US2169970A - Disazo dyestuffs - Google Patents
Disazo dyestuffs Download PDFInfo
- Publication number
- US2169970A US2169970A US236034A US23603438A US2169970A US 2169970 A US2169970 A US 2169970A US 236034 A US236034 A US 236034A US 23603438 A US23603438 A US 23603438A US 2169970 A US2169970 A US 2169970A
- Authority
- US
- United States
- Prior art keywords
- disazo
- carboxylic acid
- radicles
- stands
- dyestuffs
- 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 - Lifetime
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 239000004744 fabric Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 150000008049 diazo compounds Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- UDAQUPSJOGVPIX-UHFFFAOYSA-N 3-hydroxy-7-methoxynaphthalene-2-carboxylic acid Chemical compound C1=C(O)C(C(O)=O)=CC2=CC(OC)=CC=C21 UDAQUPSJOGVPIX-UHFFFAOYSA-N 0.000 description 1
- PHQKCVOZVPSTAF-UHFFFAOYSA-N 3-hydroxyanthracene-2-carboxylic acid Chemical compound C1=CC=C2C=C(C=C(C(C(=O)O)=C3)O)C3=CC2=C1 PHQKCVOZVPSTAF-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- LHYQAEFVHIZFLR-UHFFFAOYSA-L 4-(4-diazonio-3-methoxyphenyl)-2-methoxybenzenediazonium;dichloride Chemical compound [Cl-].[Cl-].C1=C([N+]#N)C(OC)=CC(C=2C=C(OC)C([N+]#N)=CC=2)=C1 LHYQAEFVHIZFLR-UHFFFAOYSA-L 0.000 description 1
- SXEBHIMOUHBBOS-UHFFFAOYSA-N 5-chloro-2-phenoxyaniline Chemical compound NC1=CC(Cl)=CC=C1OC1=CC=CC=C1 SXEBHIMOUHBBOS-UHFFFAOYSA-N 0.000 description 1
- 241000896693 Disa Species 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 241000933336 Ziziphus rignonii Species 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- -1 di- (aminophenyl) -diamino-benzene sulfonic acid Chemical compound 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- ZJHJWUVWYXNFLY-UHFFFAOYSA-N n-methoxy-n-phenylaniline Chemical compound C=1C=CC=CC=1N(OC)C1=CC=CC=C1 ZJHJWUVWYXNFLY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/147—Disazo dyes in which the coupling component is a bis -(-o-hydroxy-carboxylic- acid amide)
Definitions
- the present invention relates to disazo dyestuffs, a process of producing same and a process of dyeing textile materials therewith.
- disa'zo dyestufls having valuable properties are obtained by causing diazo compounds of aromatic amines to react with ortho-hydroxy-aryl carboxylic arylides containing at least one sulfonic acid group in the arylide portion, which corresponds to the following formula on HO p Ar XAI CONHB1-NH-BrNH-BaNH-CO wherein the Ar stands for arylene radicles, and wherein B1, B2 and B3 stand for phenylene radicles.
- Arylides of this type may beprepared for example by reacting two molecular proportions of an ortho-hydroxy-aryl carboxylic acid, e., g. 2-hydroxynaphthalene 3 5 carboxylic acid, their chlorides, their 'ortho-acyloxy chlorides or their esters with one molecular proportion of an N,N di- (aminophenyl) -diamino-benzene sulfonic acid corresponding to the general formula wherein B1, B2 and B3 represents phenylene radicles at 'least'one'of which contains a sulfonic' acid group.
- These diamines may be prepared by condensing phenylene-diamines, e. g.
- paraor metaphenylene diamine ortoluylene diamines with paraor orthonitrochlorbengene sulfonic acids which may be further substituted for example by alkyl or alkoxy groups or additional acid and 7.8-benzocarbazole-Bz.3-hydroxy-2-carboxylic acid.
- diazo components for the process according to this invention there may be mentioned the usual amines employed in the preparation of azo dyestuffs, inparticular those not containing solubilising groups, such as aniline, nitroaminor the fibre and developing them thereon by treatment with diazo-compounds.
- the coupling components have alfinity for animal fibres and they also go onto vegetable fibres. It is, therefore, possible to produce on mixtures of dilferent fibres, as for example on mixed yarns or mixed fabrics, especially those of wool and regenerated cellulose (staple fibre) very fast dyeings, exceptionally level on both kinds of fibres.
- 2-hydroxynaphthalene-B-carboxylic acid for the preparation of the arylides there may be mentioned in particular 2-hydroxynaphthalene-B-carboxylic acid, and also other orthohydroxy-carboxy compounds capable of coupling, as for example 2-hydroxy-6-methoxynaphthalene-3-carboxylic acid, 2-hydroxyanthracene-3- carboxylic acid, Z-hydroxytriphenylene 3 carboxylic acid, 3-hydroxydiphenylene-oxide-2-carboxylic acid, Z-hydroxycarbazole 3 carboxylic BOzNa SOaNa with an addition of 50 per cent of sodium sulphate (percentages being with reference to the weight of fibres).
- the dyed fabric is then treated for half an hour at C. in an aqueous bath containing from 1 to 5 grams of soap per litre.
- a navy-blue dyeing of excellent fastness to Washing and very good fastness to light which coversuniformly both kinds of fibre is thus obtained.
- Dyeings on wool or silk or on mixtures of both may also be prepared in the same way.
- a process of producing fast dyeings on textile material which consists in applying to said 5 material an orthohydroxyl-aryl carboxylicarylide containing in the arylide portion at least one sulfonic acid group and corresponding to the general formula wherein the Ar stands for arylene radicles, and B1, B2 and B3 stand for phenylene radicles, and converting said arylide into a disazo dyestuif by treatment with diazotized aromatic amines.
- Disazo dyestufis corresponding to the general formula wherein X stands for an aryl radicle.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Patented Aug. 15, 1939 PATENT orries DISAZO- DYESTUFFS "Wolfgang Alt and Hans Krzikalla, Ludwigsha- 'fen-on-the-Rhine, Germany,
assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application October 20, 1938, Se-
rial No. 236,034. In Germany November 19,
5- Claims.
The present invention relates to disazo dyestuffs, a process of producing same and a process of dyeing textile materials therewith.
We have found that disa'zo dyestufls having valuable properties are obtained by causing diazo compounds of aromatic amines to react with ortho-hydroxy-aryl carboxylic arylides containing at least one sulfonic acid group in the arylide portion, which corresponds to the following formula on HO p Ar XAI CONHB1-NH-BrNH-BaNH-CO wherein the Ar stands for arylene radicles, and wherein B1, B2 and B3 stand for phenylene radicles.
Arylides of this type may beprepared for example by reacting two molecular proportions of an ortho-hydroxy-aryl carboxylic acid, e., g. 2-hydroxynaphthalene 3 5 carboxylic acid, their chlorides, their 'ortho-acyloxy chlorides or their esters with one molecular proportion of an N,N di- (aminophenyl) -diamino-benzene sulfonic acid corresponding to the general formula wherein B1, B2 and B3 represents phenylene radicles at 'least'one'of which contains a sulfonic' acid group. These diamines may be prepared by condensing phenylene-diamines, e. g. paraor metaphenylene diamine ortoluylene diamines, with paraor orthonitrochlorbengene sulfonic acids which may be further substituted for example by alkyl or alkoxy groups or additional acid and 7.8-benzocarbazole-Bz.3-hydroxy-2-carboxylic acid. v v
As diazo components for the process according to this invention there may be mentioned the usual amines employed in the preparation of azo dyestuffs, inparticular those not containing solubilising groups, such as aniline, nitroaminor the fibre and developing them thereon by treatment with diazo-compounds.
The coupling components have alfinity for animal fibres and they also go onto vegetable fibres. It is, therefore, possible to produce on mixtures of dilferent fibres, as for example on mixed yarns or mixed fabrics, especially those of wool and regenerated cellulose (staple fibre) very fast dyeings, exceptionally level on both kinds of fibres.
The following example will further illustrate how our invention may be carried out in practice but the invention is not restricted to this example.
' Example A mixed fabric of 50 per cent of wool and 50 percent ofstaple fibre (viscose silk). is treated for an hour at C. in a bath with a bath ratio of 1:20 with 3 per cent of the disodium salt of the composition:
CONHQNHGNHQNHCO halogen atoms, and reducing the dinitro compounds toform diamines.
For the preparation of the arylides there may be mentioned in particular 2-hydroxynaphthalene-B-carboxylic acid, and also other orthohydroxy-carboxy compounds capable of coupling, as for example 2-hydroxy-6-methoxynaphthalene-3-carboxylic acid, 2-hydroxyanthracene-3- carboxylic acid, Z-hydroxytriphenylene 3 carboxylic acid, 3-hydroxydiphenylene-oxide-2-carboxylic acid, Z-hydroxycarbazole 3 carboxylic BOzNa SOaNa with an addition of 50 per cent of sodium sulphate (percentages being with reference to the weight of fibres). After powerful rinsing with cold water, the bottomed fabric is treated for half an hour at room temperature'in a neutral solution of the diazo compound of 4-amino-3- methoxydiphenylamine or 4-amino=-4'-methoxydiphenylamine. The dyed fabric is then treated for half an hour at C. in an aqueous bath containing from 1 to 5 grams of soap per litre. ,A navy-blue dyeing of excellent fastness to Washing and very good fastness to light which coversuniformly both kinds of fibre is thus obtained. Dyeings on wool or silk or on mixtures of both may also be prepared in the same way. By using 4-benzoy1amino -2.5-diethoxy- 1 -aminobenzene instead of the said diazo component, a fast blue dyestufi is also obtained; by using 4-chlor-2- aminodiphenyl ether a red dyestufi' is obtained.
Instead of the above described arylide there may be used as coupling component the arylide of the formula:
2. A process of producing fast dyeings on textile material which consists in applying to said 5 material an orthohydroxyl-aryl carboxylicarylide containing in the arylide portion at least one sulfonic acid group and corresponding to the general formula wherein the Ar stands for arylene radicles, and B1, B2 and B3 stand for phenylene radicles, and converting said arylide into a disazo dyestuif by treatment with diazotized aromatic amines.
YAr
3. Disazo dyestuffs corresponding to the general formula N=N-X XN=N OH HO Ar Ar wherein the Ar stands for arylene radicles, and wherein B1, B2 and B3 stand for phenylene radicles and wherein X stands for an aryl radiole.
4. Disazo dyestufis corresponding to the general formula wherein X stands for an aryl radicle.
5. The disazo dyestufl corresponding to the formula N=N--X l HO SOJH SOaH wherein X stands for the radicle of a methoxydiphenylamine.
WOLFGANG ALT. HANS KRZIKALL'A.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2169970X | 1937-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2169970A true US2169970A (en) | 1939-08-15 |
Family
ID=7988357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US236034A Expired - Lifetime US2169970A (en) | 1937-11-19 | 1938-10-20 | Disazo dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2169970A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4123455A (en) * | 1977-06-13 | 1978-10-31 | American Cyanamid Company | Phenenyltris(carbonylimino) multi-anionic substituted triphenyl acids and salts |
-
1938
- 1938-10-20 US US236034A patent/US2169970A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4123455A (en) * | 1977-06-13 | 1978-10-31 | American Cyanamid Company | Phenenyltris(carbonylimino) multi-anionic substituted triphenyl acids and salts |
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