CH419382A - Verfahren zur Herstellung von Azofarbstoffen der Phthalocyaninreihe - Google Patents

Verfahren zur Herstellung von Azofarbstoffen der Phthalocyaninreihe

Info

Publication number: CH419382A
Authority: CH; Switzerland
Prior art keywords: amino; groups; radical; acid; phthalocyanine
Prior art date: 1958-08-07

Application number

CH7663159A

Other languages

German (de)

English (en)

Inventor

Richard Dr Fleischhauer

Original Assignee

Cassella Farbwerke Mainkur 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.)

1958-08-07

Filing date

1959-08-05

Publication date

1966-08-31

1959-08-05 Application filed by Cassella Farbwerke Mainkur Ag filed Critical Cassella Farbwerke Mainkur Ag

1966-08-31 Publication of CH419382A publication Critical patent/CH419382A/de

Links

IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 title claims description 13
238000000034 method Methods 0.000 title claims description 7
239000000987 azo dye Substances 0.000 title claims description 6
238000004519 manufacturing process Methods 0.000 title claims description 5
239000000975 dye Substances 0.000 claims description 17
-1 amino compound Chemical class 0.000 claims description 14
239000007859 condensation product Substances 0.000 claims description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 6
150000003254 radicals Chemical class 0.000 claims description 6
230000003381 solubilizing effect Effects 0.000 claims description 5
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
229910006069 SO3H Inorganic materials 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
150000002790 naphthalenes Chemical class 0.000 claims description 3
125000000542 sulfonic acid group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
150000004982 aromatic amines Chemical class 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
150000005840 aryl radicals Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
235000014113 dietary fatty acids Nutrition 0.000 claims description 2
239000000194 fatty acid Substances 0.000 claims description 2
229930195729 fatty acid Natural products 0.000 claims description 2
150000004665 fatty acids Chemical class 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
238000010276 construction Methods 0.000 claims 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
229920000742 Cotton Polymers 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
238000004043 dyeing Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 5
235000002639 sodium chloride Nutrition 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
150000008049 diazo compounds Chemical class 0.000 description 4
239000005457 ice water Substances 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
238000010025 steaming Methods 0.000 description 4
229940018563 3-aminophenol Drugs 0.000 description 3
125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000835 fiber Substances 0.000 description 3
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000000725 suspension Substances 0.000 description 3
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
229920003043 Cellulose fiber Polymers 0.000 description 2
240000007817 Olea europaea Species 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
229920000297 Rayon Polymers 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000002964 rayon Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000002791 soaking Methods 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
238000003756 stirring Methods 0.000 description 2
QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 1
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
NQMHWBKYQZSSGO-UHFFFAOYSA-N 2-amino-4-(3-chloropropanoylamino)benzenesulfonic acid Chemical compound NC1=CC(NC(=O)CCCl)=CC=C1S(O)(=O)=O NQMHWBKYQZSSGO-UHFFFAOYSA-N 0.000 description 1
UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 1
OSMZXKNDQCNATJ-UHFFFAOYSA-N 3-amino-4-methyl-5-(3-methyl-5-oxo-4H-pyrazol-1-yl)benzenesulfonic acid Chemical compound CC1=C(C=C(C=C1N)S(=O)(=O)O)N1N=C(CC1=O)C OSMZXKNDQCNATJ-UHFFFAOYSA-N 0.000 description 1
DYNWNNKAUGBOOZ-UHFFFAOYSA-N 3-n-methylbenzene-1,3-diamine Chemical compound CNC1=CC=CC(N)=C1 DYNWNNKAUGBOOZ-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
ZWUBBMDHSZDNTA-UHFFFAOYSA-N 4-Chloro-meta-phenylenediamine Chemical compound NC1=CC=C(Cl)C(N)=C1 ZWUBBMDHSZDNTA-UHFFFAOYSA-N 0.000 description 1
DPIZKMGPXNXSGL-UHFFFAOYSA-N 4-nitro-1,3-phenylenediamine Chemical compound NC1=CC=C([N+]([O-])=O)C(N)=C1 DPIZKMGPXNXSGL-UHFFFAOYSA-N 0.000 description 1
ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
244000061775 Olea africana Species 0.000 description 1
235000002852 Olea africana Nutrition 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
125000000732 arylene group Chemical group 0.000 description 1
239000012267 brine Substances 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
239000003518 caustics Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 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
230000000694 effects Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000001046 green dye Substances 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
DRXLHYPPJRAJSL-UHFFFAOYSA-N n-(3-aminophenyl)formamide Chemical compound NC1=CC=CC(NC=O)=C1 DRXLHYPPJRAJSL-UHFFFAOYSA-N 0.000 description 1
KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000004552 water soluble powder Substances 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
- C09B62/0068—Azodyes dyes containing in the molecule at least one azo group and at least one other chromophore group

Landscapes

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

CH7663159A 1958-08-07 1959-08-05 Verfahren zur Herstellung von Azofarbstoffen der Phthalocyaninreihe CH419382A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEC17316A DE1095429B (de)	1958-08-07	1958-08-07	Verfahren zur Herstellung von Azofarbstoffen der Phthalocyaninreihe
DEC18340A DE1134781B (de)	1958-08-07	1959-02-05	Verfahren zur Herstellung von Azofarbstoffen der Phthalocyaninreihe

Publications (1)

Publication Number	Publication Date
CH419382A true CH419382A (de)	1966-08-31

Family

ID=25969219

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7663159A CH419382A (de)	1958-08-07	1959-08-05	Verfahren zur Herstellung von Azofarbstoffen der Phthalocyaninreihe

Country Status (3)

Country	Link
BE (1)	BE581442A (fr)
CH (1)	CH419382A (fr)
DE (2)	DE1095429B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2617062C2 (de) *	1976-04-17	1985-07-04	Cassella Ag, 6000 Frankfurt	Wasserlösliche Hydrazone der Phthalocyaninreihe, ihre Herstellung und Verwendung
US4191686A (en) *	1976-04-17	1980-03-04	Cassella Aktiengesellschaft	Process for preparing fiber-reactive phthalocyanine azo dyes

1958
- 1958-08-07 DE DEC17316A patent/DE1095429B/de active Pending
1959
- 1959-02-05 DE DEC18340A patent/DE1134781B/de active Pending
- 1959-08-05 CH CH7663159A patent/CH419382A/de unknown
- 1959-08-06 BE BE581442A patent/BE581442A/fr unknown

Also Published As

Publication number	Publication date
DE1134781B (de)	1962-08-16
DE1095429B (de)	1960-12-22
BE581442A (fr)	1959-12-01

Publication	Publication Date	Title
DE1289930B (de)	1969-02-27	Verfahren zur Herstellung von Azofarbstoffen und deren Metallkomplexverbindungen
DE1719083B2 (de)	1976-01-15	Faserreaktive, schwermetallhaltige formazanfarbstoffe, deren herstellung und verwendung
CH419382A (de)	1966-08-31	Verfahren zur Herstellung von Azofarbstoffen der Phthalocyaninreihe
DE1904113C3 (de)	1979-02-22	Faserreaktive, schwermetallhaltige Formazanfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung
DE2852037A1 (de)	1979-06-13	Neue verbindungen, verfahren zu deren herstellung und deren verwendung
DE2222639A1 (de)	1972-11-16	In Wasser schwer loesliche Azoverbindungen,ihre Herstellung und Verwendung als Dispersionsfarbstoffe
DE1419841A1 (de)	1968-10-17	Verfahren zur Herstellung von neuen schwermetallhaltigen Formazanfarbstoffen
DE1644254C3 (de)	1978-12-21	Schwermetallhaltige wasserlösliche faserreaktive und -nichtreaktive Formazanazofarbstoffe, deren Herstellung und Verwendung
DE1444591A1 (de)	1968-11-21	Verfahren zur Herstellung von neuen Monoazofarbstoffen
DE657628C (de)	1938-03-09	Herstellung von Farbstoffen
DE2621231C3 (de)	1978-10-26	Phthalocyaninverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe
DE1444719A1 (de)	1969-10-23	Verfahren zur Herstellung von metallhaltigen Formazanfarbstoffen
DE617665C (de)	1935-08-23	Verfahren zur Herstellung von Monoazofarbstoffen
DE920750C (de)	1954-11-29	Verfahren zur Herstellung neuer chromhaltiger Azofarbstoffe
DE1419840C (de)	1971-04-01	Verfahren zur Herstellung von reaktiven Färb stoffen
AT212469B (de)	1960-12-27	Verfahren zur Herstellung von neuen, wasserlöslichen Farbstoffen der Phthalocyaninreihe
DE1964148C3 (de)	1976-11-11	Chromhaltige Azo-Triazol-Komplexfarbstoffe und Verfahren zur Herstellung derselben und deren Verwendung
DE888902C (de)	1953-09-07	Verfahren zur Herstellung saurer Monoazofarbstoffe
DE1794222A1 (de)	1971-10-28	Wasserloesliche Disazofarbstoffe und deren Metallkomplexverbindungen und Verfahren zu ihrer Herstellung
DE1943904C3 (de)	1977-11-03	Wasserlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von Leder, Wolle, Seide und Zellulose
AT158260B (de)	1940-03-26	Verfahren zur Herstellung von Azofarbstoffen.
DE2745480A1 (de)	1979-04-19	Verfahren zur herstellung von faserreaktiven farbstoffen, deren verwendung sowie mit ihnen gefaerbtes leder und fasermaterialien
DE1203402B (de)	1965-10-21	Verfahren zur Herstellung von wasserloeslichen Farbstoffen der Phthalocyaninreihe
DE650556C (de)	1937-09-24	Verfahren zur Herstellung von Azofarbstoffen
AT207976B (de)	1960-03-10	Verfahren zur Herstellung neuer 1 : 2 - Chrom- oder Kobaltkomplexverbindungen von Monoazofarbstoffen