FI110187B - Uudet oniumboraatit tai organometallikompleksin boraatit, jotka ovat kationisia polymerointi-initiaattoreita - Google Patents
Uudet oniumboraatit tai organometallikompleksin boraatit, jotka ovat kationisia polymerointi-initiaattoreita Download PDFInfo
- Publication number
- FI110187B FI110187B FI931253A FI931253A FI110187B FI 110187 B FI110187 B FI 110187B FI 931253 A FI931253 A FI 931253A FI 931253 A FI931253 A FI 931253A FI 110187 B FI110187 B FI 110187B
- Authority
- FI
- Finland
- Prior art keywords
- borates
- cyclopentadienyl
- formula
- group
- groups
- Prior art date
Links
- 150000001642 boronic acid derivatives Chemical class 0.000 title claims description 15
- 125000002524 organometallic group Chemical group 0.000 title claims description 15
- 238000010538 cationic polymerization reaction Methods 0.000 title claims description 4
- 239000003505 polymerization initiator Substances 0.000 title 1
- -1 carbocyclic aryl radical Chemical class 0.000 claims description 39
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- 239000003446 ligand Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000003999 initiator Substances 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- 229910052744 lithium Inorganic materials 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000002091 cationic group Chemical group 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000010894 electron beam technology Methods 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 239000011651 chromium Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- RWGFKTVRMDUZSP-UHFFFAOYSA-N isopropyl-benzene Natural products CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- 229910021645 metal ion Inorganic materials 0.000 claims 1
- 229910052711 selenium Inorganic materials 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 20
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 9
- 150000001450 anions Chemical class 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VQVGJEIVVJBMCV-UHFFFAOYSA-N (4-octoxyphenyl)-phenyliodanium Chemical compound C1=CC(OCCCCCCCC)=CC=C1[I+]C1=CC=CC=C1 VQVGJEIVVJBMCV-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- AENNXXRRACDJAY-UHFFFAOYSA-N bis(2-dodecylphenyl)iodanium Chemical compound CCCCCCCCCCCCC1=CC=CC=C1[I+]C1=CC=CC=C1CCCCCCCCCCCC AENNXXRRACDJAY-UHFFFAOYSA-N 0.000 description 3
- LIXRCYUJVYSDRX-UHFFFAOYSA-M bis(2-dodecylphenyl)iodanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC1=CC=CC=C1[I+]C1=CC=CC=C1CCCCCCCCCCCC LIXRCYUJVYSDRX-UHFFFAOYSA-M 0.000 description 3
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LDSRDVDEPKEARF-UHFFFAOYSA-M 4-methylbenzenesulfonate;(4-octoxyphenyl)-phenyliodanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC(OCCCCCCCC)=CC=C1[I+]C1=CC=CC=C1 LDSRDVDEPKEARF-UHFFFAOYSA-M 0.000 description 2
- 229910017048 AsF6 Inorganic materials 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 101100010166 Mus musculus Dok3 gene Proteins 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- UZILCZKGXMQEQR-UHFFFAOYSA-N decyl-Benzene Chemical compound CCCCCCCCCCC1=CC=CC=C1 UZILCZKGXMQEQR-UHFFFAOYSA-N 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- HZNFSZMIMUTCGG-UHFFFAOYSA-N n-(3-hydroxypyridin-4-yl)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=NC=C1O HZNFSZMIMUTCGG-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- XEKTVXADUPBFOA-UHFFFAOYSA-N 1-bromo-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(Br)C(F)=C1F XEKTVXADUPBFOA-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- GSOLWAFGMNOBSY-UHFFFAOYSA-N cobalt Chemical compound [Co][Co][Co][Co][Co][Co][Co][Co] GSOLWAFGMNOBSY-UHFFFAOYSA-N 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- URSLCTBXQMKCFE-UHFFFAOYSA-N dihydrogenborate Chemical compound OB(O)[O-] URSLCTBXQMKCFE-UHFFFAOYSA-N 0.000 description 1
