CH624139A5 - - Google Patents
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- Publication number
- CH624139A5 CH624139A5 CH1631976A CH1631976A CH624139A5 CH 624139 A5 CH624139 A5 CH 624139A5 CH 1631976 A CH1631976 A CH 1631976A CH 1631976 A CH1631976 A CH 1631976A CH 624139 A5 CH624139 A5 CH 624139A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- dye
- free acid
- preparation
- methoxy
- Prior art date
Links
- 239000000975 dye Substances 0.000 claims description 51
- 239000000460 chlorine Substances 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 20
- -1 methoxy, acetylamino Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 150000004985 diamines Chemical class 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000985 reactive dye Substances 0.000 claims description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 241001340534 Eido Species 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004043 dyeing Methods 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 239000011230 binding agent Substances 0.000 description 12
- 229920000742 Cotton Polymers 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 8
- 239000000835 fiber Substances 0.000 description 7
- 239000002657 fibrous material Substances 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 229920003043 Cellulose fiber Polymers 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910017053 inorganic salt Inorganic materials 0.000 description 3
- 239000000661 sodium alginate Substances 0.000 description 3
- 235000010413 sodium alginate Nutrition 0.000 description 3
- 229940005550 sodium alginate Drugs 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- DIJKCUMQEPXUTK-UHFFFAOYSA-N 4,5-diamino-2-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=C(N)C=C1S(O)(=O)=O DIJKCUMQEPXUTK-UHFFFAOYSA-N 0.000 description 2
- MOMKYJPSVWEWPM-UHFFFAOYSA-N 4-(chloromethyl)-2-(4-methylphenyl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=NC(CCl)=CS1 MOMKYJPSVWEWPM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000019983 sodium metaphosphate Nutrition 0.000 description 2
- 235000019795 sodium metasilicate Nutrition 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- POWFTOSLLWLEBN-UHFFFAOYSA-N tetrasodium;silicate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-][Si]([O-])([O-])[O-] POWFTOSLLWLEBN-UHFFFAOYSA-N 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 235000019801 trisodium phosphate Nutrition 0.000 description 2
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 2
- ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 1
- DVLOIGSXYNRCNP-UHFFFAOYSA-N 2-amino-1h-naphthalene-1,2-disulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)C(N)(S(O)(=O)=O)C=CC2=C1 DVLOIGSXYNRCNP-UHFFFAOYSA-N 0.000 description 1
- HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 description 1
- MHQULXYNBKWNDF-UHFFFAOYSA-N 3,4-dimethylbenzene-1,2-diamine Chemical group CC1=CC=C(N)C(N)=C1C MHQULXYNBKWNDF-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- UCTREIIEJSFTDI-UHFFFAOYSA-N 3-aminonaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1 UCTREIIEJSFTDI-UHFFFAOYSA-N 0.000 description 1
- IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical class ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 description 1
- BXIXXXYDDJVHDL-UHFFFAOYSA-N 4-Chloro-ortho-phenylenediamine Chemical compound NC1=CC=C(Cl)C=C1N BXIXXXYDDJVHDL-UHFFFAOYSA-N 0.000 description 1
- AGAHETWGCFCMDK-UHFFFAOYSA-N 4-methoxybenzene-1,2-diamine Chemical compound COC1=CC=C(N)C(N)=C1 AGAHETWGCFCMDK-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- ORLGPUVJERIKLW-UHFFFAOYSA-N 5-chlorotriazine Chemical compound ClC1=CN=NN=C1 ORLGPUVJERIKLW-UHFFFAOYSA-N 0.000 description 1
- KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 1
- CMOLPZZVECHXKN-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 CMOLPZZVECHXKN-UHFFFAOYSA-N 0.000 description 1
- 0 CCC([C@@](C1)C(S(O)(=O)=O)=CC)C(S(O)(=O)=O)=C[C@]1N=NC(C(*)(CC)C1)=CC=C1NC1=*CC(Cl)=NC(Nc2c(*C(C)=*C(Cl)=NC(NC(C=C3)=CC(*)[C@@]3N=Nc3cc(c(*)ccc4)c4c(S(O)(=O)=O)c3)=N)cccc2)=N1 Chemical compound CCC([C@@](C1)C(S(O)(=O)=O)=CC)C(S(O)(=O)=O)=C[C@]1N=NC(C(*)(CC)C1)=CC=C1NC1=*CC(Cl)=NC(Nc2c(*C(C)=*C(Cl)=NC(NC(C=C3)=CC(*)[C@@]3N=Nc3cc(c(*)ccc4)c4c(S(O)(=O)=O)c3)=N)cccc2)=N1 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- CUBBETISFVCGIO-UHFFFAOYSA-N ethyl n-(3-aminophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC(N)=C1 CUBBETISFVCGIO-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 description 1
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010015 semi-continuous dyeing Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003918 triazines 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
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50158286A JPS5857464B2 (ja) | 1975-12-29 | 1975-12-29 | ハンノウセイアゾセンリヨウノセイホウ |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH624139A5 true CH624139A5 (en, 2012) | 1981-07-15 |
Family
ID=15668265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1631976A CH624139A5 (en, 2012) | 1975-12-29 | 1976-12-24 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4474696A (en, 2012) |
| JP (1) | JPS5857464B2 (en, 2012) |
| CH (1) | CH624139A5 (en, 2012) |
| DE (1) | DE2658268C2 (en, 2012) |
| FR (1) | FR2337183A1 (en, 2012) |
| GB (1) | GB1527949A (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0042204A3 (en) * | 1980-06-18 | 1982-03-03 | Imperial Chemical Industries Plc | Reactive dyestuffs |
| CH669305GA3 (en, 2012) * | 1981-12-11 | 1989-03-15 | ||
| EP0465420B1 (de) * | 1990-07-02 | 1996-10-30 | Ciba-Geigy Ag | Azofarbstoffe |
| GB9016448D0 (en) * | 1990-07-26 | 1990-09-12 | Ici Plc | Anionic compounds |
| US5374301A (en) * | 1990-07-26 | 1994-12-20 | Zeneca Limited | Inks suitable for use in ink jet printing |
| GB0319234D0 (en) * | 2003-08-15 | 2003-09-17 | Dystar Textilfarben Gmbh & Co | Fibre reactive azo dyes |
| US7785376B1 (en) * | 2007-11-28 | 2010-08-31 | The United States Of America As Represented By The Secretary Of Agriculture | Method for binding compounds to textiles |
| CN105273437B (zh) * | 2015-10-20 | 2017-05-17 | 湖北华丽染料工业有限公司 | 一种红色活性染料及其制备方法和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3118869A (en) * | 1960-07-14 | 1964-01-21 | Ici Ltd | Water-soluble fiber reactive dyestuffs having two chromophoric groups and linked together through triazine or pyrimidine rings |
| US3261825A (en) * | 1963-03-11 | 1966-07-19 | Martin Marietta Corp | Azo-disulfide triazine dyestuffs |
| US3639662A (en) * | 1968-03-07 | 1972-02-01 | Ici Ltd | Azo dyes of the triazine series |
| GB1243263A (en) * | 1968-03-08 | 1971-08-18 | Ici Ltd | New water-soluble reactive dyestuffs containing chlorotriazine residues |
| GB1259610A (en, 2012) * | 1968-12-31 | 1972-01-05 | ||
| GB1283771A (en) * | 1969-01-16 | 1972-08-02 | Ici Ltd | New reactive disazo dyestuffs |
| US3826799A (en) * | 1972-08-11 | 1974-07-30 | Ici Ltd | Copper containing azo triazine compounds |
| US3966705A (en) * | 1974-01-04 | 1976-06-29 | Ciba-Geigy Corporation | Disulfo naphthalene containing fiber-reactive tetrazo dyes |
-
1975
- 1975-12-29 JP JP50158286A patent/JPS5857464B2/ja not_active Expired
-
1976
- 1976-11-24 GB GB49019/76A patent/GB1527949A/en not_active Expired
- 1976-12-22 DE DE2658268A patent/DE2658268C2/de not_active Expired
- 1976-12-24 CH CH1631976A patent/CH624139A5/de not_active IP Right Cessation
- 1976-12-28 FR FR7639297A patent/FR2337183A1/fr active Granted
-
1980
- 1980-06-03 US US06/156,041 patent/US4474696A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB1527949A (en) | 1978-10-11 |
| DE2658268C2 (de) | 1986-03-06 |
| FR2337183A1 (fr) | 1977-07-29 |
| FR2337183B1 (en, 2012) | 1979-03-09 |
| US4474696A (en) | 1984-10-02 |
| JPS5857464B2 (ja) | 1983-12-20 |
| JPS5282935A (en) | 1977-07-11 |
| DE2658268A1 (de) | 1977-07-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |