GB906729A - Azo triazole dyestuffs - Google Patents
Azo triazole dyestuffsInfo
- Publication number
- GB906729A GB906729A GB9762/60A GB976260A GB906729A GB 906729 A GB906729 A GB 906729A GB 9762/60 A GB9762/60 A GB 9762/60A GB 976260 A GB976260 A GB 976260A GB 906729 A GB906729 A GB 906729A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dyes
- acid
- groups
- naphthylamine
- aniline
- 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
- WUPZAQSKRMYJNB-MDZDMXLPSA-N 1,1'-azobis-1,2,3-triazole Chemical compound N1=NC=CN1\N=N\N1N=NC=C1 WUPZAQSKRMYJNB-MDZDMXLPSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 8
- 239000000975 dye Substances 0.000 abstract 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- -1 alkali metal cation Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 239000004202 carbamide Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 239000004753 textile Substances 0.000 abstract 2
- 125000001425 triazolyl group Chemical group 0.000 abstract 2
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 abstract 1
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 abstract 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 abstract 1
- ONADZNBSLRAJFW-UHFFFAOYSA-N 3-methoxy-4-methylaniline Chemical compound COC1=CC(N)=CC=C1C ONADZNBSLRAJFW-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 1
- 229910005948 SO2Cl Inorganic materials 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 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
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001448 anilines Chemical class 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 239000004627 regenerated cellulose Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
- 150000003852 triazoles Chemical class 0.000 abstract 1
- 210000002268 wool Anatomy 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/513—Disazo or polyazo dyes
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
- C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
- C09B62/4411—Azo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
The invention comprises dyes of formula <FORM:0906729/IV (b)/1> where A is a benzenic or naphthalenic residue, B is a benzenic or naphthalenic residue in which the azo and triazole groups are in p-position, D is a benzenic or naphthalenic residue with the triazole ring N atoms in o-position, R5 is H, AlK or OAlK, m is 0 or 1, n is 1 or 2, p is 1 or 2, r is 0, 1 or 2 and R is NH-R1-OSO3X where X is H or an alkali metal cation and R1 is a straight or branched-chain member with 2 or 3 C atoms between N and O. When A and D are derived from compounds of the aniline series the benzene nuclei may possess a condensed-on heterocyclic ring. The dyes are made by conventional methods by forming appropriate triazolised dyes containing SO3H, SO2Cl or SO2NHR1OH groups and converting these groups to the SO2R group in a final stage. Representative of A components are aniline -3- and -4-sulphonic acids, 2-amino- 5-nitrobenzene- 1-sulphonic acid, 1-naphthylamine-4-sulphonic acid, 6-nitro-2-naphthylamine-4,8-disulphonic acid and 6-(naphthol[11,21,4,5]-triazolyl)- 2-naphthylamine-4,8, 51-trisulphonic acid. The residue A may contain substituents such as nitro, acylamino, alkyl, alkoxy, carboxy, azo and triazole groups. According to the groups present various other conversions such as acylation, urea and triazole formation, diazotisation, coupling, sulphonation and reduction may be carried out at different stages in the processes of production. Representative of compounds specified for B are 2-methoxy-and-methyl-aniline, 2,5-dimethoxy-aniline, N-ethylaniline and 1-naphthylamine-7-sulphonic acid. Illustrative of specified compounds D are 2-naphthylamine and its 6-mono- and 3,6-disulphonic acids, 3-methoxy-4-methyl-aniline and 2-(p-sulpho- and -chloro-phenyl)-5-aminobenztriazole. Dyes, very fast to chlorine, are obtained when the products are free from amino and hydroxyl groups. The dyes are used to colour hydroxy-group containing textile materials, especially natural and regenerated cellulose. The dyeings may be made very fast by treating with acid-binding agents, preferably at elevated temperatures. Amide-containing textiles such as wool and silk may also be coloured. Examples are provided of the preparation of the dyes, mono- and poly-azo dyes being obtained, and their use in colouring cotton in orange shades. Amongst various components used corresponding to A are dehydrothiotoluidinedisulphonic acid, 41-aminostilbene-2,21-disulphonic acid -4,111-azo-411-methoxybenzene and 41-amino-4-nitrostilbene-2,21-disulphonic acid. R1 is illustrated as ethylene and isopropylene. Some of the above indicated final and intermediate conversions are also exemplified, e.g. polyazo dyes are obtained by urea formation and by glucose reduction of nitro groups. Specifications 837,750 and 904,800 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0027994 | 1959-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB906729A true GB906729A (en) | 1962-09-26 |
Family
ID=7092694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9762/60A Expired GB906729A (en) | 1959-03-20 | 1960-03-18 | Azo triazole dyestuffs |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE588834A (en) |
| GB (1) | GB906729A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4354968A (en) * | 1972-02-25 | 1982-10-19 | Bayer Aktiengesellschaft | Azo reactive dyestuffs having an aryl-triazinyl-aryl diazo component |
-
1960
- 1960-03-18 BE BE588834A patent/BE588834A/en unknown
- 1960-03-18 GB GB9762/60A patent/GB906729A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4354968A (en) * | 1972-02-25 | 1982-10-19 | Bayer Aktiengesellschaft | Azo reactive dyestuffs having an aryl-triazinyl-aryl diazo component |
Also Published As
| Publication number | Publication date |
|---|---|
| BE588834A (en) | 1960-09-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB906729A (en) | Azo triazole dyestuffs | |
| GB899376A (en) | New naphthalene monoazo triazine dyestuffs | |
| GB838311A (en) | New copper-containing triazine monoazo dyestuffs | |
| GB952061A (en) | Novel disazo compounds | |
| GB858183A (en) | Water-soluble azo dyestuffs containing acryloylamino groups | |
| GB987740A (en) | Water-insoluble disazo dyestuffs and process for their manufacture | |
| US2077322A (en) | Process for the manufacture of azo dyestuffs for esters of cellulose and azo dyestuffs obtained therefrom | |
| GB902228A (en) | Polyazo-dyestuffs derived from barbituric acid and process for their manufacture | |
| US1849572A (en) | Disazo-dyestuffs and process of making same | |
| US3577405A (en) | Water-soluble,yellow mono-azo dyes with active methylene coupler | |
| US2155685A (en) | Azo dyes | |
| US3074926A (en) | Azo dyes for acrylic and polyester fibers | |
| US1849573A (en) | Disazo-dyestuffs and process of making same | |
| US2793205A (en) | Disazo-dyestuffs | |
| GB984904A (en) | New reactive monoazo dyestuffs | |
| GB921319A (en) | Azo dyestuffs of the benzene and naphthalene series containing triazine rings | |
| US1784617A (en) | Trisazo dyes and process of producing the same | |
| GB923887A (en) | New monoazo triazine dyestuffs | |
| US2164524A (en) | Azo dye | |
| US2786830A (en) | Tetrakisazo-dyestuffs | |
| GB248230A (en) | Process for the manufacture of trisazo dyestuffs | |
| GB347742A (en) | Manufacture of disazo-dyestuffs | |
| GB554463A (en) | Manufacture of dyestuffs | |
| GB660196A (en) | Manufacture of new monoazo-dyestuffs | |
| GB917725A (en) | Azo dyestuffs |