CA1082396A - Copolymeres sequences de fluorosiloxydiphenylsiloxyde - Google Patents

Copolymeres sequences de fluorosiloxydiphenylsiloxyde

Info

Publication number: CA1082396A
Authority: CA; Canada
Prior art keywords: solvent; reaction; formula; block copolymer; trimer
Prior art date: 1976-10-20
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

CA263,794A

Other languages

English (en)

Inventor

John S. Razzano

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.)

General Electric Co

Original Assignee

General Electric Co

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.)

1976-10-20

Filing date

1976-10-20

Publication date

1980-07-22

1976-10-20 Application filed by General Electric Co filed Critical General Electric Co

1976-10-20 Priority to CA263,794A priority Critical patent/CA1082396A/fr

1980-07-22 Application granted granted Critical

1980-07-22 Publication of CA1082396A publication Critical patent/CA1082396A/fr

Status Expired legal-status Critical Current

Links

229920001400 block copolymer Polymers 0.000 title claims abstract description 56
239000002904 solvent Substances 0.000 claims abstract description 55
238000000034 method Methods 0.000 claims abstract description 21
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
229920001577 copolymer Polymers 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052744 lithium Inorganic materials 0.000 claims abstract description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 5
229920002554 vinyl polymer Polymers 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
238000006243 chemical reaction Methods 0.000 claims description 33
-1 dilithium compound Chemical class 0.000 claims description 30
239000013638 trimer Substances 0.000 claims description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
239000003054 catalyst Substances 0.000 claims description 17
238000009835 boiling Methods 0.000 claims description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 9
239000000376 reactant Substances 0.000 claims description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
239000004305 biphenyl Substances 0.000 claims description 8
235000010290 biphenyl Nutrition 0.000 claims description 8
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
125000006267 biphenyl group Chemical group 0.000 claims description 7
150000001875 compounds Chemical class 0.000 claims description 6
230000003472 neutralizing effect Effects 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
229940117389 dichlorobenzene Drugs 0.000 claims description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 3
OFXSXYCSPVKZPF-UHFFFAOYSA-N methoxyperoxymethane Chemical compound COOOC OFXSXYCSPVKZPF-UHFFFAOYSA-N 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
URZHQOCYXDNFGN-UHFFFAOYSA-N 2,4,6-trimethyl-2,4,6-tris(3,3,3-trifluoropropyl)-1,3,5,2,4,6-trioxatrisilinane Chemical compound FC(F)(F)CC[Si]1(C)O[Si](C)(CCC(F)(F)F)O[Si](C)(CCC(F)(F)F)O1 URZHQOCYXDNFGN-UHFFFAOYSA-N 0.000 claims 1
238000006116 polymerization reaction Methods 0.000 claims 1
239000000203 mixture Substances 0.000 description 28
229920000642 polymer Polymers 0.000 description 17
229920001971 elastomer Polymers 0.000 description 10
229920002379 silicone rubber Polymers 0.000 description 10
239000004945 silicone rubber Substances 0.000 description 9
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000806 elastomer Substances 0.000 description 6
239000000945 filler Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
150000002978 peroxides Chemical class 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000004614 Process Aid Substances 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
238000012545 processing Methods 0.000 description 3
229920005604 random copolymer Polymers 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
238000013459 approach Methods 0.000 description 2
SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 2
239000004205 dimethyl polysiloxane Substances 0.000 description 2
235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
229920005645 diorganopolysiloxane polymer Polymers 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000000463 material Substances 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000003014 reinforcing effect Effects 0.000 description 2
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 2
COSWCAGTKRUTQV-UHFFFAOYSA-N 1,1,3-trimethylurea Chemical compound CNC(=O)N(C)C COSWCAGTKRUTQV-UHFFFAOYSA-N 0.000 description 1
OGNSDRMLWYNUED-UHFFFAOYSA-N 1-cyclohexyl-4-[4-[4-(4-cyclohexylcyclohexyl)cyclohexyl]cyclohexyl]cyclohexane Chemical group C1CCCCC1C1CCC(C2CCC(CC2)C2CCC(CC2)C2CCC(CC2)C2CCCCC2)CC1 OGNSDRMLWYNUED-UHFFFAOYSA-N 0.000 description 1
NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-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
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
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
JJRDHFIVAPVZJN-UHFFFAOYSA-N cyclotrisiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]1 JJRDHFIVAPVZJN-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
229910001416 lithium ion Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
239000012763 reinforcing filler Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229920005573 silicon-containing polymer Polymers 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000012360 testing method Methods 0.000 description 1
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1

Landscapes

Silicon Polymers (AREA)

CA263,794A 1976-10-20 1976-10-20 Copolymeres sequences de fluorosiloxydiphenylsiloxyde Expired CA1082396A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA263,794A CA1082396A (fr)	1976-10-20	1976-10-20	Copolymeres sequences de fluorosiloxydiphenylsiloxyde

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA263,794A CA1082396A (fr)	1976-10-20	1976-10-20	Copolymeres sequences de fluorosiloxydiphenylsiloxyde

Publications (1)

Publication Number	Publication Date
CA1082396A true CA1082396A (fr)	1980-07-22

Family

ID=4107094

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA263,794A Expired CA1082396A (fr)	1976-10-20	1976-10-20	Copolymeres sequences de fluorosiloxydiphenylsiloxyde

Country Status (1)

Country	Link
CA (1)	CA1082396A (fr)

1976
- 1976-10-20 CA CA263,794A patent/CA1082396A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-07-22	MKEX	Expiry

Publication	Publication Date	Title
US4075169A (en)	1978-02-21	Fluorosiloxydiphenylsiloxy block copolymers
US4962174A (en)	1990-10-09	Preparation of alkoxysilethylene endblocked polydiorganosiloxane
US4029629A (en)	1977-06-14	Solvent resistant room temperature vulcanizable silicone rubber composition
US4041010A (en)	1977-08-09	Solvent resistant room temperature vulcanizable silicone rubber compositions
CA1134971A (fr)	1982-11-02	Substances elastomeriques de silicone recuperables par extrusion et tres resistantes
CA1306559C (fr)	1992-08-18	Compositions autoadhesives de polyorganosiloxane
US4157337A (en)	1979-06-05	Process for the polymerization of cyclic diorganopolysiloxanes with cation-complex catalysts
US4122247A (en)	1978-10-24	Process for the polymerization of cyclic diorganopolysiloxanes with cation-complex catalysts
EP0279706B1 (fr)	1993-09-08	Compositions vulcanisables à base de siloxanes fluorés
US3944519A (en)	1976-03-16	Curable organopolysiloxane compositions
US4388449A (en)	1983-06-14	Silicone resin
CA1073586A (fr)	1980-03-11	Augmentation du poids moleculaire de polydiorganosiloxanes termines par un hydroxyle
CA1192694A (fr)	1985-08-27	Caoutchouc au silicone vulcanisable a forte resistance
US5925709A (en)	1999-07-20	Method for the preparation of silicone rubber
US4341888A (en)	1982-07-27	Diorganopolysiloxane copolymers and process for the preparation thereof
CA1055636A (fr)	1979-05-29	Melange durcissable (elastomerique) de type vinylpolydiorganosiloxane-mercaptoorganosiloxane-peroxyde organique et methode pour sa fabrication
US3975362A (en)	1976-08-17	Low temperature reversion resistant organosilicon polymers
JPS632299B2 (fr)	1988-01-18
US4130599A (en)	1978-12-19	Silanol-free resins
US4870115A (en)	1989-09-26	Foamable silicone rubber composition
US3305525A (en)	1967-02-21	Method for making organosilicon polymers
CA1082396A (fr)	1980-07-22	Copolymeres sequences de fluorosiloxydiphenylsiloxyde
US5492993A (en)	1996-02-20	Strain-crystallizing poly(methyl(3,3,3-trifluoropropyl)-siloxane) elastomers and methods for making
US2484595A (en)	1949-10-11	Synthetic elastic and elastomeric products
CA1305816C (fr)	1992-07-28	Groupes terminaux pour polymeres de silicone