US1843634A - Metal compounds of azo-dyestuffs and process of making same - Google Patents
Metal compounds of azo-dyestuffs and process of making same Download PDFInfo
- Publication number
- US1843634A US1843634A US345588A US34558829A US1843634A US 1843634 A US1843634 A US 1843634A US 345588 A US345588 A US 345588A US 34558829 A US34558829 A US 34558829A US 1843634 A US1843634 A US 1843634A
- Authority
- US
- United States
- Prior art keywords
- group
- azo
- parts
- grey
- blue
- 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
- 150000002736 metal compounds Chemical class 0.000 title description 16
- 238000000034 method Methods 0.000 title description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- 239000000975 dye Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 239000011651 chromium Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000003513 alkali Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 150000002739 metals Chemical class 0.000 description 11
- 239000000843 powder Substances 0.000 description 10
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 229910052804 chromium Inorganic materials 0.000 description 9
- 235000017550 sodium carbonate Nutrition 0.000 description 9
- 229940001593 sodium carbonate Drugs 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 8
- 238000004043 dyeing Methods 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 229920002955 Art silk Polymers 0.000 description 7
- 150000008049 diazo compounds Chemical class 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- 229910021563 chromium fluoride Inorganic materials 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 5
- 235000013311 vegetables Nutrition 0.000 description 5
- 229920000297 Rayon Polymers 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- 150000001845 chromium compounds Chemical class 0.000 description 4
- 229960000355 copper sulfate Drugs 0.000 description 4
- 229910000365 copper sulfate Inorganic materials 0.000 description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000004627 regenerated cellulose Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 244000172533 Viola sororia Species 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000010446 mirabilite Substances 0.000 description 3
- QXYMVUZOGFVPGH-UHFFFAOYSA-N picramic acid Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QXYMVUZOGFVPGH-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- AQSOTOUQTVJNMY-UHFFFAOYSA-N 7-(dimethylamino)-4-hydroxy-3-oxophenoxazin-10-ium-1-carboxylic acid;chloride Chemical compound [Cl-].OC(=O)C1=CC(=O)C(O)=C2OC3=CC(N(C)C)=CC=C3[NH+]=C21 AQSOTOUQTVJNMY-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229940013688 formic acid Drugs 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- BFDHFSHZJLFAMC-UHFFFAOYSA-L nickel(ii) hydroxide Chemical compound [OH-].[OH-].[Ni+2] BFDHFSHZJLFAMC-UHFFFAOYSA-L 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-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
- QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 101100243951 Caenorhabditis elegans pie-1 gene Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 244000154870 Viola adunca Species 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229940108928 copper Drugs 0.000 description 1
- ICIDZHMCYAIUIJ-UHFFFAOYSA-N dinaphthalen-1-yldiazene Chemical compound C1=CC=C2C(N=NC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ICIDZHMCYAIUIJ-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000012047 saturated solution Substances 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
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
- C09B45/26—Disazo or polyazo compounds containing chromium
-
- 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
- C09B33/18—Trisazo or higher polyazo dyes
- C09B33/22—Trisazo dyes of the type A->B->K<-C
-
- 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
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
-
- 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
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
Definitions
- the present invention relates to new and valuable metal compounds of azo-dyestuffs derivmg from metals of atomic weights ranging from 52 to 58,7. These metal com, pounds may contain either one metal'alone or several metals. In the latter case one or several metals may also not belong'to the above mentioned range of atomic weights.
- the dyestuffs according to the present invention are made by treating the poly-aZo-dyestuff of the general formula in which R and R are aryl residues, from which at least the one of these contains morda'nt bindinggroup.
- the sulfogroups being in meta-positionto the OH- groups, further in which, the two azo-groups are linked in ortho-position to the OH- groups and in which at most one OH-group stands 1n 8-pos1t1on,,w1th agents yielding metals of atomic Weights ranging from 52 to 58.7,.these agents being chosen in such a- Way that either one or several metals enter the dyestufi' molecule whereby in the latter case other metals may alsoenter the dyestufi molecule.
- the treatment may beapplied in the course ofthe production of the said polyazo-dy'estufi' or to the finished dyestuff, either in the fiber, in the dye-bath or in substance.
- These dy'estufi's do not dye the artificialsilks from cellulose esters or cellulose ethers.
- HOaS- Eaaamfole 2 In presence of sodium carbonate 53,5 parts of the dyestuif 2: 1-azonaphthalen e-5 5- dihydroxy-2-amino-7 7-disulfonic acid are coupled with lO parts of diazotized picramic acid and the azo-dyestuff of the formula powder which dissolves in water, dilute alkalies and concentrated sulfuric acid to greenish-grey solutions. It dyes cotton, viscose and silk fast uniform green-grey tints.
- Example 4 54 parts of thesodium salt of the monoazo-dyestuff obtained in acetic acid solution from dia-zotized 2-amino-5-hydroxynaphtha- 'lene-7-sulfonic acid are dissolved in 600 parts of Water and this solution is mixed with parts of sodium carbonate. The diazo-compound from 32 parts of anthranilic acid is then added and the dyes'tulf formed after some time is isolated. By boiling the dyestuf't' of the formula OOH parts of 4-chloro-2-amino l-phenol and after thus formed with; a solution of chromium some time the diaZo-compound from 19,9 fluoride containing 25-parts of Cr o in 3000 parts of picramic acid.
- the chro; azo-dyestufi thus produced of the-formula mium compound of the new dyestufl' is is filtered and dissolved in 4000 parts of hot water. There are then added 30 parts of @150 in the form of a chromium fluoride solution and the whole is heated for 24 hours in a reflux apparatus.
- Example 5 54 parts of the mono-azo dyestuif obtained from diazotized 2-amino 5-hydroxynaphthalene-7-sulfonic acid and 2-amino-5-hydroxynaphthalene-'Y-sulfonic acid (acetic acid coupled) are dissolved. in 500 parts of water and combined in the presence of sodium carbonate with the diazo-conipound from 22,3 parts of l-chloro 2 amino 1 phenol 6 sulfonic acid.
- the dyestuff of the formula By treating the azo 'dyestufi of the first paragraph of'this example with a solution of 25 sloin on parts of copper sulfate and 20 parts of Cr 3 in the form of a chromium salt (fluoride,
- the metal compounds deriving from a group of metaljstheatomic weights of which range general formula in which R and R are benzene radicles, from which at least the one of these contains a mordant binding group in ortho-position to the -N N- group, in which one of the ws and one of the ys stand for an OH-group and the other w and the other 3/ for a hydrogen atom, one of the ws and one of the zs represent a SO H-group, and the other a and the other a a hydrogen atom, the sulfo-groups being in meta-position to the OH-groups, further in which the two azogroups are linked in ortho-position to the OH-groups, and in which at most one OH- group stands in 8-position, which products are when dry dark colored powders, soluble in water and dilute alkalies to blue to grey-blue and grey solutions and in concentrated sulfuric acid to blackish-
- the OH-groups further in which the two azogroups are linked inortho-position to the OI-I-groups, and in which at most one UH- vgroup stands in 8-position, containing besides a group of metals the atomic weights of which range from 52 to 58.? still ther metals which products are when dry dark col.- ored powders, soluble in water and dilute alkalies to blue to grey-blueand grey soluin which R and R are benzene radicles, contions and in concentrated sulfuric'acid to blackish-blue to blue and grey solutions, and dyeing vegetable fiber and especially artificial silk from so-called regenerated cellulose fast violet to blue and grey tints.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH307705X | 1928-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1843634A true US1843634A (en) | 1932-02-02 |
Family
ID=4493250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US345588A Expired - Lifetime US1843634A (en) | 1928-03-10 | 1929-03-08 | Metal compounds of azo-dyestuffs and process of making same |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US1843634A (de) |
| CH (5) | CH133478A (de) |
| GB (1) | GB307705A (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891047A (en) * | 1955-08-20 | 1959-06-16 | Bayer Ag | Metal containing polyazo dyestuffs |
| US2984635A (en) * | 1957-06-03 | 1961-05-16 | Monsanto Chemicals | Composition comprising alumina particles coated with polymer of ethylenically unsaturated monomer |
-
1928
- 1928-03-10 CH CH133478D patent/CH133478A/de unknown
-
1929
- 1929-03-08 US US345588A patent/US1843634A/en not_active Expired - Lifetime
- 1929-03-11 GB GB7920/29A patent/GB307705A/en not_active Expired
- 1929-06-01 CH CH144214D patent/CH144214A/de unknown
- 1929-06-01 CH CH144212D patent/CH144212A/de unknown
- 1929-06-01 CH CH144215D patent/CH144215A/de unknown
- 1929-06-01 CH CH144213D patent/CH144213A/de unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891047A (en) * | 1955-08-20 | 1959-06-16 | Bayer Ag | Metal containing polyazo dyestuffs |
| US2984635A (en) * | 1957-06-03 | 1961-05-16 | Monsanto Chemicals | Composition comprising alumina particles coated with polymer of ethylenically unsaturated monomer |
Also Published As
| Publication number | Publication date |
|---|---|
| CH144212A (de) | 1930-12-15 |
| CH144215A (de) | 1930-12-15 |
| CH133478A (de) | 1929-06-15 |
| GB307705A (en) | 1930-06-11 |
| CH144213A (de) | 1930-12-15 |
| CH144214A (de) | 1930-12-15 |
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