DE1258380B - Coloring and / or printing of structures made of linear polyesters - Google Patents
Coloring and / or printing of structures made of linear polyestersInfo
- Publication number
- DE1258380B DE1258380B DEB63903A DEB0063903A DE1258380B DE 1258380 B DE1258380 B DE 1258380B DE B63903 A DEB63903 A DE B63903A DE B0063903 A DEB0063903 A DE B0063903A DE 1258380 B DE1258380 B DE 1258380B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- printing
- linear polyesters
- coloring
- 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
Links
- 229920000728 polyester Polymers 0.000 title claims description 4
- 238000004040 coloring Methods 0.000 title claims 2
- 238000004043 dyeing Methods 0.000 claims description 5
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000975 dye Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- -1 methoxyl group Chemical group 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- GTRGJJDVSJFNTE-UHFFFAOYSA-N chembl2009633 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=CC2=C1N=NC1=CC=CC=C1 GTRGJJDVSJFNTE-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000019635 sulfation Effects 0.000 description 2
- 238000005670 sulfation reaction Methods 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 1
- RCCOCRAQVOJNMG-UHFFFAOYSA-N OC1=CC=C(C=2C(C3=CC=CC(=C3C(C12)=O)SC1=CC=CC=C1)=O)N Chemical compound OC1=CC=C(C=2C(C3=CC=CC(=C3C(C12)=O)SC1=CC=CC=C1)=O)N RCCOCRAQVOJNMG-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
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
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
- C09B1/585—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals substituted by aryl 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
- 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
- C09B1/22—Dyes with unsubstituted amino groups
-
- 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. Cl.:Int. Cl .:
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:
D 06pD 06p
Deutsche KL: 8m-1/01German KL: 8m-1/01
1 258 380
B63903IVc/8m
5. September 1961
11. Januar 19681,258,380
B63903IVc / 8m
5th September 1961
January 11, 1968
Gegenstand des Patents 1 223 797 ist die Verwendung von Abkömmlingen des 1-Aminoanthrachinons der FormelThe subject of patent 1,223,797 is the use of derivatives of 1-aminoanthraquinone the formula
O NH2 O NH 2
wobei Y für ein Wasserstoffatom, eine Methylgruppe, eine Methoxylgruppe oder ein Halogenatom, wie ein Chlor- oder Bromatom, steht, als Farbstoffe zum Färben und bzw. oder Bedrucken von Gebilden aus linearen Polyestern.where Y represents a hydrogen atom, a methyl group, a methoxyl group or a halogen atom such as Chlorine or bromine atom, is available as dyes for dyeing and / or printing of structures linear polyesters.
Als Weiterentwicklung des Gegenstandes des Hauptpatents wurde gefunden, daß man als Farbstoffe auch solche Abkömmlinge des 1-Aminoanthrachinons verwenden kann, die in 5- oder 8-Stellung des Anthrachinonkerns den aromatischen Thioätherrest tragen.As a further development of the subject matter of the main patent, it was found that as dyes can also use those derivatives of 1-aminoanthraquinone that are in 5- or 8-position of the anthraquinone nucleus carry the aromatic thioether residue.
Von besonderem technischem Interesse sind Farbstoffe der allgemeinen FormelDyes of the general formula are of particular technical interest
O NH2 O NH 2
O RO R
undand
in denen R ein Wasserstoffatom oder eine Hydroxylgruppe bedeutet und Y für ein Wasserstoffatom, eine Methylgruppe, eine Methoxylgruppe, eine Hydroxylgruppe oder ein Halogenatom, wie ein Chlor- oder Bromatom, steht.in which R represents a hydrogen atom or a hydroxyl group and Y represents a hydrogen atom, a Methyl group, a methoxyl group, a hydroxyl group or a halogen atom such as a chlorine or Bromine atom, stands.
Derartige Farbstoffe können in an sich bekannter Weise durch Umsetzen entsprechend substituierter 1-Aminohalogenanthrachinone mit ArylmercaptanenSuch dyes can be appropriately substituted by reaction in a manner known per se 1-Aminohalogenanthraquinones with aryl mercaptans
Färben und bzw. oder Bedrucken von Gebilden
aus linearen PolyesternDyeing and / or printing of structures
made of linear polyesters
Zusatz zum Patent: 1 223 797Addendum to the patent: 1 223 797
Anmelder:Applicant:
Badische Anilin- & Soda-FabrikAniline & Soda Factory in Baden
Aktiengesellschaft, 6700 LudwigshafenAktiengesellschaft, 6700 Ludwigshafen
Als Erfinder benannt:Named as inventor:
Dr. Willy Braun, 6900 Heidelberg;Dr. Willy Braun, 6900 Heidelberg;
Dr. Enno Spohler, 6703 LimburgerhofDr. Enno Spohler, 6703 Limburgerhof
in organischen Lösungsmitteln und in Gegenwart von alkalischen Mitteln erhalten werden.in organic solvents and in the presence of alkaline agents.
Die erfindungsgemäß verwendeten Farbstoffe, die nach den in der Hauptpatentschrift beschriebenen Methoden benutzt werden können, ergeben Färbungen und Drucke, die sich durch sehr gute Licht- und Naßechtheiten auszeichnen. Sie sind außerdem sehr beständig gegenüber thermischen Beanspruchungen, wie sie beispielsweise beim sogenannten Thermofixieren auftreten.The dyes used in accordance with the invention, which are those described in the main patent specification Methods that can be used produce colorations and prints that are characterized by very good light and light Distinguish wet fastness properties. They are also very resistant to thermal loads, as they occur, for example, during so-called heat setting.
Es können auch Mischungen der obengenannten Farbstoffe untereinander oder mit anderen Farbstoffen verwendet werden.Mixtures of the abovementioned dyes with one another or with other dyes can also be used be used.
Die in den Beispielen angegebenen Teile und Prozentzahlen sind Gewichtseinheiten.The parts and percentages given in the examples are units of weight.
100 Teile Polyäthylenglykolterephthalatgewebe werden in einem Bad, das aus 1 Teil feinverteiltem l-Amino-5-phenylmercaptoanthrachinon, 4 Teilen feinverteiltem 2-Hydroxydiphenyl und 3000 Teilen Wasser besteht, während 90 Minuten bei Siedetemperatur gefärbt. Nach kräftigem Spülen behandelt man das Gewebe in einem Bad, das aus einer Lösung von 3 Teilen ungefähr 32°/oiger wäßriger Natriumhydroxydlösung und 3 Teilen Natriumdithionit in 3000 Teilen Wasser besteht, 15 Minuten bei 8O0C.100 parts of polyethylene glycol terephthalate fabric are dyed for 90 minutes at boiling temperature in a bath consisting of 1 part of finely divided l-amino-5-phenylmercaptoanthraquinone, 4 parts of finely divided 2-hydroxydiphenyl and 3000 parts of water. After vigorous rinsing treating the fabric in a bath consisting of a solution of 3 parts of about 32 ° / aqueous sodium hydroxide solution cent and 3 parts of sodium dithionite in 3000 parts of water, for 15 minutes at 8O 0 C.
Man erhält brillante Orangefärbungen von sehr guter Lichtechtheit und guter thermischer Beständigkeit. Brilliant orange colorations of very good lightfastness and good thermal stability are obtained.
Verwendet man Färbebäder, die an Stelle von l-Amino-5-phenylmercaptoanthrachinon die gleicheIf you use dye baths that are the same instead of l-amino-5-phenylmercaptoanthraquinone
709 718/402709 718/402
Menge 1 - Amino - 5 - (ο - tolylmercapto) - anthrachinon oder l-Amino-S-ip-tolylmercaptoi-anthrachinon enthalten, so erhält man ebenfalls orange Färbungen mit guten Echtheitseigenschaften.Quantity 1 - amino - 5 - (ο - tolylmercapto) - anthraquinone or l-amino-S-ip-tolylmercaptoi-anthraquinone contain orange dyeings with good fastness properties.
Man färbt 100 Teile Polyäthylenglykolterephthalatfäden in einem Bad, das in 1500 Teilen Wasser 0,6 Teile feinverteiltes l-Amino-5-(p-methoxyphenylmercapto)-anthrachinon und 2 Teile eines Produktes enthält, das man durch Umsetzen von 1 Mol Spermölalkohol mit 80 Mol Äthylenoxyd und nachfolgendes Sulfatieren erhalten hat, 1 Stunde bei 1300C unter Druck.100 parts of polyethylene glycol terephthalate threads are dyed in a bath containing, in 1500 parts of water, 0.6 part of finely divided l-amino-5- (p-methoxyphenylmercapto) anthraquinone and 2 parts of a product which is obtained by reacting 1 mol of sperm oil alcohol with 80 mol Ethylene oxide and subsequent sulfation has received, 1 hour at 130 0 C under pressure.
Die Fäden werden in brillanten orangefarbenen Tönen mit sehr guter Licht- und Thermofixierechtheit gefärbt.The threads are in brilliant orange tones with very good light and thermosetting fastness colored.
Verwendet man Färbebäder, die an Stelle von 0,6 Teilen l-Amino-5-(p-methoxyphenylmercapto)-anthrachinon 0,4 Teile l-Amino-4-Hydroxy-5-phenylmercaptoanthrachinon enthalten, so erhält man Bordofärbungen mit sehr guter Lichtechtheit, guter Waschechtheit und sehr guter thermischer Beständigkeit. If you use dyebaths that contain l-amino-5- (p-methoxyphenylmercapto) anthraquinone in place of 0.6 parts 0.4 parts of 1-amino-4-hydroxy-5-phenylmercaptoanthraquinone are obtained Bordo dyeings with very good lightfastness, good washfastness and very good thermal resistance.
Polyäthylenglykolterephthalatgewebe wird mit einer Paste bedruckt, die in 1000 Teilen 20 TeilePolyethylene glycol terephthalate fabric is printed with a paste containing 20 parts in 1000 parts
l-Ammo-S-phenylmercaptoanthrachinon, 600 Teile einer Gummiarabikumverdickung, 30 Teile 4-Hydroxydiphenyl und 350 Teile Wasser enthält. Sodann wird das bedruckte Gewebe getrocknet und 15 Minuten lang bei 1,5 Atm. Überdruck gedämpft. Man erhält brillante, orangefarbene Drucke von guter Lichtechtheit und guter thermischer Beständigkeit.l-Ammo-S-phenylmercaptoanthraquinone, 600 parts a gum arabic thickener, 30 parts of 4-hydroxydiphenyl and 350 parts of water. Then the printed fabric is dried and at 1.5 atm for 15 minutes. Overpressure dampened. You get brilliant, orange-colored prints of good lightfastness and good thermal resistance.
100 Teile Polyäthylenglykolterephthalatfasern werden in einem Bad, das aus !Teilen feinverteiltem100 parts of polyethylene glycol terephthalate fibers are in a bath consisting of! Parts finely divided
1 - Amino - 8 - (ρ - chlorphenylmercapto) - anthrachinon,1 - amino - 8 - (ρ - chlorphenylmercapto) - anthraquinone,
2 Teilen des durch Umsetzen von 1 Mol Spermölalkohol mit 80 Mol Äthylenoxyd und darauffolgendes Sulfatieren erhältlichen Produktes und 2000 Teilen Wasser besteht, während einer Stunde bei 125c C in einem Druckgefäß gefärbt. Man erhält kräftige orange Färbungen von guter Lichtechtheit und guter thermischer Beständigkeit.2 parts of the product obtainable by reacting 1 mole of sperm oil alcohol with 80 moles of ethylene oxide and subsequent sulfation and 2000 parts of water, colored in a pressure vessel at 125 ° C. for one hour. Strong orange colorations of good lightfastness and good thermal stability are obtained.
Claims (1)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE622153D BE622153A (en) | 1961-09-05 | ||
| DEB63903A DE1258380B (en) | 1961-09-05 | 1961-09-05 | Coloring and / or printing of structures made of linear polyesters |
| CH932362A CH441218A (en) | 1961-09-05 | 1962-08-03 | Dyebath or printing paste and their use for dyeing or printing polyesters |
| GB33805/62A GB990290A (en) | 1961-09-05 | 1962-09-04 | Improvements in dyeing or printing linear aromatic polyester products |
| FR908670A FR82238E (en) | 1961-09-05 | 1962-09-05 | Dye baths and printing colors |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB63903A DE1258380B (en) | 1961-09-05 | 1961-09-05 | Coloring and / or printing of structures made of linear polyesters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1258380B true DE1258380B (en) | 1968-01-11 |
Family
ID=6974186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB63903A Pending DE1258380B (en) | 1961-09-05 | 1961-09-05 | Coloring and / or printing of structures made of linear polyesters |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE622153A (en) |
| CH (1) | CH441218A (en) |
| DE (1) | DE1258380B (en) |
| GB (1) | GB990290A (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 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1284539B (en) * | 1964-11-21 | 1968-12-05 | Basf Ag | Process for the preparation of 1-amino-anthraquinone dyes |
| CH616442A5 (en) * | 1975-07-23 | 1980-03-31 | Ciba Geigy Ag | |
| DE3314467A1 (en) * | 1982-07-17 | 1984-01-19 | Bayer Ag, 5090 Leverkusen | DICHROITIC MATERIAL, CONTAINING ANTHRACHINONE DYES AND NEW ANTHRACHINONE DYES |
-
0
- BE BE622153D patent/BE622153A/xx unknown
-
1961
- 1961-09-05 DE DEB63903A patent/DE1258380B/en active Pending
-
1962
- 1962-08-03 CH CH932362A patent/CH441218A/en unknown
- 1962-09-04 GB GB33805/62A patent/GB990290A/en not_active Expired
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 |
|---|---|
| BE622153A (en) | |
| CH932362A4 (en) | 1964-10-31 |
| CH441218A (en) | 1968-01-15 |
| GB990290A (en) | 1965-04-28 |
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