CA1114811A - Anthraquinone-azo compounds, their preparation and their use as dyestuffs - Google Patents
Anthraquinone-azo compounds, their preparation and their use as dyestuffsInfo
- Publication number
- CA1114811A CA1114811A CA335,641A CA335641A CA1114811A CA 1114811 A CA1114811 A CA 1114811A CA 335641 A CA335641 A CA 335641A CA 1114811 A CA1114811 A CA 1114811A
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- group
- radical
- lower alkyl
- alkyl
- 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
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000002253 acid Substances 0.000 claims abstract description 41
- 238000005859 coupling reaction Methods 0.000 claims abstract description 40
- 230000008878 coupling Effects 0.000 claims abstract description 37
- 238000010168 coupling process Methods 0.000 claims abstract description 37
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 12
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 6
- 150000001989 diazonium salts Chemical class 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 238000004040 coloring Methods 0.000 claims abstract description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 3
- 239000011707 mineral Substances 0.000 claims abstract description 3
- -1 vinyl-sulfonyl Chemical group 0.000 claims description 96
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 28
- 238000004043 dyeing Methods 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 239000000306 component Substances 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 239000002657 fibrous material Substances 0.000 claims description 16
- 239000000975 dye Substances 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 238000007639 printing Methods 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 229940124530 sulfonamide Drugs 0.000 claims description 10
- 150000003456 sulfonamides Chemical class 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 2
- ZVNYYNAAEVZNDW-UHFFFAOYSA-N 2-phenylpyrazol-3-amine Chemical compound NC1=CC=NN1C1=CC=CC=C1 ZVNYYNAAEVZNDW-UHFFFAOYSA-N 0.000 claims description 2
- WREXGNDJZBDHPT-UHFFFAOYSA-N 5-naphthalen-1-yl-1h-pyrazol-3-amine Chemical compound N1N=C(N)C=C1C1=CC=CC2=CC=CC=C12 WREXGNDJZBDHPT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000012954 diazonium Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- APOQJOYBYOTQRN-UHFFFAOYSA-N 2-nitramido-2-oxoacetic acid Chemical compound [N+](=O)([O-])NC(=O)C(=O)O APOQJOYBYOTQRN-UHFFFAOYSA-N 0.000 claims 3
- 125000005521 carbonamide group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims 1
- FTCOWMWIZNVSPP-UHFFFAOYSA-N 2-phenyl-4h-pyrazol-3-one Chemical compound O=C1CC=NN1C1=CC=CC=C1 FTCOWMWIZNVSPP-UHFFFAOYSA-N 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 230000000875 corresponding effect Effects 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- LKVXQCKDIYHFGZ-UHFFFAOYSA-N n-naphthalen-1-yl-3-oxobutanamide Chemical compound C1=CC=C2C(NC(=O)CC(=O)C)=CC=CC2=C1 LKVXQCKDIYHFGZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000835 fiber Substances 0.000 abstract description 5
- 229920003043 Cellulose fiber Polymers 0.000 abstract description 4
- 239000004952 Polyamide Substances 0.000 abstract description 4
- 229920002647 polyamide Polymers 0.000 abstract description 4
- 239000004627 regenerated cellulose Substances 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 4
- 229920006306 polyurethane fiber Polymers 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 description 35
- 239000000460 chlorine Substances 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 17
- 229910052801 chlorine Inorganic materials 0.000 description 17
- 235000017168 chlorine Nutrition 0.000 description 17
- 229940060038 chlorine Drugs 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 8
