JP2018528994A - 金属−含窒素複素環式カルベン縮合反応触媒を用いたポリオルガノシロキサン組成物及びその調製方法 - Google Patents
金属−含窒素複素環式カルベン縮合反応触媒を用いたポリオルガノシロキサン組成物及びその調製方法 Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims abstract description 116
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 24
- 238000006482 condensation reaction Methods 0.000 title claims abstract description 17
- 239000007809 chemical reaction catalyst Substances 0.000 title description 7
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000002736 metal compounds Chemical class 0.000 claims abstract description 16
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims abstract description 7
- -1 zinc (II) compound Chemical class 0.000 claims description 126
- 125000000217 alkyl group Chemical group 0.000 claims description 72
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 26
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
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- 229910020175 SiOH Inorganic materials 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
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- 150000001408 amides Chemical class 0.000 claims description 4
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- 239000001257 hydrogen Substances 0.000 claims description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 4
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical group [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 150000003752 zinc compounds Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 150000003852 triazoles Chemical class 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 159000000006 cesium salts Chemical class 0.000 claims description 2
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003609 titanium compounds Chemical class 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims 2
- RGRIQGFSVJVADW-UHFFFAOYSA-N CC1=C(C)C(C)=C(C)C1(C)[Zn]C1(C)C(C)=C(C)C(C)=C1C Chemical compound CC1=C(C)C(C)=C(C)C1(C)[Zn]C1(C)C(C)=C(C)C(C)=C1C RGRIQGFSVJVADW-UHFFFAOYSA-N 0.000 claims 1
- MCEANVLGNMOODQ-UHFFFAOYSA-N OB(O)O.C1=CNC=C1.C1=CNC=C1.C1=CNC=C1 Chemical class OB(O)O.C1=CNC=C1.C1=CNC=C1.C1=CNC=C1 MCEANVLGNMOODQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 15
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- 239000003054 catalyst Substances 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 125000000962 organic group Chemical group 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 20
- 239000002184 metal Substances 0.000 description 20
- 229920002050 silicone resin Polymers 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
- 125000000753 cycloalkyl group Chemical group 0.000 description 15
- 239000000546 pharmaceutical excipient Substances 0.000 description 15
- 125000004430 oxygen atom Chemical group O* 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 12
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 229910000077 silane Inorganic materials 0.000 description 11
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 10
- 239000004971 Cross linker Substances 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 9
- 238000004132 cross linking Methods 0.000 description 9
- 229920005684 linear copolymer Polymers 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 8
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- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 description 7
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 7
- 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 7
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 7
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 description 7
- 125000003944 tolyl group Chemical group 0.000 description 7
- 0 CN1C=CN(C)C1*C1N(C)C=CN1C Chemical compound CN1C=CN(C)C1*C1N(C)C=CN1C 0.000 description 6
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
- 125000002704 decyl group Chemical group [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])* 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 125000002948 undecyl 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])[H] 0.000 description 6
- 125000005023 xylyl group Chemical group 0.000 description 6
- PCTZLSCYMRXUGW-UHFFFAOYSA-N 1,1,1,2,2-pentafluorobutane Chemical group [CH2]CC(F)(F)C(F)(F)F PCTZLSCYMRXUGW-UHFFFAOYSA-N 0.000 description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 5
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
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- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- KXJLGCBCRCSXQF-UHFFFAOYSA-N [diacetyloxy(ethyl)silyl] acetate Chemical compound CC(=O)O[Si](CC)(OC(C)=O)OC(C)=O KXJLGCBCRCSXQF-UHFFFAOYSA-N 0.000 description 3
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- JNDMLEXHDPKVFC-UHFFFAOYSA-N aluminum;oxygen(2-);yttrium(3+) Chemical compound [O-2].[O-2].[O-2].[Al+3].[Y+3] JNDMLEXHDPKVFC-UHFFFAOYSA-N 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
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- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
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- YPIFGDQKSSMYHQ-UHFFFAOYSA-M 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC([O-])=O YPIFGDQKSSMYHQ-UHFFFAOYSA-M 0.000 description 2
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- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
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Abstract
【選択図】なし
Description
本出願は、米国特許法第119条(e)に基づき、2015年7月27日に出願された米国特許仮出願第62/197,124号の優先権を主張するものであり、その開示の全容が、参照により本明細書に組み込まれる。
構成成分i)の金属化合物
構成成分ii)は、含窒素複素環式カルベン(NHC)である。理論に束縛されるものではないが、構成成分ii)のカルベン官能性(functionality)が、金属原子に配位し、及び/又はNHCが構成成分i)、すなわち上述の金属化合物中の置換基Rの1個以上の実例に取って代わり、金属−含窒素複素環式カルベン錯体(M−NHC錯体)を形成すると考えられる。
縮合反応触媒、すなわち成分(A)は、M−NHC錯体を含む。M−NHC錯体は一般式(V)、[MLn][A]y[式中、Mは上述したようにZn又はTiであり、各配位子Lは、一般式(P)中のRについて上述した任意の置換基である。ただし、少なくとも1個のLはNHC配位子で、下付き文字nは、1からLである置換基の配位数に応じた最大配位部位数までである。]を有し得る。n=6である例は、以下の組み合わせのいずれかを含む;6個の単座配位子、4個の単座配位子及び1個の二座配位子、3個の単座配位子及び1個の三座配位子、2個の単座配位子及び2個の二座配位子、2個の単座配位子及び1個の四座配位子、1個の単座配位子及び1個の五座配位子、1個の単座配位子及び1個の二座配位子及び1個の三座配位子、3個の二座配位子、2個の三座配位子、1個の六座配位子、又は1個の二座配位子及び1個の四座配位子。n=5である例は、以下の組み合わせのいずれかを含む;5個の単座配位子、3個の単座配位子及び1個の二座配位子、2個の単座配位子及び1個の三座配位子、1個の単座配位子及び2個の二座配位子、1個の単座配位子及び1個の四座配位子、1個の二座配位子及び1個の三座配位子、又は1個の五座配位子。n=4である例は、以下の組み合わせのいずれかを含む;4個の単座配位子、2個の単座配位子及び1個の二座配位子、2個の二座配位子、1個の単座配位子及び1個の三座配位子、又は1個の四座配位子。n=3である例は、以下の組み合わせのいずれかを含む;3個の単座配位子、1個の単座配位子及び1個の二座配位子、又は1個の三座配位子。n=2である例は、以下の組み合わせのいずれかを含む;2個の単座配位子、又は1個の二座配位子。n=1である例は、1個の単座配位子を含む。NHC配位子は、単座から三座であり得る。例えば、一般式(I)のNHC配位子は、単座であり得る[式中、R51及びR52は、各々メチルであり、Q、R53及びR54は、上述した通りである。]あるいは、一般式(I)のNHC配位子は、例えば、R51及びR52の一方が2個以上の炭素原子を有する場合には、二座であり得る。更に、一般式(III)のNHC配位子は、例えば、R51及びR52の両方が2個以上の炭素原子を有する場合には、三座であり得る。[A]y[式中、下付き文字yは、Znでは0〜2、Tiでは0〜4であり得る。]は、錯体の全体的な電荷をゼロにするための結合していないアニオン種を表す。一般式(V)では、Aは結合していないアニオン種を表す。Aの例としては、シアナイド、アイオダイド、ブロマイド、クロライド、フルオライド、ナイトレート、ナイトライト、ホスフェート、ホスファイト、サルフェート、サルファイト、トリフレート、トシレート、ブロシレート(brosylate)、ノシレート(nosylate)、スルホネート、ホルメート、オキサレート、アセテート、チオサルフェート、ヒドロキシド、カーボネート、バイカーボネート、バイサルフェート、バイサルファイト、クロレート、クロライト、パークロレート、ハイポクロライト、又はこれらの任意の組み合わせが挙げられるが、これらに限定されない。M−NHC錯体は、上述の構成成分i)及び構成成分ii)とは違う(異なる)。
成分(B)は、1分子あたり平均で、ケイ素に結合したヒドロキシ部分(Si−OH)を1個以上、あるいはSi−OH部分を2個以上有するシラノール官能性化合物である。成分(B)は、追加の官能基(すなわち、Si−OH以外の1個以上の官能基)、例えば、カルボキシル、アミノ、尿素、カルバメート、アミド、又はエポキシ等を含有してもよい。成分(B)は1分子あたり2個のSi−OH部分を有してもよい。あるいは、成分(B)は、平均で1分子あたり1個より多いSi−OH部分、あるいは1分子あたり2個以上のSi−OH部分、あるいは1分子あたり10〜1000個のSi−OH部分を有してもよい。成分(B)は、ポリジオルガノシロキサン等のポリオルガノシロキサン、又はOHがポリマー主鎖中及び/又は末端のSi原子に共有結合するSi−OH部分を1個以上有するシリコーン−有機コポリマーから選択されてもよい。あるいは、成分(B)は、ポリオルガノシロキサンであってもよい。成分(B)中のSi−OH部分は、化合物中の末端位、側鎖位又は末端位と側鎖位との両方に位置してもよい。成分(B)は、直鎖状、分岐状、環状又は樹脂性構造を含み得る。あるいは、成分(B)は、直鎖状、分岐状、又は環状構造を含み得る。あるいは、成分(B)は、直鎖状又は分岐状構造を含み得る。あるいは、成分(B)は、直鎖状構造を含み得る。あるいは、成分(B)は、直鎖状構造及び樹脂状構造を含み得る。成分(B)は、ホモポリマー又はコポリマー又はこれらの組み合わせを含み得る。
40〜90モル%の、式[R71 2SiO2/2]のジシロキシ単位、
10〜60モル%の、式[R72SiO3/2]のトリシロキシ単位及び
0.5〜35モル%のシラノール基[≡SiOH]
[式中、
各R71及び
R72は、独立して、1〜30個の炭素原子を有する炭化水素基又は1〜30個の炭素原子を有するハロゲン化炭化水素基である。
ここで、
ジシロキシ単位[R71 2SiO2/2]は、直鎖状ブロック中に配置されており、直鎖状ブロック1個あたり平均して10〜400個のジシロキシ単位[R71 2SiO2/2]を有し、
トリシロキシ単位[R72SiO3/2]は、少なくとも500g/モルの分子量を有する非直鎖状ブロック中に配置されており、この非直鎖状ブロックの少なくとも30%は互いに架橋されており、
各直鎖状ブロックは、少なくとも1個の非直鎖状ブロックに連結され、
オルガノシロキサンブロックコポリマーの重量平均分子量(Mw)は少なくとも20,000g/モルである。]を含むオルガノシロキサンブロックコポリマーである。本明細書で使用されるとき、「オルガノシロキサンブロックコポリマー」又は「樹脂−直鎖状オルガノシロキサンブロックコポリマー」は、「直鎖状」Dシロキシ単位を「樹脂」Tシロキシ単位と組み合わせて含有するオルガノポリシロキサンを指す。いくつかの実施形態では、オルガノシロキサンコポリマーは、「ランダム」コポリマーとは対照的に、「ブロック」コポリマーである。本開示の実施形態の「樹脂−直鎖状オルガノシロキサンブロックコポリマー」は、それ自体はD及びTシロキシ単位を含有するオルガノポリシロキサンを指し、ここでD単位(すなわち、[R1 2SiO2/2]単位)は主に互いに結合して、いくつかの実施形態において、平均で10〜400D単位(例えば、10〜400D単位、10〜300D単位、10〜200D単位、10〜100D単位、50〜400D単位、100〜400D単位、150〜400D単位、200〜400D単位、300〜400D単位、50〜300D単位、100〜300D単位、150〜300D単位、200〜300D単位、100〜150D単位、115〜125D単位、90〜170D単位又は110〜140D単位)を有するポリマー鎖を形成し、これは本明細書において「直鎖状ブロック」と称される。
(HddR2 (3−dd)SiR3 1/2)2(R2 2SiO2/2)ee(HR2SiO2/2)ffのポリオルガノハイドロジェンシロキサンを含んでもよい。
式中、各R2は、独立して一価の有機基であり、各R3は、独立して酸素原子又は二価の炭化水素基であり、各下付き文字ddは、独立して、0、1、2又は3であり、eeは0以上であり、ffは0以上であり、数量(ee+ff)は、25℃にて少なくとも5mPa・sの粘度及び/又は少なくとも1のDPを有する、ポリジオルガノシロキサンを与えるのに十分な、値を有する整数である。ただし、ddとffとの少なくとも一方は、0より大きい。DPは、ポリスチレン標準較正を使用して、GPCによって測定されてもよい。あるいは、下付き文字eeは、1〜200,000の範囲の値を有してもよい。
賦形剤(例えば、溶媒及び/又は希釈剤)が組成物中で使用されてもよい。賦形剤は、組成物の流動及びシリコーン樹脂等の特定の成分の導入を容易にし得る。本明細書で使用される賦形剤は、組成物の成分の流動化を補佐するがこれらの成分のいずれとも本質的に反応しないものである。賦形剤は、組成物中の成分の可溶性及び揮発性に基づいて選択されてもよい。「可溶性」は、賦形剤が組成物の成分を溶解及び/又は分散させるのに十分であることを指す。「揮発性」は、賦形剤の蒸気圧を指す。賦形剤の揮発性が高すぎる(高すぎる蒸気圧を有する)場合、適用温度にて組成物中に気泡が生じる場合があり、この気泡は、亀裂を生じるか、又は別の方法で硬化生成物の特性を弱めるか若しくは特性に悪影響を与える恐れがある。しかしながら、賦形剤が十分に揮発性でない(蒸気圧が低すぎる)場合には、賦形剤は、組成物の反応生成物において可塑剤のままとなるか、又は反応生成物が物理特性を発現するための時間が所望よりも長くなる恐れがある。
Claims (20)
- (A)触媒的に有効な量の反応生成物と、(B)シラノール官能性化合物と、を混合することで生成された組成物であって、
(A)が、
i)チタン化合物及び亜鉛化合物から選択される金属化合物、並びに
ii)含窒素複素環式カルベン、
を組み合わせること、を含む、方法により調製された、前記触媒的に有効な量の反応生成物であり、
(B)が、平均で1分子あたり1個以上の、ケイ素に結合したヒドロキシ部分を有する、前記シラノール官能性化合物であり、
成分(A)が、成分(B)の前記ヒドロキシ部分の縮合反応を触媒するものである、組成物。 - 前記金属化合物が、亜鉛(II)化合物である、請求項1に記載の組成物。
- 前記金属化合物が、ジアルキル亜鉛化合物、ジアリール亜鉛化合物、亜鉛ジハライド、亜鉛ジアルコキシド、亜鉛ジエステル及び亜鉛(II)ビス(トリアルキルシリル)アミドから選択される、請求項1又は2に記載の組成物。
- 前記亜鉛(II)化合物が、ビス(ペンタメチルシクロペンタジエニル)亜鉛、ジエチル亜鉛、亜鉛ジブトキシド、亜鉛ジアセチルアセトネート及びZnCl2から選択される、請求項2に記載の組成物。
- 前記含窒素複素環式カルベンが、一般式(I)
- 各破線が、二重結合を示し、R60、R61、R62及びR63は、各々独立して、水素、又はメチル、エチル、プロピル若しくはブチルから選択されるアルキル基から選択される、請求項7に記載の組成物。
- 前記含窒素複素環式カルベンが、アゾリウム塩と塩基とを組み合わせること、を含む、方法により調製された、請求項1〜9のいずれか一項に記載の組成物。
- 前記アゾリウム塩が、アゾリウムハライド及びアゾリウムボレートからなる群から選択される、請求項10に記載の組成物。
- 前記塩基が、セシウム塩、KH、K(N(SiMe3)3)2、NaOH、KOH、ピリジン、リチウムジイソプロピルアミド、カリウムt−ブトキシド、NaH又はLiN(SiMe3)2からなる群から選択される、請求項10又は11に記載の組成物。
- 成分(A)が、一般式[MLn][X]y
[式中、MはZn又はTiであり、各Lがハロゲン原子、一価の炭化水素基、アミノ基、シリルアミド基、カルボキシレートエステル基、ハイドロカーボンオキシ基及び含窒素複素環式カルベン配位子からなる群から選択され(ただし少なくとも1個のLは前記含窒素複素環式カルベン配位子である。)、下付き文字nは、前記Lの置換基の配位数又はハプト数にかかわらず、1からMへの結合点の最大数までであり、Xは、錯体の全体的な電荷をゼロにするための結合していないアニオン化学種であり、MがZnであるとき下付き文字yは0〜2であり、MがTiであるとき下付き文字yは0〜4である。]の前記錯体を含む、請求項1〜12のいずれか一項に記載の組成物。 - 成分(B)が、
40〜90モル%の式[R71 2SiO2/2]のジシロキシ単位、
10〜60モル%の式[R72SiO3/2]のトリシロキシ単位、及び
0.5〜35モル%のシラノール基[≡SiOH]
[式中、
各R71及びR72は、独立して、1〜30個の炭素原子を有する炭化水素基、又は1〜30個の炭素原子を有するハロゲン化炭化水素基であり、
前記ジシロキシ単位[R71 2SiO2/2]は、直鎖状ブロック中に配置されており、直鎖状ブロック1個あたり平均して10〜400個のジシロキシ単位[R71 2SiO2/2]を有し、
前記トリシロキシ単位[R72SiO3/2]は、分子量が少なくとも500g/モルの非直鎖状ブロック中に配置されており、前記非直鎖状ブロックの少なくとも30%は互いに架橋されており、各直鎖状ブロックは少なくとも1個の非直鎖状ブロックに結合されており、更に、
前記オルガノシロキサンブロックコポリマーは、少なくとも20,000g/モルの重量平均分子量を有する。]を含むオルガノシロキサンブロックコポリマー、を含む、請求項1〜14のいずれか一項に記載の組成物。 - 充填剤を更に含む、請求項1〜15のいずれか一項に記載の組成物。
- 前記充填剤が蛍光体を含む、請求項16に記載の組成物。
- 架橋剤を更に含む、請求項1〜17のいずれか一項に記載の組成物。
- 前記架橋剤がアルコキシシラン又はポリオルガノハイドロジェンシロキサンである、請求項18に記載の組成物。
- 請求項1〜19のいずれか一項に記載の組成物を水分に暴露することにより、反応生成物を調製すること、を含む、方法。
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