dyes - contg polyalkyleneoxyamines useful for dyeing polymers, leather and paper

Info

Publication number
CH532646A
CH532646A CH1197168A CH1197168A CH532646A CH 532646 A CH532646 A CH 532646A CH 1197168 A CH1197168 A CH 1197168A CH 1197168 A CH1197168 A CH 1197168A CH 532646 A CH532646 A CH 532646A
Authority
CH
Switzerland
Prior art keywords
formula
paper
stabilized
leather
useful
Prior art date
Application number
CH1197168A
Other languages
German (de)
Inventor
Frei Alfred
Schweizer August
Original Assignee
Sandoz 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 Sandoz Ag filed Critical Sandoz Ag
Priority to CH1197168A priority Critical patent/CH532646A/en
Priority to GB2433269A priority patent/GB1261583A/en
Priority to DE19691929418 priority patent/DE1929418C/en
Priority to ES69368290A priority patent/ES368290A1/en
Priority to BE734573D priority patent/BE734573A/xx
Priority to FR6919684A priority patent/FR2010904A1/fr
Publication of CH532646A publication Critical patent/CH532646A/en
Priority to US05/620,641 priority patent/US4083681A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing 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
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0072Preparations with anionic dyes or reactive dyes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B35/00Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02Disazo dyes
    • C09B35/039Disazo dyes characterised by the tetrazo component
    • C09B35/08Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
    • C09B35/20Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling compounds of different types
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00Complex metal compounds of azo dyes
    • C09B45/02Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/24Disazo or polyazo compounds

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Paper (AREA)
  • Coloring (AREA)

Abstract

Storage stable dye compsns. contain (a) dyes of formula (I): (where Me = Cu or Ni; Y = arylaminocarbonyl; Z = 1-4C alkyl, or Y and Z together form a naphthalene or heterocyclic ring; m = 1-3; n = 1 or 2, m + n = 3-5) and (b) cpds. of formula (II): (where R1, R2, R4 and R5 each independently = H, 1 - 3C alkyl or -R8-(O-R9)t-1-OH; E, (which may be different in each case) = 1 - 4 and the sum of the 4 t's = 4 - 30; R3 = 2 - 3C alkylene, R6, R7, R8 and R9 independently = 2 - 3C alkylene, p = 1 - 12, r and s each independently = 1 - 6, r+s = 2 - 7.). The dye compsns. are useful for dyeing wood, silk, polyamides, polyurethanes, leather, paper, and esp. natural and regenerated cellulosic fibres, and the dyeing have good fastness to light, washing, water etc.

Description

  

  
 



  Zusatzpatent zum Hauptpatent 499 607 Stabilisierte Farbstoffpräparate
Das Hauptpatent Nr. 499 607 beschreibt stabilisierte Farbstoffpräparate, welche mindestens einen Farbstoff der Formel
EMI1.1     
 und mindestens eine Verbindung der Formel
EMI1.2     
 enthalten, worin
Me ein Kupfer- oder Nickelatom,
Y einen Arylamino-carbonylrest,
Z einen niedrigmolekularen Alkylrest oder
Y und Z zusammen die zur Bildung eines Naphthalinringes oder eines heterocyclischen Ringes notwendigen Atome,
R1 Wasserstoff, einen Alkylrest mit 1 bis 3 Kohlenstoffatomen oder einen Rest der Formel  -R8-(O-R9)t-1-OH
R2 Wasserstoff, einen Alkylrest mit 1 bis 3 Kohlenstoffatomen oder einen Rest der Formel  -R8-(O-R9)u-1-OH,
R3 einen Alkylenrest mit 2 bis 3 Kohlenstoffatomen,
R4 Wasserstoff,

   einen Alkylrest mit 1 bis 3 Kohlenstoff    atomen oder einen Rest der Formel
R8(ORo)vi -OHs   
R5 Wasserstoff, einen Alkylrest mit 1 bis 3 Kohlenstoffatomen oder einen Rest der Formel  -R8-(O-Rg)w-1-OH,
R6, R7, R8 und   R9    unabhängig voneinander Alkylenreste mit 2 bis 3 Kohlenstoffatomen, m 1 bis 3, n 1 bis 2,  die Summe m + n 3 bis 5,    p 1 bis 12,    r und s unabhängig voneinander 1 bis 6, die Summe r und s 2 bis 7, t, u, v und w unabhängig voneinander 1 bis 14 und die Summe t+u+v+w 4 bis 30 bedeuten.



   Diese Farbstoffpräparate können in fester oder in flüssiger Form vorliegen. Die festen Präparate enthalten z. B. 10 bis 90 Gewichtsprozente, bzw. 50 bis 80 Gewichtsprozente, vorzugsweise 10 bzw. 15 oder vorteilhaft 30 bis 85 Gewichts prozente, aber auch 10-50 Gewichtsprozente, mindestens eines Farbstoffs der   Formel (1)    und 0,5 bis 20 Gewichtsprozente, vorzugsweise 0,5 bis 10 Gewichtsprozente oder 2 bis 10 Gewichtsprozente, aber auch 0,5 bis 1 Gewichtsprozent, mindestens einer Verbindung der Formel   (II).   



   Die flüssigen Präparate enthalten z. B. 5 bis 25   Gewichts-    prozente, vorzugsweise 5 bis 15 Gewichtsprozente, mindestens eines Farbstoffs der Formel   (1), 1    bis 20 Gewichtsprozente, vorzugsweise 2 bis 10 Gewichtsprozente, mindestens einer Verbindung der   Formel (11)    und 45 bis 92 Gewichtsprozente, vorzugsweise 70-90 Gewichtsprozente, Wasser. Daneben enthalten die Präparate anorganische Salze   (NaCI,    Na2SO4, Na2CO3, oder die entsprechenden Kaliumverbindungen), welche von der Herstellung der Farbstoffe herrühren und/oder im Falle der festen Präparate, als Stellmittel zugesetzt werden können; ferner können noch andere Zusätze anwesend sein, z. B.

  Alkali-, vorzugsweise Natriumligninsulfat, (Natriumsulfitcelluloseablauge), Alkali; vorzugsweise Natriummetaphosphat oder Gemische solcher Verbindungen, ferner z. B.   löslichkeitsfördernde    Produkte wie Harnstoff, Dextrin, die Alkalimetallsalze von Benzol-, Toluol-, Xylol- oder Naphthalinsulfonsäure, kalkfällende oder kalkkomplexverbindende Zusätze wie normale Phosphate, kondensierte Phosphate, Salze von Aminocarbonsäuren (nitrilotriessigsäure, Äthylendiamintetraessigsäure), anionische oberflächenaktive Verbindungen wie Salze der Diisopropyl oder   Di-butylnaphthalinsulfonsäure,    der Alkylbenzolsulfonsäuren oder der Di-naphthylmethandisulfonsäure, nichtiogene oberflächenaktive Verbindungen wie die wasserlöslichen Anlagerungsprodukte von Äthylenoxid an hydrophobe Verbindungen (Fettalkohole,

   Alkyl- oder Dialkylphenole, Fettsäureamide usw.) und auch deren Sulfate usw.



   Es wurde nun gefunden, dass stabilisierte Farbstoffpräparate, die ausser mindestens einem Farbstoff der   Formel (1)    und den Aminen der Formel (II) Alkalimetalligninsulfate, vorzugsweise Natriumligninsulfat enthalten, besonders wertvoll sind; insbesondere sind sie sehr lagerungsstabil und sehr gut löslich.



   Im folgenden Beispiel bedeuten die Teile Gewichtsteile und die Prozente Gewichtsprozente: die Temperaturen sind in Celsiusgraden angegeben.



  Beispiel
109 Teile des Disazofarbstoffes der Formel
EMI2.1     
 werden in Form einer salzhaltigen,   45%eigen    wässrigen Paste in ein Gemisch von 1200 Teilen entmineralisiertem Wasser von   40 ,    45 Teile   2-Amino-2'hydroxydiäthyl-äther    und 15 Teilen Natriumligninsulfat eingetragen und gelöst. Man behandelt die Farbstofflösung mit 5 Teilen Kieselgur und filtriert ab.

 

   Die so hergestellte flüssige Zubereitung ist bei Temperaturen bis zu   40     längere Zeit, z. B. mehrere Monate haltbar.



  Vorschrift zum Färben von Papier:
In einem Holländer werden 100 Teile chemisch gebleichte Sulfitcellulose in Gegenwart von Wasser gemahlen.



   Zu dieser Masse gibt man 10 Teile der Zubereitung gemäss Beispiel. Nach 15 Minuten erfolgt die Leimung und anschliessend dessen Fixierung.



   Das auf diese Weise hergestellte Papier besitzt eine grünstichig blaue Nuance von mittlerer Intensität. Die Färbung besitzt gute Echtheiten. Das Abwasser ist farblos.



   PATENTANSPRUCH 1
Stabilisierte Farbstoffpräparate nach dem Patentanspruch I des Hauptpatents 499 607, dadurch gekennzeichnet, dass sie Alkalimetalligninsulfate enthalten. 



  
 



  Additional patent to the main patent 499 607 Stabilized dye preparations
The main patent no. 499 607 describes stabilized dye preparations which contain at least one dye of the formula
EMI1.1
 and at least one compound of the formula
EMI1.2
 contain, in which
Me a copper or nickel atom,
Y is an arylamino-carbonyl radical,
Z is a low molecular weight alkyl radical or
Y and Z together are the atoms necessary to form a naphthalene ring or a heterocyclic ring,
R1 is hydrogen, an alkyl radical with 1 to 3 carbon atoms or a radical of the formula -R8- (O-R9) t-1-OH
R2 is hydrogen, an alkyl radical with 1 to 3 carbon atoms or a radical of the formula -R8- (O-R9) u-1-OH,
R3 is an alkylene radical with 2 to 3 carbon atoms,
R4 hydrogen,

   an alkyl radical having 1 to 3 carbon atoms or a radical of the formula
R8 (ORo) vi -OHs
R5 is hydrogen, an alkyl radical with 1 to 3 carbon atoms or a radical of the formula -R8- (O-Rg) w-1-OH,
R6, R7, R8 and R9 independently of one another are alkylene radicals with 2 to 3 carbon atoms, m 1 to 3, n 1 to 2, the sum m + n 3 to 5, p 1 to 12, r and s independently of one another 1 to 6, the Sum r and s are 2 to 7, t, u, v and w are independently 1 to 14 and the sum t + u + v + w is 4 to 30.



   These dye preparations can be in solid or liquid form. The solid preparations contain z. B. 10 to 90 percent by weight or 50 to 80 percent by weight, preferably 10 or 15 or advantageously 30 to 85 percent by weight, but also 10-50 percent by weight, at least one dye of the formula (1) and 0.5 to 20 percent by weight, preferably 0.5 to 10 percent by weight or 2 to 10 percent by weight, but also 0.5 to 1 percent by weight, of at least one compound of the formula (II).



   The liquid preparations contain z. B. 5 to 25 percent by weight, preferably 5 to 15 percent by weight, at least one dye of the formula (1), 1 to 20 percent by weight, preferably 2 to 10 percent by weight, at least one compound of the formula (11) and 45 to 92 percent by weight, preferably 70-90 percent by weight, water. In addition, the preparations contain inorganic salts (NaCl, Na2SO4, Na2CO3, or the corresponding potassium compounds), which originate from the manufacture of the dyes and / or, in the case of solid preparations, can be added as adjusting agents; furthermore, other additives may also be present, e.g. B.

  Alkali, preferably sodium lignin sulphate (sodium sulphite cellulose waste liquor), alkali; preferably sodium metaphosphate or mixtures of such compounds, further z. B. solubility-promoting products such as urea, dextrin, the alkali metal salts of benzene, toluene, xylene or naphthalenesulfonic acid, lime-precipitating or lime-complex-connecting additives such as normal phosphates, condensed phosphates, salts of aminocarboxylic acids, anionic di-acetic acid, anionic surface-acetic acid, ethylenediaminetetylic acid or di-butylnaphthalenesulfonic acid, alkylbenzenesulfonic acids or di-naphthylmethanedisulfonic acid, non-biogenic surface-active compounds such as the water-soluble addition products of ethylene oxide with hydrophobic compounds (fatty alcohols,

   Alkyl or dialkyl phenols, fatty acid amides etc.) and also their sulfates etc.



