CA1104305A - Process for dyeing high-molecular organic material in the melt - Google Patents
Process for dyeing high-molecular organic material in the meltInfo
- Publication number
- CA1104305A CA1104305A CA305,245A CA305245A CA1104305A CA 1104305 A CA1104305 A CA 1104305A CA 305245 A CA305245 A CA 305245A CA 1104305 A CA1104305 A CA 1104305A
- Authority
- CA
- Canada
- Prior art keywords
- triazine
- formula
- mixture
- alkyl
- melt
- 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
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000004043 dyeing Methods 0.000 title claims abstract description 13
- 239000000155 melt Substances 0.000 title claims abstract description 11
- 239000011368 organic material Substances 0.000 title claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 26
- 238000004040 coloring Methods 0.000 claims abstract description 23
- -1 anthraquinone compound Chemical class 0.000 claims abstract description 17
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 16
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 32
- 229920000728 polyester Polymers 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- FNCVZYRPXOZNSM-UHFFFAOYSA-N n-(4-chloro-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(Cl)=CC=C1NC(=O)C1=CC=CC=C1 FNCVZYRPXOZNSM-UHFFFAOYSA-N 0.000 claims description 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 2
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 claims description 2
- 229920002301 cellulose acetate Polymers 0.000 claims description 2
- 229920003086 cellulose ether Polymers 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- PXNNPGGYHAWDJW-UHFFFAOYSA-N N-(4-amino-9,10-dioxo-1-anthracenyl)benzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=C1NC(=O)C1=CC=CC=C1 PXNNPGGYHAWDJW-UHFFFAOYSA-N 0.000 claims 1
- 239000000020 Nitrocellulose Substances 0.000 claims 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 229920001220 nitrocellulos Polymers 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 150000004056 anthraquinones Chemical class 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NAMCDLUESQLMOZ-UHFFFAOYSA-N 6-ethyl-1,3,5-triazine-2,4-diamine Chemical compound CCC1=NC(N)=NC(N)=N1 NAMCDLUESQLMOZ-UHFFFAOYSA-N 0.000 description 3
- YZVJFFKAKLWXOE-UHFFFAOYSA-N 6-heptadecyl-1,3,5-triazine-2,4-diamine Chemical compound CCCCCCCCCCCCCCCCCC1=NC(N)=NC(N)=N1 YZVJFFKAKLWXOE-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- OOEGQLPPMITCBZ-UHFFFAOYSA-N 6-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound CC(C)C1=NC(N)=NC(N)=N1 OOEGQLPPMITCBZ-UHFFFAOYSA-N 0.000 description 2
- 241001589086 Bellapiscis medius Species 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002074 melt spinning Methods 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LKHJPAFRDWBJPA-UHFFFAOYSA-N 2,4-dichloro-6-(2-methylpropyl)-1,3,5-triazine Chemical compound CC(C)CC1=NC(Cl)=NC(Cl)=N1 LKHJPAFRDWBJPA-UHFFFAOYSA-N 0.000 description 1
- ADVXAMGGIRUOKU-UHFFFAOYSA-N 2,4-dichloro-6-ethyl-1,3,5-triazine Chemical compound CCC1=NC(Cl)=NC(Cl)=N1 ADVXAMGGIRUOKU-UHFFFAOYSA-N 0.000 description 1
- HXAPEHGNZVNLGR-UHFFFAOYSA-N 2,4-dichloro-6-heptyl-1,3,5-triazine Chemical compound CCCCCCCC1=NC(Cl)=NC(Cl)=N1 HXAPEHGNZVNLGR-UHFFFAOYSA-N 0.000 description 1
- BFUGAHPTVMZLAC-UHFFFAOYSA-N 2,4-dichloro-6-methyl-1,3,5-triazine Chemical compound CC1=NC(Cl)=NC(Cl)=N1 BFUGAHPTVMZLAC-UHFFFAOYSA-N 0.000 description 1
- CMTXWONGBWCHBZ-UHFFFAOYSA-N 2,4-dichloro-6-nonyl-1,3,5-triazine Chemical compound CCCCCCCCCC1=NC(Cl)=NC(Cl)=N1 CMTXWONGBWCHBZ-UHFFFAOYSA-N 0.000 description 1
- QUBZPISKVMJTKR-UHFFFAOYSA-N 2,4-dichloro-6-pentyl-1,3,5-triazine Chemical compound CCCCCC1=NC(Cl)=NC(Cl)=N1 QUBZPISKVMJTKR-UHFFFAOYSA-N 0.000 description 1
- NRGJDHUSMZIRSC-UHFFFAOYSA-N 2,4-dichloro-6-propan-2-yl-1,3,5-triazine Chemical compound CC(C)C1=NC(Cl)=NC(Cl)=N1 NRGJDHUSMZIRSC-UHFFFAOYSA-N 0.000 description 1
- VGVDKHQHGQNHLT-UHFFFAOYSA-N 2,4-dichloro-6-propyl-1,3,5-triazine Chemical compound CCCC1=NC(Cl)=NC(Cl)=N1 VGVDKHQHGQNHLT-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
- FEHVKHFORSHUKE-UHFFFAOYSA-N 2-butyl-4,6-dichloro-1,3,5-triazine Chemical compound CCCCC1=NC(Cl)=NC(Cl)=N1 FEHVKHFORSHUKE-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- MKOAJICWQJCFMS-UHFFFAOYSA-N 2-tert-butyl-4,6-dichloro-1,3,5-triazine Chemical compound CC(C)(C)C1=NC(Cl)=NC(Cl)=N1 MKOAJICWQJCFMS-UHFFFAOYSA-N 0.000 description 1
- YQLYHCPMDNHTCP-UHFFFAOYSA-N 6-(3-methylbutyl)-1,3,5-triazine-2,4-diamine Chemical compound CC(C)CCC1=NC(N)=NC(N)=N1 YQLYHCPMDNHTCP-UHFFFAOYSA-N 0.000 description 1
- FMKJZXVUCJWIIV-UHFFFAOYSA-N 6-butyl-1,3,5-triazine-2,4-diamine Chemical compound CCCCC1=NC(N)=NC(N)=N1 FMKJZXVUCJWIIV-UHFFFAOYSA-N 0.000 description 1
- JWFQDKBDSOOWTB-UHFFFAOYSA-N 6-heptyl-1,3,5-triazine-2,4-diamine Chemical compound CCCCCCCC1=NC(N)=NC(N)=N1 JWFQDKBDSOOWTB-UHFFFAOYSA-N 0.000 description 1
- BDPPZSFVSOBOIX-UHFFFAOYSA-N 6-nonyl-1,3,5-triazine-2,4-diamine Chemical compound CCCCCCCCCC1=NC(N)=NC(N)=N1 BDPPZSFVSOBOIX-UHFFFAOYSA-N 0.000 description 1
- NGYGUYRBWLUDRP-UHFFFAOYSA-N 6-propyl-1,3,5-triazine-2,4-diamine Chemical compound CCCC1=NC(N)=NC(N)=N1 NGYGUYRBWLUDRP-UHFFFAOYSA-N 0.000 description 1
- IHZNXUFURDYYKI-UHFFFAOYSA-N 6-tridecyl-1,3,5-triazine-2,4-diamine Chemical compound CCCCCCCCCCCCCC1=NC(N)=NC(N)=N1 IHZNXUFURDYYKI-UHFFFAOYSA-N 0.000 description 1
- MLCIKWISJBFZKS-UHFFFAOYSA-N 6-undecyl-1,3,5-triazine-2,4-diamine Chemical compound CCCCCCCCCCCC1=NC(N)=NC(N)=N1 MLCIKWISJBFZKS-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- XAIKOVRFTSBNNU-UHFFFAOYSA-N anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 XAIKOVRFTSBNNU-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7297/77 | 1977-06-14 | ||
| CH729777A CH625537A5 (en, 2012) | 1977-06-14 | 1977-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1104305A true CA1104305A (en) | 1981-07-07 |
Family
ID=4322921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA305,245A Expired CA1104305A (en) | 1977-06-14 | 1978-06-12 | Process for dyeing high-molecular organic material in the melt |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4211688A (en, 2012) |
| JP (1) | JPS546035A (en, 2012) |
| CA (1) | CA1104305A (en, 2012) |
| CH (1) | CH625537A5 (en, 2012) |
| DE (1) | DE2825613A1 (en, 2012) |
| FR (1) | FR2394572A1 (en, 2012) |
| GB (1) | GB2000159B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4725378A (en) * | 1982-03-22 | 1988-02-16 | The Dow Chemical Company | Systems for delayed release of bleaching agents |
| JPS60250052A (ja) * | 1984-05-28 | 1985-12-10 | Mitsubishi Chem Ind Ltd | 樹脂用着色材 |
| US6357527B1 (en) | 2000-05-05 | 2002-03-19 | Halliburton Energy Services, Inc. | Encapsulated breakers and method for use in treating subterranean formations |
| RU2580144C2 (ru) * | 2010-10-28 | 2016-04-10 | Тейджин Арамид Б.В. | Окрашенные в процессе формования арамидные волокна |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE551884C (de) * | 1930-02-20 | 1932-06-06 | Ig Farbenindustrie Ag | Verfahren zur Darstellung von Kuepenfarbstoffen der Anthrachinonreihe |
| DE553312C (de) * | 1930-06-04 | 1932-06-24 | Ig Farbenindustrie Ag | Verfahren zur Darstellung von Kuepenfarbstoffen der Anthrachinonreihe |
| BE567462A (en, 2012) * | 1957-05-08 | |||
| BE620471A (en, 2012) * | 1961-07-21 | |||
| GB950378A (en) * | 1962-02-14 | 1964-02-26 | Arthur Jack Sackville Evans | New anthraquinone dyestuffs and process for their manufacture |
| DE1274069B (de) * | 1963-09-25 | 1968-08-01 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung goldgelber Kuepenfarbstoffdrucke auf Cellulosetextilien |
| CH471852A (de) * | 1966-04-28 | 1969-04-30 | Ciba Geigy | Verfahren zum Färben organischer Erzeugnisse mit Pigmentfarbstoffen |
| US3839332A (en) * | 1967-08-18 | 1974-10-01 | Ciba Geigy Ag | Process for the manufacture of anthraquinone dyestuffs |
| US3642795A (en) * | 1968-02-19 | 1972-02-15 | Ciba Ltd | Triazinyl-anthraquinone dyestuffs |
| FR2128369A1 (en) * | 1971-03-03 | 1972-10-20 | Ciba Geigy Ag | Anthraquinone/acridone vat dyes - and pigments contg triazine grps for cellulosic fibres, plastics, paints, etc |
| CH580136A5 (en, 2012) * | 1973-01-30 | 1976-09-30 | Ciba Geigy Ag | |
| CH579613A5 (en, 2012) * | 1973-01-30 | 1976-09-15 | Ciba Geigy Ag | |
| GB1476687A (en) * | 1973-08-22 | 1977-06-16 | Ciba Geigy Ag | Vat dyes their manufacture and their use |
-
1977
- 1977-06-14 CH CH729777A patent/CH625537A5/de not_active IP Right Cessation
-
1978
- 1978-06-06 US US05/913,159 patent/US4211688A/en not_active Expired - Lifetime
- 1978-06-12 DE DE19782825613 patent/DE2825613A1/de not_active Withdrawn
- 1978-06-12 CA CA305,245A patent/CA1104305A/en not_active Expired
- 1978-06-13 GB GB7826820A patent/GB2000159B/en not_active Expired
- 1978-06-14 FR FR7817768A patent/FR2394572A1/fr active Granted
- 1978-06-14 JP JP7201978A patent/JPS546035A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2394572A1 (fr) | 1979-01-12 |
| GB2000159B (en) | 1982-01-27 |
| GB2000159A (en) | 1979-01-04 |
| US4211688A (en) | 1980-07-08 |
| JPS546035A (en) | 1979-01-17 |
| DE2825613A1 (de) | 1979-01-04 |
| CH625537A5 (en, 2012) | 1981-09-30 |
| FR2394572B1 (en, 2012) | 1980-06-06 |
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