DE1519501A1 - Process for dyeing or printing polyester fiber material - Google Patents

Process for dyeing or printing polyester fiber material

Info

Publication number
DE1519501A1
DE1519501A1 DE19601519501 DE1519501A DE1519501A1 DE 1519501 A1 DE1519501 A1 DE 1519501A1 DE 19601519501 DE19601519501 DE 19601519501 DE 1519501 A DE1519501 A DE 1519501A DE 1519501 A1 DE1519501 A1 DE 1519501A1
Authority
DE
Germany
Prior art keywords
parts
dyeing
molecular weight
low molecular
polyester fiber
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
Application number
DE19601519501
Other languages
German (de)
Inventor
Mueller Dr Curt
Lerch Dipl-Chem Urs
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.)
Sandoz AG
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
Publication of DE1519501A1 publication Critical patent/DE1519501A1/en
Pending legal-status Critical Current

Links

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
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/06Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08Amino benzenes
    • 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
    • C09B43/00Preparation of azo dyes from other azo compounds
    • C09B43/18Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
    • C09B43/20Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with monocarboxylic acids, carbamic acid esters or halides, mono- isocyanates or haloformic acid esters
    • C09B43/202Aliphatic, cycloaliphatic, araliphatic carboxylic acids
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • D06P3/54Polyesters using dispersed dyestuffs

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Description

PatentanwältePatent attorneys

Dr. W. Schalk, DipUng. P. Wir*Dr. W. Schalk, DipUng. P. We *

Di-l.-lng. G. DannenbergDi-l.-lng. G. Dannenberg

D.. V. Schmied-KowarzikD. V. Schmied-Kowarzik

Dr. ?. Weinhold, Dr. D. GüdelDr. ?. Weinhold, Dr. D. Güdel Frankfurt/M,, Gr. E*ch«nh*im»r Str. 39 Frankfurt / M ,, Gr. E * ch «nh * im» r Str. 39

P 15 19 501.4 Oase 1187/A P 15 19 501.4 Oase 1187 / A

SANDOZ AG Basel /SchweizSANDOZ AG Basel, Switzerland

Verfahren zum Färben oder Bedrucken von Polyesterfasermaterial Es wurde gefunden, dass man sehr "wertvolle Färbungen oder Drucke auf Fasern und daraus hergestellten Textilraaterialien aus Polyestern vorzugsweise linearen, aromatischen Polyestern erhält, wenn'man Process for dyeing or printing polyester fiber material It has been found that very "valuable dyeings or prints are obtained on fibers and textile materials made from polyesters, preferably linear, aromatic polyesters, if

diese mit Farbstoffen der Formelthese with dyes of the formula

Z ·Z

(I)(I)

Vi or in X Wasserstoff oder Cyan, Y 'niedrigraolekulares Acylamino, Z niedrigmolekulares Alkoxy, R-. niedrigraolekulares AcyloxyalkylVi or in X hydrogen or cyano, Y 'low molecular weight acylamino, Z low molecular weight alkoxy, R-. low molecular weight acyloxyalkyl

und R2- niedrigmolekulares Acyloxyalkyl bedeuten.and R 2 - mean low molecular weight acyloxyalkyl.

OQ 9 8 A 1 / 1 7 26 NeueUnteifagenjArf,,",^· ,. OQ 9 8 A 1/1 7 26 NeueUnteifagenjArf ,, ", ^ ·,.

BADBATH

Das Färben erfolgt nach an sich bekannten Methoden, z.B. in Gegenwart von Carriern bei 80 bis ca. 1000C oder in Abwesenheit von Car.riern, unter Druck bei 100 bis I2IO0C, wobei in beiden Fällen der Zusatz von Dispersionsmitteln von Vorteil sein kann; Das Bedrucken erfolgt vorzugsweise in Gegenwart geeigneter Verdickungsmittel, z;B. Alginate, Britischgummi, Gummi Arabicum, Hydroxyäthylcellulose, Carboxymethylcellulose, Polyacrylamide oder Polyvinylalkohol j die Drucke werden meist durch trockene Hitze oder Dampfbehandlung fixiert.The dyeing is carried out according to known methods, for example in the presence of carriers at 80 to 100 0 C or in the absence of Car.riern, under pressure at 100 to IO I 2 0 C, in both cases, the addition of dispersing agents of Can be an advantage; Printing is preferably carried out in the presence of suitable thickeners, e.g. Alginates, British gum, gum arabic, hydroxyethyl cellulose, carboxymethyl cellulose, polyacrylamides or polyvinyl alcohol j the prints are usually fixed by dry heat or steam treatment.

Unter linearen, aromatischen Polyestern sind hauptsächlich die Polykondensationsprodukte aus Terephthalsäure und Aethylenglykol zu verstehen.The main linear, aromatic polyesters are the polycondensation products of terephthalic acid and ethylene glycol to understand.

