TWI752130B - 製造氯化矽氮烷的方法 - Google Patents
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- 238000000034 method Methods 0.000 title claims abstract description 19
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 239000005046 Chlorosilane Substances 0.000 claims abstract description 8
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims abstract description 8
- -1 sulfonic acid imide Chemical class 0.000 claims abstract 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005052 trichlorosilane Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 claims description 2
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical group Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 150000003751 zinc Chemical class 0.000 abstract description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000005229 chemical vapour deposition Methods 0.000 description 10
- 238000000231 atomic layer deposition Methods 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 6
- 210000002381 plasma Anatomy 0.000 description 6
- YKLDXQARVWVJTQ-UHFFFAOYSA-N Cl[SiH](Cl)N[SiH](Cl)Cl Chemical compound Cl[SiH](Cl)N[SiH](Cl)Cl YKLDXQARVWVJTQ-UHFFFAOYSA-N 0.000 description 5
- QMMPBNFUSOIFDC-UHFFFAOYSA-N ctk0b2378 Chemical group Cl[Si](Cl)(Cl)N[Si](Cl)(Cl)Cl QMMPBNFUSOIFDC-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- SSFOKDCYTVRUAP-UHFFFAOYSA-N [dimethyl-(trichlorosilylamino)silyl]methane Chemical compound C[Si](C)(C)N[Si](Cl)(Cl)Cl SSFOKDCYTVRUAP-UHFFFAOYSA-N 0.000 description 2
- 238000000995 aerosol-assisted chemical vapour deposition Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000001505 atmospheric-pressure chemical vapour deposition Methods 0.000 description 2
- 238000000277 atomic layer chemical vapour deposition Methods 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001928 direct liquid injection chemical vapour deposition Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004050 hot filament vapor deposition Methods 0.000 description 2
- 238000002365 hybrid physical--chemical vapour deposition Methods 0.000 description 2
- 238000004518 low pressure chemical vapour deposition Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000000259 microwave plasma-assisted chemical vapour deposition Methods 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001289 rapid thermal chemical vapour deposition Methods 0.000 description 2
- 239000005049 silicon tetrachloride Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000000038 ultrahigh vacuum chemical vapour deposition Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000000407 epitaxy Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001165 gas chromatography-thermal conductivity detection Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000000869 ion-assisted deposition Methods 0.000 description 1
- 238000001659 ion-beam spectroscopy Methods 0.000 description 1
- 238000001755 magnetron sputter deposition Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005546 reactive sputtering Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000000927 vapour-phase epitaxy Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/08—Compounds containing halogen
- C01B33/107—Halogenated silanes
- C01B33/10773—Halogenated silanes obtained by disproportionation and molecular rearrangement of halogenated silanes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
- B01J31/0227—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts being perfluorinated, i.e. comprising at least one perfluorinated moiety as substructure in case of polyfunctional compounds
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/08—Compounds containing halogen
- C01B33/107—Halogenated silanes
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/08—Compounds containing halogen
- C01B33/107—Halogenated silanes
- C01B33/10778—Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
- B01J2531/26—Zinc
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- Chemical Kinetics & Catalysis (AREA)
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Abstract
一種製造氯化矽氮烷的方法。該方法包含使：(a)二矽氮烷；(b)氯矽烷；及(c)催化劑接觸，該催化劑係：(i)磺酸或(ii)磺酸醯亞胺之鋅鹽。
Description
本發明涉及一種催化轉矽烷化反應的方法。
已知藉由氯化鋅催化轉矽烷化反應，如D.E.Spielvogel & C.L.Frye,J.Organometallic Chem.,1978(161)165-169所記載。然而，本文中所記載的催化劑更有效。
本發明所解決之問題係對於轉矽烷化反應之額外催化劑的需求。
本發明提供一種製造氯化矽氮烷的方法。該方法包含使：(a)二矽氮烷；(b)氯矽烷；及(c)催化劑接觸，該催化劑係：(i)磺酸或(ii)磺酸醯亞胺之鋅鹽。
除非特別註明，否則百分比為重量百分比(wt%)且溫度使用℃。除非特別註明，否則操作是在室溫(20至25℃)下進行。烴基係衍生自藉由從C1-C20烴除去氫原子之取代基。較佳地，烴基係直鍊或分支鏈。烯基係具有至少一個碳-碳雙鍵的烴基。較佳地，烯基具有一個碳-碳雙鍵。烷基係飽和C1-C20烴基，其可係直鏈或分支鏈。
較佳地，二矽氮烷僅經烴基、氯基或其組合取代。在一較佳實施例中，二矽氮烷係全烴基二矽氮烷。較佳地，烴基係C1
-C10
烴基、較佳係C1
-C6
、較佳係C1
-C4
、較佳係甲基或乙基、較佳係甲基。較佳地，烴基係具有一個雙鍵的烷基或烯基。特別較佳的全烴基二矽氮烷包括六甲基二矽氮烷、1,1,1-三氯-3,3,3-三甲基二矽氮烷及1,1,3,3-四甲基-1,3-二乙烯基矽氮烷。
較佳地，氯矽烷係經氯取代之單矽烷或二矽烷。較佳地，氯矽烷具有至少兩個氯基，較佳地至少三個氯基。特別較佳的氯矽烷包括二氯矽烷、三氯矽烷及四氯矽烷。
較佳地，氯化矽氮烷產物具有4至6個氯基。較佳地，氯化矽氮烷產物係六氯二矽氮烷或1,1,3,3-四氯二矽氮烷。
較佳地，催化劑係具有至少一個三氟甲基之磺酸或醯亞胺的鋅鹽。較佳地，磺酸係芳族磺酸、甲磺酸、三氟甲磺酸或HO3
S(CF2
)x
CF3
，其中x係1至10的整數。較佳地芳族磺酸係對甲苯磺酸。較佳地，x係至少2、較佳地係至少3；較佳地不大於9、較佳地不大於8、較佳地不大於7、較佳地不大於6、較佳地不大於5。
較佳地，反應物(a)、(b)及(c)在20至150℃的溫度下加熱；較佳地至少40℃、較佳地至少50℃；較佳地不高於100℃，較佳地不高於80℃。較佳的加熱時間介於0.5到8小時，較佳地0.5至2小時。適當的加熱時間可輕易取決於裝置或其他參數等。較佳係由蒸餾來純化氯化矽氮烷。較佳地，反應物在75至150 kPa的壓力下接觸。蒸餾通常在低於大氣壓力下進行。
較佳地，反應物(a)、(b)及(c)在實質上不存在除反應物之外的溶劑的情況下結合，即(a)、(b)及(c)之反應混合物包含不大於5 wt%的溶劑、較佳地不大於1 wt%、較佳地不大於0.5 wt%、較佳地不大於0.2 wt%。較佳地，反應物(a)或(b)與反應物(c)結合，然後與另一反應物(a)及(b)結合。較佳地，包含(a)、(b)及(c)之反應混合物實質上不含腈溶劑（即，乙腈）；即，其包含不大於3 wt%腈溶劑、較佳地不大於0.5 wt%腈溶劑、較佳地不大於0.2 wt%腈溶劑、較佳地不大於0.1 wt%腈溶劑。
氯化矽氮烷產物可用於藉由已知技術（包括，例如物理氣相沉積、原子層沉積(ALD)、或化學氣相沉積(CVD)）形成矽-雜原子膜。該物理氣相沉積方法可包含濺鍍。適合的濺鍍方法包括直流(DC)磁控濺射法、離子束濺鍍法、反應濺鍍法、以及離子輔助濺鍍法。一般而言，該沉積方法包含ALD或CVD。較佳地，雜原子選自碳、氧及氮。
適合的ALD方法包括電漿增強原子層沉積法(PEALD)、空間原子層沉積法(SALD)以及熱原子層沉積法(TALD)。當用PEALD方法時，該電漿可以係前述電漿之任一者。該電漿可以可選地進一步含有載氣，諸如分子氮或氬氣體。電漿係由電漿形成氣體所形成，其可包含分子氮與分子氫之混合物。
適合的CVD方法包括以下之方法：簡單熱氣相沉積、電漿增強化學氣相沉積(PECVD)、電子迴旋共振(ECRCVD)、大氣壓化學氣相沉積(APCVD)、低壓化學氣相沉積(LPCVD)、超高真空化學氣相沉積(UHVCVD)、氣溶膠輔助化學氣相沉積(AACVD)、直接液體注入化學氣相沉積(DLICVD)、微波電漿輔助化學氣相沉積(MPCVD)、遠端電漿增強化學氣相沉積(RPECVD)、原子層化學氣相沉積(ALCVD)、熱絲化學氣相沉積(HWCVD)、混合物理化學氣相沉積(HPCVD)、快速熱化學氣相沉積(RTCVD)、及氣相磊晶化學氣相沉積(vapor-phase epitaxy chemical vapor deposition, VPECVD)、光輔助化學氣相沉積(photo-assisted chemical vapor disposition, PACVD)及火焰輔助化學氣相沉積(FACVD)。實例
實例1：1,1,3,3-四氯二矽氮烷的合成。
將5.00 g三氯矽烷與0.17 g三氟甲磺酸鋅及10.75 g乙腈混合，溶解大部分的三氟甲磺酸鋅。在2分鐘內加入1.49 g六甲基二矽氮烷。隨後將溶液加熱至回流(38.5℃)，隨著三氯矽烷消耗，溫度緩慢升高。加熱持續52分鐘，達到51.3℃。將該溫度保持2分鐘，然後緩慢冷卻6分鐘。將熱源移除。粗產物之GC顯示TCDZ的產率為70%。 實例2：1,1,3,3-四氯二矽氮烷的純化。
將粗產物1,1,3,3-四氯二矽氮烷通過15 cm Vigreux管柱蒸餾以得到96%的1,1,3,3-四氯二矽氮烷。 實例3：1,1,1,3,3,3-六氯二矽氮烷的合成。
將0.25 g三氟甲磺酸鋅溶於5.00 g乙腈中，這可能需要一段時間才能完全溶解。然後將該混合物加入11.75 g四氯化矽中並將該溶液加熱至回流。在5分鐘內將製備1之5.00 g的1,1,1-三氯-3,3,3-三甲基二矽氮烷加入該回流溶液中。將該反應物回流約5小時。粗產物之GC-TCD顯示該混合物的產率為47.5%。 實例4：1,1,1,3,3,3-六氯二矽氮烷的純化。
將實例3的混合物通過15 cm Vigreux管柱蒸餾以收集1.24 g之95%六氯二矽氮烷（19.4%分離產率）。 實例5：1,1,1,3,3,3-六氯二矽氮烷的合成。
裝載3%三氟甲磺酸鋅溶解於乙腈中，以使3%的反應混合物總質量進入具有四氯化矽的壓力反應器中。將該反應器加熱到140℃並在5小時內加入六甲基二矽氮烷，並冷卻到室溫，以在粗混合物中得到2.8%產率的1,1,1,3,3,3-六氯二矽氮烷。
Claims (9)
- 一種製造氯化矽氮烷的方法，該方法包含使：(a)二矽氮烷；(b)氯矽烷；及(c)催化劑接觸，該催化劑係：(i)磺酸或(ii)磺酸醯亞胺之鋅鹽。
- 如請求項1之方法，其中該二矽氮烷僅經烴基、氯基或其組合取代。
- 如請求項2之方法，其中該烴基係C1-C10烴基。
- 如請求項3之方法，其中該氯矽烷係經氯取代之單矽烷。
- 如請求項4之方法，其中該氯矽烷係四氯矽烷、三氯矽烷或二氯矽烷。
- 如請求項5之方法，其中該催化劑係具有至少一個三氟甲基之磺酸或磺酸醯亞胺的鋅鹽。
- 如請求項6之方法，其中(a)、(b)及(c)在20至150℃的溫度下接觸。
- 如請求項7之方法，其中該烴基係C1-C4烴基。
- 如請求項1之方法，其中該磺酸係芳族磺酸、甲磺酸、三氟甲磺酸或HO3S(CF2)xCF3，其中x係1至10的整數。
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| TW201602124A (zh) * | 2014-04-03 | 2016-01-16 | 信越化學工業股份有限公司 | 矽氮烷化合物的製造方法 |
| CN105694049A (zh) * | 2016-01-22 | 2016-06-22 | 中国人民解放军国防科学技术大学 | 聚硼硅氮烷的制备方法 |
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| US4540803A (en) * | 1983-11-28 | 1985-09-10 | Dow Corning Corporation | Hydrosilazane polymers from [R3 Si]2 NH and HSiCl3 |
| JPS6241228A (ja) * | 1985-08-16 | 1987-02-23 | Shin Etsu Chem Co Ltd | オルガノポリシロキサンの製造方法 |
| US5086126A (en) * | 1990-12-24 | 1992-02-04 | Dow Corning Corporation | Method for producing functional silazane polymers |
| AU2003220650A1 (en) * | 2002-04-04 | 2003-10-20 | Photon-X, Inc . | Endface preparation method for polymer optical waveguides on polymer substrates |
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| JP5820242B2 (ja) * | 2011-11-08 | 2015-11-24 | 北興化学工業株式会社 | パーフルオロアルキルスルホン酸の金属塩の製造方法 |
| KR20150002628A (ko) * | 2012-04-17 | 2015-01-07 | 모멘티브 퍼포먼스 머티리얼즈 인크. | 하이드로실릴화 반응을 위한 고 활성 촉매 및 그 제조방법 |
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| TW201602124A (zh) * | 2014-04-03 | 2016-01-16 | 信越化學工業股份有限公司 | 矽氮烷化合物的製造方法 |
| CN105694049A (zh) * | 2016-01-22 | 2016-06-22 | 中国人民解放军国防科学技术大学 | 聚硼硅氮烷的制备方法 |
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| WO2018125476A1 (en) | 2018-07-05 |
| JP2020502035A (ja) | 2020-01-23 |
| US11345604B2 (en) | 2022-05-31 |
| US20210300769A1 (en) | 2021-09-30 |
| CN110114311A (zh) | 2019-08-09 |
| TW201823149A (zh) | 2018-07-01 |
| EP3562781A1 (en) | 2019-11-06 |
| EP3562781B1 (en) | 2020-09-23 |
| KR102359491B1 (ko) | 2022-02-07 |
| JP6832432B2 (ja) | 2021-02-24 |
| KR20190091352A (ko) | 2019-08-05 |
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