- RSJLWBUYLGJOBD-UHFFFAOYSA-M diphenyliodanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[I+]C1=CC=CC=C1 RSJLWBUYLGJOBD-UHFFFAOYSA-M 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- IOEDDFFKYCBADJ-UHFFFAOYSA-M lithium;4-methylbenzenesulfonate Chemical compound [Li+].CC1=CC=C(S([O-])(=O)=O)C=C1 IOEDDFFKYCBADJ-UHFFFAOYSA-M 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- ZPIRTVJRHUMMOI-UHFFFAOYSA-N octoxybenzene Chemical compound CCCCCCCCOC1=CC=CC=C1 ZPIRTVJRHUMMOI-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/72—Complexes of boron halides
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/52—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from boron, aluminium, gallium, indium, thallium or rare earths
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Polymerization Catalysts (AREA)
- Epoxy Resins (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9203440 | 1992-03-23 | ||
| FR9203440A FR2688783A1 (fr) | 1992-03-23 | 1992-03-23 | Nouveaux borates d'onium ou de complexe organometallique amorceurs cationiques de polymerisation. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI931253A0 FI931253A0 (fi) | 1993-03-22 |
| FI931253A FI931253A (fi) | 1993-09-24 |
| FI110187B true FI110187B (fi) | 2002-12-13 |
Family
ID=9427943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI931253A FI110187B (fi) | 1992-03-23 | 1993-03-22 | Uudet oniumboraatit tai organometallikompleksin boraatit, jotka ovat kationisia polymerointi-initiaattoreita |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US5468902A (de) |
| EP (1) | EP0562897B1 (de) |
| JP (1) | JP2557782B2 (de) |
| AU (1) | AU660218B2 (de) |
| CA (1) | CA2092135C (de) |
| DE (1) | DE69325537T2 (de) |
| ES (1) | ES2133368T3 (de) |
| FI (1) | FI110187B (de) |
| FR (1) | FR2688783A1 (de) |
Families Citing this family (114)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6147184A (en) * | 1992-03-23 | 2000-11-14 | Rhone-Poulenc Chimie | Onium borates/borates of organometallic complexes and cationic initiation of polymerization therewith |
| EP1028119B1 (de) * | 1992-06-23 | 2004-05-26 | The Dow Chemical Company | Verfahren zur Herstellung von Tetrakisfluorphenylboraten |
| FR2702485B1 (fr) * | 1993-03-10 | 1995-04-14 | Rhone Poulenc Chimie | Compositions à base de polyorganosiloxanes réticulables par voie cationique et leur utilisation dans le domaine de l'antiadhérence papier, de la protection des fibres optiques et des circuits imprimés. |
| US5514728A (en) * | 1993-07-23 | 1996-05-07 | Minnesota Mining And Manufacturing Company | Catalysts and initiators for polymerization |
| FR2724660B1 (fr) * | 1994-09-16 | 1997-01-31 | Rhone Poulenc Chimie | Amorceurs de reticulation, par voie cationique, de polymeres a groupements organofonctionnels, compositions a base de polyorganosiloxanes reticulables et contenant ces amorceurs et application desdites compositions en antiadherence |
| FR2727416A1 (fr) * | 1994-11-24 | 1996-05-31 | Rhone Poulenc Chimie | Nouveaux amorceurs cationiques thermoactivables, de polymerisation et/ou de reticulation et compositions monomeres et/ou polymeres fonctionnels les mettant en oeuvre |
| US5744511A (en) * | 1995-04-19 | 1998-04-28 | Tokuyama Corporation | Visible ray polymerization initiator and visible ray polymerizable composition |
| AU717137B2 (en) * | 1995-11-24 | 2000-03-16 | Ciba Specialty Chemicals Holding Inc. | Borate coinitiators for photopolymerization |
| TW466256B (en) | 1995-11-24 | 2001-12-01 | Ciba Sc Holding Ag | Borate photoinitiator compounds and compositions comprising the same |
| JP3937466B2 (ja) * | 1995-12-28 | 2007-06-27 | 東洋インキ製造株式会社 | 感エネルギー線酸発生剤、感エネルギー線酸発生剤組成物および硬化性組成物 |
| US6291695B1 (en) | 1996-02-20 | 2001-09-18 | Northwestern University | Organo-Lewis acids of enhanced utility, uses thereof, and products based thereon |
| US6274752B1 (en) | 1996-02-20 | 2001-08-14 | Northwestern University | Organo-Lewis acid as cocatalyst for cationic homogeneous Ziegler-Natta olefin polymerizations |
| US5856256A (en) * | 1996-02-20 | 1999-01-05 | Northwestern University | Organo-Lewis acid as cocatalyst for cationic homogeneous Ziegler-Natta olefin polymerizations |
| US5703137A (en) * | 1996-03-14 | 1997-12-30 | Rhone-Poulenc Chimie | Initiators for the cationic crosslinking of polymers containing organofunctional groups |
| KR100437238B1 (ko) * | 1996-03-27 | 2004-08-16 | 다우 글로벌 테크놀로지스 인크. | 고가용성올레핀중합촉매활성화제 |
| TW460509B (en) | 1996-07-12 | 2001-10-21 | Ciba Sc Holding Ag | Curing process for cationically photocurable formulations |
| FR2757529B1 (fr) * | 1996-12-24 | 1999-03-05 | Rhodia Chimie Sa | Compositions stables a base de polyorganosiloxanes a groupements fonctionnels reticulables et leur utilisation pour la realisation de revetements anti-adherents |
| FR2766491B1 (fr) * | 1997-07-23 | 1999-10-08 | Rhodia Chimie Sa | Nouveaux systemes amorceurs de polymerisation et/ou de reticulation comprenant un borate d'onium et une benzophenone |
| FR2766490B1 (fr) * | 1997-07-23 | 1999-10-08 | Rhodia Chimie Sa | Nouveaux systemes amorceurs de polymerisation et/ou de reticulation comprenant un borate d'onium et une benzophenone |
| US6002044A (en) * | 1997-11-12 | 1999-12-14 | Showa Denko K.K. | Production method of borate compounds |
| US6022643A (en) * | 1997-12-08 | 2000-02-08 | Brookhaven Science Associates | Boron compounds as anion binding agents for nonaqueous battery electrolytes |
| FR2784024B1 (fr) * | 1998-10-02 | 2002-10-31 | Rhodia Chimie Sa | Composition dentaire a base d'une silicone fonctionnalisee reticulable/polymerisable par voie cationique en presence d'un borate d'un complexe organometallique |
| FR2784025B1 (fr) * | 1998-10-02 | 2002-10-31 | Rhodia Chimie Sa | Composition dentaire a base d'une silicone fonctionnalisee reticulable/polymerisable par voie cationique |
| US6587628B1 (en) | 1999-11-22 | 2003-07-01 | 3M Innovative Properties Company | Optical fiber with improved strength in high humidity/high temperature environments |
| US6169208B1 (en) | 1999-12-03 | 2001-01-02 | Albemarle Corporation | Process for producing a magnesium di[tetrakis(Faryl)borate] and products therefrom |
| US6162950A (en) * | 1999-12-03 | 2000-12-19 | Albemarle Corporation | Preparation of alkali metal tetrakis(F aryl)borates |
| US6377102B2 (en) * | 2000-02-29 | 2002-04-23 | Texas Instruments Incorporated | Load equalization in digital delay interpolators |
| WO2002046263A1 (de) * | 2000-12-08 | 2002-06-13 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Harzformulierung, verfahren zu ihrer härtung und ihre verwendung |
| FR2818553B1 (fr) * | 2000-12-22 | 2003-02-07 | Rhodia Chimie Sa | Composition dentaire a base d'une silicone fonctionnalisee reticulaire et/ou polymerisable par voie thermique |
| US6895156B2 (en) | 2001-10-09 | 2005-05-17 | 3M Innovative Properties Company | Small diameter, high strength optical fiber |
| FR2833484B1 (fr) * | 2001-12-18 | 2004-12-10 | Rhodia Chimie Sa | Composition dentaire a base de solution de silice colloidale en phase continue silicone |
| US6649716B2 (en) | 2001-12-18 | 2003-11-18 | Sunoco, Inc. (R&M) | Polymerization of alpha-methylstyrene |
| US6918984B2 (en) * | 2002-06-24 | 2005-07-19 | Loctite (R&D) Limited | Photocurable adhesive compositions, reaction products of which have low halide ion content |
| US20050059752A1 (en) | 2002-07-12 | 2005-03-17 | Rhodia Chimie | Stable, cationically polymerizable/crosslinkable dental compositions having high filler contents |
| US7329480B2 (en) | 2002-08-30 | 2008-02-12 | Toyo Gosei Co., Ltd. | Radiation-sensitive negative-type resist composition for pattern formation method |
| US6831200B2 (en) * | 2002-10-03 | 2004-12-14 | Albemarle Corporation | Process for producing tetrakis(Faryl)borate salts |
| WO2004058699A2 (en) * | 2002-12-23 | 2004-07-15 | Aprilis, Inc. | Fluoroarylsulfonium photoacid generators |
| US20050003216A1 (en) | 2003-06-30 | 2005-01-06 | Jean-Marc Frances | Microparticle containing silicone release coatings having improved anti-block and release properties |
| US7393627B2 (en) * | 2004-03-16 | 2008-07-01 | Cornell Research Foundation, Inc. | Environmentally friendly photoacid generators (PAGs) with no perfluorooctyl sulfonates (PFOS) |
| WO2005116038A1 (ja) * | 2004-05-28 | 2005-12-08 | San-Apro Limited | 新規なオニウムおよび遷移金属錯体のフッ素化アルキルフルオロリン酸塩 |
| KR100698917B1 (ko) * | 2004-06-22 | 2007-03-22 | 미쓰이 가가쿠 가부시키가이샤 | 이온성 화합물 및 그것을 함유하는 수지 조성물과 그 용도 |
| US7498123B2 (en) * | 2005-03-03 | 2009-03-03 | Exciton, Inc. | Infrared dye compositions |
| JP2007051193A (ja) | 2005-08-17 | 2007-03-01 | Fujifilm Corp | インク組成物、インクジェット記録方法、印刷物、平版印刷版の製造方法、及び、平版印刷版 |
| US7618683B2 (en) | 2006-01-12 | 2009-11-17 | Fujifilm Corporation | Ink composition, inkjet recording method, printed material, process for producing lithographic printing plate, and lithographic printing plate |
| DE102006005103A1 (de) * | 2006-02-04 | 2007-08-09 | Merck Patent Gmbh | Oxonium- und Sulfoniumsalze |
| WO2007124092A2 (en) * | 2006-04-21 | 2007-11-01 | Cornell Research Foundation, Inc. | Photoacid generator compounds and compositions |
| US7524614B2 (en) * | 2006-05-26 | 2009-04-28 | Eastman Kodak Company | Negative-working radiation-sensitive compositions and imageable materials |
| US8030401B1 (en) | 2006-08-03 | 2011-10-04 | Henkel Corporation | Photoinitiated cationic epoxy compositions |
| JO3598B1 (ar) | 2006-10-10 | 2020-07-05 | Infinity Discovery Inc | الاحماض والاسترات البورونية كمثبطات اميد هيدروليز الحامض الدهني |
| US7714037B1 (en) | 2006-12-15 | 2010-05-11 | Henkel Corporation | Photoinitiated cationic epoxy compositions and articles exhibiting low color |
| GB2450975B (en) | 2007-07-12 | 2010-02-24 | Ciba Holding Inc | Yellow radiation curing inks |
| US7705064B2 (en) * | 2007-07-23 | 2010-04-27 | Henkel Corporation | Photosensitive compounds, photopolymerizable compositions including the same, and methods of making and using the same |
| WO2009057600A1 (ja) | 2007-11-01 | 2009-05-07 | Adeka Corporation | 塩化合物、カチオン重合開始剤およびカチオン重合性組成物 |
| JP4901889B2 (ja) * | 2008-02-18 | 2012-03-21 | ソニーケミカル＆インフォメーションデバイス株式会社 | 磁性シート組成物、磁性シート、及び磁性シートの製造方法 |
| JP5101343B2 (ja) | 2008-03-03 | 2012-12-19 | 株式会社ダイセル | 微細構造物の製造方法 |
| TW201000107A (en) | 2008-04-09 | 2010-01-01 | Infinity Pharmaceuticals Inc | Inhibitors of fatty acid amide hydrolase |
| US8163461B2 (en) * | 2008-04-09 | 2012-04-24 | Cornell Research Foundation, Inc. | Photoacid generator compounds and compositions |
| US8309633B2 (en) * | 2008-07-17 | 2012-11-13 | Henkel Ireland Ltd. | Low temperature, cationically curable compositions with improved cure speed and toughness |
| JP5444702B2 (ja) | 2008-12-05 | 2014-03-19 | デクセリアルズ株式会社 | 新規なスルホニウムボレート錯体 |
| US8188161B1 (en) | 2009-01-23 | 2012-05-29 | Henkel Corporation | Anaerobic cure systems for anaerobic curable compositions, and anaerobic curable compositions containing same |
| JP5485583B2 (ja) * | 2009-05-08 | 2014-05-07 | 株式会社日本触媒 | ジアリールヨードニウム化合物の製造方法 |
| US8975203B2 (en) | 2009-05-08 | 2015-03-10 | Nippon Shokubai Co., Ltd. | Diaryliodonium salt mixture and process for production thereof, and process for production of diaryliodonium compound |
| WO2010140547A1 (ja) * | 2009-06-02 | 2010-12-09 | 山本化成株式会社 | ヨードニウム系光重合開始剤、その製造方法およびこれを含有してなる光硬化性組成物 |
| WO2011040531A1 (ja) | 2009-10-01 | 2011-04-07 | 日立化成工業株式会社 | 有機エレクトロニクス用材料、有機エレクトロニクス素子、有機エレクトロルミネセンス素子、及びそれを用いた表示素子、照明装置、表示装置 |
| JP5635526B2 (ja) | 2009-10-26 | 2014-12-03 | 株式会社Adeka | 芳香族スルホニウム塩化合物 |
| JP5717959B2 (ja) | 2009-11-17 | 2015-05-13 | 株式会社Adeka | 芳香族スルホニウム塩化合物 |
| KR101833078B1 (ko) * | 2009-12-17 | 2018-02-27 | 디에스엠 아이피 어셋츠 비.브이. | 적층식 제작을 위한 발광 다이오드 경화성 액체 수지 조성물 |
| RU2569061C2 (ru) | 2010-02-03 | 2015-11-20 | Инфинити Фармасьютикалз, Инк. | Ингибиторы амид-гидролазы жирных кислот |
| JP2011184506A (ja) | 2010-03-05 | 2011-09-22 | Shin-Etsu Chemical Co Ltd | 放射線硬化性シリコーン組成物 |
| FR2957604A1 (fr) | 2010-03-22 | 2011-09-23 | Bluestar Silicones France | Composition silicone reticulable pour la realisation de revetements anti-adherents pour supports souples et additif promoteur d'accrochage contenu dans cette composition |
| KR20140108701A (ko) | 2010-04-22 | 2014-09-12 | 히타치가세이가부시끼가이샤 | 유기 일렉트로닉스 재료, 중합 개시제 및 열중합 개시제, 잉크 조성물, 유기 박막 및 그 제조 방법, 유기 일렉트로닉스 소자, 유기 일렉트로 루미네센스 소자, 조명 장치, 표시 소자, 및 표시 장치 |
| TWI523882B (zh) * | 2010-07-14 | 2016-03-01 | 日本化藥股份有限公司 | 感光性樹脂組成物及其硬化物 |
| JP5494417B2 (ja) | 2010-10-28 | 2014-05-14 | 信越化学工業株式会社 | 放射線硬化性シリコーン組成物 |
| EP2723576B1 (de) | 2011-06-21 | 2017-08-09 | Basf Se | Drucken von diffraktionsgittern auf papier und karton |
| US9011983B2 (en) | 2011-07-29 | 2015-04-21 | Ideon Llc | Process for curing a composition by electron beam radiation, and by gas-generated plasma and ultraviolet radiation |
| KR20150027205A (ko) | 2012-06-14 | 2015-03-11 | 바스프 에스이 | 보안 요소 및 홀로그램의 제조 방법 |
| JP5899068B2 (ja) | 2012-06-28 | 2016-04-06 | 東京応化工業株式会社 | 厚膜用ポジ型レジスト組成物、厚膜レジストパターンの製造方法、接続端子の製造方法 |
| CA2883840C (en) | 2012-09-17 | 2021-01-26 | Basf Se | Security elements and method for their manufacture |
| EP2912075B1 (de) | 2012-10-02 | 2016-12-14 | Bluestar Silicones France SAS | Kationisch polymerisierbare/vernetzbare zusammensetzung mit einem jodoniumborat und freisetzung eines akzeptablen geruchs |
| FR2996227A1 (fr) * | 2012-10-02 | 2014-04-04 | Bluestar Silicones France | Composition de resine organique reticulable/polymerisable par voie cationique comprenant un borate de iodonium et degageant une odeur acceptable |
| JP6428600B2 (ja) | 2013-03-08 | 2018-11-28 | 日立化成株式会社 | イオン性化合物を含有する処理液、有機エレクトロニクス素子、及び有機エレクトロニクス素子の製造方法 |
| WO2014187750A1 (en) | 2013-05-21 | 2014-11-27 | Basf Se | Security elements and method for their manufacture |
| EP3052701B1 (de) | 2013-10-04 | 2017-06-28 | Basf Se | Hochglänzende metalleffektpapiere und -pappe |
| EP3104383A4 (de) | 2014-02-06 | 2017-09-20 | Adeka Corporation | Träger und element zur photoelektrischen umwandlung |
| EP2915822A1 (de) | 2014-03-06 | 2015-09-09 | Université de Haute Alsace | Lichtinduziertes freiradikalisches und/oder kationisches Photopolymerisationsverfahren |
| CN104497277A (zh) * | 2014-11-26 | 2015-04-08 | 南京凯泰化工科技有限公司 | 一种自由基光引发剂及其制备方法 |
| CN107429491A (zh) | 2015-03-30 | 2017-12-01 | 巴斯夫欧洲公司 | 高光泽金属效应纸和板 |
| MX2017013601A (es) | 2015-04-29 | 2018-07-06 | Bsn Medical Gmbh | Un proceso de etapas multiples para la produccion de no. |
| AU2016256577B2 (en) | 2015-04-29 | 2019-04-04 | Bsn Medical Gmbh | Medical bathing device |
| US10604659B2 (en) | 2015-06-08 | 2020-03-31 | Dsm Ip Assets B.V. | Liquid, hybrid UV/VIS radiation curable resin compositions for additive fabrication |
| JP6633191B2 (ja) | 2015-09-25 | 2020-01-22 | エルケム・シリコーンズ・フランス・エスアエスＥＬＫＥＭ ＳＩＬＩＣＯＮＥＳ Ｆｒａｎｃｅ ＳＡＳ | 可撓性基材用の不粘着性コーティングを製造するための架橋性シリコーン組成物及びこの組成物に含有される付着促進用添加剤 |
| JP6880416B2 (ja) | 2015-10-01 | 2021-06-02 | ディーエスエム アイピー アセッツ ビー．ブイ．Ｄｓｍ Ｉｐ Ａｓｓｅｔｓ Ｂ．Ｖ． | 付加造形用液状ハイブリッドＵＶ／ｖｉｓ線硬化性樹脂組成物 |
| JP6603127B2 (ja) | 2015-12-29 | 2019-11-06 | サンアプロ株式会社 | 感光性組成物 |
| FR3052784A1 (fr) | 2016-06-21 | 2017-12-22 | Bluestar Silicones France | Procede de lutte contre l'apparition de brouillard dans un dispositif a cylindres lors de l'enduction de supports flexibles avec une composition silicone liquide reticulable |
| CN111699204B (zh) | 2018-02-16 | 2023-07-21 | 株式会社Adeka | 自由基聚合引发剂、含有其的组合物、其固化物、其制造方法和化合物 |
| CN111936317A (zh) | 2018-04-25 | 2020-11-13 | 巴斯夫欧洲公司 | 在柔性基材上制备强粘附性(压花)膜的方法 |
| US11999865B2 (en) | 2018-09-24 | 2024-06-04 | Basf Se | UV curable composition for use in 3D printing |
| JP2022514433A (ja) | 2018-09-24 | 2022-02-10 | ビーエーエスエフ ソシエタス・ヨーロピア | ３ｄ印刷において使用するための光硬化性組成物 |
| MX2021004736A (es) | 2018-10-25 | 2021-06-04 | Basf Se | Composiciones, que comprenden nanoplaquetas de plata. |
| KR102628070B1 (ko) | 2018-12-20 | 2024-01-23 | 엘켐 실리콘즈 프랑스 에스에이에스 | 가교가능한 액체 실리콘 조성물에 의한 가요성 지지체의 코팅 동안 롤을 포함한 디바이스에서 미스트 형성의 방지를 위한 방법 |
| EP3680274A1 (de) | 2019-01-14 | 2020-07-15 | Basf Se | Hydroxyurethan-(meth)acrylatpräpolymere zur verwendung im 3d-druck |
| EP3680263A1 (de) | 2019-01-14 | 2020-07-15 | Basf Se | Limonenbasierte (meth)acrylate zur verwendung im 3d-druck |
| WO2020152021A1 (en) | 2019-01-21 | 2020-07-30 | Basf Se | Security element |
| WO2020156858A1 (en) | 2019-01-29 | 2020-08-06 | Basf Se | Security element |
| EP3965983A1 (de) | 2019-05-06 | 2022-03-16 | Basf Se | Zusammensetzungen mit silbernanoplättchen |
| CN114450631A (zh) | 2019-09-30 | 2022-05-06 | 富士胶片株式会社 | 感光化射线性或感放射线性树脂组合物、感光化射线性或感放射线性膜、图案形成方法及电子器件的制造方法 |
| JP2023500370A (ja) | 2019-11-07 | 2023-01-05 | ビーエーエスエフ ソシエタス・ヨーロピア | ３ｄ印刷で使用するための水洗可能な組成物 |
| JPWO2021095711A1 (de) | 2019-11-14 | 2021-05-20 | ||
| CN115362412A (zh) | 2020-03-30 | 2022-11-18 | 富士胶片株式会社 | 感光化射线性或感放射线性树脂组合物、感光化射线性或感放射线性膜、图案形成方法、电子器件的制造方法、光掩模制造用感光化射线性或感放射线性树脂组合物及光掩模的制造方法 |
| CN115279518A (zh) | 2020-04-23 | 2022-11-01 | 巴斯夫欧洲公司 | 包含片状过渡金属颗粒的组合物 |
| EP4166529A1 (de) | 2020-06-12 | 2023-04-19 | San-Apro Ltd. | Neuartiges oniumsalz und fotosäurebildner |
| EP4261214A4 (de) | 2020-12-14 | 2024-06-05 | San-Apro Ltd. | Fotosäuregenerator und lichtempfindliche zusammensetzung damit |
| WO2022129348A1 (fr) | 2020-12-16 | 2022-06-23 | Elkem Silicones France Sas | Composition silicone biocide applicable sur des surfaces |
| WO2023170132A1 (en) | 2022-03-10 | 2023-09-14 | Basf Se | Casting lacquer for screen printing |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US506674A (en) * | 1893-10-17 | Paper-fastener | ||
| US4378277A (en) * | 1974-05-08 | 1983-03-29 | Minnesota Mining & Manufacturing Company | Photopolymerizable epoxy-containing compositions |
| US4238619A (en) * | 1979-06-06 | 1980-12-09 | General Electric Company | Method for making aryl onium salts of group via elements |
| US5153157A (en) * | 1987-01-30 | 1992-10-06 | Exxon Chemical Patents Inc. | Catalyst system of enhanced productivity |
| SE8901048D0 (sv) * | 1989-03-23 | 1989-03-23 | Becker Wilhelm Ab | Polymerisationsinitiator |
| CA2024830A1 (en) * | 1989-09-29 | 1991-03-30 | Richard E. Campbell, Jr. | Process for preparation of syndiotactic vinyl aromatic polymers |
| US4992571A (en) * | 1989-10-31 | 1991-02-12 | General Electric Company | Method for making octyloxy substituted diphenyl iodonium hexafluoro metalloid salts |
| US5084586A (en) * | 1990-02-12 | 1992-01-28 | Minnesota Mining And Manufacturing Company | Novel initiators for cationic polymerization |
| JP2545006B2 (ja) * | 1990-07-03 | 1996-10-16 | ザ ダウ ケミカル カンパニー | 付加重合触媒 |
| DE69132693T3 (de) * | 1990-10-05 | 2010-01-21 | Idemitsu Kosan Co. Ltd. | Copolymere von Cycloolefinen, daraus hergestellte Zusammensetzungen und Formteile |
| EP0490269B1 (de) * | 1990-12-10 | 1996-02-28 | Idemitsu Kosan Company Limited | Pfropfcopolymer und Verfahren zu seiner Herstellung |
| JP2840462B2 (ja) * | 1990-12-28 | 1998-12-24 | 出光興産株式会社 | スチレン系重合体の製造方法及びその触媒 |
| FR2688790B1 (fr) * | 1992-03-23 | 1994-05-13 | Rhone Poulenc Chimie | Compositions a base de polyorganosiloxanes a groupements fonctionnels reticulables et leur utilisation pour la realisation de revetements anti-adhesifs. |
| US5514728A (en) * | 1993-07-23 | 1996-05-07 | Minnesota Mining And Manufacturing Company | Catalysts and initiators for polymerization |
-
1992
- 1992-03-23 FR FR9203440A patent/FR2688783A1/fr not_active Withdrawn
-
1993
- 1993-03-08 DE DE69325537T patent/DE69325537T2/de not_active Expired - Lifetime
- 1993-03-08 EP EP93400590A patent/EP0562897B1/de not_active Expired - Lifetime
- 1993-03-08 ES ES93400590T patent/ES2133368T3/es not_active Expired - Lifetime
- 1993-03-10 JP JP5075031A patent/JP2557782B2/ja not_active Expired - Lifetime
- 1993-03-12 AU AU35170/93A patent/AU660218B2/en not_active Expired
- 1993-03-22 CA CA002092135A patent/CA2092135C/fr not_active Expired - Lifetime
- 1993-03-22 FI FI931253A patent/FI110187B/fi not_active IP Right Cessation
- 1993-03-23 US US08/035,838 patent/US5468902A/en not_active Expired - Lifetime
-
1995
- 1995-03-08 US US08/400,970 patent/US5550265A/en not_active Expired - Lifetime
-
1996
- 1996-04-18 US US08/634,228 patent/US5668192A/en not_active Expired - Lifetime
-
1997
- 1997-05-06 US US08/851,713 patent/US6153661A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69325537D1 (de) | 1999-08-12 |
| US5468902A (en) | 1995-11-21 |
| FI931253A0 (fi) | 1993-03-22 |
| AU3517093A (en) | 1993-09-30 |
| US6153661A (en) | 2000-11-28 |
| JP2557782B2 (ja) | 1996-11-27 |
| CA2092135C (fr) | 1999-11-30 |
| AU660218B2 (en) | 1995-06-15 |
| US5550265A (en) | 1996-08-27 |
| FI931253A (fi) | 1993-09-24 |
| EP0562897A1 (de) | 1993-09-29 |
| ES2133368T3 (es) | 1999-09-16 |
| DE69325537T2 (de) | 1999-11-18 |
| US5668192A (en) | 1997-09-16 |
| CA2092135A1 (fr) | 1993-09-24 |
| FR2688783A1 (fr) | 1993-09-24 |
| EP0562897B1 (de) | 1999-07-07 |
| JPH06184170A (ja) | 1994-07-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI110187B (fi) | Uudet oniumboraatit tai organometallikompleksin boraatit, jotka ovat kationisia polymerointi-initiaattoreita | |
| JP2623426B2 (ja) | 架橋性官能基を含有するポリオルガノシロキサンを基とする組成物及び抗付着性コーティングの製造のためのその使用 | |
| EP2935289B1 (de) | Derivate von bisacylphosphinsäure, ihre herstellung und verwendung als photoinitiatoren | |
| Matsumoto et al. | Crystal engineering for topochemical polymerization of muconic esters using halogen− halogen and CH/π interactions as weak intermolecular interactions | |
| JP4226672B2 (ja) | フッ素化されたイオン性スルホニルイミド及びスルホニルメチリド、それらの製造方法並びに光開始剤としての使用 | |
| CA2034168A1 (en) | Initiators for cationic polymerization | |
| US20070225458A1 (en) | Novel Fluorinated Alkyl Fluorophosphoric Acid Salts of Onium and Ttransition Metal Complex | |
| US6147184A (en) | Onium borates/borates of organometallic complexes and cationic initiation of polymerization therewith | |
| US4374066A (en) | Method for making triarylsulfonium salts | |
| WO2004000774A1 (en) | Diaryliodonium salt catalysts made from iodotoluene and a method for preparing them | |
| Crivello et al. | Supramolecular diaryliodonium salt‐crown ether complexes as cationic photoinitiators | |
| US6166233A (en) | Onium gallates cationic initiators | |
| US5466845A (en) | Sulfonium salts and process for their preparation | |
| Toneri et al. | Cationic polymerization of epoxide by fluorenylphosphonium salts as thermally latent initiators. Substituent effect on the initiator activity | |
| CN109456242B (zh) | 硫鎓盐光引发剂、其制备方法、包含其的光固化组合物及其应用 | |
| US5354784A (en) | Cyclopentadienyliron complex salt, process for preparing the same and photopolymerizable composition containing the same | |
| CN115521463A (zh) | 三氟甲基有机硅脂环族环氧单体及其制备和应用 | |
| JP2007217672A (ja) | ポリエーテルポリオールの製造方法 | |
| KR20010042957A (ko) | 중금속 비함유 피복 조성물 | |
| Wada et al. | Tris (2-6-dimethoxephenyl) borane and its Adducts | |
| JPH05178819A (ja) | 新規なスルホキソニウム塩 | |
| JP2000344863A (ja) | 重合性組成物及びその硬化物 | |
| Preuss et al. | Crystal structure of (2-acetylferrocen-1-yl) boronic acid | |
| Kim et al. | Novel piperidinium salts as latent initiators for cationic polymerization of epoxide and vinyl ether | |
| JPS58185575A (ja) | ２−メチル−１，３−プロピレングリコ−ルモノアルキレンオキシドエ−テル |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |