DE1278391B - Dyeing and printing of fiber material made from high molecular weight polyesters - Google Patents
Dyeing and printing of fiber material made from high molecular weight polyestersInfo
- Publication number
- DE1278391B DE1278391B DEC36630A DEC0036630A DE1278391B DE 1278391 B DE1278391 B DE 1278391B DE C36630 A DEC36630 A DE C36630A DE C0036630 A DEC0036630 A DE C0036630A DE 1278391 B DE1278391 B DE 1278391B
- Authority
- DE
- Germany
- Prior art keywords
- dyeing
- printing
- anthraquinone
- molecular weight
- high molecular
- 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
- 238000004043 dyeing Methods 0.000 title claims description 9
- 229920000728 polyester Polymers 0.000 title claims description 6
- 239000002657 fibrous material Substances 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 4
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 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 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/34—Anthraquinone acridones or thioxanthrones
- C09B5/347—Anthraquinone acridones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
Int. CL:Int. CL:
D06pD06p
Deutsche Kl.: 8m-1/01 German class: 8m- 1/01
Nummer: 1278 391Number: 1278 391
Aktenzeichen: P 12 78 391.4-43 (C 36630)File number: P 12 78 391.4-43 (C 36630)
Anmeldetag: 14. Juli 1961Filing date: July 14, 1961
Auslegetag: 26. September 1968Opening day: September 26, 1968
Gegenstand der Erfindung ist die Verwendung von Farbstoffen der allgemeinen FormelThe invention relates to the use of dyes of the general formula
Färben und Bedrucken von Fasergut aus
hochmolekularen PolyesternDyeing and printing of fiber goods
high molecular weight polyesters
O NHO NH
worin R einen gegebenenfalls substituierten, aliphatischen Carbonsäurerest bedeutet und der mit Bz bezeichnete Ring noch Substituenten, wie z. B. Alkyl, Halogen, Nitro, Trifluormethyl, Acylamino, Acyl, enthalten kann und die durch Kondensation der entsprechenden 1 -Amino - anthrachinon - 3,4(N) - benzacridone mit aliphatischen Carbonsäuren, die auch Substituenten enthalten können, oder den funktioneilen Derivaten dieser Säuren, gegebenenfalls in An- , Wesenheit säurebindender Mittel, hergestellt worden sind, zum Färben und Bedrucken auf Polyesterfasermaterialien. wherein R denotes an optionally substituted, aliphatic carboxylic acid radical and that with Bz designated ring nor substituents such. B. alkyl, halogen, nitro, trifluoromethyl, acylamino, acyl, may contain and the condensation of the corresponding 1-amino - anthraquinone - 3,4 (N) - benzacridones with aliphatic carboxylic acids, which can also contain substituents, or the functional ones Derivatives of these acids, optionally in the presence of acid-binding agents, have been prepared are for dyeing and printing on polyester fiber materials.
Das Färben und Bedrucken der Polyesterfasermaterialien mit den erfindungsgemäß zu verwenden- » den Farbstoffen geschieht nach den hierfür bekannten Methoden, wie sie z.B. in Textilpraxis. 1956, S. 692 bis 697, besonders S. 697, letzter Absatz, veröffentlicht sind.The dyeing and printing of the polyester fiber materials with the inventively to be used » The dyes are done according to the methods known for this purpose, such as those used in textile practice. 1956, p. 692 to 697, especially p. 697, last paragraph, are published.
Die erfindungsgemäß zu verwendenden Farbstoffe ergeben Färbungen bzw. Drucke mit sehr guten Echtheitseigenschaften, insbesondere sehr guter Lichtechtheit. The dyes to be used according to the invention produce dyeings or prints with very good fastness properties, especially very good lightfastness.
Farbstoffe, die durch Acylierung von 1-Aminoanthrachinon-o'-chlor-S^fNJ-benzacridon erhalten , werden und einen Butyryl- bzw. Acetylrest enthalten, besitzen beim Drucken auf Polyestergewebe eine größere Farbstärke als der aus der USA.-Patentschrift 2 623 047 bekannte Farbstoff, der als Acylkomponente einen Hexahydrobenzoylrest enthält.Dyes obtained by acylation of 1-aminoanthraquinone-o'-chloro-S ^ fNJ-benzacridone obtained, and contain a butyryl or acetyl radical, have a when printing on polyester fabric greater color strength than the dye known from US Pat. No. 2,623,047, the acyl component contains a hexahydrobenzoyl radical.
Die in den nachfolgenden Beispielen beschriebenen Farbstoffe wurden jeweils durch Acylierung der entsprechenden 1 -Amino-anthrachinon-3,4 (N)-benzacridone hergestellt.The dyes described in the examples below were each obtained by acylating the corresponding 1-amino-anthraquinone-3,4 (N) -benzacridone produced.
Ein Gewebe aus Polyäthylenglykolterephthalat wird auf dem Foulard mit nachstehender Flotte geklotzt:A fabric made of polyethylene glycol terephthalate is padded on the padder with the following liquor:
Anmelder:Applicant:
Cassella Farbwerke Mainkur Aktiengesellschaft,Cassella Farbwerke Mainkur Aktiengesellschaft,
6000 Frankfurt-Fechenheim6000 Frankfurt-Fechenheim
Als Erfinder benannt:Named as inventor:
Dr. Werner Zerweck t, 6000 Frankfurt;Dr. Werner Zerweck t, 6000 Frankfurt;
Dr. Ernst Heinrich, 6000 Frankfurt-FechenheimDr. Ernst Heinrich, 6000 Frankfurt-Fechenheim
9,0 g 1 n-Butyrylamino-anthrachinon-9.0 g 1 n-butyrylamino-anthraquinone
3,4(N)-benzacridon
989,0 g Wasser3,4 (N) -benzacridone
989.0 grams of water
0,5 g eines Polyglykoläthers des Oleylalkohols 1,5 g Polyacrylamid vom K-Wert = 1200.5 g of a polyglycol ether of oleyl alcohol, 1.5 g of polyacrylamide with a K value of 120
1000,0 g1000.0 g
Nach dem Trocknen wird etwa 60 Sekunden bei 215° C im Thermofixierrahmen fixiert und anschließend wie üblich nachbehandelt. Man erhält so eine rotstichigblaue Färbung von sehr guten Echtheitseigenschaften. After drying, it is fixed in the heat-setting frame at 215 ° C. for about 60 seconds and then post-treated as usual. A reddish blue dyeing with very good fastness properties is obtained in this way.
Färbungen von ähnlichen Nuancen und von ebenfalls sehr guten Echtheitseigenschaften werden erhalten, wenn in der obigen Färbevorschrift das 1 n-Butyrylamino - anthrachinon - 3,4 (N) - benzacridon ersetzt wird durch l-Acetylamino-anthrachinon-3,4(N)-benzacridon, l-Propionylamino-anthrachinon-3,4(N)-benzacridon, 1 - Valerylamino-anthrachinon-3,4(N)-benzacridon, 1 -Capronylamino-anthrachinon-S^NJ-benzacridon, 1 -Caprylamino-anthrachinon-S^NJ-benzacridon oder durch 1-Acryloylamino-anthrachinon-3,4(N)-benzacridon. Dyeings of similar shades and also very good fastness properties are obtained, if in the above dyeing instructions the 1 n-butyrylamino - anthraquinone - 3,4 (N) - benzacridone is replaced is replaced by l-acetylamino-anthraquinone-3,4 (N) -benzacridone, l-propionylamino-anthraquinone-3,4 (N) -benzacridone, 1 - Valerylamino-anthraquinone-3,4 (N) -benzacridone, 1 -Capronylamino-anthraquinone-S ^ NJ-benzacridone, 1 -Caprylamino-anthraquinone-S ^ NJ-benzacridone or by 1-acryloylamino-anthraquinone-3,4 (N) -benzacridone.
Herstellung des in Absatz 1 dieses Beispiels
verwendeten FarbstoffsManufacture of the in paragraph 1 of this example
dye used
Ein Gemisch aus 200 Teilen Monochlorbenzol, 34,0 Teilenl-Amino-anthrachinon-3,4(N)-benzacridon und 21,2 Teilen n-Buttersäurechlorid wird unter Rühren 12 Stunden auf 1200C erhitzt. Nach dem Erkalten wird der entstandene Farbstoff abgesaugt und zunächst mit Monochlorbenzol, dann mit Methanol ausgewaschen und getrocknet. Das dunkelblaueA mixture of 200 parts of monochlorobenzene, 34.0 Teilenl-amino-anthraquinone-3,4 (N) -benzacridon and 21.2 parts of n-butyric acid chloride is heated for 12 hours to 120 0 C with stirring. After cooling, the resulting dye is filtered off with suction and washed first with monochlorobenzene and then with methanol and dried. The dark blue
809 618/526809 618/526
Farbstoffpulver löst sich in konzentrierter Schwefelsäure mit rotoranger Farbe.Dye powder dissolves in concentrated sulfuric acid with a red-orange color.
Ein Gewebe aus Polyäthylenglykolterephthalat wird mit nachstehender Druckpaste bedruckt:A fabric made of polyethylene glycol terephthalate is printed with the following printing paste:
30 g l-zS-Chlorpropionylamino-anthrachinon-3,4(N)-benzacridon 30 g of l-zS-chloropropionylamino-anthraquinone-3,4 (N) -benzacridone
150 g Natriumsalz eines sulfonierten Rizinusöls150 g of the sodium salt of a sulfonated castor oil
(etwa 50%ig)
210 g Wasser(about 50%)
210 g of water
600 g Kristallgummi-Verdickung (1:3) 10 g Entschäumer600 g crystal rubber thickening (1: 3) 10 g defoamer
1000 g1000 g
Nach dem Trocknen wird, svie unter Beispiel 1 beschrieben, weiterbehandelt.After drying, further treatment is carried out as described in Example 1.
Es wird ein rotstichigblauer Druck von sehr guten Echtheitseigenschaften erhalten.A reddish-tinged blue print with very good fastness properties is obtained.
Wird in dem obigen Beispiel das l-zS-Chlorpropionylamino-anthrachinon-3,4(N)-benzacridon ersetzt durch l-Chloracetylammo-anthrachinon-3,4(N)-benzacridon, so wird ein Druck von deutlich rotstichigerer blauer Nuance und von ebenfalls sehr guten Echtheitseigenschaften erhalten.If in the above example the l-zS-chloropropionylamino-anthraquinone-3,4 (N) -benzacridone replaced by l-chloroacetylammo-anthraquinone-3,4 (N) -benzacridone, the print is clearly more reddish blue Nuance and also obtained from very good fastness properties.
Claims (1)
USA.-Patentschrift Nr. 2 623 047.Considered publications:
U.S. Patent No. 2,623,047.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC36630A DE1278391B (en) | 1961-07-14 | 1961-07-14 | Dyeing and printing of fiber material made from high molecular weight polyesters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC36630A DE1278391B (en) | 1961-07-14 | 1961-07-14 | Dyeing and printing of fiber material made from high molecular weight polyesters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1278391B true DE1278391B (en) | 1968-09-26 |
Family
ID=7022378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC36630A Pending DE1278391B (en) | 1961-07-14 | 1961-07-14 | Dyeing and printing of fiber material made from high molecular weight polyesters |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1278391B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002051942A1 (en) * | 2000-12-22 | 2002-07-04 | Ciba Specialty Chemicals Holdings Inc. | Dyeing or printing of manufactured natural polymer and synthetic hydrophobic fibre materials |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2623047A (en) * | 1950-06-09 | 1952-12-23 | Cassella Farbwerke Mainkur Ag | Acridone vat dyestuffs |
-
1961
- 1961-07-14 DE DEC36630A patent/DE1278391B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2623047A (en) * | 1950-06-09 | 1952-12-23 | Cassella Farbwerke Mainkur Ag | Acridone vat dyestuffs |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002051942A1 (en) * | 2000-12-22 | 2002-07-04 | Ciba Specialty Chemicals Holdings Inc. | Dyeing or printing of manufactured natural polymer and synthetic hydrophobic fibre materials |
| US6893472B2 (en) | 2000-12-22 | 2005-05-17 | Ciba Specialty Chemicals Corporation | Dyeing or printing of manufactured natural polymer and synthetic hydrophobic fiber materials |
| KR100800984B1 (en) * | 2000-12-22 | 2008-02-05 | 시바 스페셜티 케미칼스 홀딩 인크. | Dyeing or printing method of manufactured natural polymer and hydrophobic synthetic fiber material |
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