DE1009595B - Process for coloring materials made from polyesters of aromatic dicarboxylic acids - Google Patents
Process for coloring materials made from polyesters of aromatic dicarboxylic acidsInfo
- Publication number
- DE1009595B DE1009595B DEC10299A DEC0010299A DE1009595B DE 1009595 B DE1009595 B DE 1009595B DE C10299 A DEC10299 A DE C10299A DE C0010299 A DEC0010299 A DE C0010299A DE 1009595 B DE1009595 B DE 1009595B
- Authority
- DE
- Germany
- Prior art keywords
- polyesters
- dicarboxylic acids
- aromatic dicarboxylic
- materials made
- coloring materials
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 229920000728 polyester Polymers 0.000 title claims description 7
- 239000000463 material Substances 0.000 title claims description 5
- -1 aromatic dicarboxylic acids Chemical class 0.000 title claims description 3
- 238000004040 coloring Methods 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 12
- 238000004043 dyeing Methods 0.000 claims description 10
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 125000001174 sulfone group Chemical group 0.000 claims description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 235000010292 orthophenyl phenol Nutrition 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 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 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
-
- 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
- C09B1/02—Hydroxy-anthraquinones; Ethers or esters thereof
-
- 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
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Es wurde gefunden, daß man. Materialien, aus Polyestern aromatischer Dicarbonsäuren in wertvoller Weise nach der Dispersionsfärbemethode färben, kann:, wenn man als Farbstoffe 1-Aminoanthrachinone verwendet, die in 7- oder vorzugsweise in. 6-Stellung eine Sulfonamid-, Sulfonsäureester- oder Sulfongruppe aufweisen.It was found that one. Materials, made of polyester color aromatic dicarboxylic acids in a valuable way according to the dispersion dyeing method, can: if the dyes used are 1-aminoanthraquinones which are in the 7- or preferably in the 6-position Have sulfonamide, sulfonic acid ester or sulfone group.
Als zu färbende Materialien kommen, beispielsweise Folien, insbesondere aber Fasern, der angegebenen Art in Betracht, vorzugsweise solche aus Polyestern der Terephthalsäure. Es können. Stapelfasern oder auch Fasern, aus endlosen Fäden, verwendet werden.The materials to be colored include, for example, films, but in particular fibers, of the specified types Kind in consideration, preferably those made from polyesters of terephthalic acid. It can. Staple fibers or fibers made from endless threads can also be used.
Die nach dem eingangs angegebenen Verfahren, verwendbaren Farbstoffe, sind zum Teil bekannt oder lassen sich nach an sich bekannten Methoden herstellen. Those which can be used according to the method specified at the beginning Some dyes are known or can be prepared by methods known per se.
Das Färben, mit den Farbstoffen der vorstehend angegebenen Zusammensetzung gemäß der Dispersionsfärbetnethode kann in an sich, bekannter Weise erfolgen. Im allgemeinen empfiehlt es sich, eine passende ao Verpastuiig der Farbstoffe vorzunehmen,. Gute Ergebnisse werden beispielsweise erzielt, wenn, man Sulfitcelluloseablauge, Tetrahydrofuran, Tetrahydrofurfurylaikohol eventuell zusammen mit Kondensationsprodukten aus höheren Alkoholen und ÄthylenO'xyd, Seife oder μ-heptadecyl-N-benzylbenzimidazoldisulfonsaures Natrium als Dispergiermittel verwendet. Es können auch zwei oder mehr Dispergiermittel getrennt verwendet werden, beispielsweise ein. erstes zur Verpastung und ein, zweites als Zusatz bei oder immittelbar vor der Bereitung des Färbebades. Außerdem kann es von Vorteil sein, vor dem Färben oder beim Vermischen mit Dispergiermitteln den. Farbstoff mit einem wasserlöslichen organischen Lösungsmittel zu behandeln, wobei er wenigstens teilweise in Lösung geht. In gewissen Fällen kann auch die Verwendung von Mischungen von, Farbstoffen, die der eingangs erwähnten Bedingung entsprechen,, von Vorteil sein.The dyeing with the dyes of the composition given above according to the dispersion dyeing method can be carried out in a manner known per se. In general, it is advisable to make a suitable paste of the dyes. Good results are achieved, for example, if sulphite cellulose liquor, tetrahydrofuran, tetrahydrofurfuryl alcohol, possibly together with condensation products of higher alcohols and ethylene oxide, soap or sodium μ-heptadecyl-N-benzylbenzimidazole disulphonic acid are used as a dispersant. Two or more dispersants can also be used separately, for example one. the first for pasting and a second as an additive during or immediately before the preparation of the dyebath. It can also be advantageous to use the before dyeing or when mixing with dispersants. To treat dye with a water-soluble organic solvent, whereby it is at least partially in solution. In certain cases, the use of mixtures of dyes which meet the condition mentioned at the beginning can also be advantageous.
Der Färl>eprozeß wird zweckmäßig bei erhöhter Temperatur, beispielsweise bei Siedetemperatur des Färbebades durchgeführt. Sofern, man in geschlossenen, Apparaten arbeitet, kann man auch bei noch höheren Temperaturen und unter Druck färben. Ge^ wünschtenfalls kann man dem Färbebad auch, eine gewisse Menge eines Quellmittels, wie Phenylmethylcarbinol, Benzoesäure, o-Phenylphenol, Chlorbenzol, zusetzen, wodurch im allgemeinen das Ziehvermögen noch erhöht wird.The dyeing process is expediently carried out at an elevated temperature, for example at the boiling point of the Dye bath carried out. If one works in closed, apparatus, one can also with still dyeing at higher temperatures and under pressure. Ge ^ if desired, you can also add a certain amount of a swelling agent, such as phenylmethylcarbinol, to the dyebath Benzoic acid, o-phenylphenol, chlorobenzene, add, which generally increases the drawability is still increased.
Es ist überraschend, daß die Verbindungen, der angegebenen Zusammensetzung, welche sich im allgemeinen nicht zum Färben anderer vollsynthetischer Fasern eignen, und auch auf Acetatseide zum großen Teil unbefriedigende Ergebnisse liefern, nicht nur ein sehr gutes Ziehvermögen gegenüber den Fasern ausIt is surprising that the compounds, of the specified composition, which in general not suitable for dyeing other fully synthetic fibers, and also on acetate silk for large Some of the results are unsatisfactory, and not just very good drawability with respect to the fibers
aus Polyestern aromatischerfrom polyesters more aromatic
DicarbonsäurenDicarboxylic acids
Anmelder:
CIBA Aktiengesellschaft, Basel (Schweiz)Applicant:
CIBA Aktiengesellschaft, Basel (Switzerland)
Vertreter: Dipl.-Ing. E. Splanemann, Patentanwalt, Hamburg 36, Neuer Wall 10Representative: Dipl.-Ing. E. Splanemann, patent attorney, Hamburg 36, Neuer Wall 10
Beanspruchte Priorität:
Schweiz vom 27. November 1953Claimed priority:
Switzerland from November 27, 1953
Dr. Jacques Wegmann, Basel,Dr. Jacques Wegmann, Basel,
und Dr. Walter Jenny, Reinach (Schweiz),and Dr. Walter Jenny, Reinach (Switzerland),
sind als Erfinder genannt wordenhave been named as inventors
Polyestern der Terephthalsäure besitzen, sondern auch Färbungen liefern, die sich durch gute' Echtheiten gegenüber den verschiedensten in Betracht kommenden. Einwirkungen und in manchen Fällen durch hervorragende Licht&chtheit auszeichnen.Polyesters of terephthalic acid, but also provide colorations that are characterized by good 'fastness properties compared to the most diverse possible ones. Actions and in some cases by excellent Characterize lightness.
Im nachfolgenden Beispiel bedeuten, die Teile, sofern nichts anderes bemerkt wird, Gewichtsteile und die Prozente Gewichtsprozente.In the following example, the parts mean, if nothing else is noted, parts by weight and percentages percentages by weight.
Beispiel
1 Teil des Farbstoffes der Formelexample
1 part of the dye of the formula
O NH,O NH,
C2H5O2SC 2 H 5 O 2 S
(l-Aminoanthrachinon-o-äthylsulfon) wird mit 2 Teilen einer 50°/i>igen wäßrigen Lösung von Sulfitcelluloseablauge naß vermählen und getrocknet.(l-Aminoanthraquinone-o-ethyl sulfone) is with 2 parts a 50% aqueous solution of sulphite cellulose waste liquor grind wet and dry.
Der Farbstoff wird mit 4 Teilen Äthylalkohol angeteigt, mit 20 Teilen einer lO°/oigen wäßrigen Lösung eines Kondensationsproduktes von Octadecylalkohol mit 20· Mol Äthylenoxyd verrührt und durch Verdünnen mit Wasser ein Färbebad von 4000 Teilen bereitet.The dye is made into a paste with 4 parts of ethyl alcohol, with 20 parts of a 10% aqueous solution a condensation product of octadecyl alcohol is stirred with 20 mol of ethylene oxide and diluted preparing a dyebath of 4000 parts with water.
, ,., 709 547694,,., 709 547694
In dieses Bad geht man bei 60° mit 100 Teilen eines Stapelgarnes aus einem Polyester der Terephthalsäure ein, steigert die Temperatur in einer halben Stunde zum Kochen und kocht während einer Stunde.100 parts of a staple yarn made from a polyester of terephthalic acid are placed in this bath at 60 ° one, raises the temperature to boil in half an hour and cooks for an hour.
Dann wird gespült und getrocknet. Man erhält eine rotorange Färbung von ausgezeichneter Liditechtheit.Then it is rinsed and dried. A red-orange coloration of excellent fastness to lidite is obtained.
Färbt man ein Gewebe aus entsprechendem, aus endlosen. Fäden bestehendem Material, so erhält man ein ähnlich gutes Ergebnis.A fabric is dyed from the corresponding, from endless ones. Threads of existing material, one obtains a similarly good result.
Führt man die gleiche Färbung in einer Apparatur aus, welche gestattet, die Temperatur auf HO1 bis 120° zu steigern, so· gelangt man zu einer noch kräftigeren Färbung von ebenfalls ausgezeichneten Echtheitsedgenschaften und insbesondere hoher Lichtechtheiit.If the same dyeing is carried out in an apparatus which allows the temperature to be increased to HO 1 to 120 °, an even stronger dyeing with excellent fastness properties and, in particular, high lightfastness is obtained.
Führt man die Färbung, wie oben beschrieben, bei 100° aus, aber unter Verwendung eines Quellmittels wie 10 g/l Phenylmethylcarbinol, 3 g/l o-Phenylphenol oder 20 g/l Benzoesäure, und seift die Färbung während einer Viertelstunde bei Kochtemperatur, so erhält man ebenfalls eine noch kräftigere Färbung mit ausgezeichneten Eigenschaften.If you carry out the staining as described above 100 ° off, but using a swelling agent such as 10 g / l phenylmethylcarbinol, 3 g / l o-phenylphenol or 20 g / l benzoic acid, and soaps the dye for a quarter of an hour at the boiling temperature, so an even stronger color with excellent properties is also obtained.
Verwendet man als Farbstoffe in der oben beschriebenen Weise l-Aminoanthrachinon-6-sulfonsäuredimethylamid oder l-Aminoanthrachinon-6-sulfonsäurephenylester, so erhält man ebenfalls orange Färbungen, die sich durch, hohe Lichtechtheit auszeichnen.Used as dyes in the above-described Way l-aminoanthraquinone-6-sulfonic acid dimethylamide or l-aminoanthraquinone-6-sulfonic acid phenyl ester, in this way, orange colorations are also obtained, which are characterized by high lightfastness.
Claims (1)
USA.-Patentschriften Nr. 2 640059, 2 640 060,
640 061;
britische Patentschriften Nr. 609 943, 659 667.Considered printing companies:
U.S. Patents Nos. 2,640,059, 2,640,060,
640 061;
British Patent Nos. 609 943, 659 667.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1167615X | 1953-11-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1009595B true DE1009595B (en) | 1957-06-06 |
Family
ID=4561072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC10299A Pending DE1009595B (en) | 1953-11-27 | 1954-11-20 | Process for coloring materials made from polyesters of aromatic dicarboxylic acids |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1009595B (en) |
| FR (1) | FR1167615A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB609943A (en) * | 1946-03-26 | 1948-10-08 | Alan Stanley Fern | Dyeing of highly polymeric linear esters |
| GB659667A (en) * | 1949-07-08 | 1951-10-24 | Stevensons Dyers Ltd | Improvements relating to dyeing processes |
| US2640061A (en) * | 1947-05-07 | 1953-05-26 | Celanese Corp | Process for the preparation of 1-amino-2-alkyl-mercapto-4 hydroxy-anthraquinones |
| US2640059A (en) * | 1949-07-20 | 1953-05-26 | Celanese Corp | Method of preparing hydroxyalkylthio anthraquinones |
| US2640060A (en) * | 1949-09-09 | 1953-05-26 | Celanese Corp | Beta-hydroxyethyl-thioanthraquinones |
-
1954
- 1954-11-12 FR FR1167615D patent/FR1167615A/en not_active Expired
- 1954-11-20 DE DEC10299A patent/DE1009595B/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB609943A (en) * | 1946-03-26 | 1948-10-08 | Alan Stanley Fern | Dyeing of highly polymeric linear esters |
| US2640061A (en) * | 1947-05-07 | 1953-05-26 | Celanese Corp | Process for the preparation of 1-amino-2-alkyl-mercapto-4 hydroxy-anthraquinones |
| GB659667A (en) * | 1949-07-08 | 1951-10-24 | Stevensons Dyers Ltd | Improvements relating to dyeing processes |
| US2640059A (en) * | 1949-07-20 | 1953-05-26 | Celanese Corp | Method of preparing hydroxyalkylthio anthraquinones |
| US2640060A (en) * | 1949-09-09 | 1953-05-26 | Celanese Corp | Beta-hydroxyethyl-thioanthraquinones |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1167615A (en) | 1958-11-27 |
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