CA2355319A1 - Accelerators useful for energy polymerizable compositions - Google Patents
Accelerators useful for energy polymerizable compositions Download PDFInfo
- Publication number
- CA2355319A1 CA2355319A1 CA002355319A CA2355319A CA2355319A1 CA 2355319 A1 CA2355319 A1 CA 2355319A1 CA 002355319 A CA002355319 A CA 002355319A CA 2355319 A CA2355319 A CA 2355319A CA 2355319 A1 CA2355319 A1 CA 2355319A1
- Authority
- CA
- Canada
- Prior art keywords
- composition
- iron
- composition according
- cyclopentadienyl
- bis
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 186
- 239000000463 material Substances 0.000 claims abstract description 46
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 21
- -1 sulfonyl methide Chemical compound 0.000 claims description 83
- 239000000654 additive Substances 0.000 claims description 64
- 230000000996 additive effect Effects 0.000 claims description 46
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 41
- 239000003999 initiator Substances 0.000 claims description 34
- 150000001768 cations Chemical class 0.000 claims description 26
- 239000003446 ligand Substances 0.000 claims description 23
- 150000001450 anions Chemical group 0.000 claims description 21
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 18
- 239000000853 adhesive Substances 0.000 claims description 18
- 230000001070 adhesive effect Effects 0.000 claims description 18
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000000758 substrate Substances 0.000 claims description 13
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 12
- 229910052742 iron Inorganic materials 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 239000000473 propyl gallate Substances 0.000 claims description 9
- 235000010388 propyl gallate Nutrition 0.000 claims description 9
- 229940075579 propyl gallate Drugs 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 7
- 229920005992 thermoplastic resin Polymers 0.000 claims description 7
- 150000003624 transition metals Chemical group 0.000 claims description 7
- XNEFYCZVKIDDMS-UHFFFAOYSA-N avobenzone Chemical compound C1=CC(OC)=CC=C1C(=O)CC(=O)C1=CC=C(C(C)(C)C)C=C1 XNEFYCZVKIDDMS-UHFFFAOYSA-N 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 6
- 230000000087 stabilizing effect Effects 0.000 claims description 6
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims description 5
- 239000001263 FEMA 3042 Substances 0.000 claims description 5
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims description 5
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 5
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 claims description 5
- 235000015523 tannic acid Nutrition 0.000 claims description 5
- 229940033123 tannic acid Drugs 0.000 claims description 5
- 229920002258 tannic acid Polymers 0.000 claims description 5
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052752 metalloid Inorganic materials 0.000 claims description 4
- 150000002738 metalloids Chemical class 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- XIROXSOOOAZHLL-UHFFFAOYSA-N 2',3',4'-Trihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C(O)=C1O XIROXSOOOAZHLL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000005463 sulfonylimide group Chemical group 0.000 claims description 3
- SHXHPUAKLCCLDV-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)C(F)(F)F SHXHPUAKLCCLDV-UHFFFAOYSA-N 0.000 claims description 2
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 claims description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- DGCTVLNZTFDPDJ-UHFFFAOYSA-N heptane-3,5-dione Chemical compound CCC(=O)CC(=O)CC DGCTVLNZTFDPDJ-UHFFFAOYSA-N 0.000 claims description 2
- QAMFBRUWYYMMGJ-UHFFFAOYSA-N hexafluoroacetylacetone Chemical compound FC(F)(F)C(=O)CC(=O)C(F)(F)F QAMFBRUWYYMMGJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 239000011253 protective coating Substances 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052713 technetium Inorganic materials 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N penta-1,3-diene Chemical compound CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims 1
- 230000000977 initiatory effect Effects 0.000 abstract description 7
- 239000004593 Epoxy Substances 0.000 description 39
- 230000000052 comparative effect Effects 0.000 description 33
- 239000002904 solvent Substances 0.000 description 32
- 239000002023 wood Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 22
- 239000003054 catalyst Substances 0.000 description 20
- 229920000647 polyepoxide Polymers 0.000 description 20
- 238000006116 polymerization reaction Methods 0.000 description 20
- 238000000113 differential scanning calorimetry Methods 0.000 description 19
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 18
- 238000004090 dissolution Methods 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 229910052782 aluminium Inorganic materials 0.000 description 15
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 15
- 239000003822 epoxy resin Substances 0.000 description 15
- 239000000178 monomer Substances 0.000 description 15
- 238000002156 mixing Methods 0.000 description 14
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- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 13
- 150000003077 polyols Chemical class 0.000 description 13
- 239000011550 stock solution Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 11
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 8
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 8
- 239000002671 adjuvant Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- LPYUENQFPVNPHY-UHFFFAOYSA-N methoxycatechol Natural products COC1=CC=CC(O)=C1O LPYUENQFPVNPHY-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 6
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 6
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- 125000005843 halogen group Chemical group 0.000 description 5
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- 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
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- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
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- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
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- QCGKUFZYSPBMAY-UHFFFAOYSA-N methyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1C(C(=O)OC)CCC2OC21 QCGKUFZYSPBMAY-UHFFFAOYSA-N 0.000 description 1
- IBKQQKPQRYUGBJ-UHFFFAOYSA-N methyl gallate Natural products CC(=O)C1=CC(O)=C(O)C(O)=C1 IBKQQKPQRYUGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 125000003357 methylseleno group Chemical group [H]C([H])([H])[Se][*] 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
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- 150000003003 phosphines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
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- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
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- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
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- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
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- 235000012424 soybean oil Nutrition 0.000 description 1
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- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical class [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- AEOGRWUNSVGMMJ-UHFFFAOYSA-N trimethylgermane Chemical compound C[GeH](C)C AEOGRWUNSVGMMJ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
-
- 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)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/223,926 | 1998-12-31 | ||
| US09/223,926 US6265459B1 (en) | 1998-12-31 | 1998-12-31 | Accelerators useful for energy polymerizable compositions |
| PCT/US1999/009309 WO2000040636A1 (en) | 1998-12-31 | 1999-04-29 | Accelerators useful for energy polymerizable compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2355319A1 true CA2355319A1 (en) | 2000-07-13 |
Family
ID=22838561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002355319A Abandoned CA2355319A1 (en) | 1998-12-31 | 1999-04-29 | Accelerators useful for energy polymerizable compositions |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6265459B1 (enExample) |
| EP (2) | EP1757633B1 (enExample) |
| JP (1) | JP4436984B2 (enExample) |
| KR (1) | KR100673923B1 (enExample) |
| CN (1) | CN1332759A (enExample) |
| AU (1) | AU4182199A (enExample) |
| BR (1) | BR9916703A (enExample) |
| CA (1) | CA2355319A1 (enExample) |
| DE (2) | DE69939958D1 (enExample) |
| WO (1) | WO2000040636A1 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7278590B1 (en) | 1992-02-24 | 2007-10-09 | Homax Products, Inc. | Systems and methods for applying texture material to ceiling surfaces |
| US6482868B1 (en) * | 1998-12-31 | 2002-11-19 | 3M Innovative Properties Company | Accelerators useful for energy polymerizable compositions |
| US6635689B1 (en) * | 2000-06-26 | 2003-10-21 | 3M Innovative Properties Company | Accelerators for cationic polymerization catalyzed by iron-based catalysts |
| US6346330B1 (en) * | 2000-12-14 | 2002-02-12 | 3M Innovative Properties Company | Form-in-place gasket for electronic applications |
| US6670017B2 (en) * | 2000-12-14 | 2003-12-30 | 3M Innovative Properties Company | Photocurable form-in-place gasket for electronic applications |
| AU2002315208A1 (en) * | 2001-06-12 | 2002-12-23 | University Of Florida | Method and device for producing near-infrared radiation |
| US20050256230A1 (en) * | 2002-04-01 | 2005-11-17 | Hiroaki Yamaguchi | Cationic polymerizable adhesive composition and anisotropically electroconductive adhesive composition |
| US6869698B2 (en) * | 2002-12-04 | 2005-03-22 | Canon Kabushiki Kaisha | Organic light-emitting device using paracyclophane |
| US6777460B2 (en) * | 2002-12-23 | 2004-08-17 | 3M Innovative Properties Company | Curing agents for cationically curable compositions |
| US7500621B2 (en) | 2003-04-10 | 2009-03-10 | Homax Products, Inc. | Systems and methods for securing aerosol systems |
| US7192991B2 (en) * | 2003-11-26 | 2007-03-20 | 3M Innovative Properties Company | Cationically curable composition |
| US20050126697A1 (en) * | 2003-12-11 | 2005-06-16 | International Business Machines Corporation | Photochemically and thermally curable adhesive formulations |
| US20050161531A1 (en) | 2004-01-28 | 2005-07-28 | Greer Lester R.Jr. | Texture material for covering a repaired portion of a textured surface |
| US20050250929A1 (en) * | 2004-05-10 | 2005-11-10 | 3M Innovative Properties Company | Ferrocenium-derived catalyst for cationically polymerizable monomers |
| US7677420B1 (en) | 2004-07-02 | 2010-03-16 | Homax Products, Inc. | Aerosol spray texture apparatus for a particulate containing material |
| US7487893B1 (en) | 2004-10-08 | 2009-02-10 | Homax Products, Inc. | Aerosol systems and methods for dispensing texture material |
| CN101175607A (zh) * | 2005-04-08 | 2008-05-07 | 圣戈本磨料股份有限公司 | 具有反应活性生色团的研磨制品 |
| US8344056B1 (en) | 2007-04-04 | 2013-01-01 | Homax Products, Inc. | Aerosol dispensing systems, methods, and compositions for repairing interior structure surfaces |
| US8469292B1 (en) | 2007-04-04 | 2013-06-25 | Homax Products, Inc. | Spray texture material compositions and dispensing systems and methods |
| US9382060B1 (en) | 2007-04-05 | 2016-07-05 | Homax Products, Inc. | Spray texture material compositions, systems, and methods with accelerated dry times |
| US8580349B1 (en) | 2007-04-05 | 2013-11-12 | Homax Products, Inc. | Pigmented spray texture material compositions, systems, and methods |
| US7651830B2 (en) * | 2007-06-01 | 2010-01-26 | 3M Innovative Properties Company | Patterned photoacid etching and articles therefrom |
| JP5383988B2 (ja) * | 2007-07-30 | 2014-01-08 | 花王株式会社 | 縮重合反応用助触媒 |
| CN101977919B (zh) * | 2008-03-24 | 2014-04-23 | 昭和电工株式会社 | 环氧化合物及其制造方法 |
| US20090288770A1 (en) * | 2008-05-23 | 2009-11-26 | Loctite (R&D) Limited | Surface-promoted cure of one-part cationically curable compositions |
| US8399099B1 (en) * | 2008-05-23 | 2013-03-19 | Henkel Ireland Limited | Coating compositions |
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| EP2288665A1 (en) * | 2008-05-23 | 2011-03-02 | Loctite (R & D) Limited | Surface-promoted cure of one-part cationically curable compositions |
| WO2010094634A1 (en) | 2009-02-17 | 2010-08-26 | Loctite (R & D) Limited | Cationically curable compositions and a primer therefor |
| US8816211B2 (en) * | 2011-02-14 | 2014-08-26 | Eastman Kodak Company | Articles with photocurable and photocured compositions |
| JP6061449B2 (ja) * | 2011-03-31 | 2017-01-18 | 太陽インキ製造株式会社 | 光硬化性熱硬化性樹脂組成物、そのドライフィルム及び硬化物並びにそれらを用いたプリント配線板 |
| US9248457B2 (en) | 2011-07-29 | 2016-02-02 | Homax Products, Inc. | Systems and methods for dispensing texture material using dual flow adjustment |
| US9156042B2 (en) | 2011-07-29 | 2015-10-13 | Homax Products, Inc. | Systems and methods for dispensing texture material using dual flow adjustment |
| US9156602B1 (en) | 2012-05-17 | 2015-10-13 | Homax Products, Inc. | Actuators for dispensers for texture material |
| US9435120B2 (en) | 2013-03-13 | 2016-09-06 | Homax Products, Inc. | Acoustic ceiling popcorn texture materials, systems, and methods |
| US9776785B2 (en) | 2013-08-19 | 2017-10-03 | Ppg Architectural Finishes, Inc. | Ceiling texture materials, systems, and methods |
| USD787326S1 (en) | 2014-12-09 | 2017-05-23 | Ppg Architectural Finishes, Inc. | Cap with actuator |
| WO2020161584A1 (en) * | 2019-02-06 | 2020-08-13 | 3M Innovative Properties Company | Cationically curable compositions |
| US20250304851A1 (en) * | 2024-03-28 | 2025-10-02 | Halliburton Energy Services, Inc. | Methods and compositions used in controlling formation sand production, proppant flowback, and fines migration |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3907706A (en) | 1973-07-06 | 1975-09-23 | Minnesota Mining & Mfg | Latent catalyst systems for cationically polymerizable materials |
| US4297458A (en) * | 1980-07-14 | 1981-10-27 | General Electric Company | Curable epoxy resins |
| DE3369398D1 (en) | 1982-05-19 | 1987-02-26 | Ciba Geigy Ag | Curable compositions containing metallocen complexes, activated primers obtained therefrom and their use |
| EP0094914B1 (de) | 1982-05-19 | 1986-09-24 | Ciba-Geigy Ag | Photopolymerisation mittels organometallischer Salze |
| US5089536A (en) | 1982-11-22 | 1992-02-18 | Minnesota Mining And Manufacturing Company | Energy polmerizable compositions containing organometallic initiators |
| US5191101A (en) | 1982-11-22 | 1993-03-02 | Minnesota Mining And Manufacturing Company | Energy polymerizable compositions containing organometallic initiators |
| US5073476A (en) | 1983-05-18 | 1991-12-17 | Ciba-Geigy Corporation | Curable composition and the use thereof |
| EP0152377B1 (de) | 1984-02-10 | 1987-12-09 | Ciba-Geigy Ag | Härtbare Zusammensetzung und deren Verwendung |
| US4503211A (en) | 1984-05-31 | 1985-03-05 | Minnesota Mining And Manufacturing Co. | Epoxy resin curing agent, process and composition |
| JPS6136302A (ja) | 1984-07-30 | 1986-02-21 | Toshiba Corp | 光重合性組成物 |
| US4677137A (en) | 1985-05-31 | 1987-06-30 | Minnesota Mining And Manufacturing Company | Supported photoinitiator |
| US4788235A (en) | 1987-11-23 | 1988-11-29 | Minnesota Mining And Manufacturing Company | Phosphite modified epoxy resin |
| DE3814876A1 (de) | 1988-05-02 | 1989-11-16 | Henkel Kgaa | Lichtinduziert dunkelhaertende klebstoffe |
| WO1991016387A1 (en) | 1990-04-23 | 1991-10-31 | Minnesota Mining And Manufacturing Company | Energy curable cationically and free-radically polymerizable pressure-sensitive compositions |
| US5059701A (en) | 1990-09-20 | 1991-10-22 | Minnesota Mining And Manufacturing Company | Methods for preparation of cyclopentadienyliron (II) arenes |
| AU661363B2 (en) | 1992-01-22 | 1995-07-20 | Minnesota Mining And Manufacturing Company | Photoactivatable, thermally curable epoxy compositions |
| US5252694A (en) | 1992-01-22 | 1993-10-12 | Minnesota Mining And Manufacturing Company | Energy-polymerization adhesive, coating, film and process for making the same |
| US5212210A (en) | 1992-03-18 | 1993-05-18 | Minnesota Mining And Manufacturing Company | Energy curable compositions having improved cure speeds |
| US7575653B2 (en) | 1993-04-15 | 2009-08-18 | 3M Innovative Properties Company | Melt-flowable materials and method of sealing surfaces |
| US5494943A (en) | 1993-06-16 | 1996-02-27 | Minnesota Mining And Manufacturing Company | Stabilized cationically-curable compositions |
| US5362421A (en) | 1993-06-16 | 1994-11-08 | Minnesota Mining And Manufacturing Company | Electrically conductive adhesive compositions |
| DE4340949A1 (de) | 1993-12-01 | 1995-06-08 | Thera Ges Fuer Patente | Lichtinitiiert kationisch härtende Epoxidmasse und ihre Verwendung |
| JPH07304846A (ja) * | 1994-05-09 | 1995-11-21 | Yuka Shell Epoxy Kk | エポキシ樹脂組成物 |
| DE69629053T2 (de) | 1995-01-13 | 2004-04-22 | Minnesota Mining And Mfg. Co., St. Paul | Verfahren und Zusammensetzung zum Verbinden von Komponenten mit Glas |
| US5554664A (en) | 1995-03-06 | 1996-09-10 | Minnesota Mining And Manufacturing Company | Energy-activatable salts with fluorocarbon anions |
| DE19534664A1 (de) | 1995-09-19 | 1997-03-20 | Thera Ges Fuer Patente | Lichtinitiiert kationisch härtende, dauerflexible Epoxidharzmasse und ihre Verwendung |
| JPH09325479A (ja) | 1996-05-31 | 1997-12-16 | Hitachi Chem Co Ltd | 感光性組成物、感光材料、レリーフパターンの製造法及びポリイミドパターンの製造法 |
| US6133335A (en) | 1998-12-31 | 2000-10-17 | 3M Innovative Properties Company | Photo-polymerizable compositions and articles made therefrom |
-
1998
- 1998-12-31 US US09/223,926 patent/US6265459B1/en not_active Expired - Lifetime
-
1999
- 1999-04-29 EP EP06017433A patent/EP1757633B1/en not_active Expired - Lifetime
- 1999-04-29 EP EP99925563A patent/EP1157057B1/en not_active Expired - Lifetime
- 1999-04-29 CA CA002355319A patent/CA2355319A1/en not_active Abandoned
- 1999-04-29 BR BR9916703-4A patent/BR9916703A/pt not_active IP Right Cessation
- 1999-04-29 DE DE69939958T patent/DE69939958D1/de not_active Expired - Lifetime
- 1999-04-29 DE DE69932947T patent/DE69932947T2/de not_active Expired - Lifetime
- 1999-04-29 WO PCT/US1999/009309 patent/WO2000040636A1/en not_active Ceased
- 1999-04-29 AU AU41821/99A patent/AU4182199A/en not_active Abandoned
- 1999-04-29 JP JP2000592343A patent/JP4436984B2/ja not_active Expired - Fee Related
- 1999-04-29 KR KR1020017008422A patent/KR100673923B1/ko not_active Expired - Fee Related
- 1999-04-29 CN CN99815320A patent/CN1332759A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1757633A1 (en) | 2007-02-28 |
| DE69932947T2 (de) | 2007-09-06 |
| CN1332759A (zh) | 2002-01-23 |
| KR100673923B1 (ko) | 2007-01-25 |
| KR20010089752A (ko) | 2001-10-08 |
| JP2002534545A (ja) | 2002-10-15 |
| EP1157057B1 (en) | 2006-08-23 |
| US6265459B1 (en) | 2001-07-24 |
| BR9916703A (pt) | 2001-09-25 |
| EP1157057A1 (en) | 2001-11-28 |
| AU4182199A (en) | 2000-07-24 |
| EP1757633B1 (en) | 2008-11-19 |
| DE69932947D1 (de) | 2006-10-05 |
| JP4436984B2 (ja) | 2010-03-24 |
| DE69939958D1 (de) | 2009-01-02 |
| WO2000040636A1 (en) | 2000-07-13 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |