DE10354259A1 - Verfahren zur Herstellung von Carbonylreste-aufweisenden Organosiliciumverbindungen - Google Patents
Verfahren zur Herstellung von Carbonylreste-aufweisenden Organosiliciumverbindungen Download PDFInfo
- Publication number
- DE10354259A1 DE10354259A1 DE2003154259 DE10354259A DE10354259A1 DE 10354259 A1 DE10354259 A1 DE 10354259A1 DE 2003154259 DE2003154259 DE 2003154259 DE 10354259 A DE10354259 A DE 10354259A DE 10354259 A1 DE10354259 A1 DE 10354259A1
- Authority
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- Germany
- Prior art keywords
- radical
- alkyl
- radicals
- carbonyl
- hydroxy
- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 59
- 150000003961 organosilicon compounds Chemical class 0.000 title claims abstract description 57
- 230000008569 process Effects 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- -1 cycloaliphatic Chemical group 0.000 claims abstract description 395
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000007800 oxidant agent Substances 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 11
- 230000003647 oxidation Effects 0.000 claims abstract description 10
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims description 115
- 150000002148 esters Chemical class 0.000 claims description 105
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 57
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 53
- CYFLXLSBHQBMFT-UHFFFAOYSA-N sulfamoxole Chemical group O1C(C)=C(C)N=C1NS(=O)(=O)C1=CC=C(N)C=C1 CYFLXLSBHQBMFT-UHFFFAOYSA-N 0.000 claims description 46
- 102000004190 Enzymes Human genes 0.000 claims description 42
- 108090000790 Enzymes Proteins 0.000 claims description 42
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229920006395 saturated elastomer Polymers 0.000 claims description 34
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 29
- 239000001301 oxygen Substances 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims description 15
- 229930195733 hydrocarbon Natural products 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 229910004283 SiO 4 Inorganic materials 0.000 claims description 8
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 8
- 125000000466 oxiranyl group Chemical group 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- XUXUHDYTLNCYQQ-UHFFFAOYSA-N 4-amino-TEMPO Chemical group CC1(C)CC(N)CC(C)(C)N1[O] XUXUHDYTLNCYQQ-UHFFFAOYSA-N 0.000 claims description 6
- MJEDTBDGYVATPI-UHFFFAOYSA-N 4-hydroxy-TEMPO benzoate Chemical group C1C(C)(C)N([O])C(C)(C)CC1OC(=O)C1=CC=CC=C1 MJEDTBDGYVATPI-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical class BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 239000000460 chlorine Chemical class 0.000 claims description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- 239000007844 bleaching agent Substances 0.000 claims description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical class [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 238000005868 electrolysis reaction Methods 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 239000003570 air Substances 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 150000004966 inorganic peroxy acids Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- YUUWVCDKDHHAFI-UHFFFAOYSA-N n-sulfanylhydroxylamine Chemical compound ONS YUUWVCDKDHHAFI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001451 organic peroxides Chemical class 0.000 claims description 2
- 150000004967 organic peroxy acids Chemical class 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 2
- 238000012546 transfer Methods 0.000 claims description 2
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical group CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 239000012048 reactive intermediate Substances 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 description 171
- 229910052757 nitrogen Inorganic materials 0.000 description 70
- 239000000370 acceptor Substances 0.000 description 32
- 150000002431 hydrogen Chemical class 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000012071 phase Substances 0.000 description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
- 150000002367 halogens Chemical group 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 15
- 229920001296 polysiloxane Polymers 0.000 description 13
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 11
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 11
- 150000002170 ethers Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 10
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 10
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 10
- 150000004053 quinones Chemical class 0.000 description 10
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- KZOWNALBTMILAP-JBMRGDGGSA-N ancitabine hydrochloride Chemical compound Cl.N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 KZOWNALBTMILAP-JBMRGDGGSA-N 0.000 description 8
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 8
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 8
- 102000018832 Cytochromes Human genes 0.000 description 7
- 108010052832 Cytochromes Proteins 0.000 description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 6
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 150000002923 oximes Chemical class 0.000 description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 5
- 108010081409 Iron-Sulfur Proteins Proteins 0.000 description 5
- 102000005298 Iron-Sulfur Proteins Human genes 0.000 description 5
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000002019 disulfides Chemical class 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 125000005358 mercaptoalkyl group Chemical group 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 4
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 4
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical class C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
- HRRVLSKRYVIEPR-UHFFFAOYSA-N 6-hydroxy-5-nitroso-1H-pyrimidine-2,4-dione Chemical compound OC1=NC(O)=C(N=O)C(O)=N1 HRRVLSKRYVIEPR-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 229910004013 NO 2 Inorganic materials 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- GMJUGPZVHVVVCG-UHFFFAOYSA-N n-hydroxy-n-phenylacetamide Chemical compound CC(=O)N(O)C1=CC=CC=C1 GMJUGPZVHVVVCG-UHFFFAOYSA-N 0.000 description 4
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000005375 organosiloxane group Chemical group 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- BUXKULRFRATXSI-UHFFFAOYSA-N 1-hydroxypyrrole-2,5-dione Chemical class ON1C(=O)C=CC1=O BUXKULRFRATXSI-UHFFFAOYSA-N 0.000 description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- SKLDEGYSXDTKMR-UHFFFAOYSA-N 4-hydroxy-3-nitroso-1H-pyridin-2-one Chemical compound OC1=CC=NC(O)=C1N=O SKLDEGYSXDTKMR-UHFFFAOYSA-N 0.000 description 3
- JDMLZFKVRURCKJ-UHFFFAOYSA-N 6-hydroxy-5-nitroso-1H-pyridin-2-one Chemical compound OC1=CC=C(N=O)C(O)=N1 JDMLZFKVRURCKJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 108010029541 Laccase Proteins 0.000 description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical class ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 102000004316 Oxidoreductases Human genes 0.000 description 3
- 108090000854 Oxidoreductases Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 150000005840 aryl radicals Chemical class 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- QOWGKOOAVPYSPT-UHFFFAOYSA-N chembl42071 Chemical compound C1=CC=C2C(O)=C(N=O)C(O)=NC2=C1 QOWGKOOAVPYSPT-UHFFFAOYSA-N 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000011067 equilibration Methods 0.000 description 3
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000001841 imino group Chemical class [H]N=* 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000005949 ozonolysis reaction Methods 0.000 description 3
- 125000000913 palmityl 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])C([H])([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 3
- 239000002245 particle Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 229920002545 silicone oil Polymers 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
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- QHMGFQBUOCYLDT-RNFRBKRXSA-N n-(diaminomethylidene)-2-[(2r,5r)-2,5-dimethyl-2,5-dihydropyrrol-1-yl]acetamide Chemical compound C[C@@H]1C=C[C@@H](C)N1CC(=O)N=C(N)N QHMGFQBUOCYLDT-RNFRBKRXSA-N 0.000 description 1
- PWIOUEAUSUBDEB-UHFFFAOYSA-N n-[3-[acetyl(hydroxy)amino]phenyl]-n-hydroxyacetamide Chemical compound CC(=O)N(O)C1=CC=CC(N(O)C(C)=O)=C1 PWIOUEAUSUBDEB-UHFFFAOYSA-N 0.000 description 1
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- JQNCCPZMHNPGBX-UHFFFAOYSA-N n-hydroxy-n-methylthiophene-2-carboxamide Chemical compound CN(O)C(=O)C1=CC=CS1 JQNCCPZMHNPGBX-UHFFFAOYSA-N 0.000 description 1
- FWUDLKMCWUETIP-UHFFFAOYSA-N n-hydroxy-n-phenylformamide Chemical compound O=CN(O)C1=CC=CC=C1 FWUDLKMCWUETIP-UHFFFAOYSA-N 0.000 description 1
- IBKOQUUOKFBMRC-UHFFFAOYSA-N n-hydroxy-n-phenylprop-2-enamide Chemical compound C=CC(=O)N(O)C1=CC=CC=C1 IBKOQUUOKFBMRC-UHFFFAOYSA-N 0.000 description 1
- IDUFGQNXJUPCJC-UHFFFAOYSA-N n-hydroxy-n-propan-2-ylbenzenesulfonamide Chemical compound CC(C)N(O)S(=O)(=O)C1=CC=CC=C1 IDUFGQNXJUPCJC-UHFFFAOYSA-N 0.000 description 1
- MHSMDNDOXXFCRC-UHFFFAOYSA-N n-hydroxy-n-propan-2-ylmethanesulfonamide Chemical compound CC(C)N(O)S(C)(=O)=O MHSMDNDOXXFCRC-UHFFFAOYSA-N 0.000 description 1
- MWSBVZLOLMRESJ-UHFFFAOYSA-N n-hydroxy-n-propan-2-ylthiophene-2-carboxamide Chemical compound CC(C)N(O)C(=O)C1=CC=CS1 MWSBVZLOLMRESJ-UHFFFAOYSA-N 0.000 description 1
- MHPZUFJZXDHMOU-UHFFFAOYSA-N n-tert-butyl-n-hydroxythiophene-2-carboxamide Chemical compound CC(C)(C)N(O)C(=O)C1=CC=CS1 MHPZUFJZXDHMOU-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- ZKATWMILCYLAPD-UHFFFAOYSA-N niobium pentoxide Inorganic materials O=[Nb](=O)O[Nb](=O)=O ZKATWMILCYLAPD-UHFFFAOYSA-N 0.000 description 1
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- 125000005574 norbornylene group Chemical group 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
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 description 1
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- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
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- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
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- NBBJYMSMWIIQGU-UHFFFAOYSA-N propionic aldehyde Natural products CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 238000010966 qNMR Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
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- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000005488 sandblasting Methods 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- 239000010935 stainless steel Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 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
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical group SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- TXBMCLDHFRIQLA-UHFFFAOYSA-N trimethyl(3-methylbuta-1,3-dienoxy)silane Chemical compound CC(=C)C=CO[Si](C)(C)C TXBMCLDHFRIQLA-UHFFFAOYSA-N 0.000 description 1
- PMTXWMFGFKYIJE-UHFFFAOYSA-N trimethyl(penta-1,3-dien-2-yloxy)silane Chemical compound CC=CC(=C)O[Si](C)(C)C PMTXWMFGFKYIJE-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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- 210000002268 wool Anatomy 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31826—Of natural rubber
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
- Cosmetics (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2003154259 DE10354259A1 (de) | 2003-11-20 | 2003-11-20 | Verfahren zur Herstellung von Carbonylreste-aufweisenden Organosiliciumverbindungen |
| DE200450005985 DE502004005985D1 (de) | 2003-11-20 | 2004-11-18 | Verfahren zur herstellung von carbonylreste-aufweisenden organosiliciumverbindungen |
| JP2006540334A JP2007512400A (ja) | 2003-11-20 | 2004-11-18 | カルボニル基を有する有機ケイ素化合物の製造方法 |
| CNB2004800407116A CN100528937C (zh) | 2003-11-20 | 2004-11-18 | 制造具有羰基的有机硅化合物的方法 |
| US10/595,955 US7700196B2 (en) | 2003-11-20 | 2004-11-18 | Method for producing carbonyl group-containing organosilicon compounds |
| PCT/EP2004/013137 WO2005049697A2 (de) | 2003-11-20 | 2004-11-18 | Verfahren zur herstellung von carbonylreste-aufweisenden organosiliciumverbindungen |
| EP04797999A EP1685183B1 (de) | 2003-11-20 | 2004-11-18 | Verfahren zur herstellung von carbonylreste-aufweisenden organosiliciumverbindungen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2003154259 DE10354259A1 (de) | 2003-11-20 | 2003-11-20 | Verfahren zur Herstellung von Carbonylreste-aufweisenden Organosiliciumverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10354259A1 true DE10354259A1 (de) | 2005-06-09 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2003154259 Withdrawn DE10354259A1 (de) | 2003-11-20 | 2003-11-20 | Verfahren zur Herstellung von Carbonylreste-aufweisenden Organosiliciumverbindungen |
| DE200450005985 Expired - Lifetime DE502004005985D1 (de) | 2003-11-20 | 2004-11-18 | Verfahren zur herstellung von carbonylreste-aufweisenden organosiliciumverbindungen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE200450005985 Expired - Lifetime DE502004005985D1 (de) | 2003-11-20 | 2004-11-18 | Verfahren zur herstellung von carbonylreste-aufweisenden organosiliciumverbindungen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7700196B2 (https=) |
| EP (1) | EP1685183B1 (https=) |
| JP (1) | JP2007512400A (https=) |
| CN (1) | CN100528937C (https=) |
| DE (2) | DE10354259A1 (https=) |
| WO (1) | WO2005049697A2 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007011465A1 (en) | 2005-07-18 | 2007-01-25 | Dow Corning Corporation | Aldehyde functional siloxanes |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7696294B2 (en) | 2006-08-02 | 2010-04-13 | Honeywell International Inc. | Siloxane polymers and uses thereof |
| WO2008016957A2 (en) * | 2006-08-02 | 2008-02-07 | Honeywell International Inc. | Siloxane polymers and uses thereof |
| DE102007047211A1 (de) * | 2007-10-02 | 2009-04-09 | Wacker Chemie Ag | Entschäumerzusammensetzungen |
| JP5413710B2 (ja) * | 2008-06-11 | 2014-02-12 | 日本電気株式会社 | 電極活物質と、その製造方法及びそれを用いた電池 |
| KR101057191B1 (ko) * | 2008-12-30 | 2011-08-16 | 주식회사 하이닉스반도체 | 반도체 소자의 미세 패턴 형성방법 |
| EP2617703B1 (en) | 2012-01-17 | 2014-07-30 | Corning Incorporated | Improved catalyzed hypohalous oxidation of alcohol groups |
| US20150209808A1 (en) * | 2014-01-24 | 2015-07-30 | The Procter & Gamble Company | Package for Light Activated Treatment Composition |
| JP2017536468A (ja) | 2014-09-23 | 2017-12-07 | モメンティブ パフォーマンス マテリアルズ ゲーエムベーハー | アミノ酸系基質の処理のためのシリコーン化合物およびその組成物 |
| US11179312B2 (en) | 2017-06-05 | 2021-11-23 | Momentive Performance Materials Inc. | Aqueous compositions for the treatment of hair |
| EP3581697B1 (en) | 2018-06-11 | 2023-02-22 | The Procter & Gamble Company | Photoactivating device for washing machine |
| US11090255B2 (en) | 2018-12-04 | 2021-08-17 | Momentive Performance Materials Inc. | Use of polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair |
| CN119053641A (zh) * | 2022-04-21 | 2024-11-29 | 信越化学工业株式会社 | 醛改性有机硅及其制造方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2803637A (en) * | 1954-01-18 | 1957-08-20 | Dow Corning | Organosiloxane aldehydes |
| US2947770A (en) * | 1955-05-13 | 1960-08-02 | Union Carbide Corp | Diformylbutyl and diformylcyclopentyl containing siloxanes |
| US2970150A (en) | 1957-12-17 | 1961-01-31 | Union Carbide Corp | Processes for the reaction of silanic hydrogen-bonded siloxanes with unsaturated organic compounds with a platinum catalyst |
| DE3632869A1 (de) | 1986-09-26 | 1988-03-31 | Bayer Ag | Polysiloxane |
| FR2636067B1 (fr) * | 1988-09-05 | 1990-05-18 | Rhone Poulenc Chimie | Polyorganosiloxane a fonction propanaldehyde et son procede de preparation par hydroformylation |
| FR2645867B1 (fr) | 1989-04-13 | 1991-06-14 | Rhone Poulenc Chimie | Procede de preparation, par hydroformylation, de polyorganosiloxane a fonction propanaldehyde |
| FR2647801B1 (fr) | 1989-06-02 | 1991-09-13 | Rhone Poulenc Chimie | Composition durcissable, sous un rayonnement, a base de polyorganosiloxane a fonction propanaldehyde |
| DE4306041A1 (de) | 1993-02-26 | 1994-09-01 | Wacker Chemie Gmbh | Glycosidreste aufweisende Organosiliciumverbindungen und Verfahren zu deren Herstellung |
| US5739246A (en) * | 1997-03-06 | 1998-04-14 | Dow Corning Corporation | Preparation of carbonyl functional polysiloxanes |
| BR9910274A (pt) * | 1998-05-07 | 2001-01-02 | Tno | Processo para a oxidação de um álcool primário |
| US6121404A (en) * | 1998-07-06 | 2000-09-19 | Dow Corning Corporation | β-diketo functional organosilicon compounds |
| JP4394230B2 (ja) * | 1999-12-13 | 2010-01-06 | 高砂香料工業株式会社 | ３−メチル−２，４−ノナンジオンの製造法 |
| DE10029597A1 (de) * | 2000-06-15 | 2002-01-03 | Degussa | Verfahren zur Oxidation von Alkoholen mit homogen löslichen polymervergrößerten Stickstoffverbindungen als Katalysator |
| JP2003073332A (ja) * | 2001-06-20 | 2003-03-12 | Kuraray Co Ltd | ２−オキソカルボン酸エステル類の製造方法 |
| ATE257136T1 (de) | 2001-10-11 | 2004-01-15 | Consortium Elektrochem Ind | Verfahren zur oxidation von alkoholen unter katalyse von nitroxylverbindungen |
-
2003
- 2003-11-20 DE DE2003154259 patent/DE10354259A1/de not_active Withdrawn
-
2004
- 2004-11-18 EP EP04797999A patent/EP1685183B1/de not_active Expired - Lifetime
- 2004-11-18 CN CNB2004800407116A patent/CN100528937C/zh not_active Expired - Fee Related
- 2004-11-18 DE DE200450005985 patent/DE502004005985D1/de not_active Expired - Lifetime
- 2004-11-18 JP JP2006540334A patent/JP2007512400A/ja active Pending
- 2004-11-18 US US10/595,955 patent/US7700196B2/en not_active Expired - Fee Related
- 2004-11-18 WO PCT/EP2004/013137 patent/WO2005049697A2/de not_active Ceased
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007011465A1 (en) | 2005-07-18 | 2007-01-25 | Dow Corning Corporation | Aldehyde functional siloxanes |
| US7999053B2 (en) * | 2005-07-18 | 2011-08-16 | Dow Corning Corporation | Aldehyde functional siloxanes |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1685183A2 (de) | 2006-08-02 |
| CN1906230A (zh) | 2007-01-31 |
| US20070129520A1 (en) | 2007-06-07 |
| DE502004005985D1 (de) | 2008-03-06 |
| US7700196B2 (en) | 2010-04-20 |
| WO2005049697A3 (de) | 2006-02-09 |
| WO2005049697A2 (de) | 2005-06-02 |
| EP1685183B1 (de) | 2008-01-16 |
| JP2007512400A (ja) | 2007-05-17 |
| CN100528937C (zh) | 2009-08-19 |
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