GB869279A - New azodyestuffs derived from cyanuric halides and processes for their manufacture and application - Google Patents
New azodyestuffs derived from cyanuric halides and processes for their manufacture and applicationInfo
- Publication number
- GB869279A GB869279A GB28928/57A GB2892857A GB869279A GB 869279 A GB869279 A GB 869279A GB 28928/57 A GB28928/57 A GB 28928/57A GB 2892857 A GB2892857 A GB 2892857A GB 869279 A GB869279 A GB 869279A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dyes
- residue
- cooh
- group
- so3h
- 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
- 150000004820 halides Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 239000000975 dye Substances 0.000 abstract 8
- 229910006069 SO3H Chemical group 0.000 abstract 5
- -1 aminoazo Chemical group 0.000 abstract 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 5
- 150000001412 amines Chemical class 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-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
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 abstract 2
- GINUIEXFKFIZSF-UHFFFAOYSA-N 1-(methylamino)ethanesulfonic acid Chemical compound CNC(C)S(O)(=O)=O GINUIEXFKFIZSF-UHFFFAOYSA-N 0.000 abstract 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 abstract 1
- LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-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
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000005578 chrysene group Chemical group 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000002169 ethanolamines Chemical class 0.000 abstract 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 abstract 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- ABOYDMHGKWRPFD-UHFFFAOYSA-N phenylmethanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC=C1 ABOYDMHGKWRPFD-UHFFFAOYSA-N 0.000 abstract 1
- 239000004627 regenerated cellulose Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises dyes containing at least two groups imparting water solubility selected from COOH and SO3H groups, which are of formula:- <FORM:0869279/IV(c)/1> where R is a residue of a diazo component containing COOH or SO3H groups as single substituents, R1 is a benzene or naphthalene residue, n is 1 or 2, Y is NH2 or the residue of an amine containing at most 12 C atoms, with a COOH or SO3H group if containing an aryl ring, and A is a benzene residue attached to the azo group in p-position to NH. The dyes are made by reacting a trihalo-triazine with appropriate aminoazo dyes and ammonia or the required amine corresponding to Y. The reaction may be effected in any sequence and intermediates may be isolated before further reaction. Preferred dyes are those where n is 1, R is a disulphonaphthyl residue and A contains an acylamino group of up to 4 C atoms #s to N2. R1 is indicated as a phenyl group which may have methyl or alkoxy substituents, or a naphthalene residue. Preferably the dyes contain more than one COOH or SO3H group per azo group. Chlorine is the preferred halogen in the halo-triazines. R is indicated as a benzene, naphthalene, pyrene or chrysene residue. Representative of amines for specified values for Y are methyl-, diethyl-, isobutyl-, cyclohexyl, b -chlorethyl- and g -methoxypropyl-amines, ethanolamines, toluene sulphonic acid amide, glycocol, ethyl aminocarbonate, amino acetic acid ethyl ester, aminoacetamide, morpholine and especially aniline-2, 5-disulphonic acid, aminonaphthalene mono- or disulphonic acids, 1-aminodiphenyl-41-sulphonic acid and N-methylamino ethane sulphonic acid. Amines containing water-solubilizing groups are used only when dyes are chosen which contain a single SO3H or COOH group. The dyes colour cellulosic materials e.g. linen, regenerated cellulose and especially cotton, particularly when used in conjunction with an alkaline treatment. Examples are provided of the preparation of the dyes and their use in colouring cellulosic materials in yellow, red, orange and brown shades. Specifications 209,723, 299,331, 774,925, 797,946, 838,337 and 864,227 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH869279X | 1956-09-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB869279A true GB869279A (en) | 1961-05-31 |
Family
ID=4543894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28928/57A Expired GB869279A (en) | 1956-09-14 | 1957-09-13 | New azodyestuffs derived from cyanuric halides and processes for their manufacture and application |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB869279A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4338092A (en) | 1979-12-21 | 1982-07-06 | Sandoz Ltd. | Disazo compounds having a 4,6,8-trisulfonaphthyl diazo components radical and a 2-amino or substituted amino-4-chloro-1,3,5-triazin-6-yl-amino substituent |
| DE3331861A1 (en) * | 1982-09-13 | 1984-03-15 | Sandoz-Patent-GmbH, 7850 Lörrach | CHLORTRIAZINYL MONOAZO COMPOUNDS |
| US5227478A (en) * | 1982-09-13 | 1993-07-13 | Sandoz Ltd. | 2-chloro-4-[4'-(4",8"-disulfonaphth-2"-ylazo)-2'-methoxy-5'-methylanilino]-6 |
| US5243033A (en) * | 1991-01-16 | 1993-09-07 | Ciba-Geigy Corporation | Fiber-reactive disazo and tetrakisazo halotriazinyl dyes |
| US5712376A (en) * | 1995-08-22 | 1998-01-27 | Ciba Specialty Chemicals Corporation | Azo reactive dyes, their preparation and use |
-
1957
- 1957-09-13 GB GB28928/57A patent/GB869279A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4338092A (en) | 1979-12-21 | 1982-07-06 | Sandoz Ltd. | Disazo compounds having a 4,6,8-trisulfonaphthyl diazo components radical and a 2-amino or substituted amino-4-chloro-1,3,5-triazin-6-yl-amino substituent |
| DE3331861A1 (en) * | 1982-09-13 | 1984-03-15 | Sandoz-Patent-GmbH, 7850 Lörrach | CHLORTRIAZINYL MONOAZO COMPOUNDS |
| US5227478A (en) * | 1982-09-13 | 1993-07-13 | Sandoz Ltd. | 2-chloro-4-[4'-(4",8"-disulfonaphth-2"-ylazo)-2'-methoxy-5'-methylanilino]-6 |
| US5243033A (en) * | 1991-01-16 | 1993-09-07 | Ciba-Geigy Corporation | Fiber-reactive disazo and tetrakisazo halotriazinyl dyes |
| EP0495753B1 (en) * | 1991-01-16 | 1997-07-16 | Ciba SC Holding AG | Reactive dyes, methods of their preparation and their use |
| US5712376A (en) * | 1995-08-22 | 1998-01-27 | Ciba Specialty Chemicals Corporation | Azo reactive dyes, their preparation and use |
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