CH642074A5 - Cumarin- und benzocumarinderivate, verfahren zu deren herstellung und deren verwendung als pigmente. - Google Patents

Cumarin- und benzocumarinderivate, verfahren zu deren herstellung und deren verwendung als pigmente. Download PDF

Info

Publication number: CH642074A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; chlorine; bromine; alkyl; alkoxy
Prior art date: 1978-02-13

Application number

CH137779A

Other languages

German (de)

English (en)

Inventor

Richard Charles Bingham

Original Assignee

Du Pont

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.)

1978-02-13

Filing date

1979-02-13

Publication date

1984-03-30

1978-04-20 Priority claimed from US05/898,443 external-priority patent/US4177195A/en

1979-02-13 Application filed by Du Pont filed Critical Du Pont

1984-03-30 Publication of CH642074A5 publication Critical patent/CH642074A5/de

Links

238000000034 method Methods 0.000 title claims description 9
239000000049 pigment Substances 0.000 title description 11
238000004519 manufacturing process Methods 0.000 title description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 84
239000000460 chlorine Substances 0.000 claims description 77
229910052739 hydrogen Inorganic materials 0.000 claims description 69
239000001257 hydrogen Substances 0.000 claims description 68
229910052801 chlorine Inorganic materials 0.000 claims description 57
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 56
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 56
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 56
229910052794 bromium Inorganic materials 0.000 claims description 56
150000002431 hydrogen Chemical class 0.000 claims description 53
125000000217 alkyl group Chemical group 0.000 claims description 46
150000001875 compounds Chemical class 0.000 claims description 45
125000003545 alkoxy group Chemical group 0.000 claims description 41
-1 carbonamido Chemical group 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
XMQOBGDXGQSRID-UHFFFAOYSA-N 2-oxochromene-3-carboxamide Chemical compound C1=CC=C2OC(=O)C(C(=O)N)=CC2=C1 XMQOBGDXGQSRID-UHFFFAOYSA-N 0.000 claims description 10
235000001671 coumarin Nutrition 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
JKOCGAMDKVAHCI-UHFFFAOYSA-N 6,7-Benzocoumarin Chemical class C1=CC=C2C=C(OC(=O)C=C3)C3=CC2=C1 JKOCGAMDKVAHCI-UHFFFAOYSA-N 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 7
229960000956 coumarin Drugs 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 5
150000004984 aromatic diamines Chemical class 0.000 claims description 4
125000005544 phthalimido group Chemical group 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
239000012860 organic pigment Substances 0.000 claims description 3
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims 6
125000005521 carbonamide group Chemical group 0.000 claims 1
125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
239000000047 product Substances 0.000 description 63
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 20
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 18
238000001914 filtration Methods 0.000 description 14
239000003973 paint Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
239000001052 yellow pigment Substances 0.000 description 11
238000004458 analytical method Methods 0.000 description 10
MMTVHLPXGYWNOJ-UHFFFAOYSA-N 2h-pyran-2-carboxamide Chemical compound NC(=O)C1OC=CC=C1 MMTVHLPXGYWNOJ-UHFFFAOYSA-N 0.000 description 9
MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 7
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 7
238000001035 drying Methods 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
LTUFGCFAPCJOFQ-UHFFFAOYSA-N 2h-pyran-3-carboxamide Chemical compound NC(=O)C1=CC=COC1 LTUFGCFAPCJOFQ-UHFFFAOYSA-N 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
239000000463 material Substances 0.000 description 5
239000004033 plastic Substances 0.000 description 5
229920003023 plastic Polymers 0.000 description 5
239000007787 solid Substances 0.000 description 5
UZXZSPGHNLGPIC-UHFFFAOYSA-N 3-oxobenzo[f]chromene-2-carbonyl chloride Chemical compound C1=CC=C2C(C=C(C(O3)=O)C(=O)Cl)=C3C=CC2=C1 UZXZSPGHNLGPIC-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
235000010290 biphenyl Nutrition 0.000 description 4
239000004305 biphenyl Substances 0.000 description 4
229910001385 heavy metal Inorganic materials 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
MYRKQWLSHLIPIH-UHFFFAOYSA-N 2-oxo-n-[4-[(2-oxochromene-3-carbonyl)amino]phenyl]chromene-3-carboxamide Chemical compound C1=CC=C2OC(=O)C(C(NC=3C=CC(NC(=O)C=4C(OC5=CC=CC=C5C=4)=O)=CC=3)=O)=CC2=C1 MYRKQWLSHLIPIH-UHFFFAOYSA-N 0.000 description 3
ZOZWADMLNMOQJH-UHFFFAOYSA-N 6,8-dichloro-2-oxochromene-3-carboxamide Chemical compound ClC1=CC(Cl)=C2OC(=O)C(C(=O)N)=CC2=C1 ZOZWADMLNMOQJH-UHFFFAOYSA-N 0.000 description 3
JJALPYSRHDYYBA-UHFFFAOYSA-N 6-chloro-2-oxochromene-3-carboxamide Chemical compound ClC1=CC=C2OC(=O)C(C(=O)N)=CC2=C1 JJALPYSRHDYYBA-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 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
238000000576 coating method Methods 0.000 description 3
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
235000011056 potassium acetate Nutrition 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 description 2
GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 2
IVEOLEMGKYWBTC-UHFFFAOYSA-N 2-oxochromene-3-carbonyl chloride Chemical compound C1=CC=C2OC(=O)C(C(=O)Cl)=CC2=C1 IVEOLEMGKYWBTC-UHFFFAOYSA-N 0.000 description 2
XGIOMPQAVKJLDA-UHFFFAOYSA-N CC1=C(C=C(C(=C1)NC(=O)C1=CC2=C(OC1=O)C=CC1=CC=CC=C12)C)NC(=O)C1=CC2=C(OC1=O)C=CC1=CC=CC=C12 Chemical compound CC1=C(C=C(C(=C1)NC(=O)C1=CC2=C(OC1=O)C=CC1=CC=CC=C12)C)NC(=O)C1=CC2=C(OC1=O)C=CC1=CC=CC=C12 XGIOMPQAVKJLDA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
150000004056 anthraquinones Chemical class 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
239000013522 chelant Substances 0.000 description 2
239000003086 colorant Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
150000004775 coumarins Chemical class 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000000374 eutectic mixture Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
238000013508 migration Methods 0.000 description 2
230000005012 migration Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
238000005507 spraying Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
229920001169 thermoplastic Polymers 0.000 description 2
239000004416 thermosoftening plastic Substances 0.000 description 2
FOVOBTLEKSQTFG-UHFFFAOYSA-N 2,5-dimethoxybenzene-1,4-diamine Chemical compound COC1=CC(N)=C(OC)C=C1N FOVOBTLEKSQTFG-UHFFFAOYSA-N 0.000 description 1
125000005826 2-chloro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(Cl)C([*:1])=C1[H] 0.000 description 1
HGUYBLVGLMAUFF-UHFFFAOYSA-N 2-methoxybenzene-1,4-diamine Chemical compound COC1=CC(N)=CC=C1N HGUYBLVGLMAUFF-UHFFFAOYSA-N 0.000 description 1
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
AKTBLLITNRMZEJ-UHFFFAOYSA-N 2H-pyran-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=COC1 AKTBLLITNRMZEJ-UHFFFAOYSA-N 0.000 description 1
GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical class C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
UDQLIWBWHVOIIF-UHFFFAOYSA-N 3-phenylbenzene-1,2-diamine Chemical class NC1=CC=CC(C=2C=CC=CC=2)=C1N UDQLIWBWHVOIIF-UHFFFAOYSA-N 0.000 description 1
ZIFXNYNQBZSHHD-UHFFFAOYSA-N 6-chloro-N-[3-chloro-4-[(6-chloro-2-oxobenzo[h]chromene-3-carbonyl)amino]phenyl]-2-oxobenzo[h]chromene-3-carboxamide Chemical compound ClC1=C(C=CC(=C1)NC(=O)C1=CC2=C(OC1=O)C1=CC=CC=C1C(=C2)Cl)NC(=O)C1=CC2=C(OC1=O)C1=CC=CC=C1C(=C2)Cl ZIFXNYNQBZSHHD-UHFFFAOYSA-N 0.000 description 1
SIGABXYVMQXSCM-UHFFFAOYSA-N 6-nitro-2-oxochromene-3-carbonyl chloride Chemical compound O1C(=O)C(C(Cl)=O)=CC2=CC([N+](=O)[O-])=CC=C21 SIGABXYVMQXSCM-UHFFFAOYSA-N 0.000 description 1
GNYBHYYPHFKXKB-UHFFFAOYSA-N 8-chloro-3-oxobenzo[f]chromene-2-carboxamide Chemical compound O=C1C(=CC2=C(O1)C=CC1=CC(=CC=C12)Cl)C(=O)N GNYBHYYPHFKXKB-UHFFFAOYSA-N 0.000 description 1
QPLQWJPXYACJNJ-UHFFFAOYSA-N 8-methyl-3-oxobenzo[f]chromene-2-carboxamide Chemical compound O=C1C(=CC2=C(O1)C=CC1=CC(=CC=C12)C)C(=O)N QPLQWJPXYACJNJ-UHFFFAOYSA-N 0.000 description 1
YZKJZLCCMXEVKW-UHFFFAOYSA-N 8-methyl-N-[4-[(8-methyl-3-oxobenzo[f]chromene-2-carbonyl)amino]phenyl]-3-oxobenzo[f]chromene-2-carboxamide Chemical compound C1(=CC=C(C=C1)NC(=O)C1=CC2=C(OC1=O)C=CC1=CC(=CC=C12)C)NC(=O)C1=CC2=C(OC1=O)C=CC1=CC(=CC=C12)C YZKJZLCCMXEVKW-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
DWOUKYZJXAQFMV-UHFFFAOYSA-N N-[3-chloro-4-[(9-methyl-3-oxobenzo[f]chromene-2-carbonyl)amino]phenyl]-9-methyl-3-oxobenzo[f]chromene-2-carboxamide Chemical compound ClC1=C(C=CC(=C1)NC(=O)C1=CC2=C(OC1=O)C=CC1=CC=C(C=C12)C)NC(=O)C1=CC2=C(OC1=O)C=CC1=CC=C(C=C12)C DWOUKYZJXAQFMV-UHFFFAOYSA-N 0.000 description 1
GEWLEHGMFZNJMO-UHFFFAOYSA-N N-[5-chloro-2-methyl-4-[(3-oxobenzo[f]chromene-2-carbonyl)amino]phenyl]-3-oxobenzo[f]chromene-2-carboxamide Chemical compound CC1=C(C=C(C(=C1)NC(=O)C1=CC2=C(OC1=O)C=CC1=CC=CC=C12)Cl)NC(=O)C1=CC2=C(OC1=O)C=CC1=CC=CC=C12 GEWLEHGMFZNJMO-UHFFFAOYSA-N 0.000 description 1
238000002083 X-ray spectrum Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
FXRDPPFLWGSMQT-UHFFFAOYSA-N benzo[f]chromen-3-one Chemical compound C1=CC=C2C(C=CC(O3)=O)=C3C=CC2=C1 FXRDPPFLWGSMQT-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052980 cadmium sulfide Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
DGXKDBWJDQHNCI-UHFFFAOYSA-N dioxido(oxo)titanium nickel(2+) Chemical compound [Ni++].[O-][Ti]([O-])=O DGXKDBWJDQHNCI-UHFFFAOYSA-N 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
XKHPEMKBJGUYCM-UHFFFAOYSA-N ethyl 2-oxochromene-3-carboxylate Chemical compound C1=CC=C2OC(=O)C(C(=O)OCC)=CC2=C1 XKHPEMKBJGUYCM-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000000976 ink Substances 0.000 description 1
239000001023 inorganic pigment Substances 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
GEQBMMJSIVOFFQ-UHFFFAOYSA-N n-[3-methoxy-4-[(3-oxobenzo[f]chromene-2-carbonyl)amino]phenyl]-3-oxobenzo[f]chromene-2-carboxamide Chemical compound C1=CC=C2C(C=C(C(O3)=O)C(=O)NC4=CC=C(NC(=O)C=5C(OC6=C(C7=CC=CC=C7C=C6)C=5)=O)C=C4OC)=C3C=CC2=C1 GEQBMMJSIVOFFQ-UHFFFAOYSA-N 0.000 description 1
239000001053 orange pigment Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
230000000485 pigmenting effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
BASFCYQUMIYNBI-BKFZFHPZSA-N platinum-200 Chemical compound [200Pt] BASFCYQUMIYNBI-BKFZFHPZSA-N 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
231100000683 possible toxicity Toxicity 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000007639 printing Methods 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000979 synthetic dye Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000012463 white pigment 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/02—Coumarine dyes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/14—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 6 and unsubstituted in position 7
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

CH137779A 1978-02-13 1979-02-13 Cumarin- und benzocumarinderivate, verfahren zu deren herstellung und deren verwendung als pigmente. CH642074A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US87746278A	1978-02-13	1978-02-13
US05/898,443 US4177195A (en)	1978-04-20	1978-04-20	Organic pigments derived from benzocoumarin

Publications (1)

Publication Number	Publication Date
CH642074A5 true CH642074A5 (de)	1984-03-30

Family

ID=27128441

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH137779A CH642074A5 (de)	1978-02-13	1979-02-13	Cumarin- und benzocumarinderivate, verfahren zu deren herstellung und deren verwendung als pigmente.

Country Status (7)

Country	Link
JP (1)	JPS54117534A (fr)
CA (1)	CA1121822A (fr)
CH (1)	CH642074A5 (fr)
DE (1)	DE2905447A1 (fr)
FR (1)	FR2416925B1 (fr)
GB (1)	GB2014180B (fr)
IT (1)	IT1121051B (fr)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1470053A (fr) *	1965-02-27	1967-02-17	Ferrania Spa	Nouvelles coumarines photoconductrices et articles de reproduction électrophotographique à base de telles coumarines
US3509177A (en) *	1968-06-24	1970-04-28	Dow Chemical Co	Alkylene and arylenebis(3-carbamoyl-4-hydroxycoumarin)s
CH565228A5 (fr) *	1972-04-18	1975-08-15	Ciba Geigy Ag
DE2226211A1 (de) *	1972-05-30	1973-12-13	Basf Ag	N-substituierte iminocumarinfarbstoffe
DE2234207A1 (de) *	1972-07-12	1974-01-31	Basf Ag	N-substituierte iminocumarin-farbstoffe
CH591546A5 (fr) *	1974-07-31	1977-09-30	Ciba Geigy Ag

1979
- 1979-02-09 CA CA000321189A patent/CA1121822A/fr not_active Expired
- 1979-02-09 GB GB7904633A patent/GB2014180B/en not_active Expired
- 1979-02-12 IT IT20136/79A patent/IT1121051B/it active
- 1979-02-12 FR FR7903475A patent/FR2416925B1/fr not_active Expired
- 1979-02-13 CH CH137779A patent/CH642074A5/de not_active IP Right Cessation
- 1979-02-13 DE DE19792905447 patent/DE2905447A1/de not_active Ceased
- 1979-02-13 JP JP1441879A patent/JPS54117534A/ja active Granted

Also Published As

Publication number	Publication date
IT7920136A0 (it)	1979-02-12
FR2416925A1 (fr)	1979-09-07
IT1121051B (it)	1986-03-26
CA1121822A (fr)	1982-04-13
GB2014180B (en)	1982-06-30
FR2416925B1 (fr)	1986-03-21
JPS54117534A (en)	1979-09-12
JPS6212823B2 (fr)	1987-03-20
DE2905447A1 (de)	1979-08-16
GB2014180A (en)	1979-08-22

Legal Events

Date	Code	Title	Description
1988-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0224445B1 (fr)	1991-09-04	Préparations des pigments pyrrolo-pyrroles, leur procédé de préparation et leur application
US4044036A (en)	1977-08-23	Metal complexes of bis-azomethines from hydroxy-aldehydes and alkylene diamines
DE2263235A1 (de)	1973-07-12	Heterocyclische metallkomplexverbindungen, ihre herstellung und verwendung
DE2260499B2 (de)	1981-06-11	Kupferkomplexe von Azomethinfarbstoffen und Verfahren zum Pigmentieren von hochmolekularem organischem Material
EP0088729B1 (fr)	1987-07-29	Utilisation de complexes métalliques d'hydrazones comme pigments
EP0035174A1 (fr)	1981-09-09	Colorants dérivés de l'isoindoline et leur utilisation
EP0101954B1 (fr)	1986-07-02	Isoindolazines, leur procédé de fabrication et leur utilisation
CH622278A5 (fr)	1981-03-31
CH642074A5 (de)	1984-03-30	Cumarin- und benzocumarinderivate, verfahren zu deren herstellung und deren verwendung als pigmente.
DE2151723B2 (de)	1973-09-20	Indigoide Pigmente, ihre Herste! lung und Verwendung
EP0190692A2 (fr)	1986-08-13	Pigments de bis-indoline et leur utilisation
KR19980018836A (ko)	1998-06-05	디케토피롤로피롤 안료의 신규 결정 변태(Novel Crystal Modification of a Diketopyrrolopyrrole Pigment)
DE2429286C2 (de)	1983-04-21	Neue Disazopigmente, Verfahren zu deren Herstellung und deren Verwendung
DE2616486A1 (de)	1977-11-03	Farbstoffe der perylentetracarbonsaeurediimidreihe
DE3911643C2 (de)	1999-09-23	Heterocyclische Farbstoffe
CH688689A5 (de)	1998-01-15	Loesungsmittelfarbstoffe.
US4240967A (en)	1980-12-23	Organic pigments derived from coumarin
DE4409902A1 (de)	1995-09-28	Isoindolinazopigmente
DE2012505B2 (de)	1977-09-15	Kupfer- und nickelphthalocyanin- mischkondensat-pigmente
EP0074559B1 (fr)	1985-01-23	Bêta-céto-amides et préparations pigmentaires contenant ces amides
EP0000505A1 (fr)	1979-02-07	Complexes de métaux, leur procédé de préparation et leur application comme pigments
CH627771A5 (de)	1982-01-29	Neue stabile modifikation eines isoindolinonpigmentes.
DE2447228A1 (de)	1976-04-22	Perinon-verbindungen, verfahren zu deren herstellung und ihre verwendung als farbmittel
EP0657507A2 (fr)	1995-06-14	Procédé de fabrication de pigments bisisoindoliniques dissymétriques
EP0015570A1 (fr)	1980-09-17	Pigments isoindoliniques et leur utilisation