- 235000017550 sodium carbonate Nutrition 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 229940001593 sodium carbonate Drugs 0.000 description 8
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical group CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 210000002268 wool Anatomy 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229940074995 bromine Drugs 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- IVIHUCXXDVVSBH-UHFFFAOYSA-N 2,4-dichloropyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(Cl)N=C1Cl IVIHUCXXDVVSBH-UHFFFAOYSA-N 0.000 description 4
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 4
- 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 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 229960000819 sodium nitrite Drugs 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 3
- GKTWIIVEUYLSCS-UHFFFAOYSA-N 5-bromo-2,4,6-trichloropyrimidine Chemical compound ClC1=NC(Cl)=C(Br)C(Cl)=N1 GKTWIIVEUYLSCS-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 3
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 3
- 125000000664 diazo group Chemical class [N-]=[N+]=[*] 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- GIKMWFAAEIACRF-UHFFFAOYSA-N 2,4,5-trichloropyrimidine Chemical compound ClC1=NC=C(Cl)C(Cl)=N1 GIKMWFAAEIACRF-UHFFFAOYSA-N 0.000 description 2
- LYBDHGMSPQBSNW-UHFFFAOYSA-N 2,4,5-trifluoropyrimidine Chemical compound FC1=NC=C(F)C(F)=N1 LYBDHGMSPQBSNW-UHFFFAOYSA-N 0.000 description 2
- OASGOHGVLUSVBZ-UHFFFAOYSA-N 2,4-dibromo-5-(bromomethyl)pyrimidine Chemical compound BrCC1=CN=C(Br)N=C1Br OASGOHGVLUSVBZ-UHFFFAOYSA-N 0.000 description 2
- UEDDCBVNWFONCB-UHFFFAOYSA-N 2,4-dibromopyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(Br)N=C1Br UEDDCBVNWFONCB-UHFFFAOYSA-N 0.000 description 2
- HTEYWULAUMDASA-UHFFFAOYSA-N 2,6-bis(methylsulfonyl)pyridine-4-carboxylic acid Chemical compound CS(=O)(=O)C1=CC(C(O)=O)=CC(S(C)(=O)=O)=N1 HTEYWULAUMDASA-UHFFFAOYSA-N 0.000 description 2
- MOXUTXQEKYPKKS-UHFFFAOYSA-N 2,6-dichloropyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=NC(Cl)=N1 MOXUTXQEKYPKKS-UHFFFAOYSA-N 0.000 description 2
- NXJLFDQKISTMGE-UHFFFAOYSA-N 2,6-dichloropyrimidine-4-sulfonic acid Chemical compound OS(=O)(=O)C1=CC(Cl)=NC(Cl)=N1 NXJLFDQKISTMGE-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- FRCXPDWDMAYSCE-UHFFFAOYSA-N 3,6-dichloropyridazine-4-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=NN=C1Cl FRCXPDWDMAYSCE-UHFFFAOYSA-N 0.000 description 2
- NZXOCWXWWQNPOF-UHFFFAOYSA-N 4,5-dichloro-6-methyl-2-methylsulfonylpyrimidine Chemical compound CC1=NC(S(C)(=O)=O)=NC(Cl)=C1Cl NZXOCWXWWQNPOF-UHFFFAOYSA-N 0.000 description 2
- OLOLDTJCNAOMQJ-UHFFFAOYSA-N 4-chloro-6-methyl-2-methylsulfonylpyrimidine Chemical compound CC1=CC(Cl)=NC(S(C)(=O)=O)=N1 OLOLDTJCNAOMQJ-UHFFFAOYSA-N 0.000 description 2
- DQNOKARDYNQFLN-UHFFFAOYSA-N 5-chloro-4,6-difluoropyrimidine Chemical compound FC1=NC=NC(F)=C1Cl DQNOKARDYNQFLN-UHFFFAOYSA-N 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 229910006069 SO3H Inorganic materials 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 235000019000 fluorine Nutrition 0.000 description 2
- 229940060037 fluorine Drugs 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 230000001180 sulfating effect Effects 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
- ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 1
- ZQHJVIHCDHJVII-OWOJBTEDSA-N (e)-2-chlorobut-2-enedioic acid Chemical compound OC(=O)\C=C(\Cl)C(O)=O ZQHJVIHCDHJVII-OWOJBTEDSA-N 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- IHCXLFVGVATAND-UHFFFAOYSA-N 1,4-dichloro-2h-phthalazine-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)(Cl)NN=C(Cl)C2=C1 IHCXLFVGVATAND-UHFFFAOYSA-N 0.000 description 1
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- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- GUYMMHOQXYZMJQ-UHFFFAOYSA-N n-ethyl-3-methylaniline Chemical compound CCNC1=CC=CC(C)=C1 GUYMMHOQXYZMJQ-UHFFFAOYSA-N 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- LVOICKNPHXSSQM-UHFFFAOYSA-N prop-2-en-1-one Chemical compound C=C[C]=O LVOICKNPHXSSQM-UHFFFAOYSA-N 0.000 description 1
- 150000003152 propanolamines Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 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
- 239000000126 substance Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 229940035339 tri-chlor Drugs 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 239000000080 wetting agent 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
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
- C09B62/0068—Azodyes dyes containing in the molecule at least one azo group and at least one other chromophore group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2840119.6 | 1978-09-15 | ||
| DE19782840119 DE2840119A1 (de) | 1978-09-15 | 1978-09-15 | Anthrachinon-azoverbindungen, ihre herstellung und verwendung als farbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1114811A true CA1114811A (en) | 1981-12-22 |
Family
ID=6049488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA335,641A Expired CA1114811A (en) | 1978-09-15 | 1979-09-14 | Anthraquinone-azo compounds, their preparation and their use as dyestuffs |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5540791A (de) |
| BE (1) | BE878817A (de) |
| CA (1) | CA1114811A (de) |
| CH (1) | CH649571A5 (de) |
| DE (1) | DE2840119A1 (de) |
| FR (1) | FR2436168A1 (de) |
| GB (1) | GB2032941B (de) |
| IN (2) | IN153568B (de) |
| IT (1) | IT1165306B (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5926641A (ja) * | 1982-07-31 | 1984-02-10 | Sanwa Tekki Corp | 和動増速型慣性制振装置 |
| JPS5940038A (ja) * | 1982-08-31 | 1984-03-05 | Sanwa Tekki Corp | 増速機構付慣性制振装置 |
| JPS6095232A (ja) * | 1983-10-31 | 1985-05-28 | Sanwa Tekki Corp | 増速機構付慣性制振装置 |
| EP1055709A1 (de) * | 1999-05-25 | 2000-11-29 | Clariant International Ltd. | Anthrachinon-Azofarbstoffe sowie Farbgebung unter Verwendung von solchen Verbindungenn |
| CN105670332B (zh) * | 2016-01-29 | 2017-11-03 | 深圳市国华光电科技有限公司 | 绿色染料及其制备方法、油墨和电润湿显示器 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB781930A (en) * | 1954-11-29 | 1957-08-28 | Ici Ltd | New anthraquinonoid dyestuffs |
| GB1019771A (en) * | 1961-05-24 | 1966-02-09 | Ici Ltd | New reactive dyestuffs containing halogenotriazine residues |
| DE1289929B (de) * | 1963-06-10 | 1969-02-27 | Hoechst Ag | Verfahren zur Herstellung von faserreaktiven organischen Farbstoffen |
| CH536349A (de) * | 1969-02-13 | 1973-04-30 | Ciba Geigy Ag | Verfahren zur Herstellung reaktiver Azoverbindungen |
| CH562305A5 (de) * | 1970-12-18 | 1975-05-30 | Ciba Geigy Ag |
-
1978
- 1978-09-15 DE DE19782840119 patent/DE2840119A1/de active Granted
-
1979
- 1979-09-10 IN IN940/CAL/79A patent/IN153568B/en unknown
- 1979-09-12 IT IT7925680A patent/IT1165306B/it active
- 1979-09-12 CH CH8260/79A patent/CH649571A5/de not_active IP Right Cessation
- 1979-09-14 GB GB7931973A patent/GB2032941B/en not_active Expired
- 1979-09-14 CA CA335,641A patent/CA1114811A/en not_active Expired
- 1979-09-14 JP JP11745579A patent/JPS5540791A/ja active Pending
- 1979-09-17 BE BE0/197169A patent/BE878817A/fr not_active IP Right Cessation
- 1979-09-17 FR FR7923096A patent/FR2436168A1/fr active Granted
-
1983
- 1983-06-04 IN IN713/CAL/83A patent/IN155239B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT7925680A0 (it) | 1979-09-12 |
| IN153568B (de) | 1984-07-28 |
| BE878817A (fr) | 1980-03-17 |
| DE2840119A1 (de) | 1980-03-27 |
| CH649571A5 (de) | 1985-05-31 |
| DE2840119C2 (de) | 1988-05-11 |
| IN155239B (de) | 1985-01-12 |
| JPS5540791A (en) | 1980-03-22 |
| GB2032941B (en) | 1982-12-01 |
| IT1165306B (it) | 1987-04-22 |
| GB2032941A (en) | 1980-05-14 |
| FR2436168A1 (fr) | 1980-04-11 |
| FR2436168B1 (de) | 1984-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |