JPS6150509B2 - - Google Patents
Info
- Publication number
- JPS6150509B2 JPS6150509B2 JP54048085A JP4808579A JPS6150509B2 JP S6150509 B2 JPS6150509 B2 JP S6150509B2 JP 54048085 A JP54048085 A JP 54048085A JP 4808579 A JP4808579 A JP 4808579A JP S6150509 B2 JPS6150509 B2 JP S6150509B2
- Authority
- JP
- Japan
- Prior art keywords
- solution
- triazine
- difluoro
- dye
- water
- 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
- -1 CH 3 Chemical group 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000975 dye Substances 0.000 description 23
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000006482 condensation reaction Methods 0.000 description 13
- 239000004744 fabric Substances 0.000 description 12
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 11
- 238000004043 dyeing Methods 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 239000000985 reactive dye Substances 0.000 description 6
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 5
- 239000001103 potassium chloride Substances 0.000 description 5
- 235000011164 potassium chloride Nutrition 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 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 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- OXYURUXRBINKGA-UHFFFAOYSA-N 1-amino-4-[(3-amino-4-methylcyclohexyl)amino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1C(N)C(C)CCC1NC1=CC(S(O)(=O)=O)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O OXYURUXRBINKGA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000039 congener Substances 0.000 description 2
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- VYWOHYIFZUKARA-UHFFFAOYSA-N 1-amino-4-[(3-amino-2-methylcyclohexyl)amino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound CC1C(N)CCCC1NC1=CC(S(O)(=O)=O)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O VYWOHYIFZUKARA-UHFFFAOYSA-N 0.000 description 1
- YPYIBUOHFSQGHQ-UHFFFAOYSA-N 1-amino-4-[(4-amino-3-methylcyclohexyl)amino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1CC(N)C(C)CC1NC1=CC(S(O)(=O)=O)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O YPYIBUOHFSQGHQ-UHFFFAOYSA-N 0.000 description 1
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- PFZWMYVCCSBLJB-UHFFFAOYSA-N 2-amino-1-(cyclohexylamino)anthracene-9,10-dione Chemical class NC1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1CCCCC1 PFZWMYVCCSBLJB-UHFFFAOYSA-N 0.000 description 1
- LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 description 1
- IMUUNYPYNWXUBO-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O IMUUNYPYNWXUBO-UHFFFAOYSA-N 0.000 description 1
- GBWNQBBVSVGAAL-UHFFFAOYSA-N 5-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1 GBWNQBBVSVGAAL-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LPYYEHAKVRDCGN-UHFFFAOYSA-N C=1C=CC(S(O)(=O)=O)=CC=1N(CC(=O)O)C1=CC(F)=NN(F)N1 Chemical compound C=1C=CC(S(O)(=O)=O)=CC=1N(CC(=O)O)C1=CC(F)=NN(F)N1 LPYYEHAKVRDCGN-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LIJJJYIJOQLUKU-UHFFFAOYSA-N FN1NC(=CC(=N1)F)N(CCS(=O)(=O)O)C Chemical compound FN1NC(=CC(=N1)F)N(CCS(=O)(=O)O)C LIJJJYIJOQLUKU-UHFFFAOYSA-N 0.000 description 1
- VXCVYVKTWMCGHO-UHFFFAOYSA-N FN1NC(=CC(=N1)F)N(CS(=O)(=O)O)C Chemical compound FN1NC(=CC(=N1)F)N(CS(=O)(=O)O)C VXCVYVKTWMCGHO-UHFFFAOYSA-N 0.000 description 1
- ICVMMNVXMFQSJV-UHFFFAOYSA-N FN1NC(=CC(=N1)F)N(CS(=O)(=O)O)C1=CC=CC=C1 Chemical compound FN1NC(=CC(=N1)F)N(CS(=O)(=O)O)C1=CC=CC=C1 ICVMMNVXMFQSJV-UHFFFAOYSA-N 0.000 description 1
- RHDVUDBGYQBCHS-UHFFFAOYSA-N FN1NC(=CC(=N1)F)NC1=C(C=C(C(=C1)S(=O)(=O)O)S(=O)(=O)O)C Chemical compound FN1NC(=CC(=N1)F)NC1=C(C=C(C(=C1)S(=O)(=O)O)S(=O)(=O)O)C RHDVUDBGYQBCHS-UHFFFAOYSA-N 0.000 description 1
- PHIGOBPDMXRQNR-UHFFFAOYSA-N FN1NC(=CC(=N1)F)NC1=CC(=CC(=C1)S(=O)(=O)O)C(=O)O Chemical compound FN1NC(=CC(=N1)F)NC1=CC(=CC(=C1)S(=O)(=O)O)C(=O)O PHIGOBPDMXRQNR-UHFFFAOYSA-N 0.000 description 1
- IIKDXYNOMBZCBC-UHFFFAOYSA-N FN1NC(=CC(=N1)F)NCC1=C(C=CC(=C1)S(=O)(=O)O)C(=O)O Chemical compound FN1NC(=CC(=N1)F)NCC1=C(C=CC(=C1)S(=O)(=O)O)C(=O)O IIKDXYNOMBZCBC-UHFFFAOYSA-N 0.000 description 1
- GCTNZAAJROBYBD-UHFFFAOYSA-N FN1NC(=CC(=N1)F)NCCS(=O)(=O)O Chemical compound FN1NC(=CC(=N1)F)NCCS(=O)(=O)O GCTNZAAJROBYBD-UHFFFAOYSA-N 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
- 239000004952 Polyamide Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- GWLWWNLFFNJPDP-UHFFFAOYSA-M sodium;2-aminoethanesulfonate Chemical compound [Na+].NCCS([O-])(=O)=O GWLWWNLFFNJPDP-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 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
- C09B62/04—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
- C09B62/06—Anthracene dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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Claims (1)
- ãç¹èš±è«æ±ã®ç¯å²ã ïŒ åŒ ïŒ»åŒäžãã¯ïŒŠåã¯Clã§ããã R1åã³R2ã¯ïŒšåã¯CH3ã§ããã R3ã¯ããšãã«åã¯ä»»æã«SO3HãCOOHãCH3ã
OCH3è¥ããã¯Clã§çœ®æãããŠããããšãã«ã§ã
ãã R4ã¯C1ãC4âã¢ã«ãã«ã§ããããããŠïœã¯ïŒå
ã¯ïŒã§ãã ã®ææã ïŒ åŒ ïŒ»åŒäžãïŒR1ïŒR4åã³ïœã¯ç¹èš±è«æ±ã®ç¯å²
第ïŒé ã«ç€ºãããŠããæå³ãæãã ã®ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«èšèŒã®ææã
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782817733 DE2817733A1 (de) | 1978-04-22 | 1978-04-22 | Anthrachinon-reaktivfarbstoffe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54139937A JPS54139937A (en) | 1979-10-30 |
| JPS6150509B2 true JPS6150509B2 (ja) | 1986-11-05 |
Family
ID=6037767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4808579A Granted JPS54139937A (en) | 1978-04-22 | 1979-04-20 | Anthraquinone reactive dye |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4214082A (ja) |
| JP (1) | JPS54139937A (ja) |
| BE (1) | BE875725A (ja) |
| BR (1) | BR7902456A (ja) |
| CH (1) | CH648980GA3 (ja) |
| DE (1) | DE2817733A1 (ja) |
| ES (1) | ES479769A1 (ja) |
| FR (1) | FR2423518B1 (ja) |
| GB (1) | GB2020307B (ja) |
| IT (1) | IT7922022A0 (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4631341A (en) * | 1983-05-23 | 1986-12-23 | Sumitomo Chemical Company, Limited | Anthraquinone compound having both monohalogenotriazinyl and vinylsulfone type fiber reactive groups |
| MY144344A (en) * | 2005-04-08 | 2011-09-15 | Ciba Holding Inc | Adsorbents comprising anthraquinone dye-ligands for the separation of biological materials |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5022826A (ja) * | 1973-06-28 | 1975-03-11 | ||
| JPS50157422A (ja) * | 1974-06-13 | 1975-12-19 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB832400A (en) * | 1954-11-29 | 1960-04-13 | Ici Ltd | New anthraquinonoid dyestuffs |
| DE1644614A1 (de) * | 1967-03-25 | 1970-12-17 | Bayer Ag | Reaktivfarbstoffe |
| DE1644616A1 (de) * | 1967-06-02 | 1970-12-17 | Bayer Ag | Anthrachinon-Reaktivfarbstoffe |
| US3974160A (en) * | 1969-02-26 | 1976-08-10 | Ciba-Geigy Ag | Water-insoluble reactive dyestuffs which are soluble in aprotic solvents |
| DE2603670A1 (de) * | 1976-01-31 | 1977-08-04 | Bayer Ag | Reaktivfarbstoffe |
-
1978
- 1978-04-22 DE DE19782817733 patent/DE2817733A1/de active Granted
-
1979
- 1979-04-18 GB GB7913439A patent/GB2020307B/en not_active Expired
- 1979-04-19 CH CH370879A patent/CH648980GA3/de unknown
- 1979-04-19 IT IT7922022A patent/IT7922022A0/it unknown
- 1979-04-20 JP JP4808579A patent/JPS54139937A/ja active Granted
- 1979-04-20 FR FR7910006A patent/FR2423518B1/fr not_active Expired
- 1979-04-20 ES ES479769A patent/ES479769A1/es not_active Expired
- 1979-04-20 BR BR7902456A patent/BR7902456A/pt unknown
- 1979-04-20 US US06/031,851 patent/US4214082A/en not_active Expired - Lifetime
- 1979-04-20 BE BE0/194727A patent/BE875725A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5022826A (ja) * | 1973-06-28 | 1975-03-11 | ||
| JPS50157422A (ja) * | 1974-06-13 | 1975-12-19 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES479769A1 (es) | 1979-11-16 |
| GB2020307B (en) | 1982-10-06 |
| JPS54139937A (en) | 1979-10-30 |
| BR7902456A (pt) | 1979-10-30 |
| BE875725A (fr) | 1979-10-22 |
| US4214082A (en) | 1980-07-22 |
| GB2020307A (en) | 1979-11-14 |
| DE2817733A1 (de) | 1979-10-31 |
| DE2817733C2 (ja) | 1987-11-26 |
| IT7922022A0 (it) | 1979-04-19 |
| FR2423518B1 (fr) | 1986-05-02 |
| CH648980GA3 (ja) | 1985-04-30 |
| FR2423518A1 (fr) | 1979-11-16 |
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