GB465138A - The manufacture of water-insoluble azodyestuffs and printing preparations - Google Patents
The manufacture of water-insoluble azodyestuffs and printing preparationsInfo
- Publication number
- GB465138A GB465138A GB3027335A GB3027335A GB465138A GB 465138 A GB465138 A GB 465138A GB 3027335 A GB3027335 A GB 3027335A GB 3027335 A GB3027335 A GB 3027335A GB 465138 A GB465138 A GB 465138A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- chloro
- aminophenol
- similar
- diazoimino
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 10
- 239000000987 azo dye Substances 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 8
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 abstract 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 abstract 5
- 230000008878 coupling Effects 0.000 abstract 5
- 238000010168 coupling process Methods 0.000 abstract 5
- 238000005859 coupling reaction Methods 0.000 abstract 5
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 abstract 4
- WOXLPNAOCCIZGP-UHFFFAOYSA-N 4-chloro-2-methoxyaniline Chemical compound COC1=CC(Cl)=CC=C1N WOXLPNAOCCIZGP-UHFFFAOYSA-N 0.000 abstract 4
- 239000005749 Copper compound Substances 0.000 abstract 4
- 108010077895 Sarcosine Proteins 0.000 abstract 4
- 150000001880 copper compounds Chemical class 0.000 abstract 4
- 229940043230 sarcosine Drugs 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 239000000975 dye Substances 0.000 abstract 3
- -1 metal complex compounds Chemical class 0.000 abstract 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 abstract 2
- 229940018563 3-aminophenol Drugs 0.000 abstract 2
- 229920000742 Cotton Polymers 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- 239000000835 fiber Substances 0.000 abstract 2
- 229940018564 m-phenylenediamine Drugs 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 230000007935 neutral effect Effects 0.000 abstract 2
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 2
- RRWZZMHRVSMLCT-UHFFFAOYSA-N 2-(butylazaniumyl)acetate Chemical compound CCCCNCC(O)=O RRWZZMHRVSMLCT-UHFFFAOYSA-N 0.000 abstract 1
- JIGMTKAVOOCLFQ-UHFFFAOYSA-N 2-(methylamino)-4-sulfobenzoic acid Chemical compound CNC1=CC(S(O)(=O)=O)=CC=C1C(O)=O JIGMTKAVOOCLFQ-UHFFFAOYSA-N 0.000 abstract 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- PFRYFZZSECNQOL-UHFFFAOYSA-N 2-methyl-4-[(2-methylphenyl)diazenyl]aniline Chemical compound C1=C(N)C(C)=CC(N=NC=2C(=CC=CC=2)C)=C1 PFRYFZZSECNQOL-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- GBPBXBUHZSOKTH-UHFFFAOYSA-N 4-chloropiperidine Chemical compound ClC1CCNCC1 GBPBXBUHZSOKTH-UHFFFAOYSA-N 0.000 abstract 1
- 241000416162 Astragalus gummifer Species 0.000 abstract 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 abstract 1
- 229920002472 Starch Polymers 0.000 abstract 1
- 229920001615 Tragacanth Polymers 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 abstract 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052804 chromium Inorganic materials 0.000 abstract 1
- 239000011651 chromium Substances 0.000 abstract 1
- 150000001869 cobalt compounds Chemical class 0.000 abstract 1
- 239000003086 colorant Substances 0.000 abstract 1
- JWEKFMCYIRVOQZ-UHFFFAOYSA-N cyanamide;sodium Chemical compound [Na].NC#N JWEKFMCYIRVOQZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 239000011572 manganese Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- VIUTVHGOAOMQHY-UHFFFAOYSA-N n-(4-amino-5-chloro-2-methoxyphenyl)benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1NC(=O)C1=CC=CC=C1 VIUTVHGOAOMQHY-UHFFFAOYSA-N 0.000 abstract 1
- VENDXQNWODZJGB-UHFFFAOYSA-N n-(4-amino-5-methoxy-2-methylphenyl)benzamide Chemical compound C1=C(N)C(OC)=CC(NC(=O)C=2C=CC=CC=2)=C1C VENDXQNWODZJGB-UHFFFAOYSA-N 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 abstract 1
- 229960001755 resorcinol Drugs 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 230000003381 solubilizing effect Effects 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 235000019698 starch Nutrition 0.000 abstract 1
- 239000008107 starch Substances 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 239000002562 thickening agent Substances 0.000 abstract 1
- 239000000196 tragacanth Substances 0.000 abstract 1
- 229940116362 tragacanth Drugs 0.000 abstract 1
- 235000010487 tragacanth Nutrition 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
- 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
-
- 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Water-insoluble azo dyes are made by coupling on the fibre metal complex compounds of the azo dyes from resorcinol, m-aminophenol, m-phenylenediamine or the homologues or substitution products thereof capable of coupling twice and o-hydroxy- or o-carboxy-diazo compounds, the azo dyes containing no further solubilizing groups, with diazo compounds suitable for the manufacture of ice-colours. Brown shades are obtained. The coupling component may be applied to the fibre together with an arylnitrosamine or an aryldiazoamino- or iminocompound, if desired, in the form of a printing composition, and the dyestuff developed according to standard methods. The metal containing o-oxyazo dyes used as coupling components can also be obtained from o-halogen or o-alkoxyamines. In the examples: (1) cotton tissue is printed with a paste containing the diazoimino compound from 4-chloro-2-anisidine and sarcosine, the copper complex compound of the azo dye 4-chloro-2-aminophenol --> resorcinol, caustic soda, glycolmonoethylether, neutral starch tragacanth thickener, dried, steamed in presence of acetic and formic acid, rinsed, boiled, rinsed and dried (full dark brown), (2) similar to (1) using the diazoimino compound from 4-benzoylamino-2 : 5 - dimethoxyaniline and n-butylaminoacetic acid or that from 4-benzoylamino-2-chloro-5-methoxyaniline and 4-sulpho-2-methylaminobenzoic acid, (3) cotton yarn is treated in a bath containing the sodium salt of the copper compound of the azo dye 4-chloro-2-aminophenol --> resorcinol, caustic soda and turkey red oil and developed with diazotized aminoazotoluene, (4) similar to (1) using the nitrosamine from 4-chloro-2-anisidine instead of the diazoimino compound with neutral chromate in addition, (5) similar to (4) using the diazoimino compound from 4-chloro-2-anisidine and piperidine-3-sodium sulphonate or that from 1-amino-4-benzoylamino-2 : 5-diethoxybenzene and methylglucamine or the compound from diazotized 1-amino-2 : 5-dimethoxy-4<1>-nitroazobenzene and sodium cyanamide, (6) similar to (1) using the copper complex compound of the azo dye 4-chloro-2-aminophenol --> 1-methyl-2 : 6-dihydroxybenzene and the diazoimino compound from 1-amino-4-benzoylamino-2-methoxy-5-methylbenzene and sarcosine (brown, yellower than the print with the dyestuff from resorcinol), (7) similar to (1) using the copper compound of the azo dye anthranilic acid --> resorcinol and the diazoimino compound from 1-amino-2 : 5-diethoxy-4-benzoylaminobenzene and sarcosine, (8)-(10) similar to (1) using the diazoimino compound from 4-chloro-2-anisidine and sarcosine and the copper compound of the azo dye 4-chloro-2-aminophenol --> (acid or alkaline) m-aminophenol or the copper compound of the azo dye 4-chloro-2-aminophenol --> m-phenylenediamine or 4<1>-methyl-3- hydroxydiphenylamine. A table of further combinations is given including the use of chromium, nickel, manganese and cobalt compounds as coupling components.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3027335A GB465138A (en) | 1935-11-01 | 1935-11-01 | The manufacture of water-insoluble azodyestuffs and printing preparations |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3027335A GB465138A (en) | 1935-11-01 | 1935-11-01 | The manufacture of water-insoluble azodyestuffs and printing preparations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB465138A true GB465138A (en) | 1937-05-03 |
Family
ID=10305027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3027335A Expired GB465138A (en) | 1935-11-01 | 1935-11-01 | The manufacture of water-insoluble azodyestuffs and printing preparations |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB465138A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0423071A1 (en) * | 1989-10-12 | 1991-04-17 | Ciba-Geigy Ag | Polyazodyes |
| US5270455A (en) * | 1989-10-12 | 1993-12-14 | Ciba-Geigy Corporation | Polyazo dyes containing resorcinol as middle component and metal complexes thereof |
-
1935
- 1935-11-01 GB GB3027335A patent/GB465138A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0423071A1 (en) * | 1989-10-12 | 1991-04-17 | Ciba-Geigy Ag | Polyazodyes |
| US5270455A (en) * | 1989-10-12 | 1993-12-14 | Ciba-Geigy Corporation | Polyazo dyes containing resorcinol as middle component and metal complexes thereof |
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