JPS6360793B2 - - Google Patents
Info
- Publication number
- JPS6360793B2 JPS6360793B2 JP55145088A JP14508880A JPS6360793B2 JP S6360793 B2 JPS6360793 B2 JP S6360793B2 JP 55145088 A JP55145088 A JP 55145088A JP 14508880 A JP14508880 A JP 14508880A JP S6360793 B2 JPS6360793 B2 JP S6360793B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- formula
- acid
- dye
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000975 dye Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- MNFZZNNFORDXSV-UHFFFAOYSA-N 4-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C=C1 MNFZZNNFORDXSV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 1
- DGPBVJWCIDNDPN-UHFFFAOYSA-N 2-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=CC=C1C=O DGPBVJWCIDNDPN-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- GZOXYNSFPWUMOH-UHFFFAOYSA-M benzyl-bis(2-hydroxyethyl)-methylazanium;chloride Chemical compound [Cl-].OCC[N+](C)(CCO)CC1=CC=CC=C1 GZOXYNSFPWUMOH-UHFFFAOYSA-M 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- CBMCXBOWQHAKJX-UHFFFAOYSA-M diethyl-bis(2-hydroxyethyl)azanium;chloride Chemical compound [Cl-].OCC[N+](CC)(CC)CCO CBMCXBOWQHAKJX-UHFFFAOYSA-M 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 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 1
- 239000011541 reaction mixture Substances 0.000 description 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000001043 yellow dye Substances 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
-
- 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
- Y10S8/916—Natural fiber dyeing
- Y10S8/919—Paper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792942185 DE2942185A1 (de) | 1979-10-18 | 1979-10-18 | Basische farbstoffe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5665048A JPS5665048A (en) | 1981-06-02 |
| JPS6360793B2 true JPS6360793B2 (en:Method) | 1988-11-25 |
Family
ID=6083803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14508880A Granted JPS5665048A (en) | 1979-10-18 | 1980-10-18 | Basic dye |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US4597912A (en:Method) |
| EP (1) | EP0027611B1 (en:Method) |
| JP (1) | JPS5665048A (en:Method) |
| CA (1) | CA1133923A (en:Method) |
| DE (2) | DE2942185A1 (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0433755U (en:Method) * | 1990-07-12 | 1992-03-19 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2942185A1 (de) * | 1979-10-18 | 1981-04-30 | Basf Ag, 6700 Ludwigshafen | Basische farbstoffe |
| DE19524134A1 (de) * | 1995-07-03 | 1997-01-09 | Bayer Ag | Verfahren zum Reduzieren der Toxizität von Restflotten und neue kationische Farbstoffe |
| BR112012013810B1 (pt) * | 2009-12-10 | 2022-01-11 | The Regents Of The Universirty Of California | Compostos agentes de ligação a amiloide, composição farmacêutica que os compreende e seus usos |
| WO2012039286A1 (ja) * | 2010-09-22 | 2012-03-29 | 株式会社Adeka | 染料及び着色感光性組成物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE794010A (fr) * | 1972-01-13 | 1973-05-02 | Du Pont | Colorants cationiques de couleur jaune-vert |
| US4063882A (en) * | 1976-04-15 | 1977-12-20 | E. I. Du Pont De Nemours And Company | Storage-stable quaternary styryl dye solutions |
| US4017486A (en) * | 1976-05-18 | 1977-04-12 | American Cyanamid Company | Cationic alpha-cyano-p-dimethylaminocinnamoyl dyes and paper dyed therewith |
| DE2747365A1 (de) * | 1976-11-01 | 1978-05-11 | American Cyanamid Co | Fluessige papierfaerbemittel |
| DE2754403A1 (de) * | 1977-12-07 | 1979-06-13 | Basf Ag | Methinfarbstoffe |
| DE2826981C2 (de) * | 1978-06-20 | 1987-04-09 | Basf Ag, 6700 Ludwigshafen | Basische Farbstoffe |
| US4235806A (en) * | 1979-04-05 | 1980-11-25 | American Color & Chemical Corporation | Cationic α-cyano-p-(N-benzyl-N-ethylamino)cinnamoyl dyes |
| DE2942185A1 (de) * | 1979-10-18 | 1981-04-30 | Basf Ag, 6700 Ludwigshafen | Basische farbstoffe |
-
1979
- 1979-10-18 DE DE19792942185 patent/DE2942185A1/de not_active Withdrawn
-
1980
- 1980-09-19 CA CA360,590A patent/CA1133923A/en not_active Expired
- 1980-10-10 DE DE8080106163T patent/DE3063360D1/de not_active Expired
- 1980-10-10 EP EP80106163A patent/EP0027611B1/de not_active Expired
- 1980-10-18 JP JP14508880A patent/JPS5665048A/ja active Granted
-
1985
- 1985-05-17 US US06/735,298 patent/US4597912A/en not_active Expired - Lifetime
-
1986
- 1986-02-07 US US06/826,987 patent/US4720568A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0433755U (en:Method) * | 1990-07-12 | 1992-03-19 |
Also Published As
| Publication number | Publication date |
|---|---|
| US4597912A (en) | 1986-07-01 |
| DE3063360D1 (en) | 1983-07-07 |
| EP0027611A3 (en) | 1981-05-06 |
| JPS5665048A (en) | 1981-06-02 |
| CA1133923A (en) | 1982-10-19 |
| DE2942185A1 (de) | 1981-04-30 |
| EP0027611B1 (de) | 1983-05-18 |
| EP0027611A2 (de) | 1981-04-29 |
| US4720568A (en) | 1988-01-19 |
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