JP5080984B2 - 有機溶媒に可溶性である染料 - Google Patents
有機溶媒に可溶性である染料 Download PDFInfo
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- JP5080984B2 JP5080984B2 JP2007548802A JP2007548802A JP5080984B2 JP 5080984 B2 JP5080984 B2 JP 5080984B2 JP 2007548802 A JP2007548802 A JP 2007548802A JP 2007548802 A JP2007548802 A JP 2007548802A JP 5080984 B2 JP5080984 B2 JP 5080984B2
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- formula
- printing
- dye
- weight
- dyes
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- 238000007639 printing Methods 0.000 claims abstract description 39
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- 239000003086 colorant Substances 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 150000002892 organic cations Chemical class 0.000 claims abstract description 6
- 239000000123 paper Substances 0.000 claims description 24
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- 239000011888 foil Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000002657 fibrous material Substances 0.000 claims description 8
- 230000002209 hydrophobic effect Effects 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 4
- 238000004043 dyeing Methods 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
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- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000305 astragalus gummifer gum Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229920003087 methylethyl cellulose Polymers 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 229940057847 polyethylene glycol 600 Drugs 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000012192 staining solution Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
- C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/3656—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing amino-1,2-diazoles
-
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
- C09B69/045—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds of anionic azo dyes
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/922—Polyester fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Coloring (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
で示される染料に関するものである。
である。
ジアゾ化
スルホン化フラスコ内で、2−スルホ−4−ニトロアニリンのナトリウム/アンモニウム塩(86%)10.94gを、脱塩水160ml中に撹拌しつつ加え、次いで、37%塩酸14mlを加えた。次いで、氷浴を用いて、0〜5℃への冷却を実施し、4M硝酸ナトリウム10mlを、15分間にわたって加えた。混合物を、更に15分間撹拌した。過剰な硝酸ナトリウムを、1Mアミノスルホン酸を用いて破壊した。
脱塩水550mlを、初期投入量としてガラスビーカーに導入した。その中に、アミノ−3−メチルフェニルピラゾール(97%)7.14gを懸濁させた。ベージュ色の懸濁液を、60℃に加熱し、約7.1のpH値を、1N塩酸10mlを用いて4.0に調整した。次いで、溶液を、750ml入りスルホン化フラスコに移し、約5℃に冷却した。次いで、ジアゾ懸濁液を、仕込みビーカーを用いて、カプラー溶液に2時間にわたって加え、その間、pH値を、水酸化ナトリウム溶液(30%)14.3mlを用いて4.5に保った。温度は、5℃の範囲内のままであった。橙赤色の懸濁液が得られて、次いで約1時間、更に撹拌した。次いで、塩化ナトリウム(10%)200mlを加え、撹拌を、更に12時間実施した。次いで、懸濁液を濾過し、次いで20%塩化ナトリウム溶液100mlで洗浄した。フィルターケーキを、真空キャビネット内で、70℃で12時間乾燥した。式(50)の化合物27.7gを含有する未精製生成物を得た:
ジアゾ化
反応フラスコ内で、2−スルホ−4−ニトロアニリン(85.5%)46.8gを、脱塩水800ml中に撹拌しつつ加え、次いで、37%塩酸5mlを加えた。次いで、氷浴を用いて、0〜5℃への冷却を実施し、4M硝酸ナトリウム45mlを、少量(約2ml)の塩酸を同時に加えつつ、40分間にわたって加えた。混合物を、更に45分間撹拌した。過剰な硝酸ナトリウムを、1Mアミノスルホン酸を用いて破壊した。
脱塩水100mlおよび2−エトキシエタノール(エチルセロソルブ/エチレングリコールモノエチルエーテル)150mlを、初期投入量としてガラスビーカーに導入した。その中に、アミノ−3−メチルフェニルピラゾール(97%)30.3gを溶解した。次いで、30%水酸化ナトリウム溶液2滴を加え、混合物を、45分間撹拌した。次いで、カプラー溶液を、氷冷ジアゾニウム溶液に30分間にわたって加え、その間、pH値を、炭酸水素ナトリウムの添加によって2.8〜3.8に保った。粘稠な橙赤色の懸濁液が得られて、脱塩水合計500mlで希釈した。次いで、希釈された懸濁液のpH値を、炭酸水素ナトリウムを用いて6.0に調整し、懸濁液を、更に90分間撹拌し、濾過し、次いで12%塩化ナトリウム溶液400mlで洗浄した。フィルターケーキを、減圧下、70℃で12時間乾燥した。式(50)の化合物94.7gを含有する未精製生成物を得た。
脱塩水620mlを、初期投入量として四つ口スルホン化フラスコに導入した。式(50)の化合物(含量53%)10gをこれに加えた。懸濁液を78℃に加熱し、水酸化ナトリウム溶液(30%)を用いて、pH7.0に調整したところ、溶液になった。次いで、イソブチルメチルケトン500mlおよび臭化テトラブチルアンモニウム(98%)4gを逐次加えた。生成物は、有機相に移動した。次いで、ギ酸(100%)を用いて、pH値を3.5に調整し、その後15〜20分間撹拌した。有機相を、分液漏斗内で分離し、ロータリーエバポレーターを用いて、完全に濃縮した。式(100):
3.0重量%の式(100):
3.0重量%の式(100)の染料を97.0重量%の配合物(14.0重量%のビニライトVYHM(UCC)[塩化ビニル/酢酸ビニル共重合体(85%/15%)]、10.0重量%のエトキシプロパノール、および76.0重量%のMEK[メチルエチルケトン]からなる)に、均質になるまで撹拌しつつ加えた。
3.0重量%の式(101)の染料を97.0重量%の配合物(12.0重量%のNC AH 27(20%ATBC)[ニトロセルロース、エタノールに可溶、20重量%のアセチルトリブチルシトラートを含有]、2.0重量%のHercolyn DE[撥水剤]、10.0重量%のエトキシプロパノール、20.0重量%の酢酸エチル、および56.0重量%のエタノールからなる)に、均質になるまで撹拌しつつ加えた。
3.0重量%の式(100)の染料を97.0重量%の配合物(11.0重量%のニトロセルロースA400、9.0重量%のDowanol PM(A)(酢酸メトキシプロピル)、20.0重量%の酢酸エチル、および60.0重量%のエチルアルコールからなる)に、均質になるまで撹拌しつつ加えた。
3.0重量%の式(101)の染料を97.0重量%の配合物(6.5重量%のMovital B20H(塩化ビニル/酢酸ビニル共重合体)、1.5重量%のForalyn 5020−F(光沢向上のための添加剤)、30.0重量%のエトキシプロパノール、40.0重量%のDowanol PM(A)(酢酸メトキシプロピル)、および22.0重量%のジアセトンアルコールからなる)に、均質になるまで撹拌しつつ加えた。
3.0重量部の式(100)のアゾ染料、40.0重量部のエチルアルコール、40.0重量部の1−メトキシ−2−プロパノール、および17.0重量部のイソプロパノール。
Claims (9)
- 請求項1又は2に記載の式(1)の染料を含むプリント用着色剤、プリント用ペースト、またはプリント用インク。
- 半合成または合成疎水性繊維材料を浸染もしくはプリントする方法であって、請求項1又は2に記載の式(1)の染料1種類またはそれ以上を、該材料に塗布もしくは混和する工程を含む方法。
- 紙、プラスチックフィルムまたは金属箔に着色もしくはプリントする方法であって、請求項1又は2に記載の式(1)の染料1種類またはそれ以上を、該材料に塗布もしくは混和する工程を含む方法。
- 請求項1又は2に記載の式(1)の染料の使用であって、半合成もしくは合成疎水性繊維材料、紙、プラスチックフィルムまたは金属箔の着色もしくはプリントの際の使用。
- 請求項5又は6に記載の方法あるいは請求項7に記載の使用により着色またはプリントされた材料。
- インクジェットプリンターにおける請求項4記載のプリント用インクの使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04107037.6 | 2004-12-29 | ||
EP04107037 | 2004-12-29 | ||
PCT/EP2005/056891 WO2006069928A2 (en) | 2004-12-29 | 2005-12-19 | Dyes that are soluble in organic solvents |
Publications (3)
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JP2008525605A JP2008525605A (ja) | 2008-07-17 |
JP2008525605A5 JP2008525605A5 (ja) | 2012-07-12 |
JP5080984B2 true JP5080984B2 (ja) | 2012-11-21 |
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Family Applications (1)
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JP2007548802A Expired - Fee Related JP5080984B2 (ja) | 2004-12-29 | 2005-12-19 | 有機溶媒に可溶性である染料 |
Country Status (7)
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US (1) | US7470780B2 (ja) |
EP (1) | EP1831315B1 (ja) |
JP (1) | JP5080984B2 (ja) |
AT (1) | ATE518920T1 (ja) |
ES (1) | ES2367650T3 (ja) |
TW (1) | TWI388633B (ja) |
WO (1) | WO2006069928A2 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2008007652A (ja) * | 2006-06-29 | 2008-01-17 | Fujifilm Corp | アゾ色素、感熱転写記録用インクシート、感熱転写記録方法、カラートナー、インクジェット用インクおよびカラーフィルタ |
US20080184910A1 (en) * | 2007-02-06 | 2008-08-07 | Xerox Corporation | Colorant compounds |
FR2990852A1 (fr) * | 2012-05-24 | 2013-11-29 | Oreal | Colorant ou azurant anionique a contre ion ammonium ou phosphonium, composition de teinture les comprenant et procede de coloration des fibres keratiniques a partir de ces colorants |
FR3090345B1 (fr) * | 2018-12-21 | 2021-06-25 | Oreal | Procédé de coloration des matières kératiniques mettant en œuvre un colorant direct et un sel ammonium aliphatique et composition les comprenant |
Family Cites Families (23)
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GB791443A (en) * | 1955-10-26 | 1958-03-05 | Ici Ltd | New disazo dyestuffs derived from bis-aminopyrazoles |
CH373842A (de) * | 1959-09-11 | 1963-12-15 | Geigy Ag J R | Verfahren zur Herstellung von in Wasser dispergierbaren, schwer löslichen Azofarbstoffen |
CH419388A (de) * | 1962-08-02 | 1966-08-31 | Geigy Ag J R | Verfahren zur Herstellung von in Wasser schwerlöslichen Azofarbstoffen |
DE1644165A1 (de) * | 1966-07-09 | 1971-02-18 | Hoechst Ag | Basische Azofarbstoffe und Verfahren zu ihrer Herstellung |
CH504511A (de) * | 1968-04-24 | 1971-03-15 | Ciba Geigy Ag | Verfahren zur Herstellung von Disazofarbstoffen |
CH535816A (de) * | 1970-07-08 | 1973-04-15 | Ciba Geigy Ag | Verfahren zur Herstellung neuer Azofarbstoffe |
US3803122A (en) * | 1971-02-19 | 1974-04-09 | Du Pont | Green-yellow monoazo acid dyes |
US3994872A (en) * | 1971-08-10 | 1976-11-30 | Ciba-Geigy Corporation | Tertiary-alkylamine salts of metal complex dyestuffs |
NL173862C (nl) * | 1971-08-10 | 1984-03-16 | Ciba Geigy | Werkwijze ter bereiding van ammoniumzouten van anionogene kleurstoffen. |
US4043752A (en) * | 1975-12-17 | 1977-08-23 | E. I. Du Pont De Nemours And Company | Phenylazoaminophenylpyrazole acid dye solutions containing two nonionic surfactants |
CH638239A5 (en) * | 1978-11-07 | 1983-09-15 | Ciba Geigy Ag | Aqueous preparations of dyes that are insoluble to sparingly soluble in water |
JPS6050393B2 (ja) * | 1980-06-13 | 1985-11-08 | 富士写真フイルム株式会社 | 水性インキ組成物 |
DE3416327A1 (de) * | 1984-05-03 | 1985-11-07 | Basf Ag, 6700 Ludwigshafen | Farbsalze sulfonsaeuregruppenhaltiger polyazofarbstoffe |
DE3417237A1 (de) * | 1984-05-10 | 1985-11-14 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von nickel-komplexfarbstoffen |
DE3417537A1 (de) * | 1984-05-11 | 1985-11-14 | Knorr-Bremse GmbH, 8000 München | Positioniervorrichtung fuer einen druckmittelbeaufschlagbaren zylinder |
JPH0794182B2 (ja) * | 1988-03-04 | 1995-10-11 | 富士写真フイルム株式会社 | 感熱転写材料 |
US5034371A (en) | 1989-03-27 | 1991-07-23 | Fuji Photo Film Co., Ltd. | Thermal transfer image recording method and thermal transfer dye donating material |
JP2652071B2 (ja) * | 1990-01-25 | 1997-09-10 | 日本化薬株式会社 | カラーフィルター |
JPH0699667A (ja) * | 1992-09-22 | 1994-04-12 | Fuji Photo Film Co Ltd | 熱転写色素供与材料 |
DE4339270A1 (de) * | 1993-11-18 | 1995-05-24 | Basf Ag | Azofarbstoffe mit einer Diazokomponente aus der Reihe der Aminobenzisothiazole |
JPH0848082A (ja) * | 1994-08-05 | 1996-02-20 | Mitsubishi Chem Corp | 感熱転写シート |
US6866706B2 (en) * | 2001-11-05 | 2005-03-15 | Mitsubishi Chemical Corporation | Ink for thermal transfer, sheet for thermal transfer, and thermal transfer recording method using the same |
CN1720298A (zh) * | 2002-12-05 | 2006-01-11 | 西巴特殊化学品控股有限公司 | 基于苯并咪唑-吡啶酮的偶氮染料 |
-
2005
- 2005-12-19 AT AT05825277T patent/ATE518920T1/de not_active IP Right Cessation
- 2005-12-19 JP JP2007548802A patent/JP5080984B2/ja not_active Expired - Fee Related
- 2005-12-19 US US11/794,131 patent/US7470780B2/en not_active Expired - Fee Related
- 2005-12-19 WO PCT/EP2005/056891 patent/WO2006069928A2/en active Application Filing
- 2005-12-19 ES ES05825277T patent/ES2367650T3/es active Active
- 2005-12-19 EP EP05825277A patent/EP1831315B1/en not_active Not-in-force
- 2005-12-28 TW TW094146994A patent/TWI388633B/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
ATE518920T1 (de) | 2011-08-15 |
TW200630440A (en) | 2006-09-01 |
JP2008525605A (ja) | 2008-07-17 |
WO2006069928A2 (en) | 2006-07-06 |
US7470780B2 (en) | 2008-12-30 |
ES2367650T3 (es) | 2011-11-07 |
WO2006069928A3 (en) | 2006-11-30 |
TWI388633B (zh) | 2013-03-11 |
US20080103313A1 (en) | 2008-05-01 |
EP1831315B1 (en) | 2011-08-03 |
EP1831315A2 (en) | 2007-09-12 |
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