DE2119745C3 - Monoazofarbstoffe, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung zum Färben von Fasern - Google Patents
Monoazofarbstoffe, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung zum Färben von FasernInfo
- Publication number
- DE2119745C3 DE2119745C3 DE19712119745 DE2119745A DE2119745C3 DE 2119745 C3 DE2119745 C3 DE 2119745C3 DE 19712119745 DE19712119745 DE 19712119745 DE 2119745 A DE2119745 A DE 2119745A DE 2119745 C3 DE2119745 C3 DE 2119745C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- toluidine
- dyes
- ethyl
- preparation
- 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 19
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 5
- 239000000835 fiber Substances 0.000 title description 11
- 238000000034 method Methods 0.000 title description 8
- 238000004043 dyeing Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N meta-toluidine Natural products CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 9
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 8
- -1 benzene amines Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical class [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920002972 Acrylic fiber Polymers 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 3
- 150000002475 indoles Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical group 0.000 description 3
- 229920002239 polyacrylonitrile Polymers 0.000 description 3
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical group O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- JRQMRDBHOIOIIL-UHFFFAOYSA-N 3-methyl-1,5-dihydropyrazol-4-one Chemical compound CC1=NNCC1=O JRQMRDBHOIOIIL-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SNLLVPIXRHTWRC-UHFFFAOYSA-N 1-[2-(n-ethyl-3-methylanilino)ethyl]pyrrolidine-2,5-dione Chemical compound C=1C=CC(C)=CC=1N(CC)CCN1C(=O)CCC1=O SNLLVPIXRHTWRC-UHFFFAOYSA-N 0.000 description 1
- KMAQZIILEGKYQZ-UHFFFAOYSA-N 1-chloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1 KMAQZIILEGKYQZ-UHFFFAOYSA-N 0.000 description 1
- JBWYXHHFYARVEZ-UHFFFAOYSA-N 1-chloro-3-nitrobenzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.[O-][N+](=O)C1=CC=CC(Cl)=C1 JBWYXHHFYARVEZ-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- NPCCPMHHNIOSHL-UHFFFAOYSA-N 3-(n-ethyl-3-methylanilino)propanenitrile Chemical compound N#CCCN(CC)C1=CC=CC(C)=C1 NPCCPMHHNIOSHL-UHFFFAOYSA-N 0.000 description 1
- 241000052343 Dares Species 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000000159 acid neutralizing agent Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- MPSZITJFIKCNBV-UHFFFAOYSA-N cyclohexa-2,4-dien-1-imine Chemical group N=C1CC=CC=C1 MPSZITJFIKCNBV-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 229960005369 scarlet red Drugs 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7015403A FR2085505B1 (enrdf_load_stackoverflow) | 1970-04-28 | 1970-04-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2119745A1 DE2119745A1 (de) | 1971-11-18 |
| DE2119745B2 DE2119745B2 (de) | 1974-05-02 |
| DE2119745C3 true DE2119745C3 (de) | 1974-12-05 |
Family
ID=9054715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712119745 Expired DE2119745C3 (de) | 1970-04-28 | 1971-04-22 | Monoazofarbstoffe, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung zum Färben von Fasern |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE765388A (enrdf_load_stackoverflow) |
| BR (1) | BR7102526D0 (enrdf_load_stackoverflow) |
| CH (1) | CH527879A (enrdf_load_stackoverflow) |
| DE (1) | DE2119745C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2085505B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1355352A (enrdf_load_stackoverflow) |
| NL (1) | NL7105344A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2315493B (en) * | 1996-07-24 | 2001-01-03 | Lexmark Int Inc | Ink jet ink dyes |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE633447A (enrdf_load_stackoverflow) * | ||||
| FR1497149A (fr) * | 1965-10-22 | 1967-10-06 | Gen Aniline & Film Corp | Colorants monoazoïques basiques, notamment pour la teinture des fibres synthétiques |
| CH557857A (de) * | 1968-05-31 | 1975-01-15 | Ciba Geigy Ag | Verfahren zur herstellung von basischen azofarbstoffen. |
-
1970
- 1970-04-28 FR FR7015403A patent/FR2085505B1/fr not_active Expired
-
1971
- 1971-04-06 BE BE765388A patent/BE765388A/xx unknown
- 1971-04-20 NL NL7105344A patent/NL7105344A/xx unknown
- 1971-04-22 DE DE19712119745 patent/DE2119745C3/de not_active Expired
- 1971-04-23 CH CH597571A patent/CH527879A/fr not_active IP Right Cessation
- 1971-04-28 GB GB1176071A patent/GB1355352A/en not_active Expired
- 1971-04-28 BR BR252671A patent/BR7102526D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2119745A1 (de) | 1971-11-18 |
| GB1355352A (en) | 1974-06-05 |
| FR2085505A1 (enrdf_load_stackoverflow) | 1971-12-24 |
| BE765388A (fr) | 1971-10-06 |
| NL7105344A (enrdf_load_stackoverflow) | 1971-11-01 |
| CH527879A (fr) | 1972-09-15 |
| FR2085505B1 (enrdf_load_stackoverflow) | 1973-07-13 |
| DE2119745B2 (de) | 1974-05-02 |
| BR7102526D0 (pt) | 1973-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |