CA1091383A - Polymeres a base de polysiloxane a groupements epoxyde fonctionnels - Google Patents

Polymeres a base de polysiloxane a groupements epoxyde fonctionnels

Info

Publication number: CA1091383A
Authority: CA; Canada
Prior art keywords: lithium; epoxy; radical; composition; group
Prior art date: 1975-04-07
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

CA249,381A

Other languages

English (en)

Inventor

Eugene R. Martin

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.)

Wacker Chemical Corp

Original Assignee

Wacker Chemical 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.)

1975-04-07

Filing date

1976-04-01

Publication date

1980-12-09

1976-04-01 Application filed by Wacker Chemical Corp filed Critical Wacker Chemical Corp

1980-12-09 Application granted granted Critical

1980-12-09 Publication of CA1091383A publication Critical patent/CA1091383A/fr

Status Expired legal-status Critical Current

Links

-1 polysiloxane Polymers 0.000 title claims abstract description 125
229920001296 polysiloxane Polymers 0.000 title claims abstract description 34
229920000642 polymer Polymers 0.000 title claims abstract description 21
229910052744 lithium Inorganic materials 0.000 claims abstract description 27
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims abstract description 24
150000003961 organosilicon compounds Chemical class 0.000 claims abstract description 20
238000006243 chemical reaction Methods 0.000 claims abstract description 16
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 11
150000002642 lithium compounds Chemical class 0.000 claims abstract description 9
230000003197 catalytic effect Effects 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 36
125000004432 carbon atom Chemical group C* 0.000 claims description 33
239000004215 Carbon black (E152) Substances 0.000 claims description 26
229930195733 hydrocarbon Natural products 0.000 claims description 26
150000003254 radicals Chemical class 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000000010 aprotic solvent Substances 0.000 claims description 12
229910000077 silane Inorganic materials 0.000 claims description 10
BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical group CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
125000003700 epoxy group Chemical group 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 8
HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical group C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000004122 cyclic group Chemical group 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
150000002430 hydrocarbons Chemical class 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
229910000103 lithium hydride Inorganic materials 0.000 claims description 4
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
150000001721 carbon Chemical group 0.000 claims 1
229920001002 functional polymer Polymers 0.000 claims 1
239000003054 catalyst Substances 0.000 abstract description 25
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
229920001577 copolymer Polymers 0.000 abstract description 3
239000003795 chemical substances by application Substances 0.000 abstract description 2
125000005375 organosiloxane group Chemical group 0.000 abstract description 2
239000011253 protective coating Substances 0.000 abstract description 2
238000004513 sizing Methods 0.000 abstract description 2
239000012048 reactive intermediate Substances 0.000 abstract 1
239000000047 product Substances 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
239000004593 Epoxy Substances 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
238000011067 equilibration Methods 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
150000004756 silanes Chemical class 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
JJRDHFIVAPVZJN-UHFFFAOYSA-N cyclotrisiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]1 JJRDHFIVAPVZJN-UHFFFAOYSA-N 0.000 description 5
238000009826 distribution Methods 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
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 4
150000002118 epoxides Chemical class 0.000 description 4
125000000524 functional group Chemical group 0.000 description 4
150000003377 silicon compounds Chemical class 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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 3
238000005481 NMR spectroscopy Methods 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
239000012530 fluid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
239000003039 volatile agent Substances 0.000 description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
239000006227 byproduct Substances 0.000 description 2
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
239000004205 dimethyl polysiloxane Substances 0.000 description 2
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
LQBLTEFMUAASOG-UHFFFAOYSA-N lithium oxido(oxo)silane Chemical compound [Li+].[O-][SiH]=O LQBLTEFMUAASOG-UHFFFAOYSA-N 0.000 description 2
SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
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 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920000647 polyepoxide Polymers 0.000 description 2
239000011591 potassium Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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 2
RSNQKPMXXVDJFG-UHFFFAOYSA-N tetrasiloxane Chemical compound [SiH3]O[SiH2]O[SiH2]O[SiH3] RSNQKPMXXVDJFG-UHFFFAOYSA-N 0.000 description 2
125000003944 tolyl group Chemical group 0.000 description 2
JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 2
LTOKKZDSYQQAHL-UHFFFAOYSA-N trimethoxy-[4-(oxiran-2-yl)butyl]silane Chemical compound CO[Si](OC)(OC)CCCCC1CO1 LTOKKZDSYQQAHL-UHFFFAOYSA-N 0.000 description 2
UEFJJFILJJDEFC-UHFFFAOYSA-N trimethoxy-[8-(oxiran-2-yl)octyl]silane Chemical compound CO[Si](OC)(OC)CCCCCCCCC1CO1 UEFJJFILJJDEFC-UHFFFAOYSA-N 0.000 description 2
PGOLTJPQCISRTO-UHFFFAOYSA-N vinyllithium Chemical compound [Li]C=C PGOLTJPQCISRTO-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
VCYDUTCMKSROID-UHFFFAOYSA-N 2,2,4,4,6,6-hexakis-phenyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound O1[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si]1(C=1C=CC=CC=1)C1=CC=CC=C1 VCYDUTCMKSROID-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
ZCUFTCUMEDALHC-UHFFFAOYSA-N CC[K] Chemical compound CC[K] ZCUFTCUMEDALHC-UHFFFAOYSA-N 0.000 description 1
NTZRDKVFLPLTPU-UHFFFAOYSA-N CC[Na] Chemical compound CC[Na] NTZRDKVFLPLTPU-UHFFFAOYSA-N 0.000 description 1
108700034893 EC 6.6.1.- Proteins 0.000 description 1
GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
239000002879 Lewis base Substances 0.000 description 1
HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910007161 Si(CH3)3 Inorganic materials 0.000 description 1
NZNQMPZXPUKVSQ-UHFFFAOYSA-N [O].C1CO1 Chemical group [O].C1CO1 NZNQMPZXPUKVSQ-UHFFFAOYSA-N 0.000 description 1
HAMCECPIHDJFPD-UHFFFAOYSA-N [dimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silyl]oxy-dimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C1OC1COCCC[Si](OC)(OC)O[Si](OC)(OC)CCCOCC1CO1 HAMCECPIHDJFPD-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
238000010539 anionic addition polymerization reaction Methods 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000000732 arylene group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
DDJSWKLBKSLAAZ-UHFFFAOYSA-N cyclotetrasiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]O[SiH2]1 DDJSWKLBKSLAAZ-UHFFFAOYSA-N 0.000 description 1
229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910052909 inorganic silicate Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000007527 lewis bases Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
229940006487 lithium cation Drugs 0.000 description 1
JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
OBTSLRFPKIKXSZ-UHFFFAOYSA-N lithium potassium Chemical compound [Li].[K] OBTSLRFPKIKXSZ-UHFFFAOYSA-N 0.000 description 1
LTRVAZKHJRYLRJ-UHFFFAOYSA-N lithium;butan-1-olate Chemical compound [Li+].CCCC[O-] LTRVAZKHJRYLRJ-UHFFFAOYSA-N 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000005702 oxyalkylene group Chemical group 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
150000003058 platinum compounds Chemical class 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
150000004819 silanols Chemical class 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical class [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 1
125000005389 trialkylsiloxy group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 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
239000008096 xylene Substances 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/306—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing silicon
- 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
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Silicon Polymers (AREA)
Epoxy Resins (AREA)

CA249,381A 1975-04-07 1976-04-01 Polymeres a base de polysiloxane a groupements epoxyde fonctionnels Expired CA1091383A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US56600075A	1975-04-07	1975-04-07
US566,000		1983-12-27

Publications (1)

Publication Number	Publication Date
CA1091383A true CA1091383A (fr)	1980-12-09

Family

ID=24261020

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA249,381A Expired CA1091383A (fr)	1975-04-07	1976-04-01	Polymeres a base de polysiloxane a groupements epoxyde fonctionnels

Country Status (10)

Country	Link
JP (1)	JPS5853655B2 (fr)
AT (1)	AT354732B (fr)
AU (1)	AU499062B2 (fr)
BE (1)	BE840471A (fr)
CA (1)	CA1091383A (fr)
DE (1)	DE2615077A1 (fr)
FR (1)	FR2307005A1 (fr)
GB (1)	GB1518591A (fr)
IT (1)	IT1058081B (fr)
NL (1)	NL7603534A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5623026A (en) *	1994-07-08	1997-04-22	Bayer Aktiengesellschaft	Siloxanes containing epoxy groups, and mixtures thereof with polycarbonates

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4576999A (en) *	1982-05-06	1986-03-18	General Electric Company	Ultraviolet radiation-curable silicone release compositions with epoxy and/or acrylic functionality
JPS61185478A (ja) *	1985-02-13	1986-08-19	Nec Corp	プリンタ用カバ−構造
JPH03255130A (ja) *	1990-03-05	1991-11-14	Shin Etsu Chem Co Ltd	エポキシ基含有オルガノポリシロキサンの製造方法
DE4234898C1 (de) *	1992-10-16	1994-04-07	Goldschmidt Ag Th	Organopolysiloxane mit einer endständigen SiH-Gruppe und einer am anderen Kettenende befindlichen weiteren funktionellen Gruppe sowie Verfahren zu ihrer Herstellung
AU2016201440A1 (en)	2015-03-10	2016-09-29	Aristocrat Technologies Australia Pty Limited	A method of gaming, a gaming system and a game controller
CN114763413A (zh) *	2021-01-14	2022-07-19	万华化学集团股份有限公司	一种制备烷基甲氧基硅油方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1420987A (fr) *	1964-01-17	1965-12-10	Bayer Ag	Procédé d'extension des chaînes des organopolysiloxanes ramifiés
US3761444A (en) *	1969-08-18	1973-09-25	Union Carbide Corp	Equilibration of epoxy substituted siloxanes in presence of water andsilanol

1976
- 1976-03-09 AU AU11798/76A patent/AU499062B2/en not_active Expired
- 1976-03-31 JP JP51034587A patent/JPS5853655B2/ja not_active Expired
- 1976-04-01 CA CA249,381A patent/CA1091383A/fr not_active Expired
- 1976-04-05 IT IT4887176A patent/IT1058081B/it active
- 1976-04-05 NL NL7603534A patent/NL7603534A/xx not_active Application Discontinuation
- 1976-04-06 AT AT247576A patent/AT354732B/de not_active IP Right Cessation
- 1976-04-06 FR FR7609898A patent/FR2307005A1/fr active Granted
- 1976-04-07 BE BE165917A patent/BE840471A/fr unknown
- 1976-04-07 GB GB1409476A patent/GB1518591A/en not_active Expired
- 1976-04-07 DE DE19762615077 patent/DE2615077A1/de not_active Withdrawn

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5623026A (en) *	1994-07-08	1997-04-22	Bayer Aktiengesellschaft	Siloxanes containing epoxy groups, and mixtures thereof with polycarbonates

Also Published As

Publication number	Publication date
AU499062B2 (en)	1979-04-05
FR2307005B1 (fr)	1978-06-23
NL7603534A (nl)	1976-10-11
IT1058081B (it)	1982-04-10
JPS5853655B2 (ja)	1983-11-30
GB1518591A (en)	1978-07-19
BE840471A (fr)	1976-10-07
FR2307005A1 (fr)	1976-11-05
ATA247576A (de)	1979-06-15
JPS51121099A (en)	1976-10-22
AU1179876A (en)	1977-09-29
AT354732B (de)	1979-01-25
DE2615077A1 (de)	1976-10-28

Legal Events

Date	Code	Title	Description
1997-12-09	MKEX	Expiry

Publication	Publication Date	Title
US4208503A (en)	1980-06-17	Epoxy-functional polysiloxane polymers
US5028679A (en)	1991-07-02	Method for preparing perfluoroalkyl group-containing organopolysiloxanes
US4689383A (en)	1987-08-25	Hydroxyl-functional disiloxanes and polysiloxane oligomers
CA1091382A (fr)	1980-12-09	Procede de preparation de polymeres de type polysiloxane a groupes thio
EP0541988B1 (fr)	1997-03-12	Organopolysiloxanes et procédé de préparation
US3878263A (en)	1975-04-15	Acrylate-functional polysiloxane polymers
EP0543384B1 (fr)	1997-05-28	Organopolysiloxane ayant des groupes époxy et son procédé de préparation
CA2022991C (fr)	1995-08-08	Organo(poly)siloxanes a fonction anhydride, procede de preparation et utilisation
US3890269A (en)	1975-06-17	Process for preparing aminofunctional polysiloxane polymers
KR100280586B1 (ko)	2001-02-01	알콕시 말단차단된 폴리디오가노실록산, 이의 제조방법 및 이로부터 제조된 실온 경화성 실리콘 엘라스토머
US5206328A (en)	1993-04-27	Process for the production of an organopolysiloxane
US3032577A (en)	1962-05-01	N-substituted derivatives of aminoalkylsiloxanes
JPH07133351A (ja)	1995-05-23	エポキシ変性シリコーンの製造方法
US4684709A (en)	1987-08-04	Organopolysiloxane compounds comprising epoxy-terminated polyoxyalkylene radicals
CA1091383A (fr)	1980-12-09	Polymeres a base de polysiloxane a groupements epoxyde fonctionnels
US5086124A (en)	1992-02-04	High heat distortion temperature epoxy siloxane/organic epoxy compositions
US3338867A (en)	1967-08-29	Silanes and siloxanes containing oxetane groups
US4694060A (en)	1987-09-15	Process for the treatment of polyorganosilazanes and/or of polyorgano(disilyl)silazanes by means of a treatment of polyorganosilazanes with a catalyst system comprising an ionic inorganic salt and a complexing compound
US20060122413A1 (en)	2006-06-08	Aminomethylene functional siloxanes
US5378789A (en)	1995-01-03	Phenol-modified silicones
US3219624A (en)	1965-11-23	Epoxy organopolysiloxanes
US5041591A (en)	1991-08-20	Organopolysiloxane and method for its preparation
US4808687A (en)	1989-02-28	Novel organopolysiloxanes derived from bis-silyl substituted heterocyclic compounds
US5693734A (en)	1997-12-02	Organosilicon compounds containing furanyl groups
US3481962A (en)	1969-12-02	Process for the production of organosiloxanes

CA1091383A - Polymeres a base de polysiloxane a groupements epoxyde fonctionnels - Google Patents

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Applications Claiming Priority (2)

Publications (1)

Family

ID=24261020

Family Applications (1)

Country Status (10)

Cited By (1)

Families Citing this family (6)

Family Cites Families (2)

Cited By (1)

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