GB2024835A - Reactive Dyes - Google Patents
Reactive Dyes Download PDFInfo
- Publication number
- GB2024835A GB2024835A GB7913395A GB7913395A GB2024835A GB 2024835 A GB2024835 A GB 2024835A GB 7913395 A GB7913395 A GB 7913395A GB 7913395 A GB7913395 A GB 7913395A GB 2024835 A GB2024835 A GB 2024835A
- Authority
- GB
- United Kingdom
- Prior art keywords
- parts
- dye
- acid
- methoxy
- dyes
- 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.)
- Granted
Links
- 239000000985 reactive dye Substances 0.000 title claims abstract description 9
- 239000000975 dye Substances 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 11
- 238000004043 dyeing Methods 0.000 claims abstract description 11
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052794 bromium Chemical group 0.000 claims abstract description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000004753 textile Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 4
- 239000010985 leather Substances 0.000 claims description 3
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 claims description 2
- GYFZMCLUPHXUDV-UHFFFAOYSA-N 2-ethoxy-5-methylaniline Chemical compound CCOC1=CC=C(C)C=C1N GYFZMCLUPHXUDV-UHFFFAOYSA-N 0.000 claims description 2
- HKTWHHAJDJCUPC-UHFFFAOYSA-N 7-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 HKTWHHAJDJCUPC-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 2
- 239000005457 ice water Substances 0.000 claims description 2
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- 235000010288 sodium nitrite Nutrition 0.000 claims description 2
- 238000001694 spray drying Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 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
- C09B62/085—Monoazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
The present invention provides reactive dyes which in the form of the free acid have the general formula I <IMAGE> where R is methoxy or ethoxy and X is chlorine or bromine, individual Xs being identical or different. The dyes are mainly used for dyeing hydroxyl-containing material, particularly cellulosic fibres.
Description
SPECIFICATION
Reactive Dyes
The present invention provides novel dyes which in the form of the free acid have the general formula
where R is methoxy or ethoxy and X is chlorine or bromine, the two X's being identical or different.
Preferably, R is methoxy and/or each X is chlorine.
The compounds of the general formula I may be prepared by acylating a compound of the general formula
with a compound of the general formula
R and X having the above meanings.
Details of a convenient way of carrying out the preparation are to be found in the Example, where parts and percentages are by weight, unless stated otherwise. Dyes of the general formula I may be used for dyeing hydroxyl-containing textile material, particularly cellulosic textile material, especially by cold dyeing processes, and for dyeing leather. The dyeings obtained are distinguished by good iightfastness and wetfastness. The dyes according to the invention have a high tinctorial strength.
Example
250 parts of ice, followed by 13.8 parts of sodium nitrite, are added to a strongly acid solution of 76.7 parts of 2-naphthylamine-4,6,8-trisulfonic acid in 400 parts of water, and the mixture is stirred for 1 2 hours at 0--3 OC. After adding 1 part of amidosulfonic acid, a solution of 27.4 parts of 2 methoxy-5-methyl-1 -aminobenzene in aqueous hydrochloric acid is run in, and the coupling is completed at a slightly acid pH. A suspension of 37 parts of cyanuric chloride in 375 parts of ice water is then added to the dye solution and the mixture is stirred for 1 5 hours at 1 5-200C and at a slightly acid pH, maintained by adding dilute sodium hydroxide solution.After completion of the reaction, 28 parts of disodium hydrogen phosphate are dissolved in the dye solution. The dye is then precipitated with 360 parts of potassium chloride at a pH of 6.8 and is filtered off after stirring for 3 hours, and the filter residue is dried at 35 C under reduced pressure. 224 parts of an orange powder, which dyes natural or regenerated cellulose in strong lightfast and wetfast golden yellow hues are obtained.
The dye can also be isolated by direct spray drying.
If the synthesis is carried out similarly with 2-ethoxy-5-methyl-1 -aminobenzene instead of 2methoxy-5-methyl-1 -aminobenzene, a dye with similar properties is obtained.
Claims
1. A reactive dye which in the form of the free acid has the formula I
where R is methoxy or ethoxy and X is chlorine or bromine, individual Xs being identical or different.
2. A reactive dye as claimed in claim 1, wherein R is methoxy and each X is chlorine.
3. A process for the preparation of a dye as claimed in claim 1, wherein a compound of the formula
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (4)
1. A reactive dye which in the form of the free acid has the formula I
where R is methoxy or ethoxy and X is chlorine or bromine, individual Xs being identical or different.
2. A reactive dye as claimed in claim 1, wherein R is methoxy and each X is chlorine.
3. A process for the preparation of a dye as claimed in claim 1, wherein a compound of the formula
is acylated with a compound of the formula
R and X having the meanings given in claim 1.
4. A process for dyeing cellulose-containing textile material or dyeing leather wherein a reactive dye as claimed in claim 1 or 2 or prepared by a process as claimed in claim 3 is used.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2816937A DE2816937C2 (en) | 1978-04-19 | 1978-04-19 | Use of reactive dyes for dyeing cellulosic textile material or leather |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2024835A true GB2024835A (en) | 1980-01-16 |
| GB2024835B GB2024835B (en) | 1982-09-02 |
Family
ID=6037375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7913395A Expired GB2024835B (en) | 1978-04-19 | 1979-04-18 | Reactive dyes |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS54158434A (en) |
| CH (1) | CH637678A5 (en) |
| DE (1) | DE2816937C2 (en) |
| FR (1) | FR2423519A1 (en) |
| GB (1) | GB2024835B (en) |
| IT (1) | IT1166715B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5227478A (en) * | 1982-09-13 | 1993-07-13 | Sandoz Ltd. | 2-chloro-4-[4'-(4",8"-disulfonaphth-2"-ylazo)-2'-methoxy-5'-methylanilino]-6 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH655734A5 (en) * | 1982-09-13 | 1986-05-15 | Sandoz Ag | CHLORTRIAZINYL MONOAZO COMPOUNDS. |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE629952A (en) * | ||||
| FR1143176A (en) * | 1954-11-29 | 1957-09-27 | Ici Ltd | New monoazo coloring matters |
| DE1045575B (en) * | 1954-11-29 | 1958-12-04 | Ici Ltd | Process for the preparation of monoazo dyes |
| DE1110783B (en) * | 1956-09-06 | 1961-07-13 | Ciba Geigy | Process for the preparation of monoazo dyes |
| GB838307A (en) * | 1957-06-05 | 1960-06-22 | Ici Ltd | New monoazo triazine dyestuffs |
| CH358530A (en) * | 1957-06-05 | 1961-11-30 | Ici Ltd | Process for the preparation of new monoazo dyes |
| CH427088A (en) * | 1962-03-26 | 1966-12-31 | Ciba Geigy | Process for the preparation of new monoazo dyes |
| NL144647C (en) * | 1962-11-13 | |||
| US3741657A (en) * | 1971-03-03 | 1973-06-26 | Raytheon Co | Laser gyroscope |
| CA1077602A (en) * | 1976-01-02 | 1980-05-13 | Raytheon Company | Electromagnetic wave ring resonator |
-
1978
- 1978-04-19 DE DE2816937A patent/DE2816937C2/en not_active Expired
-
1979
- 1979-03-08 FR FR7905926A patent/FR2423519A1/en active Granted
- 1979-03-19 IT IT21120/79A patent/IT1166715B/en active
- 1979-04-11 CH CH343679A patent/CH637678A5/en not_active IP Right Cessation
- 1979-04-16 JP JP4551079A patent/JPS54158434A/en active Pending
- 1979-04-18 GB GB7913395A patent/GB2024835B/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5227478A (en) * | 1982-09-13 | 1993-07-13 | Sandoz Ltd. | 2-chloro-4-[4'-(4",8"-disulfonaphth-2"-ylazo)-2'-methoxy-5'-methylanilino]-6 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54158434A (en) | 1979-12-14 |
| CH637678A5 (en) | 1983-08-15 |
| IT1166715B (en) | 1987-05-06 |
| GB2024835B (en) | 1982-09-02 |
| IT7921120A0 (en) | 1979-03-19 |
| FR2423519A1 (en) | 1979-11-16 |
| DE2816937A1 (en) | 1979-10-25 |
| DE2816937C2 (en) | 1982-07-15 |
| FR2423519B1 (en) | 1985-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |