JP6367913B2 - 染料としてのベンゾチアゾール−2−イルアゾ−フェニル化合物、前記染料を含む組成物、及びこのような組成物の硬化度を決定する方法 - Google Patents
染料としてのベンゾチアゾール−2−イルアゾ−フェニル化合物、前記染料を含む組成物、及びこのような組成物の硬化度を決定する方法 Download PDFInfo
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- JP6367913B2 JP6367913B2 JP2016502096A JP2016502096A JP6367913B2 JP 6367913 B2 JP6367913 B2 JP 6367913B2 JP 2016502096 A JP2016502096 A JP 2016502096A JP 2016502096 A JP2016502096 A JP 2016502096A JP 6367913 B2 JP6367913 B2 JP 6367913B2
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- alkylene
- ester
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- 239000000203 mixture Substances 0.000 title claims description 101
- 238000000034 method Methods 0.000 title claims description 29
- -1 Benzothiazol-2-ylazo-phenyl compounds Chemical class 0.000 title claims description 18
- 239000000975 dye Substances 0.000 title description 19
- 150000001875 compounds Chemical class 0.000 claims description 79
- 239000002952 polymeric resin Substances 0.000 claims description 33
- 229920003002 synthetic resin Polymers 0.000 claims description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
- 150000003254 radicals Chemical class 0.000 claims description 29
- 238000002835 absorbance Methods 0.000 claims description 28
- 239000003999 initiator Substances 0.000 claims description 27
- 239000000178 monomer Substances 0.000 claims description 26
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 24
- 125000002947 alkylene group Chemical group 0.000 claims description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 20
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 19
- 239000000919 ceramic Substances 0.000 claims description 19
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 11
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 11
- 125000000732 arylene group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 239000011347 resin Substances 0.000 claims description 10
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 8
- 239000011324 bead Substances 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- 150000007970 thio esters Chemical class 0.000 claims description 8
- 150000003568 thioethers Chemical class 0.000 claims description 8
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- 229920006337 unsaturated polyester resin Polymers 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000005504 styryl group Chemical group 0.000 claims description 5
- 229920001567 vinyl ester resin Polymers 0.000 claims description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
- 239000004927 clay Substances 0.000 claims description 4
- 239000010459 dolomite Substances 0.000 claims description 4
- 229910000514 dolomite Inorganic materials 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 239000010445 mica Substances 0.000 claims description 4
- 229910052618 mica group Inorganic materials 0.000 claims description 4
- 239000000454 talc Substances 0.000 claims description 4
- 229910052623 talc Inorganic materials 0.000 claims description 4
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 claims description 3
- 239000010456 wollastonite Substances 0.000 claims description 3
- 229910052882 wollastonite Inorganic materials 0.000 claims description 3
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000000945 filler Substances 0.000 description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 238000001723 curing Methods 0.000 description 37
- 239000000463 material Substances 0.000 description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000008439 repair process Effects 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- LVDNXHCLMAIUDS-UHFFFAOYSA-N 3-[n-(2-hydroxyethyl)-4-[(6-nitro-1,3-benzothiazol-2-yl)diazenyl]anilino]propanenitrile Chemical compound C1=CC(N(CCC#N)CCO)=CC=C1N=NC1=NC2=CC=C([N+]([O-])=O)C=C2S1 LVDNXHCLMAIUDS-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 108700042658 GAP-43 Proteins 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- 150000001451 organic peroxides Chemical group 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- FHNINJWBTRXEBC-UHFFFAOYSA-N Sudan III Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 FHNINJWBTRXEBC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 4
- 238000005562 fading Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 150000003440 styrenes Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical class O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 description 3
- ALSRTYWDWQUGNN-UHFFFAOYSA-N 2-[N-(2-cyanoethyl)-4-[(6-nitro-1,3-benzothiazol-2-yl)diazenyl]anilino]ethyl prop-2-enoate Chemical compound C(#N)CCN(CCOC(C=C)=O)C1=CC=C(C=C1)N=NC=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-] ALSRTYWDWQUGNN-UHFFFAOYSA-N 0.000 description 3
- JBQIJZUDJPCDQU-UHFFFAOYSA-N 2-[n-(2-cyanoethyl)-4-[(6-nitro-1,3-benzothiazol-2-yl)diazenyl]anilino]ethyl 2-methylprop-2-enoate Chemical compound C1=CC(N(CCC#N)CCOC(=O)C(=C)C)=CC=C1N=NC1=NC2=CC=C([N+]([O-])=O)C=C2S1 JBQIJZUDJPCDQU-UHFFFAOYSA-N 0.000 description 3
- VVGDYBMOQGSRJW-UHFFFAOYSA-N 2-[n-(2-cyanoethyl)-4-[(6-nitro-1,3-benzothiazol-2-yl)diazenyl]anilino]ethyl 4-ethenylbenzoate Chemical compound S1C2=CC([N+](=O)[O-])=CC=C2N=C1N=NC(C=C1)=CC=C1N(CCC#N)CCOC(=O)C1=CC=C(C=C)C=C1 VVGDYBMOQGSRJW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- WSLBAVQYFJUIIA-UHFFFAOYSA-N C=CC(=O)Oc1ccc2ccccc2c1N=Nc1ccc(cc1)N=Nc1ccccc1 Chemical compound C=CC(=O)Oc1ccc2ccccc2c1N=Nc1ccc(cc1)N=Nc1ccccc1 WSLBAVQYFJUIIA-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000005498 polishing Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229940099373 sudan iii Drugs 0.000 description 3
- 229920006305 unsaturated polyester Polymers 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- QLRDACXDRLGLOC-UHFFFAOYSA-N 2-[n-(2-cyanoethyl)-4-[(4-nitrophenyl)diazenyl]anilino]ethyl acetate Chemical compound C1=CC(N(CCC#N)CCOC(=O)C)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 QLRDACXDRLGLOC-UHFFFAOYSA-N 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 2
- FPBFWDHYZMVTJD-UHFFFAOYSA-N 2-methyl-2-(prop-2-enoylamino)propanoic acid Chemical compound OC(=O)C(C)(C)NC(=O)C=C FPBFWDHYZMVTJD-UHFFFAOYSA-N 0.000 description 2
- WZJJWQVBLSPALW-UHFFFAOYSA-N 3-[n-(2-hydroxyethyl)anilino]propanenitrile Chemical compound N#CCCN(CCO)C1=CC=CC=C1 WZJJWQVBLSPALW-UHFFFAOYSA-N 0.000 description 2
- GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 description 2
- 0 C=CCNC(OCCC(CCC#N)*c(cc1)ccc1N=Nc1nc(ccc([N+]([O-])=O)c2)c2[s]1)=O Chemical compound C=CCNC(OCCC(CCC#N)*c(cc1)ccc1N=Nc1nc(ccc([N+]([O-])=O)c2)c2[s]1)=O 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 238000012644 addition polymerization Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 229960005215 dichloroacetic acid Drugs 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 239000002244 precipitate Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000003573 thiols Chemical class 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
- 230000007704 transition Effects 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical class C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 1
- RQHGZNBWBKINOY-PLNGDYQASA-N (z)-4-tert-butylperoxy-4-oxobut-2-enoic acid Chemical compound CC(C)(C)OOC(=O)\C=C/C(O)=O RQHGZNBWBKINOY-PLNGDYQASA-N 0.000 description 1
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/44—Resins; Plastics; Rubber; Leather
- G01N33/442—Resins; Plastics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/346—Clay
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/38—Boron-containing compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L41/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
- C09B43/26—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with polyfunctional acylating agents
- C09B43/263—Polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
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Description
本出願は、2013年3月15日に出願された米国特許仮出願第61/793,001号の優先権を主張するものであり、その全文を参照により本明細書に援用する。
この式中、Rは、水素又はアルキルであり;Xは、アルキレンであり;Yは、結合、エーテル、チオエーテル、アミン、アミド、エステル、チオエステル、カーボネート、チオカーボネート、カルバメート、チオカルバメート、尿素、チオ尿素、アルキレン、アリールアルキレン、アルキルアリーレン、又はアリーレンであって、アルキレン、アリールアルキレン、アルキルアリーレン、及びアリーレンは、任意で、エーテル、チオエーテル、アミン、アミド、エステル、チオエステル、カーボネート、チオカーボネート、カルバメート、チオカルバメート、尿素、又はチオ尿素のうちの少なくとも1つによって中断又は終端のうちの少なくとも1つをされ;Zは、アクリレート、メタクリレート、アクリルアミド、メタクリルアミド、スチレニル、又は少なくとも3個の炭素原子を有する末端アルケニルである。
「a」、「an」、及び「the」等の用語は、1つの実体のみを指すことを意図するものではなく、具体例を例示のために用いることができる一般部類を含む。用語「a」、「an」、及び「the」は、用語「少なくとも1つの」と互換的に使用される。
第1の実施形態では、本開示は、以下の式によって表される化合物を提供する:
Rは、水素又はアルキルであり、
Xは、アルキレンであり、
Yは、結合、エーテル、チオエーテル、アミン、アミド、エステル、チオエステル、カーボネート、チオカーボネート、カルバメート、チオカルバメート、尿素、チオ尿素、アルキレン、アリールアルキレン、アルキルアリーレン、又はアリーレンであって、アルキレン、アリールアルキレン、アルキルアリーレン、及びアリーレンは、任意で、エーテル、チオエーテル、アミン、アミド、エステル、チオエステル、カーボネート、チオカーボネート、カルバメート、チオカルバメート、尿素、又はチオ尿素のうちの少なくとも1つによって中断又は終端のうちの少なくとも1つをされ;
Zは、アクリレート、メタクリレート、アクリルアミド、メタクリルアミド、スチレニル、又は少なくとも3個の炭素原子を有する末端アルケニレンである)。
−CH2CH2−O−C(O)−C(CH3)=CH2、又は−CH2CH2−O−C(O)−C6H4−CH=CH2である、第1〜第5の実施形態のいずれか1つに記載の化合物を提供する。
硬化性ポリマー樹脂と、フリーラジカル開始剤と、400ナノメートル〜700ナノメートルの波長に第1の吸光度を有する組成物を提供するのに十分な量の第1〜第6の実施形態のいずれか1つに記載の化合物とを含む組成物を提供することと、
前記組成物を硬化させて、前記第1の吸光度とは異なる波長に第2の吸光度を有する硬化組成物を提供することと、を含む、方法を提供する。
硬化性モノマーと、フリーラジカル開始剤と、400ナノメートル〜700ナノメートルの範囲の波長に第1の吸光度を有する組成物を提供するのに十分な量の第1〜第6の実施形態のいずれか1つに記載の化合物とを含む組成物を提供することと、
前記組成物を硬化させて、前記第1の吸光度とは異なる波長に第2の吸光度を有する硬化組成物を提供することと、を含む、方法を提供する。
ビニルジメチルアズラクトンは、IsoChem S.A.S.(Evry,France)から入手した。他の試薬は全て、Sigma−Aldrich Company(St.Louis,Missouri);EMD Millipore Chemicals(Billerica,Massachusetts);Alfa Aesar(Ward Hill,Massachusetts);J.T.Baker(Phillipsburg,New Jersey);BDH Merck Ltd.(Poole,Dorset,UK)、及びCambridge Isotope Laboratories,Inc.(Andover,Massachusetts)等の化学企業から入手した又は入手可能であるか;あるいは、公知の方法によって合成してもよい。特に報告しないかぎり、全ての比は、重量基準である。
250mLのフラスコ内で、ジクロロ酢酸:氷酢酸の5:1(体積)溶液66mLに2−アミノ−6−ニトロベンゾチアゾール5.00グラム(25.6mmol)を添加し、15分間かけて50℃に加熱することによって溶解させた。溶液を0℃に冷却し、次いで、10分間恒常的に撹拌しながら、0℃で保持された濃硫酸13mL中亜硝酸ナトリウム1.94グラム(28.1mmol)の溶液を収容している250mLのフラスコにゆっくりと添加した。更に30分間撹拌した後、この溶液を、これも0℃で保持された13mLの酢酸中N−(2−シアノエチル)−N−(2−ヒドロキシエチル)アニリン4.20グラム(22.1mmol)の混合物を収容している250mLのフラスコにゆっくりと添加し、1時間撹拌した。次いで、反応混合物のpHが約7になるまで炭酸ナトリウム飽和水溶液を添加することによって、反応混合物を中和し、得られた沈殿を真空濾過によって単離した。沈殿を塩化メチレン200mLに溶解させ、次いで、無水硫酸ナトリウムの床に通すことによって乾燥させ、濾過し、ロータリーエバポレータで濃縮した。3×23cmのシリカゲルカラムにロードし、次いで、溶媒の体積比を10:90から30:70に徐々に変化させたアセトン:塩化メチレン溶液で溶出することによって、得られた固体を更に精製した。純粋化合物を含有している後続画分を合わせ、減圧下で濃縮し、次いで、約21℃で0.3mm水銀(40.0Pa)の真空下で乾燥させて、4.30グラムの紫色の固体を得、これは、後にNMR分光法によって3−{(2−ヒドロキシ−エチル)−[4−(6−ニトロ−ベンゾチアゾール−2−イルアゾ)−フェニル]−アミノ}−プロピオニトリルであることが確認された。[1H NMR(500MHz,d6−DMSO)δ 9.07(d,J=2.4Hz,1H),8.32(dd,J=2.4,8.9Hz,1H),8.17(d,J=8.9Hz,1H),7.91(d,J=9.4Hz,2H),7.11(d,J=9.4Hz,2H),4.99(t,J=5.1Hz,1H),3.95(t,J=7.1Hz,2H),3.69(m,4H),2.91(t,J=6.9Hz,2H)]。
2−メチル−アクリル酸2−{(2−シアノ−エチル)−[4−(6−ニトロ−ベンゾチアゾール−2−イルアゾ)−フェニル]−アミノ}−エチルエステルの合成:
アクリル酸2−{(2−シアノ−エチル)−[4−(6−ニトロ−ベンゾチアゾール−2−イルアゾ)−フェニル]−アミノ}−エチルエステルの合成:
2−アクリロイルアミノ−2−メチル−プロピオン酸2−{(2−シアノ−エチル)−[4−(6−ニトロ−ベンゾチアゾール−2−イルアゾ)−フェニル]−アミノ}−エチルエステルの合成:
4−ビニル−安息香酸2−{(2−シアノ−エチル)−[4−(6−ニトロ−ベンゾチアゾール−2−イルアゾ)−フェニル]−アミノ}−エチルエステルの合成:
アリル−カルバミン酸2−{(2−シアノ−エチル)−[4−(6−ニトロ−ベンゾチアゾール−2−イルアゾ)−フェニル]−アミノ}−エチルエステルの合成:
約21℃の25mL中1−(4−フェニルアゾ−フェニルアゾ)−ナフタレン−2−オール0.200グラム(1.01mmol)の溶液を収容している100mLのフラスコにトリエチルアミン320μL(2.30mmol)を添加した。この溶液を、約21℃で10分間窒素雰囲気下で撹拌した。次いで、塩化アクリロイル200μL(2.46mmol)を添加した。フラスコを油浴に入れ、温度を約55℃で維持しながら、窒素雰囲気下で18時間混合物を撹拌した。反応混合物をロータリーエバポレータで濃縮した。次いで、得られた物質を水(約50mL)と塩化メチレン(約50mL)との間で分配した。次いで、有機層を除去し、水層を塩化メチレン(各回約50mL)で更に2回抽出した。次いで、有機層を合わせ、無水硫酸ナトリウムの床に通すことによって乾燥させ、濾過し、ロータリーエバポレータで濃縮した。3×40cmのシリカゲルカラムにロードし、次いで、溶媒の体積比を0:100から20:80に徐々に変化させた酢酸エチル:石油エーテル溶液で溶出することによって、得られた固体を更に精製した。純粋化合物を含有している後続画分を合わせ、減圧下で濃縮し、次いで、約21℃で0.3mm水銀(40.0Pa)の真空下で乾燥させて、96mgの固体を得、これは、後にNMR分光法によってアクリル酸1−(4−フェニルアゾ−フェニルアゾ)−ナフタレン−2−イルエステルであることが確認された。[1H NMR(500MHz,CDCl3)δ 8.74(m,1H),8.06(s,4H),7.97(m,3H),7.93(m,1H),7.62(m,6H),7.36(m,1H),6.64(dd,J=1.2,17.4Hz,1H),6.39(dd,J=10.5,17.4Hz,1H),6.08(dd,J=1.2,10.5Hz,1H)].
N−メチル−2−ピロリドン中2−メチル−アクリル酸2−{(2−シアノ−エチル)−[4−(6−ニトロ−ベンゾチアゾール−2−イルアゾ)−フェニル]−アミノ}−エチルエステルの3mg/mL溶液0.33グラムを、白色の50%ベンゾイルペルオキシド固化剤ペースト2.0グラム(商標名「BENOX B−50」としてSyrgis Performance Initiators,Inc.(Helena,Arkansas)から入手)と均一に混合した。次いで、有色固化剤0.46グラムを、商標名「3M PREMIUM BODY FILLER、部品番号50597」として3M Company(St.Paul,Minnesota)から入手したボディフィラーキットのカートリッジから分注した白色自動車用ボディフィラー20.0グラムと、21℃で45秒間パレット上で均一に混合した。得られたピンク色の物質をパレット上で約1/8〜1/4インチ(3.18〜6.35mm)の厚さに広げた。6分間後、ピンク色が残っていない固化した白色のボディフィラーが得られた。研磨ブロックを用いて、商標名「IMPERIAL GRADE P80E」として3M Companyから入手した2.75×6インチ(7.0×15.2cm)のP80等級の紙やすりを用いて、目詰まりなく、白色ボディフィラーを手で研磨することによって完全硬化が確認された。
N−メチル−2−ピロリドン中2−メチル−アクリル酸2−{(2−シアノ−エチル)−[4−(6−ニトロ−ベンゾチアゾール−2−イルアゾ)−フェニル]−アミノ}−エチルエステルの5mg/mL溶液15μLを、商標名「3M SCOTCH−WELD MEDICAL GRADE LIGHT CURE ADHESIVE MG90−77 UV」として3M Company(St.Paul,Minnesota)から入手した医療用等級の接着剤3.0グラムと均一に混合した。15mil(0.38mm)の厚さのゴムシートから直径1.2cmの円形を切り抜いた。穴の開いたゴムシートをスライドグラス上に置き、円形を上記ピンク色の接着剤製剤で充填し、第2のスライドグラスをゴムシート上に置いた。構造体をクリップでまとめた。IR分光計、モデル「NEXUS 670 FT−IR ESP」(Thermo Fischer Scientific(Minneapolis,Minnesota)製)を用いて硬化させる前に、サンプルの6202〜6102cm−1におけるIR吸光度の領域を測定した。分光計、モデル「CARY 60 UV/VIS」(Agilent Technologies(Santa Clara,California)製)を用いて硬化させる前に、サンプルの517nmにおける吸光度を測定した。次いで、320〜500nmのフィルタ、3mmの光ファイバー(部品番号806−00012)及び小さなコリメーティングレンズ(部品番号810−00016)を備えるUV光源、モデル「OMNICURE S2000」(Lumen Dynamics Group,Inc.(Mississauga,Ontario,Canada)製)を用いてサンプルを硬化させた。6202〜6102cm−1におけるIR吸光度を硬化中に測定できるように、光導体をスライドグラスの表面から2cmの所に、わずかに角度をなして配置した。サンプルを、出力設定20の光源に20秒間曝露した。20秒間の硬化後、IR吸光度は、サンプルが約96%変換されたことを示した。次いで、サンプルをCARY 60 UV/VIS分光計に戻し、517nmにおけるサンプルの吸光度を測定した。35%の吸光度低下が観察された。
N−メチル−2−ピロリドン中アクリル酸2−{(2−シアノ−エチル)−[4−(6−ニトロ−ベンゾチアゾール−2−イルアゾ)−フェニル]−アミノ}−エチルエステルの5.2mg/mL溶液200μLを、商標名「3M PREMIUM BODY FILLER部品番号50597」(3M Company製)10.1グラムと均一に混合した。得られたボディフィラーは、ピンク色であった。次いで、「BENOX B−50」固化剤0.21グラムを、ピンク色のボディフィラーと21℃で90秒間パレット上にて均一に混合した。得られたピンク色の物質をパレット上で約1/8〜1/4インチ(3.18〜6.35mm)の厚さに広げた。10分間後、ピンク色が残っていない固化した白色のボディフィラーが得られた。
N−メチル−2−ピロリドン中2−アクリロイルアミノ−2−メチル−プロピオン酸2−{(2−シアノ−エチル)−[4−(6−ニトロ−ベンゾチアゾール−2−イルアゾ)−フェニル]−アミノ}−エチルエステルの5.0mg/mL溶液75μLを、商標名「3M PREMIUM BODY FILLER部品番号50597」(3M Company製)10.1グラムと均一に混合した。得られたボディフィラーは、ピンク色であった。次いで、「BENOX B−50」固化剤0.20グラムを、ピンク色のボディフィラーと21℃で90秒間パレット上にて均一に混合した。得られたピンク色の物質をパレット上で約1/8〜1/4インチ(3.18〜6.35mm)の厚さに広げた。7.5分間後、ピンク色が残っていない固化した白色のボディフィラーが得られた。
N−メチル−2−ピロリドン中4−ビニル−安息香酸2−{(2−シアノ−エチル)−[4−(6−ニトロ−ベンゾチアゾール−2−イルアゾ)−フェニル]−アミノ}−エチルエステルの5.0mg/mL溶液75μLを、商標名「3M PREMIUM BODY FILLER部品番号50597」(3M Company製)10.1グラムと均一に混合した。得られたボディフィラーは、ピンク色であった。次いで、「BENOX B−50」固化剤0.21グラムを、ピンク色のボディフィラーと21℃で90秒間パレット上にて均一に混合した。得られたピンク色の物質をパレット上で約1/8〜1/4インチ(3.18〜6.35mm)の厚さに広げた。9分間後、ピンク色が残っていない固化した白色ボディフィラーが得られた。
N−メチル−2−ピロリドン中アリル−カルバミン酸2−{(2−シアノ−エチル)−[4−(6−ニトロ−ベンゾチアゾール−2−イルアゾ)−フェニル]−アミノ}−エチルエステルの5.0mg/mL溶液75μLを、商標名「3M PREMIUM BODY FILLER部品番号50597」(3M Company製)10.1グラムと均一に混合した。得られたボディフィラーは、ピンク色であった。次いで、「BENOX B−50」固化剤0.21グラムを、ピンク色のボディフィラーと21℃で90秒間パレット上にて均一に混合した。得られたピンク色の物質をパレット上で約1/8〜1/4インチ(3.18〜6.35mm)の厚さに広げた。7分間後、ピンク色が残っていない固化した白色ボディフィラーが得られた。
テトラヒドロフラン中アクリル酸1−(4−フェニルアゾ−フェニルアゾ)−ナフタレン−2−イルエステルの6.5mg/mL溶液100μLを、商標名「3M PREMIUM BODY FILLER部品番号50597」(3M Company製)10.0グラムと均一に混合した。得られたボディフィラーは、ベージュ色であった。次いで、「BENOX B−50」固化剤0.20グラムを、ベージュ色のボディフィラーと21℃で45秒間パレット上にて均一に混合した。得られたベージュ色の物質をパレット上で約1/8〜1/4インチ(3.18〜6.35mm)の厚さに広げた。6分間後、色が変化していない固化したベージュ色のボディフィラーが得られた。12分間後、完全に硬化したボディフィラーは、元のベージュ色から顕著に退色することなく、まだベージュ色であった。
N−メチル−2−ピロリドン中4−(4−ニトロフェニルアゾ)−N−(2−シアノエチル)−N−(アセトキシエチル)アニリンの20.0mg/mL溶液200μLを、商標名「3M PREMIUM BODY FILLER部品番号50597」(3M Company製)9.99グラムと均一に混合した。得られたボディフィラーは、薄いオレンジ色であった。次いで、「BENOX B−50」固化剤0.20グラムを、薄いオレンジ色のボディフィラーと21℃で45秒間パレット上にて均一に混合した。得られた薄いオレンジ色の物質をパレット上で約1/8〜1/4インチ(3.18〜6.35mm)の厚さに広げた。6分間後、色が変化していない固化した薄いオレンジ色のボディフィラーが得られた。12分間後、完全に硬化したボディフィラーは、元の薄いオレンジ色から顕著に退色することなく、まだ薄いオレンジ色であった。
Claims (10)
- 以下の式によって表される化合物:
Rは、水素又はアルキルであり、
Xは、アルキレンであり、
Yは、結合、エーテル、チオエーテル、アミン、アミド、エステル、チオエステル、カーボネート、チオカーボネート、カルバメート、チオカルバメート、尿素、チオ尿素、アルキレン、アリールアルキレン、アルキルアリーレン、又はアリーレンであって、アルキレン、アリールアルキレン、アルキルアリーレン、及びアリーレンは、任意で、エーテル、チオエーテル、アミン、アミド、エステル、チオエステル、カーボネート、チオカーボネート、カルバメート、チオカルバメート、尿素、又はチオ尿素のうちの少なくとも1つによって中断又は終端のうちの少なくとも1つをされ、ここで前記の「結合」とはZがXに直接結合することを指し、
Zは、アクリレート、メタクリレート、アクリルアミド、メタクリルアミド、スチレニル、又は少なくとも3個の炭素原子を有する末端アルケニルである)。 - Zが、アクリレート、メタクリレート、又はスチレニルである、請求項1に記載の化合物。
- Yが、結合、−O−、−O−C(O)−、−O−C(O)−NR1−、又は任意に少なくとも1つのエーテル、エステル、カーボネート、若しくはカルバメートによって中断若しくは終端のうちの少なくとも1つをされるアルキレンであり、R1が、水素、アルキル、アリール、アリールアルキレニル、又はアルキルアリーレニルである、請求項1又は2に記載の化合物。
- −X−Y−Zが、−CH2CH2−O−C(O)−CH=CH2、
−CH2CH2−O−C(O)−C(CH3)=CH2、又は−CH2CH2−O−C(O)−C6H4−CH=CH2である、請求項1〜3のいずれか1項に記載の化合物。 - 請求項1〜4のいずれか1項に記載の化合物と、フリーラジカル開始剤と、希釈剤とを含む、組成物。
- 請求項1〜4のいずれか1項に記載の化合物と硬化性ポリマー樹脂もしくは硬化性モノマーのうち少なくとも1種とを含む、組成物。
- 前記硬化性ポリマー樹脂が、不飽和ポリエステル樹脂又はビニルエステル樹脂である、請求項6に記載の組成物。
- スチレンモノマー、置換スチレンモノマー、アクリレートモノマー、メタクリレートモノマー、アクリルアミドモノマー、又はメタクリルアミドモノマーのうちの少なくとも1つを更に含む、請求項6又は7に記載の組成物。
- セラミックビーズ、ポリマービーズ、シリカ、中空セラミック素子、中空ポリマー素子、アルミナ、ジルコニア、マイカ、ドロマイト、ウォラストナイト(woolasonite)、繊維、タルク、炭酸カルシウム、メタホウ酸ナトリウム、又は粘土のうちの少なくとも1つを更に含む、請求項6〜8のいずれか1項に記載の組成物。
- 硬化性ポリマー樹脂における硬化を示す方法であって、
硬化性ポリマー樹脂と、フリーラジカル開始剤と、400ナノメートル〜700ナノメートルの波長に第1の吸光度を有する組成物を提供するのに十分な量の請求項1〜4いずれか1項に記載の化合物とを含む組成物を提供することと、
前記組成物を硬化させて、前記第1の吸光度とは異なる波長に第2の吸光度を有する硬化組成物を提供すること、とを含む方法。
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US201361793001P | 2013-03-15 | 2013-03-15 | |
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PCT/US2014/026289 WO2014151708A1 (en) | 2013-03-15 | 2014-03-13 | Benzothiazol-2-ylazo-phenyl compound as dye, compositions including the dye, and method of determining degree of cure of such compositions |
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CA (1) | CA2907129A1 (ja) |
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BR112015023771A2 (pt) | 2017-07-18 |
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CN105452229B (zh) | 2019-03-12 |
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KR20150130450A (ko) | 2015-11-23 |
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