JPH0326155B2 - - Google Patents
Info
- Publication number
- JPH0326155B2 JPH0326155B2 JP57014294A JP1429482A JPH0326155B2 JP H0326155 B2 JPH0326155 B2 JP H0326155B2 JP 57014294 A JP57014294 A JP 57014294A JP 1429482 A JP1429482 A JP 1429482A JP H0326155 B2 JPH0326155 B2 JP H0326155B2
- Authority
- JP
- Japan
- Prior art keywords
- bis
- group
- benzoquinone
- amine
- triphenylmethane
- 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 - Lifetime
Links
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 72
- 150000004059 quinone derivatives Chemical class 0.000 claims description 19
- 239000003352 sequestering agent Substances 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 230000001590 oxidative effect Effects 0.000 claims description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 2
- MKZHJJQCUIZEDE-UHFFFAOYSA-N 1-[(2-hydroxy-3-naphthalen-1-yloxypropyl)-propan-2-ylamino]-3-naphthalen-1-yloxypropan-2-ol Chemical compound C1=CC=C2C(OCC(O)CN(CC(O)COC=3C4=CC=CC=C4C=CC=3)C(C)C)=CC=CC2=C1 MKZHJJQCUIZEDE-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 description 49
- -1 color developers Substances 0.000 description 26
- 239000006185 dispersion Substances 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 229940005561 1,4-benzoquinone Drugs 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 239000000049 pigment Substances 0.000 description 11
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
- 239000003973 paint Substances 0.000 description 10
- 238000004040 coloring Methods 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 8
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 150000002596 lactones Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical group O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000005336 allyloxy group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000006479 redox reaction Methods 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- LWHDQPLUIFIFFT-UHFFFAOYSA-N 2,3,5,6-tetrabromocyclohexa-2,5-diene-1,4-dione Chemical compound BrC1=C(Br)C(=O)C(Br)=C(Br)C1=O LWHDQPLUIFIFFT-UHFFFAOYSA-N 0.000 description 2
- URDCARMUOSMFFI-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(2-hydroxyethyl)amino]acetic acid Chemical compound OCCN(CC(O)=O)CCN(CC(O)=O)CC(O)=O URDCARMUOSMFFI-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IPAJDLMMTVZVPP-UHFFFAOYSA-N Crystal violet lactone Chemical compound C1=CC(N(C)C)=CC=C1C1(C=2C=CC(=CC=2)N(C)C)C2=CC=C(N(C)C)C=C2C(=O)O1 IPAJDLMMTVZVPP-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000005138 alkoxysulfonyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 230000021148 sequestering of metal ion Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
- GYBIPSAIBKENIC-UHFFFAOYSA-N tetraethyl 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylate Chemical compound CCOC(=O)C1=C(C(=O)OCC)C(=O)C(C(=O)OCC)=C(C(=O)OCC)C1=O GYBIPSAIBKENIC-UHFFFAOYSA-N 0.000 description 2
