DE2913720A1 - Stable, liq. compsn. of tetra:azo dye - contg. water, ether alcohol and alkanolamine, for dyeing paper and cotton - Google Patents
Stable, liq. compsn. of tetra:azo dye - contg. water, ether alcohol and alkanolamine, for dyeing paper and cottonInfo
- Publication number
- DE2913720A1 DE2913720A1 DE19792913720 DE2913720A DE2913720A1 DE 2913720 A1 DE2913720 A1 DE 2913720A1 DE 19792913720 DE19792913720 DE 19792913720 DE 2913720 A DE2913720 A DE 2913720A DE 2913720 A1 DE2913720 A1 DE 2913720A1
- Authority
- DE
- Germany
- Prior art keywords
- weight
- alkanolamine
- water
- stable
- liq
- 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.)
- Withdrawn
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 229920000742 Cotton Polymers 0.000 title abstract description 3
- 238000004043 dyeing Methods 0.000 title abstract description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 title abstract 2
- 239000000987 azo dye Substances 0.000 title 1
- -1 polyazo Polymers 0.000 claims abstract description 10
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229940043276 diisopropanolamine Drugs 0.000 claims abstract description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 6
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims abstract description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003513 alkali Substances 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000975 dye Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 150000001412 amines Chemical class 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000005204 hydroxybenzenes Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/50—Tetrazo dyes
- C09B35/60—Tetrazo dyes of the type
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0072—Preparations with anionic dyes or reactive dyes
- C09B67/0073—Preparations of acid or reactive dyes in liquid form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Abstract
Description
Flüssige FarbstoffzubereitungLiquid dye preparation
Gegenstand der vorliegenden Erfindung sind flüssige Farbstoffzubereitungen, enthaltend 10 - 40 Gew. -% eines Farbstoffes der Formel wobei A, B, C, D = gegebenenfalls substituiertes Phenyl(en) oder Naphthyl(en), 5 - 60 Gew.-% Wasser, vorzugsweise 30 - 50 Gew.-%, 10 - 60 Gew.-%, vorzugsweise 15 - 30 Gew.- einer Verbindung der Formel R - (0-Alkylenzn-OH wobei R = H, C1-C4-Alkyl, n 2 2, und Alkylen = C2-C3-Alkylen, vorzugsweise -CH2-CH2- oder 10 - 60 Gew.-%, vorzugsweise 15 - 30 Gew.-% eines Mono-, Di- oder Tri-alkanolamins.The present invention relates to liquid dye preparations containing 10-40% by weight of a dye of the formula where A, B, C, D = optionally substituted phenyl (en) or naphthyl (en), 5 - 60% by weight of water, preferably 30 - 50% by weight, 10 - 60% by weight, preferably 15 - 30% by weight of a compound of the formula R - (0-alkylene-n-OH where R = H, C1-C4-alkyl, n 2 2, and alkylene = C2-C3-alkylene, preferably -CH2-CH2- or 10-60% by weight, preferably 15-30% by weight, of a mono-, di- or tri-alkanolamine.
A und D stellen vorzugsweise Reste von Kupplungskomponenten der Aminobenzolreihe oder der Hydroxybenzolreihe dar, z.B. 1,3-Diaminophenyl.A and D preferably represent residues of coupling components of the aminobenzene series or the hydroxybenzene series, e.g., 1,3-diaminophenyl.
B und C stehen vorzugsweise für gegebenenfalls substituiertes Phenylen. Als Substituenten kommen dabei beispielsweise Sulfo, C1-C4-Alkyl oder C1-C4-Alkoxy in Betracht.B and C preferably represent optionally substituted phenylene. Examples of substituents are sulfo, C1-C4-alkyl or C1-C4-alkoxy into consideration.
n steht beispielsweise für 2 - 10, vorzugsweise für 2 oder 3, Gegebenenfalls können die Zubereitungen weitere wassermischbare organische Lösungsmittel enthalten, beispielsweise Amide von aliphatischen Carbonsäuren wie Dimethyl- formamid, weiterhin können gegebenenfalls vorhanden sein: Oberflächenaktive Stoffe, z.B. nicht ionogene oder anionische Dispergiermittel wie Alkyl-, Alkenyl- oder Alkylphenylpolyglykolether, ein Alkyl- oder Alkenylsulfat, ein Alkylbenzolsulfonat, Fettsäureamido-ethansulfonat oder ein Ligninsulfonat mit Kationen, wie e e NH4 , Li , Na und K Die Farbstoffe können in Form der Alkali-, Ammonium-oder Aminsalze vorliegen; vorzugsweise liegen sie in Form der Alkanolaminsalze vor.n stands, for example, for 2-10, preferably for 2 or 3, optionally the preparations may contain other water-miscible organic solvents, for example amides of aliphatic carboxylic acids such as dimethyl formamide, the following may also be present: surface-active substances, e.g. not ionic or anionic dispersants such as alkyl, alkenyl or alkylphenyl polyglycol ethers, an alkyl or alkenyl sulfate, an alkylbenzenesulfonate, fatty acid amido-ethanesulfonate or a lignosulfonate with cations such as e e NH4, Li, Na and K The dyes can be in the form of the alkali, ammonium or amine salts; preferably lie they exist in the form of the alkanolamine salts.
Geeignete Verbindungen I sind beispielsweise Polyglykole und dere Monoalkylether, vorzugsweise Di- und Triethylenglykol sowie dere Monomethyl- und Monoethylether.Suitable compounds I are, for example, polyglycols and theirs Monoalkyl ethers, preferably di- and triethylene glycol and their monomethyl and Monoethyl ether.
Geeignete Alkanolamine sind beispielsweise: Ethanolamin, Diethanolamin, Triethanolamin, Diisopropanolamin, Triisopropanolamin, Tris-E2- (2-hydroxy-ethoxy) -ethyjlamin, 2-Amino-2-hydroxymethyl-propandiol-(1,3), N-Methyldiethanolamin und Mischungen aus diesen Basen.Suitable alkanolamines are, for example: ethanolamine, diethanolamine, Triethanolamine, diisopropanolamine, triisopropanolamine, tris-E2- (2-hydroxy-ethoxy) -ethylamine, 2-amino-2-hydroxymethyl-propanediol- (1,3), N-methyldiethanolamine and Mixtures of these bases.
Bevorzugt sind dabei Triethanolamin, Diisopropanolamin, N-Methyldiethanolamin.Triethanolamine, diisopropanolamine and N-methyldiethanolamine are preferred.
Die Herstellung der Zubereitung erfolgt beispielsweise folgendermaßen: Eine in üblicher Weise hergestellte wäßrige Dispersion des Na-Salzes des Farbstoffes wird durch Zusatz starker Säuren, beispielsweise Salz- oder Schwefelsäure, auf pH<1 gestellt und der Farbstoff isoliert. Der so erhaltene Preßkuchen wird anschließend mit den entsprechenden Mengen Verbindung I, Alkanolamin, sowie gegebenenfalls Wasser und weiteren Lösungsmitteln in üblicher Weise homogenisiert, gegebenenfalls unter Zusatz von Dispergiermitteln.The preparation is made, for example, as follows: One aqueous dispersion of the sodium salt of the dye prepared in a conventional manner is adjusted to pH <1 by adding strong acids, e.g. hydrochloric or sulfuric acid and the dye isolated. The press cake thus obtained is then with the appropriate amounts of compound I, alkanolamine, and optionally water and other solvents homogenized in the usual way, optionally under Addition of dispersants.
Die so erhaltenen wäßrigen Zubereitungen sind stabil und lassen sich direkt zum Färben von Baumwolle und Papier einsetzen.The aqueous preparations obtained in this way are stable and can be Use directly for dyeing cotton and paper.
Beispiel 1 100 Gew.-Teile Preßkuchen des in üblicherWeise gekuppelten und bei pH 0,8 isolierten Farbstoffes der Formel enthaltend 28 Gew.-Teile Farbstoff und 72 Gew.-Teile Wasser werden unter kräftigem Rühren mit einem Gemisch aus 23 Gew.-Teilen Diethylenglykol und 21 Gew.-Teilen Diisopropanolamin verrührt. Man erhält eine stabile Lösung. Ähnliche stabile Lösungen erhält man bei Verwendung von 21 Gew.-Teilen Triethanolamin oder 21 Gew.-Teilen N-Methyl-diethanolamin oder 10,5 Gew.-Teilen N-Methyl-diethanolamin und 10,5 Gew.-Teilen Diisopropanolamin anstelle von 21 Gew.-Teilen Diisopropanolamin.Example 1 100 parts by weight of the presscake of the dye of the formula, coupled in the customary manner and isolated at pH 0.8 containing 28 parts by weight of dye and 72 parts by weight of water are stirred with vigorous stirring with a mixture of 23 parts by weight of diethylene glycol and 21 parts by weight of diisopropanolamine. A stable solution is obtained. Similar stable solutions are obtained when using 21 parts by weight of triethanolamine or 21 parts by weight of N-methyl-diethanolamine or 10.5 parts by weight of N-methyl-diethanolamine and 10.5 parts by weight of diisopropanolamine instead of 21 Parts by weight of diisopropanolamine.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792913720 DE2913720A1 (en) | 1979-04-05 | 1979-04-05 | Stable, liq. compsn. of tetra:azo dye - contg. water, ether alcohol and alkanolamine, for dyeing paper and cotton |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792913720 DE2913720A1 (en) | 1979-04-05 | 1979-04-05 | Stable, liq. compsn. of tetra:azo dye - contg. water, ether alcohol and alkanolamine, for dyeing paper and cotton |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2913720A1 true DE2913720A1 (en) | 1980-10-16 |
Family
ID=6067535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792913720 Withdrawn DE2913720A1 (en) | 1979-04-05 | 1979-04-05 | Stable, liq. compsn. of tetra:azo dye - contg. water, ether alcohol and alkanolamine, for dyeing paper and cotton |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2913720A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0738764A1 (en) * | 1995-04-22 | 1996-10-23 | Hoechst Aktiengesellschaft | Tetrakisazo compounds, their preparation and their use as dyestuffs |
-
1979
- 1979-04-05 DE DE19792913720 patent/DE2913720A1/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0738764A1 (en) * | 1995-04-22 | 1996-10-23 | Hoechst Aktiengesellschaft | Tetrakisazo compounds, their preparation and their use as dyestuffs |
| US5668260A (en) * | 1995-04-22 | 1997-09-16 | Hoecht Aktienge Sellschaft | Tetrakisazo Compounds, the method of preparation thereof and the process of pyeing |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |