JP2004075986A

JP2004075986A - フタロシアニン化合物、これを含むインク、インクジェット記録方法、および画像形成方法

フタロシアニン化合物、これを含むインク、インクジェット記録方法、および画像形成方法 Download PDF

Info

Publication number: JP2004075986A
Authority: JP; Japan
Prior art keywords: group; ring; rings; substituent; ink
Prior art date: 2002-06-19
Legal status : Abandoned

Application number

JP2003167896A

Other languages

English (en)

Japanese (ja)

Other versions

JP2004075986A5 (enExample

Inventor

Keiichi Tateishi

立石　桂一

Yoshiharu Yabuki

矢吹　嘉治

Shigeaki Tanaka

田中　成明

Current Assignee

Fujifilm Holdings Corp

Original Assignee

Fuji Photo Film Co Ltd

Priority date

2002-06-19

Filing date

2003-06-12

Publication date

2004-03-11

2003-06-12 Application filed by Fuji Photo Film Co Ltd filed Critical Fuji Photo Film Co Ltd

2003-06-12 Priority to JP2003167896A priority Critical patent/JP2004075986A/ja

2004-03-11 Publication of JP2004075986A publication Critical patent/JP2004075986A/ja

2007-04-26 Publication of JP2004075986A5 publication Critical patent/JP2004075986A5/ja

Status Abandoned legal-status Critical Current

Links

-1 Phthalocyanine compound Chemical class 0.000 title claims abstract description 242
238000000034 method Methods 0.000 title claims abstract description 55
125000001424 substituent group Chemical group 0.000 claims abstract description 203
125000003118 aryl group Chemical group 0.000 claims abstract description 60
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 42
229910052799 carbon Inorganic materials 0.000 claims abstract description 42
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 33
125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 31
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 30
229910052751 metal Inorganic materials 0.000 claims abstract description 24
229910044991 metal oxide Inorganic materials 0.000 claims abstract description 7
150000004706 metal oxides Chemical class 0.000 claims abstract description 7
229910000000 metal hydroxide Inorganic materials 0.000 claims abstract description 6
150000004692 metal hydroxides Chemical class 0.000 claims abstract description 6
229910001507 metal halide Inorganic materials 0.000 claims abstract description 5
150000005309 metal halides Chemical class 0.000 claims abstract description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 46
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 40
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 33
239000000463 material Substances 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 25
239000002184 metal Substances 0.000 claims description 23
125000003710 aryl alkyl group Chemical group 0.000 claims description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
125000000753 cycloalkyl group Chemical group 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 13
125000004429 atom Chemical group 0.000 claims description 13
150000001721 carbon Chemical group 0.000 claims description 10
125000000304 alkynyl group Chemical group 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
239000001023 inorganic pigment Substances 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 5
239000002245 particle Substances 0.000 claims description 4
229910052698 phosphorus Inorganic materials 0.000 claims description 4
125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 3
125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 3
125000004437 phosphorous atom Chemical group 0.000 claims description 3
239000000203 mixture Substances 0.000 abstract description 43
125000004432 carbon atom Chemical group C* 0.000 abstract description 42
125000005842 heteroatom Chemical group 0.000 abstract description 9
239000000976 ink Substances 0.000 description 186
239000000975 dye Substances 0.000 description 101
150000001875 compounds Chemical class 0.000 description 91
239000007789 gas Substances 0.000 description 55
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 46
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 42
238000007254 oxidation reaction Methods 0.000 description 40
230000003647 oxidation Effects 0.000 description 39
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
239000000123 paper Substances 0.000 description 34
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 32
230000015572 biosynthetic process Effects 0.000 description 29
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 29
238000003756 stirring Methods 0.000 description 29
238000003860 storage Methods 0.000 description 29
238000003786 synthesis reaction Methods 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 25
239000000243 solution Substances 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 23
150000007524 organic acids Chemical class 0.000 description 23
239000000049 pigment Substances 0.000 description 23
239000013078 crystal Substances 0.000 description 22
229920000642 polymer Polymers 0.000 description 19
239000003795 chemical substances by application Substances 0.000 description 18
239000007788 liquid Substances 0.000 description 17
RZVCEPSDYHAHLX-UHFFFAOYSA-N 3-iminoisoindol-1-amine Chemical class C1=CC=C2C(N)=NC(=N)C2=C1 RZVCEPSDYHAHLX-UHFFFAOYSA-N 0.000 description 16
239000002253 acid Substances 0.000 description 16
238000001816 cooling Methods 0.000 description 16
HGVNXEVNBBVJGZ-UHFFFAOYSA-N O1C2=C(N(C3=CC=CC=C13)C1=CC=C(C3=CC(C#N)=C(C#N)C=C3C3=CC=C(N4C5=CC=CC=C5OC5=C4C=CC=C5)C=C3)C=C1)C=CC=C2 Chemical class O1C2=C(N(C3=CC=CC=C13)C1=CC=C(C3=CC(C#N)=C(C#N)C=C3C3=CC=C(N4C5=CC=CC=C5OC5=C4C=CC=C5)C=C3)C=C1)C=CC=C2 HGVNXEVNBBVJGZ-UHFFFAOYSA-N 0.000 description 15
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 15
239000001007 phthalocyanine dye Substances 0.000 description 15
150000003839 salts Chemical class 0.000 description 15
239000007864 aqueous solution Substances 0.000 description 14
239000000047 product Substances 0.000 description 14
125000003545 alkoxy group Chemical group 0.000 description 13
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 13
229940093915 gynecological organic acid Drugs 0.000 description 13
235000005985 organic acids Nutrition 0.000 description 13
239000002904 solvent Substances 0.000 description 13
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000006185 dispersion Substances 0.000 description 12
238000004519 manufacturing process Methods 0.000 description 12
239000003960 organic solvent Substances 0.000 description 12
238000007639 printing Methods 0.000 description 12
238000010521 absorption reaction Methods 0.000 description 11
239000000654 additive Substances 0.000 description 11
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 11
125000002252 acyl group Chemical group 0.000 description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 10
239000010949 copper Substances 0.000 description 10
125000005843 halogen group Chemical group 0.000 description 10
150000002500 ions Chemical class 0.000 description 10
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
230000001590 oxidative effect Effects 0.000 description 10
229920005989 resin Polymers 0.000 description 10
239000011347 resin Substances 0.000 description 10
239000007787 solid Substances 0.000 description 10
239000000126 substance Substances 0.000 description 10
239000004094 surface-active agent Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
235000011054 acetic acid Nutrition 0.000 description 9
125000003282 alkyl amino group Chemical group 0.000 description 9
239000002585 base Substances 0.000 description 9
238000011156 evaluation Methods 0.000 description 9
238000005562 fading Methods 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
239000004816 latex Substances 0.000 description 9
229920000126 latex Polymers 0.000 description 9
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 9
238000006467 substitution reaction Methods 0.000 description 9
229910052725 zinc Inorganic materials 0.000 description 9
239000011701 zinc Substances 0.000 description 9
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
125000004423 acyloxy group Chemical group 0.000 description 8
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 8
125000004414 alkyl thio group Chemical group 0.000 description 8
239000012736 aqueous medium Substances 0.000 description 8
125000001769 aryl amino group Chemical group 0.000 description 8
125000005162 aryl oxy carbonyl amino group Chemical group 0.000 description 8
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 8
125000005110 aryl thio group Chemical group 0.000 description 8
125000004104 aryloxy group Chemical group 0.000 description 8
230000000740 bleeding effect Effects 0.000 description 8
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 8
238000002425 crystallisation Methods 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
125000005462 imide group Chemical group 0.000 description 8
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
229910052759 nickel Inorganic materials 0.000 description 8
125000000565 sulfonamide group Chemical group 0.000 description 8
125000004149 thio group Chemical group *S* 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
239000004372 Polyvinyl alcohol Substances 0.000 description 7
229910001413 alkali metal ion Inorganic materials 0.000 description 7
239000011230 binding agent Substances 0.000 description 7
125000002091 cationic group Chemical group 0.000 description 7
230000000052 comparative effect Effects 0.000 description 7
229910052802 copper Inorganic materials 0.000 description 7
125000004093 cyano group Chemical group *C#N 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
230000007774 longterm Effects 0.000 description 7
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
229920002451 polyvinyl alcohol Polymers 0.000 description 7
125000001453 quaternary ammonium group Chemical group 0.000 description 7
239000000523 sample Substances 0.000 description 7
229910001415 sodium ion Inorganic materials 0.000 description 7
238000012360 testing method Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
125000004442 acylamino group Chemical group 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
150000007529 inorganic bases Chemical class 0.000 description 6
229910001416 lithium ion Inorganic materials 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
238000002156 mixing Methods 0.000 description 6
150000007530 organic bases Chemical class 0.000 description 6
150000002892 organic cations Chemical class 0.000 description 6
229910001414 potassium ion Inorganic materials 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
238000001454 recorded image Methods 0.000 description 6
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 6
239000003115 supporting electrolyte Substances 0.000 description 6
238000012546 transfer Methods 0.000 description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 5
238000004040 coloring Methods 0.000 description 5
229940125782 compound 2 Drugs 0.000 description 5
229960003280 cupric chloride Drugs 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
235000011187 glycerol Nutrition 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
230000006872 improvement Effects 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 5
150000002989 phenols Chemical class 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
229910052697 platinum Inorganic materials 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
230000009257 reactivity Effects 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000012463 white pigment Substances 0.000 description 5
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 4
LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
125000003368 amide group Chemical group 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
150000001448 anilines Chemical class 0.000 description 4
239000002518 antifoaming agent Substances 0.000 description 4
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
239000007853 buffer solution Substances 0.000 description 4
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
238000004140 cleaning Methods 0.000 description 4
239000003086 colorant Substances 0.000 description 4
229940125904 compound 1 Drugs 0.000 description 4
229940125898 compound 5 Drugs 0.000 description 4
229920001577 copolymer Chemical group 0.000 description 4
239000002274 desiccant Substances 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
125000006575 electron-withdrawing group Chemical group 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000010419 fine particle Substances 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Substances OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
229910052742 iron Inorganic materials 0.000 description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
229910052748 manganese Inorganic materials 0.000 description 4
239000011572 manganese Substances 0.000 description 4
150000004780 naphthols Chemical class 0.000 description 4
238000006386 neutralization reaction Methods 0.000 description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
238000003969 polarography Methods 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 4
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
239000000725 suspension Substances 0.000 description 4
229910002029 synthetic silica gel Inorganic materials 0.000 description 4
238000010998 test method Methods 0.000 description 4
229910052718 tin Inorganic materials 0.000 description 4
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