CA1080231A - Pigments complexes a base d'azomethine symmetrique, heterocyclique - Google Patents

Pigments complexes a base d'azomethine symmetrique, heterocyclique

Info

Publication number: CA1080231A
Authority: CA; Canada
Prior art keywords: carbon atoms; residue; formula; methyl; heterocyclic
Prior art date: 1976-06-30
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

CA281,560A

Other languages

English (en)

Inventor

Colin D. Campbell

James M. Mccrae

Terence R. Chamberlain

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.)

1976-06-30

Filing date

1977-06-28

Publication date

1980-06-24

1977-06-28 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1980-06-24 Application granted granted Critical

1980-06-24 Publication of CA1080231A publication Critical patent/CA1080231A/fr

Status Expired legal-status Critical Current

Links

125000000623 heterocyclic group Chemical group 0.000 title abstract 3
239000000049 pigment Substances 0.000 title description 22
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
150000001875 compounds Chemical class 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 10
239000011368 organic material Substances 0.000 claims abstract description 5
239000000203 mixture Substances 0.000 claims description 21
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 20
229910052759 nickel Inorganic materials 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
229910052802 copper Inorganic materials 0.000 claims description 4
239000010949 copper Substances 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
125000003884 phenylalkyl group Chemical group 0.000 claims description 3
WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical group O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 20
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 3
230000000485 pigmenting effect Effects 0.000 abstract description 2
229910052723 transition metal Inorganic materials 0.000 abstract description 2
125000003118 aryl group Chemical group 0.000 abstract 3
125000002947 alkylene group Chemical group 0.000 abstract 1
125000003710 aryl alkyl group Chemical group 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
150000003624 transition metals Chemical class 0.000 abstract 1
238000000034 method Methods 0.000 description 14
239000000047 product Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
238000002360 preparation method Methods 0.000 description 9
239000003446 ligand Substances 0.000 description 8
-1 su]phates Chemical class 0.000 description 7
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
239000003973 paint Substances 0.000 description 6
229920005989 resin Polymers 0.000 description 6
239000011347 resin Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
229920003023 plastic Polymers 0.000 description 5
239000004033 plastic Substances 0.000 description 5
235000017281 sodium acetate Nutrition 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000001052 yellow pigment Substances 0.000 description 5
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000001632 sodium acetate Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
239000004411 aluminium Substances 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
150000004696 coordination complex Chemical class 0.000 description 3
150000004985 diamines Chemical class 0.000 description 3
229960000443 hydrochloric acid Drugs 0.000 description 3
235000011167 hydrochloric acid Nutrition 0.000 description 3
229940078494 nickel acetate Drugs 0.000 description 3
239000002002 slurry Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000000725 suspension Substances 0.000 description 3
VMDBJBQFGBVZKR-UHFFFAOYSA-N 4-hydroxy-1-methyl-2-oxoquinoline-3-carbaldehyde Chemical compound C1=CC=C2C(O)=C(C=O)C(=O)N(C)C2=C1 VMDBJBQFGBVZKR-UHFFFAOYSA-N 0.000 description 2
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
238000010793 Steam injection (oil industry) Methods 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
238000000576 coating method Methods 0.000 description 2
230000003750 conditioning effect Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 2
238000000227 grinding Methods 0.000 description 2
229920001903 high density polyethylene Polymers 0.000 description 2
239000004700 high-density polyethylene Substances 0.000 description 2
239000000976 ink Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000001465 metallisation Methods 0.000 description 2
238000003801 milling Methods 0.000 description 2
239000000025 natural resin Substances 0.000 description 2
DWAHIRJDCNGEDV-UHFFFAOYSA-N nickel(2+);dinitrate;hydrate Chemical compound O.[Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O DWAHIRJDCNGEDV-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000005507 spraying Methods 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
IGLBZDULNHFRQQ-UHFFFAOYSA-N 1-benzyl-4-hydroxy-2-oxoquinoline-3-carbaldehyde Chemical compound C12=CC=CC=C2C(O)=C(C=O)C(=O)N1CC1=CC=CC=C1 IGLBZDULNHFRQQ-UHFFFAOYSA-N 0.000 description 1
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 1
HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 description 1
VWLLPPSBBHDXHK-UHFFFAOYSA-N 3,4-diaminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1N VWLLPPSBBHDXHK-UHFFFAOYSA-N 0.000 description 1
DMEPVFSJYHJGCD-UHFFFAOYSA-N 3,5-dimethylbenzene-1,2-diamine Chemical compound CC1=CC(C)=C(N)C(N)=C1 DMEPVFSJYHJGCD-UHFFFAOYSA-N 0.000 description 1
BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-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
SKIUVOVOIJBJPN-UHFFFAOYSA-N 4,5-dimethoxybenzene-1,2-diamine Chemical compound COC1=CC(N)=C(N)C=C1OC SKIUVOVOIJBJPN-UHFFFAOYSA-N 0.000 description 1
XSZYBMMYQCYIPC-UHFFFAOYSA-N 4,5-dimethyl-1,2-phenylenediamine Chemical compound CC1=CC(N)=C(N)C=C1C XSZYBMMYQCYIPC-UHFFFAOYSA-N 0.000 description 1
RQWJHUJJBYMJMN-UHFFFAOYSA-N 4-(trifluoromethyl)benzene-1,2-diamine Chemical compound NC1=CC=C(C(F)(F)F)C=C1N RQWJHUJJBYMJMN-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
NYNSGFOMPNKBGG-UHFFFAOYSA-N 4-chloro-5-methoxybenzene-1,2-diamine Chemical compound COC1=CC(N)=C(N)C=C1Cl NYNSGFOMPNKBGG-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
DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
RAUWPNXIALNKQM-UHFFFAOYSA-N 4-nitro-1,2-phenylenediamine Chemical compound NC1=CC=C([N+]([O-])=O)C=C1N RAUWPNXIALNKQM-UHFFFAOYSA-N 0.000 description 1
FJVIHKKXPLPDSV-UHFFFAOYSA-N 4-phenoxybenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1OC1=CC=CC=C1 FJVIHKKXPLPDSV-UHFFFAOYSA-N 0.000 description 1
NLWNEYNEOSWQGI-UHFFFAOYSA-N 4-phenyl-2-n-propan-2-ylbenzene-1,2-diamine Chemical compound C1=C(N)C(NC(C)C)=CC(C=2C=CC=CC=2)=C1 NLWNEYNEOSWQGI-UHFFFAOYSA-N 0.000 description 1
NECWXNDIPQKNCD-UHFFFAOYSA-N 5,6-diaminobenzimidazol-2-one Chemical compound C1=C(N)C(N)=CC2=NC(=O)N=C21 NECWXNDIPQKNCD-UHFFFAOYSA-N 0.000 description 1
BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
229920000178 Acrylic resin Polymers 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
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
241000282320 Panthera leo Species 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
241001510071 Pyrrhocoridae Species 0.000 description 1
KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
238000013019 agitation Methods 0.000 description 1
229910052783 alkali metal Chemical group 0.000 description 1
150000001340 alkali metals Chemical group 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
229920003180 amino resin Polymers 0.000 description 1
238000000498 ball milling Methods 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000000337 buffer salt Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
230000015556 catabolic process Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
229920001727 cellulose butyrate Polymers 0.000 description 1
229920003086 cellulose ether Polymers 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical group [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
230000022244 formylation Effects 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000009775 high-speed stirring Methods 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
150000002605 large molecules Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
VYVHKDMXSZKXSD-UHFFFAOYSA-N n-(3,4-diaminophenyl)benzamide Chemical compound C1=C(N)C(N)=CC=C1NC(=O)C1=CC=CC=C1 VYVHKDMXSZKXSD-UHFFFAOYSA-N 0.000 description 1
NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 1
XTBLDMQMUSHDEN-UHFFFAOYSA-N naphthalene-2,3-diamine Chemical compound C1=CC=C2C=C(N)C(N)=CC2=C1 XTBLDMQMUSHDEN-UHFFFAOYSA-N 0.000 description 1
150000002815 nickel Chemical class 0.000 description 1
KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 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
229920000728 polyester Polymers 0.000 description 1
229920000642 polymer 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
229940051841 polyoxyethylene ether Drugs 0.000 description 1
229920000056 polyoxyethylene ether Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
150000003097 polyterpenes Chemical class 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000007639 printing Methods 0.000 description 1
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
150000007660 quinolones Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture 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
229940087562 sodium acetate trihydrate Drugs 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical class [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
238000009987 spinning Methods 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 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
- C09B55/006—Disazomethine dyes containing at least one heteroring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Paints Or Removers (AREA)
Pigments, Carbon Blacks, Or Wood Stains (AREA)
Compositions Of Macromolecular Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA281,560A 1976-06-30 1977-06-28 Pigments complexes a base d'azomethine symmetrique, heterocyclique Expired CA1080231A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB2735576A GB1534787A (en)	1976-06-30	1976-06-30	Azomethine metal complex pigments

Publications (1)

Publication Number	Publication Date
CA1080231A true CA1080231A (fr)	1980-06-24

Family

ID=10258265

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA281,560A Expired CA1080231A (fr)	1976-06-30	1977-06-28	Pigments complexes a base d'azomethine symmetrique, heterocyclique

Country Status (5)

Country	Link
JP (1)	JPS533428A (fr)
CA (1)	CA1080231A (fr)
DE (1)	DE2728864A1 (fr)
FR (1)	FR2356700A1 (fr)
GB (1)	GB1534787A (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2917312A1 (de) *	1979-04-28	1980-11-06	Bayer Ag	Anthrachinon-derivate
US4508899A (en) *	1983-10-14	1985-04-02	Sun Chemical Corporation	Nickel complex pigments of bis-azomethines
FR2620713B1 (fr) *	1987-09-23	1992-04-17	Sandoz Sa	Procede de teinture dans la masse des polyamides synthetiques
US4866112A (en) *	1988-07-29	1989-09-12	Ciba-Geigy Corporation	Thermoplastics containing a nickel complex pigment
WO2003060019A1 (fr)	2002-01-04	2003-07-24	University Of Dayton	Pigments anticorrosion non toxiques a base de cobalt
US20040011252A1 (en)	2003-01-13	2004-01-22	Sturgill Jeffrey A.	Non-toxic corrosion-protection pigments based on manganese

1976
- 1976-06-30 GB GB2735576A patent/GB1534787A/en not_active Expired
1977
- 1977-06-27 DE DE19772728864 patent/DE2728864A1/de not_active Withdrawn
- 1977-06-28 CA CA281,560A patent/CA1080231A/fr not_active Expired
- 1977-06-29 FR FR7719936A patent/FR2356700A1/fr active Granted
- 1977-06-30 JP JP7846877A patent/JPS533428A/ja active Pending

Also Published As

Publication number	Publication date
GB1534787A (en)	1978-12-06
DE2728864A1 (de)	1978-01-05
FR2356700B1 (fr)	1980-02-15
FR2356700A1 (fr)	1978-01-27
JPS533428A (en)	1978-01-13

Legal Events

Date	Code	Title	Description
1997-06-24	MKEX	Expiry

Publication	Publication Date	Title
DE2359791C3 (de)	1979-07-12	Isoindolinonpigmente und deren Verwendung
US5424429A (en)	1995-06-13	Preparation of pigmentary 2,9-dichloroquinacridone
US3895041A (en)	1975-07-15	Metallised pigments
CA1080231A (fr)	1980-06-24	Pigments complexes a base d'azomethine symmetrique, heterocyclique
US4065481A (en)	1977-12-27	1:1-Azomethine-metal-complex dyestuffs
US3700709A (en)	1972-10-24	Azomethine pigments
JP2886567B2 (ja)	1999-04-26	アンタントロン系の顔料調製物の製造方法
US3988323A (en)	1976-10-26	Metal complexes of bishydrazides
US5755875A (en)	1998-05-26	Fluorescent chromophores containing cyanimino groups
SU628824A3 (ru)	1978-10-15	Способ крашени высокомолекул рного органического материала
JPH08231872A (ja)	1996-09-10	金属リン酸塩錯塩とアミンとでコーティングされた有機顔料
CA1083590A (fr)	1980-08-12	Preparation et emploi comme colorants de composes disazoiques de methine, insolubles dans l'eau
CA1064950A (fr)	1979-10-23	Complexes metalliques colorants a base de bis-azomethine derives de l'hydroxycoumarine ou de l'hydroxychromone et procede pour leur fabrication
US5066695A (en)	1991-11-19	High-molecular weight organic material containing a metal complex pigment basaed on hydrazone
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
JP3501296B2 (ja)	2004-03-02	新規なビスアゾ、ビスアゾメチンおよびアゾ−アゾメチン化合物
CA1115881A (fr)	1982-01-05	Methode de pigmentation de matieres organiques de forte densite
US3987023A (en)	1976-10-19	Azo pigment metal complexes
CA1052803A (fr)	1979-04-17	Composes de methine diazoique insolubles dans l'eau
US4152324A (en)	1979-05-01	Pigment copper complex of carboxyphenylazon-phenyl-β-naphthyzamine
US3971739A (en)	1976-07-27	Tri or tetradentate metal azo pigment complexes
CA1092121A (fr)	1980-12-23	Complexes pigmentaires de cuivre et de 2-quinoline azomethine
CA1064481A (fr)	1979-10-16	Pigments disazo, procede pour leur fabrication et leur utilisation
EP0183651B1 (fr)	1990-05-23	Complexes de métaux, procédé pour leur préparation et leur utilisation