US1853418A - Dyeing of viscose - Google Patents
Dyeing of viscose Download PDFInfo
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- US1853418A US1853418A US342956A US34295629A US1853418A US 1853418 A US1853418 A US 1853418A US 342956 A US342956 A US 342956A US 34295629 A US34295629 A US 34295629A US 1853418 A US1853418 A US 1853418A
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- US
- United States
- Prior art keywords
- viscose
- amino
- dyeing
- sulfonic acid
- acid
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- Expired - Lifetime
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- 229920000297 Rayon Polymers 0.000 title description 19
- 238000004043 dyeing Methods 0.000 title description 19
- -1 ZlIlC Chemical compound 0.000 description 14
- 239000000975 dye Substances 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 10
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 7
- 229910052804 chromium Inorganic materials 0.000 description 7
- 239000011651 chromium Substances 0.000 description 7
- 229910052802 copper Inorganic materials 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229910017052 cobalt Inorganic materials 0.000 description 5
- 239000010941 cobalt Substances 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 229910001385 heavy metal Inorganic materials 0.000 description 4
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000000980 acid dye Substances 0.000 description 3
- 229910052793 cadmium Inorganic materials 0.000 description 3
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 3
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920002955 Art silk Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 239000010446 mirabilite Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical group OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- YRJSLCBKZMMEPB-UHFFFAOYSA-N 2-(2-methylpropyl)naphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CC(C)C)=CC=C21 YRJSLCBKZMMEPB-UHFFFAOYSA-N 0.000 description 1
- IFXKXCLVKQVVDI-UHFFFAOYSA-N 2-amino-5-chlorobenzoic acid Chemical compound NC1=CC=C(Cl)C=C1C(O)=O IFXKXCLVKQVVDI-UHFFFAOYSA-N 0.000 description 1
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
- IQGMRVWUTCYCST-UHFFFAOYSA-N 3-Aminosalicylic acid Chemical compound NC1=CC=CC(C(O)=O)=C1O IQGMRVWUTCYCST-UHFFFAOYSA-N 0.000 description 1
- HKWPUUYEGGDLJF-UHFFFAOYSA-N 4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HKWPUUYEGGDLJF-UHFFFAOYSA-N 0.000 description 1
- YLKCHWCYYNKADS-UHFFFAOYSA-N 5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)=CC=CC2=C1S(O)(=O)=O YLKCHWCYYNKADS-UHFFFAOYSA-N 0.000 description 1
- YUNBHHWDQDGWHC-UHFFFAOYSA-N 6-aminonaphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(N)=CC=C21 YUNBHHWDQDGWHC-UHFFFAOYSA-N 0.000 description 1
- YGNDWDUEMICDLW-UHFFFAOYSA-N 7-anilino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C=1C=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=1NC1=CC=CC=C1 YGNDWDUEMICDLW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WQZGKKKJIJFFOK-VSOAQEOCSA-N L-altropyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-VSOAQEOCSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 229910021563 chromium fluoride Inorganic materials 0.000 description 1
- QOWZHEWZFLTYQP-UHFFFAOYSA-K chromium(3+);triformate Chemical compound [Cr+3].[O-]C=O.[O-]C=O.[O-]C=O QOWZHEWZFLTYQP-UHFFFAOYSA-K 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- XDBSEZHMWGHVIL-UHFFFAOYSA-M hydroxy(dioxo)vanadium Chemical compound O[V](=O)=O XDBSEZHMWGHVIL-UHFFFAOYSA-M 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 108010052322 limitin Proteins 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000005404 monopole Effects 0.000 description 1
- LVIYYTJTOKJJOC-UHFFFAOYSA-N nickel phthalocyanine Chemical compound [Ni+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 LVIYYTJTOKJJOC-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 229960005369 scarlet red Drugs 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
- WQEVDHBJGNOKKO-UHFFFAOYSA-K vanadic acid Chemical class O[V](O)(O)=O WQEVDHBJGNOKKO-UHFFFAOYSA-K 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 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
- C09B45/00—Complex metal compounds of azo dyes
Definitions
- the resent invention relates to a process of pro ucing even dyeings on viscose fabrics containing or composed of viscose of irregular physical or chemical quality and to the 5 dyed fabrics obtainable thereby.
- the azo dyestufis which are capable of forming heavy metal complex compounds group in the molecule or by having .in or,tho positlon to an azo group a hydroxy-, a caroxylic acid-, an alkoxy-, an aralkoxyor an. aldehyde-group.
- the hea metal complex compounds are enerally ibtainable by treating for some ours the aqueous solution of the dyestuff with an aqueous solution of a salt of the repective heavy metal.
- dyestuffs containing copper or iron, are obtainable by heating an aqueous solution of the dyestuif with copper sulfate or ferrous sulfate for several hours, or according to the process described in'the U. S. P. 1,690,782, issued November 6, 1928 b reacting upon the aqueous solution of the yestufi' with a copper-amine compound.
- Nickel,cob'alt, cadmium or zinc amine azo compounds are obtainable, for example, by the use of nickelous amine salts, such a nickelous tetramine sulfate, of cobalt amine salts, such as carbonato tetramine cobalti chloride, or of cadimumor zinc-amine salts, instead of the copper amine complex salts used in the prooes of U. S. P. 1,690,782.
- Dyetufls, containing chromium are obare distinguished by having a salicyclic.
- com lex vanadium compounds are obtainable by oiling the dyestuif with a water soluble vanadic acid salt, for example, the ammonium salt of the meta vanadic acid.
- the dyeing is carried out in the usual manner as is outlined in the examples, by'dissolving the dyestuffs in hot water and adding to the dye-bath Glaubers salt and monopol soap (alkali metal salt of sulfonated castor oil), if desired with the addition of a wetting agent, f. i. an alkyl-naphthalene-sulfonic acid, such as iso butyl-napthalene-disulfonic acid.
- a wetting agent f. i. an alkyl-naphthalene-sulfonic acid, such as iso butyl-napthalene-disulfonic acid.
- the viscose is introduced into the bath at about 30 0., then the bath is slowly heated to about 80 0., at which temperature the viscose is dyed for about hour to 1 hour. Then the viscoseiis washed and dried.
- the dyeings thus produced on viscose and in particular on knitted artificialv silk by means of the azo dyestuffs containing a heavy metal in complex combination possess a good fastness to light nd are distinguished by an excellent evenness.
- Example 1.2 g. of the yestufi' containing copper in complex combination obtainable according to the process of the U. S. P. 1,690,782 from amino benzene-2-carboxylic acid, 2-phenylamino-5-hydroxy-naphthalene 7-sulfonic acid and tetramine-cupric sulfate and corresponding to the following probable formula:
- the dyestuff obtainable from amino benzene-2-carboxylic acid and 2-benzoyl amino- 5-hydroxynaphthalene-7'-sulfonic acid and coppered in substance dyes, according to the same process, yellowish red shades; the copper amine complex compound of the dyestuff obtainable from 2 molecules of amino benzene-2-carboxylic acid, the urea of 2-amino-' 5-hydroxynaphthalene-7-sulfonic acid and tetramine-cupric sulfate dyes orange red shades; the copper amine complex compound of the dyestufi' obtainable from two molecules of 4-chloro-1-amino benzene-2-carboxylic acid, 5.5'-dihydroxy-2.2'-dinaphthyl ammo- 7.7 -disulfonic acid and tetramine cupric sulfate dyes bluish violet shades. All these dyestuffs yield'dyeings which are ver fast to light
- a violet shade of the same properties is produced by dyeing knitted viscose artificial silk in the manner described with a dyestuff containing COPFBI in complex combination and obtained rom 5-nitro-2-a-mino-1-methoxy benzene-4-sulfonic acid and 2(4'-methoxy benzoyl)-amino-5-hydroxynaphthalene- 7 -sulfonic acid.
