JP2018108360A - Aldehyde scavenger - Google Patents
Aldehyde scavenger Download PDFInfo
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- JP2018108360A JP2018108360A JP2017245501A JP2017245501A JP2018108360A JP 2018108360 A JP2018108360 A JP 2018108360A JP 2017245501 A JP2017245501 A JP 2017245501A JP 2017245501 A JP2017245501 A JP 2017245501A JP 2018108360 A JP2018108360 A JP 2018108360A
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- carbon atoms
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- aldehyde
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- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims abstract description 82
- 239000002516 radical scavenger Substances 0.000 title claims abstract description 44
- -1 carboxy, hydroxy, mercapto Chemical class 0.000 claims abstract description 129
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 20
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 99
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- 230000002000 scavenging effect Effects 0.000 abstract description 6
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 30
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 13
- 229920002620 polyvinyl fluoride Polymers 0.000 description 11
- 239000007789 gas Substances 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 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 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 235000019645 odor Nutrition 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- NQRKYASMKDDGHT-UHFFFAOYSA-N (aminooxy)acetic acid Chemical compound NOCC(O)=O NQRKYASMKDDGHT-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 description 2
- 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 2
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000000913 palmityl 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])C([H])([H])[H] 0.000 description 2
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000011120 plywood Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 208000008842 sick building syndrome Diseases 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- KBXIJIPYZKPDRU-UHFFFAOYSA-N (aminooxy)acetic acid hemihydrochloride Chemical compound Cl.NOCC(O)=O.NOCC(O)=O KBXIJIPYZKPDRU-UHFFFAOYSA-N 0.000 description 1
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 description 1
- ZJQIXGGEADDPQB-UHFFFAOYSA-N 1,2-bis(ethenyl)-3,4-dimethylbenzene Chemical group CC1=CC=C(C=C)C(C=C)=C1C ZJQIXGGEADDPQB-UHFFFAOYSA-N 0.000 description 1
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 description 1
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 1
- VEHLXPKUFPLBNQ-UHFFFAOYSA-N 3-methylpenta-1,4-dien-3-ylbenzene Chemical compound C=CC(C)(C=C)C1=CC=CC=C1 VEHLXPKUFPLBNQ-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-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
- 239000005909 Kieselgur Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-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
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- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005262 alkoxyamine group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
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- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002960 margaryl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical compound C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 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 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
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000120 polyethyl acrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920006216 polyvinyl aromatic Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Images
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
Abstract
Description
本発明は、アルデヒド類の捕捉剤に関する。 The present invention relates to a scavenger for aldehydes.
アセトアルデヒドやホルムアルデヒド等のアルデヒド類は、生活環境における代表的な臭気物質であり、臭い閾値が極めて低いために低濃度でも不快臭の原因となる。これらのアルデヒド類は屋内や自動車内において合成樹脂、合板、タバコの煙等から発生し、シックハウス症候群やシックカー症候群の原因となることが知られている。また、これらのアルデヒド類は発癌性も疑われており、人が日常的にこれらに曝されると、健康を害するリスクがある。そのため、厚生労働省により室内濃度指針値として、アセトアルデヒドは０．０３ｐｐｍ、ホルムアルデヒドは０．０８ｐｐｍと規定されている。したがって、アルデヒド類を速やかに且つ持続的に除去する手段が求められている。 Aldehydes such as acetaldehyde and formaldehyde are typical odorous substances in the living environment, and because of their extremely low odor threshold, they cause unpleasant odors even at low concentrations. These aldehydes are generated indoors and in automobiles from synthetic resin, plywood, cigarette smoke, etc., and are known to cause sick house syndrome and sick car syndrome. In addition, these aldehydes are also suspected to be carcinogenic, and there is a risk of harm to health if a person is exposed to them on a daily basis. Therefore, the Ministry of Health, Labor and Welfare stipulates that the indoor concentration guideline values are 0.03 ppm for acetaldehyde and 0.08 ppm for formaldehyde. Therefore, there is a need for means for quickly and continuously removing aldehydes.
アセトアルデヒドやホルムアルデヒド等の低級アルデヒドは沸点が低いため、消臭剤として汎用されるシリカゲルや活性炭等の無機系多孔質材では捕捉効率が低い。そこで、ヒドラジン誘導体、アミン、アミノ酸、又は尿素誘導体等からなるアルデヒド捕捉剤とアルデヒド類を化学反応させることによりアルデヒド類を捕捉する方法が開示されている（例えば、特許文献１〜３参照）。 Since lower aldehydes such as acetaldehyde and formaldehyde have a low boiling point, inorganic porous materials such as silica gel and activated carbon, which are widely used as deodorants, have low trapping efficiency. Thus, a method for capturing aldehydes by chemically reacting an aldehyde capturing agent composed of a hydrazine derivative, an amine, an amino acid, a urea derivative, or the like with an aldehyde is disclosed (for example, see Patent Documents 1 to 3).
しかしながら、これら特許文献に記載の方法は、捕捉効率が不十分である、捕捉剤自体が臭気源となる、又は一旦アルデヒド類を捕捉しても経時的にアルデヒド類を再放出する等の問題があった。また、これら特許文献に記載のアルデヒド捕捉剤をシックハウス症候群やシックカー症候群を予防する目的で住居内や自動車内で使用する場合、これらの場所は夏場等に高温になるため、性能が低下する点が問題であった。 However, the methods described in these patent documents have problems such as insufficient trapping efficiency, the trapping agent itself becomes an odor source, or once the aldehydes are trapped, the aldehydes are re-released over time. there were. In addition, when these aldehyde scavengers described in these patent documents are used in a house or a car for the purpose of preventing sick house syndrome or sick car syndrome, these places become hot in summer and the like, so the performance is reduced. It was a problem.
本発明は、上記の背景技術に鑑みてなされたものであって、アルデヒド類を速やかに且つ持続的に捕捉するアルデヒド捕捉剤を提供することをその目的とする。 This invention is made | formed in view of said background art, Comprising: The objective is to provide the aldehyde capture | acquisition agent which capture | acquires aldehydes rapidly and continuously.
本発明者らは、上記の課題を解決するため鋭意検討を重ねた結果、特定のＯ−置換モノヒドロキシルアミン又はこれらの化学的に許容される塩を含むアルデヒド捕捉剤がアルデヒド類を速やかに且つ持続的に捕捉することを見出し、本発明を完成するに至った。 As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that an aldehyde scavenger containing a specific O-substituted monohydroxylamine or a chemically acceptable salt thereof can quickly and quickly remove aldehydes. It has been found that it can be continuously captured, and the present invention has been completed.
すなわち、本発明は、以下の要旨を有するものである。 That is, the present invention has the following gist.
［１］
１種以上のＯ−置換モノヒドロキシルアミン又はその化学的に許容される塩を含むことを特徴とするアルデヒド捕捉剤。
[1]
An aldehyde scavenger comprising one or more O-substituted monohydroxylamine or a chemically acceptable salt thereof.
［２］
下記一般式（１）で表される１種以上のＯ−置換モノヒドロキシルアミン又はその化学的に許容される塩を含むことを特徴とする［１］に記載のアルデヒド捕捉剤。
[2]
The aldehyde scavenger according to [1], comprising one or more O-substituted monohydroxylamines represented by the following general formula (1) or a chemically acceptable salt thereof.
［上記一般式（１）において、Ｒ１は、化学的に許容される任意の位置に、
ハロゲン原子；
炭素数１〜６のアルキルオキシ基；
炭素数１〜６のハロアルキル基；
炭素数１〜６のハロアルキルオキシ基；
カルボキシ基；
ヒドロキシ基；
メルカプト基；
シアノ基；
ニトロ基；
ハロゲン原子、炭素数１〜６のアルキル基、炭素数１〜６のアルキルオキシ基、炭素数１〜６のハロアルキル基、炭素数１〜６のハロアルキルオキシ基、カルボキシ基、ヒドロキシ基、メルカプト基、シアノ基若しくはニトロ基で置換されていてもよい炭素数６〜１４のアリール基；
ハロゲン原子、炭素数１〜６のアルキル基、炭素数１〜６のアルキルオキシ基、炭素数１〜６のハロアルキル基、炭素数１〜６のハロアルキルオキシ基、カルボキシ基、ヒドロキシ基、メルカプト基、シアノ基若しくはニトロ基で置換されていてもよい炭素数４〜１４のヘテロアリール基；
下記一般式（２）で表されるアルコキシカルボニル基；
及び
下記一般式（３）で表されるカルバモイル基；
からなる群より選ばれる１つ以上の置換基で置換されていてもよい炭素数１〜１８の直鎖状、分岐状若しくは環状のアルキル基を表す。］
[In the general formula (1), R 1 is at a chemically acceptable position,
A halogen atom;
An alkyloxy group having 1 to 6 carbon atoms;
A haloalkyl group having 1 to 6 carbon atoms;
A haloalkyloxy group having 1 to 6 carbon atoms;
A carboxy group;
A hydroxy group;
A mercapto group;
A cyano group;
A nitro group;
A halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a haloalkyloxy group having 1 to 6 carbon atoms, a carboxy group, a hydroxy group, a mercapto group, An aryl group having 6 to 14 carbon atoms which may be substituted with a cyano group or a nitro group;
A halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a haloalkyloxy group having 1 to 6 carbon atoms, a carboxy group, a hydroxy group, a mercapto group, A heteroaryl group having 4 to 14 carbon atoms which may be substituted with a cyano group or a nitro group;
An alkoxycarbonyl group represented by the following general formula (2);
And a carbamoyl group represented by the following general formula (3);
Represents a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms which may be substituted with one or more substituents selected from the group consisting of: ]
［上記一般式（２）において、Ｒ２は、化学的に許容される任意の位置に、
カルボキシ基；
ヒドロキシ基；
メルカプト基；
ハロゲン原子；
炭素数１〜６のアルキルオキシ基；
炭素数１〜６のハロアルキルオキシ基；
炭素数６〜１４のアリール基；
及び
炭素数４〜１４のヘテロアリール基；
からなる群より選ばれる１つ以上の置換基で置換されていてもよい炭素数１〜１８の直鎖状、分岐状若しくは環状のアルキル基を表す。］
[In the above general formula (2), R 2 is at a chemically acceptable position,
A carboxy group;
A hydroxy group;
A mercapto group;
A halogen atom;
An alkyloxy group having 1 to 6 carbon atoms;
A haloalkyloxy group having 1 to 6 carbon atoms;
An aryl group having 6 to 14 carbon atoms;
And a heteroaryl group having 4 to 14 carbon atoms;
Represents a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms which may be substituted with one or more substituents selected from the group consisting of: ]
［上記一般式（３）において、Ｒ３は、同一又は相異なっていてもよく、各々独立して、化学的に許容される任意の位置に、
カルボキシ基；
ヒドロキシ基；
メルカプト基；
ハロゲン原子；
炭素数１〜６のアルキルオキシ基；
炭素数１〜６のハロアルキルオキシ基；
炭素数６〜１４のアリール基；
及び
炭素数４〜１４のヘテロアリール基；
からなる群より選ばれる１つ以上の置換基で置換されていてもよい炭素数１〜１８の直鎖状、分岐状若しくは環状のアルキル基、
炭素数６〜１４のアリール基、
炭素数４〜１４のヘテロアリール基、
又は
水素原子を表す。］
［３］
一般式（１）において、Ｒ１が、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ベンジル基、２−ピリジルメチル基、３−ピリジルメチル基、４−ピリジルメチル基、カルボキシメチル基、１−カルボキシエチル基、２−カルボキシエチル基、１−カルボキシプロピル基、２−カルボキシプロピル基、３−カルボキシプロピル基、α−カルボキシベンジル基、α−カルボキシフェネチル基、β−カルボキシフェネチル基、２−ヒドロキシエチル基、２−ヒドロキシプロピル基、３−ヒドロキシプロピル基、１−カルボキシ−２−ヒドロキシエチル基、α−（メトキシカルボニル）ベンジル基、α−（メトキシカルボニル）フェネチル基、β−（メトキシカルボニル）フェネチル基、カルバモイルメチル基、Ｎ−フェニルカルバモイルメチル基、Ｎ−（２−カルボキシフェニル）カルバモイルメチル基、Ｎ−（３−カルボキシフェニル）カルバモイルメチル基、Ｎ−（４−カルボキシフェニル）カルバモイルメチル基又はＮ−（２，６−ジメチルフェニル）カルバモイルメチル基のいずれかであることを特徴とする［１］又は［２］に記載のアルデヒド捕捉剤。
[In the above general formula (3), R 3 s may be the same or different, and each independently, at any chemically acceptable position,
A carboxy group;
A hydroxy group;
A mercapto group;
A halogen atom;
An alkyloxy group having 1 to 6 carbon atoms;
A haloalkyloxy group having 1 to 6 carbon atoms;
An aryl group having 6 to 14 carbon atoms;
And a heteroaryl group having 4 to 14 carbon atoms;
A linear, branched or cyclic alkyl group having 1 to 18 carbon atoms which may be substituted with one or more substituents selected from the group consisting of:
An aryl group having 6 to 14 carbon atoms,
A heteroaryl group having 4 to 14 carbon atoms,
Or represents a hydrogen atom. ]
[3]
In the general formula (1), R 1 is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, benzyl group, 2-pyridylmethyl group, 3- Pyridylmethyl group, 4-pyridylmethyl group, carboxymethyl group, 1-carboxyethyl group, 2-carboxyethyl group, 1-carboxypropyl group, 2-carboxypropyl group, 3-carboxypropyl group, α-carboxybenzyl group, α-carboxyphenethyl group, β-carboxyphenethyl group, 2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-carboxy-2-hydroxyethyl group, α- (methoxycarbonyl) benzyl group, α -(Methoxycarbonyl) phenethyl group, β- (methoxycarbonyl) phen Netyl group, carbamoylmethyl group, N-phenylcarbamoylmethyl group, N- (2-carboxyphenyl) carbamoylmethyl group, N- (3-carboxyphenyl) carbamoylmethyl group, N- (4-carboxyphenyl) carbamoylmethyl group or The aldehyde scavenger according to [1] or [2], which is any one of N- (2,6-dimethylphenyl) carbamoylmethyl groups.
［４］
［１］乃至［３］のいずれかに記載のアルデヒド捕捉剤をアルデヒド発生源に対して使用することを特徴とするアルデヒドの除去方法。
[4]
[1] A method for removing an aldehyde, comprising using the aldehyde scavenger according to any one of [3] to an aldehyde generation source.
本発明のアルデヒド捕捉剤は、アルデヒド類を速やかに且つ持続的に捕捉する。その結果、人体に有害なアルデヒド類を低減し、ヒトの生活環境を改善することができる。 The aldehyde scavenger of the present invention captures aldehydes quickly and continuously. As a result, it is possible to reduce aldehydes that are harmful to the human body and improve the human living environment.
本発明のアルデヒド捕捉剤は、１種以上のＯ−置換モノヒドロキシルアミン又はその化学的に許容される塩を含むことをその特徴とする。 The aldehyde scavenger of the present invention is characterized by comprising one or more O-substituted monohydroxylamines or chemically acceptable salts thereof.
上記一般式（１）において、Ｒ１は、化学的に許容される任意の位置に、
ハロゲン原子；
炭素数１〜６のアルキルオキシ基；
炭素数１〜６のハロアルキル基；
炭素数１〜６のハロアルキルオキシ基；
カルボキシ基；
ヒドロキシ基；
メルカプト基；
シアノ基；
ニトロ基；
ハロゲン原子、炭素数１〜６のアルキル基、炭素数１〜６のアルキルオキシ基、炭素数１〜６のハロアルキル基、炭素数１〜６のハロアルキルオキシ基、カルボキシ基、ヒドロキシ基、メルカプト基、シアノ基若しくはニトロ基で置換されていてもよい炭素数６〜１４のアリール基；
ハロゲン原子、炭素数１〜６のアルキル基、炭素数１〜６のアルキルオキシ基、炭素数１〜６のハロアルキル基、炭素数１〜６のハロアルキルオキシ基、カルボキシ基、ヒドロキシ基、メルカプト基、シアノ基若しくはニトロ基で置換されていてもよい炭素数４〜１４のヘテロアリール基；
下記一般式（２）で表されるアルコキシカルボニル基；
及び
下記一般式（３）で表されるカルバモイル基；
からなる群より選ばれる１つ以上の置換基で置換されていてもよい炭素数１〜１８の直鎖状、分岐状若しくは環状のアルキル基を表す。
In the general formula (1), R 1 is located at any chemically acceptable position,
A halogen atom;
An alkyloxy group having 1 to 6 carbon atoms;
A haloalkyl group having 1 to 6 carbon atoms;
A haloalkyloxy group having 1 to 6 carbon atoms;
A carboxy group;
A hydroxy group;
A mercapto group;
A cyano group;
A nitro group;
A halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a haloalkyloxy group having 1 to 6 carbon atoms, a carboxy group, a hydroxy group, a mercapto group, An aryl group having 6 to 14 carbon atoms which may be substituted with a cyano group or a nitro group;
A halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a haloalkyloxy group having 1 to 6 carbon atoms, a carboxy group, a hydroxy group, a mercapto group, A heteroaryl group having 4 to 14 carbon atoms which may be substituted with a cyano group or a nitro group;
An alkoxycarbonyl group represented by the following general formula (2);
And a carbamoyl group represented by the following general formula (3);
Represents a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms which may be substituted with one or more substituents selected from the group consisting of:
［上記一般式（２）において、Ｒ２は、化学的に許容される任意の位置に、
カルボキシ基；
ヒドロキシ基；
メルカプト基；
ハロゲン原子；
炭素数１〜６のアルキルオキシ基；
炭素数１〜６のハロアルキルオキシ基；
炭素数６〜１４のアリール基；
及び
炭素数４〜１４のヘテロアリール基；
からなる群より選ばれる１つ以上の置換基で置換されていてもよい炭素数１〜１８の直鎖状、分岐状若しくは環状のアルキル基を表す。］
[In the above general formula (2), R 2 is at a chemically acceptable position,
A carboxy group;
A hydroxy group;
A mercapto group;
A halogen atom;
An alkyloxy group having 1 to 6 carbon atoms;
A haloalkyloxy group having 1 to 6 carbon atoms;
An aryl group having 6 to 14 carbon atoms;
And a heteroaryl group having 4 to 14 carbon atoms;
Represents a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms which may be substituted with one or more substituents selected from the group consisting of: ]
［上記一般式（３）において、Ｒ３は、同一又は相異なっていてもよく、各々独立して、化学的に許容される任意の位置に、
カルボキシ基；
ヒドロキシ基；
メルカプト基；
ハロゲン原子；
炭素数１〜６のアルキルオキシ基；
炭素数１〜６のハロアルキルオキシ基；
炭素数６〜１４のアリール基；
及び
炭素数４〜１４のヘテロアリール基；
からなる群より選ばれる１つ以上の置換基で置換されていてもよい炭素数１〜１８の直鎖状、分岐状若しくは環状のアルキル基、
炭素数６〜１４のアリール基、
炭素数４〜１４のヘテロアリール基、
又は
水素原子を表す。］
炭素数１〜１８の直鎖状、分岐状若しくは環状のアルキル基としては、特に限定されないが、例えば、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基（セチル基）、ヘプタデシル基、オクタデシル基（ステアリル基）、オレイル基、エライジル基、イソプロピル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、３−メチルブチル基、２，２−ジメチルプロピル基、１，１−ジメチルプロピル基、２−エチルヘキシル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基、シクロノニル基、シクロデシル基等が挙げられる。
[In the above general formula (3), R 3 s may be the same or different, and each independently, at any chemically acceptable position,
A carboxy group;
A hydroxy group;
A mercapto group;
A halogen atom;
An alkyloxy group having 1 to 6 carbon atoms;
A haloalkyloxy group having 1 to 6 carbon atoms;
An aryl group having 6 to 14 carbon atoms;
And a heteroaryl group having 4 to 14 carbon atoms;
A linear, branched or cyclic alkyl group having 1 to 18 carbon atoms which may be substituted with one or more substituents selected from the group consisting of:
An aryl group having 6 to 14 carbon atoms,
A heteroaryl group having 4 to 14 carbon atoms,
Or represents a hydrogen atom. ]
The linear, branched or cyclic alkyl group having 1 to 18 carbon atoms is not particularly limited, and examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. , Nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group (cetyl group), heptadecyl group, octadecyl group (stearyl group), oleyl group, elaidyl group, isopropyl group, isobutyl group , Sec-butyl group, tert-butyl group, 3-methylbutyl group, 2,2-dimethylpropyl group, 1,1-dimethylpropyl group, 2-ethylhexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, Cycloheptyl group, cyclooctyl group, cyclononyl group, Rodeshiru group, and the like.
該アルキル基は、ハロゲン原子、カルボキシ基、ヒドロキシ基、メルカプト基、シアノ基、ニトロ基、炭素数１〜６のアルキルオキシ基、炭素数１〜６のハロアルキル基、炭素数１〜６のハロアルキルオキシ基、炭素数６〜１４のアリール基、炭素数４〜１４のヘテロアリール基、一般式（２）で表されるアルコキシカルボニル基、及び／又は一般式（３）で表されるカルバモイル基で置換されていてもよく、これらの置換基としては、以下に例示する置換基を挙げることができる。 The alkyl group is a halogen atom, a carboxy group, a hydroxy group, a mercapto group, a cyano group, a nitro group, an alkyloxy group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, or a haloalkyloxy having 1 to 6 carbon atoms. Group, an aryl group having 6 to 14 carbon atoms, a heteroaryl group having 4 to 14 carbon atoms, an alkoxycarbonyl group represented by the general formula (2), and / or a carbamoyl group represented by the general formula (3) These substituents may include the substituents exemplified below.
ハロゲン原子としては、フッ素原子、塩素原子、臭素原子等を例示することができる。 As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, etc. can be illustrated.
炭素数１〜６のアルキルオキシ基としては、直鎖状、分岐状又は環状のいずれであってもよく、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ブチルオキシ基、ペンチルオキシ基、ヘキシルオキシ基、イソブチルオキシ基、ｓｅｃ−ブチルオキシ基、ｔｅｒｔ−ブチルオキシ基、３−メチルブチルオキシ基、２，２−ジメチルプロピルオキシ基、１，１−ジメチルプロピルオキシ基、２−エチルヘキシルオキシ基、シクロプロピルオキシ基、シクロブチルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基等を例示することができる。 The alkyloxy group having 1 to 6 carbon atoms may be linear, branched or cyclic, and is a methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, pentyloxy group, hexyl. Oxy group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group, 3-methylbutyloxy group, 2,2-dimethylpropyloxy group, 1,1-dimethylpropyloxy group, 2-ethylhexyloxy group, cyclopropyl Examples thereof include an oxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group.
炭素数１〜６のハロアルキル基としては、直鎖状、分岐状又は環状のいずれであってもよく、ジフルオロメチル基、トリフルオロメチル基、２，２−ジフルオロエチル基、２，２，２−トリフルオロエチル基、３−フルオロプロピル基、１−（トリフルオロメチル）−２，２，２−トリフルオロエチル基等を例示することができる。 The haloalkyl group having 1 to 6 carbon atoms may be linear, branched or cyclic, and is a difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2- A trifluoroethyl group, a 3-fluoropropyl group, a 1- (trifluoromethyl) -2,2,2-trifluoroethyl group and the like can be exemplified.
炭素数１〜６のハロアルキルオキシ基としては、直鎖状、分岐状又は環状のいずれであってもよく、ジフルオロメチルオキシ基、トリフルオロメチルオキシ基、２，２−ジフルオロエチルオキシ基、２，２，２−トリフルオロエチルオキシ基、３−フルオロプロピルオキシ基、１−（トリフルオロメチル）−２，２，２−トリフルオロエチルオキシ基等を例示することができる。 The haloalkyloxy group having 1 to 6 carbon atoms may be linear, branched or cyclic, and is a difluoromethyloxy group, trifluoromethyloxy group, 2,2-difluoroethyloxy group, 2, Examples include 2,2-trifluoroethyloxy group, 3-fluoropropyloxy group, 1- (trifluoromethyl) -2,2,2-trifluoroethyloxy group, and the like.
炭素数６〜１４のアリール基及び炭素数４〜１４のヘテロアリール基としては、特に限定されないが、例えば、フェニル基、ナフチル基、アントリル基、トリル基、キシリル基、クメニル基、ビニルフェニル基、ビフェニリル基、フェナントリル基、ピロリル基、フリル基、チエニル基、ピリジル基、インドリル基、キノリル基、イソキノリル基等が挙げられる。 Examples of the aryl group having 6 to 14 carbon atoms and the heteroaryl group having 4 to 14 carbon atoms include, but are not limited to, for example, phenyl group, naphthyl group, anthryl group, tolyl group, xylyl group, cumenyl group, vinylphenyl group, Biphenylyl group, phenanthryl group, pyrrolyl group, furyl group, thienyl group, pyridyl group, indolyl group, quinolyl group, isoquinolyl group and the like can be mentioned.
該アリール基及びヘテロアリール基は、ハロゲン原子、炭素数１〜６のアルキル基、炭素数１〜６のアルキルオキシ基、炭素数１〜６のハロアルキル基及び／又は炭素数１〜６のハロアルキルオキシ基で置換されていてもよく、これらの置換基としては、以下に例示する置換基を挙げることができる。 The aryl group and heteroaryl group are a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms and / or a haloalkyloxy having 1 to 6 carbon atoms. It may be substituted with a group, and examples of these substituents include the substituents exemplified below.
上記一般式（２）で表されるアルコキシカルボニル基としては、特に限定されないが、例えば、メトキシカルボニル基、エトキシカルボニル基、プロピルオキシカルボニル基、イソプロピルオキシカルボニル基、ブチルオキシカルボニル基、イソブチルオキシカルボニル基、ｓｅｃ−ブチルオキシカルボニル基、ｔｅｒｔ−ブチルオキシカルボニル基、ジフルオロメチルオキシカルボニル基、トリフルオロメチルオキシカルボニル基、フェニルオキシカルボニル基、ナフチルオキシカルボニル基、ピリジルオキシカルボニル基等が挙げられる。 The alkoxycarbonyl group represented by the general formula (2) is not particularly limited, and examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butyloxycarbonyl group, and an isobutyloxycarbonyl group. , Sec-butyloxycarbonyl group, tert-butyloxycarbonyl group, difluoromethyloxycarbonyl group, trifluoromethyloxycarbonyl group, phenyloxycarbonyl group, naphthyloxycarbonyl group, pyridyloxycarbonyl group and the like.
上記一般式（３）で表されるカルバモイル基としては、特に限定されないが、例えば、カルバモイル基、Ｎ−メチルカルバモイル基、Ｎ−エチルカルバモイル基、Ｎ−プロピルカルバモイル基、Ｎ−イソプロピルカルバモイル基、Ｎ−ブチルカルバモイル基、Ｎ−イソブチルカルバモイル基、Ｎ−（ｓｅｃ−ブチル）カルバモイル基、Ｎ−（ｔｅｒｔ−ブチル）カルバモイル基、Ｎ−ジフルオロメチルカルバモイル基、Ｎ−トリフルオロメチルカルバモイル基、Ｎ−フェニルカルバモイル基、Ｎ−ナフチルカルバモイル基、Ｎ−ピリジルカルバモイル基、Ｎ，Ｎ−ジメチルカルバモイル基、Ｎ，Ｎ−ジエチルカルバモイル基、Ｎ，Ｎ−ジプロピルカルバモイル基、Ｎ，Ｎ−ジイソプロピルカルバモイル基、Ｎ，Ｎ−ジブチルカルバモイル基、Ｎ，Ｎ−ジイソブチルカルバモイル基、Ｎ，Ｎ−ジ（ｓｅｃ−ブチル）カルバモイル基、Ｎ，Ｎ−ジ（ｔｅｒｔ−ブチル）カルバモイル基、Ｎ，Ｎ−ビス（ジフルオロメチル）カルバモイル基、Ｎ，Ｎ−ビス（トリフルオロメチル）カルバモイル基、Ｎ，Ｎ−ジフェニルカルバモイル基、Ｎ，Ｎ−ジナフチルカルバモイル基、Ｎ，Ｎ−ジピリジルカルバモイル基等が挙げられる。 Although it does not specifically limit as a carbamoyl group represented by the said General formula (3), For example, a carbamoyl group, N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N -Butylcarbamoyl group, N-isobutylcarbamoyl group, N- (sec-butyl) carbamoyl group, N- (tert-butyl) carbamoyl group, N-difluoromethylcarbamoyl group, N-trifluoromethylcarbamoyl group, N-phenylcarbamoyl group Group, N-naphthylcarbamoyl group, N-pyridylcarbamoyl group, N, N-dimethylcarbamoyl group, N, N-diethylcarbamoyl group, N, N-dipropylcarbamoyl group, N, N-diisopropylcarbamoyl group, N, N A dibutylcarbamoyl group, , N-diisobutylcarbamoyl group, N, N-di (sec-butyl) carbamoyl group, N, N-di (tert-butyl) carbamoyl group, N, N-bis (difluoromethyl) carbamoyl group, N, N-bis (Trifluoromethyl) carbamoyl group, N, N-diphenylcarbamoyl group, N, N-dinaphthylcarbamoyl group, N, N-dipyridylcarbamoyl group and the like can be mentioned.
炭素数１〜６のアルキル基としては、直鎖状、分岐状又は環状のいずれであってもよく、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、ペンチル基、ヘキシル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、３−メチルブチル基、２，２−ジメチルプロピル基、１，１−ジメチルプロピル基、２−エチルヘキシル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基等を例示することができる。 The alkyl group having 1 to 6 carbon atoms may be linear, branched or cyclic, and may be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a pentyl group, a hexyl group, or an isobutyl group. , Sec-butyl group, tert-butyl group, 3-methylbutyl group, 2,2-dimethylpropyl group, 1,1-dimethylpropyl group, 2-ethylhexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc. Can be illustrated.
炭素数１〜６のアルキルオキシ基としては、直鎖状、分岐状又は環状のいずれであってもよく、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ブチルオキシ基、ペンチルオキシ基、ヘキシルオキシ基、イソブチルオキシ基、ｓｅｃ−ブチルオキシ基、ｔｅｒｔ−ブチルオキシ基、３−メチルブチルオキシ基、２，２−ジメチルプロピルオキシ基、１，１−ジメチルプロピルオキシ基、２−エチルヘキシルオキシ基、シクロプロピルオキシ基、シクロブチルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基等を例示することができる。 The alkyloxy group having 1 to 6 carbon atoms may be linear, branched or cyclic, and is a methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, pentyloxy group, hexyl. Oxy group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group, 3-methylbutyloxy group, 2,2-dimethylpropyloxy group, 1,1-dimethylpropyloxy group, 2-ethylhexyloxy group, cyclopropyl Examples thereof include an oxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group.
炭素数１〜６のハロアルキル基としては、直鎖状、分岐状又は環状のいずれであってもよく、ジフルオロメチル基、トリフルオロメチル基、２，２−ジフルオロエチル基、２，２，２−トリフルオロエチル基、３−フルオロプロピル基、１−（トリフルオロメチル）−２，２，２−トリフルオロエチル基等を例示することができる。 The haloalkyl group having 1 to 6 carbon atoms may be linear, branched or cyclic, and is a difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2- A trifluoroethyl group, a 3-fluoropropyl group, a 1- (trifluoromethyl) -2,2,2-trifluoroethyl group and the like can be exemplified.
炭素数１〜６のハロアルキルオキシ基としては、直鎖状、分岐状又は環状のいずれであってもよく、ジフルオロメチルオキシ基、トリフルオロメチルオキシ基、２，２−ジフルオロエチルオキシ基、２，２，２−トリフルオロエチルオキシ基、３−フルオロプロピルオキシ基、１−（トリフルオロメチル）−２，２，２−トリフルオロエチルオキシ基等を例示することができる。 The haloalkyloxy group having 1 to 6 carbon atoms may be linear, branched or cyclic, and is a difluoromethyloxy group, trifluoromethyloxy group, 2,2-difluoroethyloxy group, 2, Examples include 2,2-trifluoroethyloxy group, 3-fluoropropyloxy group, 1- (trifluoromethyl) -2,2,2-trifluoroethyloxy group, and the like.
これらのうち、一般式（１）において、Ｒ１が、カルボキシ基、ヒドロキシ基、メルカプト基、炭素数６〜１４のアリール基又は炭素数４〜１４のヘテロアリール基で置換されていてもよい炭素数１〜８の直鎖状若しくは分岐状のアルキル基であるＯ−置換モノヒドロキシルアミンが好しく、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ベンジル基、２−ピリジルメチル基、３−ピリジルメチル基、４−ピリジルメチル基、カルボキシメチル基、１−カルボキシエチル基、１−カルボキシプロピル基、３−カルボキシプロピル基、α−カルボキシベンジル基、α−カルボキシフェネチル基、β−カルボキシフェネチル基、２−ヒドロキシエチル基、２−ヒドロキシプロピル基、３−ヒドロキシプロピル基、１−カルボキシ−２−ヒドロキシエチル基、α−（メトキシカルボニル）ベンジル基、α−（メトキシカルボニル）フェネチル基、カルバモイルメチル基、β−（メトキシカルボニル）フェネチル基、カルバモイルメチル基、Ｎ−フェニルカルバモイルメチル基、Ｎ−（２−カルボキシフェニル）カルバモイルメチル基、Ｎ−（３−カルボキシフェニル）カルバモイルメチル基、Ｎ−（４−カルボキシフェニル）カルバモイルメチル基又はＮ−（２，６−ジメチルフェニル）カルバモイルメチル基のいずれかであるＯ−置換モノヒドロキシルアミンが特に好ましい。 Among these, in General Formula (1), R 1 may be substituted with a carboxy group, a hydroxy group, a mercapto group, an aryl group having 6 to 14 carbon atoms, or a heteroaryl group having 4 to 14 carbon atoms. An O-substituted monohydroxylamine which is a linear or branched alkyl group of 1 to 8 is preferred, and is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert group. -Butyl group, benzyl group, 2-pyridylmethyl group, 3-pyridylmethyl group, 4-pyridylmethyl group, carboxymethyl group, 1-carboxyethyl group, 1-carboxypropyl group, 3-carboxypropyl group, α-carboxyl Benzyl group, α-carboxyphenethyl group, β-carboxyphenethyl group, 2-hydroxyethyl group, 2-hydroxy group Propyl group, 3-hydroxypropyl group, 1-carboxy-2-hydroxyethyl group, α- (methoxycarbonyl) benzyl group, α- (methoxycarbonyl) phenethyl group, carbamoylmethyl group, β- (methoxycarbonyl) phenethyl group, Carbamoylmethyl group, N-phenylcarbamoylmethyl group, N- (2-carboxyphenyl) carbamoylmethyl group, N- (3-carboxyphenyl) carbamoylmethyl group, N- (4-carboxyphenyl) carbamoylmethyl group or N- ( Particularly preferred are O-substituted monohydroxylamines which are either 2,6-dimethylphenyl) carbamoylmethyl groups.
上記のＯ−置換モノヒドロキシルアミンは一部又は全てが無機酸又は有機酸との化学的に許容される塩となっていてもよい。塩の種類としては、特に限定されないが、例えば、塩酸塩、臭化水素酸塩、過塩素酸塩、ケイ酸塩、テトラフルオロホウ酸塩、ヘキサフルオロリン酸塩、硫酸塩、硝酸塩、リン酸塩等の無機酸塩、酢酸塩、クエン酸塩、フマル酸塩、マレイン酸塩、トリフルオロメタンスルホン酸塩、トリフルオロ酢酸塩、安息香酸塩、トシル酸塩等の有機酸塩が挙げられ、安価である点で無機酸塩が好ましく、塩酸塩がさらに好ましい。 The above-mentioned O-substituted monohydroxylamine may be partly or entirely a chemically acceptable salt with an inorganic acid or an organic acid. The type of salt is not particularly limited. For example, hydrochloride, hydrobromide, perchlorate, silicate, tetrafluoroborate, hexafluorophosphate, sulfate, nitrate, phosphoric acid Inorganic acid salts such as salts, organic acid salts such as acetate, citrate, fumarate, maleate, trifluoromethanesulfonate, trifluoroacetate, benzoate, tosylate, etc. In view of the above, inorganic acid salts are preferable, and hydrochlorides are more preferable.
また、Ｏ−置換モノヒドロキシルアミンがアミノ基を含む場合も、当該アミノ基の一部又は全てが上記の無機酸又は有機酸との化学的に許容される塩となっていてもよい。 Also, when the O-substituted monohydroxylamine contains an amino group, a part or all of the amino group may be a chemically acceptable salt with the above inorganic acid or organic acid.
一方、Ｏ−置換モノヒドロキシルアミンがカルボキシ基を含む場合は、当該カルボキシ基が分子内のヒドロキシルアミノ基やアミノ基と分子内塩を形成してもよい。また、当該カルボキシ基の一部又は全てがカルボン酸塩となっていてもよい。カルボン酸塩の種類としては、特に限定されないが、例えば、リチウム塩、ナトリウム塩、カリウム塩、セシウム塩等のアルカリ金属塩、アンモニウム塩等が挙げられる。 On the other hand, when the O-substituted monohydroxylamine contains a carboxy group, the carboxy group may form an intramolecular salt with a hydroxylamino group or amino group in the molecule. Moreover, a part or all of the carboxy group may be a carboxylate. Although it does not specifically limit as a kind of carboxylate, For example, alkali metal salts, such as lithium salt, sodium salt, potassium salt, cesium salt, ammonium salt, etc. are mentioned.
本発明のアルデヒド捕捉剤は、目的、用途に応じて任意の形態で使用することができる。例えば、Ｏ−置換モノヒドロキシルアミン又はその化学的に許容される塩（以下、「Ｏ−置換モノヒドロキシルアミン類」という。）を任意の溶媒に溶解させて液状アルデヒド捕捉剤として使用したり、Ｏ−置換モノヒドロキシルアミン類又は前記の液状アルデヒド捕捉剤を任意の担体に担持し、固体状アルデヒド捕捉剤として使用したり、又はゴム等に練り込んで使用することができる。また、これらの捕捉剤を合板や自動車天井材等のアルデヒド発生源となる材料に適用することで、当該材料から環境中へのアルデヒド類放出を抑制することができる。 The aldehyde scavenger of the present invention can be used in any form depending on the purpose and application. For example, O-substituted monohydroxylamine or a chemically acceptable salt thereof (hereinafter referred to as “O-substituted monohydroxylamines”) can be dissolved in an arbitrary solvent and used as a liquid aldehyde scavenger, -A substituted monohydroxylamine or the above liquid aldehyde scavenger can be supported on an arbitrary carrier and used as a solid aldehyde scavenger, or kneaded into rubber or the like. Moreover, by applying these scavengers to materials that serve as aldehyde generation sources such as plywood and automobile ceiling materials, release of aldehydes from the material into the environment can be suppressed.
本発明の液状アルデヒド捕捉剤を調製する際の溶媒へのＯ−置換モノヒドロキシルアミン類の溶解量は、目的に応じて任意に調節可能であり、特に限定するものではないが、本発明の液状アルデヒド捕捉剤に対して１〜５０重量％の範囲が好ましく、５〜３０重量％の範囲がさらに好ましい。 The amount of O-substituted monohydroxylamines dissolved in the solvent when preparing the liquid aldehyde scavenger of the present invention can be arbitrarily adjusted according to the purpose and is not particularly limited, but the liquid of the present invention The range of 1 to 50% by weight is preferable with respect to the aldehyde scavenger, and the range of 5 to 30% by weight is more preferable.
本発明の固体状アルデヒド捕捉剤を調製する際にＯ−置換モノヒドロキシルアミン類を担持する担体としては、水に不溶性のものであれば特に制限なく用いることができる。例えば、高分子担体として、ポリスチレン、架橋ポリスチレン等のスチレン系ポリマー、ポリエチレン、ポリプロピレン等のポリオレフィン、ポリ塩化ビニル、ポリテトラフルオロエチレン等のポリ（ハロゲン化オレフィン）、ポリアクリロニトリル等のニトリル系ポリマー、ポリメタクリル酸メチル、ポリアクリル酸エチル等の（メタ）アクリル系ポリマー、セルロース、アガロース、デキストラン等の高分子量多糖類等が挙げられ、無機担体として、活性炭、シリカゲル、珪藻土、ヒドロキシアパタイト、アルミナ、酸化チタン、マグネシア、ポリシロキサン等が挙げられる。 In preparing the solid aldehyde scavenger of the present invention, the carrier for supporting O-substituted monohydroxylamines can be used without particular limitation as long as it is insoluble in water. Examples of polymer carriers include styrene polymers such as polystyrene and crosslinked polystyrene, polyolefins such as polyethylene and polypropylene, poly (halogenated olefins) such as polyvinyl chloride and polytetrafluoroethylene, nitrile polymers such as polyacrylonitrile, poly Examples include (meth) acrylic polymers such as methyl methacrylate and polyethyl acrylate, and high molecular weight polysaccharides such as cellulose, agarose, and dextran. As inorganic carriers, activated carbon, silica gel, diatomaceous earth, hydroxyapatite, alumina, titanium oxide , Magnesia, polysiloxane and the like.
ここで、架橋ポリスチレンとは、スチレン、ビニルトルエン、ビニルキシレン、ビニルナフタレン等のモノビニル芳香族化合物とジビニルベンゼン、ジビニルトルエン、ジビニルキシレン、ジビニルナフタレン、トリビニルベンゼン、ビスビニルジフェニル、ビスビニルフェニルエタン等のポリビニル芳香族化合物との架橋共重合体を主体とするものであり、これらの共重合体にグリセロールメタクリレート、エチレングリコールジメタクリレート等のメタクリル酸エステルが共重合されていてもよい。 Here, cross-linked polystyrene means monovinyl aromatic compounds such as styrene, vinyl toluene, vinyl xylene, vinyl naphthalene, and divinyl benzene, divinyl toluene, divinyl xylene, divinyl naphthalene, trivinyl benzene, bis vinyl diphenyl, bis vinyl phenyl ethane, etc. The main component is a cross-linked copolymer with a polyvinyl aromatic compound, and a methacrylic acid ester such as glycerol methacrylate or ethylene glycol dimethacrylate may be copolymerized with these copolymers.
本発明の固体状アルデヒド捕捉剤の調製において用いられる担体の形状としては、特に限定するものではないが、例えば、球状（例えば、球状粒子等）、粒状、繊維状、顆粒状、モノリスカラム、中空糸、膜状（例えば、平膜など）等の一般的に分離基材として使用される形状が利用可能であり、これらのうち、球状、膜状、粒状、顆粒状、又は繊維状のものが好ましい。球状、粒状、又は顆粒状担体は、カラム法やバッチ法で使用する際、その使用体積を自由に設定できることから、特に好ましく用いられる。球状、粒状、又は顆粒状担体の粒子サイズとしては、通常、平均粒径１μｍ〜１０ｍｍの範囲のものを用いることができるが、２μｍ〜１ｍｍの範囲が好ましい。 The shape of the carrier used in the preparation of the solid aldehyde scavenger of the present invention is not particularly limited. For example, spherical (eg, spherical particles), granular, fibrous, granular, monolithic column, hollow Shapes generally used as separation substrates such as yarns, membranes (for example, flat membranes, etc.) are available, and among these, spherical, membrane-like, granular, granular, or fibrous ones are available preferable. Spherical, granular, or granular carriers are particularly preferably used because their use volume can be freely set when used in a column method or a batch method. As the particle size of the spherical, granular, or granular carrier, those having an average particle diameter in the range of 1 μm to 10 mm can be usually used, but the range of 2 μm to 1 mm is preferable.
本発明の固体状アルデヒド捕捉剤の調製において用いられる担体は多孔質でもよいし、無孔質でもよい。多孔質担体の平均細孔径としては、通常、１ｎｍ〜１μｍのものを用いることができるが、アルデヒド捕捉速度の点で１ｎｍ〜３００ｎｍの範囲が好ましい。 The carrier used in the preparation of the solid aldehyde scavenger of the present invention may be porous or nonporous. As the average pore diameter of the porous carrier, those having a diameter of 1 nm to 1 μm can be usually used, but the range of 1 nm to 300 nm is preferable in terms of the aldehyde capturing rate.
本発明の固体状アルデヒド捕捉剤を調製する方法としては、特に限定するものではないが、例えば、本発明の液状アルデヒド捕捉剤又はＯ−置換モノヒドロキシルアミン類を担体に物理的に吸着させて固定化する方法が挙げられる。 The method for preparing the solid aldehyde scavenger of the present invention is not particularly limited. For example, the liquid aldehyde scavenger of the present invention or O-substituted monohydroxylamines are physically adsorbed on a carrier and fixed. The method of making it.
Ｏ−置換モノヒドロキシルアミン類を物理的に吸着させて固定化する方法としては、特に限定されないが、例えば、Ｏ−置換モノヒドロキシルアミン類を水等の溶媒に溶解させ、次いで上記した担体を加え、Ｏ−置換モノヒドロキシルアミン類を当該担体に含浸させて、さらに溶媒を留去する方法が挙げられる。 The method for physically adsorbing and immobilizing O-substituted monohydroxylamines is not particularly limited. For example, O-substituted monohydroxylamines are dissolved in a solvent such as water, and then the above-mentioned carrier is added. , O-substituted monohydroxylamines are impregnated into the carrier, and the solvent is distilled off.
担体へのＯ−置換モノヒドロキシルアミン類の担持量は、目的に応じて任意に調節可能であり、特に限定するものではないが、Ｏ−置換モノヒドロキシルアミン類が１〜５０重量％の範囲が好ましく、５〜３０重量％の範囲がさらに好ましい。 The amount of O-substituted monohydroxylamines supported on the carrier can be arbitrarily adjusted according to the purpose, and is not particularly limited, but the range of O-substituted monohydroxylamines is 1 to 50% by weight. The range of 5 to 30% by weight is more preferable.
以下、本発明を具体的に説明するが、本発明はこれらの実施例に限定して解釈されるものではない。 Hereinafter, the present invention will be specifically described, but the present invention is not construed as being limited to these examples.
実施例１〜２６（水溶液中のアルデヒド捕捉試験）
Ｏ−置換モノヒドロキシルアミン類（０．２３ｍｍｏｌ）を水（５ｍＬ）に溶解し、アルデヒド捕捉剤を調製した。ここに、アセトアルデヒド（０．２３ｍｍｏｌ）及び内部標準物質としてジエチレングリコールジエチルエーテル（０．２重量％）を含有する水溶液５ｍＬを混合した。１分後、５分後、１０分後及び３０分後に反応液の一部（０．２ｍＬ）を抜き出し、これに水素化ホウ素ナトリウム１ｍｇを添加し、残存しているアセトアルデヒドをエタノールに還元した。この溶液をガスクロマトグラフ（ＧＣ−２０１４、島津製作所製）で分析し、エタノールとジエチレングリコールジエチルエーテルの面積比から残存アセトアルデヒド濃度を算出した。さらに、アルデヒド捕捉率を下式から算出した。
Examples 1-26 (aldehyde capture test in aqueous solution)
O-substituted monohydroxylamines (0.23 mmol) were dissolved in water (5 mL) to prepare an aldehyde scavenger. Here, 5 mL of an aqueous solution containing acetaldehyde (0.23 mmol) and diethylene glycol diethyl ether (0.2 wt%) as an internal standard substance were mixed. After 1 minute, 5 minutes, 10 minutes and 30 minutes, a part of the reaction solution (0.2 mL) was extracted, 1 mg of sodium borohydride was added thereto, and the remaining acetaldehyde was reduced to ethanol. This solution was analyzed with a gas chromatograph (GC-2014, manufactured by Shimadzu Corporation), and the residual acetaldehyde concentration was calculated from the area ratio of ethanol and diethylene glycol diethyl ether. Furthermore, the aldehyde capture rate was calculated from the following equation.
アルデヒド捕捉率（％）＝［（アセトアルデヒド初濃度−残存アセトアルデヒド濃度）÷アセトアルデヒド初濃度］×１００。 Aldehyde capture rate (%) = [(initial concentration of acetaldehyde−residual acetaldehyde concentration) ÷ initial concentration of acetaldehyde] × 100.
比較例１〜３
Ｏ−置換モノヒドロキシルアミン類に代え、既存品であるケムキャッチＨ−６０００ＨＳ（ヒドラジド系、大塚化学製）、ピペラジン（アミン系）、又はグリシン（アミノ酸系）を用いたこと以外は実施例１〜２６と同様に実施した。
Comparative Examples 1-3
Examples 1 to 3 except that in place of O-substituted monohydroxylamines, Chemcat H-6000HS (hydrazide, manufactured by Otsuka Chemical), piperazine (amine), or glycine (amino acid), which are existing products, were used. 26.
実施例１〜２６及び比較例１〜３の結果を表１、表２（１分後から３０分後の捕捉率）及び図１（１分後の捕捉率）に示した。 The results of Examples 1 to 26 and Comparative Examples 1 to 3 are shown in Tables 1 and 2 (capture rate after 1 minute to 30 minutes) and FIG. 1 (capture rate after 1 minute).
表１、表２及び図１より明らかなように、本発明のアルデヒド捕捉剤は水溶液中において既存のアルデヒド捕捉剤と比較して、特に初期段階での高いアルデヒド捕捉性能を示した。 As is apparent from Tables 1 and 2 and FIG. 1, the aldehyde scavenger of the present invention exhibited a high aldehyde scavenging performance particularly in the initial stage compared with the existing aldehyde scavenger in an aqueous solution.
実施例２７
反応時間を２４時間としたこと以外は実施例５と同様に実施した結果、２４時間経過後もアセトアルデヒド捕捉率は９９．９％であり、本発明のアルデヒド捕捉剤は長時間経過後も高いアルデヒド捕捉性能を維持した。
Example 27
As a result of carrying out in the same manner as in Example 5 except that the reaction time was 24 hours, the acetaldehyde scavenging rate was 99.9% even after 24 hours, and the aldehyde scavenger of the present invention was a high aldehyde after a long time. Capture performance was maintained.
実施例２８〜３３（気相中のアルデヒド捕捉試験）
実施例５〜７にて調製したアルデヒド捕捉剤０．５ｍＬをアドバンテック製５Ａろ紙（直径７ｃｍ）に滴下し、６０℃で１時間乾燥した。このろ紙をテドラーバッグに封入して減圧脱気した後、１００ｐｐｍ（体積濃度）のアルデヒドガスを１Ｌ注入した。室温で１時間静置後、テドラーバッグ内のガスを２，４−ジニトロフェニルヒドラジン（ＤＮＰＨ）を担持したカートリッジ（製品名：プレセップ−Ｃ ＤＮＰＨ、和光純薬工業製）に吸着させた。このカートリッジからＤＮＰＨ−アルデヒド縮合体を溶出（溶離液＝アセトニトリル）し、溶出液中のＤＮＰＨ−アルデヒド縮合体を液体クロマトグラフ（装置名：Ａｇｉｌｅｎｔ １２２０ Ｉｎｆｉｎｉｔｙ ＬＣ、アジレント・テクノロジー製）で定量して残存アルデヒド濃度を算出した。
Examples 28 to 33 (aldehyde capture test in gas phase)
0.5 mL of the aldehyde scavenger prepared in Examples 5 to 7 was dropped onto Advantech 5A filter paper (diameter 7 cm) and dried at 60 ° C. for 1 hour. After this filter paper was sealed in a Tedlar bag and degassed under reduced pressure, 1 L of 100 ppm (volume concentration) of aldehyde gas was injected. After standing at room temperature for 1 hour, the gas in the Tedlar bag was adsorbed on a cartridge (product name: Presep-C DNPH, manufactured by Wako Pure Chemical Industries) carrying 2,4-dinitrophenylhydrazine (DNPH). The DNPH-aldehyde condensate is eluted from this cartridge (eluent = acetonitrile), and the DNPH-aldehyde condensate in the eluate is quantified by a liquid chromatograph (device name: Agilent 1220 Infinity LC, manufactured by Agilent Technologies) and remains. The aldehyde concentration was calculated.
比較例４〜９
Ｏ−置換モノヒドロキシルアミン類に代え、既存品であるケムキャッチＨ−６０００ＨＳ（ヒドラジド系、大塚化学製）、ピペラジン（アミン系）又はグリシン（アミノ酸系）を用いたこと以外は実施例２８〜３３と同様に実施した。
Comparative Examples 4-9
Examples 28 to 33 except that the existing product Chemcat H-6000HS (hydrazide type, manufactured by Otsuka Chemical), piperazine (amine type) or glycine (amino acid type) was used instead of O-substituted monohydroxylamines. It carried out like.
実施例２８〜３３及び比較例４〜９の結果を表３及び図２〜３に示す。 The results of Examples 28 to 33 and Comparative Examples 4 to 9 are shown in Table 3 and FIGS.
実施例３４
室温での静置時間を２４時間としたこと以外は実施例２８と同様に実施した結果、残存アセトアルデヒド濃度は０．９ｐｐｍ（静置時間１時間）から０．２ｐｐｍまで低減し、本発明のアルデヒド捕捉剤は長時間経過後も高いアルデヒド捕捉性能を維持した。
Example 34
As a result of carrying out in the same manner as in Example 28 except that the standing time at room temperature was 24 hours, the residual acetaldehyde concentration was reduced from 0.9 ppm (1 hour standing time) to 0.2 ppm, and the aldehyde of the present invention The scavenger maintained high aldehyde scavenging performance even after a long time.
実施例３５
実施例５にて調製したアルデヒド捕捉剤にシリカゲル（ＰＳＱ６０Ｂ 富士シリシア化学製）を添加し、水を減圧留去して６０℃で１時間乾燥した（アルコキシアミン担持量＝３重量％）。この紛体０．１ｇをテドラーバッグに封入して減圧脱気した後、１００ｐｐｍ（体積濃度）のアルデヒドガスを１Ｌ注入した。室温で１時間静置後、テドラーバッグ内のガスを実施例２８〜３３と同様に定量した結果、残存アルデヒド濃度は０．１ｐｐｍであった。
Example 35
Silica gel (PSQ60B manufactured by Fuji Silysia Chemical) was added to the aldehyde scavenger prepared in Example 5, water was distilled off under reduced pressure and dried at 60 ° C. for 1 hour (alkoxyamine loading amount = 3% by weight). After 0.1 g of this powder was sealed in a Tedlar bag and degassed under reduced pressure, 1 L of 100 ppm (volume concentration) of aldehyde gas was injected. After standing at room temperature for 1 hour, the gas in the Tedlar bag was quantified in the same manner as in Examples 28 to 33. As a result, the residual aldehyde concentration was 0.1 ppm.
比較例１０
シリカゲルのみを捕捉剤としたこと以外は実施例３５と同様に実施した結果、残存アルデヒド濃度は５０．２ｐｐｍであった。
Comparative Example 10
As a result of carrying out in the same manner as in Example 35 except that only silica gel was used as the scavenger, the residual aldehyde concentration was 50.2 ppm.
表３、図２〜３、実施例３５、及び比較例１０より明らかなように、本発明のアルデヒド捕捉剤は気相中においても既存の捕捉剤と比較して高いアルデヒド捕捉性能を示した。 As is apparent from Table 3, FIGS. 2-3, Example 35, and Comparative Example 10, the aldehyde scavenger of the present invention showed high aldehyde scavenging performance even in the gas phase as compared with existing scavengers.
実施例３６（パーティクルボード由来のアルデヒド捕捉試験）
パーティクルボード（縦１０ｃｍ、横１０ｃｍ、厚さ１ｃｍ）に、（アミノオキシ）酢酸ヘミ塩酸塩を１０重量％含有する捕捉剤の水溶液を２２．２ｇ／ｍ２の割合で塗布し、室温で２４時間乾燥させた。このパーティクルボードをテドラーバッグに空気１Ｌと共に封入し、６０℃で１時間静置後、テドラーバッグ内のガスを実施例２８〜３３と同様に定量した結果、アセトアルデヒド濃度は０．６ｐｐｍ、ホルムアルデヒド濃度は０．１ｐｐｍであった。
Example 36 (Particleboard-derived aldehyde capture test)
An aqueous solution of a scavenger containing 10% by weight of (aminooxy) acetic acid hemi-hydrochloride was applied to a particle board (10 cm long, 10 cm wide, 1 cm thick) at a rate of 22.2 g / m 2 for 24 hours at room temperature. Dried. The particle board was sealed in a Tedlar bag together with 1 L of air, allowed to stand at 60 ° C. for 1 hour, and the gas in the Tedlar bag was quantified in the same manner as in Examples 28 to 33. 1 ppm.
比較例１１
捕捉剤を用いないこと以外は実施例３６と同様に実施した結果、テドラーバッグ内のアセトアルデヒド濃度は１４．９ｐｐｍ、ホルムアルデヒド濃度は０．６ｐｐｍであった。
Comparative Example 11
As a result of carrying out in the same manner as in Example 36 except that the scavenger was not used, the acetaldehyde concentration in the Tedlar bag was 14.9 ppm and the formaldehyde concentration was 0.6 ppm.
実施例３７（ウレタンフォーム由来のアルデヒド捕捉試験）
ウレタンフォーム（縦４ｃｍ、横５ｃｍ、厚さ４ｃｍ）に、（アミノオキシ）酢酸を５重量％含有する捕捉剤の水溶液を２２．２ｇ／ｍ２の割合で塗布し、室温で２４時間乾燥させた。このウレタンフォームをテドラーバッグに空気１Ｌと共に封入し、６５℃で２時間静置後、テドラーバッグ内のガスを実施例２８〜３３と同様に定量した結果、アセトアルデヒド濃度は０．１ｐｐｍ未満、ホルムアルデヒド濃度は０．１ｐｐｍであった。
Example 37 (urethane foam-derived aldehyde capture test)
An aqueous solution of a scavenger containing 5% by weight of (aminooxy) acetic acid was applied to urethane foam (length 4 cm, width 5 cm, thickness 4 cm) at a rate of 22.2 g / m 2 and dried at room temperature for 24 hours. . This urethane foam was sealed in a Tedlar bag together with 1 L of air, and allowed to stand at 65 ° C. for 2 hours. The gas in the Tedlar bag was quantified in the same manner as in Examples 28 to 33. 0.1 ppm.
比較例１２
捕捉剤を用いないこと以外は実施例３７と同様に実施した結果、テドラーバッグ内のアセトアルデヒド濃度は０．３ｐｐｍ、ホルムアルデヒド濃度は０．８ｐｐｍであった。
Comparative Example 12
As a result of carrying out in the same manner as in Example 37 except that no scavenger was used, the acetaldehyde concentration in the Tedlar bag was 0.3 ppm and the formaldehyde concentration was 0.8 ppm.
比較例１３
捕捉剤として、（アミノオキシ）酢酸水溶液の代わりにケムキャッチＨ−６０００ＨＳ（大塚化学製）水溶液を用いたこと以外は実施例３７と同様に実施した結果、テドラーバッグ内のアセトアルデヒド濃度は０．３ｐｐｍ、ホルムアルデヒド濃度は０．２ｐｐｍであった。
Comparative Example 13
As a scavenger, the same procedure as in Example 37 was performed except that Chemcat H-6000HS (manufactured by Otsuka Chemical) was used instead of the (aminooxy) acetic acid aqueous solution. As a result, the acetaldehyde concentration in the Tedlar bag was 0.3 ppm, The formaldehyde concentration was 0.2 ppm.
実施例３６〜３７と比較例１１〜１３より、本発明のアルデヒド捕捉剤はパーティクルボードやウレタンフォームのようなアルデヒド発生源に適用することで、アルデヒド発生量を低減することができ、且つ既存のアルデヒド捕捉剤と比較して優れたアルデヒド捕捉効果を示した。 From Examples 36 to 37 and Comparative Examples 11 to 13, the aldehyde scavenger of the present invention can be applied to an aldehyde generation source such as particle board or urethane foam to reduce the amount of aldehyde generated and Compared with the aldehyde scavenger, it showed an excellent aldehyde scavenging effect.
本発明のアルデヒド捕捉剤は、アルデヒド類を速やかに且つ持続的に捕捉する。その結果、人体に有害なアルデヒド類を低減し、ヒトの生活環境を改善することができる。 The aldehyde scavenger of the present invention captures aldehydes quickly and continuously. As a result, it is possible to reduce aldehydes that are harmful to the human body and improve the human living environment.
Claims (4)
ハロゲン原子；
炭素数１〜６のアルキルオキシ基；
炭素数１〜６のハロアルキル基；
炭素数１〜６のハロアルキルオキシ基；
カルボキシ基；
ヒドロキシ基；
メルカプト基；
シアノ基；
ニトロ基；
ハロゲン原子、炭素数１〜６のアルキル基、炭素数１〜６のアルキルオキシ基、炭素数１〜６のハロアルキル基、炭素数１〜６のハロアルキルオキシ基、カルボキシ基、ヒドロキシ基、メルカプト基、シアノ基若しくはニトロ基で置換されていてもよい炭素数６〜１４のアリール基；
ハロゲン原子、炭素数１〜６のアルキル基、炭素数１〜６のアルキルオキシ基、炭素数１〜６のハロアルキル基、炭素数１〜６のハロアルキルオキシ基、カルボキシ基、ヒドロキシ基、メルカプト基、シアノ基若しくはニトロ基で置換されていてもよい炭素数４〜１４のヘテロアリール基；
下記一般式（２）で表されるアルコキシカルボニル基；
及び
下記一般式（３）で表されるカルバモイル基；
からなる群より選ばれる１つ以上の置換基で置換されていてもよい炭素数１〜１８の直鎖状、分岐状若しくは環状のアルキル基を表す。］
カルボキシ基；
ヒドロキシ基；
メルカプト基；
ハロゲン原子；
炭素数１〜６のアルキルオキシ基；
炭素数１〜６のハロアルキルオキシ基；
炭素数６〜１４のアリール基；
及び
炭素数４〜１４のヘテロアリール基；
からなる群より選ばれる１つ以上の置換基で置換されていてもよい炭素数１〜１８の直鎖状、分岐状若しくは環状のアルキル基を表す。］
カルボキシ基；
ヒドロキシ基；
メルカプト基；
ハロゲン原子；
炭素数１〜６のアルキルオキシ基；
炭素数１〜６のハロアルキルオキシ基；
炭素数６〜１４のアリール基；
及び
炭素数４〜１４のヘテロアリール基；
からなる群より選ばれる１つ以上の置換基で置換されていてもよい炭素数１〜１８の直鎖状、分岐状若しくは環状のアルキル基、
炭素数６〜１４のアリール基、
炭素数４〜１４のヘテロアリール基、
又は
水素原子を表す。］ The aldehyde scavenger according to claim 1, comprising at least one O-substituted monohydroxylamine represented by the following general formula (1) or a chemically acceptable salt thereof.
A halogen atom;
An alkyloxy group having 1 to 6 carbon atoms;
A haloalkyl group having 1 to 6 carbon atoms;
A haloalkyloxy group having 1 to 6 carbon atoms;
A carboxy group;
A hydroxy group;
A mercapto group;
A cyano group;
A nitro group;
A halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a haloalkyloxy group having 1 to 6 carbon atoms, a carboxy group, a hydroxy group, a mercapto group, An aryl group having 6 to 14 carbon atoms which may be substituted with a cyano group or a nitro group;
A halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a haloalkyloxy group having 1 to 6 carbon atoms, a carboxy group, a hydroxy group, a mercapto group, A heteroaryl group having 4 to 14 carbon atoms which may be substituted with a cyano group or a nitro group;
An alkoxycarbonyl group represented by the following general formula (2);
And a carbamoyl group represented by the following general formula (3);
Represents a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms which may be substituted with one or more substituents selected from the group consisting of: ]
A carboxy group;
A hydroxy group;
A mercapto group;
A halogen atom;
An alkyloxy group having 1 to 6 carbon atoms;
A haloalkyloxy group having 1 to 6 carbon atoms;
An aryl group having 6 to 14 carbon atoms;
And a heteroaryl group having 4 to 14 carbon atoms;
Represents a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms which may be substituted with one or more substituents selected from the group consisting of: ]
A carboxy group;
A hydroxy group;
A mercapto group;
A halogen atom;
An alkyloxy group having 1 to 6 carbon atoms;
A haloalkyloxy group having 1 to 6 carbon atoms;
An aryl group having 6 to 14 carbon atoms;
And a heteroaryl group having 4 to 14 carbon atoms;
A linear, branched or cyclic alkyl group having 1 to 18 carbon atoms which may be substituted with one or more substituents selected from the group consisting of:
An aryl group having 6 to 14 carbon atoms,
A heteroaryl group having 4 to 14 carbon atoms,
Or represents a hydrogen atom. ]
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| CN201780071027.1A CN109963922B (en) | 2016-12-28 | 2017-12-27 | Aldehyde scavenger and method for removing aldehyde |
| EP17888620.6A EP3564334A4 (en) | 2016-12-28 | 2017-12-27 | Aldehyde scavenger and aldehyde removal method |
| PCT/JP2017/047018 WO2018124208A1 (en) | 2016-12-28 | 2017-12-27 | Aldehyde scavenger and aldehyde removal method |
| US16/466,232 US11439721B2 (en) | 2016-12-28 | 2017-12-27 | Aldehyde scavenger and method for removing aldehydes |
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