JP2017522364A - 多官能性アシルホスフィンオキシド光重合開始剤 - Google Patents
多官能性アシルホスフィンオキシド光重合開始剤 Download PDFInfo
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- JP2017522364A JP2017522364A JP2017514964A JP2017514964A JP2017522364A JP 2017522364 A JP2017522364 A JP 2017522364A JP 2017514964 A JP2017514964 A JP 2017514964A JP 2017514964 A JP2017514964 A JP 2017514964A JP 2017522364 A JP2017522364 A JP 2017522364A
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- 239000003999 initiator Substances 0.000 claims abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- -1 2,6-dichlorophenyl Chemical group 0.000 claims description 208
- 239000000203 mixture Substances 0.000 claims description 64
- 229920005862 polyol Polymers 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 150000003077 polyols Chemical class 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 7
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 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 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000003456 2,6-dinitrophenyl group Chemical group [H]C1=C([H])C(=C(*)C(=C1[H])[N+]([O-])=O)[N+]([O-])=O 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 5
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 5
- 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 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 4
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 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 claims description 4
- 239000003504 photosensitizing agent Substances 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- JIQNWFBLYKVZFY-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=C[C]=CC=C1 JIQNWFBLYKVZFY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 229920005989 resin Polymers 0.000 abstract description 9
- 239000011347 resin Substances 0.000 abstract description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000004519 manufacturing process Methods 0.000 description 17
- 229920001577 copolymer Polymers 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 239000000049 pigment Substances 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- YHLQQQULLOACIC-UHFFFAOYSA-N CC1=CC(C)=C(C(PC2=CC=CC=C2)=O)C(C)=C1.Cl Chemical compound CC1=CC(C)=C(C(PC2=CC=CC=C2)=O)C(C)=C1.Cl YHLQQQULLOACIC-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000005855 radiation Effects 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 230000009257 reactivity Effects 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 6
- 239000012965 benzophenone Substances 0.000 description 6
- 235000001671 coumarin Nutrition 0.000 description 6
- 229960000956 coumarin Drugs 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
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- 230000003287 optical effect Effects 0.000 description 6
- 229920000768 polyamine Polymers 0.000 description 6
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- 229920002635 polyurethane Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
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- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
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- 125000003277 amino group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
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- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 3
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- HMJBXEZHJUYJQY-UHFFFAOYSA-N 4-(aminomethyl)octane-1,8-diamine Chemical compound NCCCCC(CN)CCCN HMJBXEZHJUYJQY-UHFFFAOYSA-N 0.000 description 3
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- 239000010703 silicon Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 229940063673 spermidine Drugs 0.000 description 1
- 229940063675 spermine Drugs 0.000 description 1
- 238000010561 standard procedure Methods 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
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
- KKFOMYPMTJLQGA-UHFFFAOYSA-N tribenzyl phosphite Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 KKFOMYPMTJLQGA-UHFFFAOYSA-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 compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3229—Esters of aromatic acids (P-C aromatic linkage)
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- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3247—Esters of acids containing the structure -C(=X)-P(=X)(R)(XH) or NC-P(=X)(R)(XH), (X = O, S, Se)
- C07F9/3252—Esters of acids containing the structure -C(=X)-P(=X)(R)(XH) or NC-P(=X)(R)(XH), (X = O, S, Se) containing the structure -C(=X)-P(=X)(R)(XR), (X = O, S, Se)
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- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/36—Amides thereof
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Abstract
Description
本発明の主たる目的は、式Iの光重合開始剤を提供することである。
Aは、相互に独立して、O、SまたはNR3を表す;
Gは、多官能化合物(コア)G-(A-H)m+nの残基、ここで、A-Hは,それぞれ、アルコール系またはアミノ或いはチオール基を表す;
m及びnは、両者共整数で、m+nは、3〜10の間の整数である;
mは、3〜8の間の整数である;
R1及びR2は、それぞれ、独立して、C1-C18のアルキル基、C6-C12のアリール基及びC5-C12のシクロアルキル基で、それぞれ、1個以上の酸素及び/又は硫黄原子及び/又は1個以上の置換又は非置換イミノ基が介在しているか、又は介在していない、又は酸素及び/又は窒素及び/又は硫黄原子を含む5員〜6員複素環式基、ただし、前記基は、それぞれ、アリール、アルキル、アリルオキシ、アルコキシ、ヘテロ原子及び/又は複素環式基で置換されていてもよい;
R2は、R1 -(C=O)-でもよい;
Yは、O又はSである;
R3は、水素又はC1〜C4のアルキル基である;
ただし、式(I)の光重合開始剤は、光硬化性エチレン系不飽和基を含まない。
(a) 式1の光重合開始剤の少なくとも1種:0.05〜20質量%(%wt)、好ましくは0.2〜10質量%;
(b)少なくとも1種のエチレン系不飽和化合物:30〜99.9質量%、好ましくは50〜98.9質量%;含む光硬化性組成物を提供することである。
(1)前記光硬化性組成物を用意すること;
(2)前記性組成物を、光源で光硬化すること。
非置換又はアリール、アルキル、アリールオキシ、アルコキシ、ヘテロ原子及び/又は複素環で置換されていてもよいC1〜C18アルキルは、例えば、メチル;エチル;プロピル;イソプロピル;n-ブチル;sec-ブチル;tert-ブチル;ペンチル;ヘキシル;ヘプチル;オクチル;2-エチルヘキシル;2、4、4-トリメチルペンチル;デシル;ドデシル;テトラデシル;ヘプタデシル;オクタデシル;1、1、1-ジメチルプロピル;1、1-ジメチルブチル;1、1、3、3-テトラメチルブチル;ベンジル;1-フェニルエチル;2-フェニル−エチル;α、α-ジメチルベンジル;ベンズヒドリル;p-トリルメチル;1-(p-ブチルフェニル)エチル;p−クロロベンジル;2、4-ジクロロベンジル;p-メトキシベンジル;m-エトキシベンジル;2−ヒドロキシエチル;2-ヒドロキシプロピル;3-ヒドロキシプロピル;4-ヒドロキシブチル;6-ヒドロキシヘキシル;2-メトキシエチル;2-メトキシプロピル;3-メトキシプロピル;4-メトキシブチル;6-メトキシヘキシル;2-エトキシエチル;2-エトキシプロピル;3-エトキシプロピル;4-エトキシブチル又は6-エトキシヘキシル;2-メトキシカルボニルエチル;2-エトキシカルボニルエチル;2-ブトキシカルボニルプロピル;1、2-ジ(メトキシカルボニル)エチル;2-ブトキシエチル;ジエトキシメチル;ジエトキシエチル;1、3-ジオキソラン-2-イル;1、3-ジオサン-2-イル;2-メチル-1、3-ジオキソラン-2-イル;4-メチル-1、3-ジオサン-2-イル;2-イソプロポキシエチル;2-ブトキシプロピル;2-オクチルオキシエチル;クロロメチル;2-クロロエチル;トリクロロメチル;トリフロロメチル;1、1-ジメチル-2-クロロエチル;2-メトキシイソプロピル;ブチルチオメチル;2-ドデシルチオエチル;2-フェニルチオエチル;2、2、2-トリフロロエチル;2-アミノエチル;2-アミノプロピル;3-アミノプロピル;4-アミノブチル;6-アミノヘキシル;2-メチルアミノエチル;2-メチルアミノプロピル;3-メチルアミノプロピル;4-メチルアミノブチル;6-メチルアミノヘキシル;2-ジメチルアミノエチル;2-ジメチルアミノプロピル;3-ジメチルアミノプロピル;4-ジメチルアミノブチル;6-ジメチルアミノヘキシル;2-ヒドロキシ-2,2-ジメチルエチル;2-フェノキシエチル;2-フェノキシプロピル;3-フェノキプロピル;4-フェノキシブチル;6-フェノキシヘキシルである。
2、6-ジニトロフェニル;2、6-ジメチルシクロヘキシル;2、6-ジエチルシクロヘキシル;2、6-ジメトキシシクロヘキシル;2、6-ジエトキシシクロヘキシル又は2、6-ジクロロシクロヘキシル;tert-ブチル;ペンチル;ヘキシル;ヘプチル;オクチル及び、2-エチルヘキシルである。
R3は、水素、又はC1 〜C4のアルキル基で、例えば、メチル、エチル、プロピル、イソプロピル、n-ブチル、sec-ブチル、及びtert-ブチルである。
特に好ましい態様では、R1 は、2、4、6-トリメチルフェニル及びR2は,フェニルである。
との反応によって合成される(参照:Methoden der Organischen Chemie, vol.12/1 p.2421).さらに、式(III)のホスフィン酸クロリドは、トリエチルアミンの存在下で、G-(A-H)m+nと反応して、式(I)の生成物にまで進行する。
プロピレングリコールジアクリレート;ネオペンチルグリコールジアクリレート;ヘキサメチレングリコールジアクリレート;ビスフェノール-A-ジアクリレート;4,4’-ビス-(2-アクリロイルオキシエトキシ)-ジフェニルプロパン;トリメチロイルプロパントリアクリレート;ペンタエリトリトールトリアクリレート;又はテトラアクリレート;ビニルアクリレート;ジビニルベンゼン;ジビニルスクシネート;ジアリルフタレート;トリアリルホスフェート;トリアリルイソシアヌレート、又はトリス-(2-アクリロイルエチル)イソシアヌレートである。
プロパン-1-オン([Esacure1001]、Lamberti S. p. A.の登録商標);フェニルグリオキシレート及びその誘導体;ダイメリックフェニルグリオキシレート;PERESTERS(例えばEP126541号に記載されている「ベンゾフェノンテトラカルボン酸PERESTERS」);アシルホスフィンオキシド光重合開始剤(モノ-アシルホスフィンオキシド、ビス-アシルホスフィンオキシド、トリス-アシルホスフィンオキシド);ハロメチルトリアジン;ヘキサリルビスイミダゾール/共重合開始剤(COINITIATOR)系、例えば、2-メルカプトベンゾチアゾールとオルト-クロロヘキサフェニルビスイミダゾールの組み合わせ;フェロセニウム化合物又はチタノセン、例えば、ジシクロペンタジエニル-ビス(2、6-ジフロロ-3-ピロール-フェニル)チタニウム;O-アシロキシムエステル光重合開始剤である。
31P-NMR(CDCl3、δppm):18.2
31P-NMR(CDCl3、δppm):18.2
31P-NMR(CDCl3、δppm):18.2
[クリアーフォミュレーション]
実施例1〜6及び10の光重合開始剤を、Ebecryl 605 及びEbecryl 350(Allnex)の99.5:0.5w/wの混合物に、4wt%の濃度で溶解して本発明による光硬化性組成物を製造した。
実施例1〜5の光重合開始剤を、5.0wt%の濃度でインクジェット印刷用シアンに溶解してテスト用光硬化性組成物を製造した。
スチロールで希釈した不飽和ポリエステルと20wt%の二酸化チタンを含む白色顔料系に、実施例1〜5の光重合開始剤を、6.0wt%の濃度で溶解してテスト用光硬化性組成物を製造した。
Claims (10)
- 式Iの光重合開始剤:
Aは、相互に独立して、O、SまたはNR3を表す;
Gは、多官能化合物(コア)G-(A-H)m+nの残基、ここで、A-Hは,それぞれ、アルコール系またはアミノ或いはチオール基を表す;
m及びnは、両者共整数で、m+nは、3〜10の間の整数である;
mは、3〜8の間の整数である;
R1及びR2は、それぞれ、独立して、C1-C18のアルキル基、C6-C12のアリール基及びC5-C12のシクロアルキル基で、それぞれ、1個以上の酸素及び/又は硫黄原子及び/又は1個以上の置換又は非置換イミノ基が介在しているか、又は介在していない、又は酸素及び/又は窒素及び/又は硫黄原子を含む5員〜6員複素環式基、ただし、前記基は、それぞれ、アリール、アルキル、アリルオキシ、アルコキシ、ヘテロ原子及び/又は複素環式基で置換されていてもよい;
R2は、R1-(C=O)-でもよい;
Yは、O又はSである;
R3は、水素又はC1〜C4のアルキル基である;
ただし、式(1)の光重合開始剤は、光硬化性エチレン系不飽和基を含まない。 - 前記式Iにおいて、m+nは、3〜8の間の整数である請求項1に記載した光重合開始剤。
- 前記式Iにおいて、mは、3〜6の間の整数である請求項1に記載した光重合開始剤。
- 前記式Iにおいて、R1は、フェニル;2、6-ジクロロフェニル;2、4、6-トリクロロフェニル;2、6-ジメチルフェニル;2、4、6-トリメチルフェニル;2、6-ジエチルフェニル;2、6-ジメトキシフェニル;2、6-ジエトキシフェニル;α-ナフチル;2、6-ジニトロフェニル;2、6-ジメチルシクロヘキシル;2、6-ジエチルシクロヘキシル;2、6-ジメトキシシクロヘキシル;2、6-ジエトキシシクロヘキシル;2、6-ジクロロシクロヘキシル;tert-ブチル;ペンチル;ヘキシル:ヘプチル;オクチル;及び2-エチルヘキシルである請求項1に記載した光重合開始剤。
- 前記式Iにおいて、R2は、R1 -(C=O)で、メチル;エチル;プロピル;イソプロピル;n-ブチル;sec-ブチル;tert-ブチル;ペンチル;ヘキシル;2-エチルヘキシル;フェニル;キシリル;4-ビフェニル;2-、3-又は4-クロロフェニル;2、4-ジクロロフェニル;2-、3-又は4-メチルフェニル;2、4-ジメチルフェニル;2-、3-又は4-エチルフェニル;2-、3-又は4-メトキシフェニル;2、4-ジメトキシフェニル;2-、3-又は4-エトキシフェニル;α-ナフチル;メチルナフチル;クロロナフチル;エトキシナフチル;及び2-又は4-ニトロフェニルである請求項1に記載した光重合開始剤。
- 前記G-(A-H)m+nは、モノマー、オリゴマー、高分子ポリオール及びそれらの混合物から選択される請求項1に記載した光重合開始剤。
- (a)前記光重合開始剤:0.2〜10質量%;
(b)前記少なくとも1種のエチレン系不飽和化合物:50〜98.9質量%、含む請求項7に記載した光硬化性組成物。 - さらに、(c)他の光重合開始剤を0.5〜15質量%含む請求項7に記載した光硬化性組成物。
- さらに、(d)光増感剤を0.05〜12質量%含む請求項7に記載した光硬化性組成物。
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