GB1119326A - Water-insoluble azo dyestuffs - Google Patents
Water-insoluble azo dyestuffsInfo
- Publication number
- GB1119326A GB1119326A GB1657367A GB1657367A GB1119326A GB 1119326 A GB1119326 A GB 1119326A GB 1657367 A GB1657367 A GB 1657367A GB 1657367 A GB1657367 A GB 1657367A GB 1119326 A GB1119326 A GB 1119326A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- halogen
- alkoxy
- carboalkoxy
- optionally substituted
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000002209 hydrophobic effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 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 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises water-insoluble monoazo dyes free from sulphonic and carboxylic acid groups and having the general formula <FORM:1119326/C4-C5/1> wherein R1 is H, halogen, alkyl, alkoxy, CN, CF3, or carboalkoxy; R2 and R3 are H, halogen, alkyl, alkoxy or carboalkoxy; X and Y are H, halogen, alkyl or alkoxy; R4 is an optionally substituted alkyl group or an R5 radical which is <FORM:1119326/C4-C5/2> wherein R6-R9 are H or C1-C2 alkyl groups, and R is H or COR10 wherein R10 is an optionally substituted C1-C5 alkyl group. The optionally substituted alkyl groups may contain halogen atoms or CN or carboalkoxy groups. They are prepared by the usual diazotization and coupling methods, preferably at neutral pH values. They give yellow-brown, orange, red, scarlet and violet shades on hydrophobic fibre material, e.g. aromatic polyesters, cellulose esters, synthetic polyamides and polyacrylonitrile.ALSO:The compound <FORM:1119326/C2/1> is prepared by reacting b -chloro-b -1-acetoxy-diethyl ether with 1-N-ethyl amino-3- methyl benzene at 120 DEG to 140 DEG C. in presence of sodium acetate. The product may be isolated by means of water or methanol/water mixture.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0048967 | 1966-04-19 | ||
| DEF0050379 | 1966-10-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1119326A true GB1119326A (en) | 1968-07-10 |
Family
ID=25977143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1657367A Expired GB1119326A (en) | 1966-04-19 | 1967-04-11 | Water-insoluble azo dyestuffs |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE697218A (en) |
| CH (1) | CH477514A (en) |
| DE (2) | DE1644149A1 (en) |
| GB (1) | GB1119326A (en) |
| NL (1) | NL6705388A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2012796A (en) * | 1978-01-13 | 1979-08-01 | Bayer Ag | Azo dyestuffs |
| US4400322A (en) * | 1980-07-04 | 1983-08-23 | Imperial Chemical Industries Limited | Disperse monoazo dyestuffs |
| EP0384225A1 (en) * | 1989-02-23 | 1990-08-29 | CASSELLA Aktiengesellschaft | Use of dyestuffs in the sublimation-transfer process |
| US5266227A (en) * | 1991-02-22 | 1993-11-30 | Basf Aktiengesellschaft | Oil-soluble phenylazoaniline dyes |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4054560A (en) * | 1974-03-07 | 1977-10-18 | E. I. Du Pont De Nemours And Company | 1-(4-Acyloxyalkylaminonaphthylazo)-4-nitrobenzene disperse dyes |
-
1966
- 1966-04-19 DE DE19661644149 patent/DE1644149A1/en active Pending
- 1966-10-07 DE DE19661644174 patent/DE1644174A1/en active Pending
-
1967
- 1967-03-23 CH CH422767A patent/CH477514A/en not_active IP Right Cessation
- 1967-04-11 GB GB1657367A patent/GB1119326A/en not_active Expired
- 1967-04-17 NL NL6705388A patent/NL6705388A/xx unknown
- 1967-04-19 BE BE697218D patent/BE697218A/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2012796A (en) * | 1978-01-13 | 1979-08-01 | Bayer Ag | Azo dyestuffs |
| US4400322A (en) * | 1980-07-04 | 1983-08-23 | Imperial Chemical Industries Limited | Disperse monoazo dyestuffs |
| EP0384225A1 (en) * | 1989-02-23 | 1990-08-29 | CASSELLA Aktiengesellschaft | Use of dyestuffs in the sublimation-transfer process |
| US5093307A (en) * | 1989-02-23 | 1992-03-03 | Cassella Aktiengesellschaft | Use of water-insoluble monoazo dyes of the formula i |
| US5266227A (en) * | 1991-02-22 | 1993-11-30 | Basf Aktiengesellschaft | Oil-soluble phenylazoaniline dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1644174A1 (en) | 1971-07-08 |
| BE697218A (en) | 1967-10-19 |
| CH477514A (en) | 1969-08-31 |
| NL6705388A (en) | 1967-10-20 |
| DE1644149A1 (en) | 1971-03-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1274941A (en) | Monoazo and disazo compounds of low solubility in water which contain a dihydroxypyridine residue, their production and use as dyes | |
| GB1224413A (en) | Water-insoluble monoazo dyestuffs | |
| GB1158996A (en) | Production of Water-Insoluble Monoazo Dyes | |
| GB1119326A (en) | Water-insoluble azo dyestuffs | |
| GB1220422A (en) | Reactive yellow monoazo dyes of the phenylazo-pyrazole series and process for the preparation thereof | |
| GB1122169A (en) | Water-insoluble monoazo dyestuffs | |
| GB1005233A (en) | New monoazo dyestuffs | |
| ES337766A1 (en) | Monoazo Dyes and a process for their production | |
| US2227977A (en) | Azo compounds and material colored therewith | |
| US2231707A (en) | Azo compounds and material colored therewith | |
| GB1028564A (en) | Water-insoluble monoazo-dyestuffs and process for their manufacture | |
| GB1149035A (en) | Water-insoluble monoazo dyestuffs and process for their preparation | |
| GB959260A (en) | Water-insoluble monoazo dyestuffs | |
| GB1037164A (en) | Water-insoluble monoazo-dyestuffs and process for preparing them | |
| GB1348714A (en) | Sparingly soluble disazo compounds their production and use as pigments | |
| ES389310A1 (en) | Water-insoluble yellow monoazo dyestuffs and process for their manufacture | |
| GB1011971A (en) | Water-insoluble monoazo-dyestuffs and process for their manufacture | |
| US3254073A (en) | Disazo dyes for hydrophobic fibers | |
| GB1003448A (en) | New water-insoluble monoazo-dyestuffs | |
| GB1076049A (en) | New water-insoluble monoazo dyes containing an alkanoyl-amino-alkylamino group | |
| GB1348591A (en) | Disazo dyestuffs a process for their manufacture and their use | |
| GB1116367A (en) | Azo dyes of low solubility in water, their production and applications | |
| GB1003946A (en) | New monoazo dyes and processes for their production | |
| GB1060240A (en) | Improvements in and relating to monoazo dyes | |
| GB1026367A (en) | Water-insoluble monoazo dyestuffs and processes for their manufacture |