JP2008239489A - Novel organosilicon compound - Google Patents
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- JP2008239489A JP2008239489A JP2005203716A JP2005203716A JP2008239489A JP 2008239489 A JP2008239489 A JP 2008239489A JP 2005203716 A JP2005203716 A JP 2005203716A JP 2005203716 A JP2005203716 A JP 2005203716A JP 2008239489 A JP2008239489 A JP 2008239489A
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- 150000003961 organosilicon compounds Chemical class 0.000 title claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- -1 silane compound Chemical class 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 16
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract description 10
- 238000010511 deprotection reaction Methods 0.000 abstract description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- NKLYMYLJOXIVFB-UHFFFAOYSA-N triethoxymethylsilane Chemical compound CCOC([SiH3])(OCC)OCC NKLYMYLJOXIVFB-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 239000002210 silicon-based material Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 125000000962 organic group Chemical class 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- XPCFWBCVLSCGKE-UHFFFAOYSA-N C(C)O[Si](CCCO[SiH2]C(OCC)OCC)(OCC)OCC Chemical compound C(C)O[Si](CCCO[SiH2]C(OCC)OCC)(OCC)OCC XPCFWBCVLSCGKE-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 150000003377 silicon compounds Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- QFCSGCRCIUNXLC-UHFFFAOYSA-N C(C)O[Si](CCCC1=CC(=C(C=C1)O[SiH2]C(OCC)OCC)OC)(OCC)OCC Chemical compound C(C)O[Si](CCCC1=CC(=C(C=C1)O[SiH2]C(OCC)OCC)OC)(OCC)OCC QFCSGCRCIUNXLC-UHFFFAOYSA-N 0.000 description 1
- GRTSJMXNIQRUQG-UHFFFAOYSA-N CCOC(OCC)[SiH2]C1(C=CC(=CC1OC)CC=C)O Chemical compound CCOC(OCC)[SiH2]C1(C=CC(=CC1OC)CC=C)O GRTSJMXNIQRUQG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- FSIJKGMIQTVTNP-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C=C)C=C FSIJKGMIQTVTNP-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 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 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 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 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 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
- 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
- 239000003921 oil Substances 0.000 description 1
- 125000002524 organometallic group Chemical class 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 125000005371 silicon functional group Chemical group 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
本発明は、新規な有機ケイ素化合物に関し、さらに詳しくは、アルキルアルコキシシリル基により保護された水酸基を有するアルコキシシラン及びその製造法に関する。
The present invention relates to a novel organosilicon compound, and more particularly to an alkoxysilane having a hydroxyl group protected by an alkylalkoxysilyl group and a method for producing the same.
シリル基により保護された水酸基を含有するアルコキシシランは多数報告されている（例えば、非特許文献１）。
これまで、水酸基を保護したシリル基としてはトリアルキルシリル基であるものが多く、アルキルアルコキシシリル基であるものは知られていない。また、シリル基がトリアルキルシリル基である場合、シリル基は脱保護反応後には除去されるのみであり、脱保護により脱離したシリル基が例えばシルセスキオキサン骨格に組み込まれることは知られていない。
本発明の目的は、アルキルアルコキシシリル基により保護された水酸基を含有し、脱保護により脱離したシリル基がシルセスキオキサン骨格に組み込まれるアルコキシシランを提供することにある。
Until now, many of the silyl groups protecting the hydroxyl group are trialkylsilyl groups, and those that are alkylalkoxysilyl groups are not known. In addition, when the silyl group is a trialkylsilyl group, the silyl group is only removed after the deprotection reaction, and it is known that the silyl group eliminated by the deprotection is incorporated into, for example, a silsesquioxane skeleton. Not.
An object of the present invention is to provide an alkoxysilane containing a hydroxyl group protected by an alkylalkoxysilyl group and incorporating a silyl group eliminated by deprotection into a silsesquioxane skeleton.
本発明は、下記一般式（１）で表される有機ケイ素化合物及びその製造法である。 The present invention is an organosilicon compound represented by the following general formula (1) and a method for producing the same.
（式中、Ｒ1、Ｒ2、Ｒ4、Ｒ5およびＲ6は炭素数１から１０のアルキル基、アラルキル基またはアリール基であり、Ｒ3は炭素数２から１０のアルキレン基又は炭素数７から１０のフェニルアルキレン基を示し、ａおよびｂは、ａ≧０、ｂ≧１およびａ＋ｂ＝３を満たす整数である。）
Wherein R 1 , R 2 , R 4 , R 5 and R 6 are an alkyl group, aralkyl group or aryl group having 1 to 10 carbon atoms, and R 3 is an alkylene group or carbon number having 2 to 10 carbon atoms. 7 to 10 phenylalkylene groups, a and b are integers satisfying a ≧ 0, b ≧ 1 and a + b = 3.)
本発明によって、アルキルアルコキシシリル基により保護された水酸基を含有する新規なアルコキシシランが提供される。 According to the present invention, a novel alkoxysilane containing a hydroxyl group protected by an alkylalkoxysilyl group is provided.
本発明の新規な有機ケイ素化合物は、ケイ素原子に結合した加水分解性のアルコキシ基が存在するため、他の有機ケイ素化合物（ポリマーを含む）との反応によりシロキサン結合を形成したり、無機化合物中のシラノール基とカップリング反応させることができる。また、３官能性アルコキシシランであるため、架橋反応を利用することにより、シリコーンレジン、シルセスキオキサンを構築することができる。
一方、水酸基を保護しているアルキルアルコキシシリル基は、酸性条件下で加水分解により容易に脱離して遊離のアルコールを与え、炭素官能性基またはアルカリ水溶性基として機能する。
また、遊離の水酸基は極性官能基と強い水素結合を形成する。そのため、水素結合を利用した有機−無機ハイブリッド材料へも利用できる。すなわち、ケイ素官能性および保護された炭素官能性をもつ複反応性ケイ素化合物として機能する。また、水酸基を保護しているアルキルアルコキシシリル基自体も、脱離後は、３官能性アルコキシシランとして機能するため、架橋反応により、シリコーンレジン又はシルセスキオキサン骨格に組み込まれる。
Since the novel organosilicon compound of the present invention has a hydrolyzable alkoxy group bonded to a silicon atom, a siloxane bond is formed by reaction with another organosilicon compound (including a polymer), or in an inorganic compound. Coupling reaction with the silanol group. Moreover, since it is a trifunctional alkoxysilane, a silicone resin and silsesquioxane can be constructed by utilizing a crosslinking reaction.
On the other hand, the alkylalkoxysilyl group protecting the hydroxyl group is easily eliminated by hydrolysis under acidic conditions to give a free alcohol, and functions as a carbon functional group or an alkali water-soluble group.
The free hydroxyl group forms a strong hydrogen bond with the polar functional group. Therefore, it can be used for organic-inorganic hybrid materials using hydrogen bonds. That is, it functions as a double-reactive silicon compound with silicon functionality and protected carbon functionality. In addition, since the alkylalkoxysilyl group protecting the hydroxyl group itself functions as a trifunctional alkoxysilane after elimination, it is incorporated into a silicone resin or silsesquioxane skeleton by a crosslinking reaction.
本発明は、上記一般式（１）で表される有機ケイ素化合物、すなわち、アルキルアルコキシシリル基により保護された水酸基を含有するアルコキシシラン（以下、本発明ケイ素系化合物）に関する。以下、本発明について詳述する。 The present invention relates to an organosilicon compound represented by the above general formula (1), that is, an alkoxysilane containing a hydroxyl group protected by an alkylalkoxysilyl group (hereinafter referred to as silicon compound of the present invention). Hereinafter, the present invention will be described in detail.
上記一般式（１）において、Ｒ1、Ｒ2、Ｒ4、Ｒ5およびＲ6は炭素数１から１０のアルキル基、アラルキル基またはアリール基である。
アルキル基は直鎖状、分岐状または環状でも差し支えなく、具体例として、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基があり、アラルキル基の具体例として、ベンジル基があり、アリール基の具体例として、フェニル基等がある。これらの中でも、原料が得易く、合成が容易なことから、一般にＲ1についてメチル基またはフェニル基が好ましく、Ｒ2、Ｒ4、Ｒ5およびＲ6についてはメチル基またはエチル基が好ましい。
In the general formula (1), R 1 , R 2 , R 4 , R 5 and R 6 are an alkyl group, aralkyl group or aryl group having 1 to 10 carbon atoms.
Alkyl groups may be linear, branched or cyclic, and specific examples include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl groups. Specific examples of the aralkyl group include a benzyl group, and specific examples of the aryl group include a phenyl group. Of these, the raw material is easy to obtain, since the synthesis is easy, preferably a methyl group or a phenyl group for general R 1, R 2, R 4 , the R 5 and R 6 are preferably a methyl group or an ethyl group.
上記一般式（１）において、Ｒ3は炭素数２から１０のアルキレン基又は炭素数７から１０のフェニルアルキレン基であり、直鎖状、分岐状または環状のいずれでもよい。アルキレン基の具体例としては、ジメチレン基、トリメチレン基、テトラメチレン基、ペンタメチレン基、ヘキサメチレン基、ペンタメチレン、オクタメチレン、ノナメチレン、デカメチレン、２−メチルトリメチレン基、３−メチルトリメチレン基、１，４−シクロへキシレン基等があり、フェニルアルキレン基の具体例として、ジメチレニルフェニレン基等が例示される。これらの中で、合成の容易なことおよび原料の入手のしやすさから、該炭素数が３の直鎖状炭化水素が最も好ましい。 In the general formula (1), R 3 is an alkylene group having 2 to 10 carbon atoms or a phenylalkylene group having 7 to 10 carbon atoms, and may be linear, branched or cyclic. Specific examples of the alkylene group include dimethylene group, trimethylene group, tetramethylene group, pentamethylene group, hexamethylene group, pentamethylene, octamethylene, nonamethylene, decamethylene, 2-methyltrimethylene group, 3-methyltrimethylene group, There are 1,4-cyclohexylene groups and the like, and a specific example of the phenylalkylene group is a dimethylenylphenylene group. Among these, the straight chain hydrocarbon having 3 carbon atoms is most preferable because of easy synthesis and availability of raw materials.
本発明ケイ素系化合物の最も好ましい具体例は、下記一般式（２）で表される化合物である。 The most preferred specific example of the silicon-based compound of the present invention is a compound represented by the following general formula (2).
本発明ケイ素系化合物は、以下の反応工程［１］および［２］を順次行うことにより容易に得られる。
工程［１］：下記一般式（３）で表される化合物｛但し、Ｒ1およびＲ2は、一般式（１）における意味と同義である｝と下記一般式（４）で表されるアルコール｛但し、Ｒ8は炭素数２から１０のアルケニル基またはシクロアルケニル基を示し、工程［２］の反応後は、Ｒ3となる基である｝を反応させて下記一般式（５）で表される化合物｛但し、Ｒ1、Ｒ2、ａおよびｂは、前記一般式（１）における意味と同義であり、Ｒ8は、前記一般式（３）における意味と同義である｝を得る。
工程［２］：工程１の一般式（４）で表される化合物とシラン化合物（ＯＲ4）（ＯＲ5）（ＯＲ6）ＳｉＨ（但し、Ｒ4、Ｒ5およびＲ6は一般式（１）における意味と同義である）とをヒドロシリル化反応させる。
上記式（２）で表される化合物の場合、次のようにして製造することができる。下記一般式（６）に表される化合物（アリルアルコール）を酸存在下、下記式（７）で表されるシラン化合物（トリエトキシメチルシラン）と反応させることにより、アルキルアルコキシシリル基により保護された水酸基を含有する下記一般式（８）の化合物（アリルオキシジエトキシメチルシラン）を得る。
The silicon-based compound of the present invention can be easily obtained by sequentially performing the following reaction steps [1] and [2].
Step [1]: Compound represented by the following general formula (3) {provided that R 1 and R 2 have the same meaning as in the general formula (1)} and the alcohol represented by the following general formula (4) {Provided that R 8 represents an alkenyl group or cycloalkenyl group having 2 to 10 carbon atoms, and is a group that becomes R 3 after the reaction in step [2]}, and is represented by the following general formula (5). To obtain the compound {wherein R 1 , R 2 , a and b have the same meaning as in the general formula (1), and R 8 has the same meaning as in the general formula (3)).
Step [2]: The compound represented by the general formula (4) of the step 1 and the silane compound (OR 4 ) (OR 5 ) (OR 6 ) SiH (where R 4 , R 5 and R 6 are represented by the general formula (1) ) Having the same meaning as in).
In the case of the compound represented by the above formula (2), it can be produced as follows. By reacting the compound (allyl alcohol) represented by the following general formula (6) with a silane compound (triethoxymethylsilane) represented by the following formula (7) in the presence of an acid, it is protected by an alkylalkoxysilyl group. A compound (allyloxydiethoxymethylsilane) of the following general formula (8) containing a hydroxyl group is obtained.
当該反応は、アリルアルコールとトリエトキシメチルシランの混合物に、触媒として酸を加えて室温で攪拌すれば、容易に進行する。必要に応じて加熱してもよい。酸としては、パラトルエンスルホン酸等が例示される。酸の使用量は、上記式（６）で表されるアルコールに対して０．０１〜１０ｍｏｌ％であることが望ましい。反応終了後、減圧蒸留によってアリルオキシジエトキシメチルシランを得る。
あるいは、アリルアルコールに例えば水素化ナトリウム等の塩基を作用させてアルコラートとした後、これをトリエトキシメチルシランと反応させることによっても、アリルオキシジエトキシメチルシランを得ることが出来る。
なお、アリルアルコールとトリエトキシメチルシランとの反応において、アリルアルコールの仕込み割合を大きくすることにより、１分子当たりのアリル基の数を最大３個まで多くすることができる。
このようにして得られたアリルオキシジエトキシメチルシランを、トリエトキシシランと反応させ、上記式（８）で表される化合物を得る。
この反応は触媒の存在下で行われ、触媒としては、コバルト、ニッケル、ルテニウム、ロジウム、パラジウム、イリジウム、白金等の第８属から第１０属金属の単体、有機金属錯体、金属塩、金属酸化物等が用いられるが、通常、白金系の触媒が使用される。白金系触媒としては、塩化白金酸六水和物（H2PtCl6・６H2O）、cis-PtCl2(PhCN)2、白金カーボン、ジビニルテトラメチルジシロキサンが配位した白金錯体(Pt-dvds)等が例示され、特に好ましくはPt-dvdsである。なお、Phはフェニル基を表わす。触媒の使用量は、上記式（７）で表される化合物の量に対して、０．１〜１，０００ｐｐｍであることが好ましい。
The reaction proceeds easily if an acid is added as a catalyst to a mixture of allyl alcohol and triethoxymethylsilane and stirred at room temperature. You may heat as needed. Examples of the acid include p-toluenesulfonic acid. The amount of the acid used is desirably 0.01 to 10 mol% with respect to the alcohol represented by the above formula (6). After completion of the reaction, allyloxydiethoxymethylsilane is obtained by distillation under reduced pressure.
Alternatively, allyloxydiethoxymethylsilane can also be obtained by reacting allyl alcohol with an alcoholate such as sodium hydride to react with triethoxymethylsilane.
In the reaction between allyl alcohol and triethoxymethylsilane, the number of allyl groups per molecule can be increased to a maximum of three by increasing the charge ratio of allyl alcohol.
The allyloxydiethoxymethylsilane thus obtained is reacted with triethoxysilane to obtain a compound represented by the above formula (8).
This reaction is carried out in the presence of a catalyst. Examples of the catalyst include cobalt, nickel, ruthenium, rhodium, palladium, iridium, platinum and other group 8-10 group metals, organometallic complexes, metal salts, metal oxidation. In general, a platinum-based catalyst is used. Platinum catalysts include chloroplatinic acid hexahydrate (H 2 PtCl 6 · 6H 2 O), cis-PtCl 2 (PhCN) 2 , platinum carbon, and platinum complexes coordinated with divinyltetramethyldisiloxane (Pt- dvds) and the like are exemplified, and Pt-dvds is particularly preferable. Ph represents a phenyl group. It is preferable that the usage-amount of a catalyst is 0.1-1,000 ppm with respect to the quantity of the compound represented by the said Formula (7).
また、反応温度の制御操作は、外部からの加熱およびトリエトキシシランの供給速度に依存するため、一概に決められないが、通常、反応温度を室温〜１１０℃の範囲に保持することで、ヒドロシリル化反応を円滑に継続させることができる。反応終了後、減圧蒸留することにより本発明ケイ素系化合物を得る。
The reaction temperature control operation depends on external heating and the supply rate of triethoxysilane, and thus cannot be determined in general. Usually, the reaction temperature is kept in the range of room temperature to 110 ° C. The chemical reaction can be continued smoothly. After completion of the reaction, the silicon compound of the present invention is obtained by distillation under reduced pressure.
以下、本発明を実施例によって具体的に説明する。
＜実施例１＞
１−１）アリルオキシジエトキシメチルシランの合成
冷却器、滴下ロート、磁気撹拌子を備えたフラスコにアリルアルコール５０．６ｇ（８７２ｍｍｏｌ）およびトリエトキシメチルシラン３１０．６ｇ（１．７４ｍｏｌ）を仕込み、攪拌した。ここに室温でパラトルエンスルホン酸一水和物０．１ｇ（０．５３ｍｍｏｌ）を加えて、２０分間攪拌した。
反応終了後、反応混合物から副生したエタノール等を常圧下で留去した後、減圧蒸留し、目的のアリルオキシジエトキシメチルシラン（トリエトキシメチルシランおよびジアリルオキシエトキシメチルシランを含有する）を、無色透明の液体として得た。収量２７３ｇ、ｂｐ３２−４４℃／５３０Ｐａ。
上記のようにて得られた液体の1Ｈ ＮＭＲスペクトルのケミカルシフトは以下の通りであり、アリルオキシジエトキシメチルシランの生成が確認された。
1Ｈ ＮＭＲ（２７０ＭＨｚ，ＣＤＣｌ3）
δ５．９９−５．８５（ｍ，１Ｈ），
δ５．３０−５．２１（ｍ，１Ｈ），
δ５．１１−５．０６（ｍ，１Ｈ），
δ４．２７−４．２４（ｍ，２Ｈ），
δ３．７９（ｑ，Ｊ＝６．９Ｈｚ，４Ｈ），
δ１．２０（ｔ，Ｊ＝６．９Ｈｚ，６Ｈ），
δ０．１１（ｓ，３Ｈ）．
Hereinafter, the present invention will be specifically described by way of examples.
<Example 1>
1-1) Synthesis of allyloxydiethoxymethylsilane A flask equipped with a condenser, a dropping funnel and a magnetic stirrer was charged with 50.6 g (872 mmol) of allyl alcohol and 310.6 g (1.74 mol) of triethoxymethylsilane, Stir. To this was added 0.1 g (0.53 mmol) of paratoluenesulfonic acid monohydrate at room temperature, and the mixture was stirred for 20 minutes.
After completion of the reaction, ethanol or the like by-produced from the reaction mixture was distilled off under normal pressure, followed by distillation under reduced pressure, and the desired allyloxydiethoxymethylsilane (containing triethoxymethylsilane and diallyloxyethoxymethylsilane) was obtained. Obtained as a colorless and transparent liquid. Yield 273 g, bp 32-44 ° C./530 Pa.
The chemical shift of the 1 H NMR spectrum of the liquid obtained as described above was as follows, and the formation of allyloxydiethoxymethylsilane was confirmed.
1 H NMR (270 MHz, CDCl 3 )
δ5.99-5.85 (m, 1H),
δ 5.30-5.21 (m, 1H),
δ 5.11-5.06 (m, 1H),
δ 4.27-4.24 (m, 2H),
δ 3.79 (q, J = 6.9 Hz, 4H),
δ 1.20 (t, J = 6.9 Hz, 6H),
δ 0.11 (s, 3H).
１−２）（３−トリエトキシシリルプロピルオキシ）ジエトキシメチルシランの合成
冷却器、滴下ロート、磁気撹拌子を備えたフラスコに実施例１の１−１）で得たアリルオキシジエトキシメチルシラン（トリエトキシメチルシランおよびジアリルオキシエトキシメチルシランを含有する）２７３ｇを仕込み、攪拌した。滴下ロートにトリエトキシシラン１２９．６ｇ（７８９ｍｍｏｌ＝約１４５ｍＬ）を仕込み、約２３ｍＬを反応系内に加えた。オイルバスを８０℃に設定し、０．１ｍｏｌ／Ｌ Ｐｔ−ｄｖｄｓキシレン溶液０．０７ｍＬ（０．００７ｍｍｏｌ）を加え反応を開始させた。１７分間攪拌した後、残りのトリエトキシシランを徐々に滴下し、８０℃で４時間反応させた。反応終了後、減圧蒸留により無色透明液体の目的物１５３ｇ（仕込みのアリルアルコールに対する全収率５０％）を得た。ｂｐ９２−１０１℃／１３０Ｐａ。
上記のようにして得られた無色透明液体の1Ｈ ＮＭＲスペクトルのケミカルシフトは以下の通りであり、（３−トリエトキシシリルプロピルオキシ）ジエトキシメチルシランの生成が確認された。
1Ｈ ＮＭＲ（２７０ＭＨｚ，ＣＤＣｌ3）
δ３．７６（ｑ，Ｊ＝７．０Ｈｚ，４Ｈ），
δ３．７４（ｑ，Ｊ＝７．０Ｈｚ，６Ｈ），
δ３．６３（ｔ，Ｊ＝６．８Ｈｚ，２Ｈ），
δ１．６８−１．５７（ｍ，２Ｈ），
δ０．６１−０．５５（ｍ，２Ｈ），
δ１．１６（ｔ，Ｊ＝７．０Ｈｚ，６Ｈ），
δ０．０６（ｓ，３Ｈ）．
1-2) Synthesis of (3-triethoxysilylpropyloxy) diethoxymethylsilane Allyloxydiethoxymethylsilane obtained in 1-1 of Example 1 in a flask equipped with a condenser, a dropping funnel and a magnetic stirrer 273 g (containing triethoxymethylsilane and diallyloxyethoxymethylsilane) was charged and stirred. The dropping funnel was charged with 129.6 g (789 mmol = about 145 mL) of triethoxysilane, and about 23 mL was added to the reaction system. The oil bath was set at 80 ° C., and 0.07 mL (0.007 mmol) of a 0.1 mol / L Pt-dvds xylene solution was added to initiate the reaction. After stirring for 17 minutes, the remaining triethoxysilane was gradually added dropwise and reacted at 80 ° C. for 4 hours. After completion of the reaction, 153 g of a colorless and transparent liquid target product (total yield of 50% based on the charged allyl alcohol) was obtained by distillation under reduced pressure. bp92-101 ° C / 130Pa.
The chemical shift of the 1 H NMR spectrum of the colorless and transparent liquid obtained as described above was as follows, and the production of (3-triethoxysilylpropyloxy) diethoxymethylsilane was confirmed.
1 H NMR (270 MHz, CDCl 3 )
δ 3.76 (q, J = 7.0 Hz, 4H),
δ3.74 (q, J = 7.0 Hz, 6H),
δ 3.63 (t, J = 6.8 Hz, 2H),
δ 1.68-1.57 (m, 2H),
δ 0.61-0.55 (m, 2H),
δ 1.16 (t, J = 7.0 Hz, 6H),
δ 0.06 (s, 3H).
＜実施例２＞
２−１）ｏ−（ジエトキシメチルシリル）オイゲノール（ＥＵＤＥＭＳ）の合成
合成フローは以下の通りである。
<Example 2>
2-1) Synthesis of o- (diethoxymethylsilyl) eugenol (EUDEMS) The synthesis flow is as follows.
１００ｍＬ二口フラスコに、オイゲノール２２．０ｇ（１３４ｍｍｏｌ）およびトリエトキシメチルシラン５９．８ｇ（３３５ｍｏｌ）を仕込み、かき混ぜた。ここにｐ−トルエンスルホン酸（１水和物）１．２８１ｇ（６．７４ｍｍｏｌ）を加えて、１００℃から１６０℃に徐々に昇温し、副生したエタノール等を留去しながら８時間反応させた。反応混合物を減圧蒸留し、目的のＥＵＤＥＭＳを、無色透明の液体として得た。収量１８．３ｇ、ｂｐ９０−１００℃／１３０Ｐａ。
上記のようにして得られた無色透明液体の1Ｈ ＮＭＲスペクトルのケミカルシフトは以下の通りであり、ＥＵＤＥＭＳの生成が確認された。
1Ｈ ＮＭＲ（２７０ＭＨｚ，ＣＤＣｌ3）
δ６．９２−６．８９（ｍ，１Ｈ），
δ６．７０−６．６３（ｍ，２Ｈ），
δ６．０３０５．８８（ｍ，１Ｈ），
δ５．１１−５．０３（ｍ，２Ｈ），
δ３．８８（ｑ，Ｊ＝７．０Ｈｚ，４Ｈ），
δ３．８１（ｓ，３Ｈ），
δ３．３２（ｄ，Ｊ＝６．６Ｈｚ，２Ｈ），
δ１．２２（ｔ，Ｊ＝７．０Ｈｚ，６Ｈ），
δ０．２３（ｓ，３Ｈ）．
In a 100 mL two-necked flask, 22.0 g (134 mmol) of eugenol and 59.8 g (335 mol) of triethoxymethylsilane were charged and stirred. To this was added 1.281 g (6.74 mmol) of p-toluenesulfonic acid (monohydrate), the temperature was gradually raised from 100 ° C. to 160 ° C., and the reaction was performed for 8 hours while distilling off by-produced ethanol and the like. I let you. The reaction mixture was distilled under reduced pressure to obtain the desired EUDEMS as a colorless transparent liquid. Yield 18.3 g, bp 90-100 ° C./130 Pa.
The chemical shift of the 1 H NMR spectrum of the colorless and transparent liquid obtained as described above was as follows, and production of EUDEMS was confirmed.
1 H NMR (270 MHz, CDCl 3 )
δ 6.92-6.89 (m, 1H),
δ 6.70-6.63 (m, 2H),
δ 6.0305.88 (m, 1H),
δ 5.11-5.03 (m, 2H),
δ 3.88 (q, J = 7.0 Hz, 4H),
δ 3.81 (s, 3H),
δ 3.32 (d, J = 6.6 Hz, 2H),
δ1.22 (t, J = 7.0 Hz, 6H),
δ 0.23 (s, 3H).
２−２）トリエトキシ［３−（４−ジエトキシメチルシリルオキシ−３−メトキシフェニル）プロピル］シラン （ＴＥＳＥＵＤＥＭＳ）
合成フローは以下の通りである。
2-2) Triethoxy [3- (4-diethoxymethylsilyloxy-3-methoxyphenyl) propyl] silane (TOSEUDEMS)
The synthesis flow is as follows.
５０ｍＬ二口フラスコに１）で得たＥＵＤＥＭＳ１８．３ｇ（５９．８ｍｍｏｌ）を仕込み、かき混ぜた。滴下ロートにトリエトキシシラン１０．８ｇ（６５．７ｍｍｏｌ＝約１２ｍＬ）を仕込み、約３ｍＬを反応系内に加えた後、反応系を７０℃に加熱し、０．１ｍｏｌ／Ｌ Ｐｔ−ｄｖｄｓキシレン溶液（Ｐｔ濃度２．１−２．４％）０．２５ｍＬを加えてかきまぜた。途中で残りのトリエトキシシランを滴下し、触媒添加後８時間反応させた。反応終了後、減圧蒸留により無色透明液体の目的物１４．２ｇ（収率５２％）を得た。ｂｐ１３３−１６０℃／１３０Ｐａ。
上記のようにして得られた無色透明液体の1Ｈ ＮＭＲスペクトルのケミカルシフトは以下の通りであり、ＴＥＳＥＵＤＥＭＳの生成が確認された。
1Ｈ ＮＭＲ（２７０ＭＨｚ，ＣＤＣｌ3）
δ６．８９−６．８６（ｍ，１Ｈ），
δ６．７０−６．６９（ｍ，１Ｈ），
δ６．６５−６．６２（ｍ，１Ｈ），
δ３．８９（ｑ，Ｊ＝７．０Ｈｚ，４Ｈ），
δ３．８１（ｓ，３Ｈ），
δ３．８０（ｑ，Ｊ＝７．０Ｈｚ，６Ｈ），
δ２．５８（ｔ，Ｊ＝７．６Ｈｚ，２Ｈ），
δ１．７８−１．６６（ｍ，２Ｈ），
δ１．２２２（ｔ，Ｊ＝７．０Ｈｚ，６Ｈ），
δ１．２１７（ｔ，Ｊ＝７．０Ｈｚ，９Ｈ），
δ０．２３（ｓ，３Ｈ）．
EUDEMS 18.3 g (59.8 mmol) obtained in 1) was charged into a 50 mL two-necked flask and stirred. First, 10.8 g (65.7 mmol = about 12 mL) of triethoxysilane was charged into the dropping funnel, about 3 mL was added to the reaction system, and then the reaction system was heated to 70 ° C. to obtain a 0.1 mol / L Pt-dvds xylene solution. 0.25 mL (Pt concentration 2.1-2.4%) was added and stirred. On the way, the remaining triethoxysilane was added dropwise and reacted for 8 hours after the addition of the catalyst. After completion of the reaction, 14.2 g (yield 52%) of the objective product as a colorless and transparent liquid was obtained by distillation under reduced pressure. bp 133-160 ° C / 130Pa.
The chemical shift of the 1 H NMR spectrum of the colorless and transparent liquid obtained as described above was as follows, and the production of TESEUdem was confirmed.
1 H NMR (270 MHz, CDCl 3 )
δ 6.89-6.86 (m, 1H),
δ 6.70-6.69 (m, 1H),
δ 6.65-6.62 (m, 1H),
δ 3.89 (q, J = 7.0 Hz, 4H),
δ 3.81 (s, 3H),
δ 3.80 (q, J = 7.0 Hz, 6H),
δ2.58 (t, J = 7.6 Hz, 2H),
δ 1.78-1.66 (m, 2H),
δ 1.222 (t, J = 7.0 Hz, 6H),
δ 1.217 (t, J = 7.0 Hz, 9H),
δ 0.23 (s, 3H).
＜参考例１＞
上記実施例１で得られた（３−トリエトキシシリルプロピルオキシ）ジエトキシメチルシランを２−プロパノールに溶解させて、塩酸酸性下、室温で５時間加水分解縮合した結果、白色固体状物質を得た。前記白色固体状物質の赤外吸収スペクトルにおいて、３３３０ｃｍ-1にＯＨ基に由来する特性吸収が観測された。このことから、本発明の有機ケイ素化合物の酸性下の加水分解縮合によりシリル基が脱保護され、水酸基が生成したことが確認された。
<Reference Example 1>
(3-Triethoxysilylpropyloxy) diethoxymethylsilane obtained in Example 1 above was dissolved in 2-propanol and hydrolyzed and condensed at room temperature for 5 hours under acidic conditions of hydrochloric acid, resulting in a white solid substance. It was. In the infrared absorption spectrum of the white solid substance, characteristic absorption derived from an OH group was observed at 3330 cm −1 . From this, it was confirmed that the silyl group was deprotected by the hydrolytic condensation under the acidic condition of the organosilicon compound of the present invention to generate a hydroxyl group.
本発明の有機ケイ素化合物は、一方ではケイ素官能基を有し、他方ではシリル基で保護された炭素官能基（アルコール性水酸基）を有するために、有機合成などの中間原料、ポリマー樹脂の合成原料、各種材料のカップリング剤、ポリマーの改質剤、表面に水酸基を有する無機材料の表面処理剤、有機―無機ハイブリッド材料の原料として有用であり、特にリソグラフィー用材料の原料化合物として有用である。 The organosilicon compound of the present invention has a silicon functional group on the one hand and a carbon functional group (alcoholic hydroxyl group) protected by a silyl group on the other hand. It is useful as a raw material for a coupling agent for various materials, a polymer modifier, a surface treatment agent for an inorganic material having a hydroxyl group on the surface, and an organic-inorganic hybrid material, and particularly as a raw material compound for a lithography material.
Claims (2)
（式中、Ｒ1、Ｒ2、Ｒ4、Ｒ5およびＲ6は炭素数１から１０のアルキル基、アラルキル基またはアリール基であり、Ｒ3は炭素数２から１０のアルキレン基又は炭素数７から１０のフェニルアルキレン基を示し、ａおよびｂは、ａ≧０、ｂ≧１およびａ＋ｂ＝３を満たす整数である。）
An organosilicon compound represented by the following general formula (1).
Wherein R 1 , R 2 , R 4 , R 5 and R 6 are an alkyl group, aralkyl group or aryl group having 1 to 10 carbon atoms, and R 3 is an alkylene group or carbon number having 2 to 10 carbon atoms. 7 to 10 phenylalkylene groups, a and b are integers satisfying a ≧ 0, b ≧ 1 and a + b = 3.)
工程［１］：下記一般式（２）で表される化合物｛但し、Ｒ1およびＲ2は、請求項１記載の一般式（１）における意味と同義である｝と下記一般式（３）で表されるアルコール｛但し、Ｒ8は炭素数２から１０のアルケニル基またはシクロアルケニル基を示し、工程［２］の反応後は、Ｒ3となる基である｝を反応させて下記一般式（４）で表される化合物｛但し、Ｒ1、Ｒ2、ａおよびｂは、請求項１記載の一般式（１）における意味と同義であり、Ｒ8は、前記一般式（３）における意味と同義である｝を得る。
工程［２］：工程１の一般式（４）で表される化合物とシラン化合物（ＯＲ4）（ＯＲ5）（ＯＲ6）ＳｉＨ（但し、Ｒ4、Ｒ5およびＲ6は請求項１記載の一般式（１）における意味と同義である）とをヒドロシリル化反応させる。
The method for producing an organosilicon compound according to claim 1, wherein the following reaction steps [1] and [2] are sequentially performed.
Step [1]: Compound represented by the following general formula (2) {provided that R 1 and R 2 have the same meaning as in general formula (1) according to claim 1) and the following general formula (3) (Wherein R 8 represents an alkenyl group or a cycloalkenyl group having 2 to 10 carbon atoms, and after the reaction in step [2] is a group that becomes R 3) , the following general formula Compound represented by (4) {provided that R 1 , R 2 , a and b have the same meaning as in general formula (1) according to claim 1, and R 8 represents the same in general formula (3). Is synonymous with meaning}.
Step [2]: The compound represented by the general formula (4) in Step 1 and a silane compound (OR 4 ) (OR 5 ) (OR 6 ) SiH (wherein R 4 , R 5 and R 6 are defined in claim 1) Is synonymous with the meaning in the general formula (1).
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005203716A JP2008239489A (en) | 2005-07-12 | 2005-07-12 | Novel organosilicon compound |
| PCT/JP2006/313331 WO2007007597A1 (en) | 2005-07-12 | 2006-07-04 | Novel organosilicon compound and process for producing the same |
| TW095125266A TW200720282A (en) | 2005-07-12 | 2006-07-11 | Novel organosilicon compound and process for producing the same |
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| JP2005203716A JP2008239489A (en) | 2005-07-12 | 2005-07-12 | Novel organosilicon compound |
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| TW (1) | TW200720282A (en) |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012144445A (en) * | 2011-01-07 | 2012-08-02 | Shin-Etsu Chemical Co Ltd | Unsaturated bond-containing silyl group-protected amino acid compound, and method for producing the same |
| KR101749174B1 (en) * | 2016-01-18 | 2017-06-21 | 영창케미칼 주식회사 | Coating composition for anti-reflection and anti-reflection film using the same |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20090119903A (en) * | 2007-02-14 | 2009-11-20 | 제이에스알 가부시끼가이샤 | Material for forming silicon-containing film, and silicon-containing insulating film and method for forming the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4489029A (en) * | 1983-06-01 | 1984-12-18 | Union Carbide Corporation | Compositions based on alkylene-alkyl acrylate copolymers and silanol condensation catalysts; and the use thereof in the production of covered wires and cables |
| JP2004123793A (en) * | 2002-09-30 | 2004-04-22 | Jsr Corp | Silicon-containing compound, polysiloxane, and radiation-sensitive resin composition |
| DE10349766A1 (en) * | 2003-10-24 | 2005-06-16 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Silica polycondensates with branched-chain radicals containing urethane, acid amide and / or carboxylic acid ester groups |
| KR101007807B1 (en) * | 2003-12-13 | 2011-01-14 | 삼성전자주식회사 | Multi-functional Linear Siloxane compound, Siloxane Polymer prepared from the Compound and Process for preparing Dielectric Film by using the Polymer |
-
2005
- 2005-07-12 JP JP2005203716A patent/JP2008239489A/en active Pending
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2006
- 2006-07-04 WO PCT/JP2006/313331 patent/WO2007007597A1/en active Application Filing
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012144445A (en) * | 2011-01-07 | 2012-08-02 | Shin-Etsu Chemical Co Ltd | Unsaturated bond-containing silyl group-protected amino acid compound, and method for producing the same |
| KR101749174B1 (en) * | 2016-01-18 | 2017-06-21 | 영창케미칼 주식회사 | Coating composition for anti-reflection and anti-reflection film using the same |
| WO2017126859A1 (en) * | 2016-01-18 | 2017-07-27 | 영창케미칼 주식회사 | Anti-reflection coating composition and anti-reflection film utilizing same |
| US10717878B2 (en) | 2016-01-18 | 2020-07-21 | Young Chang Chemical Co., Ltd | Anti-reflection coating composition and anti-reflection film utilizing same |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200720282A (en) | 2007-06-01 |
| WO2007007597A1 (en) | 2007-01-18 |
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