DE1804070C - Disazo dyes - Google Patents
Disazo dyesInfo
- Publication number
- DE1804070C DE1804070C DE1804070C DE 1804070 C DE1804070 C DE 1804070C DE 1804070 C DE1804070 C DE 1804070C
- Authority
- DE
- Germany
- Prior art keywords
- same
- parts
- och
- formula
- ciu
- 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.)
- Expired
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- 239000000975 dye Substances 0.000 title claims description 13
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 7
- 229920002647 polyamide Polymers 0.000 claims description 7
- -1 cyano, carboxyl Chemical group 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000005521 carbonamide group Chemical group 0.000 claims description 3
- 238000001321 HNCO Methods 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- OWIKHYCFFJSOEH-UHFFFAOYSA-N isocyanate Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N oxygen atom Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atoms Chemical group 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 230000001808 coupling Effects 0.000 description 14
- 238000010168 coupling process Methods 0.000 description 14
- 238000005859 coupling reaction Methods 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000011528 polyamide (building material) Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N Sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (Z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- BTNSSVRIZUUYGM-UHFFFAOYSA-N 2-(4-hydroxyphenyl)propanenitrile Chemical compound N#CC(C)C1=CC=C(O)C=C1 BTNSSVRIZUUYGM-UHFFFAOYSA-N 0.000 description 1
- OEHZEBOCZWCVMK-UHFFFAOYSA-N 3-(4-hydroxyphenyl)propanamide Chemical compound NC(=O)CCC1=CC=C(O)C=C1 OEHZEBOCZWCVMK-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-Methylenedianiline Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4,4'-Oxydianiline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Di(p-aminophenyl)sulphone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- RVGZUPFMHTWADC-UHFFFAOYSA-N N,N'-bis(4-aminophenyl)butanediamide Chemical compound C1=CC(N)=CC=C1NC(=O)CCC(=O)NC1=CC=C(N)C=C1 RVGZUPFMHTWADC-UHFFFAOYSA-N 0.000 description 1
- YQUUBUNFZCCYKQ-UHFFFAOYSA-N N,N'-bis(4-aminophenyl)heptanediamide Chemical compound C1=CC(N)=CC=C1NC(=O)CCCCCC(=O)NC1=CC=C(N)C=C1 YQUUBUNFZCCYKQ-UHFFFAOYSA-N 0.000 description 1
- HVCRWARLEIATFU-UHFFFAOYSA-N N,N'-bis(4-aminophenyl)hexanediamide Chemical compound C1=CC(N)=CC=C1NC(=O)CCCCC(=O)NC1=CC=C(N)C=C1 HVCRWARLEIATFU-UHFFFAOYSA-N 0.000 description 1
- AUXFZVANYVASTP-UHFFFAOYSA-N N,N'-bis(4-aminophenyl)octanediamide Chemical compound C1=CC(N)=CC=C1NC(=O)CCCCCCC(=O)NC1=CC=C(N)C=C1 AUXFZVANYVASTP-UHFFFAOYSA-N 0.000 description 1
- RVDSRPFOMDFFAG-UHFFFAOYSA-N N,N'-bis(4-aminophenyl)oxamide Chemical compound C1=CC(N)=CC=C1NC(=O)C(=O)NC1=CC=C(N)C=C1 RVDSRPFOMDFFAG-UHFFFAOYSA-N 0.000 description 1
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 201000002674 obstructive nephropathy Diseases 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WTXWKVALMHMPRJ-UHFFFAOYSA-N prop-1-ene;urea Chemical compound CC=C.NC(N)=O WTXWKVALMHMPRJ-UHFFFAOYSA-N 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- ZTHYODDOHIVTJV-UHFFFAOYSA-N propyl 3,4,5-trihydroxybenzoate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- POECFFCNUXZPJT-UHFFFAOYSA-M sodium;carbonic acid;hydrogen carbonate Chemical compound [Na+].OC(O)=O.OC([O-])=O POECFFCNUXZPJT-UHFFFAOYSA-M 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Description
CH2CH2RCH 2 CH 2 R
CH2CH2R1 CH 2 CH 2 R 1
in der R und R1 Cyan-, Carboxyl-, Carbomethoxy-, Carboüthoxy-, Curbopropoxy-, Carbobutoxy- und ■isobutoxyreste oder die Reste der Formelnin which R and R 1 are cyano, carboxyl, carbomethoxy, carboothoxy, curbopropoxy, carbobutoxy and isobutoxy radicals or the radicals of the formulas
-COOCH2CH2OCHj
— CO(OCH2CH2)2OCH3 -COOCH 2 CH 2 OCHj
- CO (OCH 2 CH 2 ) 2 OCH 3
oder gegebenenfalls durch einen oder zwei Methyloder Äthylreste, den Butyl- oder den y-Methoxypropylrest substituierte Carbonamidgruppen, die gleich oder verschieden sein können, und — A — eine direkte Bindung, ein Sauerstoff- oder Schwefelatom oder eineor optionally by one or two methyl or ethyl radicals, the butyl or the γ-methoxypropyl radical substituted carbonamide groups, which can be the same or different, and - A - a direct bond, an oxygen or sulfur atom, or a
-NH-, -SO2-, -CO-, — NH-CO-,-NH-, -SO 2 -, -CO-, - NH-CO-,
ΟΓΙ3 C^ H5ΟΓΙ3 C ^ H5
— N — CO- — N — CO-
-SO2NH-, ■— NHCONH-,- N - CO- - N - CO-
-SO 2 NH-, ■ - NHCONH-,
CH3 CH3 CH 3 CH 3
-N-SO2-N- (li] -CH2--N-SO 2 -N- (li] -CH 2 -
CH3
— C-CH3 CH 3
- C-CH 3
HNCO — (CH2)„— CONH-GruppeHNCO - (CH 2 ) "- CONH group
CH3 CH3 CH 3 CH 3
— N —CO —N-- N —CO —N-
Qi Hj C2H5 Qi Hj C 2 H 5
— N —CO —N-CH2- - N —CO —N-CH 2 -
CH3 C2H5 CH 3 C 2 H 5
— N —CO —N-- N —CO —N-
CH2 CH2 CH 2 CH 2
— N —CO —N-- N —CO —N-
3535
40 bedeutet, wobei /1 eine der Zahlen von O bis 6 darstellt. 40 denotes, where / 1 represents one of the numbers from 0 to 6.
Bevorzugte Reste R und R1 sind Cyan, Carboxyl, Carbomethoxy, Carboäthoxy, Carbopropoxy oder Carbonamid. . - Preferred radicals R and R 1 are cyano, carboxyl, carbomethoxy, carboethoxy, carbopropoxy or carbonamide. . -
Bevorzugte Gruppen Tür A sind Reste der Formeln _s__ —o— —N —CO —N-Preferred groups for Door A are residues of the formulas _ s __ —o— —N —CO —N-
R2 R2 R 2 R 2
H HH H
-N-OC-(CH2L-CO-N--N-OC- (CH 2 L-CO-N-
— CON —- CON -
— CH — CH3 CH2 CH2 CH2 - CH - CH 3 CH 2 CH 2 CH 2
1 I I I1 I I I
— N — CO — N- — N CO N-- N - CO - N- - N CO N-
45 wobei m eine Zahl von O bis 6 und R2 ein Wasserstoffatom oder eine Methyl- oder Äthylgruppe bedeutet. 45 where m is a number from 0 to 6 and R 2 is a hydrogen atom or a methyl or ethyl group.
Als technisch bevorzugte Farbstoffe der Formel I seien beispielsweise die Verbindungen der Formeln OH OHTechnically preferred dyes of the formula I are, for example, the compounds of the formulas OH OH
N = IN = I
CH2CH2CONH2 CH 2 CH 2 CONH 2
NHCONHNHCONH
CH2CH2CONH2 CH 2 CH 2 CONH 2
OHOH
CH2CH2COOR3 CH2CH2COOR3 CH 2 CH 2 COOR 3 CH 2 CH 2 COOR 3
angeführt, wobei R3 einen Alkylrest mit I bis 4 C-Atomen oder einen Rest der Formelnlisted, where R 3 is an alkyl radical having I to 4 carbon atoms or a radical of the formulas
-CH2CH2OCH3 oder -(OCH2CH2I2OCH3 -CH 2 CH 2 OCH 3 or - (OCH 2 CH 2 I 2 OCH 3
bedeutet.means.
Die nouon Farbstoffe eignen sich zum Filrben von Celluloseestern oder Polyestern und Polyamiden, Insbesondere tiuf Polyestern und synthetischen Polyamiden erhalt mun damit sehr echte Färbungen, wobei ( die Lieht-, Nuß- und thermischen Echtheiten hervor- s zuhebon sind, Filrbcgul sind vorzugsweise Fasern und Textilmaterial, wie Gewebe, Gewirke, Füden und auch Vliese,The nouon dyes are suitable for Filrben of Celluloseestern or polyesters and polyamides, polyesters and tiuf particular synthetic poly amides obtained mun thus very fast dyeings, wherein (the Lieht-, nut and thermal fastness hervor- s are zuhebon, Filrbcgul are preferably fibers and Textile material, such as woven fabrics, knitted fabrics, threads and also fleeces,
Man kann die Farbstoffe der Formel I z. B. dadurch herstellen, daß man Tctrazovcrbindungen von 10 Diaminen der allgemeinen Formel II You can use the dyes of formula I z. B. produced by Tctrazovcrindungen of 10 diamines of the general formula II
IIII
mil Kupplungskomponenten der allgemeinen Formeln IIIwith coupling components of the general formulas III
OHOH
'5'5
2020th
IIIIII
CH2CH2R1 CH 2 CH 2 R 1
umsetzt. 35implements. 35
Im einzelnen kommen als aromatische Diamine der allgemeinen Formel II beispielsweise in Betracht:Examples of suitable aromatic diamines of the general formula II are:
4,4'-Diaminodiphenylmethan,4,4'-diaminodiphenylmethane,
2,2-(4,4'-Diaminodiphenyl)-propan, 402,2- (4,4'-diaminodiphenyl) propane, 40
1,1 -^'-DiaminodiphenylJ-cyclohexan, 4,4'-Diaminobenzophenon,1,1 - ^ '- DiaminodiphenylJ-cyclohexane, 4,4'-diaminobenzophenone,
Ben'zidin,Ben'zidine,
4,4'-Diaminodiphenyläther,4,4'-diaminodiphenyl ether,
4,4'-DiaminodiphenyIsulfid, 454,4'-diaminodiphenyl sulfide, 45
4,4'-Diaminodiphenylsulfon,4,4'-diaminodiphenyl sulfone,
4,4'-Diaminodiphenylamin,4,4'-diaminodiphenylamine,
4,4'-Diaminodiphenylharnstoff,4,4'-diaminodiphenylurea,
N,N'-Dimethyl-4,4'-diaminodiphenylhamstofT, N,N'-Diäthyl-4,4'-diaminodiphenylharnstoff, 50 N Methyl-N'-äthyM^'-diaminodiphenylharnstoff, N, N'-dimethyl-4,4'-diaminodiphenylurstoff, N, N'-diethyl-4,4'-diaminodiphenylurea, 50 N methyl-N'-ethyM ^ '- diaminodiphenylurea,
N,N'-(4,4'-diaminodiphenyl)-äthyIenharnstofT, N,N'-(4,4'-diaminodiphenyl)-propylenharnstoff, Sulfanilsäure-(p-amino)-anilid, 55N, N '- (4,4'-diaminodiphenyl) -ethylene urea, N, N '- (4,4'-diaminodiphenyl) propylene urea, sulfanilic acid (p-amino) anilide, 55
Oxalsäurc-bis-(4-aminophenylamid), Bernsteinsäure-bis-(4-aminophenyIamid), Adipinsäure-bis-(4-aminophenylamid), Pimelinsäure-bis-(4-aminophenylamid), Korksäure-bis-(4-aminophenylamid), 60Oxalic acid bis (4-aminophenylamide), succinic acid bis (4-aminophenylamide), Adipic acid bis (4-aminophenylamide), pimelic acid bis (4-aminophenylamide), Suberic acid bis (4-aminophenylamide), 60
4,4'-Diaminobcnzoesäurcanilid, N-MethyM.'t'-iliaminobenzoestiureanilicl, , ., , N-ÄthyM^'-diaminobcnzoesäureanilid,4,4'-diaminobenzoic acid canilide, N-MethyM.'t'-iliaminobenzoestiureanilicl,,.,, N-EthyM ^ '- diaminobcnzoic anilide,
Verbindungen der allgemeinen Forme! HI sind Ii ortho-Stcllung zur OH-Gruppe kuppelnde Derivate der /<-(4'- Hydroxyphenyl) - propionsäure, z. B. //■(4'-Hydroxyphenyl)-propionitril, //-(4'-Hydroxy phenyl)- propionsäure, /i-(4' - Hydroxyphenyl) - propionsäuremethylestcr, -äthylester, -propylester, -bu- tylcster, -isobutylester, -methyläthylenglykolester, -methyläthy lendiglykolester, β - (4' - Hydroxyphenyl)- propionsäureamid, -methylamid, -üthylamid, -bu- tylamid, -dimethylamtd oder -diäthylamid. Connections of general form! HI are derivatives of / <- (4'-hydroxyphenyl) propionic acid coupling ortho to the OH group, e.g. B. // ■ (4'-hydroxyphenyl) propionitrile, // - (4'-hydroxyphenyl) - propionic acid, / i- (4 ' - hydroxyphenyl) - propionic acid methyl ester, ethyl ester, propyl ester, butyl ester , -isobutyl ester, -methylethylene glycol ester, -methyläthy lendiglykolester, β - (4 '- hydroxyphenyl) - propionic acid amide, -methylamid, -üthylamid, -butylamid, -dimethylamtd or -diethylamide.
Die Verbindungen der allgemeinen Formel II können in üblicher Weise tetrazotiert werden, z. B. in verdünnter wäßriger Salz- oder Schwefelsäure, gegebenenfalls unter Zusatz von Dispergiermitteln, in organischen Lösungsmitteln, wie Eisessig, oder in Mischungen aus Wasser und organischen Lösungsmitteln. The compounds of general formula II can be tetrazotized in a customary manner , for. B. in dilute aqueous hydrochloric or sulfuric acid, optionally with the addition of dispersants, in organic solvents such as glacial acetic acid, or in mixtures of water and organic solvents.
Die Kupplung der Tetrazoniumsalze der aromatischen Amine der allgemeinen Formel II mit den Kupplungskomponenten der allgemeinen Formel II erfolgt zweckmäßigerweise in wäßrig-alkalischer Lösung unter Zusatz säurebindender Mittel, wie Natriumhydroxid, Natriumcarbonat oder Natriumhydrogencarbonat. The coupling of the tetrazonium salts of the aromatic amines of the general formula II with the coupling components of the general formula II is expediently carried out in an aqueous-alkaline solution with the addition of acid-binding agents, such as sodium hydroxide, sodium carbonate or sodium hydrogen carbonate.
Gegenüber nächstvergleichbaren aus den französischen Patentschriften 1 194 450 und 1 347 512 sowie der belgischen Patentschrift 684 584 bekannten Farbstoffen weisen die erfindungsgemäßen Farbstoffe Vorteile im Ziehvermögen, in der Lichtechtheit und der Thermofixierechtheit auf Polyamid und Polyestergewebe auf. Es war überraschend, daß die neuen Farbstoffe trotz der Molekülgröße, die allein schon durch die Disazogruppierung bewirkt wird, ein vorzügliches Ziehvermögen auf Polyester und Polyamiden aufweisen.Opposite nearest comparable from French Patents 1,194,450 and 1,347,512 and Belgian Patent 684,584 known dyes include dyes advantages of the invention in the drawability, in the light fastness and the heat setting to polyamide and polyester fabrics on. It was surprising that the new dyes, in spite of the molecular size, which is caused by the disazo grouping alone, have excellent drawability on polyesters and polyamides.
Sofern nicht anders vermerkt, beziehen sich Angaben über Teile und Prozente in den folgenden Beispielen auf das Gewicht.Unless otherwise stated, parts and percentages in the following examples relate to on weight.
20 Teile .4,4'· Diaminodiphenyläther werden in einer Mischung von 600 Teilen Eiswasser und 50 Raumteilen konzentrierter Salzsäure 1 Stunde bei 0 bis 5°C gerührt. Bei der gleichen Temperatur läßt man dann 60 Raumteile 23%ige Natriumnitritlösung langsam zulaufen. Man rührt weitere 2 Stunden und beseitigt danach einen gegebenenfalls vorhandenen Überschuß an salpetriger Säure durch Zugabe von Amidosulfonsäure. Anschließend wird die Diazolösung bei 0 bis 5° C nach und nach und unter Zugabe von 350 Teilen Eis zu einer Lösung von 37 Teilen ^'-Hydroxyphenyl) - propionsäuremethylester, 20 Teilen 50%iger Natronlauge und 30 Teilen Natriumcarbonat in 600 Teilen Wasser hinzugefügt. Nach Beendigung der Kupplung wird der gebildete Farbstoff der Formel20 parts of .4,4 '· Diaminodiphenyläther are in a mixture of 600 parts of ice water and 50 parts by volume concentrated hydrochloric acid at 0 to 5 ° C for 1 hour. At the same temperature one leaves then slowly run in 60 parts by volume of 23% sodium nitrite solution. The mixture is stirred for a further 2 hours and eliminated then any excess of nitrous acid by adding sulfamic acid. Then the diazo solution at 0 to 5 ° C gradually and with the addition of 350 parts of ice to a solution of 37 parts of methyl ^ '- hydroxyphenyl) propionate, 20 parts 50% strength sodium hydroxide solution and 30 parts of sodium carbonate in 600 parts of water were added. After completion the coupling is the resulting dye of the formula
OHOH
CH2CH2COOCH3 CH2CH2COOCH3 CH 2 CH 2 COOCH 3 CH 2 CH 2 COOCH 3
I 804 070I 804 070
abgesaugt, mit Wässer gewaschen und getrocknet. Er iHllt als geibbtoWerPulver on, das sich in Dithlfid /jil glb Fb löAspirated, washed with water and dried. It iHllt as gibbtoWerPowder, which is in Dithlfid / jil glb Fb
Er iHllt als geibtoWerPulver on, da methylformamid /njil gelber Fnfbc löst. .. F^ttrfat man, 100.feile PolyathylefUerephthaiatrasern 60 Mlnut^h' bei (25° C im Druckapparat lh 6inem Bad, das 2000 feile Wasser, 0,8 Teile dos feinverteilt™ Farbstoffes und 2fö|lq des sulfuriert Anlagerüngsprodukies von 80 Mol Aihylenöxid an 1 MoI Spermölalkohol enthalt, so efnllt rhaii eine refrf gelbe Färbung von au8|ez0icn.no(ör thörmispner Beständigkeit und hervorragender Licht- und NaßcchtHoit.It can be used as a powder because methylformamide / njil yellow Fnfbc dissolves. .. F ^ ttrfat one, 100 .file PolyathylefUerephthaiatras 60 mlnuts ^ h 'at (25 ° C in the pressure apparatus 1h 6inem bath, the 2000 file water, 0.8 part of the finely divided dyestuff and 2folq of the sulfurized addition product of 80 mol Contains ethylene oxide in 1 mole of sperm oil alcohol, so rhaii has a refrf yellow coloration of au8 | ez0icn.no (ör thörmispner resistance and excellent light and wetness.
Weitere Gelbfarbstoffe. die ^Uf Polyestern b?w. Polyamiden Färbungen mit ähnlichen Eigenschaflen ergeben, lasseh sich in gleicher Weise aus den Tetra'zokomponqntcn und Kupplungskomponenten der folgenden Tabelle herstellen:Other yellow dyes. the ^ uf polyesters b? w. Polyamide dyeings with similar properties can be derived in the same way from the tetrazo components and manufacture coupling components from the following table:
NH,NH,
NH,NH,
desgl.the same
desgl.the same
desgl.the same
desgl.the same
desgl.the same
desgl.the same
CH2CH2CN
OHCH 2 CH 2 CN
OH
CH2CH2COOC3H7(H)
OHCH 2 CH 2 COOC 3 H 7 (H)
OH
CH2CH2COO(CH2J11CH3 CH 2 CH 2 COO (CH 2 J 11 CH 3
Mischung aus gleichen Teilen der Verbindung mit η — O, 1 und 2Mixture of equal parts of the compound with η - O, 1 and 2
CH2CH2COOCH2Ch2OCH.,CH 2 CH 2 COOCH 2 Ch 2 OCH.,
Fortsetzungcontinuation
Tetrazokomponente entsprechend Formel II Kupplungskomponente entsprechend Formel IIITetrazo component according to formula II Coupling component according to formula III
10 11 12 13 1410 11 12 13 14
1515th
/V-NH1 / V-NH 1
NH2 NH 2
desgl.the same
• V-NH,• V-NH,
desgl.the same
desgl.the same
CH3 CH 3
i>—s CH3 i> -s CH 3
NH2 NH 2
desgl.the same
OHOH
CH2 — CH2COOCH2 H3CO — CH2CH2O — CH2 CH 2 - CH 2 COOCH 2 H 3 CO - CH 2 CH 2 O - CH 2
OHOH
CH2CH2COOH OHCH 2 CH 2 COOH OH
CH2CH2CNCH 2 CH 2 CN
OHOH
CH2CH2COOCH3 CH 2 CH 2 COOCH 3
OH /r OH / r
CH2CH2CONH(CH2)3OCH3 OHCH 2 CH 2 CONH (CH 2 ) 3 OCH 3 OH
CH2CH2CN OHCH 2 CH 2 CN OH
# 6.1\ 109 62S/M1# 6. 1 \ 109 62S / M1
Fortsetzungcontinuation
JLUJLU
O = CO = C
desgl.the same
/CONH (CH2),, ^CONH/ CONH (CH 2 ) ,, ^ CONH
NH,NH,
NH2 NH 2
Gemisch aus gleichen Teilen der Verbindungen mit π = 4 und η = Mixture of equal parts of the compounds with π = 4 and η =
desgl.the same
desgl.the same
desgl.the same <o<o
CH2CH2CCH 2 CH 2 C
desgl.the same
OHOH
, CH1CH1COOCH3 , CH 1 CH 1 COOCH 3
1111th
Fortsetzungcontinuation
1212th
CH3-NCH 3 -N
O =O =
NH,NH,
-NH2 -NH 2
desgl.the same
O = CO = C
NH,NH,
NH,NH,
H,CH, C
desgl.the same
OHOH
CH,CH,CONH,CH, CH, CONH,
OHOH
ι 804ι 804
3131
3232
3333
desgl.*the same. *
H2NH 2 N
24,2 Teile 4,4'-Diamino-diphenyIharnstoff werden mehrere Stunden mit 300 Raumteilen Wasser und 0,3 Teilen des Umsetzungsproduktes von Oleylamin mit ungefähr 12 Mol Athylenoxid bei Raumtemperatür verrührt. Nach Zugabe von SO Raumteilen konzentrierter Salzsäure und 300 Teilen Eis läßt man bei 0 bis 5° C 60 Raumteile 23%ige Natriumnitritlösung24.2 parts of 4,4'-diamino-diphenylurea become several hours with 300 parts by volume of water and 0.3 parts of the reaction product of oleylamine stirred with about 12 moles of ethylene oxide at room temperature. After adding 50 parts by volume of concentrated hydrochloric acid and 300 parts of ice, the mixture is left on 0 to 5 ° C 60 parts by volume 23% sodium nitrite solution langsam zulaufen. Man rührt bei der gleichen Temperatur weitere 2 Stunden und beseitigt dann einen gegebenenfalls vorhandenen Überschuß an salpetriger Säure durch Zugabe von Amidosulfonsäure. Nach dem Filtrieren kuppelt man die Diazoverbindung analog der im Beispiel 1 angegebenen Arbeitsweise aul 34 Teile /i-(4'-Hydroxyphenyl)-propionsäureamid. bs entsteht ein gelbbrauner Farbstoff entsprechend der Formelto run slowly. The mixture is stirred at the same temperature for a further 2 hours and then one is eliminated any excess of nitrous acid present by adding sulfamic acid. To the diazo compound is coupled to the filtration analogously to the procedure given in Example 1 aul 34 parts of i- (4'-hydroxyphenyl) propionic acid amide. A yellow-brown dye is produced accordingly the formula
N =N =
CH2CH2CONH2 CH 2 CH 2 CONH 2
NHCONHNHCONH
der sich in Dimethylformamid mit tiefgelber Farbe löst.which dissolves in dimethylformamide with a deep yellow color.
Zum Färben von 100 Teilen Polyamidgewebe in einem Bad, das 1 Teil dieses Farbstoffes in feinverteilter Form und 2 Teile sulfierten Spermölalkohol in 2000 Teilen Wasser enthält, wird es darin 90 MinuFor dyeing 100 parts of polyamide fabric in a bath containing 1 part of this dye in finely divided form and 2 parts of sulfated sperm oil alcohol in 2000 parts of water, it is 90 minu ten bei 95 bis 100° C behandelt. Man erhält eine reine Gelbfärbung die sehr gut licht- und naßecht ist.th treated at 95 to 100 ° C. You get a pure Yellow coloring which is very good light and wet fast.
Weitere GelblarbstofTe mit ähnlichen Eigenschaften lassen sich m gleicher Weise aus den Tetrazokomponenten. und Kupplungskomponenten der folgendenOther yellow pigments with similar properties can be m in the same way from the tetrazo components. and coupling components of the following
BeUpIeIEXAMPLE
3535
llelsplulllelsplul
Tvtrii/okompnnente cnisprcchuml Formel IlTvtrii / okompnnente cnisprcchuml formula Il
NH2 NH 2
desgl.the same
. desgl.. the same
Kupplungskomponente entsprechend Formel IIICoupling component according to formula III
Claims (2)
Family
ID=
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