DE3133391A1 - Kationische farbstoffe - Google Patents
Kationische farbstoffeInfo
- Publication number
- DE3133391A1 DE3133391A1 DE19813133391 DE3133391A DE3133391A1 DE 3133391 A1 DE3133391 A1 DE 3133391A1 DE 19813133391 DE19813133391 DE 19813133391 DE 3133391 A DE3133391 A DE 3133391A DE 3133391 A1 DE3133391 A1 DE 3133391A1
- Authority
- DE
- Germany
- Prior art keywords
- dye
- dyes
- parts
- alkyl
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000000975 dye Substances 0.000 title claims description 57
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000002091 cationic group Chemical group 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000001018 xanthene dye Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 claims description 3
- -1 2-ethyl Chemical group 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 150000004961 triphenylmethanes Chemical class 0.000 claims description 2
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 230000000740 bleeding effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UUQQGGWZVKUCBD-UHFFFAOYSA-N [4-(hydroxymethyl)-2-phenyl-1h-imidazol-5-yl]methanol Chemical compound N1C(CO)=C(CO)N=C1C1=CC=CC=C1 UUQQGGWZVKUCBD-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000000992 solvent dye Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 1
- UQOCEEQQGFOLRM-UHFFFAOYSA-N 2-methylideneimidazole Chemical group C=C1N=CC=N1 UQOCEEQQGFOLRM-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- BJRHJSBSDMOLTA-UHFFFAOYSA-N [3-(hydroxymethyl)-2-phenylimidazol-4-yl]methanol Chemical compound OCN1C(CO)=CN=C1C1=CC=CC=C1 BJRHJSBSDMOLTA-UHFFFAOYSA-N 0.000 description 1
- CIZIDJCTTRZYBO-UHFFFAOYSA-N [4-(hydroxymethyl)-2-methyl-1h-imidazol-5-yl]methanol Chemical compound CC1=NC(CO)=C(CO)N1 CIZIDJCTTRZYBO-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- JMCKWTQLJNQCTD-UHFFFAOYSA-N spirit blue Chemical compound Cl.C=1C=C(C(=C2C=CC(C=C2)=NC=2C=CC=CC=2)C=2C=CC(NC=3C=CC=CC=3)=CC=2)C=CC=1NC1=CC=CC=C1 JMCKWTQLJNQCTD-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- C09B25/00—Quinophthalones
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Coloring (AREA)
- Luminescent Compositions (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813133391 DE3133391A1 (de) | 1981-08-24 | 1981-08-24 | Kationische farbstoffe |
| US06/407,892 US4472581A (en) | 1981-08-24 | 1982-08-13 | Imidazomethylene dyes |
| JP57141778A JPS5838763A (ja) | 1981-08-24 | 1982-08-17 | カチオン性染料 |
| EP82107503A EP0073008B1 (de) | 1981-08-24 | 1982-08-18 | Kationische Farbstoffe |
| DE8282107503T DE3261203D1 (en) | 1981-08-24 | 1982-08-18 | Cationic dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813133391 DE3133391A1 (de) | 1981-08-24 | 1981-08-24 | Kationische farbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3133391A1 true DE3133391A1 (de) | 1983-03-10 |
Family
ID=6139973
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813133391 Withdrawn DE3133391A1 (de) | 1981-08-24 | 1981-08-24 | Kationische farbstoffe |
| DE8282107503T Expired DE3261203D1 (en) | 1981-08-24 | 1982-08-18 | Cationic dyestuffs |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8282107503T Expired DE3261203D1 (en) | 1981-08-24 | 1982-08-18 | Cationic dyestuffs |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4472581A (enExample) |
| EP (1) | EP0073008B1 (enExample) |
| JP (1) | JPS5838763A (enExample) |
| DE (2) | DE3133391A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0335237A3 (de) * | 1988-03-31 | 1991-03-06 | BASF Aktiengesellschaft | Tinten für Ink-Jet-Aufzeichnungsverfahren |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5212312A (en) * | 1980-12-23 | 1993-05-18 | Ciba-Geigy Ag | Vattable and non-vattable quinoid dyes |
| US20080210590A1 (en) * | 2006-01-23 | 2008-09-04 | Cieri Christopher W | Golf club cleaning device and associated storage device |
| US7841037B2 (en) * | 2006-01-23 | 2010-11-30 | Exsite Golf, Inc. | Golf club cleaning device |
| US7904986B2 (en) * | 2006-01-23 | 2011-03-15 | Exsite Golf, Inc. | Golf club cleaning device |
| US20080237087A1 (en) * | 2006-01-23 | 2008-10-02 | Cieri Christopher W | Golf club cleaning device and associated storage device |
| US8393041B2 (en) * | 2008-05-13 | 2013-03-12 | Exsite Golf, Inc. | Golf club cleaning device |
| JP6255482B2 (ja) * | 2014-03-27 | 2017-12-27 | 富士フイルム株式会社 | 化合物、着色組成物、インクジェット記録用インク、インクジェット記録方法、インクジェットプリンタカートリッジ、インクジェット記録物、カラーフィルタ、カラートナー、及び転写用インク |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1266898B (de) * | 1961-04-15 | 1968-04-25 | Basf Ag | Verfahren zur Herstellung von Farbstoffen der Azo-, Anthrachinon- und Phthalocyaninreihe |
| US3592806A (en) * | 1966-12-19 | 1971-07-13 | Hodogaya Chemical Co Ltd | Basic azo dyestuffs containing a quaternized n-alkyl-n - beta-(imidazolyl) lower alkylarylamine group |
| DE2046785A1 (en) * | 1970-09-23 | 1972-03-30 | Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen | Basic mono-azo dyes - for synthetic fibres, cotton silk, leather, paper and paints |
| GB1404595A (en) * | 1972-04-13 | 1975-09-03 | Ici Ltd | Water-sobuble quinophthalone dyes |
| DE3006013A1 (de) * | 1980-02-18 | 1981-08-20 | Basf Ag, 6700 Ludwigshafen | Imidazolylemethylengruppen enthaltende farbstoffe und deren verwendung |
-
1981
- 1981-08-24 DE DE19813133391 patent/DE3133391A1/de not_active Withdrawn
-
1982
- 1982-08-13 US US06/407,892 patent/US4472581A/en not_active Expired - Lifetime
- 1982-08-17 JP JP57141778A patent/JPS5838763A/ja active Granted
- 1982-08-18 DE DE8282107503T patent/DE3261203D1/de not_active Expired
- 1982-08-18 EP EP82107503A patent/EP0073008B1/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0335237A3 (de) * | 1988-03-31 | 1991-03-06 | BASF Aktiengesellschaft | Tinten für Ink-Jet-Aufzeichnungsverfahren |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0073008A3 (en) | 1983-05-25 |
| EP0073008A2 (de) | 1983-03-02 |
| US4472581A (en) | 1984-09-18 |
| DE3261203D1 (en) | 1984-12-13 |
| JPH044345B2 (enExample) | 1992-01-28 |
| JPS5838763A (ja) | 1983-03-07 |
| EP0073008B1 (de) | 1984-11-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |