FR2727416A1 - Nouveaux amorceurs cationiques thermoactivables, de polymerisation et/ou de reticulation et compositions monomeres et/ou polymeres fonctionnels les mettant en oeuvre - Google Patents
Nouveaux amorceurs cationiques thermoactivables, de polymerisation et/ou de reticulation et compositions monomeres et/ou polymeres fonctionnels les mettant en oeuvre Download PDFInfo
- Publication number
- FR2727416A1 FR2727416A1 FR9414321A FR9414321A FR2727416A1 FR 2727416 A1 FR2727416 A1 FR 2727416A1 FR 9414321 A FR9414321 A FR 9414321A FR 9414321 A FR9414321 A FR 9414321A FR 2727416 A1 FR2727416 A1 FR 2727416A1
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- FR
- France
- Prior art keywords
- sep
- formula
- salts
- cationic
- optionally substituted
- Prior art date
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- Granted
Links
- 239000003999 initiator Substances 0.000 title claims abstract description 66
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 30
- 238000004132 cross linking Methods 0.000 title claims abstract description 9
- 229920000642 polymer Polymers 0.000 claims abstract description 21
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 239000000178 monomer Substances 0.000 claims abstract description 11
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 150000004714 phosphonium salts Chemical class 0.000 claims abstract description 4
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 3
- 150000002148 esters Chemical class 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 54
- 229920001296 polysiloxane Polymers 0.000 claims description 26
- -1 alkenyl radicals Chemical class 0.000 claims description 25
- 239000011159 matrix material Substances 0.000 claims description 23
- 239000004593 Epoxy Substances 0.000 claims description 17
- 150000003254 radicals Chemical class 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical class C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 3
- 230000001464 adherent effect Effects 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 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 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000005023 xylyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000009877 rendering Methods 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract description 4
- 235000010290 biphenyl Nutrition 0.000 abstract description 2
- 239000004305 biphenyl Substances 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000000576 coating method Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229910052700 potassium Inorganic materials 0.000 description 9
- 239000011591 potassium Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 7
- 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 7
- 239000007787 solid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 101710137710 Thioesterase 1/protease 1/lysophospholipase L1 Proteins 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 150000001642 boronic acid derivatives Chemical class 0.000 description 5
- 230000000977 initiatory effect Effects 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 4
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 4
- 229940073608 benzyl chloride Drugs 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- QASBCTGZKABPKX-UHFFFAOYSA-N 4-(methylsulfanyl)phenol Chemical compound CSC1=CC=C(O)C=C1 QASBCTGZKABPKX-UHFFFAOYSA-N 0.000 description 2
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000010538 cationic polymerization reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000007725 thermal activation Methods 0.000 description 2
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- GIGRWGTZFONRKA-UHFFFAOYSA-N 1-(bromomethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CBr)C=C1 GIGRWGTZFONRKA-UHFFFAOYSA-N 0.000 description 1
- DQNSKXYRRRCKGH-UHFFFAOYSA-N 1-methoxy-4-methylsulfanylbenzene Chemical compound COC1=CC=C(SC)C=C1 DQNSKXYRRRCKGH-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- XWNHWKVMWOVNLQ-UHFFFAOYSA-N 2-(4-methoxyphenyl)thiolane Chemical compound C1=CC(OC)=CC=C1C1SCCC1 XWNHWKVMWOVNLQ-UHFFFAOYSA-N 0.000 description 1
- IUGOPULVANEDRX-UHFFFAOYSA-N 2-ethylhexane-1,1-diol Chemical compound CCCCC(CC)C(O)O IUGOPULVANEDRX-UHFFFAOYSA-N 0.000 description 1
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZXABMDQSAABDMG-UHFFFAOYSA-N 3-ethenoxyprop-1-ene Chemical compound C=CCOC=C ZXABMDQSAABDMG-UHFFFAOYSA-N 0.000 description 1
- PSCOCYYMRITEJO-UHFFFAOYSA-N 4-methylbenzenesulfonic acid hydroiodide Chemical compound I.CC1=CC=C(S(O)(=O)=O)C=C1 PSCOCYYMRITEJO-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 101100179093 Schizosaccharomyces pombe (strain 972 / ATCC 24843) idh2 gene Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003522 acrylic cement Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 150000001462 antimony Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
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- 239000003426 co-catalyst Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
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- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- URSLCTBXQMKCFE-UHFFFAOYSA-N dihydrogenborate Chemical compound OB(O)[O-] URSLCTBXQMKCFE-UHFFFAOYSA-N 0.000 description 1
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000004447 silicone coating Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
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- 238000003860 storage Methods 0.000 description 1
- SSTZGACKDAVIGZ-UHFFFAOYSA-N sulfanium;bromide Chemical compound [SH3+].[Br-] SSTZGACKDAVIGZ-UHFFFAOYSA-N 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 231100000402 unacceptable toxicity Toxicity 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
-
- 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
- C07F5/027—Organoboranes and organoborohydrides
-
- 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
- C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/12—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9414321A FR2727416A1 (fr) | 1994-11-24 | 1994-11-24 | Nouveaux amorceurs cationiques thermoactivables, de polymerisation et/ou de reticulation et compositions monomeres et/ou polymeres fonctionnels les mettant en oeuvre |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9414321A FR2727416A1 (fr) | 1994-11-24 | 1994-11-24 | Nouveaux amorceurs cationiques thermoactivables, de polymerisation et/ou de reticulation et compositions monomeres et/ou polymeres fonctionnels les mettant en oeuvre |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2727416A1 true FR2727416A1 (fr) | 1996-05-31 |
| FR2727416B1 FR2727416B1 (enrdf_load_stackoverflow) | 1997-02-14 |
Family
ID=9469281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR9414321A Granted FR2727416A1 (fr) | 1994-11-24 | 1994-11-24 | Nouveaux amorceurs cationiques thermoactivables, de polymerisation et/ou de reticulation et compositions monomeres et/ou polymeres fonctionnels les mettant en oeuvre |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2727416A1 (enrdf_load_stackoverflow) |
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09176112A (ja) * | 1995-12-28 | 1997-07-08 | Toyo Ink Mfg Co Ltd | 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 |
| WO1997033938A1 (en) * | 1996-03-14 | 1997-09-18 | Rhodia Chimie | Initiators for the cationic crosslinking of polymers containing organofunctional groups |
| FR2757870A1 (fr) * | 1996-12-30 | 1998-07-03 | Rhodia Chimie Sa | Utilisation de compositions silicones reticulables par voie cationique sous uv et d'un photoamorceur du type borate d'onium, pour le revetements de joints plats, notamment de joints de culasse |
| FR2782083A1 (fr) * | 1998-08-07 | 2000-02-11 | Rhodia Chimie Sa | Procede de preparation de derives de tetrakis (pentafluorophenyl)borate |
| US6162950A (en) * | 1999-12-03 | 2000-12-19 | Albemarle Corporation | Preparation of alkali metal tetrakis(F aryl)borates |
| US6169208B1 (en) | 1999-12-03 | 2001-01-02 | Albemarle Corporation | Process for producing a magnesium di[tetrakis(Faryl)borate] and products therefrom |
| FR2818553A1 (fr) * | 2000-12-22 | 2002-06-28 | Rhodia Chimie Sa | Composition dentaire a base d'une silicone fonctionnalisee reticulaire et/ou polymerisable par voie thermique |
| WO2002092665A1 (fr) * | 2001-05-15 | 2002-11-21 | Rhodia Chimie | Composition silicone polymerisable reticulable par voie cationique, sous activation thermique et au moyen d'un amorceur de type adduit acide/base de lewis |
| EP1130036A3 (en) * | 2000-02-22 | 2003-12-17 | Mitsubishi Heavy Industries, Ltd. | Composition for bulkhead of thin display panel |
| WO2007087949A3 (de) * | 2006-02-04 | 2007-10-11 | Merck Patent Gmbh | Oxonium- und sulfoniumsalze |
| US20100193228A1 (en) * | 2007-06-15 | 2010-08-05 | Sony Chemical & Information Device Corporation | Epoxy resin composition |
| US7829743B2 (en) * | 2007-06-07 | 2010-11-09 | Sony Corporation | Sulfonium borate complex |
| US20110033732A1 (en) * | 2008-02-18 | 2011-02-10 | Sony Chemical & Information Device Corporation | Magnetic sheet composition, magnetic sheet, and method for producing magnetic sheet |
| US7947663B2 (en) | 2006-10-10 | 2011-05-24 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| JP2012201611A (ja) * | 2011-03-24 | 2012-10-22 | Sanshin Chem Ind Co Ltd | スルホニウム化合物 |
| US8541581B2 (en) | 2009-04-07 | 2013-09-24 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| US8546564B2 (en) | 2009-04-07 | 2013-10-01 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| US8957049B2 (en) | 2008-04-09 | 2015-02-17 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| US9034849B2 (en) | 2010-02-03 | 2015-05-19 | Infinity Pharmaceuticals, Inc. | Fatty acid amide hydrolase inhibitors |
| CN105206184A (zh) * | 2014-06-24 | 2015-12-30 | 三星显示有限公司 | 用于显示装置的覆盖窗、包括该覆盖窗的显示装置以及制造该覆盖窗的方法 |
| US20160280873A1 (en) * | 2015-03-25 | 2016-09-29 | Samsung Display Co., Ltd. | Cover window and display device including the same |
| JP2017052759A (ja) * | 2015-09-11 | 2017-03-16 | デクセリアルズ株式会社 | オニウム化合物の製造方法、及び硬化性樹脂組成物の製造方法 |
| JPWO2016143474A1 (ja) * | 2015-03-10 | 2017-12-21 | 横浜ゴム株式会社 | カチオン重合開始剤およびエポキシ樹脂組成物 |
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| EP0343690A2 (en) * | 1988-05-27 | 1989-11-29 | Nippon Paint Co., Ltd. | Heat-latent, cationic polymerization initiator and resin compositions containing the same |
| WO1990011303A1 (en) * | 1989-03-23 | 1990-10-04 | Ab Wilh. Becker | Initiators for polymerization |
| EP0393893A1 (en) * | 1989-04-08 | 1990-10-24 | Sanshin Kagaku Kogyo Co., Ltd. | Sulfonium compound and polymerisation initator comprising the sulfonium compound as the main ingredient |
| JPH0423807A (ja) * | 1990-05-17 | 1992-01-28 | Nippon Paint Co Ltd | 熱硬化性樹脂組成物 |
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| EP0485990A2 (en) * | 1990-11-14 | 1992-05-20 | Nippon Paint Co., Ltd. | Heat-curable resin composition containing acrylic polymer having alicyclic epoxide functions |
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| EP0562897A1 (fr) * | 1992-03-23 | 1993-09-29 | Rhone-Poulenc Chimie | Nouveaux borates d'onium ou de complexe organométallique amorceurs cationiques de polymérisation |
| EP0562922A1 (fr) * | 1992-03-23 | 1993-09-29 | Rhone-Poulenc Chimie | Compositions à base de polyorganosiloxanes à groupements fonctionnels réticulables et leur utilisation pour la réalisation de revêtements antiadhésifs |
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| EP0343690A2 (en) * | 1988-05-27 | 1989-11-29 | Nippon Paint Co., Ltd. | Heat-latent, cationic polymerization initiator and resin compositions containing the same |
| US5096936A (en) * | 1989-02-09 | 1992-03-17 | Kansai Paint Company, Limited | Photo-crosslinkable resin composition |
| WO1990011303A1 (en) * | 1989-03-23 | 1990-10-04 | Ab Wilh. Becker | Initiators for polymerization |
| EP0393893A1 (en) * | 1989-04-08 | 1990-10-24 | Sanshin Kagaku Kogyo Co., Ltd. | Sulfonium compound and polymerisation initator comprising the sulfonium compound as the main ingredient |
| JPH0423807A (ja) * | 1990-05-17 | 1992-01-28 | Nippon Paint Co Ltd | 熱硬化性樹脂組成物 |
| EP0485990A2 (en) * | 1990-11-14 | 1992-05-20 | Nippon Paint Co., Ltd. | Heat-curable resin composition containing acrylic polymer having alicyclic epoxide functions |
| JPH05230190A (ja) * | 1992-02-25 | 1993-09-07 | Nippon Soda Co Ltd | 含窒素カチオン重合触媒及び含硫黄カチオン重合触媒を含有する硬化性組成物 |
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Cited By (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09176112A (ja) * | 1995-12-28 | 1997-07-08 | Toyo Ink Mfg Co Ltd | 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 |
| WO1997033938A1 (en) * | 1996-03-14 | 1997-09-18 | Rhodia Chimie | Initiators for the cationic crosslinking of polymers containing organofunctional groups |
| US6423378B1 (en) | 1996-12-30 | 2002-07-23 | Rhodia Chimie | Use of silicone compositions cross-linkable by cationic process under UV radiation and of an onium borate type photoinitiator for coating flat joints, particularly cylinder head gaskets |
| FR2757870A1 (fr) * | 1996-12-30 | 1998-07-03 | Rhodia Chimie Sa | Utilisation de compositions silicones reticulables par voie cationique sous uv et d'un photoamorceur du type borate d'onium, pour le revetements de joints plats, notamment de joints de culasse |
| WO1998029498A1 (fr) * | 1996-12-30 | 1998-07-09 | Rhodia Chimie | Utilisation de compositions silicones reticulables par voie cationique sous uv et d'un photoamorceur du type borate d'onium, pour les revetements de joints plats, notamment de joints de culasse |
| FR2782083A1 (fr) * | 1998-08-07 | 2000-02-11 | Rhodia Chimie Sa | Procede de preparation de derives de tetrakis (pentafluorophenyl)borate |
| WO2000008028A1 (fr) * | 1998-08-07 | 2000-02-17 | Rhodia Chimie | Procede de preparation de derives de tetrakis (pentafluorophenyl) borate |
| AU742623B2 (en) * | 1998-08-07 | 2002-01-10 | Rhodia Chimie | Method for preparing tetrakis (pentafluorophenyl) borate derivatives |
| US6162950A (en) * | 1999-12-03 | 2000-12-19 | Albemarle Corporation | Preparation of alkali metal tetrakis(F aryl)borates |
| US6169208B1 (en) | 1999-12-03 | 2001-01-02 | Albemarle Corporation | Process for producing a magnesium di[tetrakis(Faryl)borate] and products therefrom |
| EP1130036A3 (en) * | 2000-02-22 | 2003-12-17 | Mitsubishi Heavy Industries, Ltd. | Composition for bulkhead of thin display panel |
| WO2002051357A1 (fr) * | 2000-12-22 | 2002-07-04 | Rhodia Chimie | Composition dentaire a base d'une silicone fonctionnalisee reticulable et/ou polymerisable par voie thermique |
| FR2818553A1 (fr) * | 2000-12-22 | 2002-06-28 | Rhodia Chimie Sa | Composition dentaire a base d'une silicone fonctionnalisee reticulaire et/ou polymerisable par voie thermique |
| WO2002092665A1 (fr) * | 2001-05-15 | 2002-11-21 | Rhodia Chimie | Composition silicone polymerisable reticulable par voie cationique, sous activation thermique et au moyen d'un amorceur de type adduit acide/base de lewis |
| FR2824835A1 (fr) * | 2001-05-15 | 2002-11-22 | Rhodia Chimie Sa | Composition silicone polymerisable reticulable par voie cationique, sous activation thermique et au moyen d'un amorceur de type adduit acide/base de lewis |
| US7842804B2 (en) | 2006-02-04 | 2010-11-30 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Ionic salts comprising pyrrolidinium, triazolinium, piperidinium or morpholinium cations and alkyltrifluorophosphate anions |
| US8148443B2 (en) | 2006-02-04 | 2012-04-03 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Oxonium and sulfonium salts |
| WO2007087949A3 (de) * | 2006-02-04 | 2007-10-11 | Merck Patent Gmbh | Oxonium- und sulfoniumsalze |
| US7947663B2 (en) | 2006-10-10 | 2011-05-24 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| US8629125B2 (en) | 2006-10-10 | 2014-01-14 | Infinty Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| US9108989B2 (en) | 2006-10-10 | 2015-08-18 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| US8329675B2 (en) | 2006-10-10 | 2012-12-11 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| US8349814B2 (en) | 2006-10-10 | 2013-01-08 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| US7829743B2 (en) * | 2007-06-07 | 2010-11-09 | Sony Corporation | Sulfonium borate complex |
| CN103030659A (zh) * | 2007-06-07 | 2013-04-10 | 索尼化学&信息部件株式会社 | 新型硼酸锍络合物 |
| US20100193228A1 (en) * | 2007-06-15 | 2010-08-05 | Sony Chemical & Information Device Corporation | Epoxy resin composition |
| US8431654B2 (en) * | 2007-06-15 | 2013-04-30 | Sony Chemical & Information Device Corporation | Epoxy resin composition |
| TWI400266B (zh) * | 2008-02-18 | 2013-07-01 | Dexerials Corp | 磁性片組成物、磁性片及磁性片的製造方法 |
| US20110033732A1 (en) * | 2008-02-18 | 2011-02-10 | Sony Chemical & Information Device Corporation | Magnetic sheet composition, magnetic sheet, and method for producing magnetic sheet |
| US8668792B2 (en) | 2008-02-18 | 2014-03-11 | Dexerials Corporation | Method for producing magnetic sheet |
| US8957049B2 (en) | 2008-04-09 | 2015-02-17 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| US8802119B2 (en) | 2009-04-07 | 2014-08-12 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| US8802064B2 (en) | 2009-04-07 | 2014-08-12 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| US8546564B2 (en) | 2009-04-07 | 2013-10-01 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| US8541581B2 (en) | 2009-04-07 | 2013-09-24 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| US9034849B2 (en) | 2010-02-03 | 2015-05-19 | Infinity Pharmaceuticals, Inc. | Fatty acid amide hydrolase inhibitors |
| US9951089B2 (en) | 2010-02-03 | 2018-04-24 | Infinity Pharmaceuticals, Inc. | Methods of treating a fatty acid amide hydrolase-mediated condition |
| JP2012201611A (ja) * | 2011-03-24 | 2012-10-22 | Sanshin Chem Ind Co Ltd | スルホニウム化合物 |
| EP2960281A1 (en) * | 2014-06-24 | 2015-12-30 | Samsung Display Co., Ltd. | Cover window for display device, display device including the same, and method for manufacturing the same |
| CN105206184A (zh) * | 2014-06-24 | 2015-12-30 | 三星显示有限公司 | 用于显示装置的覆盖窗、包括该覆盖窗的显示装置以及制造该覆盖窗的方法 |
| CN105206184B (zh) * | 2014-06-24 | 2019-07-26 | 三星显示有限公司 | 用于显示装置的覆盖窗、包括该覆盖窗的显示装置以及制造该覆盖窗的方法 |
| JPWO2016143474A1 (ja) * | 2015-03-10 | 2017-12-21 | 横浜ゴム株式会社 | カチオン重合開始剤およびエポキシ樹脂組成物 |
| US20160280873A1 (en) * | 2015-03-25 | 2016-09-29 | Samsung Display Co., Ltd. | Cover window and display device including the same |
| KR20160116123A (ko) * | 2015-03-25 | 2016-10-07 | 삼성디스플레이 주식회사 | 커버 윈도우 및 이를 포함하는 표시 장치 |
| KR102352742B1 (ko) * | 2015-03-25 | 2022-01-18 | 삼성디스플레이 주식회사 | 커버 윈도우 및 이를 포함하는 표시 장치 |
| US11242438B2 (en) * | 2015-03-25 | 2022-02-08 | Samsung Display Co., Ltd. | Cover window and display device including the same |
| JP2017052759A (ja) * | 2015-09-11 | 2017-03-16 | デクセリアルズ株式会社 | オニウム化合物の製造方法、及び硬化性樹脂組成物の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2727416B1 (enrdf_load_stackoverflow) | 1997-02-14 |
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