- a remarkable even scarlet red dyeing is produced by the use of a dyestufi containing co per in complex combination and 0btamed from 2-amino-1-phenol glycerine ether and 2- (4'-methy1-benzoyl) -amino-5-hydrox na hthalene-7-sulfonic acid.
- the azo dyestuffs containing a carboxylic group in the ortho position to the azo group there can also be used quite generally such dyestuffs as contain the carbonylor hydroxy group in the ortho position to at least one azo oup; the above mentioned dyestuffs containing a methoxy group in the ortho osition to an azo group can likewise be rep aced by dyestuffs, containing in the ortho position to an azo group other alkyl hydroxy-, aralkyl hydroxyor aryl hydroxy oups, which may also be substituted, if esired.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Patented Apr. 12, 1932 UNITED STATES PATENT OFFICE Wm!) HKNTBICH AND MAX HARDTMANN, OF WIESDORF-ONJHE-RHINE JOSE! HILGEK OI COLOGNE-HULHEIM, AND RUDOLF KNOGHE, OI LEVERKUBEN-ON- THE-Rm GERMANY, ASSIGNORS 'I'O GENERAL ANILINE WORKS, INC, 01 NEW YORK, N. Y A GOBPORA'IION OF DELAWARE name or vIscosE ll'o Drawing. Application filed February 26, 1928, Serial No. 842,956, and in Germany February 87, me.
The resent invention relates to a process of pro ucing even dyeings on viscose fabrics containing or composed of viscose of irregular physical or chemical quality and to the 5 dyed fabrics obtainable thereby.
In dyeing viscose fabrics by means of the dyestuffs hitherto in use, streaky uneven dyeings are frequentlyobtained.v This disadvantage is due to the irregular physical or chemical quality of the commercial viscose used,- which displa s a very variable afiinity towards one and t e same dyestuif.
In accordance with the present invention,
the disadvantages encountered in the dyeing of viscose fabrics of irre uIar quality with the substantive dyestufi's hitherto employed, can be avoided b effecting the dyelng by means of dyestu s containing, in complex combination, heavy metals, such as copper, nickel, cobalt, chromium, cadmium, ZlIlC, vanadium and iron.
The azo dyestufis which are capable of forming heavy metal complex compounds group in the molecule or by having .in or,tho positlon to an azo group a hydroxy-, a caroxylic acid-, an alkoxy-, an aralkoxyor an. aldehyde-group.
The hea metal complex compounds are enerally ibtainable by treating for some ours the aqueous solution of the dyestuff with an aqueous solution of a salt of the repective heavy metal. For example, dyestuffs, containing copper or iron, are obtainable by heating an aqueous solution of the dyestuif with copper sulfate or ferrous sulfate for several hours, or according to the process described in'the U. S. P. 1,690,782, issued November 6, 1928 b reacting upon the aqueous solution of the yestufi' with a copper-amine compound.
Complex nickel,cob'alt, cadmium or zinc amine azo compounds are obtainable, for example, by the use of nickelous amine salts, such a nickelous tetramine sulfate, of cobalt amine salts, such as carbonato tetramine cobalti chloride, or of cadimumor zinc-amine salts, instead of the copper amine complex salts used in the prooes of U. S. P. 1,690,782. Dyetufls, containing chromium, are obare distinguished by having a salicyclic.
tainable by boiling the aqueous solution of the dyestufi for several hours with a water soluble chromium salt, such as chromium formate, and chromium fluoride; com lex vanadium compounds are obtainable by oiling the dyestuif with a water soluble vanadic acid salt, for example, the ammonium salt of the meta vanadic acid.
The dyeing is carried out in the usual manner as is outlined in the examples, by'dissolving the dyestuffs in hot water and adding to the dye-bath Glaubers salt and monopol soap (alkali metal salt of sulfonated castor oil), if desired with the addition of a wetting agent, f. i. an alkyl-naphthalene-sulfonic acid, such as iso butyl-napthalene-disulfonic acid. The viscose is introduced into the bath at about 30 0., then the bath is slowly heated to about 80 0., at which temperature the viscose is dyed for about hour to 1 hour. Then the viscoseiis washed and dried.
The dyeings thus produced on viscose and in particular on knitted artificialv silk by means of the azo dyestuffs containing a heavy metal in complex combination possess a good fastness to light nd are distinguished by an excellent evenness.
The following examples will illustrate our invention, without limitin it thereto:
. Example 1.2 g. of the yestufi' containing copper in complex combination, obtainable according to the process of the U. S. P. 1,690,782 from amino benzene-2-carboxylic acid, 2-phenylamino-5-hydroxy-naphthalene 7-sulfonic acid and tetramine-cupric sulfate and corresponding to the following probable formula:
coon on N=N 1 o H0: (N s): are dissolved in 3 liters of hot water. 100
dyeings, and-ofremarkable fastness to light.
The dyestuff obtainable from amino benzene-2-carboxylic acid and 2-benzoyl amino- 5-hydroxynaphthalene-7'-sulfonic acid and coppered in substance dyes, according to the same process, yellowish red shades; the copper amine complex compound of the dyestuff obtainable from 2 molecules of amino benzene-2-carboxylic acid, the urea of 2-amino-' 5-hydroxynaphthalene-7-sulfonic acid and tetramine-cupric sulfate dyes orange red shades; the copper amine complex compound of the dyestufi' obtainable from two molecules of 4-chloro-1-amino benzene-2-carboxylic acid, 5.5'-dihydroxy-2.2'-dinaphthyl ammo- 7.7 -disulfonic acid and tetramine cupric sulfate dyes bluish violet shades. All these dyestuffs yield'dyeings which are ver fast to light and distinguis ed by remarka le evenness.
A violet shade of the same properties is produced by dyeing knitted viscose artificial silk in the manner described with a dyestuff containing COPFBI in complex combination and obtained rom 5-nitro-2-a-mino-1-methoxy benzene-4-sulfonic acid and 2(4'-methoxy benzoyl)-amino-5-hydroxynaphthalene- 7 -sulfonic acid.
A remarkable even scarlet red dyeing is produced by the use of a dyestufi containing co per in complex combination and 0btamed from 2-amino-1-phenol glycerine ether and 2- (4'-methy1-benzoyl) -amino-5-hydrox na hthalene-7-sulfonic acid.
nstead of the azo dyestuffs containing a carboxylic group in the ortho position to the azo group there can also be used quite generally such dyestuffs as contain the carbonylor hydroxy group in the ortho position to at least one azo oup; the above mentioned dyestuffs containing a methoxy group in the ortho osition to an azo group can likewise be rep aced by dyestuffs, containing in the ortho position to an azo group other alkyl hydroxy-, aralkyl hydroxyor aryl hydroxy oups, which may also be substituted, if esired.
Ewample 2.By means of the dyestuff containing nickel in complex combination and obtained from 6-amino-1-hydroxy benzene- 2-carboxylic acid, l-amino naphthalene, 1- hydroxy naphthalene-5-sulfonic acid and nlckel tetramine sulfate which dyestufli' probably corresponds to the following formula:
HOOC OH applied to knitted viscose artificial silk in the manner described in Example 1 with the addition of 1% of isobutyl naphthalene sulfonic acid (calculated on the weight of the material) a completely even bluish black dyeing is produced, possessing excellent fastness to light. The same dyestuff containing cobalt in complex combination yields a greenish black shade of similar properties.
Instead of the dyestuffs here specifically described,other dyestuffs containing nickel and cobalt in complex combination can likewise be used.
I Example 3..,10 kgs. of knitted viscose are SOIH O:
2 of Glaubers salt and 0.2 kg. of soap.
Powerful even green shades of good fastness to light are obtained.
An even pink of good fastness properties is obtained by dyeing in the same manner as indicated above with a chromium compound of the dyestuff from diazotized 4-chloro-2-amino henol-6-sulfoni'c acid and 1-(3'- sulfo-pheny )-3'-methyl-5-pyrazolone; the chromium containing dyestuflf from diazotized 1-amino-2-naphthol-sulfonic acid andlnaphthol-S-sulfonic acid dyes an even clear blue shade; the dyestufi' containing chromium obtainable from diazotized 2-aminobenzoic acid and 2-amino-naphthalene-I-sulfonic acid dyes an even violet tint; the zinc compound prepared from the dyestufi from diazotized 5-nitro-2-amino phenol and 2-(4- methoxyzlphenyl amino) 5 -naphthol-7-sulfonic aci (coupled in the presence of alkali) dyes an even clear violet shade; the co per compound pre ared from the dyestuff rom diazotized 5-n1tro-2-aminophenol and 2-(4'- ethoxy-phenyl-amino) -5-naphthol-7-sulfonic acid dyes an even deep reddish blue shade.
We claim:
1. The process which comprises dyeing viscose of different origin with an azodyestuff containing in ortho position to an azo group at least one substituent of the oup consisting of hydroxy-, carbox lie aci alkoxy-, aralkoxyand aldehy 0 groups or containing in its molecule at least one salicylic acid group, containing in complex combination a metal of the group consisting of copper, nickel, cobalt, chromium, cadmium, zinc, vanadium and iron.
2. The process which comprises dyeing viscose of different origin with an azodyestufi containing in ortho position to an azo group at least one substituent of the group consisting of hydroxy-, carboxylic acid-, alk0xy-, aralkoxyand aldehydo groups or containing in its molecule at least one salicylic acid group, containing chromium in complex combination.
3. The process which comprises dyeing viscose of different origin with a chromium complex compound of the azodyestuff prepared from diazotized 5-nitro-2-aminophenol and 2-naphthylamine-5-sulfonic acid.
4. As new articles of manufacture viscose of diflerent origin dyed with an azodyestuif as claimed in claim 1; the dyeings being distinguished by an excellent evenness.
5. As new products of manufacture viscose of different origin dyed with an azodyestufi' as claimed in c aim 2, the dyeings being distinguished by an excellent evenness.
6. As a new article of manufacture viscose of different origin dyed with the azodyestuff as claimed in claim 3, the dyeing being distinguished by an excellent evenness.
In testimony whereof we have hereunto set our hands.
WINFRID HENTRICH. 11. 8.] MAX HARDTMANN. [1,. 5. JOSEF HILGER. [L.S.] RUDOLF KNOCHE. [1,. 5.]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1853418X | 1923-02-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1853418A true US1853418A (en) | 1932-04-12 |
Family
ID=7746101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US342956A Expired - Lifetime US1853418A (en) | 1923-02-27 | 1929-02-26 | Dyeing of viscose |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1853418A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2526106A (en) * | 1950-10-17 | Composition comprising a nitroge | ||
| US2857371A (en) * | 1954-09-10 | 1958-10-21 | Eastman Kodak Co | Benzothiazole azo diphenylamine compounds |
| US3317273A (en) * | 1964-04-16 | 1967-05-02 | Gen Aniline & Film Corp | Metallizing azoic dyeings and prints |
-
1929
- 1929-02-26 US US342956A patent/US1853418A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2526106A (en) * | 1950-10-17 | Composition comprising a nitroge | ||
| US2857371A (en) * | 1954-09-10 | 1958-10-21 | Eastman Kodak Co | Benzothiazole azo diphenylamine compounds |
| US3317273A (en) * | 1964-04-16 | 1967-05-02 | Gen Aniline & Film Corp | Metallizing azoic dyeings and prints |
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