DE1040499B - Process for dyeing structures made of polyterephthalic acid glycol esters - Google Patents

Process for dyeing structures made of polyterephthalic acid glycol esters

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Publication number
DE1040499B
DE1040499B DEF21182A DEF0021182A DE1040499B DE 1040499 B DE1040499 B DE 1040499B DE F21182 A DEF21182 A DE F21182A DE F0021182 A DEF0021182 A DE F0021182A DE 1040499 B DE1040499 B DE 1040499B
Authority
DE
Germany
Prior art keywords
structures made
acid glycol
glycol esters
dyeing
polyterephthalic acid
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
DEF21182A
Other languages
German (de)
Inventor
Dr Winfried Kruckenberg
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Priority to DEF21182A priority Critical patent/DE1040499B/en
Publication of DE1040499B publication Critical patent/DE1040499B/en
Pending 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
    • 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
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters

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

Description

Verfahren zum Färben von Gebilden aus Polyterephthalsäureglycolestern Es wurde gefunden, daß man wertvolle Färbungen auf Gebilden aus Polyestern, wie Fäden, Bändern, Fasern und dergleichen, erhält, wenn man sulfonsäure- und carbonsäuregruppenfreie Azofarbstoffe der allgemeinen Zusammensetzung: R-N=N-Rl verwendet, worin R den Rest einer Diazokomponente der Benzol- oder Naphthalinreihe und R1 den Rest eines 1-Cyanalkyl-3-methyl-5-pyrazolons bedeuten.Process for dyeing structures made from polyterephthalic acid glycol esters It has been found that valuable dyeings on structures made of polyesters, such as Threads, ribbons, fibers and the like are obtained when sulfonic acid and carboxylic acid group-free Azo dyes of the general composition: R-N = N-Rl is used, where R is the remainder a diazo component of the benzene or naphthalene series and R1 is the remainder of a 1-cyanoalkyl-3-methyl-5-pyrazolone mean.

Die Farbstoffe der obenangegebenen allgemeinen Zusammensetzung können in bekannter Weise hergestellt werden, indem man diazotierte Amine der Benzol- oder Naphthalinreihe mit 1-Cyanalkyl-pyrazolonen kuppelt. Die hierfür eingesetzten Pyrazolonkupplungskomponenten sind leicht zugänglich, beispielsweise durch Anlagerung von Hydrazin an ungesättigte, aliphatische Nitrile, wie Acylnitril, Crotonnitril oder Allylcyanid, und Umsetzung der erhaltenen aliphatischen Hydrazine mit Acetessigester oder Diketen.The dyes of the general composition given above can be prepared in a known manner by diazotized amines of the benzene or Coupling naphthalene series with 1-cyanoalkyl-pyrazolones. The pyrazolone coupling components used for this purpose are easily accessible, for example by adding hydrazine to unsaturated, aliphatic nitriles such as acyl nitrile, croton nitrile or allyl cyanide, and reaction of the aliphatic hydrazines obtained with acetoacetic ester or diketene.

Die erfindungsgemäß zur Anwendung kommenden Monoazofarbstoffe zeigen ein gutes Ziehvermögen auf Polyterephthalsäureglycolesterfasern. Man erhält klare licht- und waschechte gelbe Färbungen, die sich durch eine gute Sublimierechtheit auszeichnen. Beispiel 1 15,1 Gewichtsteile p-Aminobenzoesäuremethylester (100°/oig) werden in 30 Gewichtsteilen 30°/oiger Salzsäure und 25 Gewichtsteilen Wasser angeschlämmt. Nach Zusatz von 85 Gewichtsteilen Eis wird mit einer Lösung aus 7 Gewichtsteilen Natriumnitrit und 20 Gewichtsteilen Wasser bei einer Temperatur unterhalb +5° C diazotiert. Die erhaltene Diazoniumsalzlösung wird langsam in einer Lösung von 15,1 Gewichtsteilen 1-(ß-Cyanäthyl)-3-methyl-5-pyrazolon in 22 Gewichtsteilen 40°/oiger Natronlauge, 220 Gewichtsteilen Wasser und 160 Gewichtsteilen Eis eingetragen. Der ausgefallene Farbstoff wird abgesaugt, mit Wasser gewaschen und getrocknet. Er bildet in trockenem Zustand ein gelbes Pulver, das sich in organischen Lösungsmitteln mit grünstichiggelber bis gelber Farbe löst.The monoazo dyes used according to the invention show good drawability on polyterephthalic acid glycol ester fibers. You get clear light and washfast yellow dyeings, which are characterized by good sublimation fastness distinguish. Example 1 15.1 parts by weight of methyl p-aminobenzoate (100%) are suspended in 30 parts by weight of 30% hydrochloric acid and 25 parts by weight of water. After adding 85 parts by weight of ice, a solution of 7 parts by weight is added Sodium nitrite and 20 parts by weight of water at a temperature below + 5 ° C diazotized. The resulting diazonium salt solution is slowly dissolved in a solution of 15.1 Parts by weight of 1- (β-cyanoethyl) -3-methyl-5-pyrazolone in 22 parts by weight of 40% Sodium hydroxide solution, 220 parts by weight of water and 160 parts by weight of ice entered. Of the precipitated dye is filtered off with suction, washed with water and dried. He educates when dry a yellow powder that dissolves in organic solvents greenish yellow to yellow color dissolves.

In ein Färbebad von 41, das 4 g eines emulgierend wirkenden Polyglykoläthers und 104 des gut dispergierten Farbstoffs (berechnet auf das Gewicht des Färbematerials) sowie 16 g eines Carriers, beispielsweise Benzoesäure, und 20 g Diammoniumphosphat enthält, werden 25 g Polyesterfasern bei 50° C eingebracht. Man treibt innerhalb 30 Minuten zum Kochen und färbt weiter 11/2 bis 2 Stunden bei dieser Temperatur. Die Färbung wird anschliessend 20 Minuten bei 70° C alkalisch nachgewaschen, gespült und getrocknet. Man erhält eine klare, grünstichiggelbe Färbung mit guten Echtheitseigenschaften.In a dye bath of 41, which contains 4 g of an emulsifying polyglycol ether and 104 of the well-dispersed dye (calculated on the weight of the dye material) as well as 16 g of a carrier, for example benzoic acid, and 20 g of diammonium phosphate, 25 g of polyester fibers are placed at 50 ° C brought in. It is brought to the boil within 30 minutes and dyeing is continued for 11/2 to 2 hours at this temperature. The dye is then washed alkaline at 70 ° C. for 20 minutes, rinsed and dried. A clear, greenish yellow dyeing with good fastness properties is obtained.

In gleicher Weise, wie in diesem Beispiel angegeben, können die in der folgenden Tabelle aufgeführten Farbstoffe auf Polyesterfasern gefärbt werden, wobei ebenfalls Färbungen in gelben Tönen mit guten Echtheitseigenschaften erhalten werden: Farbton der Färbung auf Farbstoffe Polyterephthal- säureglykolesterfaser ' @-N,N-CC-CH3 H- 2. @HO-C", N ' Stark rotstichiggelb N I CH,-CH,-CN Farbton der Färbung auf Farbstoffe Polvterephthal- säuregIvkolesterfaser C,H900C-< @-N=N-CC-CH3 3. NO2 HO- C, N Rotstichiggelb N CHZ-CHZ-CN OZN-@'/ @-N=N-CC-CH3 4. HOC N Gelb N.: Ci2-CHZ-CN COOC,Ha OZN-@ `-N=N-CC-CH3 5. HOC N Rotstichiggelb U"2-Ci,-CN OCH3 I @N=N-C-C-CH3 6' C O O C H3 HOC \ ,N Rotstichiggelb N I U"2-CHZ-CN NC@ \-N = N-CC-CH3 7. HOC N Gelb N ... I CH,-CHZ-CN In the same way as indicated in this example, the dyes listed in the table below can be dyed on polyester fibers, dyeing in yellow shades with good fastness properties also being obtained: Hue of the staining Dyes polyterephthalic acid glycol ester fiber '@ -N, N-CC-CH3 H- 2. @ HO-C ", N 'Strong reddish yellow N I. CH, - CH, -CN Hue of the staining Polvterephthalic dyes acid glycol ester fiber C, H900C- < @ -N = N-CC-CH3 3. NO2 HO- C, N reddish yellow N CHZ-CHZ-CN OZN - @ '/ @ -N = N-CC-CH3 4. HOC N yellow N .: C i2 -CHZ-CN COOC, Ha OZN- @ `-N = N-CC-CH3 5. HOC N reddish yellow U "2-Ci, -CN OCH3 I. @ N = NCC-CH3 6 'COOC H3 HOC \, N Reddish yellow N I. U "2 -CHZ-CN NC @ \ -N = N-CC-CH3 7. HOC N yellow N ... I. CH, -CHZ-CN

Claims (1)

PATENT ANSPSUCH: Verfahren zum Färben von Gebilden aus Polyterephthalsäureglycolestern, dadurch gekennzeichnet, daB man sulfonsäure- und carbonsäuregruppenfreie Monoazofarbstoffe der Zusammensetzung: R-N=N-Ri worin R einen Rest der Benzol- oder Naphthalinreihe und R1 den Rest eines 1-Cyanalkyl-3-methyl-5-pyrazolons bedeutet, verwendet. In Betracht gezogene Druckschriften Deutsche Patentschriften Nr. 731403, 842 089. PATENT APPLICATION: A process for dyeing structures made of polyterephthalic acid glycol esters, characterized in that monoazo dyes free of sulfonic acid and carboxylic acid groups and having the composition: RN = N-Ri where R is a residue of the benzene or naphthalene series and R1 is the residue of a 1-cyanoalkyl-3-methyl -5-pyrazolones means used. Considered publications German patent specifications No. 731 403, 842 089.
DEF21182A 1956-09-07 1956-09-07 Process for dyeing structures made of polyterephthalic acid glycol esters Pending DE1040499B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF21182A DE1040499B (en) 1956-09-07 1956-09-07 Process for dyeing structures made of polyterephthalic acid glycol esters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF21182A DE1040499B (en) 1956-09-07 1956-09-07 Process for dyeing structures made of polyterephthalic acid glycol esters

Publications (1)

Publication Number Publication Date
DE1040499B true DE1040499B (en) 1958-10-09

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ID=7089964

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF21182A Pending DE1040499B (en) 1956-09-07 1956-09-07 Process for dyeing structures made of polyterephthalic acid glycol esters

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1164973B (en) * 1958-12-09 1964-03-12 Bayer Ag Dyeing and printing of structures made from aromatic polyesters, polyamides, polyurethanes or from cellulose esters from aqueous dye baths or printing pastes

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE731403C (en) * 1941-01-18 1943-02-09 Ig Farbenindustrie Ag Process for dyeing vegetable fibers with disazo and trisazo dyes

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE731403C (en) * 1941-01-18 1943-02-09 Ig Farbenindustrie Ag Process for dyeing vegetable fibers with disazo and trisazo dyes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1164973B (en) * 1958-12-09 1964-03-12 Bayer Ag Dyeing and printing of structures made from aromatic polyesters, polyamides, polyurethanes or from cellulose esters from aqueous dye baths or printing pastes

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