KR101726060B1 - A composition for detection of hydrogen chloride gas comprising dipyrrole derivatives and metal salts and a color conversion sensor comprising the same - Google Patents
A composition for detection of hydrogen chloride gas comprising dipyrrole derivatives and metal salts and a color conversion sensor comprising the same Download PDFInfo
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- KR101726060B1 KR101726060B1 KR1020150106548A KR20150106548A KR101726060B1 KR 101726060 B1 KR101726060 B1 KR 101726060B1 KR 1020150106548 A KR1020150106548 A KR 1020150106548A KR 20150106548 A KR20150106548 A KR 20150106548A KR 101726060 B1 KR101726060 B1 KR 101726060B1
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- hydrogen chloride
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 44
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 229910000041 hydrogen chloride Inorganic materials 0.000 title claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 21
- 229910052751 metal Chemical class 0.000 title claims abstract description 20
- 239000002184 metal Chemical class 0.000 title claims abstract description 20
- 150000003839 salts Chemical class 0.000 title claims abstract description 18
- ULUNQYODBKLBOE-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)-1h-pyrrole Chemical class C1=CNC(C=2NC=CC=2)=C1 ULUNQYODBKLBOE-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 239000000203 mixture Substances 0.000 title claims description 29
- 239000007789 gas Substances 0.000 title abstract description 33
- 238000001514 detection method Methods 0.000 title description 7
- -1 nitro, amino, hydroxyl Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 239000000835 fiber Substances 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001449 anionic compounds Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 2
- 229910001412 inorganic anion Inorganic materials 0.000 claims description 2
- 150000002891 organic anions Chemical class 0.000 claims description 2
- 239000011148 porous material Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 150000001721 carbon Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000000975 dye Substances 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VDDITHMEGHCVEK-UHFFFAOYSA-N 1-[pyrrol-1-yl-(5-thiophen-2-ylthiophen-2-yl)methyl]pyrrole Chemical compound S1C(=CC=C1C(N1C=CC=C1)N1C=CC=C1)C=1SC=CC=1 VDDITHMEGHCVEK-UHFFFAOYSA-N 0.000 description 2
- QLCJBEVYVZAAHK-UHFFFAOYSA-N 2-[1H-pyrrol-2-yl-(5-thiophen-2-ylthiophen-2-yl)methyl]-1H-pyrrole Chemical compound S1C(=CC=C1C(C=1NC=CC=1)C=1NC=CC=1)C=1SC=CC=1 QLCJBEVYVZAAHK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910010293 ceramic material Inorganic materials 0.000 description 2
- 231100000481 chemical toxicant Toxicity 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000002341 toxic gas Substances 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- 0 *C(c1ccc[n]1*)c1ccc[n]1* Chemical compound *C(c1ccc[n]1*)c1ccc[n]1* 0.000 description 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 1
- QPQKUYVSJWQSDY-CCEZHUSRSA-N 4-(phenylazo)aniline Chemical compound C1=CC(N)=CC=C1\N=N\C1=CC=CC=C1 QPQKUYVSJWQSDY-CCEZHUSRSA-N 0.000 description 1
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 229920006221 acetate fiber Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 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
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
- G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators
- G01N31/223—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators for investigating presence of specific gases or aerosols
- G01N31/224—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators for investigating presence of specific gases or aerosols for investigating presence of dangerous gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
- G01N21/783—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour for analysing gases
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/0004—Gaseous mixtures, e.g. polluted air
- G01N33/0009—General constructional details of gas analysers, e.g. portable test equipment
- G01N33/0027—General constructional details of gas analysers, e.g. portable test equipment concerning the detector
- G01N33/0036—General constructional details of gas analysers, e.g. portable test equipment concerning the detector specially adapted to detect a particular component
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
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- Combustion & Propulsion (AREA)
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- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The present invention relates to a dye for detecting hydrogen chloride gas, which comprises a dipyrrole derivative represented by the following formula (I) and a metal salt represented by the following formula (II) And a color conversion sensor for detecting hydrogen chloride gas containing the same.
(I)
[Formula II]
Description
The present invention relates to a mixed dye composition capable of detecting hydrogen chloride gas, and more particularly, to a mixed dye composition capable of selectively detecting hydrogen chloride gas, including a dipyrrole derivative and a metal salt, And a color conversion sensor for detecting hydrogen chloride gas containing the same.
Recently, as the industrial structure and working environment have changed, the use of toxic chemicals has been increasing. As a result, the problems of the manufacture, use, and disposal of chemical substances are emerging throughout the industry, and the human body is exposed to the environment where chemical substances exist not only at the worksite but also through various routes. Nevertheless, there is a lack of development of sensors that can detect changes in work environment due to the use of toxic chemicals.
However, these sensors have limitations in detecting the present gaseous state, that is, the harmful gas in the gaseous phase, and in particular, they are not easily applied to the substrate such as paper or fiber, There is a problem that the action of changing the color according to the pH change is not visible to the naked eye.
There have been attempts to prepare novel dyes for the detection of acid, and in the prior art (Acta Crystallographica Section C Crystal structure Communications Volume 65, Part 10 (2009.10)), [4- (phenyldienyl) phenyldiazenyl) aniline] reacts with 5-sulfosalicylic acid or benzenesulfonic acid to form a dark red dye, and [4- (phenyldiazenyl) aniline] is reacted with 3,5-dinitrobenzoic acid and 1 : 2 non-mobile complexes. However, these structures only describe the color change due to bonding with a specific acidic compound, and it is difficult to say that these characteristics are characteristic of pH sensing.
Therefore, the present industry is equipped with an accident prevention system by installing a gas leak detection alarm against leakage of hydrogen chloride gas, and additionally, an infrared camera or CCTV is additionally installed and used. Such a gas leak detection device is a device that detects combustible or toxic gas and displays the concentration of the gas, and automatically alerts the user of the preset gas concentration. However, this was not enough for the immediate response of the field worker since the concentration should be higher than the allowable concentration. Furthermore, it causes a serious accident due to a malfunction or the like.
Therefore, it is necessary to research and develop a method which can selectively detect only hydrogen chloride gas even at a low concentration, and can detect by simple and easy method rather than a complicated sensing system.
The inventors of the present invention have continuously developed a chemical sensing method for hydrogen chloride and have developed a chemosensor capable of selectively detecting only a low concentration of hydrogen chloride gas and easily detecting at room temperature through color conversion , Which is provided in the present invention.
In order to solve the above problems, the present invention provides a composition for detecting hydrogen chloride, which comprises a dipyrrole derivative represented by the following formula (I) and a metal salt represented by the following formula (II) Hydrogen chloride is selectively detected.
(I)
[Formula II]
Specific structures and substituents of the above formulas (I) to (II) will be described later.
According to an embodiment of the present invention, the composition for detecting hydrogen chloride comprises a dipyrrole derivative represented by the formula (I) and a metal salt represented by the formula (II) in a weight ratio of 1: 1 to 1: . ≪ / RTI >
The present invention also provides a color conversion sensor comprising the composition for detecting hydrogen chloride, wherein the sensor is capable of detecting hydrogen chloride in gaseous state even at room temperature.
According to a preferred embodiment of the present invention, the color conversion sensor may be a paper sensor in which the porous paper substrate is coated with the composition for detecting hydrogen chloride gas, so that it can be easily detected by the naked eye without expensive equipment have.
The dye composition for detecting hydrogen chloride according to the present invention is characterized in that a metal salt is added to a dipyrrole derivative dye to selectively detect hydrogen chloride gas with excellent sensitivity through color change of gas hydrogen chloride, , It can be used as a hydrogen chloride gas sensor. Further, the dye composition for detection according to the present invention is excellent in selectivity, and can be synthesized in a large amount at low cost, so that it can be applied commercially.
1 is an NMR graph showing the synthesis of a dipyrrole derivative represented by the formula (I-1) according to the present invention.
Hereinafter, the present invention will be described in more detail.
The present invention relates to a dye composition capable of detecting only hydrogen chloride through color change using an organic dye comprising a dipyrrole derivative represented by the following formula (I) and a metal salt represented by the following formula (II) Particularly hydrogen chloride in a gaseous state can be selectively detected at room temperature with excellent sensitivity.
(I)
[Formula II]
In the above formulas (I) to (II)
R 1 to R 3 are the same or different from each other and each independently selected from the group consisting of hydrogen, deuterium, nitro, amino, hydroxyl, halogen, halide, carboxyl, aldehyde, ester, An unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.
R 4 to R 5 are selected from among hydrogen, deuterium, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 5 -C 20 aryl, and substituted or unsubstituted C 3 -C 20 heteroaryl .
According to a preferred embodiment of the present invention, R 1 to R 5 are each independently selected from the group consisting of hydrogen, deuterium, nitro, amino, hydroxyl, halogen, halide, carboxyl, aldehyde, Ketone group and the like and may be an alkyl group such as methyl, ethyl, propyl, butyl, isopropyl or tertbutyl, and may also be a thiophene, bithiophene, pyridine, phenyl, biphenyl, naphthyl, anthracenyl Or a heteroaryl group.
Each of R 1 to R 5 may be further substituted with one or more substituents. The substituent may be substituted with at least one substituent selected from the group consisting of deuterium, a nitro group, an amino group, a hydroxyl group, a halogen group, a halide group, a carboxyl group, A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, and a substituted or unsubstituted C3 to C20 heteroaryl group. .
Me may be an alkali metal such as lithium, sodium or potassium or a transition metal such as titanium, chromium, manganese, iron, nickel, copper, zinc, zirconium, molybdenum, palladium, silver, cadmium, platinum, They may be modified with metals such as aluminum, gallium, indium, and tin, respectively.
X - is an organic or inorganic anion, and is not particularly limited, but is preferably a halide ion such as fluoride, chloride, bromide, or iodide, or a halide ion such as acetate, phosphate, hydro- phosphite, nitrate, carbonate, bicarbonate, Oxalate, hydroxide, dodecyl sulfate, hydrogensulfate, tetrafluoroborate, hexafluoroacetate, and the like.
According to an embodiment of the present invention, the dipyrrole derivative represented by the formula (I) and the metal salt represented by the formula (II) may be mixed in a ratio of 1: 1 to 1: 100 have.
In addition, although the scope of the present invention is not limited in this regard, the dipyrrol derivative represented by the above-mentioned formula (I) may be represented by the following formula (I-1) The metal salt represented by the above formula (II) may be represented by the following formula (II-1).
[I-1]
[II-1]
Another aspect of the present invention relates to a color conversion sensor comprising the composition for detecting hydrogen chloride, and more particularly, to a color conversion sensor characterized by detecting gaseous hydrogen chloride at room temperature.
The color conversion sensor according to the present invention may be composed of a system in which a dipyrrole derivative dye and a metal salt are mixed in an appropriate ratio, dissolved in a solvent, and then applied to a porous substrate to react with gaseous hydrogen chloride gas.
At this time, the dye and salt mixture applied to the substrate has a dried film or powder state, and this whole system can be regarded as a color conversion sensor system. In other words, it can be applied in various array form or various kit form, but it is coated on a porous substrate such as ceramic material, fiber, paper, etc. without requiring complicated and expensive equipment and is applied as a film sensor or a paper sensor .
The porous substrate may be a porous fiber such as a polyester fiber, a nylon fiber, an acetate fiber, an acrylic fiber, a polypropylene fiber, and a polyethylene fiber, as long as it is a porous material such as a porous ceramic material or a paper.
Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are intended to illustrate the invention and are not intended to limit the scope of the invention.
Synthesis Example 1: Synthesis of Dipyrrole Derivative Dyes According to the Present Invention
2,2 '- ([2,2'-bithiophen] -5-ylmethylene) bis (1H-pyrrole) according to the present invention was synthesized according to the following reaction formula.
[Reaction Scheme]
[I-1]
Example 1: Composition for detecting hydrogen chloride gas
(2,2'-bithiophen-5-ylmethylene) bis (1H-pyrrole) synthesized according to Synthesis Example 1 and Copper (I) iodide were mixed in a weight ratio of 1: A total of 2 mg of the mixture was dissolved in 0.5 mL of acetonitrile to prepare a composition for detecting hydrogen chloride gas according to the present invention.
Comparative Example 1
(2,2'-bithiophen-5-ylmethylene) bis (1H-pyrrole) synthesized in Synthesis Example 1 but not containing Copper (I) iodide, 2 mg of the dye was dissolved in 0.5 mL of acetonitrile to prepare a composition.
Experimental Example 1: Detection of color change of an acid / base gas of the composition of Example 1 and Comparative Example 1
(1) The solution of the composition of Comparative Example 1 was spotted on a porous paper and then dried to remove the solvent. At this time, as shown in Table 1, it was brown.
The reaction mixture was allowed to react in a gaseous state for 1 minute while flowing HFP, HCl and ammonia gas at a concentration of 100 ppm. Thereafter, the reaction vessel was evacuated with inert gas nitrogen and the sample was taken out of the reaction vessel to confirm the color change.
As shown in [Table 1], when the color conversion detection of the gas state was confirmed on the porous paper using the composition of Comparative Example 1 which does not include the metal salt, the color change was slightly different for all the gases, There was no selective response.
(2) The solution of the composition of Example 1 was spotted on a porous paper, followed by drying to remove the solvent. At this time, as shown in the following Table 2, it was almost colorless.
The reaction mixture was allowed to react in a gaseous state for 1 minute while flowing HFP, HCl and ammonia gas at a concentration of 100 ppm. Thereafter, the reaction vessel was evacuated with inert gas nitrogen and the sample was taken out of the reaction vessel to confirm the color change.
As can be seen from Table 2, HF, HCl acid gas and base ammonia gas showed color change which can be visually confirmed. However, as compared with HF and ammonia gas, only hydrogen chloride gas was selectively colorless to purple It was confirmed that the color difference of the HF, which is the same acidic gas, was significantly changed even though there was almost no color change.
That is, in the case of the composition comprising the pyrrole derivative dye according to the present invention in which the metal salt is mixed, it is possible to selectively detect the color change only with respect to the hydrogen chloride gas.
As described above, the present invention relates to a dye composition for a color conversion sensor capable of detecting the outflow of harmful gas hydrogen chloride through color change without complicated equipment, and is capable of detecting selectivity for a specific gas not possessed by a dye by various metal salts And the selectivity is imparted by the addition. Hydrogen chloride gas corresponding to noxious gas can be effectively detected through the dye composition having such high selectivity and the color conversion sensor including the dye composition.
Claims (8)
(I)
[Formula II]
In the above formulas (I) to (II)
R 1 to R 3 are the same or different from each other and each independently selected from the group consisting of hydrogen, deuterium, nitro, amino, hydroxyl, halogen, halide, carboxyl, aldehyde, ester, A substituted or unsubstituted aryl group having 5 to 20 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms,
R 4 to R 5 are the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms and a substituted or unsubstituted carbon number 3 to 20 heteroaryl groups,
Me is an alkali metal or a transition metal, and the alkali metal or transition metal may be modified with a metal selected from aluminum, gallium, indium and tin,
X - is an organic or inorganic anion,
The pyrrole derivative represented by the above formula (I) and the metal salt represented by the above-mentioned formula (II) are mixed in a ratio (molar ratio) of 1: 1 to 1: 100.
Wherein each of R 1 to R 5 may be further substituted with at least one substituent, and the at least one substituent is selected from the group consisting of deuterium, nitro, amino, hydroxyl, halogen, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms. / RTI >
Wherein the composition for detecting hydrogen chloride is capable of detecting hydrogen chloride in a gaseous state.
The dipyrrole derivative represented by the above-mentioned formula (I) is characterized in that it is represented by the following formula (I-1), and the metal salt represented by the above formula (II) Composition:
[I-1]
[II-1]
Wherein the sensor detects gaseous hydrogen chloride.
Wherein the substrate is a porous material, and is a porous paper or a porous fiber.
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