DD254203A5 - Verfahren zur herstellung von mon0-silyl-substituierten cyclopentadienen - Google Patents

Verfahren zur herstellung von mon0-silyl-substituierten cyclopentadienen Download PDF

Info

Publication number: DD254203A5
Authority: DD; German Democratic Republic
Prior art keywords: mol; phenyl; preparation; formula; nah
Prior art date: 1984-07-28

Application number

DD85279025A

Other languages

German (de)

English (en)

Inventor

Ulrich Deschler

Peter Panster

Peter Kleinschmidt

Siegfried Wolff

Ew-Hong Tan

Original Assignee

��@��k��

Priority date (The priority date 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 date listed.)

1984-07-28

Filing date

1985-07-26

Publication date

1988-02-17

1985-07-26 Application filed by ��@��k�� filed Critical ��@��k��

1988-02-17 Publication of DD254203A5 publication Critical patent/DD254203A5/de

Links

238000004519 manufacturing process Methods 0.000 title abstract description 3
238000000034 method Methods 0.000 claims abstract description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 38
238000006243 chemical reaction Methods 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 20
-1 mono-silyl-substituted cyclopentadienes Chemical class 0.000 claims description 15
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
229910000077 silane Inorganic materials 0.000 claims description 8
238000004821 distillation Methods 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 3
239000003495 polar organic solvent Substances 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
229910001508 alkali metal halide Inorganic materials 0.000 claims description 2
150000008045 alkali metal halides Chemical class 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
239000011261 inert gas Substances 0.000 claims 1
OHUVHDUNQKJDKW-UHFFFAOYSA-N sodium;cyclopenta-1,3-diene Chemical compound [Na+].C=1C=C[CH-]C=1 OHUVHDUNQKJDKW-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 33
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract description 32
150000002978 peroxides Chemical class 0.000 abstract description 2
229920003051 synthetic elastomer Polymers 0.000 abstract description 2
239000005061 synthetic rubber Substances 0.000 abstract description 2
229920001296 polysiloxane Polymers 0.000 abstract 1
125000005353 silylalkyl group Chemical group 0.000 abstract 1
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239000000057 synthetic resin Substances 0.000 abstract 1
229920001971 elastomer Polymers 0.000 description 27
239000005060 rubber Substances 0.000 description 25
239000000945 filler Substances 0.000 description 23
229910000104 sodium hydride Inorganic materials 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
239000007788 liquid Substances 0.000 description 13
238000005194 fractionation Methods 0.000 description 12
238000001556 precipitation Methods 0.000 description 12
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AVZCDBSGOSIHRC-UHFFFAOYSA-N 3-cyclopenta-2,4-dien-1-ylpropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCC1C=CC=C1 AVZCDBSGOSIHRC-UHFFFAOYSA-N 0.000 description 8
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
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238000005299 abrasion Methods 0.000 description 7
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238000002156 mixing Methods 0.000 description 6
150000001282 organosilanes Chemical class 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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239000000047 product Substances 0.000 description 5
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 4
239000003365 glass fiber Substances 0.000 description 4
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239000011787 zinc oxide Substances 0.000 description 4
UBRWPVTUQDJKCC-UHFFFAOYSA-N 1,3-bis(2-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC(C(C)(C)OOC(C)(C)C)=C1 UBRWPVTUQDJKCC-UHFFFAOYSA-N 0.000 description 3
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YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000003513 alkali Substances 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
239000000470 constituent Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
238000011161 development Methods 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
239000000806 elastomer Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
229920005555 halobutyl Polymers 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
150000002497 iodine compounds Chemical class 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
239000000178 monomer Substances 0.000 description 2
150000001451 organic peroxides Chemical class 0.000 description 2
239000011164 primary particle Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
238000007789 sealing Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
125000005369 trialkoxysilyl group Chemical group 0.000 description 2
238000004073 vulcanization Methods 0.000 description 2
MYOQALXKVOJACM-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy pentaneperoxoate Chemical compound CCCCC(=O)OOOC(C)(C)C MYOQALXKVOJACM-UHFFFAOYSA-N 0.000 description 1
OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical class C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
IQSUNBLELDRPEY-UHFFFAOYSA-N 1-ethylcyclopenta-1,3-diene Chemical compound CCC1=CC=CC1 IQSUNBLELDRPEY-UHFFFAOYSA-N 0.000 description 1
DKIUYAAMKFJPGB-UHFFFAOYSA-N 1-prop-2-enylcyclopenta-1,3-diene Chemical compound C=CCC1=CC=CC1 DKIUYAAMKFJPGB-UHFFFAOYSA-N 0.000 description 1
RZPAXISDLOEXPI-UHFFFAOYSA-N 1-propylcyclopenta-1,3-diene Chemical compound CCCC1=CC=CC1 RZPAXISDLOEXPI-UHFFFAOYSA-N 0.000 description 1
BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
IKBFHCBHLOZDKH-UHFFFAOYSA-N 2-chloroethyl(triethoxy)silane Chemical compound CCO[Si](CCCl)(OCC)OCC IKBFHCBHLOZDKH-UHFFFAOYSA-N 0.000 description 1
PZTIZDBYLCQIEI-UHFFFAOYSA-N 2-chloroethyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(CCCl)OCC PZTIZDBYLCQIEI-UHFFFAOYSA-N 0.000 description 1
BDCLTORUANJIBT-UHFFFAOYSA-N 3-butylperoxy-1,1,5-trimethylcyclohexane Chemical compound CCCCOOC1CC(C)CC(C)(C)C1 BDCLTORUANJIBT-UHFFFAOYSA-N 0.000 description 1
KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 1
KEZMLECYELSZDC-UHFFFAOYSA-N 3-chloropropyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(OCC)CCCCl KEZMLECYELSZDC-UHFFFAOYSA-N 0.000 description 1
WPFKMOXZMAGIOP-UHFFFAOYSA-N 3-cyclopenta-1,3-dien-1-ylpropyl(triethyl)silane Chemical compound CC[Si](CC)(CC)CCCC1=CC=CC1 WPFKMOXZMAGIOP-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
239000004604 Blowing Agent Substances 0.000 description 1
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239000004971 Cross linker Substances 0.000 description 1
MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Chemical class CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
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239000004606 Fillers/Extenders Substances 0.000 description 1
241001441571 Hiodontidae Species 0.000 description 1
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 description 1
239000005909 Kieselgur Substances 0.000 description 1
YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
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ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
230000006750 UV protection Effects 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
239000012190 activator Substances 0.000 description 1
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230000032683 aging Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001348 alkyl chlorides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
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DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
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OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
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238000013016 damping Methods 0.000 description 1
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239000004611 light stabiliser Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
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239000000391 magnesium silicate Substances 0.000 description 1
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NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 1
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239000004005 microsphere Substances 0.000 description 1
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YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
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239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
IZWIPIIVPHXLTN-UHFFFAOYSA-N potassium;cyclopenta-1,3-diene Chemical compound [K+].C1C=CC=[C-]1 IZWIPIIVPHXLTN-UHFFFAOYSA-N 0.000 description 1
KOPQZJAYZFAPBC-UHFFFAOYSA-N propanoyl propaneperoxoate Chemical compound CCC(=O)OOC(=O)CC KOPQZJAYZFAPBC-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000007870 radical polymerization initiator Substances 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000012763 reinforcing filler Substances 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000010703 silicon Substances 0.000 description 1
150000003377 silicon compounds Chemical class 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
150000003388 sodium compounds Chemical class 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229920001897 terpolymer 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
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
239000003017 thermal stabilizer Substances 0.000 description 1
230000036962 time dependent Effects 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
239000005052 trichlorosilane Substances 0.000 description 1
QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
- 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
- C07F7/18—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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Compositions Of Macromolecular Compounds (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Resistance Heating (AREA)
Vertical, Hearth, Or Arc Furnaces (AREA)
Furnace Details (AREA)
Processes Of Treating Macromolecular Substances (AREA)

DD85279025A 1984-07-28 1985-07-26 Verfahren zur herstellung von mon0-silyl-substituierten cyclopentadienen DD254203A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19843427922 DE3427922A1 (de)	1984-07-28	1984-07-28	Silyl-substituierte cyclopentadiene, verfahren zur herstellung und sie enthaltende kunststoff- und kautschukmischungen

Publications (1)

Publication Number	Publication Date
DD254203A5 true DD254203A5 (de)	1988-02-17

Family

ID=6241842

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
DD85279025A DD254203A5 (de)	1984-07-28	1985-07-26	Verfahren zur herstellung von mon0-silyl-substituierten cyclopentadienen
DD85297141A DD252610A5 (de)	1984-07-28	1985-07-26	Herstellung von mischungen auf der basis von mit peroxiden vernetzbaren mit silikatischen fuellstoffen verstaerkten kautschuken und kunststoffen
DD85313162A DD270915A5 (de)	1984-07-28	1985-07-26	Verfahren zur herstellung von bis-silyl-substituierten cyclepentadienen

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
DD85297141A DD252610A5 (de)	1984-07-28	1985-07-26	Herstellung von mischungen auf der basis von mit peroxiden vernetzbaren mit silikatischen fuellstoffen verstaerkten kautschuken und kunststoffen
DD85313162A DD270915A5 (de)	1984-07-28	1985-07-26	Verfahren zur herstellung von bis-silyl-substituierten cyclepentadienen

Country Status (8)

Country	Link
US (2)	US4645850A (cs)
EP (1)	EP0170011B1 (cs)
JP (2)	JPH0768257B2 (cs)
AT (1)	ATE38231T1 (cs)
CS (1)	CS274567B2 (cs)
DD (3)	DD254203A5 (cs)
DE (2)	DE3427922A1 (cs)
PL (3)	PL148445B1 (cs)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3837418A1 (de) *	1988-11-04	1990-05-10	Degussa	Organosiloxanamin-copolykondensate, verfahren zu ihrer herstellung und verwendung (i)
FR2654731B1 (fr) *	1989-11-21	1992-03-13	Rhone Poulenc Chimie	Silane et organopolysiloxane a reste cyclopentenyle pouvant etre obtenu par reaction de michael.
FR2676064B1 (fr) *	1991-04-30	1994-07-29	Rhone Poulenc Chimie	Polyorganosiloxanes a groupements cyclopentadienyles et/ou cyclopentadienylenes et/ou dicyclopentadienylenes, leurs preparations et leur utilisation dans des compositions reticulables en elastomeres.
DE4409140A1 (de) *	1994-03-17	1995-09-21	Degussa	Wäßrige Lösungen von Organopolysiloxan-Ammoniumverbindungen, ihre Herstellung und Verwendung
NZ303624A (en) *	1995-03-08	1999-01-28	Du Pont	Reactive organosilicons as coatings, adhesives, and sealants
CN103483370B (zh) *	2013-09-16	2016-06-15	厦门诺恩斯科技有限公司	一种异丁基三乙氧基硅烷的制备方法
US11028208B2 (en) *	2016-04-21	2021-06-08	Bridgestone Corporation	Terminal-functionalized polymer, rubber composition containing same and related processes

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL94478C (cs) *	1953-07-13	1900-01-01
US2957901A (en) *	1954-04-20	1960-10-25	Pittsburgh Plate Glass Co	Cyclopentadienyltrialkoxysilanes and derivatives thereof
US2974157A (en) *	1954-08-04	1961-03-07	Union Carbide Corp	Cyclopentadienyl vinyl silanes and process for making same
JPS5483089A (en) *	1977-12-15	1979-07-02	Sekisui Chem Co Ltd	Preparation of silane-modified ethylene resin
JPS57153004A (en) *	1981-03-19	1982-09-21	Nippon Oil Co Ltd	Production of silane-crosslinked polyolefin
US4593072A (en) *	1983-09-23	1986-06-03	Union Carbide Corporation	Relatively water-stable compositions based on thermoplastic polymers containing pendant silane moieties

1984
- 1984-07-28 DE DE19843427922 patent/DE3427922A1/de not_active Withdrawn
1985
- 1985-06-11 CS CS417985A patent/CS274567B2/cs unknown
- 1985-06-11 DE DE8585107167T patent/DE3565835D1/de not_active Expired
- 1985-06-11 EP EP85107167A patent/EP0170011B1/de not_active Expired
- 1985-06-11 AT AT85107167T patent/ATE38231T1/de not_active IP Right Cessation
- 1985-07-17 US US06/756,088 patent/US4645850A/en not_active Expired - Lifetime
- 1985-07-25 PL PL1985254679A patent/PL148445B1/pl unknown
- 1985-07-25 PL PL1985260397A patent/PL145078B1/pl unknown
- 1985-07-25 PL PL1985260398A patent/PL145061B1/pl unknown
- 1985-07-26 DD DD85279025A patent/DD254203A5/de not_active IP Right Cessation
- 1985-07-26 DD DD85297141A patent/DD252610A5/de not_active IP Right Cessation
- 1985-07-26 DD DD85313162A patent/DD270915A5/de not_active IP Right Cessation
- 1985-07-29 JP JP60166046A patent/JPH0768257B2/ja not_active Expired - Lifetime
1986
- 1986-11-21 US US06/933,136 patent/US4704428A/en not_active Expired - Lifetime
1994
- 1994-11-22 JP JP6287863A patent/JP2541787B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DE3427922A1 (de)	1986-01-30
PL148445B1 (en)	1989-10-31
JP2541787B2 (ja)	1996-10-09
US4704428A (en)	1987-11-03
JPS6147493A (ja)	1986-03-07
PL254679A1 (en)	1986-11-04
EP0170011A2 (de)	1986-02-05
JPH07173326A (ja)	1995-07-11
DD252610A5 (de)	1987-12-23
US4645850A (en)	1987-02-24
PL145061B1 (en)	1988-08-31
DE3565835D1 (en)	1988-12-01
EP0170011A3 (en)	1986-07-23
PL143325B1 (en)	1988-02-29
JPH0768257B2 (ja)	1995-07-26
DD270915A5 (de)	1989-08-16
EP0170011B1 (de)	1988-10-26
ATE38231T1 (de)	1988-11-15
CS417985A2 (en)	1990-09-12
PL145078B1 (en)	1988-08-31
CS274567B2 (en)	1991-08-13

Legal Events

Date	Code	Title	Description
2000-06-08	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0997489B1 (de)	2003-12-03	Schwefelfunktionelle Polyorganosiloxane
EP1285926B1 (de)	2004-05-12	Organosiliciumverbindungen
EP1298163B1 (de)	2005-07-06	Geblockte Mercaptosilane, Verfahren zu deren Herstellung und die enthaltenden Kautschukmischungen
DE19844607A1 (de)	2000-03-30	Sulfanylsilane
DE4415658A1 (de)	1995-11-09	Schwefelhaltige Organosiliciumverbindungen enthaltende Kautschukmischungen
DE2558191A1 (de)	1976-07-01	Arylsilan-polysulfide und -mercaptane, verfahren zu deren herstellung und ihre verwendung
DD254203A5 (de)	1988-02-17	Verfahren zur herstellung von mon0-silyl-substituierten cyclopentadienen
DE19829390A1 (de)	2000-01-05	Neue oligomere Organosiliciumverbindungen, deren Verwendung in Kautschukmischungen und zur Herstellung von Formkörpern
DE102005038794A1 (de)	2007-02-22	Kautschukmischungen
EP0683203B1 (de)	1997-07-16	Kieselsäure-gefüllte Kautschukmischungen mit verbesserter Vulkanisationskinetik
EP1394166B1 (de)	2005-11-30	Organosiliciumverbindungen
DE19950608A1 (de)	2001-05-03	Organosiliziumverbindung, Verfahren zu ihrer Herstellung und deren Verwendung
EP0737688B1 (de)	1999-07-28	Silane mit verzweigten Alkylketten
EP3621972A1 (de)	2020-03-18	Benzthiazolhaltige silane, verfahren zu deren herstellung und deren verwendung
EP0627462A2 (de)	1994-12-07	Verwendung von reinen 3-Butenyltriorganyloxysilanen in vulkanisierbaren Kautschukmischungen und diese Mischungen
EP3830095A1 (de)	2021-06-09	Thioethersilane, verfahren zu deren herstellung und deren verwendung
DE19922639A1 (de)	2000-11-23	Verfahren zur Herstellung von Mischungen aus silylgruppenhaltigen Kautschuken und Füllstoffen
DE1264783B (de)	1968-03-28	Verfahren zur Beendigung der Polymerisation von Butadien
DE3821670A1 (de)	1990-01-11	Haftvermittler fuer vulkanisierbare mischungen aus ungesaettigten kautschuken und siliciumhaltigen fuellstoffen
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DE2255577B2 (de)	1976-07-29	Verstaerkungsadditive in vulkanisierbaren kautschukmischungen
DE10210959A1 (de)	2003-10-09	Kautschukmischung, Verfahren zu deren Herstellung und deren Verwendung