   It has now been found that stabilized dye preparations which, in addition to at least one dye of the formula (1) and the amines of the formula (II), contain alkali metal lignin sulfates, preferably sodium lignin sulfate, are particularly valuable; in particular, they are very stable in storage and very soluble.



   In the following example, the parts are parts by weight and the percentages are percentages by weight: the temperatures are given in degrees Celsius.



  example
109 parts of the disazo dye of the formula
EMI2.1
 are added and dissolved in the form of a salt-containing, 45% own aqueous paste in a mixture of 1200 parts of demineralized water of 40.45 parts of 2-amino-2'hydroxydiethyl ether and 15 parts of sodium lignosulfate. The dye solution is treated with 5 parts of kieselguhr and filtered off.

 

   The liquid preparation produced in this way is at temperatures up to 40 for a longer time, for. B. durable for several months.



  Instructions for coloring paper:
100 parts of chemically bleached sulfite cellulose are ground in a hollander in the presence of water.



   10 parts of the preparation according to the example are added to this mass. After 15 minutes, the glue is applied and then it is fixed.



   The paper produced in this way has a greenish blue shade of medium intensity. The dyeing has good fastness properties. The wastewater is colorless.



   PATENT CLAIM 1
Stabilized dye preparations according to claim I of main patent 499 607, characterized in that they contain alkali metal lignin sulfates.

 

Claims (1)

UNTERANSPRUCH SUBClaim Stabilisierte Farbstoffpräparate gemäss Patentanspruch 1, dadurch gekennzeichnet, dass sie Natriumligninsulfat enthalten. Stabilized dye preparations according to claim 1, characterized in that they contain sodium lignin sulfate. PATENTANSPRUCH 11 Verwendung der stabilisierten Farbstoffpräparate gemäss Patentanspruch I zum Färben von Papier. PATENT CLAIM 11 Use of the stabilized dye preparations according to patent claim I for dyeing paper.
CH1197168A 1968-06-14 1968-08-09 Stabilized disazo dyes - contg polyalkyleneoxyamines useful for dyeing polymers, leather and paper CH532646A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
CH1197168A CH532646A (en) 1968-06-14 1968-08-09 Stabilized disazo dyes - contg polyalkyleneoxyamines useful for dyeing polymers, leather and paper
GB2433269A GB1261583A (en) 1968-06-14 1969-05-13 Stabilized dye preparations
DE19691929418 DE1929418C (en) 1968-06-14 1969-06-10 Stabilized dye preparations
ES69368290A ES368290A1 (en) 1968-06-14 1969-06-12 Procedure for obtaining preparations of stabilized dyes. (Machine-translation by Google Translate, not legally binding)
BE734573D BE734573A (en) 1968-06-14 1969-06-13
FR6919684A FR2010904A1 (en) 1968-06-14 1969-06-13
US05/620,641 US4083681A (en) 1968-06-14 1975-10-08 Compositions of metal complexes of disazo acid dyes stabilized with amino ethers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH888768A CH499607A (en) 1968-06-14 1968-06-14 Stabilized dyes
CH1197168A CH532646A (en) 1968-06-14 1968-08-09 Stabilized disazo dyes - contg polyalkyleneoxyamines useful for dyeing polymers, leather and paper

Publications (1)

Publication Number Publication Date
CH532646A true CH532646A (en) 1973-01-15

Family

ID=4345864

Family Applications (2)

Application Number Title Priority Date Filing Date
CH888768A CH499607A (en) 1968-06-14 1968-06-14 Stabilized dyes
CH1197168A CH532646A (en) 1968-06-14 1968-08-09 Stabilized disazo dyes - contg polyalkyleneoxyamines useful for dyeing polymers, leather and paper

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CH888768A CH499607A (en) 1968-06-14 1968-06-14 Stabilized dyes

Country Status (2)

Country Link
BR (1) BR6909767D0 (en)
CH (2) CH499607A (en)

Also Published As

Publication number Publication date
CH499607A (en) 1970-11-30
BR6909767D0 (en) 1973-04-12

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