GB1577318A - Water-soluble monoazo dyes based on amino-diphenyl ether sulphonic acids and phenols - Google Patents
Water-soluble monoazo dyes based on amino-diphenyl ether sulphonic acids and phenols Download PDFInfo
- Publication number
- GB1577318A GB1577318A GB3164376A GB3164376A GB1577318A GB 1577318 A GB1577318 A GB 1577318A GB 3164376 A GB3164376 A GB 3164376A GB 3164376 A GB3164376 A GB 3164376A GB 1577318 A GB1577318 A GB 1577318A
- Authority
- GB
- United Kingdom
- Prior art keywords
- water
- sulphonic acid
- soluble monoazo
- monoazo dye
- amino
- 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.)
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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
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
- C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof
-
- 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
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/12—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the benzene series
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
(54) WATER-SOLUBLE MONOAZO DYES BASED ON
AMINODIPHENYL ETHER SULPHONIC ACIDS AND PHENOLS
(71) We, IMPERIAL CHEMICAL INDUSTRIES LIMITED, Imperial
Chemical House, Millbank, London SWIP 3JF, a British Company, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- This application relates to monoazo dyes and their application to textile materials.
According to the invention, there are provided water-soluble monoazo dyes which, in the form of the free acids, have the formula:
wherein n has a value of 1 or 2 and R1, R2 and R3 each independently represents hydrogen, halogen, alkyl, alkoxy or aryl provided that R', R2 and R3 together do not contain more than eight carbon atoms.
It is preferred that n is 1 and it is also preferred that the sulphonic acid group is not ortho to the azo group. Thus, preferred dyes have the formulae:
wherein R', R2 and R3 have the meanings given above. These dyes have higher light fastness than those in which the sulphonic acid group is ortho to the azo group.
The dyes of Formula I may be prepared by diazotising the 4-aminodiphenyl ether sulphonic acid of the formula:
wherein R' and n have the meanings given above, and coupling the resulting diazo compound with a phenol of the formula:
wherein R2 and R3, which are in ortho or meta positions relative the hydroxy group, have the meanings given above, and R', R2 and R3 together do not contain more than eight carbon atoms.
Aminodiphenyl ether sulphonic acids which may be used in making the dyes of the invention include 4-aminodiphenyl ether-2-sulphonic acid, 4-amino-4'-tert.butyldiphenyl ether-2-sulphonic acid, 4-amino-4'-methoxydiphenyl ether-2sulphonic acid, 4-aminodiphenyl ether-3-sulphonic acid, 4-amino-4'-methyldiphenyl ether-3-sulphonic acid, 4-amino-4'-methoxydiphenyl ether-3-sulphonic acid, 4-amino-4'-chlorodiphenyl ether-3-sulphonic acid, 4'-aminodiphenyl ether-4sulphonic acid and 4'-amino-4-methoxydiphenyl ether-3-sulphonic acid.
Examples of phenols which may be used as coupling components in making the dyes include phenol, o- and m-cresols, 2-methoxyphenol, o- and m-chlorophenols, 3-methoxyphenol, 2,5-, 2,6- and 3,5-dimethylphenols, 6-chloro-3-methylphenol and 2-hydroxydiphenyl.
The reactions leading to the formation of the dyes of the invention may be performed using conditions that have been fully described in the prior art for such reactions. Similarly the dyes may be isolated by known methods and, as in the case of other dyes containing sulphonic acid groups, it is often convenient to isolate and use the dyes in the form of their water-soluble salts, particularly their alkali-meta; or ammonium salts and especially sodium salts. It is to be understood that the invention relates to both the free acids and their salts.
The dyes of the invention are particularly suitable for applying to synthetic polyamide textile materials, for example nylon 66, nylon 6 and nylon 11, using any of the general methods known for the application of acid dyes to such materials.
The dyes provide yellow shades having a high degree of fastness to wet treatments and to light.
The invention is illustrated but not limited by the following Examples in which all parts and percentages are by weight.
Example 1.
5.7 Parts of the sodium salt of 4-aminodiphenyl ether-2-sulphonic acid are dissolved in 100 parts of water. The stirred solution is cooled to -50C and 10 parts of 36% hydrochloric acid are added followed by 10 parts of 13.8% sodium nitrite solution. After stirring for a further 1 hour at O5 C, the diazo suspension is added to a solution of 2.2 parts of 2,6-dimethylphenol in 100 parts of water and 32% sodium hydroxide solution, maintaining the temperature below 10 C and the pH between 8 and 9 by the addition of sodium'hydroxide solution as required. The coupling suspension is stirred for a further 16 hours allowing the temperature to rise to 200C and the product is filtered off and dried.
When applied to nylon from a neutral to weakly acid bath, a yellow shade is obtained having very good fastness to wet treatments and to light.
The following Table gives further examples of dyestuffs of the invention which may be obtained by diazotising the aminodiphenylether sulphonic acid listed in the second column and coupling under alkaline conditions with the para coupling phenol listed in the third column.
Example 2 4-aminodiphenylether-2-sulphonic acid m-cresol 3 ,, 2,6-dimethylphenol 4 " 2-hydroxydiphenyl 5 4-amino-4'-tertbutyldiphenylether-2- phenol sulphonic acid 6 " o-cresol 7 " 2-methoxyphenol 8 " 2-chlorophenol 9 4-amino-4'-methoxydiphenylether-2- 3 ,Sdirnethylphenol sulphonic acid 10 " 2-hydroxydiphenyl 11 4-aminodiphenylether-3-sulphonic acid 2,5-lime thyiphenol 12 ,, 6-chlow-3methyl phenol 13 ,, 2-hydroxydiphenyl 14 4'-aminodiphenylether-4-sulphonic acid o-cresol 15 " 2,6-dimethylphenol 16 ,, 2-hydroxydiphenyl 17 4'-amino-4-methoxydiphenylether-3- m-cresol sulphonic acid 18 " 3-methoxyphenol 19 ,, 2-hydroxydiphenyl 20 4-aminodiphenylether-2-sulphonic acid 2-methoxyphenol 21 " 3-methoxyphenol
WHAT WE CLAIM IS:
1. A water-soluble monoazo dye which, in the form of the free acid, has the formula:
wherein n has a value of I or 2 and R'; R2 and R3 each independently represents hydrogen, halogen, alkyl, alkoxy or aryl provided that R1, R2 and R3 together do not contain more than eight carbon atoms.
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (10)
1. A water-soluble monoazo dye which, in the form of the free acid, has the formula:
wherein n has a value of I or 2 and R'; R2 and R3 each independently represents hydrogen, halogen, alkyl, alkoxy or aryl provided that R1, R2 and R3 together do not contain more than eight carbon atoms.
2. A water-soluble monoazo dye as claimed in claim I wherein R', R2 and R3
each independently represents hydrogen, halogen, alkyl or alkoxy.
3. A water-soluble monoazo dye as claimed in claim I or claim 2 wherein n is 1.
4. A water-soluble monoazo dye as claimed in claim 3 having the formula:
wherein R', R2 and R3 have the meanings given in claim 1.
5. A water-soluble monoazo dye as claimed in claim 3 having the formula:
wherein R', R2 and R3 have the meanings given in claim 1.
6. A water-soluble monoazo dye as claimed in claim I and specifically identified herein.
7. A method for the preparation of a water-soluble monoazo dye as defined in claim I which comprises diazotising a 4-aminodiphenyl ether sulphonic acid of the formula:
wherein R' and n have the meanings given in claim 1, and coupling the resulting diazo compound with a phenol of the formula:
wherein R2 and R3, which are in ortho or meta positions relative the hydroxy group, have the meanings given in claim 1, and R', R2 and R3 together do not contain more than eight carbon atoms.
8. A method as claimed in claim 7 conducted substantially as hereinbefore described with reference to any one of the foregoing Examples.
9. A water-soluble monoazo dye whenever prepared by a method claimed in claim 7 or claim 8.
10. A process for the coloration of synthetic polyamide textile materials which comprises applying thereto a water-soluble monoazo dye as claimed in any one of claims 1 L and 9.
II. Synthetic polyamide textile materials whenever coloured by the process claimed in claim 10.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3164376A GB1577318A (en) | 1977-07-08 | 1977-07-08 | Water-soluble monoazo dyes based on amino-diphenyl ether sulphonic acids and phenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3164376A GB1577318A (en) | 1977-07-08 | 1977-07-08 | Water-soluble monoazo dyes based on amino-diphenyl ether sulphonic acids and phenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1577318A true GB1577318A (en) | 1980-10-22 |
Family
ID=10326243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3164376A Expired GB1577318A (en) | 1977-07-08 | 1977-07-08 | Water-soluble monoazo dyes based on amino-diphenyl ether sulphonic acids and phenols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1577318A (en) |
-
1977
- 1977-07-08 GB GB3164376A patent/GB1577318A/en not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |