CN1200943C - 有机金属-酰基芳基膦 - Google Patents
有机金属-酰基芳基膦 Download PDFInfo
- Publication number
- CN1200943C CN1200943C CNB011034874A CN01103487A CN1200943C CN 1200943 C CN1200943 C CN 1200943C CN B011034874 A CNB011034874 A CN B011034874A CN 01103487 A CN01103487 A CN 01103487A CN 1200943 C CN1200943 C CN 1200943C
- Authority
- CN
- China
- Prior art keywords
- phenyl
- benzoyl
- alkyl
- phenylphosphine
- lithium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title claims description 123
- 229910000073 phosphorus hydride Inorganic materials 0.000 title claims description 100
- 125000002524 organometallic group Chemical group 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 187
- 238000002360 preparation method Methods 0.000 claims abstract description 31
- -1 xenyl Chemical group 0.000 claims description 611
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 236
- 239000002585 base Substances 0.000 claims description 168
- 229910052760 oxygen Inorganic materials 0.000 claims description 146
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 133
- 229910052736 halogen Inorganic materials 0.000 claims description 115
- 150000002367 halogens Chemical class 0.000 claims description 113
- 229910052717 sulfur Inorganic materials 0.000 claims description 105
- 239000000203 mixture Substances 0.000 claims description 102
- 239000001257 hydrogen Substances 0.000 claims description 101
- 229910052739 hydrogen Inorganic materials 0.000 claims description 101
- 229910052744 lithium Inorganic materials 0.000 claims description 86
- 150000002431 hydrogen Chemical class 0.000 claims description 72
- 238000000034 method Methods 0.000 claims description 63
- 238000006243 chemical reaction Methods 0.000 claims description 53
- 239000001301 oxygen Substances 0.000 claims description 51
- 239000000463 material Substances 0.000 claims description 47
- 238000000576 coating method Methods 0.000 claims description 39
- 239000011248 coating agent Substances 0.000 claims description 37
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 36
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 36
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 36
- 125000001118 alkylidene group Chemical class 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- 125000001624 naphthyl group Chemical group 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000004450 alkenylene group Chemical group 0.000 claims description 26
- 238000007639 printing Methods 0.000 claims description 24
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 23
- 238000000926 separation method Methods 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 230000003647 oxidation Effects 0.000 claims description 19
- 238000007254 oxidation reaction Methods 0.000 claims description 19
- 238000006116 polymerization reaction Methods 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 239000000843 powder Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- 239000000654 additive Substances 0.000 claims description 17
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 16
- 101150065749 Churc1 gene Proteins 0.000 claims description 16
- 102100038239 Protein Churchill Human genes 0.000 claims description 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 15
- 239000002994 raw material Substances 0.000 claims description 15
- 229910052698 phosphorus Inorganic materials 0.000 claims description 13
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 150000003003 phosphines Chemical class 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000004437 phosphorous atom Chemical group 0.000 claims description 11
- OKQKDCXVLPGWPO-UHFFFAOYSA-N sulfanylidenephosphane Chemical compound S=P OKQKDCXVLPGWPO-UHFFFAOYSA-N 0.000 claims description 11
- 238000005987 sulfurization reaction Methods 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000001465 metallisation Methods 0.000 claims description 9
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 238000003384 imaging method Methods 0.000 claims description 8
- 238000007645 offset printing Methods 0.000 claims description 8
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011159 matrix material Substances 0.000 claims description 7
- 238000007650 screen-printing Methods 0.000 claims description 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 6
- 239000003365 glass fiber Substances 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 5
- 238000007647 flexography Methods 0.000 claims description 5
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 5
- 125000005504 styryl group Chemical group 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000003094 microcapsule Substances 0.000 claims description 3
- 238000012360 testing method Methods 0.000 claims description 3
- HIISVQYDQWJITQ-UHFFFAOYSA-N 1h-pyrrole;quinoline Chemical class C=1C=CNC=1.N1=CC=CC2=CC=CC=C21 HIISVQYDQWJITQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000007797 corrosion Effects 0.000 claims description 2
- 238000005260 corrosion Methods 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 239000005548 dental material Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 2
- 238000010186 staining Methods 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 abstract description 3
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 182
- 125000004098 2,6-dichlorobenzoyl group Chemical group O=C([*])C1=C(Cl)C([H])=C([H])C([H])=C1Cl 0.000 description 170
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 121
- MFLDWEWCKBTVEX-UHFFFAOYSA-N lithium;phenylphosphane Chemical compound [Li].PC1=CC=CC=C1 MFLDWEWCKBTVEX-UHFFFAOYSA-N 0.000 description 90
- 150000002148 esters Chemical class 0.000 description 79
- ZGEZPSPEVXDOMG-UHFFFAOYSA-N lithium;phosphane Chemical compound [Li].P ZGEZPSPEVXDOMG-UHFFFAOYSA-N 0.000 description 76
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 55
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 50
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 49
- PBFLZIJOWRZFDC-UHFFFAOYSA-N pentoxy(phenyl)phosphane Chemical compound C(CCCC)OPC1=CC=CC=C1 PBFLZIJOWRZFDC-UHFFFAOYSA-N 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 38
- 150000003254 radicals Chemical class 0.000 description 38
- TUDSTYFYBDBDRC-UHFFFAOYSA-N C=1C=CC=CC=1P(=O)C(=O)C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1P(=O)C(=O)C1=CC=CC=C1 TUDSTYFYBDBDRC-UHFFFAOYSA-N 0.000 description 32
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- IGLPBLSAUVRWAV-UHFFFAOYSA-N 2-methylpropoxy(phenyl)phosphane Chemical compound C(C(C)C)OPC1=CC=CC=C1 IGLPBLSAUVRWAV-UHFFFAOYSA-N 0.000 description 20
- PUMCTNUKBBHWFR-UHFFFAOYSA-N [Li].C(C)C(COPC1=CC=CC=C1)CCCC Chemical compound [Li].C(C)C(COPC1=CC=CC=C1)CCCC PUMCTNUKBBHWFR-UHFFFAOYSA-N 0.000 description 20
- VFYQDQDFOPNVHK-UHFFFAOYSA-N hexoxy(phenyl)phosphane Chemical compound C(CCCCC)OPC1=CC=CC=C1 VFYQDQDFOPNVHK-UHFFFAOYSA-N 0.000 description 20
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 20
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 18
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 18
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 17
- 229960003424 phenylacetic acid Drugs 0.000 description 17
- 239000003279 phenylacetic acid Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 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 15
- 239000000049 pigment Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 239000012965 benzophenone Substances 0.000 description 12
- 238000001723 curing Methods 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- XVZXOLOFWKSDSR-UHFFFAOYSA-N Cc1cc(C)c([C]=O)c(C)c1 Chemical group Cc1cc(C)c([C]=O)c(C)c1 XVZXOLOFWKSDSR-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 11
- 239000000975 dye Substances 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- 238000000016 photochemical curing Methods 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- RQGHGCNSWDDAQH-UHFFFAOYSA-N 3-methylbutoxy(phenyl)phosphane Chemical compound C(CC(C)C)OPC1=CC=CC=C1 RQGHGCNSWDDAQH-UHFFFAOYSA-N 0.000 description 10
- TVJZTZGJTZZLSG-UHFFFAOYSA-N C(C)C(C[PH2]=O)CCCC Chemical compound C(C)C(C[PH2]=O)CCCC TVJZTZGJTZZLSG-UHFFFAOYSA-N 0.000 description 10
- APYYTKIIYAONGG-UHFFFAOYSA-N CC1=CC=CC(C(P(C2=CC=CC=C2)(Cl)=O)=O)=C1 Chemical compound CC1=CC=CC(C(P(C2=CC=CC=C2)(Cl)=O)=O)=C1 APYYTKIIYAONGG-UHFFFAOYSA-N 0.000 description 10
- QSYOEDZIGWVIRW-UHFFFAOYSA-N butoxy(phenyl)phosphane Chemical compound CCCCOPC1=CC=CC=C1 QSYOEDZIGWVIRW-UHFFFAOYSA-N 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 10
- VRIZBDXJAOERTJ-UHFFFAOYSA-N phenyl(phenylmethoxy)phosphane Chemical compound C(C1=CC=CC=C1)OPC1=CC=CC=C1 VRIZBDXJAOERTJ-UHFFFAOYSA-N 0.000 description 10
- XRIVNKJCNCNGFU-UHFFFAOYSA-N phenyl(propan-2-yl)phosphane Chemical compound CC(C)PC1=CC=CC=C1 XRIVNKJCNCNGFU-UHFFFAOYSA-N 0.000 description 10
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 10
- 229920002120 photoresistant polymer Polymers 0.000 description 10
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- VXOYERGFYQOYCN-UHFFFAOYSA-N phenyl-[phenyl(trifluoromethyl)phosphoryl]methanone Chemical compound FC(F)(F)P(C1=CC=CC=C1)(C(C1=CC=CC=C1)=O)=O VXOYERGFYQOYCN-UHFFFAOYSA-N 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 239000003973 paint Substances 0.000 description 8
- 229920003023 plastic Polymers 0.000 description 8
- 239000004033 plastic Substances 0.000 description 8
- 230000005855 radiation Effects 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 7
- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- ODNWLKMVKAGTEZ-UHFFFAOYSA-N O=[PH2]CCCCCC1=CC=CC=C1 Chemical compound O=[PH2]CCCCCC1=CC=CC=C1 ODNWLKMVKAGTEZ-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- CWHAUUCAWXYLJZ-UHFFFAOYSA-N [PH3]=O.C(CCCC)OC(CC1=CC=CC=C1)=O Chemical compound [PH3]=O.C(CCCC)OC(CC1=CC=CC=C1)=O CWHAUUCAWXYLJZ-UHFFFAOYSA-N 0.000 description 6
- 239000012752 auxiliary agent Substances 0.000 description 6
- 239000012964 benzotriazole Substances 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 6
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 229960001866 silicon dioxide Drugs 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
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- QPQBOAGIQNRLSN-UHFFFAOYSA-N lithium;(2,4,6-triethoxyphenyl)phosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound [Li].CCOC1=CC(OCC)=CC(OCC)=C1PC(=O)C1=C(C)C=C(C)C=C1C QPQBOAGIQNRLSN-UHFFFAOYSA-N 0.000 description 1
- WEKUOHNHKLNRLY-UHFFFAOYSA-N lithium;(2,4,6-trimethoxyphenyl)-(2,4,6-trimethoxyphenyl)phosphanylmethanone Chemical compound [Li].COC1=CC(OC)=CC(OC)=C1PC(=O)C1=C(OC)C=C(OC)C=C1OC WEKUOHNHKLNRLY-UHFFFAOYSA-N 0.000 description 1
- SUHPRYBESPZDQN-UHFFFAOYSA-N lithium;(2,4,6-trimethoxyphenyl)-(2,4,6-trimethylphenyl)phosphanylmethanone Chemical compound [Li].COC1=CC(OC)=CC(OC)=C1C(=O)PC1=C(C)C=C(C)C=C1C SUHPRYBESPZDQN-UHFFFAOYSA-N 0.000 description 1
- GFUUBJGZZSUENG-UHFFFAOYSA-N lithium;(2,4,6-trimethoxyphenyl)-(2,4,6-tripropoxyphenyl)phosphanylmethanone Chemical compound [Li].CCCOC1=CC(OCCC)=CC(OCCC)=C1PC(=O)C1=C(OC)C=C(OC)C=C1OC GFUUBJGZZSUENG-UHFFFAOYSA-N 0.000 description 1
- YXOUYZMOGHKYAW-UHFFFAOYSA-N lithium;(2,4,6-trimethoxyphenyl)phosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound [Li].COC1=CC(OC)=CC(OC)=C1PC(=O)C1=C(C)C=C(C)C=C1C YXOUYZMOGHKYAW-UHFFFAOYSA-N 0.000 description 1
- QYOGJWPTKYEGPL-UHFFFAOYSA-N lithium;(2,4,6-trimethylphenyl)-(2,4,6-trimethylphenyl)phosphanylmethanone Chemical compound [Li].CC1=CC(C)=CC(C)=C1PC(=O)C1=C(C)C=C(C)C=C1C QYOGJWPTKYEGPL-UHFFFAOYSA-N 0.000 description 1
- JMDCTTLOMZUFSA-UHFFFAOYSA-N lithium;(2,4,6-trimethylphenyl)-(2,4,6-tripropoxyphenyl)phosphanylmethanone Chemical compound [Li].CCCOC1=CC(OCCC)=CC(OCCC)=C1PC(=O)C1=C(C)C=C(C)C=C1C JMDCTTLOMZUFSA-UHFFFAOYSA-N 0.000 description 1
- YFBVYIICRLPMGB-UHFFFAOYSA-N lithium;(2-methyl-4-phenoxyphenyl)phosphanyl-(2,4,6-trimethoxyphenyl)methanone Chemical compound [Li].COC1=CC(OC)=CC(OC)=C1C(=O)PC(C(=C1)C)=CC=C1OC1=CC=CC=C1 YFBVYIICRLPMGB-UHFFFAOYSA-N 0.000 description 1
- HUICXINJYMCXLP-UHFFFAOYSA-N lithium;(2-methyl-4-phenoxyphenyl)phosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound [Li].CC1=CC(C)=CC(C)=C1C(=O)PC(C(=C1)C)=CC=C1OC1=CC=CC=C1 HUICXINJYMCXLP-UHFFFAOYSA-N 0.000 description 1
- JVCFKMMNPNTIST-UHFFFAOYSA-N lithium;(2-methyl-4-phenylmethoxyphenyl)phosphanyl-(2,4,6-trimethoxyphenyl)methanone Chemical compound [Li].COC1=CC(OC)=CC(OC)=C1C(=O)PC(C(=C1)C)=CC=C1OCC1=CC=CC=C1 JVCFKMMNPNTIST-UHFFFAOYSA-N 0.000 description 1
- MPMMWSVSXYHNDQ-UHFFFAOYSA-N lithium;(2-methyl-4-phenylmethoxyphenyl)phosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound [Li].CC1=CC(C)=CC(C)=C1C(=O)PC(C(=C1)C)=CC=C1OCC1=CC=CC=C1 MPMMWSVSXYHNDQ-UHFFFAOYSA-N 0.000 description 1
- OWYFAHQKRJBKCV-UHFFFAOYSA-N lithium;(2-methyl-4-propoxyphenyl)phosphanyl-(2,4,6-trimethoxyphenyl)methanone Chemical compound [Li].CC1=CC(OCCC)=CC=C1PC(=O)C1=C(OC)C=C(OC)C=C1OC OWYFAHQKRJBKCV-UHFFFAOYSA-N 0.000 description 1
- RZZLEKRKHFFMEM-UHFFFAOYSA-N lithium;(2-methyl-4-propoxyphenyl)phosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound [Li].CC1=CC(OCCC)=CC=C1PC(=O)C1=C(C)C=C(C)C=C1C RZZLEKRKHFFMEM-UHFFFAOYSA-N 0.000 description 1
- LXAUSNJHUGMVDV-UHFFFAOYSA-N lithium;(2-methyl-6-phenylphenyl)-phenylphosphanylmethanone Chemical compound [Li].C=1C=CC=CC=1PC(=O)C=1C(C)=CC=CC=1C1=CC=CC=C1 LXAUSNJHUGMVDV-UHFFFAOYSA-N 0.000 description 1
- SEKBGTTYKOBBFA-UHFFFAOYSA-N lithium;(4-phenoxyphenyl)phosphanyl-(2,4,6-trimethoxyphenyl)methanone Chemical compound [Li].COC1=CC(OC)=CC(OC)=C1C(=O)PC(C=C1)=CC=C1OC1=CC=CC=C1 SEKBGTTYKOBBFA-UHFFFAOYSA-N 0.000 description 1
- WXALESDIXWZELL-UHFFFAOYSA-N lithium;(4-phenoxyphenyl)phosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound [Li].CC1=CC(C)=CC(C)=C1C(=O)PC(C=C1)=CC=C1OC1=CC=CC=C1 WXALESDIXWZELL-UHFFFAOYSA-N 0.000 description 1
- BWCFPKTXEKVBIV-UHFFFAOYSA-N lithium;(4-phenylmethoxyphenyl)phosphanyl-(2,4,6-trimethoxyphenyl)methanone Chemical compound [Li].COC1=CC(OC)=CC(OC)=C1C(=O)PC(C=C1)=CC=C1OCC1=CC=CC=C1 BWCFPKTXEKVBIV-UHFFFAOYSA-N 0.000 description 1
- MIHAHFIXMZWXOX-UHFFFAOYSA-N lithium;(4-phenylmethoxyphenyl)phosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound [Li].CC1=CC(C)=CC(C)=C1C(=O)PC(C=C1)=CC=C1OCC1=CC=CC=C1 MIHAHFIXMZWXOX-UHFFFAOYSA-N 0.000 description 1
- LZNMJHPAICXQPJ-UHFFFAOYSA-N lithium;(4-propoxyphenyl)phosphanyl-(2,4,6-trimethoxyphenyl)methanone Chemical compound [Li].C1=CC(OCCC)=CC=C1PC(=O)C1=C(OC)C=C(OC)C=C1OC LZNMJHPAICXQPJ-UHFFFAOYSA-N 0.000 description 1
- ZUHASFNRIFJLKL-UHFFFAOYSA-N lithium;(4-propoxyphenyl)phosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound [Li].C1=CC(OCCC)=CC=C1PC(=O)C1=C(C)C=C(C)C=C1C ZUHASFNRIFJLKL-UHFFFAOYSA-N 0.000 description 1
- CHSQNPDQOHBGEV-UHFFFAOYSA-N lithium;[2-methyl-4-(2-methylpropoxy)phenyl]phosphanyl-(2,4,6-trimethoxyphenyl)methanone Chemical compound [Li].COC1=CC(OC)=CC(OC)=C1C(=O)PC1=CC=C(OCC(C)C)C=C1C CHSQNPDQOHBGEV-UHFFFAOYSA-N 0.000 description 1
- HQWRRHKYTXUIHU-UHFFFAOYSA-N lithium;[2-methyl-4-(2-methylpropoxy)phenyl]phosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound [Li].CC1=CC(OCC(C)C)=CC=C1PC(=O)C1=C(C)C=C(C)C=C1C HQWRRHKYTXUIHU-UHFFFAOYSA-N 0.000 description 1
- HCEIIHFPNZJRHT-UHFFFAOYSA-N lithium;[2-methyl-4-(3-methylbutoxy)phenyl]phosphanyl-(2,4,6-trimethoxyphenyl)methanone Chemical compound [Li].COC1=CC(OC)=CC(OC)=C1C(=O)PC1=CC=C(OCCC(C)C)C=C1C HCEIIHFPNZJRHT-UHFFFAOYSA-N 0.000 description 1
- MGDAGMPYWLRPJE-UHFFFAOYSA-N lithium;[2-methyl-4-(3-methylbutoxy)phenyl]phosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound [Li].CC1=CC(OCCC(C)C)=CC=C1PC(=O)C1=C(C)C=C(C)C=C1C MGDAGMPYWLRPJE-UHFFFAOYSA-N 0.000 description 1
- JMZBCXZBFPTSDW-UHFFFAOYSA-N lithium;[4-(2-methylpropoxy)phenyl]phosphanyl-(2,4,6-trimethoxyphenyl)methanone Chemical compound [Li].COC1=CC(OC)=CC(OC)=C1C(=O)PC1=CC=C(OCC(C)C)C=C1 JMZBCXZBFPTSDW-UHFFFAOYSA-N 0.000 description 1
- UEYWABZWWBDMNO-UHFFFAOYSA-N lithium;[4-(2-methylpropoxy)phenyl]phosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound [Li].C1=CC(OCC(C)C)=CC=C1PC(=O)C1=C(C)C=C(C)C=C1C UEYWABZWWBDMNO-UHFFFAOYSA-N 0.000 description 1
- BQBSMDNKWFEQQD-UHFFFAOYSA-N lithium;[4-(3-methylbutoxy)phenyl]phosphanyl-(2,4,6-trimethoxyphenyl)methanone Chemical compound [Li].COC1=CC(OC)=CC(OC)=C1C(=O)PC1=CC=C(OCCC(C)C)C=C1 BQBSMDNKWFEQQD-UHFFFAOYSA-N 0.000 description 1
- NXYBDADOTWOIPR-UHFFFAOYSA-N lithium;[4-(3-methylbutoxy)phenyl]phosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound [Li].C1=CC(OCCC(C)C)=CC=C1PC(=O)C1=C(C)C=C(C)C=C1C NXYBDADOTWOIPR-UHFFFAOYSA-N 0.000 description 1
- NTNGIKMHLXHMQS-UHFFFAOYSA-N lithium;phenylphosphanyl-(2,3,6-trimethoxyphenyl)methanone Chemical compound [Li].COC1=CC=C(OC)C(C(=O)PC=2C=CC=CC=2)=C1OC NTNGIKMHLXHMQS-UHFFFAOYSA-N 0.000 description 1
- CCIVQJNYTSOQRC-UHFFFAOYSA-N lithium;phenylphosphanyl-(2,3,6-trimethylphenyl)methanone Chemical compound [Li].CC1=CC=C(C)C(C(=O)PC=2C=CC=CC=2)=C1C CCIVQJNYTSOQRC-UHFFFAOYSA-N 0.000 description 1
- BBMSNXZXCXEQBU-UHFFFAOYSA-N lithium;phenylphosphanyl-(2,4,6-trimethoxyphenyl)methanone Chemical compound [Li].COC1=CC(OC)=CC(OC)=C1C(=O)PC1=CC=CC=C1 BBMSNXZXCXEQBU-UHFFFAOYSA-N 0.000 description 1
- PWFZLKWEXYJYQO-UHFFFAOYSA-N lithium;phenylphosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound [Li].CC1=CC(C)=CC(C)=C1C(=O)PC1=CC=CC=C1 PWFZLKWEXYJYQO-UHFFFAOYSA-N 0.000 description 1
- WXXMPSJCFQDCAI-UHFFFAOYSA-N lithium;phenylphosphanyl-[2,4,6-tri(propan-2-yl)phenyl]methanone Chemical compound [Li].CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C(=O)PC1=CC=CC=C1 WXXMPSJCFQDCAI-UHFFFAOYSA-N 0.000 description 1
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- ZJQKISPTWPQBSR-UHFFFAOYSA-N methanamine;toluene Chemical compound NC.CC1=CC=CC=C1 ZJQKISPTWPQBSR-UHFFFAOYSA-N 0.000 description 1
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- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-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
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
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- 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
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Classifications
-
- 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
- C07F9/50—Organo-phosphines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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| US6803392B1 (en) | 1999-10-20 | 2004-10-12 | Ciba Specialty Chemicals Corporation | Photoinitiator formulations |
| GB2365430B (en) * | 2000-06-08 | 2002-08-28 | Ciba Sc Holding Ag | Acylphosphine photoinitiators and intermediates |
| CN1264876C (zh) * | 2000-09-14 | 2006-07-19 | 西巴特殊化学品控股有限公司 | 在甲基丙烯酸酯铸模树脂中的酰基膦氧化物光引发剂 |
| KR100903939B1 (ko) * | 2001-08-21 | 2009-06-25 | 시바 홀딩 인크 | 광개시제로서의 장파장 모노- 및 비스-아실포스핀 옥사이드 및 설파이드 |
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| DE10206096A1 (de) * | 2002-02-13 | 2003-08-14 | Basf Ag | Mono- und Bisacylphosphinderivate |
| KR20050009744A (ko) * | 2002-06-11 | 2005-01-25 | 시바 스페셜티 케미칼스 홀딩 인크. | 모노- 및 비스아실포스핀 옥사이드의 다량체 형태 |
| CA2522898A1 (en) * | 2003-05-23 | 2004-12-02 | Ciba Specialty Chemicals Holding Inc. | Strongly adherent surface coatings |
| MXPA06000681A (es) * | 2003-07-18 | 2006-04-11 | Ciba Sc Holding Ag | Proceso para preparar acilfosfanos y derivados de los mismos. |
| AU2004312897B2 (en) | 2003-12-29 | 2011-01-20 | Johnson & Johnson Surgical Vision, Inc. | Intraocular lenses having a visible light-selective-transmissive-region |
| US20050154109A1 (en) * | 2004-01-12 | 2005-07-14 | Minyu Li | Floor finish with lightening agent |
| BRPI0509338B1 (pt) * | 2004-04-30 | 2017-10-17 | Abbott Medical Optics Inc. | Detached devices having a highly selective violet light transmitter and related methods |
| US20060115516A1 (en) | 2004-11-22 | 2006-06-01 | Pearson Jason C | Copolymerizable methine and anthraquinone compounds and articles containing them |
| CA2588538C (en) * | 2004-11-22 | 2014-07-29 | Advanced Medical Optics, Inc. | Copolymerizable azo compounds and articles containing them |
| EP1814891B1 (en) * | 2004-11-23 | 2011-01-26 | Basf Se | Bisacylphosphanes and their use as photoinitiators; process for preparing acylphosphanes |
| GB2422678B (en) * | 2005-01-25 | 2009-03-11 | Photocentric Ltd | Method of making a photopolymer plate |
| JP2006252787A (ja) * | 2005-03-08 | 2006-09-21 | Toppan Printing Co Ltd | 有機el素子製造方法および有機el素子 |
| JP5232365B2 (ja) * | 2005-06-01 | 2013-07-10 | 富士フイルム株式会社 | フッ素化光重合開始剤を含む光学フィルム、反射防止フィルム、偏光板、およびそれを用いた画像表示装置 |
| US8228848B2 (en) * | 2008-11-17 | 2012-07-24 | Sierra Wireless, Inc. | Method and apparatus for facilitating push communication across a network boundary |
| US8924486B2 (en) * | 2009-02-12 | 2014-12-30 | Sierra Wireless, Inc. | Method and system for aggregating communications |
| WO2010054471A1 (en) | 2008-11-17 | 2010-05-20 | Sierra Wireless, Inc. | Method and apparatus for network port and network address translation |
| WO2010121387A1 (en) * | 2009-04-20 | 2010-10-28 | ETH Zürich | Polymer nanoparticles |
| US8633258B2 (en) | 2010-06-30 | 2014-01-21 | Dsm Ip Assets B.V. | D1492 liquid BAPO photoinitiator and its use in radiation curable compositions |
| WO2012106820A1 (en) | 2011-02-08 | 2012-08-16 | Sierra Wireless, Inc. | Method and system for forwarding data between network devices |
| DE102012212429A1 (de) | 2012-07-16 | 2014-01-16 | Voco Gmbh | Dentalhandgerät, Verfahren und Verwendung desselben zum Aushärten lichthärtbaren Materials |
| GB201213163D0 (en) | 2012-07-24 | 2012-09-05 | Lambson Ltd | Photopolymerisation processes and novel compounds therefor |
| EP2903995B1 (en) * | 2012-10-01 | 2019-01-16 | ETH Zürich | A process for the preparation of acylphosphanes |
| EP2935393A4 (en) | 2012-12-18 | 2016-06-01 | Basf Se | SEMICONDUCTOR MATERIALS BASED ON NAPHTHALENDIIMIDE VINYLENE OLIGOTHIOPHENO VINYLENE POLYMERS |
| JP6400021B2 (ja) * | 2012-12-19 | 2018-10-03 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | ビスアシルホスフィン酸の誘導体、その製造および光開始剤としての使用 |
| EP3409680B1 (en) * | 2017-05-30 | 2021-01-06 | IGM Group B.V. | Synthesis of bis(acyl)phosphines by activation of unreactive metal phosphides |
| CN107082787B (zh) * | 2017-06-09 | 2019-05-17 | 江苏富比亚化学品有限公司 | 一种苯甲酰基苯基次膦酸及其衍生物的制备方法 |
| TWI782066B (zh) | 2017-08-03 | 2022-11-01 | 德商漢高股份有限及兩合公司 | 可固化的聚矽氧光學透明黏著劑及其用途 |
| JP2020531594A (ja) * | 2017-08-24 | 2020-11-05 | スージョウ・レインボー・マテリアルズ・カンパニー・リミテッドSuzhou Rainbow Materials Co., Ltd. | シリコーン高分子光開始剤およびその使用 |
| MX2020006710A (es) | 2017-12-27 | 2020-08-20 | Henkel IP & Holding GmbH | Adhesivos sensibles a la presion opticamente transparentes y usos de los mismos. |
| KR102693603B1 (ko) | 2018-10-01 | 2024-08-09 | 다우 글로벌 테크놀로지스 엘엘씨 | 유기 규소 화합물, 이의 제조 방법 및 그 사용 |
| CN115701282A (zh) * | 2020-05-14 | 2023-02-07 | 3M创新有限公司 | 包含至少一个使用氟化光引发剂制备的氟化(共)聚合物层的多层光学膜及其制备和使用方法 |
| KR102651787B1 (ko) * | 2021-07-14 | 2024-03-26 | 주식회사 엘지에너지솔루션 | 리튬 이차전지용 비수계 전해액 및 이를 포함하는 리튬 이차전지 |
| CN114349788B (zh) * | 2021-12-30 | 2023-06-20 | 华南理工大学 | 一种光引发剂及其制备方法与应用 |
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| DE2830928A1 (de) * | 1978-07-14 | 1980-01-31 | Basf Ag | Lichthaertbare form-, traenk- und ueberzugsmassen |
| DE3020092A1 (de) * | 1980-05-27 | 1981-12-10 | Basf Ag, 6700 Ludwigshafen | Acylphosphinverbindungen und ihre verwendung |
| DE3114341A1 (de) * | 1981-04-09 | 1982-11-11 | Basf Ag, 6700 Ludwigshafen | Acylphosphinverbindungen, ihre herstellung und verwendung |
| DE3133419A1 (de) * | 1981-08-24 | 1983-03-10 | Basf Ag, 6700 Ludwigshafen | Acylphosphinoxidverbindungen und ihre verwendung |
| DE3443221A1 (de) * | 1984-11-27 | 1986-06-05 | ESPE Fabrik pharmazeutischer Präparate GmbH, 8031 Seefeld | Bisacylphosphinoxide, ihre herstellung und verwendung |
| DE3878139T2 (de) * | 1987-05-01 | 1993-05-27 | Mitsubishi Rayon Co | Mit aktinischen strahlen haertbare zusammensetzung fuer giesspolymerisation und giesspolymerisationsprodukte. |
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| US5218009A (en) | 1989-08-04 | 1993-06-08 | Ciba-Geigy Corporation | Mono- and di-acylphosphine oxides |
| EP0413657B1 (de) * | 1989-08-04 | 1996-12-27 | Ciba SC Holding AG | Mono- und Diacylphosphinoxide |
| RU2091385C1 (ru) | 1991-09-23 | 1997-09-27 | Циба-Гейги АГ | Бисацилфосфиноксиды, состав и способ нанесения покрытий |
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| SE520727C2 (sv) * | 1996-03-04 | 2003-08-19 | Ciba Sc Holding Ag | Alkylfenylbisacylfosfinoxid och fotoinitiatorblandningar |
| JPH09241312A (ja) * | 1996-03-08 | 1997-09-16 | Showa Denko Kk | 光硬化性人造大理石用組成物及びその硬化方法 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10597413B2 (en) | 2016-01-11 | 2020-03-24 | Henkel Ag & Co. Kgaa | Silicone-compatible compounds |
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| GB2360283A (en) | 2001-09-19 |
| FR2804683A1 (fr) | 2001-08-10 |
| JP2011140524A (ja) | 2011-07-21 |
| ES2195706A1 (es) | 2003-12-01 |
| DE10105046A1 (de) | 2001-08-09 |
| BE1013960A3 (fr) | 2003-01-14 |
| JP2001270894A (ja) | 2001-10-02 |
| ES2195706B1 (es) | 2005-03-01 |
| BR0100910A (pt) | 2001-10-02 |
| US6579663B2 (en) | 2003-06-17 |
| US6399805B2 (en) | 2002-06-04 |
| KR20010083161A (ko) | 2001-08-31 |
| US20010031898A1 (en) | 2001-10-18 |
| NL1017310C2 (nl) | 2002-06-18 |
| CN1308081A (zh) | 2001-08-15 |
| ITMI20010242A1 (it) | 2002-08-07 |
| TW555762B (en) | 2003-10-01 |
| CA2334291A1 (en) | 2001-08-08 |
| US20020107413A1 (en) | 2002-08-08 |
| FR2804683B1 (fr) | 2005-04-08 |
| GB0102398D0 (en) | 2001-03-14 |
| NL1017310A1 (nl) | 2001-08-09 |
| KR100769838B1 (ko) | 2007-10-24 |
| GB2360283B (en) | 2002-08-21 |
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