GB2095272A - Disperse disazo dyestuffs - Google Patents
Disperse disazo dyestuffs Download PDFInfo
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- GB2095272A GB2095272A GB8108730A GB8108730A GB2095272A GB 2095272 A GB2095272 A GB 2095272A GB 8108730 A GB8108730 A GB 8108730A GB 8108730 A GB8108730 A GB 8108730A GB 2095272 A GB2095272 A GB 2095272A
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- United Kingdom
- Prior art keywords
- group
- dye
- aminoazobenzene
- signifies
- general formula
- Prior art date
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-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
- C09B31/043—Amino-benzenes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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Abstract
There are disclosed water insoluble disazo dyes having the general formula: <IMAGE> wherein R<1> signifies a hydrogen atom or a substituted or unsubstituted alkyl or alkoxy group, R<2> signifies a hydrogen atom, a substituted or unsubstituted alkyl. aryl, alkoxy or alkoxycarbonyl group, a group of formula -OCONHR<4>, or a group of -OCOO-A<3>-OR<5>, R<3> signifies an acylamino group, R<4> signifies a substituted or unsubstituted alkyl, aryl, cycloalkyl or heterocyclic group, R<5 >signifies a substituted or unsubstituted alkyl or aryl group, A<1>, A<2> and A<3> signify a straight or branched chain alkylene radical and may be same or different. By the term "acylamino group" we mean a group of the formula -NHCOR<6>, -NHCOOR<6>, or -NHSO2R<6>, wherein R<6> signifies an unsubstituted or substituted alkyl.
Description
SPECIFICATION
Disperse disazo dyestuffs
The present invention relates to disazo dyes and to process for their preparation and use.
Scarlet to red dyes are known which yield very bright dyeings particularly on polyester fibres but possess the disadvantage of high cost. The dyes of the present invention possess the advantage of brightness of shade combined with economy of manufacture.
According to the present invention therefore, water insoluble disazo dyes are provided having the general formula:
wherein Rl signifies a hydrogen atom or a substituted or unsubstituted alkyl or alkoxy group,
R2 signifies a hydrogen atom, a substituted or unsubstituted alkyl, aryl, alkoxy or alkoxycarbonyl group, a group of formula --OCONHR4, or a group of --OC000-AA3-OR5, R3 signifies an acylamino group,
R4 signifies a substituted or unsubstituted alkyl, aryl, cycloalkyl or heterocyclic group,
R5 signifies a substituted or unsubstituted alkyl or aryl group,
A1, A2 and A3 signify a straight or branched chain alkylene radical and may be same or different.
By the term "acylamino group" we mean a group of the formula --NHCORG. --NHCOORs, or -NHSO2R6, wherein R6 signifies an unsubstituted or substituted alkyl, or aryl group.
Rings X and Y may carry substituents for example: cyano, nitro, halogen, alkyl, alkoxy, thiocyano, alkoxycarbonyl, alkylcarbonyl or alkylsulphonyl groups.
The preferred dyes are those in which the alkyl alkoxy and alkylene groups contain from one or four carbon atoms and R6 represents an alkanoylamino group.
The invention includes a process for the preparation of dyes of general formula (I) which comprises coupling a diazonium derivative of an amine of general formula (II).
in which the rings X and Y are described as above, with an amine of general formula (Ill),
wherein R', R2, R3, Al and A2 have the meanings given above.
The amines of general formula (Ill) wherein R2 represents a group of formula --OCONHR4 or --OCOOA30R5, may be prepared by condensing a tertiary amine of general formula:
wherein R', R2, R3, R4, R5, A1, A2 and A3 have the meanings given above, with the appropriate chloroformate or isocyanate.
The amines of general formula (III) wherein R2 represents, for example, an alkyl or aralkyl group, are prepared from secondary amines by methods well known to those versed in the art.
Specific examples of amines of general formula (II) which may be used for preparing the diazo components include:
4-aminoazobenzene
2-methyl-4-aminoazobenzene
2-methoxy-4-aminoazobenzene Z-methyl-5-methoxy-4-a minoazobenzene 2-methoxy-5-methyl-4-a minoazobenzene
2,5-dimethyl-4-aminoazobenzene 2,5-di methoxy-4-aminoazobenzene 3-methyl-4-aminoazobenzene
3-methoxy-4-aminoazobenzene
3-chloro-4-aminoazobenzene 2',3-dimethyl-4-aminoazobenzene
4'-nitro-4-aminoazobenzene 4'-methylsulphonyl-4-aminoazobenzene
4'-methyl-4-aminoazobenzene
4'-methoxy-4-aminoazobenzene
4'-cyano-4-aminoazobenzene
4'-thiocyano-4-aminoazobenzene
4'-methoxycarbonyl-4-a minoazobenzene
4'-chloro-4-aminoazobenzene
2'-ch loro-4'-nitro-4-am inoazobenzene 4'-nitro-2-methyl-4-a minoazobenzene 4'-chloro-2-methyl-4-aminoazobenzene
4'-nitro-2-methyl-5-methoxy-4-aminoazobenzene
4'-nitro-2,5-dimethoxy-4-aminoazobenzene
4'-methoxy-2-methyl-4-aminoazobenzene
Specific examples of amines of general formula (III) include: N-P-cyanoethyl-N-methyl-3-acetylamino aniline N-p-cyanoethyl-N-ethyl-3-acetylamino aniline
N-ss-cyanoethyl-N-propyl-3-acetylamino aniline N-P-cyanoethyl-N-isopropyl-3-acetylamino aniline
N-ss-cyanoethyl-N-isobutyl-3-acetylamino aniline N-P-cyanoethyl-N-n-butyl-3-acetylamino aniline
N-y-cyanopropyl-N-ethyl-3-acetylamino aniline N-γ;-cyanopropyl-N-isopropyl-3-acetylamino aniline N-P-cyanoethyl-N-methyl-3-propionylamino aniline
N-ss-cyanoethyl-N-n-butyl-3-benzoylamino aniline N-P-cyanoethyl-N-benzyl-3-acetylamino aniline N-p-cyanoethyl-N-y-phenylpropyl-3-chloroacetylamino aniline N--cyanoethyl-N-n-butyl-2-methyl-5-acelamino aniline N-γ;-cyanopropyl-N-benyl-3-methoxycarbonylamino aniline N-,-cyanoethyl -N-P-methoxyca rbo nylethyl3-methoxyca rboxyla mino aniline N-ss-cyanoethyl-N-ss-ethoxycarbonylethyl-3-methylsulphonylamino aniline
N-y-cyanopropyl-N-benzyl-3-benzoylamino aniline
N-ss-cyanoethyl-N-ss-phenylethyl-3-acetylamino aniline
N-ss-cyanoethyl-N-methoxyethyl-2-methoxy-5-acetylamino aniline
Specific examples of other amines of general formula (IV) used to prepare coupling components of general formula (III) include:: N. -y-cyanopropyl-N y-hydroxypropyl-3-acetylamino aniline
N-ss-cyanoethyl-N-ss-hydroxyethyl-3-acetylamino aniline N-,B-cyanoethyl-N-y-hydroxypropyl-3-propionylamino aniline N-p-cyanoethyl-N-ss-hydroxyethyl-2-methoxy-5-benzoylamino aniline
N-y-cyanopropyl-N-y-hydroxypropyl-2-methyl-5-acetyla mino aniline
N-ss-cyanoethyl-N-ss-hydroxyethyl-2-methoxy-5-methoxycarbonylamino aniline N-,B-cyanoethyl-N-25-hydroxyethyl-3-chloroacetylamino aniline
Specific examples of chloroformates which may be condensed with amines of general formula (IV) to form the coupling components of general formula (III) are: 2-methoxyethylchloroformate, 2ethoxyethylchloroformate and 2-phenoxyethylchlorofomate.
Specific examples of isocyanates which may also be reacted with the same amines of formula (IV) are: n-butylisocyanate, phenylisocyanate, methylisocyanate and ethylisocyanate.
The invention further includes a process for the dyeing and printing of hydrophobic fibres, in which the dye is an azo dye of general formula (I).
Specific examples of hydrophobic fibres are cellulose acetate fibres such as secondary cellulose acetate and cellulose triacetate, polyamide fibres, polyacrylonitrile fibres such as "COURTELLE" ("COURTELLE" is a Registered Trade Mark) and in particular polyester fibres such as "TERYLENE" ("TERYLENE" is a Registered Trade Mark).
The dyes are preferably dispersed by grinding with water and a suitable dispersing agent e.g.
Dyapol SL. Dyeing may be carried out on polyester fibres from, for example, an aqueous bath at 95 1000C. containing a carrier, e.g. an emulsion of 2-phenylphenol such as that sold as "Optional B", or in pressurised vessels at 125--1400C. Alternatively the dye dispersion may be thickened with sodium alginate or other thickeners commonly used in textile printing and applied to polyester fabrics in the usual way by padding or printing with a roller or through a screen. After drying the fabric, the dye is fixed for example at 1.0-1.7 bar pressure or by heating the fabric in dry air at 160--2200C for 3090 second or by heating at 170-1 800C for 4-8 minutes with high temperature (superheated) steam.The dyes may also be applied by dyeing or printing on to secondary cellulose acetate, cellulose triacetate, polyamide and polyacrylonitrile fibres by the typical methods of application to these fibres described in the colour Index, Third Edition, 1971 (published by the Society of Dyers s Colourists,
Bradford, England). The colourations so obtained are orange to bluish red and have good fastness to light, washing, sublimation, rubbing and dry cleaning.
Alternatively, the dyes may be dispersed in an organic solvent, for example, chloroethylene, tetrachloroethylene or carbon tetrachloride, and colouration carried out from such a dispersion to the same fibres and under conditions of time and temperature similar to those used for aqueous application. The colourations so obtained are equivalent in hue and fastness properties to those obtained by aqueous methods of application.
The invention will be more closely understood by reference to the following examples; parts and percentages are by weight.
Example 1
19.7 parts of 4-aminoazobenzene are dissolved in 250 parts of glacial acetic acid. The solution is added rapidly, with stirring, to a mixture of 25 parts concentrated hydrochloric acid and 150 parts of ice. The fine suspension is cooled to 0--5 0 C and a solution of 6.9 parts of sodium nitrite in 25 parts of water is added. Stirring is continued for 2 hours at this temperature. Excess nitrous acid is destroyed by the addition of sulphamic acid and the diazo solution is filtered.
Meanwhile 23.1 parts of N-ss-cyanoethyl-N-ethyl-3-acetylaminoaniline are dissolved in 30 parts of glacial acetic acid. The solution is added dropwise to a mixture of 25 parts of concentrated hydrochloric acid and 500 parts of iced water. The diazo solution is added slowly and the mixture stirred for 1 hour at 0--5 0 C before adjusting to pH5 with sodium hydroxide solution. After stirring 4 hours at 0--50C the precipitated dye of formula:
is filtered off, washed acid free and dried.
One part of the dyestuff so obtained and two parts of Dyapol SL are added to 20 parts of water and milled in a ball mill until the average particle size of the dye is reduced to 15,um, before dilution to 1000 parts with water to form a dyebath. 100 parts of polyester yarn are introduced into the dyebath at room temperature and the temperature is then raised to 1300C and maintained for 1 hour in a pressurised dyeing machine. After this time the yarn is removed, rinsed and dried. The polyester fibres are dyed a bright scarlet shade of very good fastness to light, washing and sublimation.
Example 2
If the 23.1 parts of N-p-cyanoethyl-N-ethyl-3-acetylamino aniline used in example 1 are replaced by 34.9 parts of N-ss-cyanoethyl-N-ss-methoxyethoxycarbonyloxyethyl-3-acetylamino aniline, the dye obtained has the formula:
One part of the dyestuff so obtained and two parts of Dyapol SL are added to 20 parts of water and milled in a ball mill until the average particle size of the dye is reduced to 15Stm. This is then added to a mixture of 5 parts of a galactomannan thickening agent, such as that sold as "lndalca PA3--, and 5 parts of urea in 50 parts of water to form a paste which is then printed through a screen onto polyester fabric. After drying, the print is fixed by steaming for 20 minutes at 1.4 bar pressure.
After this time the fabric is removed, washed and dried. The scarlet print so obtained has very good fastness to list, washing and sublimation.
The coupler used in example 2 may be prepared, for example, by adding 1 5.9 parts of 2methoxyethylchloroformate, with stirring, to a solution of 24.7 parts N-p-cyanoethyl-N-,B-hydroxyethyl- 3-acetylamino aniline in 100 parts of pyridine. After stirring for 2 hours at 500C reaction is shown to be complete by thin layer chromatography.
The coupler used in example 1 may be prepared for example by dissolving 20.3 parts of N-P- cyanoethyl-3-acetylamino aniline in 80 parts of ethanol. To this is added 10.0 parts of sodium bicarbonate followed by 1 8.5 parts of diethyl sulphate. After the addition the temperature is raised to 7O0C and stirred until reaction is complete, as shown by thin layer chromatography.
In the following table. data is given referring to other disazo dyes of the present invention corresponding to general formula (I). These may be prepared, and used, in accordance with the general methods described in the previous examples.
It must be understood that the invention is not limited to the examples given in the following table.
Example No. Amine of formula II A1 A2 R1 R2 R3 Shade on Polyester 3 4-aminoazobenzene C2H4 CH2 H H NHCOCH3 Red 4 4-aminoazobenzene C2H4 C2H4 H NHCOCH3 Red 5 4-aminoazobenzene C2H4 n-C3H6 H H NHCOCH3 Red 6 4-aminoazobenzene C2H4 iso-C3H6 H H NHCOCH3 Red 7 4-aminoazobenzene C2H4 sec-C4H8 H H NHCOCH3 Red 8 4-aminoazobenzene C2H4 n-C4H8 H H NHCOCH3 Red 9 4-aminoazobenzene n-C3H6 C2H4 H H NHCOCH3 Red 10 4-aminoazobenzene C2H4 iso-C3H6 H H NHCOCH3 Red 11 4-aminoazobenzene C2H4 CH2 H H NHCOC2H6 Red 12 4-aminoazobenzene C2H4 n-C4H8 H H NHCOphenyl Red 13 4-aminoazobenzene C2H4 CH2 H phenyl NHCOCH3 Scarlet 14 4-aminoazobenzene C2H4 n-C3H8 H phenyl NHCOCH2Cl Scarlet 15 4-aminoazobenzene C2H4 CH2 CH3 phenyl NHCOCH3 Red 16 4-aminoazobenzene n-C3H8 CH2 H phenyl NHCOOCH3 Scarlet 17 4-aminoazobenzene C2H4 C2H4 H -COOCH3 NHCOOCH3 Scarlet 18 4-aminoazobenzene C2H4 C2H4 H -COOC2H5 NHSO2CH3 Scarlet 19 4-aminoazobenzene n-C3H6 CH2 H phenyl NHCOphenyl Scarlet 20 4-aminoazobenzene C2H4 C2H4 H phenyl NHCOCH3 Scarlet 21 4-aminoazobenzene C2H4 C2H4 OCH3 H NHCOCH3 Bluish-Red 22 4-aminoazobenzene C2H4 C2H4 H -OCOOC2H4OCH3 NHCOC2H5 Scarlet 23 4-aminoazobenzene n-C3H6 C2H4 H -OCOOC2H4OC2H5 NHCOCH2Cl Scarlet 24 4-aminoazobenzene C2H4 C2H4 OCH3 -OCOOC2H4Ophenyl NHCOCH2 Red 25 4-aminoazobenzene C2H4 C2H4 H -OCOOC2H4OCH3 NHCOphenyl Scarlet 26 2-methyl-4-aminoazobenzene C2H4 CH2 H H NHCOCH3 Red 27 2-methyl-4-aminoazobenzene C2H4 CH2 H phenyl NHCOCH3 Scarlet 28 2-methoxy-4-aminoazobenzene n-C3H6 C2H4 H H NHCOC2H8 Red 29 2-methyl-5-methoxy-4-aminoazobenzene C2H4 n-C3H6 CH3 H NHCOCH3 Rad 30 2-methoxy-5-methyl-4-aminoazobenzene C2H4 C2H4 H -OCOOC2H4OCH3 NHCOCH3 Scarlet 31 2,5-dimethyl-4-aminoazobenzene C2H4 C2H4 H- COOCH3 NHCOphenyl Scarlet 32 2,5-dimethoxy-4-aminoazobenzene C2H4 C2H4 H -OCONHC4H9 NHCOCH3 Scarlet 33 3-methyl-4-aminoazobenzene C2H4 C2H4 H -OCONH phenyl NHCOCH3 Reddish-Orang 34 3-chloro-4-aminoazobenzene C3H6 C2H4 H OCH3 NHCOCH3-Orange 35 2'-3-dimethyl-4-aminoazobenzene C2H4 CH2 H phenyl NHCOOCH3 Scarlet 36 2'-3-dimethyl-4-aminoazobenzene C2H4 CH2CH(CH3)H CH3 NHCOCH3 Red 37 4'-nitro-4-aminoazobenzene C2H4 C2H4 H H NHCOCH3 Bluish-Red 38 4'-nitro-4-aminoazobenzene C3H6 C2H4 H phenyl NHCOCH2Cl Red 39 4'-nitro-4-aminoazobenzene C2H4 C2H4 OCH3 -OCOOC2H4OCH3 NHCOCH3 Bluish-Red
Table (contd.)
Example No. Amine of formula II A1 A2 R1 R3 Shade on Polyester 40 4'-methylsulphonyl-4-aminoazobenzene C2H4 CH2CH(CH3) H H NHCOphenyl Bluish-Red 41 4'-methyl-4-aminoazobenzene C2H4 C2H4 H -OCONH phenyl NHCOphenyl Reddish Orange 42 4'-methoxy-4-aminoazobenzene C3H6 C2H4 CH3 p-CH3 phenyl NHCOC2H4OCH3 Scarlet 43 4'-cyano-4-aminoazobenzene C2H4 C2H4 H H NHCOCH3 Bluish-Red 44 4'-thiocyano-4-aminoazobenzene C2H4 CH2 CH3 phenyl NHCOCH3 Red 45 4'-methoxycarbonyl-4-aminoazobenzene C2H4 C3H6 H phenyl NHCOCH3 Red 46 4'-chloro-4-aminoazobenzene C3H6 C2H4 H -COOCH3 NHCOCH3 Scarlet 47 2'-chloro-4'-nitro-4-aminoazobenzene C2H4 C2H4 H -OCOOC2H4OCH3 NHCOC2H5 Scarlet 48 4'-nitro-2-methyl-4-aminoazobenzene C2H4 CH2CH(CH3) OCH3 H NHCOC2H5 Bluish-Red 49 4'-chloro-2-methyl-4-aminoazobenzene C3H6 C2H4 OCH3 -OCOOC2H4O phenyl NHCOC2H5 Red 50 4'-nitro-2-methyl-5-methoxy-4aminoazobenzene C2H4 CH2 H phenyl NHCOOCH3 Red 51 4'-nitro-2,5-dimethoxy-4-aminoazobenzene C2H4 C3H6 H H NHCOCH3 Bluish-Red 52 4'-methoxy-2-methyl-4-aminoazobenzene C3H6 C2H4 CH3 COOCH3 NHCOCH2Cl Scarlet
Claims (14)
1. A water-insoluble disazo dye having the general formula:
wherein R1 signifies a hydrogen atom or a substituted or unsubstituted alkyl or alkoxy group,
R2 signifies a hydrogen atom, a substituted or unsubstituted alkyl, aryl, alkoxy or alkoxycarbonyl group, a group of formula -OCONHR4, or a group of -0OOO-A3-OR6, R3 signifies an acylamino group,
R4 signifies a substituted or unsubstituted alkyl, aryl, cycloalkyl or heterocyclic group,
R5 signifies a substituted or unsubstituted alkyl or aryl group,
A1, A2 and A3 each independently signify a straight or branched chain alkylene radical, and
wherein rings X and Y are substituted or unsubstituted.
2. A dye as claimed in claim 1, in which each of the alkyl, alkoxy and alkylene groups contains from one to four carbon atoms and R6 represents an alkanoylamino group.
3. A dye of the general formula I as defined in claim 1, substantially as hereinbefore described in any one of the foregoing Examples.
4. A process for the preparation of a dye of general formula (I) as defined in claim 1, which comprises coupling a diazonium derivative of an amine of general formula (II)
in which the rings X and Y are as defined in claim 1, with an amine of general formula (III)
wherein R1, R2, R3, A1 and A2 have the meanings given in claim 1.
5. A process as claimed in claim 4, in which each of the alkyl, alkoxy and alkylene groups contain from one to four carbon atoms and R6 represents an alkanoylamino group.
6. A process for the preparation of a dye of the general formula I as defined in claim 1, substantially as hereinbefore described in any one of the foregoing Examples.
7. A process for the dyeing or printing of hydrophobic fibres, in which the dye is an azo dye of general formula (I) as claimed in claim 1, 2 or 3.
8. A process as claimed in claim 7, in which the hydrophobic fibres are cellulose acetate fibres, polyamide fibres, polyacrylonitrile fibres, or polyester fibres.
9. A process as claimed in claim 7 or 8, in which the dye is dispersed by grinding with water and a dispersing agent.
10. A process as claimed in claim 7, 8 or 9, in which dyeing is carried out on polyester fibres from an aqueous bath at 95-1 O00C. containing a carrier, or in a pressurised vessel at 125--1400C.
1 A process as claimed in any one of claims 7 to 9, in which the dye in the form of a dye dispersion thickened with a thickener, is applied to a polyester fabric by padding or printing with a roller or through a screen, the fabric is dried and the dye is fixed.
12. A process as claimed in claim 7 or 8, in which the dye is dispersed in an organic solvent, carried out from such a dispersion.
13. A process for the dyeing or printing of hydrophobic fibres, substantially as hereinbefore described in any one of the foregoing Examples.
14. Hydrophobic fibres whenever dyed or printed by a process as claimed in any one of claims 7 to 13.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8108730A GB2095272A (en) | 1981-03-20 | 1981-03-20 | Disperse disazo dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8108730A GB2095272A (en) | 1981-03-20 | 1981-03-20 | Disperse disazo dyestuffs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2095272A true GB2095272A (en) | 1982-09-29 |
Family
ID=10520527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8108730A Withdrawn GB2095272A (en) | 1981-03-20 | 1981-03-20 | Disperse disazo dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2095272A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117210028A (en) * | 2023-11-09 | 2023-12-12 | 上海安诺其集团股份有限公司 | Brilliant blue disperse dye and preparation method and application thereof |
-
1981
- 1981-03-20 GB GB8108730A patent/GB2095272A/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117210028A (en) * | 2023-11-09 | 2023-12-12 | 上海安诺其集团股份有限公司 | Brilliant blue disperse dye and preparation method and application thereof |
| CN117210028B (en) * | 2023-11-09 | 2024-01-30 | 上海安诺其集团股份有限公司 | Brilliant blue disperse dye and preparation method and application thereof |
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| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |