JP7456819B2 - ベンゾトリアゾール系紫外線吸収単位を含む共重合体及びその組成物 - Google Patents
ベンゾトリアゾール系紫外線吸収単位を含む共重合体及びその組成物 Download PDFInfo
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- JP7456819B2 JP7456819B2 JP2020049253A JP2020049253A JP7456819B2 JP 7456819 B2 JP7456819 B2 JP 7456819B2 JP 2020049253 A JP2020049253 A JP 2020049253A JP 2020049253 A JP2020049253 A JP 2020049253A JP 7456819 B2 JP7456819 B2 JP 7456819B2
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- 229920001577 copolymer Polymers 0.000 title claims description 118
- 239000000203 mixture Substances 0.000 title claims description 35
- 239000012964 benzotriazole Substances 0.000 title claims description 11
- 238000010521 absorption reaction Methods 0.000 title description 33
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title description 4
- 239000000178 monomer Substances 0.000 claims description 175
- -1 benzotriazole compound Chemical class 0.000 claims description 173
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000004185 ester group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000011593 sulfur Substances 0.000 claims description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
- 229920002554 vinyl polymer Polymers 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
- 125000003368 amide group Chemical group 0.000 claims description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 100
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 44
- 150000002430 hydrocarbons Chemical group 0.000 description 36
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- ASKIVFGGGGIGKH-UHFFFAOYSA-N 2,3-dihydroxypropyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(O)CO ASKIVFGGGGIGKH-UHFFFAOYSA-N 0.000 description 22
- 239000004359 castor oil Substances 0.000 description 22
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 22
- 239000010410 layer Substances 0.000 description 22
- 125000002723 alicyclic group Chemical group 0.000 description 20
- 230000003287 optical effect Effects 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
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- 125000000217 alkyl group Chemical group 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 239000004166 Lanolin Substances 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 12
- 150000005215 alkyl ethers Chemical class 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
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- 239000007787 solid Substances 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 10
- 150000003863 ammonium salts Chemical class 0.000 description 10
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 10