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 2
- BVPKYBMUQDZTJH-UHFFFAOYSA-N 1,1,1-trifluoro-5,5-dimethylhexane-2,4-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(F)(F)F BVPKYBMUQDZTJH-UHFFFAOYSA-N 0.000 description 1
- SHXHPUAKLCCLDV-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)C(F)(F)F SHXHPUAKLCCLDV-UHFFFAOYSA-N 0.000 description 1
- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 1
- ICMJHPBQTVWCNT-UHFFFAOYSA-N 1-(dibutylamino)propan-2-ol Chemical compound CCCCN(CC(C)O)CCCC ICMJHPBQTVWCNT-UHFFFAOYSA-N 0.000 description 1
- BHUXAQIVYLDUQV-UHFFFAOYSA-N 1-(diethylamino)propan-2-ol Chemical compound CCN(CC)CC(C)O BHUXAQIVYLDUQV-UHFFFAOYSA-N 0.000 description 1
- NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 description 1
- LAOZQNBBEXGXBN-UHFFFAOYSA-N 1-(dipropylamino)propan-2-ol Chemical compound CCCN(CCC)CC(C)O LAOZQNBBEXGXBN-UHFFFAOYSA-N 0.000 description 1
- GRERXOHTSMZXAV-UHFFFAOYSA-N 1-(n-phenylanilino)propan-2-ol Chemical compound C=1C=CC=CC=1N(CC(O)C)C1=CC=CC=C1 GRERXOHTSMZXAV-UHFFFAOYSA-N 0.000 description 1
- XKQMKMVTDKYWOX-UHFFFAOYSA-N 1-[2-hydroxypropyl(methyl)amino]propan-2-ol Chemical compound CC(O)CN(C)CC(C)O XKQMKMVTDKYWOX-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- PNCFAACQJCAFGT-UHFFFAOYSA-N 1-ethyl-3-[(1-ethyl-2-methylindol-3-yl)-phenylmethyl]-2-methylindole Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C(C=1C2=CC=CC=C2N(CC)C=1C)C1=CC=CC=C1 PNCFAACQJCAFGT-UHFFFAOYSA-N 0.000 description 1
- PUYGXCWFNGLZBS-UHFFFAOYSA-N 1-hexyl-3-[(1-hexylindol-3-yl)-phenylmethyl]indole Chemical compound C12=CC=CC=C2N(CCCCCC)C=C1C(C=1C2=CC=CC=C2N(CCCCCC)C=1)C1=CC=CC=C1 PUYGXCWFNGLZBS-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- XAKIZRLIXGLPBW-UHFFFAOYSA-N 1-piperazin-1-ylpropan-2-ol Chemical compound CC(O)CN1CCNCC1 XAKIZRLIXGLPBW-UHFFFAOYSA-N 0.000 description 1
- JKLYZOGJWVAIQS-UHFFFAOYSA-N 2,3,5,6-tetrafluorocyclohexa-2,5-diene-1,4-dione Chemical compound FC1=C(F)C(=O)C(F)=C(F)C1=O JKLYZOGJWVAIQS-UHFFFAOYSA-N 0.000 description 1
- YBGORPOETHYSFS-UHFFFAOYSA-N 2,3,5,6-tetraiodocyclohexa-2,5-diene-1,4-dione Chemical compound IC1=C(I)C(=O)C(I)=C(I)C1=O YBGORPOETHYSFS-UHFFFAOYSA-N 0.000 description 1
- JQODFBRFYTYNOV-UHFFFAOYSA-N 2,3,5,6-tetrakis(benzenesulfonyl)cyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(S(=O)(=O)C=2C=CC=CC=2)=C(S(=O)(=O)C=2C=CC=CC=2)C(=O)C(S(=O)(=O)C=2C=CC=CC=2)=C1S(=O)(=O)C1=CC=CC=C1 JQODFBRFYTYNOV-UHFFFAOYSA-N 0.000 description 1
- DXINWZQQYKWFHW-UHFFFAOYSA-N 2,3,5,6-tetrakis(octylsulfonyl)cyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCCCS(=O)(=O)C1=C(S(=O)(=O)CCCCCCCC)C(=O)C(S(=O)(=O)CCCCCCCC)=C(S(=O)(=O)CCCCCCCC)C1=O DXINWZQQYKWFHW-UHFFFAOYSA-N 0.000 description 1
- KSFNQTZBTVALRV-UHFFFAOYSA-N 2,3,5-trichlorocyclohexa-2,5-diene-1,4-dione Chemical compound ClC1=CC(=O)C(Cl)=C(Cl)C1=O KSFNQTZBTVALRV-UHFFFAOYSA-N 0.000 description 1
- QHBWSLQUJMHGDB-UHFFFAOYSA-N 2,3-diaminopropan-1-ol Chemical compound NCC(N)CO QHBWSLQUJMHGDB-UHFFFAOYSA-N 0.000 description 1
- USAYMJGCALIGIG-UHFFFAOYSA-N 2,3-dichlorocyclohexa-2,5-diene-1,4-dione Chemical compound ClC1=C(Cl)C(=O)C=CC1=O USAYMJGCALIGIG-UHFFFAOYSA-N 0.000 description 1
- KMTMKSXVAKBBRQ-UHFFFAOYSA-N 2,5-diacetyl-3,6-dibromocyclohexa-2,5-diene-1,4-dione Chemical compound CC(=O)C1=C(Br)C(=O)C(C(C)=O)=C(Br)C1=O KMTMKSXVAKBBRQ-UHFFFAOYSA-N 0.000 description 1
- DWAOIUMDXJWZOO-UHFFFAOYSA-N 2,5-dibenzoyl-3,6-dibromocyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(Br)=C(C(=O)C=2C=CC=CC=2)C(=O)C(Br)=C1C(=O)C1=CC=CC=C1 DWAOIUMDXJWZOO-UHFFFAOYSA-N 0.000 description 1
- VGUGAJIFFUCDKM-UHFFFAOYSA-N 2,5-dibenzoyl-3,6-dichlorocyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(Cl)=C(C(=O)C=2C=CC=CC=2)C(=O)C(Cl)=C1C(=O)C1=CC=CC=C1 VGUGAJIFFUCDKM-UHFFFAOYSA-N 0.000 description 1
- MJIIZZFKKAGVRX-UHFFFAOYSA-N 2,5-dibenzoyl-3-bromocyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=C(C(=O)C=2C=CC=CC=2)C(=O)C(Br)=C1C(=O)C1=CC=CC=C1 MJIIZZFKKAGVRX-UHFFFAOYSA-N 0.000 description 1
- CFRIKYUWAOQJPO-UHFFFAOYSA-N 2,5-dibromo-3,6-bis-(4-methylphenyl)sulfonylcyclohexa-2,5-diene-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=C(Br)C(=O)C(S(=O)(=O)C=2C=CC(C)=CC=2)=C(Br)C1=O CFRIKYUWAOQJPO-UHFFFAOYSA-N 0.000 description 1
- NOHARMNIIYJPRN-UHFFFAOYSA-N 2,5-dichloro-3,6-bis(hexylsulfonyl)cyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCS(=O)(=O)C1=C(Cl)C(=O)C(S(=O)(=O)CCCCCC)=C(Cl)C1=O NOHARMNIIYJPRN-UHFFFAOYSA-N 0.000 description 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 description 1
- SWKPGMVENNYLFK-UHFFFAOYSA-N 2-(dipropylamino)ethanol Chemical compound CCCN(CCC)CCO SWKPGMVENNYLFK-UHFFFAOYSA-N 0.000 description 1
- HCYSJBICYOIBLS-UHFFFAOYSA-N 2-(dodecylamino)ethanol Chemical compound CCCCCCCCCCCCNCCO HCYSJBICYOIBLS-UHFFFAOYSA-N 0.000 description 1
- KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 1
- VIIZJXNVVJKISZ-UHFFFAOYSA-N 2-(n-methylanilino)ethanol Chemical compound OCCN(C)C1=CC=CC=C1 VIIZJXNVVJKISZ-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 description 1
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 1
- MUVQIIBPDFTEKM-UHFFFAOYSA-N 2-aminobutane-1,3-diol Chemical compound CC(O)C(N)CO MUVQIIBPDFTEKM-UHFFFAOYSA-N 0.000 description 1
- DNTLBZRFODLVNC-UHFFFAOYSA-N 2-aminopropane-1,2-diol Chemical class CC(N)(O)CO DNTLBZRFODLVNC-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 1
- CASFZRYEWPAIHE-UHFFFAOYSA-N 2-phenyl-3-[phenyl-(2-phenyl-1-propylindol-3-yl)methyl]-1-propylindole Chemical compound C12=CC=CC=C2N(CCC)C(C=2C=CC=CC=2)=C1C(C=1C=CC=CC=1)C(C1=CC=CC=C1N1CCC)=C1C1=CC=CC=C1 CASFZRYEWPAIHE-UHFFFAOYSA-N 0.000 description 1
- ISPXBKMBAQKTNG-UHFFFAOYSA-N 3,4,5,6-tetrakis(butylsulfonyl)cyclohexa-3,5-diene-1,2-dione Chemical compound C(CCC)S(=O)(=O)C=1C(C(C(=C(C=1S(=O)(=O)CCCC)S(=O)(=O)CCCC)S(=O)(=O)CCCC)=O)=O ISPXBKMBAQKTNG-UHFFFAOYSA-N 0.000 description 1
- DNCRBMRXWNDEHB-UHFFFAOYSA-N 3,4-dibromo-5,6-dioxocyclohexa-1,3-diene-1,2-dicarbonitrile Chemical compound BrC1=C(Br)C(C#N)=C(C#N)C(=O)C1=O DNCRBMRXWNDEHB-UHFFFAOYSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- VENLFBXQEYDFEU-UHFFFAOYSA-N 3-[bis(1-butyl-2-methylindol-3-yl)methyl]-1-butyl-2-methylindole Chemical compound C12=CC=CC=C2N(CCCC)C(C)=C1C(C=1C2=CC=CC=C2N(CCCC)C=1C)C1=C(C)N(CCCC)C2=CC=CC=C12 VENLFBXQEYDFEU-UHFFFAOYSA-N 0.000 description 1
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- PCWMTXMBFZQDHV-UHFFFAOYSA-N naphthalene-1,4,5,8-tetrone Chemical class O=C1C=CC(=O)C2=C1C(=O)C=CC2=O PCWMTXMBFZQDHV-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003330 pentetic acid Drugs 0.000 description 1
- 239000012169 petroleum derived wax Substances 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- OADLSOUXZDRTMW-UHFFFAOYSA-N tetrabenzyl 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylate Chemical compound C=1C=CC=CC=1COC(=O)C=1C(=O)C(C(=O)OCC=2C=CC=CC=2)=C(C(=O)OCC=2C=CC=CC=2)C(=O)C=1C(=O)OCC1=CC=CC=C1 OADLSOUXZDRTMW-UHFFFAOYSA-N 0.000 description 1
- IXCLCQCPVHLZQC-UHFFFAOYSA-N tetrabenzyl 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetrasulfonate Chemical compound O=C1C(S(=O)(=O)OCC=2C=CC=CC=2)=C(S(=O)(=O)OCC=2C=CC=CC=2)C(=O)C(S(=O)(=O)OCC=2C=CC=CC=2)=C1S(=O)(=O)OCC1=CC=CC=C1 IXCLCQCPVHLZQC-UHFFFAOYSA-N 0.000 description 1
- LAEOGKVXCPKFQG-UHFFFAOYSA-N tetrabutyl 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylate Chemical compound CCCCOC(=O)C1=C(C(=O)OCCCC)C(=O)C(C(=O)OCCCC)=C(C(=O)OCCCC)C1=O LAEOGKVXCPKFQG-UHFFFAOYSA-N 0.000 description 1
- LTYRTECQSOEDAE-UHFFFAOYSA-N tetrabutyl 5,6-dioxocyclohexa-1,3-diene-1,2,3,4-tetracarboxylate Chemical compound CCCCOC(=O)C1=C(C(=O)OCCCC)C(C(=O)OCCCC)=C(C(=O)OCCCC)C(=O)C1=O LTYRTECQSOEDAE-UHFFFAOYSA-N 0.000 description 1
- ZGQUHUTWFOFJMI-UHFFFAOYSA-N tetradodecyl 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylate Chemical compound CCCCCCCCCCCCOC(=O)C1=C(C(=O)OCCCCCCCCCCCC)C(=O)C(C(=O)OCCCCCCCCCCCC)=C(C(=O)OCCCCCCCCCCCC)C1=O ZGQUHUTWFOFJMI-UHFFFAOYSA-N 0.000 description 1
- WOIORFMIISICAH-UHFFFAOYSA-N tetrakis(2-ethylhexyl) 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylate Chemical compound CCCCC(CC)COC(=O)C1=C(C(=O)OCC(CC)CCCC)C(=O)C(C(=O)OCC(CC)CCCC)=C(C(=O)OCC(CC)CCCC)C1=O WOIORFMIISICAH-UHFFFAOYSA-N 0.000 description 1
- OELOQOJIZZBGME-UHFFFAOYSA-N tetrakis(4-methylphenyl) 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylate Chemical compound C1=CC(C)=CC=C1OC(=O)C(C(C(C(=O)OC=1C=CC(C)=CC=1)=C(C(=O)OC=1C=CC(C)=CC=1)C1=O)=O)=C1C(=O)OC1=CC=C(C)C=C1 OELOQOJIZZBGME-UHFFFAOYSA-N 0.000 description 1
- LZMYYVFMLBATPX-UHFFFAOYSA-N tetramethyl 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylate Chemical compound COC(=O)C1=C(C(=O)OC)C(=O)C(C(=O)OC)=C(C(=O)OC)C1=O LZMYYVFMLBATPX-UHFFFAOYSA-N 0.000 description 1
- HBMXKGXEHUSMLU-UHFFFAOYSA-N tetranaphthalen-1-yl 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylate Chemical compound C1=CC=C2C(OC(=O)C3=C(C(=O)OC=4C5=CC=CC=C5C=CC=4)C(=O)C(C(=O)OC=4C5=CC=CC=C5C=CC=4)=C(C3=O)C(OC=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 HBMXKGXEHUSMLU-UHFFFAOYSA-N 0.000 description 1
- IGNXHUYTFPGQJA-UHFFFAOYSA-N tetraphenyl 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarboxylate Chemical compound C=1C=CC=CC=1OC(=O)C=1C(=O)C(C(=O)OC=2C=CC=CC=2)=C(C(=O)OC=2C=CC=CC=2)C(=O)C=1C(=O)OC1=CC=CC=C1 IGNXHUYTFPGQJA-UHFFFAOYSA-N 0.000 description 1
- XKKLTIVKLZTWBA-UHFFFAOYSA-N tetrapropyl 5,6-dioxocyclohexa-1,3-diene-1,2,3,4-tetracarboxylate Chemical compound CCCOC(=O)C1=C(C(=O)OCCC)C(C(=O)OCCC)=C(C(=O)OCCC)C(=O)C1=O XKKLTIVKLZTWBA-UHFFFAOYSA-N 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- TXBBUSUXYMIVOS-UHFFFAOYSA-N thenoyltrifluoroacetone Chemical compound FC(F)(F)C(=O)CC(=O)C1=CC=CS1 TXBBUSUXYMIVOS-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57014294A JPS58132587A (ja) | 1982-02-02 | 1982-02-02 | 感熱記録ユニツト |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57014294A JPS58132587A (ja) | 1982-02-02 | 1982-02-02 | 感熱記録ユニツト |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58132587A JPS58132587A (ja) | 1983-08-06 |
| JPH0326155B2 true JPH0326155B2 (ru) | 1991-04-09 |
Family
ID=11857068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57014294A Granted JPS58132587A (ja) | 1982-02-02 | 1982-02-02 | 感熱記録ユニツト |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58132587A (ru) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6027591A (ja) * | 1983-07-27 | 1985-02-12 | Mitsui Toatsu Chem Inc | 酸化還元発色系感熱記録ユニツト用顕色剤 |
| JPH0714911B2 (ja) * | 1985-03-18 | 1995-02-22 | 三井東圧化学株式会社 | 新規キノン誘導体 |
| KR920002741A (ko) * | 1990-07-20 | 1992-02-28 | 베르너 발데크 | 디케토피롤로피롤을 기재로 하는 전기 발색 조성물 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5355223A (en) * | 1976-10-26 | 1978-05-19 | Ciba Geigy Ag | Pressure or heat sensitized recording materials |
| JPS5355222A (en) * | 1976-10-26 | 1978-05-19 | Ciba Geigy Ag | Pressure or heat sensitized recording materials |
-
1982
- 1982-02-02 JP JP57014294A patent/JPS58132587A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5355223A (en) * | 1976-10-26 | 1978-05-19 | Ciba Geigy Ag | Pressure or heat sensitized recording materials |
| JPS5355222A (en) * | 1976-10-26 | 1978-05-19 | Ciba Geigy Ag | Pressure or heat sensitized recording materials |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58132587A (ja) | 1983-08-06 |
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