GB740862A - Improvements relating to monoazo dyestuffs and their use - Google Patents
Improvements relating to monoazo dyestuffs and their useInfo
- Publication number
- GB740862A GB740862A GB28461/53A GB2846153A GB740862A GB 740862 A GB740862 A GB 740862A GB 28461/53 A GB28461/53 A GB 28461/53A GB 2846153 A GB2846153 A GB 2846153A GB 740862 A GB740862 A GB 740862A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aminobenzoylamino
- methyl
- benzoylamino
- group
- sulphonic acid
- 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
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 abstract 4
- 239000000975 dye Substances 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 230000008878 coupling Effects 0.000 abstract 3
- 238000010168 coupling process Methods 0.000 abstract 3
- 238000005859 coupling reaction Methods 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 3
- GFNKTLQTQSALEJ-UHFFFAOYSA-N 1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C=C1 GFNKTLQTQSALEJ-UHFFFAOYSA-N 0.000 abstract 2
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 229950011260 betanaphthol Drugs 0.000 abstract 2
- 239000000460 chlorine Chemical group 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- -1 aminobenzoylamino Chemical group 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical class NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 abstract 1
- 150000004780 naphthols Chemical class 0.000 abstract 1
- 229960003742 phenol Drugs 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 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
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
-
- 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
- C09B45/38—Preparation from compounds with —OH and —COOH adjacent in the same ring or in peri position
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Amines, used as diazo components in the preparation of azo dyes (see Group IV (c)), of general formula <FORM:0740862/IV(a)/1> where X represents hydrogen, chlorine, a methyl, methoxy or sulphonic acid group, Y represents hydrogen or a methyl group, and n1 and n2 represent 0 or 1, are prepared from 5 - amino - 2 - hydroxybenzene - 1 - carboxylic acids which may be substituted in the 3-position as defined, by reaction with p-nitrobenzoyl chloride or p-nitrophenyl isocyanate, reducing the nitro group to the amino group, again reacting with p-nitrobenzoyl chloride or p-nitrophenylisocyanate and reducing the nitro group to the amino group. The acylating agents may contain methyl group ortho- or metato the nitro group. Several compounds corresponding to the general formula are specified.ALSO:The invention comprises monoazo dye stuffs corresponding to the general formula: <FORM:0740862/IV(c)/1> wherein X represents hydrogen, chlorine, a methyl, methoxy or sulphonic acid group, Y represents hydrogen or a methyl group, n1 and n2 are 0 or 1, and A represents the radical of a 2-(31- or 41-aminobenzoylamino) - 5 - hydroxynapthalene-7-sulphonic acid or a 2-[31 or41- (311-or 411-aminobenzoylamino)-benzoylamino] -5-hydroxynapthalene-7-sulphonic acid or a derivative thereof in which the -N-C-bridging members, between the benzene and napthalene nucleus, are members of a thiazole or imidazole ring fused to the napthalene ring in the 1:2- positions, the benzene nuclei of A containing, if desired, further substituents, preferably non-ionogenic (i.e. which do not form salts). The dyestuffs are prepared by diazotising the corresponding amine (see Group IV(b)) and coupling with component A. The dyestuffs may be used as direct cellulose dyestuffs and dye in red shades but are preferably diazotized on the fibre and developed with coupling components not containing sulphonic acid groups. Unsulphonated phenolic and enolic azo components are suitable developers, but naphthols coupling ortho to the hydroxy group are preferred, particularly 2-naphthol which yields red shades. As diazo components, 5-[41-(411 -aminobenzoylamino)-benzoylamino] -, 5-[41-(311-methyl-411 - aminobenzoylamino)-benzoylamino]-, 5-[41-(311-methyl-411-aminobenzoylamino) -31 - methylbenzoylamino]-, 5-[41- (411-aminobenzoylamino)-31 methylbenzoylamino]-, 5-[41-(211:511-dimethyl-411 -aminobenthoylamino) - benzoylamino]-, 5-[41-(211-methyl-411 - aminobenzoylamino)-benzoylamino]-, 5-[41-(411-aminobenzoylamino)-21 -methylbenzoylamino]- and 5-[41 -(411-aminophenylureido) - benzoylamino]-2-hydroxybenzene -1-carboxylic acid, 5-[41 -(311-methyl-411-aminobenzoylamino) - benzoylamino]- and 5-[41-(411-aminobenzoylamino) - benzoylamino]-3-sulpho-2-hydroxy-benzene-1-carboxylic acid, 5-[41-(411 aminobenzoylamino)-benzoylamino] -3-methyl-, 5-[41 - (411-aminobenzoylamino) - benzoyl - amino]-3-chloro- and 5-[41-(411-aminobenzoylamino) - benzoylamino]-3-methoxy-2-hydroxybenzene-1-carboxylic acid, 41-(411-aminophenylureido)- and 41(311-methyl-411-aminobenzoylamino) - 3 - carboxy - 4 - hydroxydiphenylurea, and 41-(311-methyl-411 aminobenzoylamino)-5-sulpho - 3 - carboxy-4-hydroxydiphenyl urea are specified. As azo components, 2-(41-aminobenzoylamino)-, 2-(31-aminobenzoylamino)-, 2-(41-methyl-31 -aminobenzoylamino)-, 2-(41-methoxy-31 -aminobenzoylamino)-, 2-(31-methyl-41 -aminobenzoylamino)-, 2-(41-chloro-31 -aminobenzoylamino)-, 2-[31 or 41-(411 -aminobenzoylamino) - benzoylamino]-, 2-[41-(411-amino-311-methyl-benzoylamino)] -2-[31-(411-aminobenzoylamino)-41 - methylbenzoylamino]- and 2-[41-(311-amino-411-methyl-benzoylamino) -benzoylamino]-, 5-hydroxynapthalene-7-sulphonic acid, 2-(411 or 311-aminophenyl)- and 2-[411- or 311- (4111- or 3111-aminobenzoylamino)-phenyl]-naphtho - 11.21:4.5-imidazole-51-hydroxy-71 -sulphonic acid, 2-(411 or 311-aminophenyl)-, and 2-[411- or 311- (4111- or 3111 -aminobenzoylamino)-phenyl]- naphtho-11.21 :4.5 -thiazole-51-hydroxy-71-sulphonic acid are specified. Examples describe the preparation of monoazo-dyes using the components described above and also the diazotization of the dyes on the fibres and development with 2-naphthol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH740862X | 1952-10-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB740862A true GB740862A (en) | 1955-11-23 |
Family
ID=4533153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28461/53A Expired GB740862A (en) | 1952-10-17 | 1953-10-15 | Improvements relating to monoazo dyestuffs and their use |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB740862A (en) |
-
1953
- 1953-10-15 GB GB28461/53A patent/GB740862A/en not_active Expired
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