GB904992A - New complex metal compounds of monoazo-dyestuffs, and their manufacture and use - Google Patents
New complex metal compounds of monoazo-dyestuffs, and their manufacture and useInfo
- Publication number
- GB904992A GB904992A GB2856159A GB2856159A GB904992A GB 904992 A GB904992 A GB 904992A GB 2856159 A GB2856159 A GB 2856159A GB 2856159 A GB2856159 A GB 2856159A GB 904992 A GB904992 A GB 904992A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- dye
- acid
- dyes
- monoazo
- 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
- 150000002736 metal compounds Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000975 dye Substances 0.000 abstract 11
- 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 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 229920003043 Cellulose fiber Polymers 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- -1 aminoazo Chemical group 0.000 abstract 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- IBHSLLQJRFOICG-UHFFFAOYSA-N 1,2-dichloro-2-oxoethanesulfonic acid Chemical compound OS(=O)(=O)C(Cl)C(Cl)=O IBHSLLQJRFOICG-UHFFFAOYSA-N 0.000 abstract 1
- CXJAFLQWMOMYOW-UHFFFAOYSA-N 3-chlorofuran-2,5-dione Chemical compound ClC1=CC(=O)OC1=O CXJAFLQWMOMYOW-UHFFFAOYSA-N 0.000 abstract 1
- ORLGPUVJERIKLW-UHFFFAOYSA-N 5-chlorotriazine Chemical compound ClC1=CN=NN=C1 ORLGPUVJERIKLW-UHFFFAOYSA-N 0.000 abstract 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 abstract 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 238000004873 anchoring Methods 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000003125 aqueous solvent Substances 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001844 chromium Chemical class 0.000 abstract 1
- 229910052804 chromium Inorganic materials 0.000 abstract 1
- 239000011651 chromium Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 150000004696 coordination complex Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000005694 halopyrimidines Chemical class 0.000 abstract 1
- 229910001385 heavy metal Inorganic materials 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 230000014759 maintenance of location Effects 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000001465 metallisation Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- MKJZRZRIEWBTMN-UHFFFAOYSA-N prop-2-ynoyl chloride Chemical compound ClC(=O)C#C MKJZRZRIEWBTMN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 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
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
- C09B62/012—Metal complex azo dyes
-
- 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
- C09B45/48—Preparation from other complex metal compounds of azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises complex heavy metal compounds of monoazo dyes of formula <FORM:0904992/IV (b)/1> wherein A is the residue of a coupling component bound to the azo linkage in o-position to a hydroxyl group and X is a reactive substituent (i.e. a substituent capable of entering into true chemical combination with the cellulose fibre thereby anchoring the dye by a definite chemical or covalent bond and not by physical absorption or mechanical retention so that the dye cannot be removed from the fibre by washing with aqueous or organic solvents). They are prepared by acylating a monoazo dye of formula <FORM:0904992/IV (b)/2> or a metal complex thereof with an anhydride or halide of an acid, the residue of which is capable of reacting with cellulose to form a covalent bond and metallising if necessary. Specified acylating agents include cyanuric halides, halopyrimidines, acrylic chloride, propiolic chloride, chloromaleic anhydride, chloroacetyl chloride, b -bromo-or-chloro-propionic acid chooride, sulpho-chloro-acetic acid chloride and a :b -dichloropropionyl chloride. The intermediate aminoazo dyes and their metal complexes are prepared by known methods. Copper, cobalt and chromium complexes are specified. If the dyestuff is readily metallisable, acylation may precede metallisation. When the dyes are acylated with cyanuric chloride to give a primary condensation product a second halogen atom may be replaced by reaction with, e.g. an amine, alcohol or phenol. The dyes may be used to colour wool, silk, leather, superpolyamides and especially cellulose fibres in the presence of an acid-binding agent in blue, green and red shades. In an example the monoazo dye 6-nitro-1-amino- 2-naphthol-4-sulphonic acid --> 6-(41-carboxymethoxyphenyl)- amino-1-naphthol-3-sulphonic acid is treated with sodium sulphide, the aminoazo dye formed is refluxed in an alkaline solution of sodium chromo-salicyeate to give the 1:2-chromium complex which is condensed successively with cyanuric chloride and ammonia to give the monochlorotriazine dyestuff. Many further examples are specified. Specifications 797,946, 822,047, 838,337, 847,635, 848,742, 852,911, 870,047, 870,985, 885,814 and 885,815 are referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6333258A CH377024A (en) | 1958-08-27 | 1958-08-27 | Process for the preparation of new metal complex compounds of monoazo dyes |
| CH7585759A CH418497A (en) | 1959-07-17 | 1959-07-17 | Process for the preparation of new metal complex compounds of monoazo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB904992A true GB904992A (en) | 1962-09-05 |
Family
ID=25737782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2856159A Expired GB904992A (en) | 1958-08-27 | 1959-08-20 | New complex metal compounds of monoazo-dyestuffs, and their manufacture and use |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE1136437B (en) |
| FR (1) | FR1235750A (en) |
| GB (1) | GB904992A (en) |
| NL (2) | NL124538C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4671799A (en) * | 1985-07-03 | 1987-06-09 | Basf Aktiengesellschaft | Dye mixtures for paper stock |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2222096C2 (en) * | 1972-05-05 | 1983-03-31 | Hoechst Ag, 6230 Frankfurt | Heavy metal complex azo dyes, process for their production and their use for dyeing and printing fiber material containing hydroxy or amide groups |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1779298A (en) * | 1927-10-08 | 1930-10-21 | Chem Ind Basel | Manufacture of dyestuffs containing metal |
-
1959
- 1959-08-18 FR FR803055A patent/FR1235750A/en not_active Expired
- 1959-08-20 GB GB2856159A patent/GB904992A/en not_active Expired
- 1959-08-26 NL NL242709A patent/NL124538C/xx active
- 1959-08-26 NL NL242709D patent/NL242709A/xx unknown
- 1959-08-26 DE DEC19684A patent/DE1136437B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4671799A (en) * | 1985-07-03 | 1987-06-09 | Basf Aktiengesellschaft | Dye mixtures for paper stock |
Also Published As
| Publication number | Publication date |
|---|---|
| NL124538C (en) | 1968-06-18 |
| NL242709A (en) | 1964-01-27 |
| FR1235750A (en) | 1960-07-08 |
| DE1136437B (en) | 1962-09-13 |
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