TWI374902B - - Google Patents
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- Publication number
- TWI374902B TWI374902B TW094124134A TW94124134A TWI374902B TW I374902 B TWI374902 B TW I374902B TW 094124134 A TW094124134 A TW 094124134A TW 94124134 A TW94124134 A TW 94124134A TW I374902 B TWI374902 B TW I374902B
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl group
- repeating unit
- mole
- reaction
- group
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 6
- 229920003257 polycarbosilane Polymers 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001555 benzenes Chemical class 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFUYDYUQFXMKFB-UHFFFAOYSA-N CC(C(Cl)(Cl)C)CCCCCCCC Chemical compound CC(C(Cl)(Cl)C)CCCCCCCC UFUYDYUQFXMKFB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000011345 viscous material Substances 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- MNXVHBFCELLVBA-UHFFFAOYSA-N 2,2-dichloropentane Chemical compound CCCC(C)(Cl)Cl MNXVHBFCELLVBA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 238000005406 washing Methods 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
- C08G77/60—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 all the silicon atoms are connected by linkages other than oxygen atoms
-
- 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
- C08G77/06—Preparatory processes
-
- 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
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- 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
- C08G77/50—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 by carbon linkages
- C08G77/52—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 by carbon linkages containing aromatic rings
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004210428 | 2004-07-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200611925A TW200611925A (en) | 2006-04-16 |
| TWI374902B true TWI374902B (enExample) | 2012-10-21 |
Family
ID=35785233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094124134A TW200611925A (en) | 2004-07-16 | 2005-07-15 | Polycarbosilane and method for producing same |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7652118B2 (enExample) |
| EP (1) | EP1770111A4 (enExample) |
| JP (1) | JP5223193B2 (enExample) |
| KR (1) | KR101156314B1 (enExample) |
| CN (1) | CN100535032C (enExample) |
| TW (1) | TW200611925A (enExample) |
| WO (1) | WO2006009123A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1867674A1 (en) * | 2005-04-08 | 2007-12-19 | Toagosei Co., Ltd. | Polycarbosilane and method for producing same |
| EP2824130B1 (en) * | 2012-03-07 | 2018-02-07 | Nippon Soda Co., Ltd. | Method for producing polydialkylsilane |
| EP2880082A4 (en) * | 2012-08-02 | 2016-03-02 | Henkel China Co Ltd | POLYCARBOSILAN AND HARDENABLE COMPOSITIONS FOR LED PACKAGING THEREOF |
| JP7366421B2 (ja) * | 2020-03-27 | 2023-10-23 | 国立研究開発法人産業技術総合研究所 | ポリカルボシランの合成法 |
| CN112062967B (zh) * | 2020-08-05 | 2022-08-30 | 福建立亚化学有限公司 | 一种聚碳硅烷陶瓷先驱体材料制备方法 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2628243A (en) * | 1950-01-09 | 1953-02-10 | Dow Corning | Preparation of organochlorosilanes |
| US4100233A (en) * | 1975-04-25 | 1978-07-11 | The Research Institute For Iron, Steel And Other Metals Of The Tohoku University | Silicon carbide fibers having a high strength and a method for producing said fibers |
| JPS5929095B2 (ja) * | 1975-12-29 | 1984-07-18 | トウホクダイガクキンゾクザイリヨウケンキユウシヨチヨウ | 耐熱性超硬複合材料およびその製造方法 |
| JPS5855007A (ja) | 1981-09-29 | 1983-04-01 | Mitsubishi Chem Ind Ltd | 気体分離膜 |
| JPS6225744A (ja) * | 1985-07-26 | 1987-02-03 | Hitachi Ltd | 複合レジスト層の形成方法 |
| US5039593A (en) * | 1986-10-31 | 1991-08-13 | Zeigler John K | Poly(silyl silane) homo and copolymers |
| US4820788A (en) * | 1986-10-31 | 1989-04-11 | John M. Zeigler | Poly(silyl silane)homo and copolymers |
| FR2617854B1 (fr) * | 1987-07-10 | 1989-10-27 | Rhone Poulenc Chimie | Composition a base d'un nouveau polycarbosilane, sa preparation et son application a la fabrication de produits et articles ceramiques a base de carbure de silicium |
| JPH03198061A (ja) * | 1989-12-27 | 1991-08-29 | Konica Corp | 電子写真感光体 |
| JP3021741B2 (ja) * | 1991-04-18 | 2000-03-15 | 三井化学株式会社 | 非線形光学材料、非線形光学素子、透明光学材料および薄膜 |
| JPH04342726A (ja) * | 1991-05-20 | 1992-11-30 | Showa Denko Kk | シリコン含有重合体およびその製造方法 |
| JPH05323330A (ja) * | 1992-05-20 | 1993-12-07 | Showa Denko Kk | 液晶配向膜 |
| DE4313130C1 (de) * | 1993-04-22 | 1994-05-26 | Goldschmidt Ag Th | Verfahren zur Herstellung von Silanen bzw. Organosiliciumhydriden durch Reduktion der entsprechenden Siliciumhalogenide bzw. Organosiliciumhalogenide |
| JP2970391B2 (ja) * | 1994-03-08 | 1999-11-02 | 信越化学工業株式会社 | 導電性重合体組成物 |
| US5500127A (en) * | 1994-03-14 | 1996-03-19 | Rohm And Haas Company | Purification process |
| US5578103A (en) * | 1994-08-17 | 1996-11-26 | Corning Incorporated | Alkali metal ion migration control |
| JP3870424B2 (ja) * | 1994-10-27 | 2007-01-17 | 住友電気工業株式会社 | 有機光伝導体および素子 |
| JPH1180362A (ja) * | 1997-08-29 | 1999-03-26 | Toray Dow Corning Silicone Co Ltd | シルフェニレンシルアルキレンポリマーの製造方法 |
| JPH11131023A (ja) * | 1997-10-31 | 1999-05-18 | Dow Corning Toray Silicone Co Ltd | コーティング材 |
| JPH11199778A (ja) * | 1997-12-29 | 1999-07-27 | Dow Corning Toray Silicone Co Ltd | 硬化性シルフェニレン系ポリマー組成物 |
| JPH11199676A (ja) * | 1997-12-29 | 1999-07-27 | Dow Corning Toray Silicone Co Ltd | シルフェニレン系ポリマーおよびその製造方法 |
| US6072016A (en) * | 1997-12-29 | 2000-06-06 | Dow Corning Toray Silicone Co., Ltd. | Silphenylene polymer and composition containing same |
| US6225238B1 (en) * | 1999-06-07 | 2001-05-01 | Allied Signal Inc | Low dielectric constant polyorganosilicon coatings generated from polycarbosilanes |
| US6761975B1 (en) * | 1999-12-23 | 2004-07-13 | Honeywell International Inc. | Polycarbosilane adhesion promoters for low dielectric constant polymeric materials |
| JP3715500B2 (ja) | 2000-03-09 | 2005-11-09 | 株式会社東芝 | 自動改札システムと自動復帰方法 |
| US6596833B2 (en) * | 2000-03-14 | 2003-07-22 | Chisso Corporation | Carbosilane and polycarbosilane |
| JP3886779B2 (ja) * | 2001-11-02 | 2007-02-28 | 富士通株式会社 | 絶縁膜形成用材料及び絶縁膜の形成方法 |
| JP2006002125A (ja) * | 2004-06-21 | 2006-01-05 | Tokyo Ohka Kogyo Co Ltd | カルボシラン系ポリマーを含んでなる被膜形成用組成物、および該組成物から得られた被膜 |
| JP2006323180A (ja) * | 2005-05-19 | 2006-11-30 | Tokyo Ohka Kogyo Co Ltd | シリルフェニレン系ポリマー含有中間層形成用組成物およびそれを用いたパターン形成方法 |
-
2005
- 2005-07-15 EP EP05766379A patent/EP1770111A4/en not_active Withdrawn
- 2005-07-15 US US11/572,178 patent/US7652118B2/en not_active Expired - Fee Related
- 2005-07-15 JP JP2006529199A patent/JP5223193B2/ja not_active Expired - Fee Related
- 2005-07-15 WO PCT/JP2005/013184 patent/WO2006009123A1/ja not_active Ceased
- 2005-07-15 KR KR1020077003677A patent/KR101156314B1/ko not_active Expired - Fee Related
- 2005-07-15 TW TW094124134A patent/TW200611925A/zh not_active IP Right Cessation
- 2005-07-15 CN CNB200580024070XA patent/CN100535032C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN100535032C (zh) | 2009-09-02 |
| KR20070032820A (ko) | 2007-03-22 |
| WO2006009123A1 (ja) | 2006-01-26 |
| US7652118B2 (en) | 2010-01-26 |
| US20070299232A1 (en) | 2007-12-27 |
| TW200611925A (en) | 2006-04-16 |
| CN1984943A (zh) | 2007-06-20 |
| JP5223193B2 (ja) | 2013-06-26 |
| EP1770111A1 (en) | 2007-04-04 |
| KR101156314B1 (ko) | 2012-06-13 |
| JPWO2006009123A1 (ja) | 2008-05-01 |
| EP1770111A4 (en) | 2011-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |