CA2483836A1 - Compositions and methods for imparting improved rheology on pigment based inks and paints - Google Patents
Compositions and methods for imparting improved rheology on pigment based inks and paints Download PDFInfo
- Publication number
- CA2483836A1 CA2483836A1 CA002483836A CA2483836A CA2483836A1 CA 2483836 A1 CA2483836 A1 CA 2483836A1 CA 002483836 A CA002483836 A CA 002483836A CA 2483836 A CA2483836 A CA 2483836A CA 2483836 A1 CA2483836 A1 CA 2483836A1
- Authority
- CA
- Canada
- Prior art keywords
- pigment
- anionic
- cationic
- red
- dye
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 103
- 239000003973 paint Substances 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims description 31
- 238000000518 rheometry Methods 0.000 title abstract description 3
- 239000001042 pigment based ink Substances 0.000 title 1
- 239000000049 pigment Substances 0.000 claims abstract description 251
- 239000000975 dye Substances 0.000 claims abstract description 90
- 125000002091 cationic group Chemical group 0.000 claims abstract description 81
- 125000000129 anionic group Chemical group 0.000 claims abstract description 79
- 239000012860 organic pigment Substances 0.000 claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 239000002002 slurry Substances 0.000 claims description 41
- -1 flavanthrone Chemical compound 0.000 claims description 17
- 239000006185 dispersion Substances 0.000 claims description 15
- 229940099800 pigment red 48 Drugs 0.000 claims description 15
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 claims description 13
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 235000019239 indanthrene blue RS Nutrition 0.000 claims description 12
- 239000003093 cationic surfactant Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000012065 filter cake Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 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 9
- 239000000654 additive Substances 0.000 claims description 9
- 239000003945 anionic surfactant Substances 0.000 claims description 9
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 8
- VPWFPZBFBFHIIL-UHFFFAOYSA-L disodium 4-[(4-methyl-2-sulfophenyl)diazenyl]-3-oxidonaphthalene-2-carboxylate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 VPWFPZBFBFHIIL-UHFFFAOYSA-L 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-UHFFFAOYSA-N 0.000 claims description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 235000010187 litholrubine BK Nutrition 0.000 claims description 6
- 239000001054 red pigment Substances 0.000 claims description 6
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 5
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical group [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 claims description 5
- 239000000980 acid dye Substances 0.000 claims description 5
- 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 description 5
- 150000004056 anthraquinones Chemical class 0.000 claims description 5
- 150000004696 coordination complex Chemical class 0.000 claims description 5
- 239000000982 direct dye Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 239000008187 granular material Substances 0.000 claims description 5
- 239000000983 mordant dye Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 239000000985 reactive dye Substances 0.000 claims description 5
- 239000001052 yellow pigment Substances 0.000 claims description 5
- IAFBRPFISOTXSO-UHFFFAOYSA-N 2-[[2-chloro-4-[3-chloro-4-[[1-(2,4-dimethylanilino)-1,3-dioxobutan-2-yl]diazenyl]phenyl]phenyl]diazenyl]-n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)C(C(=O)C)N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(C)=O)C(=O)NC1=CC=C(C)C=C1C IAFBRPFISOTXSO-UHFFFAOYSA-N 0.000 claims description 4
- CNYGFPPAGUCRIC-UHFFFAOYSA-L [4-[[4-(dimethylamino)phenyl]-phenylmethylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium;2-hydroxy-2-oxoacetate;oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)C([O-])=O.OC(=O)C([O-])=O.C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1.C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 CNYGFPPAGUCRIC-UHFFFAOYSA-L 0.000 claims description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
- 230000003750 conditioning effect Effects 0.000 claims description 4
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 claims description 4
- 238000011010 flushing procedure Methods 0.000 claims description 4
- 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 3
- 235000000177 Indigofera tinctoria Nutrition 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 229940097275 indigo Drugs 0.000 claims description 3
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 claims description 3
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 3
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 3
- BSIHWSXXPBAGTC-UHFFFAOYSA-N isoviolanthrone Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C(C4=C56)=CC=C5C5=CC=CC=C5C(=O)C6=CC=C4C4=C3C2=C1C=C4 BSIHWSXXPBAGTC-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 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 3
- PYUYQYBDJFMFTH-WMMMYUQOSA-N naphthol red Chemical group CCOC1=CC=CC=C1NC(=O)C(C1=O)=CC2=CC=CC=C2\C1=N\NC1=CC=C(C(N)=O)C=C1 PYUYQYBDJFMFTH-WMMMYUQOSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 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 description 3
- 238000005406 washing Methods 0.000 claims description 3
- MCTQNEBFZMBRSQ-UHFFFAOYSA-N (3-amino-4-phenyldiazenylphenyl)azanium;chloride Chemical compound Cl.NC1=CC(N)=CC=C1N=NC1=CC=CC=C1 MCTQNEBFZMBRSQ-UHFFFAOYSA-N 0.000 claims description 2
- ZOMLUNRKXJYKPD-UHFFFAOYSA-N 1,3,3-trimethyl-2-[2-(2-methylindol-3-ylidene)ethylidene]indole;hydrochloride Chemical compound [Cl-].C1=CC=C2C(C)(C)C(/C=C/C=3C4=CC=CC=C4NC=3C)=[N+](C)C2=C1 ZOMLUNRKXJYKPD-UHFFFAOYSA-N 0.000 claims description 2
- RTLULCVBFCRQKI-UHFFFAOYSA-N 1-amino-4-[3-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-4-sulfoanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S(O)(=O)=O)C=C1NC(C=1)=CC=C(S(O)(=O)=O)C=1NC1=NC(Cl)=NC(Cl)=N1 RTLULCVBFCRQKI-UHFFFAOYSA-N 0.000 claims description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 2
- QFVHZQCOUORWEI-UHFFFAOYSA-N 4-[(4-anilino-5-sulfonaphthalen-1-yl)diazenyl]-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C=12C(O)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=CC=1N=NC(C1=CC=CC(=C11)S(O)(=O)=O)=CC=C1NC1=CC=CC=C1 QFVHZQCOUORWEI-UHFFFAOYSA-N 0.000 claims description 2
- HNJRBCJUHORNHV-UHFFFAOYSA-N 5-[(4-hydroxyphenyl)diazenyl]-2-[2-[4-[(4-hydroxyphenyl)diazenyl]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound C1=CC(O)=CC=C1N=NC(C=C1S(O)(=O)=O)=CC=C1C=CC1=CC=C(N=NC=2C=CC(O)=CC=2)C=C1S(O)(=O)=O HNJRBCJUHORNHV-UHFFFAOYSA-N 0.000 claims description 2
- ZWONWYNZSWOYQC-UHFFFAOYSA-N 5-benzamido-3-[[5-[[4-chloro-6-(4-sulfoanilino)-1,3,5-triazin-2-yl]amino]-2-sulfophenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OC1=C(N=NC2=CC(NC3=NC(NC4=CC=C(C=C4)S(O)(=O)=O)=NC(Cl)=N3)=CC=C2S(O)(=O)=O)C(=CC2=C1C(NC(=O)C1=CC=CC=C1)=CC(=C2)S(O)(=O)=O)S(O)(=O)=O ZWONWYNZSWOYQC-UHFFFAOYSA-N 0.000 claims description 2
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims description 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 2
- IQFVPQOLBLOTPF-UHFFFAOYSA-L Congo Red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(N=NC3=CC=C(C=C3)C3=CC=C(C=C3)N=NC3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-UHFFFAOYSA-L 0.000 claims description 2
- HMEKVHWROSNWPD-UHFFFAOYSA-N Erioglaucine A Chemical compound [NH4+].[NH4+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 HMEKVHWROSNWPD-UHFFFAOYSA-N 0.000 claims description 2
- ATNOAWAQFYGAOY-UHFFFAOYSA-J Evans blue Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(S([O-])(=O)=O)=C(N)C2=C(O)C(N=NC3=CC=C(C=C3C)C=3C=C(C(=CC=3)N=NC=3C(=C4C(N)=C(C=C(C4=CC=3)S([O-])(=O)=O)S([O-])(=O)=O)O)C)=CC=C21 ATNOAWAQFYGAOY-UHFFFAOYSA-J 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- JQYMGXZJTCOARG-UHFFFAOYSA-N Reactive blue 2 Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S(O)(=O)=O)C=C1NC(C=C1S(O)(=O)=O)=CC=C1NC(N=1)=NC(Cl)=NC=1NC1=CC=CC(S(O)(=O)=O)=C1 JQYMGXZJTCOARG-UHFFFAOYSA-N 0.000 claims description 2
- UFUQRRYHIHJMPB-DUCFOALUSA-L Sirius red 4B Chemical compound [Na+].[Na+].OS(=O)(=O)c1cc2cc(NC(=O)c3ccccc3)ccc2c([O-])c1\N=N\c1ccc(cc1)\N=N\c1ccc(cc1)S([O-])(=O)=O UFUQRRYHIHJMPB-DUCFOALUSA-L 0.000 claims description 2
- YIQKLZYTHXTDDT-UHFFFAOYSA-H Sirius red F3B Chemical compound C1=CC(=CC=C1N=NC2=CC(=C(C=C2)N=NC3=C(C=C4C=C(C=CC4=C3[O-])NC(=O)NC5=CC6=CC(=C(C(=C6C=C5)[O-])N=NC7=C(C=C(C=C7)N=NC8=CC=C(C=C8)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+] YIQKLZYTHXTDDT-UHFFFAOYSA-H 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 claims description 2
- GRPFBMKYXAYEJM-UHFFFAOYSA-M [4-[(2-chlorophenyl)-[4-(dimethylamino)phenyl]methylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium;chloride Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C(=CC=CC=1)Cl)=C1C=CC(=[N+](C)C)C=C1 GRPFBMKYXAYEJM-UHFFFAOYSA-M 0.000 claims description 2
- LIKZXCROQGHXTI-UHFFFAOYSA-M acid blue 25 Chemical compound [Na+].C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S([O-])(=O)=O)C=C1NC1=CC=CC=C1 LIKZXCROQGHXTI-UHFFFAOYSA-M 0.000 claims description 2
- DGOBMKYRQHEFGQ-UHFFFAOYSA-L acid green 5 Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=CC(=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 DGOBMKYRQHEFGQ-UHFFFAOYSA-L 0.000 claims description 2
- CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 claims description 2
- VSTHNGLPHBTRMB-UHFFFAOYSA-N acridine orange Chemical compound [H+].[Cl-].C1=CC(N(C)C)=CC2=NC3=CC(N(C)C)=CC=C3C=C21 VSTHNGLPHBTRMB-UHFFFAOYSA-N 0.000 claims description 2
- WXLFIFHRGFOVCD-UHFFFAOYSA-L azophloxine Chemical compound [Na+].[Na+].OC1=C2C(NC(=O)C)=CC(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=C1N=NC1=CC=CC=C1 WXLFIFHRGFOVCD-UHFFFAOYSA-L 0.000 claims description 2
- VJDDAARZIFHSQY-UHFFFAOYSA-N basic black 2 Chemical compound [Cl-].C=1C2=[N+](C=3C=CC=CC=3)C3=CC(N(CC)CC)=CC=C3N=C2C=CC=1NN=C1C=CC(=O)C=C1 VJDDAARZIFHSQY-UHFFFAOYSA-N 0.000 claims description 2
- VUXVWHOCQSLYRN-UHFFFAOYSA-O benzyl-[4-[[4-[benzyl(ethyl)amino]phenyl]-(2,4-disulfophenyl)methylidene]cyclohexa-2,5-dien-1-ylidene]-ethylazanium Chemical compound C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=CC=CC=2)C=2C(=CC(=CC=2)S(O)(=O)=O)S(O)(=O)=O)C=CC=1N(CC)CC1=CC=CC=C1 VUXVWHOCQSLYRN-UHFFFAOYSA-O 0.000 claims description 2
- 239000001045 blue dye Substances 0.000 claims description 2
- 239000001055 blue pigment Substances 0.000 claims description 2
- PGWPNHMAKPHTMA-UHFFFAOYSA-N chembl1091601 Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N=NC3=CC=C(C=C3S(O)(=O)=O)NC(=O)NC3=CC=C(C(=C3)S(O)(=O)=O)N=NC3=C4C(O)=CC(=CC4=CC=C3N)S(O)(=O)=O)=C(N)C=CC2=C1 PGWPNHMAKPHTMA-UHFFFAOYSA-N 0.000 claims description 2
- IWWWBRIIGAXLCJ-BGABXYSRSA-N chembl1185241 Chemical compound C1=2C=C(C)C(NCC)=CC=2OC2=C\C(=N/CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC IWWWBRIIGAXLCJ-BGABXYSRSA-N 0.000 claims description 2
- ZMLWOOMWRCRLCH-UHFFFAOYSA-N chembl124855 Chemical compound C1=CC=C2C(N=NC3=C4C=CC=CC4=CC=C3O)=C(O)C=C(S(O)(=O)=O)C2=C1 ZMLWOOMWRCRLCH-UHFFFAOYSA-N 0.000 claims description 2
- HFIYIRIMGZMCPC-UHFFFAOYSA-J chembl1326377 Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(N=NC=3C=CC(=CC=3)S(=O)(=O)CCOS([O-])(=O)=O)C(O)=C2C(N)=C1N=NC1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 HFIYIRIMGZMCPC-UHFFFAOYSA-J 0.000 claims description 2
- YOCIQNIEQYCORH-UHFFFAOYSA-M chembl2028361 Chemical compound [Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=CC=C1 YOCIQNIEQYCORH-UHFFFAOYSA-M 0.000 claims description 2
- BEQIIZJSZSVJJK-UHFFFAOYSA-M chembl2028372 Chemical compound [Na+].OC1=CC=C(S([O-])(=O)=O)C=C1N=NC1=C(O)C=CC2=CC=CC=C12 BEQIIZJSZSVJJK-UHFFFAOYSA-M 0.000 claims description 2
- NLMHXPDMNXMQBY-UHFFFAOYSA-L chembl260999 Chemical compound [Na+].[Na+].C1=CC(NC(=O)C)=CC=C1N=NC(C(=CC1=C2)S([O-])(=O)=O)=C(O)C1=CC=C2NC(=O)NC1=CC=C(C(O)=C(N=NC=2C=CC=CC=2)C(=C2)S([O-])(=O)=O)C2=C1 NLMHXPDMNXMQBY-UHFFFAOYSA-L 0.000 claims description 2
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- NKLPQNGYXWVELD-UHFFFAOYSA-M coomassie brilliant blue Chemical compound [Na+].C1=CC(OCC)=CC=C1NC1=CC=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=C1 NKLPQNGYXWVELD-UHFFFAOYSA-M 0.000 claims description 2
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- BMYUQZABARGLAD-UHFFFAOYSA-L disodium;8-(4-methylanilino)-5-[[4-[(3-sulfonatophenyl)diazenyl]naphthalen-1-yl]diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC(C)=CC=C1NC(C1=C(C=CC=C11)S([O-])(=O)=O)=CC=C1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC=CC(S([O-])(=O)=O)=C1 BMYUQZABARGLAD-UHFFFAOYSA-L 0.000 claims description 2
- HBINTOQGSKHKJI-UHFFFAOYSA-L disodium;8-[[3-methyl-4-(4-methylphenyl)sulfonyloxyphenyl]diazenyl]-5-[[4-(4-nitro-2-sulfonatoanilino)phenyl]diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=C(N=NC=2C3=CC(=CC=C3C(N=NC=3C=CC(NC=4C(=CC(=CC=4)[N+]([O-])=O)S([O-])(=O)=O)=CC=3)=CC=2)S([O-])(=O)=O)C=C1C HBINTOQGSKHKJI-UHFFFAOYSA-L 0.000 claims description 2
- XPRMZBUQQMPKCR-UHFFFAOYSA-L disodium;8-anilino-5-[[4-[(3-sulfonatophenyl)diazenyl]naphthalen-1-yl]diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C3=CC=CC=C3C(N=NC=3C4=CC=CC(=C4C(NC=4C=CC=CC=4)=CC=3)S([O-])(=O)=O)=CC=2)=C1 XPRMZBUQQMPKCR-UHFFFAOYSA-L 0.000 claims description 2
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- YYGBVRCTHASBKD-UHFFFAOYSA-M methylene green Chemical compound [Cl-].C1=CC(N(C)C)=C([N+]([O-])=O)C2=[S+]C3=CC(N(C)C)=CC=C3N=C21 YYGBVRCTHASBKD-UHFFFAOYSA-M 0.000 claims description 2
- CTIQLGJVGNGFEW-UHFFFAOYSA-L naphthol yellow S Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 CTIQLGJVGNGFEW-UHFFFAOYSA-L 0.000 claims description 2
