GB1055399A - Improvements in and relating to monoazo dyes - Google Patents
Improvements in and relating to monoazo dyesInfo
- Publication number
- GB1055399A GB1055399A GB3382264A GB3382264A GB1055399A GB 1055399 A GB1055399 A GB 1055399A GB 3382264 A GB3382264 A GB 3382264A GB 3382264 A GB3382264 A GB 3382264A GB 1055399 A GB1055399 A GB 1055399A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- formula
- group
- chlorine
- atom
- 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 abstract 3
- 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 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 239000000460 chlorine Chemical group 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 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
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 230000002209 hydrophobic effect Effects 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- -1 mono-azo compound Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
- C09B43/20—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with monocarboxylic acids, carbamic acid esters or halides, mono- isocyanates or haloformic acid esters
- C09B43/22—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with monocarboxylic acids, carbamic acid esters or halides, mono- isocyanates or haloformic acid esters having the carboxylic group directly attached to an aromatic carbocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention provides monoazo water-insoluble dyes of general formula <FORM:1055399/C4-C5/1> in which R1 is a nitro or alkylsulphonyl group, R2 is a hydrogen, chlorine or bromine atom, or a cyano nitro or alkylsulphonyl group, R3 is a hydrogen or chlorine or bromine atom, R4 is an atom of hydrogen or chlorine or an alkyl or acylamino group, R5 is a hydrogen atom or an alkyl or alkoxy group, R6 is a hydrogen atom or a methoxy or ethoxy group. The dyes may be made by (a) diazotizing an amine of formula <FORM:1055399/C4-C5/2> and coupling with an amine of formula <FORM:1055399/C4-C5/3> or (b) a mono-azo compound of formula <FORM:1055399/C4-C5/4> is esterified with a functional derivative of an aromatic carboxylic acid, e.g. anhydrides and acid chlorides. Blue-red shades are obtained on hydrophobic fibres.ALSO:N - b - Cyanoethyl - N - b - benzoyloxyethylaminobenzene is prepared by adding benzoyl chloride to N-b -cyanoethyl-N-b -hydroxy-ethyl-aminobenzene in pyridine, the product being poured on to water to give an oil which solidifies on standing giving a white solid.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3382264A GB1055399A (en) | 1964-08-19 | 1964-08-19 | Improvements in and relating to monoazo dyes |
| DE19651644401 DE1644401B1 (en) | 1964-08-19 | 1965-08-18 | Monoazo dyes and processes for making and using monoazo dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3382264A GB1055399A (en) | 1964-08-19 | 1964-08-19 | Improvements in and relating to monoazo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1055399A true GB1055399A (en) | 1967-01-18 |
Family
ID=10357906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3382264A Expired GB1055399A (en) | 1964-08-19 | 1964-08-19 | Improvements in and relating to monoazo dyes |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1644401B1 (en) |
| GB (1) | GB1055399A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2013255A1 (en) * | 1968-07-19 | 1970-03-27 | Sandoz Sa | |
| FR2182782A1 (en) * | 1971-09-30 | 1973-12-14 | Gaf Corp |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1211477A (en) * | 1957-07-26 | 1960-03-16 | Basf Ag | Production and use of novel azo dyes |
| FR1330392A (en) * | 1962-06-28 | 1963-06-21 | Ici Ltd | Water soluble azo dyes for dyeing artificial textile materials |
-
1964
- 1964-08-19 GB GB3382264A patent/GB1055399A/en not_active Expired
-
1965
- 1965-08-18 DE DE19651644401 patent/DE1644401B1/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2013255A1 (en) * | 1968-07-19 | 1970-03-27 | Sandoz Sa | |
| FR2182782A1 (en) * | 1971-09-30 | 1973-12-14 | Gaf Corp |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1644401B1 (en) | 1972-02-03 |
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