DE2244061C3 - Wasserlösliche Reaktivfarbstoffe der Anthrachinonreihe und Verfahren zu deren Herstellung - Google Patents
Wasserlösliche Reaktivfarbstoffe der Anthrachinonreihe und Verfahren zu deren HerstellungInfo
- Publication number
- DE2244061C3 DE2244061C3 DE2244061A DE2244061A DE2244061C3 DE 2244061 C3 DE2244061 C3 DE 2244061C3 DE 2244061 A DE2244061 A DE 2244061A DE 2244061 A DE2244061 A DE 2244061A DE 2244061 C3 DE2244061 C3 DE 2244061C3
- Authority
- DE
- Germany
- Prior art keywords
- formula
- dye
- water
- nii
- reactive dyes
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 239000000985 reactive dye Substances 0.000 title claims description 7
- 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 title claims description 6
- 150000004056 anthraquinones Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000003973 paint Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 12
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 210000002268 wool Anatomy 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 239000001103 potassium chloride Substances 0.000 description 4
- 235000011164 potassium chloride Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229920003043 Cellulose fiber Polymers 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- ZGKCMSJTSPNFDF-UHFFFAOYSA-N 1-anilino-9,10-dioxoanthracene-2-sulfonic acid Chemical compound N(C1=CC=CC=C1)C1=C(C=CC=2C(C3=CC=CC=C3C(C12)=O)=O)S(=O)(=O)O ZGKCMSJTSPNFDF-UHFFFAOYSA-N 0.000 description 2
- MMNWSHJJPDXKCH-UHFFFAOYSA-N 9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MMNWSHJJPDXKCH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 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 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 230000001180 sulfating effect Effects 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- ZKSAJEOABNZQKM-UHFFFAOYSA-N 2-(2-chloroethylsulfonyl)benzoyl chloride Chemical compound ClCCS(=O)(=O)C1=CC=CC=C1C(Cl)=O ZKSAJEOABNZQKM-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/443—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being alternatively specified
- C09B62/445—Anthracene dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2244061A DE2244061C3 (de) | 1972-09-08 | 1972-09-08 | Wasserlösliche Reaktivfarbstoffe der Anthrachinonreihe und Verfahren zu deren Herstellung |
| IN2031/CAL/73A IN141009B (enExample) | 1972-09-08 | 1973-09-05 | |
| CH1278773A CH578038A5 (enExample) | 1972-09-08 | 1973-09-05 | |
| AU60084/73A AU474482B2 (en) | 1972-09-08 | 1973-09-06 | New water-soluble reactive dyestuffs of the anthrequinone series and process for preparing them |
| IT28654/73A IT995297B (it) | 1972-09-08 | 1973-09-06 | Coloranti reattivi idrosolubili della serie antrachinonica e processo per la loro preparazione |
| JP48100408A JPS5113490B2 (enExample) | 1972-09-08 | 1973-09-07 | |
| CA180,492A CA1019729A (en) | 1972-09-08 | 1973-09-07 | Water-soluble reactive dyestuffs of the anthraquinone series and process for preparing them |
| FR7332478A FR2198935B1 (enExample) | 1972-09-08 | 1973-09-10 | |
| GB4248673A GB1402387A (en) | 1972-09-08 | 1973-09-10 | Water-soluble reactive dyestuffs of the anthraquinone series and process for preparing them |
| BE135508A BE804678A (fr) | 1972-09-08 | 1973-09-10 | Colorants anthraquinoniques reactifs et leur preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2244061A DE2244061C3 (de) | 1972-09-08 | 1972-09-08 | Wasserlösliche Reaktivfarbstoffe der Anthrachinonreihe und Verfahren zu deren Herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2244061A1 DE2244061A1 (de) | 1974-04-04 |
| DE2244061B2 DE2244061B2 (de) | 1974-07-25 |
| DE2244061C3 true DE2244061C3 (de) | 1975-03-20 |
Family
ID=5855774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2244061A Expired DE2244061C3 (de) | 1972-09-08 | 1972-09-08 | Wasserlösliche Reaktivfarbstoffe der Anthrachinonreihe und Verfahren zu deren Herstellung |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5113490B2 (enExample) |
| AU (1) | AU474482B2 (enExample) |
| BE (1) | BE804678A (enExample) |
| CA (1) | CA1019729A (enExample) |
| CH (1) | CH578038A5 (enExample) |
| DE (1) | DE2244061C3 (enExample) |
| FR (1) | FR2198935B1 (enExample) |
| GB (1) | GB1402387A (enExample) |
| IN (1) | IN141009B (enExample) |
| IT (1) | IT995297B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3029383A1 (de) * | 1980-08-01 | 1982-03-18 | Hoechst Ag, 6000 Frankfurt | Wasserloesliche, faserreaktive verbindungen, ihre herstellung und verwendung sowie neue (beta) -chloraethylsulfonylmethyl-benzoesaeurehalogenide und deren verwendung als faserreaktive anker |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB868744A (en) * | 1957-08-31 | 1961-05-25 | Basf Ag | Dyestuffs of the anthraquinone series and their production |
-
1972
- 1972-09-08 DE DE2244061A patent/DE2244061C3/de not_active Expired
-
1973
- 1973-09-05 CH CH1278773A patent/CH578038A5/xx not_active IP Right Cessation
- 1973-09-05 IN IN2031/CAL/73A patent/IN141009B/en unknown
- 1973-09-06 AU AU60084/73A patent/AU474482B2/en not_active Expired
- 1973-09-06 IT IT28654/73A patent/IT995297B/it active
- 1973-09-07 CA CA180,492A patent/CA1019729A/en not_active Expired
- 1973-09-07 JP JP48100408A patent/JPS5113490B2/ja not_active Expired
- 1973-09-10 BE BE135508A patent/BE804678A/xx not_active IP Right Cessation
- 1973-09-10 FR FR7332478A patent/FR2198935B1/fr not_active Expired
- 1973-09-10 GB GB4248673A patent/GB1402387A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2244061B2 (de) | 1974-07-25 |
| DE2244061A1 (de) | 1974-04-04 |
| BE804678A (fr) | 1974-03-11 |
| AU474482B2 (en) | 1976-07-22 |
| JPS4967918A (enExample) | 1974-07-02 |
| IT995297B (it) | 1975-11-10 |
| CA1019729A (en) | 1977-10-25 |
| AU6008473A (en) | 1975-03-06 |
| GB1402387A (en) | 1975-08-06 |
| CH578038A5 (enExample) | 1976-07-30 |
| FR2198935B1 (enExample) | 1977-02-25 |
| FR2198935A1 (enExample) | 1974-04-05 |
| IN141009B (enExample) | 1977-01-08 |
| JPS5113490B2 (enExample) | 1976-04-30 |
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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 |