CA1038376A - Composes pigmentaires - Google Patents

Composes pigmentaires

Info

Publication number: CA1038376A
Authority: CA; Canada
Prior art keywords: parts; formula; solution; water; minutes
Prior art date: 1973-09-22
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

CA209,724A

Other languages

English (en)

Other versions

CA209724S (en

Inventor

James M. Mccrae

Alexander M. Irvine

Christopher Midcalf

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.)

Novartis AG

Original Assignee

Ciba Geigy 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.)

1973-09-22

Filing date

1974-09-20

Publication date

1978-09-12

1974-09-20 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1978-09-12 Application granted granted Critical

1978-09-12 Publication of CA1038376A publication Critical patent/CA1038376A/fr

Status Expired legal-status Critical Current

Links

239000000049 pigment Substances 0.000 title abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
150000004696 coordination complex Chemical class 0.000 claims abstract description 6
229910052802 copper Inorganic materials 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
125000003118 aryl group Chemical group 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
229910052725 zinc Inorganic materials 0.000 claims abstract description 4
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
229910002092 carbon dioxide Inorganic materials 0.000 claims abstract 2
229910052760 oxygen Inorganic materials 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 abstract description 17
239000004922 lacquer Substances 0.000 abstract description 8
239000011368 organic material Substances 0.000 abstract description 5
239000000976 ink Substances 0.000 abstract description 2
239000003973 paint Substances 0.000 abstract description 2
239000000243 solution Substances 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
235000013350 formula milk Nutrition 0.000 description 17
239000000725 suspension Substances 0.000 description 13
239000003446 ligand Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 9
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 8
ORWQBKPSGDRPPA-UHFFFAOYSA-N 3-[2-[ethyl(methyl)amino]ethyl]-1h-indol-4-ol Chemical compound C1=CC(O)=C2C(CCN(C)CC)=CNC2=C1 ORWQBKPSGDRPPA-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
230000008878 coupling Effects 0.000 description 7
238000010168 coupling process Methods 0.000 description 7
238000005859 coupling reaction Methods 0.000 description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000000034 method Methods 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
-1 2-hydroxy aniline 2-methoxy aniline 2-hydroxy-4-nitroaniline 2-methoxy-4-nitroaniline 2-methoxy-4-nitro-5-methyl aniline Chemical compound 0.000 description 5
238000007792 addition Methods 0.000 description 5
239000002184 metal Substances 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002002 slurry Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000010949 copper Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000001465 metallisation Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
229910021653 sulphate ion Inorganic materials 0.000 description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000001879 copper Chemical class 0.000 description 2
JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 2
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
229940087562 sodium acetate trihydrate Drugs 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000011701 zinc Substances 0.000 description 2
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-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
229920000877 Melamine resin Polymers 0.000 description 1
229910052779 Neodymium Inorganic materials 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
229940081735 acetylcellulose Drugs 0.000 description 1
229920003180 amino resin Polymers 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([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
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
229920003086 cellulose ether Polymers 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000003750 conditioning effect Effects 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
NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
238000000227 grinding Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000009775 high-speed stirring Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
229940078487 nickel acetate tetrahydrate Drugs 0.000 description 1
OINIXPNQKAZCRL-UHFFFAOYSA-L nickel(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Ni+2].CC([O-])=O.CC([O-])=O OINIXPNQKAZCRL-UHFFFAOYSA-L 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
150000004686 pentahydrates Chemical class 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920002050 silicone resin Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
239000011686 zinc sulphate Substances 0.000 description 1
235000009529 zinc sulphate Nutrition 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Paints Or Removers (AREA)
Plural Heterocyclic Compounds (AREA)

CA209,724A 1973-09-22 1974-09-20 Composes pigmentaires Expired CA1038376A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB4455773A GB1430811A (en)	1973-09-22	1973-09-22	Pigment azo complexes

Publications (1)

Publication Number	Publication Date
CA1038376A true CA1038376A (fr)	1978-09-12

Family

ID=10433849

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA209,724A Expired CA1038376A (fr)	1973-09-22	1974-09-20	Composes pigmentaires

Country Status (2)

Country	Link
CA (1)	CA1038376A (fr)
GB (1)	GB1430811A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0413557D0 (en) *	2004-06-17	2004-07-21	Avecia Ltd	Compounds

1973
- 1973-09-22 GB GB4455773A patent/GB1430811A/en not_active Expired
1974
- 1974-09-20 CA CA209,724A patent/CA1038376A/fr not_active Expired

Also Published As

Publication number	Publication date
GB1430811A (en)	1976-04-07

Publication	Publication Date	Title
JPS62146961A (ja)	1987-06-30	アゾレ−キ
US3895041A (en)	1975-07-15	Metallised pigments
CA1070677A (fr)	1980-01-29	Teintures de type azomethine-complexe metallique 1:1
CA1242210A (fr)	1988-09-20	Emploi de complexes metalliques d'hydrazone a titre de pigments
US3988323A (en)	1976-10-26	Metal complexes of bishydrazides
CA1038376A (fr)	1978-09-12	Composes pigmentaires
US4077953A (en)	1978-03-07	Tri-dentate metal complex azo pigments
US4340430A (en)	1982-07-20	Azo pigments, process for their production and their use
US4263197A (en)	1981-04-21	Process for dyeing linear polyamides in the melt
CA1080231A (fr)	1980-06-24	Pigments complexes a base d'azomethine symmetrique, heterocyclique
US3971739A (en)	1976-07-27	Tri or tetradentate metal azo pigment complexes
US4152324A (en)	1979-05-01	Pigment copper complex of carboxyphenylazon-phenyl-β-naphthyzamine
US3987023A (en)	1976-10-19	Azo pigment metal complexes
DE2533674A1 (de)	1976-02-19	Neue bisazomethin-metallkomplexfarbstoffe aus hydroxycumarin- bzw. hydroxychromonderivaten und verfahren zu deren herstellung
US3197457A (en)	1965-07-27	Monoazo pigments
US4231964A (en)	1980-11-04	Nitroamines, processes for their manufacture and their use as diazo components
US4097484A (en)	1978-06-27	Mixed complexes of methine dyes
US3336328A (en)	1967-08-15	Metal complexes of 2, 6-di-(2'-hydroxyaryl)-(1, 2d-4, 5d)-bisoxazole derivatives
US4144258A (en)	1979-03-13	1:1-Heterocyclic azo methine-metal complex dyestuffs
CA1156658A (fr)	1983-11-08	Complexes metalliques d'imino-iso-indolinone, leur production et leur emploi
US2829139A (en)	1958-04-01	Metalliferous azo dyestuff
CA1049000A (fr)	1979-02-20	Colorants comportant un complexe de chrome
CH626906A5 (fr)	1981-12-15
EP0064952B1 (fr)	1985-07-24	Pigments monoazoiques
US3086006A (en)	1963-04-16	Water-insoluble monoazo-dyestuffs and process for their manufacture