KR100687457B1 - 안료 조성물의 제조방법 - Google Patents
안료 조성물의 제조방법 Download PDFInfo
- Publication number
- KR100687457B1 KR100687457B1 KR1020000023988A KR20000023988A KR100687457B1 KR 100687457 B1 KR100687457 B1 KR 100687457B1 KR 1020000023988 A KR1020000023988 A KR 1020000023988A KR 20000023988 A KR20000023988 A KR 20000023988A KR 100687457 B1 KR100687457 B1 KR 100687457B1
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- pigment
- anion
- water
- quaternary ammonium
- 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 - Fee Related
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- 239000000049 pigment Substances 0.000 title claims abstract description 79
- 239000000203 mixture Substances 0.000 title claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 57
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 25
- 239000003960 organic solvent Substances 0.000 claims abstract description 20
- 150000001450 anions Chemical class 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 125000005956 isoquinolyl group Chemical group 0.000 claims abstract description 5
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
- 125000005493 quinolyl group Chemical group 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 3
- -1 2-hydroxynaphthyl group Chemical group 0.000 claims description 47
- 230000000813 microbial effect Effects 0.000 claims description 21
- 239000000843 powder Substances 0.000 claims description 20
- 238000011109 contamination Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 239000011324 bead Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 244000005700 microbiome Species 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000012065 filter cake Substances 0.000 description 11
- 239000003973 paint Substances 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- DDPJJWIKEDDECP-UHFFFAOYSA-N 4-methyl-1,2-thiazolidin-3-one Chemical compound CC1CSNC1=O DDPJJWIKEDDECP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000003139 biocide Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000000227 grinding Methods 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000012736 aqueous medium Substances 0.000 description 5
- 230000003115 biocidal effect Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000012066 reaction slurry Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- YIEDHPBKGZGLIK-UHFFFAOYSA-L tetrakis(hydroxymethyl)phosphanium;sulfate Chemical compound [O-]S([O-])(=O)=O.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO YIEDHPBKGZGLIK-UHFFFAOYSA-L 0.000 description 5
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 125000005210 alkyl ammonium group Chemical group 0.000 description 3
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- KYYRTDXOHQYZPO-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=CC=C1NC(=O)CC(C)=O KYYRTDXOHQYZPO-UHFFFAOYSA-N 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- ZGTNBBQKHJMUBI-UHFFFAOYSA-N bis[tetrakis(hydroxymethyl)-lambda5-phosphanyl] sulfate Chemical compound OCP(CO)(CO)(CO)OS(=O)(=O)OP(CO)(CO)(CO)CO ZGTNBBQKHJMUBI-UHFFFAOYSA-N 0.000 description 2
- 230000001332 colony forming effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000006916 nutrient agar Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- ICLYJLBTOGPLMC-KVVVOXFISA-N (z)-octadec-9-enoate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCC\C=C/CCCCCCCC(O)=O ICLYJLBTOGPLMC-KVVVOXFISA-N 0.000 description 1
- MIPNGBGZDGNBRC-UHFFFAOYSA-N 2-[1,3-bis(2-hydroxyethyl)-2,4-dihydrotriazin-5-yl]ethanol Chemical compound OCCN1CC(CCO)=CN(CCO)N1 MIPNGBGZDGNBRC-UHFFFAOYSA-N 0.000 description 1
- LUYIHWDYPAZCNN-UHFFFAOYSA-N 2-butyl-1,2-benzothiazol-3-one Chemical compound C1=CC=C2C(=O)N(CCCC)SC2=C1 LUYIHWDYPAZCNN-UHFFFAOYSA-N 0.000 description 1
- AVGVFDSUDIUXEU-UHFFFAOYSA-N 2-octyl-1,2-thiazolidin-3-one Chemical compound CCCCCCCCN1SCCC1=O AVGVFDSUDIUXEU-UHFFFAOYSA-N 0.000 description 1
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical compound C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 1
- MCLMZMISZCYBBG-UHFFFAOYSA-N 3-ethylheptanoic acid Chemical compound CCCCC(CC)CC(O)=O MCLMZMISZCYBBG-UHFFFAOYSA-N 0.000 description 1
- QMMKOUARLJQQNC-UHFFFAOYSA-N 4-butyl-1,2-benzothiazol-3-one Chemical compound CCCCC1=CC=CC2=C1C(=O)NS2 QMMKOUARLJQQNC-UHFFFAOYSA-N 0.000 description 1
- JUKKWTQZNPHOCO-UHFFFAOYSA-N 4-octyl-1,2-thiazolidin-3-one Chemical compound CCCCCCCCC1CSNC1=O JUKKWTQZNPHOCO-UHFFFAOYSA-N 0.000 description 1
- UQWKODATNHLJMV-UHFFFAOYSA-N 5-chloro-1,2-thiazolidin-3-one Chemical compound ClC1CC(=O)NS1 UQWKODATNHLJMV-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZLFVRXUOSPRRKQ-VHEBQXMUSA-N CI Pigment Red 3 Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 ZLFVRXUOSPRRKQ-VHEBQXMUSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- LFZDEAVRTJKYAF-UHFFFAOYSA-L barium(2+) 2-[(2-hydroxynaphthalen-1-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Ba+2].C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21.C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21 LFZDEAVRTJKYAF-UHFFFAOYSA-L 0.000 description 1
- 239000000981 basic dye Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000001687 destabilization Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical class O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000003621 hammer milling Methods 0.000 description 1
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 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 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical class C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- HGVIAKXYAZRSEG-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1C HGVIAKXYAZRSEG-UHFFFAOYSA-N 0.000 description 1
- 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- ISYWECDDZWTKFF-UHFFFAOYSA-N nonadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(O)=O ISYWECDDZWTKFF-UHFFFAOYSA-N 0.000 description 1
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N pentadecanoic acid Chemical compound CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical class C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 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 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- 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
- C09B67/006—Preparation of organic pigments
-
- 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
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/002—Influencing the physical properties by treatment with an amine
-
- 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
- C09B67/006—Preparation of organic pigments
- C09B67/0069—Non aqueous dispersions of pigments containing only a solvent and a dispersing agent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dispersion Chemistry (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
Description
부 | KLC | THPS | DN | OTW | LV | MIT |
0 | 6.0 ×103 | >105 | >105 | 4.1 ×104 | >105 | 1.0 ×104 |
0.1 | >104 | |||||
0.5 | 0 | >105 | >104 | >104 | >105 | 8.0 ×103 |
1.0 | 0 | >105 | >104 | 2.0 ×104 | >105 | 1.0 ×104 |
3.0 | 0 | >105 | >103 | >104 | >105 | 3.0 ×103 |
5.0 | 0 | >105 | 0 | 1.4 ×103 | >105 | 1.0 ×104 |
부 | KLC | DMHTB | M2HTB | 2C-75 | C-35 | EthO-12 |
0 | 6.0 ×103 | >104 | >104 | >104 | >104 | >104 |
0.5 | 0 | >104 | >104 | 8.0 ×104 | >104 | >104 |
1.0 | 0 | 0 | 0 | 0 | 4.5 ×103 | 0 |
3.0 | 0 | 0 | 0 | 0 | 0 | 0 |
5.0 | 0 | 0 | 0 | 0 | 0 | 0 |
DBS 0부 + KLC 1부 | 0 cfu/g |
DBS 1부 + KLC 1부 | 0 cfu/g |
DBS 2부 + KLC 1부 | 0 cfu/g |
DBS 3부 + KLC 1부 | 0 cfu/g |
부 | KLC | THPS | DN | OTW | LV | MIT |
0 | >104 | >105 | >104 | >104 | >104 | >104 |
0.5 | 2.7 ×103 | >105 | >104 | >104 | >104 | >104 |
1.0 | 0 | >105 | >104 | >104 | >104 | >103 |
3.0 | 0 | >105 | >104 | >104 | >104 | >103 |
5.0 | 0 | >105 | 8.0 ×102 | 0 | >104 | 0 |
부 | KLC | THPS | OTW | LV | MIT |
0 | 6.0 ×104 | >105 | >104 | >104 | >105 |
0.5 | 1.3 ×104 | >105 | >104 | >104 | >105 |
1.0 | 0 | >105 | >104 | >104 | >105 |
3.0 | 0 | >105 | >103 | >104 | >105 |
5.0 | 0 | >105 | >103 | >104 | >105 |
분쇄 기재(millbase) | 최종 페인트 | |
안료 착색 | 20% | 10% |
안료/결합제 | 1 / 1.4 | 1 / 4.7 |
고체 함량 | 35% | 54% |
안료 요구량 | |||||
실시예/안료 | 초기 | 3 주 | 6 주 | 8 주 | 강도의 상실 |
C.I. 피그먼트 옐로우 74 | 141 | 105 | 105 | 36 | |
(대조군) | 134 | 108 | 26 | ||
146 | 104 | 42 | |||
실시예 3 | 93 | 90 | 93 | 0 | |
실시예 4 | 104 | 103 | 103 | 101 | 3 |
부 | KLC | THPS | OTW | LV | MIT |
0 | >104 | >104 | >104 | >104 | >104 |
0.5 | >104 | >104 | >104 | 3.0 ×103 | >104 |
1.0 | >104 | >104 | 5.0 ×103 | 4.0 ×102 | 4.0 ×103 |
3.0 | 0 | >104 | 0 | 1.0 ×102 | 1.0 ×103 |
5.0 | 0 | >104 | 0 | 6.0 ×102 | 9.0 ×102 |
Claims (7)
- 제1항에 있어서, 안료의 수성 분산액을 수 혼화성 4급 암모늄 화합물 및 수 비혼화성 유기 용매와 혼합하는 방법.
- a) 화학식 6의 아민을 디아조화시키고, 화학식 7의 커플링 성분과 커플링시킨 다음,b) 반응 혼합물을 승온에서, 처리 온도 미만의 온도에서 액체인 하나 이상의 수 비혼화성 유기 용매 및 제1항에 기재한 하나 이상의 화학식 3의 수 혼화성 4급 암모늄 화합물의 존재하에 처리하고,c) 반응 생성물을 분리하고, 임의로 생성물을 분말 또는 비드로 전환시킴을 포함하는, 화학식 5의 안료를 포함하는 안정화된 안료 조성물의 제조방법.화학식 5화학식 6화학식 7위의 화학식 5 내지 7에서,R5, R6, R7 및 R8은 각각 독립적으로 수소, C1-C4 알킬, C1-C4 알콕시, 할로겐 또는 니트로이다.
- 제4항에 있어서, 수 비혼화성 유기 용매를 추가로 포함하는 조성물.
- 실온 및 100℃ 이하의 온도에서 액체인 하나 이상의 수 비혼화성 유기 용매와 제1항에 기재한 하나 이상의 화학식 3의 수 혼화성 4급 암모늄 화합물을 포함하는, 칼라 강도의 손실과 미생물 오염에 대해 안정한 안료 조성물.화학식 3위의 화학식 3에서,R1, R2, R3 및 R4는 각각 독립적으로 C1-C22 알킬, C2-C22 알케닐, 벤질, 피리딜, 퀴놀릴, 이소퀴놀릴 또는 폴리옥시알킬레닐을 나타내며,Xn-는 음이온이고,n은, 음이온이 1가인 경우, 1이며, 음이온이 2가인 경우, 2이고, 음이온이 3가인 경우, 3이다.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9910251.9 | 1999-05-05 | ||
GBGB9910251.9A GB9910251D0 (en) | 1999-05-05 | 1999-05-05 | Process for the preparation of pigment compositions |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20000077166A KR20000077166A (ko) | 2000-12-26 |
KR100687457B1 true KR100687457B1 (ko) | 2007-02-27 |
Family
ID=10852746
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020000023988A Expired - Fee Related KR100687457B1 (ko) | 1999-05-05 | 2000-05-04 | 안료 조성물의 제조방법 |
Country Status (8)
Country | Link |
---|---|
US (1) | US6361595B1 (ko) |
EP (1) | EP1054042B1 (ko) |
JP (1) | JP4684385B2 (ko) |
KR (1) | KR100687457B1 (ko) |
BR (1) | BR0002478A (ko) |
CA (1) | CA2307428A1 (ko) |
DE (1) | DE60004725T2 (ko) |
GB (1) | GB9910251D0 (ko) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2413341A1 (en) * | 2001-12-03 | 2003-06-03 | Toyo Ink. Mfg. Co., Ltd. | Pigment yellow 74 and printing ink composition |
US7510577B2 (en) * | 2004-06-29 | 2009-03-31 | Micardia Corporation | Adjustable cardiac valve implant with ferromagnetic material |
US20090252569A1 (en) * | 2008-04-08 | 2009-10-08 | Walker Peter J | System for securing containers with multiple embodiments |
JP6894641B2 (ja) * | 2017-12-01 | 2021-06-30 | 山陽色素株式会社 | 顔料組成物 |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
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DE1469740A1 (de) | 1965-10-08 | 1969-01-02 | Hoechst Ag | Verfahren zur Behandlung eines Azopigmentes |
GB1343606A (en) | 1971-02-11 | 1974-01-16 | Ici Ltd | Dispersing agents |
DE2302509B2 (de) | 1973-01-19 | 1975-01-09 | Farbwerke Hoechst Ag Vormals Meister Lucius & Bruening, 6000 Frankfurt | Disazopigment, Verfahren zu seiner Herstellung und seine Verwendung |
US3959276A (en) | 1973-10-05 | 1976-05-25 | Cosan Chemical Corporation | Antibacterial product |
DE3104257A1 (de) | 1981-02-07 | 1983-02-03 | Hoechst Ag, 6000 Frankfurt | Azopigmentpraeparationen, verfahren zu ihrer herstellung und ihre verwendung |
DE3113882A1 (de) | 1981-04-07 | 1982-10-21 | Hoechst Ag, 6000 Frankfurt | Azopigmentpraeparationen, verfahren zu ihrer herstellung und ihre verwendung |
