CA1104758A - Traduction non-disponible - Google Patents

Traduction non-disponible

Info

Publication number: CA1104758A
Authority: CA; Canada
Prior art keywords: formula; several; compound; mixed; mol
Prior art date: 1976-03-12
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

Application number

CA273,737A

Other languages

English (en)

Inventor

Theodor Papenfuhs

Heinrich Volk

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

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.)

1976-03-12

Filing date

1977-03-11

Publication date

1981-07-14

1977-03-11 Application filed by Hoechst AG filed Critical Hoechst AG

1981-07-14 Application granted granted Critical

1981-07-14 Publication of CA1104758A publication Critical patent/CA1104758A/fr

Status Expired legal-status Critical Current

Links

-1 metal-complex compounds Chemical class 0.000 title claims abstract description 32
239000003086 colorant Substances 0.000 title claims abstract description 8
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 70
229910052751 metal Inorganic materials 0.000 claims abstract description 23
239000002184 metal Substances 0.000 claims abstract description 23
239000004922 lacquer Substances 0.000 claims abstract description 14
239000003795 chemical substances by application Substances 0.000 claims abstract description 13
NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical class C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 claims abstract description 12
238000000034 method Methods 0.000 claims abstract description 10
150000002739 metals Chemical class 0.000 claims abstract description 9
239000000976 ink Substances 0.000 claims abstract description 6
239000004033 plastic Substances 0.000 claims abstract description 6
229920003023 plastic Polymers 0.000 claims abstract description 6
238000004040 coloring Methods 0.000 claims abstract description 5
239000003973 paint Substances 0.000 claims abstract description 4
239000000463 material Substances 0.000 claims abstract 6
238000009987 spinning Methods 0.000 claims abstract 3
229910052739 hydrogen Inorganic materials 0.000 claims description 46
239000001257 hydrogen Substances 0.000 claims description 46
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 43
125000004432 carbon atom Chemical group C* 0.000 claims description 39
125000000217 alkyl group Chemical group 0.000 claims description 36
125000003545 alkoxy group Chemical group 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 29
239000000460 chlorine Substances 0.000 claims description 28
229910052736 halogen Inorganic materials 0.000 claims description 26
150000002367 halogens Chemical class 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 22
229910052801 chlorine Inorganic materials 0.000 claims description 21
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
229910052794 bromium Chemical group 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 20
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
229910052759 nickel Inorganic materials 0.000 claims description 18
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
150000001299 aldehydes Chemical class 0.000 claims description 9
239000010949 copper Substances 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
150000004985 diamines Chemical class 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
238000009833 condensation Methods 0.000 claims description 6
230000005494 condensation Effects 0.000 claims description 6
229910052802 copper Inorganic materials 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 6
239000000376 reactant Substances 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 4
238000002955 isolation Methods 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 12
125000001589 carboacyl group Chemical group 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 1
239000000049 pigment Substances 0.000 abstract description 13
239000002904 solvent Substances 0.000 abstract description 12
238000001465 metallisation Methods 0.000 abstract description 4
150000004987 o-phenylenediamines Chemical class 0.000 abstract description 4
238000006482 condensation reaction Methods 0.000 abstract description 3
230000005012 migration Effects 0.000 abstract description 3
238000013508 migration Methods 0.000 abstract description 3
150000004696 coordination complex Chemical class 0.000 abstract description 2
150000004695 complexes Chemical class 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000000306 component Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000011701 zinc Substances 0.000 description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
150000001555 benzenes Chemical class 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
229940078494 nickel acetate Drugs 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 3
MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
230000000875 corresponding effect Effects 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 2
DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
239000004902 Softening Agent Substances 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
229910052793 cadmium Inorganic materials 0.000 description 2
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000004043 dyeing Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 2
229910000363 nickel(II) sulfate Inorganic materials 0.000 description 2
230000019612 pigmentation Effects 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
OTNKCGQLSHSABI-UHFFFAOYSA-N 2-hydroxy-6-methoxynaphthalene-1-carbaldehyde Chemical compound O=CC1=C(O)C=CC2=CC(OC)=CC=C21 OTNKCGQLSHSABI-UHFFFAOYSA-N 0.000 description 1
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical class C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
AXNUJYHFQHQZBE-UHFFFAOYSA-N 3-methylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N)=C1N AXNUJYHFQHQZBE-UHFFFAOYSA-N 0.000 description 1
IWFHBRFJOHTIPU-UHFFFAOYSA-N 4,5-dichlorobenzene-1,2-diamine Chemical compound NC1=CC(Cl)=C(Cl)C=C1N IWFHBRFJOHTIPU-UHFFFAOYSA-N 0.000 description 1
BXIXXXYDDJVHDL-UHFFFAOYSA-N 4-Chloro-ortho-phenylenediamine Chemical compound NC1=CC=C(Cl)C=C1N BXIXXXYDDJVHDL-UHFFFAOYSA-N 0.000 description 1
ZZNAYFWAXZJITH-UHFFFAOYSA-N 4-amino-3-nitrobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1[N+]([O-])=O ZZNAYFWAXZJITH-UHFFFAOYSA-N 0.000 description 1
AGAHETWGCFCMDK-UHFFFAOYSA-N 4-methoxybenzene-1,2-diamine Chemical compound COC1=CC=C(N)C(N)=C1 AGAHETWGCFCMDK-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
235000003625 Acrocomia mexicana Nutrition 0.000 description 1
244000202285 Acrocomia mexicana Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
238000005169 Debye-Scherrer Methods 0.000 description 1
229910017709 Ni Co Inorganic materials 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
241000183024 Populus tremula Species 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000001058 brown pigment Substances 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000010668 complexation reaction Methods 0.000 description 1
230000003750 conditioning effect Effects 0.000 description 1
238000011109 contamination Methods 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000000975 dye Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000022244 formylation Effects 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000000320 mechanical mixture Substances 0.000 description 1
125000004957 naphthylene group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
FAQOZARUOBFXBH-UHFFFAOYSA-N nitroformamide Chemical compound NC(=O)[N+]([O-])=O FAQOZARUOBFXBH-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
LMAZKPOSWVOFGY-FBAUPLQOSA-N orine Natural products CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C)[C@H]4C[C@@H](OC(=O)C=Cc5ccccc5)[C@]6(C)[C@@](O)(CC[C@]6(O)[C@]4(O)CC=C3C2)[C@H](C)OC(=O)C=Cc7ccccc7)O[C@H](C)[C@H]1O LMAZKPOSWVOFGY-FBAUPLQOSA-N 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
150000004986 phenylenediamines Chemical class 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
230000000063 preceeding effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
238000005086 pumping Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000005060 rubber Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000001052 yellow pigment Substances 0.000 description 1
239000004246 zinc acetate 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
- C09B55/00—Azomethine dyes
- C09B55/005—Disazomethine dyes
- C09B55/007—Disazomethine dyes containing only carbocyclic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Compositions Of Macromolecular Compounds (AREA)
Paints Or Removers (AREA)
Artificial Filaments (AREA)

CA273,737A 1976-03-12 1977-03-11 Traduction non-disponible Expired CA1104758A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19762610308 DE2610308A1 (de)	1976-03-12	1976-03-12	Wasserunloesliche disazomethin-mischkomplexe, verfahren zu ihrer herstellung und ihre verwendung als farbmittel
DEP2610308.2		1976-03-12

Publications (1)

Publication Number	Publication Date
CA1104758A true CA1104758A (fr)	1981-07-14

Family

ID=5972218

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA273,737A Expired CA1104758A (fr)	1976-03-12	1977-03-11	Traduction non-disponible

Country Status (11)

Country	Link
JP (1)	JPS52111924A (fr)
AU (1)	AU2310577A (fr)
BE (1)	BE852430A (fr)
BR (1)	BR7701508A (fr)
CA (1)	CA1104758A (fr)
DE (1)	DE2610308A1 (fr)
DK (1)	DK106477A (fr)
FR (1)	FR2343784A1 (fr)
GB (1)	GB1553441A (fr)
IT (1)	IT1085518B (fr)
NL (1)	NL7702423A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3621215A1 (de) *	1986-06-25	1988-01-07	Bayer Ag	Fluorhaltige o-phenylendiamine und o-aminophenole

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1416293A (fr) *	1963-12-04	1965-10-29	Basf Ag	Colorants pigmentaires et procédé pour leur production
DE2305071C2 (de) *	1973-02-02	1975-04-17	Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt	Wasserunlösliche Disazomethinfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2515523C3 (de) *	1975-04-09	1980-05-29	Hoechst Ag, 6000 Frankfurt	Wasserunlösliche Disazomethinverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbmittel

1976
- 1976-03-12 DE DE19762610308 patent/DE2610308A1/de not_active Withdrawn
1977
- 1977-03-07 NL NL7702423A patent/NL7702423A/xx not_active Application Discontinuation
- 1977-03-10 IT IT2115277A patent/IT1085518B/it active
- 1977-03-10 AU AU23105/77A patent/AU2310577A/en not_active Expired
- 1977-03-11 CA CA273,737A patent/CA1104758A/fr not_active Expired
- 1977-03-11 BR BR7701508A patent/BR7701508A/pt unknown
- 1977-03-11 DK DK106477A patent/DK106477A/da unknown
- 1977-03-11 JP JP2613677A patent/JPS52111924A/ja active Pending
- 1977-03-14 BE BE175761A patent/BE852430A/fr unknown
- 1977-03-14 GB GB1070777A patent/GB1553441A/en not_active Expired
- 1977-03-14 FR FR7707476A patent/FR2343784A1/fr active Pending

Also Published As

Publication number	Publication date
DE2610308A1 (de)	1977-09-15
DK106477A (da)	1977-09-13
AU2310577A (en)	1978-09-14
IT1085518B (it)	1985-05-28
FR2343784A1 (fr)	1977-10-07
NL7702423A (nl)	1977-09-14
GB1553441A (en)	1979-09-26
JPS52111924A (en)	1977-09-20
BR7701508A (pt)	1977-11-08
BE852430A (fr)	1977-09-14

Legal Events

Date	Code	Title	Description
1998-07-14	MKEX	Expiry

Publication	Publication Date	Title
US4044036A (en)	1977-08-23	Metal complexes of bis-azomethines from hydroxy-aldehydes and alkylene diamines
US4045423A (en)	1977-08-30	Chromium complexes of phenylazopyrazolyl or phenylazonaphthol dyestuffs and acetylacetone
US3988323A (en)	1976-10-26	Metal complexes of bishydrazides
US4065481A (en)	1977-12-27	1:1-Azomethine-metal-complex dyestuffs
DE2263235A1 (de)	1973-07-12	Heterocyclische metallkomplexverbindungen, ihre herstellung und verwendung
US4024125A (en)	1977-05-17	Dis-azo pigments deriving from bis-diazotized diamino-2-phenyl-benzazolones
DE2442315C2 (de)	1987-01-02	Neue Azomethinpigmente und Verfahren zur Pigmentierung
CA1083590A (fr)	1980-08-12	Preparation et emploi comme colorants de composes disazoiques de methine, insolubles dans l'eau
CA1104758A (fr)	1981-07-14	Traduction non-disponible
US4157265A (en)	1979-06-05	Water-insoluble disazomethine mixed metal-complex compounds, process for preparing them and their use as colorants
JPWO2011018994A1 (ja)	2013-01-17	フタロシアニン化合物およびその製造方法、ならびに該フタロシアニン化合物を含有する着色組成物
JPS6328109B2 (fr)	1988-06-07
Patel et al.	2002	Synthesis and application of novel heterocyclic dyes based on 11-amino-13H-acenaphtho [1, 2-e] pyridazino [3, 2-b]-quinazoline-13-one
US4077953A (en)	1978-03-07	Tri-dentate metal complex azo pigments
CA1052803A (fr)	1979-04-17	Composes de methine diazoique insolubles dans l'eau
US4734515A (en)	1988-03-29	1:2 metal complexes of 2-nitroso-acetoacetic acid and benzoylacetic acid arylamides
US4113759A (en)	1978-09-12	Metal-containing disazomethine compounds, process for preparing them and their use as colorants
CA1089869A (fr)	1980-11-18	Obtention et emploi comme colorants de composes a base de diazomethine contenant des metaux
US5965717A (en)	1999-10-12	Organic pigments from twisted benzidines
US4861898A (en)	1989-08-29	Isoindoline metal complexes
US4144258A (en)	1979-03-13	1:1-Heterocyclic azo methine-metal complex dyestuffs
US4005068A (en)	1977-01-25	Disazo compounds from diphenylene sulfones and acetoacetylbenzimidazolones
US3449425A (en)	1969-06-10	N,n'-bis(beta-benzophenone)-arylenediamines
JPS6213463A (ja)	1987-01-22	イソインドリン色素
JPS61133270A (ja)	1986-06-20	新規なイソインドリン化合物、その金属錯化合物及びその用途