GB716937A - Improvement in 1:8-dihydroxy-5-nitro-4-anilinoanthraquinone compounds - Google Patents
Improvement in 1:8-dihydroxy-5-nitro-4-anilinoanthraquinone compoundsInfo
- Publication number
- GB716937A GB716937A GB20319/52A GB2031952A GB716937A GB 716937 A GB716937 A GB 716937A GB 20319/52 A GB20319/52 A GB 20319/52A GB 2031952 A GB2031952 A GB 2031952A GB 716937 A GB716937 A GB 716937A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aniline
- aminophenyl
- propanol
- hydroxypropyl
- group
- 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
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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A number of aminophenyl propanols or propanediols are prepared by nitration, reduction and hydrolysis of the corresponding phenylpropanol or phenylpropanediol acetates or diacetates. Products specified are 3-(aminophenyl) - propanol - 1, 1- or 2-(aminophenyl)-propanol - 2, 1 - (aminophenyl) - 1,3 -, 2,3-, or 1.2-dihydroxypropane, 2-(aminophenyl)-1,3-dihydroxypropane, and 2-(aminophenyl)-propanol-1. m - (g - hydroxypropyl) aniline and 2 - methoxy - 5 - (g - hydroxypropyl) aniline are obtained from m-nitrobenzaldehyde and 3-nitro-4-methoxy-benzaldehyde respectively by Perkins reaction to give the corresponding cinnamic acid substitution products, which are reduced with Raney nickel to the m-aminophenylpropionic acids, and reducing further with lithium aluminium hydride. 3 - (2 - and/or 4 - amino - 3 - chlorphenyl) - propanol-1 is obtained from m-(g -hydroxypropyl) aniline by replacing the amino group by chlorine (Sandmeyer), acetylating, nitrating, reducing, and hydrolysing. The diacetate of 1-phenyl-2,3-propanediol-1 is obtained by phenylmagnesium bromide with epichlorhydrin and acetylating first with potassium acetate in acetic acid followed by acetic anhydride. Specification 646,459, [Group IV (c)], is referred to.ALSO:The invention comprises dyes of the formula: <FORM:0716937/IV(c)/1> where X represents a mono-b - or g - hydroxyalkyl group or dihydroxyalkyl group of three carbon atoms, a -(OCH2 CH2)n-OH group where n is 1, 2, 3, or 4 or a -(OCH2 CH2)m OR group where m is 1, 2, or 3, and R is alkyl of 1 or 2 carbon atoms, and Y is hydrogen, chlorine, hydroxy, methoxy, or methyl. They are made by condensing 1.8-dihydroxy-4.5-dinitroanthraquinone with a primary arylamine of the formula: <FORM:0716937/IV(c)/2> The reaction may be carried out in an excess of the amine, in presence of water, or in an organic solvent such as an alcohol, a phenol, a glycol or glycol ether, an N.N-dialkyl fatty acid amide, or a nitrogen compound such as nitrobenzene, pyridine, or quinoline. The products dye cellulose esters (e.g. acetate, propionate, butyrate, acetate-propionate, and acetate-butyrate) and may be applied as a dispersion made by grinding to a paste in presence of a sulphonated oil, soap, sodium, lignin sulphonate, or other dispersing agent. In examples, 1.8-dihydroxy-4.5-dinitroanthraquinone is reacted with (1) p-(b -hydroxyethoxy) aniline, (2) o- or m-(b -hydroxyethoxyethoxy) aniline, (3) o-, m-, or p-(b -hydroxyethoxyethoxyethoxy)-aniline, (4) o- or p-(b -hydroxyethoxyethoxyethoxyethoxy)-aniline, (5) m- or p-( -ethoxyethoxyethoxy)-aniline, (6) p-(b -ethoxyethoxyethoxyethoxy) aniline, (7) o-(b -methoxyethoxyethoxy)-aniline, (8) o-, m-, or p-(g -hydroxypropyl) aniline, or mixtures of them, (9) 2-(o- and p-aminophenyl) propanol-1, (10) 1-(o- and p-aminophenyl)-propanol-2, (11) 1-(aminophenyl),-1.3-dihydroxypropane, (13) 2-(aminophenyl)-propanol-2, (14) 1-(aminophenyl)-2.3-dihydroxypropane, (15) 2-methoxy-5-(g -hydroxypropyl)-anilene, (16) 3-(2- and/or 4-amino-3-chlorophenyl)-1-propanol, (17) a mixture of o- and p-(a b -dihydroxypropyl) aniline, (18) a mixture of o- and p-(sym.-dihydroxyisopropyl) aniline. Specification 646,459 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US716937XA | 1951-08-17 | 1951-08-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB716937A true GB716937A (en) | 1954-10-20 |
Family
ID=22102963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20319/52A Expired GB716937A (en) | 1951-08-17 | 1952-08-13 | Improvement in 1:8-dihydroxy-5-nitro-4-anilinoanthraquinone compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB716937A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4964876A (en) * | 1988-05-24 | 1990-10-23 | Ciba-Geigy Corporation | Blue anthraquinone disperse dyes and mixtures of blue disperse dyes |
-
1952
- 1952-08-13 GB GB20319/52A patent/GB716937A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4964876A (en) * | 1988-05-24 | 1990-10-23 | Ciba-Geigy Corporation | Blue anthraquinone disperse dyes and mixtures of blue disperse dyes |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Fujita et al. | Honokiol, a new phenolic compound isolated from the bark of Magnolia obovata Thunb | |
| US2700686A (en) | Hydroxy substituted polyfluorinated compounds | |
| GB716688A (en) | Improvements in and relating to new anthraquinone compounds | |
| GB716937A (en) | Improvement in 1:8-dihydroxy-5-nitro-4-anilinoanthraquinone compounds | |
| GB1001821A (en) | Light-sensitive elements for photomechanical reproduction | |
| GB980232A (en) | Improvements relating to cyclic azo compounds | |
| GB1287343A (en) | N-carbamoylethyl aromatic amine compounds | |
| GB722367A (en) | Improvement in 1:5-dihydroxy-8-nitro-4-aminoanthraquinone compounds | |
| US2333384A (en) | Arylaminoanthraquinone compound | |
| GB1008852A (en) | Diazotype material | |
| GB1216109A (en) | Process for the production of nitroaminodiaryl ethers | |
| GB808276A (en) | Improvements in or relating to colour couplers for colour photography | |
| US2572067A (en) | Trifluoromethyl diphenylamines | |
| US2508182A (en) | Pentachloro-2, 4-cyclopentadienylidene-1-acetic acid and derivatives thereof | |
| US2470095A (en) | Diphenylamine compounds | |
| US3391186A (en) | Benzoic acids | |
| GB490364A (en) | Improvements in the manufacture and production of amino compounds | |
| US3022354A (en) | 4-polyalkyleneoxy-1-naphthols | |
| GB1379813A (en) | Benzoylacetanilide yellow forming colour couplers for phtographic silver halide material | |
| Emerson et al. | o-and p-Nitroacetophenones by Liquid Phase Oxidation | |
| GB489697A (en) | Improvements in the manufacture and production of compounds of the anthraquinone series | |
| JPS55115853A (en) | Preparation of aromatic amine | |
| GB500118A (en) | Process for the manufacture of sulphonic acid amide compounds | |
| GB749908A (en) | Manufacture of xanthenium compounds | |
| GB441079A (en) | Manufacture of intermediates for azo dyes |