JP4013520B2 - Novel halogenosilanes and alkali-soluble resins - Google Patents
Novel halogenosilanes and alkali-soluble resins Download PDFInfo
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- JP4013520B2 JP4013520B2 JP2001325690A JP2001325690A JP4013520B2 JP 4013520 B2 JP4013520 B2 JP 4013520B2 JP 2001325690 A JP2001325690 A JP 2001325690A JP 2001325690 A JP2001325690 A JP 2001325690A JP 4013520 B2 JP4013520 B2 JP 4013520B2
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- alkali
- silicon
- resin
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- novel
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- 229920005989 resin Polymers 0.000 title claims description 42
- 239000011347 resin Substances 0.000 title claims description 42
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 17
- 229910052710 silicon Inorganic materials 0.000 description 17
- 239000002585 base Substances 0.000 description 16
- 125000004018 acid anhydride group Chemical group 0.000 description 13
- 125000004122 cyclic group Chemical group 0.000 description 13
- 239000010703 silicon Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- 239000003513 alkali Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 3
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- WUMMIJWEUDHZCL-UHFFFAOYSA-N 3-prop-2-enyloxolane-2,5-dione Chemical compound C=CCC1CC(=O)OC1=O WUMMIJWEUDHZCL-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- -1 cyclic anhydride Chemical group 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 150000003961 organosilicon compounds Chemical class 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 239000002210 silicon-based material Substances 0.000 description 2
- 238000006884 silylation reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- MJAJWLNBKCLQKH-UHFFFAOYSA-N C[SH-](C)(CCCC(CC(O1)=O)C1=O)Cl Chemical compound C[SH-](C)(CCCC(CC(O1)=O)C1=O)Cl MJAJWLNBKCLQKH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- GSKVLVXXJRJNAN-UHFFFAOYSA-N [di(propan-2-yl)-$l^{3}-silanyl]oxy-di(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)O[Si](C(C)C)C(C)C GSKVLVXXJRJNAN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 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
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- XUKFPAQLGOOCNJ-UHFFFAOYSA-N dimethyl(trimethylsilyloxy)silicon Chemical compound C[Si](C)O[Si](C)(C)C XUKFPAQLGOOCNJ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 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 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000004687 hexahydrates Chemical class 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
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- RFGGTTPASBFBTB-UHFFFAOYSA-N methyl-[methyl(diphenyl)silyl]oxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C)O[Si](C)(C=1C=CC=CC=1)C1=CC=CC=C1 RFGGTTPASBFBTB-UHFFFAOYSA-N 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002524 organometallic group Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 125000005372 silanol group Chemical group 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 125000005371 silicon functional group Chemical group 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- WILBTFWIBAOWLN-UHFFFAOYSA-N triethyl(triethylsilyloxy)silane Chemical compound CC[Si](CC)(CC)O[Si](CC)(CC)CC WILBTFWIBAOWLN-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- IVZTVZJLMIHPEY-UHFFFAOYSA-N triphenyl(triphenylsilyloxy)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 IVZTVZJLMIHPEY-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Description
【０００１】
【発明の属する技術分野】
本発明は、環状酸無水物基を有する新規なハロゲノシラン及び、それを反応させてなるアルカリ可溶性樹脂に関する。
【０００２】
【従来の技術】
カルボキシル基を有するケイ素系アルカリ可溶性樹脂は、各種の物が知られている（特開平11-130860、特開2001-5185：溶解速度0.4μｍ/ｓ）。これらの樹脂は、末端ケイ素原子に対して１当量のカルボキシル基しか持っていないため、アルカリ可溶性に課題を残している。
一方、末端ケイ素原子１個当たり２個のカルボキシル基を有するケイ素系アルカリ可溶性樹脂は知られていない。
末端ケイ素原子に対して２当量のカルボキシル基を導入できれば、従来のケイ素系アルカリ可溶性樹脂に比べ、大幅な溶解性向上が期待できる。
【０００３】
【発明が解決しようとする課題】
本発明の課題は、環状酸無水物基を有する新規なハロゲノシラン及び、それを反応してなるケイ素系アルカリ可溶性樹脂を提供し、そのことによって、有機合成その他の分野で新規な合成方法や、材料表面処理方法、樹脂改質及び新規樹脂の製造等を可能とすることにある。
【０００４】
【課題を解決するための手段】
本発明者は、環状酸無水物基を有するハロゲノシランは、一方では１個のケイ素官能基を有し、他方では環状酸無水物基を有するために、有機合成などの中間原料や各種材料カップリング剤として有用であることを見出し、本発明を完成するに至った。
即ち、本発明は、下記一般式で表されるハロゲノシラン、
【０００５】
【化２】
（式中、Ｒ1およびＲ2はメチル基を示し、Ｒ3は炭素数３の直鎖状アルキレン基を示し、Ｘは塩素を示す）及び、それをベース樹脂と反応して得られるアルカリ可溶性樹脂である。以下、本発明について詳述する。
【０００７】
【発明の実施の形態】
「環状酸無水物基を有するハロゲノシラン」
本発明の新規な化合物は、上記一般式で表されるものである。Ｒ1およびＲ2はメチル基である。原料が得易く、合成が容易なことからメチル基が好ましいのである。Ｒ3は炭素数３のアルキレン基で、直鎖状であり、具体的にはトリメチレン基である。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のである。Ｘは塩素である。原料の入手の容易さから塩素であることが最も好ましいのである。すなわち本願発明のハロゲノシランは、以下の構造式で示される化合物（Ｉ）である。
【０００８】
【化３】
本発明のケイ素系化合物は、例えば次のようにして製造することができる。
アリルコハク酸無水物をジメチルクロロシランとヒドロシリレーション反応させ、本発明のケイ素系化合物（Ｉ）を得る。
通常、この反応は触媒の存在下で行われ、好ましい触媒としては、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、金属酸化物等があり、中でも、白金系の触媒が特に好ましい。
好ましい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、ジビニルシロキサンが配位した白金錯体(PtDVTMDS)等が例示される。なお、Phはフェニル基を表わす。触媒の好ましい使用量は、化合物（Ｉ）の量に対して、0.1ｐｐｍから1,000ｐｐｍである。
また、反応温度の制御操作は、外部からの加熱およびジメチルクロロ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、ヒドロシリレーション反応を円滑に継続させることができる。反応終了後、溶媒および揮発成分を減圧下で留去し、減圧蒸留にて精製することにより化合物（Ｉ）を得る。
【００１０】
「ケイ素系アルカリ可溶性樹脂」
本発明のケイ素系アルカリ可溶性樹脂は、例えば次のようにして製造することができる。
先ず、樹脂骨格を形成させるアルコキシシランまたはハロゲノシランに、ゲル化抑制剤、触媒、水、溶媒を加え加熱攪拌することにより、ベース樹脂が得られる。
【００１１】
好ましいアルコキシシランとしては、テトラメトキシシラン、テトラエトキシシラン、トリメトキシシラン、トリエトキシシラン、メチルトリメトキシシラン、メチルトリエトキシシラン、フェニルトリメトキシシラン、フェニルトリエトキシシラン等が例示される。
【００１２】
好ましいハロゲノシランとしては、テトラクロロシラン、トリクロロシラン、メチルトリクロロシラン、フェニルトリクロロシラン等が例示される。
【００１３】
好ましいゲル化抑制剤としては、ジシロキサン誘導体が用いられ、ヘキサメチルジシロキサン、1,3-ジビニルテトラメチルジシロキサン、ヘキサエチルジシロキサン、ヘキサフェニルジシロキサン、ペンタメチルジシロキサン、1,1,3,3-テトラメチルジシロキサン、1,1,3,3-テトライソプロピルジシロキサン、1,1,3,3-テトラフェニルジメチルジシロキサン、1,1,1,3,3-ペンタメチル-3-アセトキシジシロキサン等が例示される。
【００１４】
好ましい触媒としては、塩酸、硫酸、硝酸、酢酸等の酸触媒、水酸化ナトリウム、水酸化カリウム、テトラメチルアンモニウムヒドロキシド等が例示される。
【００１５】
好ましい溶媒としては、水、アセトン、メチルイソブチルケトン、ジエチルエーテル、ジイソプロピルエーテル、ジブチルエーテル、テトラヒドロフラン、メタノール、エタノール、イソプロピルアルコール、ブタノール等の極性溶媒または、ヘキサン、ベンゼン、トルエン、キシレン、クロロホルム、塩化メチレン等の非極性溶媒が例示される。
【００１６】
上記各成分を加熱攪拌して反応させる際の好ましい温度は、室温〜１２０℃であり、アルコキシシラン又はハロゲノシラン１モル当たりの各成分の好ましい仕込み割合は、以下の通りである。
即ち、ゲル化抑制剤については、０．１〜０．５モルであり、触媒については、０．３〜６モルであり、水については、０．３〜３０モルであり、溶媒については０〜１５リットルである。
【００１７】
ベース樹脂の好ましい数平均分子量は２０００〜５０００である。２０００未満では、反応後にベース樹脂を回収する操作が煩雑になる恐れがあり、５００００を超えると後述するシリル化反応を円滑に行うことが困難になる恐れがある。
【００１８】
次いで、上記のようにして得られたベース樹脂を、溶媒、塩基存在下で本発明の有機ケイ素化合物を反応させてシリル化することにより、ケイ素系アルカリ可溶性樹脂を得る。
好ましい溶媒としては、アセトン、メチルイソブチルケトン、ジエチルエーテル、ジイソプロピルエーテル、ジブチルエーテル、テトラヒドロフラン、メタノール、エタノール、イソプロピルアルコール、ブタノール等の極性溶媒または、ヘキサン、ベンゼン、トルエン、キシレン、クロロホルム、塩化メチレン等の非極性溶媒が例示される。
【００１９】
好ましい塩基としては、トリエチルアミン、ピリジン、エチルジイソプロピルアミン、水酸化ナトリウム、水酸化カリウム、テトラメチルアンモニウムヒドロキシド等が例示される。
上記各成分を加熱攪拌してシリル化反応させる際の好ましい温度は、室温〜１２０℃であり、ベース樹脂と本発明の化合物との好ましい仕込み割合は、ベース樹脂１ｇ当たり０．５〜２００mmolである。
【００２０】
上記のようにして得られるアルカリ可溶性有機ケイ素系樹脂の好ましい数平均分子量は２０００〜５０００である。２０００未満では、樹脂の製造が困難であり、５００００を超えると十分なアルカリ可溶性を発揮できない恐れがある。
【００２１】
本発明のケイ素系アルカリ可溶性樹脂は、化学増幅型レジストのレジスト樹脂として有用である。アルカリ性水溶液に浸漬させることにより、樹脂中にジカルボン酸が生成し、優れたアルカリ可溶性を発現する。
【００２２】
【実施例】
以下、本発明を参考例および実施例によって具体的に説明する。
【００２３】
〔環状酸無水物基を有する新規なハロゲノシランの合成〕
実施例１
磁気攪拌子、冷却管、温度計、滴下ロートを備えた反応器を乾燥窒素雰囲気下にして、アリルコハク酸無水物24.7g（176mmol)を仕込み、６０℃にて攪拌させた。PtDVTMDSのキシレン溶液(10μl,0.0005mmol)を仕込み、続けてジメチルクロロシラン20.0g (211mmol)を徐々に加えた。滴下終了後、６０℃にて６時間攪拌させた。減圧下、揮発成分を留去後、減圧蒸留にて目的物を精製し、無色透明の液体を得た。〔沸点：148-150℃(267Pa)、収率：84%〕
この液体について270MHzの1Ｈ-ＮＭＲの測定を行ったところ、第１図のスペクトルを得た。δ値とその帰属は第１表のとおりであった。これにより得られた液体は、環状酸無水物基を有するハロゲノシラン（I）であることが確認できた。
【００２４】
【化４】
【表１】
【化５】
〔ベース樹脂の合成〕
実施例２
磁気攪拌子、冷却管、温度計、滴下ロートを備えた反応器に、ヘキサメチルジシロキサン1.87g（11.5mmol）、水17.5g（970mmol ）、酢酸10.8g (180mmol)を仕込み、系内を６０℃にて攪拌させた。テトラエトキシシラン6.24g (30mmol)を３０分かけて、系内に滴下させた。６０℃にて系を１時間攪拌させた後、再びテトラエトキシシラン3.12g (15mmol)を３０分かけて、系内に滴下させた。６０℃にて系を３時間攪拌させ、反応溶液をデカンテーションにて分離し、反応溶液に不溶のベース樹脂を回収した。水洗を３回繰り返し、テトラヒドロフラン100mLを加え、ベース樹脂を溶解させた。硫酸マグネシウムを加え、乾燥後、テトラヒドロフランを留去し白色固体のベース樹脂を得た（2.75g）。数平均分子量：4600
【００２８】
実施例３
磁気攪拌子、冷却管、温度計、滴下ロートを備えた反応器に、ヘキサメチルジシロキサン1.87g（11.5mmol）、水17.5g（970mmol ）、酢酸10.8g (180mmol)、テトラヒドロフラン100mLを仕込み、系内を６０℃にて攪拌させた。テトラエトキシシラン6.24g (30mmol)を３０分かけて、系内に滴下させた。６０℃にて系を１時間攪拌させた後、再びテトラエトキシシラン3.12g (15mmol)を３０分かけて、系内に滴下させた。６０℃にて系を３時間攪拌させた。メチルイソブチルケトンを加え、有機層を抽出した。有機層を水で３回洗浄し、硫酸マグネシウムを加え、乾燥させた。溶媒を留去し、白色固体のベース樹脂を得た（3.00g）。数平均分子量：2500
【００２９】
〔ケイ素系アルカリ可溶性樹脂の合成〕
実施例４
実施例２で得られたベース樹脂1.0gにトルエン10mL、トリエチルアミン0,2g (1.96 mmol)を加え、８０℃にて攪拌させた。実施例１で合成した環状酸無水物基を有するハロゲノシラン（I）0.2g (0.86mmol)をゆっくり滴下させた。系を８０℃にて１時間攪拌させ、オイルバスを外し系を室温まで冷却させた。生成した白色塩をろ別し、減圧下ろ液を留去し、白色のケイ素系アルカリ可溶性樹脂を得た（0.27g）。数平均分子量：5000
【００３０】
実施例５
実施例３で得られたベース樹脂1.0gにトルエン10mL、トリエチルアミン0,2g (1.96 mmol)を加え、８０℃にて攪拌させた。実施例１で合成した環状酸無水物基を有するハロゲノシラン（I）0.2g (0.86mmol)をゆっくり滴下させた。系を８０℃にて１時間攪拌させ、オイルバスを外し系を室温まで冷却させた。生成した白色塩をろ別し、減圧下ろ液を留去し、白色のケイ素系アルカリ可溶性樹脂を得た（0.27g）。数平均分子量：2700
【００３１】
比較例１
実施例５の環状酸無水物基を有するハロゲノシラン（I）をトリメチルクロロシランとした以外は、実施例５と同様な手法で合成を行い、白色個体を得た（0.36g）。数平均分子量：7400
【００３２】
〔アルカリ可溶性試験〕
評価方法：スピンコート法により基板上に樹脂を1μｍの厚さに塗布し、それを2.38%テトラメチルアンモニウムヒドロキシド（TMAH)水溶液に浸漬させ、基板上の塗膜が完全に溶解する時間を測定してアルカリ可溶性を評価した。
【００３３】
【表２】
【発明の効果】
本発明によって、環状酸無水物基を有する新規なハロゲノシラン及び、それを反応させてなるケイ素系アルカリ可溶性樹脂が提供される。
本発明の環状酸無水物基を有する新規なハロゲノシランは、ケイ素原子に結合した加水分解性のハロゲン原子が存在するため、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。
一方、環状酸無水物基は、加水分解により容易に開環反応が起こり、ジカルボン酸が生成し、アルカリ水溶性基として機能する。
即ち、カップリング反応と加水分解開環反応の２つの反応点を有する複反応性ケイ素化合物として機能する。
本発明の環状酸無水物基を有する新規なハロゲノシランは、そのため、有機合成の中間原料、ポリマー樹脂の合成原料、ポリマーの改質剤、無機化合物の表面処理剤として有用である。
本発明のケイ素系アルカリ可溶性樹脂は、優れたアルカリ可溶性を発現するので、化学増幅型レジストのレジスト樹脂として有用である。
【図面の簡単な説明】
【図１】 第１図は実施例１で得られた生成物の1H-NMRスペクトルを示す。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a novel halogenosilane having a cyclic acid anhydride group and an alkali-soluble resin obtained by reacting the same.
[0002]
[Prior art]
Various types of silicon-based alkali-soluble resins having a carboxyl group are known (JP-A-11-130860, JP-A-2001-5185: dissolution rate 0.4 μm / s). Since these resins have only one equivalent of a carboxyl group with respect to the terminal silicon atom, there remains a problem in alkali solubility.
On the other hand, no silicon-based alkali-soluble resin having two carboxyl groups per terminal silicon atom is known.
If 2 equivalents of a carboxyl group can be introduced with respect to the terminal silicon atom, a significant improvement in solubility can be expected as compared with conventional silicon-based alkali-soluble resins.
[0003]
[Problems to be solved by the invention]
An object of the present invention is to provide a novel halogenosilane having a cyclic acid anhydride group and a silicon-based alkali-soluble resin obtained by reacting the same, whereby a novel synthesis method in organic synthesis and other fields, It is to enable material surface treatment method, resin modification, production of a new resin, and the like.
[0004]
[Means for Solving the Problems]
The present inventor has found that halogenosilanes having a cyclic acid anhydride group have one silicon functional group on the one hand and a cyclic acid anhydride group on the other hand. It was found useful as a ring agent, and the present invention was completed.
That is, the present invention is a halogenosilane represented by the following general formula:
[0005]
[Chemical 2]
(Wherein R 1 and R 2 represent a methyl group , R 3 represents a linear alkylene group having 3 carbon atoms, and X represents chlorine ), and alkali solubility obtained by reacting it with a base resin Resin. Hereinafter, the present invention will be described in detail.
[0007]
DETAILED DESCRIPTION OF THE INVENTION
"Halogenosilanes with cyclic anhydride groups"
The novel compound of the present invention is represented by the above general formula. R 1 and R 2 are methyl groups . Raw materials are easy to obtain, synthesis is the preferred lame methyl group or trivial. R 3 is an alkylene group having 3 carbon atoms and is linear , specifically a trimethylene group . From easy task and ease of availability of synthetic, linear hydrocarbons carbon number is 3 is most preferred. X is chlorine. Is most preferred that the chlorine from the material availability viewpoint. That is , the halogenosilane of the present invention is a compound (I) represented by the following structural formula.
[0008]
[Chemical 3]
The silicon-based compound of the present invention can be produced, for example, as follows.
Allyl succinic anhydride is hydrosilylated with dimethylchlorosilane to obtain the silicon-based compound (I) of the present invention.
Usually, this reaction is carried out in the presence of a catalyst. Preferred catalysts include cobalt, nickel, ruthenium, rhodium, palladium, iridium, platinum and other group 8-10 group metals, organometallic complexes, metal salts. , And metal oxides, among which platinum-based catalysts are particularly preferable.
Preferred platinum-based catalysts include chloroplatinic acid hexahydrate (H 2 PtCl 6 · 6H 2 O), cis-PtCl 2 (PhCN) 2 , platinum carbon, platinum complex coordinated with divinylsiloxane (PtDVTMDS), etc. Illustrated. Ph represents a phenyl group. The preferred amount of catalyst used is 0.1 ppm to 1,000 ppm relative to the amount of compound (I).
In addition, the reaction temperature control operation depends on heating from the outside and the supply rate of dimethylchlorosilane, and thus cannot be determined unconditionally. However, the reaction temperature is usually maintained in the range of room temperature to 110 ° C. The relation reaction can be continued smoothly. After completion of the reaction, the solvent and volatile components are distilled off under reduced pressure, and the compound (I) is obtained by purification by distillation under reduced pressure.
[0010]
"Silicon alkali-soluble resin"
The silicon-based alkali-soluble resin of the present invention can be produced, for example, as follows.
First, a base resin is obtained by adding a gelation inhibitor, a catalyst, water, and a solvent to alkoxysilane or halogenosilane for forming a resin skeleton, followed by heating and stirring.
[0011]
Examples of preferable alkoxysilane include tetramethoxysilane, tetraethoxysilane, trimethoxysilane, triethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane, and phenyltriethoxysilane.
[0012]
Preferred halogenosilanes include tetrachlorosilane, trichlorosilane, methyltrichlorosilane, phenyltrichlorosilane, and the like.
[0013]
As preferred gelling inhibitors, disiloxane derivatives are used, such as hexamethyldisiloxane, 1,3-divinyltetramethyldisiloxane, hexaethyldisiloxane, hexaphenyldisiloxane, pentamethyldisiloxane, 1,1,3. , 3-Tetramethyldisiloxane, 1,1,3,3-tetraisopropyldisiloxane, 1,1,3,3-tetraphenyldimethyldisiloxane, 1,1,1,3,3-pentamethyl-3-acetoxy Examples include disiloxane.
[0014]
Preferred catalysts include acid catalysts such as hydrochloric acid, sulfuric acid, nitric acid and acetic acid, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide and the like.
[0015]
Preferred solvents include polar solvents such as water, acetone, methyl isobutyl ketone, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, methanol, ethanol, isopropyl alcohol, butanol, or hexane, benzene, toluene, xylene, chloroform, methylene chloride. Nonpolar solvents such as
[0016]
The preferred temperature when the above components are heated and stirred to react is from room temperature to 120 ° C., and the preferred charge ratio of each component per mole of alkoxysilane or halogenosilane is as follows.
That is, it is 0.1 to 0.5 mol for the gelation inhibitor, 0.3 to 6 mol for the catalyst, 0.3 to 30 mol for water, and 0 for the solvent. ~ 15 liters.
[0017]
The preferred number average molecular weight of the base resin is 2000 to 5000. If it is less than 2000, the operation of recovering the base resin after the reaction may be complicated, and if it exceeds 50000, it may be difficult to smoothly carry out the silylation reaction described later.
[0018]
Next, the base resin obtained as described above is silylated by reacting the organosilicon compound of the present invention in the presence of a solvent and a base to obtain a silicon-based alkali-soluble resin.
Preferred solvents include polar solvents such as acetone, methyl isobutyl ketone, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, methanol, ethanol, isopropyl alcohol, butanol, or hexane, benzene, toluene, xylene, chloroform, methylene chloride, etc. Nonpolar solvents are exemplified.
[0019]
Preferred examples of the base include triethylamine, pyridine, ethyldiisopropylamine, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide and the like.
A preferable temperature when the above components are heated and stirred to cause a silylation reaction is room temperature to 120 ° C., and a preferable charging ratio of the base resin and the compound of the present invention is 0.5 to 200 mmol per 1 g of the base resin. .
[0020]
The preferred number average molecular weight of the alkali-soluble organosilicon resin obtained as described above is 2000 to 5000. If it is less than 2000, it is difficult to produce the resin, and if it exceeds 50000, there is a possibility that sufficient alkali solubility cannot be exhibited.
[0021]
The silicon-based alkali-soluble resin of the present invention is useful as a resist resin for a chemically amplified resist. By soaking in an alkaline aqueous solution, a dicarboxylic acid is generated in the resin and exhibits excellent alkali solubility.
[0022]
【Example】
Hereinafter, the present invention will be specifically described with reference examples and examples.
[0023]
[Synthesis of novel halogenosilanes having cyclic acid anhydride groups]
Example 1
A reactor equipped with a magnetic stir bar, condenser, thermometer and dropping funnel was placed in a dry nitrogen atmosphere, and 24.7 g (176 mmol) of allyl succinic anhydride was charged and stirred at 60 ° C. A solution of PtDVTMDS in xylene (10 μl, 0.0005 mmol) was charged, and then 20.0 g (211 mmol) of dimethylchlorosilane was gradually added. After completion of dropping, the mixture was stirred at 60 ° C. for 6 hours. After evaporating volatile components under reduced pressure, the target product was purified by distillation under reduced pressure to obtain a colorless and transparent liquid. [Boiling point: 148-150 ° C (267Pa), Yield: 84%]
When this liquid was subjected to 1 H-NMR measurement at 270 MHz, the spectrum shown in FIG. 1 was obtained. The δ value and its attribution are shown in Table 1. It was confirmed that the liquid thus obtained was halogenosilane (I) having a cyclic acid anhydride group.
