JPS6212823B2 - - Google Patents

Info

Publication number: JPS6212823B2
Authority: JP; Japan
Prior art keywords: hydrogen; chlorine; carbon atoms; bromine; alkyl
Prior art date: 1978-02-13
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

JP54014418A

Other languages

English (en)

Japanese (ja)

Other versions

JPS54117534A (en

Inventor

Chaaruzu Bingamu Richaado

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.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

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

1987-03-20

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

1979-02-13 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1979-09-12 Publication of JPS54117534A publication Critical patent/JPS54117534A/ja

1987-03-20 Publication of JPS6212823B2 publication Critical patent/JPS6212823B2/ja

Status Granted legal-status Critical Current

Links

125000004432 carbon atom Chemical group C* 0.000 claims description 70
239000000460 chlorine Substances 0.000 claims description 68
229910052739 hydrogen Inorganic materials 0.000 claims description 64
239000001257 hydrogen Substances 0.000 claims description 64
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 55
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 55
229910052794 bromium Inorganic materials 0.000 claims description 55
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 53
229910052801 chlorine Inorganic materials 0.000 claims description 53
150000002431 hydrogen Chemical class 0.000 claims description 47
125000000217 alkyl group Chemical group 0.000 claims description 44
150000001875 compounds Chemical class 0.000 claims description 44
125000003545 alkoxy group Chemical group 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 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
125000001424 substituent group Chemical group 0.000 claims description 9
MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 7
125000005521 carbonamide group Chemical group 0.000 claims description 7
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 7
229940124530 sulfonamide Drugs 0.000 claims description 7
150000003456 sulfonamides Chemical class 0.000 claims description 7
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 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims 8
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 21
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 12
239000001052 yellow pigment Substances 0.000 description 12
239000003973 paint Substances 0.000 description 11
239000000049 pigment Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 8
238000000034 method Methods 0.000 description 8
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
238000001035 drying Methods 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-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
239000000376 reactant Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-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
235000001671 coumarin Nutrition 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
JKOCGAMDKVAHCI-UHFFFAOYSA-N 6,7-Benzocoumarin Chemical compound C1=CC=C2C=C(OC(=O)C=C3)C3=CC2=C1 JKOCGAMDKVAHCI-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-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
239000004033 plastic Substances 0.000 description 4
229920003023 plastic Polymers 0.000 description 4
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
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 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
229960000956 coumarin Drugs 0.000 description 3
150000004775 coumarins Chemical class 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
238000005984 hydrogenation reaction Methods 0.000 description 3
239000000463 material Substances 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
239000002904 solvent Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-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
239000004923 Acrylic lacquer Substances 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-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
150000004984 aromatic diamines Chemical class 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
239000013522 chelant Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 2
239000000374 eutectic mixture Substances 0.000 description 2
IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 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
239000004922 lacquer Substances 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
-1 naphtho[2.1-b]pyran-2-carboxamide Chemical compound 0.000 description 2
239000001053 orange pigment Substances 0.000 description 2
239000012860 organic pigment Substances 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
239000000126 substance Substances 0.000 description 2
229920001169 thermoplastic Polymers 0.000 description 2
239000004416 thermosoftening plastic Substances 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
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
IAFBRPFISOTXSO-UHFFFAOYSA-N 2-[[2-chloro-4-[3-chloro-4-[[1-(2,4-dimethylanilino)-1,3-dioxobutan-2-yl]diazenyl]phenyl]phenyl]diazenyl]-n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)C(C(=O)C)N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(C)=O)C(=O)NC1=CC=C(C)C=C1C IAFBRPFISOTXSO-UHFFFAOYSA-N 0.000 description 1
MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 description 1
GQFGHCRXPLROOF-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine sulfate Chemical compound OS(O)(=O)=O.NC1=CC=C(N)C(Cl)=C1 GQFGHCRXPLROOF-UHFFFAOYSA-N 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
WIGUZCABIKOWPD-UHFFFAOYSA-N 2-oxo-n-[2-[(2-oxochromene-3-carbonyl)amino]phenyl]chromene-3-carboxamide Chemical compound C1=CC=C2OC(=O)C(C(NC=3C(=CC=CC=3)NC(=O)C=3C(OC4=CC=CC=C4C=3)=O)=O)=CC2=C1 WIGUZCABIKOWPD-UHFFFAOYSA-N 0.000 description 1
MMTVHLPXGYWNOJ-UHFFFAOYSA-N 2h-pyran-2-carboxamide Chemical compound NC(=O)C1OC=CC=C1 MMTVHLPXGYWNOJ-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
BLYCIBKGUFWUPA-UHFFFAOYSA-N 3H-benzo[f]chromene-2-carboxamide Chemical compound C=1C2=C(OCC1C(=O)N)C=CC1=CC=CC=C12 BLYCIBKGUFWUPA-UHFFFAOYSA-N 0.000 description 1
YOJKEVXNAVNUGW-UHFFFAOYSA-N 4-n-chlorobenzene-1,4-diamine Chemical compound NC1=CC=C(NCl)C=C1 YOJKEVXNAVNUGW-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
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
241000245063 Primula Species 0.000 description 1
235000016311 Primula vulgaris Nutrition 0.000 description 1
229910010413 TiO 2 Inorganic materials 0.000 description 1
238000002083 X-ray spectrum Methods 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
238000000498 ball milling Methods 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
150000001733 carboxylic acid esters Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
229940117389 dichlorobenzene Drugs 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
239000006185 dispersion Substances 0.000 description 1
238000000921 elemental analysis 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
FYOZSKRVTISLHE-UHFFFAOYSA-N ethyl 3-oxobenzo[f]chromene-2-carboxylate Chemical compound C1=CC=C2C(C=C(C(O3)=O)C(=O)OCC)=C3C=CC2=C1 FYOZSKRVTISLHE-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000976 ink Substances 0.000 description 1
239000001023 inorganic pigment 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
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000003801 milling Methods 0.000 description 1
238000002156 mixing Methods 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
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
238000003672 processing method Methods 0.000 description 1
238000011120 smear test Methods 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000000979 synthetic dye Substances 0.000 description 1
238000012360 testing method Methods 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
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 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)

JP1441879A 1978-02-13 1979-02-13 Organic pigment Granted JPS54117534A (en)

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 (2)

Publication Number	Publication Date
JPS54117534A JPS54117534A (en)	1979-09-12
JPS6212823B2 true JPS6212823B2 (fr)	1987-03-20

Family

ID=27128441

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP1441879A Granted JPS54117534A (en)	1978-02-13	1979-02-13	Organic pigment

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
CH642074A5 (de)	1984-03-30
DE2905447A1 (de)	1979-08-16
GB2014180A (en)	1979-08-22

Publication	Publication Date	Title
JP4962812B2 (ja)	2012-06-27	フタロシアニン化合物およびその製造方法、ならびに該フタロシアニン化合物を含有する着色組成物
JP2956907B2 (ja)	1999-10-04	新規ピグメント
US4526963A (en)	1985-07-02	Dioxazine pigments
JPS6328109B2 (fr)	1988-06-07
JPS6212823B2 (fr)	1987-03-20
WO2006088140A1 (fr)	2006-08-24	Dérivé de phtalocyanine, procédé de synthèse dudit dérivé, et préparations colorées contenant ledit dérivé de phtalocyanine
JPS61215663A (ja)	1986-09-25	ナフタロシアニン化合物
US4240967A (en)	1980-12-23	Organic pigments derived from coumarin
CA2041887A1 (fr)	1991-11-09	Pigments jaunes fluorescents de 1,2,3,4-tetrachloro-11h-isoindolo-¬2,1-a\|-benzimidazol-11-one
US3357983A (en)	1967-12-12	Perylene pigments
US3496190A (en)	1970-02-17	Bis-tetrachloro-isoindolin-1-on-3-ylidene-imino pigment
JP4385985B2 (ja)	2009-12-16	フタロシアニン化合物およびそれを含有する着色組成物
US20060199882A1 (en)	2006-09-07	Heterocyclic dyes based on benzodipyrroles
US20040173777A1 (en)	2004-09-09	Fluorescent diketopyrrolopyrrole analogues
US2818410A (en)	1957-12-31	Dyes of the quinophthalone series
US4861898A (en)	1989-08-29	Isoindoline metal complexes
JPS6162564A (ja)	1986-03-31	アジン系顔料
JPS6241267B2 (fr)	1987-09-02
JPWO2021117410A1 (ja)	2021-12-09	キノフタロン化合物、顔料組成物及びカラーフィルタ
US4177195A (en)	1979-12-04	Organic pigments derived from benzocoumarin
US1065063A (en)	1913-06-17	Benzoquinone derivatives and process of making same.
US4582902A (en)	1986-04-15	3-hydroxy-8-oxoquinazolo[3,2-a]-quinoline phenyl azomethines
US4587339A (en)	1986-05-06	Nickel complex pigments of bis-azomethines
FR2553426A1 (fr)	1985-04-19	Nouveaux complexes nickeliferes de bis-azomethines utiles comme pigments, et intermediaires et procede pour leur preparation
US4581450A (en)	1986-04-08	3-hydroxy-8-oxoquinazolo[3,2-a]-quinolines