DE3029699C2 - - Google Patents
Info
- Publication number
- DE3029699C2 DE3029699C2 DE3029699A DE3029699A DE3029699C2 DE 3029699 C2 DE3029699 C2 DE 3029699C2 DE 3029699 A DE3029699 A DE 3029699A DE 3029699 A DE3029699 A DE 3029699A DE 3029699 C2 DE3029699 C2 DE 3029699C2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- alkyl
- compounds
- group
- mixtures
- 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
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 238000004043 dyeing Methods 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 150000003839 salts Chemical group 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 239000003086 colorant Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- -1 alkyl radical Chemical class 0.000 description 13
- 239000000975 dye Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000000985 reactive dye Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 125000000565 sulfonamide group Chemical group 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 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 2
- 229920000297 Rayon Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 1
- GOYNRDSJTYLXBU-UHFFFAOYSA-N 5-chloro-2,4,6-trifluoropyrimidine Chemical compound FC1=NC(F)=C(Cl)C(F)=N1 GOYNRDSJTYLXBU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 238000005457 optimization Methods 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
- 238000005185 salting out Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B62/20—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 pyrimidine ring
- C09B62/24—Azo dyes
- C09B62/25—Disazo or polyazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH751779A CH643583A5 (de) | 1979-08-16 | 1979-08-16 | Reaktivfarbstoffe sowie deren herstellung. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3029699A1 DE3029699A1 (de) | 1981-03-26 |
| DE3029699C2 true DE3029699C2 (en, 2012) | 1987-05-27 |
Family
ID=4326385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803029699 Granted DE3029699A1 (de) | 1979-08-16 | 1980-08-06 | Faser-reaktive disazoverbindungen |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4314818A (en, 2012) |
| JP (1) | JPS6025064B2 (en, 2012) |
| AU (1) | AU536602B2 (en, 2012) |
| BE (1) | BE884645A (en, 2012) |
| BR (1) | BR8005147A (en, 2012) |
| CH (1) | CH643583A5 (en, 2012) |
| DE (1) | DE3029699A1 (en, 2012) |
| ES (1) | ES8106168A1 (en, 2012) |
| FI (1) | FI69858C (en, 2012) |
| FR (1) | FR2465770A1 (en, 2012) |
| GB (1) | GB2057480B (en, 2012) |
| HK (1) | HK59686A (en, 2012) |
| IT (1) | IT1132409B (en, 2012) |
| KE (1) | KE3636A (en, 2012) |
| MY (1) | MY8600693A (en, 2012) |
| NL (1) | NL187637C (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3033611A1 (de) * | 1980-09-06 | 1982-04-29 | Hoechst Ag, 6000 Frankfurt | Wasserloesliche disazoverbindungen, verfahren zu deren herstellung und ihre verwendung als farbstoffe |
| DE3122425A1 (de) * | 1981-06-05 | 1982-12-23 | Bayer Ag, 5090 Leverkusen | Faserreaktive disazofarbstoffe, ihre herstellung und verwendung |
| DE3468694D1 (en) * | 1983-07-29 | 1988-02-18 | Ciba Geigy Ag | Reactive dyes, their preparation and their use |
| DE3420467A1 (de) * | 1984-06-01 | 1985-12-05 | Basf Ag, 6700 Ludwigshafen | Reaktivfarbstoffe |
| CH660493A5 (de) * | 1984-12-07 | 1987-04-30 | Ciba Geigy Ag | Verfahren zur herstellung konzentrierter salzarmer waessriger loesungen von aminotriazinyl-reaktivfarbstoffen. |
| DE3542025A1 (de) * | 1985-11-28 | 1987-06-11 | Hoechst Ag | Mischungen wasserloeslicher faserreaktiver farbstoffe und ihre verwendung zum faerben |
| DE3905364A1 (de) * | 1989-02-22 | 1990-08-23 | Hoechst Ag | Substituierte pyrimidin-derivate, verfahren zu ihrer herstellung und ihre verwendung als tool |
| EP0531968A1 (de) * | 1991-09-13 | 1993-03-17 | Hoechst Aktiengesellschaft | Mischung wasserlöslicher faserreaktiver Farbstoffe und ihre Verwendung |
| BR9303266A (pt) * | 1992-08-14 | 1994-03-08 | Sandoz Ag | Compostos e seus sais ou misturas de fais compostos ou sais,processos para sua preparacao,e processo para tingimento ou estampagem de um substrato organico |
| KR100831600B1 (ko) | 2007-02-09 | 2008-05-23 | (주)경인양행 | 반응성 염료 조성물 및 이를 이용한 섬유의 염색방법 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH448329A (de) * | 1961-11-21 | 1967-12-15 | Ciba Geigy | Verfahren zur Herstellung neuer Disazofarbstoffe |
| DE1644171A1 (de) * | 1966-09-10 | 1970-07-30 | Bayer Ag | Reaktivfarbstoffe und Verfahren zu deren Herstellung |
| US3966705A (en) * | 1974-01-04 | 1976-06-29 | Ciba-Geigy Corporation | Disulfo naphthalene containing fiber-reactive tetrazo dyes |
-
1979
- 1979-08-16 CH CH751779A patent/CH643583A5/de not_active IP Right Cessation
-
1980
- 1980-08-06 DE DE19803029699 patent/DE3029699A1/de active Granted
- 1980-08-06 BE BE1/9918A patent/BE884645A/fr not_active IP Right Cessation
- 1980-08-08 FI FI802507A patent/FI69858C/fi not_active IP Right Cessation
- 1980-08-11 US US06/177,017 patent/US4314818A/en not_active Expired - Lifetime
- 1980-08-13 GB GB8026315A patent/GB2057480B/en not_active Expired
- 1980-08-13 NL NLAANVRAGE8004583,A patent/NL187637C/xx not_active IP Right Cessation
- 1980-08-14 ES ES494291A patent/ES8106168A1/es not_active Expired
- 1980-08-14 AU AU61458/80A patent/AU536602B2/en not_active Ceased
- 1980-08-14 JP JP55111148A patent/JPS6025064B2/ja not_active Expired
- 1980-08-14 IT IT24170/80A patent/IT1132409B/it active
- 1980-08-15 BR BR8005147A patent/BR8005147A/pt not_active IP Right Cessation
- 1980-08-18 FR FR8018044A patent/FR2465770A1/fr active Granted
-
1986
- 1986-05-05 KE KE3636A patent/KE3636A/xx unknown
- 1986-08-14 HK HK596/86A patent/HK59686A/xx unknown
- 1986-12-30 MY MY693/86A patent/MY8600693A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE884645A (fr) | 1981-02-06 |
| MY8600693A (en) | 1986-12-31 |
| AU536602B2 (en) | 1984-05-17 |
| ES494291A0 (es) | 1981-07-16 |
| ES8106168A1 (es) | 1981-07-16 |
| NL187637C (nl) | 1991-12-02 |
| IT8024170A0 (it) | 1980-08-14 |
| IT1132409B (it) | 1986-07-02 |
| FI69858C (fi) | 1986-05-26 |
| KE3636A (en) | 1986-05-30 |
| FR2465770B1 (en, 2012) | 1984-11-09 |
| NL187637B (nl) | 1991-07-01 |
| BR8005147A (pt) | 1981-03-10 |
| HK59686A (en) | 1986-08-22 |
| AU6145880A (en) | 1981-02-19 |
| FI802507A7 (fi) | 1981-02-17 |
| FI69858B (fi) | 1985-12-31 |
| GB2057480B (en) | 1983-05-18 |
| FR2465770A1 (fr) | 1981-03-27 |
| GB2057480A (en) | 1981-04-01 |
| JPS6025064B2 (ja) | 1985-06-15 |
| NL8004583A (nl) | 1981-02-18 |
| JPS5628245A (en) | 1981-03-19 |
| US4314818A (en) | 1982-02-09 |
| DE3029699A1 (de) | 1981-03-26 |
| CH643583A5 (de) | 1984-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |