DE2258452A1

DE2258452A1 - Photographisches aufzeichnungsmaterial

Photographisches aufzeichnungsmaterial

Info

Publication number: DE2258452A1
Authority: DE; Germany
Prior art keywords: salt; isoindolium; recording material; material according; phosphine
Prior art date: 1971-12-02
Legal status : Pending

Application number

DE19722258452

Other languages

German (de)

English (en)

Inventor

George Arthur Reynolds

Current Assignee

Eastman Kodak Co

Original Assignee

Eastman Kodak Co

Priority date

1971-12-02

Filing date

1972-11-29

Publication date

1973-06-07

1972-11-29 Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co

1973-06-07 Publication of DE2258452A1 publication Critical patent/DE2258452A1/de

Status Pending legal-status Critical Current

Links

239000000463 material Substances 0.000 title claims description 98
-1 nitro, amino Chemical group 0.000 claims description 81
230000005855 radiation Effects 0.000 claims description 33
150000001540 azides Chemical class 0.000 claims description 31
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 29
150000001875 compounds Chemical class 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 26
238000004519 manufacturing process Methods 0.000 claims description 18
239000002243 precursor Substances 0.000 claims description 18
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 15
239000011230 binding agent Substances 0.000 claims description 11
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
230000003213 activating effect Effects 0.000 claims description 6
150000001450 anions Chemical class 0.000 claims description 6
229910052698 phosphorus Inorganic materials 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
150000004714 phosphonium salts Chemical group 0.000 claims description 5
UZEFHQIOSJWWSB-UHFFFAOYSA-N 4-azidobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(N=[N+]=[N-])C=C1 UZEFHQIOSJWWSB-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
238000006303 photolysis reaction Methods 0.000 claims description 4
230000015843 photosynthesis, light reaction Effects 0.000 claims description 4
DOXPTTBJQKIAQV-UHFFFAOYSA-N 4-(4-azidophenyl)morpholine Chemical compound C1=CC(N=[N+]=[N-])=CC=C1N1CCOCC1 DOXPTTBJQKIAQV-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 2
RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 claims description 2
LFNXCUNDYSYVJY-UHFFFAOYSA-N tris(3-methylphenyl)phosphane Chemical compound CC1=CC=CC(P(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 LFNXCUNDYSYVJY-UHFFFAOYSA-N 0.000 claims description 2
UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 claims description 2
WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 claims description 2
XMRHPDUAHFDSOH-UHFFFAOYSA-N (3-oxocyclohexyl)-triphenylphosphanium Chemical group C1C(=O)CCCC1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XMRHPDUAHFDSOH-UHFFFAOYSA-N 0.000 claims 1
FLDWQHRSHIHUKE-UHFFFAOYSA-N 1,2-bis(diphenylphosphanyl)ethanol Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(O)CP(C=1C=CC=CC=1)C1=CC=CC=C1 FLDWQHRSHIHUKE-UHFFFAOYSA-N 0.000 claims 1
CWHFCSKEIGMGLP-UHFFFAOYSA-N 1-(4-azidophenyl)sulfonylpyrrolidine-2,5-dione Chemical compound N(=[N+]=[N-])C1=CC=C(C=C1)S(=O)(=O)N1C(CCC1=O)=O CWHFCSKEIGMGLP-UHFFFAOYSA-N 0.000 claims 1
VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical class C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims 1
JOSGORFOUUUAHY-UHFFFAOYSA-N 5-(4-azidophenyl)-2-phenyl-1,3-oxazole Chemical compound C1(=CC=CC=C1)C=1OC(=CN1)C1=CC=C(C=C1)N=[N+]=[N-] JOSGORFOUUUAHY-UHFFFAOYSA-N 0.000 claims 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
230000000087 stabilizing effect Effects 0.000 claims 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
IQKSLJOIKWOGIZ-UHFFFAOYSA-N tris(4-chlorophenyl)phosphane Chemical compound C1=CC(Cl)=CC=C1P(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 IQKSLJOIKWOGIZ-UHFFFAOYSA-N 0.000 claims 1
239000000975 dye Substances 0.000 description 14
238000000576 coating method Methods 0.000 description 13
238000000034 method Methods 0.000 description 13
BWCCVIRGUMYIHE-UHFFFAOYSA-N phosphane;azide Chemical class P.[N-]=[N+]=[N-] BWCCVIRGUMYIHE-UHFFFAOYSA-N 0.000 description 13
239000011248 coating agent Substances 0.000 description 12
150000003254 radicals Chemical class 0.000 description 12
239000000243 solution Substances 0.000 description 12
238000010438 heat treatment Methods 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
229920001577 copolymer Polymers 0.000 description 8
230000008569 process Effects 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
UOVVGTYACLGOIL-UHFFFAOYSA-N 1-azido-4-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=C(N=[N+]=[N-])C2=C1 UOVVGTYACLGOIL-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
150000005840 aryl radicals Chemical class 0.000 description 5
230000035945 sensitivity Effects 0.000 description 5
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
229920002678 cellulose Polymers 0.000 description 4
239000012954 diazonium Substances 0.000 description 4
150000001989 diazonium salts Chemical class 0.000 description 4
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
230000006641 stabilisation Effects 0.000 description 4
238000011105 stabilization Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000004913 activation Effects 0.000 description 3
229920006217 cellulose acetate butyrate Polymers 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000000047 product Substances 0.000 description 3
230000004044 response Effects 0.000 description 3
230000003595 spectral effect Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
231100000331 toxic Toxicity 0.000 description 3
230000002588 toxic effect Effects 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
229920002284 Cellulose triacetate Polymers 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000001045 blue dye Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002301 cellulose acetate Polymers 0.000 description 2
230000000536 complexating effect Effects 0.000 description 2
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
CTRLRINCMYICJO-UHFFFAOYSA-N phenyl azide Chemical class [N-]=[N+]=NC1=CC=CC=C1 CTRLRINCMYICJO-UHFFFAOYSA-N 0.000 description 2
239000003504 photosensitizing agent Substances 0.000 description 2
229920013639 polyalphaolefin Polymers 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
229920001155 polypropylene Polymers 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
229920001897 terpolymer Polymers 0.000 description 2
YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
YQPDFPOALLAYGO-YDWXAUTNSA-N (1e,4e)-1,5-bis(4-azidophenyl)penta-1,4-dien-3-one Chemical compound C1=CC(N=[N+]=[N-])=CC=C1\C=C\C(=O)\C=C\C1=CC=C(N=[N+]=[N-])C=C1 YQPDFPOALLAYGO-YDWXAUTNSA-N 0.000 description 1
XPCUBQRMSPSPFN-UHFFFAOYSA-M (2-methyl-3-oxocyclohexyl)-tris(4-methylphenyl)phosphanium perchlorate Chemical compound Cl(=O)(=O)(=O)[O-].CC1C(CCCC1[P+](C1=CC=C(C=C1)C)(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)=O XPCUBQRMSPSPFN-UHFFFAOYSA-M 0.000 description 1
PDKQLALBHNRWDW-UHFFFAOYSA-M (3-oxocyclohexyl)-triphenylphosphanium chloride Chemical compound [Cl-].C1(CC(CCC1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O PDKQLALBHNRWDW-UHFFFAOYSA-M 0.000 description 1
BCNMNYUNSFNSSG-UHFFFAOYSA-N (4-azidophenyl)-phenylmethanone Chemical compound C1=CC(N=[N+]=[N-])=CC=C1C(=O)C1=CC=CC=C1 BCNMNYUNSFNSSG-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
DZLDWCMSPUTQJF-UHFFFAOYSA-N 1-(4-azidophenyl)-N-(4-chlorophenyl)methanimine Chemical compound N(=[N+]=[N-])C1=CC=C(C=NC2=CC=C(C=C2)Cl)C=C1 DZLDWCMSPUTQJF-UHFFFAOYSA-N 0.000 description 1
FKZLDVQRXHDCRS-UHFFFAOYSA-N 1-azido-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N=[N+]=[N-] FKZLDVQRXHDCRS-UHFFFAOYSA-N 0.000 description 1
XIZZMTXTYPGJSL-UHFFFAOYSA-N 1-azido-4-(hexoxymethyl)benzene Chemical compound C(CCCCC)OCC1=CC=C(C=C1)N=[N+]=[N-] XIZZMTXTYPGJSL-UHFFFAOYSA-N 0.000 description 1
SGDQVLYEAQRXDR-UHFFFAOYSA-N 1-azido-4-ethoxybenzene Chemical compound CCOC1=CC=C(N=[N+]=[N-])C=C1 SGDQVLYEAQRXDR-UHFFFAOYSA-N 0.000 description 1
HYISGPFBRUIUNB-UHFFFAOYSA-N 1-azidonaphthalene Chemical compound C1=CC=C2C(N=[N+]=[N-])=CC=CC2=C1 HYISGPFBRUIUNB-UHFFFAOYSA-N 0.000 description 1
FQXGHZNSUOHCLO-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1,3-cyclobutanediol Chemical compound CC1(C)C(O)C(C)(C)C1O FQXGHZNSUOHCLO-UHFFFAOYSA-N 0.000 description 1
QWWLQHYCSMVQFN-UHFFFAOYSA-N 2,3-dihydroxypropyl 4-azidobenzoate Chemical compound N(=[N+]=[N-])C1=CC=C(C(=O)OCC(O)CO)C=C1 QWWLQHYCSMVQFN-UHFFFAOYSA-N 0.000 description 1
JVSVWJWXWXUZJS-UHFFFAOYSA-N 2,5-bis(4-azidophenyl)-3H-oxadiazole Chemical compound N(=[N+]=[N-])C1=CC=C(C=C1)N1OC(=CN1)C1=CC=C(C=C1)N=[N+]=[N-] JVSVWJWXWXUZJS-UHFFFAOYSA-N 0.000 description 1
XDWRJMPZRBQXEF-UHFFFAOYSA-N 2-(4-azidophenyl)-5-phenyl-1,3-oxazole Chemical compound N(=[N+]=[N-])C1=CC=C(C=C1)C=1OC(=CN1)C1=CC=CC=C1 XDWRJMPZRBQXEF-UHFFFAOYSA-N 0.000 description 1
DCDLXRUGKUKJGT-UHFFFAOYSA-N 2-(4-azidophenyl)-6-methyl-1,3-benzothiazole Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N=[N+]=[N-])C=C1 DCDLXRUGKUKJGT-UHFFFAOYSA-N 0.000 description 1
IPUMVXGZEXYYKJ-UHFFFAOYSA-N 2-azido-1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=C(N=[N+]=[N-])C(Br)=C1 IPUMVXGZEXYYKJ-UHFFFAOYSA-N 0.000 description 1
YZZPXUJOEKTGLM-UHFFFAOYSA-N 2-azidonaphthalene Chemical class C1=CC=CC2=CC(N=[N+]=[N-])=CC=C21 YZZPXUJOEKTGLM-UHFFFAOYSA-N 0.000 description 1
IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
QPMACMZAHRVTCJ-UHFFFAOYSA-N 2H-isoindol-2-ium perchlorate Chemical compound [O-][Cl](=O)(=O)=O.[NH2+]1C=c2ccccc2=C1 QPMACMZAHRVTCJ-UHFFFAOYSA-N 0.000 description 1
DZPGXGGVNNQBGZ-UHFFFAOYSA-N 2h-isoindole;hydrochloride Chemical compound Cl.C1=CC=CC2=CNC=C21 DZPGXGGVNNQBGZ-UHFFFAOYSA-N 0.000 description 1
HGYDVAFUAGJNCB-UHFFFAOYSA-N 3-azidobenzenesulfonamide 2-azidofluoren-9-one Chemical compound N(=[N+]=[N-])C1=CC=2C(C3=CC=CC=C3C2C=C1)=O.N(=[N+]=[N-])C=1C=C(C=CC1)S(=O)(=O)N HGYDVAFUAGJNCB-UHFFFAOYSA-N 0.000 description 1
