JPH09132728A - ホストとして非対称ピロロ［３，４−ｃ］ピロールを含有する単相固溶体 - Google Patents

ホストとして非対称ピロロ［３，４−ｃ］ピロールを含有する単相固溶体

Info

Publication number: JPH09132728A
Authority: JP; Japan
Prior art keywords: formula; solid solution; pyrrole; alkyl; dihydro
Prior art date: 1995-09-26
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.): Abandoned

Application number

JP8255046A

Other languages

English (en)

Japanese (ja)

Other versions

JPH09132728A5 (2

Inventor

Zhimin Hao

ハオツィミン

Abul Iqbal

イクバルアブール

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.)

1995-09-26

Filing date

1996-09-26

Publication date

1997-05-20

1996-09-26 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1997-05-20 Publication of JPH09132728A publication Critical patent/JPH09132728A/ja

2004-09-24 Publication of JPH09132728A5 publication Critical patent/JPH09132728A5/ja

Status Abandoned legal-status Critical Current

Links

239000006104 solid solution Substances 0.000 title claims abstract description 79
YKPJEYXZEBLYCI-UHFFFAOYSA-N pyrrolo[3,4-c]pyrrole Chemical compound C1=NC=C2C=NC=C21 YKPJEYXZEBLYCI-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 26
239000013078 crystal Substances 0.000 claims abstract description 25
239000000049 pigment Substances 0.000 claims abstract description 23
229910052801 chlorine Inorganic materials 0.000 claims abstract description 18
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 18
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 15
229910052731 fluorine Inorganic materials 0.000 claims abstract description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 15
239000000243 solution Substances 0.000 claims abstract description 14
NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims abstract description 13
239000011368 organic material Substances 0.000 claims abstract description 13
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 12
229910052794 bromium Inorganic materials 0.000 claims abstract description 9
238000004040 coloring Methods 0.000 claims abstract description 9
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 64
239000000203 mixture Substances 0.000 claims description 38
238000000034 method Methods 0.000 claims description 32
-1 methoxy, methylamino Chemical group 0.000 claims description 30
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
239000000460 chlorine Substances 0.000 claims description 19
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 14
239000011737 fluorine Substances 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
125000004663 dialkyl amino group Chemical group 0.000 claims description 11
238000010438 heat treatment Methods 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 9
239000000725 suspension Substances 0.000 claims description 9
238000011282 treatment Methods 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
239000002585 base Substances 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
239000007788 liquid Substances 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 7
239000003495 polar organic solvent Substances 0.000 claims description 7
239000002243 precursor Substances 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
238000001226 reprecipitation Methods 0.000 claims description 6
238000003756 stirring Methods 0.000 claims description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 claims description 5
238000003801 milling Methods 0.000 claims description 5
125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 4
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 4
XPZQBGDNVOHQIS-UHFFFAOYSA-N 2,9-dichloro-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(Cl)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)Cl)N1)C1=C2 XPZQBGDNVOHQIS-UHFFFAOYSA-N 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 4
238000004898 kneading Methods 0.000 claims description 4
150000001540 azides Chemical class 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
239000011363 dried mixture Substances 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
238000006303 photolysis reaction Methods 0.000 claims description 2
230000015843 photosynthesis, light reaction Effects 0.000 claims description 2
150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 2
238000001953 recrystallisation Methods 0.000 claims description 2
238000010992 reflux Methods 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 5
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 1
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Chemical group 0.000 claims 1
230000002378 acidificating effect Effects 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
230000001376 precipitating effect Effects 0.000 claims 1
SSIXDIVVMZXRMJ-UHFFFAOYSA-N 2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound O=C1NC=C2C(=O)NC=C21 SSIXDIVVMZXRMJ-UHFFFAOYSA-N 0.000 abstract 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
125000001624 naphthyl group Chemical group 0.000 abstract 1
125000004076 pyridyl group Chemical group 0.000 abstract 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000002441 X-ray diffraction Methods 0.000 description 12
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000008096 xylene Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 9
239000000843 powder Substances 0.000 description 9
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
239000002904 solvent Substances 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
229920006217 cellulose acetate butyrate Polymers 0.000 description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
239000003973 paint Substances 0.000 description 5
RDSDJWURJCJSCJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-(3-methylphenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound CC1=CC=CC(C=2NC(=O)C3=C(NC(=O)C3=2)C=2C=CC(Cl)=CC=2)=C1 RDSDJWURJCJSCJ-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
239000011248 coating agent Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000000463 material Substances 0.000 description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
239000004014 plasticizer Substances 0.000 description 4
229920000915 polyvinyl chloride Polymers 0.000 description 4
239000004800 polyvinyl chloride Substances 0.000 description 4
150000003233 pyrroles Chemical class 0.000 description 4
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
ZVSSICCMWKTTLO-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-(4-methylphenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C1=CC(C)=CC=C1C(NC1=O)=C2C1=C(C=1C=CC(Cl)=CC=1)NC2=O ZVSSICCMWKTTLO-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
229920000877 Melamine resin Polymers 0.000 description 3
239000004640 Melamine resin Substances 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
239000003086 colorant Substances 0.000 description 3
239000000470 constituent Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000010408 film Substances 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000006069 physical mixture Substances 0.000 description 3
229920000098 polyolefin Polymers 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
239000002966 varnish Substances 0.000 description 3
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
TXWSZJSDZKWQAU-UHFFFAOYSA-N 2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical group N1C2=CC=C(C)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)C)N1)C1=C2 TXWSZJSDZKWQAU-UHFFFAOYSA-N 0.000 description 2
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
NKHUXLDXYURVLX-UHFFFAOYSA-N 2h-pyrrolo[3,4-c]pyrrole-4,6-dione Chemical compound N1C=C2C(=O)NC(=O)C2=C1 NKHUXLDXYURVLX-UHFFFAOYSA-N 0.000 description 2
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
CKTXMVGTOAQFAP-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-(4-phenylphenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C1=CC(Cl)=CC=C1C(NC1=O)=C2C1=C(C=1C=CC(=CC=1)C=1C=CC=CC=1)NC2=O CKTXMVGTOAQFAP-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
229920003264 Maprenal® Polymers 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
238000007605 air drying Methods 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
239000012973 diazabicyclooctane Substances 0.000 description 2
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
229940075557 diethylene glycol monoethyl ether Drugs 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
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
239000000976 ink Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
239000002923 metal particle Substances 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
239000010445 mica Substances 0.000 description 2
229910052618 mica group Inorganic materials 0.000 description 2
230000005012 migration Effects 0.000 description 2
238000013508 migration Methods 0.000 description 2
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920001225 polyester resin Polymers 0.000 description 2
239000004645 polyester resin Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000009987 spinning Methods 0.000 description 2
239000007921 spray Substances 0.000 description 2
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
UWHBZLMSPZBZHY-UHFFFAOYSA-N 1,4-diphenyl-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C=12C(=O)NC(C=3C=CC=CC=3)=C2C(=O)NC=1C1=CC=CC=C1 UWHBZLMSPZBZHY-UHFFFAOYSA-N 0.000 description 1
NHYJOGXXYQZLID-UHFFFAOYSA-N 1-phenyl-4-(4-phenylphenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C=12C(=O)NC(C=3C=CC(=CC=3)C=3C=CC=CC=3)=C2C(=O)NC=1C1=CC=CC=C1 NHYJOGXXYQZLID-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
FRFHXMFELKKMTC-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-1-phenyl-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C1=C(Cl)C(Cl)=CC=C1C(NC1=O)=C2C1=C(C=1C=CC=CC=1)NC2=O FRFHXMFELKKMTC-UHFFFAOYSA-N 0.000 description 1
DCOZERGYCYJONV-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-1-phenyl-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1C(NC1=O)=C2C1=C(C=1C=CC=CC=1)NC2=O DCOZERGYCYJONV-UHFFFAOYSA-N 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
229920003270 Cymel® Polymers 0.000 description 1
MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
239000004594 Masterbatch (MB) Substances 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 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
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
238000012644 addition polymerization Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229920003180 amino resin Polymers 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 1
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
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238000003490 calendering Methods 0.000 description 1
239000004202 carbamide Substances 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
238000005266 casting Methods 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920001727 cellulose butyrate Polymers 0.000 description 1
229920003086 cellulose ether Polymers 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000006103 coloring component Substances 0.000 description 1
238000013329 compounding Methods 0.000 description 1
238000000748 compression moulding Methods 0.000 description 1
238000005094 computer simulation Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
238000010586 diagram Methods 0.000 description 1
239000012975 dibutyltin dilaurate Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 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
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000835 fiber Substances 0.000 description 1
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 1
238000009472 formulation Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
239000010954 inorganic particle Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
239000004611 light stabiliser Substances 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
OBQVOBQZMOXRAL-UHFFFAOYSA-L magnesium;docosanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC([O-])=O OBQVOBQZMOXRAL-UHFFFAOYSA-L 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002074 melt spinning Methods 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000000465 moulding Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940094933 n-dodecane Drugs 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
GLKFBDCTMIJHDH-UHFFFAOYSA-N nitrobenzene;pyridine Chemical compound C1=CC=NC=C1.[O-][N+](=O)C1=CC=CC=C1 GLKFBDCTMIJHDH-UHFFFAOYSA-N 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
150000003021 phthalic acid derivatives Chemical class 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
238000012643 polycondensation polymerization Methods 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920006380 polyphenylene oxide Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
230000008569 process Effects 0.000 description 1
QKWILNTYPDJSME-UHFFFAOYSA-N pyrrolo[3,4-c]pyrrole-3,6-dione Chemical group C1=NC(=O)C2=C1C(=O)N=C2 QKWILNTYPDJSME-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000005060 rubber Substances 0.000 description 1
LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
150000003329 sebacic acid derivatives Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
229920002050 silicone resin Polymers 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
238000012916 structural analysis Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000979 synthetic dye Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
239000010409 thin film Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- 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
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Compositions Of Macromolecular Compounds (AREA)
Cosmetics (AREA)

JP8255046A 1995-09-26 1996-09-26 ホストとして非対称ピロロ［３，４−ｃ］ピロールを含有する単相固溶体 Abandoned JPH09132728A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH02719/95		1995-09-26
CH271995		1995-09-26

Publications (2)

Publication Number	Publication Date
JPH09132728A true JPH09132728A (ja)	1997-05-20
JPH09132728A5 JPH09132728A5 (2)	2004-09-24

Family

ID=4240067

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP8255046A Abandoned JPH09132728A (ja)	1995-09-26	1996-09-26	ホストとして非対称ピロロ［３，４−ｃ］ピロールを含有する単相固溶体

Country Status (8)

Country	Link
US (1)	US5756746A (2)
EP (1)	EP0765919B1 (2)
JP (1)	JPH09132728A (2)
KR (1)	KR100430357B1 (2)
CN (1)	CN1076744C (2)
CA (1)	CA2186319A1 (2)
DE (1)	DE59606457D1 (2)
TW (1)	TW404973B (2)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2001019870A (ja) *	1999-04-22	2001-01-23	Clariant Internatl Ltd	ハイブリッド顔料
WO2009081930A1 (ja) *	2007-12-26	2009-07-02	Toyo Ink Mfg. Co., Ltd.	赤色カラーフィルター用顔料組成物、その製造方法、及びそれを用いた着色組成物、及びカラーフィルター
JP2011500611A (ja) *	2007-10-18	2011-01-06	クラリアント・ファイナンス・（ビーブイアイ）・リミテッド	ジケトピロロピロール混晶

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EP0794235B1 (en) *	1996-03-06	2000-02-02	Ciba SC Holding AG	Ternary solid solutions of 1,4-diketo-pyrrolopyrroles and quinacridones
ES2178136T3 (es) *	1997-05-06	2002-12-16	Ciba Sc Holding Ag	Composiciones de dicetopirrolopirroles.
GB9818821D0 (en) *	1998-08-29	1998-10-21	Ciba Sc Holding Ag	Novel monophase solid solutions
ATE310775T1 (de) *	2001-05-14	2005-12-15	Ciba Sc Holding Ag	Neue kristallmodifikation einer festen lösung von einem diketopyrrolopyrrolpigment
DE60329656D1 (de) *	2002-01-31	2009-11-26	Basf Se	Herstellung und konditionierung von festen lösungen von organischen pigmenten
US8273269B2 (en)	2008-05-28	2012-09-25	Basf Se	Red colour filter composition
JP6238748B2 (ja)	2010-12-30	2017-11-29	ビーエーエスエフソシエタス・ヨーロピアＢａｓｆＳｅ	表面修飾された顔料調製物

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DE256983C (2) *
ATE22104T1 (de) *	1982-05-17	1986-09-15	Ciba Geigy Ag	Herstellung von pyrrolo-(3,4-c)-pyrrolen.
DE3584138D1 (de) *	1984-11-07	1991-10-24	Ciba Geigy Ag	Pigmentmischungen.
US4783540A (en) *	1986-08-07	1988-11-08	Ciba-Geigy Corporation	Solid solutions of pyrrolo-(3,4-C)-pyrrols
US4810304A (en) *	1987-02-02	1989-03-07	Ciba-Geigy Corporation	Solid solutions of pyrrolo-(3,4-C)-pyrroles with quinacridones
ES2058327T3 (es) *	1987-02-02	1994-11-01	Ciba Geigy Ag	Soluciones solidas de pirrolo-(3,4-c)-pirroles con quinacridonas.
EP0654506B1 (de) *	1993-11-22	2000-05-17	Ciba SC Holding AG	Verfahren zur Herstellung synergistischer Pigmentgemische
US5529623A (en) *	1994-09-28	1996-06-25	Ciba-Geigy Corporation	Pigmentary solid solutions of pyrrolo[3,4-c]pyrroles and quinacridones
DE59507427D1 (de) *	1994-09-28	2000-01-20	Ciba Sc Holding Ag	Mischkristalle und feste Lösungen von 1,4-Diketopyrrolopyrrolen
TW434296B (en) *	1994-10-12	2001-05-16	Ciba Sc Holding Ag	Process for the preparation of diaryldiketopyrrolopyrrole pigments

1996
- 1996-08-27 TW TW085110397A patent/TW404973B/zh not_active IP Right Cessation
- 1996-09-17 EP EP96810617A patent/EP0765919B1/de not_active Expired - Lifetime
- 1996-09-17 DE DE59606457T patent/DE59606457D1/de not_active Expired - Fee Related
- 1996-09-23 US US08/700,349 patent/US5756746A/en not_active Expired - Fee Related
- 1996-09-24 CA CA002186319A patent/CA2186319A1/en not_active Abandoned
- 1996-09-25 CN CN96122532A patent/CN1076744C/zh not_active Expired - Fee Related
- 1996-09-25 KR KR1019960042391A patent/KR100430357B1/ko not_active Expired - Fee Related
- 1996-09-26 JP JP8255046A patent/JPH09132728A/ja not_active Abandoned

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2001019870A (ja) *	1999-04-22	2001-01-23	Clariant Internatl Ltd	ハイブリッド顔料
JP2011500611A (ja) *	2007-10-18	2011-01-06	クラリアント・ファイナンス・（ビーブイアイ）・リミテッド	ジケトピロロピロール混晶
WO2009081930A1 (ja) *	2007-12-26	2009-07-02	Toyo Ink Mfg. Co., Ltd.	赤色カラーフィルター用顔料組成物、その製造方法、及びそれを用いた着色組成物、及びカラーフィルター
JPWO2009081930A1 (ja) *	2007-12-26	2011-05-06	東洋インキ製造株式会社	赤色カラーフィルター用顔料組成物、その製造方法、及びそれを用いた着色組成物、及びカラーフィルター

Also Published As

Publication number	Publication date
DE59606457D1 (de)	2001-03-29
EP0765919A2 (de)	1997-04-02
KR100430357B1 (ko)	2004-08-16
TW404973B (en)	2000-09-11
CN1076744C (zh)	2001-12-26
EP0765919B1 (de)	2001-02-21
EP0765919A3 (de)	1998-04-01
CA2186319A1 (en)	1997-03-27
KR970015573A (ko)	1997-04-28
US5756746A (en)	1998-05-26
CN1159464A (zh)	1997-09-17

Legal Events

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2005-10-13

A762

Written abandonment of application

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Effective date: 20051012

Publication	Publication Date	Title
US5708188A (en)	1998-01-13	Mixed crystals and solid solution of 1,4-diketopyrrolopyrroles
JP2578125B2 (ja)	1997-02-05	ピロロ−〔３，４−ｃ〕−ピロ−ルの固溶体
US6248165B1 (en)	2001-06-19	Mixed crystals and solid solutions of 1,4-diketopyrrolopyrroles
US8883889B2 (en)	2014-11-11	Pigment compositions comprising pyrrolo[3,4-c]pyrroles
JP2781796B2 (ja)	1998-07-30	ピロロ［３，４−ｃ］ピロールの改良された製法
US5821373A (en)	1998-10-13	Solid sloutions of 1,4-diketopyrrolopyrroles
KR20110108401A (ko)	2011-10-05	유기 흑색 안료 및 이의 제조 방법
US5756746A (en)	1998-05-26	Monophase solid solutions containing asymmetric pyrrolo 4,3-c! pyrroles as hosts
JPH09124649A (ja)	1997-05-13	１、４−ジケトピロロピロールの混晶および固溶体の製造方法
JPS63201189A (ja)	1988-08-19	ピロロ−〔３，４−ｃ〕−ピロールとキナクリドンとの固溶体
US5646299A (en)	1997-07-08	Two new crystal modifications of a diketopyrrolopyrrole pigment
US5817832A (en)	1998-10-06	Blue diketopyrrolopyrrole pigments
US4460768A (en)	1984-07-17	Nickel complex pigments of azines
JPH06256348A (ja)	1994-09-13	ニトロキシル基を含むジケトピロロピロール
JPH07292273A (ja)	1995-11-07	シアンイミノ基含有ピロロ［３，４−ｃピロール
JPH02113074A (ja)	1990-04-25	アゾメチン顔料の固溶体
JPH06322282A (ja)	1994-11-22	ピロロピロール顔料の安定化