CH626052A5 - Process for monodiazotising aromatic diamines - Google Patents

Process for monodiazotising aromatic diamines Download PDF

Info

Publication number: CH626052A5
Authority: CH; Switzerland
Prior art keywords: acid; parts; weight; formula; water
Prior art date: 1975-12-10

Application number

CH1543676A

Other languages

German (de)

English (en)

Inventor

Heinz Dr Milz

Hans Jakob Dr Schladetsch

Original Assignee

Hoechst 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.)

1975-12-10

Filing date

1976-12-08

Publication date

1981-10-30

1976-12-08 Application filed by Hoechst Ag filed Critical Hoechst Ag

1981-10-30 Publication of CH626052A5 publication Critical patent/CH626052A5/de

Links

238000000034 method Methods 0.000 title claims description 13
150000004984 aromatic diamines Chemical class 0.000 title 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
JDQOQWKEOLQHKB-UHFFFAOYSA-N 4-aminobenzenediazonium Chemical class NC1=CC=C([N+]#N)C=C1 JDQOQWKEOLQHKB-UHFFFAOYSA-N 0.000 claims description 15
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 11
229910052500 inorganic mineral Inorganic materials 0.000 claims description 9
239000011707 mineral Substances 0.000 claims description 9
150000007524 organic acids Chemical class 0.000 claims description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
150000004989 p-phenylenediamines Chemical class 0.000 claims description 7
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
150000001450 anions Chemical class 0.000 claims description 2
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
229940106681 chloroacetic acid Drugs 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
235000005985 organic acids Nutrition 0.000 claims description 2
235000006408 oxalic acid Nutrition 0.000 claims description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 22
239000000243 solution Substances 0.000 description 22
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 16
238000006193 diazotization reaction Methods 0.000 description 15
239000000975 dye Substances 0.000 description 15
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 12
235000010288 sodium nitrite Nutrition 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
-1 4-amino-naphthalenediazonium Chemical compound 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
239000012954 diazonium Substances 0.000 description 6
150000001989 diazonium salts Chemical class 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
230000008878 coupling Effects 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
239000012670 alkaline solution Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
239000000987 azo dye Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
OKBVMLGZPNDWJK-UHFFFAOYSA-N naphthalene-1,4-diamine Chemical compound C1=CC=C2C(N)=CC=C(N)C2=C1 OKBVMLGZPNDWJK-UHFFFAOYSA-N 0.000 description 2
150000002828 nitro derivatives Chemical class 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
150000003457 sulfones Chemical class 0.000 description 2
239000002351 wastewater Substances 0.000 description 2
MAKYXOXQLDHOFO-UHFFFAOYSA-N 2,5-dimethylbenzene-1,4-diamine;hydrochloride Chemical compound Cl.CC1=CC(N)=C(C)C=C1N MAKYXOXQLDHOFO-UHFFFAOYSA-N 0.000 description 1
NGULVTOQNLILMZ-UHFFFAOYSA-N 2-bromobenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(Br)=C1 NGULVTOQNLILMZ-UHFFFAOYSA-N 0.000 description 1
MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 description 1
VXUMJWGCPAUKTB-UHFFFAOYSA-N 2-methoxy-5-methyl-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=C(C)C=C1N VXUMJWGCPAUKTB-UHFFFAOYSA-N 0.000 description 1
KNRVAYVZVIKHHL-UHFFFAOYSA-N 2-methoxy-5-methylbenzene-1,4-diamine Chemical compound COC1=CC(N)=C(C)C=C1N KNRVAYVZVIKHHL-UHFFFAOYSA-N 0.000 description 1
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
HVHNMNGARPCGGD-UHFFFAOYSA-N 2-nitro-p-phenylenediamine Chemical compound NC1=CC=C(N)C([N+]([O-])=O)=C1 HVHNMNGARPCGGD-UHFFFAOYSA-N 0.000 description 1
NDGZCIISICKSMA-UHFFFAOYSA-N 4-amino-2,5-dimethylbenzenediazonium Chemical class CC1=CC([N+]#N)=C(C)C=C1N NDGZCIISICKSMA-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
BVPJPRYNQHAOPQ-UHFFFAOYSA-N 4-nitronaphthalen-1-amine Chemical compound C1=CC=C2C(N)=CC=C([N+]([O-])=O)C2=C1 BVPJPRYNQHAOPQ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
DQXQNAUILQJJNY-UHFFFAOYSA-N benzene-1,4-didiazonium Chemical class N#[N+]C1=CC=C([N+]#N)C=C1 DQXQNAUILQJJNY-UHFFFAOYSA-N 0.000 description 1
239000001049 brown dye Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000005352 clarification Methods 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002243 precursor Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 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
- C09B41/00—Special methods of performing the coupling reaction
- 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
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heat Sensitive Colour Forming Recording (AREA)

CH1543676A 1975-12-10 1976-12-08 Process for monodiazotising aromatic diamines CH626052A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19752555515 DE2555515C2 (de)	1975-12-10	1975-12-10	Verfahren zur Herstellung von einheitlichen 4-Aminobenzoldiazoniumsalzen

Publications (1)

Publication Number	Publication Date
CH626052A5 true CH626052A5 (en)	1981-10-30

Family

ID=5963976

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1543676A CH626052A5 (en)	1975-12-10	1976-12-08	Process for monodiazotising aromatic diamines

Country Status (10)

Country	Link
JP (1)	JPS6034534B2 (fr)
BE (1)	BE849290A (fr)
BR (1)	BR7608185A (fr)
CH (1)	CH626052A5 (fr)
DE (1)	DE2555515C2 (fr)
FR (1)	FR2334662A1 (fr)
GB (1)	GB1536320A (fr)
IT (1)	IT1070431B (fr)
MX (1)	MX143905A (fr)
NL (1)	NL7613493A (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2910199A1 (de) *	1979-03-15	1980-09-25	Hoechst Ag	Verfahren zur herstellung von diazoniumsalzloesungen
DE3412730A1 (de) *	1984-04-05	1985-10-17	Hoechst Ag, 6230 Frankfurt	Disazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung
DE3932819A1 (de) *	1989-09-30	1991-04-11	Hoechst Ag	Waessrige praeparationen von c.i. azoic diazo components, ihre herstellung und verwendung
US8288466B2 (en)	2009-05-13	2012-10-16	E I Du Pont De Nemours And Company	Composite of a polymer and surface modified hexagonal boron nitride particles
US8784980B2 (en)	2009-05-13	2014-07-22	E I Du Pont De Nemours And Company	Film prepared from a casting composition comprising a polymer and surface modified hexagonal boron nitride particles
US8440292B2 (en)	2009-05-13	2013-05-14	E I Du Pont De Nemours And Company	Multi-layer article for flexible printed circuits
US8258346B2 (en)	2009-05-13	2012-09-04	E I Du Pont De Nemours And Company	Surface modified hexagonal boron nitride particles

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE42011C (fr) *
GB1427516A (en) *	1972-03-09	1976-03-10	Ici Ltd	Fungicidal compositions and processes using azonaphthol sulphonic acid derivatives

1975
- 1975-12-10 DE DE19752555515 patent/DE2555515C2/de not_active Expired
1976
- 1976-12-03 NL NL7613493A patent/NL7613493A/xx not_active Application Discontinuation
- 1976-12-06 IT IT3018276A patent/IT1070431B/it active
- 1976-12-07 BR BR7608185A patent/BR7608185A/pt unknown
- 1976-12-08 CH CH1543676A patent/CH626052A5/de not_active IP Right Cessation
- 1976-12-09 MX MX16733576A patent/MX143905A/es unknown
- 1976-12-09 JP JP14720476A patent/JPS6034534B2/ja not_active Expired
- 1976-12-10 FR FR7637233A patent/FR2334662A1/fr active Granted
- 1976-12-10 GB GB5169676A patent/GB1536320A/en not_active Expired
- 1976-12-10 BE BE173160A patent/BE849290A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
FR2334662B1 (fr)	1982-11-19
IT1070431B (it)	1985-03-29
GB1536320A (en)	1978-12-20
MX143905A (es)	1981-07-31
DE2555515C2 (de)	1990-04-19
FR2334662A1 (fr)	1977-07-08
NL7613493A (nl)	1977-06-14
JPS5273828A (en)	1977-06-21
DE2555515A1 (de)	1977-06-23
BE849290A (fr)	1977-06-10
BR7608185A (pt)	1977-11-22
JPS6034534B2 (ja)	1985-08-09

Legal Events

Date	Code	Title	Description
1992-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2139311B2 (de)	1974-12-19	Verfahren zur einstufigen Herstellung von Azofarbstoffen
EP0012944A1 (fr)	1980-07-09	Mélanges de pigments monoazoiques, ne déteignant et ne recristallisant pas, procédé pour leur préparation et leur application
DE2503714C3 (de)	1978-05-03	Verfahren zur Herstellung von wasserlöslichen Azofarbstoffen
DE2043192C3 (de)	1974-05-16	Basische Farbstoffe, deren Herstellung und Verwendung
DE2555515A1 (de)	1977-06-23	Verfahren zur monodiazotierung von aromatischen diaminen
DE913174C (de)	1954-04-29	Verfahren zur Herstellung von neuen, zwei 1,2,3,-Triazolringe enthaltenden aromatischen Verbindungen
DE2503791B1 (de)	1976-07-29	Verfahren zur herstellung von verlackten azofarbstoffen
CH619477A5 (fr)	1980-09-30
CH639119A5 (de)	1983-10-31	Azopigmente.
EP0281920A2 (fr)	1988-09-14	Colorants à groupes N-(2-aminométhyle)-pipérazine et leur utilisation
DE2244035B2 (de)	1979-02-08	Disazopigmente, Verfahren zu deren Herstellung und ihre Verwendung zum Pigmentieren von hochmolekularem organischen Material
EP0016975B1 (fr)	1983-08-17	Colorants polyazoiques et leur utilisation pour la teinture du cuir et de matières fibreuses contenant des groupes amino et hydroxy
DE2617302C3 (de)	1979-05-03	Verfahren zur Herstellung von Disazofarbstoffen
EP0074589B1 (fr)	1984-12-05	Colorants triaziniques, leur préparation et leur utilisation
RU2415892C2 (ru)	2011-04-10	Способ получения моно- или дисазокрасителей на основе метилфлороглюцина
EP0262095B1 (fr)	1990-12-27	Composés disazoiques anioniques
EP0073387A1 (fr)	1983-03-09	Colorants polyazoiques solubles dans l'eau, leur préparation et leur utilisation
DE140690C (fr)
DE2424501B2 (de)	1979-09-13	Wasserlösliche Trisazofarbstoffe, ihre Herstellung und Verwendung zum Färben und Bedrucken von hydroxylgruppenhaltigen oder stickstoffhaltigen, natürlichen oder synthetischen Fasermaterialien
AT162598B (de)	1949-03-10	Verfahren zur Herstellung von Azofarbstoffen
EP0023955B1 (fr)	1983-09-21	Procédé de préparation de complexes de cuivre de colorants disazoiques
DE174106C (fr)
DE906809C (de)	1954-03-18	Verfahren zur Herstellung von Diazoamino-Verbindungen
DE938250C (de)	1956-01-26	Verfahren zur Herstellung von Diazoamino-Derivaten
DE959552C (de)	1957-03-07	Verfahren zur Isolierung von Diazoamino-Derivaten