[0024]
[Formula 4]
[Table 1]
[Chemical formula 5]
[Synthesis of base resin]
Example 2
A reactor equipped with a magnetic stir bar, condenser, thermometer, and dropping funnel was charged with 1.87 g (11.5 mmol) of hexamethyldisiloxane, 17.5 g (970 mmol) of water, and 10.8 g (180 mmol) of acetic acid. Stir at ° C. 6.24 g (30 mmol) of tetraethoxysilane was dropped into the system over 30 minutes. After stirring the system at 60 ° C. for 1 hour, 3.12 g (15 mmol) of tetraethoxysilane was dropped again into the system over 30 minutes. The system was stirred at 60 ° C. for 3 hours, the reaction solution was separated by decantation, and a base resin insoluble in the reaction solution was recovered. Washing with water was repeated three times, and 100 mL of tetrahydrofuran was added to dissolve the base resin. After adding magnesium sulfate and drying, tetrahydrofuran was distilled off to obtain a white solid base resin (2.75 g). Number average molecular weight: 4600
[0028]
Example 3
A reactor equipped with a magnetic stir bar, condenser, thermometer, and dropping funnel was charged with 1.87 g (11.5 mmol) of hexamethyldisiloxane, 17.5 g (970 mmol) of water, 10.8 g (180 mmol) of acetic acid, and 100 mL of tetrahydrofuran. The inside was stirred at 60 ° C. 6.24 g (30 mmol) of tetraethoxysilane was dropped into the system over 30 minutes. After stirring the system at 60 ° C. for 1 hour, 3.12 g (15 mmol) of tetraethoxysilane was dropped again into the system over 30 minutes. The system was allowed to stir at 60 ° C. for 3 hours. Methyl isobutyl ketone was added and the organic layer was extracted. The organic layer was washed 3 times with water, magnesium sulfate was added and dried. The solvent was distilled off to obtain a white solid base resin (3.00 g). Number average molecular weight: 2500
[0029]
[Synthesis of silicon-based alkali-soluble resins]
Example 4
To 1.0 g of the base resin obtained in Example 2, 10 mL of toluene and 0,2 g (1.96 mmol) of triethylamine were added and stirred at 80 ° C. 0.2 g (0.86 mmol) of halogenosilane (I) having a cyclic acid anhydride group synthesized in Example 1 was slowly added dropwise. The system was allowed to stir at 80 ° C. for 1 hour, the oil bath was removed and the system was allowed to cool to room temperature. The produced white salt was filtered off, and the filtrate was distilled off under reduced pressure to obtain a white silicon-based alkali-soluble resin (0.27 g). Number average molecular weight: 5000
[0030]
Example 5
To 1.0 g of the base resin obtained in Example 3, 10 mL of toluene and 0,2 g (1.96 mmol) of triethylamine were added and stirred at 80 ° C. 0.2 g (0.86 mmol) of halogenosilane (I) having a cyclic acid anhydride group synthesized in Example 1 was slowly added dropwise. The system was allowed to stir at 80 ° C. for 1 hour, the oil bath was removed and the system was allowed to cool to room temperature. The produced white salt was filtered off, and the filtrate was distilled off under reduced pressure to obtain a white silicon-based alkali-soluble resin (0.27 g). Number average molecular weight: 2700
[0031]
Comparative Example 1
Synthesis was carried out in the same manner as in Example 5 except that trimethylchlorosilane was used as the halogenosilane (I) having a cyclic acid anhydride group in Example 5 to obtain a white solid (0.36 g). Number average molecular weight: 7400
[0032]
[Alkali solubility test]
Evaluation method: The resin is applied to the substrate to a thickness of 1μm by spin coating, and it is immersed in 2.38% tetramethylammonium hydroxide (TMAH) aqueous solution, and the time required for the coating film on the substrate to completely dissolve is measured. Then, alkali solubility was evaluated.
[0033]
[Table 2]
【The invention's effect】
The present invention provides a novel halogenosilane having a cyclic acid anhydride group and a silicon-based alkali-soluble resin obtained by reacting the same.
Since the novel halogenosilane having a cyclic acid anhydride group of the present invention has a hydrolyzable halogen atom bonded to a silicon atom, a siloxane bond is formed by reaction with other organosilicon compounds (including polymers). Or a coupling reaction with a silanol group in the inorganic compound.
On the other hand, the cyclic acid anhydride group easily undergoes a ring-opening reaction by hydrolysis to produce a dicarboxylic acid, and functions as an alkaline water-soluble group.
That is, it functions as a double-reactive silicon compound having two reaction points, a coupling reaction and a hydrolytic ring-opening reaction.
Therefore, the novel halogenosilane having a cyclic acid anhydride group of the present invention is useful as an intermediate raw material for organic synthesis, a synthetic raw material for polymer resin, a polymer modifier, and a surface treatment agent for inorganic compounds.
Since the silicon-based alkali-soluble resin of the present invention exhibits excellent alkali solubility, it is useful as a resist resin for chemically amplified resists.
[Brief description of the drawings]
FIG. 1 shows the 1 H-NMR spectrum of the product obtained in Example 1. FIG.
Claims (2)
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| JP2001325690A JP4013520B2 (en) | 2001-10-23 | 2001-10-23 | Novel halogenosilanes and alkali-soluble resins |
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| JP2001325690A JP4013520B2 (en) | 2001-10-23 | 2001-10-23 | Novel halogenosilanes and alkali-soluble resins |
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| JP2003128679A JP2003128679A (en) | 2003-05-08 |
| JP4013520B2 true JP4013520B2 (en) | 2007-11-28 |
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