GB1559292A - Diphenyl ether sulphanic acid-azo phenol dyes - Google Patents

Diphenyl ether sulphanic acid-azo phenol dyes Download PDF

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Publication number
GB1559292A
GB1559292A GB31645/76A GB3164576A GB1559292A GB 1559292 A GB1559292 A GB 1559292A GB 31645/76 A GB31645/76 A GB 31645/76A GB 3164576 A GB3164576 A GB 3164576A GB 1559292 A GB1559292 A GB 1559292A
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GB
United Kingdom
Prior art keywords
water
monoazo dye
alkyl
soluble monoazo
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.)
Expired
Application number
GB31645/76A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB31645/76A priority Critical patent/GB1559292A/en
Priority to ZA00773621A priority patent/ZA773621B/en
Priority to IT25155/77A priority patent/IT1086241B/en
Priority to NL7707479A priority patent/NL7707479A/en
Priority to BR7704745A priority patent/BR7704745A/en
Priority to BE179467A priority patent/BE856945A/en
Priority to DE19772733962 priority patent/DE2733962A1/en
Priority to FR7723263A priority patent/FR2359882A1/en
Priority to JP9132377A priority patent/JPS5316037A/en
Publication of GB1559292A publication Critical patent/GB1559292A/en
Expired legal-status Critical Current

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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
    • C09B29/10—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
    • 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
    • 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
    • D06P1/02—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 azo dyes
    • D06P1/04—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 azo dyes not containing metal
    • D06P1/06—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 azo dyes not containing metal containing acid groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Description

(54) DIPHENYL ETHER SULPHONIC ACID-AZO-PHENOL DYES (71) We, IMPERIAL CHEMICAL INDUSTRIES LIMITED, Imperial Chemical House, Millbank, London SW1P 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 invention 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 adds, have the formula:
wherein n has a value of 1 or 2, Rl represents hydrogen, halogen, alkyl or alkoxy, R2 represents hydrogen, halogen or alkyl and R3 represents aryl optionally substituted by alkyl or alkoxy.
Particular mention may be made of those dyes in which R2 is hydrogen or alkyl and R3 is aryl optionally substituted by alkyl.
Most suitably, Rs is phenyl.
The preferred dyes are those in which n is 1.
The dyes of Formula I may be prepared by diazotising a 4-aminodiphenyl ether sulphonic acid of the formula:
wherein R' and n have the meaning given above, and coupling the resulting diazo compound with a phenol of the formula:
wherein R2 and R3 have the meanings given above.
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' - methyldiphenyl ether 2 - sulphonic acid, 4 - amino - 4' - chlorodiphenyl ether - 2 - sulphonic acid, 4aminodiphenyl ether - 3 - sulphonic acid, 4' - amino - 4 - methoxydiphenyl ether - 3sulphonic acid, 4 - amino - 4' - methoxydiphenyl ether - 3 - sulphonic acid, 4amino - 4' - chlorodiphenyl ether - 3 - sulphonic acid, 4 - amino - 4' - tert.butyldiphenyl ether - 3 - sulphonic acid and 4aminodiphenyl ether-4'-sulphonic acid.
Examples of phenols which may be used as coupling components in making the dyes include 4 - phenylphenol, 2 - methyl - 4phenylphenol, 2 - chloro - 4 - phenylphenol, 2 - tert - butyl - 4 - phenylphenol and 4 (4'-ethoxyphenyl phenol.
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 metal 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 dyes have higher tinctorial strength than corresponding dyes in which the coupling component is an alkylphenol.
The invention is illustrated but not limited by the following Examples in which all parts and percentages are by weight.
Example 1.
To a solution of 5.7 parts of the sodium salt of 4-aminodiphenyl ether-2-sulphonic acid in 100 parts of water are added at 250C 8 parts of 36% hydrochloric acid followed by 10 parts of 13.8% sodium nitrite solution.
The diazo suspension is stirred for a further 1 hour at 25 C. After cooling to 0-5"C it is added over 15 minutes to a solution of 3.4 parts of ephenylphenol in 100 parts of water and 3 parts of 32% sodium hydroxide solution at 0--50C, maintaining the pH between 8 and 9 by addition of sodium carbonate solution as required. After stirring for a further 16 hours at Q50C, the product is filtered off, washed with water and dried.
When applied to nylon from a neutral to weakly acid bath, a yellow shade is obtained having excellent fastness to wet treatments and to light.
The following Table gives further examples of dyes of the invention which are prepared by diazotising the aminodiphenylether sulphonic acids listed in the second column below and coupling with the arylphenols listed in the third column. All of the dyes give yellow shades when applied to nylon from a neutral to weakly acid dyebath.
Example Aminodiphenylether sulphonic acid Coupling Component 2 4-Aminodiphenylether-2-sulphonic acid 2-Methyl-4-phenylphenol 3 " 2-Chloro-4-phenylphenol 4 " 4(4'-ethoxy)phenylphenol 5 4-Amino-4'-tertamyldiphenylether-2-sulphonic acid 4-phenylphenol 6 " 2-chloro-4-phenylphenol 7 4-Amino-3'-chlorodiphenylether-2-sulphonic acid 2-methyl-4-phenylphenol 8 " 4-phenylphenol 9 4-Aminodiphenylether-3-sulphonic acid 4-phenylphenol 10 " 2-chloro-4-phenylphenol 11 " 2-methyl-4-phenylphenol 12 4-Amino-3'-methyldiphenylether-3-sulphonic acid " 13 " 4-phenylphenol 14 4-Amino-3'-tertbutyldiphenylether-3-sulphonic acid " 15 " 2-Chloro-4-phenylphenol 16 4'-Amino-4-methoxydiphenylether-3-sulphonic acid 4-Phenylphenol 17 " 2-Methyl-4-phenylphenol 18 4-Aminodiphenylether-4'-sulphonic acid " 19 4-Aminodiphenyl-4'-sulphonic acid 2-tertbutyl-4-phenylphenol 20 " 2-Chloro-4-phenylphyenol 21 " 4-Phenylphenol

Claims (11)

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 1 or 2, R1 represents hydrogen, halogen, alkyl or alkoxy, R2 represents hydrogen, halogen or alkyl and R3 represents aryl optionally substituted by alkyl or alkoxy.
2. A water-soluble monoazo dye as claimed in claim 1 wherein R2 is hydrogen or alkyl and R3 is aryl optionally substituted by alkyl.
3. A water-soluble monoazo dye as claimed in claim 1 or claim 2 wherein Rs is phenyl.
4. A water-soluble monoazo dye as claimed in any one of the preceding claims wherein n is 1.
5. A water-soluble monoazo dye as claimed in claim 1 and specifically identified in Example 1.
6. A water-soluble monoazo dye as claimed in claim 1 and specifically identified in any one of Examples 2 to 21.
7. A method for the preparation of a watersoluble monoazo dye as defined in claim 1 which comprises diazotising a 4-aminodiphenyl ether sulphonic acid of the formula:
wherein R1 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 have the meanings given in claim 1.
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 to 6 and 9.
11. Synthetic polyamide textile materials whenever coloured by the process claimed in claim 10.
GB31645/76A 1976-07-29 1976-07-29 Diphenyl ether sulphanic acid-azo phenol dyes Expired GB1559292A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GB31645/76A GB1559292A (en) 1976-07-29 1976-07-29 Diphenyl ether sulphanic acid-azo phenol dyes
ZA00773621A ZA773621B (en) 1976-07-29 1977-06-16 Monoazo dyes
IT25155/77A IT1086241B (en) 1976-07-29 1977-06-28 MONOAZOIC DYES
NL7707479A NL7707479A (en) 1976-07-29 1977-07-06 METHOD FOR PREPARING A MONOAZO DYE
BR7704745A BR7704745A (en) 1976-07-29 1977-07-19 MONOAZO DYE SOLUBLE IN WATER AND PROCESS FOR ITS PREPARATION
BE179467A BE856945A (en) 1976-07-29 1977-07-19 MONOAZOIC DYES
DE19772733962 DE2733962A1 (en) 1976-07-29 1977-07-27 MONOAZO DYES
FR7723263A FR2359882A1 (en) 1976-07-29 1977-07-28 MONOAZOIC DYES
JP9132377A JPS5316037A (en) 1976-07-29 1977-07-29 Waterrsoluble monoazo dyes* process for producing same and method for dyeing materials of synthetic polyamide fiber using said2dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB31645/76A GB1559292A (en) 1976-07-29 1976-07-29 Diphenyl ether sulphanic acid-azo phenol dyes

Publications (1)

Publication Number Publication Date
GB1559292A true GB1559292A (en) 1980-01-16

Family

ID=10326270

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31645/76A Expired GB1559292A (en) 1976-07-29 1976-07-29 Diphenyl ether sulphanic acid-azo phenol dyes

Country Status (9)

Country Link
JP (1) JPS5316037A (en)
BE (1) BE856945A (en)
BR (1) BR7704745A (en)
DE (1) DE2733962A1 (en)
FR (1) FR2359882A1 (en)
GB (1) GB1559292A (en)
IT (1) IT1086241B (en)
NL (1) NL7707479A (en)
ZA (1) ZA773621B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60231715A (en) * 1984-04-12 1985-11-18 Dainippon Ink & Chem Inc High-gel, particulate polymer and its production
WO1998022537A1 (en) * 1996-11-20 1998-05-28 Crompton & Knowles Corporation Acid yellow dye and method for using same

Also Published As

Publication number Publication date
BE856945A (en) 1978-01-19
DE2733962A1 (en) 1978-02-02
NL7707479A (en) 1978-01-31
FR2359882A1 (en) 1978-02-24
BR7704745A (en) 1978-04-04
ZA773621B (en) 1978-05-30
IT1086241B (en) 1985-05-28
JPS5316037A (en) 1978-02-14

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PCNP Patent ceased through non-payment of renewal fee