DE1242554B - Process for dyeing and printing fiber material made from high molecular weight polyesters - Google Patents

Process for dyeing and printing fiber material made from high molecular weight polyesters

Info

Publication number
DE1242554B
DE1242554B DEC29248A DEC0029248A DE1242554B DE 1242554 B DE1242554 B DE 1242554B DE C29248 A DEC29248 A DE C29248A DE C0029248 A DEC0029248 A DE C0029248A DE 1242554 B DE1242554 B DE 1242554B
Authority
DE
Germany
Prior art keywords
anthraquinone
dyeing
molecular weight
high molecular
fiber material
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
DEC29248A
Other languages
German (de)
Inventor
Dr Werner Zerweck
Dr Ernst Heinrich
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.)
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella Farbwerke Mainkur 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 Cassella Farbwerke Mainkur AG filed Critical Cassella Farbwerke Mainkur AG
Priority to DEC29248A priority Critical patent/DE1242554B/en
Priority to NL6401777A priority patent/NL6401777A/xx
Priority to CH231664A priority patent/CH401901A/en
Priority to GB780864A priority patent/GB1000887A/en
Priority to FR964999A priority patent/FR1383458A/en
Priority to BE644371D priority patent/BE644371A/xx
Publication of DE1242554B publication Critical patent/DE1242554B/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
    • C09B1/00Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16Amino-anthraquinones
    • C09B1/20Preparation from starting materials already containing the anthracene nucleus
    • C09B1/36Dyes with acylated amino groups
    • C09B1/42Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Int. Cl.:Int. Cl .:

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

2 Z < 2 Z <

IJ -/11IJ - / 11

Nummer: 1242554Number: 1242554

Aktenzeichen: C29248IVc/8mFile number: C29248IVc / 8m

Anmeldetag: 26. Februar 1963Filing date: February 26, 1963

Auslegetag: 22. Juni 1967Open date: June 22, 1967

Es wurde gefunden, daß man tiefe Färbungen bzw. satte Drucke auf Polyester-Fasermaterialien, insbesondere solchen auf Basis von Polyäthylenglykolterephthalaten, nach dem Thermofixierverfahren erhält, wenn man zum Färben bzw. Bedrucken Farbstoffe der allgemeinen FormelIt has been found that deep dyeings or deep prints on polyester fiber materials, in particular those based on polyethylene glycol terephthalates, obtained by the thermosetting process, if you use dyes of the general formula for dyeing or printing

O HN-CO-R
C
O HN-CO-R
C.

O HNO HN

R'R '

Verfahren zum Färben und Bedrucken von
Fasergut aus hochmolekularen Polyestern
Process for dyeing and printing
Fiber material made from high molecular weight polyesters

Anmelder:Applicant:

Cassella Farbwerke Mainkur Aktiengesellschaft, Frankfurt/M.-FechenheimCassella Farbwerke Mainkur Aktiengesellschaft, Frankfurt / M.-Fechenheim

Als Erfinder benannt:Named as inventor:

Dr. Werner Zerweck f, Frankfurt.;Dr. Werner Zerweck f, Frankfurt .;

Dr. Ernst Heinrich, Frankfurt/M.-FechenheimDr. Ernst Heinrich, Frankfurt / M.-Fechenheim

worin R einen gegebenenfalls durch Halogen, Alkyl, Alkoxy, eine Trifluormethyl- oder Nitrogruppe substituierten Phenylkern und R' Cyan oder Halogen bedeutet, verwendet.where R is optionally substituted by halogen, alkyl, alkoxy, a trifluoromethyl or nitro group Phenyl nucleus and R 'denotes cyano or halogen is used.

Die genannten Farbstoffe können in bekannter Weise erhalten werden, z. B. durch Umsetzung von l-Acylamino^-halogen-anthrachinonen mit entsprechend substituierten Anilinen bzw. durch Kondensation von l-Amino-4-halogen-anthrachinon-2-sulfonsäuren mit geeigneten Anilinen, Eliminierung der Sulfonsäuren gruppe in 2-Stellung und Acylierung der so entstandenen 1 -Amino-4-arylamino-anthrachinone.The dyes mentioned can be obtained in a known manner, for. B. by implementing l-acylamino ^ -halogen-anthraquinones with accordingly substituted anilines or by condensation of l-amino-4-halo-anthraquinone-2-sulfonic acids with suitable anilines, elimination of the sulfonic acid group in the 2-position and acylation of the resulting 1-amino-4-arylamino-anthraquinones.

Die erfindungsgemäß auf Polyester-Fasermaterialien herstellbaren, farbstarken Drucke bzw. Färbungen besitzen sehr gute Echtheitseigenschaften, insbesondere hervorragende Thermofixier- und Lichtechtheit.The strongly colored prints or dyeings which can be produced according to the invention on polyester fiber materials have very good fastness properties, in particular excellent heat-setting and lightfastness.

Gegenüber Drucken auf Polyestergewebe mit dem aus der deutschen Patentschrift 1 037 406 bekannten l-Amino-2-nitro-4-butyryl-aminoanthrachinon besitzen Drucke mit dem erfindungsgemäß zu verwendenden l-Benzoylamino-4-(m-chlor-anilido)-anthrachinon eine überlegene Heißluftfixierechtheit.Compared to printing on polyester fabric with that known from German Patent 1,037,406 Possess l-amino-2-nitro-4-butyryl-aminoanthraquinone Prints with the l-benzoylamino-4- (m-chloro-anilido) -anthraquinone to be used according to the invention a superior hot air fixation fastness.

Beispiel 1example 1

Ein Gewebe aus Polyäthylenglykolterephthalat wird mit nachstehender Druckpaste bedruckt:A fabric made of polyethylene glycol terephthalate is printed with the following printing paste:

25 g l-Benzoylaroino-4-(in-chlor-anilido)-25 g l-Benzoylaroino-4- (in-chloro-anilido) -

anthrachinon,
150 g Natriumsalz eines sulfonierten Ricinusöls
anthraquinone,
150 g of the sodium salt of a sulfonated castor oil

(etwa 50°/oig),
215 g Wasser,
(about 50 ° / o solution),
215 g water,

600 g Kristallgummiverdickung (1: 3),
IQg Entschäumer,
600 g crystal rubber thickening (1: 3),
IQg defoamer,

1000 g.1000 g.

ao Nach dem Trocknen wird etwa 60 Sekunden bei 200J C im Thermonxierrahmen fixiert. Anschließend wird gespült und dann in einer Lösung, dieao After drying, fixation is carried out for about 60 seconds at 200 J C in the thermonxing frame. It is then rinsed and then in a solution that

3 ccm/1 Natronlauge 38" Be\
2 g/l Hydrosulfit konz. PIv.,
a5 1 g/l Polyvinylpyrrolidon
3 ccm / 1 sodium hydroxide solution 38 "Be \
2 g / l hydrosulfite conc. PIv.,
a5 1 g / l polyvinylpyrrolidone

enthält, während etwa 15 Minuten bei 60 bis 70" C behandelt. Hierauf wird gut gespült, mit etwa 2 g/l eines nichtionogenen Waschmittels heiß geseift, gespült und getrocknet. Man erhält einen vollen blauvioletten Druck von sehr guten Echtheitseigenschaften. Drucke von ähnlicher Nuance und von ebenfalls sehr guten Echtheitseigenschaften werden erhalten, wenn in der obigen Druckvorschrift das 1-Benzoylamino-4-(m-chlor-anilido)-anthrachinon ersetzt wird durch 1 - Benzoylatnino - 4 - (ra - brom - anilido) - anthrachinon, l-(m-Toluylamino)-4-(m-chlor-anilido)-anthrachinon, l-(m-Methoxy-benzoylamino)-4-(m-chloranilido)-anthrachinon, l-Benzoylamino-4-(o-chloranilido) - anthrachinon, 1 - (p · Chlor - benzoylamino)-4-(o-chlor-anilido)-anthrachinon, 1 -(m-Trifluormethylbenzoylamino)-4-(o-chlor-anilido)-anthrachinon oder durch l-(m-Nitro-benzoylamino)-4-(o-chlor-anilido)- | anthrachinon. Dagegen werden rotstichigblaue Drucke erhalten bei Anwendung von l-Benzoylamino-4-(pchlor - anilido) - anthrachinon, 1 - (m - Toluylamino)-4-(p-chlor-anilido)-anthrachinon oder von l-(m-Methoxy - benzoylamino) - 4 - (p - chlor - anilido) - anthrac hiiion und blaugraue Drucke bei Verwendung von l-(p-Nitro- jjcontains, treated for about 15 minutes at 60 to 70 "C. It is then rinsed well, with about 2 g / l a non-ionic detergent soaped, rinsed and dried. A full blue-violet print with very good fastness properties is obtained. Prints of a similar shade and also of very good fastness properties are obtained, if in the above printing specification the 1-benzoylamino-4- (m-chloro-anilido) -anthraquinone is replaced by 1 - Benzoylatnino - 4 - (ra - brom - anilido) - anthraquinone, l- (m-Toluylamino) -4- (m-chloro-anilido) -anthraquinone, l- (m-methoxy-benzoylamino) -4- (m-chloroanilido) -anthraquinone, l-Benzoylamino-4- (o-chloroanilido) - anthraquinone, 1 - (p chloro - benzoylamino) -4- (o-chloro-anilido) -anthraquinone, 1 - (m-Trifluoromethylbenzoylamino) -4- (o-chloro-anilido) -anthraquinone or by l- (m-nitro-benzoylamino) -4- (o-chloro-anilido) - | anthraquinone. On the other hand, there are reddish blue prints obtained when using l-benzoylamino-4- (pchlor - anilido) - anthraquinone, 1 - (m - toluylamino) -4- (p-chloro-anilido) -anthraquinone or from l- (m-methoxy - benzoylamino) - 4 - (p - chloro - anilido) - anthrac hiiion and blue-gray prints when using l- (p-nitro- jj

benzoylamino)-4-(m-chlor-anilido)-anthrachinon und Λ von l-(p-Nitro-benzoylamino)-4-(p-chlor-anilido)- f anthrachinon.benzoylamino) -4- (m-chloro-anilido) -anthraquinone and Λ of l- (p-nitro-benzoylamino) -4- (p-chloro-anilido) - f anthraquinone.

709 607/500709 607/500

Beispiel 2Example 2

Ein Gewebe aus Polyäthylenglykolterephthalat wird auf dem Foulard mit nachstehender Flotte geklotzt:A fabric made of polyethylene glycol terephthalate is used padded on the foulard with the following liquor:

25 g l-ßenzoylamino-4-0n-cyan-anilido)-25 g l-ßenzoylamino-4-0n-cyano-anilido) -

anthrachinon,
875 g Wasser, ■
100 g Kristallgummiverdickung (1: 3),
anthraquinone,
875 g water, ■
100 g crystal rubber thickening (1: 3),

1000 g.1000 g.

Nach dem Trocknen wird, wie unter Beispiel 1 beschrieben, weiterbehandelt.After drying, further treatment is carried out as described in Example 1.

Es wird eine blauviolette Färbung — rotstichiger als die des Beispiels 1 — von sehr guten Echtheitseigenschaften erhalten. A blue-violet coloration - more reddish than that of Example 1 - with very good fastness properties is obtained.

Färbungen von ähnlicher Nuance und ebenfalls sehr guten Echtheitseigenschaften werden erhalten, wenn in der obigen Vorschrift das 1 -BenzoyIamino-4-(m-cyananilido)-anthrachinon ersetzt wird durch l-(m-Toluylamino)-4-(m-cyan-am'lido)-anthrachinon oder durch 1 - (m - Methoxy - benzoylamino) - 4 - (m - cyan - an i lido)-anthrachinon. Dyeings of a similar shade and also very good fastness properties are obtained if in the above procedure the 1 -BenzoyIamino-4- (m-cyananilido) -anthraquinone is replaced by l- (m-Toluylamino) -4- (m-cyano-am'lido) -anthraquinone or by 1 - (m - methoxy - benzoylamino) - 4 - (m - cyano - an i lido) anthraquinone.

Beispiel 3Example 3

Ein Gewebe aus Polyäthylenglykolterephthalat wird auf dem Foulard mit nachstehender Flotte geklotzt: 2^ 25 g l-Bcnzoylainino-4-(m-chlor-anilido)-A fabric made of polyethylene glycol terephthalate is padded on the padder with the following liquor: 2 ^ 25 g l-Bcnzoylainino-4- (m-chloro-anilido) -

anthrachinon,
973 g Wasser,
anthraquinone,
973 g water,

0,5 g eines Polyglykoläthers,
1,5 g Polyacrylamid,
0.5 g of a polyglycol ether,
1.5 g polyacrylamide,

1000 g.1000 g.

Nach dem Trocknen wird, wie unter Beispiel 1 beschrieben, weiterbehandelt.After drying, further treatment is carried out as described in Example 1.

Es wird eine blauviolette Färbung von sehr guten Echtheitseigenschaften erhalten.A blue-violet coloration with very good fastness properties is obtained.

Claims (1)

Patentanspruch:Claim: Verfahren zum Färben und Bedrucken von Fasergut aus hochmolekularen Polyestern nach dem Thermofixierverfahren, dadurch gekennzeichnet, daß man hierbei Farbstoffe der allgemeinen FormelProcess for dyeing and printing fiber material made from high molecular weight polyesters the thermosetting process, characterized in that dyes are used here the general formula 30 O HN-CO-R 30 O HN-CO-R O HN -' O HN - ' R'R ' worin R einen gegebenenfalls durch Halogen. Alkyl, Alkoxy, eine Trifluormethyl- oder Nitrogruppe substituierten Phenylkern und R' Cyan oder Halogen bedeutet, verwendet.wherein R is optionally substituted by halogen. Alkyl, alkoxy, a trifluoromethyl or nitro group substituted phenyl nucleus and R 'denotes cyano or halogen is used. in Betracht gezogene Druckschriften:
Deutsche Auslegeschrift Nr. 1 037 406.
Considered publications:
German interpretative document No. 1 037 406.
Bei der Bekanntmachung der Anmeldung ist eine Färbetafel mit Erläuterungen ausgelegt worden.When the application was announced, a coloring table with explanations was laid out. 709 607/500 6.67 0 Bundesdruckerei Berlin709 607/500 6.67 0 Bundesdruckerei Berlin
DEC29248A 1963-02-26 1963-02-26 Process for dyeing and printing fiber material made from high molecular weight polyesters Pending DE1242554B (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
DEC29248A DE1242554B (en) 1963-02-26 1963-02-26 Process for dyeing and printing fiber material made from high molecular weight polyesters
NL6401777A NL6401777A (en) 1963-02-26 1964-02-25
CH231664A CH401901A (en) 1963-02-26 1964-02-25 Process for dyeing or printing fiber material made of polyester
GB780864A GB1000887A (en) 1963-02-26 1964-02-25 Printing and dyeing of aromatic polyester fibre materials
FR964999A FR1383458A (en) 1963-02-26 1964-02-25 Printing and dyeing of fibrous polyester materials
BE644371D BE644371A (en) 1963-02-26 1964-02-26

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC29248A DE1242554B (en) 1963-02-26 1963-02-26 Process for dyeing and printing fiber material made from high molecular weight polyesters

Publications (1)

Publication Number Publication Date
DE1242554B true DE1242554B (en) 1967-06-22

Family

ID=7018901

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC29248A Pending DE1242554B (en) 1963-02-26 1963-02-26 Process for dyeing and printing fiber material made from high molecular weight polyesters

Country Status (6)

Country Link
BE (1) BE644371A (en)
CH (1) CH401901A (en)
DE (1) DE1242554B (en)
FR (1) FR1383458A (en)
GB (1) GB1000887A (en)
NL (1) NL6401777A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2748834A1 (en) * 1976-11-02 1978-05-03 Ciba Geigy Ag METHOD OF COLORING POLYESTERS IN BULK

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1037406B (en) * 1955-08-02 1958-08-28 Ciba Geigy Process for dyeing and printing polyethylene terephthalate fiber material and preparation suitable for carrying out the process

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1037406B (en) * 1955-08-02 1958-08-28 Ciba Geigy Process for dyeing and printing polyethylene terephthalate fiber material and preparation suitable for carrying out the process

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2748834A1 (en) * 1976-11-02 1978-05-03 Ciba Geigy Ag METHOD OF COLORING POLYESTERS IN BULK

Also Published As

Publication number Publication date
BE644371A (en) 1964-06-15
GB1000887A (en) 1965-08-11
FR1383458A (en) 1964-12-24
CH401901A (en) 1966-05-14
NL6401777A (en) 1964-08-27
CH231664A4 (en) 1965-07-30

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