GB766609A - Improvements in and relating to diazoamino derivatives - Google Patents
Improvements in and relating to diazoamino derivativesInfo
- Publication number
- GB766609A GB766609A GB34025/54A GB3402554A GB766609A GB 766609 A GB766609 A GB 766609A GB 34025/54 A GB34025/54 A GB 34025/54A GB 3402554 A GB3402554 A GB 3402554A GB 766609 A GB766609 A GB 766609A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- acid
- dicarboxylic acids
- amines
- diazoamino
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
-
- 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
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Abstract
The invention comprises compounds of formula <FORM:0766609/IV(b)/1> where R is an aryl residue and X is an alkyl or cycloalkyl group which may be substituted, and their water-soluble salts. They are made by condensing an appropriate diazo-compound in a non-acid medium with the required substituted aniline-2,4-dicarboxylic acid or a water-soluble salt thereof. Diazo compounds indicated for use may be derived from aniline, toluidines, xylidines, cresidines, anisidines optionally having halogen substituents, nitroanilines, nitrotoluidines, nitroanisidines, nitrocresidines, monoacrylated p-diamines which may have halogen, alkyl or alkoxy substituents, benzidine, tolidines, dianisidines, aromatic bases containing sulphonamido, sulphone or trifluoromethyl groups, aminobenzthiazoles, aminoindazoles, amino azo dyestuffs and "Solid Bases." Preferred diazo compounds are those which do not contain solubilizing groups such as COOH or SO3H. Specified substituents which may be present in the ethyl or cycloalkyl groups are -OH, -OCH3, -OC2H5, -C6H5, -COOH, -SO3H, -OSO3H, -OPO3H2, -OPO2H2, -COOAlk and -CON< dicarboxylic acids specified being 1-methyl-, -ethyl-, isopropyl-, -propyl-, -isobutyl-, isoamyl-, -butyl-, benzyl-, - cyclohexyl -, - hydroxyethyl -, - dihydroxypropyl -, - (21 - hydroxy - 31 - sulpho - propyl) -, - glyco -, - (21 - methoxy - and - ethoxy - ethyl) and 1 - methyl - o - sulphonic - aminobenzene - 2,4 - dicarboxylic acids, 1 - phenylglycineben-zene - 2,4 - dicarboxylic acid, N - (21,41 - dicarboxyphenyl) - b - aminopropionic acid, - glycinamide and glycine methyl and ethyl esters. The products mixed with coupling components are used in the preparation of insoluble azo dyestuffs on the fibre (c.f. Group IV (c)). Examples are provided illustrating the preparation of diazoamino compounds from certain of the above specified dicarboxylic acids and diazo compounds of the following amines 4-chloro- and 5-nitro - 2 - aminotoluene, 5 - nitro - and 4 - diethylsulphonamidoanisol and 1 - amino - 5 - dimethylsulphonamido - 2 - methylbenzene. The starting dicarboxylic acids may be made by condensing 1-halogeno-benzene-2,4-dicarboxylic acids with appropriate amines or with ammonia to yield a 1-aminobenzene-2,4-dicarboxylic acid which is condensed with compounds containing reactive halogen atoms such as glycol chlorhydrins, glycerol chlorhydrin, monochloracetic acid and its derivatives substituted at the COOH group, chloropropionic acids, 3-chloro-2-hydroxy-propane-sulphonic acid or with addition products of an aldehyde with sodium bisulphite. Examples illustrate the preparation of 1 - n - butyl -, - cyclohexyl-and-methylaminobenzene - 2,4 - dicarboxylic acids and N - (2,4-dicarboxyphenyl)-glycine by treating 1-chlorobenzene - 2,4 - dicarboxylic acid with the appropriate amine in the presence of caustic soda, copper powder and copper sulphate.ALSO:A printing paste for development on cellulosic fibres by means of steam contains a compound of the formula <FORM:0766609/IV(b)/1> where R is an aryl residue and X is an alkyl or cycloalkyl group which may be substituted, or a water-soluble salt thereof. Compounds in which R is derived from amines of accentuated basic character, e.g. chloroanilines, toluidines, cresidines, anisidines, which may be halogenated, monoacylated b -diamines, which may be halogenated, alkylated or alkoxylated, benzidine or o-dianisidine or in which X is a group containing at least 3 carbon atoms and R is derived from amines of less basic character than those listed above, e.g. nitro-analines, -toluidines, -anisidines and -cresidines and dichloranilines, may be used in neutral steaming processes. Acidsteaming increases the rate of colour development and the steaming process may be completed in from 30 seconds to 1 minute by the use of an acid vapour. Acidsteaming, or passage through an acid bath, may also be an advantage when using compounds in which X contains less than 3 carbon atoms or when using compounds obtained from amines of less basic character. The paste may be made by dissolving the diazoamino-compound in a dilute alkali, with or without the addition of alcohol or dyeing assistants, and admixing with a thickener such as starch-tragacanth. The preparation of the diazoamino-compounds is described (see Group IV(b)). In example (10) cotton or other natural or regenerated fibres are printed with a paste prepared from a diazoamino compound made from 4-chloro-2-aminotoluene and 1-n-butylamino - benzene - 2, 4 - dicarboxylic acid, caustic soda, ethanol, the sodium salt of the o-phenetidide of b -hydroxynaphthoic acid and starch-tragacanth, a red colour being developed by neutral steaming.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR766609X | 1953-12-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB766609A true GB766609A (en) | 1957-01-23 |
Family
ID=9183420
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB34025/54A Expired GB766609A (en) | 1953-12-01 | 1954-11-24 | Improvements in and relating to diazoamino derivatives |
Country Status (3)
Country | Link |
---|---|
CH (1) | CH324196A (en) |
DE (1) | DE1000392C2 (en) |
GB (1) | GB766609A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4245119A (en) * | 1977-09-27 | 1981-01-13 | American Cyanamid Company | 4-(Monoalkylamino) benzene polycarboxylic acids |
US4245120A (en) * | 1977-09-27 | 1981-01-13 | American Cyanamid Company | 4-(Monoalkylamino)benzene polycarboxylic acids |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE513209C (en) * | 1928-07-15 | 1930-11-26 | I G Farbenindustrie Akt Ges | Process for the preparation of diazoamino compounds |
-
1954
- 1954-11-20 CH CH324196D patent/CH324196A/en unknown
- 1954-11-24 GB GB34025/54A patent/GB766609A/en not_active Expired
- 1954-11-30 DE DE1954C0010341 patent/DE1000392C2/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4245119A (en) * | 1977-09-27 | 1981-01-13 | American Cyanamid Company | 4-(Monoalkylamino) benzene polycarboxylic acids |
US4245120A (en) * | 1977-09-27 | 1981-01-13 | American Cyanamid Company | 4-(Monoalkylamino)benzene polycarboxylic acids |
Also Published As
Publication number | Publication date |
---|---|
DE1000392B (en) | 1957-01-10 |
DE1000392C2 (en) | 1957-06-19 |
CH324196A (en) | 1957-09-15 |
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