CA1304875C - Methode pour la conversion de polymeres de type organosilicium contenant des unites repetees sih et des precurseurs de l'organopolysilazane, destinees a la fabrication de polymeres utiles nouveaux, et matieres ceramiques enrichies de nitrure de silicium - Google Patents

Methode pour la conversion de polymeres de type organosilicium contenant des unites repetees sih et des precurseurs de l'organopolysilazane, destinees a la fabrication de polymeres utiles nouveaux, et matieres ceramiques enrichies de nitrure de silicium

Info

Publication number: CA1304875C
Authority: CA; Canada
Prior art keywords: carbon atoms; group; substituted; lower alkyl; polymer
Prior art date: 1986-08-22
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 - Lifetime

Application number

CA000545027A

Other languages

English (en)

Inventor

Yuan-Fu Yu

Joanne M. Schwark

Dietmar Seyferth

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.)

Massachusetts Institute of Technology

Original Assignee

Massachusetts Institute of Technology

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.)

1986-08-22

Filing date

1987-08-21

Publication date

1992-07-07

1986-08-22 Priority claimed from US06/899,471 external-priority patent/US4720532A/en

1986-10-07 Priority claimed from US06/916,109 external-priority patent/US4767876A/en

1987-08-21 Application filed by Massachusetts Institute of Technology filed Critical Massachusetts Institute of Technology

1992-07-07 Application granted granted Critical

1992-07-07 Publication of CA1304875C publication Critical patent/CA1304875C/fr

2009-07-07 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 146
238000000034 method Methods 0.000 title claims abstract description 53
229920001558 organosilicon polymer Polymers 0.000 title claims abstract description 42
229910010293 ceramic material Inorganic materials 0.000 title claims description 34
229910052581 Si3N4 Inorganic materials 0.000 title description 55
HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 title description 18
239000002243 precursor Substances 0.000 title description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 72
239000000203 mixture Substances 0.000 claims abstract description 68
-1 polysiloxane Polymers 0.000 claims abstract description 50
229920003257 polycarbosilane Polymers 0.000 claims abstract description 47
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 44
125000000217 alkyl group Chemical group 0.000 claims abstract description 38
229920001296 polysiloxane Polymers 0.000 claims abstract description 31
125000003118 aryl group Chemical group 0.000 claims abstract description 22
125000003342 alkenyl group Chemical group 0.000 claims abstract description 18
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
101100237844 Mus musculus Mmp19 gene Proteins 0.000 claims abstract description 12
239000000919 ceramic Substances 0.000 claims description 106
238000000197 pyrolysis Methods 0.000 claims description 90
FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 52
229910052799 carbon Inorganic materials 0.000 claims description 49
229910052710 silicon Inorganic materials 0.000 claims description 39
239000011541 reaction mixture Substances 0.000 claims description 36
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 32
229910052757 nitrogen Inorganic materials 0.000 claims description 32
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 30
239000010703 silicon Substances 0.000 claims description 30
229910021529 ammonia Inorganic materials 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000003960 organic solvent Substances 0.000 claims description 18
239000012039 electrophile Substances 0.000 claims description 13
229920001709 polysilazane Polymers 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 12
239000012298 atmosphere Substances 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
239000003054 catalyst Substances 0.000 claims description 9
238000011065 in-situ storage Methods 0.000 claims description 9
229910052701 rubidium Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 8
229910052705 radium Inorganic materials 0.000 claims description 7
230000003197 catalytic effect Effects 0.000 claims description 6
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical group 0.000 claims description 5
238000010791 quenching Methods 0.000 claims description 5
150000004820 halides Chemical class 0.000 claims description 4
239000011261 inert gas Substances 0.000 claims description 4
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
230000000171 quenching effect Effects 0.000 claims description 3
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 228
239000000047 product Substances 0.000 description 121
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 114
238000006243 chemical reaction Methods 0.000 description 96
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 92
239000007787 solid Substances 0.000 description 68
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 53
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 51
229910010271 silicon carbide Inorganic materials 0.000 description 51
229910003465 moissanite Inorganic materials 0.000 description 42
239000003921 oil Substances 0.000 description 37
239000000243 solution Substances 0.000 description 35
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 33
239000002904 solvent Substances 0.000 description 33
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 32
238000005915 ammonolysis reaction Methods 0.000 description 30
238000004821 distillation Methods 0.000 description 27
239000000835 fiber Substances 0.000 description 27
238000002411 thermogravimetry Methods 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000000463 material Substances 0.000 description 21
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 19
239000000843 powder Substances 0.000 description 19
238000005481 NMR spectroscopy Methods 0.000 description 17
238000010992 reflux Methods 0.000 description 17
229910052786 argon Inorganic materials 0.000 description 16
239000007789 gas Substances 0.000 description 16
238000004458 analytical method Methods 0.000 description 15
239000006228 supernatant Substances 0.000 description 13
239000007788 liquid Substances 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
239000007858 starting material Substances 0.000 description 11
UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 10
101150041968 CDC13 gene Proteins 0.000 description 9
239000007795 chemical reaction product Substances 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
239000000460 chlorine Substances 0.000 description 8
239000000543 intermediate Substances 0.000 description 8
229920000548 poly(silane) polymer Polymers 0.000 description 8
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 8
229910000105 potassium hydride Inorganic materials 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
239000002585 base Substances 0.000 description 7
230000008569 process Effects 0.000 description 7
229910052783 alkali metal Inorganic materials 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
229910052681 coesite Inorganic materials 0.000 description 6
229910052906 cristobalite Inorganic materials 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052682 stishovite Inorganic materials 0.000 description 6
229910052905 tridymite Inorganic materials 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 5
239000002131 composite material Substances 0.000 description 5
JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 5
150000003961 organosilicon compounds Chemical class 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
210000002966 serum Anatomy 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
235000012239 silicon dioxide Nutrition 0.000 description 5
239000000725 suspension Substances 0.000 description 5
ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 5
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 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 4
KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 4
230000010354 integration Effects 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
239000005048 methyldichlorosilane Substances 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
238000003756 stirring Methods 0.000 description 4
230000004580 weight loss Effects 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
239000005046 Chlorosilane Substances 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
229910004721 HSiCl3 Inorganic materials 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000000576 coating method Methods 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011521 glass Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
239000011630 iodine Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
239000005055 methyl trichlorosilane Substances 0.000 description 3
UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 3
239000000178 monomer Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
229910000077 silane Inorganic materials 0.000 description 3
239000012265 solid product Substances 0.000 description 3
239000010409 thin film Substances 0.000 description 3
239000001993 wax Substances 0.000 description 3
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
241001120493 Arene Species 0.000 description 2
241000486661 Ceramica Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
241001072332 Monia Species 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
229910008045 Si-Si Inorganic materials 0.000 description 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
229910006411 Si—Si Inorganic materials 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
HLXRWTJXGMHOFN-XJSNKYLASA-N Verbenalin Chemical compound O([C@@H]1OC=C([C@H]2C(=O)C[C@H](C)[C@H]21)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HLXRWTJXGMHOFN-XJSNKYLASA-N 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910000102 alkali metal hydride Inorganic materials 0.000 description 2
150000008046 alkali metal hydrides Chemical class 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
125000005103 alkyl silyl group Chemical group 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
150000004292 cyclic ethers Chemical class 0.000 description 2
150000001983 dialkylethers Chemical class 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000009472 formulation Methods 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
230000006872 improvement Effects 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000004570 mortar (masonry) Substances 0.000 description 2
229910000069 nitrogen hydride Inorganic materials 0.000 description 2
150000001282 organosilanes Chemical class 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
229920005596 polymer binder Polymers 0.000 description 2
239000002491 polymer binding agent Substances 0.000 description 2
230000005855 radiation Effects 0.000 description 2
238000002390 rotary evaporation Methods 0.000 description 2
241000894007 species Species 0.000 description 2
GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 2
239000005050 vinyl trichlorosilane Substances 0.000 description 2
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-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
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
241000237074 Centris Species 0.000 description 1
101150090997 DLAT gene Proteins 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
229910010084 LiAlH4 Inorganic materials 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
238000004639 Schlenk technique Methods 0.000 description 1
241000872198 Serjania polyphylla Species 0.000 description 1
229910005091 Si3N Inorganic materials 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
HLXRWTJXGMHOFN-UHFFFAOYSA-N Verbenalin Natural products C12C(C)CC(=O)C2C(C(=O)OC)=COC1OC1OC(CO)C(O)C(O)C1O HLXRWTJXGMHOFN-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
244000309464 bull Species 0.000 description 1
BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000012700 ceramic precursor Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000002950 deficient Effects 0.000 description 1
PFMKUUJQLUQKHT-UHFFFAOYSA-N dichloro(ethyl)silicon Chemical compound CC[Si](Cl)Cl PFMKUUJQLUQKHT-UHFFFAOYSA-N 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010894 electron beam technology Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000012634 fragment Substances 0.000 description 1
238000013467 fragmentation Methods 0.000 description 1
238000006062 fragmentation reaction Methods 0.000 description 1
238000001754 furnace pyrolysis Methods 0.000 description 1
239000005350 fused silica glass Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
238000006459 hydrosilylation reaction Methods 0.000 description 1
208000006278 hypochromic anemia Diseases 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000008595 infiltration Effects 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000004767 nitrides Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012434 nucleophilic reagent Substances 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
238000006303 photolysis reaction Methods 0.000 description 1
230000015843 photosynthesis, light reaction Effects 0.000 description 1
229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920005591 polysilicon Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000009700 powder processing Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
239000011819 refractory material Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
238000009987 spinning Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
238000002076 thermal analysis method Methods 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
239000005052 trichlorosilane Substances 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Landscapes

Ceramic Products (AREA)

CA000545027A 1986-08-22 1987-08-21 Methode pour la conversion de polymeres de type organosilicium contenant des unites repetees sih et des precurseurs de l'organopolysilazane, destinees a la fabrication de polymeres utiles nouveaux, et matieres ceramiques enrichies de nitrure de silicium Expired - Lifetime CA1304875C (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US899,471		1986-08-22
US06/899,471 US4720532A (en)	1986-08-22	1986-08-22	Organopolysilazane precursors to silicon nitride-rich mixed SiC/Si3 N4
US06/916,109 US4767876A (en)	1985-09-30	1986-10-07	Method for converting organosilicon polymers containing SIH repeat units and organopolysilazane precursors to new and useful preceramic polymers and silicon nitride enriched ceramic materials
US916,109		1986-10-07

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000583229A Division CA1281475C (fr)	1986-08-22	1988-11-16	Precurseurs de type organopolysilazane pour la production d'un melange sic/se3n4 riche en nitrure de silicium

Publications (1)

Publication Number	Publication Date
CA1304875C true CA1304875C (fr)	1992-07-07

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ID=27129240

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA000545027A Expired - Lifetime CA1304875C (fr)	1986-08-22	1987-08-21	Methode pour la conversion de polymeres de type organosilicium contenant des unites repetees sih et des precurseurs de l'organopolysilazane, destinees a la fabrication de polymeres utiles nouveaux, et matieres ceramiques enrichies de nitrure de silicium
CA000583229A Expired - Lifetime CA1281475C (fr)	1986-08-22	1988-11-16	Precurseurs de type organopolysilazane pour la production d'un melange sic/se3n4 riche en nitrure de silicium

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CA000583229A Expired - Lifetime CA1281475C (fr)	1986-08-22	1988-11-16	Precurseurs de type organopolysilazane pour la production d'un melange sic/se3n4 riche en nitrure de silicium

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CA (2)	CA1304875C (fr)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN120988492B (zh) *	2025-10-22	2026-02-17	成都俊马密封科技股份有限公司	一种应用于900℃以上工况的抗高温密封材料及其制备方法

1987
- 1987-08-21 CA CA000545027A patent/CA1304875C/fr not_active Expired - Lifetime
1988
- 1988-11-16 CA CA000583229A patent/CA1281475C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA1281475C (fr)	1991-03-12

Legal Events

Date	Code	Title	Description
2007-07-09	MKLA	Lapsed

Publication	Publication Date	Title
US4767876A (en)	1988-08-30	Method for converting organosilicon polymers containing SIH repeat units and organopolysilazane precursors to new and useful preceramic polymers and silicon nitride enriched ceramic materials
US4820783A (en)	1989-04-11	Method for forming new preceramic polymers for SiC and Si3 N4/SiC
US4720532A (en)	1988-01-19	Organopolysilazane precursors to silicon nitride-rich mixed SiC/Si3 N4
EP0153008B1 (fr)	1989-06-28	Polymères d'organosilazane formant des matières céramiques
KR840001536B1 (ko)	1984-10-04	폴리실란의 제조방법
US6103178A (en)	2000-08-15	Method for producing ceramic fibers from blends of siloxane resins and carborane siloxane oligomers
EP0295062B1 (fr)	1992-12-02	Polysilacyclobutasilazanes
US4705837A (en)	1987-11-10	Method for converting Si-H containing polysiloxanes to new and useful preceramic polymers and ceramic materials
US5256487A (en)	1993-10-26	High char yield silazane derived preceramic polymers and cured compositions thereof
CA1287432C (fr)	1991-08-06	Polymeres preceramiques obtenus a partir de silazanes cycliques et de disilanes halogenes; methode de preparation
US4497787A (en)	1985-02-05	Branched polycarbosilanes and their use in the production of silicon carbide
EP0209360B1 (fr)	1993-01-27	Procédé de transformation de polymères de silicium ayant des groupes Si-H en polymères pré-céramiques et en matières céramiques
CA1304875C (fr)	1992-07-07	Methode pour la conversion de polymeres de type organosilicium contenant des unites repetees sih et des precurseurs de l'organopolysilazane, destinees a la fabrication de polymeres utiles nouveaux, et matieres ceramiques enrichies de nitrure de silicium
EP0278001B1 (fr)	1992-01-29	Procede d'utilisation de precurseurs d'organopolysilazane pour former de nouveaux polymeres preceramiques et des materiaux ceramiques riches en nitrure de silicium
US5070116A (en)	1991-12-03	Preceramic organosilicon-metal carbonyl polymers
Seyferth	1988	Organosilicon polymers as precursors for silicon-containing ceramics
Uhlig	1998	Convenient approach to novel functional substituted and branched poly (silylenemethylenes)
JPS6158086B2 (fr)	1986-12-10
Seyferth et al.	1987	Organosilicon Polymers as Precursors for Silicon Containing Ceramics: Recent Developments.
CA1263796A (fr)	1989-12-05	Conversion de polycarbosilanes renfermant si-h en de nouveaux et utiles polymeres preceramiques et produits ceramiques
EP0826718B1 (fr)	1999-12-01	Fibres SiCO amorphes et fibres SiC cristallins à partir de résines de polysiloxanes durcissables ayant des groupes alk-1-ényléther
JP2575280B2 (ja)	1997-01-22	酸窒化珪素繊維の製法
Blum et al.	1986	A new catalytic method for producing preceramic polysilazanes
Seyferth et al.	1987	The Preceramic Polymer Route to Silicon-Containing Ceramics
Birot et al.	1995	Sic and SiCN Based-Materials: The Model and Copolymer Ways for a Rational Approach to Their Precursors