DE1231369B - Verfahren zur Herstellung von Anthrachinon-farbstoffen - Google Patents
Verfahren zur Herstellung von Anthrachinon-farbstoffenInfo
- Publication number
- DE1231369B DE1231369B DEB75728A DEB0075728A DE1231369B DE 1231369 B DE1231369 B DE 1231369B DE B75728 A DEB75728 A DE B75728A DE B0075728 A DEB0075728 A DE B0075728A DE 1231369 B DE1231369 B DE 1231369B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- groups
- general formula
- amino
- radicals
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 239000001000 anthraquinone dye Substances 0.000 title claims description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 16
- 239000000975 dye Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- -1 carbomethoxy Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000004753 textile Substances 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 125000000565 sulfonamide group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- 150000001412 amines Chemical class 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 2
- KGLUMSGAPDSZOL-UHFFFAOYSA-N 4,6-dichloro-5-phenyltriazine Chemical compound C1(=CC=CC=C1)C=1C(=NN=NC1Cl)Cl KGLUMSGAPDSZOL-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- LVRCEUVOXCJYSV-UHFFFAOYSA-N CN(C)S(=O)=O Chemical compound CN(C)S(=O)=O LVRCEUVOXCJYSV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CSMNJYQFVCFIKS-UHFFFAOYSA-N OCCN(S(=O)=O)CCO Chemical group OCCN(S(=O)=O)CCO CSMNJYQFVCFIKS-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/46—Dyes with acylated amino groups the acyl groups being residues of cyanuric acid or an analogous heterocyclic compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB75728A DE1231369B (de) | 1964-03-05 | 1964-03-05 | Verfahren zur Herstellung von Anthrachinon-farbstoffen |
| US435715A US3297695A (en) | 1964-03-05 | 1965-02-26 | Anthraquinone dyes and their production |
| CH291765A CH474556A (de) | 1964-03-05 | 1965-03-03 | Verfahren zur Herstellung neuer Anthrachinonfarbstoffe |
| BE660634D BE660634A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-03-05 | 1965-03-04 | |
| GB9238/65A GB1031270A (en) | 1964-03-05 | 1965-03-04 | New anthraquinone dyes and their production |
| FR8096A FR1426567A (fr) | 1964-03-05 | 1965-03-05 | Nouveaux colorants anthraquinoniques et procédé pour leur préparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB75728A DE1231369B (de) | 1964-03-05 | 1964-03-05 | Verfahren zur Herstellung von Anthrachinon-farbstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1231369B true DE1231369B (de) | 1966-12-29 |
Family
ID=6978775
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB75728A Pending DE1231369B (de) | 1964-03-05 | 1964-03-05 | Verfahren zur Herstellung von Anthrachinon-farbstoffen |
Country Status (6)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3509143A (en) * | 1958-12-22 | 1970-04-28 | American Cyanamid Co | Vat dyes from chlorocarbonyl aryl dichlorotriazines |
| IT1044082B (it) * | 1975-10-30 | 1980-03-20 | Acna | Procedimento di tintura di materiali fibrosi contenenti funzioni basiche da bagni di tintura a base di solventi organici |
| US4198205A (en) * | 1976-01-21 | 1980-04-15 | Basf Aktiengesellschaft | Triazinyl-anthraquinone dye formulations for cellulose or cellulosic fibrous material |
| DE2654434C3 (de) * | 1976-01-21 | 1981-01-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zum Färben und Bedrucken von Cellulose oder Cellulose enthaltendem Fasermaterial mit in Wasser unlöslichen Farbstoffen |
| DE3325276A1 (de) * | 1983-07-13 | 1985-01-24 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von phenyltriazinylamino-anthrachinonen |
| DE3921451C2 (de) * | 1989-06-30 | 1998-02-26 | Basf Ag | Verfahren zur Herstellung von Anthrachinonfarbstoffen |
| US5961711A (en) * | 1996-12-16 | 1999-10-05 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Pigment dispersant, pigment dispersion, and pigment dispersion for color filter |
| JP3625143B2 (ja) * | 1998-12-28 | 2005-03-02 | 大日精化工業株式会社 | 顔料の分散剤、顔料分散液及びカラーフイルター |
| IL134482A (en) | 1999-02-16 | 2002-12-01 | Dainichiseika Color Chem | Pigment dispersions and stationery and printers with the dispersions stored within them |
| WO2000078757A1 (en) * | 1999-06-17 | 2000-12-28 | Shionogi Bioresearch Corp. | Inhibitors of il-12 production |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB937978A (en) * | 1960-12-01 | 1963-09-25 | Ciba Ltd | New anthraquinone dyestuffs containing aminotriazinylamino groups and process for their manufacture |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB205525A (en) * | 1922-05-13 | 1923-10-15 | Chem Ind Basel | Manufacture of condensation products of the anthraquinone series |
| US3079389A (en) * | 1958-11-21 | 1963-02-26 | Ciba Ltd | Anthraquinone vat dyestuffs derived from 1-aminoanthraquinone-2-carboxylic esters |
-
1964
- 1964-03-05 DE DEB75728A patent/DE1231369B/de active Pending
-
1965
- 1965-02-26 US US435715A patent/US3297695A/en not_active Expired - Lifetime
- 1965-03-03 CH CH291765A patent/CH474556A/de not_active IP Right Cessation
- 1965-03-04 BE BE660634D patent/BE660634A/xx unknown
- 1965-03-04 GB GB9238/65A patent/GB1031270A/en not_active Expired
- 1965-03-05 FR FR8096A patent/FR1426567A/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB937978A (en) * | 1960-12-01 | 1963-09-25 | Ciba Ltd | New anthraquinone dyestuffs containing aminotriazinylamino groups and process for their manufacture |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1031270A (en) | 1966-06-02 |
| BE660634A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-09-06 |
| FR1426567A (fr) | 1966-01-28 |
| US3297695A (en) | 1967-01-10 |
| CH474556A (de) | 1969-06-30 |
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