CH405555A - Verfahren zur Herstellung von Disazofarbstoffen - Google Patents

Verfahren zur Herstellung von Disazofarbstoffen

Info

Publication number: CH405555A
Authority: CH; Switzerland
Prior art keywords: amino; acid; sep; hydrogen sulfate; sulfonylaminoethyl
Prior art date: 1957-07-15

Application number

CH6884559A

Other languages

German (de)

English (en)

Inventor

Peter Dr Schmitz

Heinrich Dr Morschel

Gustav Dr Kleb

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1957-07-15

Filing date

1959-01-27

Publication date

1966-01-15

1957-07-15 Priority claimed from DEF23474A external-priority patent/DE1170898B/de

1958-01-31 Priority claimed from DEF27399A external-priority patent/DE1116846B/de

1959-01-27 Application filed by Bayer Ag filed Critical Bayer Ag

1966-01-15 Publication of CH405555A publication Critical patent/CH405555A/de

Links

239000000975 dye Substances 0.000 title claims description 33
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 27
238000000034 method Methods 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title description 3
230000008878 coupling Effects 0.000 claims description 12
238000010168 coupling process Methods 0.000 claims description 12
238000005859 coupling reaction Methods 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 10
-1 alkali metal cation Chemical group 0.000 claims description 9
150000004982 aromatic amines Chemical class 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
229910052802 copper Inorganic materials 0.000 claims description 4
239000010949 copper Substances 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
238000004532 chromating Methods 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000000565 sulfonamide group Chemical group 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 11
239000000243 solution Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
DTXSBIYNPOMMJY-UHFFFAOYSA-N 2-(sulfonylamino)ethyl hydrogen sulfate Chemical compound S(=O)(=O)(OCCN=S(=O)=O)O DTXSBIYNPOMMJY-UHFFFAOYSA-N 0.000 description 5
229920000742 Cotton Polymers 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
125000002843 carboxylic acid group Chemical group 0.000 description 5
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
238000004043 dyeing Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
239000004627 regenerated cellulose Substances 0.000 description 4
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 4
WSYUEVRAMDSJKL-UHFFFAOYSA-N ethanolamine-o-sulfate Chemical compound NCCOS(O)(=O)=O WSYUEVRAMDSJKL-UHFFFAOYSA-N 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [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 description 3
239000000203 mixture Substances 0.000 description 3
XRZPFCIJQNMRLG-UHFFFAOYSA-N NC(C=CC(S(NCCOS(O)(=O)=O)(=O)=O)=C1)=C1[N+]([O-])=O Chemical compound NC(C=CC(S(NCCOS(O)(=O)=O)(=O)=O)=C1)=C1[N+]([O-])=O XRZPFCIJQNMRLG-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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
229910000365 copper sulfate Inorganic materials 0.000 description 2
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
239000001103 potassium chloride Substances 0.000 description 2
235000011164 potassium chloride Nutrition 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
WFXYNZWXQMMWPV-UHFFFAOYSA-N 2-[(3-amino-4-chlorophenyl)sulfonylamino]ethyl hydrogen sulfate Chemical compound NC1=CC(S(=O)(=O)NCCOS(O)(=O)=O)=CC=C1Cl WFXYNZWXQMMWPV-UHFFFAOYSA-N 0.000 description 1
YLIALICPWNSJLH-UHFFFAOYSA-N 2-[(4-amino-2-nitrophenyl)sulfonylamino]ethyl hydrogen sulfate Chemical compound S(=O)(=O)(OCCNS(=O)(=O)C1=C(C=C(C=C1)N)[N+](=O)[O-])O YLIALICPWNSJLH-UHFFFAOYSA-N 0.000 description 1
VZLLZDZTQPBHAZ-UHFFFAOYSA-N 2-nitroaniline-4-sulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1[N+]([O-])=O VZLLZDZTQPBHAZ-UHFFFAOYSA-N 0.000 description 1
QTYQPEBQHHUSIK-UHFFFAOYSA-N 4-amino-2,5-dimethylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(C)C=C1N QTYQPEBQHHUSIK-UHFFFAOYSA-N 0.000 description 1
NEECEUZBAHTVIN-UHFFFAOYSA-N 4-amino-3-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1Cl NEECEUZBAHTVIN-UHFFFAOYSA-N 0.000 description 1
DFFMMDIDNCWQIV-UHFFFAOYSA-N 4-amino-3-methoxybenzenesulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=CC=C1N DFFMMDIDNCWQIV-UHFFFAOYSA-N 0.000 description 1
NHFKECPTBZZFBC-UHFFFAOYSA-N 4-amino-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1N NHFKECPTBZZFBC-UHFFFAOYSA-N 0.000 description 1
TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
NXKZQLNRMAJSIF-UHFFFAOYSA-N CC(C=C(C=C1)S(NCCOS(O)(=O)=O)(=O)=O)=C1N Chemical compound CC(C=C(C=C1)S(NCCOS(O)(=O)=O)(=O)=O)=C1N NXKZQLNRMAJSIF-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 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
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
229940072056 alginate Drugs 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000000987 azo dye Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000004040 coloring Methods 0.000 description 1
229940116318 copper carbonate Drugs 0.000 description 1
GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000001465 metallisation Methods 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/18—Monoazo compounds containing copper
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/22—Monoazo compounds containing other metals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)

