DE2500237C2 - Anthrachinoide dispersionsfarbstoffe, deren herstellung und deren verwendung - Google Patents
Anthrachinoide dispersionsfarbstoffe, deren herstellung und deren verwendungInfo
- Publication number
- DE2500237C2 DE2500237C2 DE19752500237 DE2500237A DE2500237C2 DE 2500237 C2 DE2500237 C2 DE 2500237C2 DE 19752500237 DE19752500237 DE 19752500237 DE 2500237 A DE2500237 A DE 2500237A DE 2500237 C2 DE2500237 C2 DE 2500237C2
- Authority
- DE
- Germany
- Prior art keywords
- hydroxy
- parts
- nitroanthraquinone
- alkylamino
- halogenation
- 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
- 239000003086 colorant Substances 0.000 title 1
- 239000006185 dispersion Substances 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 230000026030 halogenation Effects 0.000 claims description 8
- 238000005658 halogenation reaction Methods 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000012209 synthetic fiber Substances 0.000 claims description 2
- 229920002994 synthetic fiber Polymers 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- -1 ethylamino- Chemical class 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000002140 halogenating effect Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000009998 heat setting Methods 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- UVFJFPGRSPOHNB-UHFFFAOYSA-N 1,4-diamino-5-hydroxy-8-nitroanthracene-9,10-dione Chemical compound O=C1C(C(=CC=C2O)[N+]([O-])=O)=C2C(=O)C2=C1C(N)=CC=C2N UVFJFPGRSPOHNB-UHFFFAOYSA-N 0.000 description 1
- DPCKWQVALZGERS-UHFFFAOYSA-N 1-hydroxy-5,8-bis(methylamino)-4-nitroanthracene-9,10-dione Chemical compound CNC1=CC=C(C=2C(C3=C(C=CC(=C3C(C12)=O)[N+](=O)[O-])O)=O)NC DPCKWQVALZGERS-UHFFFAOYSA-N 0.000 description 1
- CAYCLMJYVQVQBB-UHFFFAOYSA-N 1-hydroxy-8-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC([N+]([O-])=O)=C2C(=O)C2=C1C=CC=C2O CAYCLMJYVQVQBB-UHFFFAOYSA-N 0.000 description 1
- OALYQUZKMXTARO-UHFFFAOYSA-N ClC=1C(=C(C=CC1)Cl)Cl.ClC1=CC=CC=C1 Chemical compound ClC=1C(=C(C=CC1)Cl)Cl.ClC1=CC=CC=C1 OALYQUZKMXTARO-UHFFFAOYSA-N 0.000 description 1
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/515—N-alkyl, N-aralkyl or N-cycloalkyl derivatives
-
- 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752500237 DE2500237C2 (de) | 1975-01-04 | 1975-01-04 | Anthrachinoide dispersionsfarbstoffe, deren herstellung und deren verwendung |
| CH1689375A CH595419A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-01-04 | 1975-12-30 | |
| IT5291775A IT1052663B (it) | 1975-01-04 | 1975-12-30 | Coloranti antrachinoidici in dispersione e procedimento per la loro produzione |
| GB3976A GB1532891A (en) | 1975-01-04 | 1976-01-02 | Anthraquinonoid disperse dyes |
| FR7600018A FR2296666A1 (fr) | 1975-01-04 | 1976-01-02 | Colorants dispersables anthraquinoniques |
| JP51000032A JPS5916577B2 (ja) | 1975-01-04 | 1976-01-05 | アントラキノン系分散染料 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752500237 DE2500237C2 (de) | 1975-01-04 | 1975-01-04 | Anthrachinoide dispersionsfarbstoffe, deren herstellung und deren verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2500237B1 DE2500237B1 (de) | 1976-05-26 |
| DE2500237C2 true DE2500237C2 (de) | 1977-01-13 |
Family
ID=5935972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752500237 Expired DE2500237C2 (de) | 1975-01-04 | 1975-01-04 | Anthrachinoide dispersionsfarbstoffe, deren herstellung und deren verwendung |
Country Status (6)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2705716C2 (de) * | 1977-02-11 | 1986-07-24 | Basf Ag, 6700 Ludwigshafen | Anthrachinoide Farbstoffe und deren Verwendung |
| DE2727331C2 (de) * | 1977-06-16 | 1986-07-24 | Basf Ag, 6700 Ludwigshafen | Anthrachinoide Dispersionsfarbstoffe und deren Verwendung |
| DE3314467A1 (de) * | 1982-07-17 | 1984-01-19 | Bayer Ag, 5090 Leverkusen | Dichroitisches material, enthaltend anthrachinonfarbstoffe und neue anthrachinonfarbstoffe |
| CN103436046A (zh) * | 2013-08-20 | 2013-12-11 | 杭州帝凯化工有限公司 | 一种环保新型分散蓝2bln的制备方法 |
-
1975
- 1975-01-04 DE DE19752500237 patent/DE2500237C2/de not_active Expired
- 1975-12-30 CH CH1689375A patent/CH595419A5/xx not_active IP Right Cessation
- 1975-12-30 IT IT5291775A patent/IT1052663B/it active
-
1976
- 1976-01-02 FR FR7600018A patent/FR2296666A1/fr active Granted
- 1976-01-02 GB GB3976A patent/GB1532891A/en not_active Expired
- 1976-01-05 JP JP51000032A patent/JPS5916577B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5916577B2 (ja) | 1984-04-16 |
| IT1052663B (it) | 1981-07-20 |
| JPS5192832A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-08-14 |
| CH595419A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-02-15 |
| FR2296666B3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-10-06 |
| FR2296666A1 (fr) | 1976-07-30 |
| DE2500237B1 (de) | 1976-05-26 |
| GB1532891A (en) | 1978-11-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8330 | Complete disclaimer |