JP6110013B2 - 架橋ポリマーを生成する方法およびこれを生成するためのキット - Google Patents
架橋ポリマーを生成する方法およびこれを生成するためのキット Download PDFInfo
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- JP6110013B2 JP6110013B2 JP2016507673A JP2016507673A JP6110013B2 JP 6110013 B2 JP6110013 B2 JP 6110013B2 JP 2016507673 A JP2016507673 A JP 2016507673A JP 2016507673 A JP2016507673 A JP 2016507673A JP 6110013 B2 JP6110013 B2 JP 6110013B2
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- alkyl
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- 238000004519 manufacturing process Methods 0.000 title description 9
- 229920006037 cross link polymer Polymers 0.000 title 1
- -1 siloxane compound Chemical class 0.000 claims description 151
- 125000003118 aryl group Chemical group 0.000 claims description 110
- 125000001072 heteroaryl group Chemical group 0.000 claims description 102
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 74
- 125000000623 heterocyclic group Chemical group 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- 125000001188 haloalkyl group Chemical group 0.000 claims description 69
- 229920005573 silicon-containing polymer Polymers 0.000 claims description 62
- 125000003107 substituted aryl group Chemical group 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 58
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 45
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 43
- 125000003342 alkenyl group Chemical group 0.000 claims description 41
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 37
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 37
- 239000003054 catalyst Substances 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 34
- 238000007142 ring opening reaction Methods 0.000 claims description 27
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 5
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 4
- 125000005107 alkyl diaryl silyl group Chemical group 0.000 claims description 3
- 230000001143 conditioned effect Effects 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000004065 semiconductor Substances 0.000 description 40
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 31
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 31
- 239000013078 crystal Substances 0.000 description 31
- 239000000463 material Substances 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 28
- 125000000524 functional group Chemical group 0.000 description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000008393 encapsulating agent Substances 0.000 description 22
- 229910052799 carbon Inorganic materials 0.000 description 20
- 229930195733 hydrocarbon Natural products 0.000 description 19
- 150000003961 organosilicon compounds Chemical class 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 14
- 150000001721 carbon Chemical group 0.000 description 14
- 239000004215 Carbon black (E152) Substances 0.000 description 13
- 150000001335 aliphatic alkanes Chemical class 0.000 description 13
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 12
- 238000006482 condensation reaction Methods 0.000 description 11
- 229920001971 elastomer Polymers 0.000 description 11
- 239000000806 elastomer Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000008096 xylene Substances 0.000 description 10
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000012855 volatile organic compound Substances 0.000 description 9
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- JJRDHFIVAPVZJN-UHFFFAOYSA-N cyclotrisiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]1 JJRDHFIVAPVZJN-UHFFFAOYSA-N 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 0 CC(*)(N(*)OC*)OO Chemical compound CC(*)(N(*)OC*)OO 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 239000011968 lewis acid catalyst Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 125000002015 acyclic group Chemical group 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910002808 Si–O–Si Inorganic materials 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000001924 cycloalkanes Chemical class 0.000 description 3
- OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 description 3
- 238000006459 hydrosilylation reaction Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000001420 substituted heterocyclic compounds Chemical class 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- BEFYLUYQGQYWBS-UHFFFAOYSA-N 2-benzyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C([SiH]1O[SiH2]O[SiH2]O[SiH2]O1)c1ccccc1 BEFYLUYQGQYWBS-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 2
- 238000013005 condensation curing Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- NPZJKOMUCXNLBN-UHFFFAOYSA-N sodium;dimethyl-oxido-phenylsilane Chemical compound [Na+].C[Si](C)([O-])C1=CC=CC=C1 NPZJKOMUCXNLBN-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910002601 GaN Inorganic materials 0.000 description 1
- JMASRVWKEDWRBT-UHFFFAOYSA-N Gallium nitride Chemical compound [Ga]#N JMASRVWKEDWRBT-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910018540 Si C Inorganic materials 0.000 description 1
- YKSADNUOSVJOAS-UHFFFAOYSA-N [bis[(dimethyl-$l^{3}-silanyl)oxy]-phenylsilyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](O[Si](C)C)(O[Si](C)C)C1=CC=CC=C1 YKSADNUOSVJOAS-UHFFFAOYSA-N 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical compound O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
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- 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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
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- 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
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- 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
- C08G77/08—Preparatory processes characterised by the catalysts used
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/50—Phosphorus bound to carbon only
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
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- 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
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- C08G77/06—Preparatory processes
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- 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
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- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2227—Oxides; Hydroxides of metals of aluminium
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/42—Wire connectors; Manufacturing methods related thereto
- H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
- H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
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- H—ELECTRICITY
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- H01L2224/42—Wire connectors; Manufacturing methods related thereto
- H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
- H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
- H01L2224/481—Disposition
- H01L2224/48151—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
- H01L2224/48221—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
- H01L2224/48245—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being metallic
- H01L2224/48247—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being metallic connecting the wire to a bond pad of the item
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Description
に一致するシクロトリシロキサン反復単位からなる群から独立に選択される、シロキサン化合物を提供する。
(a)式(XX)の構造
に一致する少なくとも1つのセグメントを含む第1のシロキサン化合物を準備する工程と、
(b)式(XXX)の構造
に一致する有機ケイ素化合物を準備する工程と、
(c)ルイス酸触媒および溶媒を含む反応相を準備する工程と、
(d)第1のシロキサン化合物および有機ケイ素化合物が縮合反応において反応して、式(XL)の構造
を含む、シロキサン化合物を製造する方法を提供する。
に一致するシクロシロキサン反復単位からなる群から独立に選択される、シロキサン化合物を提供する。
に一致する化合物を提供する。
(a)式(XL)の構造
に一致する複数の反復単位を含む、第1のシロキサン化合物を準備する工程と、
(b)開環触媒を準備する工程と、
(c)第1のシロキサン化合物と開環触媒とを合わせて、反応混合物を生成する工程と、
(d)(i)開環触媒が、第1のシロキサン化合物中の式(XL)の構造に一致する反復単位の少なくとも一部を開環して架橋基を形成し、(ii)架橋基の少なくとも一部が第1のシロキサン化合物の他の分子と反応して分子間に架橋を生成し、これにより、架橋シリコーンポリマーを形成するような条件下で、反応混合物中の成分を反応させる工程と
を含む、架橋シリコーンポリマーを製造する方法を提供する。
(a)第1の部分が、式(XL)の構造
に一致する複数の反復単位を含む、第1のシロキサン化合物を含み、
(b)第2の部分が、開環触媒を含む、
キットを提供する。
(a)半導体結晶であって、半導体結晶の第1の領域中にn型半導体材料、半導体結晶の第2の領域中にp型半導体材料、および半導体材料の第1の領域と第2の領域との間の境界にp−n接合を含む、半導体結晶、
(b)半導体結晶の第1の領域に電気的に接続されたカソード、
(c)半導体結晶の第2の領域に電気的に接続されたアノード、ならびに
(d)半導体結晶を取り囲む封入剤材料であって、
(i)式(XL)の構造
に一致する複数の反復単位を含む第1のシロキサン化合物を準備する工程と、
(ii)開環触媒を準備する工程と、
(iii)第1のシロキサン化合物と開環触媒とを合わせて、反応混合物を生成する工程と、
(iv)(A)開環触媒が、第1のシロキサン化合物中の式(XL)の構造と一致する反復単位の少なくとも一部を開環して架橋基を形成し、(B)架橋基の少なくとも一部が第1のシロキサン化合物の他の分子と反応して分子間に架橋を生成し、これにより、架橋シリコーンポリマーを形成するような条件下で、反応混合物中の成分を反応させる工程と
を含む方法によって製造される架橋シリコーンポリマーを含む、封入剤材料
を含む、発光ダイオードを提供する。
この例は、本発明による、シクロシロキサン反復単位を含むシロキサン化合物の調製を実際に示す。
695.
例2
この例は、本発明による、シクロシロキサン反復単位を含むシロキサン化合物の調製を実際に示す。
例3
この例は、本発明による、シクロシロキサン反復単位を含むシロキサン化合物の調製を実際に示す。
例4
この例は、本発明による、シクロシロキサン反復単位を含むシロキサン化合物の調製を実際に示す。
例5
この例は、式(LXX)の構造に一致するシロキサン化合物の調製を実際に示す。
例6
この例は、本発明による架橋シリコーンポリマーの調製を実際に示す。
この例は、本発明による様々な架橋シリコーンポリマーの調製、およびこれらのポリマーによって示される様々な特性を実際に示す。
この例は、本発明による架橋シリコーンポリマーの調製を実際に示す。
この例は、本発明による架橋シリコーンポリマーの調製を実際に示す。
この例は、本発明による架橋シリコーンポリマーの調製を実際に示す。
Claims (45)
- (a)第1のシロキサン化合物を準備する工程であって、前記第1のシロキサン化合物は複数のシロキサン反復単位を含み、前記シロキサン反復単位の少なくとも一部がシクロシロキサン反復単位であり、前記シクロシロキサン反復単位が、式(XL)の構造
(c)前記第1のシロキサン化合物と前記開環触媒とを合わせて、反応混合物を生成する工程と、
(d)(i)前記開環触媒が、前記第1のシロキサン化合物中の前記シクロシロキサン反復単位の少なくとも一部を開環して架橋基を形成し、(ii)前記架橋基の少なくとも一部が前記第1のシロキサン化合物の他の分子と反応して分子間に架橋を生成し、これにより、架橋シリコーンポリマーを形成するような条件下で、前記反応混合物中の成分を反応させる工程と
を含む、架橋シリコーンポリマーを製造する方法。 - 前記架橋シリコーンポリマーを加熱して、前記架橋を加速させる工程をさらに含む、請求項1に記載の方法。
- 前記第1のシロキサン化合物が、式(X)の構造
に一致する少なくとも1つのセグメントをさらに含む、請求項1に記載の方法。 - xが0であり、yが1である、請求項1に記載の方法。
- R3およびR4が、アルキル基、ハロアルキル基、およびアリール基からなる群から独立に選択される、請求項1に記載の方法。
- R3およびR4が、アリール基からなる群から独立に選択される、請求項5に記載の方法。
- R3およびR4が、それぞれフェニル基である、請求項6に記載の方法。
- R1およびR2が、アルキル基およびアリール基からなる群から独立に選択される、請求項1に記載の方法。
- R1およびR2が、アルキル基からなる群から独立に選択される、請求項8に記載の方法。
- R1およびR2がメチル基である、請求項9に記載の方法。
- シリル末端基をさらに含む、請求項1に記載の方法。
- 前記第1のシロキサン化合物中の約10mol%以上の前記反復単位が式(XL)の構造に一致する、請求項1に記載の方法。
- 前記反応混合物が、式(LX)、式(LXV)、および式(LXX)からなる群から選択される構造
- R60およびR61が、ハロアルキル基、アリール基、およびアラルキル基からなる群から選択される、請求項13に記載の方法。
- R60およびR61が、アリール基からなる群から選択される、請求項14に記載の方法。
- R60およびR61がフェニル基である、請求項15に記載の方法。
- R62およびR63が、アルキル基からなる群から選択される、請求項13に記載の方法。
- R70およびR71が、アリール基からなる群から独立に選択される、請求項13に記載の方法。
- R70およびR71が、それぞれフェニル基である、請求項18に記載の方法。
- R72、R73、R74、R75、R76、R77、R78、R80、R81、R82、R83、R84、R85、およびR86が、アルキル基およびアリール基からなる群から独立に選択される、請求項13に記載の方法。
- R72、R73、R75、R76、R77、R78、R80、R81、R83、R84、R85、およびR86が、アルキル基からなる群から独立に選択され;R74およびR82が、アリール基からなる群から独立に選択される、請求項20に記載の方法。
- R72、R73、R75、R76、R77、R78、R80、R81、R83、R84、R85、およびR86がメチル基であり;R74およびR82がフェニル基である、請求項21に記載の方法。
- cが1である、請求項13に記載の方法。
- 第1の部分と第2の部分とを含む、架橋シリコーンポリマーを製造するためのキットであって、前記第1の部分と第2の部分とが、混合されて架橋シリコーンポリマーを生成する時点まで、互いに物理的に隔てられており、
(a)前記第1の部分が第1のシロキサン化合物を含み、前記第1のシロキサン化合物が複数のシロキサン反復単位を含み、前記シロキサン反復単位の少なくとも一部がシクロシロキサン反復単位であり、前記シクロシロキサン反復単位が、式(XL)の構造
キット。 - 前記第1のシロキサン化合物が、式(X)の構造
に一致する少なくとも1つのセグメントをさらに含む、請求項24に記載のキット。 - xが0であり、yが1である、請求項24に記載のキット。
- R3およびR4が、アルキル基、ハロアルキル基、およびアリール基からなる群から独立に選択される、請求項24に記載のキット。
- R3およびR4が、アリール基からなる群から独立に選択される、請求項27に記載のキット。
- R3およびR4がそれぞれフェニル基である、請求項28に記載のキット。
- R1およびR2が、アルキル基およびアリール基からなる群から独立に選択される、請求項24に記載のキット。
- R1およびR2が、アルキル基からなる群から独立に選択される、請求項30に記載のキット。
- R1およびR2がメチル基である、請求項31に記載のキット。
- 前記第1のシロキサン化合物がシリル末端基をさらに含む、請求項24に記載のキット。
- 前記第1のシロキサン化合物中の約10mol%以上の前記反復単位が式(XL)の構造に一致する、請求項24に記載のキット。
- 前記第1の部分が、式(LX)、式(LXV)、および式(LXX)からなる群から選択される構造
- R60およびR61が、ハロアルキル基、アリール基、およびアラルキル基からなる群から選択される、請求項35に記載のキット。
- R60およびR61が、アリール基からなる群から選択される、請求項36に記載のキット。
- R60およびR61がフェニル基である、請求項37に記載のキット。
- R62およびR63が、アルキル基からなる群から選択される、請求項35に記載のキット。
- R70およびR71が、アリール基からなる群から独立に選択される、請求項35に記載のキット。
- R70およびR71が、それぞれフェニル基である、請求項40に記載のキット。
- R72、R73、R74、R75、R76、R77、R78、R80、R81、R82、R83、R84、R85、およびR86が、アルキル基およびアリール基からなる群から独立に選択される、請求項35に記載のキット。
- R72、R73、R75、R76、R77、R78、R80、R81、R83、R84、R85、およびR86が、アルキル基からなる群から独立に選択され;R74およびR82が、アリール基からなる群から独立に選択される、請求項42に記載のキット。
- R72、R73、R75、R76、R77、R78、R80、R81、R83、R84、R85、およびR86がメチル基であり;R74およびR82がフェニル基である、請求項43に記載のキット。
- cが1である、請求項35に記載のキット。
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US14/244,211 US9388284B2 (en) | 2013-04-12 | 2014-04-03 | Cross-linked silicone polymer and process for producing the same |
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KR101056432B1 (ko) | 2009-09-14 | 2011-08-11 | 삼성모바일디스플레이주식회사 | 유기 전계 발광 표시장치 및 이의 밀봉용 충전재 |
RU2447094C2 (ru) * | 2010-06-18 | 2012-04-10 | Учреждение Российской Академии Наук Институт Элементоорганических Соединений Им. А.Н. Несмеянова Ран (Инэос Ран) | СПОСОБ ПОЛУЧЕНИЯ СТЕРЕОРЕГУЛЯРНЫХ ЦИКЛОЛИНЕЙНЫХ ОЛИГОСИЛОКСАНОВ α,ω-ДИГИДРОКСИПОЛИ(ОКСИ-2,8-ДИОРГАНО-4,4,6,6,10,10,12,12-ОКТАМЕТИЛЦИКЛОГЕКСАСИЛОКСАН-2,8-ДИИЛ)ОВ |
US8865926B2 (en) | 2011-09-26 | 2014-10-21 | Sivance, Llc | Process for the production of cyclosiloxanes |
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EP2984687B1 (en) | 2017-06-14 |
CN105190919A (zh) | 2015-12-23 |
RU2630218C2 (ru) | 2017-09-06 |
US20160289390A1 (en) | 2016-10-06 |
US9718927B2 (en) | 2017-08-01 |
TW201708320A (zh) | 2017-03-01 |
US9388284B2 (en) | 2016-07-12 |
AU2014250846A1 (en) | 2015-09-10 |
TWI540156B (zh) | 2016-07-01 |
TWI610967B (zh) | 2018-01-11 |
KR20170140439A (ko) | 2017-12-20 |
MY174873A (en) | 2020-05-19 |
CA2901392A1 (en) | 2014-10-16 |
RU2015148262A (ru) | 2017-05-15 |
CN105190919B (zh) | 2018-03-13 |
WO2014169177A1 (en) | 2014-10-16 |
JP2016516120A (ja) | 2016-06-02 |
KR101993031B1 (ko) | 2019-06-25 |
TW201446841A (zh) | 2014-12-16 |
KR20150126911A (ko) | 2015-11-13 |
AU2014250846B2 (en) | 2017-03-30 |
US20140309380A1 (en) | 2014-10-16 |
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