BRPI0415608B1 - Composição de tinta para inkjet e processo de preparação da mesma - Google Patents
Composição de tinta para inkjet e processo de preparação da mesma Download PDFInfo
- Publication number
- BRPI0415608B1 BRPI0415608B1 BRPI0415608-0A BRPI0415608A BRPI0415608B1 BR PI0415608 B1 BRPI0415608 B1 BR PI0415608B1 BR PI0415608 A BRPI0415608 A BR PI0415608A BR PI0415608 B1 BRPI0415608 B1 BR PI0415608B1
- Authority
- BR
- Brazil
- Prior art keywords
- azo
- group
- reagent
- diazonium
- coupler
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 155
- 238000002360 preparation method Methods 0.000 title description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 144
- 239000000049 pigment Substances 0.000 claims abstract description 121
- 239000012954 diazonium Substances 0.000 claims abstract description 97
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims abstract description 93
- 238000000034 method Methods 0.000 claims abstract description 39
- 125000003010 ionic group Chemical group 0.000 claims abstract description 27
- 239000007788 liquid Substances 0.000 claims abstract description 19
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 12
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 239000006185 dispersion Substances 0.000 claims description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 51
- AZBNFLZFSZDPQF-UHFFFAOYSA-L disodium;[4-[4-(sulfinatomethylamino)phenyl]sulfonylanilino]methanesulfinate Chemical compound [Na+].[Na+].C1=CC(NCS(=O)[O-])=CC=C1S(=O)(=O)C1=CC=C(NCS([O-])=O)C=C1 AZBNFLZFSZDPQF-UHFFFAOYSA-L 0.000 claims description 50
- 230000008569 process Effects 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000008365 aqueous carrier Substances 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical group CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- NFTNTGFZYSCPSK-UHFFFAOYSA-N 3-hydroxynaphthalene-2-carboxamide Chemical compound C1=CC=C2C=C(O)C(C(=O)N)=CC2=C1 NFTNTGFZYSCPSK-UHFFFAOYSA-N 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical group NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical group NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 239000008135 aqueous vehicle Substances 0.000 claims 4
- 239000000376 reactant Substances 0.000 claims 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims 2
- 239000002270 dispersing agent Substances 0.000 abstract description 24
- 239000000976 ink Substances 0.000 description 70
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000002245 particle Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000654 additive Substances 0.000 description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 239000001052 yellow pigment Substances 0.000 description 7
- 125000000129 anionic group Chemical group 0.000 description 6
- -1 bis-azo compound Chemical class 0.000 description 6
- 230000000269 nucleophilic effect Effects 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000002091 cationic group Chemical group 0.000 description 5
- 238000011026 diafiltration Methods 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- 238000002604 ultrasonography Methods 0.000 description 5
- VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 4
- 229960004963 mesalazine Drugs 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000005342 ion exchange Methods 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
- 125000000962 organic group Chemical group 0.000 description 3
- 238000001226 reprecipitation Methods 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- NIPDVSLAMPAWTP-UHFFFAOYSA-N 2-methoxy-5-nitroaniline Chemical compound COC1=CC=C([N+]([O-])=O)C=C1N NIPDVSLAMPAWTP-UHFFFAOYSA-N 0.000 description 2
- KQNZKBRSEJLVEO-UHFFFAOYSA-N 3-oxo-n-(2-oxobenzimidazol-5-yl)butanamide Chemical compound C1=C(NC(=O)CC(=O)C)C=CC2=NC(=O)N=C21 KQNZKBRSEJLVEO-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910006069 SO3H Chemical group 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 238000006149 azo coupling reaction Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000003139 buffering effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000003966 growth inhibitor Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000003116 impacting effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000002500 ions Chemical class 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
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- PSDFQEVOCCOOET-UHFFFAOYSA-N 2-[2-(2-aminophenoxy)ethoxy]aniline Chemical compound NC1=CC=CC=C1OCCOC1=CC=CC=C1N PSDFQEVOCCOOET-UHFFFAOYSA-N 0.000 description 1
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
- BFWYZZPDZZGSLJ-UHFFFAOYSA-N 4-(aminomethyl)aniline Chemical compound NCC1=CC=C(N)C=C1 BFWYZZPDZZGSLJ-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 description 1
- 229910018828 PO3H2 Inorganic materials 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [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 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical class CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000005526 alkyl sulfate group Chemical group 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 239000000989 food dye Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical class [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 description 1
- 239000003906 humectant Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 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
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/689,268 US7300504B2 (en) | 2003-10-20 | 2003-10-20 | Inkjet inks and methods of preparing the same |
| US10/689.268 | 2003-10-20 | ||
| PCT/US2004/034328 WO2005042653A1 (en) | 2003-10-20 | 2004-10-18 | Inkjet inks and methods of preparing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BRPI0415608A BRPI0415608A (pt) | 2006-12-05 |
| BRPI0415608B1 true BRPI0415608B1 (pt) | 2015-08-11 |
Family
ID=34521367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0415608-0A BRPI0415608B1 (pt) | 2003-10-20 | 2004-10-18 | Composição de tinta para inkjet e processo de preparação da mesma |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7300504B2 (enExample) |
| EP (1) | EP1694785B1 (enExample) |
| JP (1) | JP5021310B2 (enExample) |
| CN (2) | CN103351706B (enExample) |
| AT (1) | ATE431842T1 (enExample) |
| BR (1) | BRPI0415608B1 (enExample) |
| DE (1) | DE602004021197D1 (enExample) |
| TR (1) | TR200602600T1 (enExample) |
| WO (1) | WO2005042653A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2936655B2 (ja) | 1990-06-20 | 1999-08-23 | 大同特殊鋼株式会社 | 真空炉 |
| DE602005025919D1 (de) * | 2004-12-03 | 2011-02-24 | Canon Kk | Herstellungsverfahren für azopigmentdispersion |
| US7972428B2 (en) * | 2005-08-31 | 2011-07-05 | Cabot Corporation | Process for preparing modified pigments |
| WO2007053563A2 (en) * | 2005-10-31 | 2007-05-10 | Cabot Corporation | Modified colorants and inkjet ink compositions comprising modified colorants |
| US8133311B2 (en) * | 2007-04-30 | 2012-03-13 | Cabot Corporation | Pigment dipsersions comprising functionalized non-polymeric dispersants |
| JP2011515535A (ja) * | 2008-03-17 | 2011-05-19 | キャボット コーポレイション | リン酸塩遊離が低減した改質顔料、ならびにそれからの分散体およびインクジェットインク組成物 |
| US8048213B2 (en) * | 2009-04-06 | 2011-11-01 | Cabot Corporation | Inkjet ink compositions comprising azo pigments |
| CN106062087B (zh) | 2013-12-17 | 2019-03-12 | 卡博特公司 | 包括增效剂和聚合物涂层的颜料复合物 |
| CN105670340B (zh) * | 2016-01-14 | 2017-05-03 | 上虞市新利化工有限公司 | 一种c.i.颜料黄180的制备方法 |
| NL2018826B1 (en) | 2017-05-02 | 2018-11-09 | Spgprints B V | One-pot synthesis of reactive deep black |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH575447A5 (enExample) | 1970-03-14 | 1976-05-14 | Hoechst Ag | |
| 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 |
| DE2854974A1 (de) * | 1978-12-20 | 1980-07-10 | Hoechst Ag | Rekristallisationsstabile farbstarke monoazopigmentgemische, verfahren zu ihrer herstellung und ihre verwendung |
