DE69933055T2 - Uv-vernetzbare elastomerzusammensetzung - Google Patents
Uv-vernetzbare elastomerzusammensetzung Download PDFInfo
- Publication number
- DE69933055T2 DE69933055T2 DE69933055T DE69933055T DE69933055T2 DE 69933055 T2 DE69933055 T2 DE 69933055T2 DE 69933055 T DE69933055 T DE 69933055T DE 69933055 T DE69933055 T DE 69933055T DE 69933055 T2 DE69933055 T2 DE 69933055T2
- Authority
- DE
- Germany
- Prior art keywords
- multifunctional
- weight
- copolymerized
- composition
- olefins
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims abstract description 179
- 229920001971 elastomer Polymers 0.000 title claims description 101
- 239000000806 elastomer Substances 0.000 title claims description 83
- 238000000034 method Methods 0.000 claims abstract description 79
- 229920001973 fluoroelastomer Polymers 0.000 claims abstract description 53
- 230000005855 radiation Effects 0.000 claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 239000003431 cross linking reagent Substances 0.000 claims description 90
- 239000003999 initiator Substances 0.000 claims description 47
- 150000001336 alkenes Chemical class 0.000 claims description 38
- 150000002170 ethers Chemical class 0.000 claims description 37
- 229920001577 copolymer Polymers 0.000 claims description 31
- 230000008569 process Effects 0.000 claims description 30
- 229920000642 polymer Polymers 0.000 claims description 27
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 24
- 239000004971 Cross linker Substances 0.000 claims description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 20
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 19
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 18
- 238000007789 sealing Methods 0.000 claims description 18
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical group FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 17
- GVCWGFZDSIWLMO-UHFFFAOYSA-N 4-bromo-3,3,4,4-tetrafluorobut-1-ene Chemical compound FC(F)(Br)C(F)(F)C=C GVCWGFZDSIWLMO-UHFFFAOYSA-N 0.000 claims description 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 15
- 150000001993 dienes Chemical class 0.000 claims description 14
- 239000000945 filler Substances 0.000 claims description 13
- 125000001246 bromo group Chemical group Br* 0.000 claims description 11
- 239000000565 sealant Substances 0.000 claims description 11
- 150000005671 trienes Chemical class 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 8
- 238000000465 moulding Methods 0.000 claims description 7
- 238000011065 in-situ storage Methods 0.000 claims description 5
- 150000004678 hydrides Chemical class 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 238000005187 foaming Methods 0.000 claims description 3
- 239000012815 thermoplastic material Substances 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000012943 hotmelt Substances 0.000 abstract description 5
- 238000013023 gasketing Methods 0.000 abstract 1
- 238000004132 cross linking Methods 0.000 description 45
- 239000000178 monomer Substances 0.000 description 23
- 239000005060 rubber Substances 0.000 description 18
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 14
- 239000005977 Ethylene Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- -1 perfluoro Chemical group 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 229920001169 thermoplastic Polymers 0.000 description 9
- 238000007906 compression Methods 0.000 description 8
- 230000006835 compression Effects 0.000 description 8
- 238000010894 electron beam technology Methods 0.000 description 8
- 230000006855 networking Effects 0.000 description 8
- 239000004416 thermosoftening plastic Substances 0.000 description 8
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001125 extrusion Methods 0.000 description 5
- 229920002313 fluoropolymer Polymers 0.000 description 5
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 229920006362 Teflon® Polymers 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000000748 compression moulding Methods 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
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- 239000004811 fluoropolymer Substances 0.000 description 4
- 239000004088 foaming agent Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 230000002028 premature Effects 0.000 description 3
- 230000002787 reinforcement Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JILAKKYYZPDQBE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluoro-1,4-diiodobutane Chemical compound FC(F)(I)C(F)(F)C(F)(F)C(F)(F)I JILAKKYYZPDQBE-UHFFFAOYSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- AYCANDRGVPTASA-UHFFFAOYSA-N 1-bromo-1,2,2-trifluoroethene Chemical group FC(F)=C(F)Br AYCANDRGVPTASA-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- OUJSWWHXKJQNMJ-UHFFFAOYSA-N 3,3,4,4-tetrafluoro-4-iodobut-1-ene Chemical compound FC(F)(I)C(F)(F)C=C OUJSWWHXKJQNMJ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 241001441571 Hiodontidae Species 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 229920000800 acrylic rubber Polymers 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 238000007033 dehydrochlorination reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229920005558 epichlorohydrin rubber Polymers 0.000 description 2
- 229920006228 ethylene acrylate copolymer Polymers 0.000 description 2
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 2
- 229920002681 hypalon Polymers 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- OJUGVDODNPJEEC-UHFFFAOYSA-N phenylglyoxal Chemical compound O=CC(=O)C1=CC=CC=C1 OJUGVDODNPJEEC-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- COHBNTMIFZGBGZ-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoro-2-iodo-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(I)C(F)(F)F COHBNTMIFZGBGZ-UHFFFAOYSA-N 0.000 description 1
- JOQDDLBOAIKFQX-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,6-diiodohexane Chemical compound FC(F)(I)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I JOQDDLBOAIKFQX-UHFFFAOYSA-N 0.000 description 1
- WIEYKFZUVTYEIY-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoro-1,3-diiodopropane Chemical compound FC(F)(I)C(F)(F)C(F)(F)I WIEYKFZUVTYEIY-UHFFFAOYSA-N 0.000 description 1
- QAERDLQYXMEHEB-UHFFFAOYSA-N 1,1,3,3,3-pentafluoroprop-1-ene Chemical group FC(F)=CC(F)(F)F QAERDLQYXMEHEB-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- ZUMAWUHJHORWHC-UHFFFAOYSA-N 1-bromo-1,1,2,2,3,3-hexafluoro-3-iodopropane 1-bromo-1,1,2,2-tetrafluoro-2-iodoethane Chemical compound BrC(C(C(I)(F)F)(F)F)(F)F.BrC(C(I)(F)F)(F)F ZUMAWUHJHORWHC-UHFFFAOYSA-N 0.000 description 1
- QFLUCTGSGZFZKK-UHFFFAOYSA-N 1-ethenoxy-1,1,2,2-tetrafluoro-2-iodoethane Chemical compound FC(F)(I)C(F)(F)OC=C QFLUCTGSGZFZKK-UHFFFAOYSA-N 0.000 description 1
- GKFAEUUIDLYIQV-UHFFFAOYSA-N 1-ethenoxy-2-iodoethane Chemical compound ICCOC=C GKFAEUUIDLYIQV-UHFFFAOYSA-N 0.000 description 1
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- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- LYIPDZSLYLDLCU-UHFFFAOYSA-N 2,2,3,3-tetrafluoro-3-[1,1,1,2,3,3-hexafluoro-3-(1,2,2-trifluoroethenoxy)propan-2-yl]oxypropanenitrile Chemical compound FC(F)=C(F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C#N LYIPDZSLYLDLCU-UHFFFAOYSA-N 0.000 description 1
- OHQSQCACEXDHAJ-UHFFFAOYSA-N 2,2-di(butan-2-yloxy)-1-phenylethanone Chemical compound CCC(C)OC(OC(C)CC)C(=O)C1=CC=CC=C1 OHQSQCACEXDHAJ-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
- LFNCSMYARNDZQT-UHFFFAOYSA-N 2-bromo-1,1-difluoro-1-iodoethane Chemical compound FC(F)(I)CBr LFNCSMYARNDZQT-UHFFFAOYSA-N 0.000 description 1
- QZGNGBWAMYFUST-UHFFFAOYSA-N 2-bromo-1,1-difluoroethene Chemical group FC(F)=CBr QZGNGBWAMYFUST-UHFFFAOYSA-N 0.000 description 1
- GONMPWKZGSRAQW-UHFFFAOYSA-N 2-chloro-1,1,2,3,3-pentafluoro-1,3-diiodopropane Chemical compound FC(F)(I)C(F)(Cl)C(F)(F)I GONMPWKZGSRAQW-UHFFFAOYSA-N 0.000 description 1
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- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- JFYZKVSETQEPKR-UHFFFAOYSA-N 3,3,4,4-tetrafluoro-1,6-diiodohexane Chemical compound ICCC(F)(F)C(F)(F)CCI JFYZKVSETQEPKR-UHFFFAOYSA-N 0.000 description 1
- LTWXOWGZFQVSKR-UHFFFAOYSA-N 3,3,4,5,5,5-hexafluoro-4-iodopent-1-ene Chemical compound FC(F)(F)C(F)(I)C(F)(F)C=C LTWXOWGZFQVSKR-UHFFFAOYSA-N 0.000 description 1
- BGRGXBWMPNEZMS-UHFFFAOYSA-N 3-bromo-1,1-difluoroprop-1-ene Chemical compound FC(F)=CCBr BGRGXBWMPNEZMS-UHFFFAOYSA-N 0.000 description 1
- BFKBHVSNXIXLCI-UHFFFAOYSA-N 3-chloro-3,4,4-trifluoro-4-iodobut-1-ene Chemical compound FC(F)(I)C(F)(Cl)C=C BFKBHVSNXIXLCI-UHFFFAOYSA-N 0.000 description 1
- NBOCQTNZUPTTEI-UHFFFAOYSA-N 4-[4-(hydrazinesulfonyl)phenoxy]benzenesulfonohydrazide Chemical compound C1=CC(S(=O)(=O)NN)=CC=C1OC1=CC=C(S(=O)(=O)NN)C=C1 NBOCQTNZUPTTEI-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- GQCQMFYIFUDARF-UHFFFAOYSA-N 4-bromo-1,1,2-trifluorobut-1-ene Chemical compound FC(F)=C(F)CCBr GQCQMFYIFUDARF-UHFFFAOYSA-N 0.000 description 1
- VPFQNCANYUNULV-UHFFFAOYSA-N 4-bromo-1,1,3,3,4,4-hexafluorobut-1-ene Chemical compound FC(F)=CC(F)(F)C(F)(F)Br VPFQNCANYUNULV-UHFFFAOYSA-N 0.000 description 1
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- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 description 1
- GXSAFSCLNMQIDS-UHFFFAOYSA-N 6-bromo-5,5,6,6-tetrafluorohex-1-ene Chemical compound FC(F)(Br)C(F)(F)CCC=C GXSAFSCLNMQIDS-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- 229940076442 9,10-anthraquinone Drugs 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- MWRWFPQBGSZWNV-UHFFFAOYSA-N Dinitrosopentamethylenetetramine Chemical compound C1N2CN(N=O)CN1CN(N=O)C2 MWRWFPQBGSZWNV-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- XLYMOEINVGRTEX-ARJAWSKDSA-N Ethyl hydrogen fumarate Chemical compound CCOC(=O)\C=C/C(O)=O XLYMOEINVGRTEX-ARJAWSKDSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
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- 239000004760 aramid Substances 0.000 description 1
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- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 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 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
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- 238000013329 compounding Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
- VLNBQUAHERCLKT-UHFFFAOYSA-N dimethylamino benzoate Chemical compound CN(C)OC(=O)C1=CC=CC=C1 VLNBQUAHERCLKT-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 208000018459 dissociative disease Diseases 0.000 description 1
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- QHZOMAXECYYXGP-UHFFFAOYSA-N ethene;prop-2-enoic acid Chemical compound C=C.OC(=O)C=C QHZOMAXECYYXGP-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
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- 239000001257 hydrogen Substances 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- BCCOBQSFUDVTJQ-UHFFFAOYSA-N octafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(F)C1(F)F BCCOBQSFUDVTJQ-UHFFFAOYSA-N 0.000 description 1
- 235000019407 octafluorocyclobutane Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical group 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
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- 229920000768 polyamine Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
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- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
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- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/0617—Polyalkenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/0617—Polyalkenes
- C09K2200/062—Polyethylene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/0625—Polyacrylic esters or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Sealing Material Composition (AREA)
- Graft Or Block Polymers (AREA)
- Polymerisation Methods In General (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Sealing Devices (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1999/016003 WO2001005885A1 (en) | 1999-07-15 | 1999-07-15 | Uv curable elastomer composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69933055D1 DE69933055D1 (de) | 2006-10-12 |
| DE69933055T2 true DE69933055T2 (de) | 2007-04-12 |
Family
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Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69933055T Expired - Lifetime DE69933055T2 (de) | 1999-07-15 | 1999-07-15 | Uv-vernetzbare elastomerzusammensetzung |
| DE69938514T Expired - Lifetime DE69938514T2 (de) | 1999-07-15 | 1999-07-15 | Verfahren zur schnellen Vernetzung einer Elastomerzusammensetzung mittels UV-Strahlung |
| DE69940032T Expired - Lifetime DE69940032D1 (de) | 1999-07-15 | 1999-07-15 | Verfahren zur in-situ Auflegung einer Dichtung auf einen Artikel |
| DE69940986T Expired - Lifetime DE69940986D1 (de) | 1999-07-15 | 1999-07-15 | UV-vernetzbare Elastomerzusammensetzung |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69938514T Expired - Lifetime DE69938514T2 (de) | 1999-07-15 | 1999-07-15 | Verfahren zur schnellen Vernetzung einer Elastomerzusammensetzung mittels UV-Strahlung |
| DE69940032T Expired - Lifetime DE69940032D1 (de) | 1999-07-15 | 1999-07-15 | Verfahren zur in-situ Auflegung einer Dichtung auf einen Artikel |
| DE69940986T Expired - Lifetime DE69940986D1 (de) | 1999-07-15 | 1999-07-15 | UV-vernetzbare Elastomerzusammensetzung |
Country Status (10)
| Country | Link |
|---|---|
| EP (4) | EP1357146B1 (enExample) |
| JP (1) | JP4847660B2 (enExample) |
| CN (1) | CN1155649C (enExample) |
| AT (4) | ATE433474T1 (enExample) |
| AU (1) | AU780862B2 (enExample) |
| BR (1) | BR9917444B1 (enExample) |
| CA (3) | CA2632778C (enExample) |
| DE (4) | DE69933055T2 (enExample) |
| ES (1) | ES2272078T3 (enExample) |
| WO (1) | WO2001005885A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6506460B2 (en) * | 1998-01-21 | 2003-01-14 | E. I. Du Pont De Nemours And Company | UV curable elastomer composition |
| DE60031148T2 (de) | 1999-08-31 | 2007-10-25 | Daikin Industries, Ltd. | Uv-vernetzbare polymerzusammensetzung |
| US7287280B2 (en) | 2002-02-12 | 2007-10-23 | Goldman Sachs & Co. | Automated security management |
| US6908586B2 (en) | 2001-06-27 | 2005-06-21 | Fusion Uv Systems, Inc. | Free radical polymerization method having reduced premature termination, apparatus for performing the method and product formed thereby |
| CN100563986C (zh) * | 2003-05-16 | 2009-12-02 | 杜邦唐弹性体公司 | 制备紫外光固化密封组件的方法 |
| US20050234158A1 (en) * | 2004-04-19 | 2005-10-20 | Scott Levi F Jr | Energy-curable coating/adhesive compositions containing chlorinated polyolefins |
| EP2033520A1 (en) | 2007-09-07 | 2009-03-11 | Cognis IP Management GmbH | Use of biocide compositions for wood preservation |
| CN102272206B (zh) * | 2009-01-16 | 2013-10-30 | 日东电工株式会社 | 交联型树脂发泡体、及其制造方法 |
| DE102009058297A1 (de) | 2009-12-01 | 2011-06-09 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | N-Allylcarbamat-Verbindungen und deren Verwendung, insbesondere in strahlungshärtenden Beschichtungen |
| WO2013067678A1 (en) | 2011-11-07 | 2013-05-16 | Lanxess Deutschland Gmbh | Uv curable flame retardant compounds, a uv curing method thereof, and the use thereof |
| CN102558719B (zh) * | 2011-12-29 | 2014-07-02 | 中昊晨光化工研究院 | 一种耐低温含氟弹性体及其制备方法 |
| KR101449124B1 (ko) * | 2012-09-17 | 2014-10-08 | 현대자동차주식회사 | 수소연료전지용 사출성형 일체화 불소계 가스켓 |
| JP6050138B2 (ja) * | 2013-02-19 | 2016-12-21 | 日本バルカー工業株式会社 | シール材用ゴム組成物及びこれを用いたシール材 |
| WO2019154765A1 (en) * | 2018-02-09 | 2019-08-15 | Solvay Specialty Polymers Italy S.P.A. | Fluoroelastomer curable composition |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS50101469A (enExample) * | 1974-01-10 | 1975-08-12 | ||
| JPS52102023A (en) * | 1976-02-21 | 1977-08-26 | Tokyo Ouka Kougiyou Kk | Novel relief photosensitive composition |
| JPS56143284A (en) * | 1980-04-09 | 1981-11-07 | Minamiura Kinzoku Kogyosho:Kk | Sealing material for making can |
| JPS57129442A (en) * | 1981-02-05 | 1982-08-11 | Toray Ind Inc | Lithographic printing plate requiring no damping water |
| JPS58162640A (ja) * | 1982-03-19 | 1983-09-27 | Kansai Paint Co Ltd | ポリオレフイン系プラスチツク用被覆組成物 |
| JPS6131411A (ja) * | 1984-07-23 | 1986-02-13 | Suriibondo:Kk | 硬化性組成物 |
| US5177143A (en) * | 1984-08-31 | 1993-01-05 | Raychem Corporation | Method of making heat stable polymeric gelloid composition |
| JP2653182B2 (ja) * | 1988-09-06 | 1997-09-10 | ダイキン工業株式会社 | 固体状高分子物質、その製法及び用途 |
| US5075028A (en) * | 1989-11-13 | 1991-12-24 | Copolymer Rubber & Chemical Corp. | Accelerator compositions |
| JPH04142322A (ja) * | 1990-10-02 | 1992-05-15 | Toyo Kasei Kogyo Kk | 合成樹脂組成物 |
| US5317074A (en) * | 1991-02-07 | 1994-05-31 | Minnesota Mining And Manufacturing Company | Stain-resistant elastomeric orthodontic force module |
| TW222650B (enExample) * | 1991-04-01 | 1994-04-21 | Dow Corning | |
| JPH0693210A (ja) * | 1992-04-30 | 1994-04-05 | Minnesota Mining & Mfg Co <3M> | 耐汚染性保護コーティング組成物 |
| EP0660849A1 (en) * | 1992-09-18 | 1995-07-05 | Minnesota Mining And Manufacturing Company | Fluorochemical polymer systems |
| JP3327016B2 (ja) * | 1994-12-06 | 2002-09-24 | ダイキン工業株式会社 | 低温シール性に優れたフッ素ゴム共重合体及びその硬化用組成物 |
| DE69617042T2 (de) * | 1995-12-28 | 2002-06-06 | Daikin Industries, Ltd. | Fluorhaltige, elastische copolymere, härtbare zusammensetzung und daraus hergestellte dichtungsmasse |
| JP3713789B2 (ja) * | 1996-03-01 | 2005-11-09 | Ｊｓｒ株式会社 | 光架橋性共重合体組成物 |
-
1999
- 1999-07-15 AU AU51035/99A patent/AU780862B2/en not_active Ceased
- 1999-07-15 DE DE69933055T patent/DE69933055T2/de not_active Expired - Lifetime
- 1999-07-15 BR BRPI9917444-8A patent/BR9917444B1/pt not_active IP Right Cessation
- 1999-07-15 EP EP03076676A patent/EP1357146B1/en not_active Expired - Lifetime
- 1999-07-15 AT AT06076196T patent/ATE433474T1/de not_active IP Right Cessation
- 1999-07-15 CN CNB998168068A patent/CN1155649C/zh not_active Expired - Fee Related
- 1999-07-15 EP EP99935585A patent/EP1198501B1/en not_active Expired - Lifetime
- 1999-07-15 AT AT03076526T patent/ATE391750T1/de not_active IP Right Cessation
- 1999-07-15 DE DE69938514T patent/DE69938514T2/de not_active Expired - Lifetime
- 1999-07-15 JP JP2001511109A patent/JP4847660B2/ja not_active Expired - Fee Related
- 1999-07-15 DE DE69940032T patent/DE69940032D1/de not_active Expired - Lifetime
- 1999-07-15 CA CA2632778A patent/CA2632778C/en not_active Expired - Fee Related
- 1999-07-15 EP EP06076196A patent/EP1700884B1/en not_active Expired - Lifetime
- 1999-07-15 AT AT99935585T patent/ATE338088T1/de not_active IP Right Cessation
- 1999-07-15 EP EP03076526A patent/EP1338623B1/en not_active Expired - Lifetime
- 1999-07-15 CA CA002377046A patent/CA2377046C/en not_active Expired - Fee Related
- 1999-07-15 DE DE69940986T patent/DE69940986D1/de not_active Expired - Lifetime
- 1999-07-15 ES ES99935585T patent/ES2272078T3/es not_active Expired - Lifetime
- 1999-07-15 AT AT03076676T patent/ATE416227T1/de not_active IP Right Cessation
- 1999-07-15 WO PCT/US1999/016003 patent/WO2001005885A1/en not_active Ceased
- 1999-07-15 CA CA2632787A patent/CA2632787C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2377046A1 (en) | 2001-01-25 |
| EP1338623A1 (en) | 2003-08-27 |
| EP1357146B1 (en) | 2008-12-03 |
| AU5103599A (en) | 2001-02-05 |
| AU780862B2 (en) | 2005-04-21 |
| DE69940032D1 (de) | 2009-01-15 |
| ATE391750T1 (de) | 2008-04-15 |
| DE69933055D1 (de) | 2006-10-12 |
| EP1700884B1 (en) | 2009-06-10 |
| BR9917444B1 (pt) | 2009-05-05 |
| ES2272078T3 (es) | 2007-04-16 |
| EP1700884A1 (en) | 2006-09-13 |
| EP1338623B1 (en) | 2008-04-09 |
| JP2003505525A (ja) | 2003-02-12 |
| DE69940986D1 (de) | 2009-07-23 |
| EP1357146A1 (en) | 2003-10-29 |
| EP1198501B1 (en) | 2006-08-30 |
| CN1361809A (zh) | 2002-07-31 |
| ATE433474T1 (de) | 2009-06-15 |
| DE69938514D1 (de) | 2008-05-21 |
| CA2632778A1 (en) | 2001-01-25 |
| CA2632787C (en) | 2010-05-18 |
| WO2001005885A1 (en) | 2001-01-25 |
| ATE416227T1 (de) | 2008-12-15 |
| CA2632778C (en) | 2012-01-03 |
| JP4847660B2 (ja) | 2011-12-28 |
| EP1198501A1 (en) | 2002-04-24 |
| ATE338088T1 (de) | 2006-09-15 |
| CN1155649C (zh) | 2004-06-30 |
| CA2632787A1 (en) | 2001-01-25 |
| BR9917444A (pt) | 2002-04-23 |
| CA2377046C (en) | 2008-11-18 |
| DE69938514T2 (de) | 2009-06-10 |
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