JPH0245179B2 - - Google Patents

Info

Publication number

JPH0245179B2

JPH0245179B2 JP57229674A JP22967482A JPH0245179B2 JP H0245179 B2 JPH0245179 B2 JP H0245179B2 JP 57229674 A JP57229674 A JP 57229674A JP 22967482 A JP22967482 A JP 22967482A JP H0245179 B2 JPH0245179 B2 JP H0245179B2

Authority

JP

Japan

Prior art keywords

group

silver

compound

dye

general formula

Prior art date

1982-12-30

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 - Lifetime

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• -1 silver halide Chemical class 0.000 claims description 124
• 150000001875 compounds Chemical class 0.000 claims description 65
• 239000000463 material Substances 0.000 claims description 60
• 229910052709 silver Inorganic materials 0.000 claims description 49
• 239000004332 silver Substances 0.000 claims description 49
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• 239000000126 substance Substances 0.000 claims description 41
• 125000001424 substituent group Chemical group 0.000 claims description 40
• 238000011161 development Methods 0.000 claims description 38
• 238000012546 transfer Methods 0.000 claims description 32
• 239000002904 solvent Substances 0.000 claims description 27
• 125000003118 aryl group Chemical group 0.000 claims description 25
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
• 125000003277 amino group Chemical group 0.000 claims description 17
• 125000003342 alkenyl group Chemical group 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 239000002243 precursor Substances 0.000 claims description 7
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
• 125000004434 sulfur atom Chemical group 0.000 claims description 3
• 239000000975 dye Substances 0.000 description 73
• 239000010410 layer Substances 0.000 description 59
• 238000000034 method Methods 0.000 description 45
• GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 36
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
• 239000013078 crystal Substances 0.000 description 31
• 239000000243 solution Substances 0.000 description 27
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 24
• 125000004432 carbon atom Chemical group C* 0.000 description 19
• 239000003638 chemical reducing agent Substances 0.000 description 17
• 239000011230 binding agent Substances 0.000 description 16
• 239000003795 chemical substances by application Substances 0.000 description 16
• 230000015572 biosynthetic process Effects 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 238000003786 synthesis reaction Methods 0.000 description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 14
• 238000001914 filtration Methods 0.000 description 14
• 238000002844 melting Methods 0.000 description 14
• 230000008018 melting Effects 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
• 239000002253 acid Substances 0.000 description 13
• 238000006243 chemical reaction Methods 0.000 description 13
• 230000000694 effects Effects 0.000 description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
• 150000003839 salts Chemical class 0.000 description 13
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 12
• 238000001816 cooling Methods 0.000 description 11
• 239000000203 mixture Substances 0.000 description 11
• IBWXIFXUDGADCV-UHFFFAOYSA-N 2h-benzotriazole;silver Chemical compound [Ag].C1=CC=C2NN=NC2=C1 IBWXIFXUDGADCV-UHFFFAOYSA-N 0.000 description 10
• 239000002585 base Substances 0.000 description 10
• 239000000839 emulsion Substances 0.000 description 10
• 239000000123 paper Substances 0.000 description 10
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 9
• 238000005859 coupling reaction Methods 0.000 description 9
• 238000009792 diffusion process Methods 0.000 description 9
• 239000006185 dispersion Substances 0.000 description 9
• 125000001624 naphthyl group Chemical group 0.000 description 9
• 238000012545 processing Methods 0.000 description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 8
• 125000005843 halogen group Chemical group 0.000 description 8
• 238000010438 heat treatment Methods 0.000 description 8
• SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 8
• 150000007513 acids Chemical group 0.000 description 7
• 150000003863 ammonium salts Chemical class 0.000 description 7
• 239000007864 aqueous solution Substances 0.000 description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical class SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
• 206010070834 Sensitisation Diseases 0.000 description 6
• 229910052801 chlorine Inorganic materials 0.000 description 6
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
• 125000000623 heterocyclic group Chemical group 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
• 238000002360 preparation method Methods 0.000 description 6
• 230000008313 sensitization Effects 0.000 description 6
• 150000003378 silver Chemical class 0.000 description 6
• 159000000000 sodium salts Chemical class 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
• 238000009835 boiling Methods 0.000 description 5
• 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 5
• 229910052751 metal Chemical group 0.000 description 5
• 239000002184 metal Chemical group 0.000 description 5
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 5
• 230000000269 nucleophilic effect Effects 0.000 description 5
• 238000007254 oxidation reaction Methods 0.000 description 5
• 229910052700 potassium Inorganic materials 0.000 description 5
• 239000011591 potassium Substances 0.000 description 5
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
• 230000008569 process Effects 0.000 description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
• 238000000859 sublimation Methods 0.000 description 5
• 230000008022 sublimation Effects 0.000 description 5
• 239000011593 sulfur Substances 0.000 description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
• 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 4
• DNMNQAUVYXEIKX-UHFFFAOYSA-N 2H-benzotriazol-4-ol silver Chemical compound [Ag].Oc1cccc2[nH]nnc12 DNMNQAUVYXEIKX-UHFFFAOYSA-N 0.000 description 4
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 4
• 108010010803 Gelatin Proteins 0.000 description 4
• 229960000583 acetic acid Drugs 0.000 description 4
• 239000000654 additive Substances 0.000 description 4
• 125000004429 atom Chemical group 0.000 description 4
• 238000000576 coating method Methods 0.000 description 4
• 229940125904 compound 1 Drugs 0.000 description 4
• 230000008878 coupling Effects 0.000 description 4
• 238000010168 coupling process Methods 0.000 description 4
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
• 229920000159 gelatin Polymers 0.000 description 4
• 239000008273 gelatin Substances 0.000 description 4
• 235000019322 gelatine Nutrition 0.000 description 4
• 235000011852 gelatine desserts Nutrition 0.000 description 4
• 239000012362 glacial acetic acid Substances 0.000 description 4
• 125000005647 linker group Chemical group 0.000 description 4
• 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
• 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 4
• 229920000642 polymer Polymers 0.000 description 4
• 238000007639 printing Methods 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
• 230000001235 sensitizing effect Effects 0.000 description 4
• 229910001961 silver nitrate Inorganic materials 0.000 description 4
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
• WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 3
• 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 3
• PLYFWZGSBMDRKW-UHFFFAOYSA-N 2h-benzotriazole-4-sulfonic acid;silver Chemical compound [Ag].OS(=O)(=O)C1=CC=CC2=NNN=C12 PLYFWZGSBMDRKW-UHFFFAOYSA-N 0.000 description 3
• BBGRQUUSRRKFSS-UHFFFAOYSA-N 5-nitro-2h-benzotriazole;silver Chemical compound [Ag].C1=C([N+](=O)[O-])C=CC2=NNN=C21 BBGRQUUSRRKFSS-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
• 150000008065 acid anhydrides Chemical class 0.000 description 3
• 125000002252 acyl group Chemical group 0.000 description 3
• 125000004442 acylamino group Chemical group 0.000 description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 3
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
• 229910052794 bromium Inorganic materials 0.000 description 3
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical group CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 229920002678 cellulose Polymers 0.000 description 3
• 239000000460 chlorine Substances 0.000 description 3
• 125000001309 chloro group Chemical group Cl* 0.000 description 3
• 229940125898 compound 5 Drugs 0.000 description 3
• PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
• 229910052737 gold Inorganic materials 0.000 description 3
• 239000010931 gold Substances 0.000 description 3
• 229910052736 halogen Inorganic materials 0.000 description 3
• 150000002367 halogens Chemical class 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 229910052742 iron Inorganic materials 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
• 150000007524 organic acids Chemical class 0.000 description 3
• 230000003647 oxidation Effects 0.000 description 3
• 238000005691 oxidative coupling reaction Methods 0.000 description 3
• 125000006678 phenoxycarbonyl group Chemical group 0.000 description 3
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
• 239000002244 precipitate Substances 0.000 description 3
• 230000001737 promoting effect Effects 0.000 description 3
• JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 3
• 230000009257 reactivity Effects 0.000 description 3
• 229910052708 sodium Inorganic materials 0.000 description 3
• 239000011734 sodium Substances 0.000 description 3
• 235000011121 sodium hydroxide Nutrition 0.000 description 3
• 230000003595 spectral effect Effects 0.000 description 3
• 239000003381 stabilizer Substances 0.000 description 3
• 229940124530 sulfonamide Drugs 0.000 description 3
• 125000003944 tolyl group Chemical group 0.000 description 3
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
• 125000006679 α-naphthoxycarbonyl group Chemical group 0.000 description 3
• VKGQPUZNCZPZKI-UHFFFAOYSA-N (diaminomethylideneamino)azanium;sulfate Chemical compound NN=C(N)N.NN=C(N)N.OS(O)(=O)=O VKGQPUZNCZPZKI-UHFFFAOYSA-N 0.000 description 2
• ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
• KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
• 125000006017 1-propenyl group Chemical group 0.000 description 2
• YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
• SGWZVZZVXOJRAQ-UHFFFAOYSA-N 2,6-Dimethyl-1,4-benzenediol Chemical compound CC1=CC(O)=CC(C)=C1O SGWZVZZVXOJRAQ-UHFFFAOYSA-N 0.000 description 2
• IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
• VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 2
• YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 2
• BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
• JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
• PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
• MLCZOHLVCQVKPI-UHFFFAOYSA-N 4-methyl-2h-benzotriazole;silver Chemical compound [Ag].CC1=CC=CC2=C1N=NN2 MLCZOHLVCQVKPI-UHFFFAOYSA-N 0.000 description 2
• UTMDJGPRCLQPBT-UHFFFAOYSA-N 4-nitro-1h-1,2,3-benzotriazole Chemical class [O-][N+](=O)C1=CC=CC2=NNN=C12 UTMDJGPRCLQPBT-UHFFFAOYSA-N 0.000 description 2
• XHQIJHOXQWEWNO-UHFFFAOYSA-N 4-nitro-2h-benzotriazole;silver Chemical compound [Ag].[O-][N+](=O)C1=CC=CC2=NNN=C12 XHQIJHOXQWEWNO-UHFFFAOYSA-N 0.000 description 2
• GDGIVSREGUOIJZ-UHFFFAOYSA-N 5-amino-3h-1,3,4-thiadiazole-2-thione Chemical compound NC1=NN=C(S)S1 GDGIVSREGUOIJZ-UHFFFAOYSA-N 0.000 description 2
• HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 2
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
• 229940126639 Compound 33 Drugs 0.000 description 2
• ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
• 239000001856 Ethyl cellulose Substances 0.000 description 2
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
• LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 2
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
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