IE42449B1 - Ethylenic silicon compounds with functional groups - Google Patents
Ethylenic silicon compounds with functional groupsInfo
- Publication number
- IE42449B1 IE42449B1 IE2115/75A IE211575A IE42449B1 IE 42449 B1 IE42449 B1 IE 42449B1 IE 2115/75 A IE2115/75 A IE 2115/75A IE 211575 A IE211575 A IE 211575A IE 42449 B1 IE42449 B1 IE 42449B1
- Authority
- IE
- Ireland
- Prior art keywords
- group
- radical
- atoms
- carbon atoms
- straight
- Prior art date
Links
- 125000000524 functional group Chemical group 0.000 title claims abstract description 19
- 150000003377 silicon compounds Chemical class 0.000 title description 4
- -1 haloaryl radical Chemical class 0.000 claims abstract description 84
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 150000003254 radicals Chemical class 0.000 claims abstract description 25
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
- 125000001118 alkylidene group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- 239000005711 Benzoic acid Substances 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 150000002641 lithium Chemical group 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 125000005023 xylyl group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000002070 alkenylidene group Chemical group 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000005462 imide group Chemical group 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- BWVXXWZPOLIIRY-UHFFFAOYSA-N 1-(4-isocyanatophenoxy)prop-2-enyl-dimethylsilane Chemical compound N(=C=O)C1=CC=C(C=C1)OC([SiH](C)C)C=C BWVXXWZPOLIIRY-UHFFFAOYSA-N 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims 1
- WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 9
- 239000002253 acid Substances 0.000 abstract description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001412 amines Chemical class 0.000 abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 4
- 229910021626 Tin(II) chloride Inorganic materials 0.000 abstract description 2
- 235000011150 stannous chloride Nutrition 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 150000004756 silanes Chemical class 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- 229910006124 SOCl2 Inorganic materials 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 229910000077 silane Inorganic materials 0.000 abstract 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 238000004821 distillation Methods 0.000 description 9
- 238000009835 boiling Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- ARCHKESRFBPGES-UHFFFAOYSA-N 4-(2-methylprop-1-enylsilylmethoxy)benzoic acid Chemical compound CC(=C[SiH2]COC1=CC=C(C(=O)O)C=C1)C ARCHKESRFBPGES-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 3
- SZZZMXFBEKWPBU-UHFFFAOYSA-N chloromethyl-ethenyl-dimethylsilane Chemical compound ClC[Si](C)(C)C=C SZZZMXFBEKWPBU-UHFFFAOYSA-N 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- NOCYAKXSNZBASX-UHFFFAOYSA-N 2-methylprop-1-enylsilylmethyl 4-aminobenzoate Chemical compound CC(=C[SiH2]COC(=O)C1=CC=C(C=C1)N)C NOCYAKXSNZBASX-UHFFFAOYSA-N 0.000 description 2
- PZHNAJWIUOBFOZ-UHFFFAOYSA-N 4-(penta-1,4-dien-3-ylsilylmethoxy)benzoic acid Chemical compound C(=C)C(C=C)[SiH2]COC1=CC=C(C(=O)O)C=C1 PZHNAJWIUOBFOZ-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- OBDCMPKZDYVYBE-UHFFFAOYSA-N chloromethyl(2-methylprop-1-enyl)silane Chemical compound CC(C)=C[SiH2]CCl OBDCMPKZDYVYBE-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- OZPWSEBUJWNHIX-UHFFFAOYSA-N methyl 4-(2-methylprop-1-enylsilylmethoxy)benzoate Chemical compound CC(=C[SiH2]COC1=CC=C(C(=O)OC)C=C1)C OZPWSEBUJWNHIX-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 150000007944 thiolates Chemical class 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- MKWJZTFMDWSRIH-UHFFFAOYSA-N (4-fluoro-3-nitrophenyl)methanol Chemical compound OCC1=CC=C(F)C([N+]([O-])=O)=C1 MKWJZTFMDWSRIH-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- FMDLULDBQDPDKN-UHFFFAOYSA-N 1-(3,4-dinitrophenoxy)prop-2-enyl-dimethylsilane Chemical compound [N+](=O)([O-])C1=C(C=C(C=C1)OC([SiH](C)C)C=C)[N+](=O)[O-] FMDLULDBQDPDKN-UHFFFAOYSA-N 0.000 description 1
- IBPDESAWRSVZCM-UHFFFAOYSA-N 1-(4-nitrophenoxy)prop-2-enyl-diphenylsilane Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)OC([SiH](C1=CC=CC=C1)C1=CC=CC=C1)C=C IBPDESAWRSVZCM-UHFFFAOYSA-N 0.000 description 1
- BPYUVPUKCKHMQZ-UHFFFAOYSA-N 2-(1-dimethylsilylprop-2-enoxy)acetic acid Chemical compound C(=C)C(OCC(=O)O)[SiH](C)C BPYUVPUKCKHMQZ-UHFFFAOYSA-N 0.000 description 1
- RJIXOOWTCNNQQD-UHFFFAOYSA-N 2-[(2-carboxyphenyl)-dimethylsilyl]benzoic acid Chemical compound C=1C=CC=C(C(O)=O)C=1[Si](C)(C)C1=CC=CC=C1C(O)=O RJIXOOWTCNNQQD-UHFFFAOYSA-N 0.000 description 1
- MKXQDMSCTKHCAQ-UHFFFAOYSA-N 2-[(2-carboxyphenyl)-methyl-trimethylsilyloxysilyl]benzoic acid Chemical compound C=1C=CC=C(C(O)=O)C=1[Si](C)(O[Si](C)(C)C)C1=CC=CC=C1C(O)=O MKXQDMSCTKHCAQ-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- MAYUMUDTQDNZBD-UHFFFAOYSA-N 2-chloroethylsilane Chemical compound [SiH3]CCCl MAYUMUDTQDNZBD-UHFFFAOYSA-N 0.000 description 1
- GKLBTTXIWKZNSZ-UHFFFAOYSA-N 2-methylprop-1-enyl-[(4-nitrophenoxy)methyl]silane Chemical compound CC(=C[SiH2]COC1=CC=C(C=C1)[N+](=O)[O-])C GKLBTTXIWKZNSZ-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 1
- CPXSRLFMOAXSPM-UHFFFAOYSA-N 4-(1-dimethylsilylprop-2-enoxy)aniline Chemical compound NC1=CC=C(C=C1)OC([SiH](C)C)C=C CPXSRLFMOAXSPM-UHFFFAOYSA-N 0.000 description 1
- HCMKCTCAMXPTKA-UHFFFAOYSA-N 4-(1-dimethylsilylprop-2-enoxy)butanoic acid Chemical compound C(=C)C(OCCCC(=O)O)[SiH](C)C HCMKCTCAMXPTKA-UHFFFAOYSA-N 0.000 description 1
- CWKFRBYUYVQPIV-UHFFFAOYSA-N 4-(2-methylprop-1-enylsilylmethoxy)aniline Chemical compound CC(=C[SiH2]COC1=CC=C(C=C1)N)C CWKFRBYUYVQPIV-UHFFFAOYSA-N 0.000 description 1
- LFZQCJLFQTXGKW-UHFFFAOYSA-N 4-[(4-nitrophenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1CC1=CC=C([N+]([O-])=O)C=C1 LFZQCJLFQTXGKW-UHFFFAOYSA-N 0.000 description 1
- OXWOIUVGAWIZQQ-UHFFFAOYSA-N 4-ethoxybenzenethiol Chemical compound CCOC1=CC=C(S)C=C1 OXWOIUVGAWIZQQ-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
- ODVBBZFQPGORMJ-UHFFFAOYSA-N 4-nitrobenzylamine Chemical compound NCC1=CC=C([N+]([O-])=O)C=C1 ODVBBZFQPGORMJ-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- AXBVSRMHOPMXBA-UHFFFAOYSA-N 4-nitrothiophenol Chemical compound [O-][N+](=O)C1=CC=C(S)C=C1 AXBVSRMHOPMXBA-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- JJAFOLHJNGDUDR-UHFFFAOYSA-N N-(2-dimethylsilylethyl)-N-ethenyl-4-nitroaniline Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)N(C=C)CC[SiH](C)C JJAFOLHJNGDUDR-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229910018557 Si O Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- RDGCOJHKQYOHIH-UHFFFAOYSA-N chloromethyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound ClC[Si](C)(C)O[Si](C)(C)C=C RDGCOJHKQYOHIH-UHFFFAOYSA-N 0.000 description 1
- JOEJYLLWXYGKID-UHFFFAOYSA-N chloromethyl-bis(ethenyl)-methylsilane Chemical compound ClC[Si](C)(C=C)C=C JOEJYLLWXYGKID-UHFFFAOYSA-N 0.000 description 1
- FTXWJNATARXVOL-UHFFFAOYSA-N chloromethyl-dimethyl-(1,2,2-trichloroethenyl)silane Chemical compound ClC[Si](C)(C)C(Cl)=C(Cl)Cl FTXWJNATARXVOL-UHFFFAOYSA-N 0.000 description 1
- AGSAAEUUKGRHHV-UHFFFAOYSA-N chloromethyl-ethenyl-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=C)(CCl)C1=CC=CC=C1 AGSAAEUUKGRHHV-UHFFFAOYSA-N 0.000 description 1
- STKYKEGVTKJLHS-UHFFFAOYSA-N chloromethyl-phenyl-prop-2-enylsilane Chemical compound C(=C)C[SiH](CCl)C1=CC=CC=C1 STKYKEGVTKJLHS-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000005724 cycloalkenylene group Chemical group 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- BSQIKQNZEGTNPA-UHFFFAOYSA-N dimethyl-[1-(4-nitrophenyl)sulfanylprop-2-enyl]silane Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)SC([SiH](C)C)C=C BSQIKQNZEGTNPA-UHFFFAOYSA-N 0.000 description 1
- YOSJLRZWXWSKSH-UHFFFAOYSA-N dimethyl-[2,3,3-trichloro-1-(4-nitrophenoxy)prop-2-enyl]silane Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)OC([SiH](C)C)C(=C(Cl)Cl)Cl YOSJLRZWXWSKSH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- PVBRSNZAOAJRKO-UHFFFAOYSA-N ethyl 2-sulfanylacetate Chemical compound CCOC(=O)CS PVBRSNZAOAJRKO-UHFFFAOYSA-N 0.000 description 1
- IBVGWNDFWMJACF-UHFFFAOYSA-N ethyl 4-(1-dimethylsilylprop-2-enylsulfanylcarbothioyl)benzoate Chemical compound C(C)OC(=O)C1=CC=C(C=C1)C(=S)SC([SiH](C)C)C=C IBVGWNDFWMJACF-UHFFFAOYSA-N 0.000 description 1
- LCTSCELUBIVWNY-UHFFFAOYSA-N ethyl 4-(2-dimethylsilylbut-3-enethioyl)benzoate Chemical compound C(C)OC(=O)C1=CC=C(C=C1)C(=S)C([SiH](C)C)C=C LCTSCELUBIVWNY-UHFFFAOYSA-N 0.000 description 1
- WCTQEHGXBKFLKG-UHFFFAOYSA-N ethyl 4-(aminomethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(CN)C=C1 WCTQEHGXBKFLKG-UHFFFAOYSA-N 0.000 description 1
- NBBWLOJCZSYDAD-UHFFFAOYSA-N ethyl 4-sulfanylbenzoate Chemical compound CCOC(=O)C1=CC=C(S)C=C1 NBBWLOJCZSYDAD-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- GXDCEABUKNGWLI-UHFFFAOYSA-N methyl 4-(penta-1,4-dien-3-ylsilylmethoxy)benzoate Chemical compound C(=C)C(C=C)[SiH2]COC1=CC=C(C(=O)OC)C=C1 GXDCEABUKNGWLI-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LQNUZADURLCDLV-IDEBNGHGSA-N nitrobenzene Chemical compound [O-][N+](=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 LQNUZADURLCDLV-IDEBNGHGSA-N 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- CURNJKLCYZZBNJ-UHFFFAOYSA-M sodium;4-nitrophenolate Chemical compound [Na+].[O-]C1=CC=C([N+]([O-])=O)C=C1 CURNJKLCYZZBNJ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 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
- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/50—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon 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 Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- 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 Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- 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 Table
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
-
- 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
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
-
- 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
- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7433041A FR2286832A1 (fr) | 1974-10-01 | 1974-10-01 | Composes silicies ethyleniques a groupements fonctionnels |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42449L IE42449L (en) | 1976-04-01 |
| IE42449B1 true IE42449B1 (en) | 1980-08-13 |
Family
ID=9143628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2115/75A IE42449B1 (en) | 1974-10-01 | 1975-09-29 | Ethylenic silicon compounds with functional groups |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS589085B2 (ru) |
| AT (1) | AT339334B (ru) |
| BE (1) | BE834044A (ru) |
| BR (1) | BR7506232A (ru) |
| CA (1) | CA1083167A (ru) |
| CH (1) | CH611907A5 (ru) |
| DD (1) | DD126967A5 (ru) |
| DE (1) | DE2543882C3 (ru) |
| DK (1) | DK439875A (ru) |
| ES (1) | ES441418A1 (ru) |
| FR (1) | FR2286832A1 (ru) |
| GB (1) | GB1517559A (ru) |
| IE (1) | IE42449B1 (ru) |
| IT (1) | IT1043033B (ru) |
| LU (1) | LU73476A1 (ru) |
| NL (1) | NL7511209A (ru) |
| SE (1) | SE426831B (ru) |
| SU (1) | SU612633A3 (ru) |
| ZA (3) | ZA756153B (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2362183A1 (fr) * | 1976-08-17 | 1978-03-17 | Rhone Poulenc Ind | Elastomeres thermoplastiques polysiloxaniques |
| IL59345A0 (en) * | 1979-02-13 | 1980-05-30 | M & T Chemicals Inc | Silicone-containing bis-ether and bis-thioether aromatic amines and their manufacture |
| US5032460A (en) * | 1989-08-14 | 1991-07-16 | Minnesota Mining And Manufacturing Company | Method of making vinyl-silicone copolymers using mercapto functional silicone chain-transfer agents and release coatings made therewith |
| SG11201603025RA (en) * | 2013-10-18 | 2016-05-30 | Trinseo Europe Gmbh | Vinylsilanes for use in functionalized elastomeric polymers |
| RU2612261C1 (ru) * | 2016-03-29 | 2017-03-03 | ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ БЮДЖЕТНОЕ ОБРАЗОВАТЕЛЬНОЕ УЧРЕЖДЕНИЕ ВЫСШЕГО ОБРАЗОВАНИЯ "КУБАНСКИЙ ГОСУДАРСТВЕННЫЙ УНИВЕРСИТЕТ" (ФГБОУ ВПО "КубГУ") | Способ получения силилкарбаматов |
-
1974
- 1974-10-01 FR FR7433041A patent/FR2286832A1/fr active Granted
-
1975
- 1975-09-23 NL NL7511209A patent/NL7511209A/xx not_active Application Discontinuation
- 1975-09-26 SU SU752175639A patent/SU612633A3/ru active
- 1975-09-26 BR BR7506232*A patent/BR7506232A/pt unknown
- 1975-09-29 ZA ZA00756153A patent/ZA756153B/xx unknown
- 1975-09-29 ZA ZA00756152A patent/ZA756152B/xx unknown
- 1975-09-29 JP JP50117584A patent/JPS589085B2/ja not_active Expired
- 1975-09-29 IE IE2115/75A patent/IE42449B1/en unknown
- 1975-09-29 ZA ZA00756154A patent/ZA756154B/xx unknown
- 1975-09-30 CH CH1266175A patent/CH611907A5/xx not_active IP Right Cessation
- 1975-09-30 DK DK439875A patent/DK439875A/da unknown
- 1975-09-30 BE BE160571A patent/BE834044A/xx not_active IP Right Cessation
- 1975-09-30 SE SE7510966A patent/SE426831B/xx unknown
- 1975-09-30 GB GB40057/75A patent/GB1517559A/en not_active Expired
- 1975-09-30 LU LU73476A patent/LU73476A1/xx unknown
- 1975-09-30 CA CA236,684A patent/CA1083167A/fr not_active Expired
- 1975-10-01 AT AT750475A patent/AT339334B/de not_active IP Right Cessation
- 1975-10-01 DD DD188669A patent/DD126967A5/xx unknown
- 1975-10-01 DE DE2543882A patent/DE2543882C3/de not_active Expired
- 1975-10-01 IT IT27848/75A patent/IT1043033B/it active
- 1975-10-02 ES ES441418A patent/ES441418A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE42449L (en) | 1976-04-01 |
| SE7510966L (sv) | 1976-04-02 |
| DK439875A (da) | 1976-04-02 |
| ATA750475A (de) | 1977-02-15 |
| ZA756153B (en) | 1976-09-29 |
| AT339334B (de) | 1977-10-10 |
| ES441418A1 (es) | 1977-03-01 |
| ZA756154B (en) | 1976-09-29 |
| DE2543882C3 (de) | 1979-08-02 |
| IT1043033B (it) | 1980-02-20 |
| SU612633A3 (ru) | 1978-06-25 |
| DE2543882B2 (de) | 1978-11-16 |
| BR7506232A (pt) | 1976-08-03 |
| CH611907A5 (en) | 1979-06-29 |
| DE2543882A1 (de) | 1976-04-08 |
| GB1517559A (en) | 1978-07-12 |
| JPS589085B2 (ja) | 1983-02-18 |
| NL7511209A (nl) | 1976-04-05 |
| FR2286832B1 (ru) | 1978-12-29 |
| JPS5163127A (ru) | 1976-06-01 |
| CA1083167A (fr) | 1980-08-05 |
| BE834044A (fr) | 1976-03-30 |
| ZA756152B (en) | 1976-09-29 |
| FR2286832A1 (fr) | 1976-04-30 |
| LU73476A1 (ru) | 1976-08-19 |
| DD126967A5 (ru) | 1977-08-24 |
| SE426831B (sv) | 1983-02-14 |
| AU8527175A (en) | 1977-04-07 |
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