CH6884559A 1957-07-15 1959-01-27 Verfahren zur Herstellung von Disazofarbstoffen CH405555A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEF23474A DE1170898B (de)	1957-07-15	1957-07-15	Verfahren zum Faerben und Bedrucken von Cellulosetextilmaterialien
DEF27399A DE1116846B (de)	1958-01-31	1958-01-31	Verfahren zur Herstellung von Disazofarbstoffen und deren Metallkomplexverbindungen

Publications (1)

Publication Number	Publication Date
CH405555A true CH405555A (de)	1966-01-15

Family

ID=25974047

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6884559A CH405555A (de)	1957-07-15	1959-01-27	Verfahren zur Herstellung von Disazofarbstoffen

Country Status (2)

Country	Link
BE (1)	BE575246A (fr)
CH (1)	CH405555A (fr)

1959
- 1959-01-27 CH CH6884559A patent/CH405555A/de unknown
- 1959-01-30 BE BE575246A patent/BE575246A/fr unknown

Also Published As

Publication number	Publication date
BE575246A (fr)	1959-07-30

Publication	Publication Date	Title
DE1544526C3 (de)	1975-08-14	Wasserlösliche Disazofarbstoffe, deren Metallkomplexverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung
CH312963A (de)	1956-03-15	Verfahren zur Herstellung von Azofarbstoffen
DE1544482C3 (de)	1975-07-17	Verfahren zur Herstellung von reaktiven, wasserlöslichen Disazofarbstoffen und ihren Metallkomplexverbindungen und die Verwendung dieser Farbstoffe zum Färben oder Bedrucken von Cellulose, Wolle, Seide oder Polyamidfasern
DE1444667C3 (de)	1973-12-13	Verfahren zur Herstellung von Azofarbstoffen
DE1046220B (de)	1958-12-11	Verfahren zur Herstellung von Monoazofarbstoffen und deren Metallkomplexverbindungen
DE940482C (de)	1956-03-22	Verfahren zur Herstellung von chromhaltigen Monoazofarbstoffen
CH405555A (de)	1966-01-15	Verfahren zur Herstellung von Disazofarbstoffen
DE698927C (de)	1940-11-20	Verfahren zur Herstellung von Tetrakisazofarbstoffen
DE741467C (de)	1943-11-11	Verfahren zur Herstellung von Disazofarbstoffen
DE848980C (de)	1952-09-11	Verfahren zur Herstellung neuer Azofarbstoffe
DE1419837C3 (de)	1975-05-22	Reaktive Monoazokupferkomplexfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung
DE849287C (de)	1952-09-15	Verfahren zur Herstellung von Trisazofarbstoffen
DE1544500B2 (de)	1973-08-16	Metallhaltige disazoreaktivfarbstoffe und verfahren zu deren herstellung
DE888907C (de)	1953-09-07	Verfahren zur Herstellung von Azofarbstoffen
AT164015B (de)	1949-09-26	Verfahren zur Herstellung metallhaltiger Azofarbstoffe
DE1285644B (de)	1968-12-19	Verfahren zur Herstellung metallhaltiger Azofarbstoffe
DE921225C (de)	1954-12-13	Verfahren zur Herstellung von Disazofarbstoffen
DE858441C (de)	1952-12-08	Verfahren zur Herstellung von kupferhaltigen Trisazofarbstoffen
AT162599B (de)	1949-03-10	Verfahren zur Herstellung von neuen Polyazofarbstoffen
AT165532B (de)	1950-03-10	Verfahren zur Herstellung neuer Azofarbstoffe
AT117029B (de)	1930-03-25	Verfahren zur Darstellung von Dis- und Polyazofarbstoffen.
DE850040C (de)	1952-09-22	Verfahren zur Herstellung von Azofarbstoffen
DE744018C (de)	1944-01-11	Verfahren zur Herstellung von Disazofarbstoffen
CH327283A (de)	1958-01-31	Verfahren zur Herstellung von chromhaltigen Monoazofarbstoffen
DE1116846B (de)	1961-11-09	Verfahren zur Herstellung von Disazofarbstoffen und deren Metallkomplexverbindungen