BE897431A - Nouveaux composes monoazoiques leur preparation et leur utilisation comme colorants - Google Patents

Nouveaux composes monoazoiques leur preparation et leur utilisation comme colorants Download PDF

Info

Publication number: BE897431A
Authority: BE; Belgium
Prior art keywords: signifies; group; compounds; alkyl group; formula
Prior art date: 1982-08-06

Application number

BE1/10842A

Other languages

English (en)

French (fr)

Original Assignee

Sandoz Sa

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.)

1982-08-06

Filing date

1983-08-01

Publication date

1984-02-01

1983-08-01 Application filed by Sandoz Sa filed Critical Sandoz Sa

1984-02-01 Publication of BE897431A publication Critical patent/BE897431A/fr

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 31
238000002360 preparation method Methods 0.000 title description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 62
239000000975 dye Substances 0.000 claims abstract description 45
239000001257 hydrogen Substances 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 20
239000000203 mixture Substances 0.000 claims abstract description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
239000002253 acid Substances 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
-1 2-hydroxy-n-propyl Chemical group 0.000 claims description 17
238000004043 dyeing Methods 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 9
125000000129 anionic group Chemical group 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 7
239000000758 substrate Substances 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
230000007935 neutral effect Effects 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000004356 hydroxy functional group Chemical group O* 0.000 claims 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 claims description 3
150000001412 amines Chemical class 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
239000000126 substance Substances 0.000 claims 1
125000005843 halogen group Chemical group 0.000 abstract description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
239000004952 Polyamide Substances 0.000 description 13
229920002647 polyamide Polymers 0.000 description 13
239000000243 solution Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
150000001768 cations Chemical class 0.000 description 9
229920002302 Nylon 6,6 Polymers 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
239000004677 Nylon Substances 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229920001778 nylon Polymers 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
229920002292 Nylon 6 Polymers 0.000 description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
238000002955 isolation Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
239000004744 fabric Substances 0.000 description 3
235000013312 flour Nutrition 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000002562 thickening agent Substances 0.000 description 3
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
244000007835 Cyamopsis tetragonoloba Species 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
238000006193 diazotization reaction Methods 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000000835 fiber Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Chemical class 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000001488 sodium phosphate Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000004753 textile Substances 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
238000005406 washing Methods 0.000 description 2
210000002268 wool Anatomy 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
ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
240000008886 Ceratonia siliqua Species 0.000 description 1
235000013912 Ceratonia siliqua Nutrition 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
239000000980 acid dye Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
NGPGDYLVALNKEG-UHFFFAOYSA-N azanium;azane;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [NH4+].[NH4+].[O-]C(=O)C(O)C(O)C([O-])=O NGPGDYLVALNKEG-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000003599 detergent Substances 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000002612 dispersion medium Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000010985 leather Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Chemical class 0.000 description 1
238000003825 pressing Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000005185 salting out Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
235000011008 sodium phosphates Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000009977 space dyeing Methods 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
239000000080 wetting agent 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
- 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)
Coloring (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

BE1/10842A 1982-08-06 1983-08-01 Nouveaux composes monoazoiques leur preparation et leur utilisation comme colorants BE897431A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3229392		1982-08-06

Publications (1)

Publication Number	Publication Date
BE897431A true BE897431A (fr)	1984-02-01

Family

ID=6170294

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE1/10842A BE897431A (fr)	1982-08-06	1983-08-01	Nouveaux composes monoazoiques leur preparation et leur utilisation comme colorants

Country Status (6)

Country	Link
JP (1)	JPS5962668A (de)
BE (1)	BE897431A (de)
CH (1)	CH654845A5 (de)
FR (1)	FR2531442A1 (de)
GB (1)	GB2125811B (de)
IT (1)	IT1169458B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0564404B1 (de) *	1992-04-01	1997-06-25	Ciba SC Holding AG	Verfahren zum Färben von Leder mit Farbstoffmischungen
DE59305111D1 (de) *	1992-06-30	1997-02-27	Ciba Geigy Ag	Verfahren zum Trichromiefärben von Leder mit Farbstoffmischungen

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR675757A (fr) *	1928-05-26	1930-02-14	Prod Chim Ci Devant Sandoz Fab	Procédé de préparation de colorants monoazoïques
FR798038A (fr) *	1934-11-21	1936-05-08	Prod Chim Fab De	Colorants monoazoïques et leur procédé de préparation
CH410232A (de) *	1959-07-24	1966-03-31	Sandoz Ag	Verfahren zur Herstellung von Azofarbstoffen
GB1037648A (en) *	1963-09-04	1966-08-03	Ici Ltd	New monoazo dyestuffs containing unsaturated carboxylic acid amide and also sulphonamide groups
DE1644189C3 (de) *	1967-01-05	1975-10-09	Bayer Ag, 5090 Leverkusen	Azofarbstoffe und deren Verwendung
CH617449A5 (en) *	1975-09-03	1980-05-30	Sandoz Ag	Process for preparing monoazo compounds
GB1557205A (en) *	1976-03-30	1979-12-05	Ici Ltd	Benzene-azo naphthalene monoazo dyes containing sulphonamide groups
PL101484B1 (pl) *	1977-02-16	1978-12-30	Os Bad Rozwojowy Przem Barwni	Sposob otrzymywania czerwonych barwnikow monoazowych
DE2724079A1 (de) *	1977-05-27	1978-12-07	Bayer Ag	Azofarbstoffe

1983
- 1983-07-25 CH CH4051/83A patent/CH654845A5/de not_active IP Right Cessation
- 1983-08-01 BE BE1/10842A patent/BE897431A/fr not_active IP Right Cessation
- 1983-08-01 FR FR8312765A patent/FR2531442A1/fr not_active Withdrawn
- 1983-08-03 GB GB08320877A patent/GB2125811B/en not_active Expired
- 1983-08-04 IT IT8322432A patent/IT1169458B/it active
- 1983-08-04 JP JP58141975A patent/JPS5962668A/ja active Pending

Also Published As

Publication number	Publication date
IT1169458B (it)	1987-05-27
FR2531442A1 (fr)	1984-02-10
GB2125811A (en)	1984-03-14
CH654845A5 (de)	1986-03-14
JPS5962668A (ja)	1984-04-10
GB8320877D0 (en)	1983-09-07
GB2125811B (en)	1986-03-19
IT8322432A0 (it)	1983-08-04

Legal Events

Date

Code

Title

Description

1987-02-28

RE

Patent lapsed

Owner name: SANDOZ S.A.

Effective date: 19860831

Publication	Publication Date	Title
FR2567531A1 (fr)	1986-01-17	Nouveaux composes monoazoiques anioniques, leur preparation et leur utilisation comme colorants
BE1003908A3 (fr)	1992-07-14	Melanges de colorants et leur utilisation dans les procedes de teinture en trichromie.
FR2674530A1 (fr)	1992-10-02	Nouveaux composes disazouiques contenant des groupes sulfo, leur preparation et leur utilisation comme colorants.
BE1006310A3 (fr)	1994-07-19	Composition de colorant reactif jaune pour fibres.
FR2572733A1 (fr)	1986-05-09	Nouveaux composes disazoiques exempts de groupes sulfo, leur preparation et leur utilisation comme colorants
FR2586250A1 (fr)	1987-02-20	Nouveaux composes azoiques basiques contenant un groupe sulfo, leur preparation et leur utilisation comme colorants
FR2640988A1 (de)	1990-06-29
FR2599747A1 (fr)	1987-12-11	Nouveaux composes monoazoiques, leur preparation et leur utilisation comme colorants
EP0038296B1 (de)	1984-05-09	Disazoverbindungen
JPS6261617B2 (de)	1987-12-22
BE897431A (fr)	1984-02-01	Nouveaux composes monoazoiques leur preparation et leur utilisation comme colorants
FR2533224A1 (fr)	1984-03-23	Nouveaux composes monoazoiques, leur preparation et leur utilisation comme colorants
FR2585715A1 (fr)	1987-02-06	Nouvelles compositions de colorants de dispersion
FR2590264A1 (fr)	1987-05-22	Nouveaux complexes cupriferes, leur preparation et leur utilisation comme colorants reactifs
FR2472003A1 (fr)	1981-06-26	Nouveaux composes chloro-triaziniques, leur preparation et leur utilisation comme colorants
FR2556358A1 (fr)	1985-06-14	Nouveaux composes bisazoiques, leur preparation et leur utilisation comme colorants
JP3657625B2 (ja)	2005-06-08	繊維反応性ジスアゾ染料
FR2578852A1 (fr)	1986-09-19	Melanges de composes formazyliques, leur preparation et leur utilisation comme colorants.
BE1004606A3 (fr)	1992-12-22	Nouveaux composes monoazoiques, leur preparation et leur utilisation comme colorants reactifs.
FR2525619A1 (fr)	1983-10-28	Nouveaux composes anthraquinoniques, leur preparation et leur utilisation comme colorants
FR2554455A1 (fr)	1985-05-10	Nouveaux composes monoazoiques, leur preparation et leur utilisation comme colorants
BE892137Q (fr)	1982-08-16	Nouveaux complexes chromiferes asymetriques 1:2 leur preparation et leur application comme colorants
JP2785372B2 (ja)	1998-08-13	複素環式化合物およびそれを用いて疎水性繊維材料を染色または捺染する方法
FR2465766A1 (fr)	1981-03-27	Nouveaux composes disazoiques utilisables comme colorants et leur preparation
FR2500465A1 (fr)	1982-08-27	Nouveaux composes bisazoiques anioniques, leur preparation et leur application comme colorants