CA1052802A - Produits intermediaires et mode de preparation des elastomeres a base de siloxane-carborane obtenus par polymerisation a haute temperature - Google Patents

Produits intermediaires et mode de preparation des elastomeres a base de siloxane-carborane obtenus par polymerisation a haute temperature

Info

Publication number: CA1052802A
Authority: CA; Canada
Prior art keywords: carborane; siloxane; bis; composition; group
Prior art date: 1973-07-24
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

Application number

CA203,804A

Other languages

English (en)

Other versions

CA203804S (en

Inventor

George T. Kwiatkowski

James H. Kawakami

Eddie Hedaya

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.)

Union Carbide Corp

Original Assignee

Union Carbide 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.)

1973-07-24

Filing date

1974-07-02

Publication date

1979-04-17

1974-07-02 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1979-04-17 Application granted granted Critical

1979-04-17 Publication of CA1052802A publication Critical patent/CA1052802A/fr

Status Expired legal-status Critical Current

Links

229920001971 elastomer Polymers 0.000 title claims abstract description 43
239000000806 elastomer Substances 0.000 title claims abstract description 40
238000000034 method Methods 0.000 title claims description 37
238000002360 preparation method Methods 0.000 title claims description 24
229920000642 polymer Polymers 0.000 claims abstract description 71
GKOZKEKDBJADSV-UHFFFAOYSA-N disilanol Chemical compound O[SiH2][SiH3] GKOZKEKDBJADSV-UHFFFAOYSA-N 0.000 claims abstract description 59
IYMSIPPWHNIMGE-UHFFFAOYSA-N silylurea Chemical compound NC(=O)N[SiH3] IYMSIPPWHNIMGE-UHFFFAOYSA-N 0.000 claims abstract description 20
239000000203 mixture Substances 0.000 claims description 35
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 claims description 14
DRNXZGJGRSUXHW-UHFFFAOYSA-N silyl carbamate Chemical class NC(=O)O[SiH3] DRNXZGJGRSUXHW-UHFFFAOYSA-N 0.000 claims description 14
229920001296 polysiloxane Polymers 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000002877 alkyl aryl group Chemical group 0.000 claims description 6
150000001412 amines Chemical group 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
125000002757 morpholinyl group Chemical group 0.000 claims description 5
125000004171 alkoxy aryl group Chemical group 0.000 claims description 4
125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000003106 haloaryl group Chemical group 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
229920002554 vinyl polymer Polymers 0.000 claims description 4
DUFWOTMOOUKVSM-UHFFFAOYSA-N 1-[dimethylcarbamoyl(dimethyl)silyl]-n,n-dimethylformamide Chemical group CN(C)C(=O)[Si](C)(C)C(=O)N(C)C DUFWOTMOOUKVSM-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
238000013007 heat curing Methods 0.000 claims 4
125000003545 alkoxy group Chemical group 0.000 claims 2
125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims 2
229910000085 borane Inorganic materials 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 1
-1 silyl diamine Chemical class 0.000 abstract description 76
239000000945 filler Substances 0.000 abstract description 20
238000006116 polymerization reaction Methods 0.000 abstract description 16
239000000654 additive Substances 0.000 abstract description 2
238000009413 insulation Methods 0.000 abstract description 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 86
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 42
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 20
239000000243 solution Substances 0.000 description 20
238000010992 reflux Methods 0.000 description 19
229910052757 nitrogen Inorganic materials 0.000 description 18
239000000047 product Substances 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000000463 material Substances 0.000 description 12
SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 12
FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
229920002379 silicone rubber Polymers 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000000523 sample Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 8
238000003760 magnetic stirring Methods 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
239000007787 solid Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
238000005345 coagulation Methods 0.000 description 6
230000015271 coagulation Effects 0.000 description 6
238000001723 curing Methods 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
JTWJUVSLJRLZFF-UHFFFAOYSA-N 2$l^{2},3$l^{2},4$l^{2},5$l^{2},6$l^{2},7$l^{2},8$l^{2},9$l^{2},11$l^{2},12$l^{2}-decaborabicyclo[8.1.1]dodecane Chemical compound [B]1C2[B]C1[B][B][B][B][B][B][B][B]2 JTWJUVSLJRLZFF-UHFFFAOYSA-N 0.000 description 5
229910021578 Iron(III) chloride Inorganic materials 0.000 description 5
SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 5
238000000113 differential scanning calorimetry Methods 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
229910002092 carbon dioxide Inorganic materials 0.000 description 4
238000006482 condensation reaction Methods 0.000 description 4
238000004132 cross linking Methods 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
238000005227 gel permeation chromatography Methods 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
239000011256 inorganic filler Substances 0.000 description 4
229910003475 inorganic filler Inorganic materials 0.000 description 4
238000002156 mixing Methods 0.000 description 4
229910000077 silane Inorganic materials 0.000 description 4
239000004945 silicone rubber Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
238000004448 titration Methods 0.000 description 4
239000008096 xylene Substances 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
235000013877 carbamide Nutrition 0.000 description 3
229920003237 carborane-containing polymer Polymers 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000013329 compounding Methods 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
229920001577 copolymer Polymers 0.000 description 3
238000010528 free radical solution polymerization reaction Methods 0.000 description 3
239000000446 fuel Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 3
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
230000003014 reinforcing effect Effects 0.000 description 3
239000005060 rubber Substances 0.000 description 3
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
239000005051 trimethylchlorosilane Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
CFNUZRMHHJZBOM-UHFFFAOYSA-N [B]1C2[B][B]C1[B][B][B][B][B][B][B]2 Chemical compound [B]1C2[B][B]C1[B][B][B][B][B][B][B]2 CFNUZRMHHJZBOM-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
229920001400 block copolymer Polymers 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
239000006229 carbon black Substances 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
229920005645 diorganopolysiloxane polymer Polymers 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
238000003801 milling Methods 0.000 description 2
150000001451 organic peroxides Chemical class 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000002516 radical scavenger Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
150000004819 silanols Chemical class 0.000 description 2
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
238000002411 thermogravimetry Methods 0.000 description 2
125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 2
239000012808 vapor phase Substances 0.000 description 2
UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 2
230000004580 weight loss Effects 0.000 description 2
WWNRKHUOXUIPKO-UHFFFAOYSA-N (1,4-dichlorocyclohexa-2,4-diene-1-carbonyl) 1,4-dichlorocyclohexa-2,4-diene-1-carboperoxoate Chemical compound C1=CC(Cl)=CCC1(Cl)C(=O)OOC(=O)C1(Cl)C=CC(Cl)=CC1 WWNRKHUOXUIPKO-UHFFFAOYSA-N 0.000 description 1
WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
UFBGZWVLKQSSJS-DEJKXBRXSA-N (3S,3aS,5aS,5bR,7aS,11aR,11bS,13aR,13bS)-3a,5a,8,8,11a,13a-hexamethyl-3-propan-2-yl-1,2,3,4,5,5b,6,7,7a,9,10,11,11b,12,13,13b-hexadecahydrocyclopenta[a]chrysene Chemical compound CC(C)[C@@H]1CC[C@H]2[C@@]1(C)CC[C@@]1(C)[C@@H]3CC[C@H]4C(C)(C)CCC[C@]4(C)[C@H]3CC[C@]21C UFBGZWVLKQSSJS-DEJKXBRXSA-N 0.000 description 1
OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 description 1
ZSGSNMURNDUYJX-UHFFFAOYSA-N 1,3-di(propan-2-yl)-1-[[propan-2-yl(propan-2-ylcarbamoyl)amino]-silylmethyl]urea Chemical compound C(C)(C)N(C(=O)NC(C)C)C(N(C(=O)NC(C)C)C(C)C)[SiH3] ZSGSNMURNDUYJX-UHFFFAOYSA-N 0.000 description 1
KKNKCSZKRNYOCD-UHFFFAOYSA-N 1,3-diethyl-1-[[ethyl(ethylcarbamoyl)amino]-methylsilyl]urea Chemical compound C(C)N(C(=O)NCC)[SiH](C)N(C(=O)NCC)CC KKNKCSZKRNYOCD-UHFFFAOYSA-N 0.000 description 1
SBAGTVQKGWYHSY-UHFFFAOYSA-N 1,3-diethyl-1-[[ethyl(ethylcarbamoyl)amino]-prop-1-enylsilyl]urea Chemical compound C(C)N(C(=O)NCC)[SiH](C=CC)N(C(=O)NCC)CC SBAGTVQKGWYHSY-UHFFFAOYSA-N 0.000 description 1
NGTQOLNHMXQESF-UHFFFAOYSA-N 1,3-dimethyl-1-[[methyl(methylcarbamoyl)amino]-phenylsilyl]urea Chemical compound CN(C(=O)NC)[SiH](C1=CC=CC=C1)N(C(=O)NC)C NGTQOLNHMXQESF-UHFFFAOYSA-N 0.000 description 1
BPEAZRNMASGWAK-UHFFFAOYSA-N 1-N,1-N,1-N',1-N'-tetraethyl-4-silylbut-3-ene-1,1-diamine Chemical compound C(C)N(CC)C(CC=C[SiH3])N(CC)CC BPEAZRNMASGWAK-UHFFFAOYSA-N 0.000 description 1
GYFQNEHKAFQLDU-UHFFFAOYSA-N 1-[[carbamoyl(methyl)amino]-silyloxymethyl]-1-methylurea Chemical compound CN(C(=O)N)C(O[SiH3])N(C(=O)N)C GYFQNEHKAFQLDU-UHFFFAOYSA-N 0.000 description 1
SKFNVEGYZVNFGY-UHFFFAOYSA-N 1-[[carbamoyl(pentyl)amino]-dimethylsilyl]-1-pentylurea Chemical compound CCCCCN(C(N)=O)[Si](C)(C)N(C(N)=O)CCCCC SKFNVEGYZVNFGY-UHFFFAOYSA-N 0.000 description 1
XSUPWZVFGZBTCR-UHFFFAOYSA-N 1-[diethylcarbamoyl(diethyl)silyl]-n,n-diethylformamide Chemical compound CCN(CC)C(=O)[Si](CC)(CC)C(=O)N(CC)CC XSUPWZVFGZBTCR-UHFFFAOYSA-N 0.000 description 1
NTMPBFZOVQBCPV-UHFFFAOYSA-N 1-[dimethyl-[methyl(methylcarbamoyl)amino]silyl]-1,3-dimethylurea Chemical compound CNC(=O)N(C)[Si](C)(C)N(C)C(=O)NC NTMPBFZOVQBCPV-UHFFFAOYSA-N 0.000 description 1
QJZVRMJMKQCVGH-UHFFFAOYSA-N 1-[dimethylcarbamoyl(dimethoxy)silyl]-n,n-dimethylformamide Chemical compound CN(C)C(=O)[Si](OC)(OC)C(=O)N(C)C QJZVRMJMKQCVGH-UHFFFAOYSA-N 0.000 description 1
MOWNNDAERZJQGG-UHFFFAOYSA-N 1-[dimethylcarbamoyl(diphenyl)silyl]-n,n-dimethylformamide Chemical compound C=1C=CC=CC=1[Si](C(=O)N(C)C)(C(=O)N(C)C)C1=CC=CC=C1 MOWNNDAERZJQGG-UHFFFAOYSA-N 0.000 description 1
OVSBSCJZEKFASA-UHFFFAOYSA-N 1-[dipentylcarbamoyl(dimethyl)silyl]-n,n-dipentylformamide Chemical compound CCCCCN(CCCCC)C(=O)[Si](C)(C)C(=O)N(CCCCC)CCCCC OVSBSCJZEKFASA-UHFFFAOYSA-N 0.000 description 1
LLBVLZWRDLCTPY-UHFFFAOYSA-N 1-[diphenylcarbamoyl(dimethyl)silyl]-n,n-diphenylformamide Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)C(=O)[Si](C)(C)C(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 LLBVLZWRDLCTPY-UHFFFAOYSA-N 0.000 description 1
INPJIJCKAOWQCL-UHFFFAOYSA-N 1-[dipropylcarbamoyl(diethyl)silyl]-n,n-dipropylformamide Chemical compound CCCN(CCC)C(=O)[Si](CC)(CC)C(=O)N(CCC)CCC INPJIJCKAOWQCL-UHFFFAOYSA-N 0.000 description 1
XBGGIBILSDOUEV-UHFFFAOYSA-N 1-butyl-1-[[butyl(carbamoyl)amino]-dimethoxysilyl]urea Chemical compound CCCCN(C(N)=O)[Si](OC)(OC)N(C(N)=O)CCCC XBGGIBILSDOUEV-UHFFFAOYSA-N 0.000 description 1
BXCKRTFSZSXWRM-UHFFFAOYSA-N 1-n,1-n,1-n',1-n'-tetramethyl-3-silylprop-2-ene-1,1-diamine Chemical compound CN(C)C(N(C)C)C=C[SiH3] BXCKRTFSZSXWRM-UHFFFAOYSA-N 0.000 description 1
NDVMCQUOSYOQMZ-UHFFFAOYSA-N 2,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)C(C(N)=O)[Si](C)(C)C NDVMCQUOSYOQMZ-UHFFFAOYSA-N 0.000 description 1
XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
PBNLPQZATZFTAN-UHFFFAOYSA-N 3-ethyl-1-[[ethylcarbamoyl(methyl)amino]-silylmethyl]-1-methylurea Chemical compound CN(C(=O)NCC)C(N(C(=O)NCC)C)[SiH3] PBNLPQZATZFTAN-UHFFFAOYSA-N 0.000 description 1
FGHPXAKHUFZDRY-UHFFFAOYSA-N 3-ethyl-3-(3-ethylpentan-3-ylperoxy)pentane Chemical compound CCC(CC)(CC)OOC(CC)(CC)CC FGHPXAKHUFZDRY-UHFFFAOYSA-N 0.000 description 1
SDEBYHVDMCQKNZ-UHFFFAOYSA-N 4-methoxy-6-piperazin-1-ylpyrimidine;hydrochloride Chemical compound Cl.C1=NC(OC)=CC(N2CCNCC2)=N1 SDEBYHVDMCQKNZ-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 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
FRPHFZCDPYBUAU-UHFFFAOYSA-N Bromocresolgreen Chemical compound CC1=C(Br)C(O)=C(Br)C=C1C1(C=2C(=C(Br)C(O)=C(Br)C=2)C)C2=CC=CC=C2S(=O)(=O)O1 FRPHFZCDPYBUAU-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
BASWICOLKLXVRR-UHFFFAOYSA-N N,N'-di(propan-2-yl)-1-silylmethanediamine Chemical compound C(C)(C)NC(NC(C)C)[SiH3] BASWICOLKLXVRR-UHFFFAOYSA-N 0.000 description 1
TUNMBSQJHAYICZ-UHFFFAOYSA-N N,N,N',N'-tetra(propan-2-yl)-1-silylmethanediamine Chemical compound C(C)(C)N(C(C)C)C(N(C(C)C)C(C)C)[SiH3] TUNMBSQJHAYICZ-UHFFFAOYSA-N 0.000 description 1
UTCNUORGKRQMGA-UHFFFAOYSA-N N,N,N',N'-tetraethyl-1-silylmethanediamine Chemical compound CCN(CC)C([SiH3])N(CC)CC UTCNUORGKRQMGA-UHFFFAOYSA-N 0.000 description 1
OHNIFWZQMCPFAH-UHFFFAOYSA-N N,N,N',N'-tetramethyl-1-silyloxymethanediamine Chemical compound CN(C)C(O[SiH3])N(C)C OHNIFWZQMCPFAH-UHFFFAOYSA-N 0.000 description 1
HAVYBJANWRFAHJ-UHFFFAOYSA-N N-[dimethylamino(phenyl)silyl]-N-methylmethanamine Chemical compound CN(C)[SiH](N(C)C)C1=CC=CC=C1 HAVYBJANWRFAHJ-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229910002656 O–Si–O Inorganic materials 0.000 description 1
239000004642 Polyimide Substances 0.000 description 1
229910018557 Si O Inorganic materials 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
241001409553 Uredo Species 0.000 description 1
238000005299 abrasion Methods 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910052570 clay Inorganic materials 0.000 description 1
230000001112 coagulating effect Effects 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000002131 composite material Substances 0.000 description 1
239000013068 control sample Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
FIRQYUPQXNPTKO-UHFFFAOYSA-N ctk0i2755 Chemical compound N[SiH2]N FIRQYUPQXNPTKO-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
VDCSGNNYCFPWFK-UHFFFAOYSA-N diphenylsilane Chemical compound C=1C=CC=CC=1[SiH2]C1=CC=CC=C1 VDCSGNNYCFPWFK-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
YOZWCVVCWGZSSF-UHFFFAOYSA-N ethenyl(ethyl)silicon Chemical compound CC[Si]C=C YOZWCVVCWGZSSF-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
239000007789 gas Substances 0.000 description 1
229920000578 graft copolymer Polymers 0.000 description 1
UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical class C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
DFWJSTNRZNMYAE-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-silylmethanediamine Chemical compound CN(C)C([SiH3])N(C)C DFWJSTNRZNMYAE-UHFFFAOYSA-N 0.000 description 1
AWYKFLRQJTXERW-UHFFFAOYSA-N n,n-dibutyl-1-[dibutylcarbamoyl(diethyl)silyl]formamide Chemical compound CCCCN(CCCC)C(=O)[Si](CC)(CC)C(=O)N(CCCC)CCCC AWYKFLRQJTXERW-UHFFFAOYSA-N 0.000 description 1
HZPQRTNJCVKJED-UHFFFAOYSA-N n-[(dipentylamino)-dimethylsilyl]-n-pentylpentan-1-amine Chemical compound CCCCCN(CCCCC)[Si](C)(C)N(CCCCC)CCCCC HZPQRTNJCVKJED-UHFFFAOYSA-N 0.000 description 1
OAGIMVANHSWAFT-UHFFFAOYSA-N n-[diethylamino(dimethoxy)silyl]-n-ethylethanamine Chemical compound CCN(CC)[Si](OC)(OC)N(CC)CC OAGIMVANHSWAFT-UHFFFAOYSA-N 0.000 description 1
125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
SWPKJPABFYFDNT-UHFFFAOYSA-N n-butyl-n-[(dibutylamino)-dimethylsilyl]butan-1-amine Chemical compound CCCCN(CCCC)[Si](C)(C)N(CCCC)CCCC SWPKJPABFYFDNT-UHFFFAOYSA-N 0.000 description 1
QMVDTSWUJMLAEG-UHFFFAOYSA-N n-ethyl-1-[[ethyl(methyl)carbamoyl]-dimethylsilyl]-n-methylformamide Chemical compound CCN(C)C(=O)[Si](C)(C)C(=O)N(C)CC QMVDTSWUJMLAEG-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
238000002103 osmometry Methods 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
238000011417 postcuring Methods 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
238000003847 radiation curing Methods 0.000 description 1
229920005604 random copolymer Polymers 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000012763 reinforcing filler Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
125000005372 silanol group Chemical group 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
LTDBAEMYQKAMHA-UHFFFAOYSA-N silylmethanediamine Chemical compound NC(N)[SiH3] LTDBAEMYQKAMHA-UHFFFAOYSA-N 0.000 description 1
230000002226 simultaneous effect Effects 0.000 description 1
238000009987 spinning Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 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
239000012085 test solution Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
239000003017 thermal stabilizer Substances 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
238000012546 transfer Methods 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000004073 vulcanization Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—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
- C08G77/56—Boron-containing linkages

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Silicon Polymers (AREA)
Compositions Of Macromolecular Compounds (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

CA203,804A 1973-07-24 1974-07-02 Produits intermediaires et mode de preparation des elastomeres a base de siloxane-carborane obtenus par polymerisation a haute temperature Expired CA1052802A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US38227873A	1973-07-24	1973-07-24

Publications (1)

Publication Number	Publication Date
CA1052802A true CA1052802A (fr)	1979-04-17

Family

ID=23508260

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA203,804A Expired CA1052802A (fr)	1973-07-24	1974-07-02	Produits intermediaires et mode de preparation des elastomeres a base de siloxane-carborane obtenus par polymerisation a haute temperature

Country Status (9)

Country	Link
JP (1)	JPS5650735B2 (fr)
BE (1)	BE818001A (fr)
CA (1)	CA1052802A (fr)
DE (1)	DE2435385A1 (fr)
DK (1)	DK396074A (fr)
FR (1)	FR2244786B1 (fr)
GB (1)	GB1479475A (fr)
IT (1)	IT1016678B (fr)
NL (1)	NL7409936A (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4959407A (en) *	1989-06-01	1990-09-25	General Electric Company	RTV silicones having bis(ureido)silane chain extenders and aminoxy siloxane crosslinkers
US5208310A (en) *	1991-12-16	1993-05-04	Hughes Aircraft Company	Method for preparation of very high molecular weight polycarborane siloxanes
EP0576812B1 (fr) *	1992-06-08	1995-11-08	Hughes Aircraft Company	Adhésif à base d'un polysiloxane à groupes carborane durcissable à basse température
JP4721364B2 (ja) *	2007-11-28	2011-07-13	日東電工株式会社	光半導体素子封止用樹脂およびそれを用いて得られる光半導体装置
WO2019149355A1 (fr) *	2018-01-31	2019-08-08	Wacker Chemie Ag	Procédé de fabrication de siloxanes à groupes fonctionnels d'urée
CN110746449B (zh) *	2018-07-23	2021-01-26	中国科学院化学研究所	一种含柔性硅氧链节的芳香胺官能化碳硼烷化合物及其制备方法与应用
CN117447909B (zh) *	2023-12-26	2024-03-12	成都虹润制漆有限公司	一种风雨棚顶用潮气固化型防腐涂层及其制备方法
CN121227199B (zh) *	2025-11-12	2026-04-21	东莞玖江纳米科技有限公司	一种注塑模具用耐疲劳抗腐蚀涂层材料及其制备方法

1974
- 1974-07-02 CA CA203,804A patent/CA1052802A/fr not_active Expired
- 1974-07-23 GB GB3250074A patent/GB1479475A/en not_active Expired
- 1974-07-23 DK DK396074A patent/DK396074A/da unknown
- 1974-07-23 BE BE146862A patent/BE818001A/fr unknown
- 1974-07-23 FR FR7425499A patent/FR2244786B1/fr not_active Expired
- 1974-07-23 JP JP8387574A patent/JPS5650735B2/ja not_active Expired
- 1974-07-23 IT IT6934874A patent/IT1016678B/it active
- 1974-07-23 NL NL7409936A patent/NL7409936A/xx not_active Application Discontinuation
- 1974-07-23 DE DE19742435385 patent/DE2435385A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
BE818001A (fr)	1975-01-23
DK396074A (fr)	1975-03-17
JPS5650735B2 (fr)	1981-12-01
GB1479475A (en)	1977-07-13
IT1016678B (it)	1977-06-20
FR2244786A1 (fr)	1975-04-18
JPS5044299A (fr)	1975-04-21
DE2435385A1 (de)	1975-02-27
NL7409936A (nl)	1975-01-28
FR2244786B1 (fr)	1979-08-17

Publication	Publication Date	Title
US4145504A (en)	1979-03-20	High temperature carborane-siloxane elastomers intermediate polymeric products and process for preparation
US5412053A (en)	1995-05-02	Polymers containing alternating silsesquioxane and bridging group segments and process for their preparation
EP0251435B1 (fr)	1990-09-12	Procédé de préparation de résines de siloxane
US4835238A (en)	1989-05-30	Polysilacyclobutasilazanes
CA1052802A (fr)	1979-04-17	Produits intermediaires et mode de preparation des elastomeres a base de siloxane-carborane obtenus par polymerisation a haute temperature
JPS6357454B2 (fr)	1988-11-11
US3037962A (en)	1962-06-05	Organosiloxanes
US3819744A (en)	1974-06-25	Polydiorganosiloxane-polycarbonate block copolymers
Hedaya et al.	1977	D2‐meta‐carborane‐siloxanes. IV. Synthesis of linear, high molecular weight polymers
JPH0730093B2 (ja)	1995-04-05	シロキサンイミドジオールおよびこれから得られるシロキサンイミド有機ブロックポリマー
JP3442123B2 (ja)	2003-09-02	ポリシラザン重合体の橋かけ法
US4235987A (en)	1980-11-25	Method for producing carborane-siloxane polymers directly from carborane
US3878168A (en)	1975-04-15	Novel silicone elastomers
US5059707A (en)	1991-10-22	Hydroxyl group-containing organosilicon compound
US6579955B2 (en)	2003-06-17	High temperature elastomers from linear poly(silarylene-siloxane-acetylene)
US3530092A (en)	1970-09-22	Process for preparing organosiliconnitrogen compounds
US3197431A (en)	1965-07-27	Novel organosilicon compounds
US5086126A (en)	1992-02-04	Method for producing functional silazane polymers
US4683320A (en)	1987-07-28	Novel organopolysiloxane, method for the preparation thereof and composition containing the same
US4877855A (en)	1989-10-31	Siloxane-amide block copolymer and process for producing the same
KR970006359A (ko)	1997-02-19	알콕시실알킬렌 말단 실록산 중합체의 제조방법
US3702317A (en)	1972-11-07	Method of making arylene modified siloxazanes incorporating cyclodisilazane structures
US5102968A (en)	1992-04-07	Method of making silethynyl-siloxane copolymers
JPS6257657B2 (fr)	1987-12-02
US5113002A (en)	1992-05-12	Polysilane copolymers and method for preparing same