US4457783A (en) | 1981-10-31 | 1984-07-03 | Ciba-Geigy Corporation | Stabilized opaque form of C.I. Pigment Yellow 74 |
JPH0759482B2 (ja) * | 1985-07-10 | 1995-06-28 | 武田薬品工業株式会社 | 殺菌消毒剤 |
JPS63255220A (ja) * | 1987-04-13 | 1988-10-21 | Sanyo Chem Ind Ltd | 歯科用ウイルス感染防止剤 |
DE3831384A1 (de) | 1988-09-15 | 1990-03-29 | Hoechst Ag | Verfahren zur gezielten beeinflussung des triboelektrischen effektes von azopigmenten |
ES2068260T3 (es) * | 1988-10-06 | 1995-04-16 | Ciba Geigy Ag | Procedimiento para la produccion de composiciones de pigmento. |
US5137568A (en) | 1989-05-02 | 1992-08-11 | J.M. Huber Corporation | Organokaolin pigments in ink formulations |
SU1763461A1 (ru) * | 1989-08-09 | 1992-09-23 | Московское научно-производственное объединение "НИОПИК" | Способ получени моноазопигментов |
DE3932157A1 (de) * | 1989-09-27 | 1991-04-04 | Desowag Materialschutz Gmbh | Holzschutzmittel und verfahren zu dessen herstellung |
JPH04215830A (ja) * | 1990-03-23 | 1992-08-06 | Dainippon Ink & Chem Inc | カチオン性界面活性剤、顔料分散剤および顔料分散液 |
GB9117766D0 (en) | 1991-08-16 | 1991-10-02 | Ciba Geigy Ag | Process for improving storage stability |
US5266110A (en) | 1991-11-01 | 1993-11-30 | Hoechst Aktiengesellschaft | Crystal modification of C.I. Pigment Yellow 16 |
JPH06157432A (ja) * | 1992-11-24 | 1994-06-03 | Kao Corp | ベンザルコニウムハライドの製造方法 |
JPH0977610A (ja) * | 1995-09-08 | 1997-03-25 | Sanyo Chem Ind Ltd | 低刺激性抗菌剤組成物 |
US5663206A (en) | 1996-05-02 | 1997-09-02 | Calgon Corporation | Synergistic antimicrobial composition of N-decyl-N-isononyl-N,N-dimethyl ammonium chloride and alkylguanidine compounds |
GB9823247D0 (en) * | 1998-10-24 | 1998-12-16 | Ciba Geigy Ag | A process for the control of microbial contamination in water-based solids suspensions |
-
1999
- 1999-05-05 GB GBGB9910251.9A patent/GB9910251D0/en not_active Ceased
-
2000
- 2000-04-10 US US09/545,749 patent/US6361595B1/en not_active Expired - Fee Related
- 2000-04-20 JP JP2000119420A patent/JP4684385B2/ja not_active Expired - Fee Related
- 2000-04-26 EP EP00810356A patent/EP1054042B1/en not_active Expired - Lifetime
- 2000-04-26 DE DE60004725T patent/DE60004725T2/de not_active Expired - Lifetime
- 2000-05-03 CA CA002307428A patent/CA2307428A1/en not_active Abandoned
- 2000-05-04 KR KR1020000023988A patent/KR100687457B1/ko not_active Expired - Fee Related
- 2000-05-05 BR BR0002478-3A patent/BR0002478A/pt not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
EP1054042A1 (en) | 2000-11-22 |
DE60004725D1 (de) | 2003-10-02 |
DE60004725T2 (de) | 2004-03-25 |
JP2000327943A (ja) | 2000-11-28 |
US6361595B1 (en) | 2002-03-26 |
BR0002478A (pt) | 2001-01-02 |
EP1054042B1 (en) | 2003-08-27 |
CA2307428A1 (en) | 2000-11-05 |
JP4684385B2 (ja) | 2011-05-18 |
GB9910251D0 (en) | 1999-06-30 |
KR20000077166A (ko) | 2000-12-26 |
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