GB755571A - Improvements relating to metallisable polyazo dyestuffs and their use - Google Patents
Improvements relating to metallisable polyazo dyestuffs and their useInfo
- Publication number
- GB755571A GB755571A GB16917/54A GB1691754A GB755571A GB 755571 A GB755571 A GB 755571A GB 16917/54 A GB16917/54 A GB 16917/54A GB 1691754 A GB1691754 A GB 1691754A GB 755571 A GB755571 A GB 755571A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- hydroxynaphthalene
- sulphonic acid
- nitro
- 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
- -1 polyazo Polymers 0.000 title abstract 5
- 239000002253 acid Substances 0.000 abstract 8
- 150000007513 acids Chemical class 0.000 abstract 5
- 239000000975 dye Substances 0.000 abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 5
- 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 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 abstract 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 3
- 230000008878 coupling Effects 0.000 abstract 3
- 238000010168 coupling process Methods 0.000 abstract 3
- 238000005859 coupling reaction Methods 0.000 abstract 3
- 125000004306 triazinyl group Chemical group 0.000 abstract 3
- SGBQUMZTGSQNAO-UHFFFAOYSA-N 2-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(O)=CC=C21 SGBQUMZTGSQNAO-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 229950011260 betanaphthol Drugs 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000004696 coordination complex Chemical class 0.000 abstract 2
- 229910052802 copper Inorganic materials 0.000 abstract 2
- 239000010949 copper Substances 0.000 abstract 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 229940124530 sulfonamide Drugs 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- PWJNDVAKQLOWRZ-UHFFFAOYSA-N 1-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(O)=C(S(O)(=O)=O)C=CC2=C1 PWJNDVAKQLOWRZ-UHFFFAOYSA-N 0.000 abstract 1
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 abstract 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 1
- ZJYJZEAJZXVAMF-UHFFFAOYSA-N 2-nitronaphthalene Chemical compound C1=CC=CC2=CC([N+](=O)[O-])=CC=C21 ZJYJZEAJZXVAMF-UHFFFAOYSA-N 0.000 abstract 1
- IQGMRVWUTCYCST-UHFFFAOYSA-N 3-Aminosalicylic acid Chemical compound NC1=CC=CC(C(O)=O)=C1O IQGMRVWUTCYCST-UHFFFAOYSA-N 0.000 abstract 1
- XFXOLBNQYFRSLQ-UHFFFAOYSA-N 3-amino-2-naphthoic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(N)=CC2=C1 XFXOLBNQYFRSLQ-UHFFFAOYSA-N 0.000 abstract 1
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 abstract 1
- MRBKRZAPGUCWOS-UHFFFAOYSA-N 3-amino-4-hydroxybenzoic acid Chemical compound NC1=CC(C(O)=O)=CC=C1O MRBKRZAPGUCWOS-UHFFFAOYSA-N 0.000 abstract 1
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 abstract 1
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 abstract 1
- ZIPJXJGTIGXUSE-UHFFFAOYSA-N 6-diazocyclohexa-2,4-dien-1-ol Chemical compound OC1C=CC=CC1=[N+]=[N-] ZIPJXJGTIGXUSE-UHFFFAOYSA-N 0.000 abstract 1
- NWYPJANFHLUNFH-UHFFFAOYSA-N 7-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=C(O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 NWYPJANFHLUNFH-UHFFFAOYSA-N 0.000 abstract 1
- HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 abstract 1
- KVHHMYZBFBSVDI-UHFFFAOYSA-N 8-aminonaphthalen-2-ol Chemical class C1=C(O)C=C2C(N)=CC=CC2=C1 KVHHMYZBFBSVDI-UHFFFAOYSA-N 0.000 abstract 1
- KMXMLAGYNHELHA-UHFFFAOYSA-N 8-hydroxynaphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 KMXMLAGYNHELHA-UHFFFAOYSA-N 0.000 abstract 1
- NNWYOMXEYRMKEU-UHFFFAOYSA-N N-(1-hydroxynaphthalen-2-yl)-3-oxobutanamide Chemical compound C(CC(=O)C)(=O)NC1=C(C2=CC=CC=C2C=C1)O NNWYOMXEYRMKEU-UHFFFAOYSA-N 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 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
- HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 150000001869 cobalt compounds Chemical class 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000001465 metallisation Methods 0.000 abstract 1
- GGXAKQQKCYFCHS-UHFFFAOYSA-N n-(4-aminophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(N)C=C1 GGXAKQQKCYFCHS-UHFFFAOYSA-N 0.000 abstract 1
- 150000002790 naphthalenes Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
-
- 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
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises dyestuffs of formula <FORM:0755571/IV(c)/1> where A is the residue of a hydroxynaphthalene sulphonic acid and containing a hydroxyl group in the o-position to the azo group, X is a substituent which forms a metal complex, Y is a direct link or - NH - CO - Ph -, - NH - CO - NH - Ph -, or <FORM:0755571/IV(c)/2> where Ph is a phenylene radicle, Cy is a triazinyl radicle and 2 a halogen atom, a hydroxyl group or an amine radicle, B is a residue of a diazo compound of the benzene or naphthalene series containing a carboxyl or hydroxyl group in the o-position to the azo group, the naphthalene radicle contains the hydroxyl group in the o-position to the azo group and the aromatic nuclei of A, B, D and Y may be further substituted, D preferably containing a sulphonic acid group. The dyestuffs may be converted to their copper or cobalt compounds and the aromatic nuclei may contain substituents such as halogen, alkyl, hydroxyl, alkoxy, nitro, acylamino, arylamino, carboxyl, sulphonic acid, sulphonamide, aryl or alkylsulphonyl, alkoyl and aroyl groups. The dyestuffs may be made by coupling the necessary tetrazotized 4, 41-diaminodiphenyl in an alkaline medium with equimolecular amount of a hydroxynaphthalene sulphonic acid and a monoazo dyestuff obtained from an an acetoacetylamino-hydroxy-naphthalene by coupling with an o-carboxy- or preferably an o-hydroxydiazo benzene or -naphthalene in a weakly acid to weakly alkaline medium and optinally in the presence of a tertiary nitrogen base. The monoazo dyestuff may also be used in the form of its metal complex. Advantageously the monoazo dyestuff contains a water-solubilizing group. Components mentioned which yield B are derivatives of 1-amino-7-hydroxynaphthalene and its 3- and 4-sulphonic acids, 1-amino-8-hydroxynaphthalen -3, 6- and -4, 6-disulphonic acids, 2-amino-6-hydroxynaphthalene-8-sulphonic acid and especially 1- or 2-amino-5-hydroxynaphthalene-7-suphonic acid, 2-amino-8-hydroxynaphthalene-6-sulphonic acid and 31 and 41 - aminobenzoyl or -aminophenyl-carbamyl derivatives thereof. These compounds on treatment with diketene, preferably in an aqueous solution of their alkali metal salts, yield the corresponding acetoacetylaminocompound. The components may also be treated with cyanuric chloride, an acetoacetylamino compound of the benzene series and, if desired, an amine, to yield the triazinyl derivative. Specified diazo components used in the preparation of the monoazo dyestuffs are 2-aminobenzene-1-carboxylic acid and its 4-chloro- and 5-nitro-, -sulpho- and -sulphonamido-derivatives, 2-aminonaphthalene-3-carboxylic acid, 2-amino-1-hydroxybenzene, 4-methyl-, -chloro-, nitro-, -methylsulphonyl-, -acetyl- and acetyllamino-, 5 nitro-, 4, 6 dichloro- and -dinitro-, 4-methyl- or -chloro-6-nitro-, 6-methyl- or -chloro-4-nitro-, 4-tert. amyl-6-nitro, 4-acetylamino-6-nitro-, 4-nitro-6-acetylamino- and 4-methyl- and -chloro-5-nitro-2-amino-1-hydroxybenzene, 4-methyl-, -chloro-, -nitro- and -benzoylamino-2-amino-1-hydroxybenzene-6-sulphonic acid, 6-methyl-, -chloro-, -nitro- and -benzoyll-amino-2-amino-1-hydroxybenzene-4- sulphonic acid, 3-amino-2-hydroxybenzene-1-carboxylic acid -5- sulphonic acid, 4-hydroxy-3-aminobenzene-1-carboxylic acid, 4 - hydroxy - 3 - aminobenzene - 1 - sulphonic acid, - sulphonamide, and sulphonic acid methyl-, dimethyl-, diethyl- and oxethylamides, 1- amino-2-hydroxynaphthalene-4- and -6-sulphonic acid and 6-nitronaphthalene -1, 2-diazoxide-4-sulphonic acid, 4, 41 - diaminodiphenyl derivatives specified are the 3, 31- dihydroxy-, di-carboxy-, -dimethoxy- and -di-carbomethyoxy compounds. Specified naphthol sulphonic acids for coupling with the diphenyl are 1-hydroxynaphthalene- 3, 6-, -4, 8- and especially -3, 8- disulphonic acids, 1-hydroxynaphthalene- 3, 6, 8- trisulphonic acid, 2-hydroxynaphthalene -3, 6- and -6, 8- disulphonic acids, 1, 8-dihydroxynaphthalene -3, 6-disulphonic acid, 1- hydroxynaphthalene -4- and -5- sulphonic acid, 2-hydroxynaphthalene -4-, -6-, -7- and -8- sulphonic acid, 2-amino-, -acetylamino- and -(31-sulphonphenyl) 8-hydroxynaphthalene-7-sulphonic acid, 2-amino-acetylamino- and -(31-sulphonphenyl) -8-hydroxynaphthalene-6-sulphonic acid and 1-amino-8-hydroxynaphthalene-3, 6- and -4, 6- disulphonic acid. Before or after metallization, which may be effected in substance or on the fibre, the dyestuffs dye cellulose material in grey-violet to grey-green shades. Treatment with copper- and cobalt-yielding substances is effected in conventional fashion. Dyestuffs containing both cobalt and copper may be made. Examples are provided illustrating the preparation of dyestuffs from certain of the above specified components and additional diazo component used in the preparation of the monoazo dyestuffs is 1-amino-2-hydroxy-5-chlorobenzene and the triazinyl portion of a dyestuff is derived from the product of the reaction between 1-amino-8-hydroxynaphthalene-3, 6-disulphonic acid, cyanuric chloride, 1-amino-4-acetoacetylaminobenzene and aniline or p-methoxyaniline.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH755571X | 1953-06-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB755571A true GB755571A (en) | 1956-08-22 |
Family
ID=4534241
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB16917/54A Expired GB755571A (en) | 1953-06-10 | 1954-06-09 | Improvements relating to metallisable polyazo dyestuffs and their use |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB755571A (en) |
-
1954
- 1954-06-09 GB GB16917/54A patent/GB755571A/en not_active Expired
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