CA1037962A - Composes metalliques complexes a base d'azamethine - Google Patents

Composes metalliques complexes a base d'azamethine

Info

Publication number: CA1037962A
Authority: CA; Canada
Prior art keywords: hydrogen; compound; carbamoyl; chlorine; nitro
Prior art date: 1974-08-28
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

CA234,235A

Other languages

English (en)

Other versions

CA234235S (en

Inventor

Klaus Hunger

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.)

1974-08-28

Filing date

1975-08-27

Publication date

1978-09-05

1975-08-27 Application filed by Hoechst AG filed Critical Hoechst AG

1978-09-05 Application granted granted Critical

1978-09-05 Publication of CA1037962A publication Critical patent/CA1037962A/fr

Status Expired legal-status Critical Current

Links

-1 metal complex compounds Chemical class 0.000 title claims abstract description 32
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 16
239000010949 copper Substances 0.000 claims abstract description 10
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052759 nickel Inorganic materials 0.000 claims abstract description 8
229910052802 copper Inorganic materials 0.000 claims abstract description 7
229910017052 cobalt Inorganic materials 0.000 claims abstract description 6
239000010941 cobalt Substances 0.000 claims abstract description 6
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052793 cadmium Inorganic materials 0.000 claims abstract description 4
229910052725 zinc Inorganic materials 0.000 claims abstract description 4
239000011701 zinc Substances 0.000 claims abstract description 4
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 26
239000000460 chlorine Chemical group 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Chemical group 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
229940124530 sulfonamide Drugs 0.000 claims description 7
150000003456 sulfonamides Chemical class 0.000 claims description 7
125000005236 alkanoylamino group Chemical group 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000003944 tolyl group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
239000003495 polar organic solvent Substances 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
229910052727 yttrium Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 15
125000005363 dialkylsulfonamide group Chemical group 0.000 claims 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims 2
229910052736 halogen Inorganic materials 0.000 claims 2
150000002367 halogens Chemical class 0.000 claims 2
125000001424 substituent group Chemical group 0.000 claims 2
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
150000001768 cations Chemical class 0.000 claims 1
238000004040 coloring Methods 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
125000005545 phthalimidyl group Chemical group 0.000 claims 1
239000000049 pigment Substances 0.000 abstract description 10
229910052751 metal Inorganic materials 0.000 abstract description 4
239000002184 metal Substances 0.000 abstract description 4
238000009833 condensation Methods 0.000 abstract description 3
230000005494 condensation Effects 0.000 abstract description 3
LPRBZICETYEWOZ-UHFFFAOYSA-N 4-formyl-3-hydroxynaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(C=O)=C(O)C(C(=O)O)=CC2=C1 LPRBZICETYEWOZ-UHFFFAOYSA-N 0.000 abstract 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical group COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
150000002431 hydrogen Chemical group 0.000 description 4
239000004922 lacquer Substances 0.000 description 4
238000001465 metallisation Methods 0.000 description 4
FDGAEAYZQQCBRN-UHFFFAOYSA-N 3-amino-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1N FDGAEAYZQQCBRN-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
150000003931 anilides Chemical class 0.000 description 3
MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical group C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 3
125000005521 carbonamide group Chemical group 0.000 description 3
HVAXPRLYMAWEBL-UHFFFAOYSA-N 4-chlorobenzimidazol-2-one Chemical compound ClC1=CC=CC2=NC(=O)N=C12 HVAXPRLYMAWEBL-UHFFFAOYSA-N 0.000 description 2
QODOLPZUMYLXKD-UHFFFAOYSA-N 4-formyl-3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound C1=C2C=CC=CC2=C(C=O)C(O)=C1C(=O)NC1=CC=CC=C1 QODOLPZUMYLXKD-UHFFFAOYSA-N 0.000 description 2
USQCUKQZXOWUDF-YWZLYKJASA-N 6-chloro-n-[(3s)-1-[(2s)-1-(4-methyl-5-oxo-1,4-diazepan-1-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]naphthalene-2-sulfonamide Chemical compound O=C([C@@H](N1C([C@@H](NS(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N1CCN(C)C(=O)CC1 USQCUKQZXOWUDF-YWZLYKJASA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
229960001760 dimethyl sulfoxide Drugs 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
239000000976 ink Substances 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000001238 wet grinding Methods 0.000 description 2
FHMMQQXRSYSWCM-UHFFFAOYSA-N 1-aminonaphthalen-2-ol Chemical compound C1=CC=C2C(N)=C(O)C=CC2=C1 FHMMQQXRSYSWCM-UHFFFAOYSA-N 0.000 description 1
VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
QQDKXJSYZGJGKJ-UHFFFAOYSA-N 2-amino-3,4,6-trichlorophenol Chemical compound NC1=C(O)C(Cl)=CC(Cl)=C1Cl QQDKXJSYZGJGKJ-UHFFFAOYSA-N 0.000 description 1
JHRIPENGTGSNPJ-UHFFFAOYSA-N 2-amino-4-bromophenol Chemical compound NC1=CC(Br)=CC=C1O JHRIPENGTGSNPJ-UHFFFAOYSA-N 0.000 description 1
AJWIWEGQLDDWQC-UHFFFAOYSA-N 2-amino-4-methyl-6-nitrophenol Chemical compound CC1=CC(N)=C(O)C([N+]([O-])=O)=C1 AJWIWEGQLDDWQC-UHFFFAOYSA-N 0.000 description 1
FZCQMIRJCGWWCL-UHFFFAOYSA-N 2-amino-5-chlorophenol Chemical compound NC1=CC=C(Cl)C=C1O FZCQMIRJCGWWCL-UHFFFAOYSA-N 0.000 description 1
QUIIUKFPLUUSGQ-UHFFFAOYSA-N 2-amino-6-chlorophenol Chemical compound NC1=CC=CC(Cl)=C1O QUIIUKFPLUUSGQ-UHFFFAOYSA-N 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
XLJMDBOKSZROPC-UHFFFAOYSA-N 2-methoxy-4,6-dinitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1N XLJMDBOKSZROPC-UHFFFAOYSA-N 0.000 description 1
GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
NIPDVSLAMPAWTP-UHFFFAOYSA-N 2-methoxy-5-nitroaniline Chemical compound COC1=CC=C([N+]([O-])=O)C=C1N NIPDVSLAMPAWTP-UHFFFAOYSA-N 0.000 description 1
INCJNDAQNPWMPZ-UHFFFAOYSA-N 3-amino-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1N INCJNDAQNPWMPZ-UHFFFAOYSA-N 0.000 description 1
VPZJHTWLWKFPQW-UHFFFAOYSA-N 3-chloro-2-methoxyaniline Chemical compound COC1=C(N)C=CC=C1Cl VPZJHTWLWKFPQW-UHFFFAOYSA-N 0.000 description 1
KWNQIIMVPSMYEM-UHFFFAOYSA-N 6,7-dimethoxy-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=C1C=C(OC)C(OC)=C2 KWNQIIMVPSMYEM-UHFFFAOYSA-N 0.000 description 1
TWLMSPNQBKSXOP-UHFFFAOYSA-N 6358-09-4 Chemical compound NC1=CC([N+]([O-])=O)=CC(Cl)=C1O TWLMSPNQBKSXOP-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
VNQABZCSYCTZMS-UHFFFAOYSA-N Orthoform Chemical compound COC(=O)C1=CC=C(O)C(N)=C1 VNQABZCSYCTZMS-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229920003180 amino resin Polymers 0.000 description 1
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical class ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
125000004799 bromophenyl group Chemical group 0.000 description 1
RDVQTQJAUFDLFA-UHFFFAOYSA-N cadmium Chemical compound [Cd][Cd][Cd][Cd][Cd][Cd][Cd][Cd][Cd] RDVQTQJAUFDLFA-UHFFFAOYSA-N 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 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
150000001805 chlorine compounds Chemical class 0.000 description 1
GSOLWAFGMNOBSY-UHFFFAOYSA-N cobalt Chemical compound [Co][Co][Co][Co][Co][Co][Co][Co] GSOLWAFGMNOBSY-UHFFFAOYSA-N 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000000986 disperse dye Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000009837 dry grinding Methods 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
238000001914 filtration Methods 0.000 description 1
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
150000002605 large molecules Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 description 1
VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000011368 organic material Substances 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
230000019612 pigmentation Effects 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
229920002239 polyacrylonitrile Polymers 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
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 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
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
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
239000008096 xylene Substances 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
- C09B55/002—Monoazomethine dyes

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Compositions Of Macromolecular Compounds (AREA)
Coloring (AREA)

CA234,235A 1974-08-28 1975-08-27 Composes metalliques complexes a base d'azamethine Expired CA1037962A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19742441092 DE2441092C3 (de)	1974-08-28	1974-08-28	Azamethin-Metallkomplex-Pigmente, Verfahren zu ihrer Herstellung und ihre Verwendung

Publications (1)

Publication Number	Publication Date
CA1037962A true CA1037962A (fr)	1978-09-05

Family

ID=5924226

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA234,235A Expired CA1037962A (fr)	1974-08-28	1975-08-27	Composes metalliques complexes a base d'azamethine

Country Status (9)

Country	Link
JP (1)	JPS5932499B2 (fr)
BE (1)	BE832856A (fr)
BR (1)	BR7505486A (fr)
CA (1)	CA1037962A (fr)
CH (1)	CH612447A5 (fr)
DE (1)	DE2441092C3 (fr)
FR (1)	FR2283181A1 (fr)
GB (1)	GB1523897A (fr)
IT (1)	IT1041928B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH085838Y2 (ja) *	1993-03-17	1996-02-21	株式会社貝印刃物開発センター	彫刻刀

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH568368A5 (fr) *	1972-06-19	1975-10-31	Ciba Geigy Ag
DE2337023C3 (de) *	1973-07-20	1979-09-06	Hoechst Ag, 6000 Frankfurt	Verfahren zur Herstellung von Aldehyden von 2-Hydroxynaphthalin-3-carbonsäurearylamiden

1974
- 1974-08-28 DE DE19742441092 patent/DE2441092C3/de not_active Expired
1975
- 1975-08-25 CH CH1098675A patent/CH612447A5/xx not_active IP Right Cessation
- 1975-08-26 IT IT2658375A patent/IT1041928B/it active
- 1975-08-26 JP JP10264575A patent/JPS5932499B2/ja not_active Expired
- 1975-08-27 BR BR7505486A patent/BR7505486A/pt unknown
- 1975-08-27 CA CA234,235A patent/CA1037962A/fr not_active Expired
- 1975-08-28 FR FR7526484A patent/FR2283181A1/fr active Granted
- 1975-08-28 BE BE159557A patent/BE832856A/fr unknown
- 1975-08-28 GB GB3553675A patent/GB1523897A/en not_active Expired

Also Published As

Publication number	Publication date
DE2441092A1 (de)	1976-03-18
JPS5932499B2 (ja)	1984-08-09
BR7505486A (pt)	1976-08-03
CH612447A5 (en)	1979-07-31
JPS5150324A (en)	1976-05-01
DE2441092C3 (de)	1980-11-20
FR2283181A1 (fr)	1976-03-26
GB1523897A (en)	1978-09-06
IT1041928B (it)	1980-01-10
FR2283181B1 (fr)	1978-10-27
DE2441092B2 (de)	1980-04-03
BE832856A (fr)	1976-03-01

Publication	Publication Date	Title
JP2609388B2 (ja)	1997-05-14	水溶性アゾ着色剤およびその用途
DE2359791C3 (de)	1979-07-12	Isoindolinonpigmente und deren Verwendung
DE2533676A1 (de)	1976-02-19	Verfahren zur herstellung von bisazomethin-metallkomplexfarbstoffen
CA1068262A (fr)	1979-12-18	Preparation de composes disazoiques; emploi comme pigments
US4065481A (en)	1977-12-27	1:1-Azomethine-metal-complex dyestuffs
CA1037962A (fr)	1978-09-05	Composes metalliques complexes a base d'azamethine
DE2244035C3 (de)	1979-10-04	Disazopigmente, Verfahren zu deren Herstellung und ihre Verwendung zum Pigmentieren von hochmolekularem organischen Material
US4096157A (en)	1978-06-20	Azamethine metal complex compounds
EP0169167B1 (fr)	1990-05-02	Procédé de coloration de matières organiques à haut poids moléculaire et complexes métalliques
DE2533674A1 (de)	1976-02-19	Neue bisazomethin-metallkomplexfarbstoffe aus hydroxycumarin- bzw. hydroxychromonderivaten und verfahren zu deren herstellung
US4077953A (en)	1978-03-07	Tri-dentate metal complex azo pigments
CA1249265A (fr)	1989-01-24	Complexes metalliques, et leur emploi
JPS60235865A (ja)	1985-11-22	カルボン酸アミド基を含むモノアゾ化合物
JPS6038422B2 (ja)	1985-08-31	アザメチン−金属錯化合物
US3878188A (en)	1975-04-15	Process for the manufacture of coloured polycyclic metal complexes
US3509123A (en)	1970-04-28	Monoazo pigments
DE1544459A1 (de)	1970-04-09	Verfahren zur Herstellung von Disazopigmenten
US3808215A (en)	1974-04-30	N alkoxyl naphthalimides
DE2544568C3 (de)	1979-02-08	Sulfonsäuregruppenfreie Azofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung als Pigmente in Lacken, Druckfarben oder Kunststoffen
DE2417217C3 (de)	1980-07-03	Pigmentfarbstoffe mit Oxidazolylresten, Verfahren zu deren Herstellung und ihre Verwendung
DE2002067B2 (de)	1978-06-15	Neue Disazopigmente, Verfahren zu deren Herstellung und Verwendung zum Pigmentieren von hochmolekularem organischem Material
CA1087173A (fr)	1980-10-07	Production de pigments azoiques
DE2415055A1 (de)	1975-10-02	Metallkomplexfarbstoffe
US3780049A (en)	1973-12-18	Nickel complexes of dioximes and processes for their manufacture
CA1053229A (fr)	1979-04-24	Colorants insolubles a l'eau, methode pour leur preparation, et leur mode d'emploi