JPS637221B2 - - Google Patents
Info
- Publication number
- JPS637221B2 JPS637221B2 JP54090463A JP9046379A JPS637221B2 JP S637221 B2 JPS637221 B2 JP S637221B2 JP 54090463 A JP54090463 A JP 54090463A JP 9046379 A JP9046379 A JP 9046379A JP S637221 B2 JPS637221 B2 JP S637221B2
- Authority
- JP
- Japan
- Prior art keywords
- dye
- methyl
- group
- hydroxypyrid
- sulfomethyl
- 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 monochlorotriazinyl Chemical group 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 238000004043 dyeing Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 5
- 238000007639 printing Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 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
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 2
- SPSSDDOTEZKOOV-UHFFFAOYSA-N 2,3-dichloroquinoxaline Chemical compound C1=CC=C2N=C(Cl)C(Cl)=NC2=C1 SPSSDDOTEZKOOV-UHFFFAOYSA-N 0.000 claims 2
- 239000002657 fibrous material Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 40
- 239000000243 solution Substances 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 11
- 238000005859 coupling reaction Methods 0.000 description 11
- 230000008878 coupling Effects 0.000 description 10
- 238000010168 coupling process Methods 0.000 description 10
- 229920000742 Cotton Polymers 0.000 description 8
- KTVWISLTJPDQQX-UHFFFAOYSA-N 2-amino-5-(aminomethyl)naphthalene-1-sulfonic acid Chemical compound NC1=CC=C2C(CN)=CC=CC2=C1S(O)(=O)=O KTVWISLTJPDQQX-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- SNHPXTMWZXFZGE-UHFFFAOYSA-N CCN1C(O)=CC(C)=C(CS(O)(=O)=O)C1=O Chemical compound CCN1C(O)=CC(C)=C(CS(O)(=O)=O)C1=O SNHPXTMWZXFZGE-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 3
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 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 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000010344 sodium nitrate Nutrition 0.000 description 3
- 239000004317 sodium nitrate Substances 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 239000001043 yellow dye Substances 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 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- OLILXFBXWWPDAC-UHFFFAOYSA-N 5-(aminomethyl)naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(CN)=CC=CC2=C1S(O)(=O)=O OLILXFBXWWPDAC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 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
- 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
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 2
- SQYUJKVKVFILNB-UHFFFAOYSA-N methyl 2-amino-4-[(2,5-dichlorophenyl)carbamoyl]benzoate Chemical compound C1=C(N)C(C(=O)OC)=CC=C1C(=O)NC1=CC(Cl)=CC=C1Cl SQYUJKVKVFILNB-UHFFFAOYSA-N 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- XMSJKCFDKWRFCO-UHFFFAOYSA-N (1-ethyl-2-hydroxy-6-oxopyridin-4-yl)methanesulfonic acid Chemical compound CCN1C(O)=CC(CS(O)(=O)=O)=CC1=O XMSJKCFDKWRFCO-UHFFFAOYSA-N 0.000 description 1
- ZZLNKHVJWGSEPT-UHFFFAOYSA-N (2-hydroxy-1-methyl-6-oxopyridin-4-yl)methanesulfonic acid Chemical compound CN1C(O)=CC(CS(O)(=O)=O)=CC1=O ZZLNKHVJWGSEPT-UHFFFAOYSA-N 0.000 description 1
- MYHXZUSMVFOVBZ-UHFFFAOYSA-N (5-benzoyl-6-hydroxy-1,4-dimethyl-2-oxopyridin-3-yl)methanesulfonic acid Chemical compound CN1C(=O)C(CS(O)(=O)=O)=C(C)C(C(=O)C=2C=CC=CC=2)=C1O MYHXZUSMVFOVBZ-UHFFFAOYSA-N 0.000 description 1
- ANYPQKPSMPQPGZ-UHFFFAOYSA-N (5-carbamoyl-1-ethyl-6-hydroxy-4-methyl-2-oxopyridin-3-yl)methanesulfonic acid Chemical compound CCN1C(O)=C(C(N)=O)C(C)=C(CS(O)(=O)=O)C1=O ANYPQKPSMPQPGZ-UHFFFAOYSA-N 0.000 description 1
- LITZXSLYAKVNBM-UHFFFAOYSA-N (5-carbamoyl-2-hydroxy-4-methyl-6-oxo-1h-pyridin-3-yl)methanesulfonic acid Chemical compound CC1=C(CS(O)(=O)=O)C(O)=NC(O)=C1C(N)=O LITZXSLYAKVNBM-UHFFFAOYSA-N 0.000 description 1
- GVBHCMNXRKOJRH-UHFFFAOYSA-N 2,4,5,6-tetrachloropyrimidine Chemical class ClC1=NC(Cl)=C(Cl)C(Cl)=N1 GVBHCMNXRKOJRH-UHFFFAOYSA-N 0.000 description 1
- LYBDHGMSPQBSNW-UHFFFAOYSA-N 2,4,5-trifluoropyrimidine Chemical compound FC1=NC=C(F)C(F)=N1 LYBDHGMSPQBSNW-UHFFFAOYSA-N 0.000 description 1
- AOEHEEBFRCAFGC-UHFFFAOYSA-N 2,4-dibromopyrimidine Chemical compound BrC1=CC=NC(Br)=N1 AOEHEEBFRCAFGC-UHFFFAOYSA-N 0.000 description 1
- PLVFHLAXDQSLCL-UHFFFAOYSA-N 2,6-dichloro-1h-triazin-4-amine Chemical compound NC1=NN(Cl)NC(Cl)=C1 PLVFHLAXDQSLCL-UHFFFAOYSA-N 0.000 description 1
- CTSJEGLSMYPRJK-UHFFFAOYSA-N 2,6-dichloro-n-methyl-1h-triazin-4-amine Chemical compound CNC1=NN(Cl)NC(Cl)=C1 CTSJEGLSMYPRJK-UHFFFAOYSA-N 0.000 description 1
- WULMCOUFBKKFQE-UHFFFAOYSA-N 2,6-dichloro-n-phenyl-1h-triazin-4-amine Chemical compound ClN1NC(Cl)=CC(NC=2C=CC=CC=2)=N1 WULMCOUFBKKFQE-UHFFFAOYSA-N 0.000 description 1
- IJXOQDQYOMRDSO-UHFFFAOYSA-N 2-(benzenesulfonyl)-4,5-dichloropyrimidine Chemical compound N1=C(Cl)C(Cl)=CN=C1S(=O)(=O)C1=CC=CC=C1 IJXOQDQYOMRDSO-UHFFFAOYSA-N 0.000 description 1
- OTEBTSPEXWSPLD-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carboxamide Chemical compound CC1=CC(=O)NC(O)=C1C(N)=O OTEBTSPEXWSPLD-UHFFFAOYSA-N 0.000 description 1
- KMFAWGFSESRBPG-UHFFFAOYSA-N 4,5-dichloro-2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC=C(Cl)C(Cl)=N1 KMFAWGFSESRBPG-UHFFFAOYSA-N 0.000 description 1
- YJPYVNMIARMZEK-UHFFFAOYSA-N 4,5-dichloro-6-(chloromethyl)-2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC(Cl)=C(Cl)C(CCl)=N1 YJPYVNMIARMZEK-UHFFFAOYSA-N 0.000 description 1
- DROUVIKCNOHKBA-UHFFFAOYSA-N 4,6-dichloro-2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC(Cl)=CC(Cl)=N1 DROUVIKCNOHKBA-UHFFFAOYSA-N 0.000 description 1
- SLCUSSPKUGKMGA-UHFFFAOYSA-N 4-bromo-2,6-difluoropyrimidine Chemical compound FC1=CC(Br)=NC(F)=N1 SLCUSSPKUGKMGA-UHFFFAOYSA-N 0.000 description 1
- ACYSJALOFWHUEX-UHFFFAOYSA-N 4-chloro-2,6-difluoropyrimidine Chemical compound FC1=CC(Cl)=NC(F)=N1 ACYSJALOFWHUEX-UHFFFAOYSA-N 0.000 description 1
- BOLIYMRNXVAWIJ-UHFFFAOYSA-N 5-bromo-2,4,6-trifluoropyrimidine Chemical compound FC1=NC(F)=C(Br)C(F)=N1 BOLIYMRNXVAWIJ-UHFFFAOYSA-N 0.000 description 1
- FATRNESSGITUQV-UHFFFAOYSA-N 5-bromo-4-chloro-2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC=C(Br)C(Cl)=N1 FATRNESSGITUQV-UHFFFAOYSA-N 0.000 description 1
- XZSZSTCLQANXKU-UHFFFAOYSA-N 5-chloro-2,4-difluoropyrimidine Chemical compound FC1=NC=C(Cl)C(F)=N1 XZSZSTCLQANXKU-UHFFFAOYSA-N 0.000 description 1
- WJPHPOIVNDQZFI-UHFFFAOYSA-N 6-hydroxy-1,4-dimethylpyridin-2-one Chemical compound CC=1C=C(O)N(C)C(=O)C=1 WJPHPOIVNDQZFI-UHFFFAOYSA-N 0.000 description 1
- RBQYBQHTZMAHHD-UHFFFAOYSA-N 6-hydroxy-4-methyl-1-propan-2-ylpyridin-2-one Chemical compound CC(C)N1C(O)=CC(C)=CC1=O RBQYBQHTZMAHHD-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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- DJVRYDWMBGJXHZ-UHFFFAOYSA-N CC(C)N1C(O)=CC(C)=C(S(O)(=O)=O)C1=O Chemical compound CC(C)N1C(O)=CC(C)=C(S(O)(=O)=O)C1=O DJVRYDWMBGJXHZ-UHFFFAOYSA-N 0.000 description 1
- VHJVFKAGGAYIKG-UHFFFAOYSA-N CC(C)N1C(O)=CC(CS(O)(=O)=O)=C(C#N)C1=O Chemical compound CC(C)N1C(O)=CC(CS(O)(=O)=O)=C(C#N)C1=O VHJVFKAGGAYIKG-UHFFFAOYSA-N 0.000 description 1
- UIGQWRYKMYQJIA-UHFFFAOYSA-N CC(C)N1C(O)=CC(CS(O)(=O)=O)=C(Cl)C1=O Chemical compound CC(C)N1C(O)=CC(CS(O)(=O)=O)=C(Cl)C1=O UIGQWRYKMYQJIA-UHFFFAOYSA-N 0.000 description 1
- IAIXIUDTSLCXDG-UHFFFAOYSA-N CC1=C(CS(O)(=O)=O)C(=O)N(C)C(O)=C1S(C)(=O)=O Chemical compound CC1=C(CS(O)(=O)=O)C(=O)N(C)C(O)=C1S(C)(=O)=O IAIXIUDTSLCXDG-UHFFFAOYSA-N 0.000 description 1
- GNJNARYVGKAGGU-UHFFFAOYSA-N CC1=C(CS(O)(=O)=O)C(=O)N(CC)C(O)=C1S(=O)(=O)C1=CC=CC=C1 Chemical compound CC1=C(CS(O)(=O)=O)C(=O)N(CC)C(O)=C1S(=O)(=O)C1=CC=CC=C1 GNJNARYVGKAGGU-UHFFFAOYSA-N 0.000 description 1
- KWTPEJWMORSDAJ-UHFFFAOYSA-N CC=1C=C(O)N(C)C(=O)C=1C(N)=O Chemical compound CC=1C=C(O)N(C)C(=O)C=1C(N)=O KWTPEJWMORSDAJ-UHFFFAOYSA-N 0.000 description 1
- LRZPOVQVWQOZJL-UHFFFAOYSA-N CC=1C=C(O)N(C)C(=O)C=1CS(O)(=O)=O Chemical compound CC=1C=C(O)N(C)C(=O)C=1CS(O)(=O)=O LRZPOVQVWQOZJL-UHFFFAOYSA-N 0.000 description 1
- ZETDSOQUFSTLRH-UHFFFAOYSA-N CC=1C=C(O)N(C)C(=O)C=1S(O)(=O)=O Chemical compound CC=1C=C(O)N(C)C(=O)C=1S(O)(=O)=O ZETDSOQUFSTLRH-UHFFFAOYSA-N 0.000 description 1
- QDKJXELZBFUUDX-UHFFFAOYSA-N CCCN1C(O)=CC(C)=C(CS(O)(=O)=O)C1=O Chemical compound CCCN1C(O)=CC(C)=C(CS(O)(=O)=O)C1=O QDKJXELZBFUUDX-UHFFFAOYSA-N 0.000 description 1
- YSAVDLIHWDDGRO-UHFFFAOYSA-N CCCN1C(O)=CC(C)=C(Cl)C1=O Chemical compound CCCN1C(O)=CC(C)=C(Cl)C1=O YSAVDLIHWDDGRO-UHFFFAOYSA-N 0.000 description 1
- CXMXIVKMHNJQPT-UHFFFAOYSA-N CCCN1C(O)=CC(C)=C(S(O)(=O)=O)C1=O Chemical compound CCCN1C(O)=CC(C)=C(S(O)(=O)=O)C1=O CXMXIVKMHNJQPT-UHFFFAOYSA-N 0.000 description 1
- VVXCEOCXNCWCPB-UHFFFAOYSA-N CCN1C(O)=C(S(C)(=O)=O)C(C)=C(CS(O)(=O)=O)C1=O Chemical compound CCN1C(O)=C(S(C)(=O)=O)C(C)=C(CS(O)(=O)=O)C1=O VVXCEOCXNCWCPB-UHFFFAOYSA-N 0.000 description 1
- RAKUNPLOQXWOFH-UHFFFAOYSA-N CCN1C(O)=C(S(N)(=O)=O)C(C)=C(CS(O)(=O)=O)C1=O Chemical compound CCN1C(O)=C(S(N)(=O)=O)C(C)=C(CS(O)(=O)=O)C1=O RAKUNPLOQXWOFH-UHFFFAOYSA-N 0.000 description 1
- IVEOCYLKEXGIPE-UHFFFAOYSA-N CCN1C(O)=CC(C)=C(C(N)=O)C1=O Chemical compound CCN1C(O)=CC(C)=C(C(N)=O)C1=O IVEOCYLKEXGIPE-UHFFFAOYSA-N 0.000 description 1
- YABXNPMYQRAWPR-UHFFFAOYSA-N CCN1C(O)=CC(C)=C(Cl)C1=O Chemical compound CCN1C(O)=CC(C)=C(Cl)C1=O YABXNPMYQRAWPR-UHFFFAOYSA-N 0.000 description 1
- DKFYGRSRNUNDOG-UHFFFAOYSA-N CCN1C(O)=CC(C)=C(F)C1=O Chemical compound CCN1C(O)=CC(C)=C(F)C1=O DKFYGRSRNUNDOG-UHFFFAOYSA-N 0.000 description 1
- XURQWPAHYKMTFY-UHFFFAOYSA-N CCN1C(O)=CC(C)=C(S(O)(=O)=O)C1=O Chemical compound CCN1C(O)=CC(C)=C(S(O)(=O)=O)C1=O XURQWPAHYKMTFY-UHFFFAOYSA-N 0.000 description 1
- HSPAJDOYRNONHY-UHFFFAOYSA-N CCN1C(O)=CC(CS(O)(=O)=O)=C(C#N)C1=O Chemical compound CCN1C(O)=CC(CS(O)(=O)=O)=C(C#N)C1=O HSPAJDOYRNONHY-UHFFFAOYSA-N 0.000 description 1
- CQMLEGCCHBBEEH-UHFFFAOYSA-N CCN1C(O)=CC(CS(O)(=O)=O)=C(C(N)=O)C1=O Chemical compound CCN1C(O)=CC(CS(O)(=O)=O)=C(C(N)=O)C1=O CQMLEGCCHBBEEH-UHFFFAOYSA-N 0.000 description 1
- CXVQQZDBQOHIIR-UHFFFAOYSA-N CCN1C(O)=CC(CS(O)(=O)=O)=C(S(C)(=O)=O)C1=O Chemical compound CCN1C(O)=CC(CS(O)(=O)=O)=C(S(C)(=O)=O)C1=O CXVQQZDBQOHIIR-UHFFFAOYSA-N 0.000 description 1
- LPZXFGGKIUAKJN-UHFFFAOYSA-N CN1C(O)=CC(CS(O)(=O)=O)=C(C(N)=O)C1=O Chemical compound CN1C(O)=CC(CS(O)(=O)=O)=C(C(N)=O)C1=O LPZXFGGKIUAKJN-UHFFFAOYSA-N 0.000 description 1
- LMSLDKJCBZMDFE-UHFFFAOYSA-N CN1C(O)=CC(CS(O)(=O)=O)=C(Cl)C1=O Chemical compound CN1C(O)=CC(CS(O)(=O)=O)=C(Cl)C1=O LMSLDKJCBZMDFE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BNNGMZFDJNRWPY-UHFFFAOYSA-N N1N(F)N=C(F)C(N)=C1C1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O Chemical compound N1N(F)N=C(F)C(N)=C1C1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O BNNGMZFDJNRWPY-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 241000219422 Urtica Species 0.000 description 1
- 235000009108 Urtica dioica Nutrition 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
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PRZVQXGFYVLBSM-UHFFFAOYSA-N ethyl 5-chloro-2-hydroxy-1,4-dimethyl-6-oxopyridine-3-carboxylate Chemical compound CCOC(=O)C=1C(C)=C(Cl)C(=O)N(C)C=1O PRZVQXGFYVLBSM-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000010020 roller printing Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012192 staining solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 238000005406 washing Methods 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
- C09B62/008—Monoazo dyes
- C09B62/0088—Monoazo dyes with heterocyclic compound as coupling component
-
- 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)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782831912 DE2831912A1 (de) | 1978-07-20 | 1978-07-20 | Azoreaktivfarbstoffe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5516090A JPS5516090A (en) | 1980-02-04 |
| JPS637221B2 true JPS637221B2 (US20110232667A1-20110929-C00004.png) | 1988-02-16 |
Family
ID=6044905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9046379A Granted JPS5516090A (en) | 1978-07-20 | 1979-07-18 | Azo reactive dyestuff*its manufacture and use |
Country Status (9)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4515716A (en) * | 1981-09-16 | 1985-05-07 | Mitsubishi Chemical Industries Limited | 2,6-Diaminopyridine-based azo dyes for cellulose-containing fibers |
| JPS58167653A (ja) * | 1982-03-29 | 1983-10-03 | Sumitomo Chem Co Ltd | モノアゾ化合物およびそれを用いるセルロ−ス繊維の染色方法 |
| JPS5891767A (ja) * | 1981-11-25 | 1983-05-31 | Sumitomo Chem Co Ltd | モノアゾ化合物およびそれを用いるセルロ−ス繊維の染色方法 |
| DE3371353D1 (en) * | 1982-08-25 | 1987-06-11 | Ciba Geigy Ag | Reactive dyes, their preparation and their use |
| JPS60166207A (ja) * | 1984-02-03 | 1985-08-29 | Toyo Soda Mfg Co Ltd | 抽出法リン酸中の硫酸イオン除去法 |
| JPH0788478B2 (ja) * | 1986-12-24 | 1995-09-27 | 住友化学工業株式会社 | モノアゾ化合物及びそれを用いる染色又は捺染方法 |
| DE3739350A1 (de) * | 1987-11-20 | 1989-06-01 | Hoechst Ag | 2-hydroxy-pyridon-azoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
| DE3900535A1 (de) * | 1989-01-10 | 1990-07-12 | Bayer Ag | Reaktivfarbstoffe |
| EP0465829B1 (de) * | 1990-06-19 | 1995-01-11 | Bayer Ag | Azoreaktivfarbstoffe |
| DE4107377A1 (de) * | 1991-03-08 | 1992-09-10 | Basf Ag | Reaktivfarbstoffe mit einer kupplungskomponente aus der hydroxypyridonreihe |
| DE4122866A1 (de) * | 1991-07-11 | 1993-01-14 | Bayer Ag | Monoreaktive mono- und disazoreaktivfarbstoffe |
| CN106349744A (zh) * | 2016-08-24 | 2017-01-25 | 天津德凯化工股份有限公司 | 一种高鲜艳度黄色活性染料及其制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH569767A5 (US20110232667A1-20110929-C00004.png) * | 1968-09-24 | 1975-11-28 | Ici Ltd | |
| CA965779A (en) * | 1970-05-15 | 1975-04-08 | Ciba-Geigy Ag | Azo compounds, their manufacture and use |
| CA972353A (en) * | 1970-12-22 | 1975-08-05 | Ciba-Geigy Ag | Azo compounds, their manufacture and use |
| DE2114158A1 (de) * | 1971-03-24 | 1972-09-28 | Bayer Ag | Reaktivfarbstoffe |
| DE2232541C3 (de) * | 1972-07-03 | 1978-06-15 | Bayer Ag, 5090 Leverkusen | Monoazo-Reaktivfarbstoffe und ihre Verwendung zum Färben und Bedrucken hydroxyl- oder amidgruppenhaltiger Textilmaterialien |
| GB1498669A (en) * | 1975-04-30 | 1978-01-25 | Ici Ltd | Azo dyestuffs |
| GB1552220A (en) * | 1975-12-17 | 1979-09-12 | Ici Ltd | Azo dyestuffs |
| LU78420A1 (de) | 1977-10-31 | 1979-06-01 | Ciba Geigy Ag | Farbstoffe,deren herstellung und verwendung |
-
1978
- 1978-07-20 DE DE19782831912 patent/DE2831912A1/de active Granted
-
1979
- 1979-07-05 US US06/054,726 patent/US4299764A/en not_active Expired - Lifetime
- 1979-07-17 GB GB7924857A patent/GB2026013B/en not_active Expired
- 1979-07-18 CH CH669879A patent/CH650892GA3/de unknown
- 1979-07-18 JP JP9046379A patent/JPS5516090A/ja active Granted
- 1979-07-18 IT IT7924461A patent/IT7924461A0/it unknown
- 1979-07-19 FR FR7918724A patent/FR2431522A1/fr active Granted
- 1979-07-19 ES ES482640A patent/ES482640A1/es not_active Expired
- 1979-07-20 BR BR7904637A patent/BR7904637A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH650892GA3 (US20110232667A1-20110929-C00004.png) | 1985-08-30 |
| DE2831912A1 (de) | 1980-02-07 |
| JPS5516090A (en) | 1980-02-04 |
| IT7924461A0 (it) | 1979-07-18 |
| GB2026013A (en) | 1980-01-30 |
| DE2831912C2 (US20110232667A1-20110929-C00004.png) | 1988-12-01 |
| FR2431522A1 (fr) | 1980-02-15 |
| ES482640A1 (es) | 1980-04-16 |
| GB2026013B (en) | 1982-09-29 |
| FR2431522B1 (US20110232667A1-20110929-C00004.png) | 1983-05-13 |
| BR7904637A (pt) | 1980-04-15 |
| US4299764A (en) | 1981-11-10 |
