US2078861A - Manufacture of azo dyestuffs - Google Patents
Manufacture of azo dyestuffs Download PDFInfo
- Publication number
- US2078861A US2078861A US54789A US5478935A US2078861A US 2078861 A US2078861 A US 2078861A US 54789 A US54789 A US 54789A US 5478935 A US5478935 A US 5478935A US 2078861 A US2078861 A US 2078861A
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- United States
- Prior art keywords
- sodium
- amino
- benzene
- red
- group
- 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
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- 238000004519 manufacturing process Methods 0.000 title description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 73
- 239000011734 sodium Substances 0.000 description 27
- 229910052708 sodium Inorganic materials 0.000 description 27
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 26
- 239000000203 mixture Substances 0.000 description 19
- 230000008878 coupling Effects 0.000 description 16
- 238000010168 coupling process Methods 0.000 description 16
- 238000005859 coupling reaction Methods 0.000 description 16
- 239000002657 fibrous material Substances 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000006149 azo coupling reaction Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- -1 acyl acetic acids Chemical class 0.000 description 8
- 238000004043 dyeing Methods 0.000 description 8
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- OGHKEDLRKQAXBB-UHFFFAOYSA-N CC1=CC=C(C=C1)Cl.[Na] Chemical compound CC1=CC=C(C=C1)Cl.[Na] OGHKEDLRKQAXBB-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- ZMJZYXKPJWGDGR-UHFFFAOYSA-N aminosulfamic acid Chemical class NNS(O)(=O)=O ZMJZYXKPJWGDGR-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 230000003381 solubilizing effect Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- ZPWQALCOMQRMRK-UHFFFAOYSA-M sodium;6-hydroxynaphthalene-2-sulfonate Chemical compound [Na+].C1=C(S([O-])(=O)=O)C=CC2=CC(O)=CC=C21 ZPWQALCOMQRMRK-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-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
- ZYXIWQMBIJJEGN-UHFFFAOYSA-M 5-chloro-2-methylbenzenediazonium;chloride Chemical compound [Cl-].CC1=CC=C(Cl)C=C1[N+]#N ZYXIWQMBIJJEGN-UHFFFAOYSA-M 0.000 description 1
- 229920002955 Art silk Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 229920000715 Mucilage Polymers 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- XCFVSYWEMCQEOH-UHFFFAOYSA-L disodium 4-amino-5-hydroxy-3-[(4-nitrophenyl)diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].NC1=C(C(=CC2=CC(=CC(=C12)O)S(=O)(=O)[O-])S(=O)(=O)[O-])N=NC1=CC=C(C=C1)[N+](=O)[O-] XCFVSYWEMCQEOH-UHFFFAOYSA-L 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- PPSSQRUPSRPZON-UHFFFAOYSA-N nitrobenzene;sodium Chemical compound [Na].[O-][N+](=O)C1=CC=CC=C1 PPSSQRUPSRPZON-UHFFFAOYSA-N 0.000 description 1
- 150000004005 nitrosamines Chemical class 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 235000013311 vegetables Nutrition 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
- C09B41/00—Special methods of performing the coupling reaction
Definitions
- the present invention relates to the production of azo-dyestufis in substance or on a fibre which also makes use of mixtures of coupling components with aromatic anti-diazosulphonates or hydrazine-sulphonates i. e. with aromatic compounds in which a sulphonic group is connected to an aryl group by a dinitrogen group.
- the mixture is caused to undergo coupling by-subjecting it to the action of an energetic oxidizing agent and then, if required, to the action of an alkaline agent.
- the invention is of special importance in its application to the production of insoluble azodyestufis on textile fibres.
- diazosulphonates or hydrazine-sulphonates prepared from aromatic amines which are free from groups which impart solubility, such as COOH or $0311 and coupling components which, are likewise free from these groups.
- the coupling components generally contain hydroxyl groups which render them soluble in alkaline media, an alkaline solution of the' mixture can be used for the impregnation of the fibre. This impregnation may extend throughout the material or may be only local so that after development there will be produced a dyeing or a print respec tively.
- the solutions may, of course, contain all the known ingredients which are used in dyeing and printing and especially in the production of insoluble azo-dyestufis on fibrous materials by means of a single mixture containing the two coupling substances (rapid solid dyestuffs, rapidogens,
- the dyestufi may be formed actually in the course of the oxidation or it may be formed in a subsequent treatment, generally an alkaline treatment which itself may be conducted in a. liquid or gaseous medium.
- an alkaline treatment which itself may be conducted in a. liquid or gaseous medium.
- the oxidation may be conducted at a temperature higher than ordinary temperature; thus the dyestufis may be formed on the fibre by treating the fibre impregnated with the selected mixture with a halogen in presence of hot water or steam.
- diazosulphonates or hydrazine-sulphonates which are best suited for carrying out the invention are those-which are prepared from feebly basic aromatic amines containing in the molecule a negative substituent such as a nitro-group or halogen and so on. 4
- azo-components of the type hitherto used industrially for a like purpose such as the arylides of organic acids capable of coupling, particularly the arylides of B-oxynaphthoic acid, of 2-hydroxyanthracene-3-carboxylic acid, of oxycarbazole and oxynaphthocarbazole carboxylic acids, of carboxylic acids having a coupling position in a methylene group which may or may not form part of a ring, such as acyl acetic acids, aroyl acetic acids and so on.
- Insoluble azo-dyestufis can be produced in accordance with the present invention on the various animal and vegetable fibres and on artificial fibres of regenerated cellulose, cellulose ethers or cellulose esters.
- Example 1 A cotton fabric isprinted with the following mixture: Y
- Coupling component Dlazosulphonate (2'-h droxy-W-naph- Shade they Sodium z-metlioxy-a-ni- Aminobenzene... Bluish bortrobenzenediazosuldeaux. pbonate.
- cry-benzene i-amino-a-nitroben- Do.
- Example 2 A cotton fabric is printed with the following mixture:
- Example 3 If in Example 1 the sodium 5-chloro-2-methylbenzene-diazosulphonate is replaced by the corresponding quantity of S-chloro-Z-methylbenzerie hydrazine sulphonic acid and the operation is conducted otherwise as therein prescribed there are obtained prints of the same shade.
- Example 4 Printing is conducted as in Example 1 but with the use of sodium 2-methoxy-4-chlorobenzene diazos ulphonate and thoyl)-amino-2-methoxybenzene.
- the dyeing is developed by passing the moist material during several seconds first through an atmosphere of chlorine and then through an atmosphere of ammonia or through a solution of sodium carbonate. Red prints are obtained.
- Example 5 A cotton fabric is impregnated with the following preparation:-
- Example 6 A current of chlorine is passed slowly through a cold solution prepared'from parts of sodium 2-methyl-5-chlorobenzene diazosulphonate, 10 parts of 1-(2'-hydroxy-3'-naphthoyl) -amino-2- methylbenzene, 10 parts of alcohol, 10 parts of caustic soda solution of 40 Be. and 960 parts of water. There is at once formed-a red precipitate which gradually increases in bulk. when no further precipitation occurs the current of chlorine is interrupted and the dyestufi is filtered and dried.
- Example 7 A solution is prepared by dissolving 1 part of sodium 2-hydroxy-naphthalene-6-sulphonate, 1 part of sodium 2-methyl-5-chlorobenzene diazopart of sodium bicarbonate and 2 parts of sodium chloride in 100 parts of water and a current of chlorine is passed through the solution. There is at once precipitated an orangered dyestufi which is isolated by saturating the solution with salt and filtering. The dyestufi is identical with that obtained by the direct action of 2-methyl-5-chlorobenzene diazonium chloride on sodium 2-hydroxynaphthalene-6-sulphonate. It dyes wool .an orange shade.
- diazosulphonates referred to herein may be prepared by any suitable process and particularly in the manner indicated in French Patent No. 760,784.
- treating with an oxidizing which comprises, treating with an oxidizing agenta mixture of an azo-coupling component and a salt of an aryl hydrazine sulphonic acid.
- a method of manufacturing azo-dyestufis which comprises, treating a mixture of an azocoupling component and a salt. oi'a sulphonic derivative of an aryl compound, in which the sulphonic group is connected to the aryl nucleus through a dinitrogen group, with an oxidizing agent and subsequently with an alkaline agent.
- said coupling component is an arylide of an organic acid capable of coupling.
- a method of producing insoluble dyestufls on fibrous material which comprises, impregnating said material simultaneously with an oxidizing agent and a mixture of an azo-coupling component and a salt of a sulphonic derivative of an aryl. compound in which the sulphonic group is connected to the aryl nucleus through a dinitrogen group, neither of these components including a solubilizing group apart from said sulphonic group, and treating said, impregnated fibrous material with a halogen in the presence of Water.
- a method for producing water insoluble azo-dyestuffs on a fibrous material which comprises applying to said fibrous material a. mixture including an azo-coupling component and a salt of a sulphonic derivative of an aryl compound in which the sulphonic group is connected to the aryl nucleus through a dinitrogen group, neither of said azo-coupling component and said salt including a water solubilizing group apart from said sulphonic group, and subjecting said mixture on the fibrous material to the action of an oxidizing agent.
- a method of dyeing a fibrous material which comprises applying to said fibrous material an alkaline mixture including an azo-coupling component and a salt of a sulphonic derivative of an aryl compound containing at least one hydroxyl group, in which the sulphonic group is connected to the aryl nucleus through a dinitrogen group, neither of said azo-coupling component and said salt including a water solubilizing 7 group apart from said sulphonic group, and subjecting said mixture on the fibrous material to the action or an oxidizing agent.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Patented Apr. 27, 1937 ce, assior a Societe Anonyme des Maties Coiorantes & Produits Chimiques de-Saint-Denis, Paris, France, a
company or France No Drawing. Application December 16, 1935, Egegial No. 54.789. In France December 22,
1d @laims.
Mixtures of aryl anti-diazosulphonates or aryl hydrazine-sulphonatm with azo coupling components are stable under ordinary conditions and their solutions do not undergo spontaneous coupling; It is known that these mixtures can be caused to undergo coupling by the action of light (see particularly French Patent No. 760,784) or in the case of certain particular diazosulphonates applied to fibrous material by impregnation, by the action of a steaming operation (see German Patents Nos. 560,797, 563,061, 560,798 and 578,648)
The present invention relates to the production of azo-dyestufis in substance or on a fibre which also makes use of mixtures of coupling components with aromatic anti-diazosulphonates or hydrazine-sulphonates i. e. with aromatic compounds in which a sulphonic group is connected to an aryl group by a dinitrogen group. In accordance with the present invention the mixture is caused to undergo coupling by-subjecting it to the action of an energetic oxidizing agent and then, if required, to the action of an alkaline agent.
The invention is of special importance in its application to the production of insoluble azodyestufis on textile fibres. For this purpose there are used diazosulphonates or hydrazine-sulphonates prepared from aromatic amines which are free from groups which impart solubility, such as COOH or $0311 and coupling components which, are likewise free from these groups. Since the coupling components generally contain hydroxyl groups which render them soluble in alkaline media, an alkaline solution of the' mixture can be used for the impregnation of the fibre. This impregnation may extend throughout the material or may be only local so that after development there will be produced a dyeing or a print respec tively. The solutions may, of course, contain all the known ingredients which are used in dyeing and printing and especially in the production of insoluble azo-dyestufis on fibrous materials by means of a single mixture containing the two coupling substances (rapid solid dyestuffs, rapidogens,
, dyestufis obtained with the aid of nitrosamines) The course of the process is quite unexpected for it was to be supposed that the oxidizing agent would first attack the azo-coupling components which are readily oxidized and would thus render coupling impracticable.
The dyestufi may be formed actually in the course of the oxidation or it may be formed in a subsequent treatment, generally an alkaline treatment which itself may be conducted in a. liquid or gaseous medium. In order to prepare the dyestuif in a single stage the oxidation may be conducted at a temperature higher than ordinary temperature; thus the dyestufis may be formed on the fibre by treating the fibre impregnated with the selected mixture with a halogen in presence of hot water or steam.
The diazosulphonates or hydrazine-sulphonates which are best suited for carrying out the invention are those-which are prepared from feebly basic aromatic amines containing in the molecule a negative substituent such as a nitro-group or halogen and so on. 4
For the production of azo-dyestufis on fibrous material in accordance with the invention there are advantageously used azo-components of the type hitherto used industrially for a like purpose, such as the arylides of organic acids capable of coupling, particularly the arylides of B-oxynaphthoic acid, of 2-hydroxyanthracene-3-carboxylic acid, of oxycarbazole and oxynaphthocarbazole carboxylic acids, of carboxylic acids having a coupling position in a methylene group which may or may not form part of a ring, such as acyl acetic acids, aroyl acetic acids and so on.
Insoluble azo-dyestufis can be produced in accordance with the present invention on the various animal and vegetable fibres and on artificial fibres of regenerated cellulose, cellulose ethers or cellulose esters.
The following examples illustrate the invention, the parts in Examples 6 and 7 being by weight:
Example 1 A cotton fabric isprinted with the following mixture: Y
Grams Sodium 2-methyl-5-chlorobenzene diazo-sul- After the material has been dried it is treated for 3 seconds in an apparatus containing steam and chlorine at 100 C. in order to develop the dyeing. Then the fabric is washed and treated in a boiling bath containing soap and sodium carbonate. There are obtained beautiful red prints.
Like prints are obtained by printing the same mixture on fabrics of artificial silk of viscose or acetyl cellulose, or natural silk or wool.
By replacing the two components in the foregoing example by other diazosulphonates and coupling components there are obtained the shades indicated in the following table:
Coupling component: Dlazosulphonate (2'-h droxy-W-naph- Shade they Sodium z-metlioxy-a-ni- Aminobenzene... Bluish bortrobenzenediazosuldeaux. pbonate.
D 1-amino-225-dimeth- Do.
cry-benzene. i-amino-a-nitroben- Do.
zene. l-arnino-z-methylben- Do.
zene. Do l-amino-Z-methoxy- Bordeaux.
benzene. Do Lamina-l-methoxy- Bluish borbenzene. deaux. Do-. 2-aminonaphthalene..- Do. Do 1-amino-2-methyl-4- Do.
chlorobenzene.
Bedlam 2-n ifl-4 mflii y aminobenzene Biuish red. benzene diazosulphonate.
Do 1-amino-2:5-dimetii- Red.
oxy-benzene.
Do l-amino-ii-nitroben- Binish red.
zone.
Sodium 2nlt -4-m i7 1-amino-2-methyl- Very bluish nz diawwlpho benzene. red. na
D0 1-amino-2-methoxy- Red.
benzene.
D0 1-amino-4-methoxy- Very bluish benzene. red.
sodium z-lflll'flfllefllyl- 2-aminonaphthaiene... Red.
beitiezene diezosulpho na D0 1-nmino-2-methyl- Very bluish benzene diazosuipho- 1-amino-225-dimeth Orange red.
oxy nzene. 1 amino 2 metbyl- Do.
benzene. 1 amino 2 methoxy- Do.
benzene. 1 amino 3 nitro- Red.
benzene. 1 amino 4 methoxy- Orange red. I benzene. Sodium 3- h1 9- -1 Bfl y Aminobenzene Yeliowish red.
benzene diazosulpho- [l8 0- Do 1-emine-2z5- dimetii Yellowish red.
oxybenzene. Do 1 amino 3 nitro- Brownish red.
benzene. Do 1 amino 2 methyl- Bright red. benzene. Do 1-amino-2-methoxy- Yellowish red.
benzene. Do.. 1 amino 4 methoxy- Scarlet. Sodi m 2 5 di m cben fi o a 11 I 0 0! mino nzene ran 0 re zene diazosulphonate. 8
Do 1-amino-2z5-dimetb- D u l l r e d oxybenzene. orange. Do 1 amino 3 nitro- D u ll orange benzene. 7 re 1-amino-2-methyl- Bright red benzene. orange. 1 amino- 2- methoxy- Orange red.
benzene. l-amino-4-methoxy- D u ll orange DZSDO. Sodium a-nitro-e-methoxy- 1-amino-2:5-dimeth- Dull red.
benrenediazosulphonate. a ry-benzene.
Do... i-emino-a-nitrobenzene. Banish red. Do l-amino-z-metbylben- Yeilowish red.
zene. Do i-amino-2-methoxy- Bright bluish benzene. scarlet. Sodium 2-nitrobenzenc- Aminobenzene Red orange.
diazosulphonate. I
Do 1-amino-2:5-dimeth- Dull red oroxy-benzene. cage;
r Bluish scarlet.
Coupling component Dinzosulphonate (2'4: roxy-3'-neph- Shade they)- Sodium Z-nitrobenzene- 1-arnino-2-methylben- Yeliowish red.
tro benzene diazosul amino)-3:3 i-
diazosulphonate. zene.
Do l-amlno-2-metboxy- Red orange. benzene.
Dlazosulphonate Coupling component Shade Sodium 2-methoxy-4-nitrol-(2-hydroxyanthra- Bluisli black hen z en e-diazosulphocene -3 carboylamviolet. nate. inol-Q-meth y i b e n zene.
Sodium 2-nitro-4-methyl- ....-.do Brown red.
benzene-diazosulphcnate.
Sodium 3-nitro-6-methyl- .--..do Duiivioiet.
benzene-diazosulphonate.
Sodiuin3-chloro-e-methyl- .-...do Do.
benzenediazosulphonate.
Sodium 2:5-dichloroben- Ydr0Xyanthra- Brown.
zene diezosulpbonate. cene-3'-carbo lamino)-2-methy -benzene.
Sodium 3-nitro-B-methoxy- .....do Dull violet.
benzene diazosulphonate.
Sodium Q-methoxy-l-nitro- 1-(2'--hydroxyeerba- Brown red.
benzene diazosulplionate. zole-3-car y ino-4-chlorobenzone.
Sodium 3-nitro-fi-methyl- Yellow brown.
benzene dinzosuiphonate.
SodiumSchloro-G-methyibenzene diazosulfabonate.
Sodium median oi-oben- 1- (2 y w r a- Ye w b zene-diazosulphonate. Z r g amino-4-chioro nzene..
$0dillm3-nitro-6-methoxydo Brown.
benzene diazosulphonate.
odium Z-nitrobenzene- .--..d0 D0- diazosuiphonate.
Sodium 2-methoxy-4-nli-(3"- y y-7':8 Yellow ish trobenzene diazosulbenzocarbazol-2-'- g phonate. carboylamino)-4- methoxybenzcne.
Do 1-(3-hydroxy-7':8'- Grey.
benzocarbazol-2"- carboylamino)-2- methoxy-s-methyl- A benzene.
sodium 2-nitro-4-methyldo Yellowieh betnzene-diazosulphog na e.
Sodium a nitro-n-methyl- ..do Reddish black betnzene-diazosulplioviolet. na 0.
Sodium 2-methoxy-4-ni- 4:4 -di(acetoacet 1- Yellow.
phonate. methyl-diphenyl. Sodium 2-nltro4-methyl- ..do Reddisb yelbenzene-diazosulpholow.
n e. Sodium S-nIt ro-(i-methyl- .....do Yellow.
benzene-dlazosulphonate. Sodium S-chlorodmeth- .-.--do D0.
vl-genzene-diazosulphonn Sodium 2-nitrobenzene- ..do Brownish yeldiazosulphonate. low. Sodium 2:5-dichloroben- 2-hydroxynephthalcne Orange.
zene-diazosulphonnte. Sodium 2-nltrobenzene- ...do Orange red.
diazosulphonate.
Example 2 A cotton fabric is printed with the following mixture:
Sodium 2-nitrobenzene-diazosulphonate- Grams 15 1 (2' hydroxy 3' naphthoyl) amino 2 methylbenzene 15 Caustic soda solution of 40 B 14 Starch tragacanth thickening 500 Water 412 water.
'sulphonate, 0.8
By using in the printing preparation sodium 2 -dichlorobenzene-diazosulphonate and 1- (2'- hydroxy-3'-naphthoyl) amino-Z-methylbenzene and developing the dyeing. by means of a boiling salt solution of 20 percent strength through which chlorine is passed there are obtained yellowish-scarlet prints.
Example 3 If in Example 1 the sodium 5-chloro-2-methylbenzene-diazosulphonate is replaced by the corresponding quantity of S-chloro-Z-methylbenzerie hydrazine sulphonic acid and the operation is conducted otherwise as therein prescribed there are obtained prints of the same shade.
Example 4 Printing is conducted as in Example 1 but with the use of sodium 2-methoxy-4-chlorobenzene diazos ulphonate and thoyl)-amino-2-methoxybenzene. The dyeing is developed by passing the moist material during several seconds first through an atmosphere of chlorine and then through an atmosphere of ammonia or through a solution of sodium carbonate. Red prints are obtained.
Example 5 A cotton fabric is impregnated with the following preparation:-
Grams Sodium 2-methyl-5-chlorobenzene diazosulphonate 20 1 (2' hydroxy- 3- naphthoyl) amino -2 methylbenzene 20 Alcohol 20 Caustic soda solution of 40 B 20 Glycerine 50 Tragacanth mucilage of 6 per cent strength- 100 Water 770 The material is dried and treated as described in Example 1 to develop the dyeing. A beautiful red dyeing is thus obtained.
Example 6 A current of chlorine is passed slowly through a cold solution prepared'from parts of sodium 2-methyl-5-chlorobenzene diazosulphonate, 10 parts of 1-(2'-hydroxy-3'-naphthoyl) -amino-2- methylbenzene, 10 parts of alcohol, 10 parts of caustic soda solution of 40 Be. and 960 parts of water. There is at once formed-a red precipitate which gradually increases in bulk. when no further precipitation occurs the current of chlorine is interrupted and the dyestufi is filtered and dried.
Example 7 A solution is prepared by dissolving 1 part of sodium 2-hydroxy-naphthalene-6-sulphonate, 1 part of sodium 2-methyl-5-chlorobenzene diazopart of sodium bicarbonate and 2 parts of sodium chloride in 100 parts of water and a current of chlorine is passed through the solution. There is at once precipitated an orangered dyestufi which is isolated by saturating the solution with salt and filtering. The dyestufi is identical with that obtained by the direct action of 2-methyl-5-chlorobenzene diazonium chloride on sodium 2-hydroxynaphthalene-6-sulphonate. It dyes wool .an orange shade.
The diazosulphonates referred to herein may be prepared by any suitable process and particularly in the manner indicated in French Patent No. 760,784.
What I claim is:
l. A method of manufacturing azo-dyestufis,
which comprises, treating with an oxidizing which comprises, treating with an oxidizing agenta mixture of an azo-coupling component and a salt of an aryl hydrazine sulphonic acid.
4. A method of manufacturing azo-dyestufis, which comprises, treating a mixture of an azocoupling component and a salt. oi'a sulphonic derivative of an aryl compound, in which the sulphonic group is connected to the aryl nucleus through a dinitrogen group, with an oxidizing agent and subsequently with an alkaline agent.
5. A method according to claim 1 in which said salt contains in the nucleus an electronegative group.
6. A method according to claim 1 in which said salt contains in the nucleus a halogen group.
7. A method according to claim 1 in which said salt contains in the nucleus a nitro-group.
8. A method according to claim 1 in which said coupling component is an arylide of an organic acid capable of coupling.
9. A method of producing insoluble dyestufls on fibrous material, which comprises, impregnating said material simultaneously with an oxidizing agent and a mixture of an azo-coupling component and a salt of a sulphonic derivative of an aryl. compound in which the sulphonic group is connected to the aryl nucleus through a dinitrogen group, neither of these components including a solubilizing group apart from said sulphonic group, and treating said, impregnated fibrous material with a halogen in the presence of Water.
10. A methodaccording to claim 9 in which said water is in the form of steam.
11. A method for producing water insoluble azo-dyestuffs on a fibrous material, which comprises applying to said fibrous material a. mixture including an azo-coupling component and a salt of a sulphonic derivative of an aryl compound in which the sulphonic group is connected to the aryl nucleus through a dinitrogen group, neither of said azo-coupling component and said salt including a water solubilizing group apart from said sulphonic group, and subjecting said mixture on the fibrous material to the action of an oxidizing agent.
12. The method of claim 11, further comprising subjecting said mixture on the fibrous material to a subsequent treatment with an alkaline agent.
13. A method of dyeing a fibrous material which comprises applying to said fibrous material an alkaline mixture including an azo-coupling component and a salt of a sulphonic derivative of an aryl compound containing at least one hydroxyl group, in which the sulphonic group is connected to the aryl nucleus through a dinitrogen group, neither of said azo-coupling component and said salt including a water solubilizing 7 group apart from said sulphonic group, and subjecting said mixture on the fibrous material to the action or an oxidizing agent.
14. The method of developing a. normally stable mixture of an azo-coupling component and a salt 5 of a suiphonic derivative of an aryl compound in which the sulphonic group is connected to the
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR2078861X | 1934-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2078861A true US2078861A (en) | 1937-04-27 |
Family
ID=9683547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US54789A Expired - Lifetime US2078861A (en) | 1934-12-22 | 1935-12-16 | Manufacture of azo dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2078861A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2593930A (en) * | 1951-09-20 | 1952-04-22 | Gen Aniline & Film Corp | Process of printing fabrics with aryl sulfonhydrazides |
| US2883258A (en) * | 1958-05-26 | 1959-04-21 | American Cyanamid Co | Stable concentrated naphthol solutions |
| US3029121A (en) * | 1959-04-08 | 1962-04-10 | Du Pont | Process of coloring by oxidizing solid polyesters of terephthalic acid and glycols and reacting with hydrazine compounds and products produced thereby |
-
1935
- 1935-12-16 US US54789A patent/US2078861A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2593930A (en) * | 1951-09-20 | 1952-04-22 | Gen Aniline & Film Corp | Process of printing fabrics with aryl sulfonhydrazides |
| US2883258A (en) * | 1958-05-26 | 1959-04-21 | American Cyanamid Co | Stable concentrated naphthol solutions |
| US3029121A (en) * | 1959-04-08 | 1962-04-10 | Du Pont | Process of coloring by oxidizing solid polyesters of terephthalic acid and glycols and reacting with hydrazine compounds and products produced thereby |
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