CA1121822A - Derives de la coumarine ou de la benzocoumarine, utilises comme pigments - Google Patents

Derives de la coumarine ou de la benzocoumarine, utilises comme pigments

Info

Publication number: CA1121822A
Authority: CA; Canada
Prior art keywords: carbon atoms; hydrogen; chlorine; 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

CA000321189A

Other languages

English (en)

Inventor

Richard C. Bingham

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

1979-02-09

Publication date

1982-04-13

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

1979-02-09 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1982-04-13 Application granted granted Critical

1982-04-13 Publication of CA1121822A publication Critical patent/CA1121822A/fr

Status Expired legal-status Critical Current

Links

239000000049 pigment Substances 0.000 title description 9
JKOCGAMDKVAHCI-UHFFFAOYSA-N 6,7-Benzocoumarin Chemical compound C1=CC=C2C=C(OC(=O)C=C3)C3=CC2=C1 JKOCGAMDKVAHCI-UHFFFAOYSA-N 0.000 title description 5
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 title description 2
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 95
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 73
239000001257 hydrogen Substances 0.000 claims abstract description 73
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 70
239000000460 chlorine Substances 0.000 claims abstract description 62
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 55
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 55
229910052794 bromium Inorganic materials 0.000 claims abstract description 55
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 54
229910052801 chlorine Inorganic materials 0.000 claims abstract description 54
235000017168 chlorine Nutrition 0.000 claims abstract description 54
229940060038 chlorine Drugs 0.000 claims abstract description 54
125000000217 alkyl group Chemical group 0.000 claims abstract description 51
125000003545 alkoxy group Chemical group 0.000 claims abstract description 44
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
-1 carbonamido Chemical group 0.000 claims abstract description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
125000005544 phthalimido group Chemical group 0.000 claims abstract description 5
SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 44
125000002496 methyl group Chemical group [H]C([H])([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 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims 8
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 2
125000005521 carbonamide group Chemical group 0.000 claims 1
239000012860 organic pigment Substances 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
239000000047 product Substances 0.000 description 19
239000000203 mixture Substances 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
239000003973 paint Substances 0.000 description 11
238000001914 filtration Methods 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 9
238000000034 method Methods 0.000 description 7
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 6
MKGAEQPPIKXYSS-UHFFFAOYSA-N 3-oxobenzo[f]chromene-2-carboxamide Chemical compound C1=CC=C2C(C=C(C(O3)=O)C(=O)N)=C3C=CC2=C1 MKGAEQPPIKXYSS-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
239000000376 reactant Substances 0.000 description 6
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
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
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
235000010290 biphenyl Nutrition 0.000 description 4
239000004305 biphenyl Substances 0.000 description 4
229960000956 coumarin Drugs 0.000 description 4
238000001035 drying Methods 0.000 description 4
229910001385 heavy metal Inorganic materials 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
239000001052 yellow pigment Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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
229910052799 carbon Inorganic materials 0.000 description 3
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000002904 solvent Substances 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
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 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
125000001246 bromo group Chemical group Br* 0.000 description 2
239000013522 chelant Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
125000001309 chloro group Chemical group Cl* 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
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 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
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
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
238000013508 migration Methods 0.000 description 2
230000005012 migration Effects 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
238000005507 spraying 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
HGUYBLVGLMAUFF-UHFFFAOYSA-N 2-methoxybenzene-1,4-diamine Chemical compound COC1=CC(N)=CC=C1N HGUYBLVGLMAUFF-UHFFFAOYSA-N 0.000 description 1
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 1
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-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
FLZMINOXPIKLBY-UHFFFAOYSA-N 6-nitro-2-oxochromene-3-carboxamide Chemical compound [O-][N+](=O)C1=CC=C2OC(=O)C(C(=O)N)=CC2=C1 FLZMINOXPIKLBY-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000004923 Acrylic lacquer Substances 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
101100536354 Drosophila melanogaster tant gene Proteins 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
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
238000002083 X-ray spectrum Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
238000000498 ball milling Methods 0.000 description 1
MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 1
150000008641 benzimidazolones 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
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
238000001816 cooling 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
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
230000005496 eutectics Effects 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
239000001056 green pigment Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000000976 ink Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 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
238000004519 manufacturing process Methods 0.000 description 1
238000003801 milling Methods 0.000 description 1
KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-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
230000019612 pigmentation Effects 0.000 description 1
229910003446 platinum oxide Inorganic materials 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
230000036647 reaction Effects 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000000126 substance Substances 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)

CA000321189A 1978-02-13 1979-02-09 Derives de la coumarine ou de la benzocoumarine, utilises comme pigments Expired CA1121822A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US87746278A	1978-02-13	1978-02-13
US877,462		1978-02-13
US05/898,443 US4177195A (en)	1978-04-20	1978-04-20	Organic pigments derived from benzocoumarin
US898,443		1997-07-22

Publications (1)

Publication Number	Publication Date
CA1121822A true CA1121822A (fr)	1982-04-13

Family

ID=27128441

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000321189A Expired CA1121822A (fr)	1978-02-13	1979-02-09	Derives de la coumarine ou de la benzocoumarine, utilises comme pigments

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 DE DE19792905447 patent/DE2905447A1/de not_active Ceased
- 1979-02-13 JP JP1441879A patent/JPS54117534A/ja active Granted
- 1979-02-13 CH CH137779A patent/CH642074A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
IT7920136A0 (it)	1979-02-12
IT1121051B (it)	1986-03-26
CH642074A5 (de)	1984-03-30
FR2416925B1 (fr)	1986-03-21
JPS54117534A (en)	1979-09-12
JPS6212823B2 (fr)	1987-03-20
FR2416925A1 (fr)	1979-09-07
GB2014180A (en)	1979-08-22
DE2905447A1 (de)	1979-08-16
GB2014180B (en)	1982-06-30

Legal Events

Date	Code	Title	Description
1999-04-13	MKEX	Expiry

Publication	Publication Date	Title
NZ273139A (en)	1997-11-24	Polyester whiteners comprising blue and red anthraquinones and anthrapyridones incorporated in the polyester polymer structure
GB1568231A (en)	1980-05-29	Substituted 2,6-dioxo-2,6-dihydrobenzo (1:2-b; 4:5-6')-difuran or dipyrrole dyestuffs
EP0975697B1 (fr)	2003-04-16	Pigments thiazine indigo, solution solides de ceux-ci et procede de preparation associe
CA1050992A (fr)	1979-03-20	Pigments d'azomethine
CA1074786A (fr)	1980-04-01	Complexes metalliques de bihydrazides
CA1121822A (fr)	1982-04-13	Derives de la coumarine ou de la benzocoumarine, utilises comme pigments
GB2131823A (en)	1984-06-27	Triphendioxazine dyes, methods for their manufacture and their use for dying cecculosic substrates
US4526963A (en)	1985-07-02	Dioxazine pigments
KR101672390B1 (ko)	2016-11-03	프탈로시아닌 화합물 및 그 제조 방법, 및 당해 프탈로시아닌 화합물을 함유하는 착색 조성물
US4099980A (en)	1978-07-11	Process for producing gamma quinacridone solid solutions
US3829439A (en)	1974-08-13	Process for preparing compounds of the benzothioxanthene series
KR20020032324A (ko)	2002-05-03	벤즈이미다졸론디옥사진 화합물의 혼합 결정
CA1093083A (fr)	1981-01-06	Composes a base d'iso-indoline
CA1052803A (fr)	1979-04-17	Composes de methine diazoique insolubles dans l'eau
US4240967A (en)	1980-12-23	Organic pigments derived from coumarin
US3336328A (en)	1967-08-15	Metal complexes of 2, 6-di-(2'-hydroxyaryl)-(1, 2d-4, 5d)-bisoxazole derivatives
JPS6241267B2 (fr)	1987-09-02
US20040173777A1 (en)	2004-09-09	Fluorescent diketopyrrolopyrrole analogues
US4088651A (en)	1978-05-09	Acylamino quinophthalone compounds
US3767361A (en)	1973-10-23	Process for dyeing polyacrylonitrile fibers with methine dyes
US3391148A (en)	1968-07-02	Reaction products of cyclic-substituted naphtholactams and arylamines
US4177195A (en)	1979-12-04	Organic pigments derived from benzocoumarin
US3715360A (en)	1973-02-06	Dyes of the 2,4-dihydroxyquinoline series
US4327024A (en)	1982-04-27	Iminoisoindolinone pigments, process for their production and use thereof
US3622582A (en)	1971-11-23	Disperse quinophthalone dyes containing a carboxylic ester group