JP2023523544A - 放射線架橋性基及び水分架橋性基を有するポリシロキサン - Google Patents
放射線架橋性基及び水分架橋性基を有するポリシロキサン Download PDFInfo
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- JP2023523544A JP2023523544A JP2022562467A JP2022562467A JP2023523544A JP 2023523544 A JP2023523544 A JP 2023523544A JP 2022562467 A JP2022562467 A JP 2022562467A JP 2022562467 A JP2022562467 A JP 2022562467A JP 2023523544 A JP2023523544 A JP 2023523544A
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- -1 Polysiloxane Polymers 0.000 title claims description 121
- 229920001296 polysiloxane Polymers 0.000 title claims description 28
- 230000005855 radiation Effects 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 92
- 125000000962 organic group Chemical group 0.000 claims abstract description 74
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004355 nitrogen functional group Chemical group 0.000 claims abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract 2
- 150000003254 radicals Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 7
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- 125000005372 silanol group Chemical group 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 238000007348 radical reaction Methods 0.000 claims description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
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- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 7
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- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 description 4
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- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 4
- BWYLUCQZPVGWLL-UHFFFAOYSA-N n-butyl-n-(triethoxysilylmethyl)butan-1-amine Chemical compound CCCCN(CCCC)C[Si](OCC)(OCC)OCC BWYLUCQZPVGWLL-UHFFFAOYSA-N 0.000 description 4
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- 229910020175 SiOH Inorganic materials 0.000 description 3
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- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- WUFHQGLVNNOXMP-UHFFFAOYSA-N n-(triethoxysilylmethyl)cyclohexanamine Chemical compound CCO[Si](OCC)(OCC)CNC1CCCCC1 WUFHQGLVNNOXMP-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- 239000007787 solid Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000004001 thioalkyl group Chemical group 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 2
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 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
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920006268 silicone film Polymers 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- KRKBPDSHHSQBKA-UHFFFAOYSA-N triethoxy(piperazin-1-ylmethyl)silane Chemical compound CCO[Si](OCC)(OCC)CN1CCNCC1 KRKBPDSHHSQBKA-UHFFFAOYSA-N 0.000 description 1
- PCFOIHAKYIHHLJ-UHFFFAOYSA-N triethoxy(piperidin-1-ylmethyl)silane Chemical compound CCO[Si](OCC)(OCC)CN1CCCCC1 PCFOIHAKYIHHLJ-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- DSKBCOYXMOWPQQ-UHFFFAOYSA-N triethoxy(pyrrol-1-ylmethyl)silane Chemical compound CCO[Si](OCC)(OCC)CN1C=CC=C1 DSKBCOYXMOWPQQ-UHFFFAOYSA-N 0.000 description 1
- ZGDJHRRJWYVMGV-UHFFFAOYSA-N triethoxy-[(4-methylpiperazin-1-yl)methyl]silane Chemical compound CCO[Si](OCC)(OCC)CN1CCN(C)CC1 ZGDJHRRJWYVMGV-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000002759 woven fabric Substances 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
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/28—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen sulfur-containing groups
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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
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing 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
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy 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
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
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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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/392—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing sulfur
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- C—CHEMISTRY; METALLURGY
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
Abstract
Description
RnSiO(4-n/2 (I)
式中、
nは、0、1、2又は3であり、いずれの場合も一般式(I)の全単位に基づいて、n=0の単位の割合は50mol%以下であり、n=1の単位の割合は60mol%以下であり、
Rは、R1、-OR2、Ru、RS及びQから選択され、ここで
R1は、1~18個の炭素原子を有する一価の置換又は非置換の炭化水素基を示し、
R2は、水素原子又は1~6個の炭素原子を有する一価の置換又は非置換の炭化水素基を示し、
Ruは、2~18個の炭素原子を有する一価の脂肪族不飽和炭化水素基を示し、
RSは、1~18個の炭素原子を有する一価のチオール官能化炭化水素基を示し、
Qは、式(II)の窒素官能基であり、
-CR5R6-NR4R3 (II)、
式中、
R3及びR4はそれぞれ独立して水素又は1~18個の炭素原子を有する置換又は非置換の炭化水素基を示し、
R5及びR6はそれぞれ独立して水素又はメチル基を示し、
ただし、オルガノ(ポリ)シロキサン(A)は、1分子当たり一般式(III)の少なくとも1つの単位、少なくとも2つの脂肪族不飽和基Ru及び少なくとも2つのチオール官能化基RSを含み、
Q-Si(OR7)2O1/2 (III)
式中、R7はR2に対し定義された通りである。
(R2O)3Si-CR5R6-NR4R3 (IV)
脂肪族不飽和基Ru及びチオール官能化基RSの両方を含むポリシロキサン(V)のシラノール基との縮合が好ましい。このシラノール含有ポリシロキサン(V)の調製については、例えば、DE4120418A1号に記載されている。チオール官能化基RSは、好ましくは、対応するチオール官能化アルコキシシランを介してポリシロキサン骨格に組み込まれるので、ポリシロキサン(V)は、それらの調製の結果として、一般式(IV)のアルコキシシランとの縮合反応において好ましくは保持されるアルコキシ基を既に含み得る。
磁気的に結合させたガラスパドル撹拌機、滴下漏斗、温度計及びカラムヘッド付き還流冷却器を備えた0.5Lフランジフラスコに、ビニルメチルジクロロシラン(99%、Wacker Chemie AG)18.7gを仕込み、平均27個のジメチルシロキシ単位を有するα,ω-ジヒドロキシジメチルポリシロキサン(Wacker Chemie AG)152.2gを25~27℃で20分間かけて計量する。3,5-ジ-tert-ブチル-4-ヒドロキシトルエン(99%、Sigma-Aldrich)0.16gを安定剤として加え、その後混合物を100℃まで加熱し、この温度で1時間撹拌する。次に「PNCl2」(Wacker Chemie AG、平衡触媒)0.54gを加える。3-チオプロピルメチルジメトキシシラン(≧95%、Sigma-Aldrich)45gを20分間かけて透明な反応混合物に計量し、さらに「PNCl2」0.54gを加える。この混合物を100℃でさらに2時間撹拌し、80℃まで冷却し、1%塩酸30gを加え、その後15分間撹拌し、次いで脱イオン水20g中の酸化マグネシウム4gの懸濁液を加える。次いで、反応混合物を80℃で1時間撹拌し、その後、全ての揮発性物質を110℃まで1hPaで留去する。残渣を室温まで冷却した後、加圧吸引フィルターで濾過する。粘度65mPa・sの透明な液が濾液として得られる。
X-Me2SiO1/2:X-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2=1.9:0.1:29.5:2:5.1
X=54%OH、46%OMe
実施例1を繰り返すが、1%塩酸30gの代わりに9%塩酸33gを用いる。
X-Me2SiO1/2:X-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2=1.8:0.2:116.6:6.6:16.4
X=95%OH、5%OMe
磁気的に結合させたガラスパドル撹拌機、滴下漏斗、温度計及びカラムヘッド付き還流冷却器を備えた1Lの四つ首フラスコに、ビニルメチルジクロロシラン(99%、Wacker Chemie AG)18.7gを仕込み、メチルビニルシロキシ単位の割合が25mol%のα,ω-ジヒドロキシジメチルポリシロキサン(Wacker Chemie AG)47.7gを24℃で10分間かけて計量する。次に平均27個のジメチルシロキシ単位を有するα,ω-ジヒドロキシジメチルポリシロキサン(Wacker Chemie AG)104.5gを20分間かけて加える。3,5-ジ-tert-ブチル-4-ヒドロキシトルエン(99%、Sigma-Aldrich)0.16gを安定剤として加え、次に混合物を100℃まで加熱し、この温度で1時間撹拌する。次にトリフルオロメタンスルホン酸(Merk)0.5gを加える。3-チオプロピルメチルジメトキシシラン(≧95%、Sigma-Aldrich)22.7gを20分間かけて透明な反応混合物中に計量し、さらにトリフルオロメタンスルホン酸0.5gを加える。この混合物を100℃でさらに2時間撹拌し、80℃まで冷却し、脱イオン水46.6g中の酸化マグネシウム4gの懸濁液を添加する。次いで、反応混合物を80℃で1時間撹拌し、その後全ての揮発性物質を110℃まで1hPaで留去する。
X-Me2SiO1/2:X-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2=1.6:0.4:48.2:6.7:4
X=67%OH、33%OMe
実施例2のポリシロキサン60gをN,N-ジ-n-ブチルアミノメチルトリエトキシシラン18.6gと撹拌しながら室温で混合する。その直後に、透明混合物の1H-NMRスペクトル及び29Si-NMRスペクトルを記録する。個々のシロキシ単位のモル比を積分値から計算する。2つの末端基に対する正規化により、以下の組成が得られる。
MeO-Me2SiO1/2:MeO-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2:(nBu)2N-CH2-Si(OEt)2O1/2:(nBu)2N-CH2-Si(OEt)3=0.5:0.2:46.3:6:3.7:1.3:3.4
実施例3の生成物10gをテトラエトキシ部分加水分解物(Wacker TES40)1g、シリコーン樹脂(MQ樹脂803)4g、及び光開始剤Darocur(R)1173(Sigma-Aldrich、2-メチル-1-フェニル-プロパン-2-オール-1-オン)0.2gと混合する。粘度が709mPa・sの透明な混合物の一部を層厚約0.1mmでガラスボウルに注ぎ、UVチャンバー(Uvacube、Hoenle、Hgハロゲン化物ランプ、290~415nm、2000W)中でUV照射すると、15秒以内に透明な加硫物に架橋する。
磁気的に結合させたガラスパドル撹拌機、滴下漏斗、温度計及びカラムヘッド付き還流冷却器を備えた0.5Lの三つ首フラスコに、平均420個のジメチルシロキシ単位を有するα,ω-ジヒドロキシジメチルポリシロキサン(Wacker Chemie AG、CT 6000)207.5gを仕込み、メチルビニルシロキシ単位の割合が25mol%のα,ω-ジヒドロキシジメチルポリシロキサン(Wacker Chemie AG)94.6gを加える。次にビニルメチルジクロロシラン(99%、Wacker Chemie AG)37.1gを25分間かけて計量する。3,5-ジ-tert-ブチル-4-ヒドロキシトルエン(99%、Sigma-Aldrich)0.3gを加え、混合物を100℃まで加熱し、この温度で約25分間撹拌する。トルエン中の「PNCl2」の10%溶液0.4gを添加し、次いで混合物を100℃でさらに2時間撹拌する。
X-Me2SiO1/2:X-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2=1.58:0.42:45.3:6.2:3.7
X=53%OH、47%OMe
実施例5のポリシロキサン20gをN,N-ジ-n-ブチルアミノメチルトリエトキシシラン4.64gと撹拌しながら室温で混合する。
実施例5のポリシロキサン20gを4.4gのN-シクロヘキシルアミノメチルトリエトキシシランと撹拌しながら室温で混合する。
<7a) (SH:Vi 約1:2のポリシロキサン(V)の調製)及び2×0.01重量%のPNCl2触媒>
磁気的に結合させたガラスパドル撹拌機、滴下漏斗、温度計及びカラムヘッド付き還流冷却器を備えた2Lフランジフラスコに、ビニルメチルジクロロシラン(99%、Wacker Chemie AG)56gを仕込み、メチルビニルシロキシ単位の割合が25mol%のα,ω-ジヒドロキシジメチルポリシロキサン(Wacker Chemie AG)143g及び平均27個のジメチルシロキシ単位を有するα,ω-ジヒドロキシジメチルポリシロキサン(Wacker Chemie AG)313.5gを、それぞれ25~27℃で30分間かけて連続的に計量する。3,5-ジ-tert-ブチル-4-ヒドロキシトルエン(99%、Sigma-Aldrich)0.5gを安定剤として加え、次に混合物を100℃まで加熱し、この温度で1時間撹拌する。次にキシレン中の10%「PNCl2」溶液(Wacker Chemie AG、平衡触媒)0.6g(全混合物に基づいて0.01重量%に相当)を加える。3-チオプロピルメチルジメトキシシラン(≧95%、Sigma-Aldrich)68gを30分間かけて透明な反応混合物に計量し、さらに10%「PNCl2」溶液0.6gを加える。混合物を100℃でさらに2時間撹拌し、80℃まで冷却し、次いで脱イオン水140g中の酸化マグネシウム12gの懸濁液を添加する。次いで、反応混合物を75℃~80℃で75分間撹拌し、その後、全ての揮発性物質を110℃まで1hPaで留去する。残渣を室温まで冷却した後、加圧吸引フィルターで濾過する。粘度42mPa・sの透明な液が濾液として得られる。生成物の組成は1H及び29Si NMRで決定する。これは以下の平均的な組成を与える。
X-Me2SiO1/2:X-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2=1.74:0.26:21:3:1.7
X=39%OH、61%OMe
同様の方法で精査すると、粘度65mPa・sの透明な液体を単離する。生成物の組成は1H及び29Si NMRで決定する。これは以下の平均的な組成を与える。
X-Me2SiO1/2:X-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2=1.67:0.33:27:3.8:2
X=64%OH、36%OMe
実施例7a)のポリマー60g(NMR分析によると、21mmol SiOH)をN,N-ジ-n-ブチルアミノトリエトキシシラン7.7g(25mmol)、ビニルトリエトキシシラン(99%、Wacker Chemie AG)11.2g(59mmol)、及び安定剤としての3,5-ジ-tert-ブチル-4-ヒドロキシトルエン(99%、Sigma-Aldrich)0.3gと撹拌しながら室温で混合する。その直後に、透明な混合物の1H-NMRスペクトル及び29Si-NMRスペクトルを記録する。個々のシロキシ単位のモル比を積分値から計算する。2つの末端基に対する正規化により、以下の組成が得られる。
MeO-Me2SiO1/2:MeO-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2:(nBu)2N-CH2-Si(OEt)2O1/2:ViSi(OEt)2O1/2:(nBu)2N-CH2-Si(OEt)3:ViSi(OEt)3=1.1:0.1:27:3.3:1.7:0.6:0.2:0.2:2=>60%MeO、30%DBA-DEO、10%Vi-DEO.
1重量%の2-メチル-1-フェニル-プロパン-2-オール-1-オン(Darocur 1173)、又は1-ヒドロキシシクロヘキシルフェニルケトン(Omnirad 184)、又はベンゾフェノン(Omnirad BP Flakes)、又は2,2-ジメトキシ-2-フェニルアセトフェノン(Omnirad BDK)(全ての光開始剤は、IGM、ノースカロライナ州から市販されている)を実施例6a又は6bのシロキサンに添加する。粘度1000mPa・s未満の無色透明の油状の混合物を、ドクターブレード(Byk Inc.製)を用いてポリエステルフィルムに層厚0.1mmで塗布する。次に、被覆されたポリエステル基材を空気の存在下で照射する。光開始剤にかかわらず、被膜はUVチャンバー(Hoenle製のUvacube 2000、ハロゲン化水銀金属(Fランプ)光源1000mJ/cm2を装備、波長範囲290nm~415nm)で30秒間の紫外線照射後に完全に硬化し、乾燥表面を形成する。別の試料を空気(相対湿度50%、23℃)の存在下及び光を排除した状態で同様にShore硬度測定用の鋳型に静置すると、40分未満でスキン形成(粘着なし)が起こる。UV架橋の直後、加硫物のShore OO硬度は50であり、その後、23℃及び50%相対湿度で1週間加硫物を保存した後、水分架橋は最大65に達する。
Omnirad BDK又はベンゾフェノンをそれぞれ1重量%含有するポリマー6a)及び6b)の混合物は、光を排除した閉鎖容器中で、70℃で2週間保存後、未変化のUV架橋挙動及び水分架橋挙動を示す。
上記の実施例を、市販のプリント基板(Uxcell(R) 3cm×7cm FR-4)を用いて試験する。これらの回路基板は、両面に錫を印刷した試作品である。被覆前に、50μlのフラックス(NC265LR)を塗布し、試験表面上で一晩乾燥させた。シロキサンP2及びPIを上記のように混合し、次いで、塗布した被膜をまずUV光で硬化させ、試料を大気湿度下で4日間保存して、完全に硬化させる。完全に硬化したプリント基板を、熱及び湿度(85℃/85%RH、2週間)の点から試験する。熱安定性(150℃、2週間)及び温度変化(1000時間-40℃/140℃)も試験する。これらの試験の後、接着性を、基板への被膜の接着性を決定するためのロバストな方法であるASTM3359-09規格クロスハッチ法に従って評価する。これは、メスで完全に硬化した被膜を基板表面までグリッドパターンで切断することによって行う。次に規格の粘着テープを加硫物表面に貼り付け、剥がす。次に、ASTM3359-09に記載されている絵表示に基づいて残っている四角形の数に従って、接着性を評価/定量化する。その結果を下表に示す。上記実施例を用いた試作板の試験では、接着促進剤を添加しなくても優れた接着性が認められ、加硫物強度及び接着性の安定性にも優れていた。その結果を表1に示す。
Claims (11)
- 一般式(I)の単位からなるオルガノ(ポリ)シロキサン(A)。
RnSiO(4-n/2 (I)
[式中、
nは、0、1、2又は3であり、いずれの場合も一般式(I)の全単位に基づいて、n=0の単位の割合は50mol%以下であり、n=1の単位の割合は60mol%以下であり、
Rは、R1、-OR2、Ru、RS及びQから選択され、ここで
R1は、1~18個の炭素原子を有する一価の置換又は非置換の炭化水素基を示し、
R1は、水素原子又は1~6個の炭素原子を有する一価の置換又は非置換の炭化水素基を示し、
Ruは、2~18個の炭素原子を有する一価の脂肪族不飽和炭化水素基を示し、
RSは、1~18個の炭素原子を有する一価のチオール官能化炭化水素基を示し、
Qは、式(II)の窒素官能基であり、
-CR5R6-NR4R3 (II)、
式中、
R3及びR4はそれぞれ独立して水素又は1~18個の炭素原子を有する置換又は非置換の炭化水素基を示し、
R5及びR6はそれぞれ独立して水素又はメチル基を示し、
ただし、オルガノ(ポリ)シロキサン(A)は、1分子当たり一般式(III)の少なくとも1つの単位、少なくとも1つの脂肪族不飽和基Ru及び少なくとも2つのチオール官能化基RSを含み、
Q-Si(OR7)2O1/2 (III)
式中、R7はR2に対し定義された通りである。] - Ruがビニル基又はアリル基である、請求項1に記載のオルガノ(ポリ)シロキサン(A)。
- 基RSが3~6個の炭素原子を有する直鎖状チオアルキル基を示す、請求項1又は2に記載のオルガノ(ポリ)シロキサン(A)。
- -NR4R3単位が、ジ-n-ブチルアミノ単位、アニリノ単位、シクロヘキシルアミノ単位、及びN-モルホリノ単位から選択される、請求項1~3のいずれか一項に記載のオルガノ(ポリ)シロキサン(A)。
- 一般式(I)の単位を10~400個有する、請求項1~4のいずれか一項に記載のオルガノ(ポリ)シロキサン(A)。
- 一般式(I)の全単位の少なくとも0.5mol%が、一般式(III)の単位である、請求項1~5のいずれか一項に記載のオルガノ(ポリ)シロキサン(A)。
- 基Ruに対する基RSのモル比が0.3~5の間の範囲内にある、請求項1~6のいずれか一項に記載のオルガノ(ポリ)シロキサン(A)。
- オルガノ(ポリ)シロキサン(A)の調製方法であって、一般式(IV)のアルコキシシランを
(R2O)3Si-CR5R6-NR4R3 (IV)
シラノール基と脂肪族不飽和基Ru及びチオール官能基RSの両方とを含むポリシロキサン(V)のシラノール基と縮合させる、方法。 - 請求項1~7に記載のオルガノ(ポリ)シロキサン(A)を含む水分架橋性及び放射線架橋性オルガノ(ポリ)シロキサン混合物(M)。
- 光開始剤(B)を含む、請求項9に記載のオルガノ(ポリ)シロキサン混合物(M)。
- 望ましくないフリー基反応を避けるための安定剤(C)を含む、請求項9又は10に記載のオルガノ(ポリ)シロキサン混合物(M)。
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