CA1336100C - Polysilanes acetyleniques preceramiques - Google Patents

Polysilanes acetyleniques preceramiques

Info

Publication number: CA1336100C
Authority: CA; Canada
Prior art keywords: carbon atoms; units; acetylenic; polysilane; chlorine
Prior art date: 1987-08-10
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA000616742A

Other languages

English (en)

Inventor

Grish Chandra

Gregg Alan Zank

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Dow Silicones Corp

Original Assignee

Dow Corning Corp

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.)

1987-08-10

Filing date

1993-09-02

Publication date

1995-06-27

1987-08-10 Priority claimed from US07/083,121 external-priority patent/US4806612A/en

1993-09-02 Application filed by Dow Corning Corp filed Critical Dow Corning Corp

1993-09-02 Priority to CA000616742A priority Critical patent/CA1336100C/fr

1995-06-27 Application granted granted Critical

1995-06-27 Publication of CA1336100C publication Critical patent/CA1336100C/fr

2008-07-25 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229920000548 poly(silane) polymer Polymers 0.000 title claims abstract description 168
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 76
239000000460 chlorine Substances 0.000 claims abstract description 50
229910052801 chlorine Inorganic materials 0.000 claims abstract description 50
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 43
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 43
229910052794 bromium Inorganic materials 0.000 claims abstract description 43
229910052710 silicon Inorganic materials 0.000 claims abstract description 41
239000010703 silicon Substances 0.000 claims abstract description 41
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
239000001257 hydrogen Substances 0.000 claims abstract description 34
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 26
238000000197 pyrolysis Methods 0.000 claims abstract description 25
150000004795 grignard reagents Chemical class 0.000 claims abstract description 20
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 17
239000007818 Grignard reagent Substances 0.000 claims abstract description 14
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052740 iodine Chemical group 0.000 claims abstract description 4
239000011630 iodine Chemical group 0.000 claims abstract description 4
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 62
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 40
238000000034 method Methods 0.000 claims description 37
150000002431 hydrogen Chemical group 0.000 claims description 26
239000002904 solvent Substances 0.000 claims description 26
239000000919 ceramic Substances 0.000 claims description 23
150000002642 lithium compounds Chemical class 0.000 claims description 13
125000001246 bromo group Chemical group Br* 0.000 claims description 11
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 9
229910010271 silicon carbide Inorganic materials 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims description 7
238000010438 heat treatment Methods 0.000 claims description 6
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
229910010293 ceramic material Inorganic materials 0.000 abstract description 8
150000002900 organolithium compounds Chemical group 0.000 abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
-1 alkyl radical Chemical group 0.000 description 79
239000000835 fiber Substances 0.000 description 52
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 28
150000003254 radicals Chemical class 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 23
229910052760 oxygen Inorganic materials 0.000 description 23
239000001301 oxygen Substances 0.000 description 23
229910052786 argon Inorganic materials 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
229910052799 carbon Inorganic materials 0.000 description 14
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 13
239000000463 material Substances 0.000 description 13
239000003054 catalyst Substances 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
PZPGRFITIJYNEJ-UHFFFAOYSA-N disilane Chemical compound [SiH3][SiH3] PZPGRFITIJYNEJ-UHFFFAOYSA-N 0.000 description 11
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 10
238000007098 aminolysis reaction Methods 0.000 description 10
229910052757 nitrogen Inorganic materials 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
238000004821 distillation Methods 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
229960004132 diethyl ether Drugs 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 7
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 6
150000002367 halogens Chemical class 0.000 description 6
239000010453 quartz Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000007858 starting material Substances 0.000 description 6
239000003039 volatile agent Substances 0.000 description 6
UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 5
150000001728 carbonyl compounds Chemical class 0.000 description 5
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 5
238000002411 thermogravimetry Methods 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
230000005587 bubbling Effects 0.000 description 4
238000002074 melt spinning Methods 0.000 description 4
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
238000010926 purge Methods 0.000 description 4
239000000376 reactant Substances 0.000 description 4
239000002002 slurry Substances 0.000 description 4
229910052723 transition metal Inorganic materials 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical class [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
150000000475 acetylene derivatives Chemical group 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 3
238000000578 dry spinning Methods 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
229940052303 ethers for general anesthesia Drugs 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000010909 process residue Substances 0.000 description 3
230000008707 rearrangement Effects 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
150000004756 silanes Chemical class 0.000 description 3
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 3
239000008096 xylene Substances 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
KQHIGRPLCKIXNJ-UHFFFAOYSA-N chloro-methyl-silylsilane Chemical class C[SiH]([SiH3])Cl KQHIGRPLCKIXNJ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000004927 fusion Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
GNSLYOGEBCFYDE-UHFFFAOYSA-N lithium;ethynylbenzene Chemical compound [Li+].[C-]#CC1=CC=CC=C1 GNSLYOGEBCFYDE-UHFFFAOYSA-N 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
150000001367 organochlorosilanes Chemical class 0.000 description 2
239000005054 phenyltrichlorosilane Substances 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
238000009987 spinning Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 description 2
ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 2
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910021012 Co2(CO)8 Inorganic materials 0.000 description 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229910017333 Mo(CO)6 Inorganic materials 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
229910007161 Si(CH3)3 Inorganic materials 0.000 description 1
229910008940 W(CO)6 Inorganic materials 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000001479 atomic absorption spectroscopy Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001723 carbon free-radicals Chemical class 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000010408 film Substances 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
239000010439 graphite Substances 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
WDDOQHLJFOUQMW-UHFFFAOYSA-N lithium;ethynyl(trimethyl)silane Chemical compound [Li+].C[Si](C)(C)C#[C-] WDDOQHLJFOUQMW-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000004570 mortar (masonry) Substances 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
239000012044 organic layer Substances 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
150000003961 organosilicon compounds Chemical class 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
238000003918 potentiometric titration Methods 0.000 description 1
230000002028 premature Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000009877 rendering Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002210 silicon-based material Substances 0.000 description 1
LFAGQMCIGQNPJG-UHFFFAOYSA-N silver cyanide Chemical compound [Ag+].N#[C-] LFAGQMCIGQNPJG-UHFFFAOYSA-N 0.000 description 1
229940098221 silver cyanide Drugs 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
238000007669 thermal treatment Methods 0.000 description 1
230000000930 thermomechanical effect Effects 0.000 description 1
239000010409 thin film Substances 0.000 description 1
PSHXOKKREKJSSN-UHFFFAOYSA-N tribromo(octyl)silane Chemical compound CCCCCCCC[Si](Br)(Br)Br PSHXOKKREKJSSN-UHFFFAOYSA-N 0.000 description 1
HPTIEXHGTPSFDC-UHFFFAOYSA-N tribromo(phenyl)silane Chemical compound Br[Si](Br)(Br)C1=CC=CC=C1 HPTIEXHGTPSFDC-UHFFFAOYSA-N 0.000 description 1
LFXJGGDONSCPOF-UHFFFAOYSA-N trichloro(hexyl)silane Chemical compound CCCCCC[Si](Cl)(Cl)Cl LFXJGGDONSCPOF-UHFFFAOYSA-N 0.000 description 1

Landscapes

Ceramic Products (AREA)
Silicon Polymers (AREA)

CA000616742A 1987-08-10 1993-09-02 Polysilanes acetyleniques preceramiques Expired - Fee Related CA1336100C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000616742A CA1336100C (fr)	1987-08-10	1993-09-02	Polysilanes acetyleniques preceramiques

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US083,121		1987-08-10
US07/083,121 US4806612A (en)	1987-08-10	1987-08-10	Preceramic acetylenic polysilanes
CA000572924A CA1328656C (fr)	1987-08-10	1988-07-25	Polysilanes acetyleniques preceramiques
CA000616742A CA1336100C (fr)	1987-08-10	1993-09-02	Polysilanes acetyleniques preceramiques

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000572924A Division CA1328656C (fr)	1987-08-10	1988-07-25	Polysilanes acetyleniques preceramiques

Publications (1)

Publication Number	Publication Date
CA1336100C true CA1336100C (fr)	1995-06-27

Family

ID=25672008

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000616742A Expired - Fee Related CA1336100C (fr)	1987-08-10	1993-09-02	Polysilanes acetyleniques preceramiques

Country Status (1)

Country	Link
CA (1)	CA1336100C (fr)

1993
- 1993-09-02 CA CA000616742A patent/CA1336100C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
2000-06-27	MKLA	Lapsed

Publication	Publication Date	Title
EP0167306B1 (fr)	1990-05-16	Matériau céramique contenant du nitrure de silicium
US4546163A (en)	1985-10-08	Silicon carbide preceramic vinyl-containing polymers
EP0161751B1 (fr)	1989-09-20	Procédé de préparation de polymétallo(disilyl)silazanes et les polymères obtenus par ce procédé
US4310651A (en)	1982-01-12	Method for preparing silicon carbide
CA1305811C (fr)	1992-07-28	Derives preceramiques de polycarbosilane
CA1328656C (fr)	1994-04-19	Polysilanes acetyleniques preceramiques
US4762895A (en)	1988-08-09	Process for the preparation of preceramic metallopolysilanes and the polymers therefrom
US5082872A (en)	1992-01-21	Infusible preceramic polymers via ultraviolet treatment in the presence of a reactive gas
EP0606150B1 (fr)	1999-07-21	Procédé de réticulation de polymères polysilazanes
US4595472A (en)	1986-06-17	Silicon carbide preceramic vinyl-containing polymers
US4889899A (en)	1989-12-26	Method of producing silicon carbide preceramic vinyl-containing polymers
CA1305812C (fr)	1992-07-28	Methode pour la production de preceramique de carbure de silicium a partir de polysilanes vinyliques
CA1336100C (fr)	1995-06-27	Polysilanes acetyleniques preceramiques
CA1121971A (fr)	1982-04-20	Methode de preparation du carbure de silicone
US4962176A (en)	1990-10-09	Polysilane preceramic polymers
US4962175A (en)	1990-10-09	Alkylpoly (polysilyl) azane preceramic polymers
US5023307A (en)	1991-06-11	Methylpolysilanes having controllable rheology and method for their preparation
US5025075A (en)	1991-06-18	Methylpolysilanes and method for their preparation