CA1081936A - Oxidation of vat and sulfur dyes with vanadate activated bromate or iodate in combination with a nitrate - Google Patents
Oxidation of vat and sulfur dyes with vanadate activated bromate or iodate in combination with a nitrateInfo
- Publication number
- CA1081936A CA1081936A CA261,786A CA261786A CA1081936A CA 1081936 A CA1081936 A CA 1081936A CA 261786 A CA261786 A CA 261786A CA 1081936 A CA1081936 A CA 1081936A
- Authority
- CA
- Canada
- Prior art keywords
- salts
- water
- soluble
- ammonium
- vanadate
- 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
Links
- 239000000984 vat dye Substances 0.000 title claims abstract description 25
- 239000000988 sulfur dye Substances 0.000 title claims abstract description 22
- -1 vanadate activated bromate Chemical class 0.000 title claims description 14
- 230000003647 oxidation Effects 0.000 title description 17
- 238000007254 oxidation reaction Methods 0.000 title description 17
- 229910002651 NO3 Inorganic materials 0.000 title description 8
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 title description 8
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 title description 5
- 230000001590 oxidative effect Effects 0.000 claims abstract description 54
- 239000007800 oxidant agent Substances 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 239000000975 dye Substances 0.000 claims abstract description 27
- 230000008569 process Effects 0.000 claims abstract description 25
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical class [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical class OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 claims abstract description 14
- ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical class OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 claims abstract description 10
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 claims description 17
- 239000011734 sodium Substances 0.000 claims description 16
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 13
- 150000002823 nitrates Chemical class 0.000 claims description 13
- 229910052708 sodium Inorganic materials 0.000 claims description 13
- 239000004753 textile Substances 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 229920000742 Cotton Polymers 0.000 claims description 10
- 150000003863 ammonium salts Chemical class 0.000 claims description 9
- 239000000835 fiber Substances 0.000 claims description 8
- 239000004627 regenerated cellulose Substances 0.000 claims description 7
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 claims description 5
- 230000006872 improvement Effects 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 12
- 229910052700 potassium Inorganic materials 0.000 claims 12
- 239000011591 potassium Substances 0.000 claims 12
- 229910052783 alkali metal Inorganic materials 0.000 claims 8
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 4
- ZRDJERPXCFOFCP-UHFFFAOYSA-N azane;iodic acid Chemical compound [NH4+].[O-]I(=O)=O ZRDJERPXCFOFCP-UHFFFAOYSA-N 0.000 claims 4
- 239000000243 solution Substances 0.000 abstract description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 239000004744 fabric Substances 0.000 description 17
- 239000002253 acid Substances 0.000 description 15
- 230000007797 corrosion Effects 0.000 description 12
- 238000005260 corrosion Methods 0.000 description 12
- 238000004043 dyeing Methods 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 9
- 235000011054 acetic acid Nutrition 0.000 description 9
- 230000000007 visual effect Effects 0.000 description 9
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 8
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 8
- 229940099408 Oxidizing agent Drugs 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 235000001508 sulfur Nutrition 0.000 description 6
- 229960005349 sulfur Drugs 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 4
- 229960002218 sodium chlorite Drugs 0.000 description 4
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 4
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- NDDLLTAIKYHPOD-ISLYRVAYSA-N (2e)-6-chloro-2-(6-chloro-4-methyl-3-oxo-1-benzothiophen-2-ylidene)-4-methyl-1-benzothiophen-3-one Chemical compound S/1C2=CC(Cl)=CC(C)=C2C(=O)C\1=C1/SC(C=C(Cl)C=C2C)=C2C1=O NDDLLTAIKYHPOD-ISLYRVAYSA-N 0.000 description 2
- KGZMABLDPNAGFQ-UHFFFAOYSA-N 1-n,4-n-bis(5-benzamido-9,10-dioxoanthracen-1-yl)benzene-1,4-dicarboxamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=1C(=O)C2=CC=C3)=CC=CC=1C(=O)C2=C3NC(=O)C(C=C1)=CC=C1C(=O)NC(C=1C(=O)C2=CC=C3)=CC=CC=1C(=O)C2=C3NC(=O)C1=CC=CC=C1 KGZMABLDPNAGFQ-UHFFFAOYSA-N 0.000 description 2
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 2
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 2
- QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- NALMPLUMOWIVJC-UHFFFAOYSA-N n,n,4-trimethylbenzeneamine oxide Chemical compound CC1=CC=C([N+](C)(C)[O-])C=C1 NALMPLUMOWIVJC-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 238000009974 package dyeing Methods 0.000 description 2
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 2
- 239000011697 sodium iodate Substances 0.000 description 2
- 235000015281 sodium iodate Nutrition 0.000 description 2
- 229940032753 sodium iodate Drugs 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- NYCVSSWORUBFET-UHFFFAOYSA-M sodium;bromite Chemical compound [Na+].[O-]Br=O NYCVSSWORUBFET-UHFFFAOYSA-M 0.000 description 2
- PGYZAKRTYUHXRA-UHFFFAOYSA-N 2,10-dinitro-12h-[1,4]benzothiazino[3,2-b]phenothiazin-3-one Chemical compound S1C2=CC(=O)C([N+]([O-])=O)=CC2=NC2=C1C=C1SC3=CC=C([N+](=O)[O-])C=C3NC1=C2 PGYZAKRTYUHXRA-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- WZSLDJBBPHUGJT-UHFFFAOYSA-N 2379-78-4 Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC(C(C2=C3NC4=5)=O)=C1C(=O)C2=CC=C3C4=CC=C(C(C1=2)=O)C=5C(=O)C1=CC=CC=2NC(=O)C1=CC=CC=C1 WZSLDJBBPHUGJT-UHFFFAOYSA-N 0.000 description 1
- ORWQBKPSGDRPPA-UHFFFAOYSA-N 3-[2-[ethyl(methyl)amino]ethyl]-1h-indol-4-ol Chemical compound C1=CC(O)=C2C(CCN(C)CC)=CNC2=C1 ORWQBKPSGDRPPA-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- 241001076939 Artines Species 0.000 description 1
- 241000422980 Marietta Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- KLCBMAACUWYFIZ-UHFFFAOYSA-N benzo[1,2-c:4,5-c']diacridine-6,9,15,18(5h,14h)-tetrone Chemical compound C1=CC=C2C(=O)C3=CC=C4C(=O)C5=C(NC=6C(=CC=CC=6)C6=O)C6=CC=C5C(=O)C4=C3NC2=C1 KLCBMAACUWYFIZ-UHFFFAOYSA-N 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- JXUKQCUPTNLTCS-UHFFFAOYSA-N vat green 1 Chemical compound C1=CC=C[C]2C(=O)C(C3=C45)=CC=C4C(C4=C67)=CC=C7C(=O)[C]7C=CC=CC7=C6C=C(OC)C4=C5C(OC)=CC3=C21 JXUKQCUPTNLTCS-UHFFFAOYSA-N 0.000 description 1
- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002759 woven fabric Substances 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/22—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using vat dyestuffs including indigo
- D06P1/222—Oxidising agents
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0077—Preparations with possibly reduced vat, sulfur or indigo dyes
-
- 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/30—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using sulfur dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/918—Cellulose textile
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63323975A | 1975-11-19 | 1975-11-19 | |
| US633,239 | 1975-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1081936A true CA1081936A (en) | 1980-07-22 |
Family
ID=24538827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA261,786A Expired CA1081936A (en) | 1975-11-19 | 1976-09-22 | Oxidation of vat and sulfur dyes with vanadate activated bromate or iodate in combination with a nitrate |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4155709A (Direct) |
| JP (1) | JPS5836113B2 (Direct) |
| BR (1) | BR7607248A (Direct) |
| CA (1) | CA1081936A (Direct) |
| DE (1) | DE2652779C3 (Direct) |
| ES (1) | ES452324A1 (Direct) |
| FR (1) | FR2332361A2 (Direct) |
| GB (1) | GB1509649A (Direct) |
| IT (1) | IT1066281B (Direct) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4321054A (en) * | 1980-04-01 | 1982-03-23 | The Dow Chemical Company | Oxidizing medium for dyes |
| US4401435A (en) * | 1980-04-14 | 1983-08-30 | The Dow Chemical Co. | Oxidizing medium for dyes |
| US4469617A (en) * | 1980-04-14 | 1984-09-04 | The Dow Chemical Company | Oxidizing medium for dyes |
| DE4215678A1 (de) * | 1991-05-23 | 1992-11-26 | Sandoz Ag | Trockene leukoschwefelfarbstoffe |
| US5647875A (en) * | 1994-12-02 | 1997-07-15 | Clariant Finance (Bvi) Limited | Method for producing a color effect on textile material |
| IT1271814B (it) * | 1994-12-28 | 1997-06-09 | Alpi Spa | Tintura di fogli di legno mediante coloranti appartenenti alla classe "al tino". |
| US7070710B1 (en) * | 1999-06-11 | 2006-07-04 | Eka Chemicals Inc. | Chemical composition and method |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB657273A (en) * | 1948-02-25 | 1951-09-12 | Gen Aniline & Film Corp | Method of printing with sulfuric acid esters of leuco vat dyes of the anthraquinone series |
| US3775047A (en) * | 1971-07-06 | 1973-11-27 | Martin Marietta Corp | Oxidizing sulfur dyes on cellulose with sodium iodate or potassium iodate |
-
1976
- 1976-09-22 CA CA261,786A patent/CA1081936A/en not_active Expired
- 1976-09-23 IT IT51421/76A patent/IT1066281B/it active
- 1976-10-11 ES ES452324A patent/ES452324A1/es not_active Expired
- 1976-10-29 BR BR7607248A patent/BR7607248A/pt unknown
- 1976-11-01 GB GB45323/76A patent/GB1509649A/en not_active Expired
- 1976-11-17 JP JP51138282A patent/JPS5836113B2/ja not_active Expired
- 1976-11-18 FR FR7634748A patent/FR2332361A2/fr active Granted
- 1976-11-19 DE DE2652779A patent/DE2652779C3/de not_active Expired
-
1978
- 1978-07-24 US US05/927,314 patent/US4155709A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES452324A1 (es) | 1977-12-16 |
| DE2652779B2 (de) | 1978-09-21 |
| GB1509649A (en) | 1978-05-04 |
| FR2332361B2 (Direct) | 1979-08-31 |
| US4155709A (en) | 1979-05-22 |
| DE2652779A1 (de) | 1977-05-26 |
| JPS5266783A (en) | 1977-06-02 |
| JPS5836113B2 (ja) | 1983-08-06 |
| IT1066281B (it) | 1985-03-04 |
| BR7607248A (pt) | 1977-09-13 |
| DE2652779C3 (de) | 1979-05-17 |
| FR2332361A2 (fr) | 1977-06-17 |
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