- IPSIPYMEZZPCPY-UHFFFAOYSA-N new fuchsin Chemical compound [Cl-].C1=CC(=[NH2+])C(C)=CC1=C(C=1C=C(C)C(N)=CC=1)C1=CC=C(N)C(C)=C1 IPSIPYMEZZPCPY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- HSXUHWZMNJHFRV-QIKYXUGXSA-L orange G Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1\N=N\C1=CC=CC=C1 HSXUHWZMNJHFRV-QIKYXUGXSA-L 0.000 claims description 2
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- XWZDJOJCYUSIEY-YOYNBWDYSA-L procion red MX-5B Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=CC(NC=3N=C(Cl)N=C(Cl)N=3)=C2C(O)=C1\N=N\C1=CC=CC=C1 XWZDJOJCYUSIEY-YOYNBWDYSA-L 0.000 claims description 2
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- DHHGSXPASZBLGC-VPMNAVQSSA-L remazole orange-3R Chemical compound [Na+].[Na+].OC=1C2=CC(NC(=O)C)=CC=C2C=C(S([O-])(=O)=O)C=1\N=N\C1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 DHHGSXPASZBLGC-VPMNAVQSSA-L 0.000 claims description 2
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 2
- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 claims description 2
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- RRETZLLHOMHNNB-UHFFFAOYSA-M sodium;1-amino-9,10-dioxo-4-(2,4,6-trimethylanilino)anthracene-2-sulfonate Chemical compound [Na+].CC1=CC(C)=CC(C)=C1NC1=CC(S([O-])(=O)=O)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O RRETZLLHOMHNNB-UHFFFAOYSA-M 0.000 claims description 2
- RWVGQQGBQSJDQV-UHFFFAOYSA-M sodium;3-[[4-[(e)-[4-(4-ethoxyanilino)phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]-2-methylcyclohexa-2,5-dien-1-ylidene]methyl]-n-ethyl-3-methylanilino]methyl]benzenesulfonate Chemical compound [Na+].C1=CC(OCC)=CC=C1NC1=CC=C(C(=C2C(=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=2C(=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=C1 RWVGQQGBQSJDQV-UHFFFAOYSA-M 0.000 claims description 2
- FJBHGWADYLMEJG-UHFFFAOYSA-M sodium;3-[[4-[[4-(diethylamino)phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]cyclohexa-2,5-dien-1-ylidene]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC=1C=C(C=CC=1)S([O-])(=O)=O)=C(C=C1)C=CC1=[N+](CC)CC1=CC=CC(S([O-])(=O)=O)=C1 FJBHGWADYLMEJG-UHFFFAOYSA-M 0.000 claims description 2
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- WTPOYMNMKZIOGO-UHFFFAOYSA-K trisodium;2,5-dichloro-4-[4-[[5-[[4-chloro-6-(4-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-2-sulfonatophenyl]diazenyl]-3-methyl-5-oxo-4h-pyrazol-1-yl]benzenesulfonate Chemical compound [Na+].[Na+].[Na+].CC1=NN(C=2C(=CC(=C(Cl)C=2)S([O-])(=O)=O)Cl)C(=O)C1N=NC(C(=CC=1)S([O-])(=O)=O)=CC=1NC(N=1)=NC(Cl)=NC=1NC1=CC=C(S([O-])(=O)=O)C=C1 WTPOYMNMKZIOGO-UHFFFAOYSA-K 0.000 claims description 2
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- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 230000019612 pigmentation Effects 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- 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 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 238000010793 Steam injection (oil industry) Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000001905 inorganic group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- NWKBFCIAPOSTKG-UHFFFAOYSA-M trimethyl-[3-[(3-methyl-5-oxo-1-phenyl-4h-pyrazol-4-yl)diazenyl]phenyl]azanium;chloride Chemical compound [Cl-].CC1=NN(C=2C=CC=CC=2)C(=O)C1N=NC1=CC=CC([N+](C)(C)C)=C1 NWKBFCIAPOSTKG-UHFFFAOYSA-M 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
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
-
- 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
-
- 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
- C09B67/0004—Coated particulate pigments or dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02405349.8 | 2002-04-29 | ||
| EP02405349 | 2002-04-29 | ||
| PCT/EP2003/004259 WO2003093373A1 (en) | 2002-04-29 | 2003-04-24 | Compositions and methods for imparting improved rheology on pigment based inks and paints |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2483836A1 true CA2483836A1 (en) | 2003-11-13 |
Family
ID=29286251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002483836A Abandoned CA2483836A1 (en) | 2002-04-29 | 2003-04-24 | Compositions and methods for imparting improved rheology on pigment based inks and paints |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7074267B2 (https=) |
| EP (1) | EP1499683A1 (https=) |
| JP (1) | JP2005523985A (https=) |
| KR (1) | KR20050006208A (https=) |
| CN (1) | CN100343342C (https=) |
| AU (1) | AU2003224122A1 (https=) |
| BR (1) | BR0309630A (https=) |
| CA (1) | CA2483836A1 (https=) |
| MX (1) | MXPA04010752A (https=) |
| WO (1) | WO2003093373A1 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1215251B1 (en) * | 2000-12-12 | 2005-06-15 | Konica Corporation | Pigment dispersion liquid for ink jetting |
| US20080282931A1 (en) * | 2003-11-11 | 2008-11-20 | Stuart Cook Niven | Pigment Compositions for Oil-Based Lithographic Printing Ink System |
| JP4649291B2 (ja) * | 2005-08-11 | 2011-03-09 | 東洋インキ製造株式会社 | 着色組成物の製造方法、および該方法で製造された着色組成物を用いたカラーフィルタ |
| CN101730724A (zh) * | 2007-04-24 | 2010-06-09 | 太阳化学公司 | 用于非水性油墨和涂料的颜料 |
| GB2450975B (en) * | 2007-07-12 | 2010-02-24 | Ciba Holding Inc | Yellow radiation curing inks |
| US8270063B2 (en) * | 2007-09-07 | 2012-09-18 | Basf Se | Encapsulated dispersions comprising electrophoretically mobile organic colorants |
| US8857963B2 (en) | 2008-04-29 | 2014-10-14 | Hewlett-Packard Development Company, L.P. | Inks and ink sets for improved performance and image quality |
| US7972425B2 (en) * | 2008-12-29 | 2011-07-05 | Pitney Bowes Inc. | Postal blue ink with improved durability |
| US8328922B2 (en) * | 2008-12-29 | 2012-12-11 | Pitney Bowes Inc. | Postal blue ink with high reliability |
| TW201111447A (en) * | 2009-07-14 | 2011-04-01 | Sumitomo Chemical Co | Production method of pigment dispersion solution |
| JP5481647B2 (ja) * | 2009-07-17 | 2014-04-23 | 山陽色素株式会社 | トリアリールメタン系及びローダミン系顔料組成物並びにこれらを用いた顔料分散体 |
| WO2011159298A1 (en) * | 2010-06-16 | 2011-12-22 | Hewlett-Packard Development Company, L.P. | Blue ink for postage printing |
| CN102250492A (zh) * | 2011-03-11 | 2011-11-23 | 郭长虹 | 多功能染色剂及其配制方法以及本剂对织物染色补色方法 |
| WO2013150622A1 (ja) * | 2012-04-04 | 2013-10-10 | 三菱鉛筆株式会社 | 油性インク組成物 |
| CN104073025A (zh) * | 2013-03-29 | 2014-10-01 | 日本化药株式会社 | 着色分散液、油墨组合物、喷墨记录方法以及着色体 |
| JP2016034994A (ja) * | 2014-08-01 | 2016-03-17 | クラリアント・インターナシヨナル・リミテツド | 彩度と色相が改良されたイエロー着色剤組成物、そのための顔料組成物およびそれらの使用 |
| US10364366B2 (en) * | 2015-09-30 | 2019-07-30 | Brother Kogyo Kabushiki Kaisha | Water-based ink for ink-jet recording and ink cartridge |
| DE102015121562B4 (de) * | 2015-12-10 | 2021-05-06 | Coroplast Fritz Müller Gmbh & Co. Kg | Hochtemperaturbeständiges farbiges, insbesondere orangefarbiges, Klebeband, Verfahren zu seiner Herstellung, Verwendung eines Trägers zu seiner Herstellung sowie Verwendung des Klebebandes zur Herstellung von Kabelbäumen |
| CN120476177A (zh) * | 2023-01-13 | 2025-08-12 | 卡博特公司 | 用于二聚类颜料的增效剂 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2012152C3 (de) * | 1970-03-14 | 1974-03-21 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Verfahren zur Herstellung von Pigmentfarbstoffgemischen aus Disazofarbstoffen und deren Verwendung |
| GB1356253A (en) * | 1970-05-06 | 1974-06-12 | Ciba Geigy Uk Ltd | Azo pigment compositions |
| GB1356254A (en) * | 1970-07-16 | 1974-06-12 | Ciba Geigy Uk Ltd | Pigment compositions |
| US4162348A (en) * | 1973-04-02 | 1979-07-24 | Sumitomo Chemical Company, Limited | Coloring of inorganic substrates and mineral materials |
| JPS5463132A (en) * | 1977-10-31 | 1979-05-21 | Shiseido Co Ltd | Production of red-coloring pigment |
| JPS565552A (en) * | 1979-06-28 | 1981-01-21 | Toyo Ink Mfg Co Ltd | Photoreceptor for electrophotography |
| NZ201300A (en) * | 1981-08-11 | 1985-12-13 | Ici Plc | Pigment:fluidising compositions containing disazo compounds |
| DE3906525A1 (de) * | 1989-03-02 | 1990-09-06 | Basf Ag | Farbmittelmischungen, enthaltend azoverbindungen auf basis von phenyloxdiazolylanilin |
| GB9112155D0 (en) * | 1991-06-06 | 1991-07-24 | Ciba Geigy Ag | Production of pigments |
| ES2088070T5 (es) * | 1991-10-23 | 2001-04-01 | Clariant Gmbh | Preparados de pigmentos. |
| EP0648816B1 (de) * | 1993-10-15 | 2000-01-26 | Ciba SC Holding AG | Färben von Leder mit Farbstoffmischungen |
| DE19547800A1 (de) * | 1994-12-23 | 1996-06-27 | Ciba Geigy Ag | Wässrige Drucktinten für den Tintenstrahldruck |
| WO1997035927A1 (de) * | 1996-03-26 | 1997-10-02 | Basf Aktiengesellschaft | Stabile farbmittelzusammensetzungen |
| AU5561198A (en) * | 1996-12-20 | 1998-07-17 | Ciba Specialty Chemicals Holding Inc. | Complex polymethine dyes and their use |
| EP1047739B1 (en) | 1998-05-28 | 2009-11-04 | Sun Chemical Corporation | Dye based aqueous pigment dispersions |
| EP1218457A1 (en) * | 1999-08-09 | 2002-07-03 | Cabot Corporation | Ink compositions having modified pigments with high or low treatment levels |
| US6123758A (en) * | 1999-09-22 | 2000-09-26 | Xerox Corporation | Ink compositions containing undecylenoyl sarcosinate salts |
| US6672717B2 (en) * | 2001-11-13 | 2004-01-06 | Xerox Corporation | Ink jet printing with inks containing cationic-anionic monomer pairs |
-
2003
- 2003-04-24 BR BR0309630-0A patent/BR0309630A/pt not_active Application Discontinuation
- 2003-04-24 EP EP03720522A patent/EP1499683A1/en not_active Withdrawn
- 2003-04-24 CN CNB038095777A patent/CN100343342C/zh not_active Expired - Fee Related
- 2003-04-24 CA CA002483836A patent/CA2483836A1/en not_active Abandoned
- 2003-04-24 AU AU2003224122A patent/AU2003224122A1/en not_active Abandoned
- 2003-04-24 MX MXPA04010752A patent/MXPA04010752A/es not_active Application Discontinuation
- 2003-04-24 WO PCT/EP2003/004259 patent/WO2003093373A1/en not_active Ceased
- 2003-04-24 KR KR10-2004-7017393A patent/KR20050006208A/ko not_active Ceased
- 2003-04-24 US US10/512,013 patent/US7074267B2/en not_active Expired - Fee Related
- 2003-04-24 JP JP2004501511A patent/JP2005523985A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA04010752A (es) | 2005-03-07 |
| KR20050006208A (ko) | 2005-01-15 |
| BR0309630A (pt) | 2005-03-08 |
| AU2003224122A1 (en) | 2003-11-17 |
| CN1649972A (zh) | 2005-08-03 |
| WO2003093373A1 (en) | 2003-11-13 |
| JP2005523985A (ja) | 2005-08-11 |
| EP1499683A1 (en) | 2005-01-26 |
| CN100343342C (zh) | 2007-10-17 |
| US20050115464A1 (en) | 2005-06-02 |
| US7074267B2 (en) | 2006-07-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |