JP2020522382A - ヒドロシリル化における触媒としての白金化合物及びロジウム化合物の相乗的組み合わせ - Google Patents
ヒドロシリル化における触媒としての白金化合物及びロジウム化合物の相乗的組み合わせ Download PDFInfo
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- 238000006459 hydrosilylation reaction Methods 0.000 title claims abstract description 58
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 150000003284 rhodium compounds Chemical class 0.000 title claims abstract description 30
- 239000003054 catalyst Substances 0.000 title claims abstract description 18
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 11
- 239000011885 synergistic combination Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 88
- 239000010948 rhodium Substances 0.000 claims abstract description 29
- 150000003058 platinum compounds Chemical class 0.000 claims abstract description 24
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 claims abstract description 11
- BUYVJWVYKPKZEX-DWVXZKBMSA-N (1z,5z)-cycloocta-1,5-diene;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].C\C(O)=C\C(C)=O.C\1C\C=C/CC\C=C/1 BUYVJWVYKPKZEX-DWVXZKBMSA-N 0.000 claims abstract description 7
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 claims abstract description 6
- IETKMTGYQIVLRF-UHFFFAOYSA-N carbon monoxide;rhodium;triphenylphosphane Chemical compound [Rh].[O+]#[C-].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 IETKMTGYQIVLRF-UHFFFAOYSA-N 0.000 claims abstract description 6
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 31
- 239000003960 organic solvent Substances 0.000 claims description 31
- 239000003112 inhibitor Substances 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 11
- -1 silane compound Chemical class 0.000 claims description 10
- 229910000510 noble metal Inorganic materials 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 4
- 229920001971 elastomer Polymers 0.000 claims description 4
- 239000000806 elastomer Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000008393 encapsulating agent Substances 0.000 claims description 2
- 239000000565 sealant Substances 0.000 claims description 2
- 150000003384 small molecules Chemical class 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 229910000077 silane Inorganic materials 0.000 claims 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract description 6
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 abstract 2
- 238000010586 diagram Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 5
- 239000004971 Cross linker Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- VYXHVRARDIDEHS-QGTKBVGQSA-N (1z,5z)-cycloocta-1,5-diene Chemical compound C\1C\C=C/CC\C=C/1 VYXHVRARDIDEHS-QGTKBVGQSA-N 0.000 description 1
- BPJCMTVVQHQNIK-UHFFFAOYSA-N C(=O)(Cl)Cl.[Rh+] Chemical compound C(=O)(Cl)Cl.[Rh+] BPJCMTVVQHQNIK-UHFFFAOYSA-N 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000002152 aqueous-organic solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000005844 autocatalytic reaction Methods 0.000 description 1
- 229940001981 carac Drugs 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000011111 cardboard Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000001864 heat-flux differential scanning calorimetry Methods 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 150000005359 phenylpyridines Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229940024463 silicone emollient and protective product Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- 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
- C08G77/08—Preparatory processes characterised by the catalysts used
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0086—Platinum compounds
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0073—Rhodium compounds
-
- 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
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- 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
- C08G77/58—Metal-containing linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
Abstract
Description
実施例1
2.07gのHeraeus製のKarstedt Concentrate(白金分率20重量%)及びEVONIK製のPolymer VS 500の混合物(この混合物の白金分率は0.52重量%であった)の全体を、ロジウム分率が0.52重量%である0.548gのキシレン含有Rh(acac)(CO)2溶液と混合し、触媒組成物を製造した。
手順は、白金分率が0.52重量%である上記混合物1.06g及び上記キシレン含有Rh(acac)(CO)2溶液0.290gを別個に上記ヒドロシリル化可能な混合物に加えたこと以外は、実施例1と同様であった。
実施例3〜29で使用した手順は、実施例1と同様であった。
Claims (16)
- Pt[(Me2SiCH=CH2)2O]2及びPt2[(Me2SiCH=CH2)2O]3からなる群から選択される少なくとも1種の白金化合物と、Rh(acac)(CO)2、Rh2(CO)4Cl2、[Rh(cod)Cl]2、Rh(acac)(cod)、RhH(CO)(PPh3)3、Rh(CO)(PPh3)(acac)、RhCl(CO)(PPh3)2及びRh−2−エチルヘキサノエートからなる群から選択される少なくとも1種のロジウム化合物とを、0.1〜100の範囲のPt/Rhのモル比で含む組成物。
- 前記Pt/Rhのモル比が0.3〜5の範囲にある請求項1に記載の組成物。
- 前記少なくとも1種のロジウム化合物が、Rh(acac)(CO)2、Rh2(CO)4Cl2及び[Rh(cod)Cl]2からなる群から選択される請求項1又は請求項2に記載の組成物。
- 前記少なくとも1種の白金化合物及び前記少なくとも1種のロジウム化合物に加えて少なくとも1種の有機溶媒を含む有機溶液の形態にある請求項1から請求項3のいずれか一項に記載の組成物。
- 前記少なくとも1種の有機溶媒が、ヒドロシリル化に関して反応性である溶媒及びヒドロシリル化に関して非反応性である溶媒からなる群から選択される請求項4に記載の組成物。
- 少なくとも1種の阻害剤を含む請求項1から請求項5のいずれか一項に記載の組成物。
- 阻害剤以外の1種以上の添加剤を含む請求項1から請求項6のいずれか一項に記載の組成物。
- ヒドロシリル化に関して反応性であり、かつ低分子化合物、オリゴマー化合物及びポリマー化合物からなる群から選択される少なくとも1種の化合物を含む請求項1から請求項7のいずれか一項に記載の組成物。
- ヒドロシリル化に関して反応性である前記少なくとも1種の化合物が、ヒドロシリル化に関して好適な少なくとも1つのHSi基を有する化合物、ヒドロシリル化に関して好適な少なくとも1つのオレフィン性二重結合を有する化合物、並びにヒドロシリル化に関して好適な少なくとも1つのHSi基及びヒドロシリル化に関して好適な少なくとも1つのオレフィン性二重結合を有する化合物からなる群から選択される請求項8に記載の組成物。
- 前記少なくとも1種の白金化合物及び前記少なくとも1種のロジウム化合物に由来する貴金属分率が、組成物全体に対して10重量ppm〜45重量%であることを特徴とする請求項1から請求項9のいずれか一項に記載の組成物。
- ヒドロシリル化に関して好適な少なくとも1つのHSi基を有する1種以上の化合物、並びにヒドロシリル化に関して好適な少なくとも1つのオレフィン性二重結合を有する1種以上の化合物、並びに/又はヒドロシリル化に関して好適な少なくとも1つのHSi基及びヒドロシリル化に関して好適な少なくとも1つのオレフィン性二重結合を有する1種以上の化合物を含む請求項9に記載のヒドロシリル化可能な組成物。
- 前記少なくとも1種の白金化合物及び前記少なくとも1種のロジウム化合物に由来する貴金属分率が、ヒドロシリル化可能な組成物全体に対して10〜1,000重量ppmであることを特徴とする請求項11に記載の組成物。
- 請求項1から請求項12のいずれか一項に記載の組成物の製造のための多成分系であって、少なくとも1種の有機溶媒及び前記少なくとも1種の白金化合物を含み、前記少なくとも1種のロジウム化合物を含まない有機溶液の形態の成分(i)と、少なくとも1種の有機溶媒及び前記少なくとも1種のロジウム化合物を含み、前記少なくとも1種の白金化合物を含まない有機溶液の形態の別個の成分(ii)と、必要に応じて、成分(i)及び成分(ii)とは異なる少なくとも1種の別個の成分とを含むか、又は少なくとも1種の有機溶媒、前記少なくとも1種の白金化合物、及び前記少なくとも1種のロジウム化合物を含む有機溶液の形態の成分(i’)と、成分(i’)とは異なる少なくとも1種のさらなる別個の成分とを含む多成分系。
- ヒドロシリル化における触媒としての請求項1から請求項10のいずれか一項に記載の組成物の使用、又はヒドロシリル化可能な組成物としての請求項11若しくは請求項12に記載の組成物の使用。
- 前記ヒドロシリル化が、低分子シラン化合物の化学合成又はポリマーネットワークを形成する重付加である請求項14に記載の使用。
- 前記重付加が、印象、シーリング剤、包埋剤、封止材、含浸剤、エラストマー成形部品若しくは基材上のコーティングの形成のために作用するか、又はそれらの製造からなる請求項15に記載の使用。
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EP17178145.3 | 2017-06-27 | ||
EP17178145 | 2017-06-27 | ||
PCT/EP2017/083477 WO2019001754A1 (de) | 2017-06-27 | 2017-12-19 | Synergistische kombinationen von platin- und rhodiumverbindungen als katalysatoren bei hydrosilylierungen |
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Country Status (7)
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US (1) | US11180613B2 (ja) |
EP (1) | EP3645543B1 (ja) |
JP (1) | JP2020522382A (ja) |
KR (1) | KR102412026B1 (ja) |
CN (1) | CN110753696A (ja) |
CA (1) | CA3061805A1 (ja) |
WO (1) | WO2019001754A1 (ja) |
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WO2022010858A1 (en) * | 2020-07-06 | 2022-01-13 | Dow Silicones Corporation | Catalyst, redox-switchable catalyst system, and related methods involving hydrosilylation |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2004519544A (ja) * | 2001-01-03 | 2004-07-02 | ヘンケル ロックタイト コーポレイション | 低温高速硬化シリコーン組成物 |
JP2009114240A (ja) * | 2007-11-02 | 2009-05-28 | Shin Etsu Chem Co Ltd | 透明材料用含フッ素硬化性組成物 |
JP2014076924A (ja) * | 2012-10-11 | 2014-05-01 | Asahi Kasei E-Materials Corp | 表面修飾された複合金属酸化物微粒子 |
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US3814730A (en) * | 1970-08-06 | 1974-06-04 | Gen Electric | Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes |
US3775452A (en) | 1971-04-28 | 1973-11-27 | Gen Electric | Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes |
DE10035644C1 (de) | 2000-07-20 | 2001-12-20 | Heraeus Gmbh W C | Verfahren zur Herstellung von Platin-Alkenylpolysiloxan-Komplexen, insbesondere von Platin-Divinyltetramethyldisiloxan |
DE10150489B4 (de) | 2001-10-16 | 2004-02-05 | W. C. Heraeus Gmbh & Co. Kg | Herstellungsverfahren von Platin-Alkenylpolysiloxan-Komplexe, insbesondere Platin-Divinyltetramethyldisiloxan |
CN102417981B (zh) | 2011-11-22 | 2013-05-01 | 中国科学院过程工程研究所 | 一种离子液体基三液相体系萃取分离铂钯铑的方法 |
-
2017
- 2017-12-19 KR KR1020207001555A patent/KR102412026B1/ko active IP Right Grant
- 2017-12-19 WO PCT/EP2017/083477 patent/WO2019001754A1/de unknown
- 2017-12-19 CN CN201780092248.7A patent/CN110753696A/zh active Pending
- 2017-12-19 CA CA3061805A patent/CA3061805A1/en not_active Abandoned
- 2017-12-19 US US16/626,485 patent/US11180613B2/en active Active
- 2017-12-19 EP EP17821878.0A patent/EP3645543B1/de active Active
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JP2004519544A (ja) * | 2001-01-03 | 2004-07-02 | ヘンケル ロックタイト コーポレイション | 低温高速硬化シリコーン組成物 |
JP2009114240A (ja) * | 2007-11-02 | 2009-05-28 | Shin Etsu Chem Co Ltd | 透明材料用含フッ素硬化性組成物 |
JP2014076924A (ja) * | 2012-10-11 | 2014-05-01 | Asahi Kasei E-Materials Corp | 表面修飾された複合金属酸化物微粒子 |
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Title |
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CN110753696A (zh) | 2020-02-04 |
EP3645543B1 (de) | 2021-03-17 |
US20200115504A1 (en) | 2020-04-16 |
EP3645543A1 (de) | 2020-05-06 |
KR20200019214A (ko) | 2020-02-21 |
CA3061805A1 (en) | 2019-01-03 |
US11180613B2 (en) | 2021-11-23 |
KR102412026B1 (ko) | 2022-06-22 |
WO2019001754A1 (de) | 2019-01-03 |
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