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- FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000000600 sorbitol Substances 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 238000000862 absorption spectrum Methods 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 235000021317 phosphate Nutrition 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 229930182558 Sterol Natural products 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 150000003432 sterols Chemical class 0.000 description 4
- 235000003702 sterols Nutrition 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
- JPPRXACMNPYJNK-UHFFFAOYSA-N 1-docosoxydocosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCCCCCC JPPRXACMNPYJNK-UHFFFAOYSA-N 0.000 description 3
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 3
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- XJRLKUOFBZMRBR-UHFFFAOYSA-N 2-phenylbenzotriazole Chemical group C1=CC=CC=C1N1N=C2C=CC=CC2=N1 XJRLKUOFBZMRBR-UHFFFAOYSA-N 0.000 description 3
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 229920001214 Polysorbate 60 Polymers 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 125000003172 aldehyde group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
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- 125000001651 cyanato group Chemical group [*]OC#N 0.000 description 3
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- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 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 3
- 125000005462 imide group Chemical group 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
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- 238000004519 manufacturing process Methods 0.000 description 3
- 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 3
- 238000000034 method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 125000000101 thioether group Chemical group 0.000 description 3
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- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 2
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- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
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- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 2
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- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 2
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- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
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- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 238000002845 discoloration Methods 0.000 description 1
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical group 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- JLHMVTORNNQCRM-UHFFFAOYSA-N ethylphosphine Chemical group CCP JLHMVTORNNQCRM-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- QAOXMQCWUWZZNC-UHFFFAOYSA-N gamma-Methyl-alpha-butylen-alpha-carbonsaeure Natural products CC(C)C=CC(O)=O QAOXMQCWUWZZNC-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229940074050 glyceryl myristate Drugs 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- PNLSTDKQAPNMDU-UHFFFAOYSA-N hept-1-enylbenzene Chemical compound CCCCCC=CC1=CC=CC=C1 PNLSTDKQAPNMDU-UHFFFAOYSA-N 0.000 description 1
- KETWBQOXTBGBBN-UHFFFAOYSA-N hex-1-enylbenzene Chemical compound CCCCC=CC1=CC=CC=C1 KETWBQOXTBGBBN-UHFFFAOYSA-N 0.000 description 1
- JYVPKRHOTGQJSE-UHFFFAOYSA-M hexyl(trimethyl)azanium;bromide Chemical compound [Br-].CCCCCC[N+](C)(C)C JYVPKRHOTGQJSE-UHFFFAOYSA-M 0.000 description 1
- FZCCKDYTOZQJJR-UHFFFAOYSA-M hexyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCC[N+](C)(C)C FZCCKDYTOZQJJR-UHFFFAOYSA-M 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- KKSDGJDHHZEWEP-UHFFFAOYSA-N m-hydroxycinnamic acid Natural products OC(=O)C=CC1=CC=CC(O)=C1 KKSDGJDHHZEWEP-UHFFFAOYSA-N 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- SAWKFRBJGLMMES-UHFFFAOYSA-N methylphosphine Chemical group PC SAWKFRBJGLMMES-UHFFFAOYSA-N 0.000 description 1
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 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
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 1
- ZEMHQYNMVKDBFJ-UHFFFAOYSA-N n-(3-hydroxypropyl)prop-2-enamide Chemical compound OCCCNC(=O)C=C ZEMHQYNMVKDBFJ-UHFFFAOYSA-N 0.000 description 1
- YBWQZBVPWXXJKQ-UHFFFAOYSA-N n-(4-hydroxybutyl)prop-2-enamide Chemical compound OCCCCNC(=O)C=C YBWQZBVPWXXJKQ-UHFFFAOYSA-N 0.000 description 1
- BHVGUZQGBGRQMU-UHFFFAOYSA-N n-(5-hydroxypentyl)prop-2-enamide Chemical compound OCCCCCNC(=O)C=C BHVGUZQGBGRQMU-UHFFFAOYSA-N 0.000 description 1
- PSJKLCSUGFKSDR-UHFFFAOYSA-N n-(6-hydroxyhexyl)prop-2-enamide Chemical compound OCCCCCCNC(=O)C=C PSJKLCSUGFKSDR-UHFFFAOYSA-N 0.000 description 1
- CPHCIYGRSFZNRD-UHFFFAOYSA-N n-methyl-1-(4,5,6,7-tetrahydro-1h-indazol-3-yl)methanamine Chemical compound C1CCCC2=C1NN=C2CNC CPHCIYGRSFZNRD-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- KNZIIQMSCLCSGZ-UHFFFAOYSA-N non-1-enylbenzene Chemical compound CCCCCCCC=CC1=CC=CC=C1 KNZIIQMSCLCSGZ-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- RCALDWJXTVCBAZ-UHFFFAOYSA-N oct-1-enylbenzene Chemical compound CCCCCCC=CC1=CC=CC=C1 RCALDWJXTVCBAZ-UHFFFAOYSA-N 0.000 description 1
- XCOHAFVJQZPUKF-UHFFFAOYSA-M octyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](C)(C)C XCOHAFVJQZPUKF-UHFFFAOYSA-M 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical compound C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 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 1
- KHMYONNPZWOTKW-UHFFFAOYSA-N pent-1-enylbenzene Chemical compound CCCC=CC1=CC=CC=C1 KHMYONNPZWOTKW-UHFFFAOYSA-N 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
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical group PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 229940093625 propylene glycol monostearate Drugs 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 229940071139 pyrrolidone carboxylate Drugs 0.000 description 1
- DCBSHORRWZKAKO-UHFFFAOYSA-N rac-1-monomyristoylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(O)CO DCBSHORRWZKAKO-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 229940083575 sodium dodecyl sulfate Drugs 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 229940057950 sodium laureth sulfate Drugs 0.000 description 1
- 229950005425 sodium myristyl sulfate Drugs 0.000 description 1
- GOZDTZWAMGHLDY-UHFFFAOYSA-L sodium picosulfate Chemical compound [Na+].[Na+].C1=CC(OS(=O)(=O)[O-])=CC=C1C(C=1N=CC=CC=1)C1=CC=C(OS([O-])(=O)=O)C=C1 GOZDTZWAMGHLDY-UHFFFAOYSA-L 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 description 1
- MWZFQMUXPSUDJQ-KVVVOXFISA-M sodium;[(z)-octadec-9-enyl] sulfate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCOS([O-])(=O)=O MWZFQMUXPSUDJQ-KVVVOXFISA-M 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- UPUIQOIQVMNQAP-UHFFFAOYSA-M sodium;tetradecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCOS([O-])(=O)=O UPUIQOIQVMNQAP-UHFFFAOYSA-M 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 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 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- WXBXVVIUZANZAU-CMDGGOBGSA-N trans-2-decenoic acid Chemical compound CCCCCCC\C=C\C(O)=O WXBXVVIUZANZAU-CMDGGOBGSA-N 0.000 description 1
- PAWGRNGPMLVJQH-ZHACJKMWSA-N trans-2-dodecenoic acid Chemical compound CCCCCCCCC\C=C\C(O)=O PAWGRNGPMLVJQH-ZHACJKMWSA-N 0.000 description 1
- KKSDGJDHHZEWEP-SNAWJCMRSA-N trans-3-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=CC(O)=C1 KKSDGJDHHZEWEP-SNAWJCMRSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- IGBBVTAVILYDIO-MDZDMXLPSA-N trans-undec-2-enoic acid Chemical compound CCCCCCCC\C=C\C(O)=O IGBBVTAVILYDIO-MDZDMXLPSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical group CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical group C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 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
- SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 0.000 description 1
- AQZSPJRLCJSOED-UHFFFAOYSA-M trimethyl(octyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(C)C AQZSPJRLCJSOED-UHFFFAOYSA-M 0.000 description 1
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical group CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical group CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
Description
(モノマー(A))
下記式(I):
(モノマー(B))
カルボキシ基含有ビニルモノマー又はその塩
(モノマー(C))
ヒドロキシアルキル基含有ビニルモノマー
(モノマー(A))
本発明の共重合体において、モノマー(A)は、上記式(I)で表わされるベンゾトリアゾール化合物である。
本発明において、置換基とは「芳香族基、不飽和基、窒素含有基、硫黄含有基、酸素含有基、リン含有基、脂環式基、及びハロゲン原子から選ばれる1価もしくは2価の基」等の耐熱性、屈折率、融点、耐光性、樹脂に対する相溶性等を調整できる基が含まれ、例えば、次のものが挙げられる。
[2] [1]において、置換基が炭素数1~10の炭化水素基、及びヒドロキシ基から選ばれる少なくとも1種である。
[3] [2]において、置換基が炭素数1~8の炭化水素基、及びヒドロキシ基から選ばれる少なくとも1種である。
[4] [1]~[3]のいずれかにおいて、置換基の炭化水素基が直鎖又は分岐のアルキル基である。
[5] [4]において、置換基がメチル基、t-ブチル基、及びヒドロキシ基から選ばれる少なくとも1種である。
[6] [5]において、置換基がメチル基、t-ブチル基、及びヒドロキシ基から選ばれる少なくとも1種であり、かつヒドロキシ基は1つ以下である。
[7] [1]から[6]のいずれかにおいて、置換基の数が2~4個である。
[8] [1]から[7]のいずれかにおいて、R1~R4のいずれかの位置に置換基を有し、それ以外のR1~R5は水素原子である。
[9] [1]から[8]のいずれかにおいて、R1、R2、R4のいずれかの位置に置換基を有し、それ以外のR1~R5は水素原子である。
[10] [9]において、R1はヒドロキシ基、R2はt-ブチル基、R4はメチル基であり、R3、R5は水素原子である。
本発明の共重合体において、モノマー(B)は、カルボキシ基含有ビニルモノマー又はその塩である。
本発明の共重合体において、モノマー(C)は、ヒドロキシアルキル基含有ビニルモノマーである。
本発明の共重合体には、モノマー(A)、(B)、(C)以外に、その他のモノマーを用いることができる。このようなモノマーとしては、特に限定されないが、例えば、次のモノマー等が挙げられる。
アクリロニトリル、メタクリロニトリル、α-クロロアクリロニトリル、フマロニトリルが挙げられる。
モノマー(E)は、エステル基含有ビニルモノマーである。
エステル基含有ビニルモノマーは、RA9RA10C=CRA11RA12で表され、RA9~RA12のうち少なくとも1つ、好ましくは1つがエステル基である。RA9~RA12のうちエステル基含有基以外は、水素原子、炭素数1~18の炭化水素基から選ばれるいずれかの基である。炭化水素基は、アルキル基が好ましく、エステル基含有基以外は、水素原子、炭素数が1~4が好ましく、水素原子、炭素数1がより好ましい。
上記以外のモノマーである。具体的には、特に限定されないが、例えば、スチレン系モノマー、酢酸ビニル、プロピオン酸ビニル、塩化ビニル、塩化ビニリデン、ジメチルアクリルアミド、ヘキサジエン等が挙げられる。スチレン系モノマーとしては、特に限定されないが、例えば、スチレン、α-メチルスチレン、メチルスチレン、ジメチルスチレン、トリメチルスチレン、エチルスチレン、ジエチルスチレン、トリエチルスチレン、プロピルスチレン、イソプロピルスチレン、ブチルスチレン、イソブチルスチレン、t-ブチルスチレン、s-ブチルスチレン、ペンチルスチレン、ヘキシルスチレン、ヘプチルスチレン、オクチルスチレン等のアルキルスチレン;クロロスチレン、フルオロスチレン、ブロモスチレン、ジブロモスチレン、ヨードスチレン等のハロゲン化スチレン;p-メトキシスチレン等のアルコキシスチレン;p-フェニルスチレン等のアリールスチレン;スチレンスルホン酸又はそのアルカリ金属塩、ニトロスチレン、アミノスチレン、ヒドロキシスチレン、4(トリメトキシシリル)スチレン等が挙げられる。これらの中でもスチレン、酢酸ビニル、プロピオン酸ビニル、ジメチルアクリルアミドが好ましい。
以下、本発明の共重合体について説明する。
本発明の共重合体は、モノマー(A)と、モノマー(B)及び/又はモノマー(C)とを含むモノマー成分の共重合体である。
第1の例では、モノマー成分が、モノマー(A)と、モノマー(B)とを含む。この場合、モル比(A)/(B)は0.7以下が好ましく、0.5以下がより好ましく、0.09以下が更に好ましく、0.05以下が特に好ましい。
第2の例では、モノマー成分が、モノマー(A)と、モノマー(C)とを含む。この場合、モル比(A)/(C)は0.7以下が好ましく、0.5以下がより好ましく、0.09以下が更に好ましく、0.05以下が特に好ましい。
第3の例では、モノマー成分が、モノマー(A)と、モノマー(B)と、モノマー(C)とを含む。この場合、モル比(A)/((B)+(C))は0.7以下が好ましく、0.5以下がより好ましく、0.09以下が更に好ましく、0.05以下が特に好ましい。
第1の例では、モノマー成分が、モノマー(A)と、モノマー(B)とを含む。この場合、モル比(A)/(B)は、0.001以上が好ましく、0.01以上がより好ましく、0.05以上が更に好ましく、0.1以上が特に好ましい。
第2の例では、モノマー成分が、モノマー(A)と、モノマー(C)とを含む。この場合、モル比(A)/(C)は、0.001以上が好ましく、0.01以上がより好ましく、0.05以上が更に好ましく、0.1以上が特に好ましい。
第3の例では、モノマー成分が、モノマー(A)と、モノマー(B)と、モノマー(C)とを含む。この場合、モル比(A)/((B)+(C))は、0.001以上が好ましく、0.01以上がより好ましく、0.05以上が更に好ましく、0.1以上が特に好ましい。
本発明の共重合体において、モノマー(A)、(B)、(C)の合計モル比は、特に限定されないが、全モノマーを基準として90モル%以上、80モル%以上、又は50モル%以上であってよい。
本発明の水性組成物は、本発明の共重合体と、水とを含む、液状、分散液又は乳化物の水性組成物である。
界面活性剤は、特に限定されず、一般的な界面活性剤を使用することができる。界面活性剤としては、カチオン性界面活性剤、アニオン性界面活性剤、非イオン性界面活性剤、両性イオン界面活性剤及びシリコーン系界面活性剤から適宜選択して用いることができ、これらは1種単独で使用してもよく、2種以上を組み合わせて使用してもよい。
下記原料を用い、各モノマーからなる共重合体を合成した。
モノマーA1、2は、国際公開第2019/087983号に記載の方法で合成した。モノマーA3、4は、以下に示す方法で合成した。表1、2中のそれぞれのモノマーはアクリル酸、メタクリル酸2-ヒドロキシエチル、アクリル酸メチル、アクリロニトリル、スチレン、2-[2-ヒドロキシ-5-[2-(メタクリロイルオキシ)エチル]フェニル]-2H-ベンゾトリアゾールは東京化成工業(株)、28%アンモニア水は関東化学(株)の試薬を用いた。
2-(2-ヒドロキシ-3-tert-ブチル-5-メチルフェニル)-5-クロロベンゾトリアゾール(50g、0.16mol)、3-メルカプト-1-プロパノール(22g、0.24mol)、炭酸カリウム(48g、0.35mol)を、DMF125g中で、12時間加熱撹拌を行った。反応終了後、イオン交換水を加え、濾過、精製をすることで、黄色固体の中間体1を得た。
FT-IR(KBr):2956cm-1:O-H伸縮振動 1726cm-1:C=O伸縮振動 1485, 1392cm-1:トリアゾール環伸縮振動
1H-NMR (CDCl3 400MHz): δ 1.49 (S, 9H, -Ph-OH-CH3-C(CH 3)3) , 2.11 (quin, 2H, -O-CH2CH 2CH2-S-) , 2.39 (s, 3H, -Ph-OH-CH 3-C(CH3)3) , 3.13 (t, 2H, -O-CH2CH2CH 2-S-), 4.32 (t, 2H, -O-CH 2CH2CH2-S-), 5.85 (d, 1H, CH 2=CH-C(=O)-O-), 6.14 (quin, 1H, CH2= CH-C(=O)-O-), 6.42 (d, 1H, CH 2=CH-C(=O)-O-), 7.17 (s, 1H), 7.40 (d, 1H), 7.76 (s, 1H), 7.82 (d, 1H), 8.05 (s, 1H), (insg.5arom. CH), 11.58 (s, 1H, -Ph-OH-CH3-C(CH3)3)
13C-NMR (CDCl3 400MHz): δ 20.9 (-Ph-OH-CH3-C(CH3)3), 28.0 (-Ph-OH-CH3-C(CH3)3), 29.5 (-Ph-OH-CH3-C(CH3)3) , 29.9 (-O-CH2 CH2CH2-S), 35.4 (-O-CH2CH2 CH2-S), 62.8 (-O-CH2CH2CH2-S), 114.6, 117.8, 119.3, 128.9, 129.4 (CHarom), 125.4, 141.4, 143.3 (C arom), 128.3 (Carom-CH3), 136.8 (C arom-S), 139.2 (C arom-C(CH3)3), 146.7(C arom-OH), 128.3 (CH2=CH -C(=O)-O-), 131.1 (CH2=CH-C(=O)-O-), 166.1 (CH2=CH-C(=O)-O-)
2-(2-ヒドロキシ-3-tert-ブチル-5-メチルフェニル)-5-クロロベンゾトリアゾール(5.6g、18mmol)、4-ヒドロキシベンゼンチオール(2.9g、23mmol)、炭酸カリウム(5.4g、39mmol)を、DMF17g中で、8時間、加熱撹拌を行った。反応終了後、イオン交換水を加え結晶を析出させ、濾過、精製をすることで、黄色固体の中間体2を得た。
FT-IR(KBr):2959cm-1:O-H伸縮振動 1747cm-1:C=O伸縮振動 1487, 1403cm-1:トリアゾール環伸縮振動
1H-NMR (CDCl3 400MHz): δ 1.48 (s, 9H, -Ph-OH-CH3-C(CH 3)3) , 2.37 (s, 3H, -Ph-OH-CH 3 -C(CH3)3), 6.04 (d, 1H, CH 2=CH-C(=O)-O-), 6.34 (quin, 1H, CH2= CH-C(=O)-O-), 6.61 (d, 1H, CH 2=CH-C(=O)-O-), 7.17‐7.19 (m, 3H), 7.35 (d, 1H), 7.50 (d, 2H), 7.71 (s, 1H), 7.82 (d, 1H), 8.04 (s, 1H), (insg.9arom. CH), 11.55 (s, 1H, -Ph-OH-CH 3 -C(CH3)3)
13C-NMR (CDCl3 400MHz): δ 20.9 (-Ph-OH-CH3-C(CH3)3), 29.5 (-Ph-OH-CH3-C(CH3)3), 29.5 (-Ph-OH-CH3-C(CH3)3) ,
116.9, 118.1, 119.4, 129.0, 129.7, 125.3, 133.9 (CHarom), 125.3, 141.7, 143.2 (C arom), 128.2 (Carom-CH3), 128.9 (C arom-S), 137.1 (C arom-S), 139.2 (C arom-C(CH3)3), 150.7(C arom-O-), 146.7(C arom-OH), 128.3 (CH2=CH-C(=O)-O-), 131.0 (CH2=CH-C(=O)-O-), 164.2 (CH2=CH-C(=O)-O-)
モノマーB1:アクリル酸
モノマーB2:アクリル酸アンモニウム塩
共重合体中のアクリル酸(B1)のカルボキシ基をアンモニア水でアンモニウム塩化した構成成分(繰り返し単位)
モノマー(C)
モノマーC1:メタクリル酸2-ヒドロキシエチル
モノマー(D)
モノマーD1:アクリル酸メチル
モノマー(E)
モノマーE1:アクリロニトリル
モノマー(F)
モノマーF1:スチレン
モノマー(G)
モノマーG1:2-[2-ヒドロキシ-5-[2-(メタクリロイルオキシ)エチル]フェニル]-2H-ベンゾトリアゾール
<共重合体1>
モノマーA1(4.2mmol)、アクリル酸(42mmol)、イソプロピルアルコール:IPA(3.8g)を入れ、窒素置換した後、重合開始剤として2,2’-アゾビス(イソブチロニトリル)(0.18mmol)を加え、100℃で3時間加熱攪拌することで共重合反応を行った。反応後、真空乾燥器にてIPAを除去し共重合体1が得られ、さらに、その共重合体が固形分20質量%となる様、イオン交換水を添加、混合し、モノマーA1とモノマーB1からなる共重合体の水性組成物1を得た。
上記共重合体1の合成と同様な方法で、表1、2に示すモノマーA1~4、B1、C1、D1、E1、F1を、各モル比で共重合反応し各共重合体を、さらに、表1、2の固形分となる様、イオン交換水を添加、混合し、各共重合体の水性組成物2、6~8、10~18を得た。
モノマーA1(2.1mmol)、アクリル酸(42mmol)、イソプロピルアルコール:IPA(3.8g)を入れ、窒素置換した後、2,2’-アゾビス(イソブチロニトリル)(0.18mmol)を加え、100℃で3時間加熱攪拌することで共重合反応を行った。反応後、真空乾燥器にてIPAを除去し、乾燥した共重合体中のモノマーB1のカルボキシル基1molに対して、アンモニアが0.25molのモル比となるよう28%アンモニア水を添加、反応し共重合体3(水性組成物)が得られ、さらに、その共重合体が固形分20質量%となる様、イオン交換水を添加、混合し、モノマーA1、モノマーB1、モノマーB2からなる共重合体の水性組成物3を得た。
上記共重合体溶液3の合成と同様な方法で、表1、2に示すモノマーA1、B1、F1、G1を、各モル比で共重合反応した後、モノマーB1とB2の比率が表1、2となるように28%アンモニア水を添加、反応し、各重合体(水性組成物)を、さらに、表1、2の固形分となる様、イオン交換水を添加、混合し、各共重合体の水性組成物4、5、9、19~22を得た。
3-1.水性組成物の外観
上記で得られた共重合体溶液の外観を観察し、表1、2に記載した。
実施例1~20(共重合体1~20)の共重合体は、親水性が高く、沈殿がない安定性が高い水溶液、分散液が得られた。これら共重合体の水溶液、分散液は、1ヶ月間、25℃の恒温槽で保管し、沈殿を生じず経時安定性に優れていることを確認した。
上記で得られた各共重合体の水性組成物1~20を固形分0.02~0.08質量%にイオン交換水で希釈し、紫外可視赤外分光光度計(日立ハイテクサイエンス製UH4150V)を用いて吸収スペクトルを測定し、最大吸収波長を確認した(表1)。また、共重合体5の水性組成物(0.08質量%水溶液)のスペクトルを図1に示す。
|330~390nmの波長領域にある吸収ピークの長波長側の傾き|=|(ピークエンドの吸光度-330~390nmの波長領域にある吸収ピークの吸光度)/(ピークエンドの吸収波長-330~390nmの波長領域にある吸収ピークの波長)|
Claims (10)
- 次のモノマー(A)と、モノマー(B)及び/又はモノマー(C)とを含み、モノマー(B)を含む場合、モノマー(A)とモノマー(B)とのモル比(A)/(B)が0.01以上0.5以下であり、モノマー(C)を含む場合、モノマー(A)とモノマー(C)とのモル比(A)/(C)が0.01以上0.09以下であるモノマー成分の共重合体。
(モノマー(A))
下記式(I):
(モノマー(B))
下記式:
(モノマー(C))
下記式:
- 前記モノマー成分が、前記モノマー(A)と、前記モノマー(B)とを含む請求項1に記載の共重合体。
- 前記モノマー成分が、前記モノマー(A)と、前記モノマー(C)とを含む請求項1に記載の共重合体。
- 前記モノマー成分が、前記モノマー(A)と、前記モノマー(B)と、前記モノマー(C)とを含む請求項1に記載の共重合体。
- 更にモノマー成分としてアクリロニトリルを含む請求項1~4のいずれか一項に記載の共重合体。
- 更にモノマー成分としてエステル基含有ビニルモノマーを含む請求項1~5のいずれか一項に記載の共重合体。
- 更にモノマー成分としてスチレン系モノマーを含む請求項1~6のいずれか一項に記載の共重合体。
- 式(i-1)におけるlが0である請求項1~7のいずれか一項に記載の共重合体。
- 式(i-2)におけるXは、アルキレン基-(CH2)n-(nは1以上の整数を示す。)又はフェニレン基である請求項1~8のいずれか一項に記載の共重合体。
- 請求項1~9のいずれか一項に記載の共重合体と、水とを含む水性組成物。
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WO2019087983A1 (ja) | 2017-10-31 | 2019-05-09 | ミヨシ油脂株式会社 | ベンゾトリアゾール化合物 |
WO2019216266A1 (ja) | 2018-05-08 | 2019-11-14 | 株式会社Adeka | 化合物、潜在性添加剤、組成物、硬化物、硬化物の製造方法及び組成物の製造方法 |
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