KR101494850B1 - 관능기를 가지는 케이지 개열형 실록산수지와 그 제조방법 - Google Patents

관능기를 가지는 케이지 개열형 실록산수지와 그 제조방법 Download PDF

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Publication number: KR101494850B1
Authority: KR; South Korea
Prior art keywords: group; cage; meth; reaction; solvent
Prior art date: 2007-02-16

Application number

KR1020097017813A

Other languages

English (en)

Korean (ko)

Other versions

KR20090111341A (ko

Inventor

아키코 야마사키

타카시 사이토

토시히로 카와타니

히데키 안도

Original Assignee

신닛테츠 수미킨 가가쿠 가부시키가이샤

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2007-02-16

Filing date

2008-02-13

Publication date

2015-02-23

2008-02-13 Application filed by 신닛테츠 수미킨 가가쿠 가부시키가이샤 filed Critical 신닛테츠 수미킨 가가쿠 가부시키가이샤

2009-10-26 Publication of KR20090111341A publication Critical patent/KR20090111341A/ko

2015-02-23 Application granted granted Critical

2015-02-23 Publication of KR101494850B1 publication Critical patent/KR101494850B1/ko

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KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims abstract description 85
239000011347 resin Substances 0.000 title claims abstract description 70
229920005989 resin Polymers 0.000 title claims abstract description 70
125000000524 functional group Chemical group 0.000 title claims abstract description 13
238000004519 manufacturing process Methods 0.000 title description 8
238000006243 chemical reaction Methods 0.000 claims abstract description 81
-1 disiloxane compound Chemical class 0.000 claims abstract description 42
239000003054 catalyst Substances 0.000 claims abstract description 37
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 34
239000012454 non-polar solvent Substances 0.000 claims abstract description 33
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 28
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 27
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 20
239000002904 solvent Substances 0.000 claims abstract description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 14
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238000011067 equilibration Methods 0.000 claims abstract description 13
239000002798 polar solvent Substances 0.000 claims abstract description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
238000009833 condensation Methods 0.000 claims abstract description 6
230000005494 condensation Effects 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
238000000034 method Methods 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
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150000003377 silicon compounds Chemical class 0.000 claims description 6
239000000463 material Substances 0.000 claims description 4
239000006087 Silane Coupling Agent Substances 0.000 claims 3
239000003795 chemical substances by application Substances 0.000 claims 1
238000009826 distribution Methods 0.000 abstract description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 28
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 22
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 19
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
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XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 4
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VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
230000007704 transition Effects 0.000 description 4
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ZIFLDVXQTMSDJE-UHFFFAOYSA-N 3-[[dimethyl-[3-(2-methylprop-2-enoyloxy)propyl]silyl]oxy-dimethylsilyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(C)O[Si](C)(C)CCCOC(=O)C(C)=C ZIFLDVXQTMSDJE-UHFFFAOYSA-N 0.000 description 3
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 3
NOKUWSXLHXMAOM-UHFFFAOYSA-N hydroxy(phenyl)silicon Chemical class O[Si]C1=CC=CC=C1 NOKUWSXLHXMAOM-UHFFFAOYSA-N 0.000 description 3
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LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 3
KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 2
MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 2
URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 2
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FKPSBYZGRQJIMO-UHFFFAOYSA-M benzyl(triethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC1=CC=CC=C1 FKPSBYZGRQJIMO-UHFFFAOYSA-M 0.000 description 2
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
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238000006297 dehydration reaction Methods 0.000 description 2
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BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
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BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
YQJPWWLJDNCSCN-UHFFFAOYSA-N 1,3-diphenyltetramethyldisiloxane Chemical compound C=1C=CC=CC=1[Si](C)(C)O[Si](C)(C)C1=CC=CC=C1 YQJPWWLJDNCSCN-UHFFFAOYSA-N 0.000 description 1
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AMZNFNXOVYDPBW-UHFFFAOYSA-N 3-[[dimethyl(3-prop-2-enoyloxypropyl)silyl]oxy-dimethylsilyl]propyl prop-2-enoate Chemical compound C=CC(=O)OCCC[Si](C)(C)O[Si](C)(C)CCCOC(=O)C=C AMZNFNXOVYDPBW-UHFFFAOYSA-N 0.000 description 1
XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
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YIIAFYZYURUBMN-UHFFFAOYSA-N [dimethyl(propyl)silyl]oxy-dimethyl-propylsilane Chemical compound CCC[Si](C)(C)O[Si](C)(C)CCC YIIAFYZYURUBMN-UHFFFAOYSA-N 0.000 description 1
MFIBZDZRPYQXOM-UHFFFAOYSA-N [dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silyl]oxy-dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C1OC1COCCC[Si](C)(C)O[Si](C)(C)CCCOCC1CO1 MFIBZDZRPYQXOM-UHFFFAOYSA-N 0.000 description 1
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BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
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235000019270 ammonium chloride Nutrition 0.000 description 1
238000000668 atmospheric pressure chemical ionisation mass spectrometry Methods 0.000 description 1
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XUKFPAQLGOOCNJ-UHFFFAOYSA-N dimethyl(trimethylsilyloxy)silicon Chemical compound C[Si](C)O[Si](C)(C)C XUKFPAQLGOOCNJ-UHFFFAOYSA-N 0.000 description 1
ICYXLXKMZOOGPX-UHFFFAOYSA-N dimethylsilyloxy-dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C[SiH](C)O[Si](C)(C)CCCOCC1CO1 ICYXLXKMZOOGPX-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- 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
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/10—Equilibration processes

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Silicon Polymers (AREA)

KR1020097017813A 2007-02-16 2008-02-13 관능기를 가지는 케이지 개열형 실록산수지와 그 제조방법 KR101494850B1 (ko)

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JPJP-P-2007-036006		2007-02-16
JP2007036006		2007-02-16
PCT/JP2008/052352 WO2008099850A1 (ja)	2007-02-16	2008-02-13	官能基を有するかご開裂型シロキサン樹脂とその製造方法

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JP (1)	JP5346593B2 (zh)
KR (1)	KR101494850B1 (zh)
CN (1)	CN101636433B (zh)
TW (1)	TWI431041B (zh)
WO (1)	WO2008099850A1 (zh)

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JP5385832B2 (ja) *	2010-03-23	2014-01-08	新日鉄住金化学株式会社	硬化型樹脂組成物及びこれから得られる成形体
JP5844796B2 (ja) *	2011-03-31	2016-01-20	新日鉄住金化学株式会社	硬化性シリコーン樹脂組成物及びシリコーン樹脂硬化物
JP6021605B2 (ja) *	2012-11-19	2016-11-09	新日鉄住金化学株式会社	かご型シルセスキオキサン化合物、それを用いた硬化性樹脂組成物及び樹脂硬化物
KR102280925B1 (ko) *	2014-07-25	2021-07-26	에스케이이노베이션 주식회사	하드코팅층 형성용 조성물
CN113087907B (zh) *	2019-12-23	2023-01-13	万华化学集团股份有限公司	一种硅醇锂及其制备方法和应用

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JPH10251407A (ja) *	1997-03-14	1998-09-22	Nippon Steel Chem Co Ltd	シリコーン化合物及びその製造方法
JP2003137944A (ja) *	2001-11-05	2003-05-14	Nippon Steel Chem Co Ltd	シリコーン樹脂組成物及びシリコーン樹脂成形体
JP2004123936A (ja)	2002-10-03	2004-04-22	Nippon Steel Chem Co Ltd	シリコーン樹脂組成物及びシリコーン樹脂成形体
JP2007031321A (ja)	2005-07-25	2007-02-08	Shin Etsu Chem Co Ltd	オルガノシロキサンが結合したイミドの製造方法、及びオルガノシロキサンが結合したアミド酸トリオルガノシリルエステルとその製造方法

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JP5362160B2 (ja) *	1999-08-04	2013-12-11	ハイブリッド・プラスチックス・インコーポレイテッド	多面体オリゴマーシルセスキオキサンの形成方法

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- 2008-02-13 KR KR1020097017813A patent/KR101494850B1/ko active IP Right Grant
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Patent Citations (4)

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JPH10251407A (ja) *	1997-03-14	1998-09-22	Nippon Steel Chem Co Ltd	シリコーン化合物及びその製造方法
JP2003137944A (ja) *	2001-11-05	2003-05-14	Nippon Steel Chem Co Ltd	シリコーン樹脂組成物及びシリコーン樹脂成形体
JP2004123936A (ja)	2002-10-03	2004-04-22	Nippon Steel Chem Co Ltd	シリコーン樹脂組成物及びシリコーン樹脂成形体
JP2007031321A (ja)	2005-07-25	2007-02-08	Shin Etsu Chem Co Ltd	オルガノシロキサンが結合したイミドの製造方法、及びオルガノシロキサンが結合したアミド酸トリオルガノシリルエステルとその製造方法

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KR20090111341A (ko)	2009-10-26
TWI431041B (zh)	2014-03-21
TW200904857A (en)	2009-02-01
JP5346593B2 (ja)	2013-11-20
JPWO2008099850A1 (ja)	2010-05-27
CN101636433B (zh)	2012-08-15
CN101636433A (zh)	2010-01-27
WO2008099850A1 (ja)	2008-08-21

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