| US4334932A (en) * | 1980-04-23 | 1982-06-15 | Ciba-Geigy Corporation | Pigment formulations, processes for their preparation and their use for pigmenting aqueous, alcoholic or aqueous-alcoholic printing ink systems and colored lacquer systems |
| IN172052B (enExample) * | 1987-12-01 | 1993-03-27 | Hoechst Ag | |
| US5062894A (en) * | 1991-02-12 | 1991-11-05 | Sun Chemical Corporation | Poly (alkylene oxide)-modified diarylide pigment composition |
| US5145997A (en) * | 1991-02-12 | 1992-09-08 | Sun Chemical Corporation | Poly (alkylene oxide) substituted acetoacetanilides |
| US5246494A (en) * | 1991-07-23 | 1993-09-21 | Engelhard Corporation | Mixed coupled azo pigments |
| US5176745A (en) | 1991-12-11 | 1993-01-05 | Milliken Research Corporation | Aqueous ink composition and colorants useful therein |
| DE4229207C2 (de) * | 1992-09-02 | 1998-12-17 | Clariant Gmbh | Verfahren zur Herstellung von Disazopigmenten und deren Verwendung |
| CA2258189A1 (en) * | 1996-06-14 | 1997-12-18 | Cabot Corporation | Modified carbon adsorbents and processes for adsorption using the same |
| US5837045A (en) * | 1996-06-17 | 1998-11-17 | Cabot Corporation | Colored pigment and aqueous compositions containing same |
| JPH10279824A (ja) * | 1997-03-31 | 1998-10-20 | Nippon Kayaku Co Ltd | 水溶性ジスアゾ化合物、水性インク組成物および着色体 |
| JP3055673B2 (ja) * | 1997-12-12 | 2000-06-26 | 大日精化工業株式会社 | 画像記録用着色組成物 |
| DE69901944T3 (de) * | 1998-04-03 | 2009-05-14 | Cabot Corp., Boston | Modifizierte pigmente mit verbesserten dispergierenden eigenschaften |
| US6136087A (en) * | 1998-11-04 | 2000-10-24 | Uhlich Color Company, Inc. | Crystal growth inhibitor |
| AU1353401A (en) * | 1999-10-28 | 2001-05-08 | Cabot Corporation | Ink jet inks, inks, and other compositions containing colored pigments |
| GB2356866B (en) | 1999-11-30 | 2004-01-28 | Ilford Imaging Uk Ltd | Bis-azo compounds derived from diazotised sulphoanilines & 1,4-bis(acetoacetamido)phenylenes and their use in pigment and ink compositions |
| US6648954B2 (en) * | 2000-03-06 | 2003-11-18 | Toyo Ink Mfg. Co., Ltd. | Water-based pigment dispersion, use thereof and process for the production thereof |
| US6451103B1 (en) * | 2000-09-22 | 2002-09-17 | Toyo Ink Mfg. Co., Ltd. | Self-dispersible aqueous pigment dispersion |
| JP4452420B2 (ja) * | 2001-04-24 | 2010-04-21 | 富士フイルム株式会社 | 新規化合物 |
| JP2003165919A (ja) * | 2001-12-03 | 2003-06-10 | Toyo Ink Mfg Co Ltd | ピグメントイエロー７４および印刷インキ組成物 |
| CA2413341A1 (en) * | 2001-12-03 | 2003-06-03 | Toyo Ink. Mfg. Co., Ltd. | Pigment yellow 74 and printing ink composition |
| CN100575426C (zh) * | 2003-01-17 | 2009-12-30 | 卡伯特公司 | 含水有色颜料分散体的制备方法、及喷墨组合物 |
| KR101121277B1 (ko) | 2003-09-11 | 2012-04-26 | 디아이씨 가부시끼가이샤 | 잉크젯 잉크용 수성 안료 분산액 및 잉크젯 잉크 조성물 |
-
2003
- 2003-10-20 US US10/689,268 patent/US7300504B2/en not_active Expired - Lifetime
-
2004
- 2004-01-18 TR TR2006/02600T patent/TR200602600T1/xx unknown
- 2004-10-18 AT AT04795484T patent/ATE431842T1/de not_active IP Right Cessation
- 2004-10-18 EP EP04795484A patent/EP1694785B1/en not_active Expired - Lifetime
- 2004-10-18 CN CN201310316458.3A patent/CN103351706B/zh not_active Expired - Lifetime
- 2004-10-18 WO PCT/US2004/034328 patent/WO2005042653A1/en not_active Ceased
- 2004-10-18 DE DE602004021197T patent/DE602004021197D1/de not_active Expired - Lifetime
- 2004-10-18 JP JP2006535400A patent/JP5021310B2/ja not_active Expired - Lifetime
- 2004-10-18 BR BRPI0415608-0A patent/BRPI0415608B1/pt not_active IP Right Cessation
- 2004-10-18 CN CNA2004800368164A patent/CN1890331A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1694785B1 (en) | 2009-05-20 |
| ATE431842T1 (de) | 2009-06-15 |
| DE602004021197D1 (de) | 2009-07-02 |
| CN1890331A (zh) | 2007-01-03 |
| US20050081749A1 (en) | 2005-04-21 |
| WO2005042653A1 (en) | 2005-05-12 |
| TR200602600T1 (tr) | 2006-10-26 |
| JP2007510762A (ja) | 2007-04-26 |
| EP1694785A1 (en) | 2006-08-30 |
| BRPI0415608A (pt) | 2006-12-05 |
| JP5021310B2 (ja) | 2012-09-05 |
| CN103351706B (zh) | 2016-09-07 |
| CN103351706A (zh) | 2013-10-16 |
| US7300504B2 (en) | 2007-11-27 |
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