DE1010214B - Verfahren zur Herstellung von Disazofarbstoffen und ihren komplexen Kupferverbindungen - Google Patents
Verfahren zur Herstellung von Disazofarbstoffen und ihren komplexen KupferverbindungenInfo
- Publication number
- DE1010214B DE1010214B DEG17988A DEG0017988A DE1010214B DE 1010214 B DE1010214 B DE 1010214B DE G17988 A DEG17988 A DE G17988A DE G0017988 A DEG0017988 A DE G0017988A DE 1010214 B DE1010214 B DE 1010214B
- Authority
- DE
- Germany
- Prior art keywords
- oxynaphthalene
- sulfonic acid
- parts
- copper
- sulfoacetylamino
- 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
- 239000000975 dye Substances 0.000 title claims description 25
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 9
- 239000005749 Copper compound Substances 0.000 title claims description 4
- 150000001880 copper compounds Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 18
- -1 sulfoacetylamino group Chemical group 0.000 claims description 16
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical group C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- DBNPDRYVYQWGFW-UHFFFAOYSA-N N.[Cu]=O Chemical compound N.[Cu]=O DBNPDRYVYQWGFW-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- ZTXONRUJVYXVTJ-UHFFFAOYSA-N chromium copper Chemical compound [Cr][Cu][Cr] ZTXONRUJVYXVTJ-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- HEWDOWUUTBCVJP-UHFFFAOYSA-N naphthalene-1,6-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 HEWDOWUUTBCVJP-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 239000000725 suspension 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH786918X | 1954-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1010214B true DE1010214B (de) | 1957-06-13 |
Family
ID=4536650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG17988A Pending DE1010214B (de) | 1954-09-17 | 1955-09-16 | Verfahren zur Herstellung von Disazofarbstoffen und ihren komplexen Kupferverbindungen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2824867A (enExample) |
| BE (1) | BE541338A (enExample) |
| CH (1) | CH328082A (enExample) |
| DE (1) | DE1010214B (enExample) |
| FR (1) | FR1139323A (enExample) |
| GB (1) | GB786918A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2970137A (en) * | 1958-09-09 | 1961-01-31 | Verona Pharma Chemical Corp | Metallized mixed azo-dyestuffs |
| DE1233518B (de) * | 1961-12-14 | 1967-02-02 | Bayer Ag | Verfahren zur Herstellung metallhaltiger Azofarbstoffe |
| DE1444671C3 (de) * | 1963-11-27 | 1975-05-07 | Bayer Ag, 5090 Leverkusen | Metallhaltige Azofarbstoffe und ihre Verwendung zum Färben vegetabilischer Fasern |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB333573A (en) * | 1929-05-10 | 1930-08-11 | Ig Farbenindustrie Ag | Process for the manufacture of substantive ª¤-carboxyazo dyestuffs containing copper |
| DE858438C (de) * | 1945-03-22 | 1952-12-08 | Ciba Geigy | Verfahren zur Herstellung von kupferhaltigen Disazofarbstoffen |
| DE889662C (de) * | 1949-08-05 | 1953-09-14 | Ciba Geigy | Verfahren zur Herstellung kupferhaltiger Disazofarbstoffe |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2620331A (en) * | 1944-08-24 | 1952-12-02 | Sandoz Ltd | Copper-containing azo dyestuffs |
| CH268766A (de) * | 1947-06-26 | 1950-05-31 | Ciba Geigy | Verfahren zur Herstellung eines kupferhaltigen Farbstoffes. |
| US2720518A (en) * | 1950-08-01 | 1955-10-11 | Ciba Ltd | Azo-dyestuffs |
-
0
- BE BE541338D patent/BE541338A/xx unknown
-
1954
- 1954-09-17 CH CH328082D patent/CH328082A/de unknown
-
1955
- 1955-09-06 US US532773A patent/US2824867A/en not_active Expired - Lifetime
- 1955-09-16 FR FR1139323D patent/FR1139323A/fr not_active Expired
- 1955-09-16 DE DEG17988A patent/DE1010214B/de active Pending
- 1955-09-16 GB GB26541/55A patent/GB786918A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB333573A (en) * | 1929-05-10 | 1930-08-11 | Ig Farbenindustrie Ag | Process for the manufacture of substantive ª¤-carboxyazo dyestuffs containing copper |
| DE858438C (de) * | 1945-03-22 | 1952-12-08 | Ciba Geigy | Verfahren zur Herstellung von kupferhaltigen Disazofarbstoffen |
| DE889662C (de) * | 1949-08-05 | 1953-09-14 | Ciba Geigy | Verfahren zur Herstellung kupferhaltiger Disazofarbstoffe |
Also Published As
| Publication number | Publication date |
|---|---|
| BE541338A (enExample) | |
| FR1139323A (fr) | 1957-06-27 |
| CH328082A (de) | 1958-02-28 |
| US2824867A (en) | 1958-02-25 |
| GB786918A (en) | 1957-11-27 |
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