DE1794398A1 - MONOAZO CONNECTIONS, THEIR PRODUCTION AND USE - Google Patents
MONOAZO CONNECTIONS, THEIR PRODUCTION AND USEInfo
- Publication number
- DE1794398A1 DE1794398A1 DE19651794398 DE1794398A DE1794398A1 DE 1794398 A1 DE1794398 A1 DE 1794398A1 DE 19651794398 DE19651794398 DE 19651794398 DE 1794398 A DE1794398 A DE 1794398A DE 1794398 A1 DE1794398 A1 DE 1794398A1
- Authority
- DE
- Germany
- Prior art keywords
- cyano
- compound
- amino
- azobenzene
- nitro
- 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
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 15
- -1 chloroacetoxy, cyanoacetoxy, hydroxyacetoxy, Methoxyacetoxy, methoxycarbonyloxy Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 238000004043 dyeing Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 239000000835 fiber Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 230000002209 hydrophobic effect Effects 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229920000591 gum Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZMESHQOXZMOOQQ-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)naphthalene Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZMESHQOXZMOOQQ-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 description 1
- NJXPYZHXZZCTNI-UHFFFAOYSA-N 3-aminobenzonitrile Chemical compound NC1=CC=CC(C#N)=C1 NJXPYZHXZZCTNI-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 229920001612 Hydroxyethyl starch Polymers 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 229940050526 hydroxyethylstarch Drugs 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 235000019960 monoglycerides of fatty acid Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0813—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
SANDOZ A.G IW^w'*, Case 150-1933/ASANDOZ A.G IW ^ w '*, Case 150-1933 / A
, S!r 35 , S! R 35
Monoazoverbindungen, ihre Herstellung und Verwendung Monoazo compounds , their production and use
Es wurde gefundenΛ dass sich die Monoazoverbindungen der Formel IIt was found Λ is that the monoazo compounds of the formula I
.CH CH -R CN 2 2 R4.CH CH -R CN 2 2 R 4
worin R, Chlor oder Cyan,where R, chlorine or cyano,
R Wasserstoff, Chlor oder Brom und R_ und R. Chloracetoxy, Cyanacetoxy, Hydroxyacetoxy,R is hydrogen, chlorine or bromine and R_ and R. chloroacetoxy, cyanoacetoxy, hydroxyacetoxy,
•J TE• J TE
Methoxyacetoxy, Methoxycarbonyloxy oder Aethoxycarbonyloxy bedeuten,Methoxyacetoxy, methoxycarbonyloxy or ethoxycarbonyloxy mean,
ausgezeichnet als Dispersionsfarbstoffe, zum Färben oder Bedrucken von Fasern oder Fäden oder daraus hergestellten Materialien aus voll- oder halbsynthetischen, hydrophoben, hochmolekularen organischen Stoffen eignen.excellent as disperse dyes, for dyeing or printing of fibers or threads or materials made from them made of fully or semi-synthetic, hydrophobic, high molecular weight organic substances.
Bevorzugt sind die Diazokomponenten der FormelThe diazo components of the formula are preferred
.-CN.-CN
undand
R5 ClR 5 Cl
V'obei Rg Wasserstoff oder Brom bedeutet. Die Herstellung der neuen Verbindungen erfolgt durch 'Diazotieren eines Amins der FormelV 'where Rg is hydrogen or bromine. The new compounds are prepared by diazotizing an amine of the formula
0„N-\O/~NH 0 "N- \ O / ~ NH
7
\
R2 7th
\
R 2
509819/1053509819/1053
- 2 - Case 150-1933/A - 2 - Case 150-1933 / A
und Kuppeln der erhaltenen Diazomiumverbindung mit einem Ämin der Formeland coupling the obtained diazomium compound with an amin the formula
CH CH -RCH CH -R
Diazotieren und Kuppeln werden nach allgemein bekannten Verfahren durchgeführt.Diazotization and coupling are carried out according to well-known methods carried out.
Die so hergestellten Farbstoffe werden im allgemeinen vor ihrer Anwendung in Färbepräparate übergeführt. Dazu werden sie zerkleinert, bis die Teilchengrösse im Mittel etwa 0,01 bis.10 Mikron und insbesondere etwa 0,1 bis 5 Mikron beträgt. Das Zerkleinern kann in Gegenwart von Dispergiermitteln oder Füllmitteln erfolgen. Beispielsweise wird der getrocknete Farbstoff mit einem Dispergiermittel, gegebenenfalls in Gegenwart von Füllmitteln, gemahlen oder in Pastenform mit einem Dispergiermittel geknetet und hierauf im Vakuum oder durch Zerstäuben getrocknet. Mit den so erhaltenen Präparaten kann man, nach Zugabe von mehr oder weniger Wasser, in sogenannter langer oder kurzer Flotte färben, klotzen oder bedrucken. Beim Färben in langer Flotte wendet man im allgemeinen bis zu etwa 20 g Farbstoff im Liter an, beim Färben in kurzer Flotte bis zu etwa 80 g im Liter, beim Klotzen bis zu etwa 150 g im Liter, vozugsweise 0,1 bis 100 g im Liter, und beim Drucken bis zu etwa 150 g im Kilogramm Druckpaste. Das Flottenverhältnis kann innerhalb weiter Grenzen gewählt werden, z.B. zwischen etwa 1:3 und 1:200, vorzugsweise zwischen 1:3 und 1:80.The dyes produced in this way are generally converted into coloring preparations before they are used. To do this, they are crushed, until the average particle size is about 0.01 to 10 microns, and especially about 0.1 to 5 microns. That Comminution can take place in the presence of dispersants or fillers take place. For example, the dried dye is mixed with a dispersant, optionally in the presence of fillers, ground or kneaded in paste form with a dispersant and then in a vacuum or by atomization dried. With the preparations obtained in this way, after adding more or less water, in so-called dye, pad or print long or short liquors. When dyeing in a long liquor one generally applies up to to about 20 g of dye per liter, when dyeing in a short liquor up to about 80 g per liter, when padding up to about 150 g per liter, preferably 0.1 to 100 g per liter, and when printing up to about 150 g per kilogram of printing paste. That The liquor ratio can be chosen within wide limits, e.g. between about 1: 3 and 1: 200, preferably between 1: 3 and 1:80.
Die Farbstoffe ziehen aus wässeriger Suspension ausgezeichnet auf Formkörper aus vollsynthetischen oder halbsynthetischen hochmolekularen. Stoffen auf. Besonders geeignet sind sie zum Färben, Klotzen oder Bedrucken von Fasern, Fäden oder Vliesen, Geweben oder Gewirken ausThe dyes are excellent for molded bodies made of fully synthetic or semisynthetic ones from aqueous suspension high molecular weight. Fabrics on. They are particularly suitable for dyeing, padding or printing Fibers, threads or fleeces, woven or knitted fabrics
5 0 9 819/10535 0 9 819/1053
- 3 - Case 150-1933/A- 3 - Case 150-1933 / A
linearen, aromatischen Polyestern, sowie aus Cellulose-2 1/2-acetat oder Cellulosetriacetat. Auch synthetische Polyamide, Polyolefine, Acrylnitrilpolymerisationsprodukte und PoIyvinylverbindungen lassen sich mit ihnen färben. Besonders wertvolle Färbungen werden auf linearen, aromatischen Polyestern erhalten. Diese sind im allgemeinen Polykondensationsprodukte aus Terephthalsäure und Glykolen, besonders Aethylenglykol.linear, aromatic polyesters, as well as cellulose-2 1/2 acetate or cellulose triacetate. Also synthetic polyamides, polyolefins, acrylonitrile polymerisation products and Polyvinyl compounds can be colored with them. Particularly valuable colorations are obtained on linear, aromatic polyesters. These are generally polycondensation products from terephthalic acid and glycols, especially ethylene glycol.
Man färbt nach an sich bekannten Verfahren. Polyesterfasern können in Gegenwart von Carriern bei Temperaturen zwischen etwa 80° und 125°C oder in Abwesenheit von Carriern unter Druck bei etwa 100° bis 1400C nach dem Ausziehverfahren gefärbt werden. Ferner kann man sie mit den wässerigen Dispersionen der neuen Farbstoffe klotzen, foulardieren oder bedrucken und die erhaltene Imprägnierung bei etwa 140° bis 2300C fixieren, z.B. mit Hilfe von Wasserdampf, Kontakthitze oder heisser Luft. Im besonders günstigen Temperaturbereich zwischen 180° und 2200C diffundieren die Farbstoffe schnell in die Polyesterfaser ein und sublimieren nicht wieder, auch wenn man diese hohen Temperaturen längere Zeit einwirken lässt. Dadurch wird das lästige Verschmutzen der Färbe-, apparaturen vermieden. Cellulose-2 1/2-acetat färbt man vorzugsweise zwischen ungefähr 65° und 800C und Cellulosetriacetat bei Temperaturen bis zu etwa 115°C, der günstigste pH-Bereich liegt zwischen 2 und 9 und besonders zwischen 4 und 8.It is dyed according to methods known per se. Polyester fibers can be dyed in the presence of carriers at temperatures between about 80 ° and 125 ° C or in the absence of carriers under pressure at about 100 ° to 140 0 C by the exhaust method. Further, they can with the aqueous dispersions of the novel dyes padding, padding or printing, and the impregnation obtained fix at about 140 ° to 230 0 C, for example with the aid of steam, contact heat or hot air. In particularly favorable temperature range between 180 ° and 220 0 C, the dyes diffuse rapidly into the polyester fiber and not sublimate again, even if these high temperatures a longer time to act leaves. This avoids annoying soiling of the dyeing equipment. Cellulose-2 1/2 acetate is preferably dyed between about 65 ° and 80 0 C and cellulose triacetate at temperatures up to about 115 ° C, the most favorable pH range is between 2 and 9, and particularly 4 to 8
Meist gibt man die üblichen Dispergiermittel zu, die vorzugsweise anionisch oder nichtionogen sind und auch im Gemisch miteinander verwendet werden können. Etwa 0,5 g Dispergiermittel je Liter Farbstoffzubereitung sind oft genügend, doch können auch grössere Mengen, z.B. bis zu etwa 3 g im Liter, angewandt werden. 5g übersteigende Mengen ergeben meist keinen weiteren Vorteil. Bekannte anionische Dispergiermittel, die für das Verfahren in Betracht kornmem,Usually the usual dispersants are added, which are preferred are anionic or non-ionic and can also be used in a mixture with one another. About 0.5 g Dispersants per liter of dye preparation are often sufficient, but larger amounts can also be used, e.g. up to about 3 g per liter can be used. Amounts in excess of 5g usually do not result in any further advantage. Known anionic dispersants which are suitable for the process,
- 4 - Case 150-1933/A- 4 - Case 150-1933 / A
sind beispielsweise Kondensationsprodukte aus Naphthalinsulfonsäuren und Formaldehyd, insbesondere Dinaphthylmethandisulfonate, Ester von sulfonierter Bernsteinsäure, Türkischrotöl und Alkalisalze von Schwefelsäureestern der Fettalkohole, z.B. Natriumlaurylsulfat oder Natriumcetylsulfat, Sulfitcelluloseablauge bzw. deren Alkalisalze, Seifen oder Alkalisulfate von Monoglyceriden von Fettsäuren. Beispiele bekannter und besonders geeigneter nichtionogener Dispergiermittel sind Anlagerungsprodukte von etwa 3-40 Mol Aethylenoxid an Alkylphenole, Fettalkohole oder Fettamine und deren neutrale Schwefelsäureester.are for example condensation products from naphthalenesulfonic acids and formaldehyde, especially dinaphthylmethane disulphonates, esters of sulphonated succinic acid, Turkish red oil and alkali salts of sulfuric acid esters of fatty alcohols, e.g. sodium lauryl sulfate or sodium cetyl sulfate, Sulphite cellulose waste liquor or its alkali salts, soaps or alkali sulphates of monoglycerides of fatty acids. Examples of known and particularly suitable nonionic Dispersants are addition products of about 3-40 mol of ethylene oxide with alkylphenols, fatty alcohols or fatty amines and their neutral sulfuric acid esters.
Beim Klotzen und Bedrucken wird man die üblichen Verdickungsmittel verwenden, z,B. modifizierte oder nicht modifizierte natürliche Produkte, beispielsweise Alginate, Britischgummi, Gummi arabicum, Kristal!gummi, Johannisbrotkernmehl, Tragant, Carboxymethylcellulose, Hydroxyathylcellulose, Stärke oder synthetische Produkte, beispielsweise Polyacrylamide oder Polyvinylalkohol.The usual thickening agents are used in padding and printing use, e.g. modified or unmodified natural products, for example alginates, British gum, Gum arabic, crystal gum, locust bean gum, tragacanth, Carboxymethyl cellulose, hydroxyethyl cellulose, starch or synthetic products, for example polyacrylamides or Polyvinyl alcohol.
Die erhaltenen Färbungen sind ausserordentlich echt, z.B. hervorragend thermofixier-, sublimier-, plissier-, rauchgas-, überfärbe-, trockenreinigungs-, chlor- und nassecht, z.B. wasser-, wasch- und schweissecht. Aetzbarkeit und Reserve von Wolle und Baumwolle sind gut. Hervorragend ist die Lichtechtheit, selbst in hellen Tonnen, sodass die neuen Farbstoffe auch als Mischungskomponenten für die Herstellung pastellfarbener Modetöne sehr geeignet sind. Die Farbstoffe sind bei*Temperaturen bis zu mindestens 2200C und besonders bei 80° bis 1400C verkoch-ünd reduktionsbeständig. Diese Beständigkeit wird weder durch das Flottenverhältnis noch äurch die Gegenwart von Färbebeschleunigern ungünstig beeinflusst.The dyeings obtained are extraordinarily fast, for example outstandingly heat-setting, subliming, pleating, smoke gas, over-dyeing, dry cleaning, chlorine and wet fast, for example water, washing and perspiration fast. The etchability and reserve of wool and cotton are good. The lightfastness is excellent, even in light colored bins, so that the new dyes are also very suitable as mixing components for the production of pastel-colored fashion shades. The dyes are temperatures up to at least 220 0 C and especially at 80 ° verkoch-Uend resistant to reduction by * to 140 0 C. This resistance is not adversely affected either by the liquor ratio or by the presence of dye accelerators.
5098 19/10 535098 19/10 53
Case 150-1933/ACase 150-1933 / A
Im folgenden Beispiel bedeuten die Teile Gewichtsteile, die Temperaturen sind in Celsiusgraden angegeben.In the following example, the parts mean parts by weight that Temperatures are given in degrees Celsius.
Be i s ρ i e 1 Be is ρ ie 1
Zu 120 Teilen konzentrierter Schwefelsäure werden bei 60-70° unter kräftigem Rühren 6,9 Teile gepulvertes Natriurcnitrit gegeben. Man rührt noch 10 Minuten bei 60°, kühlt dann auf 10° ab und fügt bei 10-20° 100 Teile Eisessig und danach 16,3 Teile 2-AmIno-5-nitrobenzonitril und 100 Teile Eisessig zu. Man rührt 2 Stunden nach und giesst die erhaltene Diazoniurusalz lösung zu einem Gemisch aus 35 Teilen Di-[ß-(methoxyacetoxy)-äthyl]-amino-3-cyanbenzol 100 Teilen .Eisessig,· 150 Teilen Eis und 10 Teilen Aminosulfonsäure. Die Kupplung wird in gepuffertem Medium (pH 3-4) zu Ende geführt. Der erhaltene Farbstoff wird abfiltriert, säurefrei gewaschen und getrocknet. Er färbt synthetische Fasern in roten Tönen mit ausgezeichneten Echtheiten.6.9 parts of powdered sodium nitrite are added to 120 parts of concentrated sulfuric acid at 60-70 ° with vigorous stirring given. The mixture is stirred for a further 10 minutes at 60 °, then cooled 10 ° and adds 100 parts of glacial acetic acid and then 16.3 parts of 2-amino-5-nitrobenzonitrile and 100 parts of glacial acetic acid at 10-20 ° to. The mixture is stirred for a further 2 hours and the diazoniuro salt obtained is poured solution to a mixture of 35 parts of di- [ß- (methoxyacetoxy) ethyl] amino-3-cyanobenzene 100 parts of glacial acetic acid, 150 parts of ice and 10 parts of aminosulfonic acid. the Coupling is completed in a buffered medium (pH 3-4). The dye obtained is filtered off, washed free of acid and dried. It dyes synthetic fibers in red tones with excellent fastness properties.
In der folgenden Tabelle sind weitere, analog zur Arbeitsvorschrift des Beispiels 1 herstellbare Farbstoffe der Formel 1 und die Nuancen ihrer Ausfärbung auf Polyesterfasermaterial angegeben.The table below shows further dyes of the formula which can be prepared analogously to the procedure of Example 1 1 and the nuances of their coloration on polyester fiber material specified.
No.E.g.
No.
Polyesterfaser
materialNuance on
Polyester fiber
material
Claims (9)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19651794398 DE1794398A1 (en) | 1965-08-20 | 1965-08-20 | MONOAZO CONNECTIONS, THEIR PRODUCTION AND USE |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19651794398 DE1794398A1 (en) | 1965-08-20 | 1965-08-20 | MONOAZO CONNECTIONS, THEIR PRODUCTION AND USE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1794398A1 true DE1794398A1 (en) | 1975-05-07 |
Family
ID=5707973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651794398 Pending DE1794398A1 (en) | 1965-08-20 | 1965-08-20 | MONOAZO CONNECTIONS, THEIR PRODUCTION AND USE |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1794398A1 (en) |
-
1965
- 1965-08-20 DE DE19651794398 patent/DE1794398A1/en active Pending
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