Die Farbstoffe werden meist vor Ihrer Verwendung zu Färbe-Präparaten verarbeitet, dazu kann beispielsweise der getrocknete Farbstoff mit ei nem Dispergiermittel, gegebenenfalls in Gegenwart von Füllmitteln, gemahlen oder in Pastenform mit einem Dispergiermittel geknetet und hierauf im Vakuum oder durch Zerstäuben getrocknet werden. ·The dyes are mostly turned into coloring preparations before they are used processed, for example, the dried dye with a dispersant, optionally in the presence of fillers, ground or in paste form with a The dispersant is kneaded and then dried in vacuo or by atomization. ·

Die erhaltenen Färbungen zeichnen sich durch sehr gute Echtheiten', Insbesondere gute Licht-, Wasch-, Schweiss-, Meerwasser-, Rauchgas-, Sublimier-, Plissier-, Dämpf- und Bügelechtheit aus. Beim ' Färben von Mischgeweben werden Wolle , Baumwolle und Viskose gut reserviert.The dyeings obtained are characterized by very good fastness properties', In particular, good light, washing, perspiration, sea water, smoke gas, sublimation, pleating, steaming and ironing fastness. At the 'Wool, cotton, and viscose are good at dyeing blended fabrics reserved.

0 0 9 8 4 1/17 2 6 - BAD ORIGINAL0 0 9 8 4 1/17 2 6 - BAD ORIGINAL

Iia folgenden.Beispiel sind unter Teilen Gewichtsteile und unter. Prozenten Gewichtsprozente zu verstehen. Die Temperaturen sind in Celsiüsgraden angegeben.In the following example, parts are parts by weight and below. Percentages to understand percentages by weight. The temperatures are given in degrees Celsius.

Beispiel ·· Example ··

7 Teile des Farbstoffs der Formel ^,^-Dinitro-S'-acetylamino- '■.7 parts of the dye of the formula ^, ^ - Dinitro-S'-acetylamino- '■.

V-diaoetoxyäthyl-S'-äthoxy-l^l'-azobenzol werden mit 4 Teilen D inaphthylmethandi sulfonsäuren! Natrium, 4 Teilen Natriumcetyl-V-diaoetoxyäthyl-S'-ethoxy-l ^ l'-azobenzene are with 4 parts D inaphthylmethanedisulphonic acids! Sodium, 4 parts sodium cetyl

sulfat und 5 Teilen Natriumsulfat in einer Kugelmühle 48 Stunden " zu einem feinen Pulver gemahlen.sulfate and 5 parts of sodium sulfate in a ball mill for 48 hours " ground to a fine powder.

2 Teile des so erhaltenen Färbepräparates werden in 3000 Teilen2 parts of the dye preparation thus obtained are in 3000 parts

Wasser, welches 3 Teile einer BO^igen Lösung eines hochsulfonierten-Ricinusöls und 20 Teile einer Emulsion eines chlorierten Benzols enthält, dispergiert. Bei 2Ö-25Q bringt man 100 Teile Polyesterfasergewebe "Dacron" (eingetragene *Marke) ein, erhitzt das Bad in etwa 30 Minuten auf 95-100° und färbt 1 Stunde bei 95-100° . Das Färbegut wird aus dem 3ad genommen, gespült, 15.Minuten'"bei 70° mit einer 0,l#igen lösung eines Alkylphenylpolyglykoläthers geseift, nochmals gespüly und·getrocknet. Man erhält eine blaue Färbung mit ausgezeichneten Echtheiten.Water, which contains 3 parts of a BO ^ solution of a highly sulfonated castor oil and 20 parts of an emulsion of a chlorinated benzene, dispersed. 100 parts of polyester fiber fabric "Dacron" (registered * trademark) are put in at 20-25 Q , the bath is heated to 95-100 ° in about 30 minutes and dyed at 95-100 ° for 1 hour. The material to be dyed is removed from the 3ad, rinsed, soaped for 15 minutes at 70 ° with a 0.1 solution of an alkylphenyl polyglycol ether, rinsed again and dried. A blue dyeing with excellent fastness properties is obtained.

Der verwendete Farbstoff wird, folgendermassen hergestellt: Zu 105 Teilen Schwefelsäure (9o£ig) fügt man langsam bei 60-70° unter Rühren 6,9 Teile fein pulverisiertes, wasserfreies Xa^riumnitrit. Die klare Lösung wird auf 10-15° gekühlt und bei r.aximal 20° mit 100 Teilen Eisessig versetzt. Anschließend werden 1.3,5 Teile 2,4-DinitroanilinnU^4_d£saca ^LDO, Teile Eisessig zu'ge~e'ben.The dye used is prepared as follows: 6.9 parts of finely powdered, anhydrous xa ^ rium nitrite are slowly added to 105 parts of sulfuric acid (90 °) at 60 ° -70 ° with stirring. The clear solution is cooled to 10-15 ° and 100 parts of glacial acetic acid are added at a maximum of 20 °. Subsequently 1.3,5 parts of 2,4-dinitroaniline n U ^ 4_d £ ^ saca LDO, parts are e'ben zu'ge glacial acetic acid ~.

BAD ORIGINALBATH ORIGINAL

Man rührt 2 Stunden bei 15-20° und zerstört dann das überschüssige Nitrit durch Zugabe von 5 Teilen Harnstoff. Die so hergestellte "Diazoniumsalzlösung wird zu einem Gemisch aus 37 Teilen 3-Di-. acetoxyäthylamino-^-äthoxy-acetanilid, die in 200 Teilen Eisessig gelöst sind, und 100 Teilen Eis gegeben. Die Temperatur· von wird durch Zugabe, von Eis aufrechterhalten. Nach kurzer Zeit wird filtriert, mit Wasser säurefrei gewaschen und getrocknet. Das dunkelblaue Pulver schmilzt bei 158-101° und nach einmaligem Umkristallisieren aus einem Gemisch aus Alkohol und Aceton beiThe mixture is stirred for 2 hours at 15-20 ° and then the excess nitrite destroyed by addition of 5 parts of urea. The diazonium salt solution prepared in this way is added to a mixture of 37 parts of 3-di-. Acetoxyethylamino- ^ - ethoxyacetanilide, which are dissolved in 200 parts of glacial acetic acid, and 100 parts of ice. The temperature is maintained by adding ice After a short time it is filtered, washed acid-free with water and dried. The dark blue powder melts at 158-101 ° and after recrystallizing once from a mixture of alcohol and acetone

Ιββ-1βδ° .Ιββ-1βδ °.

Mit dem Farbstoff der Formel 2,it--Dinitro-2'-acetylamino-'ii f-diacetoxyäthyl-5'-methoxy-l,l'-azobenzol erhält man,-wenn dieser gemäss. dem obigen Beispiel auf Polyestermaterial ausgefärbt wird, grünstichig blaue Färbungen mit ausgezeichneten Echtheitseigen- schäften. . .With the dye of the formula 2, i t - dinitro-2'-acetylamino- ' i i f -diacetoxyethyl-5'-methoxy-l, l'-azobenzene is obtained - if this according to. the above example is dyed on polyester material, greenish blue dyeings with excellent fastness properties. . .

00 98 41/17 2 6 ' bad00 98 41/17 2 6 'bathroom

Claims (2)

PatentansprücheClaims 1. Verfahren zum Färben oder Bedrucken von Fasern oder daraus her-. gestellten Textilrriäterlallenaus Polyestern, vorzugsweise aus linearen, aromatischen Polyestern, dadurch gekennzeichnet, dass man Farbstoffe der Formel1. Process for dyeing or printing fibers or from them. made of polyester, preferably made of linear, aromatic polyesters, characterized in that there are dyes of the formula NO2 NO 2 (I)(I) verwendet,used, worin X Wasserstoff oder Cyan, Y niedrigmolekulares Acylamino/where X is hydrogen or cyano, Y low molecular weight acylamino / Z niedrigmolekulares Alkoxy, und Rt niedrigmolekulares Acyloxyalkyl und R niedrigmolekulares Acyloxyalkyl bedeuten.Z low molecular weight alkoxy, and Rt low molecular weight acyloxyalkyl and R is low molecular weight acyloxyalkyl. 2. Das gemäss Patentanspruch 1 gefärbte oder bedruckte Material.2. The material dyed or printed according to claim 1. Neue Untertagen ^u^a*i ·*3 New underground ^ u ^ a * i * 3 ' BAD' BATH 009841/172 6009841/172 6
DE19601519501 1959-07-01 1960-06-24 Process for dyeing or printing polyester fiber material Pending DE1519501A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH7516559 1959-07-01

Publications (1)

Publication Number Publication Date
DE1519501A1 true DE1519501A1 (en) 1970-10-08

Family

ID=4533943

Family Applications (2)

Application Number Title Priority Date Filing Date
DE19601419879 Pending DE1419879A1 (en) 1959-07-01 1960-06-24 Process for dyeing or printing polyester fiber material
DE19601519501 Pending DE1519501A1 (en) 1959-07-01 1960-06-24 Process for dyeing or printing polyester fiber material

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DE19601419879 Pending DE1419879A1 (en) 1959-07-01 1960-06-24 Process for dyeing or printing polyester fiber material

Country Status (2)

Country Link
DE (2) DE1419879A1 (en)
GB (1) GB952468A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3840065A1 (en) * 1988-11-28 1990-05-31 Cassella Ag MONOAZO DYES, THEIR PRODUCTION AND USE
KR101118496B1 (en) * 2003-09-25 2012-03-12 다이스타 텍스틸파르벤 게엠베하 운트 콤파니 도이칠란트 카게 Adsorbable organic halogen aox - free navy and black disperse dyes

Also Published As

Publication number Publication date
DE1419879A1 (en) 1969-04-24
GB952468A (en) 1964-03-18

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Legal Events

Date Code Title Description
E77 Valid patent as to the heymanns-index 1977