JPH0360336B2 - - Google Patents
Info
- Publication number
- JPH0360336B2 JPH0360336B2 JP21539082A JP21539082A JPH0360336B2 JP H0360336 B2 JPH0360336 B2 JP H0360336B2 JP 21539082 A JP21539082 A JP 21539082A JP 21539082 A JP21539082 A JP 21539082A JP H0360336 B2 JPH0360336 B2 JP H0360336B2
- Authority
- JP
- Japan
- Prior art keywords
- molecular weight
- type
- polyphenylsiloxane
- reaction
- catalyst
- Prior art date
- 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
Links
- -1 polyphenylsiloxane Polymers 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 150000002222 fluorine compounds Chemical class 0.000 claims description 5
- NOKUWSXLHXMAOM-UHFFFAOYSA-N hydroxy(phenyl)silicon Chemical class O[Si]C1=CC=CC=C1 NOKUWSXLHXMAOM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 claims description 2
- 229910001634 calcium fluoride Inorganic materials 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- 238000000034 method Methods 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000009826 distribution Methods 0.000 description 9
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
- 238000005266 casting Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 241000251468 Actinopterygii Species 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000007796 conventional method Methods 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
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- 238000009864 tensile test Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KBXJHRABGYYAFC-UHFFFAOYSA-N octaphenylsilsesquioxane Chemical group O1[Si](O2)(C=3C=CC=CC=3)O[Si](O3)(C=4C=CC=CC=4)O[Si](O4)(C=5C=CC=CC=5)O[Si]1(C=1C=CC=CC=1)O[Si](O1)(C=5C=CC=CC=5)O[Si]2(C=2C=CC=CC=2)O[Si]3(C=2C=CC=CC=2)O[Si]41C1=CC=CC=C1 KBXJHRABGYYAFC-UHFFFAOYSA-N 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 229920006389 polyphenyl polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 238000011088 calibration curve Methods 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- POPVULPQMGGUMJ-UHFFFAOYSA-N octasilsesquioxane cage Chemical compound O1[SiH](O[SiH](O2)O[SiH](O3)O4)O[SiH]4O[SiH]4O[SiH]1O[SiH]2O[SiH]3O4 POPVULPQMGGUMJ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Landscapes
- Silicon Polymers (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP21539082A JPS59108033A (ja) | 1982-12-10 | 1982-12-10 | 高分子量ラダ−型ポリフエニルシロキサンの製造方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP21539082A JPS59108033A (ja) | 1982-12-10 | 1982-12-10 | 高分子量ラダ−型ポリフエニルシロキサンの製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59108033A JPS59108033A (ja) | 1984-06-22 |
JPH0360336B2 true JPH0360336B2 (zh) | 1991-09-13 |
Family
ID=16671512
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP21539082A Granted JPS59108033A (ja) | 1982-12-10 | 1982-12-10 | 高分子量ラダ−型ポリフエニルシロキサンの製造方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS59108033A (zh) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59129230A (ja) * | 1983-01-14 | 1984-07-25 | Dainippon Ink & Chem Inc | 高分子量ラダ−型ポリオルガノシロキサン共重合体の製造方法 |
JPH02107638A (ja) * | 1988-10-17 | 1990-04-19 | Shin Etsu Chem Co Ltd | ラダー型オルガノポリシロキサンの製造方法 |
JPH0539357A (ja) * | 1991-08-06 | 1993-02-19 | Toray Dow Corning Silicone Co Ltd | フエニルポリシルセスキオキサンおよびその製造方法 |
DE69425473T3 (de) * | 1993-11-05 | 2005-11-03 | Shin-Etsu Chemical Co., Ltd. | Verfahren zur Herstellung von Organo-funktionelle Gruppen enthaltenden Organopolysiloxanen und daraus hergestellte Organopolysiloxane, Mercapto- und Alkoxygruppen enthaltende Organopolysiloxane und Verfahren zu deren Herstellung |
DE4436536A1 (de) * | 1994-04-20 | 1995-10-26 | Bayer Ag | Verfahren zur Herstellung von Umsetzungsprodukten aus Poly(diorganosiloxanen) |
ATE189687T1 (de) * | 1994-04-20 | 2000-02-15 | Ge Bayer Silicones Gmbh & Co | Verfahren zur herstellung von umsetzungsprodukten aus poly(diorganosiloxanen) |
JP4761139B2 (ja) * | 2006-03-10 | 2011-08-31 | 独立行政法人産業技術総合研究所 | シロキサン系ポリマーの効率的製造方法 |
JP2009233540A (ja) * | 2008-03-26 | 2009-10-15 | Hiroshima Univ | 分離膜および分離膜の製造方法 |
JP6236222B2 (ja) * | 2012-06-11 | 2017-11-22 | 株式会社日本触媒 | シアネートエステル系組成物及びその用途 |
KR102363819B1 (ko) * | 2014-02-28 | 2022-02-17 | 주식회사 동진쎄미켐 | 실세스퀴옥산 복합 고분자 및 이의 제조방법 |
KR102325278B1 (ko) * | 2014-03-07 | 2021-11-16 | 주식회사 동진쎄미켐 | 실세스퀴옥산 복합 고분자를 포함하는 열가소성 수지 조성물 |
-
1982
- 1982-12-10 JP JP21539082A patent/JPS59108033A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS59108033A (ja) | 1984-06-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0121257B1 (en) | Polyarylnitrile polymers and a method for their production | |
JPS63295631A (ja) | ベンゾフェノンとジフェニルスルホンとヒドロキノンとのブロック・ターポリマーの製法 | |
CN107459652B (zh) | 一种可室温固化的耐热硅树脂及其制备方法 | |
JPH0360336B2 (zh) | ||
JPS58147426A (ja) | 線状ポリ(3−アルキル2、5−チエニレン)重合体およびその製造方法 | |
US3000858A (en) | Organopolysiloxane composition | |
US5081202A (en) | High purity phenyl silicone ladder polymer and method for producing the same | |
JP3652151B2 (ja) | 硬化性ポリメチルシルセスキオキサンの製造方法 | |
JPS6137289B2 (zh) | ||
US6914119B2 (en) | Heat-resistant polyether, curable polyether, and coating liquid for forming a polyether film | |
JP3942201B2 (ja) | フェニルポリシルセスキオキサンの製造方法 | |
WO2006009123A1 (ja) | ポリカルボシラン及びその製造方法 | |
TWI520987B (zh) | Cage silsesquioxane silicone resin and siloxane cage silsesquioxane silicone siloxane copolymer, and manufacturing method thereof | |
JPH0725996A (ja) | ペルフルオロポリオキシアルキレン配列を含む熱可塑性ポリエステル | |
KR20180071165A (ko) | 폴리아릴렌 수지 | |
JPH05230215A (ja) | フッ素含有ポリオルガノシルセスキオキサンとその製造方法 | |
JP3165172B2 (ja) | フルオロシリコーンレジンおよびその製造方法 | |
JPS5984920A (ja) | ポリジハイドロジエンシロキサンの製法 | |
TWI393733B (zh) | Polysilane and its manufacturing method | |
US4912192A (en) | Polyarylnitrile polymers and a method for their production | |
JP3541075B2 (ja) | ポリメチルシロキサン樹脂の製造法 | |
TWI652254B (zh) | 化合物的製備方法及包含其之聚合物製備方法 | |
US20020006999A1 (en) | Polyether copolymer | |
JPH0379378B2 (zh) | ||
JPH03227983A (ja) | プロペニル基含有エポキシ樹脂 |