WO2009106717A2 - Composes a structure guanidine et leurs utilisations comme catalyseurs de polycondensation d'organopolysiloxanes - Google Patents
Composes a structure guanidine et leurs utilisations comme catalyseurs de polycondensation d'organopolysiloxanes Download PDFInfo
- Publication number
- WO2009106717A2 WO2009106717A2 PCT/FR2008/001767 FR2008001767W WO2009106717A2 WO 2009106717 A2 WO2009106717 A2 WO 2009106717A2 FR 2008001767 W FR2008001767 W FR 2008001767W WO 2009106717 A2 WO2009106717 A2 WO 2009106717A2
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- Prior art keywords
- group
- linear
- substituted
- branched
- alkyl group
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- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 150000001875 compounds Chemical class 0.000 title claims abstract description 41
- 239000003054 catalyst Substances 0.000 title claims description 71
- 238000006068 polycondensation reaction Methods 0.000 title claims description 33
- 229920001296 polysiloxane Polymers 0.000 title claims description 30
- 239000000203 mixture Substances 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 238000004132 cross linking Methods 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 24
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 20
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 20
- 229920001971 elastomer Polymers 0.000 claims description 19
- 239000000806 elastomer Substances 0.000 claims description 19
- 239000003431 cross linking reagent Substances 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 150000001718 carbodiimides Chemical class 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000002318 adhesion promoter Substances 0.000 claims description 9
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 150000003973 alkyl amines Chemical class 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000012764 mineral filler Substances 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 229920002379 silicone rubber Polymers 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010021118 Hypotonia Diseases 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 abstract description 5
- 230000003000 nontoxic effect Effects 0.000 abstract description 5
- -1 polydimethylsiloxane Polymers 0.000 description 29
- 239000003921 oil Substances 0.000 description 18
- 239000000945 filler Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 150000002357 guanidines Chemical class 0.000 description 6
- 0 *NC(N(*)*)=N* Chemical compound *NC(N(*)*)=N* 0.000 description 5
- SSNNPVRFMKLDQZ-UHFFFAOYSA-N 1,3-di(propan-2-yl)-2-(3-trimethoxysilylpropyl)guanidine Chemical compound CO[Si](OC)(OC)CCCNC(NC(C)C)=NC(C)C SSNNPVRFMKLDQZ-UHFFFAOYSA-N 0.000 description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000003961 organosilicon compounds Chemical group 0.000 description 5
- 239000012974 tin catalyst Substances 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- OZPYWVUFNDGJMD-UHFFFAOYSA-N 1-[3-[dimethoxy(methyl)silyl]propyl]-1-methyl-2,3-di(propan-2-yl)guanidine Chemical compound CO[Si](C)(OC)CCCN(C)C(NC(C)C)=NC(C)C OZPYWVUFNDGJMD-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 229920002545 silicone oil Polymers 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- FGSVCSDSZNQSHH-UHFFFAOYSA-N 1-[3-[bis(trimethylsilyloxy)methylsilyl]propyl]-1-methyl-2,3-di(propan-2-yl)guanidine Chemical compound CC(C)NC(=NC(C)C)N(C)CCC[SiH2]C(O[Si](C)(C)C)O[Si](C)(C)C FGSVCSDSZNQSHH-UHFFFAOYSA-N 0.000 description 2
- GBSOPLJZEKADPV-UHFFFAOYSA-N 1-butyl-2,3-di(propan-2-yl)-1-(3-trimethoxysilylpropyl)guanidine Chemical compound CCCCN(C(NC(C)C)=NC(C)C)CCC[Si](OC)(OC)OC GBSOPLJZEKADPV-UHFFFAOYSA-N 0.000 description 2
- QGBNLWSXOXMZNK-UHFFFAOYSA-N 1-methyl-2,3-di(propan-2-yl)-1-(3-trimethoxysilylpropyl)guanidine Chemical compound CO[Si](OC)(OC)CCCN(C)C(NC(C)C)=NC(C)C QGBNLWSXOXMZNK-UHFFFAOYSA-N 0.000 description 2
- LUEJLDONRFHSNE-UHFFFAOYSA-N 2,3-di(propan-2-yl)-1,1-bis(3-trimethoxysilylpropyl)guanidine Chemical compound CO[Si](OC)(OC)CCCN(C(NC(C)C)=NC(C)C)CCC[Si](OC)(OC)OC LUEJLDONRFHSNE-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- ZNSHMQWLNWPDRT-UHFFFAOYSA-N C1(CCCCC1)N=C(N(CCC[Si](OC)(OC)OC)CC)NC1CCCCC1 Chemical compound C1(CCCCC1)N=C(N(CCC[Si](OC)(OC)OC)CC)NC1CCCCC1 ZNSHMQWLNWPDRT-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- 239000012080 ambient air Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
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- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
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- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 2
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- 150000002739 metals Chemical class 0.000 description 2
- DVYVMJLSUSGYMH-UHFFFAOYSA-N n-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCCC[Si](OC)(OC)OC DVYVMJLSUSGYMH-UHFFFAOYSA-N 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- 239000002243 precursor Substances 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- PFWAKOJJMPDUGF-UHFFFAOYSA-N 1,1,2,3-tetramethyl-3-(3-trimethoxysilylpropyl)guanidine Chemical compound CO[Si](OC)(OC)CCCN(C)C(=NC)N(C)C PFWAKOJJMPDUGF-UHFFFAOYSA-N 0.000 description 1
- MODGBGCMMLUAIQ-UHFFFAOYSA-N 1,3-dicyclohexyl-2-(3-triethoxysilylpropyl)guanidine Chemical compound C1CCCCC1NC(=NCCC[Si](OCC)(OCC)OCC)NC1CCCCC1 MODGBGCMMLUAIQ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
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- GGZBCIDSFGUWRA-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]-n-methylpropan-1-amine Chemical compound CNCCC[Si](C)(OC)OC GGZBCIDSFGUWRA-UHFFFAOYSA-N 0.000 description 1
- TZZGHGKTHXIOMN-UHFFFAOYSA-N 3-trimethoxysilyl-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCCC[Si](OC)(OC)OC TZZGHGKTHXIOMN-UHFFFAOYSA-N 0.000 description 1
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- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000011325 microbead Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- XCOASYLMDUQBHW-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)butan-1-amine Chemical compound CCCCNCCC[Si](OC)(OC)OC XCOASYLMDUQBHW-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 150000001367 organochlorosilanes Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical class [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- IALUUOKJPBOFJL-UHFFFAOYSA-N potassium oxidosilane Chemical compound [K+].[SiH3][O-] IALUUOKJPBOFJL-UHFFFAOYSA-N 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JSECNWXDEZOMPD-UHFFFAOYSA-N tetrakis(2-methoxyethyl) silicate Chemical compound COCCO[Si](OCCOC)(OCCOC)OCCOC JSECNWXDEZOMPD-UHFFFAOYSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- IZRJPHXTEXTLHY-UHFFFAOYSA-N triethoxy(2-triethoxysilylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CC[Si](OCC)(OCC)OCC IZRJPHXTEXTLHY-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- JCGDCINCKDQXDX-UHFFFAOYSA-N trimethoxy(2-trimethoxysilylethyl)silane Chemical compound CO[Si](OC)(OC)CC[Si](OC)(OC)OC JCGDCINCKDQXDX-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- QLNOVKKVHFRGMA-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group [CH2]CC[Si](OC)(OC)OC QLNOVKKVHFRGMA-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OLTVTFUBQOLTND-UHFFFAOYSA-N tris(2-methoxyethoxy)-methylsilane Chemical compound COCCO[Si](C)(OCCOC)OCCOC OLTVTFUBQOLTND-UHFFFAOYSA-N 0.000 description 1
- 101150046896 trm1 gene Proteins 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08872749.0A EP2222688B1 (fr) | 2007-12-20 | 2008-12-18 | Composes a structure guanidine et leurs utilisations comme catalyseurs de polycondensation d'organopolysiloxanes |
CN200880125419.2A CN101998960B (zh) | 2007-12-20 | 2008-12-18 | 具有胍结构的化合物及其作为有机聚硅氧烷缩聚催化剂的用途 |
KR1020107013592A KR101271994B1 (ko) | 2007-12-20 | 2008-12-18 | 구아니딘 구조를 갖는 화합물 및 이의 오르가노폴리실록산 중축합 촉매로서의 용도 |
US12/809,024 US8372935B2 (en) | 2007-12-20 | 2008-12-18 | Compounds with a guanidine structure and use thereof for as organopolysiloxane polycondensation catalysts |
JP2010538834A JP5352594B2 (ja) | 2007-12-20 | 2008-12-18 | グアニジン構造を有する化合物及びそのオルガノポリシロキサン重縮合触媒としての使用 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0708925A FR2925496A1 (fr) | 2007-12-20 | 2007-12-20 | Composes a structure guanidine et leurs utilisations comme catalyseurs de polycondensation d'organopolysiloxanes. |
FR0708925 | 2007-12-20 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2009106717A2 true WO2009106717A2 (fr) | 2009-09-03 |
WO2009106717A3 WO2009106717A3 (fr) | 2009-10-22 |
Family
ID=39711124
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2008/001767 WO2009106717A2 (fr) | 2007-12-20 | 2008-12-18 | Composes a structure guanidine et leurs utilisations comme catalyseurs de polycondensation d'organopolysiloxanes |
Country Status (7)
Country | Link |
---|---|
US (1) | US8372935B2 (fr) |
EP (1) | EP2222688B1 (fr) |
JP (1) | JP5352594B2 (fr) |
KR (1) | KR101271994B1 (fr) |
CN (1) | CN101998960B (fr) |
FR (1) | FR2925496A1 (fr) |
WO (1) | WO2009106717A2 (fr) |
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WO2014131695A1 (fr) | 2013-02-26 | 2014-09-04 | Akzo Nobel Coatings International B.V. | Compositions antisalissure avec un polymère ou oligomère contenant un oxyalkylène fluoré |
WO2015082408A2 (fr) | 2013-12-03 | 2015-06-11 | Akzo Nobel Coatings International B.V. | Procédé de revêtement d'une vieille couche de revêtement sur un substrat, et composition de revêtement pouvant être utilisée dans ce procédé |
WO2018134124A1 (fr) | 2017-01-17 | 2018-07-26 | Akzo Nobel Coatings International B.V. | Composition de revêtement antisalissure, substrat revêtu d'une telle composition de revêtement et utilisation de cette composition de revêtement |
WO2019115020A1 (fr) | 2017-12-14 | 2019-06-20 | Akzo Nobel Coatings International B.V. | Composition de revêtement antisalissure, substrat revêtu d'une telle composition de revêtement et utilisation de cette composition de revêtement |
WO2020011839A1 (fr) | 2018-07-13 | 2020-01-16 | Akzo Nobel Coatings International B.V. | Composition de couche d'accrochage |
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- 2008-12-18 US US12/809,024 patent/US8372935B2/en active Active
- 2008-12-18 EP EP08872749.0A patent/EP2222688B1/fr active Active
- 2008-12-18 KR KR1020107013592A patent/KR101271994B1/ko active IP Right Grant
- 2008-12-18 JP JP2010538834A patent/JP5352594B2/ja active Active
- 2008-12-18 WO PCT/FR2008/001767 patent/WO2009106717A2/fr active Application Filing
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Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2492323A1 (fr) | 2011-02-23 | 2012-08-29 | Akzo Nobel Coatings International B.V. | Composition résistante au bio-encrassement |
WO2013024106A1 (fr) | 2011-08-18 | 2013-02-21 | Akzo Nobel Coatings International B.V. | Composition anti-encrassement comprenant des stérols et/ou des dérivés de ceux-ci |
US9388316B2 (en) | 2011-08-18 | 2016-07-12 | Akzo Nobel Coatings International B.V. | Fouling-resistant composition comprising sterols and/or derivatives thereof |
WO2014131695A1 (fr) | 2013-02-26 | 2014-09-04 | Akzo Nobel Coatings International B.V. | Compositions antisalissure avec un polymère ou oligomère contenant un oxyalkylène fluoré |
WO2015082408A2 (fr) | 2013-12-03 | 2015-06-11 | Akzo Nobel Coatings International B.V. | Procédé de revêtement d'une vieille couche de revêtement sur un substrat, et composition de revêtement pouvant être utilisée dans ce procédé |
WO2018134124A1 (fr) | 2017-01-17 | 2018-07-26 | Akzo Nobel Coatings International B.V. | Composition de revêtement antisalissure, substrat revêtu d'une telle composition de revêtement et utilisation de cette composition de revêtement |
WO2019115020A1 (fr) | 2017-12-14 | 2019-06-20 | Akzo Nobel Coatings International B.V. | Composition de revêtement antisalissure, substrat revêtu d'une telle composition de revêtement et utilisation de cette composition de revêtement |
WO2019115021A1 (fr) | 2017-12-14 | 2019-06-20 | Akzo Nobel Coatings International B.V. | Substrat revêtu d'un système de revêtement multicouche et procédé de lutte contre l'encrassement biologique aquatique sur des objets fabriqués par l'homme à l'aide d'un tel système de revêtement multicouche |
WO2020011839A1 (fr) | 2018-07-13 | 2020-01-16 | Akzo Nobel Coatings International B.V. | Composition de couche d'accrochage |
WO2022207681A1 (fr) | 2021-03-30 | 2022-10-06 | Akzo Nobel Coatings International B.V. | Compositions de revêtement antisalissure |
Also Published As
Publication number | Publication date |
---|---|
KR20100087390A (ko) | 2010-08-04 |
US20110046299A1 (en) | 2011-02-24 |
WO2009106717A3 (fr) | 2009-10-22 |
JP5352594B2 (ja) | 2013-11-27 |
CN101998960B (zh) | 2014-11-12 |
EP2222688B1 (fr) | 2013-08-21 |
JP2011506584A (ja) | 2011-03-03 |
KR101271994B1 (ko) | 2013-06-05 |
EP2222688A2 (fr) | 2010-09-01 |
FR2925496A1 (fr) | 2009-06-26 |
US8372935B2 (en) | 2013-02-12 |
CN101998960A (zh) | 2011-03-30 |
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