JPS6226672B2 - - Google Patents
Info
- Publication number
- JPS6226672B2 JPS6226672B2 JP994880A JP994880A JPS6226672B2 JP S6226672 B2 JPS6226672 B2 JP S6226672B2 JP 994880 A JP994880 A JP 994880A JP 994880 A JP994880 A JP 994880A JP S6226672 B2 JPS6226672 B2 JP S6226672B2
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- compound
- group
- resistance
- pigment according
- Prior art date
- 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
Links
- 239000000049 pigment Substances 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 27
- 238000000921 elemental analysis Methods 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003086 colorant Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000012916 structural analysis Methods 0.000 description 6
- LOZJNNNVLREXGU-UHFFFAOYSA-N 3-amino-4,5,6,7-tetrachloroisoindol-1-one Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C1C(N)=NC2=O LOZJNNNVLREXGU-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000000976 ink Substances 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 4
- -1 diisocyanate compound Chemical class 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 238000013508 migration Methods 0.000 description 4
- 230000005012 migration Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- NIRVMFYQRUGDNS-UHFFFAOYSA-N 1,4-dichloro-2,5-diisocyanatobenzene Chemical compound ClC1=CC(N=C=O)=C(Cl)C=C1N=C=O NIRVMFYQRUGDNS-UHFFFAOYSA-N 0.000 description 2
- XCYAYYRYTNCXQL-UHFFFAOYSA-N 1,4-diisocyanato-2,5-dimethylbenzene Chemical compound CC1=CC(N=C=O)=C(C)C=C1N=C=O XCYAYYRYTNCXQL-UHFFFAOYSA-N 0.000 description 2
- GBGORBREQNJWLW-UHFFFAOYSA-N 2-chloro-1,4-diisocyanatobenzene Chemical compound ClC1=CC(N=C=O)=CC=C1N=C=O GBGORBREQNJWLW-UHFFFAOYSA-N 0.000 description 2
- OQHXZZGZASQSOB-UHFFFAOYSA-N 3,4,5,6-tetrachlorobenzene-1,2-dicarbonitrile Chemical compound ClC1=C(Cl)C(Cl)=C(C#N)C(C#N)=C1Cl OQHXZZGZASQSOB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000001052 yellow pigment Substances 0.000 description 2
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CPUKVNMTTMDHNT-UHFFFAOYSA-N 1,4-diisocyanato-2-methoxybenzene Chemical compound COC1=CC(N=C=O)=CC=C1N=C=O CPUKVNMTTMDHNT-UHFFFAOYSA-N 0.000 description 1
- DKBHJZFJCDOGOY-UHFFFAOYSA-N 1,4-diisocyanato-2-methylbenzene Chemical compound CC1=CC(N=C=O)=CC=C1N=C=O DKBHJZFJCDOGOY-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- NTIBQHYQJUDIBL-UHFFFAOYSA-N 1-chloro-2,5-diisocyanato-4-methoxybenzene Chemical compound COC1=CC(N=C=O)=C(Cl)C=C1N=C=O NTIBQHYQJUDIBL-UHFFFAOYSA-N 0.000 description 1
- LAAFHKVUSAHPFY-UHFFFAOYSA-N 2-ethoxy-1,4-diisocyanatobenzene Chemical compound C(C)OC1=C(C=CC(=C1)N=C=O)N=C=O LAAFHKVUSAHPFY-UHFFFAOYSA-N 0.000 description 1
- VRWKQLPUQYWLAK-UHFFFAOYSA-N 2-ethyl-1,4-diisocyanatobenzene Chemical compound CCC1=CC(N=C=O)=CC=C1N=C=O VRWKQLPUQYWLAK-UHFFFAOYSA-N 0.000 description 1
- OJELSGMHUFIREM-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3h-isoindol-1-amine Chemical compound ClC1=C(Cl)C(Cl)=C2CNC(=N)C2=C1Cl OJELSGMHUFIREM-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
- Indole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP994880A JPS56109254A (en) | 1980-02-01 | 1980-02-01 | Azomethine pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP994880A JPS56109254A (en) | 1980-02-01 | 1980-02-01 | Azomethine pigment |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56109254A JPS56109254A (en) | 1981-08-29 |
| JPS6226672B2 true JPS6226672B2 (US07652168-20100126-C00068.png) | 1987-06-10 |
Family
ID=11734199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP994880A Granted JPS56109254A (en) | 1980-02-01 | 1980-02-01 | Azomethine pigment |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56109254A (US07652168-20100126-C00068.png) |
-
1980
- 1980-02-01 JP JP994880A patent/JPS56109254A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56109254A (en) | 1981-08-29 |
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