ZA200202149B - UV-curable compositions. - Google Patents
UV-curable compositions. Download PDFInfo
- Publication number
- ZA200202149B ZA200202149B ZA200202149A ZA200202149A ZA200202149B ZA 200202149 B ZA200202149 B ZA 200202149B ZA 200202149 A ZA200202149 A ZA 200202149A ZA 200202149 A ZA200202149 A ZA 200202149A ZA 200202149 B ZA200202149 B ZA 200202149B
- Authority
- ZA
- South Africa
- Prior art keywords
- oxabicyclo
- compound
- bis
- group
- ester
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 63
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- -1 oxetane compound Chemical class 0.000 claims abstract description 40
- 239000004593 Epoxy Substances 0.000 claims abstract description 38
- 150000002440 hydroxy compounds Chemical class 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 27
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 12
- 150000002009 diols Chemical class 0.000 claims description 10
- 239000004632 polycaprolactone Substances 0.000 claims description 10
- 229920005862 polyol Polymers 0.000 claims description 10
- 150000003077 polyols Chemical class 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- 229920001610 polycaprolactone Polymers 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 7
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 6
- 235000011037 adipic acid Nutrition 0.000 claims description 6
- 229960000250 adipic acid Drugs 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- VFFFESPCCPXZOQ-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;oxirane Chemical compound C1CO1.OCC(CO)(CO)CO VFFFESPCCPXZOQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 5
- CGRJJOYCFCCGPX-UHFFFAOYSA-N 3-ethyloxetane Chemical compound CCC1COC1 CGRJJOYCFCCGPX-UHFFFAOYSA-N 0.000 claims description 4
- AMNPXXIGUOKIPP-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl]thiourea Chemical compound NC(=S)NC1=CC=C(NC(N)=S)C=C1 AMNPXXIGUOKIPP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 238000005266 casting Methods 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 2
- 238000009413 insulation Methods 0.000 claims description 2
- 238000010030 laminating Methods 0.000 claims description 2
- 238000000465 moulding Methods 0.000 claims description 2
- 238000004382 potting Methods 0.000 claims description 2
- 238000007789 sealing Methods 0.000 claims description 2
- 108010021119 Trichosanthin Proteins 0.000 claims 1
- 238000009472 formulation Methods 0.000 description 29
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 28
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000004411 aluminium Substances 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 12
- 235000010210 aluminium Nutrition 0.000 description 12
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 11
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 7
- 229940126062 Compound A Drugs 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000012952 cationic photoinitiator Substances 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 4
- 238000003848 UV Light-Curing Methods 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000012936 correction and preventive action Methods 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical group C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000002921 oxetanes Chemical class 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000012779 reinforcing material Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- FQXGHZNSUOHCLO-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1,3-cyclobutanediol Chemical compound CC1(C)C(O)C(C)(C)C1O FQXGHZNSUOHCLO-UHFFFAOYSA-N 0.000 description 1
- MQXNNWDXHFBFEB-UHFFFAOYSA-N 2,2-bis(2-hydroxyphenyl)propane Chemical class C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1O MQXNNWDXHFBFEB-UHFFFAOYSA-N 0.000 description 1
- AOGNACZDZNOTSN-UHFFFAOYSA-N 2,3-dihydroxy-1,2-diphenylpropan-1-one Chemical compound C=1C=CC=CC=1C(O)(CO)C(=O)C1=CC=CC=C1 AOGNACZDZNOTSN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AYHLPQOWRMPEKH-UHFFFAOYSA-N 2-(6-methylheptoxymethyl)oxirane Chemical compound CC(C)CCCCCOCC1CO1 AYHLPQOWRMPEKH-UHFFFAOYSA-N 0.000 description 1
- QHOMCUUGNPEUCT-UHFFFAOYSA-N 2-(7-oxabicyclo[4.1.0]heptan-4-yl)spiro[1,3-dioxane-5,4'-7-oxabicyclo[4.1.0]heptane] Chemical compound C1CC2OC2CC1(CO1)COC1C1CCC2OC2C1 QHOMCUUGNPEUCT-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- WHNIMRYJAUUVQJ-UHFFFAOYSA-N 2-hydroxy-1,2-diphenylethanone;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 WHNIMRYJAUUVQJ-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 1
- IJUVMGPZIADWRM-UHFFFAOYSA-N 4-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)-1,3-dioxan-5-yl]-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2CC1C(OC1)OCC1C1CCC2OC2C1 IJUVMGPZIADWRM-UHFFFAOYSA-N 0.000 description 1
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical class [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
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- RBTOVELVJLGISG-UHFFFAOYSA-N benzenesulfonic acid;2-hydroxy-1,2-diphenylethanone Chemical compound OS(=O)(=O)C1=CC=CC=C1.C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 RBTOVELVJLGISG-UHFFFAOYSA-N 0.000 description 1
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- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- QCRFMSUKWRQZEM-UHFFFAOYSA-N cycloheptanol Chemical compound OC1CCCCCC1 QCRFMSUKWRQZEM-UHFFFAOYSA-N 0.000 description 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
- RLMGYIOTPQVQJR-UHFFFAOYSA-N cyclohexane-1,3-diol Chemical compound OC1CCCC(O)C1 RLMGYIOTPQVQJR-UHFFFAOYSA-N 0.000 description 1
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 1
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000001227 electron beam curing Methods 0.000 description 1
- 150000002118 epoxides Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000001812 iodosyl group Chemical group O=I[*] 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical class 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920001568 phenolic resin Chemical class 0.000 description 1
- 239000005011 phenolic resin Chemical class 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid group Chemical group C(C=1C(C(=O)O)=CC=CC1)(=O)O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- NPANDVNCRMZSFT-UHFFFAOYSA-N propane-1,2-diol;propane-1,3-diol Chemical compound CC(O)CO.OCCCO NPANDVNCRMZSFT-UHFFFAOYSA-N 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 231100000489 sensitizer Toxicity 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N terephthalic acid group Chemical group C(C1=CC=C(C(=O)O)C=C1)(=O)O KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005590 trimellitic acid group Chemical group 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/18—Oxetanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Polyethers (AREA)
- Sealing Material Composition (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9921779.6A GB9921779D0 (en) | 1999-09-16 | 1999-09-16 | UV-Curable compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200202149B true ZA200202149B (en) | 2003-05-28 |
Family
ID=10860943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200202149A ZA200202149B (en) | 1999-09-16 | 2002-03-15 | UV-curable compositions. |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6855748B1 (de) |
| EP (1) | EP1232198B1 (de) |
| JP (1) | JP4828063B2 (de) |
| KR (1) | KR100686369B1 (de) |
| AT (1) | ATE328936T1 (de) |
| AU (1) | AU771573B2 (de) |
| CA (1) | CA2384176C (de) |
| DE (2) | DE20023994U1 (de) |
| ES (1) | ES2260050T3 (de) |
| GB (1) | GB9921779D0 (de) |
| TW (1) | TW546322B (de) |
| WO (1) | WO2001019895A1 (de) |
| ZA (1) | ZA200202149B (de) |
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|---|---|---|---|---|
| US20040077745A1 (en) * | 2002-10-18 | 2004-04-22 | Jigeng Xu | Curable compositions and rapid prototyping process using the same |
| EP1518899A3 (de) * | 2003-09-18 | 2005-08-03 | Fuji Photo Film Co., Ltd. | Photohärtbare Klebstoffe und Verfestigungsverfahren |
| JP2005320491A (ja) * | 2004-05-11 | 2005-11-17 | Hitachi Chem Co Ltd | 接着剤組成物、それを用いたフィルム状接着剤及び回路接続材料、並びに回路部材の接続構造及びその製造方法 |
| KR20070043817A (ko) * | 2004-08-02 | 2007-04-25 | 후지필름 가부시키가이샤 | 광학 필름, 이의 제조 방법 및 편광판 및 화상 표시 장치 |
| JP4810155B2 (ja) * | 2004-08-02 | 2011-11-09 | 富士フイルム株式会社 | 光学フィルム及びその製造方法並びに偏光板及び画像表示装置 |
| SE529306C2 (sv) * | 2005-03-18 | 2007-06-26 | Perstorp Specialty Chem Ab | Ultravioletthärdande hartskomposition |
| US8017795B2 (en) * | 2005-04-21 | 2011-09-13 | Ndsu Research Foundation | Radiation curable polymer films having improved laser ablation properties and radiation curable sensitizers therefor |
| JP5539605B2 (ja) * | 2006-04-19 | 2014-07-02 | 株式会社ダイセル | 活性エネルギー線硬化性コーティング剤およびその用途 |
| JP4135119B2 (ja) * | 2006-09-29 | 2008-08-20 | Ｄｉｃ株式会社 | 多分岐ポリエーテルポリオール含有のカチオン重合性樹脂組成物、それを含む接着剤、ならびにそれを用いた積層体及び偏光板 |
| JP2008111105A (ja) * | 2006-10-06 | 2008-05-15 | Dainippon Ink & Chem Inc | プラスチック基材用カチオン重合性接着剤、それを用いた積層体及び偏光板 |
| US20080103226A1 (en) * | 2006-10-31 | 2008-05-01 | Dsm Ip Assets B.V. | Photo-curable resin composition |
| KR101512862B1 (ko) * | 2007-01-11 | 2015-04-16 | 도요세이칸 그룹 홀딩스 가부시키가이샤 | 가스 배리어재 형성용 조성물, 가스 배리어재 및 그 제조방법 및 가스 배리어성 포장재 |
| US8088566B2 (en) | 2007-03-26 | 2012-01-03 | Fujifilm Corporation | Surface-treating agent for pattern formation and pattern-forming method using the surface-treating agent |
| DE102007043559B4 (de) * | 2007-09-13 | 2012-05-31 | Carl Zeiss Vision Gmbh | Verwendung eines lichthärtenden thermoplastischen Epoxidharzklebstoffs zum Blocken oder Kleben von optischen Bauelementen |
| US20100190881A1 (en) * | 2009-01-28 | 2010-07-29 | 3D Systems, Incorporated | Radiation Curable Compositions Useful in Solid Freeform Fabrication Systems |
| US20140264165A1 (en) * | 2013-03-15 | 2014-09-18 | Henkel Corporation | Oxetane-containing compounds and compositions thereof |
| KR102381767B1 (ko) * | 2014-05-06 | 2022-04-04 | 훈츠만 어드밴스트 머티리얼스 라이센싱 (스위처랜드) 게엠베하 | 광경화성 밀봉제 조성물, 그의 제조 및 그의 용도 |
| TWI519560B (zh) | 2014-11-24 | 2016-02-01 | 財團法人工業技術研究院 | 含氧雜環丁烷基與環氧基之樹脂與樹脂組成物 |
| WO2017196855A1 (en) * | 2016-05-09 | 2017-11-16 | Arconic Inc. | Sla resins and methods of making and using the same |
| CN110799168B (zh) | 2017-06-20 | 2023-06-23 | 3M创新有限公司 | 用于增材制造方法的可辐射固化组合物 |
| KR102172568B1 (ko) * | 2017-09-22 | 2020-11-02 | 주식회사 엘지화학 | 접착제 조성물 및 이를 이용하여 형성된 접착제층을 포함하는 편광판 |
| CN111234749A (zh) * | 2020-01-16 | 2020-06-05 | 交通运输部科学研究院 | 混凝土早期裂缝修复材料、制备方法及使用方法 |
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| US1516351A (en) | 1921-08-02 | 1924-11-18 | Keystone Reamer & Tool Co | Combination screw die and collet |
| US1539192A (en) | 1923-08-06 | 1925-05-26 | Gustav A Jaeger | Pocket for pool tables |
| US3835003A (en) * | 1968-08-20 | 1974-09-10 | American Can Co | Photopolymerization of oxetanes |
| DE2150691C2 (de) | 1971-10-12 | 1982-09-09 | Basf Ag, 6700 Ludwigshafen | Lichtempfindliches Gemisch und Verwendung eines lichtempfindlichen Gemisches zur Herstellung einer Flachdruckplatte |
| US4058400A (en) | 1974-05-02 | 1977-11-15 | General Electric Company | Cationically polymerizable compositions containing group VIa onium salts |
| GB1516352A (en) | 1974-05-02 | 1978-07-05 | Gen Electric | Halonium salts |
| US4058401A (en) | 1974-05-02 | 1977-11-15 | General Electric Company | Photocurable compositions containing group via aromatic onium salts |
| GB1539192A (en) | 1975-01-27 | 1979-01-31 | Ici Ltd | Photopolymerisable compositions |
| US3991033A (en) | 1975-01-30 | 1976-11-09 | E. I. Du Pont De Nemours & Company | Photosensitive and degradable polyoxymethylene polymers and their application in imaging |
| US4086210A (en) | 1976-05-10 | 1978-04-25 | Eastman Kodak Company | Radiation sensitive polymeric o-nitrophenyl acetals |
| US4299938A (en) | 1979-06-19 | 1981-11-10 | Ciba-Geigy Corporation | Photopolymerizable and thermally polymerizable compositions |
| US4339567A (en) | 1980-03-07 | 1982-07-13 | Ciba-Geigy Corporation | Photopolymerization by means of sulphoxonium salts |
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| US4368256A (en) | 1980-07-22 | 1983-01-11 | Ciba-Geigy Ag | Process for production of masked positive color images by the silver dye bleach process and the silver dye bleach material used in this process |
| US4398014A (en) | 1980-11-04 | 1983-08-09 | Ciba-Geigy Corporation | Sulfoxonium salts and their use as polymerization catalysts |
| US4368253A (en) | 1981-01-28 | 1983-01-11 | Ciba-Geigy Corporation | Image formation process |
| US4518676A (en) | 1982-09-18 | 1985-05-21 | Ciba Geigy Corporation | Photopolymerizable compositions containing diaryliodosyl salts |
| GB8413395D0 (en) | 1984-05-25 | 1984-07-04 | Ciba Geigy Ag | Production of images |
| GB8414525D0 (en) | 1984-06-07 | 1984-07-11 | Ciba Geigy Ag | Sulphoxonium salts |
| DE3660255D1 (en) | 1985-04-12 | 1988-07-07 | Ciba Geigy Ag | Oxime sulphonates containing reactive groups |
| US5463084A (en) * | 1992-02-18 | 1995-10-31 | Rensselaer Polytechnic Institute | Photocurable silicone oxetanes |
| JP3161583B2 (ja) * | 1995-07-21 | 2001-04-25 | 東亞合成株式会社 | 活性エネルギー線硬化型組成物 |
| JP3162634B2 (ja) * | 1995-10-02 | 2001-05-08 | 関西ペイント株式会社 | 紫外線硬化型缶用塗料組成物 |
| KR100418453B1 (ko) | 1995-10-02 | 2005-02-07 | 간사이 페인트 가부시키가이샤 | 캔용자외선-경화코팅조성물 |
| US5882842A (en) | 1996-02-16 | 1999-03-16 | Kansai Paint Co., Ltd. | Active energy ray-curable resin composition |
| JP3626302B2 (ja) | 1996-12-10 | 2005-03-09 | Ｊｓｒ株式会社 | 光硬化性樹脂組成物 |
| JP3765896B2 (ja) | 1996-12-13 | 2006-04-12 | Ｊｓｒ株式会社 | 光学的立体造形用光硬化性樹脂組成物 |
| JPH10330717A (ja) * | 1997-05-27 | 1998-12-15 | Nippon Kayaku Co Ltd | 接着剤組成物、接着体及び液晶表示パネル |
| DE19736471A1 (de) * | 1997-08-21 | 1999-02-25 | Espe Dental Ag | Lichtinduziert kationisch härtende Zusammensetzungen und deren Verwendung |
| JPH11152441A (ja) * | 1997-11-21 | 1999-06-08 | Kansai Paint Co Ltd | 紫外線硬化型缶用塗料組成物 |
| JPH11181391A (ja) * | 1997-12-22 | 1999-07-06 | Nippon Kayaku Co Ltd | 接着剤組成物、接着体、接着方法及び光ディスクの製造方法 |
| US6287745B1 (en) * | 1998-02-18 | 2001-09-11 | Dsm N.V. | Photocurable liquid resin composition comprising an epoxy-branched alicyclic compound |
| JPH11241055A (ja) * | 1998-02-24 | 1999-09-07 | Nippon Kayaku Co Ltd | 接着剤組成物、接着体、接着方法及び光ディスクの製造方法 |
| JP4350832B2 (ja) | 1999-04-19 | 2009-10-21 | Ｊｓｒ株式会社 | 立体造形用光硬化性樹脂組成物およびこれを硬化してなる造形物 |
-
1999
- 1999-09-16 GB GBGB9921779.6A patent/GB9921779D0/en not_active Ceased
-
2000
- 2000-08-11 TW TW089116197A patent/TW546322B/zh not_active IP Right Cessation
- 2000-09-07 KR KR1020027003319A patent/KR100686369B1/ko active IP Right Grant
- 2000-09-07 AU AU72850/00A patent/AU771573B2/en not_active Expired
- 2000-09-07 DE DE20023994U patent/DE20023994U1/de not_active Expired - Lifetime
- 2000-09-07 ES ES00960620T patent/ES2260050T3/es not_active Expired - Lifetime
- 2000-09-07 JP JP2001523670A patent/JP4828063B2/ja not_active Expired - Lifetime
- 2000-09-07 DE DE60028600T patent/DE60028600T2/de not_active Expired - Lifetime
- 2000-09-07 CA CA2384176A patent/CA2384176C/en not_active Expired - Lifetime
- 2000-09-07 US US10/088,564 patent/US6855748B1/en not_active Expired - Lifetime
- 2000-09-07 AT AT00960620T patent/ATE328936T1/de not_active IP Right Cessation
- 2000-09-07 WO PCT/EP2000/008748 patent/WO2001019895A1/en active IP Right Grant
- 2000-09-07 EP EP00960620A patent/EP1232198B1/de not_active Revoked
-
2002
- 2002-03-15 ZA ZA200202149A patent/ZA200202149B/en unknown
-
2005
- 2005-02-08 US US11/054,208 patent/US7202286B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1232198A1 (de) | 2002-08-21 |
| KR100686369B1 (ko) | 2007-02-23 |
| JP2003509553A (ja) | 2003-03-11 |
| DE60028600T2 (de) | 2007-05-31 |
| AU771573B2 (en) | 2004-03-25 |
| JP4828063B2 (ja) | 2011-11-30 |
| DE20023994U1 (de) | 2008-12-18 |
| AU7285000A (en) | 2001-04-17 |
| US6855748B1 (en) | 2005-02-15 |
| TW546322B (en) | 2003-08-11 |
| WO2001019895A1 (en) | 2001-03-22 |
| KR20020030818A (ko) | 2002-04-25 |
| ATE328936T1 (de) | 2006-06-15 |
| CA2384176C (en) | 2011-11-22 |
| EP1232198B1 (de) | 2006-06-07 |
| US20050171228A1 (en) | 2005-08-04 |
| DE60028600D1 (de) | 2006-07-20 |
| GB9921779D0 (en) | 1999-11-17 |
| US7202286B2 (en) | 2007-04-10 |
| ES2260050T3 (es) | 2006-11-01 |
| CA2384176A1 (en) | 2001-03-22 |
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