JP2994937B2

JP2994937B2 - 有機ポリマー複合無機微粒子の製造方法

有機ポリマー複合無機微粒子の製造方法

Info

Publication number: JP2994937B2
Authority: JP; Japan
Prior art keywords: organic polymer; inorganic fine; group; fine particles; polymer composite
Prior art date: 1993-11-09
Legal status : Expired - Lifetime

Application number

JP33649893A

Other languages

English (en)

Japanese (ja)

Other versions

JPH07178335A (ja

Inventor

大成富久

成史倉本

知史石田

忠弘米田

雅也吉田

一郎名村

Current Assignee

Nippon Shokubai Co Ltd

Original Assignee

Nippon Shokubai Co Ltd

Priority date

1993-11-09

Filing date

1993-12-28

Publication date

1999-12-27

1993-12-28 Application filed by Nippon Shokubai Co Ltd filed Critical Nippon Shokubai Co Ltd

1994-11-04 Priority to US08/334,052 priority Critical patent/US5683501A/en

1994-11-08 Priority to KR1019940029182A priority patent/KR0152119B1/ko

1994-11-08 Priority to TW083110344A priority patent/TW272220B/zh

1994-11-09 Priority to DE69411258T priority patent/DE69411258T2/de

1994-11-09 Priority to EP94308248A priority patent/EP0661311B1/en

1995-07-18 Publication of JPH07178335A publication Critical patent/JPH07178335A/ja

1999-12-27 Application granted granted Critical

1999-12-27 Publication of JP2994937B2 publication Critical patent/JP2994937B2/ja

2014-12-27 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

229920000620 organic polymer Polymers 0.000 title claims abstract description 405
239000010419 fine particle Substances 0.000 title claims abstract description 361
239000002131 composite material Substances 0.000 title claims description 298
238000004519 manufacturing process Methods 0.000 title claims description 42
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238000000034 method Methods 0.000 claims abstract description 45
239000007788 liquid Substances 0.000 claims description 63
150000002736 metal compounds Chemical class 0.000 claims description 44
239000002994 raw material Substances 0.000 claims description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
238000006243 chemical reaction Methods 0.000 claims description 36
238000006460 hydrolysis reaction Methods 0.000 claims description 34
230000007062 hydrolysis Effects 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 16
125000002252 acyl group Chemical group 0.000 claims description 13
229910052751 metal Inorganic materials 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
239000002184 metal Substances 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 7
229910052710 silicon Inorganic materials 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
229910052782 aluminium Inorganic materials 0.000 claims description 4
229910052719 titanium Inorganic materials 0.000 claims description 3
229910052726 zirconium Inorganic materials 0.000 claims description 3
239000006185 dispersion Substances 0.000 abstract description 167
239000000203 mixture Substances 0.000 abstract description 113
239000002245 particle Substances 0.000 abstract description 104
238000000576 coating method Methods 0.000 abstract description 56
239000011248 coating agent Substances 0.000 abstract description 53
238000009826 distribution Methods 0.000 abstract description 22
239000000654 additive Substances 0.000 abstract description 7
230000003301 hydrolyzing effect Effects 0.000 abstract description 6
239000011159 matrix material Substances 0.000 abstract description 6
239000000463 material Substances 0.000 abstract description 5
239000012778 molding material Substances 0.000 abstract description 5
230000000996 additive effect Effects 0.000 abstract description 4
229910000765 intermetallic Inorganic materials 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
229920005989 resin Polymers 0.000 description 69
239000011347 resin Substances 0.000 description 69
239000000243 solution Substances 0.000 description 53
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
229920000642 polymer Polymers 0.000 description 42
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 39
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125000003545 alkoxy group Chemical group 0.000 description 38
239000000126 substance Substances 0.000 description 36
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 33
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238000003786 synthesis reaction Methods 0.000 description 32
125000000524 functional group Chemical group 0.000 description 29
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238000001816 cooling Methods 0.000 description 24
239000003054 catalyst Substances 0.000 description 23
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
238000001035 drying Methods 0.000 description 20
239000012948 isocyanate Substances 0.000 description 20
229920001296 polysiloxane Polymers 0.000 description 19
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
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239000002244 precipitate Substances 0.000 description 17
230000000052 comparative effect Effects 0.000 description 16
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LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
235000011114 ammonium hydroxide Nutrition 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 12
239000007789 gas Substances 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
239000006087 Silane Coupling Agent Substances 0.000 description 11
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
229910000077 silane Inorganic materials 0.000 description 11
LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 11
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 10
239000007822 coupling agent Substances 0.000 description 10
238000011056 performance test Methods 0.000 description 10
239000000758 substrate Substances 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
238000005227 gel permeation chromatography Methods 0.000 description 9
150000002513 isocyanates Chemical class 0.000 description 9
239000011259 mixed solution Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000011521 glass Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
239000002253 acid Substances 0.000 description 7
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 7
238000011156 evaluation Methods 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000003973 paint Substances 0.000 description 7
239000002002 slurry Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
229920000178 Acrylic resin Polymers 0.000 description 6
239000004925 Acrylic resin Substances 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
229920000877 Melamine resin Polymers 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
125000004429 atom Chemical group 0.000 description 6
239000008199 coating composition Substances 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 6
229920005906 polyester polyol Polymers 0.000 description 6
239000011342 resin composition Substances 0.000 description 6
239000006228 supernatant Substances 0.000 description 6
125000003396 thiol group Chemical group [H]S* 0.000 description 6
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 5
125000003277 amino group Chemical group 0.000 description 5
229920003180 amino resin Polymers 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
238000004132 cross linking Methods 0.000 description 5
239000002612 dispersion medium Substances 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 5
125000003700 epoxy group Chemical group 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
238000005259 measurement Methods 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
238000004381 surface treatment Methods 0.000 description 5
238000005406 washing Methods 0.000 description 5
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 4
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
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
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
229910001209 Low-carbon steel 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 4
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
239000004793 Polystyrene Substances 0.000 description 4
229910004298 SiO 2 Inorganic materials 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
238000005119 centrifugation Methods 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
230000007423 decrease Effects 0.000 description 4
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical group 0.000 description 4
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
230000000704 physical effect Effects 0.000 description 4
230000000379 polymerizing effect Effects 0.000 description 4
229920002223 polystyrene Polymers 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000004576 sand Substances 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 4
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
YZVRVDPMGYFCGL-UHFFFAOYSA-N triacetyloxysilyl acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)OC(C)=O YZVRVDPMGYFCGL-UHFFFAOYSA-N 0.000 description 4
BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229910000831 Steel Inorganic materials 0.000 description 3
BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
TVJPBVNWVPUZBM-UHFFFAOYSA-N [diacetyloxy(methyl)silyl] acetate Chemical compound CC(=O)O[Si](C)(OC(C)=O)OC(C)=O TVJPBVNWVPUZBM-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
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150000001412 amines Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
VGWJKDPTLUDSJT-UHFFFAOYSA-N diethyl dimethyl silicate Chemical compound CCO[Si](OC)(OC)OCC VGWJKDPTLUDSJT-UHFFFAOYSA-N 0.000 description 3
JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 3
CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 3
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 3
RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 description 3
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 3
BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 3
150000002894 organic compounds Chemical class 0.000 description 3
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
238000011160 research Methods 0.000 description 3
239000010959 steel Substances 0.000 description 3
150000005846 sugar alcohols Polymers 0.000 description 3
UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 3
QHUNJMXHQHHWQP-UHFFFAOYSA-N trimethylsilyl acetate Chemical compound CC(=O)O[Si](C)(C)C QHUNJMXHQHHWQP-UHFFFAOYSA-N 0.000 description 3
238000000108 ultra-filtration Methods 0.000 description 3
238000001291 vacuum drying Methods 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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AHEQEPCAIFTNHE-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol butan-1-olate zirconium(4+) Chemical compound N(CCO)(CCO)CCO.[O-]CCCC.[Zr+4].[O-]CCCC.[O-]CCCC.[O-]CCCC AHEQEPCAIFTNHE-UHFFFAOYSA-N 0.000 description 2
KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 description 2
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DUFCMRCMPHIFTR-UHFFFAOYSA-N 5-(dimethylsulfamoyl)-2-methylfuran-3-carboxylic acid Chemical compound CN(C)S(=O)(=O)C1=CC(C(O)=O)=C(C)O1 DUFCMRCMPHIFTR-UHFFFAOYSA-N 0.000 description 2
GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical class NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 2
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
KLQSRTKDOLFPQJ-UHFFFAOYSA-M CCCCO[Ti+](OCCCC)OCCCC.CCCCCCCCCCCCCCCCCC([O-])=O Chemical compound CCCCO[Ti+](OCCCC)OCCCC.CCCCCCCCCCCCCCCCCC([O-])=O KLQSRTKDOLFPQJ-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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