JPH11286489A - ペリレン化合物および顔料調製物 - Google Patents
ペリレン化合物および顔料調製物Info
- Publication number
- JPH11286489A JPH11286489A JP11041984A JP4198499A JPH11286489A JP H11286489 A JPH11286489 A JP H11286489A JP 11041984 A JP11041984 A JP 11041984A JP 4198499 A JP4198499 A JP 4198499A JP H11286489 A JPH11286489 A JP H11286489A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- formula
- group
- parts
- perylene
- 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.)
- Withdrawn
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 429
- 238000002360 preparation method Methods 0.000 title claims abstract description 123
- -1 Perylene compound Chemical class 0.000 title claims description 36
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 title claims description 19
- 239000002270 dispersing agent Substances 0.000 claims abstract description 171
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000001412 amines Chemical class 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000000843 powder Substances 0.000 claims abstract description 12
- 239000003086 colorant Substances 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 81
- 239000000203 mixture Substances 0.000 claims description 61
- 239000002966 varnish Substances 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000003973 paint Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000000976 ink Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 150000007530 organic bases Chemical class 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052799 carbon Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000008187 granular material Substances 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 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 description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 238000010298 pulverizing process Methods 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 2
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical group CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical compound C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 2
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical compound C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000000485 pigmenting effect Effects 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 238000007639 printing Methods 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000009987 spinning Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000005627 triarylcarbonium group Chemical group 0.000 claims description 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 150000004056 anthraquinones Chemical class 0.000 claims 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 1
- 239000006229 carbon black Substances 0.000 claims 1
- 235000019239 indanthrene blue RS Nutrition 0.000 claims 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 claims 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 claims 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 claims 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 claims 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 8
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 abstract description 7
- 239000011248 coating agent Substances 0.000 abstract description 5
- 238000004040 coloring Methods 0.000 abstract description 4
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 239000000725 suspension Substances 0.000 description 26
- 238000005259 measurement Methods 0.000 description 24
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 22
- 238000003756 stirring Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 239000002585 base Substances 0.000 description 20
- 229920005989 resin Polymers 0.000 description 20
- 239000011347 resin Substances 0.000 description 20
- 230000007935 neutral effect Effects 0.000 description 18
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 16
- 239000012065 filter cake Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 239000000344 soap Substances 0.000 description 10
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000001110 calcium chloride Substances 0.000 description 8
- 229910001628 calcium chloride Inorganic materials 0.000 description 8
- 238000004220 aggregation Methods 0.000 description 7
- 230000002776 aggregation Effects 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 229920000297 Rayon Polymers 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 238000007605 air drying Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 238000003801 milling Methods 0.000 description 5
- 239000012860 organic pigment Substances 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 239000004972 Polyurethane varnish Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 238000000518 rheometry Methods 0.000 description 4
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 3
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 2
- YOOSAIJKYCBPFW-UHFFFAOYSA-N 3-[4-(3-aminopropoxy)butoxy]propan-1-amine Chemical compound NCCCOCCCCOCCCN YOOSAIJKYCBPFW-UHFFFAOYSA-N 0.000 description 2
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 2
- PONZBUKBFVIXOD-UHFFFAOYSA-N 9,10-dicarbamoylperylene-3,4-dicarboxylic acid Chemical class C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=N)C2=C1C3=CC=C2C(=N)O PONZBUKBFVIXOD-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FHNINJWBTRXEBC-UHFFFAOYSA-N Sudan III Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 FHNINJWBTRXEBC-UHFFFAOYSA-N 0.000 description 2
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 230000019612 pigmentation Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- SCHTXWZFMCQMBH-UHFFFAOYSA-N pentane-1,3,5-triamine Chemical compound NCCC(N)CCN SCHTXWZFMCQMBH-UHFFFAOYSA-N 0.000 description 1
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- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
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- 229920000915 polyvinyl chloride Polymers 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
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- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
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- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07D471/06—Peri-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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
-
- 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)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19807422 | 1998-02-21 | ||
| DE19835757A DE19835757A1 (de) | 1998-08-06 | 1998-08-06 | Perylenverbindungen und Pigmentzubereitungen |
| DE19807422:0 | 1998-08-06 | ||
| DE19835757:5 | 1998-08-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11286489A true JPH11286489A (ja) | 1999-10-19 |
| JPH11286489A5 JPH11286489A5 (enExample) | 2006-02-23 |
Family
ID=26044056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11041984A Withdrawn JPH11286489A (ja) | 1998-02-21 | 1999-02-19 | ペリレン化合物および顔料調製物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6221150B1 (enExample) |
| EP (1) | EP0937724B1 (enExample) |
| JP (1) | JPH11286489A (enExample) |
| KR (1) | KR100588884B1 (enExample) |
| DE (1) | DE59912690D1 (enExample) |
| ES (1) | ES2252880T3 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001261987A (ja) * | 2000-02-05 | 2001-09-26 | Clariant Gmbh | 透明顔料形態のペリレン−３，４，９，１０−テトラカルボン酸ジイミドの製造方法 |
| JP2006518400A (ja) * | 2003-02-21 | 2006-08-10 | クラリアント・プロドゥクテ（ドイチュラント）ゲーエムベーハー | ペリレン−３，４，９，１０−テトラカルボン酸ジイミンを主成分とする透明色素調製物の製造方法 |
| JP2008502613A (ja) * | 2004-06-17 | 2008-01-31 | ウエラ アクチェンゲゼルシャフト | 人間の毛髪処理のための蛍光ペリレン化合物の使用 |
| US7754881B2 (en) | 2006-01-23 | 2010-07-13 | Samsung Electronics Co., Ltd. | Aromatic imide-based dispersant for carbon nanotubes and carbon nanotube composition comprising the same |
| JP2011504519A (ja) * | 2007-10-17 | 2011-02-10 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | カラーフィルターでの使用のためのジケトピロロピロール顔料組成物 |
| JP2011116840A (ja) * | 2009-12-02 | 2011-06-16 | Fujifilm Corp | 顔料微粒子分散体、これを用いた光硬化性組成物及びカラーフィルタ |
| JP2012507619A (ja) * | 2008-11-05 | 2012-03-29 | 韓国生産技術研究院 | リオトロピッククロモニック液晶組成物、リオトロピッククロモニック液晶コーティング膜の製造方法及びそれによって製造されたリオトロピッククロモニック液晶コーティング膜 |
| JP2014214244A (ja) * | 2013-04-26 | 2014-11-17 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | 顔料組成物及び顔料樹脂混合物 |
| WO2018051875A1 (ja) * | 2016-09-16 | 2018-03-22 | Dic株式会社 | 顔料分散剤、顔料組成物及び塗料 |
| KR20180076452A (ko) * | 2016-12-28 | 2018-07-06 | 문승호 | 형광 수성 에나멜 조성물 및 이의 제조 방법 |
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| DE19902907A1 (de) * | 1999-01-26 | 2000-07-27 | Clariant Gmbh | Pigmentzubereitungen mit mehreren Perylenverbindungen |
| DE19906494A1 (de) * | 1999-02-17 | 2000-08-24 | Clariant Gmbh | Pigmentzubereitungen auf Basis von Diketopyrrolopyrrolpigmenten mit basischen Perylendispergatoren |
| JP4689913B2 (ja) | 1999-10-01 | 2011-06-01 | キャボット コーポレイション | 立体基および両親媒性基を有する修飾顔料 |
| JP2002020673A (ja) | 2000-04-10 | 2002-01-23 | Seiko Epson Corp | 顔料分散液の製造方法、その方法により得られた顔料分散液、その顔料分散液を用いたインクジェット記録用インク、並びに、そのインクを用いた記録方法および記録物 |
| ATE495224T1 (de) * | 2002-11-01 | 2011-01-15 | Seiko Epson Corp | Tintenkombination, aufzeichnungsverfahren unter verwendung der tintenkombination, aufzeichnungsgerät, aufzeichnungssystem sowie aufgezeichnetes objekt |
| CN1333020C (zh) | 2002-11-01 | 2007-08-22 | 精工爱普生株式会社 | 油墨组、以及记录方法、记录装置、记录系统和记录品 |
| GB0312067D0 (en) * | 2003-05-24 | 2003-07-02 | Avecia Ltd | Inks |
| DE102005050512A1 (de) * | 2005-10-21 | 2007-04-26 | Clariant Produkte (Deutschland) Gmbh | Pigmentzubereitungen auf Basis von Diketopyrrolopyrrolen |
| KR100970941B1 (ko) | 2008-06-11 | 2010-07-21 | 한국생산기술연구원 | 키랄성 페릴렌계 크로모닉 유방성 액정화합물, 이의제조방법, 이로부터 제조된 액정 및 액정박막 |
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| CN108862264B (zh) * | 2018-07-24 | 2021-08-17 | 浙江省海洋开发研究院 | 一种石墨烯分散剂及其制备方法、应用 |
| CN110820074B (zh) * | 2019-11-27 | 2022-07-15 | 中原工学院 | 碱催化制备脲类化合物改性蜜胺纤维的方法 |
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| KR20250011176A (ko) * | 2022-05-19 | 2025-01-21 | 호이바흐 홀딩 스위처런드 아게 (엘티디) | C.i. 피그먼트 바이올렛 23을 기반으로 한 안료 제제 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE299733C (enExample) | ||||
| JPS56118462A (en) | 1980-02-25 | 1981-09-17 | Toyo Ink Mfg Co Ltd | Pigment composition |
| DE3016765A1 (de) * | 1980-04-30 | 1981-11-05 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V., 8000 München | Verwendung von perylenderivaten fuer fluoreszenzzwecke und neue perylenderivate |
| DD299733A7 (de) * | 1980-12-23 | 1992-05-07 | Bitterfeld Chemie | Verfahren zur herstellung von schwarzen tarnpigmenten |
| DE3436206A1 (de) * | 1984-10-03 | 1986-04-03 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von mischkristallpigmenten auf der basis von perylentetracarbonsaeurediimiden und deren verwendung |
| US4762569A (en) * | 1987-08-07 | 1988-08-09 | Sanyo Color Works, Ltd. | Easily dispersible pigment composition and dispersing method |
| DE3740280A1 (de) * | 1987-11-27 | 1989-06-01 | Hoechst Ag | Verfahren zur herstellung von n,n'-dimethyl-perylen-3,4,9,10-tetracarbonsaeurediimid in hochdeckender pigmentform |
| DE3838814A1 (de) | 1987-12-22 | 1989-07-06 | Hoechst Ag | Neue pigmente und ihre verwendung |
| DE3926564A1 (de) * | 1989-08-11 | 1991-02-14 | Hoechst Ag | Neue pigmentzubereitungen auf basis von perylenverbindungen |
| DE3926563A1 (de) * | 1989-08-11 | 1991-02-14 | Hoechst Ag | Sulfonsaeuregruppenhaltige perylenverbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| JPH05117541A (ja) * | 1991-10-24 | 1993-05-14 | Toyo Ink Mfg Co Ltd | 顔料組成物および顔料分散体 |
| DE19501737A1 (de) * | 1995-01-20 | 1996-07-25 | Basf Ag | Verfahren zur Herstellung und Reinigung von Perylen-3,4-dicarbonsäureimiden |
| US5753030A (en) * | 1996-05-13 | 1998-05-19 | Bayer Corporation | Crystal growth modifiers for perylene pigments |
| DE19709798A1 (de) * | 1997-03-10 | 1998-09-17 | Clariant Gmbh | Pigmentzubereitungen und Verfahren zu ihrer Herstellung |
-
1999
- 1999-02-13 ES ES99102917T patent/ES2252880T3/es not_active Expired - Lifetime
- 1999-02-13 DE DE59912690T patent/DE59912690D1/de not_active Expired - Fee Related
- 1999-02-13 EP EP99102917A patent/EP0937724B1/de not_active Expired - Lifetime
- 1999-02-19 JP JP11041984A patent/JPH11286489A/ja not_active Withdrawn
- 1999-02-20 KR KR1019990005687A patent/KR100588884B1/ko not_active Expired - Fee Related
- 1999-02-22 US US09/255,252 patent/US6221150B1/en not_active Expired - Fee Related
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001261987A (ja) * | 2000-02-05 | 2001-09-26 | Clariant Gmbh | 透明顔料形態のペリレン−３，４，９，１０−テトラカルボン酸ジイミドの製造方法 |
| JP2006518400A (ja) * | 2003-02-21 | 2006-08-10 | クラリアント・プロドゥクテ（ドイチュラント）ゲーエムベーハー | ペリレン−３，４，９，１０−テトラカルボン酸ジイミンを主成分とする透明色素調製物の製造方法 |
| JP2008502613A (ja) * | 2004-06-17 | 2008-01-31 | ウエラ アクチェンゲゼルシャフト | 人間の毛髪処理のための蛍光ペリレン化合物の使用 |
| US8269021B2 (en) | 2006-01-23 | 2012-09-18 | Samsung Electronics Co., Ltd. | Aromatic imide-based dispersant for carbon nanotubes and carbon nanotube composition comprising the same |
| US7754881B2 (en) | 2006-01-23 | 2010-07-13 | Samsung Electronics Co., Ltd. | Aromatic imide-based dispersant for carbon nanotubes and carbon nanotube composition comprising the same |
| JP2014088554A (ja) * | 2007-10-17 | 2014-05-15 | Clariant Finance (Bvi) Ltd | カラーフィルターでの使用のためのジケトピロロピロール顔料組成物 |
| JP2011504519A (ja) * | 2007-10-17 | 2011-02-10 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | カラーフィルターでの使用のためのジケトピロロピロール顔料組成物 |
| JP2012507619A (ja) * | 2008-11-05 | 2012-03-29 | 韓国生産技術研究院 | リオトロピッククロモニック液晶組成物、リオトロピッククロモニック液晶コーティング膜の製造方法及びそれによって製造されたリオトロピッククロモニック液晶コーティング膜 |
| US8580143B2 (en) | 2008-11-05 | 2013-11-12 | Korea Institute Of Industrial Technology | Lyotropic chromonic liquid crystal composition, method for manufacture of lyotropic chromonic liquid crystal coating film, and lyotropic chromonic liquid crystal coating film manufactured thereby |
| JP2011116840A (ja) * | 2009-12-02 | 2011-06-16 | Fujifilm Corp | 顔料微粒子分散体、これを用いた光硬化性組成物及びカラーフィルタ |
| JP2014214244A (ja) * | 2013-04-26 | 2014-11-17 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | 顔料組成物及び顔料樹脂混合物 |
| WO2018051875A1 (ja) * | 2016-09-16 | 2018-03-22 | Dic株式会社 | 顔料分散剤、顔料組成物及び塗料 |
| KR20180076452A (ko) * | 2016-12-28 | 2018-07-06 | 문승호 | 형광 수성 에나멜 조성물 및 이의 제조 방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR19990072803A (ko) | 1999-09-27 |
| EP0937724A1 (de) | 1999-08-25 |
| KR100588884B1 (ko) | 2006-06-13 |
| EP0937724B1 (de) | 2005-10-26 |
| DE59912690D1 (de) | 2005-12-01 |
| ES2252880T3 (es) | 2006-05-16 |
| US6221150B1 (en) | 2001-04-24 |
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