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 polyestersInfo
- 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
Links
Classifications
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes 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
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
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
CO HN-CO-R
C.
O HNO HN
R'R '
Verfahren zum Färben und Bedrucken von
Fasergut aus hochmolekularen PolyesternProcess 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.
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 Ricinusölsanthraquinone,
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 Polyvinylpyrrolidon3 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
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.
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)
Deutsche Auslegeschrift Nr. 1 037 406.Considered publications:
German interpretative document No. 1 037 406.
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 | |
| 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 |
| CH231664A CH401901A (en) | 1963-02-26 | 1964-02-25 | Process for dyeing or printing fiber material made of polyester |
| 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)
| 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)
| 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 |
-
1963
- 1963-02-26 DE DEC29248A patent/DE1242554B/en active Pending
-
1964
- 1964-02-25 CH CH231664A patent/CH401901A/en unknown
- 1964-02-25 NL NL6401777A patent/NL6401777A/xx unknown
- 1964-02-25 GB GB780864A patent/GB1000887A/en not_active Expired
- 1964-02-25 FR FR964999A patent/FR1383458A/en not_active Expired
- 1964-02-26 BE BE644371D patent/BE644371A/xx unknown
Patent Citations (1)
| 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)
| 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 |
| NL6401777A (en) | 1964-08-27 |
| FR1383458A (en) | 1964-12-24 |
| CH401901A (en) | 1966-05-14 |
| GB1000887A (en) | 1965-08-11 |
| CH231664A4 (en) | 1965-07-30 |
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