XBYIWVXXQSZTFY-UHFFFAOYSA-N 3-azidobenzoic acid Chemical compound OC(=O)C1=CC=CC(N=[N+]=[N-])=C1 XBYIWVXXQSZTFY-UHFFFAOYSA-N 0.000 description 1
OXMKHJYMSGIUBV-UHFFFAOYSA-N 4-(4-azido-2-methoxyphenyl)morpholine Chemical compound N(=[N+]=[N-])C1=CC(=C(C=C1)N1CCOCC1)OC OXMKHJYMSGIUBV-UHFFFAOYSA-N 0.000 description 1
LVOCUUFXGPZXBH-UHFFFAOYSA-N 4-(4-azido-3-methoxyphenyl)morpholine Chemical compound N(=[N+]=[N-])C1=C(C=C(C=C1)N1CCOCC1)OC LVOCUUFXGPZXBH-UHFFFAOYSA-N 0.000 description 1
DKXMGJYWTGCBIW-UHFFFAOYSA-M 4-[2-(4-azidophenyl)ethenyl]-1-methyl-2,6-diphenylpyridin-1-ium perchlorate Chemical compound Cl(=O)(=O)(=O)[O-].C[N+]1=C(C=C(C=C1C1=CC=CC=C1)C=CC1=CC=C(C=C1)N=[N+]=[N-])C1=CC=CC=C1 DKXMGJYWTGCBIW-UHFFFAOYSA-M 0.000 description 1
DPHXRSQRSGVLNX-UHFFFAOYSA-N 4-azido-2-chloro-N,N-diethylaniline Chemical compound C(C)N(C1=C(C=C(C=C1)N=[N+]=[N-])Cl)CC DPHXRSQRSGVLNX-UHFFFAOYSA-N 0.000 description 1
VJWRRATVLQNNTI-UHFFFAOYSA-N 4-azido-4-methyl-N-phenylcyclohexa-1,5-diene-1-carboxamide Chemical compound CC1(CC=C(C(=O)NC2=CC=CC=C2)C=C1)N=[N+]=[N-] VJWRRATVLQNNTI-UHFFFAOYSA-N 0.000 description 1
MLYGBJUZQXAFHZ-UHFFFAOYSA-N 4-azido-N-(2,6-dimethylphenyl)benzamide Chemical compound CC1=C(C(=CC=C1)C)NC(C1=CC=C(C=C1)N=[N+]=[N-])=O MLYGBJUZQXAFHZ-UHFFFAOYSA-N 0.000 description 1
VHJUSNJVFVQBBE-UHFFFAOYSA-N 4-azido-n-naphthalen-1-ylbenzamide Chemical compound C1=CC(N=[N+]=[N-])=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 VHJUSNJVFVQBBE-UHFFFAOYSA-N 0.000 description 1
ZKCVIWAHVMYDIM-UHFFFAOYSA-N 4-azidobenzamide Chemical compound NC(=O)C1=CC=C(N=[N+]=[N-])C=C1 ZKCVIWAHVMYDIM-UHFFFAOYSA-N 0.000 description 1
PQXPAFTXDVNANI-UHFFFAOYSA-N 4-azidobenzoic acid Chemical compound OC(=O)C1=CC=C(N=[N+]=[N-])C=C1 PQXPAFTXDVNANI-UHFFFAOYSA-N 0.000 description 1
YURUKVUJGYBZDU-UHFFFAOYSA-N 4-azidobenzonitrile Chemical compound [N-]=[N+]=NC1=CC=C(C#N)C=C1 YURUKVUJGYBZDU-UHFFFAOYSA-N 0.000 description 1
LGWXBHNBDLTXFM-UHFFFAOYSA-N 5-azido-2-methoxybenzonitrile Chemical compound N(=[N+]=[N-])C1=CC(=C(C=C1)OC)C#N LGWXBHNBDLTXFM-UHFFFAOYSA-N 0.000 description 1
CPMFRNOJQBSXRL-UHFFFAOYSA-N 5-azido-2-morpholin-4-ylbenzonitrile Chemical compound N(=[N+]=[N-])C1=CC(=C(C=C1)N1CCOCC1)C#N CPMFRNOJQBSXRL-UHFFFAOYSA-N 0.000 description 1
OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical class C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
FOBKYNDTXHCQBK-UHFFFAOYSA-M CC(C=C1)=CC=C1[P+](C(CC(C1=CC=CC=C1)=O)C1=CC=CC=C1)(C1=CC=C(C)C=C1)C1=CC=C(C)C=C1.[Cl-] Chemical compound CC(C=C1)=CC=C1[P+](C(CC(C1=CC=CC=C1)=O)C1=CC=CC=C1)(C1=CC=C(C)C=C1)C1=CC=C(C)C=C1.[Cl-] FOBKYNDTXHCQBK-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
QWJQBHZEGQKXCC-UHFFFAOYSA-M Cl(=O)(=O)(=O)[O-].C[N+]1=C(C=C(C=C1C1=CC=CC=C1)C1=CC=C(C=C1)N=[N+]=[N-])C1=CC=CC=C1 Chemical compound Cl(=O)(=O)(=O)[O-].C[N+]1=C(C=C(C=C1C1=CC=CC=C1)C1=CC=C(C=C1)N=[N+]=[N-])C1=CC=CC=C1 QWJQBHZEGQKXCC-UHFFFAOYSA-M 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
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 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
241001082241 Lythrum hyssopifolia Species 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
UCUZZGDZDHGMSK-UHFFFAOYSA-N N(=[N+]=[N-])C1=CC=C(C(=O)OCCCO)C=C1 Chemical compound N(=[N+]=[N-])C1=CC=C(C(=O)OCCCO)C=C1 UCUZZGDZDHGMSK-UHFFFAOYSA-N 0.000 description 1
229920001328 Polyvinylidene chloride Polymers 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
DCVGVWVHEPVPJT-UHFFFAOYSA-N [Br-].C=1[NH2+]C=C2C=CC=CC=12 Chemical compound [Br-].C=1[NH2+]C=C2C=CC=CC=12 DCVGVWVHEPVPJT-UHFFFAOYSA-N 0.000 description 1
PSXAEUJKMVCIKV-UHFFFAOYSA-N [N-]=[N+]=NC(C=C1)=CC(C2=CC(O)=CC3=CC=CC=C23)=C1C(O)=O Chemical compound [N-]=[N+]=NC(C=C1)=CC(C2=CC(O)=CC3=CC=CC=C23)=C1C(O)=O PSXAEUJKMVCIKV-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000009471 action Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000005250 alkyl acrylate group Chemical group 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000003321 amplification Effects 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
239000000987 azo dye Substances 0.000 description 1
229950011260 betanaphthol Drugs 0.000 description 1
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
230000001680 brushing 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
OSPMKIFLYSESOG-UHFFFAOYSA-N butyl(dimethoxy)phosphane Chemical compound CCCCP(OC)OC OSPMKIFLYSESOG-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
229920001727 cellulose butyrate Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000009918 complex formation Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
125000004986 diarylamino group Chemical group 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000005670 electromagnetic radiation Effects 0.000 description 1
RUFXXUICVBVRCX-UHFFFAOYSA-N ethyl 2-azidobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1N=[N+]=[N-] RUFXXUICVBVRCX-UHFFFAOYSA-N 0.000 description 1
CDFRXIVAGKDWGY-UHFFFAOYSA-N ethyl 4-azidobenzoate Chemical compound CCOC(=O)C1=CC=C(N=[N+]=[N-])C=C1 CDFRXIVAGKDWGY-UHFFFAOYSA-N 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
229920001600 hydrophobic polymer Polymers 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
238000007654 immersion Methods 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000000976 ink Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 1
LIXGZTMJRCYCFX-UHFFFAOYSA-N n-bis(n-phenylanilino)phosphanyl-n-phenylaniline Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)P(N(C=1C=CC=CC=1)C=1C=CC=CC=1)N(C=1C=CC=CC=1)C1=CC=CC=C1 LIXGZTMJRCYCFX-UHFFFAOYSA-N 0.000 description 1
JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
238000003199 nucleic acid amplification method Methods 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
238000010422 painting Methods 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
PIJRLNIZKMOPGM-UHFFFAOYSA-N phenyl 4-azidobenzoate Chemical compound N(=[N+]=[N-])C1=CC=C(C(=O)OC2=CC=CC=C2)C=C1 PIJRLNIZKMOPGM-UHFFFAOYSA-N 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
229920003213 poly(N-isopropyl acrylamide) Polymers 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000139 polyethylene terephthalate Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
JAOZKJMVYIWLKU-UHFFFAOYSA-N sodium 7-hydroxy-8-[(4-sulfonaphthalen-1-yl)diazenyl]naphthalene-1,3-disulfonic acid Chemical compound C1=CC=C2C(=C1)C(=CC=C2S(=O)(=O)O)N=NC3=C(C=CC4=CC(=CC(=C43)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] JAOZKJMVYIWLKU-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
GETTZEONDQJALK-UHFFFAOYSA-N trifluorotoluene Substances FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1