DE1131639B - Process for dyeing and printing shaped structures made of linear aromatic polyesters, in particular polyethylene terephthalates, or of polyamides - Google Patents

Process for dyeing and printing shaped structures made of linear aromatic polyesters, in particular polyethylene terephthalates, or of polyamides

Info

Publication number
DE1131639B
DE1131639B DEF30026A DEF0030026A DE1131639B DE 1131639 B DE1131639 B DE 1131639B DE F30026 A DEF30026 A DE F30026A DE F0030026 A DEF0030026 A DE F0030026A DE 1131639 B DE1131639 B DE 1131639B
Authority
DE
Germany
Prior art keywords
dyeing
polyamides
aromatic polyesters
shaped structures
structures made
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
DEF30026A
Other languages
German (de)
Inventor
Dr Rudolf Kuehne
Dr Helmut Lindner
Dr Wilhelm Happe
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 DEF30026A priority Critical patent/DE1131639B/en
Priority to GB4161760A priority patent/GB917611A/en
Priority to CH1364860A priority patent/CH366026A/en
Priority to BE597953A priority patent/BE597953A/en
Publication of DE1131639B publication Critical patent/DE1131639B/en
Pending legal-status Critical Current

Links

Classifications

    • 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
    • D06P1/00General 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
    • D06P1/16General 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
    • D06P1/18Azo 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
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/10Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/18Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
    • C09B29/20Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
    • 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)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

Es wurde gefunden, daß man echte rotorange Färbungen und Drucke auf geformten Gebilden, wie Fasern, Geweben oder Folien, aus linearen aromatischen Polyestern, insbesondere Polyäthylenterephthalaten, oder aus Polyamiden erhält, wenn man diese Gebilde mit einer wäßrigen Dispersion des Farbstoffes der nachstehenden FormelIt has been found that real red-orange dyeings and prints on shaped structures such as Fibers, fabrics or films, made of linear aromatic polyesters, in particular polyethylene terephthalates, or obtained from polyamides when these structures are mixed with an aqueous dispersion of the dye the formula below

Verfahren zum Färben und Bedrucken
von geformten Gebilden aus linearen
Method of dyeing and printing
of shaped structures made of linear

aromatischen Polyestern,aromatic polyesters,

insbesondere Polyäthylenterephthalaten,in particular polyethylene terephthalates,

oder aus Polyamidenor from polyamides

N=N ■/ N = N ■ /

OH CO-NH-OH CO-NH-

OCH, Anmelder:OCH, applicant:

Farbwerke Hoechst AktiengesellschaftFarbwerke Hoechst Aktiengesellschaft

vormals Meister Lucius & Brüning,formerly Master Lucius & Brüning,

Frankfurt/M., Brüningstr. 45Frankfurt / M., Brüningstr. 45

behandelt.treated.

Das Färben der genannten Gebilde aus linearen aromatischen Polyestern erfolgt zweckmäßig in Gegenwart oder Abwesenheit von Carriern bei Temperaturen zwischen etwa 95 und 1050C, vorzugsweise von etwa 1000C, oder nach dem Hochtemperaturverfahren in Abwesenheit von Carriern bei Temperaturen zwischen etwa 120 und 1400C, vorzugsweise zwischen etwa 125 und 13O0C, während man beim Drucken die bedruckte Ware zweckmäßig kurzfristig einer trockenen Hitzebehandlung bei höheren Temperaturen, beispielsweise bei etwa 2000C, unterwirft.The said structures made of linear aromatic polyesters are appropriately colored in the presence or absence of carriers at temperatures between about 95 and 105 ° C., preferably of about 100 ° C., or by the high-temperature process in the absence of carriers at temperatures between about 120 and 140 ° C, preferably between about 125 and 13O 0 C, while during printing the printed product useful for shipping a dry heat treatment at higher temperatures, for example at about 200 0 C, is subjected.

Der genannte Farbstoff besitzt bei den vorstehend beschriebenen Färbebedingungen ein gutes Ziehvermögen auf den genannten Gebilden aus linearen aromatischen Polyestern, und die damit erzielten Färbungen und Drucke zeichnen sich durch eine gute Lichtechtheit aus.The aforesaid dye has good drawability under the dyeing conditions described above on the said structures made of linear aromatic polyesters, and the colorations achieved with them and prints are characterized by good lightfastness.

Während sich beim Färben bei dem genannten tieferen Temperaturbereich in Gegenwart von Carriern und beim genannten höheren Temperaturbereich in Abwesenheit von Carriern farbtiefe echte Färbungen erzielen lassen, erhält man beim Arbeiten bei dem genannten tieferen Temperaturbereich in Abwesenheit von Carriern ebenfalls einen echten, aber helleren Farbton, der je nach Verwendungszweck des Färbegutes als Pastellton sehr geschätzt ist.While dyeing at the lower temperature range mentioned in the presence of carriers and at the higher temperature range mentioned, in the absence of carriers, depth of color and true colorations can be achieved when working at the lower temperature range mentioned in the absence from carriers also a real, but lighter shade, depending on the intended use of the dyed material is much appreciated as a pastel shade.

Der verfahrensgemäß zur Anwendung gelangende Farbstoff zeichnet sich gegenüber den aus der französischen Patentschrift 1 187 252 bekannten Farbstoffen ähnlicher Struktur, die jedoch eine Alkoxygruppe in o-Stellung zur Carbonsäureamidbindung im Arylidrest aufweisen, durch eine bessere Lichtechtheit der Färbung aus.The dye used according to the process differs from that used in the French Patent specification 1 187 252 known dyes of similar structure, but which have an alkoxy group in have o-position to the carboxamide bond in the arylide residue, due to better lightfastness of the Coloring off.

Dr. Rudolf Kühne, Frankfurt/M.-Unterliederbach,Dr. Rudolf Kühne, Frankfurt / M.-Unterliederbach,

Dr. Helmut Lindner, Frankfurt/M.-Sindlingen,Dr. Helmut Lindner, Frankfurt / M.-Sindlingen,

und Dr. Wilhelm Happe, Schwalbach (Taunus),and Dr. Wilhelm Happe, Schwalbach (Taunus),

sind als Erfinder genannt wordenhave been named as inventors

In der französischen Patentschrift 1164365 sind zum Färben von Polyesterfasern Farbstoffe offenbart, die sich von dem verfahrensgemäß zur Anwendung gelangenden Farbstoff dadurch unterscheiden, daß der Benzolkern des Anilidrestes durch eine Methylgruppe und bzw. oder durch ein Chloratom substituiert ist. Diese Farbstoffe zeigen jedoch ein schlechteres Ziehvermögen auf Polyesterfasern, und damit hergestellte Färbungen weisen eine verminderte Lichtechtheit auf.In the French patent 1164365 dyes are disclosed for dyeing polyester fibers, the differ from the dye used according to the process in that the Benzene nucleus of the anilide residue is substituted by a methyl group and / or by a chlorine atom. However, these dyes show poor drawability on polyester fibers and those produced therewith Dyeings show a reduced lightfastness.

Aus der französischen Patentschrift 667167 ist ein Verfahren zum Färben von Materialien aus Acetylcellulose bekannt, wobei eine Dispersion eines Arylids der 2,3-Oxynaphthoesäure entweder (a) allein oder(b) zusammen mit einem Amin angewandt wird und anschließend (im Falle b) auf dem zu färbenden Material diazotiert wird oder (im Falle a) das mit der Azokomponente behandelte Material mit einer Diazoverbindung behandelt wird. Ein derartiges Verfahren ist zum Färben von Polyestermaterialien ungeeignet.From the French patent specification 667167 there is a method for coloring materials made of acetyl cellulose known, wherein a dispersion of an arylide of 2,3-oxynaphthoic acid either (a) alone or (b) is applied together with an amine and then (in case b) on the material to be colored is diazotized or (in case a) the material treated with the azo component with a diazo compound is treated. Such a process is unsuitable for dyeing polyester materials.

Beispiel 1example 1

5 g Polyäthylenterephthalatfasern in Form eines Gewirkes werden 1 Stunde bei 1200C in einem Bad5 g of polyethylene terephthalate fibers in the form of a knitted fabric 1 hour at 120 0 C in a bath

209 610/350209 610/350

gefärbt, das 1 Gewichtsprozent des feindispergierten Farbstoffes der Formelcolored, which is 1 percent by weight of the finely dispersed dye of the formula

OH CO NH-/OH CO NH- /

OCH3 OCH 3

(erhältlich durch Kuppeln von diazotierteni Anilin mit N-[2'-Oxy-3'-naphthoyl]-4-methoxyanilin) in 200 ml Wasser enthält. Die erhaltene Orangefärbung wird zur Verbesserung der Reibechtheit mit 2 g Natriumdithionit, 2 ml Natronlauge (380Be) sowie 1 g eines nicbtionogenen Waschmittels (Polyglykoläther) im Liter 15 Minuten bei 9O0C nachbehandelt. Die erhaltene Orangefärbung besitzt gute Echtheitseigenschaften.(obtainable by coupling diazotized aniline with N- [2'-oxy-3'-naphthoyl] -4-methoxyaniline) in 200 ml of water. The orange color is obtained (38 0 Be) and 1 g of nicbtionogenen detergent (polyglycol ether) per liter for 15 minutes at 9O 0 C post-treated to improve the fastness to rubbing with 2 g of sodium dithionite, 2 ml of sodium hydroxide solution. The orange dyeing obtained has good fastness properties.

