GB2034760A - Process for Dyeing Wool and Leather in a Solid Navy Blue Shade - Google Patents
Process for Dyeing Wool and Leather in a Solid Navy Blue Shade Download PDFInfo
- Publication number
- GB2034760A GB2034760A GB7937064A GB7937064A GB2034760A GB 2034760 A GB2034760 A GB 2034760A GB 7937064 A GB7937064 A GB 7937064A GB 7937064 A GB7937064 A GB 7937064A GB 2034760 A GB2034760 A GB 2034760A
- Authority
- GB
- United Kingdom
- Prior art keywords
- leather
- carries
- wool
- blue
- parts
- 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.)
- Granted
Links
- 210000002268 wool Anatomy 0.000 title claims abstract description 21
- 238000004043 dyeing Methods 0.000 title claims abstract description 19
- 239000010985 leather Substances 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims abstract description 9
- 230000008569 process Effects 0.000 title claims abstract description 9
- 239000007787 solid Substances 0.000 title description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract 2
- 230000003381 solubilizing effect Effects 0.000 claims abstract 2
- 239000000975 dye Substances 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 7
- 230000015556 catabolic process Effects 0.000 claims description 5
- 238000006731 degradation reaction Methods 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 3
- 239000002253 acid Substances 0.000 description 8
- 239000001045 blue dye Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 4
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 4
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
- FDXOYIGOUGEQBC-UHFFFAOYSA-N 8-(4-methylanilino)naphthalene-1-sulfonic acid Chemical compound C1=CC(C)=CC=C1NC1=CC=CC2=CC=CC(S(O)(=O)=O)=C12 FDXOYIGOUGEQBC-UHFFFAOYSA-N 0.000 description 2
- QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical class C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- XPRMZBUQQMPKCR-UHFFFAOYSA-L disodium;8-anilino-5-[[4-[(3-sulfonatophenyl)diazenyl]naphthalen-1-yl]diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C3=CC=CC=C3C(N=NC=3C4=CC=CC(=C4C(NC=4C=CC=CC=4)=CC=3)S([O-])(=O)=O)=CC=2)=C1 XPRMZBUQQMPKCR-UHFFFAOYSA-L 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- -1 monoazo compound of formula II Chemical compound 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 235000018553 tannin Nutrition 0.000 description 2
- 229920001864 tannin Polymers 0.000 description 2
- 239000001648 tannin Substances 0.000 description 2
- YKOLZVXSPGIIBJ-UHFFFAOYSA-N 2-Isopropylaniline Chemical compound CC(C)C1=CC=CC=C1N YKOLZVXSPGIIBJ-UHFFFAOYSA-N 0.000 description 1
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- FWEOQOXTVHGIFQ-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid Chemical compound C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 description 1
- VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- ZRYQXQUPWQNYSX-UHFFFAOYSA-L disodium;5-[(3-methyl-5-oxo-1-phenyl-4h-pyrazol-4-yl)diazenyl]-2-[4-[(3-methyl-5-oxo-1-phenyl-4h-pyrazol-4-yl)diazenyl]-2-sulfonatophenyl]benzenesulfonate Chemical compound [Na+].[Na+].CC1=NN(C=2C=CC=CC=2)C(=O)C1N=NC(C=C1S([O-])(=O)=O)=CC=C1C(C(=C1)S([O-])(=O)=O)=CC=C1N=NC(C1=O)C(C)=NN1C1=CC=CC=C1 ZRYQXQUPWQNYSX-UHFFFAOYSA-L 0.000 description 1
- BMYUQZABARGLAD-UHFFFAOYSA-L disodium;8-(4-methylanilino)-5-[[4-[(3-sulfonatophenyl)diazenyl]naphthalen-1-yl]diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC(C)=CC=C1NC(C1=C(C=CC=C11)S([O-])(=O)=O)=CC=C1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC=CC(S([O-])(=O)=O)=C1 BMYUQZABARGLAD-UHFFFAOYSA-L 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/32—Material containing basic nitrogen containing amide groups leather skins
- D06P3/3206—Material containing basic nitrogen containing amide groups leather skins using acid dyes
- D06P3/3226—Material containing basic nitrogen containing amide groups leather skins using acid dyes dis-polyazo
-
- 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
- C09B31/041—Disazo dyes from a coupling component "C" containing a directive amino group 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/06—Material containing basic nitrogen containing amide groups using acid dyes
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Process for dyeing wool or leather in blue or navy blue shades, using at least one dye of the formula <IMAGE> in which the benzene ring A carries 1 or 2 alkyl, preferably methyl, groups, the naphthalene ring B carries a sulfonic acid solubilizing group in the 6- or 7-position and the benzene ring C carries 0, 1 or 2 methyl groups.
Description
SPECIFICATION
Process for Dyeing Wool and Leather in a Solid
Navy Blue Shade
This invention relates to a process for dyeing goods of animal origin, such as wool and leather, by means of acid disazo navy blue dyes, which do not undergo the reduction phenomenons occuring usually in these cases.
The art-worker knows that the use of acid disazo navy blue dyes, such as those described in the Colour Index as Acid Blue dyes C.I. 113, 116 or even 120, particularly for dyeing wool, causes a degradation of the shade, mainly under the influence of reducing elements derived from the wool cystine, if no preliminary precautions are taken. Such a degradation appears mainly in clear shade dyeings and even more in pastel shade dyeings, where mixtures of dyes are used, said mixtures containing a small proportion of a blue dye which is substantially completely destroyed during the dyeing operation.
This reduction causing an at least partial destruction of the dye molecule is somewhat less apparent when a synthetic polyamide is dyed.
For removing these reduction effects appearing when wool is dyed, it is frequently necessary to add to the dyeing bath an oxidizing agent, such as potassium dichromate, so that the polluting load of the sewage is increased.
In respect of leather, it is known that the latter is generally treated with vegetable or synthetic tannins which are strong reducing agents of azo dyestuffs. The abovenamed navy blue disazo dyes are particularly sensitive to this reduction effect of the tannins and, as in the case of wool dyeing, lose an important part of their dyeing yield.
Applicant has found that it is possible to avoid said drawbacks by using a dye or mixture of dyes of the following general formula:
in which m=1, or 2, n=0, 1 or 2, the benzene ring
A being substituted by at least one alkyl group R of a low molecular weight, preferably by a methyl group; when there is only one methyl substituent, the latter is preferably in the ortho position with
respect to the azo moeity; when there are two
methyl substituents, one of these substituents
must be in the ortho position. Applicant has discovered the favourable action of this methyl group, in comparison with the usually used substituents, such as the halogens and the alkoxy groups. The naphthalene ring B carries a sulfonic
acid group in the 6 or 7 position.Applicant has found that the resistance of the molecule is surprisingly improved, when a mixture of 1 aminonaphthalene-6-sulfonic and 1
aminonaphthalene-7-sulfonic acids is used for
the synthesis of the dye.
The benzene ring C may also be substituted by
one or two methyl groups; a molecule containing
a single methyl substituent in the para position of
the amino group is preferably used.
It has been found that the presence of the alkyl - group in the benzene ring, which increases the
acidity of the molecule, is essentially favourable in
respect of the resistance of the dye to the
reduction phenomenons appearing when wool or
leather is dyed.
Moreover, it is possible, when using the dyes
according to this invention described in the
present specification, to correct imperfect colours
or to make further shadings, this being very
difficult when Acid Blue 113 or 1 16 dyes are
used, since the latter cannot be submitted to a
long boiling either in a reducing medium as alrady
pointed out or in the usual acid dyeing medium; in
this case, the dye undergoes a hydrolysis which
causes its degradation. Furthermore, the dyes
according to this invention are remarkably more
stable in respect of their hydrolysis.
Another advantage gained by using the dyes according to this invention is of toxicological and ecological nature. Unlike the Acid Blue 113 or
120 dyes, the dyes according to this invention are not synthesized from a-naphthalene, the toxicity of which has been proved.
The dyes used in accordance with this
invention may be prepared in a manner known per
se, by coupling, in a weakly acid aqueous
medium, one mole of a diazonium salt of an amine of the general formula:
with one mole of a coupling compound of the formula
The monoazo compound of formula II may be prepared by reacting, in a weakly acid aqueous medium, one mole of a diazonium salt of an amine of the formula:
with one mole of a coupling compound of the formula:
Examples of amines of the general formula IV,
which may be used for preparing diazonium salts
are the 2-methylaniline, the 4-methylaniline, the
2,4-dimethylaniline, the 2,5-dimethylaniline, the
2,6-dimethylaniline, the 2-methyl-6-ethylaniline, the 2-isopropylaniline and the like, as well as the
mixtures of these various amines.
The following examples illustrate the invention, without limiting its scope. The parts and percentages are by weight and the temperatures are in Celsius degrees.
Example 1
34.1 parts of the monoazo compound, prepared from 10.7 parts of ortho-toluidine and 22.3 parts of an equimolecular mixture of 1aminonaphthalene-6-sulfonic and 1aminonaphthalene-7-sulfonic acids, are suspended into 700 parts of water. After addition of 29 parts of a 30% hydrochloric acid solution, the compound is diazotized at 3O350 by adding 7 parts of sodium nitrite dissolved in 14 parts of water. After stirring for two hours, the formed diazonium salt is filtered and suspended in 500 parts of ice water. The obtained suspension is poured into 31.3 parts of N-(4'-methyl-phenyl)- 1aminonaphthalene-8-sulfonic acid dissolved in 500 parts of ice water containing 11 parts of crystallized sodium acetate.
After separation and filtration of the dye of the formula:
a black powder is obtained, such a powder yielding on wool and possibly synthetic polyamide fibres a greenish navy blue shade.
Example 2
When, in the example 1, the final coupling agent, i.e. N-(4'-methyl-phenyl)-1aminonaphthalene-8-sulfonic acid, is replaced by 29.9 parts of N-(phenyl)-1-aminonaphthalene-8- sulfonic acid, a dye is obtained which gives to wool a more reddish shade, while having the same resistance to degradation by reduction.
Example 3
When the ortho-toluidine is replaced by a mixture of 2,4-dimethylaniline and 2,6dimethylaniline in the process of example 1, a navy blue dye is obtained. When applied on wool, this dye gives a pure and solid navy blue shade.
Example 4
To 2,000 parts of an aqueous solution containing 40 parts of a 80% acetic acid solution and 100 parts of anhydrous sodium sulfate, 100 parts of wool previously treated in a bath containing 1 part by litre of sodium carbonate and dried are added. 0.5 parts of the dye prepared as described in example 1 and previously dissolved in water are then added. The bath is heated to 1000 and maintained at this temperature during about 90 minutes. The wool is then removed from the bath, rinsed and dried. The wool is coloured in a clear and pure navy blue shade.
When an equivalent amount of the Blue Acid 113 dye is used instead of the dye of example 1 under the same dyeing conditions, the treated wool has a greyish blue shade; for obtaining a suitable result, it is necessary to add 0.3 parts by litre of potassium dichromate to the dyeing bath.
Example 5
When 0.1 part of Acid Yellow 42, 0.2 parts of
Acid Red 128 and 0.2 parts of the navy blue dye prepared as described in example 1 are added in a dyeing bath prepared as described in example 4, a beige shade is obtained on wool.
When this navy blue dye of example 1 is replaced by an equivalent amount of Acid Blue 1 13, a dull orange brown shade is obtained, due to the destruction of the navy blue 113 dye by the reducing groups of the wool.
Example 6
100 parts of leather of the chromium velvet flesh split quality (previously remade green by treatment in 700 parts of water at 400 and 1 part of ammonia and rinsed) are introduced into a dyeing bath made of 500 parts of water at 600 containing 2 parts of ammonia. 200 parts of water at 600, in which 1 part of the dye according to example 1, are added. The bath is maintained at 500 during 30 minutes, and 0.7 parts of 85% formic acid are added in two times at a time interval of 10 minutes. After removal of the dyeing bath, the leather is rinsed and dried. In this manner, a dyed leather having a pure and bright navy blue shade is obtained.
When the dye of example 1 is replaced by an equivalent amount of Acid Blue C.1.1 16, a more dull and less intense shade is obtained.
Claims (6)
1. A process for dyeing wool or leather in blue or navy blue shades, without risk of shade degradation by reduction, in which is used a dye or mixture of dyes of the general formula
in which: The benzene ring A carries one or two alkyl groups
R (m=1 or 2) having a low molecular weight;
the naphthalene ring B carries a sulfonic acid solubilizing group in the 6 or 7 position;
the benzene ring C is unsubstituted or carries one or two methyl groups, one of which is in the para position of the amino bridge (n=O, 1 or 2).
2. A process according to claim 1, in which R is a methyl group.
3. A process according to any one of claims 1 and 2, in which the benzene ring A carries a single alkyl substituent in the ortho position of the azo bridge.
4. Natural polyamid fibres, particularly wool fibres, dyed by means of any one of the dyes described in claims 1,2, or 3.
5. Leather dyed by means of any one of the dyes described in claims 1, 2 or 3.
6. A process for dyeing wool or leather in blue or heavy blue shades substantially as herein described with reference to the Examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE191602A BE871849A (en) | 1978-11-08 | 1978-11-08 | SOLID NAVY BLUE DYE PROCESS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2034760A true GB2034760A (en) | 1980-06-11 |
| GB2034760B GB2034760B (en) | 1982-10-20 |
Family
ID=3843162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7937064A Expired GB2034760B (en) | 1978-11-08 | 1979-10-25 | Process for dyeing wool and leather in a solid navy blue shade |
Country Status (3)
| Country | Link |
|---|---|
| FR (1) | FR2442910A1 (en) |
| GB (1) | GB2034760B (en) |
| IT (1) | IT1126316B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2236767A (en) * | 1989-10-09 | 1991-04-17 | Sandoz Products Ltd | Wool dyeing |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1039462B (en) * | 1974-07-10 | 1979-12-10 | Crompton & Knowles Corp | GROUP OF DISAZOCOMPOSED TO DYE FIBERS AND POLYAMIDE FABRICS |
| GB1508136A (en) * | 1975-09-05 | 1978-04-19 | Yorkshire Chemicals Ltd | Colouration of synthetic polyamides process |
-
1979
- 1979-10-25 GB GB7937064A patent/GB2034760B/en not_active Expired
- 1979-10-26 FR FR7926589A patent/FR2442910A1/en active Granted
- 1979-11-05 IT IT27048/79A patent/IT1126316B/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2236767A (en) * | 1989-10-09 | 1991-04-17 | Sandoz Products Ltd | Wool dyeing |
Also Published As
| Publication number | Publication date |
|---|---|
| IT7927048A0 (en) | 1979-11-05 |
| GB2034760B (en) | 1982-10-20 |
| FR2442910B1 (en) | 1984-10-12 |
| FR2442910A1 (en) | 1980-06-27 |
| IT1126316B (en) | 1986-05-21 |
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