GB2030167A - Dyestuffs - Google Patents
Dyestuffs Download PDFInfo
- Publication number
- GB2030167A GB2030167A GB7927359A GB7927359A GB2030167A GB 2030167 A GB2030167 A GB 2030167A GB 7927359 A GB7927359 A GB 7927359A GB 7927359 A GB7927359 A GB 7927359A GB 2030167 A GB2030167 A GB 2030167A
- Authority
- GB
- United Kingdom
- Prior art keywords
- monoazo dyestuff
- dyestuff
- disperse
- textile materials
- disperse monoazo
- 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.)
- Withdrawn
Links
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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
- C09B43/42—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms by substituting radicals containing hetero atoms for —CN radicals
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/081—Amino benzenes free of acid groups characterised by the amino group substituted amino group unsubstituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino, aralkylamino or arylamino
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Disperse monoazo dyestuffs having the general formula: <IMAGE> wherein X represents hydrogen, a C1-C4 alkyl or C1-C4 alkoxy group and Y and Z each represent alkyl groups. The dyes are applicable to synthetic textile materials, e.g. cellulose acetates polyamides and especially aromatic polyester textile materials.
Description
SPECIFICATION
Dyestuffs
This invention relates to dyestuffs and more particularly to disperse monoazo dyestuffs based on secondary amine coupling components.
According to the present invention there are Drovided disperse monoazo dyestuffs having the general formula:
wherein X represents hydrogen, a lower alkyl or lower alkoxy group and each of Y and Z represents an alkyl group.
It is preferred that the alkyl groups represented by Y and Z are lower alkyl groups.
In this specification the terms "lower alkyl" and "lower alkoxy" mean alkyl and alkoxy groups respectively which contain from 1 to 4 carbon atoms.
Examples of the alkyl groups represented by X, Y and Z are methyl, ethyl, n-propyl, iso-propyl and n-butyl.
Examples of lower alkoxy groups represented by X are methoxy and ethoxy.
According to a further feature of the invention there is provided a process for the manufacture of disperse monoazo dyestuffs having the above-defined formula which comprises reacting a monoazo compound having the formula:
wherein each W represents a halogen atom selected from chlorine, bromine and iodine and which may be the same or different, and X, Y and Z have the meanings stated above, with cuprous cyanide.
The reaction can be carried out in aqueous or organic medium and advantageously in a polar aprotic solvent.
It is preferred that each W represents a bromine atom.
Examples of suitable polar aprotic solvents for carrying out the above process are dimethylformamide, dimethyl-acetamide and dimethylsulphoxide.
When W represents a bromine or iodine atom, the replacement by the cyano group proceeds readily at normal room temperature and a reaction time of 4 hours is generally sufficient to ensure completion of the reaction, although longer times may be used without adverse effect. When W is chlorine, an elevated temperature and/or longer reaction time may be necessary. Cuprous cyanide is required in amount to provide approximately one cyano group for each halogen atom W to be replaced, a slight excess of cuprous cyanide, for example, a 5% excess, being preferred.
The dyestuff may be isolated from its solution in the polar aprotic solvent by filtering the solution and precipitating the dyestuff by addition of water. The precipitated dyestuff is collected and may be freed from any residual copper salts by treatment with acidified aqueous ferric chloride solution. The dyestuff may then be washed with water and dried. If desired the dyestuff so obtained may be further purified by recrystallisation.
Examples of monoazo compounds of formula (II) which may be used in the above process are 2,6-dibrnmo-4-methyl-2'-aceWl-amino-4'-N-(1 "-ethylpropyl)aminoazobenzene, 2,6-dibromo-4-methyl-2' acelamino-4'-N-isoprnpylaminoazobenzene, 2,6-dibromo-4-methyl-2'-acetylamino-4'-N-sec- butylaminoazobenzene, 2,6-dibromo-4-methyl-2'-formylamino-4'-N-sec-butylaminOazobenzene, 2,6 dibromo-4.methyl-2'-propionylamino-4'-N-sec-butylaminoazobenzene, 2,6-dibromo-4-methyl-2' butyrylamino-4'-N-sec-butyl a m i noazo benzene, 2,6-dibromo-4-methyl-2'-methoxycarbonylamino-4'-N-secbutylaminoazobenzene and 2,6-dibrnmo-4-methyl-2'-ethoxycarbonylamino-4'-N-sec- butylaminoazobenzene.
The monoazo compounds of formula (II) may themselves be obtained by diazotising an arylamine of formula:
and coupling the diazonium compound so obtained on to a coupling component of formula:
wherein W, X, Y and Z have the meanings stated above.
The above-mentioned diazotisation and coupling are carried out by the conventional methods for such
reactions.
According to a yet further feature of the invention there is provided a method for the colouration of synthetic textile materials which comprises applying to the said synthetic textile materials from an aqueous
medium a monoazo dyestuff as hereinbefore defined.
The dyestuffs of the present invention may be applied to synthetic textile materials by dyeing, padding or printing methods in the form of aqueous dispersions which are prepared by conventional methods, for example, by milling the dyestuffs with water and a suitable dispersing agent such as the sodium salt of a naphthalene-2-sulphonic acid/formaldehyde condensate.
Examples of synthetic textile materials to which the dyestuffs may be applied are textile materials fabricated from secondary cellulose acetate, cellulose triacetate, polyamides such as poly(hexamethylene adipamide) and above all aromatic polyesters such as polyethylene terephthalate.
The dyestuffs may also be applied to synthetic textile materials by known methods of transfer colour printing such as sublimation transfer printing, optionally under reduced pressure, and wet transfer printing.
The dyestuffs also find application for the melt colouration of polymers such as aromatic polyesters.
When applied to synthetic textile materials as indicated above, the dyestuffs of the present invention provide bright bluish-red shades having good fastness to the tests conventionally applied to coloured synthetic textile materials, and in particular good dyeing properties and tinctorial strength.
The invention is illustrated but not limited by the following Examples in which parts and percentages are by weight.
Example 1 2-Acetylamino4-(N-l "-ethylpropyl)am ino-2',6'-dibromo-4'-methylazobenzene (3.4 parts) is dissolved in dimethylsulphoxide (60 parts) and the solution is added to a slurry of cuprous cyanide (1.47 parts) in dimethylsulphoxide (20 parts). The mixture is stirred for 4 hours at room temperature and filtered. Addition of water to the solution precipitates the dyestuff, which is collected, treated with acidified aqueous ferric chloride solution to remove copper salts washed with water and dried. The dyestuff is recrystallised from aqueous acetone.
When applied in the form of an aqueous dispersion to aromatic polyester textile material a bright bluish-red shade is obtained.
The following table gives further Examples of dyestuffs of the invention which may be obtained by methods analogous to that described in Example 1. The second column identifies the residue -E present in the structure:
The third column shows the shades obtained on aromatic polyester textile material.
Ex.n S Shade B1i,h 'NH;I- C F -i aH 3 NHCOCH) ..
/NH - CL'(CH3,2 4 :iiiCuCH.. " NdC{(CF.5)r: 5 hliiUCHj t.c}.rc4H9) e tHcCaH > X7~hHCH - & BR< 3 3
2,",'ple H shede ;CFiO Blui8b tv | z 5 red 8 NHCOC9 HH-,,e(() 32 9 NH'SaH aH(CH ) 2 32 nH 10 NHOOOW NH OH C H I - 25
Claims (9)
1. A disperse monoazo dyestuff having the general formula:
wherein X represents hydrogen, a lower alkyl or lower alkoxy group and each of Y and Z represents an alkyl group.
2. A disperse monoazo dyestuff as claimed in claim 1 wherein each of Y and Z is lower alkyl.
3. A disperse monoazo dyestuff as claimed in claim 1 and specifically identified herein.
4. A process for the manufacture of a disperse monoazo dyestuff as defined in claim 1 which comprises reacting a monoazo compound having the formula:
wherein each W represents a halogen atom selected from chlorine, bromine and iodine and which may be the same or different, and X, Y and Z have the meanings stated in claim 1, with cuprous cyanide.
5. A process as claimed in claim 4 conducted substantially as hereinbefore described with reference to any one of the foregoing Examples.
6. A disperse monoazo dyestuff whenever manufactured by a method claimed in claim 4 or claim 5.
7. A process for the coloration of synthetic textile materials which comprises applying thereto a disperse monoazo dyestuff as claimed in any one of claims 1 to 3 and 6.
8. A process as claimed in claim 7 wherein the synthetic textile material is an aromatic polyester textile material.
9. Synthetic textile materials whenever coloured by the process claimed in claim 7 or claim 8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7927359A GB2030167A (en) | 1978-09-08 | 1979-08-06 | Dyestuffs |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7836179 | 1978-09-08 | ||
| GB7927359A GB2030167A (en) | 1978-09-08 | 1979-08-06 | Dyestuffs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2030167A true GB2030167A (en) | 1980-04-02 |
Family
ID=26268797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7927359A Withdrawn GB2030167A (en) | 1978-09-08 | 1979-08-06 | Dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2030167A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0152005A3 (en) * | 1984-02-13 | 1985-12-11 | Cassella Aktiengesellschaft | Mixtures of monoazo dyes |
| US4968318A (en) * | 1988-12-28 | 1990-11-06 | Bayer Aktiengesellschaft | Red mixtures of disperse azo dyestuffs |
| EP0444529A1 (en) * | 1990-02-26 | 1991-09-04 | CASSELLA Aktiengesellschaft | Use of dyestuffs for sublimation transfer process |
| US5279621A (en) * | 1991-02-28 | 1994-01-18 | Cassella Ag | High temperature dyeing of polyester and polyester-containing textile materials under alkaline conditions |
-
1979
- 1979-08-06 GB GB7927359A patent/GB2030167A/en not_active Withdrawn
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0152005A3 (en) * | 1984-02-13 | 1985-12-11 | Cassella Aktiengesellschaft | Mixtures of monoazo dyes |
| US4582509A (en) * | 1984-02-13 | 1986-04-15 | Cassella Aktiengesellschaft | Mixtures of monoazo dyestuffs |
| US4968318A (en) * | 1988-12-28 | 1990-11-06 | Bayer Aktiengesellschaft | Red mixtures of disperse azo dyestuffs |
| EP0444529A1 (en) * | 1990-02-26 | 1991-09-04 | CASSELLA Aktiengesellschaft | Use of dyestuffs for sublimation transfer process |
| US5169404A (en) * | 1990-02-26 | 1992-12-08 | Cassella Ag | Monoazo dyestuffs for the sublimation transfer process |
| US5279621A (en) * | 1991-02-28 | 1994-01-18 | Cassella Ag | High temperature dyeing of polyester and polyester-containing textile materials under alkaline conditions |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |