DE1168862B - Process for dyeing and printing shaped structures made of aromatic polyesters, in particular polyethylene terephthalates - Google Patents

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

Info

Publication number
DE1168862B
DE1168862B DEF24023A DEF0024023A DE1168862B DE 1168862 B DE1168862 B DE 1168862B DE F24023 A DEF24023 A DE F24023A DE F0024023 A DEF0024023 A DE F0024023A DE 1168862 B DE1168862 B DE 1168862B
Authority
DE
Germany
Prior art keywords
dyeing
aromatic polyesters
polyethylene terephthalates
particular polyethylene
prints
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
DEF24023A
Other languages
German (de)
Inventor
Dr Norbert Ottawa
Kurt Roth
Dr Rudolf Weingarten
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
Priority to DENDAT1252168D priority Critical patent/DE1252168B/en
Application filed by Hoechst AG filed Critical Hoechst AG
Priority to DEF24023A priority patent/DE1168862B/en
Priority to GB3071658A priority patent/GB870680A/en
Priority to FR1202744D priority patent/FR1202744A/en
Publication of DE1168862B publication Critical patent/DE1168862B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • 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
    • C09B25/00—Quinophthalones
    • 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

Landscapes

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

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Internat. Kl.: D 06 ρBoarding school Class: D 06 ρ

Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:

Deutsche Kl.: 8m-1/01 German class: 8m-1/01

1168 862 F24023IVc/8m 25. September 1957 30. April 1964 1 168 862 F24023IVc / 8m September 25, 1957 April 30, 1964

Es ist bekannt, daß man geformte Gebilde aus aromatischen Polyestern mit den zum Färben von Acetatseide geeigneten Dispersionsfarbstoffen anfärben kann. In neuerer Zeit wurden auch andere Farbstoffgruppen ermittelt, die sich zum Färben von aromatischen Polyestern eignen.It is known that molded articles made of aromatic polyesters with the for dyeing of Acetate silk can dye suitable disperse dyes. In more recent times others have also been Determined dye groups that are suitable for dyeing aromatic polyesters.

Es wurde nun gefunden, daß man geformte Gebilde, wie Fasern, Fäden, Gewebe oder Folien aus aromatischen Polyestern, insbesondere Polyäthylenterephthalaten, vorteilhaft färben und bedrucken kann, wenn man sie mit wässerigen Dispersionen von durch Kondensation von Phthalsäureanhydrid mit Verbindungen mit aktivierter Methylgruppe erhaltenen Farbstoffen vom Chinophthal ri.yp, die die folgende allgemeine Zusammensetzung uaben:It has now been found that shaped structures such as fibers, threads, fabrics or films can be made from aromatic polyesters, especially polyethylene terephthalates, advantageously dye and print can, if you use them with aqueous dispersions by condensation of phthalic anhydride with Compounds with activated methyl group obtained dyes from the quinophthal ri.yp which the the following general composition:

Verfahren zum Färben und Bedrucken
von geformten Gebilden aus aromatischen
Polyestern, insbesondere
PolyäthylenterephthalatenMethod of dyeing and printing
of formed structures from aromatic
Polyesters, in particular
Polyethylene terephthalates

Anmelder:Applicant:

Farbwerke Hoechst Aktiengesellschaft
vormals Meister Lucius & Briining,
Frankfurt/M.,Farbwerke Hoechst Aktiengesellschaft
formerly Master Lucius & Briining,
Frankfurt / M.,

CH-RCH-R

worin R einen Pyridin- oder Chinolinring bedeutet, der noch Substituenten enthalten kann, bei erhöhter Temperatur, vorzugsweise bei Temperaturen von etwa 100 bis 1300C, färbt oder hiermit bedruckt und die Drucke bei der erhöhten Temperatur fixiert.where R denotes a pyridine or quinoline ring, which may also contain substituents , dyes or imprints with it at elevated temperature, preferably at temperatures of about 100 to 130 ° C., and fixes the prints at the elevated temperature.

Als Verbindungen mit aktivierter Methylgruppe kommen z. B. Chinaldin oder substituierte Chinaldine, wie 3-Oxychinaldm oder 6-Chlorchinaldin, ferner Pyridinderivate, wie a-Picolin und substituierte Picoline, wie z. B. 2-Methyl-5-äthylpyridin oder andere heterocyclische Verbindungen mit aktivierter Methylgruppe in Frage.As compounds with an activated methyl group, for. B. quinaldine or substituted quinaldine, like 3-Oxychinaldm or 6-Chlorquinaldin, also pyridine derivatives, such as a-picoline and substituted ones Picoline, such as B. 2-methyl-5-ethylpyridine or other heterocyclic compounds with activated Methyl group in question.

Die erfindungsgemäß verwendeten Farbstoffe, die zum Teil schon als spritlösliche Farbstoffe und nach Sulfonierung als saure Farbstoffe bekannt sind (vgl. zum Beispiel deutsche Patentschriften 23 188, 25 144, 158 761, 204 255, 286 237 und 688 504), färben Fasern und Folien aus aromatischen Polyestern, insbesondere Polyäthylenterephthalaten, in grünstichiggelben bis rotstichiggelben Tönen, die sich durch gute Echtheitseigenschaften auszeichnen.The dyes used according to the invention, some of them already as fuel-soluble dyes and after Sulfonation are known as acidic dyes (see, for example, German patents 23 188, 25 144, 158 761, 204 255, 286 237 and 688 504), dye fibers and films made of aromatic polyesters, in particular polyethylene terephthalates, in greenish yellow to reddish yellow tones, the are characterized by good fastness properties.

Beispiel 1example 1

Man bringt 1 Gewichtteil des Kondensationsproduktes aus Phthalsäureanhydrid und 3-Oxy- Als Erfinder benannt:
Dr. Norbert Ottawa, Frankfurt/M.-Höchst,
Dr. Rudolf Weingarten, Schwalbach (Taunus),
Kurt Roth, Hofheim (Taunus)1 part by weight of the condensation product of phthalic anhydride and 3-oxy- named as inventor:
Dr. Norbert Ottawa, Frankfurt / M.-Höchst,
Dr. Rudolf Weingarten, Schwalbach (Taunus),
Kurt Roth, Hofheim (Taunus)

chinaldin von der folgenden Formel
Oquinaldin of the following formula
O

nach Zusatz eines geeigneten Dispergiermittels, wie z. B. des Kondensationsproduktes aus Naphthalin-2-sulfonsäure und Formaldehyd, nach bekannten Verfahren in ausreichende Feinverteilung und disper-after adding a suitable dispersant, such as. B. the condensation product of naphthalene-2-sulfonic acid and formaldehyde, according to known processes in sufficient fine distribution and dispersible

4<) giert in 3000 Gewichtsteilen Wasser. In dieses Färbebad bringt man 100 Gewichtsteile einer Polyäthylenterephthalatware in Form von losem Material, Kammzug, Garn oder Stück und färbt P/2 Stunden bei 12O0C. Anschließend behandelt man die gefärbte Ware 15 Minuten bei 8O0C in einem Bade nach, das in 1000 Volumteilen Wasser 2 Gewichtsteile kalziniertes Natriumcarbonat, 2 Gewichtsteile Natriumdithionit und 2 Gewichtsteile eines waschaktiven Mittels, z. B. eines Alkylarylsulfonats, zur Entfernung des oberflächlich anhaftenden Farbstoffes enthält. Man erhält eine klare gelbe Färbung von guten Echtheitseigenschaften.4 <) yeasts in 3000 parts by weight of water. This dyebath 100 parts by weight brings a Polyäthylenterephthalatware in the form of loose material, slubbing, yarn or piece and dyes P / 2 hours at 12O 0 C. then treated to the dyed goods 15 minutes at 8O 0 C in a bath to which in 1000 parts by volume of water, 2 parts by weight of calcined sodium carbonate, 2 parts by weight of sodium dithionite and 2 parts by weight of a detergent, e.g. B. an alkylarylsulfonate to remove the dye adhering to the surface. A clear yellow dyeing with good fastness properties is obtained.

409 587/388409 587/388

Eine vergleichbar gute Färbung wird auch erhalten, wenn man bei 10O0C unter Zusatz eines Carriers, ζ. B. einer Benzylbenzoatemulsion, färbt.A comparably good coloration is also obtained if one takes place at 10O 0 C with the addition of a carrier, ζ. B. a benzyl benzoate emulsion, colors.

Beispiel 2Example 2

20 Gewichtsteile des durch Kondensation von Phthalsäureanhydrid mit 3-Oxychinaldin~4-carbonsäure unter Decarboxylierung erhältlichen Farbstoffes von der folgenden Formel20 parts by weight of the by condensation of phthalic anhydride with 3-oxychinaldine ~ 4-carboxylic acid obtainable by decarboxylation dye of the following formula

werden unter Zusatz eines geeigneten Dispergiermittels, beispielsweise des Kondensationsproduktes aus 2-Naphthol-6-sulfonsäure, Kresol und Formaldehyd, in feine Verteilung gebracht, in 380 Gewichtsteilen Wasser dispergiert und dann in 600 Gewichtsteile einer Verdickung, beispielsweise einer geeigneten Naturgummisorte, eingerührt. Mit der so erhaltenen Druckpaste werden Gewebe, Gewirke oder Kammzüge aus Polyäthylenterephthalatfasern bedruckt, getrocknet und während 15 Minuten bei einem Druck von 1,5 bis 2 atü fixiert. Anschließend wird die Verdickung ausgewaschen und zur Erzielung der optimalen Reibechtheit, wie im Beispiel 1 angegeben, reduktiv nachbehandelt. Man erhält einen gelben Druck von guter Wasch-, Thermofixier- und Bügelechtheit.with the addition of a suitable dispersant, for example the condensation product from 2-naphthol-6-sulfonic acid, cresol and formaldehyde, brought into fine distribution, in 380 parts by weight Water dispersed and then in 600 parts by weight of a thickener, for example one suitable type of natural rubber, stirred in. The printing paste obtained in this way is used to create woven and knitted fabrics or tops made of polyethylene terephthalate fibers printed, dried and for 15 minutes at fixed at a pressure of 1.5 to 2 atmospheres. Then the thickening is washed out and used to achieve the optimal rub fastness, as indicated in Example 1, reductively aftertreated. You get one yellow print of good fastness to washing, heat setting and ironing.

Die nachstehende Tabelle enthält noch eine Anzahl von weiteren erfindungsgemäß verwendbaren Farbstoffen vom Chinophthalontyp, die ebenfalls gute Echtheitseigenschaften besitzen, sowie deren Farbtöne.The table below also contains a number of other usable according to the invention Quinophthalone type dyes, which also have good fastness properties, as well as their Shades.

Anhydrid
komponenteanhydride
component Komponente
mit aktivierter
Methylgruppecomponent
with activated
Methyl group Farbtonhue 5 Phthalsäure
Phthalsäure
Phthalsäure 5 phthalic acid
Phthalic acid
Phthalic acid Chinaldin
2-Methyl-
5-äthyIpyridin
6-ChlorchinaldinQuinaldin
2-methyl
5-ethyIpyridine
6-chloroquinaldine Grünstichiggelb
Grünstichiggelb
GelbGreenish yellow
Greenish yellow
yellow

Claims (2)

Patentansprüche:Patent claims: 1. Verfahren zum Färben und Bedrucken von geformten Gebilden aus aromatischen Polyestern, insbesondere Polyäthylenterephthalaten, dadurch gekennzeichnet, daß man die Gebilde mit wässerigen Dispersionen von durch Kondensation von Phthalsäureanhydrid mit Verbindungen mit aktivierter Methylgruppe erhaltenen Farbstoffen vom Chinophthalontyp, die die folgende allgemeine Zusammensetzung haben:1. Process for dyeing and printing molded articles made of aromatic polyesters, in particular polyethylene terephthalates, characterized in that the Formed with aqueous dispersions of phthalic anhydride condensation with compounds quinophthalone type dyes obtained with activated methyl group, which have the following general composition: CH-RCH-R worin R einen Pyridin- oder Chinolinring bedeutet, der noch Substituenten enthalten kann, bei erhöhter Temperatur färbt oder hiermit bedruckt und die Drucke bei erhöhter Temperatur fixiert.where R is a pyridine or quinoline ring which may still contain substituents, dyes or prints with it at elevated temperature and the prints at elevated temperature fixed. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß die Färbung bzw. die Fixierung der Drucke bei 100 bis 1300C erfolgt.2. The method according to claim 1, characterized in that the coloring or the fixing of prints is carried out at 100 to 130 0 C. In Betracht gezogene Druckschriften:
USA.-Patentschrift Nr. 2 795 582.Considered publications:
U.S. Patent No. 2,795,582. 4095S7/34S 4.64 θ Bundesdruckerei Berlin4095S7 / 34S 4.64 θ Bundesdruckerei Berlin
DEF24023A 1957-09-25 1957-09-25 Process for dyeing and printing shaped structures made of aromatic polyesters, in particular polyethylene terephthalates Pending DE1168862B (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DENDAT1252168D DE1252168B (en) 1957-09-25 Process for dyeing and printing shaped articles made of aromatic polyesters, in particular polyethylene terephthalates
DEF24023A DE1168862B (en) 1957-09-25 1957-09-25 Process for dyeing and printing shaped structures made of aromatic polyesters, in particular polyethylene terephthalates
GB3071658A GB870680A (en) 1957-09-25 1958-09-25 Process for dyeing or printing shaped structures of aromatic polyesters
FR1202744D FR1202744A (en) 1957-09-25 1958-09-25 Process of dyeing and printing polyesters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF24023A DE1168862B (en) 1957-09-25 1957-09-25 Process for dyeing and printing shaped structures made of aromatic polyesters, in particular polyethylene terephthalates

Publications (1)

Publication Number Publication Date
DE1168862B true DE1168862B (en) 1964-04-30

Family

ID=7091073

Family Applications (2)

Application Number Title Priority Date Filing Date
DENDAT1252168D Pending DE1252168B (en) 1957-09-25 Process for dyeing and printing shaped articles made of aromatic polyesters, in particular polyethylene terephthalates
DEF24023A Pending DE1168862B (en) 1957-09-25 1957-09-25 Process for dyeing and printing shaped structures made of aromatic polyesters, in particular polyethylene terephthalates

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DENDAT1252168D Pending DE1252168B (en) 1957-09-25 Process for dyeing and printing shaped articles made of aromatic polyesters, in particular polyethylene terephthalates

Country Status (3)

Country Link
DE (2) DE1168862B (en)
FR (1) FR1202744A (en)
GB (1) GB870680A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3767357A (en) * 1970-05-23 1973-10-23 Hoechst Ag Mixture of quinophthalone dispense dyestuffs

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH407943A (en) * 1963-08-02 1966-09-15 Sandoz Ag Process for dyeing textile fibers made of hydrophobic organic material with quinophthalone dyes
US9708465B2 (en) * 2013-05-29 2017-07-18 Sabic Global Technologies B.V. Color-stable thermoplastic composition
CN107001782B (en) 2014-11-25 2019-07-05 沙特基础工业全球技术有限公司 Weather resistant thermoplastic composition, preparation method and its product

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2795582A (en) * 1956-07-25 1957-06-11 Du Pont Quinophthalone dyes for hydrophobic fibers

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2795582A (en) * 1956-07-25 1957-06-11 Du Pont Quinophthalone dyes for hydrophobic fibers

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3767357A (en) * 1970-05-23 1973-10-23 Hoechst Ag Mixture of quinophthalone dispense dyestuffs

Also Published As

Publication number Publication date
DE1252168B (en) 1967-10-19
GB870680A (en) 1961-06-14
FR1202744A (en) 1960-01-12

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