Beispiel 2Example 2

25 g Polyäthylenterephthalatgewebe werden mit einer Druckpaste bedruckt, die 50 g des im Beispiel 1 genannten Farbstoffes, 200 g Nafkagummi, 50 g Naphtholdiglykoläther und 700 g Wasser im Kilogramm enthält. Nach dem Trocknen wird 30 Sekunden bei 2000C fixiert und schließlich gemäß Beispiel 1 reduktiv nachbehandelt. Man erhält einen orangefarbenen Druck von guten Echtheitseigenschaften.25 g of polyethylene terephthalate fabric are printed with a printing paste containing 50 g of the dye mentioned in Example 1, 200 g of Nafka gum, 50 g of naphthol diglycol ether and 700 g of water per kilogram. After drying, it is fixed at 200 ° C. for 30 seconds and finally after-treated reductively according to Example 1. An orange-colored print with good fastness properties is obtained.

Beispiel 3Example 3

5 g eines Gewebes aus polymeren! ε-Caprolactam werden im Flottenverhältnis 1 :40 in einem Bad gefärbt, das 2 Gewichtsprozent des feindispergierten Farbstoffes der im Beispiel 1 genannten Formel enthält. Man färbt 1 Stunde bei 100° C und spült anschließend bei 600C. Die so erhaltene Färbung besitzt gute Echtheitseigenschaften.5 g of a fabric made of polymer! ε-caprolactam are dyed in a liquor ratio of 1:40 in a bath which contains 2 percent by weight of the finely dispersed dye of the formula mentioned in Example 1. Dyeing 1 hour at 100 ° C and then rinsed at 60 0 C. The dyeing thus obtained has excellent fastness properties.

Claims (1)

PATENTANSPRUCH:PATENT CLAIM: Verfahren zum Färben und Bedrucken von geformten Gebilden aus linearen aromatischen Polyestern, insbesondere Polyäthylenterephthalaten, oder aus Polyamiden, dadurch gekennzeichnet, daß man diese mit einer wäßrigen Dispersion des Farbstoffes der FormelProcess for dyeing and printing shaped structures made of linear aromatic polyesters, in particular polyethylene terephthalates, or of polyamides, characterized in that they are mixed with an aqueous dispersion of the dye of the formula \ N=N\ N = N behandelt.treated. OH CO-NH-OH CO-NH- OCH»OCH » In Betracht gezogene Druckschriften:
Französische Patentschriften Nr. 667 167, 1 164 365.
Considered publications:
French patents nos. 667 167, 1 164 365.
DEF30026A 1959-12-08 1959-12-08 Process for dyeing and printing shaped structures made of linear aromatic polyesters, in particular polyethylene terephthalates, or of polyamides Pending DE1131639B (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DEF30026A DE1131639B (en) 1959-12-08 1959-12-08 Process for dyeing and printing shaped structures made of linear aromatic polyesters, in particular polyethylene terephthalates, or of polyamides
GB4161760A GB917611A (en) 1959-12-08 1960-12-02 Process for dyeing or printing shaped structures of linear aromatic polyesters or polyamides
CH1364860A CH366026A (en) 1959-12-08 1960-12-06 Process for dyeing and printing textile structures made of linear aromatic polyesters, in particular polyethylene terephthalates, or of polyamides
BE597953A BE597953A (en) 1959-12-08 1960-12-08 A process for producing dyes and prints for articles made from linear aromatic polyesters, more particularly from polymers of ethylene glycol terephthalate, or from polyamides.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF30026A DE1131639B (en) 1959-12-08 1959-12-08 Process for dyeing and printing shaped structures made of linear aromatic polyesters, in particular polyethylene terephthalates, or of polyamides

Publications (1)

Publication Number Publication Date
DE1131639B true DE1131639B (en) 1962-06-20

Family

ID=7093569

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF30026A Pending DE1131639B (en) 1959-12-08 1959-12-08 Process for dyeing and printing shaped structures made of linear aromatic polyesters, in particular polyethylene terephthalates, or of polyamides

Country Status (4)

Country Link
BE (1) BE597953A (en)
CH (1) CH366026A (en)
DE (1) DE1131639B (en)
GB (1) GB917611A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3445930A1 (en) * 1984-12-17 1986-06-26 Cassella Ag, 6000 Frankfurt DYE MIXTURES, METHOD FOR THEIR PRODUCTION AND METHOD FOR COLORING AND PRINTING HYDROPHOBIC FIBER MATERIALS

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1164365A (en) * 1957-01-05 1958-10-08 Cfmc New process for coloring polyester fibers

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1164365A (en) * 1957-01-05 1958-10-08 Cfmc New process for coloring polyester fibers

Also Published As

Publication number Publication date
GB917611A (en) 1963-02-06
BE597953A (en) 1961-06-08
CH366026A (en) 1963-01-31
CH1364860A4 (en) 1962-06-30

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