DE3309726C1 - Verfahren zur Herstellung saurer,elektrolytarmer Farbstoffe der Triphenylmethan-Reihe - Google Patents
Verfahren zur Herstellung saurer,elektrolytarmer Farbstoffe der Triphenylmethan-ReiheInfo
- Publication number
- DE3309726C1 DE3309726C1 DE3309726A DE3309726A DE3309726C1 DE 3309726 C1 DE3309726 C1 DE 3309726C1 DE 3309726 A DE3309726 A DE 3309726A DE 3309726 A DE3309726 A DE 3309726A DE 3309726 C1 DE3309726 C1 DE 3309726C1
- Authority
- DE
- Germany
- Prior art keywords
- sulfonaphthyl
- group
- disulfonaphthyl
- dyes
- solution
- 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
- 239000000975 dye Substances 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 6
- 239000003792 electrolyte Substances 0.000 title claims description 5
- 230000002378 acidificating effect Effects 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000004961 triphenylmethanes Chemical class 0.000 title description 2
- -1 sulfobenzyl group Chemical group 0.000 claims description 44
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 11
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 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 description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 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
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002002 slurry Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 6
- 239000007900 aqueous suspension Substances 0.000 description 5
- JLUGKDWGQPNDGX-UHFFFAOYSA-L azanium;manganese(2+);phosphate Chemical compound [NH4+].[Mn+2].[O-]P([O-])([O-])=O JLUGKDWGQPNDGX-UHFFFAOYSA-L 0.000 description 5
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 5
- 239000000920 calcium hydroxide Substances 0.000 description 5
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 210000002268 wool Anatomy 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000001046 green dye Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 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
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
- UDPWNJVGOHGQFG-UHFFFAOYSA-N azane;phosphoric acid Chemical compound [NH4+].OP(O)(O)=O.OP(O)([O-])=O UDPWNJVGOHGQFG-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 239000008395 clarifying agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000010626 work up procedure 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
-
- 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3309726A DE3309726C1 (de) | 1983-03-18 | 1983-03-18 | Verfahren zur Herstellung saurer,elektrolytarmer Farbstoffe der Triphenylmethan-Reihe |
| EP84102719A EP0120399B1 (de) | 1983-03-18 | 1984-03-13 | Verfahren zur Herstellung saurer, elektrolytarmer Farbstoffe der Triphenylmethan-Reihe |
| US06/589,883 US4566999A (en) | 1983-03-18 | 1984-03-15 | Process for the preparation of acid dyestuffs of low electrolyte content of the triphenylmethane series |
| JP59049358A JPS59179562A (ja) | 1983-03-18 | 1984-03-16 | 電解質に乏しいトリフェニルメタン系酸性染料の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3309726A DE3309726C1 (de) | 1983-03-18 | 1983-03-18 | Verfahren zur Herstellung saurer,elektrolytarmer Farbstoffe der Triphenylmethan-Reihe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3309726C1 true DE3309726C1 (de) | 1984-09-20 |
Family
ID=6193848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3309726A Expired DE3309726C1 (de) | 1983-03-18 | 1983-03-18 | Verfahren zur Herstellung saurer,elektrolytarmer Farbstoffe der Triphenylmethan-Reihe |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4566999A (enExample) |
| EP (1) | EP0120399B1 (enExample) |
| JP (1) | JPS59179562A (enExample) |
| DE (1) | DE3309726C1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4536367A (en) * | 1983-12-09 | 1985-08-20 | The Hilton-Davis Chemical Co. | Method for sanitizing toilets |
| JPS62296A (ja) * | 1985-06-26 | 1987-01-06 | Kyowa Medetsukusu Kk | 過酸化水素の定量方法 |
| US5198558A (en) * | 1990-12-18 | 1993-03-30 | Basf Corporation | Process for the preparation of triphenylmethane dyes |
| JP4744029B2 (ja) * | 2001-07-31 | 2011-08-10 | 三菱鉛筆株式会社 | 油性インキ組成物及びその用途 |
| US7834213B2 (en) * | 2005-02-15 | 2010-11-16 | Canon Kabushiki Kaisha | Colorant compound and method of manufacturing the same as well as blue resist composition for use in color filter containing the same |
| CN102040853B (zh) * | 2010-11-30 | 2013-07-10 | 上海染料研究所有限公司 | 一种三芳甲烷型食用染料的制备方法 |
| JP6350245B2 (ja) * | 2014-02-10 | 2018-07-04 | 三菱ケミカル株式会社 | 着色樹脂組成物、カラーフィルタ、液晶表示装置及び有機ｅｌ表示装置 |
| CN104327533A (zh) * | 2014-09-04 | 2015-02-04 | 恒升化工有限公司 | 一种酸性蓝9号染料的清洁生产工艺 |
| CN105348846B (zh) * | 2015-09-25 | 2017-07-11 | 恒升化工有限公司 | 一种低盐含量酸性蓝9号染料的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US331964A (en) * | 1885-12-08 | Hugo hassencamp | ||
| US353266A (en) * | 1886-11-23 | Gael ludwig mullee | ||
| US353264A (en) * | 1886-11-23 | Gael ludwig mullee | ||
| DE609704C (de) * | 1931-06-07 | 1935-02-26 | I G Farbenindustrie Akt Ges | Verfahren zur Erzeugung leicht loeslicher basischer Farbstoffe |
| US2192118A (en) * | 1938-03-23 | 1940-02-27 | Gen Aniline & Film Corp | Acid diamino-trjphenyl-methane dyestuffs |
| US2337425A (en) * | 1941-10-21 | 1943-12-21 | Du Pont | Manufacture of triamino-diphenylnaphthyl-methane dyestuffs |
| US2555603A (en) * | 1946-12-20 | 1951-06-05 | Allied Chem & Dye Corp | Amino-cyclohexylcyclohexane salts of dyestuff acids |
| US2542544A (en) * | 1948-06-14 | 1951-02-20 | American Cyanamid Co | Process of producing polyaryl methane dyes of the rosaniline type |
| US2567965A (en) * | 1948-11-12 | 1951-09-18 | Sterling Drug Inc | Blue printing ink |
| US2755420A (en) * | 1954-01-08 | 1956-07-17 | Du Pont | Transfer inks for duplication processes |
| DE2555747A1 (de) * | 1975-12-11 | 1977-06-16 | Bayer Ag | Verfahren zur gewinnung von triarylmethanfarbstoffen |
-
1983
- 1983-03-18 DE DE3309726A patent/DE3309726C1/de not_active Expired
-
1984
- 1984-03-13 EP EP84102719A patent/EP0120399B1/de not_active Expired
- 1984-03-15 US US06/589,883 patent/US4566999A/en not_active Expired - Fee Related
- 1984-03-16 JP JP59049358A patent/JPS59179562A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| Beyer, H.: Lehrbuch der organischen Chemie, Leipzig 1967, 13./14. Aufl., S. 518 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0449874B2 (enExample) | 1992-08-12 |
| JPS59179562A (ja) | 1984-10-12 |
| EP0120399B1 (de) | 1989-05-24 |
| EP0120399A2 (de) | 1984-10-03 |
| US4566999A (en) | 1986-01-28 |
| EP0120399A3 (en) | 1987-03-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8100 | Publication of the examined application without publication of unexamined application | ||
| D1 | Grant (no unexamined application published) patent law 81 | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: CASSELLA AG, 6000 FRANKFURT, DE |
|
| 8339 | Ceased/non-payment of the annual fee |