DE1810463A1 - 1H-Pyrazolo-[3,2-c]-s-triazole - Google Patents
1H-Pyrazolo-[3,2-c]-s-triazoleInfo
- Publication number
- DE1810463A1 DE1810463A1 DE19681810463 DE1810463A DE1810463A1 DE 1810463 A1 DE1810463 A1 DE 1810463A1 DE 19681810463 DE19681810463 DE 19681810463 DE 1810463 A DE1810463 A DE 1810463A DE 1810463 A1 DE1810463 A1 DE 1810463A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- dye
- dyes
- pyrazolo
- formula
- 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
- UDFSJHJKINSRFV-UHFFFAOYSA-N N1N=CN2N=CC=C21 Chemical class N1N=CN2N=CC=C21 UDFSJHJKINSRFV-UHFFFAOYSA-N 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
- 239000001632 sodium acetate Substances 0.000 claims description 4
- 235000017281 sodium acetate Nutrition 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 2
- 241000728904 Iais Species 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 230000007717 exclusion Effects 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
- 239000000243 solution Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- -1 methyl- Chemical group 0.000 description 22
- 239000000203 mixture Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000007795 chemical reaction product Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 150000003852 triazoles Chemical class 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 150000007857 hydrazones Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000001043 yellow dye Substances 0.000 description 4
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- CQAOCWVRDYSQRD-UHFFFAOYSA-N 5-azabicyclo[3.1.0]hexa-1,3-diene Chemical compound C1=CN2CC2=C1 CQAOCWVRDYSQRD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- ZIIXGFGLSRAQBK-UHFFFAOYSA-N ethene;1h-indole Chemical compound C=C.C1=CC=C2NC=CC2=C1 ZIIXGFGLSRAQBK-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000001047 purple dye Substances 0.000 description 2
- MCSKRVKAXABJLX-UHFFFAOYSA-N pyrazolo[3,4-d]triazole Chemical compound N1=NN=C2N=NC=C21 MCSKRVKAXABJLX-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- GPXDNWQSQHFKRB-UHFFFAOYSA-N (2,4-dinitrophenyl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=C(SCl)C([N+]([O-])=O)=C1 GPXDNWQSQHFKRB-UHFFFAOYSA-N 0.000 description 1
- IFKPLJWIEQBPGG-QGZVFWFLSA-N (5s)-6-(dimethylamino)-5-methyl-4,4-diphenylhexan-3-one Chemical compound C=1C=CC=CC=1C([C@H](C)CN(C)C)(C(=O)CC)C1=CC=CC=C1 IFKPLJWIEQBPGG-QGZVFWFLSA-N 0.000 description 1
- SYIPIVAOEFWMBA-HYXAFXHYSA-N (z)-3-ethoxyprop-2-enal Chemical compound CCO\C=C/C=O SYIPIVAOEFWMBA-HYXAFXHYSA-N 0.000 description 1
- KJFGAMOXXHKTHU-UHFFFAOYSA-N 1,3-diethyl-5-methylidene-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound CCN1C(=O)C(=C)C(=O)N(CC)C1=S KJFGAMOXXHKTHU-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- DQNVJWKDCCSMLW-UHFFFAOYSA-N 2-methylideneindole Chemical compound C1=CC=CC2=NC(=C)C=C21 DQNVJWKDCCSMLW-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 description 1
- XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- NLEBPRONINNFAC-UHFFFAOYSA-N Cl.NCC1=CC=CC(=C1)N(CC)CC Chemical compound Cl.NCC1=CC=CC(=C1)N(CC)CC NLEBPRONINNFAC-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000907514 Entebbe bat virus Species 0.000 description 1
- 241001115725 Sinea Species 0.000 description 1
- 241001377894 Trias Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 108010021119 Trichosanthin Proteins 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000002951 depilatory effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YUZILKLGVPUFOT-YHPRVSEPSA-L disodium;5-[(6-anilino-4-oxo-1h-1,3,5-triazin-2-yl)amino]-2-[(e)-2-[4-[(6-anilino-4-oxo-1h-1,3,5-triazin-2-yl)amino]-2-sulfonatophenyl]ethenyl]benzenesulfonate Chemical compound [Na+].[Na+].C=1C=C(\C=C\C=2C(=CC(NC=3NC(NC=4C=CC=CC=4)=NC(=O)N=3)=CC=2)S([O-])(=O)=O)C(S(=O)(=O)[O-])=CC=1NC(N1)=NC(=O)N=C1NC1=CC=CC=C1 YUZILKLGVPUFOT-YHPRVSEPSA-L 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- UVKKGVAKIXSZMY-UHFFFAOYSA-N ethene;1h-pyrrole Chemical compound C=C.C=1C=CNC=1 UVKKGVAKIXSZMY-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 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
- 239000005457 ice water Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-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
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YUWVDIIHTJLPRI-UHFFFAOYSA-N phenylhydrazine;sulfuric acid Chemical compound OS(O)(=O)=O.NNC1=CC=CC=C1 YUWVDIIHTJLPRI-UHFFFAOYSA-N 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
- G03C7/30511—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the releasing group
- G03C7/30517—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution
- G03C7/30529—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution having the coupling site in rings of cyclic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—Colour coupling substances
- G03C7/36—Couplers containing compounds with active methylene groups
- G03C7/38—Couplers containing compounds with active methylene groups in rings
- G03C7/381—Heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5355967A GB1247493A (en) | 1967-11-24 | 1967-11-24 | Photographic colour processes |
| GB5356067 | 1967-11-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1810463A1 true DE1810463A1 (de) | 1970-10-29 |
Family
ID=26267289
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681810464 Withdrawn DE1810464A1 (de) | 1967-11-24 | 1968-11-22 | Farbphotographisches Entwicklungsverfahren |
| DE19681810462 Pending DE1810462A1 (de) | 1967-11-24 | 1968-11-22 | 1H-Pyrazolo-[3,2-c]-s-triazolfarbstoffe sowie die Verwendung der Farbstoffe zur Herstellung photographischer Materialien und zum Faerben von Textilien |
| DE19681810463 Pending DE1810463A1 (de) | 1967-11-24 | 1968-11-22 | 1H-Pyrazolo-[3,2-c]-s-triazole |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681810464 Withdrawn DE1810464A1 (de) | 1967-11-24 | 1968-11-22 | Farbphotographisches Entwicklungsverfahren |
| DE19681810462 Pending DE1810462A1 (de) | 1967-11-24 | 1968-11-22 | 1H-Pyrazolo-[3,2-c]-s-triazolfarbstoffe sowie die Verwendung der Farbstoffe zur Herstellung photographischer Materialien und zum Faerben von Textilien |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE724427A (enrdf_load_stackoverflow) |
| DE (3) | DE1810464A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1597630A (enrdf_load_stackoverflow) |
| GB (2) | GB1247493A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4540654A (en) * | 1983-03-18 | 1985-09-10 | Fuji Photo Film Co., Ltd. | Method of forming color image comprising heterocyclic magenta dye-forming coupler |
| US4576910A (en) * | 1983-06-09 | 1986-03-18 | Fuji Photo Film Co., Ltd. | Silver halide color light-sensitive material containing magenta color image-forming polymer or copolymer coupler latex |
| EP2533639A4 (en) * | 2010-02-11 | 2013-08-21 | Univ Vanderbilt | PYRAZOLOPYRIDIN, PYRAZOLOPYRZIN, PYRAZOLOPYRIMIDIN, PYRAZOLOTHIOPHEN AND PYRAZOLOTHIAZOL COMPOUNDS AS ALLOSTERIC MGLUR4 POTENTRANS AND COMPOUNDS AND METHODS OF TREATING NEUROLOGICAL DYSFUNCTIONS |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59116647A (ja) | 1982-12-13 | 1984-07-05 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料 |
| JPS59125732A (ja) * | 1983-01-07 | 1984-07-20 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| JPS59188641A (ja) | 1983-04-11 | 1984-10-26 | Fuji Photo Film Co Ltd | ハロゲン化銀写真乳剤 |
| JPS6057838A (ja) * | 1983-09-09 | 1985-04-03 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| JPS6097353A (ja) * | 1983-11-01 | 1985-05-31 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| JPS60143331A (ja) | 1983-12-29 | 1985-07-29 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
| JPS60168143A (ja) * | 1984-02-10 | 1985-08-31 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| JPS60232550A (ja) | 1984-05-02 | 1985-11-19 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| JPS60262159A (ja) * | 1984-06-08 | 1985-12-25 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| JPS6161160A (ja) * | 1984-08-31 | 1986-03-28 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料の処理方法 |
| JPS6165245A (ja) | 1984-09-06 | 1986-04-03 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| JPS61120154A (ja) * | 1984-11-15 | 1986-06-07 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| AU4743985A (en) * | 1984-09-14 | 1986-04-10 | Konishiroku Photo Industry Co., Ltd. | Silver halide photographic material with magenta coupler |
| AU4744085A (en) * | 1984-09-14 | 1986-03-27 | Konishiroku Photo Industry Co., Ltd. | Pyrazolo-triazole magenta couplers and their use in silver halide colour photography |
| US4639415A (en) * | 1984-09-17 | 1987-01-27 | Konishiroku Photo Industry Co., Ltd. | Silver halide color photographic material containing a magenta color image-forming coupler |
| EP0182486A1 (en) * | 1984-10-09 | 1986-05-28 | Konica Corporation | Silver halide color photographic material |
| US4623617A (en) * | 1984-10-09 | 1986-11-18 | Konishiroku Photo Industry Co., Ltd. | Silver halide color photographic material |
| US4675280A (en) * | 1984-10-09 | 1987-06-23 | Konishiroku Photo Industry Co., Ltd. | Silver halide color photographic material containing a 1H-pyrazolo [3,2-C]-S |
| DE3579420D1 (de) * | 1984-11-15 | 1990-10-04 | Konishiroku Photo Ind | Farbphotoempfindliches silberhalogenidmaterial. |
| US4684603A (en) * | 1984-12-12 | 1987-08-04 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide color photographic material |
| JPS61196242A (ja) * | 1985-02-27 | 1986-08-30 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| GB8508756D0 (en) * | 1985-04-03 | 1985-05-09 | Kodak Ltd | Synthesis of photographic couplers |
| JPS61243452A (ja) * | 1985-04-19 | 1986-10-29 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料 |
| JPH0812388B2 (ja) * | 1985-04-22 | 1996-02-07 | コニカ株式会社 | ハロゲン化銀カラー写真感光材料 |
| US5278038A (en) * | 1985-04-22 | 1994-01-11 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide color photographic material |
| JPS61246749A (ja) * | 1985-04-24 | 1986-11-04 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料 |
| JPS61250645A (ja) * | 1985-04-30 | 1986-11-07 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料 |
| JPH0746215B2 (ja) * | 1985-05-01 | 1995-05-17 | コニカ株式会社 | ハロゲン化銀写真感光材料 |
| AU590563B2 (en) | 1985-05-16 | 1989-11-09 | Konishiroku Photo Industry Co., Ltd. | Method for color-developing a silver halide color photographic light-sensitive material |
| US4752561A (en) * | 1985-05-17 | 1988-06-21 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide photographic material incorporating metal complex with high quenching constant and an oil soluble dye |
| DE3681347D1 (de) | 1985-05-31 | 1991-10-17 | Konishiroku Photo Ind | Verfahren zur herstellung eines direkt positiven farbbildes. |
| JPS628148A (ja) * | 1985-07-04 | 1987-01-16 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料 |
| DE3666984D1 (en) * | 1985-09-12 | 1989-12-21 | Konishiroku Photo Ind | Silver halide photographic material |
| JPH0756566B2 (ja) * | 1985-11-06 | 1995-06-14 | 富士写真フイルム株式会社 | ハロゲン化銀カラ−写真感光材料の処理方法 |
| JPS62123461A (ja) * | 1985-11-22 | 1987-06-04 | Fuji Photo Film Co Ltd | 画像形成方法 |
| AU591540B2 (en) | 1985-12-28 | 1989-12-07 | Konishiroku Photo Industry Co., Ltd. | Method of processing light-sensitive silver halide color photographic material |
| CH675420A5 (enrdf_load_stackoverflow) * | 1986-03-29 | 1990-09-28 | Agfa Gevaert Ag | |
| JPS63184743A (ja) * | 1986-09-16 | 1988-07-30 | Konica Corp | 直接ポジハロゲン化銀写真感光材料 |
| DE3706202C2 (de) * | 1987-02-26 | 1996-09-26 | Agfa Gevaert Ag | Farbfotografisches Aufzeichnungsmaterial |
| EP0284239B1 (en) | 1987-03-09 | 1992-06-10 | EASTMAN KODAK COMPANY (a New Jersey corporation) | Photographic silver halide materials and process comprising a pyrazoloazole coupler |
| US5183728A (en) * | 1987-03-09 | 1993-02-02 | Eastman Kodak Company | Photographic silver halide materials and process comprising new pyrazoloazole couplers |
| US4992361A (en) * | 1987-03-09 | 1991-02-12 | Eastman Kodak Company | Photographic silver halide materials and process comprising a pyrazolotriazole coupler |
| US4959480A (en) * | 1987-03-09 | 1990-09-25 | Eastman Kodak Company | Photographic silver halide materials and process comprising a pyrazoloazole coupler |
| US4942118A (en) * | 1987-03-09 | 1990-07-17 | Eastman Kodak Company | Photographic silver halide materials and process comprising a pyrazoloazole coupler |
| US5645981A (en) * | 1987-03-09 | 1997-07-08 | Eastman Kodak Company | Photographic silver halide materials and process comprising a pyrazolotriazole coupler |
| US4943518A (en) * | 1987-12-23 | 1990-07-24 | Konica Corporation | Direct-positive silver halide photographic light-sensitive material and method of processing it |
| US4942117A (en) * | 1988-03-21 | 1990-07-17 | Eastman Kodak Company | Photographic silver halide materials and process comprising a pyrazoloazole coupler |
| US4871652A (en) * | 1988-09-07 | 1989-10-03 | Eastman Kodak Company | Photographic silver halide material and process |
| JPH0766168B2 (ja) * | 1988-10-04 | 1995-07-19 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
| US4892805A (en) * | 1988-10-31 | 1990-01-09 | Eastman Kodak Company | Photographic element and process |
| US4948722A (en) * | 1988-10-31 | 1990-08-14 | Eastman Kodak Company | Photographic material and process comprising a pyrazoloazole dye-forming coupler |
| JPH0339956A (ja) * | 1989-01-04 | 1991-02-20 | Konica Corp | ハロゲン化銀カラー写真感光材料 |
| DE3913404A1 (de) * | 1989-04-24 | 1990-10-25 | Agfa Gevaert Ag | Farbfotografisches aufzeichnungsmaterial mit einem farbkuppler vom pyrazoloazol-typ |
| JPH02308248A (ja) * | 1989-05-24 | 1990-12-21 | Fuji Photo Film Co Ltd | アミノピリミジン系色素形成カプラーおよび該カプラーを含有するハロゲン化銀カラー写真感光材料 |
| JPH03186840A (ja) * | 1989-12-18 | 1991-08-14 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| US5021325A (en) * | 1989-12-19 | 1991-06-04 | Eastman Kodak Company | Photographic material and process comprising a pyrazolotriazole coupler |
| US5235058A (en) * | 1990-09-20 | 1993-08-10 | Fuji Photo Film Co., Ltd. | 3(5)-hydrazinopyrazole compounds |
| US5424179A (en) * | 1994-08-11 | 1995-06-13 | Eastman Kodak Company | Photographic element with a cyclic azole coupler having a saccharin substituent |
| US6140033A (en) * | 1998-12-22 | 2000-10-31 | Eastman Kodak Company | Photographic element |
| JP5109739B2 (ja) | 2008-03-14 | 2012-12-26 | コニカミノルタビジネステクノロジーズ株式会社 | 電子写真用トナー |
| JP5555979B2 (ja) | 2008-03-14 | 2014-07-23 | コニカミノルタ株式会社 | ピラゾロトリアゾール系化合物 |
| EP2618217A4 (en) | 2010-09-14 | 2015-08-12 | Konica Minolta Business Tech | ELECTROPHOTOGRAPHY TONER AND IMAGE MANUFACTURING METHOD |
| WO2012165387A1 (ja) * | 2011-05-31 | 2012-12-06 | 富士フイルム株式会社 | 着色硬化性組成物、着色硬化膜、カラーフィルタ及びその製造方法、及び表示装置、並びに、新規化合物 |
-
1967
- 1967-11-24 GB GB5355967A patent/GB1247493A/en not_active Expired
- 1967-11-24 GB GB1252418D patent/GB1252418A/en not_active Expired
-
1968
- 1968-11-22 DE DE19681810464 patent/DE1810464A1/de not_active Withdrawn
- 1968-11-22 DE DE19681810462 patent/DE1810462A1/de active Pending
- 1968-11-22 DE DE19681810463 patent/DE1810463A1/de active Pending
- 1968-11-25 BE BE724427D patent/BE724427A/xx unknown
- 1968-11-25 FR FR1597630D patent/FR1597630A/fr not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4540654A (en) * | 1983-03-18 | 1985-09-10 | Fuji Photo Film Co., Ltd. | Method of forming color image comprising heterocyclic magenta dye-forming coupler |
| US4576910A (en) * | 1983-06-09 | 1986-03-18 | Fuji Photo Film Co., Ltd. | Silver halide color light-sensitive material containing magenta color image-forming polymer or copolymer coupler latex |
| EP2533639A4 (en) * | 2010-02-11 | 2013-08-21 | Univ Vanderbilt | PYRAZOLOPYRIDIN, PYRAZOLOPYRZIN, PYRAZOLOPYRIMIDIN, PYRAZOLOTHIOPHEN AND PYRAZOLOTHIAZOL COMPOUNDS AS ALLOSTERIC MGLUR4 POTENTRANS AND COMPOUNDS AND METHODS OF TREATING NEUROLOGICAL DYSFUNCTIONS |
| US9108963B2 (en) | 2010-02-11 | 2015-08-18 | Vanderbilt University | Pyrazolopyridine, pyrazolopyrazine, pyrazolopyrimidine, pyrazolothiophene and pyrazolothiazole compounds as MGLUR4 allosteric potentiators, compositions, and methods of treating neurological dysfunction |
| US9163015B2 (en) | 2010-02-11 | 2015-10-20 | Vanderbilt University | Pyrazolopyridine, pyrarolopyrazine, pyrazolopyrimidine, pyrazolothiophene and pyrazolothiazole compounds as MGLUR4 allosteric potentiators, compositions, and methods of treating neurological dysfunction |
| AU2011215638B2 (en) * | 2010-02-11 | 2016-04-28 | Vanderbilt University | Pyrazolopyridine, pyrazolopyrazine, pyrazolopyrimidine, pyrazolothiophene and pyrazolothiazole compounds as mGluR4 allosteric potentiators, compounds, and methods of treating neurological dysfunction |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1247493A (en) | 1971-09-22 |
| DE1810462A1 (de) | 1971-09-02 |
| GB1252418A (enrdf_load_stackoverflow) | 1971-11-03 |
| DE1810464A1 (de) | 1969-07-24 |
| BE724427A (enrdf_load_stackoverflow) | 1969-05-27 |
| FR1597630A (enrdf_load_stackoverflow) | 1970-06-29 |
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