FR2471401A1 - Nouveaux composes halogeno-triaziniques, leur preparation et leur utilisation comme colorants - Google Patents
Nouveaux composes halogeno-triaziniques, leur preparation et leur utilisation comme colorants Download PDFInfo
- Publication number
- FR2471401A1 FR2471401A1 FR8025882A FR8025882A FR2471401A1 FR 2471401 A1 FR2471401 A1 FR 2471401A1 FR 8025882 A FR8025882 A FR 8025882A FR 8025882 A FR8025882 A FR 8025882A FR 2471401 A1 FR2471401 A1 FR 2471401A1
- Authority
- FR
- France
- Prior art keywords
- carbon atoms
- group
- alkyl
- group containing
- hydrogen atom
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 239000003086 colorant Substances 0.000 title abstract 2
- -1 HYDROXY GROUPS Chemical group 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000758 substrate Substances 0.000 claims abstract description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 77
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- 125000002947 alkylene group Chemical group 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000000975 dye Substances 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229920000742 Cotton Polymers 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 238000004043 dyeing Methods 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 5
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 229910052757 nitrogen Chemical group 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 239000010985 leather Substances 0.000 claims description 3
- 150000002829 nitrogen Chemical group 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 239000004627 regenerated cellulose Substances 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 101150035983 str1 gene Proteins 0.000 claims description 2
- 150000003918 triazines Chemical class 0.000 claims 2
- 229910006069 SO3H Inorganic materials 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 239000000985 reactive dye Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 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
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N iodoform Chemical compound IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- 239000010930 yellow gold Substances 0.000 description 2
- 229910001097 yellow gold Inorganic materials 0.000 description 2
- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 102100037328 Chitotriosidase-1 Human genes 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 101100134925 Gallus gallus COR6 gene Proteins 0.000 description 1
- 101000879661 Homo sapiens Chitotriosidase-1 Proteins 0.000 description 1
- 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 1
- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KBRLUWNROJMNFW-UHFFFAOYSA-N N,N-diethylethanamine tetramethylazanium Chemical compound C(C)N(CC)CC.C[N+](C)(C)C KBRLUWNROJMNFW-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 208000004590 nanophthalmos 1 Diseases 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000001043 yellow dye 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/09—Disazo or polyazo dyes
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/043—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring containing two or more triazine rings linked together by a non-chromophoric link
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1083379A CH651583A5 (en) | 1979-12-06 | 1979-12-06 | Halotriazinyldisazo compounds, preparation thereof, and process for dyeing leather |
| CH270080A CH647256A5 (en) | 1980-04-08 | 1980-04-08 | Halotriazinedisazo compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2471401A1 true FR2471401A1 (fr) | 1981-06-19 |
| FR2471401B1 FR2471401B1 (en, 2012) | 1984-11-09 |
Family
ID=25691182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8025882A Granted FR2471401A1 (fr) | 1979-12-06 | 1980-12-05 | Nouveaux composes halogeno-triaziniques, leur preparation et leur utilisation comme colorants |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4502866A (en, 2012) |
| BR (1) | BR8007928A (en, 2012) |
| DE (1) | DE3043915A1 (en, 2012) |
| ES (1) | ES8205837A1 (en, 2012) |
| FR (1) | FR2471401A1 (en, 2012) |
| GB (1) | GB2064571B (en, 2012) |
| IT (1) | IT1188969B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0458743A3 (en) * | 1990-05-21 | 1992-10-21 | Ciba-Geigy Ag | Reactive dyestuffs, methods of their preparation and use |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5395925A (en) * | 1980-10-07 | 1995-03-07 | Sandoz Ltd. | Asymmetric sulfo group-containing disazo compounds containing two 6-halo-1,3,5-triazinyl groups |
| CH669305GA3 (en, 2012) * | 1981-12-11 | 1989-03-15 | ||
| US4575142A (en) * | 1984-09-13 | 1986-03-11 | Witco Chemical Corporation | Safety grip handle for a hose |
| DE3575571D1 (de) * | 1985-01-08 | 1990-03-01 | Ici Plc | Wasserloeslicher farbstoff. |
| DE59109196D1 (de) * | 1990-09-25 | 2000-10-05 | Ciba Sc Holding Ag | Faserreaktive Farbstoffe und deren Verwendung |
| GB9122318D0 (en) * | 1991-10-21 | 1991-12-04 | Courtaulds Plc | Treatment of elongate members |
| GB9304887D0 (en) * | 1993-03-10 | 1993-04-28 | Courtaulds Plc | Fibre treatment |
| GB9407496D0 (en) * | 1994-04-15 | 1994-06-08 | Courtaulds Fibres Holdings Ltd | Fibre treatment |
| GB9408742D0 (en) * | 1994-05-03 | 1994-06-22 | Courtaulds Fibres Holdings Ltd | Fabric treatment |
| GB9410912D0 (en) * | 1994-06-01 | 1994-07-20 | Courtaulds Plc | Fibre treatment |
| TW406117B (en) * | 1995-06-14 | 2000-09-21 | Ciba Sc Holding Ag | Fibre-reactive dyes containing two triazinyl radicals which are linked via an aliphatic bridge member |
| EP1189983B1 (en) | 1999-05-19 | 2010-04-21 | Bridgestone Corporation | Low molecular weight high-cis polybutadienes |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1228184A (fr) * | 1958-03-05 | 1960-08-26 | Ici Ltd | Nouvelles matières colorantes azoïques |
| FR2028479A1 (en, 2012) * | 1969-01-16 | 1970-10-09 | Ici Ltd | |
| FR2304651A1 (fr) * | 1976-03-18 | 1976-10-15 | Ciba Geigy Ag | Colorants reactifs vis-a-vis de la fibre, leur procede de preparation et leur utilisation |
| GB1461125A (en) * | 1974-10-02 | 1977-01-13 | Ici Ltd | Fluorotriazinyl reactive dyestuff |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB774925A (en) * | 1954-11-29 | 1957-05-15 | Ici Ltd | New monoazo dyestuffs derived from cyanuric chloride |
| GB785222A (en) * | 1954-11-29 | 1957-10-23 | Ici Ltd | New monoazo dyestuffs derived from cyanuric chloride |
| GB854432A (en) * | 1958-03-05 | 1960-11-16 | Ici Ltd | New triazine azo dyestuffs |
| CH422196A (de) * | 1958-08-11 | 1966-10-15 | Ciba Geigy | Verfahren zur Herstellung neuer Azofarbstoffe |
| GB1015932A (en) * | 1961-05-24 | 1966-01-05 | Ici Ltd | New reactive dyestuffs containing triazine residues |
| GB1272291A (en) * | 1969-01-16 | 1972-04-26 | Ici Ltd | New reactive metallised disazo dyestuffs |
| BE787122A (fr) * | 1971-08-04 | 1973-02-05 | Ciba Geigy | Composes azoiques, leur preparation et leur utilisation |
| US4148790A (en) * | 1973-05-24 | 1979-04-10 | Sumitomo Chemical Company Limited | Metallized triazine reactive dyes |
| JPS50107277A (en, 2012) * | 1974-02-01 | 1975-08-23 | ||
| JPS5126386A (en) * | 1974-08-24 | 1976-03-04 | Mitsubishi Chem Ind | Seruroosukeisenino senshokuhoho |
| DE2611550C2 (de) * | 1975-03-20 | 1987-03-26 | Ciba-Geigy Ag, Basel | Faserreaktive Farbstoffe, deren Herstellung und Verwendung |
-
1980
- 1980-11-21 DE DE19803043915 patent/DE3043915A1/de active Granted
- 1980-11-28 US US06/210,770 patent/US4502866A/en not_active Expired - Lifetime
- 1980-12-02 GB GB8038641A patent/GB2064571B/en not_active Expired
- 1980-12-04 BR BR8007928A patent/BR8007928A/pt unknown
- 1980-12-05 FR FR8025882A patent/FR2471401A1/fr active Granted
- 1980-12-05 IT IT50315/80A patent/IT1188969B/it active
- 1980-12-05 ES ES497525A patent/ES8205837A1/es not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1228184A (fr) * | 1958-03-05 | 1960-08-26 | Ici Ltd | Nouvelles matières colorantes azoïques |
| FR2028479A1 (en, 2012) * | 1969-01-16 | 1970-10-09 | Ici Ltd | |
| GB1461125A (en) * | 1974-10-02 | 1977-01-13 | Ici Ltd | Fluorotriazinyl reactive dyestuff |
| FR2304651A1 (fr) * | 1976-03-18 | 1976-10-15 | Ciba Geigy Ag | Colorants reactifs vis-a-vis de la fibre, leur procede de preparation et leur utilisation |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0458743A3 (en) * | 1990-05-21 | 1992-10-21 | Ciba-Geigy Ag | Reactive dyestuffs, methods of their preparation and use |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2064571B (en) | 1983-07-06 |
| IT1188969B (it) | 1988-01-28 |
| DE3043915C2 (en, 2012) | 1989-07-20 |
| IT8050315A0 (it) | 1980-12-05 |
| FR2471401B1 (en, 2012) | 1984-11-09 |
| GB2064571A (en) | 1981-06-17 |
| DE3043915A1 (de) | 1981-06-11 |
| IT8050315A1 (it) | 1982-06-05 |
| ES497525A0 (es) | 1982-07-01 |
| US4502866A (en) | 1985-03-05 |
| ES8205837A1 (es) | 1982-07-01 |
| BR8007928A (pt) | 1981-06-16 |
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| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |