DE1807302A1 - Phthalocyaninfarbstoffe - Google Patents
PhthalocyaninfarbstoffeInfo
- Publication number
- DE1807302A1 DE1807302A1 DE19681807302 DE1807302A DE1807302A1 DE 1807302 A1 DE1807302 A1 DE 1807302A1 DE 19681807302 DE19681807302 DE 19681807302 DE 1807302 A DE1807302 A DE 1807302A DE 1807302 A1 DE1807302 A1 DE 1807302A1
- Authority
- DE
- Germany
- Prior art keywords
- acid chloride
- methylsulfonyl
- pyrimidinyl
- radicals
- methyl
- 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.)
- Pending
Links
- 239000001007 phthalocyanine dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000985 reactive dye Substances 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- -1 alkyl radicals Chemical class 0.000 description 92
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
- 239000000975 dye Substances 0.000 description 23
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 14
- 235000011121 sodium hydroxide Nutrition 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- FNDILMSPYLBYIG-UHFFFAOYSA-N 2-amino-4-(2-aminoethyl)benzenesulfonic acid Chemical compound NCCC1=CC=C(S(O)(=O)=O)C(N)=C1 FNDILMSPYLBYIG-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- NGCRLFIYVFOUMZ-UHFFFAOYSA-N 2,3-dichloroquinoxaline-6-carbonyl chloride Chemical compound N1=C(Cl)C(Cl)=NC2=CC(C(=O)Cl)=CC=C21 NGCRLFIYVFOUMZ-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- WDEQGLDWZMIMJM-UHFFFAOYSA-N benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound OCC1CC(O)CN1C(=O)OCC1=CC=CC=C1 WDEQGLDWZMIMJM-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000005185 salting out Methods 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- 239000010981 turquoise Substances 0.000 description 3
- YXYCPKOAGWDZKX-UHFFFAOYSA-N 2,4-difluoro-5-(trifluoromethyl)pyrimidine Chemical compound FC1=NC=C(C(F)(F)F)C(F)=N1 YXYCPKOAGWDZKX-UHFFFAOYSA-N 0.000 description 2
- LTDKUDFNWBIWIO-UHFFFAOYSA-N 2-amino-4-(aminomethyl)benzenesulfonic acid Chemical compound NCC1=CC=C(S(O)(=O)=O)C(N)=C1 LTDKUDFNWBIWIO-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- HWSXHIPWMYCQPD-UHFFFAOYSA-N 5-amino-2-(2-aminoethyl)benzenesulfonic acid Chemical compound NCCC1=CC=C(N)C=C1S(O)(=O)=O HWSXHIPWMYCQPD-UHFFFAOYSA-N 0.000 description 2
- WVRFOWUCHMXFRU-UHFFFAOYSA-N 5-amino-2-(aminomethyl)benzenesulfonic acid Chemical compound NCC1=CC=C(N)C=C1S(O)(=O)=O WVRFOWUCHMXFRU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 108010077895 Sarcosine Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 229960002449 glycine Drugs 0.000 description 2
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229940043230 sarcosine Drugs 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 229960003080 taurine Drugs 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-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
- HAZJTCQWIDBCCE-UHFFFAOYSA-N 1h-triazine-6-thione Chemical compound SC1=CC=NN=N1 HAZJTCQWIDBCCE-UHFFFAOYSA-N 0.000 description 1
- KESAPMAPWGLLQL-UHFFFAOYSA-N 2,2,3,3-tetrafluorocyclobutane-1-carbonyl chloride Chemical compound FC1(F)CC(C(Cl)=O)C1(F)F KESAPMAPWGLLQL-UHFFFAOYSA-N 0.000 description 1
- BYVKICLDZSJHAA-UHFFFAOYSA-N 2,3-dibromoquinoxaline-6-carbonyl bromide Chemical compound N1=C(Br)C(Br)=NC2=CC(C(=O)Br)=CC=C21 BYVKICLDZSJHAA-UHFFFAOYSA-N 0.000 description 1
- VZLILCJJQCJIRS-UHFFFAOYSA-N 2,3-dichloroquinoxaline-6-sulfonyl chloride Chemical compound C1=C(S(Cl)(=O)=O)C=C2N=C(Cl)C(Cl)=NC2=C1 VZLILCJJQCJIRS-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- FYSHPROTETTWKB-UHFFFAOYSA-N 2,4,5,6-tetrabromopyrimidine Chemical compound BrC1=NC(Br)=C(Br)C(Br)=N1 FYSHPROTETTWKB-UHFFFAOYSA-N 0.000 description 1
- GVBHCMNXRKOJRH-UHFFFAOYSA-N 2,4,5,6-tetrachloropyrimidine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=N1 GVBHCMNXRKOJRH-UHFFFAOYSA-N 0.000 description 1
- KZMWBUVUQLGBBP-UHFFFAOYSA-N 2,4,5,6-tetrafluoropyrimidine Chemical compound FC1=NC(F)=C(F)C(F)=N1 KZMWBUVUQLGBBP-UHFFFAOYSA-N 0.000 description 1
- OQNKONMCYMWUGP-UHFFFAOYSA-N 2,4,5,6-tetrakis(methylsulfonyl)pyrimidine Chemical compound CS(=O)(=O)C1=NC(S(C)(=O)=O)=C(S(C)(=O)=O)C(S(C)(=O)=O)=N1 OQNKONMCYMWUGP-UHFFFAOYSA-N 0.000 description 1
- BIMGULMREAFXSC-UHFFFAOYSA-N 2,4,5-trifluoro-6-methylpyrimidine Chemical compound CC1=NC(F)=NC(F)=C1F BIMGULMREAFXSC-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
- VHYBUUMUUNCHCK-UHFFFAOYSA-N 2,4,6-tribromo-1,3,5-triazine Chemical compound BrC1=NC(Br)=NC(Br)=N1 VHYBUUMUUNCHCK-UHFFFAOYSA-N 0.000 description 1
- XJNDXSGINZSFDF-UHFFFAOYSA-N 2,4,6-trichloropyrimidine-5-carbonyl chloride Chemical compound ClC(=O)C1=C(Cl)N=C(Cl)N=C1Cl XJNDXSGINZSFDF-UHFFFAOYSA-N 0.000 description 1
- LUOWQRCVEYJUJS-UHFFFAOYSA-N 2,4,6-trifluoro-5-(trifluoromethyl)pyrimidine Chemical compound FC1=NC(F)=C(C(F)(F)F)C(F)=N1 LUOWQRCVEYJUJS-UHFFFAOYSA-N 0.000 description 1
- AZVALKSFVWAVOL-UHFFFAOYSA-N 2,4,6-trifluoro-5-methylpyrimidine Chemical compound CC1=C(F)N=C(F)N=C1F AZVALKSFVWAVOL-UHFFFAOYSA-N 0.000 description 1
- CZHWBISSOIPPNL-UHFFFAOYSA-N 2,4,6-trifluoro-5-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=C(F)N=C(F)N=C1F CZHWBISSOIPPNL-UHFFFAOYSA-N 0.000 description 1
- MLLSXQLOUGEEGV-UHFFFAOYSA-N 2,4,6-trifluoro-5-nitropyrimidine Chemical compound [O-][N+](=O)C1=C(F)N=C(F)N=C1F MLLSXQLOUGEEGV-UHFFFAOYSA-N 0.000 description 1
- VFIWQBCLEGAHDR-UHFFFAOYSA-N 2,4,6-tris(benzenesulfonyl)-1,3,5-triazine Chemical compound N=1C(S(=O)(=O)C=2C=CC=CC=2)=NC(S(=O)(=O)C=2C=CC=CC=2)=NC=1S(=O)(=O)C1=CC=CC=C1 VFIWQBCLEGAHDR-UHFFFAOYSA-N 0.000 description 1
- VAOWDUICNHWGRL-UHFFFAOYSA-N 2,4,6-tris(methylsulfonyl)pyrimidine Chemical compound CS(=O)(=O)C1=CC(S(C)(=O)=O)=NC(S(C)(=O)=O)=N1 VAOWDUICNHWGRL-UHFFFAOYSA-N 0.000 description 1
- MIVVPUZFDSCZJE-UHFFFAOYSA-N 2,4-bis(methylsulfonyl)-1,3,5-triazine Chemical compound CS(=O)(=O)C1=NC=NC(S(C)(=O)=O)=N1 MIVVPUZFDSCZJE-UHFFFAOYSA-N 0.000 description 1
- FNSNECVCDMIFBA-UHFFFAOYSA-N 2,4-bis(methylsulfonyl)-6-phenoxy-1,3,5-triazine Chemical compound CS(=O)(=O)C1=NC(S(=O)(=O)C)=NC(OC=2C=CC=CC=2)=N1 FNSNECVCDMIFBA-UHFFFAOYSA-N 0.000 description 1
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 1
- NIAMELKDNLLWRH-UHFFFAOYSA-N 2,4-difluoro-5-methylpyrimidine Chemical compound CC1=CN=C(F)N=C1F NIAMELKDNLLWRH-UHFFFAOYSA-N 0.000 description 1
- GIBOHPZCGYRPBS-UHFFFAOYSA-N 2,4-difluoro-5-nitropyrimidine Chemical compound [O-][N+](=O)C1=CN=C(F)N=C1F GIBOHPZCGYRPBS-UHFFFAOYSA-N 0.000 description 1
- GJOGRJUICNPNSV-UHFFFAOYSA-N 2,4-difluoro-5-phenylpyrimidine Chemical compound FC1=NC(F)=NC=C1C1=CC=CC=C1 GJOGRJUICNPNSV-UHFFFAOYSA-N 0.000 description 1
- FKSSZHRRUUZKCM-UHFFFAOYSA-N 2,4-difluoro-6-(trifluoromethyl)pyrimidine Chemical compound FC1=CC(C(F)(F)F)=NC(F)=N1 FKSSZHRRUUZKCM-UHFFFAOYSA-N 0.000 description 1
- YKLOPWRWWFKUBX-UHFFFAOYSA-N 2,4-difluoro-6-methylpyrimidine Chemical compound CC1=CC(F)=NC(F)=N1 YKLOPWRWWFKUBX-UHFFFAOYSA-N 0.000 description 1
- AOSHQVWIJNXEMB-UHFFFAOYSA-N 2,4-difluoropyrimidine-5-carbonitrile Chemical compound FC1=NC=C(C#N)C(F)=N1 AOSHQVWIJNXEMB-UHFFFAOYSA-N 0.000 description 1
- YSKSNCNLMXAQLP-UHFFFAOYSA-N 2,6-bis(methylsulfonyl)pyridine-4-carbonyl chloride Chemical compound CS(=O)(=O)C1=CC(C(Cl)=O)=CC(S(C)(=O)=O)=N1 YSKSNCNLMXAQLP-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
- NUYJCMGJLNVOML-UHFFFAOYSA-N 2,6-dichloropyrimidine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC(Cl)=NC(Cl)=N1 NUYJCMGJLNVOML-UHFFFAOYSA-N 0.000 description 1
- WFJGZGDYFGUMCA-UHFFFAOYSA-N 2,6-difluoropyrimidine-4-carbonitrile Chemical compound FC1=CC(C#N)=NC(F)=N1 WFJGZGDYFGUMCA-UHFFFAOYSA-N 0.000 description 1
- IDDLHNUKISKRRT-UHFFFAOYSA-N 2-(4-chloro-6-methylpyrimidin-2-yl)sulfonylethanesulfonic acid Chemical compound CC1=CC(Cl)=NC(S(=O)(=O)CCS(O)(=O)=O)=N1 IDDLHNUKISKRRT-UHFFFAOYSA-N 0.000 description 1
- FAUYZTIBIRCNPZ-UHFFFAOYSA-N 2-(benzenesulfonyl)-4,5-dichloro-6-methylpyrimidine Chemical compound ClC1=C(Cl)C(C)=NC(S(=O)(=O)C=2C=CC=CC=2)=N1 FAUYZTIBIRCNPZ-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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WCBVOPMSONYWEB-UHFFFAOYSA-N 2-aminoacetyl chloride Chemical compound NCC(Cl)=O WCBVOPMSONYWEB-UHFFFAOYSA-N 0.000 description 1
- XVKLMYQMVPHUPN-UHFFFAOYSA-N 2-bromoquinoxaline Chemical compound C1=CC=CC2=NC(Br)=CN=C21 XVKLMYQMVPHUPN-UHFFFAOYSA-N 0.000 description 1
- ZYVDXPBGWGSPGT-UHFFFAOYSA-N 2-chloro-4-methylpyrimidine-5-carbonyl chloride Chemical compound CC1=NC(Cl)=NC=C1C(Cl)=O ZYVDXPBGWGSPGT-UHFFFAOYSA-N 0.000 description 1
- PDFCTNCUMKYOCB-UHFFFAOYSA-N 2-quinolin-2-ylsulfonylacetic acid Chemical compound C1=CC=CC2=NC(S(=O)(=O)CC(=O)O)=CC=C21 PDFCTNCUMKYOCB-UHFFFAOYSA-N 0.000 description 1
- CTSAKABLTRMUQJ-UHFFFAOYSA-N 2-sulfonyl-3h-1,3-benzothiazole Chemical class C1=CC=C2SC(=S(=O)=O)NC2=C1 CTSAKABLTRMUQJ-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- CIOZSHPCPJZSOS-UHFFFAOYSA-N 3,6-bis(benzenesulfonyl)pyridazine Chemical compound C=1C=C(S(=O)(=O)C=2C=CC=CC=2)N=NC=1S(=O)(=O)C1=CC=CC=C1 CIOZSHPCPJZSOS-UHFFFAOYSA-N 0.000 description 1
- QTAGZDNCORZVNJ-UHFFFAOYSA-N 3,6-bis(trichloromethylsulfonyl)pyridazine Chemical compound ClC(Cl)(Cl)S(=O)(=O)C1=CC=C(S(=O)(=O)C(Cl)(Cl)Cl)N=N1 QTAGZDNCORZVNJ-UHFFFAOYSA-N 0.000 description 1
- QPZGKMLYCRNKCK-UHFFFAOYSA-N 3-(benzenesulfonyl)propanoyl chloride Chemical compound ClC(=O)CCS(=O)(=O)C1=CC=CC=C1 QPZGKMLYCRNKCK-UHFFFAOYSA-N 0.000 description 1
- USABLKDPCXBPRX-UHFFFAOYSA-N 3-[[4,6-bis(methylsulfonyl)-1,3,5-triazin-2-yl]amino]benzenesulfonic acid Chemical compound CS(=O)(=O)C1=NC(S(=O)(=O)C)=NC(NC=2C=C(C=CC=2)S(O)(=O)=O)=N1 USABLKDPCXBPRX-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 1
- QIMCIIVGSIZXFU-UHFFFAOYSA-N 3-chloroquinoxaline-2-carbonyl chloride Chemical compound C1=CC=C2N=C(Cl)C(C(=O)Cl)=NC2=C1 QIMCIIVGSIZXFU-UHFFFAOYSA-N 0.000 description 1
- CGIHHZTTZZMCRK-UHFFFAOYSA-N 3-chloroquinoxaline-6-carbonyl chloride Chemical compound N1=CC(Cl)=NC2=CC(C(=O)Cl)=CC=C21 CGIHHZTTZZMCRK-UHFFFAOYSA-N 0.000 description 1
- WQKQLSHSOYSQIU-UHFFFAOYSA-N 3-chloroquinoxaline-6-carboxylic acid Chemical compound N1=CC(Cl)=NC2=CC(C(=O)O)=CC=C21 WQKQLSHSOYSQIU-UHFFFAOYSA-N 0.000 description 1
- MNRJWEIGUPDQQW-UHFFFAOYSA-N 3-ethylsulfonylpropanoyl chloride Chemical compound CCS(=O)(=O)CCC(Cl)=O MNRJWEIGUPDQQW-UHFFFAOYSA-N 0.000 description 1
- NEWJTMRGYKBXMK-UHFFFAOYSA-N 3-methylsulfonylprop-2-enoyl chloride Chemical compound CS(=O)(=O)C=CC(Cl)=O NEWJTMRGYKBXMK-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
- NHTURKUJYDHMIQ-UHFFFAOYSA-N 4,5-dichloropyrimidine Chemical compound ClC1=CN=CN=C1Cl NHTURKUJYDHMIQ-UHFFFAOYSA-N 0.000 description 1
- FBDGJZXFKQZWLX-UHFFFAOYSA-N 4,6-bis(methylsulfonyl)pyrimidine Chemical compound CS(=O)(=O)C1=CC(S(C)(=O)=O)=NC=N1 FBDGJZXFKQZWLX-UHFFFAOYSA-N 0.000 description 1
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- KJTDCVJXCVSZBB-UHFFFAOYSA-N 4-amino-2-(2-aminoethyl)benzenesulfonic acid Chemical compound S(=O)(=O)(O)C1=C(CCN)C=C(C=C1)N KJTDCVJXCVSZBB-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
- WOQIMJVYLVUMGO-UHFFFAOYSA-N 4-chloro-2,6-difluoro-5-nitropyrimidine Chemical compound [O-][N+](=O)C1=C(F)N=C(F)N=C1Cl WOQIMJVYLVUMGO-UHFFFAOYSA-N 0.000 description 1
- POWFLCAWHSPOHP-UHFFFAOYSA-N 4-chloro-2-methylpyrimidine-5-carbonyl chloride Chemical compound CC1=NC=C(C(Cl)=O)C(Cl)=N1 POWFLCAWHSPOHP-UHFFFAOYSA-N 0.000 description 1
- NDHIIWMVAUTCNX-UHFFFAOYSA-N 4-chloro-2-methylsulfonylpyrimidine-5-sulfonic acid Chemical compound CS(=O)(=O)C1=NC=C(S(O)(=O)=O)C(Cl)=N1 NDHIIWMVAUTCNX-UHFFFAOYSA-N 0.000 description 1
- WGNKUINKIVFGBC-UHFFFAOYSA-N 4-chloro-6-methyl-2-methylsulfonyl-5-nitropyrimidine Chemical compound CC1=NC(S(C)(=O)=O)=NC(Cl)=C1[N+]([O-])=O WGNKUINKIVFGBC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LNJVTFNEAPYZIU-UHFFFAOYSA-N 4-chloro-6-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=CC(Cl)=NC=N1 LNJVTFNEAPYZIU-UHFFFAOYSA-N 0.000 description 1
- VCPXZIUQCXEVCU-UHFFFAOYSA-N 4-ethylpyrimidine Chemical compound CCC1=CC=NC=N1 VCPXZIUQCXEVCU-UHFFFAOYSA-N 0.000 description 1
- UYCCTQPHCSKTTN-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfonyl)pyrimidine Chemical compound CC1=CC(S(C)(=O)=O)=NC(S(C)(=O)=O)=N1 UYCCTQPHCSKTTN-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- FRSCGYMSBBDAKE-UHFFFAOYSA-N 5-(chloromethyl)-2,4,6-trifluoropyrimidine Chemical compound FC1=NC(F)=C(CCl)C(F)=N1 FRSCGYMSBBDAKE-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
- ZBTCTILYGQNVOJ-UHFFFAOYSA-N 5-bromo-2,4-difluoro-6-methylpyrimidine Chemical compound CC1=NC(F)=NC(F)=C1Br ZBTCTILYGQNVOJ-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
- HLWJZTCAFDZNCD-UHFFFAOYSA-N 5-chloro-2,4,6-tris(methylsulfonyl)pyrimidine Chemical compound CS(=O)(=O)C1=NC(S(C)(=O)=O)=C(Cl)C(S(C)(=O)=O)=N1 HLWJZTCAFDZNCD-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
- WZUPWJVRWIVWEF-UHFFFAOYSA-N 5-chloro-2-methylsulfonylpyrimidine-4-carboxylic acid Chemical compound CS(=O)(=O)C1=NC=C(Cl)C(C(O)=O)=N1 WZUPWJVRWIVWEF-UHFFFAOYSA-N 0.000 description 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- JNYLMODTPLSLIF-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical group OC(=O)C1=CC=C(C(F)(F)F)N=C1 JNYLMODTPLSLIF-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- GXMXHMIDNVJBAF-UHFFFAOYSA-N ClC1=NN=C(C2=CC=CC=C12)Cl.Cl Chemical compound ClC1=NN=C(C2=CC=CC=C12)Cl.Cl GXMXHMIDNVJBAF-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 241000083869 Polyommatus dorylas Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 229940039407 aniline Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 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
- 230000001588 bifunctional effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- GEKOHRZGXRUJIN-UHFFFAOYSA-N chloromethane;sulfurochloridic acid Chemical compound ClC.OS(Cl)(=O)=O GEKOHRZGXRUJIN-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 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
- 229940043237 diethanolamine Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical class F* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-O hydrazinium(1+) Chemical compound [NH3+]N OAKJQQAXSVQMHS-UHFFFAOYSA-O 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- USPGWRYCHDAJCB-UHFFFAOYSA-N methyl 2,4-difluoropyrimidine-5-carboxylate Chemical compound COC(=O)C1=CN=C(F)N=C1F USPGWRYCHDAJCB-UHFFFAOYSA-N 0.000 description 1
- FSQBCNBFHWRUGG-UHFFFAOYSA-N methyl 6-chloro-2-methylsulfonylpyrimidine-4-carboxylate Chemical compound COC(=O)C1=CC(Cl)=NC(S(C)(=O)=O)=N1 FSQBCNBFHWRUGG-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 229940113083 morpholine Drugs 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000003973 paint Substances 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
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-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
- 229920002647 polyamide Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- XVIAPHVAGFEFFN-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=CN=CN=C1 XVIAPHVAGFEFFN-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- YXZRCLVVNRLPTP-UHFFFAOYSA-J turquoise blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Cu+2].NC1=NC(Cl)=NC(NC=2C=C(NS(=O)(=O)C3=CC=4C(=C5NC=4NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)NC=4NC(=C6C=C(C=CC6=4)S([O-])(=O)=O)NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)N5)C=C3)C(=CC=2)S([O-])(=O)=O)=N1 YXZRCLVVNRLPTP-UHFFFAOYSA-J 0.000 description 1
- 230000003245 working effect Effects 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
- C09B62/016—Porphines; Azaporphines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Cosmetics (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681807302 DE1807302A1 (de) | 1968-11-06 | 1968-11-06 | Phthalocyaninfarbstoffe |
| CH1561169A CH529821A (de) | 1968-11-06 | 1969-10-17 | Verfahren zur Herstellung von Phthalocyaninfarbstoffen |
| GB1250383D GB1250383A (enrdf_load_stackoverflow) | 1968-11-06 | 1969-11-05 | |
| CA066701A CA925502A (en) | 1968-11-06 | 1969-11-05 | Phthalocyanine dyestuffs |
| NL6916706A NL6916706A (enrdf_load_stackoverflow) | 1968-11-06 | 1969-11-05 | |
| AT1042369A AT289985B (de) | 1968-11-06 | 1969-11-06 | Verfahren zur Herstellung von neuen Phthalocyanin-Reaktivfarbstoffen |
| FR6938252A FR2022724A1 (enrdf_load_stackoverflow) | 1968-11-06 | 1969-11-06 | |
| BE741344D BE741344A (enrdf_load_stackoverflow) | 1968-11-06 | 1969-11-06 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681807302 DE1807302A1 (de) | 1968-11-06 | 1968-11-06 | Phthalocyaninfarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1807302A1 true DE1807302A1 (de) | 1970-05-27 |
Family
ID=5712519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681807302 Pending DE1807302A1 (de) | 1968-11-06 | 1968-11-06 | Phthalocyaninfarbstoffe |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT289985B (enrdf_load_stackoverflow) |
| BE (1) | BE741344A (enrdf_load_stackoverflow) |
| CA (1) | CA925502A (enrdf_load_stackoverflow) |
| CH (1) | CH529821A (enrdf_load_stackoverflow) |
| DE (1) | DE1807302A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2022724A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1250383A (enrdf_load_stackoverflow) |
| NL (1) | NL6916706A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1182481B (de) * | 1960-05-18 | 1964-11-26 | Torfit Werke G A Haseke & Co | Muffenverbindung fuer Rohre aus sproedem Werkstoff |
| DE1182482B (de) * | 1960-06-01 | 1964-11-26 | Torfit Werke G A Haseke & Co | Muffenverbindung fuer Rohre aus sproedem Werkstoff |
| DE1183753B (de) * | 1960-07-25 | 1964-12-17 | Eternit Ag | Rohrkupplung |
| DE1188879B (de) * | 1960-05-18 | 1965-03-11 | Torfit Werke G A Haseke & Co | Muffenverbindung fuer Rohre aus sproedem Werkstoff |
| EP0037986A3 (en) * | 1980-04-16 | 1982-03-31 | Bayer Ag | Process for the preparation of phthalocyanine dyestuffs |
| EP0038453A3 (en) * | 1980-04-16 | 1982-03-31 | Bayer Ag | Process for the preparation of water soluble phthalocyanine dyestuffs |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2729011C2 (de) * | 1977-06-28 | 1987-01-15 | Bayer Ag, 5090 Leverkusen | Reaktivfarbstoffe |
| DE19517503A1 (de) * | 1995-05-12 | 1996-11-14 | Bayer Ag | Phthalocyaninreaktivfarbstoffmischung |
-
1968
- 1968-11-06 DE DE19681807302 patent/DE1807302A1/de active Pending
-
1969
- 1969-10-17 CH CH1561169A patent/CH529821A/de not_active IP Right Cessation
- 1969-11-05 CA CA066701A patent/CA925502A/en not_active Expired
- 1969-11-05 NL NL6916706A patent/NL6916706A/xx unknown
- 1969-11-05 GB GB1250383D patent/GB1250383A/en not_active Expired
- 1969-11-06 BE BE741344D patent/BE741344A/xx unknown
- 1969-11-06 FR FR6938252A patent/FR2022724A1/fr not_active Withdrawn
- 1969-11-06 AT AT1042369A patent/AT289985B/de not_active IP Right Cessation
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1182481B (de) * | 1960-05-18 | 1964-11-26 | Torfit Werke G A Haseke & Co | Muffenverbindung fuer Rohre aus sproedem Werkstoff |
| DE1188879B (de) * | 1960-05-18 | 1965-03-11 | Torfit Werke G A Haseke & Co | Muffenverbindung fuer Rohre aus sproedem Werkstoff |
| DE1182482B (de) * | 1960-06-01 | 1964-11-26 | Torfit Werke G A Haseke & Co | Muffenverbindung fuer Rohre aus sproedem Werkstoff |
| DE1183753B (de) * | 1960-07-25 | 1964-12-17 | Eternit Ag | Rohrkupplung |
| EP0037986A3 (en) * | 1980-04-16 | 1982-03-31 | Bayer Ag | Process for the preparation of phthalocyanine dyestuffs |
| EP0038453A3 (en) * | 1980-04-16 | 1982-03-31 | Bayer Ag | Process for the preparation of water soluble phthalocyanine dyestuffs |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1250383A (enrdf_load_stackoverflow) | 1971-10-20 |
| AT289985B (de) | 1971-05-10 |
| CH529821A (de) | 1972-10-31 |
| FR2022724A1 (enrdf_load_stackoverflow) | 1970-08-07 |
| BE741344A (enrdf_load_stackoverflow) | 1970-04-16 |
| NL6916706A (enrdf_load_stackoverflow) | 1970-05-11 |
| CA925502A (en) | 1973-05-01 |
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